Paper No. ___
`Filed: January 8, 2016
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`UNITED STATES PATENT AND TRADEMARK OFFICE
`_____________________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`_____________________________
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`MYLAN PHARAMACEUTICALS INC.,
`Petitioner,
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`v.
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`ASTRAZENECA AB,
`Patent Owner.
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`_____________________________
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`Case IPR2015-01340
`Patent RE44,186
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`_____________________________
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`PETITIONER MYLAN PHARMACEUTICALS INC.’S
`REQUEST FOR REHEARING PURSUANT TO 37 C.F.R. §42.71
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`Filed: January 8, 2016
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`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`_____________________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`_____________________________
`
`
`MYLAN PHARAMACEUTICALS INC.,
`Petitioner,
`
`v.
`
`ASTRAZENECA AB,
`Patent Owner.
`
`_____________________________
`
`Case IPR2015-01340
`Patent RE44,186
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`_____________________________
`
`PETITIONER MYLAN PHARMACEUTICALS INC.’S
`REQUEST FOR REHEARING PURSUANT TO 37 C.F.R. §42.71
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`Case IPR2015-01340
`Patent RE44,186
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`TABLE OF CONTENTS
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`I.
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`INTRODUCTION ........................................................................................ 1
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`II.
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`BASIS FOR REHEARING........................................................................... 1
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`A.
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`Legal Standards .................................................................................. 1
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`B.
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`C.
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`Erroneous Interpretation of Law ......................................................... 2
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`Factual Findings Not Supported by Substantial Evidence ................... 5
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`III.
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`PANEL COMPOSITION ........................................................................... 12
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`IV. CONCLUSION .......................................................................................... 13
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`I.
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`INTRODUCTION
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`In response to the Decision Denying Institution of Inter Partes Review
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`entered December 9, 2015, (Paper 12, hereinafter “Decision”) and pursuant to 37
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`C.F.R. § 42.71(d), Mylan Pharmaceuticals Inc. (“Petitioner”) hereby respectfully
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`requests the Patent Trial and Appeal Board (“Board”) reconsider its decision
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`denying institution for inter partes review of U.S. Patent No. RE44,186 E (“the
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`’186 patent”).
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`II. BASIS FOR REHEARING
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`A. Legal Standards
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`Pursuant to 37 C.F.R. § 42.71(d), a party may request rehearing of a decision
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`by the Board whether to institute a trial. “The request must specifically identify all
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`matters the party believes the Board misapprehended or overlooked, and the place
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`where each matter was previously addressed in a motion, opposition, or reply.” Id.
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`The Board will review the previous decision for an abuse of discretion. 37 C.F.R. §
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`42.71(c). “An abuse of discretion may be indicated if a decision is based on an
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`erroneous interpretation of law, if a factual finding is not supported by substantial
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`evidence, or if the decision represents an unreasonable judgment in weighing
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`relevant factors.” IPR 2013-00369, Paper 39 at 2-3 (citing Star Fruits S.N.C. v.
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`United States, 393 F.3d 1277, 1281 (Fed. Cir. 2005)).
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`The Petition asserted in Ground 1 that a combination of Ashworth I,
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`Villhauer I, Raag and Hanessian rendered obvious the compound of claim 25 of
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`the ’186 patent, and this compound was encompassed by each of the other
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`challenged claims. Decision, p. 5. According to the ʼ186 patent, the compound of
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`claim 25 (referred to for convenience in the Petition as saxagliptin) was said to be
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`an inhibitor of the enzyme dipeptidyl peptidase IV (DP-IV) and therefore useful to
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`ameliorate the diabetic condition. Id., p. 3.
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`The Decision states that, “we accept Petitioner’s assertion that a person[] of
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`ordinary skill would have chosen compound 25 as a lead compound . . . [and]
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`focus on whether the evidence of record supports Petitioner’s contention that one
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`of ordinary skill in the art would have been motivated to replace the 6-carbon
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`cyclohexyl group at the 2-position of compound 25 with a 10-carbon adamantyl
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`moiety.” Dec., pp. 7-8.
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`B.
