Paper 8
`
`Entered: October 1, 2014
`
`Trials@uspto.gov
`571-272-7822
`
`
`
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________
`
`TORRENT PHARMACEUTICALS LIMITED,
`Petitioner,
`
`v.
`
`MERCK FROSST CANADA & CO.,
`Patent Owner.
`____________
`
`Case IPR2014-00559
`Patent 6,448,274 B2
`____________
`
`
`Before LORA M. GREEN, ERICA A. FRANKLIN, and
`ZHENYU YANG, Administrative Patent Judges.
`
`YANG, Administrative Patent Judge.
`
`DECISION
`Denying Institution of Inter Partes Review
`37 C.F.R. § 42.108
`
`
`
`
`
`
`
`
`
`
`
`
`
`Entered: October 1, 2014
`
`Trials@uspto.gov
`571-272-7822
`
`
`
`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________
`
`TORRENT PHARMACEUTICALS LIMITED,
`Petitioner,
`
`v.
`
`MERCK FROSST CANADA & CO.,
`Patent Owner.
`____________
`
`Case IPR2014-00559
`Patent 6,448,274 B2
`____________
`
`
`Before LORA M. GREEN, ERICA A. FRANKLIN, and
`ZHENYU YANG, Administrative Patent Judges.
`
`YANG, Administrative Patent Judge.
`
`DECISION
`Denying Institution of Inter Partes Review
`37 C.F.R. § 42.108
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`IPR22014-00559
`
`
`Patennt 6,448,2774 B2
`
`I.
`
`
`
`1. A commpound reepresented by Formulla (I):
`
`
`
`INTRODDUCTIONN
`
`
`
`
`
`
`Torrent Pharmaceuuticals Limmited (“Pettitioner”) fifiled a Petittion for an
`
`
`
`interr partes revview of claaims 1 and
`2 of U.S.
`
`
`Patent No.. 6,448,2744 (“the
`
`
`
`
`
`
`
`’2744 patent”). Paper 1 (““Pet.”). MMerck Frossst Canada && Co. (“Paatent
`
`
`
`
`Ownner”) did noot file a Prreliminary Response.
` We have
`
` jurisdictioon under
`
`
`35 UU.S.C. § 314.
`
`
`
`
`
`
`For the rreasons proovided beloow, we dettermine Peetitioner haas not
`
`
`
`
`
`
`
`estabblished a reeasonable likelihood that it wouuld prevaill in showinng the
`
`
`
`
`
`unpaatentabilityy of at leastt one of thee challengeed claims.
`
`
`
`
`
`
`
`
`fails to meet thhe threshold requiremment set forrth in 35 UU.S.C. § 31
`4(a), we
`
`
`denyy the Petitioon.
`A.
`
`
`Thhe ’274 Paatent
`
`
`
`
`The ’2744 patent is directed too N-(3,5-DDichloro-1--oxido-pyr
`
`idin-4-yl)-
`
`
`
`
`
`
`
`4-diffluoromethhoxy-3-cycclopropylmmethoxybennzamide, wwhich is a ccAMP
`
`
`
`
`
`
`
`phossphodiesterrase-4 (PDDE4) inhibiitor. Ex. 10001, 1:12––15. Accorrding to th
`
`
`
`
`
`
`
`’2744 patent, inhhibition off PDE4 “caan beneficiially affectt allergy annd
`
`
`inflaammation ssymptoms..” Id. at 1:46–49.
`
`
`
`
`Claims 11 and 2 reaad:
`
`
`
`
` Because tthe Petitionn
`
`- h
`
`e
`
`
`2. A pharmaceuticcal composition commprising a
`
`
`
`
`
`therapeutiically
`
`to claim
`
`
`
`
`
`
`effectivee amount oof
`
`
`the coompound aaccording
`
`
`acceptabble salt therreof; and
`
`
`
`
`2
`
`
`
`1 or a phharmaceutiically
`
`
`
`a pharmmaceuticallly acceptaable carrierr.
`
`
`
`
`
`IPR2014-00559
`Patent 6,448,274 B2
`
`
`Asserted Grounds of Unpatentability
`B.
