`571.272.7822
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` Paper No. 9
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` Entered: June 8, 2018
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`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________
`
`FLATWING PHARMACEUTICALS, LLC,
`Petitioner,
`
`v.
`
`ANACOR PHARMACEUTICALS, INC.,
`Patent Owner.
`____________
`
`Case IPR2018-00168
`Patent 9,549,938 B2
`____________
`
`
`Before GRACE KARAFFA OBERMANN, TINA E. HULSE, and
`JACQUELINE T. HARLOW, Administrative Patent Judges.
`
`HULSE, Administrative Patent Judge.
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`
`
`DECISION TO INSTITUTE
`35 U.S.C. § 314(a)
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`IPR2018-00168
`Patent 9,549,938 B2
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`I. INTRODUCTION
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`Flatwing Pharmaceuticals, LLC (“Petitioner”) filed a Petition
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`requesting an inter partes review of claims 1–6 of U.S. Patent No.
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`9,549,938 B2 (Ex. 1001, “the ’938 patent”). Paper 1 (“Pet.”). Anacor
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`Pharmaceuticals, Inc. (“Patent Owner”) did not file a Preliminary Response
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`to the Petition.
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`We have authority under 35 U.S.C. § 314, which provides that an
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`inter partes review may not be instituted “unless . . . there is a reasonable
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`likelihood that the petitioner would prevail with respect to at least 1 of the
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`claims challenged in the petition.” 35 U.S.C. § 314(a). Upon considering
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`the argument and evidence presented in the Petition, we determine that
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`Petitioner has established a reasonable likelihood that it would prevail in
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`showing the unpatentability of at least one claim challenged in the Petition.
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`Accordingly, we institute an inter partes review of all claims and all grounds
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`asserted in the Petition.
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`A.
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`Related Proceedings
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`Petitioner has filed three other petitions for inter partes review of
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`related patents: U.S. Patent No. 9,566,289 (IPR2018, 00169), U.S. Patent
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`No. 9,566,290 (IPR2018-00170), and U.S. Patent No. 9,572,823 (IPR2018-
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`00171). Paper 4, 2.
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`Case IPR2015-01776 is an inter partes review of U.S. Patent No.
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`7,582,621 (“the ’621 patent”), which, according to Patent Owner, “asserts
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`substantially the same claim of priority as U.S. Patent No. 9,549,938.” Id.
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`The Board determined each of the claims of the ’621 patent was
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`unpatentable over the prior art. Coalition for Affordable Drugs X LLC v.
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`Anacor Pharms., Inc., Case IPR2015-01776, slip op. at 42 (PTAB Feb. 23,
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`2
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`IPR2018-00168
`Patent 9,549,938 B2
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`2017) (Paper 70). The Federal Circuit recently affirmed the Board’s final
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`written decision as to claim 6 of the ’621 patent (the only claim on appeal) in
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`Anacor Pharmaceuticals, Inc. v. Iancu, No. 2017-1947, 2018 WL 2187768,
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`at *9 (Fed. Cir. May 14, 2018).
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`The parties also identify U.S. Patent Application Nos. 15/355,393 and
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`15/355,813 as administrative matters that may be affected by this
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`proceeding. Pet. x; Paper 4, 3.
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`B.
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`The ’938 Patent
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`The ’938 patent relates to boron-containing compounds useful for the
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`topical treatment of onychomycosis and/or cutaneous fungal infections.
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`Ex. 1001, Abstract. The claimed invention is directed to compounds that are
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`active against fungi and have physicochemical properties that facilitate
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`penetration of the nail plate. Id. According to the Specification, current
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`treatment for ungual and/or periungual infections generally falls into three
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`categories: systemic administration of medicine; surgical removal of the
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`nail or hoof followed by topical treatment of the exposed tissue; or topical
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`application of medicine with bandages to keep the medication in place on
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`the nail or hoof. Id. at 1:49–55.
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`Each of the approaches has major drawbacks. Id. at 1:55–56.
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`Systemic administration of medicine typically requires long-term, high-dose
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`therapy, which can have significant adverse effects on, for example, the liver
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`and testosterone levels, which further negatively affects patient compliance.
