Petition For Inter Partes Review
`Patent No. 8,476,010
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`UNITED STATES PATENT AND TRADEMARK OFFICE
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`
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`J KYLE BASS and ERICH SPANGENBERG
`
`Petitioner
`
`v.
`
`FRESENIUS KABI USA, LLC
`
`Patent Owner
`
`
`
`U.S. Patent No. 8,476,010 B2
`
`Mailed: November 25, 2015
`
`
`
`PETITION FOR INTER PARTES REVIEW OF
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`U.S. PATENT NO. 8,476,010
`
`AND MANDATORY NOTICES UNDER 37 C.F.R. § 42.8
`
`
`Patent No. 8,476,010
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`
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`
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`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`
`
`J KYLE BASS and ERICH SPANGENBERG
`
`Petitioner
`
`v.
`
`FRESENIUS KABI USA, LLC
`
`Patent Owner
`
`
`
`U.S. Patent No. 8,476,010 B2
`
`Mailed: November 25, 2015
`
`
`
`PETITION FOR INTER PARTES REVIEW OF
`
`U.S. PATENT NO. 8,476,010
`
`AND MANDATORY NOTICES UNDER 37 C.F.R. § 42.8
`
`
`
`Petition For Inter Partes Review
`Patent No. 8,476,010
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`
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`TABLE OF CONTENTS
`
`I.
`
`II.
`
`INTRODUCTION ........................................................................................... 1
`
`SUMMARY OF ARGUMENT ...................................................................... 1
`
`III. MANDATORY NOTICES UNDER 37 C.F.R. § 42.8(a)(1) ......................... 2
`
`A.
`
`Real Party-In-Interest Under 37 C.F.R. § 42.8(b)(1) ........................... 2
`
`B.
`
`Related Matters Under 37 C.F.R. § 42.8(b)(2) ..................................... 3
`
`C.
`
`Lead And Back-Up Counsel Under 37 C.F.R. § 42.8(b)(3) ................. 4
`
`D.
`
`Service Information Under 37 C.F.R. § 42.8(b)(4) .............................. 4
`
`IV. PAYMENT OF FEE UNDER 37 C.F.R. § 42.103 ......................................... 4
`
`V.
`
`REQUIREMENTS FOR INTER PARTES REVIEW UNDER 37 C.F.R. §
`42.104 .............................................................................................................. 4
`
`
`
`A. Grounds For Standing Under 37 C.F.R. § 42.104(a) ............................ 4
`
`
`
`Identification of Challenge Under 37 C.F.R. § 42.104(b) And
`B.
`Statement of Precise Relief Requested ........................................................... 5
`
`VI. THRESHOLD REQUIRMENT FOR INTER PARTES REVIEW ............... 6
`
`VII. THE LEVEL OF ORDINARIRY SKILL IN THE ART ............................... 7
`
`VIII. HOW THE CHALLENGED CLAIMS ARE TO BE CONSTRUED ........... 8
`
`IX. STEMENT OF REASONS FOR RELIEF REQUESTED ........................... 12
`
`BACKGROUND AND STATE OF THE ART ........................................... 13
`
`X.
