BEFORE CONTROLLER OF PATENTS
THE PATENT OFFICE, MUMBAI
In the matter of section
25(2) of The Patents Act,
1970 as
amended
by
The Patents( Amendment)
Act, 2005
And
In
the
matter
of
The
Patents Rules, 2003 as
amended by The Patents
(Amendment)Rules, 2006
And
In the matter of:
Patent
No.IN236630 (Application
No: 897/MUM/2007)
PATENTEE : SHOGUN ORGANICS LIMITED, MUMBAI
OPPONENTS : ENDURA SPA, ITALY AND MANAKSIA LIMITED, KOLKATA
Hearing held on 29th September, 2015
Present in hearing:
Dr.Rajeshwari Hariharan (Agent representing the Patentee)
Ms.Karuna Goleria (Agent representing the Opponents)
Dr.Suman Verma (Examiner of Patents & Designs)
897/MUM/2007 (IN236630) Page 1 DECISION
1. An application for a patent bearing number 897/MUM/2007 was filed
in Patent Office, Mumbai on 10th May, 2007 entitled "PROCESS OF
MANUFACTURING D-TRANS ALLETHRIN”. A request for examination
under Section11-B was filed on 10th May, 2007 and was assigned a
Request No. 772/RQ-MUM/2007. As per the provision under Section 11A of Patents Act, the said application was published on 15th June,
2007.
2. The said application was examined according to the provisions in force
of the Act. A pre-grant opposition under Section 25(1) was filed by
Opponent no.2 Manaksia Limited, Mumbai on 05th February, 2009. The
said pre-grant opposition was heard by the then Learned Controller
Mr.M.A.Hafeez. Applicant filed Form 13 on 24th June 2009 adding an
example, which Controller allowed as per Section 59. On 30th June,
2009 Controller passed order rejecting the representation of pre-grant
opposition and granted the patent to the Patentee. On 28th August, 2009
the Opponent No.2 filed a review petition under Section 77 for review of the
Controller’s order dated 30th June, 2009. Subsequently on 25th
September, 2009 Controller passed order refusing review petition and
simultaneously
ordering
the
grant
of
Patent
to
the
Patentee
in
consequence whereof Patent Office granted a patent on the subject
application under Patent No. 236630. On 20th November 2009, the grant
was published in the Official Journal of the Patent Office.
3.Endura S.P.A and Manaksia Ltd. Opponents, in the present proceedings,
filed post grant opposition under Section 25(2) together with Written
Statement and affidavit of Mr. Valerio Borzatta (dated 17th November,
2010) on 22nd November, 2010. Patentee filed its Reply Statement on 8th
897/MUM/2007 (IN236630) Page 2 April, 2011 together with the affidavit of Dr. Prabuddha Ganguli dated 8th
April, 2011 as evidence in support of the patent on 8th April, 2011.
Certain other document were filed which shall be referred to, at
appropriate place. Subsequent to that, the matter was heard on the dates
5th December 2012 and 27th – 28th February 2013. Let it also be noted that
an Opposition Board was constituted in the subject matter as per Rule 56
of the Patents Rules 2003 and the report of the Opposition Board was
made available to both the parties on 2nd November, 2012. After the
hearing was over, written note of arguments were submitted by the
opponent on 28.12.2012 and 08.04.2013 and by the patentee on
15.01.2013 and 08.03.2013 by the patentee. Subsequent to hearing the
hearing controller revoked the patent.
4. The patentee filed an appeal before Hon’ble IPAB. The Hon’ble IPAB
allowed the appeal, setting aside the order passed by the learned Deputy
Controller. As per the directions issued by the Intellectual Property
Appellate Board (IPAB) order OA/7/2014/PT/MUM & Miscellaneous
Petition No.05/2014 in OA/7/2014/PT/MUM dated 18/08/2014 wherein
it was directed to constitute the Opposition Board again and thereafter
consider the expert evidence given by both the parties viz. the applicant
and the opponents and give their recommendations by furnishing their
report and to enable them to give their reply for the same. On receipt of
opposition Board recommendation, the learned Deputy Controller shall
afford a reasonable opportunity to both sides viz. the applicant and the
opponents to put forth their case and thereafter pass to pass the order in
the Patent application filed by the applicant in accordance with law and
on merits by considering each and every point raised in the matter and by
assigning valid reasons.
Accordingly a fresh opposition board was reconstituted. The opposition
submitted its fresh findings. The recommendations of the Opposition
897/MUM/2007 (IN236630) Page 3 board were forwarded to both the parties. Hearing was fixed on 08th May,
2015.
5. Miscellaneous Petition
The agent for the patentee at this instance filed a miscellaneous petition
under Rule 60 to furnish external expert affidavit of Dr. Raghavan Soman
in support of patentability on 30th April, 2015 with a humble prayer that
this document being technically important to decide the case. The
opponents initially objected but finally agreed when their prayer of
taking Documents D9 and D10 on record, which were not taken on
record earlier, was also considered. Both
the
parties
mutually
consented to taking the all the documents on record.
As the case was at the very early stage of prosecution and hearing in this
case was not conducted and the affidavit being so technical & important,
also adhering to the principles of natural justice & also in public
interest this expert evidence along with all other documents of the
opponents (i.e. Documents D9 and D10 of Opponents along with reply
affidavit filed by Valerio Borzatta) were taken on record. Both the parties
were given reasonable opportunity to present their case. The scheduled
hearing was adjourned. All these documents (i.e. external expert
affidavit of Dr. Raghavan Soman of Patentee and Documents D9 & D10
of Opponents along with reply affidavit filed by Valerio Borzatta) were
referred to the opposition board to submit their recommendations. The
board after considering all these documents submitted its revised
recommendations. After receiving the revised report from the opposition
board under Rule, 56. A notice of hearing along with revised board
recommendations were forwarded to both the parties and the date of
hearing was fixed on 29 th September, 2015.
897/MUM/2007 (IN236630) Page 4 In view of these facts, I hereby dispose the miscellaneous petition holding
that in the present case the final hearing was yet to be taken and also
giving both the parties a reasonable opportunity to present their case as
per direction of Hon’ble IPAB. Care was taken strictly to observe that
there should not be any procedural lapse which will lead again to
reconstitute an Opposition Board, as this fact is neither supported by
the Order of the Hon’ble IPAB nor is acceptable under the Scheme of
Law.
6. Preliminary issues:
Before going into the detailed arguments and counter arguments of the
learned agents with respect to the substantive issues, I would like to deal
with preliminary issues involved in this matter. The issue aroused for
consideration where as follows:
a) Whether the principle of 'res-judicata' bars the Opponent from
relying on cited prior art documents D1 and D2 and the ground of
insufficiency in the Post-grant proceedings;
b) Whether the principle of 'stare decisis 'operates in respect of cited
prior art documents D1 and D2 and whether the judgement rendered
in the pre-grant proceedings has any bearing on the Post-grant
proceedings.
ISSUE 1 : RES-JUDICATA
Whether opponent is barred from relying on documents Dl-D2 and the
grounds of insufficiency as being barred by 'res-judicata' or 'ressubjudice'?
897/MUM/2007 (IN236630) Page 5 PATENTEE’S SUBMISSIONS :
The patentee contended that the opponent is barred from relying on
documents Dl-D2 and the grounds of insufficiency as being barred by 'resjudicata' or 'res-subjudice'. Patentee explained that the principle of resjudicata is well known: that if a decision has been rendered in a
proceeding between two parties; the same shall not reopened by either of
the parties by initiating another or similar proceeding. Thus the Ld.
Controller shall not be called upon in a post-grant opposition to try and
decide any issues in an opposition which were directly substantially in
issue in the pre-grant opposition between the same parties or their privies
i.e. the Applicant/Patentee on one hand and the Opponents on the other
hand.
In the present case, the parties, the issues and grounds of Opposition are
the same as can be seen from table below:
Note: *Endura and Manaksia have formed a Joint Venture (Refer: reply evidence) and
therefore their interests have merged and they are a single economic entity. They are also
being represented jointly by one Patent attorney for the post grant opposition. No separate
pleadings filed by these parties.
In this case, Dl has been cited against Claim 1, steps (a) to (f) and
897/MUM/2007 (IN236630) Page 6 therefore, forms the bulk of the opposition. D2 is cited against Claim 1
step (h). D3 to D7 are cited only against Claim 1 step (g). Therefore, D1 is
the prime and the basis of the entire· opposition and Opponent is barred
from relying on this document.
The Patentee submitted that the principle of res-judicata which is set out
in Section 11 of the Code of Civil Procedure is explained in the case of
Ishwar Dutt vs. Land Acquisition Collector & Anr. [(2005) 7 SCC 190, para
18-20] as well as in the case of State of U.P. Vs. Nawab Hussain [(1977) 2
SCC 806, paras 3 and 7]. Patentee also relied on the case of Sulochana
Amma Vs. Narayanan Nair (AIR 1994 SC 152) paragraph 5-"5. Patentee
also submitted that in USA, if certain documents are already cited before
the Examiner, the third party is barred from citing these very documents
in a re-examination proceeding, which occurs after grant of patent. This is
because the issues that have been resolved prior to grant are not to be revisited after grant. Reliance was placed on IN RE PORTOLA Packing Inc.
[110 F.3d 789] - pg: 5
In view of the above case laws, the Patentee contended that the principles
of Res-judicata is applicable and Opponents are barred from relying on the
documents Dl and D2 in the Post-grant Opposition either alone or in
combination with other documents.
Referring to Opponents argument relating to Claim amendments, the
Opponents had argued that the complete specification was amended
subsequent to the pre-grant opposition, the claims are different and the
Opponents therefore did not have any opportunity to deal with the
amended
specification.
Patentee
submitted
that
this
argument
of
Opponents is completely misplaced, as the claim in pre-grant and postgrant are identical. As per pre-grant order, these changes in specification
were filed by filing Form-13. These changes were argued by Opponent in
897/MUM/2007 (IN236630) Page 7 'Review Petition' at pre-grant stage. All the alleged changes/amendments
have been raised by same Opponent at pre-grant stage itself. These have
already been argued and dismissed at pre-grant stage. Hence, this
argument is misconceived.
Patentee also contended that Opponents should not be given opportunity
to raise same issues again in order to avoid multiplicity of proceedings.
The Opponents only argument against 'Res-judicata' was that the law
permits an interested party who has failed in pre-grant proceeding can file
a post-grant opposition. Without going into the merits of the contention,
Patentee submitted that even if an interested person files a Post-grant
opposition, the principle of Res-judicata bars Opponents relying on same
documents Dl, D2 and the ground of insufficiency in these proceedings.
This would amount to granting the Opponent an opportunity to play a
second innings by way of post-grant opposition or a de: facto appeals
against pre-grant orders or re-opening the pre-grant orders. Patentee
submitted that in view of the above, the grounds of opposition contained in
Sections 25(2) (e), (1) & (g) with respect to D 1 and D2 cannot be
entertained by the Controller and as being barred by the principle of res
judicata.
OPPONENTS SUBMISSIONS :
To counter the legal arguments of the Patentee, Opponents submitted that
the principle of res-judicata cannot apply to post-grant opposition
proceedings under the Act for the following reasons:
The Patent Act, 1970 ('Act') specifically provides for two options for filing
opposition proceedings under section 25 viz.:
(i) Pre-grant opposition under S.25 (1) can be filed by 'any person' prior to
the grant of patent,
(ii) Post-grant opposition under S.25 (2) is allowed to be filed by 'any
897/MUM/2007 (IN236630) Page 8 person interested'
(iii) Section 25(1) and 25(2) of the Act are two independent legal provisions.
Section 25(2) is neither made subservient to section 25(1) nor has been
made subject to any other provisions of the Act (unlike section 64 of the
Act)
(iv) "Person interested" can file a post grant opposition on any or all of the
grounds made available in the section and such grounds are not subject to
the provisions of section 25(1)
(v) The legislative intent of the amendment of 2005 was very clear and the
Act does not preclude a "pre-grant" opponent from filing a post grant
opposition provided he fulfills the criteria of "being "an interested person".
(vi) The fora in both the pre-grant opposition proceeding and post-grant
opposition proceeding is different. The pre-grant opposition proceeding is a
summary proceeding which is conducted solely by the Learned Controller,
whereas in a post-grant opposition proceeding the Controller is assisted by
a specially constituted Opposition Board, and wherein the latter studies
the case and gives its Recommendation Report to the Controller. The
statutory authority is exercised under two different provisions
(vii) The post grant opposition cannot be equated with an "attempt to
obtain a second judgment in respect of the same issue”.
(viii) In the instant case, the subject in issue is also different. The pregrant opposition was filed and disposed of on the claims as filed whereas
the post grant opposition was filed against the claims as granted. The
cause of action is thus different in both the opposition proceedings.
The opponents placed their defense on the following case laws:
1. Re J. Mitra ("Exhibit A")
2. Delhi High Court decision dated 8 February 2010 in the cases UCB
Farchim SA v Cipla Limited and ors; Colorcon Inc v Ideal Cures Pvt Ltd &
Ors; Colorcon Inc v Ideal Cures Pvt Ltd & Ors; Yeda Research &
Development Co. Ltd vs Natco Pharma Limited; Eli Lilly & Co. v Ajanta
897/MUM/2007 (IN236630) Page 9 Pharma Limited. Ors; Eli Lilly & Co v Ranbaxy Laboratories Ltd & Ors,
considering the situation – Where the pre-grant opposition is rejected and
patent is granted has observed at paras 15;16, 18- where the pre-grant
opposition is rejected and the person who has filed that opposition
happens to be a person interested has in fact two remedies - the remedy of
either filing a post-grant opposition under S.25(2) or an application before
the IP AB under Section 64 of the Patents Act for revocation of the patent .
Opponents further submitted that above stand of Delhi High Court has
been followed by IPAB, as reflected in its various orders passed on 30
November 2010 in various cases viz. - Colgate-Palmolive Company v. The
Asstt Controller of Patents & Designs; Millennium Pharmaceuticals v Natco
Pharma Limited & Ors, Acme Tele Power Ltd v Controller of Patents and
Designs & Ors; Gilead Sciences Inc v Controller of Patents and Designs
and Anr.
In view of the above decisions, Opponents contended that the principle of
res-judicata does not apply to this post-grant opposition.
The Opponent also submitted his defense in relation to a "person
interested" as contemplated by the Patents Act, 1970. The opponents
submitted that Section 2(t) of the Patents Act, 1970 ('Act') defines
expression "persons interested" as-:- person interested includes a person
engaged in, or in promoting, research in the same field as that to which
the invention relates . The Opponents also relied on their reply statement
dated 10 June 2011, paragraph 6, where they have specifically mentioned
that the following patent/patent applications are filed by Opponent no. 2
in the Indian Patent Office. This clearly establishes Opponent's locus
standi as person interested as envisaged by the Act.
• IP no. 225276 (IPA 1397/KOLNP/2003): Title: Process For The Synthesis
Of 5-Benzyl-3-Furfuryl Alcohol
• IPA No.180/CHENP/2007: Title: Catalysts Based On Metal Complexes
897/MUM/2007 (IN236630) Page 10 For The Synthesis Of Optically Active Chrysanthemic Acid
• IPA No.1872/CHENP/2006: (IP No.248072) Title: Formulation Of A
Synergistic Insecticidal Composition As A Cyclodextrin-Complex
•IPA No.4093/CHENP/2007: Title: Process For Obtaining Enantiomers Of
Chrysanthemic Acid
• IPA No.5308/ CHENP /2007: Title: Innovative Formulation
• IPA No.2144/CHENP/2010:Title:Polyenylcyclopropane carboxylic Esters
with High Insecticidal Activity
Opponents also pointed that during the hearing the Patentee's agent
admitted that she had no objection that Opponent had filed the post-grant
opposition under section 25(2) of the Patents Act, 1970 after pre-grant
opposition proceedings. However, the Patentee has objected the documents
D1 and D2 being relied upon by the Opponent in post-grant opposition
proceedings which were relied on by the Opponent also in the pre-grant
opposition proceedings and on that ground the principle of res judicata
still applies.
To counter the case laws cited by Patentee, Opponents in rebuttal cited :
a) Section 11 of C.P.C,
b) Saroja v Chinnusamy: AIR 2007 S.C. 3067: (2007) 8 S.C.C.329,
c) Patent and Trademark Office Authorization Act of 2002 ("Act of2002"),
d) re Swanson,
e) Supreme Court 1680: State of Uttar Pradesh vs. Nawab Hussain,
f) Chiron Corporation vs Organon Teknika Limited
In view of the above rebuttal, the Opponents contended that the principle
of res judicata does not apply to this post-grant opposition proceedings.
897/MUM/2007 (IN236630) Page 11 CONCLUSION ON RES-JUDICATA
The concept of “res judicata” is applied to avoid repetitive litigations in a
irksome manner. After going through the arguments of both the parties
and from the decisions cited by the learned agent of the opponents it is
clear that the Supreme Court, High Court of Delhi and IPAB are of the
opinion that the post-grant opposition is the only remedy for a ‘person
interested’, after his failure at pre-grant stage.
The agent of the opponent also argued that the claims under analysis are
different at pre-grant and post-grant stages. The agent of the patentee
pointed out that even after the pre-grant opposition; the matter went
through a process of review.
I herein refer to the landmark decision of Delhi High Court in the cases UCB Farchim SA v Cipla Limited and ors; Colorcon Inc v Ideal Cures Pvt
Ltd & Ors; Colorcon Inc v Ideal Cures Pvt Ltd & Ors; Yeda Research &
Development Co. Ltd vs Natco Pharma Limited; Eli Lilly & Co. v Ajanta
Pharma Limited. Ors; Eli Lilly & Co v Ranbaxy Laboratories Ltd & Ors,
wherein the High Court considering the situation - Where the pre-grant
opposition is rejected and patent is granted.
The Delhi High Court in this case clearly pointed out differences between
the pre and post grant oppositions, on para 13 :
“13.In the first instance a distinction has to be drawn between a pre-grant
opposition and a post-grant opposition. While a pre-grant opposition can be
filed under Section 25 (1) of the Patents Act at any time after the publication
of the patent application but before the grant of a patent, a post-grant
opposition under Section 25(2) of the Patents Act has to be filed before the
expiry of one year from the date of the publication of the grant of patent.
897/MUM/2007 (IN236630) Page 12 A second significant difference, after the amendment of 2005, is that a pregrant opposition can be filed by “any person” whereas a post-grant
opposition under Section 25(2) can be filed only by “any person interested”. It
may be noticed that the application for revocation of a patent in terms of
Section 64 of the Patents Act can also to be filed only by “any person
interested”. In other words, the post-grant opposition and the application for
revocation cannot be filed by just about any person who is not shown to be a
person who is “interested”. A third significant difference is that the
representation at the stage of pre-grant is considered by the Controller
himself. Rule 55 of the Patents Rules requires the Controller to consider the
statement and evidence filed by the applicant and thereafter either refuse to
grant the patent or require the complete specification to be amended to his
satisfaction. Of course, in that event notice will be given to the applicant for
grant of patent who can file his reply and evidence. This Court finds merit in
the contention that the pre-grant opposition is in fact “in aid of the
examination of the patent application” by the Controller. The procedure is
however different aspect as far as the post-grant opposition is concerned.
There in terms of Section 25(3), the Controller has to constitute an Opposition
Board consisting of such officers as he may determine and refer to such
Opposition Board the notice of opposition along with other documents for its
examination and recommendations. After receiving the recommendations of
the Opposition Board, the Controller gives the patentee and the opponent an
opportunity of being heard. The Controller then takes a decision to maintain,
amend or revoke the patent. The fourth major difference between the pregrant and the post-grant opposition is that while in terms of Section 117 A an
appeal to the IPAB is maintainable against the order of the Controller in a
post-grant opposition under Section 25(4) of the Patents Act, an appeal has
not been expressly been made available against an order made under
Section 25(1) of the Patents Act”.
897/MUM/2007 (IN236630) Page 13 The Delhi High Court also in the same case has observed at paragraphs
15-16, 18 - where the pre-grant opposition is rejected and the person who
has filed that opposition happens to be a person interested has in fact two
remedies a) the remedy of either filing a post-grant opposition u/s 25(2) or
b) an application before the IPAB under Section 64 of the Patents Act for
revocation of the patent.
The relevant paragraphs 15, 16 and 18 of this decision are reproduced as
below:
“15. In the eventuality, where the pre-grant opposition is rejected, it is
apparent from the decision in J. Mitra and from a reading of Section 25 with
section 117A that as long as the person who has filed that opposition
happens to be a person interested, he would, after 1st January 2005 [the
date with effect from which section 25(2) came into force although the
provision was introduced only on 4th April 2005] have the remedy of filing a
post-grant opposition. He can, after 2nd April 2007, also file an application
before the IPAB under Section 64 of the Patents Act for revocation of the
patent. In other words, as explained by the Supreme Court in J.Mitra & co. as
long as that person is able to show that he is a ‘person interested’, he is not
without a remedy after his pre-grant opposition is rejected. He in fact has two
remedies. Even if his post-grant opposition is rejected, he can thereafter file
an appeal to the (PAR under Section 117A. Against the decision of the IPAB in
either event he will have the remedy of seeking judicial review in accordance
with law by filing a petition in the High Court. At this juncture it may be
noticed that in an order dated 2nd March 2009 in SLP (C) No. 3522 of 2009
(Indian Network for People with HI V/AIDS v. F. Hoffman-La Roche) the
Supreme Court permitted the unsuccessful pre-grant opposer, who had
challenged the rejection of his opposition by the Controller, to participate in
the post-grant stage.”
897/MUM/2007 (IN236630) Page 14 “16. The law is well settled that notwithstanding that a High Court has the
power and the jurisdiction under Article 226 of the Constitution to interfere
with the orders of any statutory authority which is of a quasi-judicial nature,
it will decline to exercise such jurisdiction where there is an efficacious
alternative statutory remedy available to the aggrieved person. See for e.g.,
Special Director v. Mohd. Ghulam Ghouse (2004) 3 5CC 440 [para 5 at page
443] Uttaranchal Forest Development Corp. v. Jabar Singh (2007) 2 SCC 112
[paras 43-45 at page 137], U. P. State Spinning Company Ltd. v. R.S.Pandey
(2005) 8 SCC 264 [paras 11-24 at pages 270-275], Titaghur Paper Mills
Company Ltd. v. State of Orissa (1983) 2 5CC 433 [para 6 at pages 437-438;
paras 8 & 9 at page 439; para U at page 441], Karnatalca Chemical
Industries v. Union of India (2000) 1OSCC 13 [para 2 at page 14] Assistant
Collector of Central Excise v. Jainson Hosiery Industries (1979) 4 SCC 22
[para I at page 23] and U.P. Slate Bridge Ltd. v. U.P. Rajya Setu Nigam S.
Karamchari Sangh (2004) 4 5CC 268 [para ii at pages 275-276; para 17 at
page 278].”
“18. To summarise this part of the discussion, as regards persons who have
not succeeded in the pre-grant opposition stage to prevent the grant of a
patent, and are persons ‘interested’ within the meaning of Section 25(2) and
Section 64 of the Patents Act, their remedy against the rejection of their pregrant opposition is to file a post-grant opposition under Section 25(2) and
await the decision of the Controller. If they are still aggrieved by that decision
under Section 25(4) of the Patents Act, they can file an appeal before the
IPAB in terms of Section 1 17A of the Patents Act.”
Thus the Delhi High Court, has clearly identified, three important
distinguishing features between pre-and post-grant procedures :
a) The first distinguishing feature, a pre-grant opposition under Section 25
(1) is before the grant of a patent whereas a post-grant opposition under
897/MUM/2007 (IN236630) Page 15 Section 25(2) of the Patents Act has to be filed before the expiry of one year
from the date of the publication of the grant of patent.
b) The second, a pre-grant opposition can be filed by “any person” whereas
a post-grant opposition can be filed only by “any person interested”.
c) The third significant difference is that “the representation at the stage of
pre-grant is considered by the Controller himself”, therefore, pre-grant
opposition is in fact “in aid of the examination” of the patent application by
the Controller, whereas in post-grant opposition, in terms of Section 25 (3),
the Controller has to constitute an Opposition Board and after receiving
the recommendations of the Opposition Board, the Controller gives the
patentee and the opponent an opportunity of being heard. The Controller
then takes a decision to maintain, amend or revoke the patent.
Also from the combined reading of the paragraph 13 with that of
paragraphs 15 to 18 of the cited decision of the Delhi High Court it is clear
that the procedures and the manner of analysis are totally different.
Hon’ble Court has clearly expressed its view that where the litigant is the
“person interested”, he can reappear in the post-grant proceedings. The
review, as referred by the learned agent of the patentee, was a review
under
pre-grant
and
thus
stands
separated
from
the
post-grant
procedures. Therefore the principle of Res Judicata is not applicable to this
case.
As regards to the question of person interested
As regards to question related to the person interested is concerned
Section 2(t) of the Patents Act, 1970 defines “persons interested” as –
person interested includes a person engaged in, or in promoting, research
in the same field as that to which the invention relates.
897/MUM/2007 (IN236630) Page 16 As regards to the patentee’s contention that the opponents are not the
person interested, the opponents submitted that they are engaged in
manufacturing mosquito repellents. Opponent 1 is a manufacturer and
holder of several patents related to insecticides. Opponent 2 is a leading
manufacturer
of
insecticides
and
chemical
components
used
for
manufacturer of insecticides.
The opponent cited the Indian patents owned by them, namely:
IP no. 225276 (IPA 1397/KOLNP/2003): Title: Process for the Synthesis of
5-Benzyl-3-Furfuryl Alcohol.
