Filed on Behalf of Willowood USA, LLC
`
`By: Steven E. Tiller
`stiller@wtplaw.com
`Peter J. Davis
`pdavis@wtplaw.com
`Whiteford, Taylor & Preston LLP
`7 St. Paul Street
`Baltimore, MD 21202
`Tel: (410) 347-9425
`Fax: (410) 223-4325
`
`IN THE UNITED STATES PATENT
`AND TRADEMARK OFFICE
`(Patent Trial and Appeal Board)
`
`_________________________
`
`WILLOWOOD USA, LLC
`Petitioner
`
`v.
`
` BASF SE
`Patent Owner
`
`_______________________
`
`Case No: To Be Assigned
`U.S. Patent No.: 7,816,392
`________________________
`
`PETITION FOR INTER PARTES REVIEW
`PURSUANT TO 37 C.F.R. § 42.100 et.seq.
`
`
`
`By: Steven E. Tiller
`stiller@wtplaw.com
`Peter J. Davis
`pdavis@wtplaw.com
`Whiteford, Taylor & Preston LLP
`7 St. Paul Street
`Baltimore, MD 21202
`Tel: (410) 347-9425
`Fax: (410) 223-4325
`
`IN THE UNITED STATES PATENT
`AND TRADEMARK OFFICE
`(Patent Trial and Appeal Board)
`
`_________________________
`
`WILLOWOOD USA, LLC
`Petitioner
`
`v.
`
` BASF SE
`Patent Owner
`
`_______________________
`
`Case No: To Be Assigned
`U.S. Patent No.: 7,816,392
`________________________
`
`PETITION FOR INTER PARTES REVIEW
`PURSUANT TO 37 C.F.R. § 42.100 et.seq.
`
`
`
`TABLE OF CONTENTS
`
`I.
`
`Mandatory Notices Under 37 C.F.R. §42.8(a)(1) ........................
`
`A.
`
`B.
`
`C.
`
`D.
`
`Real Parties in Interest .......................................................
`
`Related Matters ..................................................................
`
`Lead and Back-up Counsel ................................................
`
`Service Information ............................................................
`
`II.
`
`Fees ...............................................................................................
`
`III. Requirements for IPR under 37 C.F.R.§42.104 ...........................
`
`A.
`
`B.
`
`Grounds for Standing (37 C.F.R.§42.104(a)) ....................
`
`Basis for Challenge and Relief Requested
`(37 C.F.R.§42.104(b)) ........................................................
`
`1.
`
`2.
`
`Claims for Which Review is Requested ....................
`
` Priority Date of the ‘392 Patent .............................
`
`IV. Overview of the ‘392 Patent .........................................................
`
`A.
`
`B.
`
`C.
`
`Person of Ordinary Skill in the Art ....................................
`
`The Specification and Claims .............................................
`
`Prosecution History ............................................................
`
`V.
`
`Prior Art on Which Challenge is Based .......................................
`
`A.
`
`B.
`
`Crystalline Modification IV of Pyraclostrobin ..................
`
`Processes for Crystallizing Organic Compounds ..............
`
`2
`
`2
`
`2
`
`2
`
`3
`
`3
`
`3
`
`3
`
`4
`
`4
`
`4
`
`4
`
`4
`
`5
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`9
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`12
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`13
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`15
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`i
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`VI. Claim Construction .......................................................................
`
`A.
`
`“Crystalline Modification IV of Pyraclostrobin” ..............
`
`VII. Statutory Grounds on Which Challenge is Based ........................
`
`VIII. Scientific Overview .......................................................................
`
`A.
`
`B.
`
`C.
`
`Crystal Structures of Chemical Compounds ......................
`
`Pyraclostrobin ....................................................................
`
`Thermal Methods of Analysis .............................................
`
`D. Determination of Melting Point .........................................
`
`E.
`
`F.
`
`Differential Scanning Calorimetry .....................................
`
`Utility of DSC in Studies of Polymorphism ........................
`
`IX. Grounds of Unpatentability ..........................................................
`
`A.
`
`B.
`
`Legal Standard ...................................................................
`
`Ground 1 – Australian Anticipates Claims 1-3 and 15-17
`
`C. Ground 2 – Claims 4-14 are Obvious over Australian in
`View of Vogel and in Further View of Beckman ................
