Paper No. ______
Filed:
UNITED STATES PATENT AND TRADEMARK OFFICE
______
BEFORE THE PATENT TRIAL AND APPEAL BOARD
______
Petitioner
v.
GRüNENTHAL GMBH
Patent Owner
______
Case No.: UNASSIGNED
Patent No. 7,994,364
Filed: DECEMBER 10, 2009
Issued: AUGUST 9, 2011
Inventors: ANDREAS FISCHER, ET AL.
Title: CRYSTALLINE FORMS OF (-)-(1r,2r)-3-(3-DIMETHYLAMINO-1-ETHYL-2-METHYLPROPYL)-PHENOL HYDROCHLORIDE
______
PETITION FOR INTER PARTES REVIEW
OF U.S. PATENT NO. 7,994,364
Patent No. 7,994,364
TABLE OF CONTENTS
Table of Authorities
tABLE OF eXHIBITS
Exhibit No. / Description /Exhibit 1001 / U.S. Patent No. 7,994,364 to Andreas Fische et al., filed on Dec. 10, 2009, and issued on Aug. 9, 2011 (“the ’364 Patent”)
Exhibit 1002 / Relevant Excerpts of U.S. Patent No. 7,994,364 Prosecution History (“’364 prosecution history”)
Exhibit 1003 / EP1799633 A2 Bibliographic Data (“EP 633 Data”)
Exhibit 1004 / Grünenthal GmbH Apr. 18, 2008 Reply to EPO Communication Re: Patent App. No. 05 770 026.2 (“Apr. 18 EPO Communication”)
Exhibit 1005 / EPO Nov. 14, 2007 Communication to Grünenthal GmbH Re: Patent App. No. 05 770 026.2 (“Nov. 14 EPO Communication”)
Exhibit 1006 / Certified English Translation of European Patent No. EP 0 693 475 A1 (“EP 475”)
Exhibit 1007 / European Patent No. EP 0 693 475 A1, by Dr. Helmut Bushmann et al., to Grünenthal GmbH, issued Jan. 24, 1996 (“German EP 475”)
Exhibit 1008 / Translator Certification for EP 0 693 475 A1 (“EP 475 Certification”)
Exhibit 1009 / Certified English Translation of International Patent App. No. WO 03/035053 A1 (“Bartholomaeus”)
Exhibit 1010 / International Patent App. No. WO 03/035053 A1, by Johannes Bartholomӓus and Iris Ziegler, published May 1, 2003 (“German Bartholomaeus”)
Exhibit 1011 / Translator Certification for International Patent App. No. WO 03/035053 A1 (“Bartholomaeus Certification”)
Exhibit 1012 / Expert Declaration of Dr. Expert
Exhibit 1013 / CV of Dr. Expert
Exhibit 1014 / Expert Declaration of Dr. Expert2
Exhibit 1015 / CV of Dr. Expert2
Exhibit 1016 / U.S. Patent No. RE39,593 E to Helmut Bushmann et al., filed Jun. 17, 2003, and issued Apr. 24, 2007 (“Bushmann 593”)
Exhibit 1017 / U.S. Patent No. 6,248,737 to Helmut Bushmann et al., issued Jun. 19, 2001 (“Bushmann 737”)
Exhibit 1018 / U.S. Patent No. 6,344,558 to Helmut Bushmann et al., issued Feb. 5, 2002 (“Bushmann 558”)
Exhibit 1019 / Plaintiffs’ Opening Claim Construction Brief, Janssen Pharms., Inc. et al. v. Actavis Elizabeth LLC et al., 2-13-cv-04507 (D. NJ), D.I. No. 141 (“Janssen Claim Construction Brief”)
Exhibit 1020 / July 15, 2015 Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations listing for Nucynta (“Orange Book”)
iv
Patent No. 7,994,364
I. Introduction
Petitioner requests an Inter Partes Review (“IPR”) of claims 1–4 and 24–27 (collectively, the “Challenged Claims”) of U.S. Patent No. 7,994,364 (the “’364 Patent”) (Ex. 1001) in accordance with 35 U.S.C. §§311–19 and 37 C.F.R. §§ 42.100 et seq.
