PaperNo. __
`
`Filed on behalf of: Junior Party Levin
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`By:
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`Gary J. Gershik
`Registration No. 39,992
`Cooper & Dunham LLP
`30 Rockefeller Plaza, 201h Floor
`New York, New York 10112
`Tel: (212) 278-0400
`Fax: (212) 391-0525
`E-mail: ggershik@cooperdunham.com
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`ANATLEVIN
`and MICHAEL GRABARNICK,
`Junior Pmty,
`(Application No. 13/926,389)
`
`v.
`
`ANDREA PASTORIO
`and PAOLO BETTI,
`Senior Pmty,
`(Patent 8,304,559)
`
`Patent Interference No. 105,995 (SGL)
`(Technology Center 1600)
`
`LEVIN REPLY 4
`(For Judgment Based on Invalidity of the Pastorio Claims over the Prior Ali)
`
`FINCHIMICA EXHIBIT 2009
`ADAMA MAKHTESHIM v. FINCH/MICA
`CASE IPR2016-00577
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`Interference No. 105,995
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`TABLE OF CONTENTS
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`TABLE OF AUTHORITIES…………………………………………………………
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`I. ARGUMENT…………………………………………………………………….. 1
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`A. WO ‘440 DISCLOSED DCA AS A MEDIUM FOR OXIDATION OF
`FIPRONIL SULFIDE PRECURSOR TO FIPRONIL……………………………….
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`1. WO ‘440 is entirely and only about the oxidation of the sulfide precursor
`of fipronil……………………………………………………………………..
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`2. Pastorio’s proposed interpretation of the word “poor” is not based on any
`underlying fact………………………………………………………………..
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`3. Pastorio’s claims do not require that DCA or DCPA oxidize the sulfide
`precursor of fipronil. …………………………………………………….…...
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`B. WO ‘440 RENDERS PASTORIO’S BROAD CLAIMS OBVIOUS……………. 4
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`1. Pastorio’s claims encompass poor results vitiating all assertions of
`advantageous discovery………………………………………………………
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`2. Use of a mixture of DCA and TFA is encompassed by the Pastorio claims 5
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`3. Use of a mixture of DCA and TFA was obvious…………………………. 6
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`4. Use of DCA and sulfuric acid was obvious and encompassed by the
`Pastorio claims…………………………………………………..……..……..
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`5. DCA is structurally similar to TCA and known to function in the same
`manner………………………………………………………………………..
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`6. DCA was known to be strong enough to form DCPA and to oxidize
`sulfides…………………………………………………………………..……
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`C. CLAIMS 11 AND 12 ARE ANTICIPATED BY OR OBVIOUS OVER WO
`‘440…………………………………………………………………………………..
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`APPENDIX 1: LIST OF EXHIBITS………………………………..………………. APP-1-1
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`APPENDIX 2A: LEVIN STATEMENT OF MATERIAL FACTS....…..………….. APP-2A-1
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`APPENDIX 2B: PASTORIO STATEMENT OF MATERIAL FACTS …………… APP-2B-1
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`APPENDIX 2C: LEVIN REPLY STATEMENT OF MATERIAL FACTS ……….. APP-2C-1
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`Cases
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`Interference No. 105,995
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`TABLE OF AUTHORITIES
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`Allergan, Inc. v. Apotex Inc.
` 754 F.3d 952 (Fed. Cir. 2014) …………………………………………………………… 1
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`Allergan v. Sandoz,
` 726 F.3d 1286, 1292 (Fed. Cir. 2013) …………………………………………………… 1
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`Celeritas Technologies Ltd. v. Rockwell International Corp.,
` 150 F.3d 1354 (Fed. Cir. 1998)…………………………………………………..………2
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`In re Cuozzo Speed Technologies, LLC,
` 793 F.3d 1268 (Fed. Cir. 2015) ……………………………………………….…….….. 6
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`In re Heck,
` 699 F.2d 1331, 1332-33, (Fed. Cir. 1983)………………………………………….….... 2, 6
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`KSR Int’l v. Teleflex Inc.,
` 550 U.S. 398 (2007)…………………………………………………………………….. 1
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`Pfizer Inc. v. Apotex, Inc.,
` 480 F.3d 1348 (Fed. Cir. 2007)……………………….…………………….…………… 1
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`Thorner v. Sony Computer Entm't Am. LLC,
` 669 F.3d 1362, 1366-1367 (Fed. Cir. 2012)…………………………………………..….5
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`Rules
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`Bd.R. 158(a)………………………………………………………….…...………………….... 2
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`I.