IPA No.180/CHENP/2007: Title: Catalysts Based On Metal Complexes for
the Synthesis of Optically Active Chrysanthemic Acid.
IPA
No.1872/CHENP/2006:
(IP
No.248072)
Title:
Formulation
ofa
Synergistic Insecticidal Composition as a Cyclodextrin-Complex.
IPA No.4093/CHENP/2007: Title: Process for Obtaining Enantiomers of
Chrysanthemic Acid.
IPA No.5308/ CHENP /2007: Title: Innovative Formulation.
IPA No.2144/CHENP/2010: Title: Polyenylcyclopropanecarboxylic Esters
with High Insecticidal Activity.
After verifying the above cited patent applications I found that the
opponents are the persons interested engaged in, or in promoting,
research in the same field as that to which the invention relates.
Also referring to the opponent’s submission wherein the opponent referred
to the Patent Law, by P Narayanan (Fourth edition) at p.183 – para 8-13.
In the context of the locus standi of person interested, Narayanan cites the
case of Merron’s Appln (1944)61 RPC at 92 (Assistant Controller) wherein
it was observed that there are three clear grounds upon which an
opponent can establish locus standi to oppose:
-first, the possession of patents relating to the same matter as the
897/MUM/2007 (IN236630) Page 17 application opposed;
-second, a manufacturing interest; and
-third, a trading interest.
I am fully agree with this citation quoted from “P Narayanan”. Patents are
for development of technology and are one of the major driving forces of
trades and industries. Therefore, a person need not be a researcher alone
in order to oppose a patent. It would be sufficient, if he is a manufacturer
or trader of the same substances or of substances which are derived from
the substances of impugned patent.
I therefore, reject the contention of the patentee and hold that the
opponents are persons interested within the meaning of the Patents Act
1970. Thus, having reached to the conclusion that the opponents are
“persons interested”, I am of the opinion that the opponents possess the
right to appear in the post-grant hearing as per the decision of the Delhi
High Court as cited above.
Therefore I state that the concept of ‘Res-judicata’ is not applicable
in this case.
ISSUE 2 : DOCTRINE OF ‘STARE DECISIS’
Whether the principle of 'stare decisis 'operates in respect of cited
prior art documents D1 and D2 and whether the judgement rendered
in the pre-grant proceedings has any bearing on the Post-grant
proceedings.
897/MUM/2007 (IN236630) Page 18 PATENTEE’S SUBMISSIONS:
Patentee contended that the principle of stare decisis has any effect qua
D1-D2 and the ground of insufficiency. Patentee submitted that :
a) The parties in the pre-grant proceeding and post-grant proceeding are
same.
b) The grounds and documents relied upon in pre-grant and post-grant
proceeding are same
c) Controller and this office has already taken a view in respect of these
documents and the ground of insufficiency at pre-grant stage,
Patentee contended that with regard to the documents D1-D2, Ld.
Controller of this same office at post-grant, is bound by the earlier view
taken by Ld. Controller of the same office at pre-grant. Present Authority
cannot take a different view unless a larger bench is formed. Patentee
contended that this present Authority is bound by the principle of 'stare
decisis' and 'Ressub-judice' and relied upon :
a) Shanker Raju V Lt Governor 2011(2) SCC 132 (paras 10 to 18);
b) SI Roopal Vs Lt Gov AIR 2000 SC 594 (paras12 to 14).
Patentee contended that Pre-grant and post-grant, both these proceedings
are within this same office and review of same issues amounts to Revision
or appeal which powers lies with a larger bench.
OPPONENTS’ SUBMISSIONS:
The Opponents in rebuttal, referred to page 139-140, para 10 of Shankar
Raju vs. Union of India, stated that this case is not at all relevant as the
doctrine of stare decisis does not apply to this case. It is stated therein
that . . . . . "The doctrine of stare decisis is expressed in the maxim stare
decisis et non quieta movere, which means "to stand by decisions and not
to disturb what is settled." ..... It is, therefore, sufficient for invoking the
rule of stare decisis that a certain decision was arrived at on a question
897/MUM/2007 (IN236630) Page 19 which arose or was argued, no matter on what reason the decision rests or
what is the basis of the decision". It is pertinent to note that in post-grant
opposition the granted claims of the impugned patent were challenged by
the Opponents, whereas in the pre-grant opposition the claims as filed
were challenged. As the impugned claims challenged in both the pregrant
and post-grant opposition proceedings were different; by no stretch of
imagination it can be said that the "order allowing the impugned
application" can invoke the doctrine of stare decisis, especially when the
statute has given liberty to the Opponent to challenge the granted claims
in the post-grant opposition proceedings. Based on this, the Opponent
contended that doctrine of stare decisis, does not apply to this post-grant
opposition proceedings.
CONCLUSION ON STARE DECISIS
The doctrine of stare decisis is expressed in the maxim stare decisis et non
quieta movere, which means "to stand by decisions and not to disturb what
is settled." For invoking the rule of stare decisis, it is sufficient that a
certain decision was arrived at on a question which arose or was argued,
no matter on what reason the decision rests or what is the basis of the
decision.
I am not convinced with the patentees contention, because the claims as
filed were disputed in the pre-grant proceedings, whereas the granted
claims were disputed in post-grant opposition. As the claims disputed in
pre-grant and post-grant opposition were different, the doctrine of stare
decisis cannot be evoked.
Therefore I state that doctrine of stare decisis is not applicable in
this case.
897/MUM/2007 (IN236630) Page 20 SUBSTANTIVE ISSUES
Having dealt with the miscellaneous petition and preliminary issues, I
further proceed on the substantive grounds on which the actual
opposition is based.
THE CLAIMS UPON WHICH THE PATENT IS GRANTED:
The claims of the impugned patent as granted are:
1) Process of manufacturing d-trans Allethrin comprising of following
steps:
a) Charging d-trans Ethyl chrysanthmate into a reactor at a temperature of
5 to 10 degrees C along with 75 grams of Sodium Hydroxide, 154gms of
water and 96gms of methyl alcohol.
b) Subjecting reactants for saponification and distilled off methyl alcohol at
atmospheric pressure of 4kg.
c) Cooling of contents at 20 degrees C and further acidification with
sulphuric acid wherein sodium chrysanthmate is converted into d-trans
chrysanthemic acid.
d) Adding 1.70kgs quantity of petroleum ether which forms two layers,
petroleum layer containing d-trans chrysanthemic acid and water layer
with dissolved sodium sulphate.
e) Allowing two layers to settle for 1 hour, water layer is drained to effluent
tank and d-trans crysathemic acid remains in the reactor,
f) Carrying distillation of d-trans chrysanthemic acid at 20 degrees
g) Treating d-trans crysathemic with 150 grams thionyl chloride, thus
forming d-trans chrysanthemic acid chloride which further is dissolved in
N-H-heptane solvent.
h) Adding 540 grams d-allehtrolne (72:21) 230 grams pyridine and 600
897/MUM/2007 (IN236630) Page 21 grams toluene with d-trans chrysanthanic acid chloride in a reactor
gradually resulting to desired d-trans allethrin.
2) The process of manufacturing d-trans allethrin as claimed in claim 1
wherein hydrogen chloride gas is scrubbed using caustic scrubber directly.
3) The process for manufacturing d-trans allethrin as claimed in claim 1
and 2 wherein the organic layer containing d-trans allethrin is distilled off
to yield desired end product.
GROUNDS OF OPPOSITION
Initially the opponent filed the following grounds of opposition under
section 25(2)(a), 25(2)(b), 25(2)(c), 25(2)(d), 25(2)(e), 25(2)(f), 25(2)(g),
25(2)(h), 25(2)(i), 25(2)(j) and 25(2)(k).
During hearing, grounds under section 25(2)(a), 25(2)(b), 25(2)(c), 25(2)(d),
25(2)(f), 25(2)(h), 25(2)(i), 25(2)(j) and 25(2)(k) were not pressed by the
Opponents and accordingly these
grounds
are
treated
as withdrawn
and therefore I am not going into these grounds.
I am considering the following grounds:
a) U/S 25(2)(e) : that the invention so far as claimed in any claim
of the complete specification is obvious and clearly does not involve
any inventive step, having regard to the matter published as mentioned
in section 25(2)(b) or having regard to what was used in India before the
priority date of the Patentee's claim;
b) U/S 25(2)(g) : that the complete specification does not sufficiently and
clearly describe the invention or the method by which it is to be performed;
The chronological order of the events and documents is as follows :
897/MUM/2007 (IN236630) Page 22 DATE
1.
EVENT
22nd November, Endura S.P.A and Manaksia Ltd. (Opponents) filed
2010
post grant opposition under Section 25(2) along with
Written Statement and affidavit of Mr. Valerio
Borzatta dated 17thNovember, 2010 as and by way
of evidence in support of the said opposition.
2.
6th
January, Opponents
2011
filed
an
Interlocutory
Petition
for
correction of clerical errors together with together
with
affidavits
of
Mr.
Valerio
Borzatta
dated
1stDecember, 2010. (D9 and D10)
3.
8th April, 2011
Patentee filed its Reply Statement on 8th April, 2011
together with the affidavit of Dr. Prabuddha Ganguli
dated 8th April, 2011 as evidence in support of the
patentee.
4.
10th
June, Opponents filed their Reply Statement dated 10th
2011
June, 2011 along with affidavit of Mr. Valerio
Borzatta dated 24th May, 2011 as further evidence.
5.
2nd
November, Notice of hearing along with report of the Opposition
2012
Board and its joint recommendation were forwarded
to both the parties. Hearing was fixed on 5th
December, 2012.
6.
20th November, Opponents notice under rule 62(4) that they shall
2012
refer to and rely upon GB Patent No. 2169293
corresponding to French Patent No. 2575746 (D-5).
7.
5th
December, Hearing of the matter was held at Patent Office,
2012
Mumbai and the same being part heard, was
adjourned.
897/MUM/2007 (IN236630) Page 23 8.
28th December, Opponents submitted its written submission on
2012
9.
15th
arguments made by them on 5th December, 2012.
January, Patentee
2013
10. 22nd
submitted
its
written
submission
on
arguments made by them on 5th December, 2012.
February Another affidavit dated 12th Feb 2013 of opponent
2013
was filed (incl annexure Certificate from Fraunhofer
Institute of chemical technology) was filed
11. 27th
-28th Hearing of the matter was held at Patent Office,
February, 2013
12. 8th March 2013
Mumbai and arguments were concluded.
Patentee’s
written
submission,
Synopsis
and
along
with
Annexure
13. 8th April, 2013
Opponent
Written
Submission
Annexures and case laws with reference to hearing
held on 27th -28th Feb, 2013.
14. 26th June 2013
Order passed by Dy Controller of Patents revoking
Patent
15. 26thSeptember
IPAB Appeal filed by Patentee
2013
16. 18th
August IPAB order setting aside the revocation order dated
2014
26th June 2013, with
constitution of opposition
board again and hearing to be conducted.
17. 23rd April 2015
Recommendations of the Opposition board were
forwarded to both the parties. Hearing was fixed on
08th May, 2015
18. 5th May 2015
Miscellaneous Petition filed by Patentee to furnish
external expert affidavit of Dr. Raghavan Soman in
support of patentability
19. 08th May, 2015
Expert affidavit of Dr. Raghavan Soman evidence,
and all other documents of the Opponents (i.e.
Documents D9 & D10 along with opportunity to
897/MUM/2007 (IN236630) Page 24 file reply affidavit to Dr. Soman afidavit) were
taken on record. The scheduled hearing was
adjourned.
20. 29th May 2015
Reply affidavit of Dr. Valerio Borzatta in reply to
expert affidavit of Dr. Raghavan Soman dated 26th
May 2015 was filed. The same was also forwarded
to the Opposition Board for its recommendations.
21. 09thJuly 2015
Revised
Opposition
board
recommendations
considering all the documents was forwarded to
both parties. Hearing was fixed on 29th September,
2015 after both the parties mutually consent to
this date.
22. 29th September
Hearing was conducted
2015
ISSUE 3 : INVENTIVE STEP/OBVIOUSNESS, Section 25(2)(e)
OPPONENTS’ SUBMISSIONS:
Opponents contended that impugned patent is liable to be revoked
because the invention as claimed in the granted claims of the impugned
patent is neither sufficiently described nor inventive and is clearly
anticipated by the prior art documents cited by the Opponents in the
Notice of Opposition. Opponents explained in detail how the claims are
anticipated by the prior art documents cited by us, as follows:
897/MUM/2007 (IN236630) Page 25 Opponents submitted that the process claimed in claim 1 of the impugned
patent 236630 is a three stage process:
i] Converting d-trans ethyl chrysanthemate to d-trans chrysanthemic acid
(steps a to e)
ii] Converting d-trans chrysanthemic acid to d-trans chrysanthemic acid
chloride (step g)
iii] Converting d-trans chrysanthemic acid chloride to d-trans allethrin
(step h)
Opponents then specifically dealt with each and every step of claim 1 as
follows:
Claim 1 step ‘a’: Charging d-trans Ethyl chrysanthmate into a
reactor at a temperature of 5 to 10 degrees C along with 75 gms of
Sodium Hydroxide, 154 gms of water and 96 gms of Methyl Alcohol
Opponents refer to D1 for preparation of trans-chrysanthemic acid from
trans-chrysanthemate. D1 relates to a process for preparing D1 transchrysanthemic acid which comprises reacting a mixture of alkyl transchrysanthemate and alkyl cis-chrysanthemate with an equimolar amount
or less of an alkali with respect to the trans-isomer in the presence of
water or an alcohol to hydrolyze the trans-isomer predominantly and
separating the hydrolyzed trans-isomer from the unreacted cis-isomer.
Opponents submit that step “a” of claim 1 is carried out with sodium
hydroxide in methyl alcohol maintaining the temperature at 5 to 10oC.
However, all these conditions are taught and/or suggested by the
disclosure of US 3,943,167 (D1). Further claim 2 of D1 states “The
process according to claim 1, wherein the alkali metal hydroxide is
sodium hydroxide or potassium hydroxide.
Specifically, D1 on col. 3 lines 9, 10 teaches that “the use of sodium
hydroxide or potassium hydroxide is industrially advantageous” and
then on lines 38-42 “the
897/MUM/2007 (IN236630) reaction
is
normally
effected
at
a
Page 26 temperature of form about 10oC …when a lower temperature is
adopted the selectively to the trans-isomer is increased”.
The temperature range of 5 to 10oC of step a) of claim 1 is also suggested
by D1. D1 teaches in col. 3 lines 39-42 to use a temperature of 10oC or
lower to increase selectively to the trans isomer of chrysanthemic acid.
Accordingly, the man skilled in the art, being aware that the use of transisomer of chrysanthemic acid is more advantageous (please see D1 col.
1, lines 23, 26), would have been motivated to use a temperature lower
than 10oC and falling in the range of 5 to 10oC of claim 1 to increase the
selectivity of the reaction toward the trans-isomer.
It is pertinent to note that, the specification of D1 also encourages the
selectivity of the disclosed process towards the trans-isomer of Allethrin by
saying that “the use of the trans isomer of chrysanthemic acid for the
pyrethrodis (such as d-trans Allethrin) is more advantageous and
favourable than that of the corresponding cis-isomer.”
Claim 1 Step ‘b’: Subjecting reactants for saponification and
distilled off methyl alcohol at atmospheric pressure of 4kg.
Opponents submit that step ‘b’ of claim 1 is also anticipated by D1.
D1
teaches (col. 3 1.38-42) that the saponification step “a” is normally carried
out at a temperature of from 10oC (i.e.at a temperature of the claimed
range). In addition, D1 by stating (col. 3 1.40-42) that “when a lower
temperature is adopted, the selectively to the trans-isomer becomes
increased”, also teaches to use a temperature which is lower than 10oC,
that is a temperature falling in the claimed range of 5 to 10oC of step “a” of
claim 1 of the subject patent 236630. Thus, D1 would have easily
prompted a person skilled in the art to carry out the saponification step “a”
at temperatures lower than 10 degrees, that is falling in the claimed range
of 5 to 10oC, indeed to increase the selectively of the process toward the
trans-isomer.
Regarding
897/MUM/2007 (IN236630) distillation
of
alcohol
produced
during
Page 27 saponification Opponents refer to Example 1 of D1 which is reproduced
below:
EXAMPLE 1
In a 300 ml volume four-necked flask equipped with a stirrer, a
thermometer and a reflux condenser, there were charged ethyl
chrysanthemate consisting of 35.2 % of the cis-isomer and 64.8 % of
the trans-isomer (100 g; trans-isomer, 0.33 mol) and a 25 % aqueous
solution of sodium hydroxide (48 g; NaOH, 0.30 mol), and the
mixture was stirred at 85°C for 4 hours. After distilling off ethanol
produced during the hydrolysis, the reaction mixture was admixed
with water (200 g) and extracted with n-hexane (60 g) two times. The
n-hexane layer was separated, washed, dried and evaporated, and
the residue was distilled under reduced pressure to give unreacted
ethyl chrysanthemate (41.3 g; cis/trans = 55.4/44.6). B.P. 112 to
116°C/19 mmHg.
Oponents reiterate that the expression “atmospheric pressure of 4kg”is
technically incorrect.
Claim 1 step ‘c’: Cooling of contents at 20 degrees C and further
acidification with sulphuric acid wherein sodium chrysanthmate is
converted into d-trans crysanthemic acid,
Opponents submit that the Patentee has tried to emphasize the
importance of cooling the mixture at 20oC before acidification to step c) of
claim 1. However, a man skilled in the art would understand that cooling
at 20oC (that is at room temperature) the mixture, before adding sulfuric
acid, is necessary because the reaction with sulfuric acid is exothermic. It
should be also noted that the addition of a mineral acid, such as sulfuric
acid, to separate the free trans-chrysantemic acid is taught by D1 on col.3
lines 66-68 and col 4 lines 1-3. Accordingly, the features of step c) of claim
1 of the impugned patent are taught or easily derivable from D1.
897/MUM/2007 (IN236630) Page 28 Claim 1 step ‘d’: Adding 1.70 kgs quantity of petroleum ether which
forms layers, petroleum layer containing d-trans crysathemic acid
and water layer with dissolved sodium sulphate.
Opponents submit that use of petroleum ether in extraction step d) of
claim 1 is derivable from D1. D1 teaches in col. 3, lines 54-57 the use of
hexane as extraction solvent. However, hexane is commonly used as
replacement solvent for petroleum ether (vide GB 1 448 228 (D3), p.5, lines
27-31, wherein petroleum ether is used for extracting difluoro-2,2dimethyl-cyclopropanecarboxylic acid, which has the same chemical
structure of chrysanthemic acid, specifically where two fluoro groups
substitute two methyl groups). Thus, D1 teaches the use of a solvent
which is fully equivalent to petroleum ether.
Accordingly, it would be a routine practice, for one of ordinary skill, to use
petroleum ether as replacement of hexane in the extraction step of D1 thus
arriving at step d) of claim1 of the patent under opposition. The
submission of Patentee regarding the criticality of the solvent (petroleum
ether) used in the extraction step d) of claim 1 of the patent under
opposition is baseless and without any credibility.
Opponents submit that in fact, D1 teaches (cfr. D1, col.3 lines 56,57) to
carry out the extraction step by using organic solvents such as ether,…and
hexane which is a solvent fully equivalent to the claimed “petroleum ether”
being the petroleum ether a mixture of alkanes and their isomers. For
example GB 1 448 228 (D3) discloses (p.5, 1.29) the use of “petroleum
ether”
in
an
extraction
step
of
difluoro-2,2-dimethyl-
cyclopropanecarboxylic acid, which has the same chemical structure of
chrysanthemic acid, specifically where two fluoro groups substitute two
methyl groups.
Opponents submit that the Patentee’s allegation that the use of
“petroleum ether” as solvent in step d) of the patent under opposition is
not disclosed in D1 is baseless and misleading. It has been demonstrated
that use of petroleum ether is easily derivable from the available prior art.
897/MUM/2007 (IN236630) Page 29 In addition, the specification of the impugned patent is silent (and the
Patentee has not provided any experimental evidence during proceedings)
on the advantages (if any) offered by the use of petroleum ether in respect
of the other suitable organic solvents disclosed in D1.
Claim 1 step ‘e’: Allowing two layers to settle for 1 hour, water layer
is drained to effluent tank and d-trans crysathemic acid remains to
the reactor,
Opponents submit that with regard to the step of recovery of transchrysanthemic acid, D1 teaches (vide col.4, lines 1-3) that the free transchrysanthemic acid may be recovered by a conventional procedure, such
as extraction. This statement makes irrelevant – to the aim of assessing
the inventive step of the subject patent- whether the recovery of the acid is
done from the water or organic layer. In fact in both the cases the
technique of recovery is conventional and the extraction from one or other
of the two available phases is a routine practice for one of ordinary skill in
the art.
Claim 1 step ‘f: Carrying distillation of d-trans crysathemic acid at
20 degrees
Opponents submit that D-trans chrysathemic acid has b.p. of 246°C at
atmospheric pressure (760mmHg). (enclosed document A or as reported in
US 4049706 –document B –column 5 ex. 19, chrysanthemic acid has b.p.
110-112° at 1.5 Torr equivalent to 1.5 mmHg equivalent in turn to 20,4
Kg/square meter ) Therefore, this step of distillation is wrong. If the
distillation of methyl alcohol takes place then such is disclosed in D1 col 5
Example 6 lines 29-30. However, the same (distillation of methyl alcohol) is
not supported by Example of granted claim.
897/MUM/2007 (IN236630) Page 30 Claim 1 step ‘g’: Treating d-trans crysathemic with 150 grams
thiunyl chloride, thus forming d-trans crysathemic acid chloride
which further is dissolved in N-H-heptane solvent
Opponents submit that the use of N-heptane as solvent in chlorination
step g) is derivable from D7. D7 discloses on page 30 the use of N-hexane,
that is the lower homolog of N-heptane as solvent in the treatment of
chrysanthemic acid with thionyl chloride. It would have been obvious for a
man of ordinary skill in the art to use the superior hydrocarbon
homologous N-heptane as solvent in the same chlorination step thus
arriving at step g) of claim 1 of the subject patent.
Opponents further submit that D4 (US 3723469) (vide para 13 lines 7-17)
discloses:
Stage A : 1-trans-chrysanthemic (1S,2S) acid chloride into 140 cc of
petroleum ether (b.pt. = 35o- 70o C), one introduces 73.5 g. of 1-transchrysanthemic (1S,2S) acid (see Note) then, drop by drop over several
minutes, 35 cc of thionyl chloride, agitates for 2 hours at ambient
temperature, eliminates the volatile fractions by distillation under reduced
pressure, then redistills under a more powerful vacuum, and obtains 80 g.
of 1-trans-chrysanthemic (1S,2S) acid chloride, b.pt. = 65oC under 0.4 mm
of mercury”
Claim 1 step ‘h’: Adding 540 grams d-allethrolne (72:21) 230 grams
pyridine and 600 grams toluene with d-trans chrysanthanic acid
chloride in a reactor gradually resulting to desired d-trans allethrin
Opponents submit that 1 the step h) is anticipated by Example 7 of US
3,934,023 (D2).
Example 7 at para 5 of D2 discloses:
18.7 Grams of (+)- cis, trans-chrysanthemic acid chloride containing 19.0% by
weight of (+)-cis-chrysanthemic acid chloride were dissolved in 20 ml of
toluene. the solution was added to a mixture of 16.0 g of (+)-2-allyl-3methylcyclopent-2-ene-1-one-4-ol, 11.9 g of pyridine and 30 ml of toluene
897/MUM/2007 (IN236630) Page 31 over 30 minutes while maintaining the reaction temperature at from 40° to
50°. The solution was further maintained at the same temperature for 4
hours. Thereafter the reaction solution was treated in the same manner as
described in Example 1to give 29.4 g of (+)-2-allyl-3-methylcyclopent-2-ene-1one-4-yl-(+)-cis,trans -chrysanthemate as an oily matter.
Example 2 at paragraph 4 of D2 discloses
“(+_)2-allyl-3-methylciclopent-2-ene-1-one-4-yl-(+)-cis,trans
-
chrysanthemate as an oil.”
Opponents further submit that step “h” of claim 1 is anticipated by D7 at
page 30 and 31, wherein it has been stated:
“(4) Allethrin I.
Allethrin I (3.2g) was prepared from technical dl-Allethrolone 2.5 g (.016M)
and chrysanthemoyl chloride in benzene solution, 10 ml (0.014 M), in the
presence of pyridine (1.8ml).”
Opponents state, step “h” of the impugned patent, which relates to
obtaining d-trans allethrin by adding d-allethrolone, pyridine and toluene
with d-trans chrysanthemic acid chloride is clearly anticipated by the
teachings of D2 and D7.
With regard to the features of dependent claim 2 (which refers to the use of
caustic scrubber to scrub hydrogen chloride gas) and dependent claim 3
(which refers to the distillation of the organic layer containing d-transallethrin to yield the desired product) Opponents submit that these are
routine technique well known to the skilled person in the art to eliminate
the hydrogen chloride gas and to make the final distillation.
Opponents submitted that the invention as claimed by the impugned
patent is obvious and does not involve any inventive step in view of the
documents cited by Opponents and on that ground alone, the patent is
liable to revoked. Further Opponents state the invention claimed in the
impugned patent is not an invention within the meaning of this Act.
897/MUM/2007 (IN236630) Page 32 Further, Opponents written submissions from page 13 to page 49 is
nothing but rebuttal to Dr.Soman’s affidavit by Dr.Borzatta. I have
studied the affidavits of Dr.Soman and Dr.Borzatta independently.