`
`X.
`
`Conclusion ....................................................................................
`
`19
`
`20
`
`23
`
`23
`
`23
`
`26
`
`27
`
`28
`
`30
`
`32
`
`33
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`33
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`35
`
`37
`
`50
`
`ii
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`
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`
`TABLE OF AUTHORITIES
`
`CASES
`
`Alza Corp. v. Mylan Labs., Inc., 464 F. 3d 1286(Fed. Cir. 2006) ..........
`
`Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342 (Fed. Cir. 1999) ........
`
`Brown v. 3M, 265 F.3d 1349 (Fed. Cir. 2001) ........................................
`
`Custom Accessories, Inc. v. Jeffrey-Allan Indus., Inc.,
`807 F. 2d 955 (Fed. Cir. 1986)................................................................
`
`In re Aller, 220 F. 2d 454, 456 (C.C.P.A. 1955) ....................................
`
`In re Best, 562 F.2d 1252, 1255 n.4 (CCPA 1977) ................................
`
`In re Morris, 127 F.3d 1048 (Fed. Cir. 1997) .........................................
`
`KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 406,
`127 S. Ct. 1727, 167 L. Ed. 2d 705 (2007) .............................................
`
`nXn Partners, LLC v. Nissan Chemical Industries, Ltd,
`IPR2016-00694 (Patent No. 8,796,464) (August 31, 2016) ...................
`
`Pfizer, Inc. v. Apotex, Inc. 480 F. 3d 1348 (Fed. Cir. 2007) ...................
`
`Soft Gel Technologies, Inc. v. Jarrow Formulas, Inc.,
`864 F. 3d 1334 (Fed. Cir. 2017)..............................................................
`
`Titanium Metals Corp. of Am. v. Banner,
`778 F.2d 775 (Fed. Cir. 1985) .................................................................
`
`STATUTES AND RULES
`
`37 C.F.R. §42.8(a)(1) ..............................................................................
`
`37 C.F.R. §42.15(a) ................................................................................
`
`38
`
`34
`
`40
`
`5
`
`41
`
`10
`
`19
`
`37
`
`35
`
`41
`
`38
`
`34
`
`2
`
`3
`
`37 C.F.R. §42.100 ................................................................................... 1, 19
`
`iii
`
`
`
`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`
`37 C.F.R. §42.104 ................................................................................... 3, 4
`
`35 U.S.C. §§102 ...................................................................................... passim
`
`35 U.S.C. §§103 ...................................................................................... passim
`
`35 U.S.C. §§311-319 ..............................................................................
`
`35 U.S.C. §371 ........................................................................................
`
`1
`
`9
`
`iv
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`
`EXHIBIT LIST
`
`WW 1001
`
`BASF Aktiengesellschaft’s Name Change to BASF SE Filed with
`USPTO
`
`WW 1002
`
`US Patent No. 7,816,392
`
`WW 1003
`
`Declaration of Harry Brittain
`
`WW 1004
`
`January 12, 2010 Non-Final Rejection of Application No.
`11/917,976
`
`WW 1005
`
`U.S. Patent Publ. No. US 2003/0199394
`
`WW 1006
`
`WW 1007
`
`WW 1008
`
`April 23, 2010 Reply to Office Action regarding Application No.
`11/917,976
`
`Notice of Allowance dated June 17, 2010 of Application No.
`11/917,976
`
`Public Release Summary on Evaluation of the New Active
`Pyraclostrobin in the Product Cabrio Fungicide, Australian
`Pesticides and Veterinary Medicines Authority, September, 2003
`
`WW 1009
`
`Declaration of J. Hindah Weissbrot
`
`WW 1010
`
`WW 1011
`
`Excerpt from A Textbook of Practical Organic Chemistry
`Including Qualitative Organic Analysis, Arthur I. Vogel, Third
`Ed. (1956)
`
`Wolfgang Beckmann, Seeding the Desired Polymorph:
`Background, Possibilities, Limitations, and Case Studies, Organic
`Process Research & Development 2000, 4, 372-383
`
`WW 1012
`
`Label for BASF’s Headline Product
`
`WW 1013
`
`Declaration of Randy C. Ploetz
`
`v
`
`
`
`Willowood USA, LLC (“Petitioner” or “Willowood”) respectfully petitions
`
`the Patent Trial and Appeal Board for inter partes review (“IPR”) under 35 U.S.C.
