Delhi High Court
Fmc Corporation & Ors. vs Natco Pharma Limited on 19 September, 2022
$~
* IN THE HIGH COURT OF DELHI AT NEW DELHI
% Date of decision: 19th September, 2022
+ CS(COMM) 349/2022 & I.A. 8132/2022, 9519/2022, 10886/2022
FMC CORPORATION & ORS. ..... Plaintiffs
Through: Mr. Sandeep Sethi, Senior Advocate
with Dr. Sanjay Kumar, Ms. Arpita Sawhney,
Mr. Arun Kumar Jana, Ms. Meenal Khurana,
Mr. Harshit Dixit and Mr. Priyansh Sharma,
Advocates.
versus
NATCO PHARMA LIMITED ..... Defendant
Through: Mr. Chander M. Lall, Senior
Advocate with Mr. J. Sai Deepak, Mr. G.Nataraj,
Mr. Avinash K. Sharma, Mr. Ankur Vyas,
Ms. Ananya Chugh, Mr. Shashikant Yadav and
Ms. Harshita Agarwal, Advocates.
CORAM:
HON'BLE MS. JUSTICE JYOTI SINGH
JUDGEMENT
JYOTI SINGH, J.
I.A. 8130/2022 (under Order 39 Rules 1 and 2 CPC, by Plaintiffs) in
CS(COMM) 349/2022
1. This judgment shall dispose of the present application filed by the
Plaintiffs under Order 39 Rules 1 and 2 CPC.
2. The suit out of which the application arises has been filed seeking a
decree of permanent injunction against the Defendant and those acting on its
behalf inter alia from infringing the patent rights of the Plaintiffs under
Indian Patent No. 298645 (IN'645), by using directly or indirectly any
process(s) covered by the said patent, granted by the Controller of Patents,
in favour of the Plaintiffs on 06.12.2005.
Signature Not Verified
By:KAMAL KUMAR
Signing Date:20.09.2022
20:54:04
3. It is averred in the plaint that E. I. DU PONT DE NEMOURS AND
COMPANY, a US based company, was granted the suit patent on
09.07.2018 under Section 43 of the Patents Act, 1970 (hereinafter
referred to as the 'Act') titled 'METHOD FOR PREPARING
N-PHENYLPYRAZOLE-1-CARBOXAMIDES'. By a confirmatory
Assignment Agreement dated 01.05.2018, the rights in the suit patent were
assigned in favour of the Plaintiffs with effect from 01.11.2017 and the
patent is currently valid and subsisting. The date of expiry of IN'645 is
06.12.2025 and indisputably, no pre-grant and/or post-grant opposition or a
revocation petition has been filed against IN'645, which fortifies the quality
and strength of the suit patent.
4. From the narrative in the plaint, the factual score is that Plaintiff
No. 1/FMC Corporation is a Company incorporated under the laws of the
State of Delaware, United States of America and Plaintiff No. 2/FMC Agro
Singapore Pte. Ltd., is a Company registered under the laws of Singapore.
Founded in 1883, Plaintiff No. 1 is engaged in the production and sale of
chemicals including agrochemicals for more than a century and provides
innovative and cost-effective solutions for enhancement of crop yield and
quality by controlling a broad spectrum of insects, diseases etc. as well as in
non-agricultural markets for pest control. It carries on business in several
parts of the world. By virtue of the Assignment Agreements, each of the
Plaintiffs is registered and recorded as patentee of the suit patent in the
Register of Patents and conduct their agrochemical business in India through
Plaintiff No. 3, which holds license to import and market the final product,
'Chlorantraniliprole' (CTPR).
5. IN'645, the suit patent relates to a novel method for preparing
anthranilic diamide insecticide compounds and a total of 12 claims have
been granted in the suit patent. IN'645 discloses and claims inter alia a
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By:KAMAL KUMAR
Signing Date:20.09.2022
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method for preparing a compound of formula 1 including CTPR, in
particular claim 1. The said method involves combining (1) a carboxylic
acid compound, (2) an aniline compound and (3) a sulfonyl chloride, to
prepare or manufacture CTPR. Thus, in the patented method, a pyrazole
carboxylic acid of Formula 2, and aniline of Formula 3 and a sulfonyl
chloride are combined (contacted) to prepare CTPR. The process of
invention is depicted as follows:
6. It is further averred that from a document titled 'Environmental
Management Plan for obtaining consent for establishment (CEF)-
Expansion', submitted by the Defendant to A.P. State Pollution Control
Board, Plaintiffs learnt of the process adopted by the Defendant for
synthesis of CTPR and a perusal of the same reflects that Defendant is
employing patented method claimed by claims 1, 5 to 8 and 11 to
prepare the identical product, CTPR and, therefore, infringes the process of
the suit patent. The route of synthesis as brought forth in the plaint is as
follows:
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By:KAMAL KUMAR
Signing Date:20.09.2022
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7. As the chronology goes, on 23.05.2022, summons were issued to the
Defendant in the suit and on the said date while seeking time to file reply to
the present application, learned counsel for the Defendant, on instructions,
had stated that the Defendant does not intend to launch the product CTPR
until the expiry of patents ending with numbers IN'307 and IN'332, which
were expiring on 13.08.2022 and would launch the product post expiry of
the said patents, using a process which does not infringe the suit patent
IN'645.
8. With the consent of the parties, vide order dated 29.07.2022,
Dr. Gopakumar G. Nair and Dr. Raghavan Soman were appointed as
Scientific Advisors to examine the two processes, and Terms of Reference
were framed separately, on behalf of both the parties. On 08.08.2022,
Prof. Bhalchandra Bhanage, was appointed in place of Dr. Soman, who
expressed his inability to accept the assignment on account of other prior
commitments. The Scientific Advisors rendered their respective Reports,
copies of which were given to the learned counsels for the parties. Findings
in the Reports shall be adverted to in later part of the judgment.
9. Contentions articulated on behalf of the Plaintiffs can be captured as
follows:
Signature Not Verified
By:KAMAL KUMAR
Signing Date:20.09.2022
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A. Defendant/Natco is guilty of infringing the suit patent IN'645. The
alleged manufacturing process disclosed by Natco is 'equivalent' to
the process claimed in IN'645. Both processes describe an amide
bond formation and implement the activation of a carboxylic acid
moiety to facilitate the amide formation, to yield CTPR. Compared
with IN'645, Defendant's process (hereinafter referred to as 'Natco
process') performs substantially the same function, i.e., activation of
carboxylic acid moiety, in substantially the same way, i.e., coupling
of carboxylic acid (Formula 2) with aniline (Formula 3), to achieve
the same result, i.e., yield CTPR. IN'645 discloses that the invention
relates to method for preparing compounds of Formula 1 by coupling
carboxylic acids of Formula 2 with anthranilamides of Formula 3
using a sulfonyl chloride, in presence of a base and a solvent. Thus,
the IN'645 and the Defendant's process, both rely on activation of 3-
Bromo-1-(3-Chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid into
an activated intermediate, which reacts with 2-Amino-5-chloro-3, N-
dimethylbenzamide to produce CTPR and are 'equivalent'. Plaintiffs
have relied on the following schematic presentation:
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By:KAMAL KUMAR
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B. Both these processes employ a similar synthetic strategy, i.e.,
stoichiometric activation of carboxylic acid moiety and judged from
this perspective also, are equivalent. 'Doctrine of Equivalents'
propounds that despite an absence of literal infringement of a patent
claim, infringement can be proven if an element of the accused
product or service and a claimed element of patented invention are
found to be substantially equivalent. This prevents a person from
practicing a fraud on a patent by substituting obvious equivalents of
elements in the claims in order to avoid their literal language. If the
proposition made by the Defendant that scope of a patent is limited to
its literal elements is accepted, it would allow a competitor to make an
unimportant or insubstantial change to a patented invention and defeat
the patent. Moreover, where a patentee describes his invention and
claims it in that form, which most perfectly embodies it, he is deemed
to claim every form in which his invention may be copied. In
Warner- Jenkinson Co., Inc. v. Hilton Davis Chemical Co., 520 U.S.
17 (1997), it is observed that equivalency must be determined against
the context of the patent, the prior art and the circumstances of the
case and is neither a prisoner of a formula nor an absolute to be
considered in a vacuum.