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`Id. at 1:60–2:2. Surgical treatment is painful and undesirable cosmetically
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`(or not realistic for animals such as horses). Id. at 2:12–18. And topical
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`dosage forms cannot keep the drug in contact with the infected area for
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`therapeutically effective periods of time and, because of the composition of
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`the nail, topical therapy for fungal infections have generally been
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`IPR2018-00168
`Patent 9,549,938 B2
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`ineffective. Id. at 2:19–43. Accordingly, the Specification states that “there
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`is a need in the art for compounds which can effectively penetrate the nail.
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`There is also need in the art for compounds which can effectively penetrate
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`the nail . . . [and] effectively treat ungual and/or periungual infections.” Id.
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`at 3:1–5.
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`Dermatophytes are the most common cause of onychomycosis. Id. at
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`129:51–53. Onychomycosis caused by a dermatophyte is called Tinea
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`unguium. Id. at 129:53–54. The most frequently isolated dermatophyte in
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`Tinea unguium is Trichophyton rubrum followed by T. mentagophytes. Id.
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`at 129:55–56.
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`The ’938 patent claims a method of treating a Tinea unguium
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`infection by topically administering 1,3-dihydro-5-fluoro-l-hydroxy-2, 1-
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`benzoxaborole, which is referred to as either compound 1 (see id. at 135:56–
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`65) or compound C10 (see id. at 178:13) in the Specification, and has the
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`following chemical structure:
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`C.
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`Illustrative Claim
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`Petitioner challenges claims 1–6 of the ’938 patent. Claim 1,
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`the only independent claim, is illustrative and is reproduced below:
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`IPR2018-00168
`Patent 9,549,938 B2
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`1. A method of treating a Tinea unguium infection of a
`toenail of a human, the method comprising:
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`topically administering to the toenail of the human a
`pharmaceutical composition comprising 1,3-dihydro-5-
`fluoro-l-hydroxy-2,1-benzoxaborole, or a
`pharmaceutically acceptable salt thereof, in an amount
`sufficient to treat the infection.
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`D.
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`The Asserted Grounds of Unpatentability
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`Petitioner challenges the patentability of claims 1–6 of the ’938 patent
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`on the following grounds:
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`References
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`Austin1 and Brehove2
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`Basis
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`§ 103
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`Claims challenged
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`1 and 2
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`Austin, Brehove, and Samour3 § 103
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`3–6
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`Austin and Freeman4
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`§ 103
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`1 and 2
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`Austin, Freeman, and Samour
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`§ 103
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`3–6
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`Petitioner also relies on the Declarations of Stephen Kahl Ph.D.
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`(“Kahl Decl.,” Ex. 1003) and S. Narasimha Murthy Ph.D. (“Murthy Decl.,”
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`Ex. 1005).
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`
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`1 Austin et al., WO 95/33754, published Dec. 14, 1995 (“Austin,” Ex. 1007).
`2 Brehove, US 2002/0165121 A1, published Nov. 7, 2002 (“Brehove,”
`Ex. 1008).
`3 Samour et al., US 6,224,887 B1, issued May 1, 2001 (“Samour,”
`Ex. 1010).
`4 Freeman et al., WO 03/009689 A1, published Feb. 6, 2003 (“Freeman,”
`Ex. 1009).
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`IPR2018-00168
`Patent 9,549,938 B2
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`II. ANALYSIS
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`A.
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`Person of Ordinary Skill in the Art
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`Petitioner asserts that a person of ordinary skill in the art at the time of
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`the invention would have had either a Master’s degree or Ph.D. in chemistry,
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`pharmacology, or biochemistry, and at least two years of experience with the
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`research, development, or production of pharmaceuticals. Pet. 21 (citing Ex.
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`1005 ¶¶ 19–21; Ex. 1003 ¶ 24).
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`At this stage of the proceeding, and absent opposition from Patent
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`Owner, we adopt Petitioner’s definition of the level of ordinary skill in the
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`art. Moreover, the prior art itself is sufficient to demonstrate the level of
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`skill in the art at the time of the invention. See Okajima v. Bourdeau, 261
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`F.3d 1350, 1355 (Fed. Cir. 2001) (explaining that specific findings regarding
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`ordinary skill level are not required “where the prior art itself reflects an
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`appropriate level and a need for testimony is not shown”) (quoting Litton
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`Indus. Prods., Inc. v. Solid State Sys. Corp., 755 F.2d 158, 163 (Fed. Cir.
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`1985)).