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`Erroneous Interpretation of Law
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`The Decision first found that there was insufficient motivation for one of
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`ordinary skill to increase the stability of compound 25 by substituting a larger
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`cycloalkane—in particular adamantyl—for the cyclohexyl group of compound 25.
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`The Decision concludes that Villhauer I, Ex. 1008, which discloses the adamantyl,
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`“fails to cure the lack of rationale for substituting adamantyl at the 2-position of
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`compound 25.” Dec., p. 11. The Decision bases its conclusion on the following
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`statement, which contradicts the substantial evidence and errs as a matter of law:
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`“[A]lthough Villhauer I identifies adamantyl as a possible moiety in ‘[e]ven more
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`preferred compounds,’ adamantyl groups are conspicuously absent from the
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`preferred examples of Villhauer [I]—‘Examples 1, 3, 5, 8, and 12 [, which] are
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`the preferred agents of the invention.’ Ex. 1008, 5, 21; see Pet. 26” (Dec., p. 11,
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`emphasis added).
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`An obviousness analysis under § 103 does not require that a prior art
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`reference, such as Villhauer I, identify a compound as a most preferred or
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`exemplified agent of the invention. Merck & Co. v. Biocraft Labs., Inc., 874 F.2d
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`804, 807 (Fed. Cir. 1989). “In a section 103 inquiry, ‘the fact that a specific
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`[embodiment] is taught to be preferred is not controlling, since all disclosures of
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`the prior art, including unpreferred embodiments, must be considered.’” (Merck,
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`quoting In re Lamberti, 545 F.2d 747, 750 (C.C.P.A. 1976)); see also Boston Sci.
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`Scimed, Inc. v. Cordis Corp., 554 F.3d 982, 991 (Fed. Cir. 2009) (citing Merck in
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`holding that a prior art reference containing two separate embodiments that when
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`combined taught the claimed invention, “need not have recognized the additional
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`benefit of one embodiment to have rendered the claim obvious”).
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`Thus, it was legal error for the Board to observe as particularly noteworthy
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`in its obviousness analysis that adamantyl groups were “conspicuously absent from
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`the preferred examples of Villhauer [I].” Dec., p. 11. Not only does Villhauer I
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`expressly state that an adamantylated compound is an “even more preferred
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`compound of the invention,” but, in addition and contrary to the statement in the
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`Decision, three different examples of adamantylated compounds are identified in
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`Villhauer I, see Examples 47, 49 and 53 (Ex. 1008, p. 13) (see Pet., p. 9, pointing
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`to the synthesis and characterization of an adamantyl-containing compound,
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`Example 47, in Villhauer I). Patent Owner’s evidence corroborates Petitioner’s
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`evidence: Villhauer (Novartis) was pursuing its own patent to DP-IV inhibitor
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`compounds containing the very same adamantyl groups. See, U.S. Patent No.
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`6,166,063 (Ex. 2013; “Villhauer II”), Abstr. (“wherein R is substituted
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`adamantyl”); col. 2, ll. 20-35 (depicting compounds of formula Ia and Ib), and
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`elsewhere throughout the patent disclosure. Villhauer II has a priority date of Dec.
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`10, 1998, well prior to the March 10, 2000, priority date of the ’186 patent.
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`Villhauer II further discloses an adamantyl group that is hydroxylated in exactly
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`the same position as saxagliptin. Ex. 2013, Example 1, p. 5. Thus, again, Petitioner
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`and Patent Owner provided substantial evidence supporting Ground 1 of the
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`Petition. Simply put, the Board’s decision not only lacks substantial evidence, it
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`contradicts the substantial evidence of record. The prior art indisputably discloses
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`adamantylated (and hydroxylated adamantyl) DP-IV inhibitors.
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`When Villhauer I is correctly interpreted and accorded appropriate weight in
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`a legally correct obviousness analysis, the requisite teaching and rationale for
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`substituting adamantyl at the 2-position of compound 25 of Ashworth I are clearly
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`provided. It was legal error for the Board to base its Decision on what it perceived
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`to be the “conspicuous[] absen[ce]” (Dec., p. 11) of a preferred Example of an
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`adamantylated compound in Villhauer I, and to draw inferences adverse to a
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`conclusion of obviousness.
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`C.
