Filed on behalf of: Senior Party P ASTORIO
`
`PaperNo. __
`
`Date filed: October 6, 2015
`
`By:
`
`E. Anthony Figg, Esq.- Lead Counsel
`R. Danny Huntington, Esq.- Backup Counsel
`ROTHWELL, FIGG, ERNST & MANBECK, P.C.
`607 14th St., N.W., Suite 800
`Washington, DC 20005
`efigg@rfem.com
`dhuntington@rfem.com
`Main Telephone: (202) 783-6040
`Main Facsimile: (202) 783-6031
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`PATENT TRIAL AND APPEAL BOARD
`
`ANATLEVIN
`and MICHAEL GRABARNICK,
`Junior Patty,
`(Application 13/926,389)
`
`v.
`
`ANDREA PASTORIO
`and PAOLO BETTI
`Senior Party,
`(Patent 8,304,559)
`
`Patent Interference No. I 05,995 (SGL)
`(Technology Center 1600)
`
`PASTORIO OPPOSITION 4
`
`FINCHIMICA EXHIBIT 2010
`ADAMA MAKHTESHIM v. FJNCHIMICA
`CASE IPR2016-00577
`
`

`
`TABLE OF CONTENTS
`TABLE OF CONTENTS
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`I. PRECISE RELIEF REQUESTED .......................................................................................... 1
`I.
`PRECISE RELIEF REQUESTED ........................................................................................ .. 1
`II. LIST OF APPENDIXES ......................................................................................................... 1
`11. LIST OF APPENDIXES ....................................................................................................... .. 1
`III. ARGUMENT ........................................................................................................................... 1
`III. ARGUMENT ......................................................................................................................... .. 1
`A. The Invention Described in the Pastorio ʼ559 Patent is the Use of DCA
`A. The Invention Described in the Pastorio ’559 Patent is the Use of DCA
`as an Oxidation Reagent .................................................................................................. 3
`as an Oxidation Reagent ................................................................................................ .. 3
`1. The DCA in Pastorio’s Claimed Process is Not Simply a Spectator .......................... 4
`1. The DCA in Pastorio’s Claimed Process is Not Simply a Spectator ........................ .. 4
`2. The Pastorio ʼ559 Patent Distinguishes the Use of DCA from the Prior.................... 5
`2. The Pastorio ’559 Patent Distinguishes the Use of DCA from the Prior.................. .. 5
`B. Gharda Does Not Disclose the Use of DCA in the Absence of TCA and Does Not
`B. Gharda Does Not Disclose the Use of DCA in the Absence of TCA and Does Not
`Anticipate the Pastorio Claims......................................................................................... 6
`Anticipate the Pastorio Claims ....................................................................................... .. 6
`C. Gharda Does Not Render the Use of DCA as a Reagent for the Oxidation
`C. Gharda Does Not Render the Use of DCA as a Reagent for the Oxidation
`of the Fipronil Sulfide Precursor Obvious ....................................................................... 9
`of the Fipronil Sulfide Precursor Obvious ..................................................................... .. 9
`1. Pastorio Has Disclaimed the Use of TFA in its Patented Process ............................ 10
`1. Pastorio Has Disclaimed the Use of TFA in its Patented Process .......................... .. 10
`2. Gharda Taught Away from the Inclusion of TFA .................................................... 11
`2. Gharda Taught Away from the Inclusion of TFA .................................................. .. 11
`3. The Prior Art Does Not Suggest that DCA Is an Effective Reagent for the
`3. The Prior Art Does Not Suggest that DCA Is an Effective Reagent for the
`Oxidation of the Fipronil Sulfide Precursor............................................................ 12
`Oxidation of the Fipronil Sulfide Precursor.......................................................... .. 12
`4. A Person of Ordinary Skill in the Art Would Not Have Been Motivated
`4. A Person of Ordinary Skill in the Art Would Not Have Been Motivated
`to Utilize DCA as an Oxidation Reagent for Fipronil ............................................. 14
`to Utilize DCA as an Oxidation Reagent for Fipronil ........................................... .. 14
`D. The Prior Art Did Not Teach the Use of Strong Acid Catalysts
`D. The Prior Art Did Not Teach the Use of Strong Acid Catalysts
`for the Fipronil Oxidation .............................................................................................. 16
`for the Fipronil Oxidation ............................................................................................ .. 16
`E. Levin Has Failed to Introduce Any Evidence that Claims 11 and 12
`E.
