Purdue Pharma L.P. v. Teva Pharms., United States, Inc. (In re Oxycontin Antitrust Litig.), Nos. 04 Md. 1603(SHS), 11 Civ.2037(SHS), 12 Civ. 5083(SHS).

• Court: United States District Courts. 2nd Circuit. United States District Courts. 2nd Circuit. Southern District of New York
• Writing for the Court: SIDNEY H. STEIN
• Citation: 994 F.Supp.2d 367
• Parties: In re OXYCONTIN ANTITRUST LITIGATION. Purdue Pharma L.P., et al., Plaintiffs, v. Teva Pharmaceuticals, USA, Inc., Defendant.
• Docket Number: Nos. 04 Md. 1603(SHS), 11 Civ.2037(SHS), 12 Civ. 5083(SHS).
• Decision Date: 14 January 2014

994 F.Supp.2d 367

In re OXYCONTIN ANTITRUST LITIGATION.
Purdue Pharma L.P., et al., Plaintiffs,
v.
Teva Pharmaceuticals, USA, Inc., Defendant.

Nos. 04 Md. 1603(SHS), 11 Civ.2037(SHS), 12 Civ. 5083(SHS).

United States District Court,
S.D. New York.

Jan. 14, 2014.

[994 F.Supp.2d 373]

Crystal Lohmann Parker, Pablo Daniel Hendler, Sona De, Vikram Alexander Mathrani, Ropes & Gray LLP, New York, NY, Kelly L. Baxter, Rebecca R. Hermes, Robert J. Goldman, Thomas A. Wang, Ropes & Gray, LLP, East Palo Alto, CA, Anthony C. Tridico, Basil James Lewris, Erin McGeehan Sommers, Jennifer Howe Roscetti, Joann M. Neth, Marianne Simone Terrot, Sarah Emily Craven, Finnegan, Henderson, Farabow, Garrett & Dunner LLP, Washington, DC, Stephen D. Hoffman, Wilk Auslander LLP, New York, NY, for Plaintiffs.

Alexandra J. Olson, Jennell C. Bilek, Mark David Schuman, Samuel T. Lockner, Sarah M. Stensland, Carlson, Caspers, Vandenburgh, Lindquist & Schuman, P.A., Minneapolis, MN, Angela Verrecchio, Barbara L. Mullin, Matthew A. Pearson, Steven D. Maslowski, Todd S. Werner, Akin Gump Strauss Hauer & Feld LLP, Philadelphia, PA, David M. Hashmall, Goodwin Procter, LLP, New York, NY, for Defendant.

FINDINGS OF FACT AND CONCLUSIONS OF LAW
SIDNEY H. STEIN, District Judge.

CONTENTS

TABLE OF ABBREVIATIONS
375

PART 1. INTRODUCTION
376

I. The Record and Relevant Proceedings
377

A.	The Asserted Patent Claims	377
B.	The 2012 Ranbaxy Trial	377
C.	Claim Construction	378
D.	The 2013 Trial	378
E.	This Opinion	378

II. Legal Standards
378

A.	Procedural Context and the Hatch–Waxman Act	378
B.	Claims of Patent Infringement	379
C.	The Affirmative Defense of Patent Invalidity	380

1.	Novelty and Anticipation	380
2.	Obviousness and Nonobviousness	381
3.	Written Description and Enablement	382
4.	Definiteness	383

D.	Product–by–Process Claims	383
E.	Attorneys Fees	384

PART 2. THE LOW–ABUK PATENTS
384

I. Findings of Fact
384

A.	Purdue's development of low-ABUK oxycodone	384
B.	Purdue obtains the '799, '800, and '072 Patents	387

1.	The Chapman Application	388
2.	Further proceedings before the PTO	389
3.	The low-ABUK patents-in-suit	389

C.
The Noramco process
391

1.	Teva plans to sell tablets containing oxycodone hydrochloride API and a sustained release carrier	391
2.	Teva's tablets contain a non-zero amount of 14–hydroxy	391
3.	8a forms during the Noramco process	392
4.	8a converts to 14–hydroxy during the Noramco process	393