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`B.
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`Claim Construction
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`In an inter partes review, the Board interprets claim terms in an
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`unexpired patent according to the broadest reasonable construction in light
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`of the specification of the patent in which they appear. 37 C.F.R. § 100(b);
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`In re Cuozzo Speed Techs., LLC, 793 F.3d 1268, 1278–79 (Fed. Cir. 2015),
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`cert. granted sub nom. Cuozzo Speed Techs., LLC v. Lee, 84 U.S.L.W. 3218
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`(U.S. Jan. 15, 2016) (No. 15-446). Under that standard, and absent any
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`special definitions, we give claim terms their ordinary and customary
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`meaning, as would be understood by one of ordinary skill in the art at the
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`time of the invention. See In re Translogic Tech., Inc., 504 F.3d 1249, 1257
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`IPR2018-00168
`Patent 9,549,938 B2
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`(Fed. Cir. 2007). Any special definitions for claim terms must be set forth
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`with reasonable clarity, deliberateness, and precision. See In re Paulsen,
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`30 F.3d 1475, 1480 (Fed. Cir. 1994).
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`1.
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`“1,3-dihydro-5-fluoro-1-hydroxy-2,1-benzoxaborole”
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`Each of the claims recite the compound 1,3-dihydro-5-fluoro-1-
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`hydroxy-2,1-benzoxaborole. 1,3-dihydro-5-fluoro-1-hydroxy-2,1-
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`benzoxaborole has the following structure:
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`
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`Petitioner notes that the claimed compound may also be referred to as
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`“5-fluoro-1,3 dihydro-1-hydroxy-2,1-benzoxaborole,” as in Austin. Pet. 28;
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`Ex. 1005, ¶¶ 34–39. Petitioner’s declarant further notes that the short name
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`for the claimed compound is “tavaborole.” Ex. 1005, ¶ 34.
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`We determine that the broadest reasonable interpretation of 1,3-
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`dihydro-5-fluoro-1-hydroxy-2,1-benzoxaborole includes “5-fluoro-1,3-
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`dihydro-1-hydroxy-2,1-benzoxaborole” and “tavaborole.” Accordingly, for
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`ease of reference, we refer to the claimed compound as “tavaborole” in this
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`Decision.
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`2.
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`Remaining Claim Terms
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`At this stage of the proceeding, we determine that it is unnecessary to
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`expressly construe the remaining claim terms for purposes of this Decision.
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`See Wellman, Inc. v. Eastman Chem. Co., 642 F.3d 1355, 1361 (Fed. Cir.
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`2011) (“[C]laim terms need only be construed ‘to the extent necessary to
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`Patent 9,549,938 B2
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`resolve the controversy.’”) (quoting Vivid Techs., Inc. v. Am. Sci. & Eng’g,
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`Inc., 200 F.3d 795, 803 (Fed. Cir. 1999)).
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`C. Obviousness over Austin and Brehove
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`Petitioner asserts that claims 1 and 2 are unpatentable as obvious over
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`Austin and Brehove. Pet. 23–42. Based on the current record, we determine
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`that Petitioner has established a reasonable likelihood that it would prevail in
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`showing claims 1 and 2 are unpatentable as obvious over Austin and
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`Brehove.
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`1.
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`Austin (Ex. 1007)
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`Austin relates to the use of oxaboroles as industrial biocides, and
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`especially as fungicides for the protection of plastic materials. Ex. 1007, 1
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`(Abstract). The Abstract further states that “[p]referred compounds are 5-
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`and 6-fluoro or bromo-1,3-dihydro-1-hydroxy-2,1-benzoxaborole including
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`O-esters thereof.” Id. Austin notes that it has been found that compounds
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`containing an oxaborole ring are “particularly effective against micro-
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`organisms such as bacteria, algae, yeasts and particularly fungi, especially
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`fungi which cause degradation of plastics materials.” Id. at 3:35–38.
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`Along with a number of different preferred oxaboroles, Austin
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`discloses tavaborole as Example 64, as well as the results of a study showing
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`tavaborole has effective antifungal activity against five different fungi:
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`Aspergillus niger (AN), Candida albicans (CA), Aureobasidium pullulans
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`(AP), Gliocladium roseum (GR), and Penicillium pinophylum (PP). Id. at 39
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`(Table 9). Of the preferred compounds tested (i.e., Examples 64, 68, and
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`70), tavaborole had the lowest Minimum Inhibitory Concentration (“MIC”)
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`value of five parts per million for Candida albicans. Id.; Ex. 1003 ¶ 36.