`Levin Has Failed to Introduce Any Evidence that Claims 11 and 12
`are Unpatentable ............................................................................................................ 17
`are Unpatentable .......................................................................................................... .. 17
`IV. CONCLUSION ..................................................................................................................... 18
`IV. CONCLUSION ................................................................................................................... .. 18
`APPENDIX 1 – LIST OF EXHIBITS ............................................................................... APP 1 - 1
`APPENDIX 1 — LIST OF EXHIBITS ............................................................................. ..APP 1 - 1
`APPENDIX 2 – STATEMENT OF MATERIAL FACTS ................................................ APP 2 - 1
`APPENDIX 2 — STATEMENT OF MATERIAL FACTS .............................................. ..APP 2 - l
`
`
`
`i
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`

`
`Cases 
`
`TABLE OF AUTHORITIES
`
`Allergan, Inc., v. Sandoz, Inc.,
`796 F.3d 1293 (Fed. Cir. 2015)................................................................................................. 12
`Astrazeneca AB, v. Mutual Pharma. Co., Inc.,
`384 F.3d 1333 (Fed. Cir. 2004)................................................................................................. 11
`DePuy Spine, Inc., v. Medtronic Sofamor Danek, Inc.,
`567 F.3d 1314 (Fed. Cir. 2009)................................................................................................. 13
`Honeywell Int’l, Inc. v. ITT Indus., Inc.,
`452 F.3d 1312 (Fed. Cir. 2006)................................................................................................. 11
`In re Turley,
`304 F.2d 893 (C.C.P.A. 1962) .................................................................................................... 7
`Phillips Petroleum Co., v. Huntsman Polymers Corp.,
`157 F.3d 866 (1998) .................................................................................................................... 5
`Praxair, Inc. v. ATMI, Inc.,
`543 F.3d 1306 (Fed. Cir. 2008)................................................................................................... 4
`
`
`
`Regulations 
`
`37 C.F.R. 41.158(a)....................................................................................................................... 17
`37 C.F.R. 41.207(c)……………………………………………………………………………….1
`
`
`
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`I.
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`PRECISE RELIEF REQUESTED
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`
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`Senior Party, Pastorio (“Pastorio”), requests that the Board deny Motion No. 4 filed by
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`Junior Party, Levin (“Levin”). Levin argues that Pastorio’s involved claims 1 – 12 of U.S. patent
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`8,304,559 (the “ʼ559 patent, Ex. 2001) are unpatentable in view of WO 2007/122440 A1 (“WO
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`ʼ440 or “Gharda”) – a reference that was extensively discussed in the background section of the
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`Pastorio ʼ559 patent, considered by the Examiner during prosecution, and over which the process
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`of Pastorio’s involved claims constitutes a major improvement. Levin has failed to prove that
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`Pastorio’s involved claims are unpatentable over Gharda.
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`II. LIST OF APPENDIXES
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`
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`A list of exhibits on which Pastorio relies in this opposition is in Appendix 1. Material
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`Facts (“MF”) 1 – 70 alleged by Levin, and Pastorio’s responses thereto, are set forth in Appendix
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`2. Pastorio’s additional material facts 71 - 136 are also set forth in Appendix 2.
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`III. ARGUMENT
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`Levin’s argument that Pastorio’s claims are anticipated or obvious relies on an
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`unreasonable interpretation of the claims that completely ignores the teachings of Pastorio’s
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`patent.1 Pastorio’s invention was based on the discovery that dichloroacetic acid (“DCA”) is an
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`excellent reagent for production of the pesticide, fipronil, through oxidation of its sulfide
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`precursor. The Pastorio process is economical and efficient and overcame significant problems
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`associated with prior art processes – processes that are criticized and distinguished in the ʼ559
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`patent. Those prior art processes do not utilize DCA, but instead use expensive, corrosive and
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`inconvenient reagents, such as trifluoroacetic acid (“TFA”) and trichloroacetic acid (“TCA”).
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`1 If Levin’s unpatentability arguments had merit, Levin has failed to rebut the presumption that
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`its claims would also be unpatentable. 37 C.F.R. 41.207(c).