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`ARGUMENT
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`Interference No. 105,995
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`Party Pastorio’s Opposition 4 fails to rebut the unpatentability showing in Levin Motion
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`4 at least because it fails to address the implications of claim breadth and relies on unsupported
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`opinions of its new technical expert. Pastorio is effectively arguing for the patentability of some
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`non-existent tailored claims to which the real claims bear little relation.
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`Obviousness cannot be avoided by arguing lack of reasonable expectation of success of
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`merely a preferred embodiment or result. Allergan, Inc. v. Apotex Inc. 754 F.3d 952, 962-63
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`(Fed. Cir. 2014); Pfizer Inc. v. Apotex, Inc., 480 F.3d 1348, 1364 (Fed. Cir. 2007). The burden on
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`the patent challenger is correspondingly lower in case of a broad claim. Allergan, Inc. v. Sandoz,
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`Inc. 726 F.3d 1286, 1292 (Fed. Cir. 2013).
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`Pastorio claims a process involving a well-known reagent, dichloroacetic acid (DCA) in a
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`well-known sulfide oxidation reaction to make a known sulfoxide, fipronil. Given the facts,
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`debating reaction mechanisms and how well DCA would have been expected to make fipronil in
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`the manner of the Opposition is a distraction. KSR Int’l v. Teleflex Inc., 550 U.S. 398 (2007).
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`With respect to claim anticipation, the Opposition distracts again with its reliance on the
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`so-called “purpose” of and examples in the prior art. That WO ‘440 (Ex. 2009) disclosed DCA
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`to be an oxidation medium for making fipronil is not rebutted.
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`A. WO ‘440 DISCLOSED DCA AS A MEDIUM FOR OXIDATION OF FIPRONIL
`SULFIDE PRECURSOR TO FIPRONIL
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`On page 6, line 12 to page 7, line 14 of the Opposition, Pastorio acknowledged that WO
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`‘440 contains the statement that “dichloro acetic acid is a poor medium for oxidation,” but
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`argued that “Levin’s reliance on this single sentence is contrary to the actual disclosure of
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`Gharda and turns the teaching of the reference on its head.” The response is that Pastorio’s
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`arguments are irrelevant to the question of anticipation. Celeritas Technologies Ltd. v. Rockwell
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`International Corp., 150 F.3d 1354, 1361 (Fed. Cir. 1998). Moreover, a disclosure need not be
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`Interference No. 105,995
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`found in the examples or the claims or stated as being a solution the particular problem the prior
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`art is concerned with. In re Heck, 699 F.2d 1331, 1333 (Fed. Cir. 1983).
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`1. WO ‘440 is entirely and only about the oxidation of the sulfide precursor of fipronil
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`On page 8, lines 5-17 of the Opposition, Pastorio argued a distinction between
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`“oxidation” and “the oxidation” as used in WO ‘440. The response is that the entirety of WO
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`‘440 is concerned only with oxidation of the compound of formula-II, particularly to provide
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`fipronil. No other oxidation is discussed. WO ‘440 uses “oxidation” and “the oxidation”
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`interchangeably throughout to refer to that same oxidation reaction. (Ex. 2009, 7:21 to 9:25).
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`DCA was known in the art to be a good medium for oxidation, even a preferred medium
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`in several oxidation reactions. (Ex. 1014, 3:48-53; Ex. 1024, 2:56-59, 3:7-11, MF 141, Ex.
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`1052, 16:22-17:1, 19-21). To be consistent with the art, the statement must be understood to be
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`specific to the discussion of oxidation of the sulfide precursor of fipronil. Pastorio’s proposed
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`theory that the statement would be understood to be a general teaching that DCA is a poor
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`medium for oxidation is unreasonable and inconsistent with the evidence of record.
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`2. Pastorio’s proposed interpretation of the word “poor” is not based on any facts
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`On page 7, line 15 to page 8, line 17 of the Opposition, Pastorio argued that WO ‘440’s
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`characterization of DCA as “poor” should be interpreted to be a general statement that DCA is
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`not at all suitable for oxidation reactions. The response is Pastorio’s proposed interpretation of
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`the word “poor” ignores the context of WO ‘440 and relies solely on Pastorio’s expert Dr.
