Trials@uspto.gov
`571-272-7822
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`Paper No. 14
`Entered: June 25, 2015
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________
`
`APOTEX INC.,
`Petitioner,
`
`v.
`
`MERCK SHARP & DOHME CORP.,
`Patent Owner.
`____________
`
`Case IPR2015-00419
`Patent 5,691,336
`____________
`
`Before LORA M. GREEN, ZHENYU YANG, and
`ROBERT A. POLLOCK, Administrative Patent Judges.
`
`YANG, Administrative Patent Judge.
`
`DECISION
`Denying Institution of Inter Partes Review
`37 C.F.R. § 42.108
`
`
`
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`NOVARTIS EXHIBIT 2078
`Par v Novartis, IPR 2016-00084
`Page 1 of 14
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`571-272-7822
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`Paper No. 14
`Entered: June 25, 2015
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________
`
`APOTEX INC.,
`Petitioner,
`
`v.
`
`MERCK SHARP & DOHME CORP.,
`Patent Owner.
`____________
`
`Case IPR2015-00419
`Patent 5,691,336
`____________
`
`Before LORA M. GREEN, ZHENYU YANG, and
`ROBERT A. POLLOCK, Administrative Patent Judges.
`
`YANG, Administrative Patent Judge.
`
`DECISION
`Denying Institution of Inter Partes Review
`37 C.F.R. § 42.108
`
`
`
`
`
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`NOVARTIS EXHIBIT 2078
`Par v Novartis, IPR 2016-00084
`Page 1 of 14
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`IPR2015-00419
`Patent 5,691,336
`
`
`INTRODUCTION
`Apotex Inc. (“Petitioner”) filed a Petition for an inter partes review of
`claims 1, 3–8, and 10–25 of U.S. Patent No. 5,691,336 (“the ’336 patent,”
`Ex. 1001). Paper 1 (“Pet.”). Merck Sharp & Dohme Corp. (“Patent
`Owner”) timely filed a Preliminary Response. Paper 13 (“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. See 35 U.S.C. § 314(a).
`Therefore, we deny the Petition for an inter partes review.
`
`
`Related Proceedings
`According to the parties, Patent Owner previously asserted the ’336
`patent against several entities, but not Petitioner, in district court
`proceedings. Pet. 1, 2; Paper 9, 1–2.
`
`
`The ’336 Patent
`The ’336 patent is directed to a genus of tachykinin receptor
`antagonists useful in treating inflammatory diseases, pain or migraine,
`asthma, and emesis. Ex. 1001, 5:15–39. The compounds are prodrugs of
`their parent compounds. Id. at 12:26–27.
`According to the ’336 patent,
`Prodrugs are entities structurally related to a[] biologically
`active
`substance
`(the
`“parent drug”)[,] which,
`after
`administration, release the parent drug in vivo as the result of
`some metabolic process, such as enzymatic or chemical
`2
`
`
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`
`hydrolysis of a carboxylic, phosphoric or sulfate ester or
`reduction or oxidation of a susceptible functionality.
`Id. at 12:38–43. “[T]he activity exhibited upon administration of the
`prodrug is principally due to the presence of the parent compound that
`results from cleavage of the prodrug.” Id. at 12:31–34. Compared with their
`parent compounds, the prodrugs of the ’336 patent have enhanced solubility.
`Id. at 12:27–29, 13:9–12.
`The ’336 patent discloses 2-(R)-(1-(R)-(3,5-
`bis(trifluoromethyl)phenyl)ethoxy)-3-(S)-(4-fluoro)phenyl-4-(3-(1-
`phosphoryl-5-oxo-4H-1,2,4-triazolo)methylmorpholine as “a particularly
`preferred compound” within the scope of its invention. Id. at 43:19–23.