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`Factual Findings Not Supported by Substantial Evidence
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`As noted in the Decision, the Petition identifies a rationale to substitute the
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`cyclohexyl group of Ashworth I with the even larger adamantyl group of Villhauer
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`I. Dec., p. 8. Adamantyl is, after all, simply an enlarged version of cyclohexyl:
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`effectively four interconnected cyclohexyls, in which each cyclohexyl shares two
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`bonds with each of the other three. Depicted in Pet., p. 8. Further, Villhauer uses it
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`in their own DP-IV inhibitors, as discussed above. Ex. 1008; Ex. 2013. But the
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`Decision, reading Ashworth I in view of Ashworth II (Ex. 2001), concludes that
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`together they do not support a motivation to increase the stability of lead
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`compound 25. Dec., p. 8. When Ashworth II is correctly considered, however,
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`particularly in the context of Ashworth I’s teachings, the Board’s factual findings
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`are contradicted by substantial evidence. As explained below, Ashworth I and II’s
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`teachings provide ample rationale for substitution of a larger group, one already
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`used with DP-IV inhibitors (i.e., adamantyl) for the cyclohexyl group of compound
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`25. This request is Petitioner’s first opportunity to address this aspect of Ashworth
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`II and is thus timely.
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`The Decision finds compound 25 is stable in its original form, and finds no
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`motivation to further modify it to increase its stability. Dec., p. 10. This finding is
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`based on long-overturned law and less than a scintilla of probative evidence: that
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`the Ashworth II publication focused on increasing potency, not stability (“Not
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`surprisingly, the resulting publication, Ashworth II, [footnote omitted] was not
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`directed to increasing stability, but ‘to improv[ing] the potency of this class of
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`inhibitors.’ Ex. 2001, 2746 [. . .] Ashworth II, therefore, further suggests that
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`compound 25 is stable in its original form”). Dec., p. 10. The absence of a
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`suggestion to further improve stability in a single paper is not evidence that the
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`authors of the paper rejected the possibility of further stability optimization. There
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`is no evidence to support such an inference. In effect, the Decision’s finding
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`erroneously requires Ashworth II to provide the motivation for modifying
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`Ashworth I. Long before even KSR, the Federal Circuit rejected any requirement
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`that the prior art must suggest its own modification. In re Dillon, 919 F.2d 688,
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`692 (Fed. Cir. 1990) (en banc).
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`In any case, the Decision’s factual findings regarding Ashworth II (Ex.
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`2001) and its purported affirmance of the stability of compound 25 in Ashworth I
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`(Ex. 1007) are incorrect in several aspects and lack substantial evidence. If
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`anything, as explained below, Ashworth II highlights the potential instability of
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`compound 25 when making changes to the pyrrolidine ring portion of the molecule
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`(e.g., to improve potency) and motivates further improvement to the stability of
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`compound 25 of the kind established in the Petition.
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`Once again, the Patent Owner’s evidence actually supports the Petition:
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`compounds 13 and 14 of Ashworth II (Ex. 2001, p. 2748, Table II) are identical to
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`compounds 24 and 25 of Ashworth I, but for the inclusion of sulfur in the
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`pyrrolidine ring. Compare compound 13 (cyclopentylglycine in the Xaa position;
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`Table II of Ashworth II, p. 2748) with compound 24 (cyclopentylglycine in the
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`Xaa position; Table II of Ashworth I, p. 1166); and compare compound 14
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`(cyclohexylglycine in the Xaa position; Table II of Ashworth II, p. 2748) with
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`compound 25 (cyclohexylglycine in the Xaa position; Table II of Ashworth I, p.
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`1166). The structures are set forth below for ease of comparison:
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`Comparing the stability of compound 25 with compound 14 of Ashworth II,
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`it can be seen that the half-life, t1/2, falls dramatically with modification of the
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`pyrrolidine ring: from ˃48 hours for compound 25, to 16 hours for compound 14.
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`The same holds true for compound 24; when the pyrrolidine ring is modified,
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`creating compound 13, the t1/2 falls from 48 hours to 5 hours.
