PaperNo. __
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`Filed on behalf of: Junior Party Levin
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`By:
`
`Gary J. Gershik
`Registration No. 39,992
`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
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`ANATLEVIN
`and MICHAEL GRABARNICK,
`Junior Party,
`(Application 13/926,389)
`
`v.
`ANDREA PASTORIO
`and PAOLO BETTI
`Senior Party,
`(Patent 8,304,559)
`
`Patent Interference No. 105,995 (SGL)
`(Technology Center 1600)
`
`LEVIN MOTION NO. 4
`(Judgment Based on Invalidity of the Pastorio Claims over the Prior Art)
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`1
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`FINCHIMICA EXHIBIT 2008
`ADAMA MAKHTESHIM v. FINCHIMICA
`CASE IPR2016-00577
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`Interference No. 105,995
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`TABLE OF CONTENTS
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`APPENDICES ................................................................................................................................ 1
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`REQUEST FOR RELIEF ............................................................................................................... 1
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`REAL PARTY IN INTEREST ....................................................................................................... 1
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`REASONS THAT THE RELIEF SHOULD BE GRANTED ........................................................ 1
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`INTRODUCTORY STATEMENT ................................................................................................ 1
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`APPLICABLE LAW ...................................................................................................................... 2
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`ARGUMENT .................................................................................................................................. 5
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`Level of Ordinary Skill ................................................................................................................... 6
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`Claim Construction ......................................................................................................................... 6
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`Secondary Considerations Point to Obviousness .......................................................................... 13
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`APPENDIX 1 (LIST OF EXHIBITS RELIED UPON IN LEVIN MOTION 4) ......................... 15
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`APPENDIX 2 (STATEMENT OF MATERIAL FACTS IN SUPPORT OF MOTION) ............ 16
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`The Pastorio Claimed Invention: .................................................................................................. 16
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`Background of the Art and the Claimed Invention: ...................................................................... 16
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`Oxidations to Produce Fipronil With Halogenated Acetic Acid Derivatives Were Known ......... 19
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`APPENDIX 3 ................................................................................................................................ 26
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`CERTIFICATE OF SERVICE ..................................................................................................... 34
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`TABLE OF AUTHORITIES
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`Cases
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`Allergan v. Sandoz
`726 F.3d 1286 (Fed. Cir. 2013)....................................................................................................... 4
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`Allergan, Inc. v. Apotex Inc.
`754 F.3d 952 (Fed. Cir. 2014)......................................................................................................... 4
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`Ex Parte Ang
`2014 WL 880141, Appeal No. 2011-013423 (P.T.A.B. Mar. 4, 2014) ........................................ 11
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`Aventis v. Lupin
`499 F.3d 1293 (Fed. Cir. 2007)....................................................................................................... 4
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`Bayer Schering Pharma AG v. Barr Labs
`575 F.3d 1341 (Fed. Cir. 2009)....................................................................................................... 4
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`Daiichi Sankyo Co., Ltd. v. Apotex, Inc.
`501 F.3d 1254 (Fed. Cir. 2007)..................................................................................................... 10
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`In re Dillon
`919 F.2d 688 (Fed. Cir. 1990)................................................................................................. 3, 5, 9
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`Ecolochem v. S. Cal. Edison Co.
`227 F.3d 1361, 56 USPQ2d 1065 (Fed. Cir. 2000) .................................................................. 5, 14
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`Graham v. John Deere Co.
`383 U.S. 1 (1966) ............................................................................................................................ 3
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`In re Gurley
`27 F.3d 551, 31 USPQ2d 1130 (Fed. Cir. 1994) .............................................................. 2, 5, 8, 12
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`KSR Int’l v. Teleflex Inc.
`550 U.S. 398 (2007) ................................................................................................................ 2, 3, 4
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`Lamont v. Berguer
`7 USPQ2d 1580 (B.P.A.I. 1988)..................................................................................................... 2
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`In re Mouttet
`686 F.3d 1322 (Fed. Cir. 2012); ................................................................................................... 11
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`In re Payne
`606 F.2d 303 (CCPA 1979) ............................................................................................................ 4
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`Pfizer Inc. v. Apotex, Inc.