`
`XI. SUMMARY OF ‘010 PATENT ................................................................... 18
`
`XII. GROUND 1: CLAIMS 1, 13-15,17, 18, 20, AND 24-28 ARE OBVIOUS
`OVER THE PRIOR ART OF THE DIPRIVAN PDR, FARINOTTI, AND
`THE ‘864 PATENT ...................................................................................... 22
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`XIII. GROUND 2: CLAIMS 1, 13-15,17, 18, 20, AND 24-28 ARE OBVIOUS
`OVER THE PRIOR ART OF THE DIPRIVAN PDR, FARINOTTI, AND
`THE WO’043 PATENT ................................................................................ 34
`
`
`XIV. SECONDARY CONSIDERATIONS, EVEN IF CONSIDERED, FAIL TO
`OVERCOME THE EVIDENCE OF OBVIOUSNESS................................ 38
`
`
`XV. CONCLUSION ............................................................................................. 39
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`CASES CITED
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`Alcon Research, Ltd. v. Apotex Inc.,
`687 F.3d 1362 (Fed. Cir. 2012),
`cert denied, 133 S. Ct. 1736 (2013)..............................................................23, 26
`
`Daiichi Sankyo Co. v. Apotex Inc.,
`501 F.3d 1254 (Fed. Cir. 2007) ........................................................................... 8
`
`KSR Int'l Co. v. Teleflex Inc.,
`550 U.S. 398 (2007)......................................................................................22, 33
`
`Leapfrog Enters. Inc. v. Fisher-Price Inc.,
`485 F.3d 1157 (Fed. Cir. 2007) .......................................................................... 39
`
`Par Pharm. Inc. v. TWI Pharms., Inc.,
`773 F.3d 1186, No. 2014-1391,
`2014 U.S. App. LEXIS 22737 (Fed. Cir. Dec. 3, 2014) ................................... 22
`
`Richardson-Vicks, Inc. v. Upjohn Co.,
`122 F.3d 1476 (Fed. Cir. 1997) .......................................................................... 39
`
`Zeneca, Inc. v. Shalala,
`213 F.3d 161 (4th Cir. 2000) .............................................................................. 17
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`
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`STATUTES, RULES & OTHER AUTHORITIES
`
`35 U.S.C. § 102(b) ......................................................................................passim
`
`35 U.S.C. § 103(a) ..........................................................................................3, 17
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`35 U.S.C. § 314(a)................................................................................................4
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`37 C.F.R. § 42.100(b)..........................................................................................13
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`EXHIBIT LIST
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`
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`
`
`Exhibit
`#
`1001
`1002
`1003
`
`1004
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`1005
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`1006
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`1007
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`1008
`
`1009
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`1010
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`1011
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`1012
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`1013
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`1014
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`1015
`
`1016
`
`1017
`
`1018
`
`1019
`
`Reference
`U.S. Patent No. 8,476,010
`Declaration of Thomas N. Feinberg, Ph.D
`Curriculum Vitae of Thomas N. Feinberg, Ph.D
`Smith et al., "Siliconization of Parenteral Drug Packaging
`Components," 1988, 42 J. of Parenteral Sci. and Tech. (1988
`Supp.)
`Entry for Diprivan® in the Physician's Desk Reference, 51st
`Edition, 1997, pp. 341, 2939-2945
`R. Farinotti, "Physio-chemical Interactions and Storage of
`Diprivan®," Ann. Fr. Anesth. Reanim., 1994 (French
`Publication)
`Certified English-LanguageTranslation of Exhibit 1006
`
`®
`FAQs
`August 3, 2001 Web page for Diprivan
`Han et al., "Physical properties and stability of two emulsion
`formulations of propofol," Int'l J.of Pharmaceutics, 215 (2001)
`207-220
`U.S. Patent No. 5,383,864
`West Technical Support Bulletin 1999/013, "Evaluating B2-
`Coating as an Alternative to Silicone Oil," January 26, 1999
`West Technical Report 2000/026, "B2-Coating Quantitative
`Particle Analysis," November 15, 2000
`"Siliconization: As Applied to Containers and Closures,"
`Bulletin
`of the Parenteral Drug Association, Vol. 22, No. 2 March/April
`1968
`U.S. Patent No. 5,714,520
`Complaint from Civil Action No. 14-cv-00160-RGA (D. Del.),
`Dkt. 1 (filed February 6, 2014)
`Waiver of Service of Summons from Civil Action No. 14-cv-
`00160-RGA (D. Del.), Dkt. 5 (filed March 10, 2014)
`September 6, 2007 Response to Office Action, U.S. Serial
`No. 10/616,709
`July 13, 2012 Office Action, U.S. Serial No. 10/616,709
`December 16, 2010 Response to Office Action, U.S. Serial
`No. 10/616,709
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`iv
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`1020
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`February 4, 2013 Response to Office Action, U.S. Serial
`No. 10/616,709
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`1021
`
`May 15, 2013 Interview Summary, U.S. Serial No. 10/616,709
`
`1022
`
`1023
`
`1024
`
`1025
`
`1026
`
`1027
`
`1028
`
`1029
`
`1030
`
`1031
`
`1032
`
`1033
`
`May 15, 2013 Notice of Allowability and Examiner's
`Amendment,
`U.S. Serial No. 10/616,709
`Excerpts from "Plaintiff Fresenius Kabi USA, LLC's Opening
`Claim Construction Brief" in Civil Action No. 14-cv-00160-RGA
`(D. Del.)
`Webster's Third New International Dictionary (2002) selected
`page
`Colas, "Silicones in Pharmaceutical Applications," Dow Corning
`Healthcare Industries (2001)
`Hawley's Condensed Chemical Dictionary (13th ed. 1997)
`
`Dutch Diprivan® Registration, 10 mg SmPC RVG 25809
`
`Certified English-Language Translation of Exhibit 1027
`
`Excerpts from file history of U.S. Patent No. 6,576,245
`(Lundgren et al.)