`Today this compound is referred to as fosaprepitant. Pet. 5. The ’336 patent
`also discloses 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(S)-
`(4-fluoro)pheny l-4-(3-(1-phosphoryl-5-oxo-4H-1,2,4-
`triazolo)methylmorpholine, bis(N-methyl-D-glucamine) as “a specific
`particularly preferred compound” within the scope of its invention. Id. at
`43:23–27. It has the structure:
`
`
`
`3
`
`
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`Id. at 159:23–45. Today this compound is referred to as fosaprepitant
`dimeglumine, which is the active ingredient in Patent Owner’s FDA-
`approved product, Emend®
` for Injection. Prelim. Resp. 1.
`Among the challenged claims, claims 15, 16, 18, and 19 are directed
`to the compound fosaprepitant dimeglumine; and claim 23 is directed to a
`pharmaceutical composition comprising fosaprepitant dimeglumine. The
`other claims are broader in scope, but each encompasses fosaprepitant
`dimeglumine, the composition thereof, or the use thereof.
`
`
`Asserted Grounds of Unpatentability
`Petitioner asserts the following grounds of unpatentability:
`Claims
`Basis
`References
`Dorn ’6991 and Murdock ’0822
`1, 3–8, and 10–25
`§ 103
`1, 3–8, and 10–25
`§ 103
`Dorn ’699, Murdock ’082,
`Atanassova,3 and Van Den Bos4
`Dorn ’699, Murdock ’082,
`Atanassova, Van Den Bos,
`Sommer,5 Veronesi,6 and Chromy7
`
`12, 15, 16, 18, 19,
`and 23
`
`§ 103
`
`
`1 Dorn et al., U.S. Patent No. 5,637,699, issued June 10, 1997 (Ex. 1003,
`“Dorn ’699”).
`2 Murdock et al., U.S. Patent No. 5,070,082, issued December 3, 1991
`(Ex. 1004, “Murdock ’082”).
`3 Atanassova, T. et al., Synthesis of N-substituted derivatives of 2-
`imidazolidinone, 46 PHARMAZIE 670–71 (1991) (Ex. 1007, “Atanassova”).
`4 Van Den Bos et al., U.S. Patent No. 3,661,926, issued May 9, 1972
`(Ex. 1006, “Van Den Bos”).
`5 Sommer, F.G., et al., Pain Accompanying Leg Venography: A
`Comparison of Sodium and Methylglucamine Diatrizoates,
`133 RADIOLOGY 790–91 (1979) (Ex. 1017, “Sommer”).
`4
`
`
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`According to Petitioner, Dorn ’699 is prior art under 35 U.S.C.
`§ 102(e) because it has an effective filing date of at least December 17,
`1993, before the priority date of the challenged claims.8 Pet. 32. Petitioner
`asserts that the other references are prior art under 35 U.S.C. § 102(b). Id. at
`33, 48, 53.
`In support of its patentability challenge, Petitioner relies on the
`Declaration of Dr. Longqin Hu. 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).
`Under that standard, and 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
`
`
`
`
`6 Veronesi, U.S. Patent No. 4,748,174, issued May 31, 1988 (Ex. 1022,
`“Veronesi”).
`7 Chromy, V., et al., D(–)-N-Methylglucamine Buffer for pH 8.5 to 10.5,
`24 CLIN. CHEM. 379–81 (1978) (Ex. 1018, “Chromy”).
`8 The earliest possible priority date of the ’336 patent is March 4, 1994.
`Ex. 1001, 1:9–10. For purposes of its Preliminary Response, Patent Owner
`asserts February 28, 1995 as the priority date. Prelim. Resp. 9–10 & n.2.
`5
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`entire patent disclosure. In re Translogic Tech., Inc., 504 F.3d 1249, 1257
`(Fed. Cir. 2007).
`We agree with the parties that for purposes of this Decision, none of
`the terms requires express construction. See Pet. 8; Prelim. Resp. 10.
`
`
`Patentability Analysis
`
`Prior Art Disclosures
`Dorn ’699 teaches a genus of tachykinin receptor antagonists with the
`structure:
`
`
`wherein R1, R2, R3, R4, R5, and X are defined therein. Ex. 1003, 4:66–11:67.
`It specifies preferred substituents. Id. at 12:51–13:55. It also lists 601
`specific compounds as within the scope of its invention. Id. at 17:66–41:12.