`480 F.3d 1348 (Fed. Cir. 2007)............................................................................................. 2, 4, 12
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`Ex Parte Xue
`2014 WL 5590756, Appeal No. 2012-007667 (P.T.A.B. Oct. 10, 2014) .................................... 11
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`Trustees of Columbia University in City of New York v. Illumina, Inc.,
`Fed. Appx. ----, 2015 WL 4385761 (Fed. Cir. July 17, 2015) ........................................................ 5
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`Velander v. Garner
`348 F.3d 1359 (Fed. Cir. 2003)....................................................................................................... 2
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`Whitserve, LLC v. Computer Packages, Inc.
`694 F.3d 10 (Fed. Cir. 2012)........................................................................................................... 3
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`Wm. Wrigley Jr. Co. v. Cadbury Adams USA LLC
`683 F.3d 1356 (Fed. Cir. 2012)..................................................................................................... 10
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`In re Zletz
`893 F.2d 319 (Fed. Cir. 1989)......................................................................................................... 3
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`Statutes and Rules
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`35 USC § 102(b) ......................................................................................................................... 1, 7
`35 USC § 103(a) ......................................................................................................................... 1, 9
`35 USC § 282 .................................................................................................................................. 2
`37 CFR § 1.637(a)........................................................................................................................... 2
`37 CFR §§ 1.601(f) ......................................................................................................................... 3
`37 CFR §§ 1.601(n) .................................................................................................................. 3, 16
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`APPENDICES
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`Attached to this Motion are the following three Appendices:
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`1. Appendix 1: List of exhibits relied upon in support of this motion;
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`2. Appendix 2: Statement of material facts in support of this motion; and
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`3. Appendix 3: Claim Chart for Claims 1-12 of US Pat. No. 8,304,559 B2.
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`REQUEST FOR RELIEF
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`
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`Levin moves for judgment against Pastorio on the ground of invalidity of all Pastorio
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`claims (claims 1-12) over the prior art.
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`REAL PARTY IN INTEREST
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`Adama Makhteshim Ltd.
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`REASONS THAT THE RELIEF SHOULD BE GRANTED
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`Relief should be granted at least because:
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`1. Claims 1-12 of Party Pastorio are invalid under 35 USC § 102(b) over WO 2007/122440
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`A1 (“WO ‘440”).
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`2. Claims 1-12 of Party Pastorio are invalid under 35 USC § 103(a) over WO ‘440.1
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`Introductory Statement
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`1 With reference to the Order – Authorizing Motion (Paper 155) of August 4, 2015, Party Levin
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`would like to clarify a statement regarding the second proposed motion. Levin indicated that
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`because all of the elements of Pastorio’s claims can be found in WO ‘440, the other references
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`merely represent the state of the art and knowledge of a person of ordinary skill in the art.
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`This case concerns a simple and well-known oxidation reaction that has been used for many
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`years to produce the pesticide fipronil. Pastorio is claiming the well-known oxidation reaction
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`when it is conducted in the presence of dichloroacetic acid (DCA). However, this is not new.
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`Dichloroacetic acid (DCA) is a known halogenated derivative of acetic acid. DCA is analogous
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`with other known halogenated derivatives of acetic acid, trichloroacetic acid (TCA) and
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`trifluoroacetic acid (TFA). DCA, TCA and TFA were known to have analogous acid properties
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`and each was known to be useful in a sulfur oxidation reaction. The common sense policies
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`embodied in KSR and Pfizer v. Apotex dictate that the selection of DCA from within this small
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`group of candidate acids for a simple chemical oxidation reaction was within the ordinary skill in
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`the art. DCA is a slightly weaker acid than TCA and TFA but a known or obvious composition
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`does not become patentable simply because it is described in the art as somewhat inferior for the
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`same use. The claims recite no additional limitations to support patentability, and all Pastorio
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`claims have been designated to correspond to the Count.
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`APPLICABLE LAW
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`A known or obvious composition does not become patentable simply because it has been
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`described as somewhat inferior to some other product for the same use. In re Gurley, 27 F.3d 551,
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`554, 31 USPQ2d 1130, 1132 (Fed. Cir. 1994).
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`A party filing a motion in an interference has the burden of proof, by a preponderance of
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`the evidence, to show that is entitled to the relief sought in the motion. 37 CFR § 1.637(a);
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`Velander v. Garner, 348 F.3d 1359, 1370 (Fed. Cir. 2003). However, the presumption of validity
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`under 35 USC § 282 does not apply to patent claims involved in an interference. Lamont v.
