Purdue Pharma L.P. v. Endo Pharmaceuticals Inc.

Citation438 F.3d 1123
Decision Date01 February 2006
Docket NumberNo. 04-1347.,No. 04-1189.,No. 04-1357.,04-1189.,04-1347.,04-1357.
PartiesPURDUE PHARMA L.P., the Purdue Frederick Company, the P.F. Laboratories, Inc., and the Purdue Pharma Company, Plaintiffs/Counterclaim Defendants-Appellants, and Euroceltique S.A., Counterclaim Defendant, v. ENDO PHARMACEUTICALS INC., Defendant/Counterclaimant-Cross Appellant, and Endo Pharmaceuticals Holdings Inc., Defendant-Cross Appellant.
CourtU.S. Court of Appeals — Federal Circuit

Herbert F. Schwartz, Fish & Neave LLP [now known as Fish & Neave IP group of Ropes & Gray LLP], New York, New York, filed a combined petition for panel rehearing and rehearing en banc for plaintiffs/counterclaim defendants-appellants. Of counsel were Edward C. DuMont, Jonathan G. Cedarbaum, and Seth P. Waxman, Wilmer Cutler Pickering Hale and Dorr LLP, Washington, DC; Pablo D. Hendler, Duane-David Hough, Gerald J. Flattmann, Jr., Richard A. Inz, and Denise L. Loring, Ropes & Gray LLP, New York, New York. Of counsel was Robert J. Goldman, Palo Alto, California.

Edward V. Filardi, Skadden, Arps, Slate, Meagher & Flom LLP, New York, New York, filed a response to the petition for defendant-cross appellant defendant/counterclaimant-cross appellant and defendant-cross appellant. With him on the response were Constance S. Huttner, and Douglas R. Nemec. Of counsel were David L. Cohen, and Mark D. Baker. Of counsel on the response were Nicholas L. Coch and Donald L. Rhoads, Kramer Levin Naftalis & Frankel LLP, New York, New York.

Michael A. O'Shea, Akin Gump Strauss Hauer & Feld, LLP, Washington, DC, for amicus curiae International Intellectual Property Institute. With him on the brief was Shari F. Esfahani.

W. Murray Spruill, Alston & Bird LLP, Raleigh, North Carolina, for amicus curiae Biotechnology Industry Organization.

Richard A. Samp, Washington Legal Foundation, Washington, DC, for amicus curiae Washington Legal Foundation.

Richard L. Rainey, Finnegan, Henderson, Farabow, Garrett & Dunner, L.L.P., Washington, DC, for amicus curiae Pharmaceutical Research and Manufacturers of America. With him on the brief was Darrel C. Karl.

John F. Duffy, George Washington University Law School, Washington, DC, for amici curiae Law Professor John F. Duffy, et al.

Eric J. Lobenfeld, Hogan & Hartson L.L.P., New York, New York, for amicus curiae Congressman Darrell Issa.

Milton M. Oliver, Ware, Fressola, Van der Sluys & Adolphson LLP, Monroe, Connecticut, for amicus curiae Richard L. Edelson, M.D.

Before GAJARSA, Circuit Judge, PLAGER, Senior Circuit Judge, and LINN, Circuit Judge.

PLAGER, Senior Circuit Judge.

This is a patent case. It arose when Purdue Pharma L.P., The Purdue Frederick Company, The P.F. Laboratories, Inc., and The Purdue Pharma Company (collectively, "Purdue") filed an infringement suit against Endo Pharmaceuticals Inc. and Endo Pharmaceuticals Holdings Inc. (collectively, "Endo") in the United States District Court for the Southern District of New York. Plaintiffs alleged that Endo's proposed generic versions of OxyContin®, Purdue's controlled release oxycodone product, would infringe three Purdue patents.

After a bench trial, the trial court found that Endo would infringe Purdue's patents, but determined that the patents were unenforceable due to inequitable conduct that occurred during prosecution before the United States Patent and Trademark Office ("PTO").1 Purdue appealed the inequitable conduct judgment; Endo cross-appealed the infringement judgment. On appeal, we initially affirmed the trial court's judgment that the patents were unenforceable due to the inequitable conduct by Purdue.2 The cross-appeal was deemed moot.

On petition for rehearing, we have further examined the issues in the case. The trial judge had provided us with a thorough and complete opinion, explaining the case and his view of it. Our further examination suggested, nevertheless, that there were some issues that needed more development. In addition to fact-finding regarding materiality and intent, inequitable conduct requires a special kind of balancing, weighing the level of materiality against the weight of the evidence of intent.

