Paper No. __
`
`Filed on behalf of: Senior Party Levin
`
`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 PA TENT TRIAL AND APPEAL BOARD
`
`ANDREA PASTORIO
`and PAOLO BETTI
`Junior Party,
`(Patent 8,304,559)
`
`V.
`
`ANATLEVIN
`and MICHAEL GRABARNICK,
`
`Senior Party,
`(Application 13/926,3 89)
`
`Patent Interference No. 105,995 (SGL)
`(Technology Center 1600)
`
`FOURTH DECLARATION OF GORDON W. GRIBBLE, PH.D.
`
`FINCHIMICA EXHIBIT 2019
`ADAMA MAKHTESHIM v. FINCH/MICA
`CASE IPR2016-00577
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`

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`Filed on behalf of: Senior Party Levin
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`By: Gary J. Gershik
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`Registration No. 39,992
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`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
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` Paper No. _____
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`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`_______________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`_______________
`
`ANDREA PASTORIO
`and PAOLO BETTI
`Junior Party,
`(Patent 8,304,559)
`
`v.
`
`ANAT LEVIN
`and MICHAEL GRABARNICK,
`
`Senior Party,
`(Application 13/926,389)
`_______________
`
`Patent Interference No. 105,995 (SGL)
`(Technology Center 1600)
`_______________
`
`FOURTH DECLARATION OF GORDON W. GRIBBLE, PH.D.
`
`LEVIN EXHIBIT 1022
`Pastorio v. Levin
`Interference No. 105,995
`
`

