`Tel: 571-272-7822
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`Paper 9
`Entered: February 4, 2016
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`UNITED STATES PATENT AND TRADEMARK OFFICE
`_______________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`_______________
`
`SAWAI USA, INC. AND SAWAI PHARMACEUTICAL CO., LTD.,
`Petitioners,
`
`v.
`
`NISSAN CHEMICAL INDUSTRIES LTD.,
`Patent Owner.
`____________
`
`Cases IPR2015-01647
`Patent No. 5,856,336 B2
`_______________
`
`Before JACQUELINE WRIGHT BONILLA, SHERIDAN K. SNEDDEN,
`and TINA E. HULSE, Administrative Patent Judges.
`
`SNEDDEN, Administrative Patent Judge.
`
`
`
`
`DECISION
`Denying Institution of Inter Partes Review
`37 C.F.R. § 42.108
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`
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`IPR2015-01647
`Patent 5,856,336 B2
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`I. INTRODUCTION
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`Sawai USA Inc. and Sawai Pharmaceutical Co., Ltd. (“Petitioner”)
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`filed a Petition to institute an inter partes review of claims 1 and 2 (Paper 1,
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`“Pet.”) of U.S. Patent No. 5,856,336 B2 (Ex. 1001, “the ’336 patent”).
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`Nissan Chemical Industries, Ltd. (“Patent Owner”) filed a Patent Owner
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`Preliminary Response. Paper 8 (“Prelim. Resp.”).
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`Upon consideration of the Petition and Patent Owner Preliminary
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`Response, we conclude that Petitioner has not established that there is a
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`reasonable likelihood that it will prevail with respect to at least one of the
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`challenged claims. For the reasons that follow, we do not institute an inter
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`partes review.
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`A. Related Proceedings
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`The parties inform us of no related litigation between them involving
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`the ’336 patent. Pet. 56; Paper 4. Concurrent with the filing of the present
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`Petition, Petitioner also filed a different Petition requesting inter partes
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`review of claims 12 of the ’336 patent (IPR2015-01648).
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`B. The ’336 patent (Ex. 1001)
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`The ’336 patent discloses mevalonolactone derivatives having a
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`quinoline ring and their use as a pharmaceutical for reducing hyperlipidemia,
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`hyperlipoproteinemia, or atherosclerosis. Ex. 1001, 1:635. The
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`compounds are active against the enzyme HMG-CoA (or 3-hydroxy-3-
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`methylglutaryl-coenzyme A). Id. at Abstract.
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` 2
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`IPR2015-01647
`Patent 5,856,336 B2
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`C. Challenged claims
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`Challenged claims 1 and 2 are reproduced below:
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`1. A compound of the formula,
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`
`
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`Z= —CH(OH)—CH2—CH(OH) —CH2—COO. ½Ca.
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`2. A method for reducing hyperlipidemia, hyperlipoproteinemia
`or atherosclerosis, which comprises administering an effective
`amount of the compound of formula A as defined in claim 1.
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`Ex. 1001, 32:2040.
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`D. Asserted Grounds of Unpatentability
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`Petitioner challenges claims 1 and 2 of the ’336 patent on the
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`following ground. Pet. 20–57.
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`References
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`Basis
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`Claim[s] challenged
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`Picard1 and Kesseler2
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`§ 103(a)
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`1 and 2
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`
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`1 Joseph A. Picard et al., U.S. Patent No. 4,761,419, issued Aug. 2, 1988.
`Ex. 1009 (“Picard”).
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` Kurt Kesseler et al., U.S. Patent No. 4,925,852, issued May 15, 1990.
`Ex. 1010 (“Kesseler”).
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` 3
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` 2
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`IPR2015-01647
`Patent 5,856,336 B2
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`Petitioner relies also on the Declaration of Dr. Milton Brown in
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`support of the proposed ground of unpatentability. Ex. 1012 (“Brown
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`Declaration” or “Brown Decl.”).
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`II. ANALYSIS
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`A. Claim Interpretation
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`We interpret claims using the “broadest reasonable construction in
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`light of the specification of the patent in which [they] appear[].” 37 C.F.R.