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`Curran’s opinion of the word “poor,” which is itself unsupported by evidence or underlying fact
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`(Ex. 2085, ¶¶36-39) and contrary to Bd.R. 158(a), which provides that an expert opinion that
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`does not disclose the underlying facts or data is entitled to little or no weight.
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`In the absence of supporting evidence, Dr. Curran uses hyperbole to provide an abstract
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`example of usage of the word “poor” consistent with his desired meaning: “‘poor’ can include
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`non-functional, e.g., a hot air balloon would be a poor choice for flying to the moon.” (Ex. 2085,
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`¶39). Hyperbole is not used in technical writing. Notably, Dr. Curran provided not a single
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`citation from technical literature to support his opinion of the meaning of the word “poor.” In
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`contrast, Dr. Gribble’s testimony regarding the disclosure of WO ‘440 is based on facts and data.
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`(Ex. 1044, ¶¶77-79, see also, ¶¶34, 35, 41-83).
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`On page 7, lines 18-20 of the Opposition, Pastorio argued that Dr. Gribble equivocated
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`during his deposition regarding the meaning of the term “poor”. The response is that Dr. Gribble
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`was unequivocal, and consistent throughout. Dr. Gribble never agreed that in the context of WO
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`‘440 the word “poor” would mean “does not work at all.” (Ex. 2083, 68:21-70:3).
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`Dr. Curran’s own scientific usage of the word “poor” admits to Dr. Gribble’s
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`understanding of the word “poor” and the importance of the context. Dr. Curran acknowledged
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`that “poor” would not be used in technical writing to mean there was no result. (Ex. 1052, 78:16-
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`22, see full discussion at 77:11-78:22). In at least three papers in prestigious journals reviewed
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`by persons skilled in the art to assure clarity and substance, Dr. Curran used the word “poor” to
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`report results well above zero. (Ex. 1052, 79:1-86:6; especially, 80:20-81:11; 83:4-9; and
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`85:13-86:6. See, MF 144, Exs. 1047, 1048 and 1049.). Indeed, Dr. Curran volunteered that the
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`word “poor” was used to make a “comparison”. (Ex. 1052, 83:4-9).
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`On page 8, line 18 to page 9, line 5 of the Opposition, Pastorio cited two judicial
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`decisions and argued that the WO ‘440 disclosure is not sufficient for anticipation. The response
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`is that Pastorio has not even attempted to show whether the facts of the two decisions are
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`analogous to the facts of the instant case. They are not, at least because in both decisions there
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`was evidence supporting multiple interpretations, unlike in the instant case.
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`It would be inconsistent with its normal usage in technical literature to interpret the word
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`“poor” to mean that DCA does not work at all to make fipronil. Pastorio has even used the word
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`“poor” on the present record when describing a reaction that produced at least 30 g of fipronil.
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`(Paper 116, 2:13-19; Paper 144, 14:5-12).
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`3. Pastorio’s claims do not require that DCA or DCPA oxidize the sulfide precursor of
`fipronil.
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`On page 3, lines 12 to page 5, line 20 of the Opposition, Pastorio argued that the phrase
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`“in the presence of [DCA]” in Pastorio’s claim 1 requires DCA to form DCPA and act as the
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`oxidizing agent to form fipronil. The response is that Pastorio’s claims do not recite anything
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`which requires that DCA or DCPA be the oxidation reagent. Pastorio deliberately broadened
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`claim 1 to recite “in the presence of [DCA]” from an earlier version of the claim in its Italian
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`priority document which expressly required that “the oxidising agent is dichloroperacetic acid”.
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`(Ex. 2010, Claim 1). Pastorio’s claims cannot now reasonably be construed to require
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`dichloroperacetic acid to be the oxidizing agent. Thus, the claims of the ‘559 patent permit the
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`DCA to be merely a solvent, a medium for oxidation, or even a melting point depressant.
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`Pastorio’s Opposition did not dispute that claims 2-10 also stand or fall with claim 1.