`
`§§311-319 and 37 C.F.R. §42.100 et seq. of Claims 1 through 17 of US Patent No.
`
`7,816,392 (“the ‘392 patent”) titled Crystalline Modifications to Pyraclostrobin.
`
`According to PTO records, the ‘392 patent is assigned to BASF SE (“BASF” or
`
`“Patent Owner”).1 As explained in this Petition, inter partes review should be
`
`instituted as there is a reasonable likelihood that Willowood will establish that at
`
`least one claim challenged in this Petition is invalid under 35 U.S.C. §§102 or 103.
`
`The ‘392 patent (a copy of which is provided as WW 1002) claims a
`
`particular crystalline modification of the agrochemical compound pyraclostrobin
`
`and certain processes to prepare it. As set forth below, this claimed crystalline
`
`form of pyraclostrobin was well known in the art more than one year prior to the
`
`filing of the earliest application to which the ‘392 patent claims priority.
`
`Moreover, the claimed processes to manufacture that crystalline form of
`
`1
`
`BASF Aktiengesellschaft is listed as the assignee on the face of the ‘392
`
`patent. On June 17, 2015, a document dated March 13, 2008 entitled Certificate in
`
`Conformity with Sec. 21 of the Federal German Ordinance for Notaries
`
`Concerning the Conversion of BASF Aktiengesellschaft was filed with the United
`
`States Patent & Trademark Office providing that BASF Aktiengesellschaft’s name
`
`had been changed to BASF SE. A copy of this filing is attached as WW 1001.
`
`1
`
`
`
`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`pyraclostrobin are nothing but common processes to crystallize organic compounds
`
`known for decades before the earliest priority of the ‘392 patent. Accordingly,
`
`each claim of the ‘392 patent should be found unpatentable pursuant to 35 U.S.C.
`
`§§102 and/or 103.
`
`I. Mandatory Notices Under 37 C.F.R. §42.8(a)(1)
`
`A.
`
`Real Parties in Interest
`
`The real parties in interest are the Petitioner, Willowood USA, LLC, as well
`
`as Willowood, LLC and Greenfields Marketing, Limited.
`
`B.
`
`Related Matters
`
`BASF Corporation, which claims to be the exclusive licensee of the ‘392
`
`patent from the Patent Owner, filed suit against Willowood USA, LLC,
`
`Willowood, LLC, Willowood Limited, and Greenfields Marketing, Limited in the
`
`United States District Court for the District of Colorado, Case No. 1:18-cv-00268,
`
`on February 1, 2018 claiming that the Defendants infringe the ‘392 patent with
`
`their importation, testing, formulation, and sale of pyraclostrobin. The Defendants
`
`deny those allegations and Willowood USA, Willowood, LLC and Greenfield
`
`Marketing filed a counterclaim seeking, among other things, a declaration that the
`
`‘392 patent is invalid or otherwise unenforceable.
`
`C.
`
`Lead and Back-up Counsel
`
`Petitioner provides the following designation of counsel:
`
`2
`
`
`
`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`Lead Counsel:
`
`Steven E. Tiller, Whiteford, Taylor & Preston, LLP,
`
`Seven Saint Paul Street, Suite 1500, Baltimore, Maryland 21202-1636; 410-347-
`
`9425; stiller@wtplaw.com; Reg No.: 39,859.
`
`Back-up Counsel: Peter Davis, Whiteford, Taylor & Preston, LLP, Seven
`
`Saint Paul Street, Suite 1500, Baltimore, Maryland 21202-1636; 410-347-8738;
`
`pdavis@wtplaw.com; Reg. No.: 36,119.
`
`D.
`
`Service Information
`
`Please address all correspondence and service to counsel at the addresses
`
`provided above. Petitioner further consents to service by electronic mail at the
`
`email addresses provided above.
`
`II. Fees
`
`Petitioner authorizes the Patent and Trademark Office to charge Deposit
`
`Account No. 501479 for the fees set in 37 C.F.R. §42.15(a) for this Petition and
`
`further authorizes any additional fees to be charged to this same account.
