In re '639 Patent Litigation, CIV.A.97-12416-RCL.

• Decision Date: 14 August 2001
• Docket Number: No. CIV.A.97-12416-RCL.,CIV.A.97-12416-RCL.
• Parties: In Re: '639 PATENT LITIGATION
• Court: U.S. District Court — District of Massachusetts

154 F.Supp.2d 157

In Re: '639 PATENT LITIGATION

No. CIV.A.97-12416-RCL.

United States District Court, D. Massachusetts.

August 14, 2001.

COPYRIGHT MATERIAL OMITTED

Thomas Creel, Kaye, Scholer, Firman, Hays and Handlar, LLP, New York City, for Special Master.

Bernard J. Bonn, III, Timothy C. Blank, Kara W. Swanson, Barry S. Pollack, Dechert, Price & Rhoads, Boston, MA, Henry J. Renk, Stevan J. Bosses, Diego, Scambia, Robert L. Baechtold, David F. Ryan, Fitzpatrick, Cella, Harper & Scinto, New York City, for Plaintiffs.

Thomas M. Hemnes, Philip C. Swain, Foley, Hoag & Eliot, Robert J. Muldoon, Jr., Sherin & Lodgen, Boston, MA, John J. Normile, Anthony M. Insogna, Pennie & Edmonds, New York City, Sherin & Lodgen, Boston, MA, Stanton T. Lawrence, Pennie & Edmonds, Washington, DC, Michael A. Albert, Wolf, Greenfield & Sacks, Boston, MA, Steven J. Lee, Elizabeth J. Holland, Frederick H. Rein, Lawrence B. Ebert, Kenyon & Kenyon, New York City, Mark C. Rosenthal, Joshua W. Leichter, Steven N. Farber, Palmer & Dodge, Boston, MA, for Defendants.

MEMORANDUM OF FINDINGS OF FACT AND CONCLUSIONS OF LAW

LINDSAY, District Judge.

I. Introduction

This case concerns United States Patent No. 4,420,639 (the "'639 patent"), issued with respect to the chemical compound known as nabumetone to Anthony W. Lake and Carl J. Rose on December 13, 1983 and assigned to Beecham Group, p.l.c. ("Beecham"), one of two plaintiffs herein.¹ Stipulated Facts ¶¶ 6, 82. The '639 patent contains four claims covering nabumetone. Only two of those claims are at issue in this case: claim 2, which recites the compound in solid form; and claim 4, which recites the compound per se. See Stipulated Facts ¶¶ 7, 84. Since February, 1992, pursuant to its New Drug Application ("NDA") No. 19-583, SmithKline Beecham Corporation ("SmithKline Beecham"), the second plaintiff,² has marketed an anti-inflammatory drug product called Relafen, the active ingredient of which is nabumetone. Stipulated Facts ¶¶ 8-10. The defendants, Copley Pharmaceutical, Inc., Teva Pharmaceuticals U.S.A., and Eon Labs Manufacturing, Inc., (the "defendants"), seek to market a generic version of Relafen.

Each of the defendants, pursuant to 21 U.S.C. § 355(j), has filed with the United States Food and Drug Administration ("FDA") an abbreviated new drug application ("ANDA"), by which each seeks the FDA's approval for the commercial manufacture, use and sale of a drug product containing nabumetone. With its ANDA, each defendant also filed with the FDA a certificate, pursuant to 21 U.S.C. § 355(j)(2)(A)(vii)(IV), asserting that the '639 patent is invalid (a "Category IV Certification"). The Category IV Certifications for the defendants Copley Pharmaceutical, Inc., and Eon Labs Manufacturing, Inc., also asserted that the '639 patent is unenforceable. Stipulated Facts ¶¶ 11-19.

The defendants each gave written notice ("notice of certification") to Beecham, pursuant to 21 U.S.C. § 355(j)(2)(B)(i) and (ii), that the ANDA and the accompanying certification had been filed with the FDA. In accordance with 21 U.S.C. § 355(j)(2)(B)(ii), the defendants' notices also set forth the legal and factual bases for their claims that the '639 patent is invalid and/or unenforceable. Id. With regard to each defendant, within forty-five days of receipt of notice, Beecham, as permitted by 21 U.S.C. § 355(j)(5)(B)(iii), brought suit, together with SmithKline Beecham, to enjoin the infringement of the '639 patent.³ The three suits have been consolidated for all purposes in the present action. Stipulated Facts ¶ 20.

By way of defenses and counterclaims to the plaintiffs' infringement action, the defendants first claim that the '639 patent is invalid because nabumetone was anticipated by prior art, namely a 1973 article by scientists J.N. Chatterjea and R. Prasad entitled "Condensation of Mannich Base Salts with Phenols: Orientation of Adducts," published in the Indian Journal of Chemistry, Volume 11 at 214-18 (March 1973) (the "Chatterjea & Prasad publication"). The Chatterjea & Prasad publication identified and enabled nabumetone, the defendants argue, and therefore anticipated all claims set forth in the '639 patent, either explicitly or inherently. The defendants claim, in addition, that the '639 patent is unenforceable because Beecham breached its duty of candor to, and engaged in inequitable conduct before, the United States Patent and Trademark Office ("PTO").