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`(Paper 175, 7:14-18; 26:1-32:1; Ex. 1044, ¶81)
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`B. WO ‘440 RENDERS PASTORIO’S BROAD CLAIMS OBVIOUS
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`On page 9, lines 17-21 of the Opposition, Pastorio argued “A person of ordinary skill in
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`the art would not have been able to predict whether the oxidation of the sulfide precursor
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`utilizing DCA as a reagent would have been successful.” The response is that the level of
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`“success” needed to arrive at Pastorio’s claims is low. Pastorio’s claims have a scope well
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`beyond the certain embodiments that Pastorio emphasizes. (Paper 174, 17:15-18). That
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`Pastorio’s claim 1 is not limited with respect to any of commercial suitability, selectivity, yield,
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`scale, time, reaction rate, temperature or proportion of components is not rebutted. Consequently,
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`an expectation that DCA would produce any amount of fipronil, and do so poorly, would be a
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`sufficient expectation of success establishing obviousness of Pastorio’s broad claims.
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`1. Pastorio’s claims encompass poor results vitiating all assertions of advantageous
`discovery
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`On page 1, lines 18-19 and page 3, lines 15-16 of the Opposition, Pastorio argued that
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`Pastorio’s process is an “economical and efficient” process and on page 1, lines 16-18 and page
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`3, line 18 to page 4, line 4 of the Opposition, argued that DCA is an “excellent” reagent for
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`production of fipronil through oxidation of its sulfide precursor. The response is that Pastorio’s
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`claims cover poor results. Pastorio has asserted in its priority motion that processes showing
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`admittedly poor results are within the scope of Pastorio’s claims. (Paper 177, 9:22-10:4; Exs.
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`2037, 2039, 2040, MF 150, Ex. 1052, 70:17-71:3, 73:3-22). The purported “excellent” results in
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`the ‘559 patent upon which the Opposition and Dr. Curran rely are not shown to have been
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`actually obtained. (Paper 144, 11:2-11; MF 137, Ex. 1052, 9:15-19, 51:16-52:5).
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`2. Use of a mixture of DCA and TFA is encompassed by the Pastorio claims
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`On page 2, lines 7-11 and pages 10-11 of the Opposition, Pastorio argued that there is a
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`“clear and unmistakable disavowal of the use of TFA in Pastorio’s specification.” The response
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`is Pastorio did not provide a clear and express disavowal of a process which also involves TFA.1
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`Thorner v. Sony Computer Entm't Am. LLC, 669 F.3d 1362, 1366-1367 (Fed. Cir. 2012).
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`1 Even if TFA/TFPA were excluded from Pastorio’s claims, Levin’s prima facie case set forth in Motion 4 still
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`holds. TFA was just one example of an acid which a person of ordinary skill would have known to use; as 3-
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`chlorobenzoic acid and H2SO4 were other examples. (Paper 175, 11:3-7) Other examples of acids were within the
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`knowledge of a person of ordinary skill at the time. (Ex. 1044; ¶31, Paper 81, 9:1-10:3).
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`Pastorio’s specification disparages both TFA and TCA, and could have supported a claim
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`expressly excluding both. Nonetheless, Pastorio’s claims only expressly exclude TCA/TCPA,
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`but not TFA/TFPA.2 It is logically inconsistent to say that Pastorio’s explicit statement in the
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`claims excluding TCA/TCPA has the same meaning and effect as saying nothing in the claims
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`whatsoever with respect to TFA/TFPA. (Ex. 1052, 45:22-47:13).
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`The only decisions cited by Pastorio are infringement cases where the standard of claim
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`interpretation is not the broadest reasonable interpretation. In re Cuozzo Speed Technologies,
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`LLC, 793 F.3d 1268 (Fed. Cir. 2015).3
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`3. Use of a mixture of DCA and TFA was obvious
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`On page 11, line 28 to page 12, line 17 of the Opposition, Pastorio argued that it would
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`not have been obvious to use DCA with TFA to prepare fipronil commercially. The response is
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`that a POSA need not have the same purpose or motivation as that of the prior art authors. In re
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`Heck, 699 F.2d 1331, 1333 (Fed. Cir. 1983) (Paper 175, 11:1-7).
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`4. Use of DCA and sulfuric acid was obvious and encompassed by the Pastorio claims
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`On page 17, lines 1-18 of the Opposition, Pastorio argued that it would not have been
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`obvious to use sulfuric acid with DCA to prepare fipronil because the Chinese reference (Ex.