C. In order to examine the application of the doctrine, Courts have
developed five legal tests: (a) all elements rule; (b) Tri-partite test;
(c) insubstantial differences test; (d) obviousness test and (e) known-
interchangeability test. In Sotefin SA v. Indraprastha Cancer Society
and Research Center and Others, 2022 SCC OnLine Del 516, this
Court observed that in order to determine infringement, it is
imperative to reach a finding that 'all essential elements' of the suit
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By:KAMAL KUMAR
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patent are present in the infringing process and applied the Doctrine
of Equivalents to test if Defendant's process infringed the suit patent.
Court also relied on the pith and marrow doctrine to examine if the
substituted element in the infringing product does the same task, in
substantially the same way, to accomplish substantially the same
result. In Raj Parkash v. Mangat Ram Chowdhry & Others, 1977
SCC OnLine Del 33, it was held that a minor variation cannot be
treated as a shield from piracy, relying on the judgment of the
Supreme Court of Canada in Free World Trust v. Electro Sante Inc.,
(2000) 2 SCR 1024, wherein it was held that non-essential elements
may be omitted or substituted but that too would not shield
infringement.
D. The issue that the Court needs to determine is whether Defendant's
process covers all the essential features of the patented process and
only omits, varies or adds some non-essential features. Analysis of the
two processes leads to a conclusion that the answer to the question is
in the affirmative and the difference that the Defendant endeavours to
carve out between the reagents, i.e., thionyl chloride and sulfonyl
chloride per se is immaterial. In Line 10 of Page 9 of WO
2019/207595 it is disclosed that the process can use both organic and
inorganic chloride, including thionyl chloride (inorganic) and oxalyl
chloride (organic). The specific properties of these compounds, i.e.,
physical and chemical, are also irrelevant for the present purpose as
chlorides serve only one purpose, i.e., stoichiometric activation of
carboxylic acid group, which then reacts with the amino group to
form CTPR and no material difference can be urged between the two
processes, merely on account of use of a different chloride. The
reagent sulfonyl chloride is a reactant which facilitates coupling
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By:KAMAL KUMAR
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reaction between compound of Formula 2 and compound of
Formula 3. The complete specification of IN'645 also contemplates
various other equivalent reagents to facilitate the coupling reaction,
which is evident from Page 8 Lines 13 to 25 of the Patent
Specification IN'645, wherein it is clearly stated that sulfonyl chloride
is 'preferred' because of its commercial availability. It is thus wholly
irrelevant if thionyl chloride is different from sulphonyl chloride, as a
minor variation cannot shield the Defendant from infringement.
E. Stand of the Defendant that its process involves a difference sequence
is also of no avail to the Defendant and it is deliberately attempting to
introduce limitations into claim 1 of the suit patent, which do not
exist. There is no base mentioned in claim 1 and certainly, no
limitation with respect to sequence of combining the reactants. The
reactants can be combined in a variety of orders, as stated on page 8
of IN'645, such as combining sulfonyl chloride with carboxylic acid
of Formula 2 to form a mixture and then combining the mixture with
aniline of Formula 3.
F. CIBRC Registration Certificate of the Defendant states 'Methane
Sulphonic acid impurities' are present in Defendant's approved
process. These can be formed only if sulfonyl chloride is used. In any
case, thionyl chloride stated to be used by the Defendant is equivalent
to sulfonyl chloride since both are Reagents and have the same
function. In essence, the starting materials are the same i.e. the acid
and amide intermediates, the end result is the same i.e. CTPR and the
Reagents are equivalent, leaving no doubt that the process of the
Defendant infringes IN'645. IN'645 description is not limited to any
sequence or any choice of reagent and any chloride can be used which
explicitly shows that sulfonyl chloride is a non-essential element of
Signature Not Verified
By:KAMAL KUMAR
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IN'645 process and the change of sequencing in the Defendant's
process would have no impact.
G. Dr. Nair, in his report, clearly notes that there is equivalence in the
two processes. In answer to question no. 7 (iv) of the FMC Terms of
Reference, it is stated 'Yes, though not literally' and this is the
essence of Doctrine of Equivalents. Infringement is not to be
determined by the resultant characteristics of the by-products but by
equivalence of processes and Dr. Nair's report acknowledges that
impugned process is equivalent to IN' 645 process.
H. Dr. Vikrant Arun Adsool, who is presently a Chemistry Team Leader
at FMC Agro Singapore Pte. Limited and an expert in organic and
process chemistry, has filed an affidavit, after comparing and
analysing the two processes and has categorically stated that the two
processes are equivalent and that the process/routes employed by
Natco falls within the scope of claim 1 of the suit patent.
10. The arguments urged on behalf of the Defendant/NATCO, the
litigation adversary, are encapsulated as follows:
A. IN'645 process and Natco process are for preparing anthranilic acid
derivatives and compounds obtained include CTPR. IN'645 process
involves using a specific organic chloride viz. sulfonyl chloride
(R8SO2Cl) reagent for coupling carboxylic acid intermediate with
aniline intermediate in a single step. The scope of protection vide
claim 1 is expressly limited to this coupling using sulfonyl chloride in
the light of Section 10(4)(c) and Section 48(b) of the Act. The only
sulfonyl chloride exemplified is methane SO2Cl and IN'645 does not
identify/refer/disclose any other organic or inorganic chloride, which
could be used as a reagent. Per contra, Natco process, for which
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By:KAMAL KUMAR
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approval was obtained for Technical Indigenous Manufacture under
Section 9(3) of the Insecticides Act and disclosed in its EMP and
Process Patent Application, involves two separate and discrete stages:
(a) carboxylic acid intermediate is converted to an acid chloride using
thionyl chloride in a first reactor and the bio-products so formed viz.
SO2 and HCl gases are scrubbed in caustic soda solution to give NaCl
and NaHSO3, which are useful in food and cosmetic industries; and
(b) acid chloride of step (a) is reacted with amide intermediate in a
second reactor to obtain CTPR.
B. Natco process, approved by CIBRC, for manufacture of CTPR is
different from IN'645 process and there is no infringement, since not
only is the reagent used by Natco, i.e., inorganic thionyl chloride
different from organic sulfonyl chloride, but even the sequence of
reaction is different and the process is completely outside the scope of
claims of IN'645. The Certificate of Analysis of Ross Laboratories, an
independent laboratory certified by CIBRC, states that there is no
methane sulfonic acid impurity in the Natco Approved process, which
shows that the process does not use any sulfonic acid, let alone
methane sulfonic acid. The scope of protection given by the claims of
IN'645 is limited to coupling by using sulfonyl chloride, which is
evident from its specification read with the objectives of the invention
and the end result can only be achieved by using methane sulfonic
chloride. Section 10(4) of the Act expressly states that the claim
defines the scope of protection and claim 1 of IN'645 is limited to
acid + amide + sulfonyl chloride. Section 48(b) militates against any
broad extension of application of Doctrine of Equivalents since it uses
the language 'that process' and 'product obtained directly by that
process in India'.
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By:KAMAL KUMAR
Signing Date:20.09.2022
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C. The Supreme Court in Martin F. D'Souza v. Mohd. Ishfaq, (2009) 3
SCC 1, has expressly observed that where independent experts are
appointed by a Court, their opinion should be considered binding.
Both the Scientific Advisors appointed by this Court, with the consent
of the parties have opined that Natco process is different from IN'645
process and the former is not within the scope of claims 1 to 5 of the
latter, including the finding that Natco uses SOCl2, which is not
covered in claims of IN'645. Both the Advisors have specifically
opined that the use of sulfonyl chloride to couple the acid and amide
is essential to the process of IN'645.
D. In answer to a specific question, if any Methane Sulfonic acid
impurity is present in CTPR formed in Natco process, the answer by
Dr. Nair is 'No', while Prof. Bhanage has stated that it is not present
in the dossier provided (Pages 73 to 96) and if it is present then it will
arise only from methane sulfonyl chloride hydrolysis to acid and
cannot be formed in the Natco process. Both Advisors agree that
thionyl chloride is different from sulfonyl chloride. Insofar as
equivalence of the processes is concerned, Dr. Nair has stated that
they are not literally equivalent and that the impurity profile
distinguishes the processes. Prof. Bhanage has elaborated on another
aspect by showing differences between thionyl and sulfonyl
chlorides in terms of reactivity and physical properties of the two
reagents.