`
`III. Requirements for IPR under 37 C.F.R. §42.104
`
`A. Grounds for Standing (37 C.F.R. § 42.104(a))
`
`Willowood and its undersigned counsel certify that the ‘392 patent is
`
`available for inter partes review and that Willowood is not barred or estopped from
`
`requesting such review. Willowood has not initiated a civil action challenging the
`
`validity of any claim of the ‘392 patent, and no complaint alleging infringement of
`
`3
`
`
`
`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`the ‘392 patent was served on Willowood more than one year before the date of
`
`this Petition. The ‘392 patent issued more than nine months prior to the date of
`
`this Petition.
`
`B.
`
`Basis for Challenge and Relief Requested (37 C.F.R. § 42.104(b))
`
`1.
`
`Claims for Which Review is Requested
`
`Willowood respectfully requests inter partes review of claims 1 through 17
`
`of the ‘392 patent on the grounds below and requests that each claim be found
`
`unpatentable pursuant to 35 USC §§ 102(b) and/or 103.
`
`2.
`
`Priority Date of the ‘392 Patent
`
`The ‘392 patent, entitled “Crystalline Modifications to Pyraclostrobin,”
`
`issued on October 19, 2010 from application number 11/917,976 which was
`
`nationalized from PCT number PCT/EP2006/005869 filed June 19, 2006. This
`
`PCT application claimed priority to German application DE 10 2005 028 493 filed
`
`June 20, 2005. Accordingly, and solely for purposes of this Petition, Petitioner
`
`assumes that the earliest date to which the Patent Owner is entitled to claim
`
`priority is June 20, 2005.
`
`IV. Overview of the ‘392 Patent
`
`A.
`
`Person of Ordinary Skill in the Art
`
`A person of ordinary skill in the art (“POSITA”) is a hypothetical person
`
`presumed to have known the relevant art at the time of the alleged invention. See,
`
`4
`
`
`
`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`e.g., Custom Accessories, Inc. v. Jeffrey-Allan Indus., Inc., 807 F. 2d 955, 962
`
`(Fed. Cir. 1986) (“The person of ordinary skill is a hypothetical person who is
`
`presumed to be aware of all the pertinent prior art.”). A POSITA at the time of the
`
`alleged invention claimed by the ‘392 patent would have a Bachelor of Science
`
`degree in chemistry or chemical engineering with one to three years’ experience
`
`preparing or analyzing crystal structures of chemical compounds. Additional
`
`graduate education would likely substitute for relevant experience, while additional
`
`experience in the field of preparing or analyzing crystal structures would likely
`
`substitute for formal education. See, Declaration of Harry Brittain, attached as
`
`WW 1003 at ¶24. Such a person would have been capable of understanding the
`
`‘392 patent and applying the prior art references discussed below.
`
`B.
`
`The Specification and Claims
`
` As set forth in its abstract, the ‘392 patent “relates to novel crystalline
`
`modifications of pyraclostrobin, to processes for their preparation and to the use of
`
`[these] novel modifications for preparing crop protection compositions.” WW
`
`1002 at Abstract. According to the ‘392 patent, the commercially available form
`
`of pyraclostrobin at the time of filing was “an amorphous substance characterized
`
`by a low melting point.” Id. at 1:13-15. Consequently, pyraclostrobin
`
`commercially available at the time was purportedly not suitable for preparing
`
`aqueous suspension concentrates using conventional technology. Id. at 1:15-23. It
`
`5
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`was therefore the applicants’ objective to identify pyraclostrobin in a form that
`
`would allow the preparation of suspension concentrates having improved stability.
`
`Id. at 1:46-48. This objective was achieved through the purported discovery of
`
`various crystal (i.e., polymorphic) forms of pyraclostrobin identified in the patent
`
`as pyraclostrobin crystalline modifications I, II, III, and IV.