Cognizance of these documents and points therein, is taken as and
when required in the order.
Further, the Opponents on page 50 submitted that the Patentee has failed
to establish that the invention is sufficiently described in the description
and is inventive over the documents cited by the Opponents. Moreover, the
Patentee has tried to mislead the Hon’ble Board by arguing that starting
material of the process claimed in the impugned patent is not the same as
that in the documents relied upon by the Opponents.
Opponents submit that the Patentee has tried to mislead the Hon’ble
Board by arguing that the uniqueness of their invention is that they have
been able to maintain “optical purity” in their invented process. The
argued that by judicious selection of reactants solvents in each steps, the
patentee have succeeded in prevention conversion from trans isomer to cis
isomer. In this regard we submit that it is well established fact that any
trans isomer of an organic compound is thermodynamically more stable
than its cis counterpart. Opponents would respectfully invite the kind
attention of the Hon’ble Board to column 5 lines 45 to 47 of D4 (US
3,723,469) in this regard which reads as follows:
“One knows in fact that in the chrysanthemic series, the compounds
of
trans configuration are
thermodynamically more stable than the
corresponding compounds of cis configuration,”
Accordingly, the contention of the Patentee about preventing conversion of
trans isomer to cis isomer is baseless, frivolous, misleading and against
well-established principle of stereo chemistry.
897/MUM/2007 (IN236630) Page 33 Further, the Opponents contended that the Patentee has tried to mislead
the Hon’ble Board by arguing that by using petroleum ether to dissolve dtrans chrysanthemic acid in step “d” of claim 1 of the impugned patent,
the
Patentee
has
succeeded
in
preventing
conversion
of
d-trans
chrysanthemic acid to d-cis chrysanthemic acid. According to the
patentee, this would not have been possible if any other organic solvent
was used in place of petroleum ether. Opponents reiterated that
conversion of d-trans chrysanthemic acid to d-cis chrysanthemic acid is
impossible from point of view of stereochemistry. Further, Opponents
contended that the Patentee has not mentioned this point anywhere in the
specification, neither in the description nor in the claims, of the impugned
patent 236630. The Patentee has not produced any authentic test result to
substantiated their contention. Thus the contention of the Patentee
regarding judicious selection of petroleum ether as a solvent in step d is
totally frivolous, baseless and devoid of any scientific reasoning.
Opponents further contended that Patentee has tried to mislead the
Hon’ble Board by arguing that by using N-heptane in step “g” of claim 1 of
the impugned patent, the Patentee has succeeded in preventing conversion
of d-trans chrysanthemic acid to d-cis chrysanthemic acid. According to
the Patentee, this would not have been possible if any other organic
solvent was used in place of N-heptane. Opponents
reiterated that
conversion of d-trans chrysanthemic acid to d-cis chrysanthemic acid is
impossible from point of view of stereochemistry. Further, the Patentee has
not mentioned this point anywhere in the specification, neither in the
description nor in the claims, of the impugned patent 236630. The
Patentee has not produced any authentic test result to substantiated their
contention. Thus the contention of the Patentee regarding judicious
selection of petroleum ether as a solvent in step d is totally frivolous,
baseless and devoid of any scientific reasoning.
897/MUM/2007 (IN236630) Page 34 Opponents further contended that the Patentee has tried to mislead the
Hon’ble Board by arguing that the critical aspect of the process claimed in
the
impugned
patent
236630
is
saponification
of
d-trans
Ethyl
chrysanthemate at 5°C. In this regard we would respectfully invite the kind
attention of the Hon’ble Board to the wording of steps “a” and “b” of the
impugned patent 236630:
a) Charging d-trans Ethyl chrysanthmate into a reactor at a temperature of 5
to 10 degrees C alongwith 75 gms of Sodium Hydroxide, 154 gms of water
and 96 gms of Methyl Alcohol
b) Subjecting reactants for saponification and distilled off methyl alcohol at
atmospheric pressure of 4kg
As
evident
from
abovementioned
steps
“a”
and
“b”
of
claim
1,
saponification of d-trans Ethyl chrysanthemate at 5°C is not at all
mentioned. Further the example at page 6 of the specification of the
impugned patent 236630 neither mentions of saponification at 5°C. Thus
the contention of the patentee that “critical aspect of the process claimed
in the impugned patent 236630 is saponification of d-trans Ethryl
chrysanthemate at 5°C” is frivolous and baseless.
Opponents further contended that the Patentee has tried to mislead the
Hon’ble Board by arguing that the critical aspect of the process claimed in
the
impugned
patent
236630
is
in
the
chlorination
of
d-trans
chrysanthemic acid with thionyl chloride. We respectfully submit that a
skilled person in the art immediately acknowledges the trivial and usual
conditions for a chlorination step of an acid with thionyl chloride, with no
possible inventive aspects in the specific ingredients stated in step g of the
impugned patent 236630. Further, the patentee has not mentioned
anywhere in the specification the technical advancement that is accrued
over prior art from this chlorination step. Thus chlorination step do not
attribute any inventive ingenuity to the impugned patent. Accordingly, the
contention of the Patentee regarding chlorination of d-trans chrysanthemic
897/MUM/2007 (IN236630) Page 35 acid with thionyl chloride is totally frivolous, baseless and devoid of any
scientific reasoning.
Opponents further contended that the Patentee has tried to mislead the
Hon’ble Board by arguing that the molar ratio of sodium hydroxide is
higher than suggested in US 3,943,167. In this regard we would
respectfully invite the kind attention of the Hon’ble Board to the wording of
steps “a”. It is pertinent to note that the mass of d-trans Ethyl
chrysanthemate is missing from step “a” of claim 1 of the impugned patent
236630. In absence of a mass of a key ingredient (d-trans Ethyl
chrysanthemate) of the process claimed in 236630 it is not possible to
calculate the molar ratio of d-trans Ethyl chrysanthemate with sodium
hydroxide. Further, patentee has not mentioned anywhere in the
specification the technical advancement that is accrued over prior art from
selecting higher molar ratio of d-trans Ethyl chrysanthemate to sodium
hydroxide in step “a”. Accordingly, the contention of the Patentee regarding
molar ratio of d-trans Ethyl chrysanthemate to sodium hydroxide is totally
frivolous, baseless and devoid of any scientific reasoning.
Opponents further contended that the Patentee has tried to mislead the
Hon’ble Board by arguing that in the process claimed in the impugned
patent 236630 there is no unreacted starting material. It is pertinent to
note that the mass of d-trans Ethyl chrysanthemate is missing from step
“a” of claim 1 of the impugned patent 236630; accordingly the question of
unreacted of d-trans Ethyl chrysanthemate does not arise. Further,
patentee has not mentioned anywhere in the specification that an object
of the invention was to have zero unreacted d-trans Ethyl chrysanthemate
Accordingly, the contention of the Patentee regarding zero unreacted dtrans Ethyl chrysanthemate is totally frivolous, baseless and devoid of any
scientific reasoning.
897/MUM/2007 (IN236630) Page 36 Opponents further contended that the Patentee has tried to mislead the
Hon’ble Board by arguing that process claimed in the impugned patent
236630 has high yield. It is pertinent to note no yield can be calculated in
absence of mass of d-trans Ethyl chrysanthemate from step “a” of claim 1
of the impugned patent 236630. Further, obtaining higher yield was never
an object of the invention of the impugned patent 236630. Opponents
contended that without any prejudice to their above submission, if molar
conversion of the reactants and product mentioned in the example at 6 is
carried out then one would infer as follows:
Starting d-Trans ethyl chrysanthemate 297.5 g corresponding to 1.516
mol. 75 g of NaOH corresponds to 1.875 moles. Concentrated sulphuric
acid (if 98% w/w corresponding to18.35 M or mol/l; if 96% w/w
corresponding to17.97 M o mol/l) 0.123 ml, i.e.0.0022 mol on the basis of
sulphuric acid 98% w/w. After acidification, there is an extraction step
with petroleum ether and distillation (probably of the solvent since it is not
specified), thus obtaining d-trans chrysanthemic acid corresponding to
251.2 g (with a purity of 98.4%.) On the basis of the above data
chrysanthemic acid is considered 98.4%%, i.e. 251.2 g x 0.984 = 247.18 g
corresponding to 1.469 moles. However, the amount of sulphuric acid is
0.0022 mol, which can acidified at most 0.0044 mol of sodium sat of
chrysanthemic acid (since the sulphuric acid is diprotic); therefore the
yield should be calculated on the basis of this amount. Contrarily, the
amount reported in the example is 1.469 moles. If compared to D1, the
yield therefore should be calculated on the basis of the limitative reactant,
i.e. sulphuric acid. The yield calculated on the basis of 0.0022 mol of
sulphuric acid is 0.3%. Therefore, the comparison with D1 shows that the
opposed patent is not inventive at all. The Patentee underlined also the
high yield obtained in the second part of the process step, i.e. the
obtainment of chrysanthemic chloride. Starting chrysanthemic acid: 175 g
with a purity of 98.4%, that correspond to 172.2 g, 1.0235 mol, thionyl
chloride: 150 g that correspond to 1.26 moles. Obtained chloride of
897/MUM/2007 (IN236630) Page 37 chrysanthemic acid ( or chrysanthemic acid chloride) : 204.75 g with
purity of 98.7% corresponding to 202.088 g, i.e.1.0825 moles. Therefore,
starting from 1.0235 moles of acid , 1.0825 moles of chloride are obtained.
This is against the law of conservation of mass. Accordingly, the
contention of the patentee about higher yield is frivolous, baseless and
devoid of any scientific reasoning.
Opponents further contended that Patentee has tried to mislead the
Hon’ble Board by arguing that the duration of the process claimed in the
impugned patent 236630 is lesser than prior art. Opponents respectfully
submit that the duration of each steps (except step “e”) of claim 1 has not
been mentioned in the claims. Opponents submit that minimizing the
duration of the process was never an object of the invention. The
specification of the impugned patent 236630 nowhere mentions about any
technical problem associated with the duration of known processes for
obtaining d-trans allethrin. The Patentee has not substantiated their
contention with any comparative test result. Accordingly, the contention
of the Patentee with regard to duration is frivolous, baseless and devoid of
any scientific reasoning.
Opponents further contended that Patentee has tried to mislead the
Hon’ble Board by arguing that the Opponents have successfully carried
out the process claimed in 236630 and the example at page 6 of the
specification. Opponents respectfully submit that it is impossible to carry
out the process as claimed in claim 1 of the impugned patent because of
the following reasons:
i.Mass of d-trans Ethyl chrysanthemate is missing from step “a”
ii. Atmospheric pressure of 4 kg as mentioned in step “b” is not correct
iii. Quantity and strength of sulphuric acid in missing in step “c”.
iv. It is not possible to carry out distillation of chrysanthemic acid at 20°C
as mentioned in step “g”.
897/MUM/2007 (IN236630) Page 38 v. D-allethrone (72:21) is an unknown compound. Step “h” cannot be
carried out.
Without any prejudice to Opponents’ above submission, Opponents
submitted that the laboratory experiment conducted by Dr. Valerio
Borzatta and as reported under D9 and D10 are different from claim 1 as
well as from the example at page 6 of the specification with regard to
difference in mass of d-trans ethyl chrysanthemate, mass of methanol,
mass of sodium hydroxide, volume of water, and volume and strength of
sulphuric acid. Further, Opponents submitted that the experiments
conducted by Dr. Borzatta as reported in D9 was only hydrolysis of d-trans
ethyl chrysanthemate by sodium hydroxide to obtain d-trans sodium
chrysanthemate
followed
by
acidification
of
d-trans
sodium
chrysanthemate to d-trans chrysanthemic acid using sulphuric acid. In
D10, Dr. Borzatta has carried out synthesis of chrysanthemoyl chloride in
n-heptane and n-hexane. Dr. Borzatta has not conducted any experiment
to obtain d trans allethrin from d-trans chrysanthemic acid. A compound
by the name of D-allethrolone (72:21) is not mentioned in any dictionary of
organic chemistry. Therefore the carrying out step “h” is impossible. A
comparison between the experiment conducted by Dr. Borzatta as reported
in D9 and claim 1 and example at page 6 of the specification of 236630 is
provided in the table below.
Ingredient/Parameter
Granted claim
Example
1
page 6
at
Experiment
conducted by Dr.
Borzatta
as
reported in D9
Mass of d-trans Ethyl
Missing
297.5 gms
49.9 gms
75 gms
75 gms
15.4 gms
chrysanthemate
Mass
of
sodium
hydroxide
897/MUM/2007 (IN236630) Page 39 Strength of sodium
Missing
Missing
97% w/w
154 gms
154 gms
28 gms
96 gms
81.0 gms
20.1 gms
hydroxide
Mass of water
Mass
of
methyl 96 gms
alcohol
Mass
of
sulphuric
Missing
0.123ml
Strength of sulphuric
Missing
Missing
acid
96% w/w
acid
A comparison between the experiment conducted by Dr. Borzatta as
reported in D10 and claim 1 and example at page 6 of the specification of
236630 is provided in the table below.
Ingredient/Parameter
Granted claim
Example
1
page 6
at
Experiment
conducted by Dr.
Borzatta
as
reported in D10
Mass
of
n-
Missing
350 ml
200 ml
150 gms
42.0 gms
heptane/n-hexane
Mass
of
thionyl 150 gms
chloride
Thus on the basis of the above submissions, Opponents submitted that
the contention of the Patentee that the Opponents have successfully
carried out the process claimed in the impugned patent 236630 is
frivolous and baseless.
Regarding selection of d-trans Ethyl Chrysanthemate as a starting
material,
Opponents
submitted
that
selection
of
d-trans
Ethyl
Chrysanthemate as a starting material for obtaining d-trans Allethrin does
not involve any inventive merit, as explained hereinafter. It is a general
897/MUM/2007 (IN236630) Page 40 knowledge that if one starts with trans-Ethyl Chrysanthemate, following
the same steps as outlined in the claim 1 of the impugned patent, he
would land up with trans-Allethrin. Similarly, if one starts with cis-Ethyl
Chrysanthemate he would, following the same steps as outlined in the
claim 1 of the impugned patent, land up with cis-Allethrin. And if one
starts with a racemic mixture of cis and trans Ethyl Chrysanthemate a
racemic mixture of cis and trans Allethrin would be obtained. Moreover
Opponents submitted that, there is a clear indication in D2 (vide para 2
lines 11-17) that (+)-trans-chrysanthemic acid is known to give its esters of
the highest insecticidal activity”. Opponents further submit that D1 at
para 1 lines 24-26 mentions that the use of trans-isomer of chrysanthemic
acid for the production of pyrethroidsis more advantageous and favorable
than that of the corresponding cis-isomer. Furthermore, it is well known
that the trans-isomer is more stable than the cis isomer, as reported in
D4(US3,723,469), column 5, lines 45-47. Therefore starting from trans
ethyl-chrysanthemate, that is more stable and more favorable for this
insecticidal activity is clearly the only mandatory choice of the skilled
person who desires to obtained the trans- isomer of allethrin. This is a
clear indication of higher insecticidal property of trans-isomer of
chrysanthemic acid over its cis-isomer. Accordingly, it can be clearly
conferred that selection of d-trans Ethyl Chrysanthemate as starting
material for obtaining d-trans Allethrin does NOT INVOLVE ANY
INVENTIVE MERIT. It is pertinent to note that the Patentee is well aware
of this and in fact the Flow Chart being Figure 1 provided by the Patentee
in the impugned patent supports Opponents argument.
Figure 1 of the impugned patent is reproduced below for easy reference:
897/MUM/2007 (IN236630) Page 41 It is thus evident from the above diagram that the group (with double
bond)
is not participating in any of the steps I to VI and all reactions are taking
place only in the carboxyl group.
897/MUM/2007 (IN236630) Page 42 PATENTEE’S SUBMISSIONS:
Technical aspects of the patented invention:
Patentee submitted that the invention of Indian Patent 236630 relates to a
novel process for manufacturing ‘D-trans Allethrin’ (a Chiral pyrethroid). It
is a sequential process of synthesizing d-trans Allethrin having a minimum
purity of 93%. The process can be replicated in both small scale
experiments as well as large commercial scale production. Patentee states
process according to the present invention comprises essentially of three
stages:
I] Step a) to Step f) : Conversion of d-trans Ethyl Chrysanthmate to d-trans
Chrysanthemic acid,
II] Step g) : Conversion of d-trans Chrysanthemic acid to d-trans
Chrysanthemic acid chloride,
III] Step h) : Conversion of d-trans Chrysanthemic acid chloride to d-trans
Allethrin.
As per the Patentee, the inventive step of the present invention lies the
following features:
i] Using D-trans ethyl chrysanthemate as starting material:
Patentee submitted that Ethyl Chrysanthemate and Chrysanthemic acid
exists asisomers – in Cis and Trans form, and within Cis and Trans
isomers, there are stereo-isomers of D and L- spatial arrangement. The
different isomers and forms of each of these are capable of changing state
or becoming inactive when subjected to elevated temperatures, shift in
equilibrium, or use of harsh solvents. High temperature and other
conditions were anyway required in the reaction which would promote
conversion of isomers from one form to another. Chrysanthemic Acid
having 80% Trans isomer and 20% Cis isomer has boiling point around
250 degrees C. But Chrysanthemic Acid having 98% or more of Trans
897/MUM/2007 (IN236630) Page 43 isomers has boiling point around 238 degrees C. Individual stereo-isomers
like ‘D-trans’ or ‘L-trans’ present in different ratios and mix also have
different boiling points. Their solubility in various solvents will also be
different based on the mix of isomer content. That is the reason why
traditionally all theprocesses for preparation of ‘Chrysanthemic Acid’ and
‘Allethrin’ have started with racemic mixture and eventually at the later or
last stage extracted ‘trans’ isomer. These processes have compromised on
yield and purity. If the final product (allethrin) is formed as racemic
mixture, then the properties of the compound change and affects the
efficacy thereof, including the knock-down effect etc. Patentee submitted
that this invention found that if the process is carefully controlled, the cis
and trans isomers can be prevented from getting converted from one form
to the other (or between D and L). Going completely against this thought of
all the prior art (from D1 of 1970 till date of this invention), the inventors
have
devised
a
process
that
starts
with
‘D-trans’isomer
ethyl
chrysanthemate. From 1976 till date, no prior art has thought of or
suggested the use of only particular D-trans ethyl chrysanthemateisomer a
staring material.
ii] Maintaining optical purity all through the reaction:
Patentee submitted that scheme of the invented process is that,it is the
only process reported so far that maintains optical purity (D-trans state)
not only of the starting material but also of each intermediate product at
each stage. “D-trans ethyl chrysanthemate” to “D-trans chrysanthemic
acid” to “D-trans chrysanthemic acid chloride” to “D-trans allethrin”.
Patentee stated that this is possible only though judicious choice of
solvents and reaction conditions which are unique to the invented process.
Patentee submitted that there is no prior art that even suggests that the
reaction can be started with optically pure d-trans ethyl chrysanthemate
and that such optical purity should be maintained all through the reaction
897/MUM/2007 (IN236630) Page 44 till desired end product, i.e. as in the present Patent invention and the
conditions for doing so.
iii] Yield:
Patentee pointed out that the process of the invention gives high yield of dtrans allethrin of more than 96%, while still maintaining starting material
and all the intermediate products in D-trans state only. Till step (f) i.e.
formation of D-trans Chrysanthemic Acid, the yield is more than 96%, This
has never been achieved before, in combination with maintaining D-trans
isomer. The high yield is the result of the process design and combination
of various factors; such as:
iv] Low temperature:
Patentee submitted that first step of the reaction, step (a) wherein d-trans
ethyl chrysanthemate is reacted with sodium hydroxide, water and methyl
alcohol at a temperature between 5 to 10°C. In complete contrast, all the
art uses high temperature in fact the entire process of prior art is
conducted at high temperature and this invention is done at low
temperature.
v] Different solvent in each step – No adverse effect on yield:
Patentee submitted that at each step of the invented process uses different
solvents of different polarity and solubility taking into account the
reactants, the physiochemical properties of each reactant, the equilibrium
and condition of that step. The solvents used are also based on the
reaction time and the amount of solvent is carefully chosen taking into
account these factors. Yet such use has not affected the final yield. In the
patented invention, the Inventor has used a different combination of
solvents: Claim 1 Step a): Methanol(methyl alcohol) + Water with starting
ingredient D-trans ethyl chrysanthemate, resulting in in-situ formation of
Ethanol. A mixture of Methanol, Ethanol and Water is combined in this
897/MUM/2007 (IN236630) Page 45 reaction which leads to better reactivity. Small quantity formation of
Ethanol helps in reaction and improves yield, and later gets distilled off
with Methanol. Claim 1 Step d) to f): Addition of water + petroleum ether
for extraction of D-trans Chrysanthemic Acid. Solvent Petroleum Ether has
never been used before this, to extract ‘D-trans Chrysanthemic Acid’. This
low temperature evaporating solvent, is to maintain purity, give better
layer separation, prevent cis-trans conversion, and at same time result in
high yield of D-trans chrysanthemic acid; which is not suggested by any
prior art. Claim 1 Step g):
Solvent
n-Heptane
for
Chlorination:
A
solvent easily miscible with D-trans Chrysanthemic Acid and Thionyl
Chloride, assists in good reaction progress and D-trans Chrysanthemic
Acid Chloride is formed. It is a stable solvent with less passive evaporation
loss therefore gives good solvent recovery. Thus, if solvent can be
recovered, it can be recycled. This has technical and economic advantages.
Solvent n-Heptane has never been used before for chlorination and
conversion of ‘D-trans Chrysanthemic Acid’ to ‘D-trans Chrysanthemic
Acid Chloride’. Patentee highlighted that no prior art discloses use of
Heptane solvent for preparation of D-trans Chrysanthemic Acid Chloride. A
study conducted using various solvents has revealed that only n-Heptane
is the solvent that gives yield of more than 98%. Patentee then relied upon
Study conducted by M/s. Aura Biotechnologies Lab which has been filed
as annexures with affidavit of Dr.R. Soman dated 30th April, 2015/5th
May, 2015. Comparison of experiments conducted with other solvents is as
below :
897/MUM/2007 (IN236630) Page 46 Claim 1 Step h): Solvent Toluene was combined with Pyridine. An ideal
combination in which reactants ‘D-trans Chrysanthemic Acid Chloride’
and ‘d-allethrolone’ are soluble. The resulting product ‘D-trans Allethrin is
also soluble in Toluene. This combination of Toluene and Pyridine,
assisted the reaction and gave good yield as well as maintains equilibrium
of reaction. It also maintained the desired ‘D-trans isomer’ and prevented
any possible conversion.
Patentee further submitted that in a multi-step reactions, and each step
has an impact on the next step, then in such reactions, changing the
‘conventionally’ used solvents, finding a different solvent which eventually
results in high yield of final product is an invention. This requires careful
choice, experimentation and research and application of creativity. One
cannot change solvents or use just any solvent for any step of the process.
Thus, the judicious choice of these solvents in optimum quantity, for each
897/MUM/2007 (IN236630) Page 47 specific step of the present invention with a specific goal, is not taught by
prior art and is inventive.
vi] Acidification and extraction :
Patentee submitted that in the invented process, as against the prior art,
chrysanthemic acid is formed, and then extracted in petroleum ether layer.
Patent IN236630 states “acidification with sulphuric acid wherein entire
sodium chrysanthemate is to be converted into d-trans chrysanthemic acid”.
Cited document D1 states “For recovery of trans chrysanthemic acid from
water layer it may be made acidic with a mineral acid such as sulphuric acid
or hydrochloric acid to separate free-trans chrysanthemic acid”.
Patentee therefore submitted that the use of the sulphuric acid in the
patented process is not for the same purpose as in prior art document D1.
Patentee states that as per patented process, Sulphuric acid is added
before Chrysanthemic Acid is formed, purpose to perform acidification.
Patentee also submits that as per document D1, Sulphuric acid is added
after Chrysanthemic Acid is formed, to make water acidic to separate free
trans acid that is already formed. Patentee further submitted that apart
from other inventive merits, uniqueness of the present invention patent
process is the intent and purpose of using sulphuric acid and then in
subsequent step use of Petroleum Ether for extraction. This use of
Sulphuric acid for forming D-trans Chrysanthemic acid (acidification) and
subsequent extraction of D-trans Chrysanthemic acid with Petroleum
Ether solvent has not been tried before.
Regarding Lack of inventive step in comparison with cited prior art
documents D1 to D7, Patentee submitted as follows:
Patentee contended that during the hearing and proceedings, the
Opponent has given up the ground of anticipation; hence, no rebuttal
arguments are required.
897/MUM/2007 (IN236630) Page 48 Further the Patentee stated that Opponents have relied on documents D1D7 to demonstrate that the process as claimed is not inventive. In this
regard, it is submitted that the Opponent has merely used the Patentee’s
patented process as a blue print and tried to map each step into a specific
prior art, albeit without much success. The following illustration shows
how the prior art documents were mapped to the Patent claims Step (a) to
(h):
Document D1 covers steps (a) to (f). D2 covers step (h). Documents D3 to
D7 cover step (g). Without prejudice to the argument that the Opponent is
barred from relying on D1 as well as D2 documents being barred by Resjudicata, Patentee submitted as follows :
897/MUM/2007 (IN236630) Page 49 Document D1 – US 3,943,167 :
The Opponents argued that D1 relates to a process for preparing transchrysanthemic acid which comprises, reacting a mixture of alkyl transchrysanthemateand alkyl cis-chrysantehmate, with an alkali and that all
the steps of the patented claims are published in D1. To counter the
argument of Opponents , Patentee submitted that such arguments are
completely misplaced, misconceived and wrong for the reasons below:
Parameter
D1
Patent
236630
process
Starting material Mixture of Cisand Trans D-trans
ethyl
ethyl
chrysanthemate+ chrysanthemate
Sodium Hydroxide
+
Sodium Hydroxide +
Methyl
alcohol
solvent + water
Solvent system
Does not have a mixed Mix solvent system :
solvent system
Methanol+water
+
insitu
of
formation
Ethanol
Temperature
Higher than 50 degrees C. Between
5-10
Teaches away from using degrees C
lower temperature
Ratio of isomer- Equimolar or less amount Excess
amount
alkali
used
with
respect
to
trans
isomer.
i.e.
more
of an alkali with respect alkali
to trans isomer.
of
than equimolar.