E. The judgment in Sotefin SA (supra), relied upon by the Plaintiffs is
inapplicable to the present case as the same is in the context of a
product patent and not a process patent. While for a product patent, an
overall comparison of the product to the claims may be permissible to
determine equivalence, in a process patent separate considerations
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apply and the relevant guidelines are to be found in the case of
Warner-Jenkinson Co., Inc. (supra). The relevant test is 'all
elements' test i.e. not only the starting materials and the end product,
but all reagents and each step must be equivalent between the
patented and the impugned process. This is supported by the Article
Doctrine of Equivalents: Scope & Limitations by D. Patodia, S. Jain
and U. Shukla, published in Journal of Intellectual Property Right
(VOL. 12, May 2007, pp 314-329), relied upon by the Plaintiffs. In
any event, the judgement in Sotefin SA (supra) does not aid the
Plaintiffs as in the facts of that case the Scientific Advisors had
opined that 17 out of the 19 elements were common in the competing
products and after analysis the Court found that the distinction sought
to be brought out in the remaining 2 'non-essential' elements was
insubstantial, in contrast to the present case, where both Advisors
have opined that use of sulfonyl chloride is 'essential' to the process
claimed in IN'645 and the reagent used in Natco process differs,
considerably in most properties. The case of Raj Parkash (supra) also
does not support the Plaintiffs' case since it was under the 1911
Indian Patents and Designs Act, which did not have any provision
pari materia to Section 10(4) of the Act.
F. The product patent IN'307 has already expired on 13.08.2022 and
given the clear findings of the two Scientific Advisors, in support of
Natco as also considering that CTPR is a seasonal product with the
primary season being the Kharif Season, from September to
December, Natco be permitted to launch the product, subject to
maintaining monthly statement of accounts and an assurance that
Natco will not use the process claimed in IN'645 or any other process
that infringes the suit patent. It is a settled law that no interim relief
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should be granted unless there is a clear case of irretrievable harm
which cannot be compensated in terms of damages. Plaintiffs do not
work the suit patent IN'645 in India and are only trying to extend the
monopoly over the product CTPR despite the product patent having
lapsed on 13.08.2022. No equitable relief can, therefore, be granted to
the Plaintiffs in terms of the judgment in Franz Xaver Humer v. New
Yash Engineers, 1996 SCC OnLine Del 243, and in any case, if the
Plaintiffs succeed, monetary compensation and damages would be an
adequate remedy. In suit being CS(COMM) 608/2022, a Co-ordinate
Bench of this Court had declined to grant an injunction on a process
patent as the Court was of the view that the damages will ultimately
suffice. Natco has already suffered a loss of at least Rs. 100 crores on
account of the restraint order and any further restraint will destroy the
entire investment and would also be detrimental to public interest.
Plaintiffs have over 25 patents and applications for CTPR and will
continue to litigate till 2041 while grave prejudice will be caused to
Natco in case launch of its product is not permitted. Be it noted that
even the process patent IN'332 with respect to which the Plaintiffs
have an injunction in another suit has also expired on 13.08.2022.
ANALYSIS
11. At the outset and before proceeding to examine the case on merits, it
is pertinent to note that Plaintiffs had an injunction in their favour in respect
of the product patent IN 201307 (IN'307) and its process patent IN 213332
(IN'332) in CS(COMM) 611/2019 with respect to CTPR, however, both
patents have expired on 13.08.2022.
12. In the present application, this Court is concerned with the alleged
infringement of the suit patent IN'645, which is a process patent and this
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would entail a prima facie examination of the process under IN'645 and the
process of the Defendant. For a prima facie comparison of the two
processes, a brief backdrop of the two processes is essential.
13. IN'645 Process:
a) The patent was granted on 09.07.2018, titled
'METHOD FOR PREPARING N-PHENYLPYRAZOLE-
1-CARBOXAMIDES'. A total of 12 claims have been granted
in the said patent. The Bibliographic details are as follows:
TABLE 1
Indian Patent No IN 298645
Patent Application No. 3548/DELNP/2007
Title Method for preparing N-
PHENYLPYRAZOLE-1-
CARBOXAMIDES
Applicant E. I. DU PONT DE NEMOURS
AND COMPANY
Date of filing in India 11.05.2007
International Application PCT/US2005/0444131
No.
International filing date 06.12.2005
Priority Dates 07.12.2004
WO Publication No WO 2006/062978 A1 published
on 15.06.2006
Section 11A Publication 31.08.2007 - The application
was published in the official
gazette issued by the Patent
Office thereby being open for
public to file pre-grant
opposition.
Date of grant 09.07.2018
Grantee E. I. DU PONT DE NEMOURS
AND COMPANY
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By:KAMAL KUMAR
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Section 43 (2) publication 13.07.2018 Accordingly, the
timeline to file post-grant
opposition on the suit patent
IN'645 expired on 13.07.2019.
Date of expiry of the 06.12.2025
patent
Patentee/Assignee FMC Corporation
FMC Agro Singapore Pte. Ltd.
By virtue of confirmatory
assignment agreement dated
May 1, 2018 with effective date
of November 1, 2017 assigning
absolute rights in the invention
of the suit patent to the Patentees
i.e., Plaintiff no. 1& 2 herein,
taken on record by the Indian
Patent Office on August 7, 2018.
b) The process is depicted as follows:
1. The patent discloses and claims inter alia, a method for
preparing a compound of Formula 1 including CTPR, in
particular Claim 1. The method combines (1) a carboxylic
acid compound, (2) an aniline compound and (3) a sulfonyl
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chloride, to manufacture CTPR. Thus, in the patented method,
a pyrazole carboxylic acid of Formula 2, and an aniline of
Formula 3 and a sulfonyl chloride combine and CTPR is
manufactured. Method as claimed in Claims 1, 5 to 8 and 11,
which have been granted, is as follows:
1. A Method for preparing a compound of Formula 1,
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c) Patent description explains the meaning of the term
'Combining' as 'contacting the chemicals with each other'. The
written description also provides reference to various
embodiments relating inter alia, to the sequence of addition of
carboxylic acid of Formula 2 with aniline of Formula 3 and the
sulfonyl chloride as follows:
"Embodiments of the present innovation include:
Embodiment M 14. The method wherein the
carboxylic acid of Formula 2, aniline of Formula 3
and sulfonyl chloride are combined at a
temperature is between about - 70 and 100℃.
Embodiment M 17. The method wherein the
carboxylic acid of Formula 2 is combined with the
aniline of Formula 3 to form a mixture, and then
the mixture is combined with the sulfonyl chloride.
Embodiment M 18. The method of Embodiment
M17 wherein a base is combined with the mixture
either before or after combining with the sulfonyl
chloride. Embodiment M 19. The method of
Embodiment M 17 wherein a base is combined
with the compounds of Formulae 2 and 3 to form
the mixture before combining with the sulfonyl
chloride.
Embodiment M 20. The method wherein a base is
combined with the compounds of Formulae 2 and
3 and the sulfonyl chloride.
Embodiment M29. The method of Embodiment M 17
wherein a solvent is combined with the compounds
of Formulae 2 and 3 to form the mixture before
combining with the sulfonyl chloride."
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d) The various embodiments, as rightly pointed out by the
Defendant have one common factor, i.e., the sequence, where
the carboxylic acid of Formula 2 and aniline of Formula 3 are
first mixed, whether with the base or a solvent etc. and
thereafter sulfonyl chloride is added to the mixture so obtained.
In fact, emphasis on the sequence is further evident from the
following:
"In the present method, the sulfonyl chloride is
combined with the pyrazolecarboxylic acid of
Formula 2 and the aniline of Formula 3. The
reactants can be combined in a variety of orders,
such as combining the sulfonyl chloride with the
carboxylic acid of Formula 2 to form a mixture and
then combining the mixture with the aniline of
Formula 3. However, for preparing the particular
N-phenylpyrazole- 1-carboxamides of Formula 1,
the most preferable order of combination has been
found to comprise combining the carboxylic acid of
Formula 2 with the aniline of Formula 3 to form a
mixture and then combining the sulfonyl chloride
with the mixture (e.g., adding the sulfonyl chloride
to the mixture of the compounds of Formulae 2
and 3), because this order of the addition allows
convenient control of the coupling process. The
rate of reaction is readily controlled by simply
controlling the rate of addition of the sulfonyl
chloride compound. Therefore, an embodiment of
note of the present method comprises the
sequential steps of (1) combining a carboxylic acid
of Formula 2 and an aniline of Formula 3 to form
a mixture, and (2) then combining the mixture with
a sulfonyl chloride. Although addition of the
sulfonyl chloride to the mixture containing the
aniline of Formula 2 potentially could result in
undesirable side reactions, it has been discovered
that the particular stereoelectronic profiles of the
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compounds of Formulae 2 and 3 facilitate
obtaining remarkably high yields of compounds of
Formula 1 using the present method." [emphasis
added]"
e) Significantly, it is noted in the detailed description that though
the reactants can be combined in a variety of orders, such as
combining sulfonyl chloride with carboxylic acid to form a
mixture and then combining the mixture with aniline,
however, for preparing the particular N-Phenylpyrazole-1-
Carboxamide of Formula 1, the most preferable order of
combination is to combine the acid and aniline to form a
mixture and then combine the sulfonyl chloride with the
mixture, as this order allows convenient control of the coupling
process and the rate of reaction is readily controlled by simply
controlling the rate of addition of sulfonyl chloride compound.
