Glaxo Group Ltd v. Ranbaxy Pharmaceuticals

• Decision Date: 20 August 2001
• Citation: 59 USPQ2d 1950,262 F.3d 1333
• Parties: (Fed. Cir. 2001) GLAXO GROUP LIMITED and GLAXO WELLCOME, INC., Plaintiffs-Appellees, v. RANBAXY PHARMACEUTICALS, INC., Defendant-Appellant. 01-1151
• Court: U.S. Court of Appeals — Federal Circuit

Page 1333

262 F.3d 1333 (Fed. Cir. 2001)

GLAXO GROUP LIMITED and GLAXO WELLCOME, INC., Plaintiffs-Appellees, v. RANBAXY PHARMACEUTICALS, INC., Defendant-Appellant.

01-1151

United States Court of Appeals for the Federal Circuit

August 20, 2001

Rehearing Denied September 17, 2001

Appealed from: U.S. District Court for the District of New Jersey Judge Mary L. Cooper

Stephen B. Judlowe, Hopgood, Calimafde, Judlowe & Mondolino, L.L.P., of New York, New York, argued for plaintiffs-appellees. With him on the brief were Dennis J. Mondolino, Janet B. Linn, Esther H. Steinhauer, and Brian W. Nolan.

Darrell L. Olson, Knobbe, Martens, Olson & Bear, LLP, of Newport Beach, California, argued for defendant-appellant. With him on the brief was William R. Zimmerman.

Before MAYER, Chief Judge, NEWMAN, and RADER, Circuit Judges.

RADER, Circuit Judge.

The United States District Court for the District of New Jersey entered a preliminary injunction against Ranbaxy Pharmaceuticals, Inc. The order enjoined Ranbaxy from offering for sale or selling in the United States any cefuroxime axetil product under its Abbreviated New Drug Application (ANDA). Because Glaxo Group Limited and Glaxo Wellcome, Inc., (collectively "Glaxo") would not likely succeed in proving that Ranbaxy's proposed cefuroxime axetil product infringes U.S. Patent No. 4,562,181 (the '181 patent), this court vacates the preliminary injunction and remands.

I.

On May 12, 1981, Glaxo obtained United States Patent No. 4,267,320 (the '320 patent) on a family of cephalosporin antibiotics, including esters of the antibiotic cefuroxime. Cefuroxime-a broad spectrum antibiotic-treats many conditions, including tonsillitis, sinusitis, and skin infections. The esters of cefuroxime deliver the active drug, also referred to as the active moiety, to the patient. The '320 patent discloses that one specific ester of cefuroxime, cefuroxime axetil, is "particularly preferred" and expressly claims this compound in claim 4. Glaxo obtained a two-year term extension for the '320 patent under 35 U.S.C. 156. The '320 patent expired on May 12, 2000.

Cefuroxime axetil has two physical forms: (1) amorphous (without molecules in an ordered arrangement); and (2) crystalline (with molecules in an ordered arrangement). On December 31, 1985, Glaxo obtained the '181 patent which discloses that the amorphous form of cefuroxime axetil provides various advantages over the crystalline form. Claim 1 of the '181 patent recites: "Cefuroxime axetil in amorphous form essentially free from crystalline material, and having a purity of at least 95% aside from residual solvents." (Emphasis added). The '181 patent will expire on June 29, 2003.

Glaxo obtained approval from the Food and Drug Adminsitration (FDA) on its New Drug Application for cefuroxime axetil. In 1988, Glaxo began marketing Ceftin(r), the commercial embodiment of the '320 and '181 patents.

On April 19, 1999, Ranbaxy filed an ANDA with the FDA seeking approval to market a generic tablet form of cefuroxime axetil in anticipation of the '320 patent's expiration. Ranbaxy's proposed cefuroxime axetil product contains about 10 to 15% crystalline cefuroxime axetil, with the balance of the content amorphous. Glaxo opposed Ranbaxy's ANDA by filing a citizen's petition in the FDA and by filing suit against Ranbaxy in the district court under 35 U.S.C. 271(e)(2).

The district court interpreted the limitation "essentially free from crystalline material" of claim 1 of the '181 patentas "excluding from the claimed invention any item having sufficient crystalline cefuroxime axetil that materially affects the basic characteristics of the invention." Glaxo Group Ltd. v. Ranbaxy Pharm., Inc., No. 00-5172, slip op. at 26-27 (D. N.J. Dec. 21, 2000). The district court determined that claim 1's scope encompassed cefuroxime axetil with a 10 to 15% crystalline content. Based on this claim construction, the district court found that Glaxo was likely to succeed on the merits in proving that Ranbaxy's proposed product infringes the '181 patent. The district court also found that Glaxo stood to lose more money in sales of Ceftin(r) before the '181 patent expired than Ranbaxy's total net worth. Balancing the hardships in Glaxo's favor and finding a public interest in preventing the launch of Ranbaxy's product, the district court entered a preliminary injunction, precluding Ranbaxy from marketing any cefuroxime axetil product under its ANDA.

Ranbaxy appeals the district court's grant of the preliminary injunction. This court has jurisdiction to hear this interlocutory appeal under 28 U.S.C. 1292(c)(1).