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`Not only was it not obvious to the prior art researchers to use DCA – a much more
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`convenient reagent – but the reference on which Levin relies for its unpatentability arguments
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`expressly teaches away from the use of DCA except in a reaction that includes TCA as the active
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`reagent. Thus it cannot anticipate because the Pastorio claims expressly exclude TCA. That
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`reference also expressly teaches away from the Pastorio process, stating that DCA is a “poor
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`medium for oxidation,” and its only function is to act as a melting point depressant or solvent for
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`the active TCA. Notwithstanding the clear and unmistakable disavowal of the use of TFA in
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`Pastorio’s specification, Levin’s obviousness argument depends on an argument that Pastorio’s
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`claims should be read to encompass a process employing a mixture of DCA and TFA. The
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`broadest reasonable claim interpretation cannot include a TFA process that was expressly and
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`unambiguously disavowed by Pastorio.
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`As Levin’s expert candidly acknowledged in his deposition, Levin cannot cite a single
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`piece of prior art that discloses the use of DCA for the production of fipronil, despite what we
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`know in hindsight to be significant advantages of that reagent. In the absence of such prior art,
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`Levin cites two references that have nothing to do with fipronil. The first – U.S. Patent 6,013,761
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`“the ʼ761 patent” – deals with a completely different oxidation of a polyarylene sulfide polymer,
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`which contains much more easily oxidized sulfide groups and which does not have the complex
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`structure and multiple potential sites for oxidation present in fipronil and its sulfide precursor.
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`The second – U.S. Patent 3,928,372 (“the ʼ372 patent”) – was actually described incorrectly by
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`Levin and its expert as showing the oxidation of a sulfur atom in a thiazole ring in a
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`pharmaceutical compound using DCA. What the reference actually discloses is that the use of
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`DCA resulted in the oxidation of the thiazole nitrogen atom, not the sulfur. Fipronil and its
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`sulfide precursor contain oxidizable nitrogens, and a person of ordinary skill would have been
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`discouraged by this reference from using DCA for the production of fipronil.
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`Levin distorts the teachings of the prior art and relies on the unsupported conclusory
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`opinions of its expert that the invention was obvious. Those conclusory opinions are entitled to
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`no weight. Levin’s unpatentability arguments were clearly formulated after it became apparent
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`that Levin would not prevail on priority. Before that realization, Levin has argued that his claims,
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`which the Board has determined are patentably indistinct from Pastorio’s, were novel and
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`unobvious. (MF 71) (Ex. 2084) (Levin’s counsel arguing that, “[s]tarting from [Gharda], the
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`person skilled in the art would not arrive at the present invention as she/he would not be
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`motivated to replace trichloroacetic acid by a different solvent, specifically dichloroacetic
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`acid.”).
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`A. The Invention Described in the Pastorio ʼ559 Patent is the Use of DCA as an
`Oxidation Reagent
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`The Pastorio ʼ559 patent describes a novel, economical and efficient process for the
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`synthesis of fipronil, which is an important pesticide. The Pastorio process utilizes DCA as a
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`reagent for the oxidation of the fipronil sulfide precursor to fipronil.2 (MF 72; Ex. 2001, 9:2-
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`10:44; Ex. 2085, ¶¶21, 26). Pastorio found that, in the presence of an oxidation agent, such as
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`hydrogen peroxide, DCA is transformed into dichloroperacetic acid (“DCPA”), and that DCPA
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`is an excellent oxidant for the compound of formula II. (MF 73; Ex. 2001, 4:32-38). The reaction
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`avoids the use of the hazardous and inconvenient reagents that were used in the prior art
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`2 The fipronil sulfide precursor and fipronil are represented by formula II and formula I,
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`respectively, in the Pastorio ‘559 patent when each of the R1 and R2 substituents is chlorine. The
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`fipronil sulfide precursor is designated “compound 420” by Levin. (MF 14)
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`processes, and allows convenient recovery and re-cycling of unreacted sulfide precursor. (MF
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`74; Ex. 2001, 5:29-36, 6:16-31; Ex. 2085, ¶¶22-28, 54-55). It is also selective for fipronil
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`without producing excessive quantities of the undesired sulfone over-oxidation product, which
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`results in good yields. (MF75; Ex. 2001, 5:18-22; Ex. 2085, ¶27).