It is further described that as the starting materials of Formula 2
and 3 are typically solids at ordinary ambient temperatures, the
method is most satisfactorily conducted using a solvent in
which the starting compounds have significant solubility and
thus the method is conducted in a liquid phase comprising a
solvent. It needs emphasis that the written description also
explains the role of sulfonyl chloride and notes that its
compounds preferred for the present method, because of the
commercial availability, include methanesulfonyl chloride and
p-toluenesulfonyl chloride, however, methanesulfonyl chloride
is more preferred for the reasons of lower cost, ease of addition
and/or less waste.
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By:KAMAL KUMAR
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14. Natco Process:
a) The process relates to 'AN IMPROVED PROCESS FOR THE
PREPARATION OF ANTHRANILAMIDE DERIVATIVES'.
The stated objective of the invention is to provide a simple and
cost-effective process for preparation of CTPR of Formula-Ia
and Cyantraniliprole of Formula-Ib with high purity and good
yield on a commercial scale.
b) The process as explained by Natco is in two stages:
Stage 1:
In reactor-1, 3-Bromo-1-(3-Chloro-2-pyridinyl)-1H-
pyrazole-5-carboxylic acid is reacted with thionyl chloride in
acetonitrile 75-80℃ to get corresponding acid chloride
intermediate. The reaction mass is directly taken to the next
step without isolation of the intermediate. Sulphur dioxide and
hydrogen chloride gases will be liberated during the reaction
and are scrubbed.
Stage 2:
In reactor 2, 2-Amino-5-chloro-3, N-dimethylbenzamide,
acetonitrile and 3-picoline are charged and then reaction mass
from reactor 1 is added at 25-35℃ to the above reaction mass.
Hydrogen chloride gas, liberated during the reaction, is
quenched with 3-picoline and the product is filtered to separate
acetonitrile organic layer. The resulting product is further
purified to obtain CTPR. The two stages are represented as
follows in a condensed form:
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15. Plaintiffs have asserted their right of enforcement of the suit patent
against the Defendant under Section 48 of the Act, which provides that
subject to the other provisions of the Act and conditions specified in Section
47, a patent granted under the Act shall confer upon the patentee, where the
subject matter of the patent is a process, the exclusive right to prevent third
parties, who do not have his consent, from the act of using that process and
from the act of using, selling, offering for sale product obtained directly by
that process. It is a settled position in the Patents law that a product claim, if
granted, confers monopoly on the patentee for the product, irrespective of
the process by which the product was obtained. However, in a process claim,
the monopoly is restricted to the method by which the product is
manufactured and if the same product is manufactured through a different
process/method, the patentee cannot extend its monopoly to the different
process. It is an equally settled proposition that the scope of invention for
which protection is claimed by the patentee is defined by the claims. Section
10(4) of the Act provides that specifications of a patent should fully and
particularly describe the invention. Claim construction has to be done as a
whole and there is also no quarrel that all essential elements of the suit
patents claimed are required to be found in the infringing process to
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establish infringement. In order to substantiate the case of infringement
against the Defendant, Plaintiffs endeavoured to map the elements of
Natco's process with the process under the suit patent.
16. In order to reach a prima facie finding on the essentiality of the
reagent used in the suit patent and equivalence of the 2 processes and
looking at the technicalities of the issues involved, with the consent of the
parties, this Court had appointed two Scientific Advisors, as
aforementioned, for an expert opinion and both have rendered their
respective Reports. In order to appreciate the findings in the Reports, I may
first allude to the Terms of Reference, which are extracted hereunder for
ready reference:
"Terms of Reference (I) (NATCO)
1. Are 3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-
carboxylic acid and 2-Amino-5-chloro-N,3-
dimethylbenzamide intermediates used in suit patent
IN'645 disclosed in prior art IN 215218 and IN 284017
and also in WO'518?
2. Are 3-Bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-
carboxylic acid and 2-Amino-5-chloro-N,3-
dimethylbenzamide intermediates coupling disclosed in
prior art WO'518 for example, in the pages and
scheme and description reproduced above in Paragraph
VI (A)?
3. Is the reagent thionyl chloride used in the Natco
process for converting the pyrazole carboxylic acid to acid
chloride the same as the reagent used for coupling the
pyrazole carboxylic acid with aniline as set out in Claims 1
to 11 of IN 298645? Do thionyl chloride which is an
inorganic chloride, and sulfonyl chlorides which are
organic chlorides, have different physical and chemical
characteristics?
4. Is Methane Sulfonic acid impurity present in Natco
product as per data given in CIBRC dossier?
5. Are the following two process distinct or the same?
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NATCO Process IN298645 process
(1).
(1). +
+ Thionyl Chloride
(SOCl2)
+
(acid chloride).
Mixture I (2 + 3)
(2).
(2). Mixture I (2+3) + Base
+ 3-Picoline (base)
Mixture of benzamide and 3-picoline base Mixture II (2 + 3 + Base)
(3).
(3).
Mixture II + Sulfonyl chloride
(2+3+Base) (R8S(O)2Cl)
+ Mixture of
and 3-Picoline base from
(2) above
(If X= Cl, Chlorantraniliprole of formula-Ia; and
if If X= CN, Cyantraniliprole of formula-Ib)
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6. In the process of IN'645 when sulfonyl chloride is
used the chloride is knocked off and sulfonyl group
attached to the pyrazole carboxylic acid to form mixed
anhydride. Is this statement correct?
7. In the NATCO Process when thionyl chloride is used
the chloride group is attached to the carboxylic acid group
in the pyrazole carboxylic acid to form carbonyl chloride
which is not a mixed anhydride. Is this correct?
8. Is the NATCO process which requires reacting a
pyrazole carboxylic acid with thionyl chloride to obtain an
acid chloride and then reacting the acid chloride so
formed with an aniline within the scope of Claims 1 to 5 of
IN'645? Is that correct?
Terms of Reference (II) (FMC)
(i) Whether the Defendant's process is disclosed in the
complete specification of the suit patent IN'645?;
(ii) What are the essential feature(s) of the process
covered and claimed by the suit patent IN'645?
(iii) Whether the Defendant's process for preparing
Chlorantraniliprole (CTPR) is covered and claimed by the
process claimed by the suit patent IN'645?;
(iv) Whether the Defendant's process for preparing
Chlorantraniliprole (CTPR) is equivalent to the process
claimed by the suit patent IN'645?;
(v) Whether 3-Bromo-1-(3-chloro-2-pyridinyl)-1H-
pyrazole-5 carboxylic acid and 2-Amino-5-chloro-N,3-
dimethylbenzamide used in the Defendant's process for
preparing Chlorantraniliprole (CTPR) are same as
claimed by the suit patent IN'645?;
(vi) Whether 3-Bromo-1-(3-chloro-2-pyridinyl)-1H-
pyrazole-5 carboxylic acid and 2-Amino-5-chloro-N,3-
dimethylbenzamide used in the Defendant's process for
preparing Chlorantraniliprole (CTPR) are equivalent as
claimed by the suit patent IN'645?;
(vii) Whether the Defendant's process for preparing
Chlorantraniliprole (CTPR) as disclosed in the document
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"Environment Management Plan for obtaining consent for
establishment (CFE)- Expansion" submitted to AP State
Pollution control Board is same as disclosed by the
Defendant at the Central Insecticides Board and
Registration Committee (CIB&RC) in light of the
documents submitted by the Defendant by virtue of the
disclosure/discovery?;
(viii) Whether the impurity profile of the end product,
CTPR obtained in the Defendant's process is same as the
impurity profile of the product, CTPR, submitted by the
Defendant at the Central Insecticides Board and
Registration Committee (CIB&RC) in light of the
documents submitted by the Defendant by virtue of the
disclosure/ discovery?
(ix) Whether Annexure VII shows identical impurity
profile to the Plaintiffs' registered CTPR made by patented
process IN'645. Attention is drawn to same Annexure VII
at page 7, section 15 shows the Defendant's alleged
process for manufacture.