II

This court sustains the grant of a preliminary injunction unless the district court abused its discretion, or based its decision on an erroneous legal standard or clearly erroneous findings of fact. Mentor Graphics Corp. v. Quickturn Design Sys., Inc., 150 F.3d 1374, 1377, 47 USPQ2d 1683, 1685 (Fed. Cir. 1998). This court reviews claim construction without deference. Cybor Corp. v. FAS Techs., Inc., 138 F.3d 1448, 1454, 46 USPQ2d 1169, 1172 (Fed. Cir. 1998) (en banc). Applying the claim construction to the accused device to determine infringement is a question of fact, which receives substantial deference on review. Embrex, Inc. v. Serv. Eng'g Corp., 216 F.3d 1343, 1348-49, 55 USPQ2d 1161, 1164 (Fed. Cir. 2000).

To obtain an injunction, a party must prove four factors: (1) its reasonable likelihood of success on the merits; (2) irreparable harm to its interests; (3) the balance of hardships tipping in its favor and (4) public interest in favor of the injunction. Chrysler Motors Corp. v. Auto Body Panels, Inc., 908 F.2d 951, 952, 15 USPQ2d 1469, 1410 (Fed. Cir. 1990). This court turns first to Glaxo's likelihood of success in showing that Ranbaxy's proposed cefuroxime axetil product would infringe the '181 patent.

In review of Glaxo's likelihood of success, this court examines the construction of claim 1 and its application to Ranbaxy's proposed product. Bell & Howell Document Mgmt. Prods. Co. v. Altek Sys., 132 F.3d 701, 704, 45 USPQ2d 1033, 1036 (Fed. Cir. 1997). Claim language defines claim scope. York Prods., Inc. v. Cent. Tractor Farm & Family Ctr., 99 F.3d 1568, 1572, 40 USPQ2d 1619, 1622 (Fed. Cir. 1996). To determine the meaning of disputed claim terms, however, a construing court may consider the patent specification and the administrative record leading to patent issuance. Whittaker Corp. v. UNR Indus., Inc., 911 F.2d 709, 711, 15 USPQ2d 1742, 1744 (Fed. Cir. 1990).

As found by the district court, "essentially" means "fundamentally." Webster's Third New Int'l Dictionary 777 (1986). "Free from" means "without." Thus, in other words, "essentially free from crystalline material" means "fundamentally without crystalline material." See In re Marosi, 710 F.2d 799, 803, 218 USPQ 289, 291-292 (Fed. Cir. 1983) (interpreting "essentially free" to mean that a material is present only as an unavoidable impurity). The claims do not further enlighten the amount of crystalline material permitted within the scope of claim 1.

The written description of the '181 patent discloses in several places that cefuroxime axetil should be "substantially amorphous." E.g., Col. 2, ll. 24-25. The written description further discloses: "The cefuroxime axetil ester in accordance with the invention is preferably essentially free from crystalline material." Col. 2, ll. 38-40. The examples in the written description also shed little further quantitative light on the meaning of "essentially free from crystalline material."

According to Example 1, an analysis of the prepared product by the Debye- Scherrer x-ray method "gave a plain halo (absence of crystals, confirming the amorphous nature of the product)." Col. 8, ll. 8-9. The same analysis of the Example 18 product "showed a few faint lines which may suggest the presence of a few crystals." Example 21 states: "Microscopic examination suggested Col. 10, ll. 4-5. Tests of several other examples by x-ray crystallography, microscopic examination, and infrared analyses showed a "substantially amorphous" product. No example specifically quantifies "substantially amorphous" or "essentially free from crystalline material."

The prosecution history of the '181 patent, however, is more illuminating. As originally filed on June 29, 1983, claims 1 and 4 of the application which led to the '181 patent recited:

1.Cefuroxime axetil in highly pure, substantially amorphous form.

. . . .

4.The product of claim 1 essentially free from crystalline material.

Dependent claims are generally narrower in scope than the claims from which they depend. Lampi Corp. v. Am. Power Prods., Inc., 228 F.3d 1365, 1376, 56 USPQ2d 1445, 1453 (Fed. Cir. 2000). Accordingly, "essentially free from crystalline material," as recited in original dependent claim 4, would apparently carry a narrower meaning than "substantially amorphous." Example 22 of the written description states: "X-ray crystallography revealed the product was substantially amorphous with a small content of crystalline material." Col. 10, ll. 26-28. Thus, cefuroxime axetil that is "essentially free from crystalline material" must have less than "a small content of crystalline material."

During the prosecution of Glaxo's United States Patents Nos. 4,994,567 and 5,013,833, both related to the '181 patent and containing the same Example 22, Glaxo explained: "Example 22 of the specification has shown that the product contains approximately 10% crystalline material." Further, during trial, Glaxo conceded that Example 22 does indeed contain 10% crystalline material. As noted above, the written description characterizes Example 22 as "substantially amorphous." In the original application, the independent claim 4 used the term "substantially amorphous," while a dependent claim used the narrower term "essentially free from crystalline material." This chain of reasoning suggests that "essentially free...