`Petitioner challenges claims 1 and 2 as anticipated by PCT Publication
`No. WO 94/02465 (published on February 3, 1994) (Ex. 1002, “Fenton”).
`Pet. 13. Petitioner also alleges that Fenton, together with PCT Publication
`No. WO 92/12961(published on August 6, 1992) (Ex. 1003, “Ashton”) and a
`skilled artisan’s general knowledge, renders claims 1 and 2 obvious. Id.
`Both Fenton and Ashton were published more than one year before the
`priority date (May 25, 2000) of ’274 patent and thus, qualify as art under
`35 U.S.C. § 102(b).
`
`II. ANALYSIS
`A.
`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).
`Under this standard, we assign claim terms their ordinary and customary
`meaning, as understood by a person of ordinary skill in the art, in the context
`of the entire patent disclosure. In re Translogic Tech., Inc., 504 F.3d 1249,
`1257 (Fed. Cir. 2007).
`Petitioner proposes a construction for the chemical formula recited in
`claim 1. Pet. 10. Petitioner also asks us to construe the terms
`“pharmaceutical composition comprising a therapeutically effective amount”
`and “pharmaceutically acceptable carrier.” Id. at 10–11. Petitioner does not
`explain how the constructions of these terms are material to our decision of
`whether to institute a trial, and we conclude that such constructions are not
`
`
`
`3
`
`
`
`
`
`neceessary at thhis time. Thus, we deecline to coonstrue theese terms eexpressly
`
`
`
`
`
`9
`
`IPR22014-0055
`
`
`Patennt 6,448,2774 B2
`
`
`
`
`
`
`
`for ppurposes off this Deci
`sion.
`B.
`
`Prrior Art
`1.
`
`Feenton
`
`
`
`
`
`Fenton tteaches commpounds inn the followwing formmula:
`
`
`
`
`
`
`
`
`
`R2 is alkkyl, alkenyll, cycloalkkyl, cycloallkenyl, cycclothioalkyyl or
`
`
`
`
`
`
`
`
`wherrein
`
`R1 is lowwer alkyl;
`
`
`
`
`cycloothioalkennyl;
`
`
`R3 is aryyl or heterooaryl;
`
`
`
`
`
`Z, Z1, annd Z2 are inndependenntly oxygenn or sulfur;;
`
`
`
`
`
`
`Z3 is -CHH=CH-, -CC≡C-, -CH22-CZ-, -CZZCH2-, -CCZ-CZ-, -CCH2-NH-,
`
`
`
`
`
`
`
`NH-,.-NH-C-O-, -CZN-CH2-O-, -CH2-S-, -CX2 CH2-, -O-CCH2-, -SCHH2-,
`-SOC
`
`
`
`
`
`
`N-, -NH-SO-CZ-, -N=NCZ-, -NH-CH2-, -SO22CH2-, -O--CX2-, -O-C O2-,
`
`
`
`
`O-O-, -O-C-, -NH-COZ-CZ-NH--SO22-NH- , -CZ
`O-NH- or
`
`-NH-CO-NNH-; and
`
`X is haloo.
`
`
`
`
`
`
`
`
`
`
`
`
`
`acceeptable saltt thereof.” Id. Accorrding to Feenton, thesee compounnds,
`
`
`
`
`
`
`
`
`
`
`
`
`autoimmune diiseases. Idd.
`
`2.