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`1016 at 7) employs a two-phase system that utilizes a phase transfer catalyst. The response is
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`that Pastorio has not even alleged that the use of a two-phase system or the use of a phase
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`transfer catalyst is outside the scope of its claims. Furthermore, Pastorio has already admitted
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`2 Pastorio’s own specification recites “According to a particularly advantageous embodiment, the oxidation of the
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`compound having the general formula (II) occurs in the presence of an acid catalyst, advantageously homogenous.”
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`(Ex. 2001, 6:32-35) Thus, it is not at all clear that Pastorio intended to disclaim catalytic use of TFA in the
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`embodiments which employed an acid catalyst.
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`3 Pastorio can pursue amended claims in pending Reissue Serial No. 14/534,001, prosecution suspended.
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`that a POSA was aware that the addition of a strong acid, e.g. sulfuric acid, was conventional in
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`the art for the purpose of speeding up chemical reactions. (Ex. 1017, 46:22-24; Ex. 2003, ¶37;
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`Paper 25, 8:9-16; Paper 144, 9, 10 and 22).
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`5. DCA is structurally similar to TCA and known to function in the same manner
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`On page 12, line 18 to page 14, line 20 of the Opposition, Pastorio argued that oxidation
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`of fipronil is complex and a POSA could not predict how DCPA would act on fipronil. The
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`response is the technical basis of Pastorio’s argument is solely the difference in acidity between
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`TCA and DCA – this is a difference of degree, not function. There is no evidence of a functional
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`difference between TCA and DCA, rather the record reflects functional similarity (Ex. 1044,
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`¶¶32-34; MF 140, Ex. 1052, 13:5-20, 14:1-10, 15:21-16:12, 23:15-27:9).
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`6. DCA was known to be strong enough to form DCPA and to oxidize sulfides
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`On page 15, line 21 to page 16, line 7 of the Opposition, Pastorio argued “TCA results in
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`a significantly stronger oxidizing agent than DCA,” and a POSA would not have been able to
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`predict that DCPA would also be able to successfully oxidize the precursor to firponil. (MF 125;
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`Ex. 2085, ¶¶57-58).” The response is that a POSA would not have considered the acidity of
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`DCA to preclude it from producing at least some fipronil. The POSA knew that DCA was able to
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`form DCPA when exposed to hydrogen peroxide, and oxidize sulfides via DCPA (Ex. 1014,
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`3:48-53; Ex. 1024, 2:56-59, 3:7-11; Ex. 1052, 17:6-11). Moreover, even weaker peracids were
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`known to oxidize difficult-to-oxidize sulfides. (Paper 227, 16:1-3; Ex. 1019, 1:29-2:5; MF 143,
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`Ex. 1046, 1557, Ex. 1052, 13:5-20; 16:22-17:21; 22:5-15; 97:5-101:15; MF 82; MF 124).
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`Pastorio over-emphasizes the effect of the difference in acidity between DCA and TCA.
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`DCA has a pKa of 1.29 and TCA has a pKa of 0.65 (Ex. 1044, 10:18-11:1), which is within one
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`order of magnitude. The scale of pKa values has a “range over 10 to the 50 power,” i.e., at least
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`fifty (50) orders of magnitude, as admitted by Dr. Curran (MF 142, Ex. 1052, 101:16-102:2).
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`On page 16, lines 8-22 of the Opposition, Pastorio argued that acetic acid, which is much
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`weaker than DCA, was not disclosed to make firponil. The response is that acetic acid, which is
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`2,900 times weaker than DCA has been reported to oxidize the fipronil sulfide precursor. (Ex.
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`1019, 1:29-2:5; Ex. 1044, 10:9-11:7; Ex. 1052, 102:19-103:10). Dr. Curran admitted that WO
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`‘760 (Ex. 1019) provides a list of oxidizing agents, including peracetic acid and TCPA, which
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`were investigated for large scale preparations of fipronil. (Ex. 1052, 105:3-112:6). Dr. Curran
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`admitted that WO ‘760 cannot be understood to mean that no fipronil formed when peracetic
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`acid, TCA and the other listed oxidants were used. (Ex. 1052, 111:14-17, see excerpt below.)
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`Q: Well, does this sentence tell you that no fipronil formed whatsoever?
`A: No, but it doesn't tell me that fipronil formed in unsatisfactory purity, either.
