`571-272-7822
`
`Paper No. 14
`Entered: April 13, 2016
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`AGILA SPECIALTIES INC. and MYLAN LABORATORIES LIMITED,
`
`Petitioner,
`
`.V.
`
`CEPHALON, INC,
`Patent Owner.
`
`Case IPR2016—00026
`
`Patent 8,791,270 B2
`
`Before JACQUELINE WRIGHT BONILIIA, ZHENYU YANG, and
`TINA E. HULSE, Administrative Patent Judges.
`
`YANG, Administrative Patent Judge.
`
`DECISION
`
`Denying Institution of Inter Partes Review
`37 CFR. § 42.108
`
`
`
`IPR2016-00026
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`Patent 8,791,270 B2
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`INTRODUCTION
`
`Agila Specialties Inc. and Mylan Laboratories Limited (collectively,
`
`“Petitioner”) filed a Petition for an inter partes review of claims 1—23 of
`
`US. Patent No. 8,791,270 B2 (“the ’270 patent,” EX. 1001). Paper 3
`
`(“Pet”). Cephalon, Inc. (“Patent Owner”) timely filed a Preliminary
`
`Response. Paper 12 (“Prelim Resp”). We have jurisdiction under
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`35 U.S.C. § 314.
`
`For the reasons provided below, we determine Petitioner has not
`
`established a reasonable likelihood that it would prevail in showing the
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`unpatentability of at least onc challenged claim. Therefore, we deny the
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`Petition for an inter partes review. See 35 U.S.C. § 314(a).
`
`Related Proceedings
`
`According to the parties, Patent Owner previously asserted the ’270
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`patent against Petitioner in Cephalon,- Inc. v. Agila Specialties Inc. , Case
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`No. 1:14-cv-01237 (D. Del.). Pet. 10; Paper 6. This case later was
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`consolidated with several other cases filed by Patent Owner, asserting the
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`’270 patent against several other entities. Pet. 9—10; Paper 6.
`
`Petitioner previously filed a Petition for an inter partes review of US.
`
`Patent No. 8,436,190 B2, a patent in the same family as the ’270 patent.
`
`Agila Specialties Inc. V. Cephalon, Ina, IPR2015—00503, Paper 4. We
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`instituted trial to review the patentability of certain claims, but denied
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`review of others. Id., Paper 10 (PTAB July 20, 2015). The parties
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`subsequently settled, and we terminated the case. Id., Paper 21 (PTAB
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`Nov. 16, 2015).
`
`
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`IPR2016—00026
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`Patent 8,791,270 B2
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`The ’2 70 Patent
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`The ’270 patent is directed to stable pharmaceutical compositions of
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`nitrogen mustards, in particular, lyophilized bendamustine, which can be
`
`used to treat various disease states, especially neoplastic diseases and
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`autoimmune diseases. Ex. 1001, 3:20—24.
`
`Bendamustine was first synthesized in East Germany in 1963. Id. at
`
`2: 1—2. At the time of the ’270 patent invention, bendamustine was marketed
`
`in Germany under the name Ribomustin® to treat chronic lymphocytic
`
`leukemia, Hodgkin’s disease, non—Hodgkin’s lymphoma, multiple myeloma,
`
`and breast cancer. Id. at 25—9.
`
`According to the ’270 patent, “[b]endarnustine degrades rapidly in
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`water alone and forms predominantly the hydrolysis product, HPl
`
`(monohydroxy bendamustine).” Id. at 2123—5. Other degradants include the
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`dimer of bendamustine (BMl dimer), bendamustine ethylester (BMlEE),
`
`and BMIDCE. Id. at 21:30—50.
`
`The ’270 patent discloses stable pharmaceutical compositions
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`prepared from bendamustine, in particular, “formulations for the
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`lyophilization of bendamustine HCl.” Id. at 12:27~30. According to the
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`’270 patent, the lyophilized powder obtained from such formulations is more
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`easily reconstituted and has a better impurity profile than Ribomustin®. Id.
`
`at 12:30—37.
`
`Illustrative Claims
`
`Among the challenged claims, claims 1 and 7 are independent. They
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`'
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`read as follows:
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`
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`IPR2016-00026
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`Patent 8,791,270 B2
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`A pharmaceutical composition that has been reconstituted
`1.