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`Berguer, 7 USPQ2d 1580, 1582 (B.P.A.I. 1988).
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`In the context of patent examination and interference practice, the claims of an involved
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`patent and interference counts are to be given their broadest reasonable interpretation possible. In
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`re Zletz, 893 F.2d 319 (Fed. Cir. 1989). Claims corresponding to the count are directed to the
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`same patentable invention. 37 CFR §§ 1.601(f), (n).
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`A claim is anticipated if each and every element as set forth in the claim is found, either
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`expressly or inherently, in a single prior art reference. Whitserve, LLC v. Computer Packages,
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`Inc., 694 F.3d 10, 21 (Fed. Cir. 2012).
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`With respect to obviousness, the Supreme Court in KSR reaffirmed The Graham
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`framework for determining obviousness, while requiring a more flexible, common sense analysis.
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`KSR Int’l v. Teleflex Inc., 550 U.S. 398 (2007); Graham v. John Deere Co., 383 U.S. 1 (1966).
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`Thus, a proper analysis involves (a) determining the scope and content of the prior art, (b)
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`ascertaining the differences between the claimed invention and the prior art, (c) resolving the level
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`of ordinary skill in the pertinent art, and (d) considering any objective indicia of nonobviousness.
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`The KSR Court rejected a rigid application of the teaching-suggestion-motivation test in favor of
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`more flexible approach based on its precedent that the combination of familiar elements according
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`to known methods is obvious when it does no more than yield predictable results. KSR, supra, at
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`415-16.
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`One rationale supporting a finding obviousness is simple substitution of one known
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`element for another to obtain predictable results; another is the “obvious to try” rationale –
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`choosing from a finite number of identified, predictable solutions with a reasonable expectation of
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`success. When chemical compounds have very similar structures motivation of one skilled in the
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`art to make or use a claimed compound is coupled with the expectation that compounds of similar
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`structure will have similar properties. In re Dillon, 919 F.2d 688, 692-93 (Fed. Cir. 1991); In re
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`Payne, 606 F.2d 303, 313 (CCPA 1979); Daiichi Sankyo Co., Ltd. v. Apotex, Inc., 501 F.3d 1254,
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`1258-59 (Fed. Cir. 2007).
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`In Pfizer Inc. v. Apotex, Inc., 480 F.3d 1348 (Fed. Cir. 2007), the court found both
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`motivation and reasonable expectation of success where the prior art contained only a finite
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`number of salts to be tested. Thus, the claims to one of the salt forms were invalid even under a
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`clear and convincing standard. In Bayer Schering Pharma AG v. Barr Labs, 575 F.3d 1341 (Fed.
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`Cir. 2009), the prior art focused the skilled artisan toward a finite number of predictable solutions,
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`also rendering the claims obvious.
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`While alleged unpredictability can be relevant to obviousness, it can be overcome by
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`simply establishing that there was a reasonable expectation of success. Allergan v. Sandoz, 726
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`F.3d 1286, 1292 (Fed. Cir. 2013). Any objective evidence of non-obviousness must be
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`commensurate in scope with the claims which the evidence is offered to support. Allergan, Inc. v.
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`Apotex Inc., 754 F.3d 952, 965 (Fed. Cir. 2014).
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`Accordingly, rigid application of the teaching-suggestion-motivation test is not
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`appropriate, especially where there are a finite number of reasonably available options and a
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`reasonable expectation of success. Aventis v. Lupin, 499 F.3d 1293 (Fed. Cir. 2007). The Federal
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`Circuit pointed out that “[r]equiring an explicit teaching to purify the 5(S) stereoisomer from a
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`mixture in which it is the active ingredient is precisely the sort of rigid application of the TSM test
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`that was criticized in KSR.” Id. at 1301. In the chemical arts, the Court noted that it has long been
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`held that “structural similarity between claimed and prior art subject matter, proved by combining
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`references or otherwise, where the prior art gives reason or motivation to make the claimed
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`compositions, creates a prima facie case of obviousness.” Id. (citation omitted). The Federal
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`Circuit explained that the necessary “reason or motivation” may be established by showing that
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`“the claimed and prior art compounds possess a ‘sufficiently close relationship . . . to create an
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`expectation,’ in light of the totality of the prior art, that the new compound will have ‘similar
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`properties’ to the old.” Id. (quoting In re Dillon, 919 F.2d 688, 692 (Fed. Cir. 1990) (en banc)).