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`The POSA also knew that another acid, 3-chlorobenzoic acid, which is also weaker than
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`DCA and also forms a corresponding peracid (MF 82; Ex. 2009, 4:14-16; Paper 175, 11:3-7), is
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`sufficiently strong to make fipronil, as admitted by Pastorio (MF 82; Ex. 2001, 1:61-62).
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`The POSA would have found it obvious and easy to try using DCA, having a strength
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`greater than acetic acid and 3-chlorobenzoic acid, to make fipronil. (Ex. 1052, 22:5-15; 9:20-
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`30:5; MF 124). The POSA would have been motivated to do so based on an expectation of
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`success and other advantages already admitted on the record with respect to DCA. (Ex. 2009
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`2:6-9; 10:10-25; Ex. 1014, 3:48-53; Ex. 1024, 2:56-59, 3:7-11, MF 151, Ex. 1052, 30:3-5)
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`C. CLAIMS 11 AND 12 ARE ANTICIPATED BY OR OBVIOUS OVER WO ‘440
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`On page 17, lines 23-25 of the Opposition, Pastorio argues that WO ‘440 neither
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`anticipated nor rendered obvious claims 11 and 12. The response is that a POSA was aware that
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`the process of WO ‘440 required purification and would have immediately envisaged common
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`purification techniques, including recrystallization with common solvents, to recover the reaction
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`components. (Paper 175, 7:16-18; Ex. 1016, page 7, Example 6; Ex. 1044, ¶¶81-83; Ex. 2083,
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`75:14-84:3). Pastorio admitted in the Background of its ‘559 Patent that the drawbacks of the
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`Interference No. 105,995
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`
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`WO ‘440 process would have been understood to require expensive purification. (Ex. 2001,
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`2:50-54). Dr. Curran admitted that certain embodiments of WO ‘440 required expensive
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`purification. (Ex. 1052, 47:1-13, 50:15-22); and recrystallization was a generally known
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`technique in the art. (Ex. 1052, 51:6-14).
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`Respectfully submitted,
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`
`/Gary J. Gershik/
`
`
`Gary J. Gershik
`
`
`Registration No. 39,992
`Attorney for Junior Party Levin
`Cooper & Dunham LLP
`30 Rockefeller Plaza, 20th Floor
`New York, New York 10112
`Tel: (212) 278-0400
`Fax: (212) 391-0525
`E-mail: ggershik@cooperdunham.com
`
`
`
`Norman H. Zivin
`
`Registration No. 25,385
`Attorney for Junior Party Levin
`Cooper & Dunham LLP
`30 Rockefeller Plaza, 20th Floor
`New York, New York 10112
`Tel: (212) 278-0400
`Fax: (212) 391-0525
`E-mail: nzivin@cooperdunham.com
`
`
`
`
`Date: November 10, 2015
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`9
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`

`

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`
`
`Exhibit No.
` 1014
` 1016
` 1017
` 1019
` 1024
` 1044
` 1046
`
` 1047
`
` 1048
`
` 1049
`
` 1052
` 2001
` 2003
` 2009
` 2010
` 2037
`
` 2039
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` 2040
` 2083
` 2085
`
`
`
`
`Interference No. 105,995
`
`APPENDIX 1: LIST OF EXHIBITS
`
`Description
`U.S. Patent No. 3,928,372 to Bochis et al.
`Chinese Patent Application Publication No. CN 101250158A, including certified
`English translation
`Transcript of October 13, 2014 Deposition of Barry M. Trost, Ph.D.
`PCT International Application Publication No. WO 01/30760 (Clavel et al.)
`U.S. Patent No. 6,013,761 to Zierer et al.
`Sixth Declaration of Gordon W. Gribble, Ph.D.
`H. Harry Szmant, Chapter 16, "Chemistry Of The Sulfoxide Group." Organic
`Sulfur Compounds (1961): 154-69.
`Dennis P. Curran and Sung-Bo Ko. "Synthesis of Optically Active a-Hydroxy
`Lactones by Sharpless Asymmetric Dihydroxylations of Ketene Acetals, Enol
`Ethers, and Ene Lactones." The Journal of Organic Chemistry J. Org. Chem.
`59.21 (1994): 6139-141.
`Dennis P. Curran, Ulf Diederichsen, and Michael Palovich. "Radical Cyclizations
`of Acylgermanes. New Reagent Equivalents of the Carbonyl Radical Acceptor
`Synthon." J. Am. Chem. Soc. Journal of the American Chemical Society 119.21
`(1997): 4797-804.