Our further review has persuaded us that the trial judge may have erred in how he viewed certain of the evidence, and that this may have caused an error in the balancing step. Accordingly, we have withdrawn the earlier opinion and replaced it with this one. The judgment of inequitable conduct is now vacated, and the matter is remanded to the trial court for further proceedings in accordance with this opinion. Since the ultimate issue of patent unenforceability remains open, it is necessary for us to address the cross-appeal on the infringement issue; we affirm the trial court's determination that Endo's product would infringe Purdue's patents.

BACKGROUND

The three patents asserted by Purdue against Endo are directed to controlled release oxycodone medications for the treatment of moderate to severe pain. The patents are related: U.S. Patents No. 5,656,295 (the "'295 patent") and No. 5,508,042 (the "'042 patent") are, respectively, a continuation-in-part and a divisional of U.S. Patent No. 5,549,912 (the "'912 patent"). The '912 patent itself is a continuation-in-part of U.S. Patent No. 5,266,331 (the "'331 patent"), which Purdue has not asserted against Endo. The '331 patent is the parent patent, and for ease of reference will be identified as such from time to time.

The written descriptions of the '912, '295 and '042 patents are virtually identical. The asserted claims include composition claims (claims 1-4 of the '912 patent and claims 1-4 and 6-7 of the '295 patent) and method claims (claims 8-10 of the '295 patent and claims 1 and 2 of the '042 patent). Claim 1 of the '912 patent is representative of the composition claims and reads:

A controlled release oxycodone formulation for oral administration to human patients, comprising from about 10 to about 40 mg oxycodone or a salt thereof, said formulation providing a mean maximum plasma concentration of oxycodone from about 6 to about 60 ng/ml from a mean of about 2 to about 4.5 hours after administration, and a mean minimum plasma concentration from about 3 to about 30 ng/ml from a mean of about 10 to about 14 hours after repeated administration every 12 hours through steady-state conditions.

Claim 1 of the '042 patent is representative of the method claims and reads:

A method for reducing the range in daily dosages required to control pain in human patients, comprising administering an oral controlled release dosage formulation comprising from about 10 to about 40 mg oxycodone or a salt thereof which provides a mean maximum plasma concentration of oxycodone from about 6 to about 60 ng/ml from a mean of about 2 to about 4.5 hours after administration, and a mean minimum plasma concentration from about 3 to about 30 ng/ml from a mean of about 10 to about 14 hours after repeated administration every 12 hours through steady-state conditions.

The "Detailed Description" section of the written description in each asserted patent opens with the following statement, which played a prominent role in the trial court's inequitable conduct determination:

It has now been surprisingly discovered that the presently claimed controlled release oxycodone formulations acceptably control pain over a substantially narrower, approximately four-fold [range] (10 to 40 mg every 12 hours — around-the-clock dosing) in approximately 90% of patients. This is in sharp contrast to the approximately eight-fold range required for approximately 90% of patients for opioid analgesics in general.

'912 patent, col. 3, ll. 34-41 (emphasis added).3

The thrust of this language is that the invented oxycodone formulation using a four-fold range of dosages (e.g., between 10 mg and 40 mg) achieves the same clinical results as the prior art opioid formulations using an eight-fold range of dosages (e.g., between 10 mg and 80 mg). The written description later explains that the "clinical significance" of the four-fold dosage range of the oxycodone formulations of the present invention, as compared to other opioid analgesics, such as morphine, requiring twice the dosage range, is a more efficient titration process, which is the process of adjusting a patient's dosage to provide acceptable pain relief without unacceptable side effects. Id., col. 4, ll. 51-63.

In December 1995, after obtaining FDA approval, Purdue introduced its controlled release oxycodone product under the name OxyContin®. In September 2000, pursuant to the procedures of the Hatch-Waxman Act, 21 U.S.C. § 355(j), Endo filed an Abbreviated New Drug Application ("ANDA") with the FDA seeking approval to make and sell a generic version of Purdue's OxyContin® formulation. The patents-in-suit had issued by this time, and Purdue had listed them in the Orange Book4 as covering OxyContin®. Endo notified Purdue it had filed a paragraph IV certification asserting that Purdue's patents either would not be infringed by Endo's generic drug or were invalid.5 In October 2000 Purdue initiated a patent infringement suit under 35 U.S.C. § 271(e)(2) on the basis of Endo's ANDA filing, alleging that Endo's generic drug would infringe the '912, '295, and '042 patents. Endo subsequently twice amended its ANDA to seek approval for additional dosage strengths. Purdue filed two additional infringement suits, which the trial court consolidated with the original action.

Endo filed counterclaims seeking a declaratory judgment that Purdue's patents were invalid, unenforceable, and not infringed. Endo also filed counterclaims under federal antitrust and New York unfair trade practice laws. The trial court bifurcated the patent claims from the antitrust and unfair trade claims and in June 2003 held an 11-day bench trial on the patent issues.

In an extensive opinion, the trial court found that Purdue had shown by a preponderance of the...

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