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`In In re Gurley, supra, the applicant claimed an epoxy-based printed circuit material. 27
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`F.3d at 552. The prior art reference described a similar material comprising a fibrous substrate
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`impregnated with a polyester-imide resin instead of epoxy. The nature of the resin was the only
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`significant difference from the prior art. However, epoxy was also disclosed in the reference as
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`known for the same use, albeit as inferior. Id. at 553. Because the reference taught that epoxy
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`was usable, albeit inferior, the applicant was found to not have made a patentable contribution. Id.
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`Finally, simultaneous invention occurring within a short space of time from the date of
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`invention is strong evidence of what constitutes the level of ordinary skill in the art rather than
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`inventiveness. Trustees of Columbia University in City of New York v. Illumina, Inc., ---
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`Fed.Appx. ----, 2015 WL 4385761, *11-*12 (Fed. Cir. July 17, 2015); Ecolochem v. S. Cal. Edison
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`Co., 227 F.3d 1361, 1379, 56 USPQ2d 1065 (Fed. Cir. 2000).
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`
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`ARGUMENT
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`All of Pastorio claims 1-12 have been designated as corresponding to the count.
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`
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`Background of the Claimed Invention
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`Fipronil
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`is a pesticide whose chemical name
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`is 5-amino-1-(2,6-dichloro-4-
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`trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl pyrazole. The Pastorio involved ‘559
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`patent pertains primarily to the oxidation of a precursor sulfide, 5-amino-1-(2,6-dichloro-4-
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`trifluoromethylphenyl)-3-cyano-4-trifluoromethylthio pyrazole (“Compound 420”), to obtain
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`fipronil.
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`It was known in the art to oxidize Compound 420 by various methods, including using
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`peracids derived from acetic acid derivatives, in particular halogenated acetic acid derivatives.
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`(Ex. 2001 at cols. 1-3; Ex. 2009 at p. 1, ll. 4-19).
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`The ‘559 patent claims the oxidation of 420 in the presence of dichloroacetic acid (DCA)
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`and an oxidizing agent. The application that issued as the ‘559 patent was given a first action
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`allowance. The examiner’s Reasons for Allowance stated that WO 2007/122440 was considered
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`to be the closest prior art, and “[a] person of ordinary skill in the art would not have expected that
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`making modifications would retain identical activity as disclosed in the prior art.” Pastorio claims
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`1-12 do not require “identical activity” and are, in fact, much broader in scope.
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`Level of Ordinary Skill
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`A person having ordinary skill in the art (POSA) would have had (1) a bachelor’s or
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`master’s degree in chemistry or a related discipline and have at least five years of experience in
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`synthetic organic chemistry, including sulfide oxidation or (2) a Ph.D. degree or equivalent in
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`organic chemistry and two years of experience in synthetic organic chemistry, including sulfide
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`oxidation. (Fact No. 12; Ex. 1044 at ¶ 11).
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`Claim Construction
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`The language of the ‘559 patent claim 1 is set forth in Appendix 3. The term “in the
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`presence of [DCA]” in claim 1 means that oxidation takes place with at least some amount of DCA
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`present. The claim does not require that DCA perform any specified function or role in the
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`oxidation. (Fact. No. 16; Ex. 1044 at ¶ 22).
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`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. (Fact. No. 17; Ex. 1044 at ¶ 24).
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`Accordingly, for example, any oxidation of Compound 420 in the presence of any amount of any
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`oxidant, DCA, and any additional materials, that produces any amount of fipronil would fall within
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`claim 1 as long as trichloroacetic acid (TCA) and/or trichloroperacetic acid TCPA are not present.
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`(Id.)
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`Claims 1-12 reads on reactions that produce fipronil in any amount and with any reaction
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`by-products, and does not require a strong acid such as sulfuric acid. (Fact Nos. 18-19; Ex. 1044
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`at ¶¶ 25-26)
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`Pastorio Claim 1-12 are Anticipated under 35 USC § 102(b) by WO ‘440
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`WO ‘440, which was published November 1, 2007, is available as 35 USC § 102(b) prior
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`art to Pastorio claims 1-12. WO ‘440 is directed to preparing fipronil and close analogs thereof
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`and discloses all of the limitations of claims 1-10. The features of claims 11 and 12 would have
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`been immediately apparent to a POSA from the disclosure of WO ‘440. See claim chart for
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`claims 1-12 (Appendix 3); Ex. 1044 at ¶¶ 81-83.