`Ali Ates and Dennis P. Curran. "Synthesis of Enantioenriched Axially Chiral
`Anilides from Atropisomerically Enriched Tartarate Ortho-Anilides." J. Am.
`Chem. Soc. Journal of the American Chemical Society 123.21 (2001): 5130-131.
`Deposition transcript of Dennis P. Curran, Ph.D. dated October 27, 2015.
`U.S. Patent No. 8,304,559 to Pastorio et al.
`Declaration of Barry M. Trost, Ph.D.
`WO 2007/122440 to Gharda et al.
`Italian Patent Application No. BS2010A0118.
`December 22, 2009 experiment report PS/43/2009/PB; English translation;
`certification of translation.
`December 22, 2009 experiment report PS/44/2009/PB; English translation;
`certification of translation.
`December 23, 2009 experiment report PS/45/2009/PB; English translation;
`certification of translation.
`Deposition transcript of Gordon W. Gribble, Ph.D. dated September 17, 2015.
`Declaration of Dennis P. Curran, Ph.D.
`
`
`1
`
`APP-1-1
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`

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`Interference No. 105,995
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`APPENDIX 2A: LEVIN STATEMENT OF MATERIAL FACTS
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`1. Pastorio’s involved U.S. Patent No. 8,304,559 patent contains claims 1-12, with former claims
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`13-15 having been statutorily disclaimed.
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`Pastorio’s Response: Admitted.
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`2. The count is defined as claim 1 of the ‘559 patent or claim 2 of Levin.
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`Pastorio’s Response: Admitted.
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`3. All of claims 1-12 correspond to the count.
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`Pastorio’s Response: Admitted.
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`4. ‘559 patent claim 1 corresponds exactly to the count.
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`Pastorio’s Response: Admitted.
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`5. ‘559 patent claims 1-12 define the same patentable invention. 37 CFR §§ 1.601(n); 1.606.
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`Pastorio’s Response: Pastorio objects to MF 5 as calling for a legal conclusion; Admit that
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`claims 1 – 12 have been determined to correspond to the Count; otherwise denied.
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`6. ‘559 patent claims 1-12 stand or fall together with respect to the prior art.
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`Pastorio’s Response: Pastorio objects to MF 5 as calling for a legal conclusion; otherwise,
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`Denied.
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`7. ‘559 patent Claim 1 is set forth in Appendix 3.
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`Pastorio’s Response: Admitted.
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`8. Thus, the claims relate to a sulfide oxidation step in the preparation of fipronil and closely
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`related compounds.
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`Pastorio’s Response: Admit that the claims require the oxidation of a compound with the
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`general formula ( II) to produce the compound of general formula (I); otherwise denied.
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`9. The ‘559 patent claims July 7, 2010 as its earliest priority date.
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`APP-2A-1
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`Pastorio’s Response: Admitted that the ʼ559 patent claims July 7, 2010 as its priority date.
`
`Interference No. 105,995
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`
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`10. During prosecution of the ‘559 patent, only three publications were cited.
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`Pastorio’s Response: Denied.
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`11. In a first-action allowance, the examiner’s reasons for allowance stated that WO 2007/122440
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`was considered to be the closest prior art, and included the statement “[a] person of ordinary skill
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`in the art would not have expected that making modifications would retain identical activity as
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`disclosed in the prior art.”
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`Pastorio’s Response: Admit that the Notice of Allowance stated “[t]he closest prior art is WO
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`2007/122440, which does not teach the claimed methods. This reference does not encompass
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`the scope of the instant application. This reference lacks identical or obvious limitations in the
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`process steps. A person of ordinary skill in the art would not have expected that making
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`modifications would retain identical activity as disclosed in the prior art.”
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`12. A person having ordinary skill in the art as of July 7, 2010 or May 6, 2011 would have had (1)
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`a bachelor’s or master’s degree in chemistry or a related discipline and have at least five years of
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`experience in synthetic organic chemistry, including sulfide oxidation or (2) a Ph.D. degree or
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`equivalent in organic chemistry and two years of experience in synthetic organic chemistry,
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`including sulfide oxidation. (Ex. 1044 at ¶ 11).
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`Pastorio’s Response: Admit that is Dr. Gribble’s definition of a person of ordinary skill in the
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`art; otherwise, denied.