`Declaration of Peggy Frandolig with attached Exhibits A and B
`(Exhs. 1011, 1012).
`Publication WO 20000012043 (Lundgren)
`In re Cuozzo Speed Techs., LLC, No. 2014-1301, 2015 U.S.
`App.
`LEXIS 1699, Slip. Op. at 16, 19 (Fed. Cir. Feb. 4, 2015)
`U.S. Patent No. 2,649,090
`
`1034
`
`U.S. Patent No. 3,958,572
`
`1035
`
`U.S. Patent No. 3,464,414
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`1036
`
`U.S. Patent No. 2,652,182
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`I. INTRODUCTION
`
`J Kyle Bass and Erich Spangenberg (collectively, "Petitioner") requests
`
`inter partes review of claims 1, 13-15, 17, 18, 20, and 24-28 of U.S. Patent
`
`No. 8,476,010 ("the '010 Patent") (Exh. 1001).
`
`
`
`II. SUMMARY OF ARGUMENT
`
`Propofol, the subject pharmaceutical of the ‘010 Patent, is a well-known
`
`intravenous anesthetic agent that was first approved for marketing in the United
`
`States in 1989 and is sold under the proprietary name of “Diprivan”. Specifically,
`
`the '010 Patent is directed to a propofol formulation that is “stored in containers
`
`having non-reactive, or inert closures” (Exh. 1001 col 1:8-10). Likewise, the non-
`
`reactive closures claimed by the ‘010 Patent as siliconized rubber stoppers, were
`
`also very well known at the time of the alleged invention. In addition to being inert
`
`toward the contents of pharmaceutical containers (see, e.g., U.S. 2,649,090 to
`
`Parsons, Ex. 1033) non-reactive closures, such as, specifically, siliconized butyl-
`
`rubber stoppers were known to have significant advantages over unsiliconized
`
`stoppers, exhibiting such desirable characteristics as such as lubricity (see, e.g.,
`
`U.S. 3,958,572 to Lawhead, Exh. 1034), resistance to moisture transfer (see, e.g.
`
`U.S. 3,464,414 to Sponnoble, Exh. 1035) and ease of manufacture (see, e.g. U.S.
`
`2,652,182 to Umbdenstock, Exh. 1036). These important advantages permitted
`
`siliconized stoppers, inter alia, to be used with a wide variety of pharmaceutical
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`Petition For Inter Partes Review
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`composition due to their inert characteristics, to be more easily inserted into and
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`removed from containers, and to be manufactured more efficiently.
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`Such design advantages provided ample motivation to modify prior art to
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`replace unsilconized stoppers with siliconized stoppers. This minor and routine
`
`substitution would have been readily obvious to a person of ordinary skill in the art
`
`("POSA") and not at all outside the realm of routine experimentation or design
`
`optimization. There would have been a reasonable expectation of being able to use
`
`such closures successfully in a propofol container system without extraordinary
`
`testing and research.
`
`III. MANDATORY NOTICES UNDER 37 C.F.R § 42.8(a)(1)
`
`A. REAL-PARTY-IN-INTEREST UNDER 37 C.F.R § 42.8(b)(1)
`
`Pursuant to 37 C.F.R. § 42.8(b)(1), Petitioner certifies the following
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`information: Other than J Kyle Bass and Erich Spangenberg, no other person
`
`(including any entity) has authority to direct or control (i) the timing of, filing
`
`of, content of, or any decisions or other activities relating to this Petition or (ii)
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`any timing, future filings, content of, or any decisions or other activities
`
`relating to the future proceedings related to this Petition. All of the costs
`
`associated with this Petition are to be borne by J Kyle Bass and Erich
`
`Spangenberg. None of the RPI has any financial interest in any securities of
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`Fresnius Kabi USA or its parent corporation, Fresnius SE & Co KGaA.
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`B. RELATED MATTERS UNDER 37 C.F.R. § 42.8(b)(2)
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`Patent Owner has asserted the '010 Patent against Dr. Reddy's
`
`Laboratories, Ltd., in a litigation (dismissed) in the United States District Court
`
`for the District of Delaware. Fresenius Kabi USA, LLC v. Dr. Reddy's Labs.,
`
`Ltd. et al., 14 160-RGA (D. Del.) ("the Litigation").