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`Interference No. 105,995
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`I, Gordon W. Gribble, hereby declare as follows:
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`1.
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`I have previously provided a Declaration (Ex. 1001) in connection with the above-
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`identified interference in support of Levin Substantive Motion 1 (Paper No. 52), and
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`provided a Second Declaration (Ex. 1013) in connection with the above-identified
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`interference in support of Levin Responsive Motion 2 (Paper No. 63). The statements
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`from paragraphs 1-8 of my first Declaration and paragraphs 2-9 of my Second
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`Declaration are restated below in paragraphs 2-9. The statements from paragraphs 10-11
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`of my Second Declaration are restated below in paragraphs 10-11.
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`2.
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`I received an A.A. degree in Chemistry from San Francisco City College in 1961, a B.S.
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`in Chemistry from the University of California at Berkeley in 1963, and a Ph.D. in
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`Organic Chemistry from the University of Oregon in 1967.
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`3.
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`After receiving my Ph.D., I was a Postdoctoral Fellow at the University of California,
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`Los Angeles (1967-1968), Assistant Professor of Chemistry at Dartmouth College (1968-
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`1974), and Associate Professor of Chemistry at Dartmouth College (1974-1980). I have
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`been Professor of Chemistry at Dartmouth College since 1980. I was Chair of the
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`Department of Chemistry from 1988-1991. I was the first individual named as “The
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`Dartmouth Professor of Chemistry,” an endowed chair in the Department of Chemistry at
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`Dartmouth College, in 2005.
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`4.
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`I have significant experience in synthetic organic chemistry as well as experience in
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`sulfide oxidation. Details about my professional experience are described in my
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`curriculum vitae (Exhibit 1002).
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`2
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`Interference No. 105,995
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`5.
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`I have been informed that a patent interference (Interference No. 105,995) has been
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`declared between Senior Party Anat Levin and Michael Grabarnick (“Levin”), U.S.
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`Patent Application Serial No. 13/926,389 (Ex. 1010, as filed; Ex. 2002, as published),
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`and Junior Party Andrea Pastorio and Paolo Betti (“Pastorio”), U.S. Patent No.
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`8.304,559 (“the ‘559 patent”) (Ex. 2001).
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`6.
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`I have been retained by Cooper & Dunham LLP, the law firm representing Levin in the
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`patent interference, and am being compensated at my standard hourly rate of $400 per
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`hour and $600 per hour for deposition testimony.
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`7.
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`I have been informed that the real party in interest for Senior Party Levin is Adama
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`Makhteshim Ltd., and that the real party in interest for Junior Party Pastorio is
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`Finchimica, S.p.A. I do not have any financial interest in either Adama Makhteshim Ltd.
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`or Finchimica, S.p.A., and I do not have any financial interest in the outcome of this
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`patent interference.
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`8.
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`9.
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`I have had no contact with the Levin inventors or the Pastorio inventors.
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`My opinions provided in this declaration are as an independent technical expert.
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`10.
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`I have been informed that the ‘389 application is a continuation of U.S. Serial No.
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`13/809,327, which is a §371 national stage entry of PCT International Application No.
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`PCT/IL2011/000546, filed July 10, 2011 (“the Levin PCT application”) (Ex. 1011),
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`which claims benefit of U.S. Provisional Application No. 61/363,366, filed July 12, 2010
`
`(“the Levin priority application”) (Ex. 1012).
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`3
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`Interference No. 105,995
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`11.
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`I have been informed that the ‘559 patent (Ex. 2001) issued on November 6, 2012 from
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`U.S. Serial No. 13/498,245, which was a national stage entry of PCT International
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`Application No. PCT/IB2011/052304, filed May 6, 2011, and published as PCT
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`International Application Publication No. WO 2012/004692 on January 12, 2012 (“the
`
`Pastorio PCT”), which claims priority to Italian Patent Application No. BS2010A0118,
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`filed July 7, 2010 (Ex. 2010) (“the Pastorio priority application”).
`
`12.
`
`I have been informed that Pastorio has filed a reissue application of the ‘559 patent (Ex.
`
`2012) which includes proposed new claims 16-18.
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`13.
`
`I have been asked to review documents, identified below, which were published before
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`the July 7, 2010 filing date of the Pastorio priority application and provide my opinions
`
`on what a person having ordinary skill in the art as of July 7, 2010 would have
`
`understood from these documents. Specifically, I have asked to comment on whether
`
`Australian Patent No. AU 2010100462 A4 to Gharda (Ex. 1023) (“the ‘462 AU patent”)
`
`describes the process of Pastorio’s proposed claims 16-18. I have also been asked
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`whether a person having ordinary skill in the art would have been motivated to modify
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`the process for making Fipronil described in PCT International Application Publication
`
`No. WO 01/30760 (“the ‘760 PCT application”) (Ex. 1019) to use dichloroacetic acid
`
`(“DCA”) as a solvent in view of the teachings of the ‘760 PCT application and U.S.
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`Patent No. 6,013,761 (“the ‘761 patent) (Ex. 1024), and whether a person having
`
`ordinary skill in the art would have had a reasonable expectation of success if they were
`
`to do so. I have also been asked whether PCT International Application Publication No.
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`WO 2007/122440 (“the ‘440 PCT application”) (Ex. 2009) teaches away from using
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`DCA as a solvent in the process for making Fipronil described in the ‘760 PCT
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`application.
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`14.
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`I have also been asked to provide my opinion on whether the oxidizing agents described
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`in the ‘559 patent are representative of the genus defined by the claim term “oxidizing
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`agent” recited in Pastorio’s proposed claim 16.
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`15.
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`A person having ordinary skill in the art as of July 7, 2010 would have had (1) a
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`bachelor’s or master’s degree in chemistry or a related discipline and have at least 5 years
`
`of experience in synthetic organic chemistry, including sulfide oxidation or (2) a Ph.D.
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`degree or equivalent in organic chemistry and 2 years of experience in synthetic organic
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`chemistry, including sulfide oxidation. The knowledge of a person having ordinary skill
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`in the art as of the July 12, 2010 filing date of the Levin priority application, the May 6,
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`2011 filing date of the Pastorio PCT application, and the July 10, 2011 filing date of the
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`Levin PCT application would have been substantially the same as on the July 7, 2010
`
`filing date of the Pastorio priority application.
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`A.
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`Australian Patent No. AU 2010100462 A4 describes the process of Pastorio’s proposed
`claims 16-18
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`16.
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`Each of Pastorio’s proposed claims 16-18 recites a method for the preparation of a
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`compound having the general formula (I) “through oxidation of a compound having the
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`general formula (II) in the presence of dichloroacetic acid and of an oxidizing agent.”
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`The “oxidizing agent” is undefined in claim 16, is “selected from the group consisting of
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`benzoyl peroxides, sodium peroxides, t-butyl peroxides and hydrogen peroxide” in claim
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`17, and is hydrogen peroxide in claim 18. Ex. 2012, claims 16-18. DCA functions as a
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`solvent or co-solvent in the claimed reaction. Ex. 2001, col. 4, l. 55-60.
`5
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`