II. Grounds for Standing (37 C.F.R. § 42.104(a))
Pursuant to 37 C.F.R. § 42.104(a), Petitioner certifies that the ’364 Patent is available for IPR and that Petitioner is not barred or estopped from requesting IPR challenging the claims of the ’364 Patent on the grounds identified in this Petition.
III. Mandatory Notices (37 C.F.R. § 42.8)
A. Real Parties-in-Interest (37 C.F.R. § 42.8(b)(1))
Pursuant to 37 C.F.R. § 42.8(b)(1), Petitioner certifies that it has authority to direct or control (i) the timing of, filing of, content of, or any decisions or other activities relating to this Petition or (ii) any timing, future filings, content of, or any decisions or other activities relating to the future proceedings related to this Petition.
B. Related Judicial and Administrative Matters (37 C.F.R. § 42.8(b)(2))
Pursuant to 37 C.F.R. § 42.8(b)(2), Petitioner states that the ’364 Patent has been the subject of the following lawsuits: Janssen Pharms., Inc. et al. v. Actavis Elizabeth LLC et al., D. NJ.-2-13-cv-04507 (filed Jul. 25, 3013); Janssen Pharms., Inc. et al. v. Sandoz Inc. et al., D. NJ.-2-13-cv-06929 (filed Nov. 14, 2013); Janssen Pharms., Inc. et al. v. Roxane Labs., Inc., D. Nev.-3-13-cv-00639 (filed Nov. 15, 2013); Janssen Pharms., Inc. et al. v. Alkem Labs. Ltd., D. NJ-2-13-cv-07803 (filed Dec. 23, 2013); Janssen Pharms., Inc. et al. v. Roxane Labs., Inc., D. NJ-2-14-cv-03941 (filed Jun. 19, 2014); and Janssen Pharms., Inc. et al. v. Watson Labs., Inc., D. NJ-2-14-cv-04617 (filed Jul. 23, 2014).
C. Lead and Back-Up Counsel (37 C.F.R. § 42.8(b)(3)) and Service Information (37 C.F.R. § 42.8(b)(4))
Lead counsel is Attorney 1. Back-up counsel is Attorney 2. Petitioner consents to electronic service.
IV. Payment of Fees (37 C.F.R. § 42.15(a) and § 42.103)
The required fees are submitted herewith in accordance with 37 C.F.R. §§42.103(a) and 42.15(a). If any additional fees are due during this proceeding, the Office is authorized to charge such fees to Deposit Account No. ______. Any overpayment or refund of fees may also be deposited in this Deposit Account.
V. Identification of Challenge
A. Overview of U.S. Patent No. 7,994,364
The ’364 Patent is titled “Crystalline Forms of (-)-(1R,2R)-3-(3-Dimethylamino-1-Ethyl-2-Methylpropyl)-Phenol Hydrochloride.” (Ex. 1001 at Front Cover.) The underlying application, U.S. Patent App. No. 12/364,777 (the “’777 Application”) was filed on Dec. 10, 2009. The ’777 Application is a continuation of U.S. Patent App. No. 12/274,747, filed on Nov. 20, 2008 (now abandoned), which is a continuation of U.S. Patent App. No. 11/646,232, filed on Dec. 28, 2006 (now abandoned), which is a continuation of Application No. PCT/EP2005/006884, filed on Jun. 27, 2005. (Id.) The ’777 Application claims priority back to European Patent App. No. 04015091, filed on Jun. 28, 2004. (Id.)
1. The ’364 Patent Specification
The ’364 Patent claims the crystalline Form A of (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride (“tapentadol HCl”), pharmaceutical compositions containing Form A, methods of producing Form A compounds, and methods of treating conditions by administering the compound, including methods for the treatment of pain. (Id. at Abstract.) The ’364 Patent acknowledges that “U.S. Pat. Nos. 6,248,737 and 6,344,558 as well as European Patent EP 693 475 B1 [German EP 475; EP 475] disclose the substance and the synthesis of (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride in example 25.” (Id. at 1:46-49.)[1] However, the ’364 Patent purports to disclose “a new form (Form A) of (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride which is different from the form already known (Form B) obtained by the procedure described in example 25 of U.S. Pat. No. 6,248,737 and U.S. Pat. No. 6,344,558 as well as EP 693 475 B1.” (Id. at 1:58-63.)