`from a lyophilized preparation of bendamustine or bendamustine
`hydrochloride, said composition containing not more than about
`0.9% (area percent of bendamustine) of HPl:
`
`(UPI)
`
`HOd N
`O
`I \C[ \>—\—>—OH.
`N\
`
`Cl
`
`bendamustine
`of
`composition
`A pharmaceutical
`7.
`to 4.0% (area
`hydrochloride, containing less than or equal
`percent of bendamustine) of bendamustine degradants.
`
`Dependent claims 2—6 and 8—19 also are directed to pharmaceutical
`
`compositions. Claims 2—6 depend, directly or indirectly, from claim 1,
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`while claims 8—19 depend, directly or indirectly, from claim 7.
`
`Claim 20 is a method claim that depends from claim 7. It reads:
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`20. A method of treating cancer in a patient comprising
`administering to the patient a pharmaceutical composition of
`bendamustine hydrochloride according to claim 7.
`
`Each of claims 21 —23 is a method claim that depends directly from
`
`claim 20.
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`Asserted Grounds of Unpatentability
`
`Petitioner asserts the following grounds of unpatentability:
`
`
`
`Claims m Reference 5
`1, 2, 7—10, 13—16,
`.
`§ 102(b)
`Maas'
` __—__—__—_—-—
`
`19, and 20
`
`
`
`1 Maas et al., Stability ofBendamustine Hydrochloride in Infusion Solutions,
`49 PHARMAZIE 775—77 (1994) (Ex. 1007, “Maas”).
`4
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`Patent 8,791,270 B2
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`
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`_m Reference s
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`
`~ 103
`Maas and Teagarden 2
`~ 103
`Maas, Teaarden, and Gust3
`§ 102
`Maas, Teagarden, and The Rote
`Liste4
`
`
`13 and 19
`20—23
`
`
`
`
`
`
`In support of its patentability challenge, Petitioner relies on the
`
`Declaration of Dr. Samuel H. Yalkowsky. Ex. 1002.
`
`ANALYSIS
`
`Claim Construction
`
`In an inter partes review, the Board interprets a claim term in an
`
`unexpired patent according to its broadest reasonable construction in light of
`
`the specification of the patent in which it appears. 37 CPR. § 42.100(b); In
`
`re Cuozzo Speed Techs, LLC, 778 F.3d 1271, 1278—81 (Fed. Cir. 2015),
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`cert, granted sub nom. Cuozzo Speed Techs. LLC v. Lee, 136 S. Ct. 890
`
`(mem.) (2016). Under that standard, absent any special definitions, we
`
`assign claim terms their ordinary and customary meaning, as would be '
`
`understood by one of ordinary skill in the art at the time of the invention, in
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`the context of the entire patent disclosure. In re Translogic Tech., Inc, 504
`
`F.3d 1249, 1257 (Fed. Cir. 2007).
`
`2 Teagarden and Baker, Practical Aspects ofLyophilization Using Non—
`Aqueous Co-Solvent Systems, 15 EUR. J. PHARM. SCI. 115—33 (2002)
`(Ex. 1006, “Teagarden”).
`3 Gust and Krauser, Investigations on the Stability ofBendamustin, a
`Cytostatic Agent ofthe Nitrogen Mustard Type, 1. Synthesis, Isolation, and
`Characterization ofReference Substances, 128 CHEMICAL MONTHLY 291—
`99 (1997) (Ex. 1008, “Gust”).
`4 The Rote Liste 2003 (Ex. 1005, “the Rote Liste”).
`5
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`Patent 8,791,270 BZ
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`Petitioner proposes to construe the terms “lyophilized preparation”
`99 6‘
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`and “lyophilized composition,” “pharmaceutical composition,
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`area percent
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`of bendamustine,” “bendamustine degradants,” “time zero after
`
`reconstitution,” and “about.” Pet. 13~16. Patent Owner states that for the
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`purpose of this Decision, it accepts Petitioner’s proposed constructions.
`
`Prelim. Resp. 16. We similarly accept Petitioner’s proposed constructions
`
`for purposes of this Decision. Specifically, we accept that “in the context of
`
`the claims and specification of the ’270 patent, one of ordinary skill in the
`
`art would construe the claim term ‘about 0.9% (area percent of
`
`bendamustinc)’ to include ‘0.96% (area percent of bendamustine).”’ Pet. 16.