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`Interference No. 105,995
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`17.
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`Pastorio’s proposed claims 16-18 allow for the presence of a solvent in addition to DCA,
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`except that trichloroacetic acid (“TCA”) is specifically excluded from the claims. Ex.
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`2012, claims 16-18.
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`18.
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`The ‘462 AU patent disclosed a process for preparing trifluoromethylsulfinyl pyrazole
`
`derivatives, and in particular Fipronil. Ex. 1023, page 4, lines 5-9.1 The process disclosed
`
`in the ‘462 AU patent is a nine step process having steps (a)-(i). Ex. 1023, page 7, line 21
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`to page 11, line 11. The final step of the process, step (i), is an oxidation reaction in
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`which a thiopyrazole compound of formula IX, corresponding to the compound of
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`formula (II) recited in Pastorio’s claims 16-18, is oxidized to a sulfoxide of formula I,
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`corresponding to the sulfoxide of formula (I) recited in Pastorio’s claims 16-18:
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`i) oxidizing the isolated thio pyrazole compound of formula IX in a
`reaction medium comprising a oxidizing agent , a solvent system and a
`corrosion inhibitor to yield a product mixture containing trifluoromethyl
`sulfinyl pyrazole compound of formula I.
`
`Ex. 1023, page 11, lines 8-11.
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`19.
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`The ‘462 AU patent taught that “[t]he oxidizing agent is a peroxide compound selected
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`from the group consisting of hydrogen peroxide, tert-butyl hydrogen peroxide, benzoyl
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`peroxide and sodium peroxide.” Ex. 1023, page 13, lines 24-26. The ‘462 AU patent
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`further taught that “[t]ypically, the oxidizing agent is hydrogen peroxide.” Ex. 1023, page
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`14, line 1.
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`1 The ‘462 AU patent contains two sets of page numbers. I will refer to the page numbers which
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`begin on the first page of Ex. 1023.
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`Interference No. 105,995
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`20.
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`The ‘462 AU patent disclosed an embodiment in which the solvent system used in the
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`oxidation reaction is a mixture of at least two solvents selected from a group of six
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`solvents, where one of the six solvents of the group is DCA:
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`In [a] preferred embodiment of the present invention, the solvent system in
`oxidation step (i) is a mixture of at least two solvents selected from a
`group of halogenated solvents consisting of
`trifluoroacetic acid,
`trichloroacetic acid, dichloroacetic acid, chlorobenzene, dichloromethane
`and dichloroethane.
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`Ex. 1023, page 12, lines 21-24 (emphasis added).
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`21.
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`A person having ordinary skill in the art would immediately envision each of the possible
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`combinations of the six solvents described by the ‘462 AU patent because there are only
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`15 combinations of two solvents (5 of which contain DCA), 20 combinations of three
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`solvents (10 of which contain DCA), 15 combinations of four solvents (10 of which
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`contain DCA), 6 combinations of five solvents (5 of which contain DCA) and 1
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`combination of six solvents (which contains DCA).2 Thus, there are 57 combinations of
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`2 When representing the six solvents as A, B, C, D, E, and F, the combinations are as follows:
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`2 solvents: {A,B}, {A,C}, {A,D}, {A,E}, {A,F}, {B,C}, {B,D}, {B,E}, {B,F}, {C,D}, {C,E},
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`{C,F}, {D,E}, {D,F}, and {E,F}.
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`3 solvents: {A,B,C}, {A,B,D}, {A,B,E}, {A,B,F}, {A,C,D}, {A,C,E}, {A,C,F}, {A,D,E},
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`{A,D,F}, {A,E,F}, {B,C,D}, {B,C,E}, {B,C,F}, {B,D,E}, {B,D,F}, {B,E,F}, {C,D,E}, {C,D,F},
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`{C,E,F}, and {D,E,F}.
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`4 solvents: {A,B,C,D}, {A,B,C,E}, {A,B,C,F}, {A,B,D,E}, {A,B,D,F}, {A,B,E,F}, {A,C,D,E},
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`{A,C,D,F}, {A,C,E,F}, {A,D,E,F}, {B,C,D,E}, {B,C,D,F}, {B,C,E,F}, {B,D,E,F}, and
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`{C,D,E,F}.
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`Interference No. 105,995