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`§ 42.100(b); see also Office Patent Trial Practice Guide, 77 Fed. Reg.
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`48,756, 48,766 (Aug. 14, 2012); In re Cuozzo Speed Techs., LLC, 793 F.3d
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`1268, 1278–79 (Fed. Cir. 2015), cert. granted sub nom. Cuozzo Speed
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`Techs., LLC v. Lee, 84 U.S.L.W. 3218 (U.S. Jan. 15, 2016) (No. 15-446).
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`Under the broadest reasonable construction standard, claim terms are given
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`their ordinary and customary meaning, as would be understood by one of
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`ordinary skill in the art at the time of the invention. In re Translogic Tech.,
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`Inc., 504 F.3d 1249, 1257 (Fed. Cir. 2007). “Absent claim language
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`carrying a narrow meaning, the PTO should only limit the claim based on
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`the specification . . . when [it] expressly disclaim[s] the broader definition.”
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`In re Bigio, 381 F.3d 1320, 1325 (Fed Cir. 2004). “Although an inventor is
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`indeed free to define the specific terms used to describe his or her invention,
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`this must be done with reasonable clarity, deliberateness, and precision.” In
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`re Paulsen, 30 F.3d 1475, 1480 (Fed. Cir. 1994).
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`We determine that no explicit construction of any specific claim term
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`is necessary to determine whether to institute a trial in this case. See, e.g.,
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`Wellman, Inc. v. Eastman Chem. Co., 642 F.3d 1355, 1361 (Fed. Cir. 2011)
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`IPR2015-01647
`Patent 5,856,336 B2
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`(“[C]laim terms need only be construed ‘to the extent necessary to resolve
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`the controversy.’”) (quoting Vivid Techs., Inc. v. Am. Sci. & Eng’g, Inc.,
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`200 F.3d 795, 803 (Fed. Cir. 1999)). At this stage of the proceeding, we
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`have not made a final determination as to the construction of any claim term.
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`B. Effective Filing Date of Claims 1 and 2 of the ʼ336 Patent
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`The ʼ336 Patent claims the benefit of Japanese Patent Applications JP
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`63-193606 (“JP ’606,” filed August 3, 1988),3 JP 63-15585 (“JP ’585,” filed
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`January 26, 1988),4 and JP 62-207224 (“JP ’224,” filed August 20, 1987).5
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`Petitioner contends that neither JP ʼ585 nor JP ʼ224 provides written
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`description for a ½ calcium salt, as specifically required by claims 1 and 2 of
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`the ʼ336 patent. Pet. 1015. Thus, Petitioner contends that the earliest
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`effective filing date for the ʼ336 Patent is no earlier than the filing date of JP
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`’606, or August 3, 1988. Id.
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`In its Preliminary Response, Patent Owner does not direct us to any
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`portion of either JP ʼ585 or JP ʼ224 that provides written description for a ½
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`calcium salt, instead arguing that the Board need not address priority at this
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`time in light of the deficiencies in Petitioner’s arguments. Prelim. Resp. 2
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`n.1. For the purposes of this Decision, we treat Picard and Kesseler as prior
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`art references and consider the patentability challenge set forth in the
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`Petition.
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`3 Certified English translation provided as Ex. 1013.
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`4 Certified English translation provided as Ex. 1014.
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`5 Certified English translation provided as Ex. 1015.
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` 5
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`IPR2015-01647
`Patent 5,856,336 B2
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`C. Petitioner’s Asserted Obviousness Ground
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`1. Petitioner’s Contentions
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`Petitioner contends that claims 1 and 2 of the ’336 patent are obvious
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`over the combination of Picard and Kesseler. Pet. 2539. Petitioner
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`contends that a person of ordinary skill in the art would have selected
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`Picard’s Example 3 compound (Ex. 1009, 17:4966) as a lead compound
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`and would have found it obvious to change the R2 isopropyl group to a
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`cyclopropyl group in order to achieve the compound of claim 1 of the ’336
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`patent. Pet. 2630.