According to the ’364 Patent, “[t]he new crystalline Form A of (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride can be identified by X-ray powder diffraction. The X-ray diffraction (“XRPD”) pattern is shown in FIG. 1 [copied below] with the peak listing showing in Table 1 [also copied below].” (Id. at 2:14-18.)
The ’364 Patent explains:
To discriminate crystalline Form A of (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride from Form B it is more advantageous to look at the unique peaks in the X-ray diffraction diagram, i.e. e.g. the lines with sufficient intensity at 2-theta values, where Form B does not show lines with significant intensity. Such characteristic X-ray lines (2-theta values) for Form A in a powder diffraction pattern when measured using Cu Kα radiation at ambient temperature are: 15.1±0.2, 16.0±0.2, 18.9±0.2, 20.4±0.2, 22.5±0.2, 27.3±0.2, 29.3±0.2 and 30.4±0.2 [highlighted in Table 1, above].
(Id. at 2:27-36.) The ’364 Patent claims at least this “crystalline Form A of (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride” displaying the above “X-ray lines (2-theta values) for Form A” in each of the Challenged Claims, as shown below.
Additionally, the ’364 Patent allegedly provides procedures for obtaining tapentadol HCl’s Form A—found in Examples 1-6, as well as for obtaining tapentadol HCl’s Form B—found in Examples 7-9. Of note, Example 7 purports to obtain Form B by following Example 25 of EP 475—the anticipatory prior art reference relied upon in Ground 1, and discussed in more detail below.
2. The ’364 Claims
The ’364 Patent’s Challenged Claims includes 3 independent claims and 5 dependent claims. Claim 1 is representative and is reproduced below.
A crystalline Form A of (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 15.1±0.2, 16.0±0.2, 18.9±0.2, 20.4±0.2, 22.5±0.2, 27.3±0.2, 29.3±0.2 and 30.4±0.2.
(Ex. 1001 at 18:66-19:4.)
Claim 2 depends from claim 1 and adds the limitation that Form A exhibits “at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 14.5±0.2, 18.2±0.2, 20.4±0.2, 21.7±0.2 and 22.5±0.2. (Id. at 19:7-10.)
Claim 3 depends from claim 1 and adds the limitation that Form A exhibits “an X-ray pattern (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation essentially the same as that provided in FIG. 1” (copied below). (Id. at 19:13-15.)
Claim 4 depends from claim 1 and adds the limitation that the Form A crystal has a monoclinic form. (Id. at 19:18-19.)
Claim 24 depends from claim 1 and is a product-by-process claim that adds the limitation that Form A is
produced by the process of:
dissolving (−) (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride of Form B in acetonitrile together with active carbon,
heating the solution to the boiling point,
removing the active carbon by filtering,
stirring the solution at a temperature below 40o C.,
removing part of the solvent residue by filtering and removing part of the solvent,
leaving (−) (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride of Form A to crystalize,
redissolving the resulting crystals in acetonitrile,
removing insoluble residue by filtering and removing part of the solvent, and
leaving (−) (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride of Form A to crystalize.
(Id. at 19:38-55.)
Independent claim 25 requires a “solid pharmaceutical composition comprising, as an active ingredient,” the crystalline Form A of claim 1, “and at least one suitable additive or auxiliary substance.” (Id. at 19:56-63.)
Claim 26 depends from claim 25 and adds the limitation that Form A is
produced by the process of:
dissolving (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride of Form B in acetonitrile together with active carbon,
heating the solution to the boiling point,
removing the active carbon by filtering,
stirring the solution at a temperature below 40o C.,
removing insoluble residue by filtering and removing part of the solvent, and
leaving (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride of Form A to crystalize, and
at least one suitable additive or auxiliary substance.