Unreacted
Unreacted
material
chrysanthemateis left and material
897/MUM/2007 (IN236630) Cis
-
ethyl No
unreacted
left
,
so
Page 50 requires to be separated does
out
not
require
additional steps of
separation
and
distillation
Acidification
/ Sulphuric
acid
is Sulphuric
use of sulphuric addedafterChrysanthemic
acid
Acid
is
formed,
Acid
is
added before the D-
for TransChrysanthemic
making water layer acidic acid is formed, to
to
separate
free
trans convert
Chrysanthemic Acid
sodium
chrysanthemate
form
to
D-Trans
chrysanthemic acid
Hexane and its Unreacted
distillation
ethyl No
chrysanthemate
extracted
in
such
step
is
is required
solvent
Hexane and distilled
Layer separation Layer separation is not Petroleum
and Extraction
taught.
acid
is
Ether
Chrysanthemic solvent is used with
extracted
solvent Toluene
in D-trans
Chrysanthemicacid
for layer separation.
Separated
layer
sodium
Extraction
water
contains
sulphate.
of
D-
trans
Chrysanthemic acid
is done in Petroleum
Ether.
Conversion
897/MUM/2007 (IN236630) Not taught by D1
Process starts from
Page 51 ofChrysanthemic
D-trans
ethyl
acid to D-trans
chrysanthemate and
allethrin
prepares
D-trans
allethrin
Yield
Examples
showed
best D-trans
yield obtained around 74 Chrysanthemic acid
to 75%
yield more than 96%
Different Starting material : D1 – Mixture of cis/trans; patented process
uses only D-trans ethyl chrysanthemate:
Patentee stated that D1 recognizes the relevance of obtaining Trans
chrysanthemic acid as a product. But It does not mention ‘D-trans isomer’
of chrysanthemic acid. However, D1 admits and understands that
obtaining only trans chrysanthemic acid is difficult (column 1, lines 2636): “For the production of alkyl chrysanthemate, there has heretofore been
widely adopted the reaction of 2,5-dimethyl-2,4-hexadiene with alkyl
diazoacetate. However, the product in this reaction is a mixture of alkyl cischrysanthemate and alkyl trans-chrysanthemate. Therefore, it is necessary
to separate the trans-isomer from the said mixture and to covert the cisisomer into the corresponding trans-isomer from the industrial viewpoint.”
Patentee pointed out that D1 uses a mixture (consisting of ‘cis’ and ‘trans’
isomers) of ethyl chrysanthemate as starting material along with sodium
hydroxide and water with the intent to ‘separate’ Cis and Trans ethyl
chrysanthemate
from
the
reaction
mixture
using
the
differential
hydrolysing rates and eventually separate out trans-chrysanthemic acid.
Patentee
submitted
that
D1
is
silent
as
to
whether
the
trans-
chrysanthemic acid separated is D-trans or L-trans, or a mixture of D and
L. On the other hand, the invented process starts with D-trans ethyl
chysanthemate and all the intermediate products are maintained in ‘Dtrans isomer’ state, avoiding unnecessary distillation and additional
897/MUM/2007 (IN236630) Page 52 separation steps asemployed by D1. Therefore costs are reduced. Entire
prior art including D1 does not disclose such a strategy, no inspiration or
suggestion can be found in D1 as to whether one can start a process with
just d-trans material. This idea stems only from the patented process and
marks a fundamental and conceptual difference between the present
invention patent and D1.
Solvent system – patented invention – mixed solvent system; D1 –alcohol +
water: Patentee points out that patented invention employs a ‘mixed
solvent system’ i.e. Water and Methyl alcohol is added along with D-trans
‘ethyl’ Chrysanthemate. This results in formation of Ethanol during the
process. So during the reaction, there is a mixture of Water, Methanol and
Ethanol in the reactor. All these factors assist in providing better reactivity
and
therefore
better
purity
and
yield
of
D-trans
Chrysanthemic
Acid.Patented invention is confined to use of methyl alcohol with ‘ethyl’
chrysanthemate. D1 does not use such a combination of solvents during
the reaction. Examples number 1 to 5 of D1 have Ethanol. Example
number 6 of D1 has Methanol.
Patentee pointed out that in D1,“ETHYL”Chrysanthemate and “ETHANOL”
are used together, and “METHYL” Chrysanthemateand Methanol is used
together. So,all examples of D1 are drawn to a single solvent systemi.e.
either methanol or ethanol. Only in the patented patent process “Ethyl”
chrysanthemate is used with Methanol resulting in mixed solvent system
of “Methanol + Ethanol+ Water” in the reactor. Such a mixed solvent
system (ethanol); methanol and water) results in high yield and purity
much better than process of D1.
Use of lower temperature:
Patentee submitted that the first step of the patented process is performed
at low temperature i.e. between 5 to 10 degrees C. Such selection of low
temperature is purposeful. The reaction of sodium hydroxide, d-trans ethyl
897/MUM/2007 (IN236630) Page 53 chrysanthemate and methanol is exothermic giving out heat which may
disturb
the
equilibrium
and
promote
conversionof
isomers.
Lower
temperature avoids any such conversion and maintains D-trans product in
same state. D1 uses high temperature of above 50 Degrees C. Infact, the
reaction in some examples of D1 is conducted also around 80 degrees C.
D1 further states at Column 3, Lines 40-43 that “when a lower temperature
is adopted, the selection of the trans-isomer becomes increased but a longer
reaction time is required”.
Patentee submitted that D1 thus teaches away from using lower
temperature. It discourages the use of lower temperature as it could
increase the reaction time and such increase in reaction time is not
desirable at commercial level.
Patentee submitted that despite using lower temperature of 5 to 10 degrees
C,the overall yield is more than 96% yield in the patented invention
whereas in D1 examples the maximum yield is around 74 to 75%. In fact,
patented invention uses low temperature to obtain high yield. On the other
hand, D1 is completely oblivious to such co-relation, as is evident from the
table below:
897/MUM/2007 (IN236630) Page 54 Example 1 of D1 yield is calculated as follows: Molecular weight of trans
ethyl chrysanthemate is 196.29. Quantity 64.8 grams divided by 196.29 =
0.33 moles input. Molecular weight of transchrysanthemic acid is 168.23.
Quantity 37.91 grams divided by 168.23 = 0.225 moles output. Yield % =
output moles / input moles x 100. So 0.225 / 0.33 x 100 = 68.18%. All
examples yield has been calculated on this basis.
The above table illustrates that the yield at 60°C (Example 2) is 45%, at
50°C (Example 3) the yield is 66.67% but at 85°C (Example 4) yield
increases to 74.33%. At 60°C the yield is 45% and at higher temperature
80°C (example 5) it is 59.17%. This clearly demonstrates that there is no
co-relation between the temperature and yield of transchrysanthemic acid
as per D1 process. According to the alleged teaching of D1 at Column 3,
lines 40-43, the selectivity and yield of trans isomer of chrysanthemic acid
should increase at lower temperature. However, from the above table, no
such inference can be drawn of Dl – the teachings of D1 are inconsistent
with its own Examples 1-6.
Ratio of isomer-alkali:
Patentee pointed out that in the patented invention, ratio of alkali to trans
isomer of ethyl chrysanthemate is 1.23:1. In this reaction and with such
process parameters and with mixed solvent system, higher than equimolar
alkaligives quicker reaction and yield. This is another unique feature of the
invention. Example in present Patent, 297.50 grams of D-trans ethyl
chrysanthemate (molecular weight 196.29) is 1.52 moles starting material
trans. ( i.e. 297.50 grams divided by 196.29 = 1.52 moles ) Sodium
hydroxide 75 grams (molecular weight 40) is 1.875 moles of alkali( i.e 75
grams divided by 40 = 1.875 moles ). Ratio of alkali sodium hydroxide
1.875 moles to d-trans ethyl chrysanthemate 1.52 moles = 1.23:1. This is
more than equimolar use of alkali. On the other hand, D1 at Column 3
lines 16-18 states that quantity of alkali required to be used should be in
897/MUM/2007 (IN236630) Page 55 equimolar amount or less with respect to the trans-isomer in the starting
material. D1 also states that use of larger amount of alkali may result in
cis-formation and selectivity to trans is inferior. It also says selection and
controlling reaction conditions may be difficult if higher quantity of alkali
is used.
Going against this suggestion of D1, Patentee in present patent has used
higher amount of alkali, and yet controlled the reaction conditions to
obtain high yield of D-trans Chrysanthemic acid, while maintaining isomer
state. Examples of D1 makes no logical relationship of moles of alkali and
starting material trans isomer and the yield of trans chrysanthemic acid.
NaOH = Sodium Hydroxide; KOH = Potassium Hydroxide; NaOEt = Sodium
Ethylate (refer table below)
Patented process despite using higher than equimolar amount of alkali,
surprisingly achieves higher yields (96% or more) of d-trans chrysanthemic
acid as compared to the yields reported by D1.
Residue of unreacted ethyl chrysanthemate:
897/MUM/2007 (IN236630) Page 56 Patentee submitted that as noted from all the examples of D1, certain
amount of unreacted ethyl chrysanthemate is left as residue in the
reaction pot (column 4, example 1, lines 23-26). Whereas in the patented
process, there is no unreacted cis-ethyl chrysanthemate left as no ‘cis’
isomer is formed at all. Therefore, in present patent invention no
additional steps are required to manage the unwanted residue left in the
reaction.
Acidification:
Patentee submitted that in the patented process, sodium chrysanthemate
is
converted
to
D-trans
chrysanthemic
acid
with
sulphuric
acid,
i.e.Sulphuric acid is added BEFORE Chrysanthemic Acid is formed. On
the other hand, in D1, the trans-chrysanthemic acid is already formed and
present in the aqueous medium prior to addition of mineral acid such as
sulphuric acid. So Patentee points out that in D1,Sulphuric acid is added
AFTER Chrysanthemic Acid is formed. So the use of sulphuric acid in D1
is for a different purpose, and hence cannot be compared to patented
process.
Extraction of trans chrysanthemic acid with solvent Petroleum Ether:
Patentee submitted that patented process in claim 1 step (d) and step (e)
uses petroleum ether for extraction of d-trans chrysanthemic acid.
Although petroleum ether is a light solvent, with chrysanthemic acid,
reaction mixture forms two layers, of which petroleum ether layer
comprises of wholly of d-trans chrysanthemic acid and the water layer has
dissolved sodium sulphate. Further, the extraction using petroleum ether
in case of the patented invention is carried out in aqueous alcoholic
system. D1 does not disclose ‘Layer separation’ using Petroleum Ether for
extraction
of
D-trans
chrysanthemic
acid.
Also
in
the
patented
invention,solvent petroleum ether is removed at 20 degrees C in step (f),
which helps in maintain isomer purity. Hence, many factors have been
897/MUM/2007 (IN236630) Page 57 intelligently combined in the use of specific type of petroleum ether at this
step (d) and step (e) of the patented process.
Multiple extractions and distillations in D1:
Patentee stated that In D1 the process involves five
evaporation/distillations to obtain Trans chrysanthemic acid, which are:
•
Distillation of Ethanol at high temperature;
•
Evaporation of n-hexane;
•
Distillation of unreacted ethyl chrysanthemateat high temperature;
•
Evaporation of Toluene;
•
Distillation of trans chrysanthemic acid,
Whereas in Patented process involves only two instances of distillations:
•
Distillation of Methanol
•
Distillation of Petroleum Ether
Patentee submitted that it is not desirable to involve multiple distillation /
evaporation steps as it could lead to loss of product and compromise on
the final yield and purity. This shows why present Patent process is clean
and efficient and gives better yield compared to D1.
Yield:
Patentee stated that there is a huge improvement in yield in the patented
process. Yield has been calculated in following table based on the input
material Trans isomer content (trans ethyl chrysanthemate) and output
material Trans isomer content (trans chrysanthemic acid). Patentee
submits that best yield in examples of D1 is 74% to 75%, where as in
patented process the yield is 96.66%.
The same is shown in the table
below:
897/MUM/2007 (IN236630) Page 58 YIELD CALCULATION EXAMPLE-1 – D1:
Molecular weight – transethyl chrysanthemate – 196.29
Molecular weight – D-trans chrysanthemic acid – 168.23
Patentee submits that till Claim 1 step(f) of the Patent 236630, Yield is
more than 20% higher than cited prior art D1. This yield benefit is carried
forward to subsequent steps in the multiple step reaction process.
Opponent gave a calculation of yield of D1 example 1. This was given in
opponent affidavit dated 26th May 2015, page numbers 4 and 5. Opponent
has givenmisleading calculation and changed the figures of D1.The
897/MUM/2007 (IN236630) Page 59 following table shows the quantities as given in D1, and the quantities
stated by opponent:
Yield of Trans Chrysanthemic Acid
Calculation
As in D1
Opponents
Comments
Affidavit
dated26th
May 2015
Input :
Total qty of Ethyl
100
-
Chrysanthemate
Trans % of Ethyl
64.8
Chrysanthemate
Total grams of trans
64.8
58.87
Ethyl Chrysanthemate
Opponent has
reduced input
grams
Mol. Weight of Trans
196.29
196.29
0.33
0.30
Ethyl Chrysanthemate
Moles of Trans Ethyl
Chrysanthemate input
Opponent has
reduced input
moles
Output :
Total grams of trans
47.1
47
80.5
----
Chrysanthemic Acid Cis
+ Trans
% of Trans Isomer in
this
Opponent has not
considered Trans
% of total output
quantity
897/MUM/2007 (IN236630) Page 60 Actual Trans
37.92
47
As per D1, 80.5 %
Chrysanthemic Acid
of 47.1 grams =
obtained in Grams
37.92 grams
Mol. Weight of trans
168.23
168.23
0.225
0.279
68
93
Chrysanthemic Acid
Moles of trans
Chrysanthemic Acid
actually obtained
Yield %
ouptut moles / input
moles x 100
Patentee submitted that Opponents have given misleading and incorrect
calculation to make it appear that D1 has high yield. Opponents have not
followed what is clearly stated in D1. The objective is to calculate input
material Trans isomer moles and output material Trans isomer moles,
then calculate yield of output material i.e. Trans chrysanthemic acid. D1
example 1, states 100 grams input out of which 64.8% is trans. So it is
clear that 64.8 grams of Trans material is input, i.e. 0.33 moles.
(64.8/196.29 = 0.33) By using wrong basis, Opponent has started with
58.87 grams,i.e. 0.30 moles. Instead of 0.33 moles opponent has used 0.3
moles, which is lower input than what is stated in D1. In the output
material D1 clearly states 47.10 grams of Chrysanthemic Acid, out of
which only 80.50% is Trans. So the actual “trans” Chrysanthemic Acid is
80.50% of 47.10 grams=37.92 grams, which is 0.225 moles (37.92/168.23
= 0.225). Opponent has ignored the 80.5% Trans purity in his calculation.
Opponent has taken entire 47.10 grams as yield, which is wrong because
this entire 47.10 grams is not “Trans” isomer. Only 80.50% of this is Trans
as stated in D1. So instead of 37.92 grams Trans output, Opponent has
taken 47.10 gram which is not the correct output Trans % given in D1. In
897/MUM/2007 (IN236630) Page 61 effect, Opponent has reduced the quantity of input material and increased
the quantity of output material, to mislead and show higher yield in D1.
The yields of D1, Trans Chrysanthemic acid range from 45% to 75%. The
above is yield table showing 6 examples of D1 and present Patent 236630
is reflected in the affidavit dated 30th April 2015 of Dr.Soman. Present
invention patent D-trans chrysanthemic acid has 96.66% yield, which is
substantially higher than D1. In fact, the Opponents have also conducted
experiments as set out in their document D9,and in all experiments
opponents have obtained yields of around 96%. Thus, the Opponents
confirm the claim of high yield of Patentee i.e. 96%.
Patentee submitted that Opponents’ argument was higher starting input
‘trans’ material would automatically result in high yield of ‘trans’ output
chrysanthemic acid. However, from the table above examples of D1, it is
apparent that this is not correct. D1 shows that there is no co-relation
between input Trans and output Trans material. Example 1 of D1 starting
with 64.8% has obtained output 68.18%. But in example 4 of D1, starting
with 90.1% they have obtained lower output 74.33%. Patentee submits
that the relation between input Trans and output Trans is dependent on
process conditions.
897/MUM/2007 (IN236630) Page 62 Hence, the present invention has made a judicious choice of the reaction
conditions and solvents to produce the most optimum yield of d-trans
chrysanthemic acid of 96.66%. A new feature that is not derivable from
D1.
D1 teaches away :
Patentee submitted that D1 is not a document that renders the present
patent invention obvious; rather it is a document that teaches away and
discourages a person skilled in the art because:
a) D1 recommends use of higher temperature and specifically states that
at lower temperature, the reaction time would be longer (column 3, lines
40-43). In support of such proposition, all the examples of D1 are carried
out at temperature higher than 10 ºC i.e. 80, 50, 60, 85ºC.Because none of
the examples are carried out at below 10 ºC, there is no expectation of
success at such temperature. The patented invention employs such low
temperature between 5-10ºC and yet the patented process succeeds in dtrans chrysanthemic acid with more than 96% yield, which was never
contemplated or suggested by D1.
b) D1 teaches that the ratio of isomer to alkali must be equimolar or less
with respect to the trans isomer in the starting first step. On the other
hand, the patented process goes against this teaching and uses higher
amount of alkali i.e. 1.23 moles of NaOH to 1 mole of d-trans ethyl
chrysanthemate. Yet, surprisingly, higher yield of d-trans chrysanthemic
acid as compared to the yield of D1 is achieved by the patented process i.e.
96%against maximum yield in D1 examples of 75%.
In this regard, Patentee relied upon case of IN re Gurley – [27 F.3d 551]-pg.
3 : “....A reference may be said to teach away when a person of ordinary
skill, upon reading the reference, would be discouraged from, following the
path set out in the reference, or would be led in a direction divergent from the
897/MUM/2007 (IN236630) Page 63 path that was taken by the applicant. The degree of teaching away will of
course depend on the particular facts; in general, a reference will teach away
if it suggests that the line of development flowing from the reference’s
disclosure is unlikely to be productive of the result sought by the
applicant....”
Thus, the patented invention has gone away from and far ahead of
teachings of the prior art and is innovative and inventive.
Document D2 – US 3,934,023:
Without prejudice to the submission that D2 cannot be argued by the
Opponent as being barred by res-judicata, the Patentee submitted :
D2,the process suggests the preparation of dextro rotary form of the
chrysanthemic acid and maintaining Cis to Trans isomer ratio unchanged
before and after optical resolution under appropriate conditions.Assuming
without admitting, as alleged by the Opponent, the process of D2 appears
relevant only for Claim 1 step (h), it does not renders the entire
Patentprocess obvious. The essential differences between D2 and the
patented process are as under:
The starting material used in D2 and the present invention is different. In
D2 the starting material is a mixture of cis and transchrysanthemic
chloride i.e. (+)-cis-trans-chrysanthemic acid chloride which has 17.7% by
weight of (+)-cis-chrysanthemic acid chloride.
Patented invention uses in Step (h) ingredient D-allethrolone (72:21).
D2 does not teach combination of pyridine and toluene for “D-trans
isomer” Allethrin preparation as in present invention patent.
The D-Allethrolone used in the present invention has very specific isomer
ratio which is not disclosed by D2. Selection of d-allethrolone with specific
isomer ratio gives the desired end product in the present invention.
897/MUM/2007 (IN236630) Page 64 In D2, the mole ratio of Pyridine to chrysanthemic acid chloride is 1.51, i.e.
is high and used in excess. In the patented process, the mole ratio of
Pyridine to d-trans chrysanthemic acid chloride is 1.14. Lesser quantity of
pyridine is required in the present invention which is advantageous.
Without prejudice, the complicated process set out in Example 2 of D2 is
not followed by the patented invention step.
Sequence of addition of reactants and the temperature of reaction and
distillation are different. Duration of the addition and reaction is different ,
D2 requires drying over anhydrous magnesium sulphate, and 33 g of
alumina and 16g of silica gel addition, stirring for 30 minutes at room
temperature, then removing alumina and silica gel by filtration, then
concentrating solution under reduced pressure. None of this is required in
present Patent invention process. The process is shorter and more
efficient. In view of the above submissions, the Patentee submits that
document D2 does not render obvious Step (h) of the present invention.
Regarding Documents D1 and D2 in combination :
Without prejudice to the submission that D1 + D2 combination cannot be
argued by the Opponent as being barred by res-judicata, the Patentee
stated as under.
As per the Opponent, D1 and D2 together teach the process claimed by the
patent. This is completely incorrect because:
D1 deals with step (a) to (f) of Claim 1 of the patent, that too with different
isomer reactants and very different process. D2 deals with step (h) of claim
1 of the patented process. Again with different isomer reactants and
different process. Step (g) of Claim 1 is missed out even if these two
documents are read together. Step (g) of claim 1 of the patent "D-trans
Chrysanthemic Acid to Acid Chloride" step.
Chrysanthemic
acid
to
d-trans
Conversion of d-trans
Chrysanthemic
acid
chloride,is
an
important step. This is done with ideal solvent and reaction conditions as
in the patented process. If this step is skipped then end product 'D-trans
897/MUM/2007 (IN236630) Page 65 allethrin' cannot be formed. There is no indication or suggestion in D1 that
the route of D2 be adopted after the reaction of D1 is completed. D1 and
D2 together do not teach that the reaction should be conducted at low
temperature this knowledge is available only from the patent. Assuming for
argument’s sake that D1 and D2 could be combined, Lab experiment
conducted by external Lab M/s. Aura Biotechnologies shows otherwise.
This experiment took the output material of Step (f) and proceeded to
process Step (h) directly, omitting Step (g) of claim 1. It did not lead to
product D-trans allethrin. This experiment and its results EX no. 5 Code:
SOL-5 was filed as annexure to affidavit of Dr. R.Soman dated 30th April,
2015/5th May, 2015. Thus, it is proved that D1 and D2 together cannot
lead to making D-trans Allethrin.
Therefore Step (g) of claim 1 cannot said to be obvious or common in a
multiple step reaction process. It acts as a bridge between the previous
step and subsequent step and enables to make the product “D-trans
allethrin”.
Patentee submitted that D1 and D2 do not disclose use of “D-trans isomer”
of Ethyl chrysanthemate, or Chrysanthemic acid. They all deal with
different isomer composition, mixtures of Cis and Trans isomers. The
physico-chemical properties of other mixtures are different and hence
those process are not relevant to the patented process that uses reactant
D-trans
isomer
of
Ethyl
chrysanthemate,
or
D-trans
isomer
Chrysanthemic acid. Using those isomer mixtures it is not possible to
arrive at product D-trans Allethrin. The physico-chemical properties of Dtrans isomer Chrysanthemic acid are different from other isomer mixtures
/ composition of Chrysanthemic acid. Hence any general other “Acid to
Acid chloride” processes are not relevant to the specific reactant /
intermediate in Patentee’s process. D1 or D2 do not teach or suggest
conversion of D-trans Chrysanthemic acid to acid chloride in solvent nHeptane. It is only the patented process that teaches this conversion in nHeptane with certain process conditions. Better yield and purity of D-trans
897/MUM/2007 (IN236630) Page 66 Chrysanthemic acid chloride will lead to better yield and purity of product
D-trans allethrin. The superiority of the product of the step of
“chlorination”, pertaining to D-trans isomer Chrysanthemic acid is
important. This has also been overlooked by opposition board.
“Chlorination” process of “d-trans isomer Chrysanthemic acid” in solvent
n-Heptane is not disclosed earlier in any prior art.
This mosaic or clubbing of D1 and D2 by opposition board and opponents
further shows that individual parts of a multiple step process cannot be
randomly mapped to prior art declared obvious. Each step is important
and relevant in a multi-step process. This also rules out obviousness and
workability of D1 and D2 considered together to make “D-trans allethrin”.
Document D3 - GB 1,448,228:
According to Patentee, Opponents allege that D3 renders obvious step (g)
of Claim 1. D3 is a process for preparation of cyclopropane carboxylic acid
which
is
completely
different
in
structure
and
properties
from
chrysanthemic acid. Hence, the process and conditions for preparation
thereof cannot be extrapolated to chrysanthemic acid. The Opponents have
mentioned that the acid obtained according to Example 2 of D3 is
([1R,trans]-3-(2,2-difluorovinyl)-2,2-dimethyl
cyclopropane
carboxylic.
acid, i.e. a molecule wherein the two methyl groups of the vinyl group of
trans-chrysanthemic acid are substituted with two fluoro atoms. The
patentee
submitted
that
the
present
invention
refers
to
‘D-trans
chrysanthemic acid’ and is totally different from the carboxylic acid
disclosed in D3. It is too far-fetched for the Opponents and mischievous to
state that the process of the present invention can be arrived at on the
basis of D3 as the reactants, solvents, reaction conditions, sequence of
steps and the end product are completely different from those disclosed in
the present invention. Present patent invention uses n-Heptane solvent for
step (g), i.e. Acid to Acid Chloride. The Opponents while citing this
897/MUM/2007 (IN236630) Page 67 document have deliberately generalized the reaction sequence without
quoting the detailed process parameters in terms of the reactants, the
solvent systems, the temperatures, and the time required for the reaction,
and the process followed for the purification of the prepared compounds.