`
`Prior Art Disclosures
`
`. Maas discloses bendamustine as “very unstable in an aqueous
`
`solution.” Ex. 1007, 4. It explains that “[d]ue to the rapidly progressing
`
`hydrolysis of aqueous bendamustine hydrochloride solutions, only freshly
`
`made up solutions .
`
`.
`
`. must be injected immediately after their preparation.”
`
`Id. at 5. In a stability test, Maas identified bendamustine hydrochloride by
`
`reverse-phase. HPLC . Id.
`
`Teagarden teaches that using non-aqueous co—solvent systems in
`
`freeze-drying pharmaceutical products has numerous advantages, including
`
`“increased pre-dried bulk solution or dried product stability.” Ex. 1006, 115.
`
`Specifically, according to Teagarden, the tert-butanol (“TBA”)/water
`combination “possesses a high vapor pressure, freezes completely in most
`
`commercial freeze-dryers, readily sublimes during primary drying, can
`
`increase sublimation rates, and has low toxicity.” Id.
`
`In contrast, other co-
`
`solvent systems do not freeze completely in commercial freeze—dryers, are
`6
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`Patent 8,791,270 B2
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`more difficult to use, and often result in unacceptable freeze-dried cakes. Id.
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`In addition, Teagarden teaches that the TBA/water co-solvent system
`
`“significantly reduced” the degradation rate of certain water unstable drugs.
`
`Id. at 117—18.
`
`Gust teaches the synthesis, isolation, and characterization of
`
`bendamustine and its derivatives. Ex. 1008, 291_99_ According to Gust,
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`bendamustine is synthesized by cleaving dichloroester5 with HCl, whereas
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`dichloroester can be formed by esterification of bendamustine in ethanolic
`
`HCl. Id. at 292—93. Gust also teaches that dichloroester is present in crude
`
`bendamustine samples. Id. at 298.
`
`The Rotc Liste teaches Ribomustin® is a dry substance and specifies
`
`that “1 injection vial with 55 mg .
`
`.
`
`. dry substance” contains “bendamustine
`
`HCl 25 mg.” Ex. 1005, 3. It also lists “M. Hodgkin (Stages II — IV), Non—
`
`Hodgkin lymphoma, Plasmacytoma, Chron. lymphat. leukemia, mammary
`
`carcinoma” under “Treatment Indications.” Id.
`
`Anticipation Ground
`
`Petitioner argues that Maas anticipates claims 1, 2, 7—10, 13—16, 19,
`
`and 20. Pet. 22—33. Based on the current record, we determine Petitioner
`
`has not established a reasonable likelihood that it would prevail in this
`
`assertion.
`
`5 According to Dr. Yalkowsky, dichloroester in Gust is the same as
`bendamustine ethylester in the ’270 patent. Ex. 1002 11 87.
`7
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`Patent 8,791,270 B2
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`Claimsl 2 10 and 16
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`Each of claims 1, 2, 10, and 16 requires the bendamustine
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`composition to contain “not more than about 0.9% (area percent of
`
`bendamustine) of HP] .” According to Petitioner, Maas shows an HPLC
`
`chromoatogram of reconstituted Ribomustin® with a “characteristic peak of
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`bendamustine” and a peak for a decomposition product, “presumably the
`
`monohydrolysis product,” i.e., HP1. Pet. 23 (citing Ex. 1007, 5). Petitioner
`
`contends that “[t]he peak corresponding to HPl is small relative to the peak
`
`corresponding to bendamustine in the figure of Maas.” Id.
`
`Petitioner acknowledges “[t]hough Maas shows a small amount of
`
`HPl present, Maas does not state a precise percent (area percent of
`
`bendamustine) amount of the degradants present in Ribomustin®.” Id. at
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`21. Nevertheless, Petitioner argues that the ’270 patent provides the
`
`requisite data. Id. Specifically, Petitioner refers to Table 13 of the ’270
`
`patent and points out that one batch of Ribomustin®, 02K27, contains
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`0.93% area of HP1. Id. at 23. This, according to Petitioner, is equal to
`
`0.96% (area percent of bendamustine), and, under Petitioner’s proposed
`
`construction, satisfies “about 0.9% (area percent of bendamustine),” as
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`required by claim 1. Id. at 24.