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`In support of this contention, Petitioner directs us to the following
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`teachings of Picard. Id. Picard discloses purported compound inhibitors of
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`3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase)
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`having the structure of the following Formula I (“Picard Formula I”):
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`and X is —CH2CH2— or —CH═CH—. Ex. 1009, Abstract, 2:629. With
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`regard to R1, R2, R3, R4, R5, and R6, Picard discloses as follows:
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`IPR2015-01647
`Patent 5,856,336 B2
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`R1 and R2 are independently hydrogen; alkyl of from one
`to six carbons;
`trifluoromethyl; cyclopropyl; cyclohexyl;
`cyclohexylmethyl; phenyl; phenyl substituted with fluorine,
`chlorine, bromine, hydroxy, trifluoromethyl, alkyl of from one to
`four carbon atoms, or alkoxy of from one to four carbon atoms;
`phenylmethyl; phenylmethyl substituted with fluorine, chlorine,
`bromine, hydroxy, trifluoromethyl, alkyl of from one to four
`carbon atoms, or alkoxy of from one to four carbon atoms; 2-, 3-
`, or 4-pyridinyl; or 2-, -, or 5-pyrimidinyl; provided that when X
`is in the 2-position, R1 is hydrogen and is attached in the 4-
`position.
`
`R3, R4, R5, and R6 are independently selected from
`hydrogen; alkyl of from one to six carbon atoms; trifluoromethyl;
`cyclopropyl; fluorine; chlorine; bromine; hydroxy; alkoxy of
`from one to four carbon atoms; cyano; nitro; amino; acetylamino;
`aminomethyl; phenyl; phenyl substituted with fluorine, chlorine,
`bromine, hydroxy, trifluoromethyl, alkyl of from one to four
`carbon atoms, or alkoxy of from one to four carbon atoms;
`phenylmethyl; or phenylmethyl substituted with fluorine,
`chlorine, bromine, hydroxy, trifluoromethyl, or alkyl of from one
`to four carbon atoms.
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`Id. at 2:3053.
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`
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`Picard also discloses compound inhibitors of HMG-CoA reductase
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`having the structure of the following Formula II (“Picard Formula II”):
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`where X, R1, R2, R3, R4, R5, and R6 are as defined above. Id. at 2:5867.
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`Table 1 of Picard (“Picard Table 1”), reproduced below, discloses the
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`IPR2015-01647
`Patent 5,856,336 B2
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`activities of two compounds encompassed by Formula I. Id. at 11:2541.
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`Example 3 describes the preparation of a compound according to
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`Formula II (“Picard Example 3 Compound”): Id. at 17:4966. Petitioner
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`provides a comparison of the structure of Picard’s Example 3 compound and
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`the claimed compound, reproduced in the table below. Pet. at 28.
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`
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`With reference to the above table, Petitioner contends that Picard Example 3
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`Compound differs from a compound of claim 1 by the presence of an
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`isopropyl at the R2 position, instead of a cyclopropyl group. Id.
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`Petitioner further contends that the data provided in Picard Table 1
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`describes preferred lactones in which R1 is 4-fluorophenyl and R2 is methyl
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`IPR2015-01647
`Patent 5,856,336 B2
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`or isopropyl. Pet. 27 (citing Brown Decl. ¶ 32). According to Petitioner,
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`Picard indicates in Table 1 that a R2 isopropyl substituted compound is
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`about 10 times more potent than its methyl-substituted counterpart. Pet. 27.
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`Based on that data, according to Petitioner, a person of ordinary skill in the
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`art would have reasonably expected “that derivatives having an isopropyl
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`group would be more active than those having a methyl group.” Pet. 27, 30
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`(citing Brown Decl. ¶¶ 32, 37.)
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`Petitioner further contends that Picard discloses “that cyclopropyl is a
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`preferred alternate propyl group at this position, a POSA would naturally
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`have prepared cyclopropyl as the next isomeric propyl alternative.” Id. at 30
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`(citing Brown Decl. ¶ 38).