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`Patent 9,549,938 B2
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`2.
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`Brehove (Ex. 1008)
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`Brehove relates to the topical treatment of nail infections such as
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`onychomycosis caused by bacteria, fungi, and other pathogens. Ex. 1008
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`¶ 3. Brehove explains that onychomycosis is a nail disease typically caused
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`by Candida albicans, Trichophyton mentagrophytes, Trichophyton rubrum,
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`or Epidermpophyton floccusum. Id. ¶ 5. Brehove states that Candida
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`albicans is the most common pathogen causing onychomycosis. Id. ¶ 18.
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`Brehove teaches that to be effective for onychomycosis, the topical
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`treatment should exhibit a powerful potency for pathogens, be permeable
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`through the nail barrier, and be safe for patient use. Id. ¶ 6. According to
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`Brehove, “[t]here exists a need in the art for a topical application that
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`combines these traits in high degree.” Id.
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`Brehove states that the “safety and non-toxicity of organo-boron
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`compounds has been questioned.” Id. ¶ 13. On the one hand, Brehove
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`describes one reference that states that boron compounds are “very toxic,”
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`while on the other hand, Brehove describes references that found the toxicity
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`of a certain boron-containing compound to be “very low” and another
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`industrial fungicide compound called Biobor® JF to cause “mild irritation.”
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`Id. ¶¶ 14–15.
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`Biobor® JF contains a combination of 2,2’-(1-methyltrimethylene
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`dioxy) bis-(4-methyl-1, 3, 2-dioxaborinane) (referred to by Brehove as “S1”)
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`and 2,2’-oxybis (4, 4, 6-trimethyl-1, 3, 2-dioxaborinane) (referred to by
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`Brehove as “S2”). Id. ¶¶ 15, 30. Brehove describes the results of in vitro
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`testing of the antifungal activity of S1 and S2 against Candida albicans. Id.
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`¶¶ 30–33. Brehove also describes in vivo testing of S1 and S2 on various
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`patients with onychomycosis of the toenails. Id. ¶¶ 34–38.
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`Patent 9,549,938 B2
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`3.
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`Analysis
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`Petitioner argues that claims 1 and 2 are unpatentable as obvious over
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`the combination of Austin and Brehove. Claim 1 recites a method of
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`treating a Tinea unguium infection comprising “topically administering to
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`the toenail of a human a pharmaceutical composition comprising
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`[tavaborole] or a pharmaceutically acceptable salt thereof in an amount
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`sufficient to treat the infection.” Petitioner asserts that Austin teaches that
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`tavaborole is an effective fungicide against C. albicans. Pet. 33 (citing
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`Ex. 1007, Abstract, Table 9). Petitioner further asserts that Brehove teaches
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`topical application of boron-containing compounds to treat onychomycosis
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`of human toenails. Id. (citing Ex. 1008 ¶¶ 34–38; Ex. 1005 ¶ 95).
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`According to Petitioner’s declarant, determining a therapeutically effective
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`amount of an active ingredient such as tavaborole in a topically applied
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`pharmaceutical composition was routine in the art. Id. (citing Ex. 1005 ¶¶
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`110).
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`Regarding the limitation that the infection be a Tinea unguium
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`infection (claim 1) caused by T. rubrum or T. mentagrophytes (claim 2),
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`Brehove identifies C. albicans, T. rubrum, and T. mentagrophytes as typical
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`causes of onychomycosis. Ex. 1008 ¶¶ 3, 5. Petitioner asserts it would have
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`been obvious to combine the teachings of Austin and Brehove to treat Tinea
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`unguium with tavaborole in light of tavaborole’s efficacy against C.
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`albicans, as taught by Austin. Pet. 34 (citing Ex. 1007, 35–39; Ex. 1008 ¶¶
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`3, 5). According to Petitioner’s declarant, a person of ordinary skill in the
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`art would have understood “inhibitory activity against yeasts such as
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`Candida albicans to be predictive of antifungal activity against
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`dermatophytes, including T. rubrum and T. mentagrophytes.” Ex. 1005
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`¶ 92.