(x) Whether Annexure VIII which is an independent
analysis of the Defendant's CTPR, shows the same
impurity profile as the Plaintiffs' CTPR?
(xi) Whether Annexure IV which is the Defendant's TIM
registration certificate shows the exact impurity profile of
the Plaintiffs' CTPR.
(xii) On reviewing the documents submitted, as the
Defendant has tied its raw materials (including, thionyl
chloride) with the Plaintiffs' impurity profile, whether the
process of the Defendant can still be considered to be
different than the process of the Plaintiff's patented
process covered by IN'645."
17. Case of the Plaintiffs is primarily predicated on the Doctrine of
Equivalents and it is sought to be contended that even if the Natco process
does not literally infringe the suit patent, it may be found to infringe on the
bedrock of 'equivalence'. Contention of the Defendant is that element-to-
element test must be applied and tested on that anvil, in the present case
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there is no infringement since the reagent i.e. sulfonyl chloride is an
essential element in Plaintiffs' process and the Natco process admittedly
uses thionyl chloride as the reagent, which has different and distinct role in
achieving the same task and accomplishing substantially, the same result.
Use of a different reagent and a completely different sequence of reactions
in the Natco process cannot be termed as a minor or insubstantial variation,
so as to accuse the Defendant of infringement and piracy.
18. Insofar as the law on the subject is concerned, in my view, the same is
well-settled and no longer res integra. I may usefully allude to the
observations in a recent decision of this Court in Sotefin SA (supra), where
the Court has held that in order to determine infringement, it is imperative to
reach a finding that 'all essential elements' of the suit patent are present in
the infringing process. It was also held that in order to examine if the
substituted element in the infringed product does the same task, in
substantially the same way, to accomplish substantially the same result, the
pith and marrow doctrine, also known as Doctrine of Purposive
Construction, needs to be applied by the Court. Reliance was placed on the
judgement in Rodi & Wienenberger A.G. v. Henry Showell Ltd., 1966 RPC
(441), wherein it was propounded that all essential elements of the suit
patent must be found in the process alleged to be infringing. Relevant para is
as follows:
"If the language which the patentee has used in the claims
which follow the description upon its true construction
specifies a number of elements or integers acting in a
particular relation to one another as constituting the
essential features of his claim, the monopoly which he
obtains is for that specified combination of elements or
integers so acting in relation to one another-and for
nothing else. There is no infringement of his monopoly
unless each and every one of such elements is present in
the process or article which is alleged to infringe his
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patent and such elements also act in relation to one
another in the manner claimed. The law as to the
principles of construction of claims in specifications in the
modern form seems to me so laid down clearly and
authoritatively in the Judgment of Upjohn, L.I. in Van de
Leiy v. Bamfords 20 Ltd. [1961] R.P.C. 296, which was
approved by the majority of the House of Lords on appeal:
[1963] R.P.C. 61."
19. In order to avoid prolixity, I may refer to relevant passages from the
judgment in Sotefin SA (supra), wherein the judgments in cases of Raj
Parkash (supra) and Free World Trust (supra), have been noted and the
Court has observed that for determining the question of infringement, it
must be borne in mind that the non-essential or trifling variations or
additions in the product would not be germane, so long as substance of the
invention is found to be copied. Relevant paras are as follows:
"33. The critical question is whether the elements not
found in the Smart Dollies, are essential or not, so as to
construe an infringement. For determining the question of
infringement, it must be borne in mind that the non-
essential or trifling variations or additions in the product
would not be germane, so long as the substance of the
invention is found to be copied. Pure literal construction is
not be adopted, rather, doctrine of purposive construction
should be applied. The court shall also apply Doctrine of
Equivalence to examine if the substituted element in the
infringing product does the same work, in substantially the
same way, to accomplish substantially the same result. On
this aspect, lets first take note of the judicial precedence.
In the case of Raj Prakash v. Mangat Ram, a division
bench of this court held that a minor variation cannot be
treated as a shield from piracy, in the following words:
"12. We have, therefore, to read the specifications
and the claims from the point of view of the persons in
the trade manufacturing film strip viewers. It is the
pith and marow of the invention claimed that has to
be looked into and not get bogged down or involved in
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the detailed specifications and claims made by the
parties who claim to be patentee or alleged violaters.
(See Birmingham Sound Reproducers Ld. v. Collaro
Ld. and Collaro Ld. v. Birmingham Sound
Reproducers Ld, 1956 RP.C 232)(2)."
34. Next at para 16 it was noted that:
"A.I.R. 1969 Bombay 255(8), held that the main
function of the court is to construe the claims (stated
at the end of specifications in the patent) which are
alleged to have been infringed without reference to
the body of the specifications and to refer to the
specification only if there is any ambiguity or
difficulty in the construction of the cliams in question.
He further observed that where one of the claims in
respect of which infringement is alleged is wide
enough to cover all methods for achieving particular
result, the question is not as to the method actually
followed by the plaintiffs but is whether the method
followed by the defendants is covered by the claim in
the plaintiff's patent. The onus as to the invalidity of a
plaintiff's patent and the grounds of insufficiency of
description, want of novelty, absence of inventive
steps and want of utility was rightly placed on the
defendants. The learned Judge further observed that
in an action for infringment of patent to meet the
defence under Section 29(2) read with Section 26, that
the patent was invalid due to insufficiency of
description, the claim in the specifications of the
patent need only be as clear as the subject admits, and
the patentee need not so simplify his claim as to make
it easy for infringers to evade it."
35. Further at para 25 and 26 it was observed as follows:
"25. The patented article or where there is a process
then the process has to be compared with the
infringing article or process to find out whether the
patent has been infringed. This is the simplest way
and indeed the only sure way to find out whether there
is a piracy. This is what was done in the hair-pin
case, above-referred to, and is, indeed, always done.
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Unessential features in an infringing article or
process are of no account. If the infringing goods are
made with the same object in view which is attained
by the patented article, then a minor variation does
not mean that there is no piracy. A person is guilty of
infringement if he makes what is in substance the
equivalent of the patented article. Some trifling or
unessential variation has to be ignored. There is a
catena of authority in support of this view. We need
not cite all those cases which were brought to our
notice at the Bar. Suffice it to quote the words of Lord
Denning, M. R. in Beecham Group Limited v. Bristol
Laboratories Ltd. and another, 1967 (16) R.P.C. 406
(12):-
"The evidence here shows that in making
hetacillin in the United States the defendants
use a principal part of the processes which are
protected here by the English patents. The
importation and sale here is prima facie
infringement.
"There is a further point. A person is guilty of
infringement, if he makes what is in substance
the equivalent of the patented article. He
cannot get out of it by some trifling or
unessential variation...... On the evidence as it
stands, there is ground for saying that hetacillin
is medically equivalent to ampicillin. As soon
as it is put into the human body, it does, after
an interval, by delayed action, have the same
effect as ampicillin. In these circumstances, I
think there is a prima facie case for saying
there was an infringement. The process is so
similar and the product so equivalent that it is
in substance the same as ampicillin."
26. We have seen the viewers marketed by the
defendants and the viewers produced by the plaintiff.
The viewers marked and kept on record as (1), (1A)
Mecorama and a fourth viewer are definitely objects
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produced by piracy of the plaintiff's patent. The
defendants have made certain variations in its viewers
but these are unessential; and what the defendants
market is substantially the same thing, as was
conceived by the plaintiff. By trifle variations if the
effect obtained by the defendants is the same, and we
hold that it is the same, then according to the rule
enunciated in the Ampicillin case, referred to above,
there is a clear piracy. The idea of the plaintiff which
is a novelty is clearly infringed. In any case, the
infringement is admitted by defendants 1 and 2. We
have dealt with this matter in detail because the
defendant No. 3 has put in appearance at the last
stage but does not admit infringement. Therefore, we
hold that there is clear infringement of the plaintiff's
patent, which we have delineated above."
36. Reliance is also placed upon the decision of the
Supreme Court of Canada in the case of Free World Trust
v. Electro Sante Inc., wherein the court formed the view
that non-essential elements may be omitted or substituted,
but that too would not shield infringement. It summarized
the issue as follows:
"31. The appeal thus raises the fundamental issue of
how best to resolve the tension between "literal
infringement" and "substantive infringement" to
achieve a fair and predictable result. There has been
considerable discussion of this issue in Canada and
elsewhere, which I will discuss briefly in support of
the following propositions:
(a) The Patent Act promotes adherence to the
language of the claims.