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`solvents within the genus described by the ‘462 AU patent, 31 of which contain DCA.
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`Consequently, a person having ordinary skill in the art would have understood the ‘462
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`AU patent to describe a process for making Fipronil through oxidation of the
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`corresponding sulfide of formula (II) in the presence of DCA and hydrogen peroxide.
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`22.
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`Thus, the ‘462 AU patent describes the process of Pastorio’s proposed claims 16-18.
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`Appendix A shows where each element of Pastorio’s proposed claims 16-18 is found in
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`the ‘462 AU patent.
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`B.
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`A person having ordinary skill in the art would have been motivated by Australian
`Patent No. AU 2010100462 A4 to select DCA as a solvent when making Fipronil and
`would have had a reasonable expectation of success
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`23.
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`As noted above, the ‘462 AU patent (Ex. 1023) taught making Fipronil by oxidizing the
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`corresponding sulfide of formula (II) using a solvent system which is a “mixture of two
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`or more solvents.” Ex. 1023, page 12, lines 21-24. The ‘462 AU patent listed six solvents
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`which may be used in the solvent mixture, one of which is DCA. Ex. 1023, page 12, lines
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`21-24. A person having ordinary skill in the art would have been motivated to try each of
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`the 15 two solvent combinations because persons having ordinary skill in the art optimize
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`reactions by trying different solvents. A person having ordinary skill in the art would
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`have expected that Fipronil could be successfully made using each two solvent
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`combination because the ‘462 AU patent identified each of the six solvents as a suitable
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`{B,C,D,E,F}.
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`6 solvents: {A,B,C,D,E,F}.
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`Interference No. 105,995
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`solvent for use in the solvent mixture. The ‘462 AU patent even provided an example in
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`which Fipronil was successfully made using a solvent system containing DCA. Ex. 1023,
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`page 30, Example 17.
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`24.
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`I am not aware of any reason why a solvent mixture containing DCA and one or more
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`additional solvents selected from those listed in the ‘462 AU patent would provide a
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`result that would have been unexpected to a person having ordinary skill in the art. The
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`advantages of using DCA described in the ‘559 patent (Ex. 2001) relate to the use of
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`DCA as the sole solvent, not as a co-solvent with one or more additional solvents. See,
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`e.g., Ex. 2001 col. 5, l. 29-36. The ‘440 PCT application (Ex. 2009) had shown prior to
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`July 2010 that a solvent mixture of TCA and DCA could be used to successfully make
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`Fipronil. Ex. 2009, page 10, lines 10-25.
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`C.
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`A person having ordinary skill in the art would have motivated to use DCA as a solvent
`in the process for making Fipronil described in PCT International Application
`Publication No. WO 01/30760 and would have had a reasonable expectation of success
`
`25.
`
` PCT International Application Publication No. WO 01/30760 (“the ‘760 PCT
`
`application”) (Ex. 1019) disclosed a process for producing Fipronil and other compounds
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`of formula (I) through oxidation of a compound of formula (II) in the presence of
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`trifluoroacetic acid (“TFA”) and hydrogen peroxide. Ex. 1019, page 7, line 23 to page 8,
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`line 2; Example 1 on pages 16-17. The ‘760 PCT application reported that oxidizing a
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`compound of formula (II) to a compound of formula (I) using a mixture of TFA and
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`hydrogen peroxide “gives excellent results in terms of both selectivity and yield.” Ex.
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`1019, page 2, lines 6-8. However, TFA was known to be both expensive and corrosive.
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`Ex. 1019, page 2, lines 9-11 and page 9, lines 3-5. Thus, a person having ordinary skill in