`
`The ‘010 Patent was also the subject of the below litigations: Fresenius Kabi
`
`USA, LLC v. Watson Laboratories, Inc. et al., DED-1-14-cv-00161 (Dismissed);
`
`Fresenius Kabi USA, LLC v. Emcure Pharmaceuticals USA, Inc. et al., DED-1-14-
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`cv-01141 (Dismissed); Fresenius Kabi USA, LLC v. Emcure Pharmaceuticals
`
`USA, Inc. et al., NJD-1-14-cv-05584 (Dismissed); Fresenius Kabi USA, LLC v.
`
`Agila Specialties Private Ltd. et al., DED-1-14-cv-01438 (Dismissed); Fresenius
`
`Kabi USA, LLC v. Mylan Laboratories Limited et al., WVND-1-14-cv-00205
`
`(Dismissed); Fresenius Kabi USA, LLC v. Claris Lifesciences Ltd. et al., NJD-1-
`
`14-cv-07953 (Dismissed); Fresenius Kabi USA, LLC v. Claris Lifesciences Ltd. et
`
`al., DED-1-14-cv-01498 (Dismissed); Petition for Inter Partes Review by Dr.
`
`Reddy's Laboratories, Inc., PTAB-IPR2015-00715 (Terminated); Dr. Reddy's
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`Laboratories, Inc. et al v. Fresenius Kabi USA, LLC., DED-1-15-cv-00714
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`(Terminated).
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`Patent No. 8,476,010
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`C. NOTICE OF LEAD AND BACKUP COUNSEL UNDER 37
`C.F.R. § 42.8(b)(3)
`
`Lead Counsel:
`Dr. Gregory J. Gonsalves
`Reg. No. 43,639
`2216 Beacon Lane
`Falls Church, VA 22043 (571) 419-7252
`gonsalves@gonsalveslawfirm.com
`
`Backup Counsel:
`Christopher Casieri
`McNeely, Hare & War LLP
`12 Roszel Road, Suite C104
`Princeton, NJ 08540
`Phone: 609 731 3668
`chris@miplaw.com
`
`
`
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`D. NOTICE OF SERVICE INFORMATION UNDER 37
`C.F.R. § 42.8(b)(4)
`
`Please address all correspondence to the lead and backup counsel at
`
`the addresses shown above. Petitioner also consents to electronic service by e-
`
`mail at: gonsalves@gonsalveslawfirm.com.
`
`IV.
`
`PAYMENT OF FEES UNDER 37 C.F.R. § 42.103
`
`The required fees are submitted herewith in accordance with 37 C.F.R. §§
`
`42.103(a) and 42.15(a). If any additional fees are due during this proceeding, the
`
`Office is authorized to charge such fees to Deposit Account No. 506831.
`
`V. REQUIREMENTS FOR INTER PARTES REVIEW UNDER 37
`C.F.R. § 42.104
`
`A. GROUNDS FOR STANDING UNDER 37 C.F.R. § 42.104(a)
`
`Petitioner certifies that the patent for which review is sought is available
`
`for inter partes review, and that Petitioner is not barred or estopped from
`
`requesting an inter partes review on the grounds identified in the petition
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`because: (1) Petitioner is not the patent owner; (2) Petitioner has not filed a civil
`
`action challenging the validity of a claim in the patent; (3) Petitioner has not
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`been served with a complaint alleging infringement of the patent; (4) the
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`estoppel provisions of 35 U.S.C. § 315(e)(1) do not prohibit this IPR; and (5)
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`the patent is not described in § 3(n)(1) of the Leahy-Smith America Invents Act
`
`and so is available for IPR pursuant to 37 C.F.R. § 42.102(a)(2).
`
`B.
`IDENTIFICATION OF CHALLENGE UNDER 37 C.F.R. §
`42.104(a) AND STATEMENT OF PRECISE RELIEF REQUESTED
`
`Petitioner requests that claims 1, 13-15, 17, 18, 20, and 24-28 of the '010
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`Patent be held unpatentable based on the following.
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`IPR of the ‘010 Patent is requested in view of the following prior art: (1) the
`
`1997 Physician’s Desk Reference entry for Diprivan
`
`
`(“Diprivan PDR”) (Exh.