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`1. The DCA in Pastorio’s Claimed Process is Not Simply a Spectator
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`
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`At page 6, line 21 – page 7, line 2, Levin incorrectly asserts that the claim term “in the
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`presence of DCA” means only that the reaction must contain some amount of DCA, but the DCA
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`does not have to perform any function in the oxidation. That interpretation of the claims is
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`unreasonable, and the response is that the DCA in the Pastorio process performs two functions:
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`(1) it acts as a reaction medium, and (2) is integral to the formation of DCPA, which is the
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`oxidizing agent that acts upon the compound of formula II to form fipronil. Levin’s assertion that
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`DCA need not perform any role in the reaction ignores the teachings of the ʼ559 specification,
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`and is contrary to how a person of ordinary skill in the art would have understood the claims.
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`The Pastorio ʼ559 patent explains that in the Pastorio process, DCA performs “the dual
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`function of transferring oxygen to the compound having the general formula (II), and acting as a
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`reaction solvent.” (MF 76; Ex. 2001, 4:55-60; Ex. 2085, ¶¶26-27). With respect to transferring
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`oxygen to the formula II, the Pastorio ʼ559 patent explains that it is DCPA, which is formed by
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`oxidation of DCA in the presence of an oxidizing agent such as hydrogen peroxide, that acts as
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`the oxidizing agent for the conversion of formula II to fipronil. (MF 77; Ex. 2001, 4:26-30; Ex.
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`2085, ¶¶26-27). The Pastorio inventors explain that it was surprising that DCPA would prove to
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`be an excellent oxidant for the conversion of formula II to fipronil. (MF 73; Ex. 2001, 4:32-38).
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`It is clear from the specification that the DCA in the claimed Pastorio process is not merely a
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`spectator molecule in the reaction. The Pastorio claims should not be so interpreted. Praxair,
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`Inc. v. ATMI, Inc., 543 F.3d 1306, 1324 (Fed. Cir. 2008) (“The claims of the patent must be read
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`in light of the specification’s consistent emphasis on this fundamental feature of the invention.”);
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`Phillips Petroleum Co., v. Huntsman Polymers Corp., 157 F.3d 866 (1998) (holding that in view
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`of the specification and prosecution history, the term “block copolymer” is properly construed so
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`that the claimed composition requires a threshold amount of block copolymer). Levin’s argument
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`that the claims should be construed to mean that the use of DCA – the centerpiece of Pastorio’s
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`invention – should be relegated to a trivial and meaningless process component is unreasonable
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`and contrary to Federal Circuit precedent.
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`Moreover, Levin’s expert has previously taken the position that the phrase “in the
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`presence of dicloroacetic acid, of an oxidizing agent, and of a strong acid” in Levin’s claim 2
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`means that the reaction, “necessarily proceeds via a mechanism wherein (1) dichlorperactic acid
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`(“DPA”) is formed in the reaction mixture by the reaction of dichloroacetic acid (“DCA”) and
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`hydrogen peroxide, and (2) the DPA oxidizes the sulfide of Formula II to the sulfoxide of
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`Formula I.” (MF 78; Ex. 1013, ¶18). Dr. Gribble even cites to the specification of the Pastorio
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`ʼ559 patent as confirmation of that reaction mechanism. (MF 79; Ex. 1013, ¶¶18, 21). But Dr.
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`Gribble now takes the contrary position in a transparent attempt to support his unpatentability
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`theory. (MF 80; Ex. 1044, ¶22). In addition, to support his new arguments, Dr. Gribble
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`admittedly misquoted Pastorio’s expert, Dr. Trost by truncating Dr. Trost’s prior testimony to
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`change its meaning. (MF 81; Ex. 2083, 85:6-87:25). Such inconsistent and disingenuous
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`testimony is entitled to no weight.
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`2. The Pastorio ʼ559 Patent Distinguishes the Use of DCA from the Prior Art
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`At page 6, lines 3 – 5 of the motion, Levin asserts that the production of fipronil through
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`the oxidation of formula II by various methods, including the use of peracids derived from acetic
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`acid derivatives was known. The response is that the only peracids that have been described in
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`the prior art for the production of fipronil through oxidation of formula II are a 3-chlorobenzoic
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`acid derivative, trifluoroperacetic acid (“TFPA”) and trichloroperacetic acid (“TCPA”). (MF82-
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`84; Ex. 2001, 1:23-2:29; Ex. 1019, 2:6-8; Ex. 2009, 8:21-24; Ex. 2085, ¶¶22-24). The Pastorio
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`ʼ559 patent identifies these reactions, describes their disadvantages, and explains how the
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`Pastorio process overcomes those disadvantages. (MF 85; Ex. 2001, 1:23-2:63, 5:18-36, 8:10-
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`44; Ex. 2085, ¶¶31-37). Thus, it is again clear from the specification that the Pastorio inventors
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`regarded the use of DCA after conversion to DCPA, to be an oxidation agent in their invention.