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`Interference No. 105,995
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`the art would have been motivated to optimize the process described in the ‘760 PCT
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`application by replacing some or all of the TFA with a less expensive and/or less
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`corrosive solvent, preferably a solvent which was known to be a suitable solvent for
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`sulfide oxidation reactions.
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`26.
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`DCA is less expensive than TFA, is less corrosive than TFA, and was identified in the
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`prior art as being a suitable solvent for sulfide oxidation reactions. U.S. Patent No.
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`6,013,761 (“the ‘761 patent) (Ex. 1024) described a process for preparing polyarylene
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`sulfoxides though oxidation of the corresponding sulfide in the presence of an acid and
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`hydrogen peroxide. Ex. 1024, col. 9, claim 1. Claim 4 of the ‘761 patent taught that the
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`acid can be “trifluoroacetic acid, trichloroacetic acid or dichloroacetic acid.” Ex. 1024,
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`col. 9-10, claim 4. Examples 13-16 of the ‘761 patent described experiments in which
`
`DCA was successfully used as the solvent for the selective oxidation of polyphenylene
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`sulfide to polyphenylene sulfoxide by hydrogen peroxide. Ex. 1024, col. 7, l. 16 to col. 9,
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`l. 22. A person having ordinary skill in the art as of July 2010 would have been motivated
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`by the ‘761 patent to replace some or all of the TFA in the process of the ‘760 PCT
`
`application with DCA because such person would have expected that DCA could
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`similarly be used as a solvent for the oxidation of a sulfide of formula (II) to Fipronil.
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`Appendix B shows where each feature of Pastorio’s claims 16-18 is found in the ‘760
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`PCT application and the ‘761 patent.
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`27.
`
`A person having ordinary skill in the art would have had a reasonable expectation of
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`success when replacing some or all of the TFA in the process of the ‘760 PCT application
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`with DCA because the ‘761 patent demonstrated the suitability of DCA as an oxidation
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`solvent and identified TFA and DCA as equivalents. Ex. 1024, col. 9-10, claim 4.
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`28.
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`In my opinion, the process of Pastorio’s proposed claims 16-18 is no more than the
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`optimization of the process described in the ‘760 PCT application – the process was
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`optimized to reduce the cost of reagents and to reduce the use of a corrosive solvent. I am
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`unaware of any reason why using DCA as a co-solvent with TFA in the oxidation
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`reaction would provide a result that would have been unexpected to a person having
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`ordinary skill in the art. The advantages of using DCA described in the ‘559 patent (Ex.
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`2001) relate to the use of DCA as the sole solvent, not as a co-solvent with TFA. See,
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`e.g., Ex. 2001 col. 5, l. 29-36.
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`29.
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`I am aware that the ‘440 PCT application (Ex. 2009) states that “dichloro acetic acid is a
`
`poor medium for oxidation.” Ex. 2009, page 9, lines 17-21. However, the ‘440 PCT
`
`application does not explain why the inventors considered DCA to be a poor medium,
`
`and provided an example which used a “solvent mixture” containing 70% TCA and 30%
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`DCA . Ex. 2009, page 10, lines 10-25. Thus, the ‘440 PCT application actually shows the
`
`suitability of DCA as a solvent (or at least as a co-solvent) for the reaction.
`
`D.
`
`The peroxide containing oxidizing agents described in the ‘559 patent are not
`representative of the diverse genus defined by “oxidizing agent.”
`
`30.
`
`The ‘559 patent (Ex. 2001) describes the following oxidizing agents: “dichloroperacetic
`
`acid” (abstract); “benzoyl peroxides, sodium peroxides, t-butyl peroxides, and/or
`
`hydrogen peroxides” (col. 5, l. 37-40); “hydrogen peroxide” (col. 5, l. 42-43); “a peracid
`
`and/or a persulphate” (col. 8, l. 59-61). Each of these agents contains a peroxide (O-O)
`
`functional group. Peroxide containing oxidizing agents are only one class of oxidizing
`
`agents. Many oxidizing agents do not contain a peroxide functional group but instead
`
`contain different functional groups and function by different mechanisms. Chapter 7 of
`
`11
`
`