`
`1005); (2) the article entitled "Physio-chemical Interactions and Storage of
`
`Diprivan," by Farinotti, Ann. Fr. Anesth. Reanim., 1994, 13:453-456
`
`("Farinotti") (Exh. 1006)1; (3) U.S. Patent No. 5,383,864 to van den Heuvel issued
`
`January 24, 1995 ("the ’864 Patent") (Exh. 1010); and (4) WO 2000/012043 to
`
`Lundgren et al. issued March 9, 2000 (“the WO’043 Patent”) (Exh. 1031). Each of
`
`the publications listed above is available as prior art against the ‘010 Patent under
`
`
`1 A certified English-language translation of this French publication is included as
`
`Exhibit 1007.
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`Patent No. 8,476,010
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`pre-AIA 35 U.S.C. § 102(b) because each was published more than one year
`
`before July 10, 2003, which is the filing date of the earliest application to which
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`the ‘010 Patent claims priority.
`
`The following combinations of the above-listed publications renders claims
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`1, 13-15, 17, 18, 20, and 24-28 of the ‘010 Patent obvious under pre-AIA 35
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`U.S.C. § 103(a):
`
`Ground 1. Claims 1, 13-15, 17, 18, 20, and 24-28 are obvious over the
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`Diprivan PDR, in view Farinotti, and the ’864 Patent.
`
`Ground 2. Claims 1, 13-15, 17, 18, 20, and 24-28 are obvious over the
`
`Diprivan PDR, in view of Farinotti and the WO’043 Patent.
`
`Copies of the documents cited above are all filed herewith. The above
`
`grounds for unpatenability are supported by the Declaration of Dr. Thomas N.
`
`Feinberg (“the Feinberg Declaration”) (Exh. 1002) also filed herewith.
`
`VI.
`THRESHOLD REQUIREMENT FOR INTER PARTES
`REVIEW
`
`“A patent may not be obtained though the invention is not identically
`
`disclosed or described as set forth in section 102 of this title, if the differences
`
`between the subject matter sought to be patented and the prior art are such that the
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`subject matter as a whole would have been obvious at the time the invention was
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`made to a person having ordinary skill in the art to which said subject matter
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`Patent No. 8,476,010
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`pertains.” 35 U.S.C. § 103(a). Underlying factual determinations in an obviousness
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`analysis include (1) the scope and content of the prior art, (2) the level of ordinary
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`skill in the art, (3) the differences between the claimed invention and the prior art,
`
`and (4) objective indicia of nonobviousness. See Merck & Co. v. Teva Pharms.
`
`USA, Inc., 395 F.3d 1364, 1369 (Fed. Cir. 2005) (citing Graham v. John Deere
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`Co., 383 U.S. 1, 17-18 (1966)). The scope and content of the prior art, the level of
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`ordinary skill in the art, and the differences between the claimed invention and the
`
`art relevant to this Petition are addressed for each statutory ground of rejection
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`upon which this Petition is based.
`
`In this regard, Inter Partes Review of the claims identified below is
`
`requested on the grounds that these claims are unpatentable for failing to meet the
`
`requirements of 35 U.S.C. § 103(a). All of the limitations of claims 1, 13-15, 17,
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`18, 20, and 24-28 of the '010 Patent are taught or suggested in the prior art and one
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`of ordinary skill in the art would have been motivated to combine the teachings of
`
`the cited references with a reasonable expectation of success, as explained in detail
`
`below. Copies of the references rendering these claims unpatentable are filed
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`herewith. 37 C.F.R. § 42.6(c).
`
`VII.
`
`THE LEVEL OF ORDINARY SKILL IN THE ART
`
`Factors relevant to determining the level of skill in the art include: the
`
`educational level of the inventors, the types of problems encountered in the art,
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`Patent No. 8,476,010
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`prior art solutions to those problems, the rapidity with which innovations are made,
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`the sophistication of the technology, and the educational level of active workers in
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`the field. Daiichi Sankyo Co. v. Apotex Inc., 501 F.3d 1254, 1256 (Fed. Cir. 2007).
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`In the field of the alleged invention, a person of ordinary skill in the art at
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`the time of the invention would have been someone with substantial research or
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`industry experience in pharmaceutical drug product development, including
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`experience with sterile drugs and their packaging, and having at least a master's
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`degree or doctorate in a related technical field, such as analytical, physical or
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`organic chemistry, chemical engineering, pharmaceutics or related subject matter
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`or having equivalent experience in such fields. (Exh. 1002, Feinberg Decl. ¶ 8.)