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`Having considered the arguments and evidence set forth in the
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`Petition, we are persuaded that Petitioner has shown sufficiently that each
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`limitation of claims 1 and 2 is taught or suggested by the combination of
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`Austin and Brehove.
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`Petitioner then asserts that a person of ordinary skill in the art would
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`have administered an effective amount of Austin’s tavaborole in Brehove’s
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`method of topically treating Tinea unguium with a reasonable expectation of
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`success. Pet. 35–44. Specifically, Petitioner asserts that a person of
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`ordinary skill in the art would have combined Austin and Brehove because
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`both references teach the use of boron-containing compounds as effective
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`fungicides. Pet. 36; Ex. 1005 ¶ 98.
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`Petitioner also notes that both references teach the efficacy of boron-
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`containing compounds against onychomycosis-causing Candida albicans.
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`Pet. 36; Ex. 1005 ¶ 98. Moreover, because it was known in the art that
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`antifungal activity against yeasts such as C. albicans is predictive against
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`dermatophytes such as T. rubrum and T. mentagrophytes, Petitioner asserts a
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`person of ordinary skill in the art would have been motivated to combine the
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`effective antifungal tavaborole taught by Austin with the topical composition
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`taught by Brehove to treat all primary causes of onychomycosis: C. albicans,
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`T. rubrum, and T. mentagrophytes. Pet. 36–37 (citing Ex. 1005 ¶ 98).
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`Finally, Petitioner asserts that a person of ordinary skill in the art
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`would have been motivated to replace the topical compositions of Brehove
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`with Austin’s tavaborole because of tavaborole’s lower molecular weight.
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`Pet. 37 (citing Ex. 1005 ¶¶ 99–100). According to Petitioner’s declarant, it
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`was known in the art that smaller, lower molecular weight molecules are
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`more effective at penetrating the human nail barrier and therefore have a
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`greater likelihood of reaching the underlying nail plate at lower
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`concentrations. Pet. 37 (citing Ex. 1005 ¶¶ 99–100).
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`We note that the Federal Circuit affirmed our conclusion that claim 6
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`of the ’621 patent is unpatentable as obvious over Austin and Brehove.
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`Anacor Pharms., 2018 WL 2187768, at *9. Claim 6 is similar to claim 1 of
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`the ’938 patent, as both claims recite a method of treating Tinea unguium
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`with a therapeutically effective amount of tavaborole. Compare Ex. 1012,
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`68:25–26 (claim 6) with Ex. 1001, 319:51–57 (claim 1). The Federal Circuit
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`concluded that “substantial evidence supports the Board’s findings that a
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`person of ordinary skill in the art would have been motivated to combine the
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`pertinent teachings of Austin and Brehove and would have had a reasonable
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`expectation of success in doing so.” Anacor Pharms., 2018 WL 2187768, at
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`*7.
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`Accordingly, having considered the arguments and evidence at this
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`stage of the proceeding, we determine Petitioner has shown a reasonable
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`likelihood of prevailing on its assertion that claims 1 and 2 are unpatentable
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`as obvious over Austin and Brehove.
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`D. Obviousness over Austin, Brehove, and Samour
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`Petitioner argues that claims 3–6 are unpatentable as obvious over
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`Austin, Brehove, and Samour. Pet. 44–49. Based on the current record, we
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`determine that Petitioner has established a reasonable likelihood that it
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`would prevail in showing claims 3–6 are unpatentable over Austin, Brehove,
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`and Samour. We incorporate here our earlier findings and discussion
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`regarding the disclosures of Austin and Brehove.
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`1.
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`Samour (Ex. 1010)
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`Samour relates to a nail lacquer formulation effective for treating or
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`preventing fungal infections, such as onychomycosis. Ex. 1010, Abstract.
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`Samour states that onychomycosis is frequently caused by dermatophytes,
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`but can also be caused by molds and Candida. Id. at 1:22–24. Samour
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`further provides examples of lacquer formulations containing 5% w/w active
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`antifungal ingredient with propylene glycol and ethanol (id. at 23:53–24:8).
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`2.
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`Analysis
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`Petitioner asserts that the combination of Austin, Brehove, and
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`Samour render the subject matter of claims 3–6 obvious. Pet. 44–49.