(Id. at 19:67-22:4.)
Independent claim 27 requires a “method of treating or inhibiting pain or urinary incontinence, said method comprising the step of administering a pharmaceutically effective amount of “the crystalline Form A of claim 1 “to a subject in need thereof.” (Id. at 22:5-13.)
3. Prosecution History of the ’364 Patent and European Counterpart
The ’777 Application that led to the ’364 Patent received light treatment during prosecution. The only claims to ever receive a rejection were as-filed claims 26 and 27. (Ex. 1002 at 50.) For these two claims, the Examiner stated that the a pending 35 U.S.C. 112 rejection could “be removed by adding the word ‘solid’ in front of the word ‘pharmaceutical.’” (Id. at 51-53.) The applicant therefore amended claims 26 and 27 according to the Examiner’s suggestion. (Id. at 58-64.)
Additionally, the applicant submitted an IDS containing information about “four clinical trials of a crystalline form of (−)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride (CG5503) [that] were conducted in the United States through contract research organizations from 2001 to January 2003.” (Id. at 64.) The applicant explained that “[a]t the time of these clinical trials, the crystalline material used to prepare the pharmaceutical dosage forms for these clinical trials was not tested to determine which crystalline form it was.” (Id. at 54.) The applicant went on to state that, “[a]lthough tests have shown that even when the crystalline form B, produced as disclosed in US patent no. 6,248,737, is subjected to tableting, it retains its form B crystalline structure and does not convert to the crystalline form A ….” (Id. at 65.) Additionally, the applicant remarked that “[e]xtreme stress tests of crystalline form B alone (i.e., in the absence of any other tablet ingredients) for extended durations of 60 seconds have yielded mixtures of crystalline forms B and A, but under normal tableting conditions, no conversion to crystalline form A can be detected.” (Id. at 65.) Importantly, these statements were made without any provocation from the Examiner, and without providing any data to support their veracity.
In direct contrast to the applicant’s statements above, during prosecution of the ’364 Patent’s European counterpart Application No. 05 770 026.2, the European applicant (and owner of the ’364 Patent)—Grünenthal GmbH—stated that “[t]he crystalline form B disclosed in D1 [EP 475] has the disadvantage that under the influence of pressure (which occurs e.g. in the manufacturing process for the drug tablet) polymorph B (crystalline form of D1 [EP 475]) is transformed in a mixture of the crystalline forms A and B.” (Ex. 1004 at 1; see Ex. 1003 at 1 (“Also published as: … US799364”).)
After the applicant’s amendment to claims 26 and 27, the Examiner issued a Notice of Allowance. With authorization from a telephone interview, the Examiner further amended (1) claim 5 to require that “during the process the temperature is kept below + 40oC, (2) claim 25 to require that Form A be “according to claim 1,” and (3) claim 26 to require that Form be “according to claim 26.” (Id. at 77-78.)
B. Claim Construction of Challenged Claims
A claim subject to IPR receives the “broadest reasonable construction in light of the specification of the patent in which it appears.” 37 C.F.R. § 42.100(b); see In re Cuozzo Speed Techs., LLC, 778 F.3d 1271, 1279 (Fed. Cir. 2015). In applying such a standard, the broadest reasonable construction of claim language is not one that permits any reading, but instead is one that must be made “in light of the specification as it would be interpreted by one of ordinary skill in the art.” In re Am. Acad. of Sci. Tech. Ctr., 367 F.3d 1359, 1364 (Fed. Cir. 2004) (citation omitted).
Unless otherwise noted, Petitioner accepts, for purposes of this IPR only, that the claim terms of the ’364 Patent are presumed to take on the ordinary and customary meaning that they would have to one of ordinary skill in the art.
C. Statement of Precise Relief Requested for Each Claim Challenged
1. Claims for Which Review is Requested
Petitioners request IPR under 35 U.S.C. § 311 of claims 1–4 and 24–27 of the ’364 Patent, and cancellation of these 8 claims as unpatentable.