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`Example 1 (p. 10) of WO ‘440 discloses the oxidation of Compound 420 to fipronil in the
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`presence of DCA, TCA, and hydrogen peroxide. (Ex. 2009). Accordingly, each and every
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`limitation of Pastorio claim 1 is present in Example 1, except for the proviso excluding TCA and/or
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`TCPA. Ex. 1044 at ¶ 84. The only issue remaining to establish anticipation is whether another
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`portion of WO ‘440 discloses the oxidation reaction “in the absence of trichloroacetic acid and/or
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`trichloroperacetic acid.” It does.
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`WO ‘440 also discloses on page 9 that DCA is a poor medium for the oxidation reaction
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`that produces fipronil - thus disclosing that DCA is nevertheless an oxidation medium on its own
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`and in its own right. Page 9 of WO ‘440 contains the following statement:
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`“For example, the preferred melting point depressant dichloro acetic acid is a poor
`medium for oxidation and the purpose of its addition is only to sufficiently depress
`the melting point of trichlor acetic acid to facilitate ease of processing.”
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`(Ex. 2009). The disclosure that DCA without TCA is a “poor medium” is a disclosure that DCA
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`can be used alone as a medium to oxidize Compound 420 to fipronil. A POSA knew that DCA,
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`while a weaker acid than TCA, is nonetheless a strong acid in its own right, being about 2,900
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`times more acidic than acetic acid. (Ex. 1044 at ¶¶ 34, 35, 97). Given their broadest reasonable
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`interpretation, claims 1-12 contain no limitation with regard to superiority or inferiority of the
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`oxidation reaction; indeed, Pastorio has admitted that superior results would be obtained if sulfuric
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`acid is added to the reaction of claims 1-12 (Paper 25 at p. 5, ll. 13-22, p. 8, ll. 3-6 and 17-20)
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`and has disclaimed claims 13-15 which recited embodiments that could provide such superior
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`results. (Paper 26). To the extent that DCA may be a “poor medium” for the oxidation reaction,
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`that is exactly what is encompassed by Pastorio’s claims 1-12. See In re Gurley, supra.
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`Accordingly, each and every limitation of Pastorio claims 1-10 are disclosed in WO ‘440,
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`and the features recited in claims 11 and 12 would have been immediately apparent to a POSA
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`from the disclosure of WO ‘440.
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`Pastorio Claims 1-12 are invalid under 35 USC § 103(a) over WO ‘440
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`Fipronil production by oxidation of its sulfide precursor was well known before 2010. (Ex.
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`2001, col. 1, l. 60 to col. 2, l. 42; Ex. 2009; pp. 1-5). The sulfide precursor of fipronil, 5-amino-
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`1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylthio pyrazole, also referred to
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`as “compound 420” or “420” by Levin and as the “sulphide” by Pastorio, contains a sulfide group
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`which upon oxidation becomes a sulfoxide group; with the sulfoxide group, the compound is
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`fipronil. (Ex. 2001; Ex. 1044 at ¶ 14).
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`The oxidation reaction turning sulfides to sulfoxides is a general and widely known
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`reaction (Ex. 1044 at ¶ 14). In the context of making fipronil, commercially viable versions of
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`the reaction have been reported using a mixture of TCA and DCA (Ex. 2001 at col. 2, l. 21-42;
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`Ex. 2009), and using TFA (Ex. 2001 at col. 1, l. 66 to col. 2, l. 20; Ex. 1019). Each of these
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`versions of the oxidation reaction has its own advantages and disadvantages (Ex. 2001 at cols. 1-
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`3; Ex. 1044 at ¶¶ 34-35, 37-39, 46, 50, 55, 57-60, 62-66, 68-70, 72).
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`TFA, TCA and DCA are all halogenated derivatives of acetic acid. Each differs from acetic
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`acid by containing one or more halogen atoms instead of certain hydrogen atoms in acetic acid.