In fact, the process in patent 236630 clearly obviates the use of hazardous
solvents such as benzene and uses n-Heptane thereby making the process
industrially scalable, economical and safe to operate. Table showing
comparison of Patent 236630 and D3 :
Patent 236630 Claim
D3 , Experiment B, line
42
Claim 1 Step (g): Treating [1R,-Trans]-3-(2,2d-trans chrysanthemicacid difluorovinyl)-2,2 dimethyl
with
150
grams
thionyl cyclopropane
carboxylic
chloride, thus forming d- acid. Solution of Acid (110
trans chrysanthemic acid mg) in benzene 5(ml) was
chloride which further is treated with pyridine and
dissolved
in
n-heptane thionyl chloride and left to
solvent.
stand for 3 hours and end
of which acid has been
converted to acid chloride.
Document D4 - GB 3,723,469 :
Patentee submitted that this document has been cited by the Opponents
as being relevant in respect of Step (g) i.e. treating D-trans-chrysanthemic
acid with thionyl chloride for forming D-trans chrysanthemic acid chloride
in n-Heptane solvent.
897/MUM/2007 (IN236630) Page 68 The first important difference lies in solvents used. n-Heptane is not used
or disclosed in D4. Instead if employs petroleum ether. Given below is a
table comparison:
Patent 236630 Claim
Example of D4
Claim 1 Step (g): Treating d-trans 140 cc of petroleum ether
chrysanthemic acid with 150 grams (b.pt. = 35 deg-70 deg C), one
thionylchloride,
thus
forming
d- introduces 73.5 g. of 1-trans-
trans chrysanthemic acid chloride chrysanthemic (1S, 2S) acid
which further is dissolved in n- then,
Heptane solvent.
drop
by
drop
over
several minutes, 35 cc of
thionyl chloride, agitates for 2
hours
at
ambient
temperature, eliminates the
volatile
fractions
distillation
under
reduced
pressure,
then
redistills
under
more
powerful
a
by
vacuum, and obtains 80 g. of
1-trans-chrysanthemic
(1S,2S) acid chloride, under
0.4 mm of mercury.
Further, in the patented process, after obtaining D-trans chrysanthemic
acid with 98.4% purity, this D-trans chrysanthemic acid is charged in
glass addition flask. Thionyl Chloride is charged in another adding flask
and n-Heptane is charged in main glass flask which is heated to 65
degrees C. Thionyl chloride and Acid (D-trans chrysanthemic acid) is
added gradually in the main glass alternatively. It is further refluxed for 2
hours
at
higher
temperature
897/MUM/2007 (IN236630) to
obtain
204.75
gms
of
d-trans
Page 69 chrysanthemic acid chloride. As disclosed in example in present patent
process. Patentee submitted that alternative addition of Thionyl chloride
and Acid is not suggested by D4. Reaction of patented invention is carried
out under reflux conditions at 70°C and not at ambient temperature like in
D4. Under these conditions the reaction goes to completion faster. Thus,
the manner of carrying out the process, the reaction, temperature, the
time, solvents and other conditions are completely different in patented
process from D4 and therefore, D4 is not relevant at all.
Document D5 -, GB 2,169,293:
Patentee submitted that this document has been cited by the Opponent as
being relevant to step (g) of Claim 1 wherein D-trans chrysanthemic acid is
treated with thionyl chloride to form D-trans chrysanthemic acid chloride
in n-Heptane solvent. Patentee submitted that in example 4 of D5, some
other compound is treated with thionyl chloride in the presence of
pyridine. Pyridine which is used as catalyst in D5 process for Chlorination,
is not required in the patented process. It is submitted that if the reactants
including the solvent system and temperature as defined in the patented
process are different from D5, then obviously the patented process is
entirely different from D5. D5 also does not teach the use of solvent nHeptane, and process conditions of the present invention patent.
Comparison table:
Patent 236630 Claim
Example 4 of D5
Claim 1 Step (g): Treating d-trans 16.82 g 2-(2,2-dimethyl-vinyl)chrysanthemicacid with 150 grams 3-3-dimethyl-cyclopropane
thionyl chloride, thus forming d- carboxylic acid are dissolved
trans chrysanthemic acid chloride in 50 ml benzene and to the
which further is dissolved in n- solution 0.5 ml pyridine is
897/MUM/2007 (IN236630) Page 70 Heptane solvent.
added under stirring at room
temperature,
7.6ml
thionyl
chloride are added dropwise.
Mixture is then heated for 3
hours
and
evaporated
in
vacuum. Residue is dissolved
in
25ml
pyridine
under
stirring at 20 degrees C. 18.7g
3-bromo-benzyl-alcohol
dissolved in 25ml pyridine is
added
dropwise
minutes.
within
Reaction
30
mixture
stirred for 4 hours at room
temperature,
filtered
and
filtrate is evaporated. 32.38 g
3-bromo-benzyl
2-(2,2-
dimethyl-vinyl)-3-3-dimethylcyclopropanecarboxylate
are
obtained
Patentee stated that the starting material and output material are different
in D5. It is not even remotely related to D-trans Chrysanthemic Acid.
Benzene is not used in present invention, it is used in D5 process.
Benzene is not a safe solvent. Pyridine is not required in present invention
process at this step. Temperature and duration of reaction is different in
present invention process. As can be seen from the comparison table,
there is nothing in common between D5 and present invention patent
236630
Document D6 - Crombie et. al. :
897/MUM/2007 (IN236630) Page 71 Patentee submitted that this document has been cited as being relevant to
Claim 1 step (g) of the patented process. However, D6 does not teach the
use of solvent n-Heptane, and process conditions of the patented process.
The process given in D6 requires more than 15 hours for completion, in
comparison to Patent 236630 Claim 1 Step (g) which requires just 4 hours
and 30 minutes. It may be observed from comparison table below that the
solvents used, temperature, reaction time, conditions ofD6 are different
from the process disclosed in the present invention. In D6, quinoline and
linseed oil is used and the solution is kept overnight. Further, distillation
step in the process of D6 causes frothing and difficulties which are
overcome by the patented process.
897/MUM/2007 (IN236630) Page 72 Document D7 – Matsui et. al. :
Patentee submitted that this document has been cited as being relevant to
Claim 1 step (g) of present patent. Again n-Heptane and the process
conditions of the present patent are not disclosed in D7. D7 does not use
“D-trans” Chrysanthemic Acid. D7 is completely different from present
invention step (g), as can be seen from this comparison table:
Patentee submitted that the patented process does not merely substitute
n-Hexane solvent with n-Heptane. The reactants and the process
conditions are entirely different in present patent. It may be noted that the
reaction time in D7 is 8 hours at room temperature whereas in case of
patented process, the reaction time is 2 hours at 70 degrees C. It is always
desirable to have short duration process in commercial scale. It makes it
897/MUM/2007 (IN236630) Page 73 more economical and efficient. Benzene is added in D7 which is again not
required in patented process. Patentee further submitted that both
processes are entirely different from each other, which includes the
temperature of reaction, quantity of reactants, reaction time and solvent
system. All of these impact the final outcome, and the two processes are
entirely different.
Patentee submitted that Document D8 is the Order of the Ld. Controller
in Pre-grant opposition.
Patentee submitted that Opponent did not rely on D9 and D10 for grounds
of inventive step. Therefore under this ground of inventive step, Patentee
has not made any submmissions with respect to D9 and D10.
Patentee also relied upon Dr. Soman’s affidavit and the experiments
conducted by M/s. Aura Biotechnologies Lab for D3 to D7. In order to
test whether the processes disclosed in cited documents D3 to D7 could be
relevant toStep (g) of claim 1 of Patent 236630, Lab experiments were
conducted by an independent Lab. Step (g) of claim 1 is D-trans
chrysanthemic Acid to Acid Chloride. The test was conducted to see if the
process and methods mentioned in D3 to D7 would be relevant or
applicable to D-trans Chrysanthemic Acid and the solvents suggested
could be used. Patentee relied upon the results :
897/MUM/2007 (IN236630) Page 74 Patentee submitted that the results are unchallenged by Dr.Borzatto.
Patentee submitted that Process disclosed in the present patent gave
99.84% yield and 99.08% purity. This was the best yield and purity among
all the experiments conducted. Patentee submitted that the process of D3
did not work with D-trans Chrysanthemic Acid. The process of D4 gave
dark color output with low yield 76% and low purity 73.16%. The process
of D5 did not work for D-trans Chrysanthemic Acid. The process of D6
gave lower yield 82.90%, while taking 15 hours and 25 minutes to
perform. Process of present patent invention required just 4 hours and 30
minutes. In D6 process, even after this long 15 hour duration process the
yield and purity were lower than process of present patent invention. D7
uses solvent n-Hexane, but the process gave low yield 36.04% and low
purity 49.94%. It also gave dark color output. The duration of D7 was 12
hours and 50 minutes compared to present patent invention duration 4
hours and 30 minutes. Relying on these experiments, Patentee further
stated that
cited art D3 to D7 are not relevant to the present patent
invention.
Patentee further submitted that that opposition board report also
mentioned that this step Chlorination (Acid to Acid Chloride) was easy and
897/MUM/2007 (IN236630) Page 75 known. But the important point is that this process as disclosed in present
patent invention is relating to ‘D-trans Chrysanthemic Acid Chloride’ and
uses ‘n-Heptane’ solvent with ideal process conditions. Any normal general
thionyl chloride reaction or any other general chlorination process cannot
be automatically applicable to D-trans Chrysanthemic Acid. Patentee
pointed out that failure of the solvents and process set out in D3 to D7 is
proof that step (g) of patented process is specifically and creatively
designed for preparing d-trans chrysanthemic acid chloride.
Patentee
pointed out that this shows the inventive merit of Claim 1 Step (g) of the
present patent 236630. It gives best yield and purity of D-trans
Chrysanthemic Acid Chloride.
Therefore Patentee submitted that none of the cited art D1-D7 are relevant
and the suggested patch works D1-D2, D1-D2 with D3-D7 are also
irrelevant and a mere application of hindsight.
Patentee further submitted that the entire case of obviousness as argued
by the Opponents rests wholly on hindsight analysis and theory of possible
patch-work of various processes (D1 to D7), using the patented invention
as a blueprint. Also, Patentee submitted that the invention should be
considered “as a whole” and a part by part evaluation of the invention
should be prevented.
Patentee also contended that Hindsight analysis is prohibited in law.
Patentee submitted that the Opponents have used the patent of the
Patentee as a blue print in order to find prior art and show that the
invention is obvious. The fact that the hindsight analysis has been used is
evident from the chart below:
897/MUM/2007 (IN236630) Page 76 897/MUM/2007 (IN236630) Page 77 Patentee relied upon the following case laws to support the fact that such
hindsight analysis is prohibited in law :
a) Richard Ruiz and Foundation Anchoring Systems, Inc. Vs. A.B. Chance
Company [357 F.3d 1270)]:
b) Technograph Printed Circuits Ltd. V. Mills & Rockley (Electronics) Ltd.
[1972] R.P.C. 346
Patentee further submitted that any doubt is to be resolved in favour
of Patentee. Patentee submitted that the Opponent is required to show
“clearly” that the claims as patented lack inventive step. “Clearly” has been
interpreted as being beyond “balance of probabilities”. In view of the
differences and arguments set out in the foregoing paragraphs, it is clear
that the Opponent has failed to make out any case of lack of inventive
step. Assuming that there is any doubt in case of obviousness, the same
should be resolved in favour of the Patentee. Patentee relied upon the case
of E.I Du Pont de Nemours & Co [1971] RPC 7 at 21]Sir Lionel.
Therefore Patentee submitted that the Opponents have miserably failed to
prove obviousness and accordingly, this ground be dismissed in toto.
OPPOSITION BOARD’S RECOMMENDATIONS
As pointed earlier that there are two oppositions boards report in this
case. The first opposition report is before the earlier learned
Controller
decision
while
the
second
opposition
board
report
submitted after the direction of Hon’ble IPAB (Hereinafter called as
Opposition Board 1 & Opposition Board 2)
As required under the Rules, an opposition board was constituted to
examine the documents submitted in connection with the opposition
proceedings as under Rule 56. The recommendation of the report of the
897/MUM/2007 (IN236630) Page 78 ‘Board was made available to both the parties. The relevant aspects of the
recommendation are quoted herein below:
Opposition Board 1
D1: The Board placed both side’s argument side by side and commented
that: We have compared the cited prior art, the statement of the opponents
and the patentee and finds that the allegation of the opponents that Steps
a), b), c), d), e) and f) are anticipated, by the teachings of D1 can’t be
withstand.
D2: The board compared the arguments and held that the patentee in his
reply statement submits that there is difference between two processes in
terms of starting material used to carry out the process. The starting
material used by the patentee is d-trans chrysanthanic acid whereas,
example 2 in the cited documents indicated the staring material is (+)-cistrans-chrysanthemic acid chloride. We are not convinced with the
argument of the opponents that step h) is anticipated from the teachings of
D2, since the starting materials are not alike.
D3: We are not convinced with the argument of the opponents that step ah) is anticipated from the teachings of D3 since, (i) the temperature of step
a); (ii) the starting cyclopropane carboxylic acid; (iii) the use of n-heptane
in step g) and the kind of alcohol in step h) are not alike to D3. How can a
person skilled in the art from the teachings of D3 would easily have started
from trans- isomer of chrysanthemic acid chloride in order to obtain only
the trans- isomer of allethrin?
D4: We are not convinced with the argument of the opponents that step g)
of the patentees claim is anticipated from the teachings of D3 since; a
different solvent is used whose teaching is not available in D4.
D5: Being a French document was not taken into cognizance.
D6-D7: are exclusively related to the step (g) of claim 1 of the claimed
invention and not as a whole the process the patentee has been granted.
Under such circumstances, for a specific step of the process of the
897/MUM/2007 (IN236630) Page 79 patentee, a mosaic of D6 and D7 can’t make the invention as a whole noninventive. Documents D6 and D7 relied by the opponents are in piece mill
and for one step of the whole process and not relating to the said technical
field. So, we can’t take the cognizance of these two documents D6-D7,
while giving recommendation on whether the granted claim is obvious and
do not involve an inventive step as relied by the opponent.
D8: which is the decision of the Controller in pre-grant opposition
proceedings; we can’t have any view on it.
D9 and D10: relates to some experimental data submitted by the
opponents which are filed for consideration in the opposition proceedings.
However, the authenticity of such submission is questionable and the
opponents have not filed the same as required u/s 79 of Patents Act. The
opponents have not taken the onus of authenticity of these documents and
have thrown it to the burden to Controller. Hence, the credibility of these
documents can’t be recognized by us. Any other document or submission
either the opponents or the patentee have made and there is no explicit
elaboration from either side, we can’t take cognizance of that.
We are also not convinced by the contention of the opponents on
combination of documents like (i) D1, D7 and D2; (ii) D1, D4 and D2;
(iii) D1, D6 and D2; (IV) D1 and D5 and; ((v) D3, D1 and D7 that the
claim of the patent lack inventive step. The reason for the same is
already attributed in the detailed analysis provided above.
Opposition Board 2
The findings of Opposition Board 2 are follows
D1: The closest document D1 (US3943167) teaches a Process for preparing
trans-chrysanthemic acid, which discloses process of a process for
preparing an enriched trans-chrysanthemic acid from a mixture of alkyl
trans-chrysanthemate and alkyl cis-chrysanthemate which comprises
reacting said mixture with an alkali metal hydroxide or an alkali metal
alcoholate in an amount of from 0.5 to 1 mole based on 1 mole of the
897/MUM/2007 (IN236630) Page 80 trans-isomer in the presence of water or an alcohol at a temperature of
from 10OC
to 150OC to hydrolyze the trans-isomer predominantly and
separating
the
hydrolyzed
product
from
the
unreacted
alkyl
chrysanthemate to obtain an enriched trans-chrysanthemic acid (claim 1);
Document D1 further discloses that reaction mixture thus obtained, there
are included the hydrolyzed product of alkyl trans-chrysanthemate, i.e.
trans-chrysanthemic acid, and the unhydrolyzed alkyl cis-chrysanthemate.
Trans-Chrysanthemic acid is quite soluble in an aqueous alkaline solution
in the form of the carboxylate ion. On the other hand, alkyl cischrysanthemate is not soluble in water and can be dissolved in organic
solvents such as ether, benzene, toluene and hexane. Therefore, the said
reaction mixture, which is alkaline, may be treated with an appropriate
water-immiscible organic solvent in the presence of water, whereby transchrysanthemic acid is retained in the aqueous layer and alkyl cischrysanthemate is extracted in the organic solvent layer. When desired,
the reaction mixture may be concentrated to remove the reaction medium
and/or the alcohol produced in the course of the hydrolysis prior to the
treatment
with
the
organic
solvent.
For
recovery
of
the
trans-
chrysanthemic acid from the water layer, it may be made acidic with a
mineral acid such as sulfuric acid or hydrochloric acid to separate the free
trans-chrysanthemic acid, which may be recovered by a conventional
procedure such as extraction. The alkyl cis-chrysanthemate in the organic
solvent
layer
may
be
subjected
to
epimerization
to
produce
the
corresponding trans-isomer (column 3 lines 55-65 to column 4 lines 1-10).
Document D1 is the closest prior art for the claimed subject-matter of the
Patent Number 236630 having similarity in the sense of the step (a) to (e)
of instant claim 1, however the pressure applied for the separation by
distillation is 4kg, and the temperature for the step (a) where the instant
claim 1 starts with an isomer resulting in synthesis of d-trans allethrin as
final product, moreover, Document D1 and the subject-matter of claimed
in claim 1 until step (a) to (e) is having similar reactants with an optimized
897/MUM/2007 (IN236630) Page 81 quantity which restricts the scope of the claim 1 strictly to the claimed
amount of the reactant, further the claimed instant claim having an
additional steps (f) to (h), for the conversion of d-trans chrysanthemic acid
chloride by reacting with thionyl chloride and reacting the d-trans
chrysanthemic acid chloride by reacting with d-allethrolne and pyridine in
toluene;
D2: Document D2 (US3934023) relates to a (+)-cis, trans-chrysanthemate,
an insecticidal composition containing the following first component or the
first and second components as an active ingredient, and to the
preparation thereof, in which it discloses 35.2 Grams of (+)-cis, transchrysanthemic acid chloride containing 18.8 % by weight of (+)-cischrysanthemic acid chloride were dissolved in 90 ml of toluene (example 1
to 7),
Example 7 of the document D2 teaches 18.7 Grams of (+)-cis, transchrysanthemic acid chloride containing 19.0 % by weight of (+)-cischrysanthemic acid chloride were dissolved in 20 ml of toluene. the
solution was added to a mixture of 16.0 g of (+)-2-allyl-3-methylcyclopent2-ene-1-one-4-ol, 11.9 g of pyridine and 30 ml of toluene over 30 minutes
while maintaining the reaction temperature at from 40 OC to 500C. The
solution was further maintained at the same temperature for 4 hours.
Thereafter the reaction solution was treated in the same manner as
described in Example 1to give 29.4 g of (+)-2-allyl-3-methylcyclopent-2ene-1-one-4-yl-(+)-cis,trans-chrysanthemat e as an oily matter ( example
7).
Therefore document D2 teaches the step (h) of instant claim 1, which along
with the disclosure of D1 which discloses step (a) to (e) rendering the
difference of the conversion d-trans chrysanthemic acid to d-trans
chrysanthemic acid chloride , which is prepared in step (g) of instant claim
1 by reacting the d-trans chrysanthemic acid with thionyl chloride,
Therefore, subject-matter claimed in claim 1 of the instant claim 1 is
differs in the sense of conversion of conversion d-trans chrysanthemic acid
897/MUM/2007 (IN236630) Page 82 to d-trans chrysanthemic acid chloride , which is prepared in step (g) of
instant claim 1 by reacting the d-trans chrysanthemic acid with thionyl
chloride, such conversion for the purpose of enhancing the reactivity of dtrans chrysanthemic acid. The use of thionyl chloride as an organic
chlorinating agent is known practice to person skilled in the art, therefore
step (g) of the instant claim 1 is obvious to person skilled in art,
Therefore, with reference to teaching from documents D1 and D2 make the
subject-matter of claim 1 obvious to person skilled in the art, thus, no
inventive step is acknowledged;
As the document D1 & D2 renders to subject-matter of instant claim 1
obvious , therefore other cited documents are not discussed in details,
however all remaining documents are considered for the purpose of
obviousness;
Therefore the ground for opposition raised under section 25 (2) (e) is
upheld.
ISSUE 4 : INSUFFICIENCY, Section 25(2)(g)
OPPONENTS SUBMISSIONS :
Opponents submitted their contentions in aspect of lack of sufficiency and
clarity in the specification
Regarding clarity in claims:
Opponents stated that in step “a” of claim 1 the quantity of
d-trans
Ethyl chrysanthemate that is being charged into a reaction has not been
mentioned. Step “a” mentions of charging the reactants and does not
mention the temperature at which the reaction takes place.
In step “c” of claim 1 the strength of sulphuric acid has not been
mentioned. The strength, i.e. the concentration of sulphuric acid is very
crucial because the strength, i.e. the concentration, that could be
897/MUM/2007 (IN236630) Page 83 expressed in the application as mol/l. eq/l or % by weight, of the sulphuric
acid would determine the amount of sodium chrysanthemate that would
be converted into d-trans chrysanthemic acid.
In step
“f”
of
claim
1 which relates to distillation of d-trans
chrysanthemic acid at 20 degrees is out rightly wrong since the boiling
point of d-trans chrysanthemic acid at 760 mm of Hg is 246°C as
previously mentioned.
Regarding clarity in specification:
At the outset Opponents submitted that the Example provided at amended
page 6 is against the law of conservation of mass. It is pertinent to note
that if molar calculation is carried out with respect to the quantity of
various ingredients and products that have been mentioned in the example
provided at amended page 6 of the specification, then we get the following:
297.5 gms of d-trans Ethyl chrysanthemate ≡ 1.518 moles
75 gms of NaOH ≡ 1.875 moles
0.123 ml of concentrated (98% w/w) H2SO4 ≡ 0.002284 moles
(taking into consideration that conc. H2SO4 of 98% w/w (density of 1.82
has been used)
251.2 gms of d-trans chrysanthemic acid (title 98,4% purity)≡ 1.469 moles
175 gms of d-trans chrysanthemic acid (taking into account a purity of
98.4% as reported in the line before ≡ 172.2 grams ≡ 1.0233 moles)
150 gms of thionyl chloride ≡ 1.26 moles
204.75 gms of chrysanthemic acid chloride with 98.7 % purity ≡ 1.083
moles
204 gms of chrysanthemic acid chloride(title 98.7% purity) ≡ 1.078moles
340 gms of d-trans Allethrin ≡ 1.099 moles (taking into account the purity
of 97.8% as suggested by the patentee)
This clearly shows that from 1.023 moles of chrysanthemic acid one
can obtain 1.083 moles of chrysanthemic acid chloride and from
897/MUM/2007 (IN236630) Page 84 1.078 moles of chrysanthemic acid chloride one can obtain 1.099
moles of d-trans Allethrin. This is clearly against the law of
conservation of mass.
Lack of clarity with regard to the nature and role of “catalyst” :
Opponents submitted that para 2 of example at the amended page 6 of the
complete specification of the impugned patent mentions of a catalyst.
Strangely, neither the name of the catalyst nor the specific function carried
out by the catalyst has been provided by the Patentee. Surprisingly, no
catalyst has been mentioned in the claim 1.
Opponents submitted that Order of addition of ingredients of step g:
Step g) of IN236630 cannot be reproduced on the basis of the
Example of page 6, since the order to addition of ingredients of step g) is
evidently different from the Example of page 6.
Use of thionyl chloride:
Opponents submitted that a skilled person in the art immediately
acknowledges the trivial and usual conditions for a chlorination step of an
acid with thionyl chloride, with no possible inventive aspects in the specific
ingredients stated in step g).
Opponents further submitted that the amount of the involved ingredients
of step g) are incoherent with respect to what is obtained as it will be clear
by reading the following table:
Example
Chrysanthemic
IN236630
acid
Thionyl
(purity chloride (mol)
98.4%) (mol)
Chrysanthemic
acid
(purity
chloride
98.7%)
(mol)
Page 6
1.025
897/MUM/2007 (IN236630) 1.26
1.082
Page 85 Opponents submitted that from a chemical and stoichiometric point of
view, it is not possible to start from 1.025 mol of chrysanthemic acid to
obtain 1.082 mol of chloride !!! Again it is affirmed that the example seems
to be fictitious and surely not capable to fill the requirement of sufficiency
of disclosure.
PATENTEE’S SUBMISSIONS
Patentee submitted that the main argument of the Opponent is that
certain amounts of certain ingredients as mentioned in the Specification
are not coherent with the claims or vice-versa. The Opponents also urged
that the patent is ‘not workable’. The Patentee responds to these
allegations, without prejudice to the submission the Opponent is barred by
Res-judicata from raising this ground of insufficiency.