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`Petitioner further contends that “Kesseler (Ex. 1010) expressly
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`teaches that a cyclopropyl group is preferred to an isopropyl group at the R2
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`position.” Id. at 3031 (citing Brown Decl. ¶ 40). With reference to the
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`table reproduced below, Petitioner directs our attention to compounds Ie and
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`Iac disclosed by Kesseler. Id. at 31; Ex. 1010, 14:2047. According to
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`Petitioner, “Kesseler . . . discloses that changing isopropyl to cyclopropyl in
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`the R2 position (circled) results in a nearly threefold increase in the IC50
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`values.” Pet. 31 (citing Brown Decl. ¶ 41-42).
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`IPR2015-01647
`Patent 5,856,336 B2
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`Petitioner concludes as follows:
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` In view of the clear structural similarity between these
`compounds, a POSA would have understood that each was
`described as an active HMG-CoA reductase inhibitor, and would
`have considered Kesseler’s ring-cracked compounds (i.e., those
`of formulae I and II in Kesseler) to be “analogs” of the ring-fused
`structure of compactin.
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`Accordingly, a POSA would have expected that the activity of
`the compound of Picard Example 3 would have been improved
`by the similar substitution of a cyclopropyl for its isopropyl
`group.
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`Pet. 36 (citations omitted); Brown Decl. ¶¶ 4648, 5152.
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`2. Patent Owner’s Contentions
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`Patent Owner contends that the evidence presented by Petitioner
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`shows that there were many potentially beneficial compounds disclosed in
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`the prior art. Prelim. Resp., 1425 (citing Pet. 15, 1718; Brown Decl. ¶ 25
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`n.1; Ex. 1009, 11:3940 (Table 1); Ex. 1010, 1:3554, 14:2445). Patent
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`Owner further contends that Petitioner’s rationale fails to establish why the
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`Picard Example 3 Compound would have been an obvious choice of a “lead
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`compound” for an HMGCoA reductase inhibitor and thus “is the epitome of
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`10
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`Patent 5,856,336 B2
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`impermissible hindsight reconstruction.” Id. at 14.
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`Patent Owner contends that Picard only provides functional activity
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`data for the compounds provided in Picard Table 1, which does not include
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`the compound disclosed in Example 3 of Picard. Id. at 1718 (citing Ex.
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`1009, col. 11 (Table 1)). Patent Owner argues that the Petitioner fails to
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`provide a sufficient reason for why a person of ordinary skill in the art
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`would “jump to the conclusion that the compound of Example 3 (for which
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`not a shred of in vitro data is provided) would be a better inhibitor of HMG-
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`CoA reductase than the 4-chloro compounds disclosed in Table 1 (for which
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`in vitro data is provided).” Id. at 20.
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`With regard to Kesseler, Patent Owner contends that Kesseler
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`discloses “an entire class of non-quinoline compounds . . . with better
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`activity against HMG-CoA reductase than anything disclosed in Picard.” Id.
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`at 24. According to Patent Owner, Kesseler discloses at least 14 compounds
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`having IC50 values against HMG-CoA reductase between 0.95.0
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`nanomolar, whereas the IC50 values disclosed in Picard were between 32 and
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`350 nanomolar. Id. (citing Ex. 1010, 14:2445; Ex. 1009, 11 (Table 1)).
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`Patent Owner further contends Petitioner fails to provide a sufficient
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`rationale as to why a person of ordinary skill in the art would have equated
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`results from the pyridine and pyrimidine cores of Kesseler to the quinoline
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`cores of Picard. Id. at 3437.
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`3. Analysis
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`We generally follow a two-part inquiry to determine whether a new
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`chemical compound would have been obvious over particular prior art
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`compounds. Otsuka Pharm. Co. v. Sandoz, Inc., 678 F.3d 1280, 1291–93
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`(Fed. Cir. 2012). First, we determine “whether a chemist of ordinary skill
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`would have selected the asserted prior art compounds as lead compounds, or
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`starting points, for further development efforts.” Id. at 1291. Second, we
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`analyze whether there was a reason to modify a lead compound to make the
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`claimed compound with a reasonable expectation of success. Id. at 1292.