`Dorn ’699 teaches that the compounds of its invention are useful in treating
`inflammatory diseases, pain or migraine, asthma, and emesis. Id. at 1:28–
`30.
`
`Murdock ’082 teaches N-phosphorylation of basic nitrogenous drug
`compounds to produce prodrugs. Ex. 1004, Abstract. Atanassova teaches
`the synthesis of N-substituted derivatives of 2-imidazolidinone, including N-
`phosphorylated imidazolidinone. Ex. 1007, 670. Van Den Bos teaches
`oxadiazoline or thiadiazoline derivatives of phosphoric or thiophosphoric
`acid. Ex. 1006, 1:16–17. Sommer reports lower incidence of pain at the
`
`6
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`injection site in patients receiving meglumine diatrizoate as compared to
`those receiving sodium diatrizoate. Ex. 1017, 790–91. Veronesi teaches
`that the acid addition salts of meglumine are “admirably water soluble.”
`Ex. 1022, 1:24–26. Chromy teaches that meglumine has a pKa of 9.6.
`Ex. 1018, 380.
`
`Obviousness over Dorn ’699 and Murdock ’082
`Petitioner asserts that claims 1, 3–8, and 10–25 would have been
`obvious over Dorn ’699 and Murdock ’082. Pet. 14–48. According to
`Petitioner, it would have been obvious for one of ordinary skill in the art to
`select the parent compound of fosaprepitant, disclosed in Dorn ’699, to
`prepare a prodrug for intravenous administration. Id. at 33. In addition, a
`skilled artisan would have looked to Murdock ’082, which teaches using
`phosphoramidate prodrugs to improve the aqueous solubility of a parent
`nitrogenous compound, to modify the parent compound of fosaprepitant to
`arrive at the claimed invention. Id. at 44. Based on the current record, we
`determine that Petitioner has not established a reasonable likelihood it would
`prevail in this assertion.
`We generally follow a two-part inquiry to determine whether a new
`chemical compound would have been obvious over particular prior art
`compounds. Otsuka Pharm. Co. v. Sandoz, Inc., 678 F.3d 1280, 1291–93
`(Fed. Cir. 2012). First, we determine “whether a chemist of ordinary skill
`would have selected the asserted prior art compounds as lead compounds, or
`starting points, for further development efforts.” Id. at 1291. Second, we
`
`7
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`analyze whether there was a reason to modify a lead compound to make the
`claimed compound with a reasonable expectation of success. Id. at 1292.
`Even “post-KSR, a prima facie case of obviousness for a chemical
`compound still, in general, begins with the reasoned identification of a lead
`compound.” Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 1359
`(Fed. Cir. 2008). Petitioner asserts that a skilled artisan seeking a tachykinin
`receptor antagonist prodrug would have selected the parent compound of
`fosaprepitant,9 disclosed in Dorn ’699 as compound 96, to develop a
`prodrug. Pet. 33–35. Petitioner argues that Dorn ’699 “specifies a narrowed
`range of preferred substituents, which encompass [compound 96].” Id. at
`33–34. Dorn ’699 also specifically identifies compound 96 by its chemical
`name 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(S)-(4-fluoro)-
`phenyl-4-(3-(5-oxo-1,2,4-triazolo)methyl-morpholine, and states it is a
`“specific compound[] within the scope of the [Dorn ’699] invention.” Id. at
`35 (citing Ex. 1003, 17:66, 21:32–34). Petitioner further refers to claim 2 of
`Dorn ’699 for reciting a process for producing compound 96. Id. at 35.
`Patent Owner counters that given the content and scope of the prior art
`at the time of the invention, one of ordinary skill in the art would not have
`looked to Dorn ’699 to develop tachykinin receptor antagonists. Prelim.
`Resp. 16–18. And even if starting from Dorn ’699, a skilled artisan would
`
`
`9 The generic name of the parent compound of fosaprepitant is aprepitant.
`Pet. 14–15. Petitioner uses the term aprepitant throughout the Petition. See
`id., in passim. Patent Owner asserts that the generic name did not exist until
`2000, years after the issuance of the ’336 patent. See Prelim. Resp. 20–21
`n.6 (citing Ex. 2009, 83).