`
`All claims of the ‘392 patent relate to what the applicants labeled
`
`“crystalline modification IV of pyraclostrobin,” defined as having a melting point
`
`“in the range of 62 to 72°C, in particular in the range from 64 to 68°C, and
`
`especially in the range from 65 to 67°C” while having a heat of fusion of 72 to 78
`
`J/g, as well as a distinct X-ray pattern diffraction pattern. Id. at 1:51-2:2. Three
`
`other crystalline forms of pyraclostrobin were also disclosed (but not claimed) by
`
`the ‘392 patent (labeled as crystalline modification I, II, and III, respectively, of
`
`pyraclostrobin), each having a melting point distinct from the melting points of the
`
`other identified forms. In this regard, crystalline modification I was defined as
`
`having a melting point in the range of 55 to 56°C (Id. at 8:52-53), crystalline
`
`modification II was defined as having a melting point in the range of 57 to 58°C
`
`(Id. at 9:24-25), and crystalline modification III was defined as having a melting
`
`point of 59 to 60°C (Id. at 10:41-42). The ’392 further claims “customary”
`
`methods of preparing crystals of organic compounds like pyraclostrobin. Id. at
`
`4:22-32.
`
`6
`
`
`
`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`The ‘392 patent’s independent claims state:
`
`1.
`
`A crystalline modification IV of pyraclostrobin which, in an X-
`ray powder diffractogram at 25°C, shows at least three of the
`following reflexes:
`
`d = 6.02 ± 0.01 Å
`d = 4.78 ± 0.01 Å
`d = 4.01 ± 0.01 Å
`d = 3.55 ± 0.01 Å
`d = 3.01 ± 0.01 Å.
`
`4. A process for preparing a crystalline modification IV of
`pyraclostrobin according to any of the preceding claims,
`comprising:
`
`i) dissolving a pyraclostrobin form different from modification
`IV in an organic solvent or solvent mixture,2 where the organic
`
`2
`
`Preferred L1 solvents are disclosed by the ‘392 patent to be C1 through C4-
`
`alkanols, such as methanol, ethanol, n-propanol,
`
`isopropanol, n-butanol,
`
`isobutanol, 2-butanol, and tert-butanol, as well as mixtures of certain of these. Id.
`
`at 3:5-11. Two ketone solvents (acetone and butanone a/k/a methyl ethyl ketone)
`
`are also included in the L1 listing. Id. The ‘392 patent goes on to identify a
`
`number of solvents in addition to the L1 solvents effective for dissolving
`
`pyraclostrobin. Id. at 3:12-51. On a volume basis, the proportion of the solvents
`
`7
`
`
`
`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`solvent or solvent mixture comprises at least 70% by volume of
`at least one fully water-miscible organic solvent L1 and up to
`30% by volume of water; and
`
`ii) effecting crystallization of pyraclostrobin over a period of at
`least 10 hours and/or in the presence of seed crystals of
`modification IV.3
`
`12. A process for preparing a crystalline modification IV of
`pyraclostrobin according to claim 1, comprising:
`
`i) preparing a suspension of a pyraclostrobin form different
`from modification IV in an organic solvent;
`
`different from L1 (in particular the C1 through C4-alkanols) shall not exceed 30%
`
`by volume, in particular 20% by volume, particularly 10% by volume, and
`
`especially 5%. Id. at 3:52-57.
`
`3
`
`The ‘392 patent describes the amount of added seed crystals to be typically
`
`from 0.001 to 10% by weight, frequently from 0.005 to 5%, in particular from 0.01
`
`to 1%, and especially from 0.05 to 0.5%. Id. at 4:42-45. The use of seeding, the
`
`‘392 patent explains, serves to shorten the duration of crystallization to typically at
`
`least 2 hours, in particular at least 4 hours, and especially at least 5 hours. Id. at
`
`4:46-40.
`
`8
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`ii) optionally, adding seed crystals of modification IV to the
`suspension; and
`
`iii) agitating the suspension until at least 90% of the
`pyraclostrobin comprised therein is present in the form of
`modification IV.
`
`15. A composition for crop protection, comprising pyraclostrobin
`in the form of modification IV, carriers, and/or auxillaries.
`
`17. A method of controlling phytopathogenic fungi comprising
`contracting a plant, seed, or soil in need of treatment with a
`crystalline form of modification IV of pyraclostrobin.
`
`Id. at 25:42 – 26:57.
`
`C.