`

`Interference No. 105,995
`
`Modern Oxidation Methods, J.E. Backvall, ed., WILEY-VCH Verlag GmbH & Co.
`
`KGaA (2004) (Ex. 1009) at page 194, section 7.2.1 describes a few exemplary oxidizing
`
`agents having different functional groups: “[a] large number of methods are available in
`
`the literature for the oxidation of sulfides (thioethers) to sulfoxides by electrophilic
`
`reagents. These include the use of peracids, NaIO4, MnO2, CrO3, SeO2 and
`
`iodosobenzene.” None of the oxidizing agents NaIO4, MnO2, CrO3, SeO2, and
`
`iodosobenzene contain a peroxide functional group, and each contains a different
`
`functional group from the others. This short list of oxidizing agents shows that the
`
`peroxide containing oxidizing agents described by the ‘559 patent are not representative
`
`of the diverse genus defined by “oxidizing agent.”
`
`E.
`
`The ‘559 patent does not show that Pastorio possessed a process in which DCA is a co-
`solvent together with one or more additional solvents
`
`31.
`
`The ‘559 patent describes advantages of “the present invention” which purportedly result
`
`from using DCA as the sole solvent for the reaction. See Ex. 2001, col. 5, l. 29-30 (“[t]he
`
`present invention therefore allows to operate in the absence of solvents [other than
`
`DCA]”) (emphasis added); Ex. 2001, col. 8, l. 22-25 (“[a]dvantageously, the use of the
`
`oxidising agent of the present invention [dichloroperacetic acid formed from DCA]
`
`does not require the use of solvents for the reaction, making the entire process much
`
`simpler and economically advantageous in industrial applications”) (emphasis added);
`
`Ex. 2001, col. 8, lines 30-33 (“[a]dvantageously, the function performed by DCA in the
`
`method of the present invention enables economies in terms of costs of reagents, and
`
`simplification of the plant for implementing the teaching”). Each of Examples 1-3 of the
`
`1
`
`2
`
`3
`
`4
`
`5
`
`6
`
`7
`
`8
`
`9
`
`10
`
`11
`12
`
`13
`
`14
`
`15
`
`16
`
`17
`
`18
`
`19
`
`20
`
`21
`
`22
`
`12
`
`

`

`Interference No. 105,995
`
`1
`
`2
`
`3
`
`4
`
`5
`
`6
`
`7
`
`8
`
`9
`
`10
`
`11
`
`12
`
`13
`
`14
`
`15
`
`16
`
`17
`
`‘559 patent describe a reaction in which DCA is the only solvent used. Ex. 2001, col. 6, l.
`
`60 to col. 8, l. 65.
`
`32.
`
`The only solvent mixtures mentioned in the ‘559 patent are the prior art TCA/DCA and
`
`TCA/monochloroacetic acid solvent mixtures described in the ‘440 PCT application. Ex.
`
`2001, col. 2, l. 30-37. The ‘559 patent identifies drawbacks of the mixtures described in
`
`the ‘440 PCT application before describing advantages of using DCA alone. Ex. 2001,
`
`col. 2, l. 43 to col. 3, l. 3. The specification of the ‘559 does not describe any solvent
`
`mixture containing DCA and one or more solvents for use in its purported inventive
`
`oxidation process. Consequently, a person having ordinary skill in the art would not have
`
`found Pastorio to be in possession of a process in which DCA is present, in any amount,
`
`as a co-solvent together with one or more additional solvents.
`
`In signing this Fourth Declaration, I understand that the Fourth Declaration will be filed as
`
`evidence in a contested case before the Patent Trial and Appeal Board of the United States Patent
`
`and Trademark Office. I acknowledge that I may be subject to cross examination in the case and
`
`that cross examination will take place within the United States. If cross examination is required
`
`of me, I will appear for cross examination within the United States during the time allotted for
`
`cross examination.
`
`13
`
`