`
`VIII. HOW THE CHALLENGED CLAIMS ARE TO BE
`CONSTRUED
`
`In inter partes review, a claim term is to be given its "broadest reasonable
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`construction in light of the specification as understood by one of ordinary skill in
`
`the art. See 37 C.F.R. § 42.100(b)
`
`Claim 1 of the ‘010 reads as follows:
`
`1.
`
`A sterile pharmaceutical composition of propofol in a
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`container, comprising:
`
`-a container which includes a closure and a composition in the container, and
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`Petition For Inter Partes Review
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`-the composition in the container comprising from 0.5% to 10% by weight
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`propofol and from about 0 to about 10% by weight solvent for propofol,
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`-where when the composition in the container sealed with the closure is
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`agitated at a frequency of 300-400 cycles/minute for 16 hours at room temperature,
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`the composition maintains a propofol concentration (w/v) measured by HPLC that
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`is at least 93% of the starting concentration (w/v) of the propofol;
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`-where the closure is selected from the group consisting of siliconized
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`bromobutyl rubber, metal, and siliconized chlorobutyl rubber.
`
`A.
`
`"From About Zero To About 10%"
`
`Claim 1 requires that the propofol composition have "from about 0 to about
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`10% by weight solvent for propofol." The patent owner recently construed this
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`phrase in the Litigation to mean approximately 0 to approximately 10% solvent by
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`weight, including compositions with 10% soybean oil. (See Exh. 1023, at 5 (citing
`
`Merck & Co. v. Teva Pharms. USA, Inc., 395 F.3d 1364, 1369-70 (Fed. Cir. 2005))
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`for the proposition that "about" means "approximately"; id. at 5-6 (asserting that
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`"there is no support in the intrinsic record" for a construction that excludes exactly
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`10% by weight solvent).
`
`To support this construction, the patent owner cited certain intrinsic
`
`evidence, including a passage from the specification that states that "the water
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`miscible solvent or the water-immiscible solvent is present in an amount that is
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`preferably from 0 to 10% by weight of the composition" (Exh. 1001, at 5:36-38)
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`(Exh. 1023, at 6.) The patent owner also cited portions of the prosecution history
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`in which the examiner amended the term "less than 10% by weight solvent for
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`propofol" (see Exh. 1019, at 2) to "from about 0 to about 10% by weight solvent
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`for propofol" (Exh. 1022, at 2). (Exh. 1023, at 7.)
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`Petitioner accepts the patent owner's position as the broadest reasonable
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`interpretation of the phrase in inter partes review. Accordingly, Petitioner accepts
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`as the broadest reasonable construction for purposes of this proceeding the patent
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`owner's construction of "from about zero to about 10% by weight solvent for
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`propofol" to mean from approximately zero to approximately 10% solvent by
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`weight, a range that includes 10%. The reference to "about 10% by weight
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`solvent," in accordance with the explanation in the patent, is "meant to be weight
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`percent by volume of the composition." (Exh. 1001, 5:33-35.)
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`B.
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`"Siliconized"
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`Although "siliconized" is not defined in the specification or prosecution
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`history of the '010 Patent, its definition is well known, and it means surface-treated
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`or coated with a silicone. (Exh. 1002, Declaration of Thomas Feinberg ("Feinberg
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`Decl.") ¶ 10; Webster’s Third New Int’l Dictionary 2118 (2002) (Exh. 1024, at
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`2118), defining "siliconize" as "to treat or coat (as with a lens) with a silicone";
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`Colas, "Silicones in Pharmaceutical Applications," Dow Corning Corporation
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`(2001) (Exh. 1025), at 19 ("Siliconisation encompasses the surface treatment of
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`many parenteral packaging components with silicones."); Smith et al.,
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`Siliconization of Parenteral Drug Packaging Components, 1988, 42 J. of
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`Parenteral Sci. and Tech. (1988 Supp.) ("Smith et al.") (Exh. 1004), at S4, S8-S9,
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`describing "siliconization" of parenteral drug packaging components by applying
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`silicones.) "Silicone," in turn, refers to polymer substances including siloxanes, and
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`thus having silicon-oxygen-silicon bonds. (Exh. 1002, Feinberg Decl. ¶ 10; Exh.
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`1004, at S12, defining "silicone" as "a general term describing a solid or liquid
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`polymer made up of silicon-oxygen-silicon bonds in which hydrocarbon groups are
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`bonded directly to all or a portion of the silicon atoms"; Hawley's Condensed
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`Chemical Dictionary 997 (13th ed. 1997) (Exh. 1026), defining "silicone" as "any
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`of a large group of siloxane polymers based on a structure consisting of alternate
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`silicon and oxygen atoms with various organic radicals attached to the silicon.").