`
`Prosecution History
`
`BASF nationalized its PCT application in the United States pursuant to 35
`
`U.S.C. §371(c)(1), (2), and (4) on December 18, 2007. On January 12, 2010, all
`
`twenty-one pending claims were rejected under 35 U.S.C. §102(b) as anticipated
`
`by, or, in the alternative, under 35 U.S.C. §103(a), as obvious, over U.S. Patent
`
`Publ. No. US 2003/0199394 (“the ‘394 publication”) having a publication date of
`
`October 23, 2003. The examiner asserted that the ‘394 publication disclosed
`
`pyraclostrobin crystal forms, a process for making such crystals, and a method of
`
`using a compound containing such crystals for controlling pathogenic fungi. See,
`
`9
`
`
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`Jan. 12, 2010 Non-Final Rejection attached as WW 1004 at 4. A copy of the ‘394
`
`publication is attached as WW 1005. The examiner contended that even though the
`
`‘394 publication was silent as to any X-ray diffraction data, the compound
`
`prepared by the disclosed procedure was taught by the ‘392 publication. Id. Based
`
`on the ‘394 publication’s disclosure of the precise manufacturing method disclosed
`
`and claimed in the application, the examiner contended that by practicing the prior
`
`art procedure, pyraclostrobin crystalline modification IV would have to have been
`
`included in any resulting mixture. Id.
`
`The examiner further concluded that the claimed pyraclostrobin crystalline
`
`structure was taught by the prior art and that the methods of preparing this
`
`structure would have been “obvious to try” for one skilled in the art. Id. The
`
`examiner relied on MPEP §2112(III) for this rejection, which states, “where [an]
`
`applicant claims a composition in terms of a function, property or characteristic
`
`and the composition of the prior art is the same as that in the claim but the function
`
`is not explicitly disclosed by the reference, the examiner may make a rejection
`
`under both 35 U.S.C. §102 and 103, expressed as a 102/103 rejection.” Id. at 5.4
`
`4
`
`As further discussed in the MPEP, “[t]here is nothing inconsistent in
`
`concurrent rejections for obviousness under 35 U.S.C. §103 and for anticipation
`
`under 35 U.S.C. §102.” In re Best, 562 F.2d 1252, 1255, n.4 (CCPA 1977). This
`
`10
`
`
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`On April 23, 2010, the applicants responded by arguing that only
`
`pyraclostrobin crystalline modification I was obtained by the melt crystallization
`
`method disclosed in the ‘394 publication. See, April 23, 2010 Reply to Office
`
`Action attached as WW 1006 at p. 5. In contrast, the applicants argued, crystalline
`
`modification IV is prepared using a solution-recrystallization process. Id. at p. 6.
`
`Because of the allegedly inherent differences between solution-recrystallization
`
`and melt-crystallization (which were not explained), the applicants argued that
`
`there would be no reason to believe that the crystalline modification obtained from
`
`the solution-recrystallization would be the same crystalline modification obtained
`
`from the melt crystallization process. Id. at p. 7.
`
`Importantly, the applicants emphasized the different melting points of
`
`crystalline modifications I and IV as an important distinction between the ‘394
`
`publication’s alleged disclosure of only crystalline modification I and their claim of
`
`crystalline modification IV.
`
`Indeed, crystal modification I obtained from the melt-crystallization
`has a melting point in the range [of] 55-56°C…whereas modification
`IV obtained from the solution-recrystallization has a melting point in
`
`same rationale, the MPEP states, also applies to product, apparatus, and process
`
`claims claimed in terms of function, property or characteristic.
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`the range of 65-67°C….Thus, it is clear that [the ‘394 publication]
`discloses crystal modification I and not crystal modification IV.
`
`Id.
`
`In responding to the examiner’s alternative argument that the methods used
`
`for preparing crystalline modification IV were “obvious to try,” the applicants did
`
`not argue that the ‘394 publication failed to disclose these methods. Rather, they
`
`argued that the “obvious to try” standard requires the existence of a finite number
`
`of solutions from which the skilled artisan can choose. Id. Because the existence
`
`of crystalline modification IV was purportedly not known in the prior art, the
`
`applicants argued that it would not have been obvious to try the methods disclosed
`
`in the ‘392 publication to prepare crystalline modification IV since no solution can
`
`exist to make that which is not known. Id. Therefore, the applicants argued, the
`
`‘394 publication did not render the claimed processes for preparing crystalline
`
`modification IV of pyraclostrobin obvious. The examiner then issued a notice of
`
`allowance on June 17, 2010. See, Notice of Allowance dated June 17, 2010
`
`attached as WW 1007.