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`B. Gharda Does Not Disclose the Use of DCA in the Absence of TCA and Does Not
`Anticipate the Pastorio Claims
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`Gharda discloses a fipronil synthesis method that utilizes TCA together with a melting
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`point depressant. (MF 86; Ex. 2009, 6:23-7:4; Ex. 2085, ¶¶31-34). Every example of Gharda
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`utilizes TCA. (MF 87; Ex. 2009, 10:10 – 11:21). Each claim in Gharda requires the use of TCA.
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`(MF 88; Ex. 2009, 12:1 – 15:10). A person of ordinary skill in the art would have understood
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`that the entire purpose of Gharda was to develop a process that replaced TFA with TCA. (MF 89;
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`Ex. 2085, ¶¶31-34). In short, every embodiment of Gharda requires the use of TCA, which upon
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`oxidation with hydrogen peroxide yields the active oxidant TCPA. Accordingly, Gharda simply
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`cannot anticipate the Pastorio claims because those claims specifically exclude TCA and TCPA.
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`At page 8, lines 3 – 13 of the motion, Levin argues that Gharda’s statement that “the
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`preferred melting point depressant dichloro acetic acid is a poor medium for oxidation…” is a
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`disclosure that DCA alone can be used to oxidize formula II to fipronil and therefore anticipates
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`Pastorio’s claims. The response is that Levin’s reliance on this single sentence is contrary to the
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`actual disclosure of Gharda and turns the teaching of the reference on its head. Accordingly,
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`Gharda does not anticipate the Pastorio claims.
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`Gharda clearly does not disclose the use of DCA as an active reagent for the oxidation of
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`the fipronil sulfide precursor. Nor does Gharda teach the use of DCA in the absence of TCA or
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`TCPA. Gharda’s “purpose of [DCA’s] addition is only to sufficiently depress the melting point
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`of trichloro acetic acid.” (MF 50; Ex. 1044, ¶75; Ex. 2009, 9:17-21). In fact, the only discussion
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`of DCA in Gharda is in reference to its function as a melting point depressant. (MF 90; Ex. 2009,
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`2:5-9, 7:8-11, 9:17-23; Ex. 2085, ¶34-37, 40). Levin’s expert, Dr. Gribble, admits that the
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`authors of Gharda only saw the function of DCA as a melting point depressant. (MF 91; Ex.
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`2083, 26:7-13). The sentence on which Levin relies appears in a paragraph that describes how
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`much TCA to use in the oxidation reaction, and, more importantly, how much DCA must be
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`combined with the TCA so that the melting point of TCA is sufficiently depressed. (MF 92; Ex.
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`2009, 9:10-25; Ex. 2085, ¶37). A person of ordinary skill reading this sentence in context would
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`have understood that because DCA was only added to reduce the melting point of TCA, the
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`reference does not teach the use of DCA in the absence of TCA as required by the Pastorio
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`claims. (MF 93; Ex. 2085, ¶¶36-40).
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`Dr. Gribble asserts that the statement, “the preferred melting point depressant dichloro
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`acetic acid is a poor medium for oxidation…” means DCA is a functional, albeit poor medium
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`for the oxidation of formula II to fipronil as compared to TCA:DCA. (MF 94; Ex. 1044, ¶77).
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`Dr. Gribble reads too much into the word “poor.” While he admitted in his deposition that in
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`general usage “poor” includes something that does not work at all (MF 95; Ex. 2083, 69:22-
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`70:3), he argues that in the Gharda sentence, it must mean that DCA is functional to some extent.
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`This argument is pure conjecture. Gharda discloses only one function of DCA – as a melting
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`point depressant. Dr. Gribble’s assertion also is contradicted by his deposition testimony in
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`which he admitted that the Gharda reference does not disclose an experiment in which DCA is
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`used by itself. (MF 96; Ex. 2083, 70:11-15). Dr. Gribble also admitted that there is no reference
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`describing the oxidation of the compound of formula II to fipronil using DCPA. (MF 97; Ex.