Patentee submitted that “insufficiency” is different from “workability” of a
patent. The Opponents have mischievously mixed up both issues. Further,
and without prejudice, Patentee submitted that the Opponent has argued
that the invention is obvious, i.e. it can be worked, but is obvious. In the
light thereof, Opponent is barred from alleging that the invention is not
workable or insufficient.
To counter the arguments of Opponents, Regarding working of the
Patent invention, the Patentee made the following submissions:
a) Invention worked – Form 27 filed:
Patentee submitted that they have been working the invention by following
the patented process and filed working statements in support thereof for
last five years. A copy of the Form 27 filed is being submitted herewith, as
Annexure-A.
897/MUM/2007 (IN236630) Page 86 b) Opponent having performed the patented process in D9 and D10
are estopped from alleging non-working of patent:
The Opponent has repeated the invention of the Patentee and the results
are reported in their documents D9 and D10. In D9, there were nine
experiments successfully performed by the Opponent and they obtained
the product D-trans Chrysanthemic acid with yield around 96%. In D10,
Opponents were able to successfully obtain D-trans Chrysanthemic Acid
Chloride. Thus, just by reading the Patent 236630 complete specification,
Opponents were able to work the invention, without any further
explanation from the Patentee. The very fact that the Opponent has been
able to replicate the invention as described in the patent specification is
sufficient
proof
that
the
invention
is
infact
workable.
Had
they
encountered any problems in working the invention, the same would find
mention in the Post-grant Opposition. This issue is a new ground raised at
the time of arguments.
Summary of results reported by Opponents in document D9 are given in
table below:
897/MUM/2007 (IN236630) Page 87 Document D9 of Opponent covers Claim 1 Step (a) to Step (f). D-trans
Chrysanthemic Acid is obtained by Opponent.
As per example given in present invention patent the yield of D-trans
Chrysanthemic Acid is 96.66%. The opponents have successfully worked
the invention process to get the same results yield around 96% as per D9.
From the above, it is clear that a person skilled in the art can refer to the
Patent complete specification and successfully arrive at same results.
Hence, the Opponent is estopped from alleging that the patented process is
not workable or insufficient. The patent is complete specification detailed
and can be worked.
c) One working example: Patent provides one working example – which is
sufficient to show how the invention is performed. As long as one working
example is given which works, there is no question of insufficiency as held
in Tata Beverages case by the IPAB. To support this argument Patentee
relied on the following judgement: Tata Global Beverages Limited Vs.
Hindustan Unilever Limited
Patentee’s response to other alleged ‘insufficiency’ issues:
Opponent: The amount ofthe starting chrysanthemic ester and the relative
chrysanthemic acid are not indicated in thedescription and that these
amounts are essential in order to justify the declared yield of thefinal
product
Patentee’s reply: In this regard, the Patentee submits that the quantities
of these chemicals can be arrived at easily by a personskilled in the art.
The quantity of starting material i.e. d-trans ethyl chrysanthemate has
beenclearly disclosed in the Patent No. 236630 in the example and the
claims are to be readtogether with the complete description.
897/MUM/2007 (IN236630) Page 88 Further, in Document D9, opponent has successfully replicated Claim 1
Step (a) to (f), and found no problems; Opponent even got around 96%
yield, same as that disclosed in example in present Patent.
Opponent: The amount ofthionyl chloride is not coherent with the amount
of d-allethrolone, which in turn is incoherentwith the amount of pyridine.
It is incoherent that 1.26 moles of chloride (if so) are reacted with 5.55
moles
of
alcohol
(d-allethrolone)
i.e.
4.40
times
more
than
the
stoichiometric amount (1.26 moles) and in the presence of2.91 moles of
pyridine that means 2.31 times more than the stoichiometric amount
(1.26moles). In such a case, the excess of unreacted d-allethrolone should
be recovered if not, the process is industrially not applicable.
Patentee’s reply: The Patentee submits that Thionyl chloride and dallethroloneare used in separate stages of the process:
Step (g):
Thionyl Chloride;
Step (h):
D-allethrolone.
Hence, no coherence between these reactants is needed since they are
being used in separate steps of the process. These two reactants are not
used together for a reaction. This further shows that Opponentshave not
understood the invention and the detailed steps of the patented process.
The Opponent having replicated the patented process successfully in D9
and D10 are estopped from alleging incoherence.
Opponent:That the claims are for 150g of thionyl chloride 0.26 moles) are
reacted with d-trans chrysanthemicacid(amount not reported) allowed
chrysanthemoyl chloride (Not reported but presumably, if theyield is
quantitative, 1.26 moles), which was reacted with 540 g (5.55 moles) of dallethrolonein the presence of 230 g (2.91 moles) of pyridine.
Patentee’s reply: Patentee submits that d-transChrysanthemic acid
quantity is disclosed in the example of Patent No. 236630.All the
quantities are disclosed or the numbers inthe claims are easily derivable
897/MUM/2007 (IN236630) Page 89 from the disclosure. A detailed working example is given in the Patent
complete specification. Opponents have been able to work the invention
process as evident from D9 and D10 and no difficulty in carrying out the
patented process disclosed and claimed in Patent No.236630 is reported.
The Patentee submits that the said allegations are therefore baseless, false
and haveno merit.
Opponent:“pyridine in excess gives the use of HCL scrubber has
nosignificance as all HCI formed during the reaction of the acid with thionyl
chloride would becaptured by the excess of pyridine. It is clear that the
comment is based on the assertion thatchrysanthemic acid was reacted with
an equimolaramount of thionyl chloride on the basis ofthe stoichiometry of
step g)”.
Patentee’s reply: Example at page 6 of patent clearly discloses quantities
used. Opponents admit that this is based on their ‘assumptions’ and
‘assertions’ and these assumptions are incorrect and misconceived.
Opponent:"the indicated amounts in the claims are incoherent eachother and
with the declared result of providing a convenient process from an industrial
pointof view".
Patentee’s reply: Ratios and proportions between d-allethrolone,d-trans
chrysanthemic acid chloride, pyridine and toluene in Patent No. 236630,
areconsistent in the Claims and Example. The same is illustrated in the
table given below:
897/MUM/2007 (IN236630) Page 90 The ratios between each ingredient are same in Example and Claims. This
shows that the Example and Claims of Patent 236630 are consistent.
Based on this, all the quantities can be easily derived in the claims and
example. It is a matter of elementary knowledge.
Opponent:In such a case the excess of unreacted d-allethrolone should be
recovered if not the process is industrially not applicable
Patentee’s reply: Patentee has not claimed recovery of unreacted dallethrolone as their unique feature; assuming such unreacted material is
found, person skilled in the art would be well equipped to recover the
same.
Further, the Patentee has pointed out that the Opponents have made New
arguments and issues beyond the Pleadings.
Patentee submitted that the Opponent has argued several issues that are
not part of the original pleadings i.e. the written statement post-grant
Opposition, despite objections by the Patentee. Patentee relied upon
judgment of Supreme Court in the case of Shankar Chakaravarti Vs.
Britannia Biscuit Co. Ltd. &Anr. [(1979) 3 SCC 371] (para 32), any
argument or contention which has no basis in the pleadings cannot be
897/MUM/2007 (IN236630) Page 91 considered by any Court or Tribunal, even if, there is evidence on record in
support thereof. Infact, the Tribunal would be without jurisdiction to consider
the same. The Patentee is responding to the same, without prejudice to the
above.
The Patentee submitted that the following issues were beyong pleadings:
Opponent: Quantity of sulphuric acid given in example in the patent is
insufficient for output of d-trans chrysanthemic acid.
Patentee’s reply: Patentee submits that this plea is frivolous and merits
no consideration. Opponent has never questioned the yield or output
quantity of D-trans chrysanthemic acid in the post-grant opposition.
Claim 1, step (c) of Patent states that sulphuric acid “is used
foracidification,conversion
of
sodium
chrysanthemate
to
D-trans
Chrysanthemic Acid”. Page 4 of the complete specification (Process of
Manufacture Step III) also states that material is acidified by addition of
sulphuric acid, meaning sufficient amount must be added in order to
achieve acidification.Sodium Chrysanthemateis entirely converted to Dtrans Chrysanthemic Acid. Hence, the amount of sulphuric acid added
should be sufficient to complete the conversion. This is a matter which is
within the routine skills of a person skilled in the art. It is pertinent to note
that the Opponent has conducted lab experiments reported in their
Document D9. Opponent has worked the invention by conducting
experiments i.e. nine experiments (yield around 96%). This is same as yield
obtained in example given in present invention patent, yield of D-trans
Chrysanthemic Acid as per present invention patent Step (f) is 96.66%.
Now, the Opponent is estopped from arguing that quantity of sulphuric
acid given is insufficient for output yield of d-trans chrysanthemic acid.
897/MUM/2007 (IN236630) Page 92 Opponent: Conservation of Mass .i.e. certain steps shown in example
showslightly more than 100% yield
Patentee’s reply: Opponent has nowhere contested or demonstrated in
their Opposition that the overall yield or output quantity of any of the
steps of the patented process is incorrect. No scientific evidence has been
submitted to demonstrate that in some steps of the example, the yield is
more than 100%. For arguments sake, Patentee presumed that Opponent
has raised this point to Claim 1 Step (g) and (h). Patentee submitted that
the variations in yield % are within range of experimental errors and
permitted standard deviations. These are some variations which occur
from batch to batch and they are within permissible limits. The issues
pointed out by Opponent for Step (g) and (h), are not errors of Mass or
Yield. At worst, these are minor analytical errors, analysis computation
errors, and weighing errors. This does not change or affect the Claims of
the present invention Patent 236630. It is pertinent to note that Opponent
has replicated the patented process in D9 and they have also faced such
issues. Some experiments conducted by the Opponent also show more
than 100% yield as can be seen from the table below:
897/MUM/2007 (IN236630) Page 93 The yield despite these alleged issues is 96% or more which demonstrates
that the aforesaid errors are inconsequential. Output material D-trans
Chrysanthemic Acid has molecular weight of 168.23. Therefore, in example
no. 6 of above table: 42.4 grams output divided by 168.23 = 0.252 moles
yield. Same basis of calculation has been done for each of the 9 examples.
Opponent states in D9 that they started with input material D-trans Ethyl
Chrysanthemate 0.250 moles. As per Law of conservation of mass, if the
input material is 0.250 moles, then output of D-trans Chrysanthemic Acid
can be only 0.250 moles or lesser. However, the Opponent in D9 reports
some examples output as “0.251 to 0.252”, even though output should not
exceed “0.250”. Example Nos. 1, 6, 7, and 9 show more than 0.250 moles
yield.
A person skilled in the art will understand and acknowledge that these are
within range of experimental errors and permitted human error standard
deviations. The output yield can vary from batch to batch. These are just
lab experimental variations that are routine. This issue raised by opponent
does not affect process of Patent 236630 or its Claims in any manner.
Further, in step (g), Patentee submits that purity of D-trans chrysanthemic
acid is estimated by GC (Gas Chromatography) and in GC analysis the
exact quantity of unreacted Thionyl Chloride cannot always be estimated.
This would mean that weight in grams of output may show bit higher in
any AcidChloride product. In products where there can be unreacted
thionyl chloride present, the purity and yield cannot be directly co-related.
So the opponent’s assumption and yield calculation is incorrect.
Subsequently, Lab experiments were also conducted at external lab M/s.
Aura Biotechnologies, Chennai. Step (g) of Claim 1 was reproduced by this
Lab in Ex no. 1 (SOL-1). Results of experimentis given as annexure to
affidavit filed by Dr R.Soman earlier. The yield of D-trans Chrysanthemic
Acid Chloride in this experiment was 99.84%. This shows that there is no
issues of mass and yield in the process and claims of Patent 236630.
897/MUM/2007 (IN236630) Page 94 Opponent: Catalyst mentioned in process example is not disclosed
Patentee’s reply: This is a new issue which the Opponent has urged
during arguments. Catalyst is not important and does not have any effect
on process yield. It is optional.Catalyst has not been claimed in Patent
claims. Hence, this does not change the claims of the patent. Process can
be completed without catalyst, as can be seen by the Lab experiments
conducted by opponent themselves in D9. Claim 1 Step (a) to (f)is covered
by opponent in D9. Step (f) output is D-trans Chrysanthemic Acid. This
has been reproduced by Opponent by Lab experiments in their submitted
document D9.
Patent 236630 process example shows yield of D-trans
Chrysanthemic
Acid
96.66%.
The
nine
experiments
conducted
by
opponent in D9 have obtained around same yield 96%. Therefore, the
above issue does not merit any consideration.
The Patentee relied upon the following case law to substantiate their stand
that errors in calculation or errors in amounts of certain ingredients in the
Specification does not amount to insufficiency: Dual Manufacturing &
Engineering Inc’s patent – [1977] R.P.C. 189:
Patentee further submitted that in case of Patent 236630, the Patentee has
been working the invention. The opponents also have successfully
replicated the patented process in their documents D9 and D10. Assuming
without admitting that there are any errors in example given in Patent
236630, these calculation errors do not amount to insufficiency, as can be
seen from cited judgement.
The Patentee further made some submissions and clarifications as follows
regarding the claims:
897/MUM/2007 (IN236630) Page 95 As per Claim 1 of the present invention, there is disclosed a process of
manufacturing d-trans Allethrin in the following sequential steps:
a) Charging D-trans Ethyl chrysanthemate into a reactor at a temperature
of 5 to 10 degrees C along with 75 grams of Sodium Hydroxide, 154 grams
of water and 96 grams of methyl alcohol,
Patentee’s Comments: The starting material is with D-trans isomer is
new. This D-trans isomer state is maintained till end of the multiple step
process obtaining D-trans Allethrin. Lower temperature of 5 to 10 degrees
C has not been tried before. Combination of Methyl alcohol and Water with
Ethyl chrysanthemate, forming Ethanol in reactor. Leading to Water +
Ethanol + Methanol has never been done before.
b) Subjecting reactants for saponification and distilled off methyl alcohol at
atmospheric pressure of 4kg,
Patentee’s Comments: The “4 Kg” mentioned, is a unit of measurement of
pressure in the reactor. ‘Kilogram’ or ‘Kilogram Force per Square
Centimeter’ (denoted as kg/cm2 or kgf/cm2) is a pressure unit that has
been largely superseded by the SI unit system of Pascal units.
Reference Source: This website gives the detailed explanation of Kg as
pressure unit:
http://www.sensorsone.com/kgcm2-kilogram-per-square-centimetrepressure-unit/
So, 1 kg as 1kg/cm2 = 98,066.5 Pascals. The calculation of units of
pressure in Kilograms or Kilograms/cm2 can also be done in many
different units. There are many calculations tools and charts available that
convert kg/cm2 this into different units of measurement of pressure.
There are many online websites that do conversion calculations. For
example:
http://www.unitconversion.org/unit_converter/pressure.html
897/MUM/2007 (IN236630) Page 96 When the data of patented process is entered: 4 Kilograms, force/ square
centimeter this is equal to
= 392266 Pa (Pascals),
= 3.922 Bar,
= 2942.23Torr,
= 3.87 standard atmosphere
The Kilogram or Kilogram force/square centimeter unit is close to Bar unit
and to atmosphere pressure unit. Pressure reactors and its benefits are
known in chemistry. It is being tried for the first time in conversion of Dtrans ethyl chrysanthemate to D-trans Chrysanthemic Acid process.
c) Cooling of contents at 20°C and further acidification with sulphuric acid
wherein sodium chrysanthemate is converted into D-trans chrysanthemic
acid,
Patentee’s Comments:The benefit of cooling gives better yield and results.
Page 4 of the complete specification (Process of Manufacture Step III) also
states that Sodium Chrysanthematematerial is acidified by addition of
sulphuric acid to convert to D-trans Chrysanthemic Acid. Purpose and use
of Sulphuric acid is to convert entire sodium chrysanthemate to D-trans
chrysanthemic acid.
This use and addition of sulphuric acid before
chrysanthemic acid is formed has never been done before. Complete
conversion will give better yield in Step (f), i.e. higher yield of D-trans
Chrysanthemic Acid.
d) Adding 1.70 kgs quantity of petroleum ether which forms two layers.
Petroleum layer containing D-trans chrysanthemic acid and water layer
with dissolved sodium sulphate,
Patentee’s Comments: Petroleum Ether has never been used before for
extraction of D-trans Chrysanthemic Acid. The grade and quantity
Petroleum Ether used is also beneficial. This enables better layer
897/MUM/2007 (IN236630) Page 97 separation and lower temperature distillation, thereby enabling to
maintain D-trans isomer state.
e) Allowing two layers to settle for 1 hour, water layer is drained to effluent
tank and D-trans chrysathemic acid remains in the reactor,
Patentee’s Comments: This layer separation with Petroleum Ether layer
containing D-trans Chrysanthemic Acid, and water layer containing
sodium sulphate has not been done before. The choice of solvent and its
quantity suitable to ingredient D-trans isomer of Chrysanthemic Acid,
gives ideal layer separation. This helps in better extraction and yield.
f) Carrying distillation of d-trans chrysanthemic acid at 20 degrees C.
Patentee’s Comments: The description given in the patent (Page 5, Step
V) explains that Solvent is distilled to obtain pure acid. This is also
demonstrated in the example in the Patent specification. Solvent Petroleum
Ether is removed at 20 degrees. Low temperature distillation helps to
maintain D-trans isomer state of Chrysanthemic Acid. The grade of solvent
Petroleum Ether chosen allows for this low temperature removal of solvent
by distillation.
g) Treating D-trans chrysanthemic with 150 grams thionyl chloride, thus
forming d-trans chrysanthemic acid chloride which further is dissolved in
N-H-heptane solvent,
Patentee’s Comments: Patent complete specification (page 5, Step V)
discloses Acid is treated with thionyl chloride to make Chrysanthemic acid
chloride. Example on page 6 of specification also discloses clearly 150
grams thionyl chloride. 350ml n-Heptane solvent is also clearly disclosed
in the example. Heating of n-Heptane solvent and process conditions are
disclosed in the example. Output obtained from this step Chrysanthemic
Acid Chloride is also mentioned. D-trans Chrysanthemic Acid to D-trans
897/MUM/2007 (IN236630) Page 98 Chrysanthemic Acid Chloride using n-Heptane as solvent with this ideal
process conditions has never been done before.
h) Adding 540 grams d-allethrolne (72:21), 230 grams pyridine and 600
grams toluene with d-trans chrysanthanic acid chloride in a reactor
gradually resulting to desired D-trans allethrin.
Patentee’s Comments: Complete specification of Patent (page 5, Step VI)
mentions reactant d-allethrolone (72:21). This is a new external ingredient
added in the process at this Step (h). This is reacted with intermediate
formed in Step (g) which is D-trans Chrysanthemic Acid Chloride. This
reaction forms product D-trans Allethrin. D-allethrolone is commercially
available in the market and mostly imported from China.Allethrolone can
be purchased from various traders who can be contacted online at
http://www.buyersguidechem.com/AliefAus.php?pnumm=772172521087
&modus=einprod&anzahl_produkte_cas=3
Allethrolone also exists in various isomer forms like: D, L, and mix of these
forms DL. The (72:21) represents the isomers present in the d-allethrolone.
D-allethrolone means that predominant isomer in product is‘d’ isomer.
References can be found online on Allethrolone:
https://www.chem.wisc.edu/areas/reich/syntheses/allethrolonekawamoto.htm [compound structure]
http://www.chemspider.com/Chemical-Structure.10612.html- [compound
structure]
Patentee further submitted that the Patent complete specification also has
a diagram depicting the chemical structures and reaction diagram for each
step of the process. This page has heading “Reactions for formation of DTrans Allethrin”. This further explains and clarifies the starting material
D-trans ethyl chrysanthemate, to D-trans Chrysanthemic Acid, to D-trans
897/MUM/2007 (IN236630) Page 99 Chrysanthemic Acid Chloride, to D-trans Allethrin. The structure of the
Acid and the Acid Chloride is given. The last step of the process in this
page shows the addition of this additional ingredient D-Allethrolone. The
other reactant D-trans Chrysanthemic Acid Chloride is carried forward
from earlier step. Reacted with this ingredient d-allethrolone to form Dtrans Allethrin in the last step.
Patentee submitted that this process with sequential steps and reaction
scheme, process starting from D-trans ethyl chrysanthemate to D-trans
allethrin has not been done before.
OPPOSITION BOARD’S RECOMMENDATIONS
As pointed earlier that there are two oppositions boards report in this
case. The first opposition report is before the earlier learned
Controller
decision
while
the
second
opposition
board
report
submitted after the direction of Hon’ble IPAB (Hereinafter called as
Opposition Board 1 & Opposition Board 2)
Opposition Board 1 has rejected the ground of insufficiency of the
Opponents in toto in its findings, stating that “As far as lack of clarity and
insufficiency in the opposed patent application is concerned, we would like to
say that in case of process chemistry disclosure of examples in a
specification are the best method of performing the invention and are the
most preferred embodiment of the invention. These examples are also very
concise to define the restricted scope of invention for which protection is
sought. From the disclosure in examples, a person skilled in art is expected
to perform the invention without any technical assistance or ambiguity. The
opponent has relied under this ground of opposition and states that some
essential amounts of the ingredients are missing or incoherent in the
description as filed.
897/MUM/2007 (IN236630) Page 100 Reference is made to the example disclosed in page 6 of the specification of
the granted application wherein there is a clear disclosure of performing the
invention. We find that such disclosure is sufficient and would be enabling a
person skilled in the art to perform the invention without any ambiguity. Even
if the mole of some of the reactants is not disclosed in the present case, a
person skilled in the art be able to perform the disclosed invention without
any ambiguity”
The opponents have failed to establish this ground of opposition”
Opposition Board 2 in their findings relating to insufficiency has wrongly
mentioned that addition of new material as an example on page number 6
is incorporated with prescribed procedure without Form 13.
CONCLUSIONS ON SUBSTANTIVE ISSUES :
From the above pleadings, it appears that both the opponents and the
patentee have cited a number of grounds and case laws to establish
their stand. Some of the points are irrelevant/superfluous and some of
the points are relevant and worth discussing in the instant patent
application under post-grant opposition. As far as the time line and
procedural part of the procedure as defined in the law are concerned,
both the opponents and the patentee are well disciplined. However, the
plethora of grounds, prior art documents and case laws put forth by both
the parties
are
irrelevant
in
nature
need
not
be addressed. Both
the parties have unnecessarily over burdened the Controller in citing
different case laws.
However, I am concerned with the relevant documents, relevant
grounds of opposition and relevant case laws. My decision is based on
897/MUM/2007 (IN236630) Page 101 the outcome of
invention disclosed, analysis of
the
relevant
documents and case laws, and the argument made by both the
opponents and patentee.
Having considered the detailed arguments of both the parties, the pregrant opposition & its review decisions, the two opposition board
recommendations, the teachings of the various prior art documents on
record, the affidavit(s) filed by both the parties, I shall now deal with
each ground of the opposition as discussed during the hearing.
The Opponents in written statement of opposition, had pressed grounds
under section 25(2)(a), 25(2)(b), 25(2)(c), 25(2)(d), 25(2)(e), 25(2)(f), 25(2)(g),
25(2)(h), 25(2)(i), 25(2)(j) and 25(2)(k). During hearing, grounds under
section 25(2)(a), 25(2)(b), 25(2)(c), 25(2)(d), 25(2)(f), 25(2)(h), 25(2)(i), 25(2)(j)
and 25(2)(k) were not pressed by the Opponents and accordingly these
grounds are treated as withdrawn and therefore I am not going into
these grounds.
I shall now deal with Inventive step ground of the opposition as
discussed during the hearing.
INVENTIVE STEP (Section 25(2)(e)
Section 25(2)(e) Claims obvious and lacking in inventive step:
According to Section 2(1)(ja) of the Act, " "inventive step" means a feature
of an invention that involves technical advance as compared to the existing
knowledge or having economic significance or both and that makes the
invention not obvious to a person skilled in the art".
897/MUM/2007 (IN236630) Page 102 From all the cited documents D1-D10, affidavits of Dr. Soman and
Dr.Borzatta, disclosures & evidences filed the teachings that flow from
them is as follows:
It is evident from the Complete Specification, description and claims of the
present patent that the invention relates to the process for manufacturing
D-trans Allethrin. The product is used as an active ingredient in mosquito
repellant and control products. The process includes the esterification of
an optically active alcohol with an acid chloride. The ester so formed has
high insect repellant properties. This special synthesis route has been
developed for specific use in household insecticide products as an Active
ingredient against mosquitoes. The process essentially consists of the
three stages
The principal claim of the granted patent is :
Process of manufacturing d-trans Allethrin comprising of following steps:
a) charging d-trans Ethyl chrysanthemate into a reactor at a temperature
of 5 to 10 degrees C along with 75gms of Sodium Hydroxide, 154 grams of
water and 96 grams of Methyl Alcohol,
b) subjecting reactants for saponification and distilled off methyl alcohol at
897/MUM/2007 (IN236630) Page 103 atmospheric pressure of 4kg,
c) cooling of contents at 20 degrees C and further acidification with
sulphuric acid wherein sodium chrysanthemate is converted into d-trans
chrysanthemic acid,
d) adding 1.70 kgs quantity of petroleum ether which forms two layers,
petroleum layer containing d-trans chrysanthemic acid and water layer
with dissolved sodium sulphate,
e) Allowing two layers to settle for 1 hour, water layer is drained effluent
tank and d-trans chrysanthemic acid remains in the reactor,
f) Carrying distillation of d-trans chrysanthemic acid at 20 degrees,
g) Treating d-trans chrysanthemic with 150 grams thionyl chloride, thus
forming d-trans chrysanthemic acid chloride which further is dissolved in
N- H-heptane solvent,
h) adding 540 grams d-allethrolne(72:21) 230 grams pyridine and 600
grams toluene with d-trans chrysanthemic acid chloride in a reactor
gradually resulting to desired d-trans allethrin.