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`The replacement of one or more hydrogen atoms in acetic acid with a halogen, e.g. chlorine of
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`fluorine, results in an acid that is more acidic than acetic acid. (Ex. 1044 at ¶ 32). A property of
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`Interference No. 105,995
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`acetic acid and each of TFA, TCA and DCA is that each can form a corresponding peracid when
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`mixed with hydrogen peroxide. (Ex. 1044 at 32). Thus, in the presence of hydrogen peroxide,
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`TFA forms trifluoroperacetic acid (TFPA), TCA forms trichloroperacetic acid (TCPA), and DCA
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`forms dichloroperacetic acid (DCPA) (Ex. 2001, col. 2, ll. 1-3 and 21-27, and col. 2, l. 65-col. 3,
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`l. 3; Ex. 1044 at ¶ 32). The oxidation of the sulfide precursor into fipronil can proceed through
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`oxidation by the peracid. (Ex. 1044 at ¶ 32)
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`WO ‘440 reported a commercially viable oxidation of the sulfide precursor into fipronil
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`using a mixture of 70-80% TCA and 30-20% DCA together with hydrogen peroxide (Ex. 2009 at
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`pp. 12-14, claim 9, including claims 1-8 on which it may depend; Ex. 1044 at ¶ 70). Pastorio
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`claims 1-12 differ from the disclosure of WO ‘440 by excluding the use of TCA and/or TCPA
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`during the oxidation process.
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`TCA, however, was known to be solid at room temperature (requiring a co-solvent), and
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`was known to also be corrosive and expensive. (Ex. 1044 at ¶¶ 37-38, 57). Therefore, a POSA
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`reading WO ‘440 would be motivated to try the oxidation reaction in the absence of TCA and/or
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`its peracid, TCPA, as recited by Pastorio Claims 1-12. The POSA would have been motivated to
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`try the oxidation reaction in the absence of TCA and/or TCPA, as recited by Pastorio Claims 1-
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`12, simply to find an alternative process. Wm. Wrigley Jr. Co. v. Cadbury Adams USA LLC, 683
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`F.3d 1356, 1365 (Fed. Cir. 2012) (obvious to use alternative cooling agent); Daiichi Sankyo Co.,
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`Ltd. v. Apotex, Inc., 501 F.3d 1254, 1258-59 (Fed. Cir. 2007) (obvious to use alternative antibiotic
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`in the same family); In re Dillon, 919 F.2d 688, 692 (Fed. Cir. 1990) (obvious to use alternative,
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`closely related ester in fuel composition where it was known to use both types a similar type of
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`chemical reaction.)
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`Interference No. 105,995
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`The POSA would have expected to produce fipronil by the process that excluded TCA
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`and/or TCPA because TCA and/or TCPA was known to not be required for producing fipronil.
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`For example, fipronil was known to be successfully produced by a process using TFA or a process
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`using 3-chlorobenzine, in both cases without TCA and/or TCPA. (Ex. 1044 at ¶ 89; Ex. 2001 at
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`col. 1, ll. 23-67). Thus, substitution of TCA in the process of WO ‘440 by, e.g. TFA, would have
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`been expected by a POSA to result in a process that successfully produced fipronil. (Ex. 1044 at
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`¶ 90). Pastorio claims 1-12 read on a process with such substitution. (Ex. 1044 at ¶ 91).
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`Separately, the POSA would have expected to produce fipronil by the oxidation reaction
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`that merely excluded TCA and/or TCPA without substituting it by anything. DCA is in its own
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`right a fairly acidic material. (Ex. 1044 at ¶ 97). A POSA was aware that DCA, like TFA and
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`TCA, also forms its corresponding peracid, and has itself been used to oxidize sulfides to form
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`sulfoxides such as fipronil. (Ex. 1044 at ¶ 32). A POSA was aware that DCA is a less acidic
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`alternative to TCA and TFA, and that all three were reported as alternatives of each other for use
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`in oxidation reactions to prepare sulfoxides by oxidation of sulfides. (Ex. 1044 at ¶ 45-46). The
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`fact that DCA is less acidic than TFA or TCA does not change the fact that it was known to be
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`acidic enough to successfully oxidize sulfides to sulfoxides. (Id.) Indeed, WO ‘440 expressly
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`taught that DCA is acidic enough to successfully oxidize at least some of the sulfide precursor to
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`fipronil: “dichloro acetic acid is a poor medium for oxidation….” (Ex. 2009 at p. 9, ll. 15-23; Ex.
