PURDUE PHARMA L.P., THE P.F. LABORATORIES, INC., PURDUE PHARMACEUTICALS L.P., RHODES TECHNOLOGIES, Plaintiffs-Appellants
EPIC PHARMA, LLC, Defendant; PURDUE PHARMA L.P., THE P.F. LABORATORIES, INC., PURDUE PHARMACEUTICALS L.P., RHODES TECHNOLOGIES, Plaintiffs-Appellants
MYLAN PHARMACEUTICALS INC., MYLAN INC., Defendants-Appellees; PURDUE PHARMA L.P., THE P.F. LABORATORIES, INC., PURDUE PHARMACEUTICALS L.P., RHODES TECHNOLOGIES, GRUNENTHAL GMBH, Plaintiffs-Appellants
AMNEAL PHARMACEUTICALS, LLC, Defendant-Appellee; GRUNENTHAL GMBH, PURDUE PHARMA L.P., THE P.F. LABORATORIES, INC., PURDUE PHARMACEUTICALS L.P., RHODES TECHNOLOGIES, Plaintiffs-Appellants
TEVA PHARMACEUTICALS USA, INC., Defendant-Appellee
[Copyrighted Material Omitted]
Appeal from the United States District Court for the Southern District of New York in No. 1:13-cv-00683-SHS, Senior Judge Sidney H. Stein. Appeal from the United States District Court for the Southern District of New York in No. 1:12-cv-02959-SHS, Senior Judge Sidney H. Stein. Appeals from the United States District Court for the Southern District of New York in No. 1:11-cv-08153-SHS, Senior Judge Sidney H. Stein. Appeals from the United States District Court for the Southern District of New York in Nos. 1:11-cv-02037-SHS, 1:12-cv-05083-SHS, Senior Judge Sidney H. Stein.
GREGORY A. CASTANIAS, Jones Day, Washington, DC, argued for all plaintiffs-appellants. Plaintiffs-appellants Purdue Pharma L.P., The P.F. Laboratories, Inc., Purdue Pharmaceuticals L.P., Rhodes Technologies also represented by JENNIFER LORAINE SWIZE; JOHN JOSEPH NORMILE, JR., New York, NY; ROBERT J. GOLDMAN, Ropes & Gray LLP, East Palo Alto, CA; SONA DE, CHRISTOPHER J. HARNETT, New York, NY.
BASIL J. LEWRIS, Finnegan, Henderson, Farabow, Garrett & Dunner, LLP, Washington, DC, for plaintiff-appellant Grunenthal GmbH. Also represented by JENNIFER HOWE ROSCETTI, ERIN MCGEEHAN SOMMERS; CHARLES E. LIPSEY, Reston, VA.
WILLIAM A. RAKOCZY, Rakoczy Molino Mazzochi Siwik LLP, Chicago, IL, argued for defendants-appellees Mylan Pharmaceuticals Inc., Mylan Inc. Also represented by AMY D. BRODY, ERIC R. HUNT, NATASHA L. WHITE.
BARBARA MULLIN, Akin, Gump, Strauss, Hauer & Feld, LLP, Philadelphia, PA, argued for defendant-appellee Amneal Pharmaceuticals, LLC. Also represented by STEVEN D. MASLOWSKI, MATTHEW A. PEARSON, ANGELA VERRECCHIO, JASON WEIL; EMILY CURTIS JOHNSON, Washington, DC; KENNETH E. CROWELL, STUART D. SENDER, Budd Larner, P.C., Short Hills, NJ.
MARK DAVID SCHUMAN, Carlson, Caspers, Vandenburgh, Lindquist & Schuman, P.A., Minneapolis, MN, argued for defendant-appellee Teva Pharmaceuticals USA, Inc. Also represented by M. JEFFER ALI, JENNELL CHRISTINE BILEK, ALEXANDRA JANE OLSON, CHRISTOPHER A. PINAHS, SARAH STENSLAND, TODD S. WERNER.
DONALD E. KNEBEL, Barnes & Thornburg LLP, Indianapolis, IN, for amici curiae Donald E. Knebel, Mark David Janis. Also represented by MARK DAVID JANIS, Indiana University Maurer School of Law, Bloomington, IN.
BENJAMIN CONRAD BLOCK, Covington & Burling LLP, Washington, DC, for amicus curiae Center for Lawful Access and Abuse Deterrence.
Before PROST, Chief Judge, REYNA, Circuit Judge, and STARK, Chief District Judge.[*]
[117 U.S.P.Q.2d 1735] Prost, Chief Judge.
This appeal arises from consolidated Hatch-Waxman proceedings involving the reformulated version of the pain reliever OxyContin® . The Appellants, Purdue Pharma L.P., The P.F. Laboratories, Inc., Purdue Pharmaceuticals L.P., and Rhodes Technologies (collectively, " Purdue" ) and Grunenthal GmbH (" Grunenthal" ) asserted a number of claims from multiple different patents against the Appellees, Amneal Pharmaceuticals, LLC (" Amneal" ), Epic Pharma, LLC (" Epic" ), Mylan Pharmaceuticals Inc. and Mylan Inc. (collectively, " Mylan" ), and Teva Pharmaceuticals USA, Inc. (" Teva" ), all of whom have filed Abbreviated New Drug Applications (" ANDAs" ) seeking to sell generic versions of OxyContin® . The United States District Court for the Southern District of New York held a three-week bench trial in the case against Teva, following which it held all of the asserted patent claims invalid. In re OxyContin Antitrust Litig., 994 F.Supp.2d 367, 377 (S.D.N.Y. 2014) (" District Court Decision " ). The court then entered orders of dismissal in the three remaining cases against Amneal, Epic, and Mylan based on collateral estoppel. Purdue and Grunenthal appeal the final judgment in the Teva action, and Purdue also appeals the orders of dismissal in the three other cases. For the reasons stated below, we affirm the district court's rulings.