Now, I consider the cited prior art documents.
Document D1 (US 3943167)
D1 is the closest prior art and is being cited as disclosing the steps (a-f) of
the patented process. D1 does not disclose process steps (g) and (h) of the
patented process. D1 does not disclose the process to prepare D-trans
Allethrin.
1. D1 relates to a process for the preparing trans-chrysanthemic acid.
Claim 1 and column 2 lines 15-23 disclose a process for preparing transchrysanthemic acid which comprises reacting a mixture of alkyl transchrysanthemate and alkyl cis-chrysanthemate with an alkali metal
hydroxide or an alkali metal alcoholate in the presence of water/alcohol at
a temperature of from 10° to 150° C in order to hydrolyze and separate
897/MUM/2007 (IN236630) Page 104 trans isomer from unreacted cis isomer.
2. The object of the patented process is to synthesize d-trans allethrin from
d-trans ethyl chrysanthemate, whereas the main objective of D1 is to
provide a process for preparation of enriched trans chrysanthemic acid
from
the
mixture
of
alkyl
trans-chrysanthemate
and
alkyl
cis-
chrysanthemate. Document D1 on Para 5 in column 1 states that “It has
now unexpectedly been found that, when treated with an alkali under certain
conditions, alkyl trans-chrysanthemate and alkyl cis-chrysanthemate are
hydrolyzed in different rates with respect to each other. It has also been
found that, by the utilization of such a difference in the hydrolyzing rate,
alkyl trans-chrysanthemate can be predominantly hydrolyzed to the
corresponding free acid, which may be readily separated from unreacted
alkyl cis-chrysanthemate. The present invention is based on these findings”.
Thus, the main objective of D1 is to utilize the difference in hydrolysis rate
of alkyl trans-chrysanthemate and alkyl cis-chrysanthemate to isolate trans
chrysanthemic acid in the hydrolysis step, which can be readily separated
from unreacted alkyl cis-chrysanthemate and thereby enriching the
hydrolyzed product with trans chrysanthemic acid. The patented process
does
not
involve
use
of
racemic
mixture
of
cis
&
trans
ethyl
chrysanthemate or chrysanthemic acid. Further, the patented process
does not involve additional steps corresponding to separation of unreacted
ethyl chrysanthemate, as shown in example 1 of D1. In working examples
1 to 6 of D1, there is unreacted “cis chrysanthemate” which is separated
out in its process with additional steps like extraction or removal of
unreacted alkyl cis and trans chrysanthemate, whereas there is no
unreacted material left in Steps (a-f) of Claim 1 of the patented process. So
no additional steps are required to be carried out, thereby resulting in
higher yields of D-trans chrysanthemic acid.
3. The process of granted patent uses starting material as ‘D-trans’ isomer
897/MUM/2007 (IN236630) Page 105 and maintains this isomer till end product D-trans allethrin. It is known
that the process and reaction parameters affect isomer content and can
also cause changes in isomer content as is evident from D1. It is also
observed in the working examples 1-6 of D1, that there is no co-relation
between input material isomer content and the output material isomer
content. Thus, this also addresses the inventive merit of starting material
used in the patented process.
4. D1 highlights the problem that obtaining only trans chrysanthemic acid
is difficult (column 1, lines 26-36): “For the production of alkyl
chrysanthemate, there has heretofore been widely adopted the reaction of 2,
5-dimethyl-2, 4-hexadiene with alkyl diazoacetate. However, the product in
this reaction is a mixture of alkyl cis-chrysanthemate and alkyl transchrysanthemate. Therefore, it is necessary to separate the trans-isomer from
the said mixture and to covert the cis-isomer into the corresponding transisomer from the industrial viewpoint.”. Due to the above mentioned problem,
D1 uses a racemic mixture (consisting of ‘cis’ and ‘trans’ isomers) of ethyl
chrysanthemate as starting material along with sodium hydroxide and
water with the intent to ‘separate’ Cis and Trans ethyl chrysanthemate
from the reaction mixture using the differential hydrolysing rates and
eventually separate out trans-chrysanthemic acid whereas the invented
process starts with D-trans ethyl chrysanthemate and all the intermediate
products are maintained in ‘D-trans isomer’ state, avoiding unnecessary
distillation and additional separation steps as employed by D1 thereby
reducing the costs.
5. D1 as a whole does not suggest or inspire to start a process with just ‘dtrans’ isomer material. It is clear that this concept has only been
conceptualized in the patented process and this is fundamental difference
between the present invention patent and D1. These clearly marks that the
patentee has applied his inventive skills in selecting ideal and novel
897/MUM/2007 (IN236630) Page 106 process conditions to ensure that the isomer profile remains the same
right from the beginning of the process till end in such a multiple step
process.
6. The other major difference noted between the patented process and D1
is that D1 uses single solvent system i.e. either methanol or ethanol with
water whereas the patented invention employs a ‘mixed solvent system’ i.e.
Water
and
Methyl
alcohol
is
added
along
with
D-trans
‘ethyl’
Chrysanthemate. As a result of which there is formation of Ethanol during
the process. As such during the reaction, there is a mixture of Water,
Methanol and Ethanol in the reactor. All these factors contribute in
providing better reactivity, better purity and increased yield of D-trans
Chrysanthemic Acid.
7. Another important difference noted between the patented process and
D1 is that the first step of the patented process is performed at low
temperature i.e. between 5 to 10 degrees C. The use of low temperature is
of importance as the reaction between sodium hydroxide, d-trans ethyl
chrysanthemate and methanol is exothermic and it may disturb the
equilibrium and further leads to conversion of isomers. Lower temperature
as such avoids any such conversion and maintains D-trans product in
same state. The temperature as disclosed in examples in D1 is in the range
above 50-85 Degrees C. D1, highlights at Column 3, Lines 40-43 that
“when a lower temperature is adopted, the selection of the trans-isomer
becomes increased but a longer reaction time is required”. Thus, D1
teaches away from using lower temperature. It does not suggest the use of
lower temperature as this could increase the reaction time and as such not
feasible commercially. In fact, this careful selection of low temperature is
the inventive contribution of patentee that has resulted in high yield of Dtrans Chrysanthemic Acid.
897/MUM/2007 (IN236630) Page 107 8. Another important aspect of the patented process is the ratio of alkali to
trans isomer of ethyl chrysanthemate. D1 at Column 3 lines 16-18 states
that quantity of alkali required to be used should be in equimolar amount
or less with respect to the trans-isomer in the starting material. D1 also at
column 3 lines 21-28 states that use of larger amount of alkali may result in
maintaining cis-isomer unreacted, the selectivity is
inferior & selection of
appropriate reaction conditions is difficult.
The patentee going against this teaching used higher than equimolar
amount of alkali, and yet controlled the reaction conditions obtaining high
yield of D-trans Chrysanthemic acid.
9. Document D1 at lines 66 of Column 3 to line 3 of Column 4 states that
“For Recovery of the trans-chrysanthemic acid from water layer, it may be
made acidic with a mineral acid such as sulphuric acid or hydrochloric acid
to separate the free trans-chrysanthemic acid, which may be recovered by a
conventional process such as extraction”. This makes it clear that in D1,
sulphuric acid is used after the trans-chrysanthemic acid is formed. In
contrast to this, in Step (c) of Claim 1 of the patented process, sodium
chrysanthemate
is
converted
to
D-trans
chrysanthemic
acid
with
sulphuric acid, i.e. Sulphuric acid is added before trans-chrysanthemic
Acid is formed. Thus the use of sulphuric acid in D1 is for a different
purpose, and hence cannot be compared to patented process.
10. The process as disclosed in D1 is cumbersome and requires as much
as five evaporation/distillations to obtain Trans chrysanthemic acid at
certain stages of reaction, i.e. Distillation of Ethanol at high temperature;
Evaporation of n-hexane; Distillation of unreacted ethyl chrysanthemate at
high
temperature;
Evaporation
of
Toluene;
Distillation
of
trans
chrysanthemic acid. It is therefore not feasible to carry out the process as
these steps would result in loss of yield. In contrast the patented process
897/MUM/2007 (IN236630) Page 108 only involves two distillations i.e. Distillation of Methanol & Distillation of
Petroleum Ether leading to better yield of D-trans Chrysanthemic acid.
11. As regards to yields of D1, calculated by both the opponents &
patentee, I am not convinced with the way the results are calculated by the
opponents.
Example
1
of
D1
(in
Column
4)
shows
input
ethyl
chrysanthemate 100 grams, consisting of 35.2% of the cis isomer and
64.8% of trans isomer. D1 clearly mentions 100 grams, trans isomer 0.33
moles (i.e.64.8 grams). The Opponent in his affidavit has taken input as
0.3 moles (58.87 grams). D1 mentions output trans-chrysanthemic acid as
47.1 grams containing trans isomer 80.5%. Opponent has considered
entire 47 grams not considering the 80.5% mentioned in D1. Therefore, I
am convinced from the patentee’s submission that the best yield of trans
chrysanthemic acid in examples of D1 is just 74% to 75%, whereas in the
patented process the yield is 96.66%.
It is clear from the above findings that D1 document neither teaches nor
inspires to lead to the Steps (a-f) of the patented process. D1 document
clearly teaches away from what has been carried out in patented process.
I hereby rely on IN re Gurley – [27 F.3d 551]-pg. 3
“....A reference may be said to teach away when a person of ordinary skill,
upon reading the reference, would be discouraged from, following the path
set out in the reference, or would be led in a direction divergent from the path
that was taken by the applicant. The degree of teaching away will of course
depend on the particular facts; in general, a reference will teach away if it
suggests that the line of development flowing from the reference’s disclosure
is unlikely to be productive of the result sought by the applicant....”
897/MUM/2007 (IN236630) Page 109 In view of these differences, the patented process is certainly different,
technically advanced and economically significant when compared
with the process disclosed under D1.
Document D2 (US 3934023)
Document D2 relates to a (+)-cis,trans-chrysanthemate, insecticidal
composition. This document is being cited to disclose Step (h) of Claim 1 of
the patented process. D2 does not disclose Steps (a-g) of Claim 1 of
patented process. D2 does not disclose the process from D-trans ethyl
chrysanthemate to prepare D-trans Allethrin.
The following differences were observed between D2 and the patented
process as under :
1. Document D2 in example 2 discloses the reaction of (+)-trans, cischrysanthemic acid chloride with 17.7% by weight of cis chrysanthemic
acid
chloride
with
(±)-2-allyl-3-methylcyclopent-2-ene-l-one-4-ol
in
presence of pyridine and toluene at temperature of 40-50°C to obtain (±)-2allyl-3-methylcyclopent-2-ene-l-one-4-yl-(+)-cis,trans chrysanthemate.
In example 7, (+)-cis,trans-chrysanthemic acid chloride with 19.0% by
weight
of
(+)-cis-chrysanthemic
acid
chloride
with
(+)-2-allyl-3-
methylcyclopent-2-ene-l-one-4-ol in presence of pyridine and toluene at
temperature of 40-50°C to obtain (+)-2-allyl-3-methylcyclopent-2-ene-lone-4-yl-(+)-cis,trans chrysanthemate.
In Patented process Step (h) of Claim 1, the starting material is D-trans
chrysanthemic acid chloride and (R)-3-allyl-2-methyl-4-oxocyclopent-2enyl (d-allethrolone). The final product in Step (h) of patent process is (R)3-allyl-2-methyl-4-oxocyclopent-2-enyl,2,2-dimethyl-3-(2-methylprop-1enyl) cyclopropanecarboxylate (D-trans allethrin).
Thus, the staring material and final product in both the examples of D2
897/MUM/2007 (IN236630) Page 110 are different from that of the patented process in Step (h) of claim 1.
2. In D2 the ratio of Pyridine to chrysanthemic acid chloride is 1.51,
whereas in the patented process the ratio of Pyridine to d-trans
chrysanthemic acid chloride as 1.14. Lower quantity Pyridine is used in
the patented process as compared to D2. As such Pyridine is known to be
a hazardous chemical, hence it is beneficial that its use should be
minimized. It is also difficult to remove from the reaction mixture.
3. The temperature and time for carrying out the reaction in D2 examples
2 and 7 is 40 to 50 degrees C for 4 hours, whereas the temperature &
time of Step (h) of Claim 1 of the patented process example is at 20
degrees C for 3 hours.
4. The process as disclosed in D2 is very lengthy and complicated. In D2,
toluene layer is dried over anhydrous magnesium sulfate, and 33 g of
alumina and 16 g of silica gel are added to the solution, which is then
stirred for 30 minutes at room temperature. After removing alumina and
the silica gel by filtration, the solution was concentrated under reduced
pressure. All these process steps are not required to be carried out in
Step (h) of Claim 1 in the patented process. Thus the patented process
is different, simple and has economic edge over D2.
Considering the above differences of patented process over D2, it is clear
that the process under Step (h) in Claim 1 of patented process is different
from D2. D2 also does not disclose Step (a-g) of Claim 1 of patented
process. Hence, Claim 1 of patented process is not disclosed in view of the
teachings of examples 2 and 7 of D2.
897/MUM/2007 (IN236630) Page 111 Document D3 (GB1448228)
Document D3 deals with substituted 2,2-dimethyl cyclopropane carboxylic
acid esters, processes for their preparation & their use as insecticides.
Document D3 on page 2 lines 44-46 discloses synthesis of dihalovinyl
cyclopropane
carboxylates
formally
derived
from
(+)-trans-(1R,
3R]
chrysanthemates by replacement of the vinyl methyl groups. D3 is being
cited as disclosing Steps (a-h), of Claim 1 of patented process in example
2. D3 does not disclose the process from D-trans ethyl chrysanthemate to
prepare D-trans Allethrin. After going through the Example 2 in D3,
following differences were noted:
1. The starting material as used in the D3 is methyl [1R,-trans]-3-(2,2difluorovinyl)-2,2-dimethyl cyclopropane carboxylate whereas the staring
material in the patented process is D-trans ethyl chrysanthemate. Product
of
D3
is
[1R,-trans]-3-(2,2-difluorovinyl)-2,2-dimethyl
cyclopropane
carboxylic acid whereas the product under Steps (a-h) of claim 1 of
patented process is D-trans Allethrin.
2. D3 does not relate to the preparation of D-trans allethrin.
3. D3 does not disclose any of the reactants, reagents, solvents, reaction
temperature and the process of the reaction as disclosed in patented
process.
4. I am also not convinced with the argument that Step (a-h) of patented
process is obvious from the teachings of D3, for the following reasons:
i] the temperature of step (a) is different;
ii] the starting cyclopropane carboxylic acid is different;
iii] the use of n-Heptane in step (g)
iv] the kind of alcohol in step (h) is different;
897/MUM/2007 (IN236630) Page 112 In view of the above distinct differences, the process as disclosed in D3 is
entirely a different process from that claimed in patented process. Further,
the solvents and the alcohol used in Claim 1 of patented process are not
disclosed in Example 2 of D3. In view of the above mentioned differences,
Claim 1 of patented process is not taught or disclosed by Example 2 of D3.
It is practically impossible for a skilled artisan by any stretch of
imagination, to refer to D3, in order to make D-trans Allethrin from Dtrans ethyl chrysanthemate.
US 3723469 (D4)
Document D4 relates to a process for the preparation of cyclopropane
derivatives and compounds therein. This document has been cited as
being relevant in respect of Step (g) of Claim 1 of patented process. D4
does not disclose Steps (a-f) and Step (h) of Claim 1 of patented process.
D4 does not disclose the process from D-trans ethyl chrysanthemate to
prepare D-trans Allethrin.
The following differences were noted:
1. D4 on Column 3 lines 16-18 states “It is in fact an object of the invention
to disclose a process for the preparation of acids with cis-configuration, of
formula I.”. Thus, the object of D4 is preparation of cis-configuration of
internal hemiacylals of racemic or optically-active cis-3,3-dimethyl-2formyl-cyclopropane-1-carboxylic
acids,
whereas,
the
object
of
the
patented process is the synthesis of D-trans allethrin.
2. The most important difference, among others, between D4 and the
patented process, is in solvent used. D4 uses Petroleum Ether whereas
patented process uses n-Heptane in Step (g) of Claim 1.
897/MUM/2007 (IN236630) Page 113 3. The process in D4 is carried out at ambient temperature whereas the
patented process Step (g) is 65 to 70 degrees C.
4. D4 nowhere mentions the use of n-heptane solvent.
Hence, Step (g), of Claim 1 of patented process is not obvious in view
disclosure found in D4. D4 also does not disclose Steps (a-f) and Step (h)
of Claim 1 of patented process.
Document D5 - FR2575746 (D5) Corresponding to GB2169293:
Document D5 relates to the process for the preparation of Pyrethroids
Example 4 of D5 has been cited as disclosing only Steps (g) and (h) of
Claim 1 of patented process. D5 does not disclose Steps (a-f) of Claim 1 of
patented process. D5 does not disclose the process from D-trans ethyl
chrysanthemate to prepare D-trans Allethrin.
Example
4
of
D5
states
that
“2-(2,2.-dimethyl-vinyl)-3,3-dimethyl-
cyclopropane-carbaxylic acid are dissolved in 50ml benzene and to the
solution 0.5ml Pyridine is added and under stirring at room temperature 7.6
ml thionyl chloride are added drop wise. The mixture is then heated for 3
hours and evaporated in vacuo. The residue is dissolved in 25 ml. pyridine
and under stirring at 200 C 18.7g. 3-bromo-benzyl-alcohol dissolved in 25 ml.
pyridine is added drop wise within 30 minutes. The reaction mixture is
stirred for 4 hours at room temperature, filtered and the filtrate is evaporated.
32.38g.
(96%)
3-bromo-benzyl-2-(2,2-dimethyl-vinyl)-3,3-dimethyl-
cyclopropane-carboxylate are obtained”.
Following differences were noted :
1. The process as disclosed in Example 4 of D5 discloses synthesis of 3bromo-benzyl-2-(2,2-dimethyl-vinyl)-3,3-dimethyl-cyclopropane
897/MUM/2007 (IN236630) Page 114 carboxylate whereas the patented process deals with the synthesis of
different product in steps (g) and (h) of Claim 1, i.e. D-trans chrysanthemic
acid chloride and D-trans allethrin respectively.
2. Patented Process in Steps (g) and (h) of claim 1 does not use benzene,
whereas D5 uses benzene as the solvent.
3. Pyridine is used in D5 process for Chlorination. Pyridine is not required
in patented process during the Step (g) of Claim 1 (i.e. Chlorination).
4. In D5, there is no mention of solvent n-Heptane and process conditions
of the patented process.
5. The starting material and output material are different in D5 as
compared to patent process. The reactants mentioned in D5 are not
related to D-trans Chrysanthemic Acid.
6. The reactants, solvents, temperature and other process steps mentioned
in D5 are different and irrelevant to Step (g) and (h) of patented process.
Therefore, D5 in no way makes steps (g) and (h) of Claim 1 obvious. It also
does not teach Steps (a-f) of Claim 1 of patented process.
Document D6 - Crombie et. al. J. Chem. Soc. (1963), 4957-69 (D6):
Document D6 relates to synthesis, absolute configuration and ring-fission
of Cis- and trans-Homocaronic acid, whereas the object of patented
process is to make D-trans Allethrin. This document has been cited as
being relevant in respect of Step (g) of Claim 1 of patented process. D6
does not disclose Steps (a-f) and Step (h) of Claim 1 of patented process.
D6 does not disclose the process from D-trans ethyl chrysanthemate to
prepare D-trans Allethrin.
897/MUM/2007 (IN236630) Page 115 The process under Experimental part of D6 on page 4962 is as follows:
“(+)-trans-Chrysanthemic acid (100 g.) in light petroleum (b. p. 40-60°) (250
ml.) was treated slowly with thinoyl chloride (56 ml.) which had been purified
by distillation first from quinoline and then from linseed oil. The solution was
kept overnight and the solvent was removed at 20° under reduced pressure.
Distillation (frothing usually causes difficulty) gave (+)-trans-chrysanthemoyl
chloride (82.1 g.), b.p. 113-114°mm. 1.4856 (lit., b. p. 100-101°/175 mm,
1.4856).”
From the above experiment it is clear that that the process of D6 as
disclosed on page 4962 is different from the process as disclosed under
Step (g) of Claim 1 of patented process.
Following differences were noted:
1. In the process of D6 the solution is kept overnight then solvent is
removed, whereas in the patented process there is no need to keep the
solution overnight thereby reducing the reaction time under Step (g) of
Claim 1 and working example of patented process.
2. The solvents used, temperature, reaction time, conditions used in D6
are different from Step (g) of Claim 1 and working example in the patented
process.
3. There is no mention of solvent n-Heptane in D6.
Hence, neither Step (g) nor any other steps of claim 1 in patented process
is disclosed in D6. D6 does not teach the process to make D-trans
allethrin from D-trans ethyl chrysanthemate.
897/MUM/2007 (IN236630) Page 116 Document (D7) - Agr. Biol. Chem. Vol.28 No.1, p.27-31, 1964 (D7):
D7 discloses studies on chrysanthemic Acid: Part XIII: Preparation of
Rethrins II and Rethrins II isomers and their relative toxicities to Rethrins
I. This document has been cited as being relevant in respect of Step (g) of
Claim 1 of patented process. D7 does not disclose Steps (a-f) and Step (h)
of Claim 1 of patented process. D7 does not disclose the process from Dtrans ethyl chrysanthemate to prepare D-trans Allethrin.
The process disclosed on page 30 of D7 is reproduced below:
Chrysanthemoyl Chloride:
Chrysanthemic acid (3g. 0.03 M) was dissolved in 20 ml. of n-hexane and
thionyl chloride (4.2 g. 0.035 M) was added and the mixture allowed to stand
for eight hours at room temperature and then refluxed for 4 hours on a water
bath.
Following differences were noted:
1. The patented process uses the solvent n-Heptane in Step (g) whereas D7
uses n-Hexane.
2. D7 uses Benzene whereas there is no mention of Benzene in the
patented process.
3. The reaction time as stated in D7 is 8 hours at room temperature and
D7 further refluxes on water bath for 4 hours with subsequent addition of
dry benzene. There is no need of these additional steps of D7 with
reference to the patented process. The total process time of D7 is
approximately more than 12 hours, whereas the process duration in
patented process is much shorter.
897/MUM/2007 (IN236630) Page 117 4. Reactants, temperature, time and conditions in which the reaction is
done in D7 are different from that of Claim 1 in patented process.
Thus, the major advantage of the patented process, amongst several other
advantages, is the choice of solvent and process conditions which are
ideal, new and essential to obtain D-trans chrysanthemic acid chloride in
Step (g) of claim 1. The process claimed under Step (g) of Clam 1 of
patented process is more economically advantageous as compared to
process disclosed in D7.
D7 does not teach or disclose the patented process. Neither Step (g) nor
any other steps of claim 1 in patented process is disclosed in D7.
Document D8
Document D8 is Order and decision of the Learned Controller in pre-grant
opposition proceedings. As such, no comments can be made on this.
Document D9
Document D9 relates to Lab experiments conducted by Opponents
reproducing Step (a-f) of Claim 1 of patented process. The fact that the
Opponents were able to obtain ‘D-trans Chrysanthemic Acid’ successfully,
shows that the claims are sufficiently enabled with description, for a
skilled artisan to perform the patented process.
Document D10
Document D10 relates to Lab experiments conducted by Opponents
reproducing Step (g) of Claim 1 of Patented process. The fact that the
Opponents were able to obtain ‘D-trans Chrysanthemic Acid Chloride’
successfully, shows that the claims are sufficiently enabled with
description, for a skilled artisan to perform the patented process.
897/MUM/2007 (IN236630) Page 118 It is pertinent to note that the grounds of opposition pressed by Opponents
are “inventive step” and “insufficiency”. The lab experiments in D9 and
D10 are contradictory with reference to the grounds of opposition pressed
by the Opponents. It appears that the Opponents are in a state of
confusion. On one hand Opponents are stating that patented process is
obvious (i.e. known) and they have carried out the process, but on the
other hand they are stating that there is insufficient disclosure in the
complete specification.
The Affidavit of Dr. Borzatta who is a technical expert of the Opponents
has relied on the following documents D1 to D7 to substantiate the stand
taken by the Opponent to render the claim of the subject patent as
obvious. The Affidavit filed by Dr. R. Soman, who is a technical expert of
the Patentee, has submitted his expert opinion in support of patentability.
He has pointed out the differences and drawbacks of D1 to D7 and also
relied on Lab experiments conducted at external lab to substantiate his
stand. Dr.Borzatta then filed his reply Affidavit to counter the findings
of Dr. Soman. All these documents have been considered in deciding this
case.
As regards to the Opponents contention about combining the teachings of
various cited documents, leading to anticipation of patented process, now I
deal with combination of these cited documents.
The opposition board 1 in its findings stated “We are also not convinced
by the contention of the opponents on combination of documents like (i) D1,
D7 and D2; (ii) D1, D4 and D2; (iii) D1, D6 and D2; (iv) D1 and D5 and; ((v)
D3, D1 and D7 that the claim of the patent lack inventive step.
The opposition board 1 has denied in toto that the combined teachings of
these documents anticipates all steps of claim 1 of patented process.