On January 20, 1999, I entered an order referring this case to Thomas Creel, as special master, for management of pre-trial discovery. In July of 1999, the defendants filed two motions for summary judgment: one on the ground that all claims in the patent were invalid; and the second on the ground that inequitable conduct rendered the patent unenforceable. By order dated November 5, 1999, I referred both motions to special master Creel for a report and recommendation as to the disposition of the issues raised by the motions. On January 31, 2000, the special master issued two reports and recommendations. The first recommended that the defendants' motion for summary judgment, based upon invalidity of all claims, be granted. The second recommended that the defendants' motion for summary judgment of unenforceability, based upon inequitable conduct, be denied because there remained triable issues of fact as to the intent element of the inequitable conduct claim.

After a de novo review of the issues raised by the motions, I issued a memorandum and order on August 16, 2000 that (1) rejected the special master's recommendation and denied the motion for summary judgment as to invalidity (because the record demonstrated material issues of fact in dispute); and (2) adopted the special master's recommendation and denied the motion for summary judgment on unenforceability. As noted in that order, with regard to the motion for summary judgment on unenforceability, I specifically accepted and adopted the special master's analysis and conclusions.

A non-jury trial of this case commenced on January 8, 2001 and consumed sixteen trial days. Because the defendants bore the burden of overcoming, by clear and convincing evidence, the presumption, under 35 U.S.C. § 282, that the patent was valid and enforceable, I set the order of trial so that the defendants presented their case-in-chief first.

At the close of the defendants' case, the plaintiffs moved for entry of judgment in their favor pursuant to Fed.R.Civ.P. 52(c). After hearing argument, I declined to rule on the plaintiffs' motion. The plaintiffs then presented their case.

II. Findings of Background Facts

A. The Parties

Beecham is a corporation of the United Kingdom and the owner of the '639 patent. Stipulated Facts ¶¶ 2, 6. SmithKline Beecham is a corporation of the Commonwealth of Pennsylvania, and the owner of New Drug Application No. 19-583, pursuant to which it has marketed Relafen in the United States since February, 1992. Stipulated Facts ¶¶ 1, 8-9. The defendants all are corporations of the State of Delaware. Stipulated Facts ¶¶ 3-5.

B. Nabumetone

Nabumetone is the generic name that has been given to the chemical compound at issue in this case. The structure of nabumetone may be indicated in words, using various accepted chemical naming conventions. For example, nabumetone may be validly described either as "Συ-(2-methoxy-6-naphthyl) ethyl methyl ketone" (or, in abbreviated form: "methoxy ketone"); or as "4-(6'-methoxy-2'-naphthyl) butan-2-one." Stipulated Facts ¶¶ 33-34.

C. Level of Ordinary Skill in the Art

The category of art into which the '639 patent falls is that of synthetic organic chemistry. Testimony of Dr. Edward C. Taylor ("Taylor"), Day 1 at 54:18-19; Testimony of Dr. Paul Bartlett ("Bartlett"), Day 15 at 107:3-6. One of ordinary skill in the art of synthetic organic chemistry in 1973 was a person having either a doctoral degree in organic chemistry, primarily synthetic organic chemistry, with a year or two of post-doctoral experience, either industrial or academic; or a masters degree in synthetic organic chemistry with four or five years of industrial experience in that field. Taylor, Day 1 at 89:4-14; Bartlett, Day 15 at 106:14-107:15. The person of ordinary skill in the art in 1973 (sometimes referred to herein as the "ordinary chemist") knew how to conduct standard reactions, such as reduction reactions; reactions named in the Chatterjea & Prasad publication, such as the Grignard reaction;⁴ and could apply standard organic chemical methods to the synthesis of simple organic molecules. Taylor, Day 1 at 89:15-90:7. The ordinary chemist in 1973 was familiar with nuclear magnetic resonance ("NMR") spectroscopy, a tool for determining chemical structure. Taylor Day 1 at 90:7-22. The ordinary chemist in 1973 also was familiar with standard chemistry and organic synthesis textbooks, and was able to do a literature search using Chemical Abstracts, an index of developments in chemistry periodically published by The American Chemical Society. Taylor, Day 1 at 90:22-91 3; Stipulated Facts ¶ 123. Beecham chemists Drs. Alex Goudie, Ms. Laramie Gaster (later Dr. Laramie Gaster), and Dr. Marta Marton all were persons of ordinary skill in the art in the mid-1970s. Testimony of Dr. Carl Rose ("Rose"), Day 10 at 75:15-77:7.

D. The Chatterjea & Prasad publication

The Chatterjea & Prasad publication was published more than one year prior to the date of Beecham's application in the United States for the '639 patent and was listed in Volume 79 of Chemical Abstracts. In that volume of Chemical Abstracts, the Chatterjea & Prasad publication was indexed under 4-(6'-methoxy-2'-naphthyl) butan-2-one, one of the chemical names for nabumetone. Stipulated Facts ¶¶ 122-25.

Nabumetone is referenced on two of the five pages in the Chatterjea & Prasad publication. First, at page 215, the article refers to the methyl ether of compound XX, a hydroxy compound; the structure of that methyl ether is that of...