`

`Inte1ference No. 105,995
`
`1
`
`I hereby declare that all statements made herein of my own knowledge are true and that all
`
`2
`
`3
`
`4
`
`statements made herein on information and belief are believed to be true; and furtner that these
`
`statements were rnade . with the knowledge that willful false statements and the like so made are
`
`punishable by fme or imprisonment, or both, under Section 1001 of tide 18 of the United States
`
`5 Code, and that such willful false statements may jeopardize the validity of the above.-identified
`
`6
`
`Levin application or any patent issuing thereon.
`
`7
`
`8
`
`9 Gordon W. Gribble, Ph.D.
`
`Date
`
`14
`
`

`

`APPENDIX A: CLAIM CHART COMPARING PASTORIO’S PROPOSED CLAIMS 16-
`18 WITH AUSTRALIAN PATENT NO. AU 2010100462 A4
`
`Interference No. 105,995
`
`Claim 16
`A method for the
`preparation of the
`compound having the
`following general
`formula (I):
`
`Claim 17
`17. A method for the
`preparation of the
`compound having the
`following general
`formula (I):
`
`Claim 18
`18. A method for the
`preparation of the
`compound having the
`following general
`formula (I):
`
`wherein R1 and R2 are
`independently
`hydrogen or halogen;
`through oxidation of a
`compound having the
`general formula (II) in
`the presence of
`dichloroacetic acid and
`of an oxidizing agent:
`
`wherein R1 and R2 are
`independently
`hydrogen or halogen;
`through oxidation of a
`compound having the
`general formula (II) in
`the presence of
`dichloroacetic acid and
`of an oxidizing agent:
`
`wherein R1 and R2 are
`independently
`hydrogen or halogen;
`through oxidation of a
`compound having the
`general formula (II) in
`the presence of
`dichloroacetic acid and
`of an oxidizing agent:
`
`wherein R1 and R2 are
`defined as above, and
`
`wherein R1 and R2 are
`defined as above, and
`
`wherein R1 and R2 are
`defined as above, and
`
`‘462 AU Patent
`Page 4, lines 7-9:
`“Particularly, the
`present invention
`envisages a
`process for
`preparing 5-
`Amino-1-(2,6-
`dichloro-4-
`trifluoromethyl
`phenyl)-3-cyano-
`4-trifluoromethyl
`sulfinyl pyrazole
`also known as
`Fipronil.”
`
`Page 11, lines 9-
`11:
`“i) oxidizing the
`isolated thio
`pyrazole
`compound of
`formula IX in a
`reaction medium
`comprising a
`oxidizing agent , a
`solvent system and
`a corrosion
`inhibitor to yield a
`product mixture
`containing
`trifluoromethyl
`sulfinyl pyrazole
`compound of
`formula I.”
`
`Page 12, lines 21-
`24:
`“In preferred
`embodiment of the
`present invention,
`
`APP-A-1
`
`

`

`Claim 16
`
`Claim 17
`
`Claim 18
`
`wherein the oxidizing
`agent is hydrogen
`peroxide, and
`
`
`
`wherein the oxidation
`is conducted in the
`absence of
`trichloroacetic and/or
`trichloroperacetic acid.
`
`where the oxidizing
`agent is selected from
`the group consisting of
`benzoyl peroxide,
`sodium peroxides,
`t-butyl peroxides and
`hydrogen peroxide, and
`wherein the oxidation
`is conducted in the
`absence of
`trichloroacetic and/or
`trichloroperacetic acid.
`
`Interference No. 105,995
`
`‘462 AU Patent
`the solvent system
`in oxidation step
`(i) is a mixture of
`at least two
`solvents selected
`from a group of
`halogenated
`solvents consisting
`of
`trifluoroaceticacid,
`trichloroaceticacid,
`dichloroaceticacid,
`chlorobenzene,
`dichloromethane
`and
`dichloroethane.”
`Page 11, line 1:
`“Typically, the
`oxidizing agent is
`hydrogen
`peroxide.”
`
`wherein the oxidation
`is conducted in the
`absence of
`trichloroacetic and/or
`trichloroperacetic acid.
`
`15 combinations
`of 2, 3, 4, or 5
`solvents from the
`genus of the ‘462
`AU patent contain
`DCA but not TCA
`
`APP-A-2
`
`