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`Thus, Ashworth II’s attempt to increase the DP-IV inhibition potency of
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`Ashworth I compounds 24 and 25, by modifying the pyrrolidine ring to include a
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`sulfur, dramatically decreases the stability of the compounds. The statement in the
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`Decision that “Ashworth II, therefore, further suggests that compound 25 is stable
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`in its original form” (Dec., p. 10) overlooks the very significant fact that the
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`attempt in Ashworth II to improve potency of compound 25 substantially
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`diminished the stability of the compound. In view of the teachings of Ashworth II,
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`one of ordinary skill would have been highly motivated to improve the stability of
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`compound 25 while improving potency. It is worth noting that the Decision did not
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`reach evidence in the Petition that it would have been obvious to improve the
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`potency of compound 25 by modifying the pyrrolidine ring, as was done by both
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`Ashworth I and Villhauer I, by adding cyclopropyl (as taught by Hanessian), which
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`was added in the same place as the sulfur as disclosed in Ashworth II.
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`Apart from Ashworth II’s support for increasing the stability of lead
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`compound 25, factual errors are made in the Decision regarding Ashworth I. These
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`errors lead to a lack of substantial evidence for the Decision’s conclusion that a
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`person of ordinary skill would not have been motivated to substitute a larger
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`cycloalkyl moiety, i.e., adamantyl, for the cyclohexyl group of compound 25. Dec.,
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`p. 12.
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`As noted above, the Decision determines that Villhauer I, “fails to cure the
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`lack of rationale for substituting adamantyl at the 2-position of compound 25.”
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`(Dec., p. 11) This conclusion contradicts the substantial evidence of record and errs
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`as a matter of law. For example, Lin states, “[DP-IV] substrates require the
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`presence of a . . . free N-terminus.” Pet., p. 19, citing Ex. 1015, p. 14020
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`(emphasis added). Ashworth I further states, “[N-terminal] α-amino acid
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`derivatives were the most potent compounds.” Pet., p. 25, citing Ex. 1007, p. 1165.
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`Had the Board properly considered the teachings of Villhauer I in the context of
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`the art as a whole, i.e., Lin and Ashworth I, it would have found direct motivation
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`to substitute the adamantyl moiety at the 2-position of compound 25.
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`At page 13, the Decision notes the express statement in Ashworth I that “as
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`can be seen in Table I, lipophilic amino acids gave more potent compounds.” But
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`the Decision finds two exceptions in the many compounds shown in Table 1, such
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`that it concludes that Ashworth I’s express statement “does not invariably hold.”
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`Dec., p. 13. First, the general trend does not have to invariably hold to provide a
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`clear and direct teaching. Second, compound 9 (substituted with valine) being
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`more potent than compound 11 (substituted with tert-butyl) is identified as an
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`exception because valine “contains less ‘beta-branching.’” Dec., p. 13. However,
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`Ashworth I simply identifies that β-branched derivatives were the most potent
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`compounds. Ashworth I does not suggest that more β-branching produces even
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`more potent compounds. Thus, this alleged exception is the result of a
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`misconstruction of Ashworth’s teachings and lacks substantial evidence in support.
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`The actual trend, that large, β-branched and more lipophilic amino acids provide
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`more potent compounds, is clearly taught by Ashworth I to apply to Table II: “[w]e
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`then applied these findings [from Table I] to a series of 2-cyanopyrrolidides [of
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`Table II] . . . The [Structure-Activity Relationship] for the N-terminal residue
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`developed in the pyrrolidide series [of Table I] correlated well for the dipeptide
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`nitrile series [of Table II].” Ex. 1007, p. 1165 (bold added); Pet., p. 26. The
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`Decision (p. 13), however, considered the compounds of Table I less pertinent to
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`the analysis than compounds 24 and 25 found in Table II, when its teachings were
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`actually supportive of Table II.
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`Accepting only for the purpose of this Rehearing Request the Board’s
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`Decision that Table I of Ashworth I is less pertinent, the findings regarding Table
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`II of Ashworth I, particularly compounds 24 and 25, are factually incorrect. The
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`Decision states, “[A]s Patent Owner points out, Ashworth I compounds 24-27
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`exhibit comparable stabilities with half-lives of at least 48 hours despite having
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`substituents of varying size and composition in the 2-position.” Dec., pp. 10-11.