D.
Facts pertinent to obviousness
394

1.	The ordinary skill in the art is impressive	394
2.	The prior art disclosed the fact that 8ß converted to 14– hydroxy and it disclosed methods of using hydrogenation to reduce 14hydroxy levels in free base and salt compositions	395
3.	Differences between the prior art and the claims	397
4.	The objective indicia of nonobviousness	398

II. Conclusions of Law
401

A.
Infringement
401

1.	Teva's ANDA infringes claims 30–34 and 76–79 of the '800 Patent	401
2.	Teva's ANDA infringes claims 1, 4, and 5 of the '072 Patent	402
3.	Teva's ANDA infringes claims 3 and 19 of the '799 Patent	402
4.	Teva's use of the Noramco API constitutes an act of infringement	403

B.
Obviousness pursuant to 35 U.S.C. § 103
403

1.	The invention would have been obvious to a skilled artisan	403
2.	The asserted claims are invalid pursuant to 35 U.S.C. § 103	407

C.
Invalidity pursuant to 35 U.S.C. § 112
409

1.	The written description of the '799, '800, and '072 Patents satisfies 35 U.S.C. § 112	409
2.	The patents meet the enablement requirement of 35 U.S.C. § 112.60	410

D.
Collateral estoppel does not apply
411

III. Conclusion
413

PART 3. THE ABUSE–PROOF PATENTS
413

I.	Factual Background: Abuse of OxyContin became tragically rampant, generating a public health crisis and responses	413
II.	The '383 Patent: Thermoforming Technology	416

A.
Teva's ANDA infringes the '383 Patent
417

1.	Grunenthal's search for abuse-deterrent formulations led it to a thermoformed, PEO-based tablet	417
2.	Teva compresses and then cures its tablets, making them extremely hard	419
3.	Comparing Teva's process to that of the '383 Patent, the asserted claims read on Teva's tablets	419

B.
The '383 Patent is invalid as anticipated and obvious
421

1.	The McGinity Application anticipates the '383 Patent	421
2.	At the time of the '383 Patent's development, the prior art made the process obvious	426

C.
Conclusion
428

III. The '314 Patent: Gel Test Technology
428

A.
Teva's ANDA does not infringe the '314 Patent, because Purdue has not put forward reliable and relevant evidence of infringement
429

1.	Purdue's evidence of infringement is based on a gel test that is not designed to replicate the '314 Patent's gel test	429
2.	Purdue's evidence of infringement is based on a gel test conducted in an unreliable manner	430
3.	To the extent that any experimental evidence is probative, it suggests that Teva's tablets do not infringe	432

B.
The '314 Patent is invalid as indefinite
433

1.	The “gel test” gives a skilled artisan insufficient guidance to conduct a replicable experiment	433
2.	The '314 Patent is both novel and nonobvious	435

C.
Conclusion
437

PART 4. CONCLUSION AND RELIEF
437

TABLE OF ABBREVIATIONS

'072 Patent	U.S. Patent No. 7,683,072
'314 Patent	U.S. Patent No. 7,776,314
'383 Patent	U.S. Patent No. 8,114,383
'799 Patent	U.S. Patent No. 7,674,799
'800 Patent	U.S. Patent No. 7,674,800
'963 Patent	U.S. Patent No. 6,488,963
14–hydroxy	14–hydroxycodeinone
2013 Stip.	Stipulations or Agreed Statements of Fact or Law, Joint Pretrial Order, Case No. 04 Md. 1603, Dkt. No. 572, filed Aug. 28, 2013
2012 Stip.	Stipulations or Agreed Statements of Fact or Law, Joint Pretrial Order, Case No. 10 Civ. 3734, Dkt. No. 168, filed Oct. 12, 2012
8,14–dihydroxy	8,14–dihydroxy–7,8–dihydrocodeinone
8a	8a, 14–dihydroxy–7,8–dihydrocodeinone
8ß	8ß, 14–dihydroxy–7,8–dihydrocodeinone
8–acetoxy	8–acetoxy–14–hydroxydihydrothebaine
ABUK	a,ß-unsaturated ketone
ANDA	Abbreviated New Drug Application
API	active pharmaceutical ingredient
Bastin	International Application No. WO 95/20947
Casner	U.S. Patent No. 7,153,966
Chiu	U.S. Patent No. 6,177,567
COB	crude oxycodone base
Da	Daltons
DMF	Drug Master File
FDA	U.S. Food and Drug Administration
HCl	hydrochloride
Hoffmeister	U.S. Patent No. 4,070,494
HPLC	high-performance liquid chromatography
N	Newtons
NDA	New Drug Application
OROS	osmotically controlled-release oral delivery system
ppm	parts per million
PEO	polyethylene oxide
POB	purified oxycodone base
PTO	U.S. Patent and Trademark Office
Teva Mem.	Defs.' Post–Trial Mem. dated Nov. 6, 2013
Wright–Oshlack	U.S. Provisional Patent Application No. 60/310,534 [994 F.Supp.2d 376]