`
`1n sum, Petitioner contends, because “Maas shows a small amount of
`
`HPl degradant, relative to bendamustine, present in reconstituted
`
`Ribomustin®,” and because “[t]he ’270 patent quantifies HPl present in
`
`reconstituted Ribomustin®, including lot 02K27, which had an amount of
`
`HPl that falls within the scope of claim 1,” Maas anticipates claim 1. Id. at
`
`25. We are not persuaded.
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`Patent 8,791,270 B2
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`To anticipate a claim, a single prior art reference must expressly or
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`inherently disclose each claim limitation. Scherz’ng Corp. v. Geneva Pharm,
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`339 F.3d 1373, 1379 (Fed. Cir. 2003). Petitioner bases its anticipation
`
`argument on an inherency theory. Pet. 24—25. Under the principles of
`
`inherency, if the prior art necessarily functions in accordance with, or
`
`includes, the claimed limitations, it anticipates. In re Cruciferous Sprout
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`Litig, 301 F.3d 1343, 1349 (Fed. Cir. 2002). “Inherency, however, may not
`
`be established by probabilities or possibilities. The mere fact that a certain
`
`thing may result from a given set of circumstances is not sufficient.” In re
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`Robertson, 169 F.3d 743, 745 (Fed. Cir. 1999).
`
`Here, Table 13 of the ’270 patent reports the impurity profile of four
`
`batches of Ribomustin®. Ex. 1001, 30:33—45. As Patent Owner correctly
`
`points out, Petitioner relies on the data from only a single batch with the
`
`lowest HP1 content. See Prelim. Resp. 21. Petitioner fails to mention that
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`for each of the other three batches of Ribomustin® tested, the HP1 content is
`
`over 1% (area percent of bendamustine), outside of the required range of
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`“not more than about 0.9% (area percent of bendamustinc).” In other words,
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`Table 13 shows that the amount of HP1 in reconstituted Ribomustin® is not
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`necessarily “not more than about 0.9% (area percent of bendamustine),” as
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`required by claims 1, 2, 10, and 16.6 As a result, based on the current
`
`record, we are not persuaded that Maas inherently anticipates those claims.
`
`6 Moreover, even if the other three batches of Ribomustin® tested in Table
`13 contained the claimed range of HP1, Petitioner’s argument still would fail
`because Petitioner presents an insufficient connection between the
`Ribomustin® samples disclosed in Table 13 of the ’270 patent with the
`'
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`Patent 8,791,270 B2
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`Claims 7—-10 13—16 19, and 20
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`Claim 7 requires the composition of bendamustine hydrochloride to
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`contain “less than or equal to 4.0% (area percent of bendamustine) of
`
`_ bendamustine degradants.” Petitioner concedes that Maas itself “does not
`
`state a precise percent (area percent of bendamustine) amount of the
`
`degradants present in Ribomustin®.” Pet. 21. Instead, Petitioner again
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`refers to the test data in Table 13 of the ’270 patent to support its argument
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`that Maas inherently anticipates the challenged claim 7. Id. at 26.
`
`According to Petitioner, Ribomustin® compositions tested in the ’270 patent
`
`“contained from 1.68% to 2.56% (area percent of bendamustine) of
`
`bendamustine hydrochloride degradants.” Id. (citing Ex. 1001, 30:35—45).
`
`Thus, Petitioner concludes, “the composition disclosed by Maas contained
`
`amounts of bendamustine hydrochloride degradants falling well within the
`
`‘less than or equal to 4.0% (area percent of bendamustine)’ recited in claim
`
`7.” Id. at 26—27.
`
`Patent Owner counters that Table 13 of the ’270 Patent does not shed
`
`light on the contents of the reconstituted pharmaceutical composition
`described in Maas because “[u]nlike Maas, Table 13 does not report the
`
`content of a reconstituted pharmaceutical composition.” Prelim. Resp. 24.
`
`We agree.
`
`Ribomustin® samples analyzed in Maas. That is, Petitioner has not
`established that the Ribomustin® analyzed in Maas necessarily has the
`claimed amount of HPl.