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`13. The language of US ‘559 claim 1 is set forth in Appendix 3.
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`Pastorio’s Response: Admitted.
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`14. Formula
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`I covers
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`fipronil and Formula
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`II covers 5-amino-1-(2,6-dichloro-4-
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`trifluoromethylphenyl)-3-cyano-4-trifluoromethylthio pyrazole (“Compound 420”).
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`APP-2A-2
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`Pastorio’s Response: Admitted that in the Pastorio ʼ559 patent, the compound of formula I
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`Interference No. 105,995
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`
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`includes fipronil, and the compound of formula II includes the fipronil sulfide precursor,
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`which is also referred to by Levin as compound 420; otherwise, denied.
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`15. The oxidizing agent in claim 1 can be hydrogen peroxide.
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`Pastorio’s Response: Admitted that an oxidizing agent in claim 1 of the Pastorio ʼ559 patent
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`can be hydrogen peroxide; otherwise, denied.
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`16. The language “oxidation … in the presence of dichloroacetic acid” means that oxidation of the
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`sulfide takes place with at least some amount of DCA present in the reaction mixture but does not
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`require that DCA have any function or role. (Ex. 1044 at ¶ 22). Thus, Dr. Trost stated, “Nothing
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`in claim 1 … requires that … the dichloroacetic acid recited in claim 1 … be oxidized to
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`dichloroperacetic acid through the oxidizing agent. (Ex. 2018 at ¶ 23).
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`Pastorio’s Response: Pastorio objects to MF 16 as failing to comply with SO ¶ 121.5.2 because
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`MF 16 is not “a single…declaratory sentence”; Pastorio further objects to MF 16 as calling for
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`a legal conclusion on claim construction; otherwise, denied.
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`17. Claim 1 is not at all limited in terms of, e.g., proportion of components, time, reaction rate,
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`yield, selectivity, temperature, commercial suitability or scale. (Ex. 1044 at ¶ 24).
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`Accordingly, for example, any reaction process that produces some fipronil by oxidizing 5-amino-
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`1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthio pyrazole in the presence
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`of an oxidizing agent and DCA, and in the absence of trichloroacetic acid (TCA) and/or
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`trichloroperacetic acid (TCPA) would fall within the scope of claim 1. (Id.)
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`Pastorio’s Response: Pastorio objects to MF 17 as failing to comply with SO ¶ 121.5.2 because
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`MF 17 is not “a single…declaratory sentence”; Pastorio further objects to MF 17 as calling for
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`a legal conclusion on claim construction; otherwise, denied.
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`APP-2A-3
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`18. The POSA would understand claims 1-12 as encompassing a process in which any amount or
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`Interference No. 105,995
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`
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`yield of fipronil is produced and with any level of selectivity or lack thereof. (Ex. 1044 at ¶ 25)
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`Pastorio’s Response: Denied.
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`19. Notably, claims 1-12 do not recite or require a strong acid such as sulfuric acid. (Ex. 1044
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`at ¶ 26)
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`Pastorio’s Response: Pastorio objects to MF 19 as calling for a legal conclusion on claim
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`construction; Admitted that claims 1 – 12 of the Pastorio ʼ559 patent do not require sulfuric
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`acid; otherwise, denied.
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`20. Oxidation of heteroatoms in organic compounds such as sulfur is a common application for
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`organic peracids, and a POSA would have understood that stronger parent acids result in more
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`highly reactive peracids when treated with a peroxide. (Ex. 1044 at ¶ 28; Ex. 1009 at §7.2.1.1.;
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`Exs. 1014, 1015, 1024).
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`Pastorio’s Response: Admit that, in general, when treated with a peroxide stronger parent
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`acids will result in a peracids that are stronger oxidizing agents; otherwise, denied.
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`21. Furthermore, stronger acids such as sulfuric acid in sulfide oxidations were known to the
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`POSA, including in conjunction with the use of hydrogen peroxide. (Ex. 1044 at ¶ 31; Ex. 1016).
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`Pastorio’s Response: Denied.
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`22. In the context of the subject oxidation process, a POSA would be considering to a finite set of
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`halogenated derivatives of acetic acid derivatives as possible choices for an oxidation medium.
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`(Ex. 1044 at ¶ 92-93).
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`Pastorio’s Response: Denied.
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`23. Thus, trichloroacetic acid (TCA) is about 4.5 times mo