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`Claims 3–6 depend, either directly or indirectly, from claim 1 and further
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`recite wherein the pharmaceutical composition is in the form of a solution
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`comprising 5% w/w of tavaborole, wherein the composition further
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`comprises ethanol and propylene glycol, and/or where the infection is due to
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`T. rubrum or T. mentagrophytes. Ex. 1001, 319:61–32:61.
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`Petitioner contends that the combination of Austin, Brehove, and
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`Samour teaches each limitation of the claims. Pet. 44–47; Ex. 1005 ¶¶ 119–
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`132. Having reviewed the arguments and evidence, we are persuaded that
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`Petitioner has shown sufficiently that each limitation of claims 3–6 is taught
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`by the combination of cited references for the reasons stated in the Petition.
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`Pet. 44–47; Ex. 1005 ¶¶ 119–132.
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`Petitioner also asserts that a person of ordinary skill in the art would
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`have had a reason to combine Austin’s tavaborole with the improved
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`pharmaceutical composition of Samour in Brehove’s method of topically
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`treating onychomcosis for the same reasons asserted with respect to Austin
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`and Brehove alone. Pet. 47 (citing Ex. 1005 ¶¶ 96–101, 133). Moreover,
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`Petitioner argues that formulating pharmaceutical compositions and amounts
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`of active ingredients was well known in the art of topical pharmaceuticals,
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`involving nothing more than routine experimentation based on well-known
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`protocols. Id. at 48 (citing Ex. 1005 ¶ 134). Petitioner further notes that
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`Samour teaches formulations including 5% w/w active fungicidal ingredient,
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`which falls within the concentration ranges taught in Austin and Brehove.
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`Id. (citing Ex. 1005 ¶ 134).
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`Finally, Petitioner argues that a person of ordinary skill in the art
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`would have had a reason to replace the preferred antifungal of Samour with
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`tavaborole because tavaborole has a lower molecular weight than econazole.
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`Pet. 48 (citing Ex. 1005 ¶136). According to Petitioner, a person of ordinary
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`skill in the art would have understood that lower molecular weight
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`fungicidal compounds are more effective at penetrating the nail plate. Thus,
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`a person of ordinary skill in the art would have had a reasonable expectation
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`of success that such topical compositions would effectively treat Tinea
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`unguium. Id. at 48–49 (citing Ex. 1005 ¶¶ 134–135).
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`Having considered the arguments and evidence presented in the
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`Petition, we determine that Petitioner has established a reasonable likelihood
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`that it would prevail in showing claims 3–6 are unpatentable as obvious over
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`Austin, Brehove, and Samour.
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`On April 24, 2018, the Supreme Court held that a decision to institute
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`under 35 U.S.C. § 314 may not institute on fewer than all claims challenged
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`in the petition. SAS Inst. Inc. v. Iancu, No. 16-969, 2018 WL 1914661, at
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`*10 (U.S. Apr. 24, 2018). After considering the evidence and arguments
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`presented in the Petition, we determine that Petitioner has demonstrated a
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`reasonable likelihood of success in proving that claims 1–6 of the ’938
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`patent are unpatentable.
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`III. CONCLUSION
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`We conclude that Petitioner has established a reasonable likelihood of
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`prevailing on its assertions that claims 1–6 of the ’938 patent are
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`unpatentable as obvious.
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`Patent 9,549,938 B2
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`At this stage of the proceeding, the Board has not made a final
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`determination as to the patentability of any challenged claim or the
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`construction of any claim term.
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`IV. ORDER
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`In consideration of the foregoing, it is hereby:
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`ORDERED that pursuant to 35 U.S.C. § 314(a), an inter partes
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`review of claims 1–6 of the ’938 patent is instituted with respect to all
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`grounds set forth in the Petition; and
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`FURTHER ORDERED that, pursuant to 35 U.S.C. § 314(c) and
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`37 C.F.R. § 42.4(b), inter partes review of the ’938 patent shall commence
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`on the entry date of this Order, and notice is hereby given of the institution
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`of a trial.
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`15
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`IPR2018-00168
`Patent 9,549,938 B2
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`PETITIONER:
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`Philip Segrest
`philip.segrest@huschblackwell.com
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`Eric Rakestraw
`ptab-erakestraw@huschblackwell.com
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`PATENT OWNER:
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`Aaron Maurer
`amaurer@wc.com
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`David Berl
`dberl@wc.com
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`16
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