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`Patent 8,791,270 B2
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`As Petitioner recognizes, Maas discloses “a pharmaceutical
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`composition (Ribomustin®) reconstituted from a lyophilized preparation of
`
`bendamustine hydrochloride.” Pet. 26 (citing Ex. 1007, 4—5). In Maas,
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`bendamustine hydrochloride “was dissolved first in 10 mL of water and then
`
`diluted with 0.9% sodium chloride solution to 100 mL.” EX. 1007, 5. In
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`contrast, samples of Ribomustin® tested in Table 13 of the ’270 patent were
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`dissolved with 200 mL ofmethanol. EX. 1001, 29:29—31, 30:33—34. Maas
`
`acknowledges that bendamustine “is very unstable in an aqueous solution.”
`
`Ex. 1007, 4. And the ’270 patent confirms this: “Bendamustine degrades
`
`quickly in watcr but the stability of bendamustine increase with increasing
`
`alcohol concentrations.” Ex. 1001, 31:55 57.
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`Thus, we agree with Patent Owner that “[i]f the Ribomustin analyzed
`
`in the ’270 Patent had (as in Maas) been dissolved in water and diluted in a
`
`solution of sodium chloride and water, instead of being dissolved in pure
`
`methanol, the bendamustine would have degraded further.” Prelim. Resp.
`
`20. In other words, the fact that Table 13 of the ’270 patent reports
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`Ribomustin® compositions containing “from 1.68% to 2.56% (area percent
`
`of bendamustine) of bendamustine hydrochloride degradants” does not mean
`
`reconstituted Ribomustin® in Maas necessarily would also contain “less
`
`than or equal to 4.0% (area percent of bendamustine) of bendamustine
`
`degradants,” as claim 7 requires. As a result, based on the current record,
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`we are not persuaded that Maas inherently anticipates claim 7 or its
`
`dependent claims, claims 8—10, 13—16, 19 and 20.
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`Patent 8,791,270 B2
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`Obviousness Grounds
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`Petitioner asserts that claims 1—20 would have been obvious over
`
`Maas and Teagarden, claims 13 and 19 would have been obvious over Maas
`
`Teagarden, and Gust, and claims 20—23 would have been obvious over Maas
`
`Teagarden, and the Rote Liste. Pet. 33—57. Based on the current record, we
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`determine that Petitioner has not shown a reasonable likelihood that it would
`
`prevail in these assertions.
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`Petitioner refers to Maas for teaching that “bendamustine
`
`hydrochloride is highly unstable in water, resulting in the presence of the
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`IlPl degradant in the reconstituted Ribomustin® composition.” Id. at 35.
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`As a result, Petitioner argues, an ordinary artisan would have had a reason to
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`“minimize the amount of HPl and other degradants in a pharmaceutical
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`composition of bendamustine hydrochloride.” Id.
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`Petitioner next refers to .Teagarden for teaching using TBA to improve
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`the stability of unstable drugs in solution. Id. at 36 (citing Ex. 1006, 1 17,
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`118). Specifically, Petitioner points to Teagarden for describing using
`
`TBA/water in five drug formulations.
`
`Id. According to Petitioner,
`
`Teagarden teaches that the TBA/water co—solvent system improves the
`
`stability of those water unstable drugs. Id. (citing Ex. 1006, 117 (reporting
`
`that for one drug, the first-order degradation rate constant “was significantly
`
`reduced compared to water”), 118 (reporting that using TBA slowed solution
`state degradation of another drug “by a factor of approximately 4—5”)). Also
`
`according to Petitioner, Teagarden predicts that this stabilizing effect “would
`
`be expected to be observed for many other drug products which are
`
`degraded in the presence of water.” Id. (citing Ex. 1006, 118). Thus,
`12
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`Patent 8,791,270 B2
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`Petitioner argues, one of ordinary skill in the art would have lyophilized
`
`bendamustine hydrochloride from a TBA/water solution with a reasonable
`
`expectation of success “in reducing the small amount of HPl present in
`
`Ribomustin® up to four- to five-fold, which would fall well below 0.9%
`
`(area percent of bendamustine), as recited in claim 1” (id), and “in arriving
`
`at a composition containing substantially less than the amount of
`
`bendamustine degradants in Ribomustin®,” as recited in claim 7 (id. at 41).
`
`We are not persuaded.