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`This assessment is incorrect. The cyclohexylated (Chg) compound 25 is more
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`stable than the smaller, cyclopentylated compound 24 (i.e., a half-life of >48 hours,
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`versus precisely 48 hours). The extent to which it is more stable is unknown based
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`on the data presented in Ashworth I, as the data simply show compound 25 as
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`having a longer half-life, i.e., >48 hours, and thus being more stable than
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`compound 24.
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`This is also the case for compound 27, containing tert-butyl glycine (Tbg).
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`The tert-butyl substituent of compound 27 is bulkier than the isoleucine of
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`compound 26, having one more degree of beta-branching than isoleucine. That
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`compound 27 is more stable than compounds 24 and 26 is consistent with its
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`increased bulk and lipophilicity, as taught by Ashworth I. But again, the degree to
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`which compound 27 is more stable than compounds 24, 26, or even perhaps 25, is
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`unknown. There is, however, a clear trend apparent from Table II of Ashworth I:
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`larger, more lipophilic substituents at the 2-position yield more stable compounds.
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`The extent to which stability is enhanced is not assessed, but nonetheless the trend
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`is readily apparent.
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`The Decision further incorrectly asserts that isoleucine (found in compound
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`26) is less bulky than cyclopentane, when there is no data to support this factual
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`finding. Dec., p. 11. Cyclopentane (Chg) and isoleucine (Ile) are comparable in
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`terms of steric bulk and lipophilicity; while cyclopentane has one more methylene
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`unit and isoleucine has more freely rotatable bonds and thus is comparable to
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`cyclopentane. That compounds 24 and 26 have the same stability (i.e., half-lives of
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`48 hours) in Table II is consistent with their similar three-dimensional shapes, and
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`does not negate the clear trend of Table II, that larger, more lipophilic substituents
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`yield more stable compounds.
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`Thus, the Decision’s factual determination that “Ashworth I compounds 24-
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`27 exhibit comparable stabilities” (Dec., p. 10) is incorrect; only the stability of
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`compound 24 and 26 are comparable. The stability of compound 25 and 27 are
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`reported only as something greater than 48 hours, and thus indeterminate.
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` In incorrectly analyzing the data of Ashworth I (and Ashworth II, as
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`discussed above), the Decision’s conclusions contradict the substantial evidence.
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`Ashworth I teaches a strong and clear trend: larger substituents at the α-position of
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`the N-terminal amino acid residue of DP-IV inhibitor compounds result in
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`heightened stability. Ashworth II teaches that perturbations to the pyrrolidine
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`decrease stability. This trend leads those in the art to adamantyl as a bulkier
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`version of the cyclohexyl in compound 25. Villhauer I expressly recites adamantyl
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`is an “even more preferred” substituent on the N-terminus of DP-IV inhibitors. The
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`Decision’s erroneous interpretation of law regarding Villhauer I were combined
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`with key factual findings in Ashworth I and II that are not supported by substantial
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`evidence. When corrected, the combination of art leads to compound 25 of
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`Ashworth I having a substituted adamantyl group at the precise position found in
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`saxagliptin, the compound of claim 25 of the ʼ186 patent.
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`III. PANEL COMPOSITION
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`A new panel may be appropriate to consider this rehearing request and,
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`should the Board determine to institute trial, to conduct the trial. Petitioner learned
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`after the entry of the Decision that the authoring administrative patent judge was a
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`partner at opposing counsel’s law firm as of June 2014. 1 When the Petition was
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`filed, Petitioner identified a related lawsuit filed on June 2, 2014 for AstraZeneca
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`against Mylan for infringement of the ’186 patent. Pet., p. 16, citing AstraZeneca
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`AB v. Mylan Pharmaceuticals Inc., 14-cv-00696 (DED 2014). Counsel for
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`AstraZeneca in the District Court litigation against Mylan is also lead counsel for
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`AstraZeneca in this proceeding. The administrative patent judge who was a partner
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`at opposing counsel’s firm in June 2014 had also appeared as co-counsel with
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`AstraZeneca’s lead counsel in several other lawsuits against generic drug
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`companies. E.g., Cephalon, Inc. v. Apotex Corp., 10-cv-01078 (DED) & 10-cv-
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`22997 (FLSD); Astellas US LLC et al. v. Nycomed U.S. Inc., 10-cv-08274 (NYSD)
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`& 10-cv-05599 (NJD).