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`Accordingly "siliconized," in the context of the challenged claims and the
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`applicable claim construction standard, refers to a closure that is surface-treated,
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`coated, or manufactured with silicone or one or more siloxane polymers. (Exh.
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`1002, Feinberg Decl. ¶ 10.)
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`C.
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`"Inert To Propofol"
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`The phrase "inert to propofol" in challenged claims 17 and 18 means having
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`no significant reactivity to propofol. This interpretation is consistent with how a
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`POSA would have understood this phrase in light of the specification, which uses
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`the terms "inert" and "non-reactive" interchangeably. (Exh. 1002, Feinberg Decl. ¶
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`12; Exh. 1001, at 1:8-10 ("the invention pertains to propofol formulations that are
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`stored in containers having non-reactive, or inert closures"); see also id. 3:63-4:2,
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`4:47-48, 8:41-42.) As the specification further explains, an "inert" closure does not
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`cause "significant" degradation of the propofol formulation. (Id. at 4:46-50.)
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`Thus, in the context of the '010 Patent, "inert" means having no significant
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`reactivity to propofol. (Exh. 1002, Feinberg Decl. ¶ 12.)
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`IX.
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`STATEMENT OF REASONS FOR RELIEF REQUESTED
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`
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`In the specification of the '010 Patent and during patent prosecution, the
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`patentee focused on the putative instability of propofol formulations containing
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`less than 10% of a soybean oil solvent when exposed to some uncoated rubber
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`stoppers. But because the challenged claims include solvent concentrations of
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`10%, the instability problem identified by the patentee is not pertinent to the
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`challenged claims. As the '010 Patent admits, at 10% w/v of soybean oil, propofol
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`formulations, including commercial Diprivan, are completely stable with different
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`types of stoppers. Thus, there is no stability "problem" to be solved. Given that a
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`POSA would have had ample motivation to replace the Diprivan unsilconized
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`stopper with a siliconized version for reasons separate and apart from stability (e.g.
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`ease of insertion, ease of manufacture, etc.), the use of a different stopper was
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`readily obvious and an unpatentable modification.
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`Furthermore, given the relatively small number of available closure options,
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`it would have been obvious to try any one of them and it would have been
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`reasonable to expect that siliconized rubber stoppers would prove successful.
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`X. Background and State of the Art
`
`The '010 Patent confirms that commercial Diprivan was previously well
`
`known and exhibited several features claimed in the ‘010 Patent at the time of
`
`filing (Exh. 1001, 2:33-39). A Diprivan formulation was described in prior art U.S.
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`Patent No. 5,714,520 ("the '520 Patent") (Exh. 1014) as a sterile propofol emulsion
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`containing 1% propofol w/v and 10% soybean oil w/v, along with other excipients.
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`(Exh. 1001, 2:33-39; Exh. 1014, 7:5-15; Exh. 1002, Feinberg Decl. ¶ 24.) The
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`'520 Patent also discloses other claimed elements of the ‘010 Patent, including that
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`the composition is sterile (Exh. 1014, 4:38-39) and that it may be packaged in 50
`
`mL or 100 mL vials (id., 7:65-67).
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`The ’010 Patent also claims a requirement for propofol stability based on an
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`accelerated stability test. Diprivan had already met that test at the time of filing.
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`(Exh. 1002, Feinberg Decl. ¶ 15; Exh. 1001, 25:15-32.) As reported in example 34
`
`of the '010 Patent, the patentee tested "[c]ommercially available Diprivan,"
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`containing 10% soybean oil, 1.2% lecithin, 1% propofol and a "Rubber 1" stopper,
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`- 13 -
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`made of bromobutyl rubber. (Id at 23:51, 25:27-37.) Diprivan exhibited 99.3%
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`retention of propofol following shaking in its container at a frequency of 300-400
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`cycles/minute for 16 hours -- the same accelerated stability test recited in the
`
`claims (Id., 23:21-34, 25:10-31). Further, this test methodology was known in the
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`prior art. (Han et al., "Physical properties and stability of two emulsion
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`formulations of propofol," Int'l Journal of Pharmaceutics, 215 (2001) 207-220, at
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`217 (Exh. 1009); Exh. 1002, Feinberg Decl. ¶ 16.) A registration document for a
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`1% Diprivan product in the Netherlands similarly stated that the product had at
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`least three years of shelf stability. (Exh. 1028, at 13 and at 12, Section 6.3.2)
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`Because Diprivan, in the real world, was stable for several years, the patentee's
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`reliance on an arbitrary test that merely simulates actual stability (Exh. 1001, 4:51-
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`58, 27:45-52) cannot make the composition any more stable for physician or
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`patient use, or confer patentability.