`
`For purposes of this Decision, we assume, without deciding, that
`
`(1) one of ordinary skill in the art would have had a reason to combine the
`
`teachings of Maas, Teagarden, and other asserted prior art references; and
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`(2) lyophilizing Ribomustin® from a TBA/water solution would reduce the
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`degradation rate by “a factor of approximately 4—5.” We nevertheless are
`
`not persuaded that the prior art would have rendered the challenged claims
`
`obvious.
`
`As Petitioner acknowledges, “Maas does not state a precise percent
`
`(area percent of bendamustine) amount. of the degradants present in
`
`Ribomustin®” (Pet. 21), and “Teagarden does not teach a composition of
`
`bendamustine hydrochloride” (id. at 22). Rather, Petitioner characterizes
`
`that the HPLC chromatogram shows “a small amount of HPI” in
`
`reconstituted Ribomustin®. Id. Reducing an unspecified “small amount of
`
`HPl” by “a factor of approximately 4—5,” however, does not translate into
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`“not more than about 0.9% (area percent of bendamustine) of HPl,” as
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`recited in claim 1, or “less than or equal to 4.0% (area percent of
`
`bendamustine) of bendamustine degradants,” as recited in claim 7. Thus, we
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`agree with Patent Owner that “Maas and Teagarden taken together still
`
`would not suggest specific limits on the amounts of the degradants in
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`reconstituted Ribomustin formulations,” as recited in claims 1 and 7. See
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`Prelim. Resp. 34. Petitioner also does not otherwise argue that the general
`
`knowledge of a skilled artisan would have suggested the specific amounts of
`
`the degradants in reconstituted Ribomustin® recited in claims 1 and 7.
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`For claims 13 and 19, Petitioner relies on Gust solely for the teaching
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`that bendamustine ethylester is present as an impurity in crude bendamustine
`
`and that it is formed when bendamustine reacts with ethanol. Pet. 53 (citing
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`Ex. 1008, 292, 293, 298, 299). For claims 20—23, Petitioner relies on the
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`Rote Liste solely for teaching the treatment indications for Ribomustin®.
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`Id. at 55—56. In other words, neither Gust nor the Rote Liste remedies the
`
`deficiencies of Mass and Teagarden, as discussed above.
`
`Thus, based on the current record, we determine that Petitioner has
`
`not shown a reasonable likelihood that it would prevail in showing the
`
`challenged claims would have been obvious over Mass, Teagarden, Gust,
`
`and the Rote Liste. See In re Kan, 639 F.3d 1057, 1066 (Fed. Cir. 2011)
`
`(“[I]t matters greatly whether anything the skilled artisan would be prompted
`
`by the prior art to do is in fact within the scope of the .
`
`.
`
`. claim”).
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`Real Party-in-Interest
`
`Patent Owner urges that we deny the Petition because Petitioner fails
`
`to identify Mylan Inc. and Mylan Pharmaceuticals Inc. as real parties—in-
`
`interest with respect to the Petition. Prelim. Resp. 10—15. Because
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`Petitioner has not established a reasonable likelihood that it would prevail in
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`Patent 8,791,270 B2
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`showing the unpatentability of at least one challenged claim, we need not
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`reach the real party-in-interest issue.
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`CONCLUSION
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`For the foregoing reasons, the information presented in the Petition
`
`and accompanying evidence does not establish a reasonable likelihood that
`
`Petitioner would prevail in showing the unpatentability of any of the
`
`challenged claims.
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`Accordingly, it is
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`ORDER
`
`ORDERED that Petitioner’s request for an inter partes review of
`
`claims 1—23 of the ’270 patent is denied.
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`IPR2016—00026
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`Patent 8,791,270 B2
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`PETITIONER:
`
`Steven W. Parmelee
`
`Michael T. Rosato
`
`Nicole W. Stafford
`
`WILSON SONSINI GOODRICH & ROSATI
`
`sparmelee@wsgr.com
`mrosato@wsgr.com
`nstafford@wsgr.com
`
`PATENT OWNER:
`
`Soumilra (Sam) Deka
`Aaron Stiefel
`
`KAYE SCHOLER LLP
`
`soumitra.deka@kayescholer.com
`aaron;3ticfcl@kayeseholel .00111
`
`16
`
`