`
`AAshton
`
`
`
`formmula:
`
`Ex. 11002, 7. FFenton alsoo teaches “aan N-oxidee thereof oor a pharmaaceuticallyy
`
`throuugh their aability to innhibit PDE4, are usefful in treatiing inflammmatory andd
`
`
`
`depicted inn the followwing
`
`
`
`Ashton tteaches bennzamide d
`
`erivatives
`
`
`
`4
`
`
`
`
`
`IPR22014-00559
`
`
`Patennt 6,448,2774 B2
`
`
`
`
`
`
`
`“wheerein Rl reppresents allkyl, R2 reppresents alk
`
`kyl or monno-, bi- or
`
`
`
`
`
`
`tricyycloalkyl, RR3 represennts an optioonally subsstituted phhenyl, naphhthyl or
`
`
`
`or sulphurr.”1 Ex. 10003,
`
`
`
`
`heterrocyclyl grroup, and ZZ representts oxygen
`
`
`
`
`
`Absttract, 1–2. Ashton allso teachess the N-oxiides of the
`
`compoundds “when
`
`nitrogen rring atoms..” Id. at
`
`
`
`
`said heterocycllyl groups contain onne or more
`
`
`
`
`
`
`
`Absttract, 2. AAccording to Ashton, compositioons containning these
`
`
`
`
`
`comppounds, annd their pharmaceuticcally accepptable saltss, are usefuul, for
`
`
`
`
`
`
`
`
`exammple, as bronchodilattors and asthma-propphylactic aggents, in trreating
`
`
`condditions thatt can be ammeliorated bby adminisstering a PPDE inhibittor. Id. at
`
`
`
`
`
`
`10.
`
`
`
`
`
`
`
`Ashton ddiscloses thhat “[e]speecially impportant commpounds” iinclude
`
`
`
`
`
`thosee wherein at least one of R1, R22, and R3 iss selected ffrom the foollowing:
`
`
`
`
`l represents a methyl group;
`(i)
`R
`
`
`
`
`
`
`R22 representts a propyl, butyl, nonnyl, dodeccyl, cycloheexyl,
`(ii)
`
`
`
`
`
`8,9,10-trrinorbornyyl or, more especiallyy, cyclopenntyl group;
`and/or
`
`
`
`3 representts an optionnally substtituted pyra
`(iii)
`azinyl,
`R
`
`
`
`
`
`pyrimidiinyl, isoxazolyl, prefferably pyrridyl groupp, or an N-
`
`
`
`
`
`oxide thereof, or ann optionallly substitutted phenyll group.
`
`Id. aat 3.
`
`
`
`
`
`
`
`
`
`1 According to the Petitioon, R1 in AAshton and
`
`
`
`samee position. Pet. 26. SSimilarly, R2 and R3
`
`
`
`
`
`in the twoo referencess
`
`
`
`
`
`
`
`correespond to tthe same reespective ppositions.
`
`
`correesponds to Z3 in Fentton. Id. at
`26–27.
`
`
`R1 in Fentton corresppond to thee
`
`Id. Furtheer, -CZNHH- in Ashtonn
`
`
`
`5
`
`
`
`IPR2014-00559
`Patent 6,448,274 B2
`
`
`Anticipation
`C.
`Referring to various excerpts in Fenton that teach preferred classes of
`substituents at the positions of R1, R2, R3, Z1, Z2, and Z3, Petitioner asserts
`that Fenton discloses each and every limitation of claims 1 and 2 “arranged
`as claimed,” and thus, anticipates the challenged claims. Pet. 13–23. We
`disagree.
`For example, according to Petitioner, challenged claim 1 has
`difluorinated methyl at the position corresponding to R1 in Fenton. Id. at 16.
`Petitioner asserts that Fenton discloses “lower alkyl substituted by halo” as
`preferred R1 (id. at 16 (citing Ex. 1002, 12:17–21, 12:36–37, 13:7–10)), with
`lower alkyl being “about 1 to about 4 carbon atoms in the chain which may
`be straight or branched” (Ex. 1002, 8:9–10).2 Petitioner also points out that
`Fenton discloses:
`Compounds of the invention wherein R1 is substituted by halo,
`preferably fluoro, are preferred. It is also preferred that the halo
`substitution is on positions of the R1 that are adjacent to the
`position of R1 that is attached respectively to Z1.
`Pet. 16 (citing Ex. 1002, 14:1–4). Based on these disclosures, Petitioner
`concludes “Fenton prefers [R1] as a fluorinated methyl group – including
`difluoro – as recited in [the challenged] claim 1.” Id.
`
`
`2 Petitioner cites Ex. 1002, 8:27–28 for the proposition that “Fenton
`discloses R1 as a lower alkyl (lower alkyls are about 1–4C).” Pet. 16. The
`cited portion of Fenton, however, in its entirety, reads “‘Cycloalkyl’ means a
`non-aromatic mono- or multicyclic ring system of about 3 to about 10
`carbon atoms. Preferred monocyclic cycloalkyl rings,” and thus, does not
`support Petitioner’s statement. See Ex. 1002, 8:27–28.