(b) Adherence to the language of the claims in turn
promotes both fairness and predictability.
(c) The claim language must, however, be read in an
informed and purposive way.
(d) The language of the claims thus construed defines
the monopoly. There is no recourse to such vague
notions as the "spirit of the invention" to expand it
further.
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(e) The claims language will, on a purposive
construction, show that some elements of the
claimed invention are essential while others are non-
essential. The identification of elements as essential
or non-essential is made:
(i) on the basis of the common knowledge of the
worker skilled in the art to which the patent
relates;
(ii) as of the date the patent is published;
(iii) having regard to whether or not it was
obvious to the skilled reader at the time the
patent was published that a variant of a
particular element would not make a difference
to the way in which the invention works; or
(iv) according to the intent of the inventor,
expressed or inferred from the claims, that a
particular element is essential irrespective of its
practical effect;
(v) without, however, resort to extrinsic
evidence of the inventor's intention.
(f) There is no infringement if an essential element
is different or omitted. There may still be
infringement, however, if non-essential elements are
substituted or omitted.
32. Based on the foregoing principles, I conclude
that the appellant's arguments must be rejected. As
stated, the ingenuity of the patent lies not in the
identification of a desirable result but in teaching one
particular means to achieve it. The claims cannot be
stretched to allow the patentee to monopolize
anything that achieves the desirable result. It is not
legitimate, for example, to obtain a patent for a
particular method that grows hair on bald men and
thereafter claim that anything that grows hair on bald
men infringes. I turn then to the first of the
propositions listed above.""
20. The principles that can be culled out from the conspectus of the
aforesaid judgments, in the context of the present case involving a process
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patent are that the patented process has to be compared with the infringing
process to find out if the patent has been infringed. This is the simplest way
and indeed the only sure way to find out whether there is a piracy.
Unessential features in an infringing article or process are of no account. If
the infringing goods are made with the same object in view which is attained
by the patented article, then a minor variation does not mean that there is no
piracy. A person is guilty of infringement if he makes what is in substance
the equivalent of the patented article. Some trifling or unessential variation
has to be ignored and if the two processes are the same, a minor variation by
the infringer will not shield him from piracy and an apt example of this was
in the case of Beecham Group Ltd. v. Bristol Laboratories Ltd., 1967 (16)
R.P.C. 406 (12), referred to above.
21. Plaintiffs heavily relied on an article on Doctrine of Equivalents from
a Journal of Intellectual Property Right, Vol. 12, May, 2007, Pages 314-329,
which in my view states nothing different from what has been held in the
aforesaid judgments, i.e., the Doctrine of Equivalents mandates that in the
absence of literal infringement, a product may be found to infringe a
patented product, if it is found to be its substantial equivalent and if the
proposition that the scope of a patent is limited to its literal elements is
accepted, it would allow a competitor to make an unimportant or
insubstantial change to a patented invention and defeat the patent. Thus, the
scope of a patent is not limited to its literal terms but embraces all
equivalents to the claims described.
22. I may also allude to the judgment in Warner-Jenkinson Co., Inc.
(supra), relevant paras of which are as under:
"
...
We concur with this apt reconciliation of our two lines of
precedent. Each element contained in a patent claim is
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deemed material to defining the scope of the patented
invention, and thus the doctrine of equivalents must be
applied to individual elements of the claim, not to the
invention as a whole. It is important to ensure that the
application of the doctrine, even as to an individual
element, is not allowed such broad play as to effectively
eliminate that element in its entirety. So long as the
doctrine of equivalents does not encroach beyond the
limits just described, or beyond related limits to be
discussed infra this page and 31-34, 39, n. 8, and 39-40,
we are confident that the doctrine will not vitiate the
central functions of the patent claims themselves.
xxx xxx xxx
...
In our view, the particular linguistic framework used is
less important than whether the test is probative of the
essential inquiry: Does the accused product or process
contain elements identical or equivalent to each claimed
element of the patented invention? Different linguistic
frameworks may be more suitable to different cases,
depending on their particular facts. A focus on individual
elements and a special vigilance against allowing the
concept of equivalence to eliminate completely any such
elements should reduce considerably the imprecision of
whatever language is used. An analysis of the role played
by each element in the context of the specific patent claim
will thus inform the inquiry as to whether a substitute
element matches the function, way, and result of the
claimed element, or whether the substitute element plays a
role substantially different from the claimed element. With
these limiting principles as a backdrop, we see no purpose
in going further and micromanagaing the Federal
Circuit's particular word choice for analyzing
equivalence. We expect that the Federal Circuit will refine
the formulation of the test for equivalence in the orderly
course of case-by-case determinations, and we leave such
refinement to that court's sound judgment in this area of
its special expertise."
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23. Relevant it is to note that learned counsels for the Defendant had
specifically urged that the judgment in Warner- Jenkinson Co., Inc.
(supra), by the US Supreme Court is perhaps the only decision on the
Doctrine of Equivalents on Chemical Processes. The submission to this
effect is unrebutted on behalf of the Plaintiffs and nothing was shown
contrary thereto. In Warner- Jenkinson Co., Inc. (supra), the Supreme
Court held that in cases of process patent infringement, the Doctrine of
Equivalents must be applied to individual elements of the claim and an
analysis of the role played by each element in the context of the specific
patent claim will thus inform the enquiry as to whether a substitute element
matches the function, way and result of the claimed element or whether the
substitute element plays a role substantially different from the claimed
element. The determination of equivalents should be applied as an objective
inquiry on an element-by-element basis.
24. Seen in this backdrop and examining on an element-to-element basis
and also keeping in view the undisputed fact that 3-Bromo-1-(3-Chloro-2-
pyridinyl)-1H-pyrazole-5-carboxylic acid and 2-Amino-5-chloro-3, N-
dimethylbenzamide, used in Defendant's process for preparing CTPR are
the same as claimed in the suit patent, the first question that begs an answer
is what are the essential feature(s) of the process covered and claimed by the
suit patent.
25. In order to answer this question, I may refer to the Reports of the
Advisors, more specifically question (ii) in the Terms of Reference (II)/
(FMC). The question as formulated is as under:
"ii. What are the essential feature(s) of the process covered
and claimed by the suit patent IN'645?
a) The answer by Prof. Bhanage, is as follows:
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"Reacting 2 and 3 in presence of R-sulfonyl chloride
to form a compound to form final product."
b) The reply by Dr. Nair, is as under:
"The essential features of the process covered in the
suit patent IN'645 comprises combining the
carboxylic compound of Formula 2 with the aniline
compound of Formula 3 in the base to form a
mixture and then addition of the sulfonyl chloride
R8S(O)2Cl of Formula 4 to the mixture in a single
reactor."
26. In view of the said findings coupled with the specification of IN'645
and the detailed description therein, in my prima facie view, sulfonyl
chloride, more particularly, methanesulfonyl chloride is an essential and
integral part of the suit patent and on this count, the stand of the Defendant
is correct.
27. The settled law for determining the question of infringement is that it
has to be kept in mind that non-essential or trifling variations in the
allegedly infringing process would not be germane, so long as the substance
of the suit patent is copied. Doctrine of Equivalents should be applied to
examine if the substituted element(s) in the infringing product does the same
work, in substantially the same way, to accomplish the same result. Seen in
this light, it is now required to be considered, if the use of thionyl chloride in
the Natco process is a minor/trivial change from use of sulfonyl chloride,
which as a reagent is critical to the novelty and functionality of the suit
patent, so as to infringe the suit patent, applying the Doctrine of Equivalents.
Both Advisors agree that thionyl chloride and sulfonyl chloride are different.
Relevant would it be in this regard to refer to question no. (iii) in Terms of
Reference (I)/Natco. The question formulated is as under:
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"3. Is the reagent thionyl chloride used in the Natco
process for converting the pyrazole carboxylic acid to acid
chloride the same as the reagent used for coupling the
pyrazole carboxylic acid with aniline as set out in Claims 1
to 11 of IN 298645? Do thionyl chloride which is an
inorganic chloride, and sulfonyl chlorides which are
organic chlorides, have different physical and chemical
characteristics?"
In response to the said question, Prof. Bhanage has found that the two
reagents are not the same. Dr. Nair, has given a detailed answer, elaborating
on the physical and chemical properties of thionyl chloride (inorganic
chloride) in comparison to sulfonyl chloride (organic chloride). The reply is
as follows:
"Reply: No, the reagents, thionyl chloride and sulfonyl
chlorides are different. The said reagents have different
physical and chemical characteristics.