Oxycodone hydrochloride--the active pharmaceutical ingredient (" API" ) in OxyContin® --is an opioid analgesic used to treat moderate to severe pain. This consolidated appeal concerns four patents associated with the reformulated version of OxyContin® : U.S. Patent No. 7,674,799 (" '799 patent" ), U.S. Patent No. 7,674,800 (" '800 patent" ), U.S. Patent No. 7,683,072 (" '072 patent" ) (collectively, " the low-ABUK patents" ), and U.S. Patent No. 8,114,383 patent (" '383 patent" ).
I. The Low-ABUK Patents
The low-ABUK patents recite an improved formulation of oxycodone hydrochloride. 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 alpha, beta unsaturated ketones (" ABUKs" ). The prior art method of synthesizing oxycodone hydrochloride involved three steps: first, thebaine, a derivative of the opium poppy, was oxidized to form 14-hydroxy; second, the 14-hydroxy was converted to oxycodone free base through hydrogenation; and third, the oxycodone free base was reacted with hydrochloric acid to form oxycodone hydrochloride. The end product created by that process, however, contained high levels of 14-hydroxy, on the order of 1500 parts per million (" ppm" ).
In January 2004, the U.S. Food and Drug Administration (" FDA" ) became concerned that 14-hydroxy was potentially toxic and thus mandated that oxycodone hydrochloride manufacturers either provide evidence that the 14-hydroxy levels in their formulations were safe or reduce the amount of 14-hydroxy to less than 10 ppm. Even before the FDA's mandate, however, Rhodes Technologies--a subsidiary of Purdue--had begun researching methods to reduce 14-hydroxy levels in its oxycodone API. The scientists initially hypothesized that the 14-hydroxy present in the final salt was leftover 14-hydroxy that had not been hydrogenated in the second step. Thus,
[117 U.S.P.Q.2d 1736] they extended the hydrogenation reaction to completion, confirming that every molecule of 14-hydroxy converted to oxycodone free base at step two. But the scientists found that after step three--transforming the oxycodone free base into oxycodone hydrochloride--the 14-hydroxy had returned.
The scientists thus shifted their focus to step three. It was well known in the art that an impurity, 8,14--dihydroxy--7,8--dihydrocodeinone (" 8,14-dihydroxy" ) was produced as a byproduct of the oxidation of thebaine (step one). More specifically, it was known that a particular isomer of 8,14-dihydroxy was formed: 8β, 14--dihydroxy--7,8--dihydrocodeinone (" 8β " ). Scientists did not know with certainty, however, whether 8α, 14--dihydroxy--7,8--dihydrocodeinone (" 8α " )--a diastereomer of 8β --was also produced during the oxidation step. Purdue scientists had previously noted the potential existence of 8α, but no scientific literature discussed that particular isomer. Through experimentation, the scientists determined that 8α was indeed being produced at step one and, in fact, was transforming into 14-hydroxy during the acid-catalyzed dehydration at step three. To remove the 14-hydroxy from the oxycodone API, the scientists added another hydrogenation step at the end of step three to convert the remaining 14-hydroxy into oxycodone free base. By June 2003, Rhodes's laboratory could routinely produce oxycodone API with 14-hydroxy levels less than 10 ppm using the double-hydrogenation process. Purdue and Rhodes thus sought approval from the FDA and patent protection for their low-ABUK oxycodone product.
The low-ABUK patents continue from application No. 11/391,897, known as the " Chapman Application." The claims of the Chapman Application have previously been before us; we authored a non-precedential decision affirming the Board of Patent Appeals and Interferences' determination that the Chapman claims were obvious. Chapman v. Casner, 315 Fed.Appx. 294, 295 (Fed. Cir. 2009) (Rader, CJ., dissenting). In that case, the Board declared an interference between the Chapman Application and U.S. Patent No. 7,153,966 (" Casner" ). The relevant claims in the Chapman Application related to a method for making oxycodone API using a hydrogenation step to remove 14-hydroxy, but they did not require that some of the remaining 14-hydroxy be derived from the 8α isomer. Id. The Board compared Chapman's claims to the prior art and concluded that they were obvious. Chapman appealed directly to us, and we agreed with the Board. We reasoned that, because the claims did not specify the source of the 14-hydroxy, any prior art reference that disclosed conditions under which either 8α or 8β converted to 14-hydroxy would render the claim obvious. Id. at 297. We further noted that the prior art references did just that--they disclosed the conversion of 8β to 14-hydroxy under certain conditions. Id. Thus we affirmed the Board's decision to reject the Chapman claims as obvious. Id. at 297-98.
Purdue eventually amended the Chapman claims to include the claims now on appeal. Unlike the claims in the Chapman Application, the claims at issue here are product claims instead of process claims, and they explicitly recite 8α as the source of at least a portion of the minimal amounts of 14-hydroxy remaining in the oxycodone API. In 2010, the U.S. Patent and Trademark Office allowed the claims and issued the low-ABUK patents.
II. The '383 Patent
The '383 patent covers abuse-resistant formulations. Original OxyContin® was a popular opioid analgesic which delivered a large dose of oxycodone over a twelve-hour period. In the early 2000s, however, reports of widespread abuse of Original OxyContin® emerged, and the problem began to garner significant public attention. Original OxyContin® was susceptible to tampering because abusers could crush the tablets easily into powder, which could then be swallowed, snorted, or injected for an instant opioid " high." In 2001, Purdue and the FDA changed the label of Original
OxyContin® to warn doctors about the potential for abusers to tamper ...