Trials@uspto.gov
`571-272-7822
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`Paper No. 14
`Entered: April 13, 2016
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`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 BONILLA, ZHENYU YANG, and
`TINA E. HULSE, Administrative Patent Judges.
`
`YANG, Administrative Patent Judge.
`
`
`
`
`DECISION
`Denying Institution of Inter Partes Review
`37 C.F.R. § 42.108
`
`
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`571-272-7822
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`
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`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 BONILLA, ZHENYU YANG, and
`TINA E. HULSE, Administrative Patent Judges.
`
`YANG, Administrative Patent Judge.
`
`
`
`
`DECISION
`Denying Institution of Inter Partes Review
`37 C.F.R. § 42.108
`
`
`
`
`
`
`
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`IPR2016-00026
`Patent 8,791,270 B2
`
`
`INTRODUCTION
`Agila Specialties Inc. and Mylan Laboratories Limited (collectively,
`“Petitioner”) filed a Petition for an inter partes review of claims 1–23 of
`U.S. 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
`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
`unpatentability of at least one challenged claim. Therefore, we deny the
`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
`patent against Petitioner in Cephalon, Inc. v. Agila Specialties Inc., Case
`No. 1:14-cv-01237 (D. Del.). Pet. 10; Paper 6. This case later was
`consolidated with several other cases filed by Patent Owner, asserting the
`’270 patent against several other entities. Pet. 9–10; Paper 6.
`Petitioner previously filed a Petition for an inter partes review of U.S.
`Patent No. 8,436,190 B2, a patent in the same family as the ’270 patent.
`Agila Specialties Inc. v. Cephalon, Inc., IPR2015-00503, Paper 4. We
`instituted trial to review the patentability of certain claims, but denied
`review of others. Id., Paper 10 (PTAB July 20, 2015). The parties
`subsequently settled, and we terminated the case. Id., Paper 21 (PTAB
`Nov. 16, 2015).
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`IPR2016-00026
`Patent 8,791,270 B2
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`The ’270 Patent
`The ’270 patent is directed to stable pharmaceutical compositions of
`nitrogen mustards, in particular, lyophilized bendamustine, which can be
`used to treat various disease states, especially neoplastic diseases and
`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 2:5–9.
`According to the ’270 patent, “[b]endamustine degrades rapidly in
`water alone and forms predominantly the hydrolysis product, HP1
`(monohydroxy bendamustine).” Id. at 21:3–5. Other degradants include the
`dimer of bendamustine (BM1 dimer), bendamustine ethylester (BM1EE),
`and BM1DCE. Id. at 21:30–50.
`The ’270 patent discloses stable pharmaceutical compositions
`prepared from bendamustine, in particular, “formulations for the
`lyophilization of bendamustine HCl.” Id. at 12:27–30. According to the
`’270 patent, the lyophilized powder obtained from such formulations is more
`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
`read as follows:
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`3
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`IPR2016-00026
`Patent 8,791,270 B2
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`1.
`A pharmaceutical composition that has been reconstituted
`from a lyophilized preparation of bendamustine or bendamustine
`hydrochloride, said composition containing not more than about
`0.9% (area percent of bendamustine) of HP1:
`
`
`composition of bendamustine
`A pharmaceutical
`7.
`hydrochloride, containing less than or equal to 4.0% (area
`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,
`while claims 8–19 depend, directly or indirectly, from claim 7.
`Claim 20 is a method claim that depends from claim 7. It reads:
`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.
`
`Asserted Grounds of Unpatentability
`Petitioner asserts the following grounds of unpatentability:
`Claims
`Basis
`Reference(s)
`1, 2, 7–10, 13–16,
`§ 102(b)
`Maas1
`19, and 20
`
`1 Maas et al., Stability of Bendamustine Hydrochloride in Infusion Solutions,
`49 PHARMAZIE 775–77 (1994) (Ex. 1007, “Maas”).
`4
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`IPR2016-00026
`Patent 8,791,270 B2
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`Claims
`1–20
`13 and 19
`20–23
`
`Basis
`§ 103
`§ 103
`§ 102
`
`Reference(s)
`Maas and Teagarden 2
`Maas, Teagarden, and Gust3
`Maas, Teagarden, and The Rote
`Liste4
`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 C.F.R. § 42.100(b); In
`re Cuozzo Speed Techs., LLC, 778 F.3d 1271, 1278–81 (Fed. Cir. 2015),
`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
`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 of Lyophilization 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 of Bendamustin, a
`Cytostatic Agent of the Nitrogen Mustard Type, I. Synthesis, Isolation, and
`Characterization of Reference 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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`IPR2016-00026
`Patent 8,791,270 B2
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`Petitioner proposes to construe the terms “lyophilized preparation”
`and “lyophilized composition,” “pharmaceutical composition,” “area percent
`of bendamustine,” “bendamustine degradants,” “time zero after
`reconstitution,” and “about.” Pet. 13–16. Patent Owner states that for the
`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
`bendamustine)’ 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
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`IPR2016-00026
`Patent 8,791,270 B2
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`more difficult to use, and often result in unacceptable freeze-dried cakes. Id.