`
`8
`
`
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`not have picked compound 96 from the hundreds of compounds listed
`therein. Id. at 18–23. We agree with Patent Owner.
`Citing several research articles and patent literature, Patent Owner
`contends that, by the time of the ’336 patent invention, a body of well-
`studied, potent tachykinin receptor antagonists had been extensively
`explored and discussed in the literature. Prelim. Resp. 16–18 (citing
`Exs. 2001–05, 2007, 2008). In contrast, there was no biological or
`pharmacokinetic data reported for compound 96 of Dorn ’699. Id. at 16. As
`a result, Patent Owner argues, a skilled artisan would have pursued those
`more promising lead compounds, not compound 96, and thus, would not
`have arrived at fosaprepitant dimeglumine, the prodrug of compound 96. Id.
`at 18. We find Patent Owner’s argument persuasive.
`A lead compound is “a compound in the prior art that would be most
`promising to modify in order to improve upon its . . . activity and obtain a
`compound with better activity.” Takeda Chem. Indus., Ltd. v. Alphapharm
`Pty., Ltd., 492 F.3d 1350, 1357 (Fed. Cir. 2007). “In determining whether a
`chemist would have selected a prior art compound as a lead, the analysis is
`guided by evidence of the compound’s pertinent properties.” Otsuka
`Pharm., 678 F.3d at 1292. Here, absent any reported activity data,
`compound 96 could not have served as “a natural choice for further
`development efforts.” Altana Pharma AG v. Teva Pharm. USA, Inc., 566
`F.3d 999, 1008 (Fed. Cir. 2009).
`Even within Dorn ’699, Petitioner does not explain sufficiently why a
`skilled artisan would have picked compound 96 over hundreds of other
`compounds. We disagree with Petitioner for characterizing the preferred
`9
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`substituents in Dorn ’699 as “a narrowed range.” See Pet. 33. For example,
`according to Petitioner, Dorn ’699 specifies R2 and R3 as independently
`hydrogen. Id. at 34. In fact, Dorn ’699 states:
`[The preferred] R2 and R3 are independently selected from the
`group consisting of:
`(1) hydrogen,
`(2) C1-6 alkyl,
`(3) C2-6 alkenyl, and
`(4) phenyl.
`Ex. 1003, 13:26–31. According to Dorn ’699,
`[T]he term “alkyl” includes those alkyl groups of a designated
`number of carbon atoms of either a straight, branched, or cyclic
`configuration. Examples of “alkyl” include methyl, ethyl,
`propyl, isopropyl, butyl, iso-[,] sec-[,] and tert-butyl, pentyl,
`hexyl,
`heptyl,
`3-ethylbutyl,
`cyclopropyl,
`cyclobutyl,
`cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, and the like.
`. . . “Alkenyl” is intended to include hydrocarbon chains of a
`specified number of carbon atoms of either a straight- or
`branched- configuration and at least one unsaturation, which
`may occur at any point along the chain, such as ethenyl,
`propenyl, butenyl, pentenyl, dimethylpentyl, and the like, and
`includes E and Z forms, where applicable.
`Id. at 12:11–26. In other words, the scope of R2 and R3 each includes
`possibly hundreds of preferred substituents—hardly the “narrowed range”
`suggested by Petitioner. Petitioner also does not explain why one skilled in
`the art would have chosen hydrogen independently for each position, let
`alone simultaneously for both R2 and R3 to arrive at compound 96.
`Similarly, Petitioner does not adequately explain why a skilled artisan would
`have chosen any of the preferred substituents for each of R1, R4 (which
`further includes R6, R7, R8, and Z), and R5 according to compound 96, not to
`
`10
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`mention all of them at the same time. Thus, we reject Petitioner’s contention
`that the substituents for compound 96 “were preferred.” See Pet. 35.