`
`V.
`
`Prior Art on Which Challenge is Based
`
`The ‘392 patent claims the purportedly novel crystalline modification of
`
`pyraclostrobin (crystalline modification IV) used in the agricultural industry to
`
`prevent and treat fungal diseases in certain row crops, including wheat, soybeans
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`and corn, as well as certain fruits and vegetables. This purportedly novel form of
`
`pyraclostrobin is defined by its melting point in the range of 62 to 72°C. The ‘392
`
`patent further claims standard processes to prepare this particular crystalline form
`
`of pyraclostrobin. Each of the references cited in this Petition is prior art to the
`
`‘392 patent as each was published before the June 19, 2005 critical date and each,
`
`alone or in combination, specifically discloses all elements recited by the claims of
`
`the ‘392 patent. The cited references are as follows:
`
`A.
`
`Crystalline Modification IV of Pyraclostrobin
`
`Public Release Summary on Evaluation of the New Active Pyraclostrobin
`
`in the Product Cabrio Fungicide, Australian Pesticides and Veterinary
`
`Medicines Authority, September, 2003 (“Australian”), attached as WW 1008.5
`
`Pyraclostrobin crystalline modification IV having a melting point in the range from
`
`62 to 72°C was known well before June 19, 2005. In this regard, Australian
`
`discloses a summary of certain information submitted by BASF Australia Ltd6
`
`(“BASF Australia”) regarding pyraclostrobin.
`
` Australian discloses BASF
`
`5
`
`The Declaration of J. Hindah Weissbrot declaring to the public availability
`
`of Australian in 2003 is attached as WW 1009.
`
`6
`
`Upon information and belief, BASF Australia is an affiliate of Patent Owner
`
`BASF SE.
`
`13
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`Australian’s proposal to register an emulsifiable concentrate fungicide containing
`
`pyraclostrobin as the sole active ingredient – which it intended to market under the
`
`name Cabrio - to be applied to bananas and grapevines as a foliar spray to control
`
`leaf speckle, leaf spot, and powdery mildew fungi. WW 1008 at 1. Australian
`
`describes the pyraclostrobin compound for which BASF Australia was seeking
`
`approval to market as a “white to light beige…crystalline powder” having a
`
`melting point in the range of “63.7-65.2°C.” Id. at 2. (Emphasis added).
`
`Australian further discloses pyraclostrobin of at least 95% purity suspended
`
`in an aqueous suspension.
`
`Pyraclostrobin is a new active constituent and there is no compendial
`specification available for pyraclostrobin. On the basis of the data
`provided, the following minimum compositional standard has been
`established for pyraclostrobin.
`
`Active constituent
`
`Pyraclostrobin
`
`
`
`Minimum content
`
`Not less than 950 g/kg
`
`Formulated Product
`
`…
`
`Distinguishing name:
`Formulation type:
`Active constituent concentration:
`
`
`
`Cabrio Fungicide
`Emulsifiable Concentrate (EC)
`250 g/L pyraclostrobin
`
`Physical and Chemical Properties of the Product
`
`Physical State:
`
`
`
`Liquid
`
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`
`Id. at 3-4. (Emphasis in original).
`
`B.
`
`Processes for Crystallizing Organic Compounds
`
`Solid organic compounds when isolated from organic reactions are seldom
`
`pure. Rather, they are usually contaminated with small amounts of other
`
`compounds (“impurities”) produced as byproducts during synthesis of the desired
`
`compound. Accordingly, chemists have long worked on developing methods to
`
`purify solid organic compounds. One of the oldest methods is known as
`
`“crystallization” (or “recrystallization” as it is sometimes referred), defined as the
`
`isolation of crystalline compounds from a suitable solvent or mixture of solvents.
