Purdue Pharma L.P. v. Teva Pharms., United States, Inc. (In re Oxycontin Antitrust Litig.)

• Decision Date: 14 January 2014
• Docket Number: Nos. 04 Md. 1603(SHS), 11 Civ.2037(SHS), 12 Civ. 5083(SHS).,s. 04 Md. 1603(SHS), 11 Civ.2037(SHS), 12 Civ. 5083(SHS).
• 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.
• Court: U.S. District Court — Southern District of New York

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.

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

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 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, 5, 7, and 8 from the '383 Patent. These...