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`Petitioner does not suggest there was an actual impropriety: the mere
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`appearance of possible impropriety is sufficient to justify reconsideration by a
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`1 See LinkedIn page listing employment at Finnegan in June 2014. June 2 was
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`the first weekday of the month.
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`newly composed panel. 2 Aetna Life Ins. Co. v. Lavoie, 475 U.S. 813, 825 (1986)
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`(explaining actual bias is not required); Caperton v. AT Massey Coal Co., Inc.,
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`129 S. Ct. 2252, 2264 (2009) (same). Petitioner is raising the issue at its first
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`opportunity after discovery. Lavoie, 475 U.S. at 817-19 (holding timely challenge
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`first raised after request for reconsideration filed); see also Liljeberg v. Health
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`Servs. Acquisition Corp., 486 U.S. 847, 868-69 (1988).
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`Petitioner respectfully suggests rehearing by a newly composed panel.
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`IV. CONCLUSION
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` The Decision erred as a matter of law in relying on a finding that adamantyl
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`groups were “conspicuously absent” from the preferred examples of a prior art
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`reference, Villhauer I (Ex. 1008), contradicting precedent holding that a
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`modification need not even be preferred. The Decision’s finding that Villhauer I
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`lacked examples of adamantyl-containing compounds was also lacking in
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`substantial evidence: the Petition also noted that Villhauer provided the compound
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`of Example 47, an adamantyl-containing DP-IV inhibitor. Pet., p. 9.
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`In addition, in assessing the impact of Ashworth II (Ex. 2001), the Decision
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`lacks substantial evidence for concluding that Ashworth II discourages further
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`improvements to the stability of lead compound 25 identified in Ashworth I (Ex.
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`2 See, e.g., 28 U.S.C. 455(b)(2) (barring participation of a district court judge
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`where former firm worked on matter in controversy while judge was still there).
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`1007). In fact, Ashworth II shows that small perturbations to the pyrrolidine ring of
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`compound 25 can significantly diminish the stability of the compound, which
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`would have motivated offsetting improvements to compound stability. A person of
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`ordinary skill in the art would have found it obvious to modify compound 25 by
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`replacing the cyclohexyl group with an even larger interconnected cyclohexyl
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`group, adamantyl, as described in Villhauer I.
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` Petitioner respectfully suggests rehearing by a newly composed panel and
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`Respectfully submitted,
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`/ Steven W. Parmelee /
` Steven W. Parmelee
` Reg. No. 31,990
` Rick Torczon
` Reg. No. 34,448
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`requests institution of trial.
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`Dated: January 8, 2016
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`CERTIFICATE OF SERVICE
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`This is to certify that I caused to be served a true and correct copy of the
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`foregoing Petitioner Mylan Pharmaceuticals Inc.’s Request for Rehearing, on this
`
`8th day of January, 2016, on the Patent Owner at the correspondence address of the
`
`M. David Weingarten
`Finnegan, Henderson, Farabow,
`Garret & Dunner, L.L.P.
`3500 SunTrust Plaza
`303Peachtree Street, N.E.
`Atlanta, GA 3038
`Tel: 404-653-6400
`Fax: 404-653-6444
`Email:
`david.weingarten@finnegan.com
`
`Patent Owner as follows:
`
`
`Charles E. Lipsey
`Finnegan, Henderson, Farabow,
`Garret & Dunner, L.L.P.
`11955 Freedom Drive
`Reston, VA 20190
`Tel: 571-203-2700
`Fax: 202-208-4400
`Email: charles.lipsey@finnegan.com
`
`Eric E. Grondahl
`McCarter & English LLP
`City Place I
`185 Asylum St.
`Hartford, CT
`Tel: 860-275-6704
`Fax: 860-724-3397
`Email: egrondahl@mccarter.com
`
`
`
`
`Dated: January 8, 2016
`
`
`
`
`
`
`Respectfully submitted,
`
`/ Steven W. Parmelee /
` Steven W. Parmelee, Lead Counsel
` Reg. No. 31,990
`
`
`
`
`
`-15-
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