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`1044 at ¶ 74) Pastorio claims 1-12 read on a process making fipronil even if the process uses a
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`poor medium for oxidation.
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`Disclosed inferiority does not negate a showing of obviousness. In re Mouttet, 686 F.3d
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`1322, 1333-1334 (Fed. Cir. 2012); Ex Parte Xue, 2014 WL 5590756 at *2, Appeal No. 2012-
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`007667 (P.T.A.B. Oct. 10, 2014) (“a disclosure that larger adsorbent granules have lower filtering
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`Interference No. 105,995
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`efficiency does not suggest such granules are unlikely to work . . . A known system . . . does not
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`become patentable simply because it has been described as somewhat inferior to some other
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`product for the same use.”) (citations and internal marks omitted); Ex Parte Ang, 2014 WL 880141
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`at *2-*3, Appeal No. 2011-013423 (P.T.A.B. Mar. 4, 2014).
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`Of course a POSA was not handicapped with the use of only DCA and hydrogen peroxide
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`in the oxidation process. As Pastorio has admitted, the POSA was well aware that the addition of
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`a strong acid, e.g. sulfuric acid, was conventional in the art for the purpose of speeding up chemical
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`reactions. (Ex. 1017, at 46:22-24). Knowing that DCA is not as strong as TFA or TCA, and that
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`it “is a poor medium” for the oxidation reaction producing fipronil, the POSA would have sought
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`to make DCA a stronger oxidizing agent. (Ex. 1044 at ¶ 80). Pastorio has also admitted that a
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`POSA would have known that the addition of a sulfuric acid would make DCA a considerably
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`stronger oxidizing agent. (Ex. 2003 at ¶ 37; Paper 25 at 8:9-16). Thus, merely conventional
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`skill and design choice would have led the POSA to add a strong acid, e.g. sulfuric acid, in place
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`of the TCA in the process of WO ‘440, for the purpose of accelerating the oxidation. (Ex. 1044
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`at ¶ 80). Pastorio claims 1-12 read on such process as well.
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`This case is on all fours with Pfizer v. Apotex but with easier facts. The skilled artisan
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`performing an oxidation of Compound 420 would look to the halogenated acetic acid derivatives.
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`However, there were very few choices. (Ex. 1044 at ¶¶ 53-56, 92). Of the possibilities, the
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`fluorinated acids were known to have substantial disadvantages. (Ex. 1044 at ¶¶ 36, 38, 59, 94-
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`95). TFA was known to be highly corrosive and expensive, while TCA was known to be solid at
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`room temperature. (Ex. 1044 at ¶¶ 37-38, 57, 96). DCA is a convenient liquid and although
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`slightly less acidic, it would have been obvious to use a strong acid such as sulfuric acid to
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`compensate. (Ex. 1044 at ¶¶ 58, 60, 80, 88, 97, 98). DCA was a well-known medium for oxidation
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`Interference No. 105,995
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`and provided the advantages of safety, lower cost, and good acid strength. (Ex. 1044 at ¶¶ 48, 87,
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`98). It would have been obvious try DCA with confidence in success because DCA is known for
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`this purpose. (Ex. 1044 at ¶¶ 74, 78-79, 85-90). Claims 1-12 do not require any level of reaction
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`efficiency.
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`Structurally, TCA and DCA differ by only the replacement of one hydrogen atom with a
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`chlorine. Despite this difference the compounds do work for the same purpose and are both used
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`as such. (Ex. 1044 at ¶ 98).
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`Sulfide oxidation is not an unpredictable art. (Ex. 1044 at ¶ 40). Although there may be
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`some variations in outcome, the skilled artisan would reasonably expect fipronil to form from the
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`oxidation of Compound 420 in the presence of DCA and hydrogen peroxide. Just as in Gurley,
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`supra, a reference does not “teach away” merely because it discloses an inferior method that is
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`then claimed.
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`Secondary Considerations Point to Obviousness
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`Finally, the scope of Pastorio claims 1-12 is broad. (Paper 144 at p. 17, ll. 15-18).
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`Consequently, Levin is unaware of any objective indicia of unobviousness that would be
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`commensurate in scope with Pastorio claims 1-12. Moreover, the data in the Examples of the
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`Pastorio ‘559 patent is insufficient to show that the purported results were actually obtained.
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`(Paper 144 at p. 11, lines 2-11). Thus, Pastorio has nei