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`A lead compound is defined as “‘a compound in the prior art that
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`would be most promising to modify in order to improve upon its . . . activity
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`and obtain a compound with better activity.”’ Id. at 1291 (citing Takeda
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`Chem. Indus., Ltd. v. Alphapharm Pty., Ltd., 492 F.3d 1350, 1357 (Fed. Cir.
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`2007)). Stated another way, “a lead compound is ‘a natural choice for
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`further development efforts.”’ Id. (citing Altana Pharma AG v. Teva Pharm.
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`USA, Inc., 566 F.3d 999, 1008 (Fed. Cir. 2009)). The analysis of whether a
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`chemist of ordinary skill would have chosen the prior art compound as a lead
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`compound “is guided by evidence of the compound’s pertinent properties”
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`including “positive attributes such as activity and potency,” “adverse effects
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`such as toxicity,” “and other relevant characteristics in evidence.” Id. at
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`1292.
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`Importantly, “[a]bsent a reason or motivation based on such prior art
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`evidence, mere structural similarity between a prior art compound and the
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`claimed compound does not inform the lead compound selection.” Id.; see
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`also Daiichi Sankyo Co., Ltd. v. Matrix Laboratories, Ltd., 619 F.3d 1346,
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`1354 (“[P]roving a reason to select a compound as a lead compound depends
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`on more than just structural similarity, but also knowledge in the art of the
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`functional properties and limitations of the prior art compounds”).
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`Establishing that a chemical compound would have been obvious over a
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`structurally similar compound requires “a showing that the ‘prior art would
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`have suggested making the specific molecular modifications necessary to
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`achieve the claimed invention.’” Takeda Chem. Indus., Ltd. v. Alphapharm
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`Pty., Ltd., 492 F.3d 1350, 1356 (Fed. Cir. 2007) (internal quotations
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`omitted).
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`In the present case, Petitioner identifies the Picard Example 3
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`Compound as a “lead compound” and then proceeds to walk us through the
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`steps a person of ordinary skill in the art would have had to perform in order
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`to arrive at the compound of the claims. Pet. 26–36. These steps involve
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`concluding from the data provided in Picard Table 1 that an isopropyl group
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`at position R2 of Picard Formula I is important for improved compound
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`activity (i.e., IC50). As the Picard Example 3 Compound is not a compound
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`according to Picard Formula I, a person of ordinary skill in the art would
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`have had to predict that this improved activity, attributed to the R2
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`substituent, would have also been exhibited by a compound according to
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`Picard Formula II having an isopropyl group at the R2 position. A person of
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`ordinary skill in the art would then have replaced the isopropyl at the R2
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`position of the Picard Example 3 Compound with a cyclopropyl group to
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`achieve the compound of the challenged claims. Petitioner reasons that
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`Kesseler would have informed a person of ordinary skill in the art that such
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`a change would improve the activity of the compound based on a
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`comparison of Kesseler’s Ie and Iac compounds. Pet. 31 (citing Brown
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`Decl. ¶¶ 41–42).
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`We are not persuaded that Petitioner has established that a person of
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`ordinary skill in the art would have been motivated to perform the necessary
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`modifications to the Picard Example 3 Compound in order to achieve the
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`claimed compound. We note that Picard does not disclose any biological or
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`pharmacokinetic data for the Picard Example 3 Compound, and as such,
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`provides no suggestion that this compound has any particular functional
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`activity to suggest that the compound should serve as a lead compound.
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`Rather, the data disclosed in Picard relates to compounds according to
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`Picard Formula I (Ex. 1009, 11:3940 (Table 1)), which differs significantly
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`from the Example 3 compound, a compound of Picard Formula II.
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`Petitioner’s asserted obviousness ground is based primarily on the
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`structural similarity of the Example 3 compound and the compound of the
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`challenged claims. As stated in Otsuka, structural similarities alone are not
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`enough to inform the lead compound selection. 678 F.3d at 1292.
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`Accordingly, we determine that Petitioner has not provided sufficient reason
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`to show that it would have been obvious to select the Picard Example 3
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`Compound from the genus of compounds disclosed in Picard.