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`2083, 24:7-13; Ex. 2085, ¶29). Dr. Gribble’s interpretation of the Gharda reference is simply
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`inconsistent with his own admissions.
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`In addition, the phrase on which Dr. Gribble relies does not say what Dr. Gribble argues
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`it says. As even Dr. Gribble agrees, the sentence does not say that DCA is a “poor medium for
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`the oxidation,” or “poor medium for oxidation of a fipronil precursor.” (MF 98; Ex. 2083, 62:22-
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`63:8). There is simply no basis for interpreting Gharda’s characterization of DCA as a “poor
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`medium for oxidation” as anything other than a general statement that DCA is not suitable for
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`oxidation reactions. Rather, a person of skill in the art would have understood the Gharda
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`reference simply to be commenting generally that DCA is a poor medium for oxidation
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`reactions, and therefore is used only as a melting point depressant for TCA. (MF 99; Ex. 2085,
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`¶¶38-43). This statement would discourage a person of skill in the art from using DCA as
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`anything other than a melting point depressant for TCA. (MF 100, Ex. 2085, ¶39). In fact, had
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`Gharda tested DCA by itself as a medium for the oxidation of formula II to fipronil, Gharda
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`would have discovered – like Pastorio – that it was actually a good medium for that oxidation.
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`(MF 101; Ex. 2085, ¶36)
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`Gharda’s characterization of DCA as a “poor medium” as interpreted by Levin and its
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`expert is far from the clear and explicit disclosure that is required for anticipation. In re Turley,
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`304 F.2d 893, 899 (C.C.P.A. 1962) (“Statements in a prior application relied on to prove
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`anticipation must be so clear and explicit that those skilled in the art will have no difficulty in
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`ascertaining their meaning. Where they are so vague, involved, intricate, and contradictory that
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`experts disagree radically as to their meaning and, following the instructions given, construct
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`devices differing in fundamental features, it is safe to reject such a document as an
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`anticipation.”); Ex parte Yu-Piao Wang, 2013 Pat. App. LEXIS 8918 (Pat. App. 2013) (“An
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`anticipation rejection cannot be predicated on an ambiguous reference. Rather, disclosures in a
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`reference relied on to prove anticipation must be so clear and explicit that those skilled in the art
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`will have no difficulty ascertaining their meaning.”)
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`C. Gharda Does Not Render the Use of DCA as a Reagent for the Oxidation of the
`Fipronil Sulfide Precursor Obvious
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`At page 13, lines 8-10 of the motion Levin argues that sulfide oxidation is not an
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`unpredictable art, and a person of ordinary skill would have reasonably expected fipronil to form
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`from the oxidation of the sulfide precursor in the presence of DCA and hydrogen peroxide. The
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`response is that Levin’s obviousness theory is based entirely on impermissible hindsight
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`reconstruction. Otsuka Pharm. Co. v. Sandoz, Inc., 678 F.3d 1280, 1296 (Fed. Cir. 2012) (“The
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`inventor’s own path itself never leads to a conclusion of obviousness; that is hindsight. What
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`matters is the path that the person of ordinary skill in the art would have followed, as evidenced
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`by the pertinent prior art.”); Interconnect Planning Corp. v. Feil, 774 F.2d 1132, 1138 (Fed. Cir.
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`1985) (“The invention must be viewed not with blueprint drawn by the inventor…”). A person of
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`ordinary skill in the art would not have been able to predict whether the oxidation of the sulfide
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`precursor utilizing DCA as a reagent would have been successful. Nor would the skilled artisan
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`have been motivated to select DCA as a possible reagent given Gharda’s characterization of
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`DCA as “a poor medium for oxidation.” (MF 102, Ex. 2085, ¶¶46-49).
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`The fact that sophisticated researchers chose to use expensive, hazardous and
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`inconvenient reagents such as TFA and TCA rather than DCA belies Levin’s hindsight argument
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`that the use of DCA would have been obvious. DCA overcame the problems of the prior art by
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`providing an economical and effective oxidation process. Even Levin has argued the use of DCA
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`would not have been obvious over the Gharda reference. (MF 71; Ex. 2084).
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`1. Pastorio Has Disclaimed the Use of TFA in its Patented Process
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`At page 11, lines 6-7, Levin argues that the Pastorio claims are broad enough to
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`encompass the use of a mixture in which DCA is present along with TFA which would function
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`as the active reagent in the oxidation. Thus, Levin argues that process would have been obvious
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`over WO 01/030760 (“WO ʼ760”), which describes the use of TFA.3 What Levin ignores is that
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`Pastorio has expressly disavowed a process that employs TFA as the active reagent.