`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,
`bendamustine is synthesized by cleaving dichloroester5 with HCl, whereas
`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 Rote 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 ¶ 87.
`7
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`IPR2016-00026
`Patent 8,791,270 B2
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`Claims 1, 2, 10, and 16
`Each of claims 1, 2, 10, and 16 requires the bendamustine
`composition to contain “not more than about 0.9% (area percent of
`bendamustine) of HP1.” According to Petitioner, Maas shows an HPLC
`chromoatogram of reconstituted Ribomustin® with a “characteristic peak of
`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 HP1 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
`HP1 present, Maas does not state a precise percent (area percent of
`bendamustine) amount of the degradants present in Ribomustin®.” Id. at
`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
`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
`required by claim 1. Id. at 24.
`In sum, Petitioner contends, because “Maas shows a small amount of
`HP1 degradant, relative to bendamustine, present in reconstituted
`Ribomustin®,” and because “[t]he ’270 patent quantifies HP1 present in
`reconstituted Ribomustin®, including lot 02K27, which had an amount of
`HP1 that falls within the scope of claim 1,” Maas anticipates claim 1. Id. at
`25. We are not persuaded.
`
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`IPR2016-00026
`Patent 8,791,270 B2
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`To anticipate a claim, a single prior art reference must expressly or
`inherently disclose each claim limitation. Schering Corp. v. Geneva Pharm.,
`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
`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
`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
`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
`“not more than about 0.9% (area percent of bendamustine).” In other words,
`Table 13 shows that the amount of HP1 in reconstituted Ribomustin® is not
`necessarily “not more than about 0.9% (area percent of bendamustine),” as
`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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`IPR2016-00026
`Patent 8,791,270 B2
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`Claims 7–10, 13–16, 19, and 20
`Claim 7 requires the composition of bendamustine hydrochloride to
`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
`refers to the test data in Table 13 of the ’270 patent to support its argument
`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 HP1.
`
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`IPR2016-00026
`Patent 8,791,270 B2
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`
`As Petitioner recognizes, Maas discloses “a pharmaceutical
`composition (Ribomustin®) reconstituted from a lyophilized preparation of
`bendamustine hydrochloride.” Pet. 26 (citing Ex. 1007, 4–5). In Maas,
`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
`contrast, samples of Ribomustin® tested in Table 13 of the ’270 patent were
`dissolved with 200 mL of methanol. 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 water but the stability of bendamustine increase with increasing
`alcohol concentrations.” Ex. 1001, 31:55–57.
`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
`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,
`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
`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
`determine that Petitioner has not shown a reasonable likelihood that it would
`prevail in these assertions.
`Petitioner refers to Maas for teaching that “bendamustine
`hydrochloride is highly unstable in water, resulting in the presence of the
`HP1 degradant in the reconstituted Ribomustin® composition.” Id. at 35.
`As a result, Petitioner argues, an ordinary artisan would have had a reason to
`“minimize the amount of HP1 and other degradants in a pharmaceutical
`composition of bendamustine hydrochloride.” Id.
`Petitioner next refers to Teagarden for teaching using TBA to improve
`the stability of unstable drugs in solution. Id. at 36 (citing Ex. 1006, 117,
`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 HP1 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
`(2) lyophilizing Ribomustin® from a TBA/water solution would reduce the
`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 HP1” in
`reconstituted Ribomustin®. Id. Reducing an unspecified “small amount of
`HP1” by “a factor of approximately 4–5,” however, does not translate into
`“not more than about 0.9% (area percent of bendamustine) of HP1,” as
`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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`Patent 8,791,270 B2
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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
`reconstituted Ribomustin formulations,” as recited in claims 1 and 7. See
`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.
`For claims 13 and 19, Petitioner relies on Gust solely for the teaching
`that bendamustine ethylester is present as an impurity in crude bendamustine
`and that it is formed when bendamustine reacts with ethanol. Pet. 53 (citing
`Ex. 1008, 292, 293, 298, 299). For claims 20–23, Petitioner relies on the
`Rote Liste solely for teaching the treatment indications for Ribomustin®.
`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 Kao, 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.”).
`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
`Petitioner has not established a reasonable likelihood that it would prevail in
`
`14
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`IPR2016-00026
`Patent 8,791,270 B2
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`showing the unpatentability of at least one challenged claim, we need not
`reach the real party-in-interest issue.
`CONCLUSION
`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.
`
`ORDER
`
`Accordingly, it is
`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
`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:
`
`Soumitra (Sam) Deka
`Aaron Stiefel
`KAYE SCHOLER LLP
`soumitra.deka@kayescholer.com
`aaron.stiefel@kayescholer.com
`
`16
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