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`Moreover, even assuming one would have started with Picard
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`Example 3 Compound (based on its disclosure as an example compound),
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`Petitioner does not persuade us sufficiently that an ordinary artisan would
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`have had reason to substitute the isopropyl at the R2 position in particular in
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`that compound with a cyclopropyl group. Table 1 in Picard, which relates to
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`entirely different compounds, does not disclose a cyclopropyl group at that
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`position. Consequently, Petitioner necessarily relies on Kesseler in its
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`reasoning for the substitution—a reference that also discloses a number of
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`entirely different compounds. Petitioner does not explain adequately why
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`one would have chosen this particular substitution in relation to Picard
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`Example 3 Compound in particular, in view of the large number of possible
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`substitution options when considering the different compounds disclosed in
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`Kesseler and Table 1 of Picard.
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`D. Interference Estoppel
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`Petitioner contends that “[t]he grandparent application of the ’336
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`patent was involved in two interferences,” both of which the Patent Owner
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`lost. Pet. 41 (citing Ex. 1005 and Ex. 1006). Petitioner attempts to use
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`arguments made in those interferences to support arguments that the Patent
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`Owner disclaimed or otherwise lost the right to claim the compound of
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`claims 1 and 2 of the ’336 patent. Id. at 4160. It thus appears that
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`Petitioner is attempting to rely on estoppel based on prior judgments in the
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`above-mentioned interferences (Ex. 1005 and Ex. 1006), not on asserted
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`unpatentability under 35 U.S.C. §§ 102, 103 based on prior art.
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`Under 35 U.S.C. § 311(b), a petitioner in an inter partes review “may
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`request to cancel as unpatentable 1 or more claims of a patent only on a
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`ground that could be raised under section 102 or 103 and only on the basis of
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`prior art consisting of patents or printed publications.” Petitioner has not
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`directed us to any authority that allows this Board to cancel claims in an
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`inter partes review based on arguments by a Petitioner that the Patent Owner
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`may have disclaimed the subject matter of challenged claims in a related
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`grandparent application, which is the relief requested by Petitioner (see Pet.
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`4160).
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`The ’336 patent itself was not involved in the two interference cases
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`cited by Petitioner. Pet. 41–42. Nonetheless, Petitioner relies on alleged
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`“estoppel” based on judgments in those interferences, and specifically
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`Petitioner’s assertion that certain claims at issue in those cases recite subject
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`matter that “is not patentably distinct” from the subject matter recited in the
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`challenged claims. Pet. 46, 48. Thus, Petitioner does not assert
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`unpatentability under 35 U.S.C. §§ 102, 103 based on prior art. See also
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`W. L. Gore & Associates, Inc. v. LifePort Sciences LLC, Case IPR2014-
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`01319, Paper 7, slip op. at 14–15 (PTAB Feb. 23, 2015) (addressing a
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`similar type of argument regarding asserted “interference estoppel”).
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`Accordingly, we do not institute an inter partes review based on the alleged
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`interference estoppel asserted by Petitioner.
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`III.
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` CONCLUSION
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`Petitioner does not persuade us that there is a reasonable likelihood
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`that at least one of the challenged claims is unpatentable based on the
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`asserted ground. We deny the petition for inter partes review and decline to
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`institute trial on the asserted ground as to any of the challenged claims.
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`IV. ORDER
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`In consideration of the foregoing, it is hereby ORDERED that the
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`petition is denied as to all challenged claims and no trial is instituted.
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`PETITIONER:
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`Kenneth Burchfiel
`kburchfiel@sughrue.com
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`Travis Ribar
`tribar@sughrue.com
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`Chid Iyer
`ciyer@sughrue.com
`
`Michael Dzwonczyk
`mdzwonczyk@sughrue.com
`
`Azy Kokabi
`akokabi@sughrue.com
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`
`
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`PATENT OWNER:
`
`David Conlin
`dgconlin@mintz.com
`
`Kathleen Carr
`KBCarr@mintz.com
`
`David Cotta
`DCotta@mintz.com
`
`Peter Cuomo
`PJCuomo@mintz.com
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`17
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