PART 1. INTRODUCTION

This consolidated trial concerns six patents associated with the pa in reliever OxyContin. Plaintiffs, led by the OxyContin manufacturer Purdue, allege that Teva, which manufactures generic pharmaceutical products, has infringed these patents by seeking approval from the U.S. Food and Drug Administration (“FDA”) to sell bioequivalents of OxyContin. In response, Teva argues that its proposed products do not infringe plaintiffs' patents and that, in any event, the asserted patents are invalid. These arguments played out over the course of extensive litigation, culminating in a twenty-day-long bench trial before this Court. These findings of fact and conclusions of law are the results of that litigation.

Three patents-in-suit—United States Patent Nos. 7,674,799 (“the '799 Patent”), 7,647,800 (“the 800 Patent”), and 7,683,072 (“the '072 Patent”) (collectively, “the low-ABUK patents”)—recite an improved formulation of oxycodone, the active pharmaceutical ingredient in OxyContin. Those patents describe an oxycodone salt with extremely low levels of a particular impurity, 14–hydroxycodeinone (“14–hydroxy”), which belongs to a class of potentially dangerous compounds known as a,(3–unsaturated ketones (“ABUKs”)). Purdue was the first to succeed in developing a low-ABUK oxycodone salt as an active pharmaceutical ingredient (“API”). Its low-ABUK patents reflect that work.

Also in suit are two patents—United States Patent Nos. 7,776,314 (“the ' 314 Patent”) and 8,114,383 (“the '383 Patent”) (collectively, “the abuse-proof patents”)—that claim technology making tablets resistant to abuse. The technology disclosed in these patents is intended to hinder would-be abusers from crushing tablets into powder, converting the powder into a liquid, and then injecting the solution intravenously in order to experience an opioid “high.”

The parties in these actions play various roles in the scientific and pharmaceutical

[994 F.Supp.2d 377]

communities. Universities provide the infrastructure for the advancement of human knowledge; pharmaceutical manufacturers seeking patents and marketing branded drugs discover new frontiers of medication and health; and generic pharmaceutical companies make those frontiers available to the public. This circle of invention, medicine, health, and profit depends on principles of intellectual property—the law's allocation of restrictions and liberties.

Applying those principles and the evidence presented at trial, the Court concludes that Teva has not infringed any valid patent asserted by plaintiffs. As explained below, plaintiffs have not carried their burden of proving infringement of the '314 Patent. Although plaintiffs have proved by a preponderance of the evidence that Teva's proposed products infringe the ' 799, '800, '072, and '383 Patents, Teva has proved by clear and convincing evidence that the asserted claims of those patents are invalid.

I. The Record and Relevant ProceedingsA. The Asserted Patent Claims

Purdue ¹ alleges that Teva's proposed formulations infringe several claims of the patents-in-suit. In the low-ABUK portion of the trial, Purdue accuses Teva of infringing claims 3 and 19 from the ' 799 Patent, claims 30–34 and 76–79 from the ' 800 Patent, and claims 1, 4, and 5 from the ' 072 Patent. These claims are directed to an oxycodone salt API that contains 14–hydroxy at extremely low levels, and some of the claims specifically refer to an oral dosage form of that API.

In the abuse-proof portion of the litigation, Purdue accuses Teva of infringing claims 1, 2,...