The reagent thionyl chloride (SOCl2) used in Defendant's
process is different from the reagent sulfonyl chloride of
formula 4 i.e. R8S(O)2Cl claimed in claims 1 to 11 of
IN298645. The suit patent IN'645 particularly uses
methane sulfonyl chloride as claimed in claim 3.
The inorganic chloride i.e. thionyl chloride (SOCl2) has
different physical and chemical properties in comparison
to the organic chloride i.e. sulfonyl chloride (RSO2Cl)
which comprises an alkyl group.
Thionyl chloride Methane sulfonyl chloride
Boiling point: 79℃ Boiling point: 161℃
Melting point: -105℃ Density: 1.480 g/mL
Density: 1.631 g/mL at 25℃
(lit.)
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It is a dense, volatile liquid. It is a colourless liquid
Soluble in most aprotic that dissolves in polar
solvents: toluene, organic solvents but is
chloroform, diethyl ether. reactive toward water,
Reacts with protic solvents alcohols, and many
such as alcohols and water. amines.
The by-products are SO2 The by-product is methane
(gas) and HCl (gas) which sulfonic acid which needs
can be trapped in alkali to be removed through
leaving behind pure alkyl purification.
chloride.
28. From the above findings, the prima facie conclusions are (1) sulfonyl
chloride is an essential element of the suit patent and (2) thionyl chloride
used as a reagent in the Natco process, differs from sulfonyl chloride in its
physical and chemical properties. Additionally, it requires a mention that in
the Natco process, thionyl chloride is used as a chlorinating agent to react
with carboxylic acid to displace the -OH group present in the acid and
replace it with the chlorine atom to form an acid chloride, while in the
Plaintiffs' process sulfonyl chloride is added to the mixture of a Carboxylic
acid, Amide, Analine and a Base to activate the process and thus acts as a
'coupling agent' to control the rate of reaction as well as the yield produced
by it. In fact, it the case of the Plaintiffs that the advantages of sulfonyl
chloride according to IN'645 reside in its utility for acid-amide coupling
besides its convenience to use, low cost and the advantage of being able to
control the rate of coupling. 'Chlorination' is a process in which chlorine is
introduced into a molecule while 'coupling reaction' refers to class of
organic reactions that involve joining of two chemical species, usually with
the help of a metal catalyst. Coupling Agent is a compound which provides
a chemical bond between two dissimilar materials, usually an inorganic and
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an organic. These chemicals usually modify the surface functionality of
filler effectively to aid easy bonding with polymer chains.
29. In the context of sequence and nature of the chemical reaction, I may
refer to the answers given by Dr. Nair, in response to questions (7) and (8)
[Terms of Reference (I)/NATCO], which are as under:
"7. In the NATCO Process when thionyl chloride is used
the chloride group is attached to the carboxylic acid
group in the pyrazole carboxylic acid to form carbonyl
chloride which is not a mixed anhydride. Is this correct?
Reply: Yes, it is correct.
In Defendant's process R-CO-Cl the corresponding
carbonyl chloride (acid chloride) is formed which is not an
anhydride.
8. Is the NATCO process which requires reacting a
pyrazole carboxylic acid with thionyl chloride to obtain
an acid chloride and then reacting the acid chloride so
formed with an aniline within the scope of Claims 1 to 5
of IN'645? Is that correct?
Reply: No
Defendant's Process is distinct from the process claimed in
claims 1 to 5 of IN'645. Moreover, in IN'645 sulfonyl
chloride is used and also all the three reagents i.e. the
acid, the aniline compound and sulfonyl chloride are
added in a single reactor. In Defendant's process the
carboxylic acid is first converted to its acid chloride using
thionyl chloride in a first reactor. The acid chloride so
obtained is reacted with 2-Amino-5-chloro-N,3-
dimethylbenzaraide in another reactor to obtain the final
product.."
30. Since much has been argued on behalf of the Plaintiffs on the
equivalence of the two processes, I may refer to the findings on question (iv)
[Terms of Reference (II)/(FMC)] which are extremely relevant and are as
follows:
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"(a). (iv) Whether the Defendant's process for preparing
Chlorantraniliprole (CTPR) is equivalent to the process
claimed by the suit patent IN'645?
Dr. Nair's Report:
Reply: Yes, though not literally. The equivalence is
distinguished in resultant impurity profile of the final
product (CTPR) obtained by using thionyl chloride in
place of methane sulfonyl chloride in the Defendant's two-
step process as against the Plaintiff's process in a single
reactor.
In the suit patent IN'645, the process for preparing
Chlorantraniliprole(CTPR) comprises reacting carboxylic
acid of Formula 2, the aniline compound of Formula 3 and
the sulfonyl chloride of Formula (4) particularly methane
sulfonyl chloride in single reactor.
Moreover, in IN'645 process due to the use of methane
sulfonyl chloride there is formation of the solid toxic by-
product methane sulfonic acid which is harzardous to the
environment. In Defendant's process the use of thionyl
chloride results in liberation of SO2 (gas) and HCl (gas).
The liberated gases are scrubbed and absorbed in
caustic soda solution to give sodium chloride and
sodium bisulfite having use in food and cosmetic
industry.
The results of the reaction using methane sulfonyl chloride
in the suit patent IN'645 compared to the reaction using
thinoyl chloride in the defendant's process does not
produce the same result in view of the resultant
characteristics of the by-products and impact of the
impurity profile of the final product.
As such there is no literal equivalence between
the Defendant's process and the Plaintiff's IN'645
process."
(b). Additionally, in the earlier Report dated 05.08.2022,
Dr. Nair, had observed as under:
"Moreover, in IN'645 process due to the use of
methane sulfonyl chloride there is formation of the
solid toxic by-product methane sulfonic acid which
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is harzardous to the environment. In Natco's process
the use of thionyl chloride results in SO2 (gas) and
HCl (gas) which are released and may be collected
and converted to respective acids. There is no
formation of solid by-products that could cause
harm to the environment in the Natco's process.
Further, IN'645 employs costly reagent methane
sulfonyl chloride, compared to thinoyl chloride used
by the Defendant.
The results of the reaction using methane sulfonyl
chloride compared to the reaction using thinoyl chloride
does not produce the same result in view of the resultant
characterstics of the by-products and impact of the
impurity profile of the final product. As such there is no
equivalence.
(c). Prof. Bhanage's Report:
Answer: 'No. Though starting materials are same, one
process uses thionyl chloride (SOCl2) (NATCO) and
another process uses R-sulfonyl chloride (FMC) for
conversion to CTPR are different. They are different
compound with different reactivity and physical
properties'."
31. It would be apposite at this stage to mention that a specific question
was posed to the Advisors as to whether the Defendant's process is covered
and claimed by the process claimed by the suit patent and the answer was
'No'. Dr. Nair has stated 'The Defendant's process for preparing
Chlorantraniliprole (CTPR) is not covered by the process claimed by the suit
patent IN'645'. Prof. Bhanage stated 'No, as they are using SOCl2 and
which is not covered claims of IN'645'.
32. Pertinently, in response to a specific term viz. if the two processes are
'distinct or same', the finding by Prof. Bhanage is as follows:
"Are the following two process distinct or the same?
Answer: They are distinct.
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NATCO Process IN298645 process
(1).
(1). +
+ Thionyl Chloride
(SOCl2)
+
(acid chloride).
Mixture I (2 + 3)
(2).
(2). Mixture I (2+3) + Base
+ 3-Picoline (base)
Mixture of benzamide and 3-picoline base Mixture II (2 + 3 + Base)
(3).
(3).
Mixture II + Sulfonyl chloride
(2+3+Base) (R8S(O)2Cl)
+ Mixture of
and 3-Picoline base from
(2) above
(If X= Cl, Chlorantraniliprole of formula-Ia; and
If X= CN, Cyantraniliprole of formula-Ib)
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33. Reply given by Dr. Nair is as follows:
"5. Are the following two process distinct or the same?
Reply: Distinct as explained below.
The processes of Defendant (Defendant) and of the suit
Patent IN298645 are distinct.
In the Defendant's process, 3-Bromo-1-(3-Chloro-2-
pyridinyl)-1H-pyrazole-5-carboxylic acid is reacted in the
first reactor with thionyl chloride (SOCl2) to obtain the
intermediate acid chloride. The sulphur dioxide and
hydrogen chloride gases liberated during the reaction
were scrubbed out during the reaction. In reactor-2 2-
Amino-5-chloro-N,3-dimethyl benzamide, acetonitrile and
3-picoline were charged and then the reaction mass from
the reactor -1 were added to the above reaction mass to
yield the final product chlorantraniliprole of Formula-Ia
wherein X is Cl.