`Petitioner is correct that Dorn ’699 identifies compound 96 as a
`specific compound within the scope of its invention. Pet. 35 (citing
`Ex. 1003, 17:66, 21:32–34). Petitioner, however, neglects to mention that
`Dorn ’699 also discloses a laundry list of 600 other specific compounds by
`their chemical names as specific compounds within the scope of its
`invention. Ex. 1003, 17:66–41:12. Petitioner does not explain, and we do
`not find any reason, why a skilled artisan, having no reported activity data
`on any of the 601 enumerated compounds, would have picked compound 96
`for further development. See Otsuka Pharm., 678 F.3d at 1295 (affirming
`the rejection of a proposed lead compound, when the prior art lists the
`compound as one among hundreds of examples that may be useful).
`Petitioner is also correct that claim 2 of Dorn ’699 is directed to a
`process for producing compound 96. Pet. 35. But, as filed, the parent
`application, to which Dorn ’699 claims priority in order to qualify as prior
`art under 35 U.S.C. 102(e), did not include any claim directed specifically to
`compound 96. Ex. 1025, 240–360. Instead, it included claim 14, which
`recites 601 compounds listed in the specification. Id. at 263–316. As Patent
`Owner points out, a claim specifically directed to compound 96 was added
`by amendment dated May 19, 1995, several months after the February 28,
`1995 priority date of the ’336 patent. Prelim. Resp. 23 (citing Ex. 1029,
`529). As a result, at the time of the ’336 patent invention, one of ordinary
`skill in the art would not have had the benefit of claim 2 of Dorn ’699 to
`focus on compound 96.
`
`11
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`In sum, Petitioner has failed to sufficiently explain why, at the time of
`the ’336 patent invention, a skilled artisan would have chosen compound 96
`of Dorn ’699 to further develop its prodrug, which is the subject matter of
`the challenged claims. Therefore, we conclude that Petitioner has not
`established a reasonable likelihood it would prevail in showing any of the
`challenged claims would have been obvious over Dorn ’699 and Murdock
`’082.
`
`
`The Other Obviousness Grounds
`Petitioner also argues that claims 1, 3–8, and 10–25 would have been
`obvious over Dorn ’699, Murdock ’082, Atanassova, and Van Den Bos. Pet.
`48–53. Petitioner further contends that claims 12, 15, 16, 18, 19, and 23
`would have been obvious over Dorn ’699, Murdock ’082, Atanassova, and
`Van Den Bos, and further in view of Sommer, Veronesi, and Chromy. Id. at
`53–56. In both these grounds, Petitioner solely relies on Dorn ’699 for
`selecting compound 96 as the lead compound. Id. at 48, 54. As explained
`above, we are not persuaded by Petitioner’s argument on this issue. Thus,
`we conclude that Petitioner has not established a reasonable likelihood it
`would prevail in showing any of the challenged claims would have been
`obvious on either of these grounds.
`
`
`CONCLUSION
`For the foregoing reasons, the information presented in the Petition
`and accompanying evidence does not establish a reasonable likelihood that
`
`12
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`Petitioner would prevail in showing the unpatentability of claims 1, 3–8, and
`10–25 of the ’336 patent.
`
`
`ORDER
`
`Accordingly, it is
`ORDERED that Petitioner’s request for an inter partes review of
`claims 1, 3–8, and 10–25 of the ’336 patent is denied.
`
`
`
`
`
`13
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`PETITIONER:
`
`Kenneth J. Burchfiel
`Grant S. Shackelford
`SUGHRUE MION, PLLC
`kburchfiel@sughrue.com
`gshackelford@sughrue.com
`
`
`
`PATENT OWNER:
`
`Bruce M. Wexler
`Gregory A. Morris
`Preston K. Ratliff II
`Naveen Modi
`PAUL HASTINGS LLP
`brucewexler@paulhastings.com
`gregorymorris@paulhastings.com
`prestonratliff@paulhastings.com
`naveenmodi@paulhastings.com
`
`Gerard M. Devlin
`Richard C. Billups
`MERCK SHARP & DOHME CORP.
`gerard_devlin@merck.com
`richard_billups@merck.com
`
`14
`
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`NOVARTIS EXHIBIT 2078
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`Page 14 of 14
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