`
`
`2 Exh. 1028 is a certified English-language translation of Exh. 1027, a Dutch
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`registration document for Diprivan, stating that the product registration in the
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`Netherlands was issued on December 5, 2000. (Exh. 1028, at 13.) This document
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`was obtained from the drug information database of the Dutch Medicines
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`Authority, publicly available at www.geneesmiddeleninformatie-bank.nl, which is
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`updated on a weekly basis with new registrations.
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`Regarding the supposed invention of the use of a siliconized rubber stopper,
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`as far back as 1950, U.S. Patent No. 2,649,090 recognized the utility of siliconizing
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`rubber stoppers in order “to provide a surface sealing substance on the rubber
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`stoppers to render the rubber more inert towards the contents of … vials” useful in
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`“pharmaceutical work” (Exh. 1033 col 1:18-21 and col 3:47). Other advantages
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`delineated in the art included ease of manufacture, better sealing of closed
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`containers, reduce moisture permeability, greater lubricity, and the ability of the
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`stoppers to be sterilized (Exh. 1033 col 1: 9-27, col 2:46-49).
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` U.S. 2,652,182 (Exh. 1036) issued in 1953 taught siliconized rubber
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`stoppers “having improved properties which [are] adapted for use in machines for
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`automatically and mechanically stoppering vials or bottles. In particular, …to
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`rubber stoppers having improved properties and which are adapted for use in
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`packaging certain drugs and therapeutic materials in bottles or vials under sterile
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`conditions” (Exh. 1036 col 1:4-9) The improvement was accomplished by a
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`“lubricating coating of a polymeric silicone on the surface of the rubber” (Exh.
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`1036 col 2:3-11 and col 3:40-45) The siliconized rubber stoppers exhibited ease of
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`manufacture (i.e. they did not stick together during production runs) and were
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`easier to assemble into the final pharmaceutical bottle or vial. (Exh. 1002 ¶ 21).
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`In 1968, the art recognized that "rubber closures may also be siliconized to
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`provide 'machinability' in order to maintain economical rates of production." (Exh.
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`1013, at 69, Abstract.) Similarly, Smith taught in 1988 that "[m]achinability is
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`greatly improved through the use of lubricated packaging components.
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`Siliconization of rubber products reduces the friction present between the rubber
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`closure and the metallic machinery." (Exh. 1004, at S4; Exh. 1002, Feinberg Decl.
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`¶ 21.) A Dow Corning article published in 2001 likewise taught the siliconization
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`of parenteral packaging components, such as stoppers, "to ease machinability."
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`(Exh. 1025, at 19, 22.) The West publications noted the "benefits" of "lubricity and
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`processability" conferred by siliconized closures such as the B2. (Exh. 1011.)
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`Thus, the art recognized that siliconization was known to provide improved
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`economical rates of production, reduced clumping and a reduction in other costly
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`line disruptions that might occur with unsiliconized stoppers. (Exh. 1002, Feinberg
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`Decl. ¶¶ 20-21.)
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`Smith confirms an additional advantage of siliconization, noting that it
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`"lowers the friction between the vial and the closure. This decrease in friction
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`reduces the force necessary to insert vial stoppers properly." (Exh. 1004, at S4;
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`Exh. 1002, Feinberg Decl. ¶ 21.) Smith also notes that sealability -- the integrity of
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`the closure seal -- "is improved by siliconization of the closure." (Exh. 1004, at S4;
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`Exh. 1002, Feinberg Decl. ¶ 21.)
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`In 1969 U.S. Patent 3,464,414 indicated that butyl rubber stoppers,
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`specifically, were amenable to siliconization in order to “prevent[] moisture
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`Petition For Inter Partes Review
`Patent No. 8,476,010
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`transmission” to a pharmaceutical composition as well as to increase lubricity by
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`exhibiting “easy displacement of the butyl plug” that was siliconized (Exh. 1035
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`Abstract and col 1:14-17).
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`Furthe
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