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`The Pastorio ʼ559 specification makes clear that the inventors considered the use of DCA
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`as reagent for the subsequent oxidation of the fipronil sulfide precursor to fipronil to be their
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`invention. The ʼ559 patent repeatedly touts the benefits of the novel process while criticizing the
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`prior art processes – including those of WO ’760 and Gharda WO ʼ440. Levin’s expert, Dr.
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`Gribble, admits that the Pastorio ʼ559 patent discusses the drawbacks of TFA while describing
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`the advantages of the Pastorio process over the use of TFA. (MF 103; Ex. 2083, 9:22-11:13).
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`Thus, the prior art solvents, i.e., TFA and TCA, and their associated peracids, i.e., TFPA and
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`TCPA, are not within the scope of the Pastorio claims. Honeywell Int’l, Inc. v. ITT Indus., Inc.,
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`3 Although the Board has restricted Levin to one prior art reference – Gharda WO ʼ440 – as the
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`basis for its anticipation and obviousness arguments (Paper 155, 3:19-22), Levin nevertheless
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`bases substantive obviousness arguments on a combination of references under the guise of
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`explaining what would have been known to a person of ordinary skill. Pastorio submits that
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`Levin’s reliance on other references to support its unpatentability arguments is improper and
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`should be disregarded, but out of an abundance of caution responds to those arguments in this
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`opposition.
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`452 F.3d 1312, 1320 (Fed. Cir. 2006) (finding that “repeated derogatory statements concerning
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`one type of material are the equivalent of disavowal of that subject matter from the scope of the
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`patent’s claims.”). The criticism of the prior art TFA (and TCA) methods, combined with the
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`description of the advantages of using DCA amounts to an unmistakable disavowal of TFA and
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`TCA from the scope of the Pastorio claims. Astrazeneca AB, v. Mutual Pharma. Co., Inc., 384
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`F.3d 1333, 1340 (Fed. Cir. 2004) (“Where the general summary or description of the invention
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`describes a feature of the invention and criticizes other products that lack the same feature, this
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`operates as a clear disavowal of these other products.”) (internal parentheticals omitted).
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`The ʼ559 patent could not be clearer in its disavowal of the use of TFA, stating that
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`this method [using TFA] is unsatisfactory given the following drawbacks: first of all the
`trifluoroacetic acid is an extremely expensive reagent which, as a consequence,
`negatively affects the sale price of the product therewith obtained. Moreover, during the
`reaction, hydrogen fluoride is released, which eats into the vitreous coatings used in
`industrial reactors despite operating at temperatures close to ambient temperature . . .
`Moreover, the use of a corrosion inhibitor would not be adequate to protect all the
`equipment needed for the recovery process . . . TFA recovery and subsequent
`reutilization is a necessary operation dictated by the high cost of TFA compared to
`common oxidants.
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`Ex. 2001, 2:4-20 (emphasis added). The ʼ559 patent further discloses “[t]he present invention
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`therefore allows to operate in the absence of solvents at the same temperature and to achieve
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`excellent selectivity similar to the ones achieved with trifluoroperacetic acid but without having
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`to use an extremely expensive solvent such as TFA . . . .” Ex. 2001, 5:29-33. The fact that the
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`Pastorio claims expressly exclude TCA and TCPA does not alter the fact that Pastorio also
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`disavowed the use of TFA and TFPA.
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`2. Gharda Taught Away from the Inclusion of TFA
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`At page 10, lines 12 – 17 of the motion, Levin argues that a person of ordinary skill in the
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`art would have been motivated to try the Gharda reaction without TCA. At page 11, lines 1-7 of
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`the motion, Levin argues that a person of ordinary skill would have been motivated to substitute
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`the TCA used in Gharda with TFA. The response is that the entire purpose of the Gharda process
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`is to replace TFA with TCA. Gharda states that “[t]he main object of the present invention is
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`successfully to substitute the corrosive and expensive solvent trifluoro acetic acid with an
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`inexpensive and easily available but effective alternative solvent.” (MF 104; Ex. 2009, 1:23-26).
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`Gharda also describes that TCA has advantages over TFA because it is “commercially available
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`at about one tenth the cost of trifluro acetic acid and is