`

`APPENDIX B: CLAIM CHART COMPARING PASTORIO’S PROPOSED CLAIMS 16-
`18 WITH PCT INTERNATIONAL APPLICATION PUBLICATION NO. WO 01/30760
`AND U.S. PATENT NO. 6,013,761
`
`Interference No. 105,995
`
`Claim 16
`
`Claim 17
`
`Claim 18
`
`A method for the
`preparation of the
`compound having the
`following general
`formula (I):
`
`17. A method for the
`preparation of the
`compound having the
`following general
`formula (I):
`
`18. A method for the
`preparation of the
`compound having the
`following general
`formula (I):
`
`wherein R1 and R2 are
`independently
`hydrogen or halogen;
`through oxidation of a
`compound having the
`general formula (II) in
`the presence of
`dichloroacetic acid and
`of an oxidizing agent:
`
`wherein R1 and R2 are
`independently
`hydrogen or halogen;
`through oxidation of a
`compound having the
`general formula (II) in
`the presence of
`dichloroacetic acid and
`of an oxidizing agent:
`
`wherein R1 and R2 are
`independently
`hydrogen or halogen;
`through oxidation of a
`compound having the
`general formula (II) in
`the presence of
`dichloroacetic acid and
`of an oxidizing agent:
`
`wherein R1 and R2 are
`defined as above, and
`
`wherein R1 and R2 are
`defined as above, and
`
`wherein R1 and R2 are
`defined as above, and
`
`‘760 PCT and ‘761
`Patent
`‘760 PCT, page 16,
`lines 24-25:
`Example 1
`“Preparation of 5-amino-
`1-(2,6-dichloro-4-
`trifluoromethylphenyl)-
`3-cyano-4-trifluoro-
`methylsulphinylpyrazole
`[Fipronil]”
`
`‘760 PCT, page 16,
`lines 26-28:
`“Trifluoroacetic acid
`(1660g, 14.5mol) was
`added to a stirred
`solution of 5-amino-1-
`(2,6-dichloro-4-
`trifluoromethylphenyl)-
`3-cyano-
`4-trifluoro-
`methylthiopyrazole [of
`formula (II)] (436g,
`l.03mol) and boric acid
`(5g, 0.08mol) in a glass
`reactor at 12°C.”
`
`‘761 patent, claim 4:
`“wherein an acid of the
`formula R1-CR2R3-
`COOH in the form of
`concentrated
`
`APP-B-1
`
`

`

`Interference No. 105,995
`
`Claim 16
`
`Claim 17
`
`Claim 18
`
`
`
`wherein the oxidation
`is conducted in the
`absence of
`trichloroacetic and/or
`trichloroperacetic acid.
`
`where the oxidizing
`agent is selected from
`the group consisting of
`benzoyl peroxide,
`sodium peroxides,
`t-butyl peroxides and
`hydrogen peroxide, and
`wherein the oxidation
`is conducted in the
`absence of
`trichloroacetic and/or
`trichloroperacetic acid.
`
`wherein the oxidizing
`agent is hydrogen
`peroxide, and
`
`wherein the oxidation
`is conducted in the
`absence of
`trichloroacetic and/or
`trichloroperacetic acid.
`
`‘760 PCT and ‘761
`Patent
`trifluoroacetic acid,
`trichloroacetic acid or
`dichloroacetic acid is
`used.”
`‘760 PCT, page 16,
`lines 29-30:
`“Hydrogen peroxide
`(131.5g of 35%w/w,
`l.35mol) was added
`over 2 hours.”
`‘760 PCT, page 16,
`line 24 to page 17,
`line 23:
`the oxidation is
`conducted in the
`absence of
`trichloroacetic and/or
`trichloroperacetic acid.
`
`APP-A-2
`
`