`
`
`
`6
`
`
`
`IPR2014-00559
`Patent 6,448,274 B2
`
`
`Through similar analyses, Petitioner argues that Fenton prefers
`cyclopropylmethyl at the R2 position (id. at 17); 3,5-dihalopyrid-4-yl N-
`oxide at R3 (id. at 18); oxygen at both Z1 and Z2 (id. at 19–20); and -CZNH-
`(where Z is O) at Z3 (id. at 21–22). A combination of these preferred
`substituents at these positions, according to Petitioner, results in the same
`formula as the compound recited in challenged claim 1. Id. at 14.
`Petitioner’s argument runs afoul of well-settled law on anticipation.
`To anticipate, a prior art reference “must not only disclose all elements of
`the claim within the four corners of the document, but must also disclose
`those elements ‘arranged as in the claim.’” Net MoneyIN, Inc. v. VeriSign,
`Inc., 545 F.3d 1359, 1369 (Fed. Cir. 2008) (quoting Connell v. Sears,
`Roebuck & Co., 722 F.2d 1542, 1548 (Fed. Cir. 1983)).
`Fenton, the purported anticipatory reference, does not satisfy this
`requirement. It does not show the specific combination as illustrated in the
`challenged claim 1, but only demonstrates classes of possible substituents at
`various positions. Ex. 1002, 9–16. Fenton does teach certain subclasses of
`substituents as preferred; but the scope and content of these subclasses are
`not so specific as to be deemed a disclosure of the claimed combination. In
`particular, Fenton does not present so short and selective a list of these
`subclasses that a person of ordinary skill would, as Petitioner asserts, “at
`once envisage” the claimed compound. Pet. 23; see Eli Lilly & Co. v. Zenith
`Goldline Pharm., Inc., 471 F.3d 1369, 1376 (Fed. Cir. 2006).
`In sum, Petitioner has not shown Fenton discloses all of the
`limitations of claim 1 “arranged or combined in the same way as in the
`claim.” Net MoneyIN, 545 F.3d at 1370. Therefore, we conclude Petitioner
`
`
`
`7
`
`
`
`IPR2014-00559
`Patent 6,448,274 B2
`
`has not established a reasonable likelihood that it would prevail in showing
`Fenton anticipates claims 1 or 2.
`D. Obviousness
`Petitioner asserts that claims 1 and 2 would have been “obvious over
`Fenton, including in view of Ashton, and a [skilled artisan’s] general
`knowledge.” Pet. 25. Petitioner’s argument is unpersuasive.
`Petitioner bases its asserted obviousness ground on the structural
`similarities between the claimed compound and the prior art compounds.
`See id. at 25–31. Generally, in such cases, to establish obviousness of a
`claimed compound, a challenger of the claim needs to identify some reason
`that would have led a skilled artisan to select and then modify a known
`compound. Takeda Chem. Indus., Ltd. v. Alphapharm Pty., Ltd., 492 F.3d
`1350, 1357 (Fed. Cir. 2007). The requisite motivation can come from any
`number of sources, and need not necessarily be explicit in the art. Eisai Co.
`Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 1359 (Fed. Cir. 2008).
`Petitioner repeats that Fenton’s “hierarchy of preferred substituents”
`at the positions of R1, R2, R3, Z1, Z2, and Z3 would have led one skilled in the
`art to the exact compound recited in claim 1. Pet. 25. In addition, Petitioner
`contends, “Ashton would have solidly reinforced Fenton’s teaching.” Id.
`For example, as discussed above, Petitioner asserts that Fenton prefers “a
`fluorinated methyl group – including difluoro” as R1. See supra Section
`II.C. Petitioner also observes that the exemplary compounds in Ashton
`exclusively have methyl as R1. Pet. 30. According to Petitioner, one skilled
`in the art “would thus favor this methyl moiety, but make the fluorine
`substitutions that Fenton favors.” Id. Through similar analyses, Petitioner
`contends that “using Fenton and Ashton,” a skilled artisan would have
`8
`
`
`
`
`
`IPR2014-00559
`Patent 6,448,274 B2
`
`chosen the claimed substituents as “the most promising moieties” and
`“would easily and directly arrive at the claimed N-Oxide compound.” Id. at
`28–31.