In the Defendant's process, 3-Bromo-1-(3-Chloro-2-
pyridinyl)-1H-pyrazole-5-carboxylic acid is converted to
its chloride prior to the reaction with 2-Amino-5-chloro-
N,3-dimethyl benzamide.
In suit patent IN298645, the carboxylic acid of formula 2
(e.g. 3-Bromo-1-(3-Chloro-2-pyridinyl)-1H-pyrazole-5-
carboxylic acid) and the aniline of formula 3 (e.g. 2-
Amino-5-chloro-3, N-dimethylbenzamide) are first mixed
in base to obtain the mixture followed by addition of
sulfonyl chloride (R8S(O)2Cl) in the same reactor to yield
the final product of formula 1, as claimed in claim 1,
claims 5 to 9 and described in the specification.
In the suit patent IN'645, the base is combined with the
compounds of Formulae 2 and 3 to form the mixture before
combining with sulfonyl chloride. All the three reagents
are added for the reaction to occur in a single reactor.
It is noted that the by-products in Defendant process are
SO2 (gas) and HCl (gas) which are scrubbed and
absorbed in caustic soda solution to give sodium bisulfite
and sodium chloride respectively, whereas, in the suit
patent IN298645 the by-product is solid methane sulphonic
acid.
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Hence, the Defendant's process is different and distinct
from the suit Patent IN298645."
34. For a ready reference, a comparative of the reactions components
between FMC and Natco process for CTPR synthesis is scanned and placed
below:
35. It will also be useful to allude at this stage to the conclusion of Prof.
Bhanage, as follows:-
"Conclusion:
1. The processes mentioned in these two patents are different.
2. Impurity profile provided by Natco in various annexures
mentioned in points 9, 10 and 11 is possible with Patent
IN'645.
3. More particularly impurity methane sulfonic acid is not
possible with Natco Process."
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Signing Date:20.09.2022
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36. From the aforesaid analysis and the categorical findings of the both
the Scientific Advisors and applying the principles enunciated in the
judgements, aforementioned, this Court is of the prima facie view that the
suit patent process and the Natco process are distinct and different.
Sulphonyl chloride is an essential element of suit patent and use of thionyl
chloride as a reagent coupled with a different sequence of the reaction, as
brought forth by the Scientific Advisors, cannot be termed as an
insignificant or trivial or insubstantial change in the Natco process and thus
the process prima facie does not come under the rigors of Doctrine of
Equivalents. The Advisors were appointed with the consent and agreement
of the parties and needless to state their opinion and findings needs to be
respected. Moreover, there is no challenge to the findings of the Advisors.
Learned counsel for the Defendant has rightly relied on the judgment of the
Supreme Court in Martin F. D'Souza (supra), for the proposition that
Courts are not experts and should not substitute their views or opinion for
those of the experts or specialists in the field.
37. This Court also finds prima facie merit in the submissions on behalf
of the Defendant that IN'645 focuses on acid-amide coupling where both the
acid and amide intermediates are known compounds for which patent
protection expired on 13.08.2022 and where the only reagent used is
sulfonyl chloride. The product CTPR obtained at the end of process of
claim 1 in IN'645 is not new since it was already known and was disclosed
and claimed in IN'978 and thereafter again in IN'307, both of which were
published before the priority date of IN'645. The Reports of the Scientific
Advisors supports the fact that the acid and bromide intermediates used in
the suit patent are disclosed in prior art IN'218, IN'017 and WO'518.
38. An argument was also raised on behalf of the Plaintiffs with regard to
presence of impurity methane sulfonic acid in CTPR formed in Natco
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process. Dr. Nair, in response to Natco's Terms of Reference has stated that
the documents/extracts of the Defendant's application for approval by
CIBRC show methane sulfonic acid impurity as 'Nil', though Certificate of
Registration issued by CIBRC shows impurity not exceeding (maximum)
0.30%. Prof. Bhanage has stated that the impurity will arise only from
methane sulfonyl chloride hydrolysis to acid (from the patent IN'645).
39. Plaintiffs have also relied on an affidavit filed by Dr. Vikram Adsool,
to which the Defendant responded by arguing that Dr. Adsool is an FMC
employee and thus much credence cannot be given to his opinion. Suffice
would it be to state at this stage that in the light of the opinions given by two
Scientific Advisors, as aforementioned, the affidavit filed by Dr. Adsool
cannot be placed on a higher pedestal, besides the fact that he is an
employee of the Plaintiffs. In my prima facie view, even otherwise the
conclusion drawn by Dr. Adsool does not seem to be correct in view of the
fact that when sulfonyl chloride is used in a reaction, the process proceeds
differently as compared to when thionyl chloride is used i.e. equating the
formation of acid chloride in the Natco process to coupling of carboxylic
acid and amide intermediates in the FMC process is wholly incorrect, as
opined by both the Scientific Advisors. It bears repetition to state that
Section 10(4) of the Act expressly states that claims define the scope of
protection. Claim 1 of IN'645 is limited to acid+amide+sulfonyl chloride.
On a pointed query, the Advisors have opined that the Natco process is
outside the scope of claims of IN'645, where the suit patent is limited to
coupling of carboxylic acid intermediate with analine using sulfonyl
chloride. This is apparent from the complete specification of IN'645 which
sets out the objective of the invention which can only be achieved by using
sulfonyl chloride, particularly, methane sulfonic chloride.
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40. Plaintiffs have thus been unable to discharge the burden of proving
that the Natco process is equivalent to the suit patent process and prima
facie no case of infringement is made out. Balance of convenience also lies
in favour of Natco. It was stated on behalf of the Natco that it has already
suffered a loss of nearly 100 crores on account of not being able to launch its
product. The product patent IN'307 has already expired on 13.08.2022. The
product in question is an insecticide and as rightly pointed out by the learned
counsels for the Defendant, is required between September to December in
the Kharif season. Seen holistically, the restraint order passed against the
Defendant from launching the product CTPR deserves to be vacated.
41. Learned Senior Counsel for the Plaintiffs heavily relied on the
judgment in Sotefin SA (supra), for the proposition that it is imperative to
reach a finding that all essential elements of the suit patent are present in the
infringing process, in order to determine infringement. The proposition of
law is beyond any debate, however, on facts the said judgment is
distinguishable from the present case. Bare reading of the judgment shows
that in the said case the independent Scientific Advisors had opined that 17
of the 19 elements of claim No. 1 of the suit patent were found in the
infringing product. On an analysis of the Report as well as having examined
the two elements, i.e., 'hinges' and 'immobilization of rear wheels' in the
infringing product, Court was of the view that these elements did not make
any substantial difference in the functionality and did not have material
effect on the working of the invention, as asserted by the Defendants therein.
In this background, the Court found that the changes were insignificant and
prima facie case of infringement of suit patent was made out by the Plaintiff
therein. In contrast to the said facts, in the present case both Scientific
Advisors have opined that the competing processes are distinct, different and
not 'equivalent'. The judgment, therefore, does not aid the Plaintiffs.
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42. In Raj Parkash (supra), relying on the settled proposition of law that
a person is guilty of infringement if he makes an equivalent patented article
and trifling or unessential variation has to be ignored, Division Bench of this
Court found in the facts of the case that Defendants had made variations
which were unessential and were marketing a product which was
substantially the same as the one conceived by the Plaintiff, which is
diametrically opposite to the facts of the present case. Therefore, the
Plaintiffs cannot seek refuge under the said judgment.
43. In view of the aforesaid, Natco is permitted to launch its product, i.e.,
CTPR, with a caveat that it shall remain bound by the undertaking and
assurance given to the Court that it will not use a process claimed under
IN'645 or any other process, which infringes the suit patent IN'645.
Additionally, Natco shall keep accounts of the sales and shall file the same
on an affidavit on a quarterly basis in this Court.
44. Present application is accordingly dismissed in the aforesaid terms.
CS(COMM) 349/2022 & I.A. 8132/2022, 9519/2022, 10886/2022
45. List before learned Joint Registrar for further proceedings on
28.11.2022.
JYOTI SINGH, J
th
SEPTEMBER 19 , 2022/shivam/rk
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By:KAMAL KUMAR
Signing Date:20.09.2022
20:54:04