`
`WW 1003 at ¶72. By dissolving organic compounds in particular solvents (most
`
`often heated solvents), and then obtaining these compounds in solid crystalline
`
`form (most often by cooling these solvents), purer crystalline forms of these
`
`compounds are obtained. Id. No matter what physical form these compounds
`
`might happen to have prior to the crystallization process (whether amorphous or
`
`polymorphs of another form), their dissolution in the solvent destroys all
`
`“memory” of the prior crystal form with the resulting crystal form often being
`
`another, more stable crystal structure of that compound. Id. at ¶73. As will be
`
`seen below, the crystallization methods claimed by the ‘392 patent have been well
`
`known and used by chemists long before the earliest priority date on which the
`
`‘392 patent may rely.
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`A Textbook of Practical Organic Chemistry Including Qualitative Organic
`
`Analysis, Arthur I. Vogel, Third Ed. (1956) (“Vogel”), attached as WW 1010. In
`
`the section of Vogel entitled Purification of Solid Organic Compounds by
`
`Crystallization, Vogel describes the crystallization process as: (i) dissolving the
`
`substance in a suitable solvent at or near the boiling point of the chosen solvent;7
`
`(ii) filtering the heated solution from particles of insoluble material; (iii) cooling
`
`the heated solution, thus causing the dissolved substance to crystallize; and (iv)
`
`separating the crystals from the supernatant solution (also known as the mother
`
`liquor). WW 1010 at 123. The resulting solid, after drying, is tested for purity
`
`(usually by a melting point determination) and if found to be not sufficiently pure,
`
`is again recrystallized using fresh solvent. Id. This process is repeated until the
`
`desired degree of purity of the compound is obtained. Id.
`
`7
`
`Vogel discloses use of a number of common solvents to crystallize organic
`
`compounds with boiling points higher than 50°C, including water (100°C), acetone
`
`(56°C), chloroform (61°C), methanol (64-65°C), ethyl acetate (78°C), ethanol
`
`(78°C), benzene (80°C), and acetic acid (118°C). Id. at 124. Accordingly, when
`
`using any of these solvents to crystallize a compound pursuant to the method
`
`recited in Vogel, such crystallization will be conducted by dissolving the original
`
`solid at a temperature above 50°C. WW 1003 at ¶76.
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`16
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`Vogel also discusses the practice of adding a second solvent to a solution
`
`containing the dissolved substance to be crystallized.
`
`If the substance is found to be far too soluble in one solvent and much
`too
`insoluble
`in another solvent
`to allow [for] satisfactory
`recrystallization, mixed solvents or “solvent pairs” may frequently be
`used with excellent results. The two solvents must, of course, be
`completely miscible. Recrystallization from mixed solvents is
`carried out near the boiling point of the solvent. The compound is
`dissolved in the solvent in which it is very soluble, and the hot
`solvent, in which the substance is only sparingly soluble, is added
`cautiously until a slight turbidity is produced. The turbidity is then
`just cleared by the addition of a small quantity of the first solvent and
`the mixture is allowed to cool to room temperature; crystals will
`separate. Pairs of liquid which may be used include: alcohol and
`water; alcohol and benzene; benzene and petroleum ether; acetone
`and petroleum ether; glacial acidic acid and water.
`
`Id. at 125. (Emphasis added). Accordingly, Vogel further teaches the use of
`
`alcohols (as well as alkanols) and water as solvents in the crystallization process.
`
`Finally, Vogel further teaches agitating the suspension in order to prompt
`
`crystallization.
`
`“The tube should be scratched below the surface of the solution with a
`glass rod; the fine scratches on the walls (and the minute fragments of
`glass produced) may serve as excellent nuclei for crystal growth. If
`crystals do not separate, even after scratching for several minutes and
`
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`Petition for Inter Partes Review
`U.S. Pat. No. 7,816,392
`cooling in an ice-salt mixture, the solvent is rejected. If crystals
`separate, the amount of these should be noted.”
`
`Id.
`
`Wolfgang Beckmann, Seeding the Desired Polymorph: Background,
`
`Possibilities, Limitations, and Case Studies, Organic Process Research &
`
`Development 2000, 4, 372-383 (“Beckmann”), attached as WW 1011. Beckmann
`
`teaches techniques for seeding a desired polymorph during cry
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