`Petitioner’s arguments are tenuous at best. In order to illustrate our
`reasoning, however, we treat them as if they were correct. Even with such a
`head start, Petitioner cannot meet its burden. A proper obviousness inquiry
`analyzes the differences between the prior art and the claimed invention as a
`whole. Hybritech Inc. v. Monoclonal Antibodies, Inc., 802 F.2d 1367, 1383
`(Fed. Cir. 1986) (“Focusing on the obviousness of substitutions and
`differences instead of on the invention as a whole . . . was a legally improper
`way to simplify the difficult determination of obviousness.”). Here, even
`assuming, as Petitioner contends, one skilled in the art would have chosen,
`separately, difluoromethyl at R1, cyclopropylmethyl at R2, 3,5-dihalopyrid-
`4-yl N-oxide at R3, oxygen at both Z1 and Z2, and CONH- at Z3, Petitioner
`has not sufficiently explained why one skilled in the art would have selected
`the claimed substituents at each of the six independent positions all at once.
`In other words, Petitioner has not shown some objective teaching in the prior
`art or some general knowledge in the art that would have led one of ordinary
`skill to combine the relevant teachings of the references to arrive at the
`claimed invention. See In re Johnston, 435 F.3d 1381, 1385 (Fed. Cir.
`2006).
`Petitioner also argues that secondary considerations do not render the
`challenged claims unobvious. Pet. 3, 33–48. Because Petitioner has not
`shown that one of ordinary skill would have had a reason or motivation to
`modify the Fenton and/or Ashton prior art compounds, we need not examine
`the argument on secondary considerations. Nevertheless, we note that
`9
`
`
`
`
`
`IPR2014-00559
`Patent 6,448,274 B2
`
`Petitioner directs our attention to two compounds expressly listed in Fenton:
`DI (3-cyclopentylmethoxy-N-(3,5-dichloropyrid-4-yl)-4-
`methoxybenzamide) and DJ (3-cyclopropylmethoxy-N-(3,5-dichloropyrid-4-
`yl)-4-methoxybenzamide). Pet. 40. Petitioner appears to argue that the N-
`oxides of these two compounds are the closest prior art compounds. Id.
`Assuming, without deciding, that is the case, Petitioner fails to explain how
`a skilled artisan would have identified those two compounds from the list of
`147 exemplary compounds (A through EQ) as the lead compounds,
`especially because Fenton does not identify either DI or DJ in its list of 16
`“[p]referred compounds.” See Ex. 1002, 26. Moreover, Petitioner does not
`provide any evidence or reasoning as to why a skilled artisan would have
`modified those two compounds to arrive at the claimed compound.
`In sum, Petitioner has failed to advance some articulated reasoning
`with some rational underpinning to support the legal conclusion of
`obviousness. See KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 418 (2007).
`Therefore, we conclude Petitioner has not established a reasonable
`likelihood that it would prevail in showing Fenton and Ashton would have
`rendered claims 1 or 2 obvious.
`
`III. CONCLUSION
`Petitioner has failed to establish a reasonable likelihood that it would
`prevail in showing the unpatentability of at least one challenged claim of the
`’274 patent.
`
`
`
`
`
`
`
`
`10
`
`
`
`IPR2014-00559
`Patent 6,448,274 B2
`
`IV. ORDER
`Accordingly, it is
`ORDERED that the Petition is denied.
`
`
`
`For PETITIONER:
`
`Miles A. Finn
`Bryan J. Vogel
`ROBINS, KAPLAN, MILLER & CIRESI, L.L.P.
`mafinn@rkmc.com
`bjvogel@rkmc.com
`
`
`
`For PATENT OWNER:
`
`Lisa A. Jakob
`Gerard M. Devlin
`MERCK & CO., INC.
`lisa.jakob@merck.com
`gerard.devlin@merck.com
`
`
`
`
`11
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