897/MUM/2007 (IN236630) Page 119 The opposition board 2 in its findings have agreed that document D2
teaches the step (h) of instant claim 1, which along with the disclosure of D1
which discloses step (a) to (e) rendering the difference of the conversion dtrans crysathemic acid to d-trans crysanthemic acid chloride , which is
prepared in step (g) of instant claim 1 by reacting the d-trans crysathemic
acid with thionyl chloride. Therefore, subject-matter claimed in claim 1 of the
instant claim 1 is differs in the sense of conversion of conversion d-trans
crysathemic acid to d-trans crysanthemic acid chloride , which is prepared in
step (g) of instant claim 1 by reacting the
d-trans crysathemic acid with
thionyl chloride, such conversion for the purpose of enhancing the reactivity
of d-trans crysathemic acid.
Combination of D1 and D2
It is admitted fact by the Opponents that the cited document D1 discloses
only Steps (a-f) of the Claim 1 of the patented invention and D2 discloses
only Step (h) of the claim 1 of the patented invention process.
1. There is no reference or mention of ‘Chlorination’ or use of ‘thionyl
chloride’ in cited documents D1 and D2. Without such mention or
evidence, I am not convinced with baseless statement made by Opposition
Board 2, that use of thionyl chloride as an organic chlorinating agent is
known practice to person skilled in the art.
2. It is also evident that from the findings of Dr. Soman’s affidavit that
when D1 and D2 are read together, the combined teachings do not disclose
or teach the chlorination step (i.e. conversion of d-trans chrysanthemic
acid to d-trans chrysanthemic acid chloride). Conversion of d-trans
chrysanthemic acid to d-trans chrysanthemic acid chloride is claimed in
Step (g) of Claim 1 of patented process. Further, from Lab experiments
conducted by M/s. Aura Biotechnologies, omitting the Step (g) of Claim 1
897/MUM/2007 (IN236630) Page 120 of patented process, did not lead to completion of reaction and did not lead
to the formation of “D-trans allethrin”.
3. From the above findings it is clear that by combining teachings of D1
and D2, do not disclose the Claim 1 of patented process as a whole. The
chlorination step is an important step in the synthesis of D-trans allethrin.
If this step (g) of Claim 1 is omitted, the end product ‘D-trans allethrin’
cannot be obtained.
Therefore, teachings of documents D1 and D2, individually or in
combination, does not make the subject matter of claim 1 of patented
process obvious to person skilled in the art. D1 and D2, in isolation or in
combination,
do
not
disclose
the
process
from
D-trans
ethyl
chrysanthemate to prepare D-trans Allethrin.
Combination of D1, D7 and D2
It is clear from the above findings relating to D1 and D2, considered in
isolation and in combination, that they do not disclose the patented
process as a whole. (i.e. to prepare D-trans Allethrin starting from D-trans
ethyl chrysanthemate). Attempt is made by Opponents to cite document
D7 in combination with D1 and D2. D7 is not relevant document as the
patented process uses the solvent n-Heptane in Step (g) whereas D7 uses
n-Hexane. As such, D7 does neither suggests nor promotes the use of nHeptane which is the key solvent in the patented process. The total
process time of D7 is approximately more than 12 hours, whereas the
process duration in patented process is much shorter. Reactants,
temperature, time and conditions in which the reaction is done in D7 are
different from that of the patented process. D7 is being cited only for Step
(g) of Claim 1 of patented process.
As such, the combined teachings of D1, D7 and D2 do not teach or lead to
897/MUM/2007 (IN236630) Page 121 the patented process as a whole. Therefore the claims of the patented
process are inventive.
Combination of D1, D4 and D2
It is clear from the above findings relating to D1 and D2, considered in
isolation and in combination, that they do not disclose the patented
process as a whole. (i.e. to prepare D-trans Allethrin starting from D-trans
ethyl chrysanthemate). Attempt is made by Opponents to cite document
D4 in combination with D1 and D2. The field of invention of D4 is different
from that of the patented process. D4 uses Petroleum Ether whereas
patented process uses n-Heptane in Step (g) of Claim 1. As such, D4
neither suggests nor promotes the use of n-Heptane which is the key
solvent in the patented process. The process in D4 is carried out at
ambient temperature whereas the patented process Step (g) is 65 to 70
degrees C. D4 is being cited only for Step (g) of Claim 1 of patented
process.
As such, the combined teachings of D1, D4 and D2 do not teach or lead to
the patented process as a whole. Therefore the claims of the patented
process are inventive.
Combination of D1, D6 and D2
It is clear from the above findings relating to D1 and D2, considered in
isolation and in combination, that they do not disclose the patented
process as a whole. (i.e. to prepare D-trans Allethrin starting from D-trans
ethyl chrysanthemate). Attempt is made by Opponents to cite document
D6 in combination with D1 and D2. There is no mention of solvent nHeptane in D6, which is the solvent used in patented process. The solvents
used, temperature, reaction time, conditions used in D6 are different from
Step (g) of Claim 1 in the patented process. In the process of D6 the
solution is kept overnight then solvent is removed, whereas in the patented
897/MUM/2007 (IN236630) Page 122 process there is no need to keep the solution overnight thereby reducing
the reaction time. As such, D6 neither suggests nor promotes the use of nHeptane, which is the key solvent in the patented process. D6 is being
cited only for Step (g) of Claim 1 of patented process.
As such, the combined teachings of D1, D6 and D2 do not teach or lead to
the patented process as a whole. Therefore the claims of the patented
process are inventive.
Combination of D1 and D5
It is clear from the above findings relating to D1, that it does not disclose
the patented process as a whole. (i.e. to prepare D-trans Allethrin starting
from D-trans ethyl chrysanthemate). Attempt is made by Opponents to cite
document D5 in combination with D1 and D5. The field of invention of D5
is different from that of the patented process. The starting materials and
end product of D5 are different. The reactants mentioned in D5 are not
related to D-trans Chrysanthemic Acid, which is the reactant of the
patented process. The process as disclosed in Example 4 of D5 discloses
synthesis of 3-bromo-benzyl-2-(2,2-dimethyl-vinyl)-3,3-dimethyl-cyclopro
pane carboxylate whereas the patented process deals with the synthesis of
D-trans allethrin. Patented Process does not use benzene, whereas D5
uses benzene as the solvent. Pyridine is used in D5 process for
Chlorination whereas Pyridine is not required in patented process during
the Step (g) of Claim 1 (i.e. Chlorination). D5 also does not mention of
solvent n-Heptane and process conditions of the patented process. The
reactants, solvents, temperature and other process steps mentioned in D5
are different and irrelevant to Step (g) and (h) of patented process.
As such, the combined teachings of D1 and D5 do not teach or lead to the
patented process as a whole. Therefore the claims of the patented process
are inventive.
897/MUM/2007 (IN236630) Page 123 Combination of D3, D1 and D7
It is clear from the above findings relating to D1, that it does not disclose
the patented process as a whole. It is also clear from above findings
relating to D3 and also D7, that they do not disclose the patented process
as a whole. (i.e. to prepare D-trans Allethrin starting from D-trans ethyl
chrysanthemate). Field of invention of these documents are different from
the patented process. D1, D3 and D7 do not relate to the preparation of Dtrans allethrin. In D3, starting material is methyl [1R,-trans]-3-(2,2difluorovinyl)-2,2-dimethyl cyclopropane carboxylate whereas the staring
material in the patented process is D-trans ethyl chrysanthemate. Output
product
of
D3
is
[1R,-trans]-3-(2,2-difluorovinyl)-2,2-dimethyl
cyclopropane carboxylic acid whereas the output product of patented
process is D-trans Allethrin. D3 does not disclose any of the reactants,
reagents, solvents, reaction temperature and the process of the reaction as
disclosed in patented process. D7 is not relevant because the patented
process uses the solvent n-Heptane in Step (g) whereas D7 uses n-Hexane.
Also, Benzene is being used in D7. The total process time of D7 is
approximately more than 12 hours, whereas the process duration in
patented process is much shorter. Reactants, temperature, time and
conditions in which the reaction is done in D7 are different from that of
the patented process. D7 is being cited only for Step (g) of Claim 1 of
patented process.
As such, the combined teachings of D3, D1 and D7 do not teach or lead to
the patented process as a whole. Therefore the claims of the patented
process are inventive.
897/MUM/2007 (IN236630) Page 124 Overall conclusion, regarding combination of documents :
1. In view of the elaborative study and differences stated above, between
patented process and D1 to D7, it is not possible for a skilled artisan to try
any of the combinations a) Combination of D1, D7 and D2, b) Combination
of D1, D4,and D2, c) Combination of D1, D6 and D2, d) Combination of
D1 and D5, e) Combination of D3, D1 and D7, f) D1 and D2, to lead to
the
preparation
of
D-trans
allethrin
starting
from
D-trans
ethyl
chrysanthemate.
2. Prior art documents may suggest several solvents or process conditions.
Mere suggestion or disclosure of a specific step or certain conditions or
particular solvents, by itself does not lead to the conclusion that the
claimed process as a whole is obvious.
3. As such while judging inventive step, invention has to be considered as
a whole. In other words, it is not sufficient to draw the conclusion that a
claimed invention is obvious merely because individual parts of the claim
taken separately are known or might be found to be obvious.
4.
The
patented
process
deals
with
D-trans
Allethrin,
D-trans
Chrysanthemic Acid and D-trans ethyl chrysanthemate. None of the cited
documents D1 to D7, considered in isolation and/or in combination,
mention ‘D-trans isomer’ separately.
5. Hindsight is the tendency to see the event as having been predictable,
after the event has occurred, despite there being no objective basis for this
prediction. Hindsight bias is clearly evident in the selection of these cited
documents. Therefore, D1 to D7 is nothing more than a conscious pick
and choose exercise by the opponents, to find documents in hindsight.
897/MUM/2007 (IN236630) Page 125 6. The documents appear to have been cited by Opponents as a mosaic,
using the steps of the patented process as the basis. The documents are
produced in piecemeal relating to some specific steps of the patented
process and this cannot be used while adjudging the inventive step as a
whole. The entire patent claim as a whole has not been made available in
any of the cited documents considered together or in isolation.
7. Such hindsight analysis is prohibited under Patent Law as can be seen
from following citations and case laws:
a) Bilcare Ltd. v. Amartara Pvt. Ltd: 2007 (34) PTC 419 (Del),
The learned Judge noted that as per the legal position set out in the said
decision, it would not be a defence to show that various components in the
patented product are known separately. The combination of such components
may be patentable. The Court concluded that it would not be permissible for
a defendant to rely on different documents disclosing different components /
features of the product to plead that the product of the patent was known.
b) In paragraph 43 of ORA/08/2009/PT/CH, the Hon’ble IPAB held
Para 43 : “The mere existence in the prior arts, of each of the elements in the
invention, will not ipso facto mean obviousness. For after all most inventions
are built with prior known puzzle-pieces. There must be a coherent thread
leading from the prior arts to the invention, the tracing of the thread must be
an act which follows obviously. We must apply this reasoning to test if
indeed it is obvious, or if it seems to us to be obvious to the person skilled in
the art because of what we know now. If it is the latter, it is hindsight
deduction and is not acceptable, but if it is the former, then the patent must
go”
c) In F.Hoffman La Roche & Anr. vs. Cipla Ltd. , The Hon’ble Delhi
High Court in RFA(OS) 92/2012, in para 139 on page number 74 of 106,
897/MUM/2007 (IN236630) Page 126 held as under : “While conducting an enquiry into obviousness, hindsight is
impermissible and the legal conclusion must be reached on the basis of facts
gleaned from the prior art and should not include knowledge gleaned from
patent disclosure. Teachings in prior art documents have to be considered as
a whole. Teachings away from patent claim are treated as non-obvious. To
inquire into obviousness, two fold inquiry is required to be conducted i.e.
motivation to select and motivation to modify”
d) Commentary of Terrel on the “Law of Patent”, 16th Edition para 762 at page 250 which reads as under:
“Mosaicing 7-62 The “mosaicking” of individual documents or prior uses is
not permissible, unless it can be shown that the skilled person, confronted
with a particular citation, would turn to some other citation to supplement the
information provided by the first. Whether he would do so is a question of
fact.
e) In the Windsurfing International Inc. v. Tabur Marine (Great
Britain) Ltd, [1985] RPC 59, the Court of Appeal held that the question of
obviousness “has to be answered, not by looking with the benefit of
hindsight at what is known now and what was known at the priority date
and asking whether the former flows naturally and obviously from the latter,
but by hypothesizing what would have been obvious at the priority date to a
person skilled in the art to which the patent in suit relates”.
I would like to comment that in this present case the Opponents have
clearly used the patented invention process as the basis for picking and
choosing prior art documents in mosaic, based on hindsight. However, the
Opponents have failed miserably to prove their point.
In view of this, claims of the patented process have inventive merit.
897/MUM/2007 (IN236630) Page 127 According to Section 2(1)(ja) of the Act, " "inventive step" means a feature
of an invention that involves technical advance as compared to the existing
knowledge or having economic significance or both and that makes the
invention not obvious to a person skilled in the art".
The claimed invention thus satisfies both the tests of "technical advance"
and "economic significance" of Section 2(1)(ja) as quoted above, whereas
only one of them is enough to establish the inventive merit of the claimed
subject matter. This novel "process for manufacturing of D-trans allethrin "
is neither within the scope of the skilled artisan nor implied in the prior art
documents cited by the opponent. The claims therefore involve inventive
step. The patented invention therefore satisfies the statutory definition
thereof as laid down under Section 2(1)(ja) of The Patents Act.
Thus, this ground of opposition is not validly established by
the Opponents.
I shall now deal with Insufficiency ground of the opposition as discussed
during the hearing.
INSUFFICIENCY, Section 25(2)(g)
Insufficiency - Section 25(2)(g): that the complete specification does not
sufficiently and clearly describe the invention or the method by which it is
to be performed.
897/MUM/2007 (IN236630) Page 128 Having considered the detailed arguments of both the parties, the pregrant opposition and its review decisions, the two opposition board
recommendations, post-grant decision, the teachings of the various prior
art documents on record, the affidavit(s) filed by both the parties, I shall
now deal with Insufficiency ground of the opposition as discussed
during the hearing.
1. Opposition Board 1 in their findings has denied in toto that there is
insufficient disclosure in the patent complete specification. The Opposition
Board 1 further commented that Opponents have failed to establish this
ground of opposition validly. 2. Opposition Board 2 in their findings relating to insufficiency has
wrongly mentioned that addition of new material as an example on page
number 6 is incorporated with prescribed procedure without Form 13.
After verifying the facts, it is found that the Form 13 was filed by
applicant/patentee within prescribed manner. This is also recorded in the
Orders of the Learned Controller dated 30th June 2009 and 25th September
2009, at pre-grant stage.
3. After going through the complete patent specification meticulously, I
have noted that there is clear mention of :
a) Background of invention on pages 2-3,
b) Object of the invention and disclosure of the invention on pages 3-5,
c) Working example on page 6,
d) Claims on page 7 and 8,
e) Abstract on page 9.
f) Drawing showing the chemical reactions on page 10.
897/MUM/2007 (IN236630) Page 129 The complete specification thus meets the statutory requirements as
mandated under Section 10 of The Patents Act, 1970.
4. It is evident from the Form 27 filed by the Patentee of last 5 years
that the invention has been worked successfully using the patented
process.
5. Opponents have performed experiments using the disclosure provided
in patent complete specification, which have been reported in their
documents D9 and D10. Document D9 relates to Lab experiments
conducted by Opponents reproducing Step (a-f) of Claim 1 of patented
process to obtain ‘D-trans Chrysanthemic Acid’ successfully. Document
D10 relates to Lab experiments conducted by Opponents reproducing Step
(g) of Claim 1 of Patented process to obtain ‘D-trans Chrysanthemic Acid
Chloride’ successfully. This clearly marks that the claims are sufficiently
enabled with description, for a skilled artisan to perform the patented
process.
6. The question of insufficiency of disclosure does not arise even if a single
working example of performing the invention is disclosed in the
specification. This fact is supported by relevant case law as cited below:
Tata Global Beverages Limited Vs. Hindustan Unilever Limited,
where it has been held that “the sufficiency requirement is met if at least one
way of working the invention is clearly indicated enabling the skilled person
to carry out the invention. The order further goes on to state that it is not
necessary for the purpose of Section 10(4) that the disclosure of a patent be
adequate to enable the skilled person to carry out all conceivable ways of
operating the invention. If the best method known to the Patentee is disclosed
it satisfies the requirement of sufficiency.”
897/MUM/2007 (IN236630) Page 130 In the present case, the complete specification is supported with one
working example which sufficiently describes the invention and the
manner in which it is to be performed.
7. Conservation of Mass
As regards to Opponents contention relating to ‘conservation of mass’ in
the example reported in the patent complete specification, it is an accepted
fact in chemistry that there may be variation in results if the analytical
tests are performed by different chemists. I do agree with the patentee’s
submissions that the variations are within range of experimental errors
and permitted standard deviations. This may be attributed to analytical
errors, weighing variations, computational errors. Such errors can be
easily understood or acknowledged by a person skilled in the art. Such
errors are also observed in experiments conducted by Opponents in their
Document D9. As such these variations do not amount to insufficient
disclosure. Workability of the process is different from insufficiency of
disclosure.
8. Claim Step 1(f) of patented process
As regards to Opponents contention regarding distillation temperature of
20 degrees C in this step, as such this information is disclosed in the
patent complete specification. Description on Page 5, Step V states that
that Solvent is distilled to obtain pure acid. A skilled artisan can easily
understand that petroleum ether used in prior steps of the process is
distilled at 20 degrees C, not D-trans chrysanthemic acid.
9. Sulphuric Acid quantity in Claim Step (c) of Claim 1 of patented
process
As regards to Opponents contention regarding quantity of sulphuric acid
not mentioned correctly in Example provided in complete specification.
After
going
through
897/MUM/2007 (IN236630) the
complete
specification
and
description
Page 131 meticulously, it was found that the purpose and use of sulphuric acid can
easily be understood. The complete specification on Page 4 Step III
discloses that sodium chrysanthemate is acidified by addition of sulphuric
acid to convert it to D-trans Chrysanthemic Acid. Thus, on reading Step (c)
of Claim 1 and the description, it is clearly understood that the use of
sulphuric acid is to convert entire sodium chrysanthemate to D-trans
chrysanthemic acid. The Opponents have also performed experiments
using the patented process, as reported in their document D9, in which
they have performed Steps (a-f), covering this Step (c) of Claim 1 without
any ambiguity. Therefore it is easily within reach of a skilled artisan to
calculate the quantity of sulphuric acid required to complete acidification.
10. Catalyst mentioned in Example not disclosed
As regards to Opponents contention regarding catalyst not being disclosed.
After going through the complete specification meticulously, and based on
submissions of the patentee, it is clear that catalyst for this process is not
so important as it does not have any effect on yield and its use was also
optional, therefore it is not claimed. As is evident from Opponents
document D9, the Opponents were successful in performing the patented
process without using catalyst.
Therefore in my view, such issues relating to amounts of ingredients or
their calculations, does not amount to insufficiency.
Further, I admit the fact that there are some clerical or typographical
errors in the complete specification. Certain doubts were raised by
Opponents during the hearing. The Patentee in rebuttal clear these doubts
as follows:
897/MUM/2007 (IN236630) Page 132 a) Quantity of D-trans Ethyl chrysanthemate not mentioned in claim. The
doubt was resolved as there was specific mention of the quantity of Dtrans Ethyl chrysanthemate in the working example on page number 6.
The fact is also cleared further in subsequent paragraph of this Order
wherein it is stated that the claims should be read along with the
specification.
b) Atmospheric pressure of 4kg in Step (b) of Claim 1 is not clear. The
patentee explained that 4 Kg is a unit of measurement of pressure in the
reactor. ‘Kilogram’ or ‘Kilogram Force per Square Centimeter’ is a pressure
unit.
c) There were typographical errors in names of ingredients. As regards to
these typographical errors Patentee stated that “Ethyl chrysanthmate” to
be read as “Ethyl chrysanthemate”, “sodium chrysanthmate” to be read as
“sodium chrysanthemate”, “d-trans crysathemic acid” to be read as “Dtrans Chrysanthemic Acid”, “thiunyl chloride” to be read as “thionyl
chloride”, “d-trans chrysathemic acid chloride” to be read as “d-trans
chrysanthemic acid chloride”, “N-H-heptane” to be read as “n-Heptane”,
“d-allethrolne” to be read as “d-allethrolone”, “d-trans chrysanthanic acid
chloride” to be read as “D-trans chrysanthemic acid chloride”. As such all
these doubts were resolved.
d) In step (g) of Claim 1, the word “acid” has been inadvertently missed out
and it should not be read as “d-trans chrysathemic” but as “D-trans
Chrysanthemic Acid”. This doubt was cleared since there is specific
mention of D-trans Chrysanthemic Acid in the rest of specification and the
example.
e) As regards to ingredient “d-allethrolne (72:21)”, the patentee stated that
(72:21) refers to the isomers of this ingredient ‘Allethrolone’, which exists
897/MUM/2007 (IN236630) Page 133 in various isomer forms (like: D, L, and mix of these forms DL) and is
commercially available. Allethrolone mixture of D and L (72:21), was used
by Patentee in this patented process.
All these errors in the complete specification are of such nature that
can be easily understood and addressed by any person skilled in the
art.
At this juncture, I rely on the following important case laws and citations:
1. Dual Manufacturing & Engineering Inc’s patent – [1977] R.P.C. 189:
“They may not be consistent with the corresponding passages of claim 1, and
on that basis the claim may be wholly bad, but it does not mean that the
description is in any way insufficient. Further, the specification may
possibly provide no explanation of the operation of the parts
concerned
or
it
may
indeed
even
possibly
provide
a
wrong
explanation of the parts concerned; but that in itself does not
necessarily lead to a finding of insufficiency. The question so far as
insufficiency is concerned is whether, following the detailed description and
the drawings, it would have been possible for the man in the art to produce a
reclining chair which would achieve the promised object. If it did, the fact that
the explanation of the way in which the object was in fact achieved might be
wrong would be really neither here nor there.”
2. Eminent authority on patent Law, P.Narayanan quoted (1977 RPC 189
at 192, 196) on the ground of insufficiency as “that the Sole question under
an objection of insufficiency is whether or not the description which has been
given is going to be sufficient to enable a person who is reasonably skilled in
the particular field to make an embodiment of the invention which will have
feature which make it fall within the objects of the invention. The fact that
the scope of the monopoly claimed is unclear or that there is inconsistence
897/MUM/2007 (IN236630) Page 134 between the description and claims or that the specification
provides no explanation of the operation of parts concerned, or
provides a wrong explanation of the parts concerned, are not
relevant in considering the question of insufficiency”
Further, in regards to contention of the Opponents that amounts of
certain ingredients are not mentioned in claims or are incoherent.
After going through the complete specification, it is clear that all this
quantities have been disclosed in the example on page 6 of complete
specification. One fundamental rule of Patent Law is that the Claims of the
Specification should be read together with the description, which in this
case, is supported by one working example. To support this fact, I further
rely upon :
1. The landmark decision issued by the Hon’ble Supreme Court in case of
Biswanath Prasad Radhey Shyam Vs. Hindustan Metal Industries
(1979) 2 SCC, 511 “…the proper way to construe a specification is not
to read the claims first and then see what the full description of the
invention is, but first to read the description of the invention, in order that
the mind may be prepared for what it is, that the invention is to be claimed,
for the patentee cannot claim more than he desires to patent.
2. Parkinson v. Simon Lord Esher M. R. enunciated that as far as
possible the claims must be so construed as to give an effective meaning to
each of them, but the specification and the claims must be looked at
and construed together”.
Thus on the alleged ground of insufficiency of description, under Section
25(2)(g) of the Act, it is clear that the allegations/contentions of the
opponents are not legally tenable and therefore denied.
897/MUM/2007 (IN236630) Page 135 The specification bears the nature of a purposive construction and is
addressed to persons with practical knowledge and experience in the field
in which the invention is intended to be used. The disclosure is sufficient
to enable the whole width of the invention to be performed. The claims
define the scope of protection sought to be covered by the applicant, and
the preceding description is deemed to be enabling disclosure for
understanding of the claimed invention sought to be protected, as per The
Indian Patents Act. The invention is not limited to the statement of claims
but is intended to cover all the process steps in the working example that
fall within its scope. Significantly, the description of the invention in the
specification was not considered to be in any manner insufficient or
inadequate by the Opposition Board 1. The complete specification
describes the invention to the fullest extent, together with the best possible
method of working, and is enabling to persons skilled in the art of the
invention. This fact is further proved from the form 27 filed for the last five
years where the Patentee has been working the invention in its entirety.
This ground of opposition is not validly established by the
Opponents.
897/MUM/2007 (IN236630) Page 136 ORDER
Considering the detailed pleadings of both the parties, the two opposition
board
recommendations,
the
teachings
of
the
various
prior
art
documents on record, the affidavit(s) filed by both the parties, and in
view of my above findings, I conclude that the opponents have failed to
establish both the grounds of opposition (i.e. Inventive step and
Insufficiency) validly. I hereby dismiss the post grant opposition filed
in this case and maintain the patent as it is. There is no order as to
costs.
Dated this 16th February 2016
(Dr.Ajay S.Thakur)
Assistant Controller of Patents and Designs
897/MUM/2007 (IN236630) Page 137 Copy to:
1. Ms. Karuna Goleria,
De Penning & De Penning,
Alaknanda Building,
16, Nepean Sea Road,
Mumbai - 400036
2. Dr. Rajeshwari Hariharan,
Gopakumar Nair Associates,
3rd Floor, 'Shivmangal',
Akurli Road,
Kandivali (East),
Mumbai - 400101
897/MUM/2007 (IN236630) Page 138