Ortho-Mcneil Pharmaceutical v. Mylan Laboratories

Citation348 F.Supp.2d 713
Decision Date23 December 2004
Docket NumberNo. CIV.A. 1:02CV32.,CIV.A. 1:02CV32.
CourtU.S. District Court — Northern District of West Virginia
PartiesORTHO-MCNEIL PHARMACEUTICAL, INC., Johnson & Johnson Pharmaceutical Research & Development, LLC, and Daiichi Pharmaceutical Co., Ltd., Plaintiffs, v. MYLAN LABORATORIES, INC. and Mylan Pharmaceuticals, Inc., Defendants.

George F. Pappas, Vicki Margolis, Jeffrey B. Elikan, Ryan M. Walsh, Jeffrey A. Dunn, Mary Ellen R. Himes, Venable, Baetjer, Howard & Civiletti, LLP, Steven P. Berman, Johnson & Johnson, New Brunsick, NJ, Mary Jane Saunders, Eugene Purvis, Jr., Justin E. Pierce, Kali N. Murray, Venable Baetjer and Howard, LLP, Vienna, VA, Frank E. Simmerman, Jr., Simmerman Law Office, PLLC, Richard W. Gallagher, Robinson & McElwee, Clarksburg, WV, Mary H. Sanders, Huddleston, Bolen, Beatty, Porter & Copen, Charleston, WV, Brett Smith Sylvester, Paul Joseph Wilson, Brian Hannon, Michael R. Dzwonczyk, Paul M. Higgins, Keiko K. Takagi, Sughrue Mion, PLLC, Washington, DC, J. Warren Lytle, Jr., Sughrue Mion, PLLC, for Plaintiffs.

Robert A. Bourque, Jeremy S. Pitcock, Noah M. Leibowitz, Jordan N. Malz, Henry B. Gutman, Amy E. Semet, Simpson, Thacher & Bartlett, New York, NY, Mark Boland, W. Mack Webner, Sheldon I. Landsman, Sughrue Mion, PLLC, Washington, DC, Jeffrey E. Ostrow, Harrison J. Frahn, Simpson Thacher & Bartlett, Palo Alto, CA, for Plaintiffs and Defendants.

Gordon H. Copland, Megan D. Dortenzo, Steptoe & Johnson, Clarksburg, WV, Michael T. Smith, Steptoe & Johnson, Martinsburg, WV, Gregory R. Lyons, Christopher L. Hale, John B. Wyss, Wiley, Rein & Fielding, E. Anthony Figg, Joseph A. Hynds, Glen Karta, Martin M. Zoltick, Rothwell, Figg, Ernst & Manbeck, James H. Wallace, Jr., Mark I. Bowditch, Wiley Rein & Fielding, LLC, Washington, DC, Terry L. Schnell, William P. Smith, Roberta R. Wilson, DKW Law Group, PC, Pittsburgh, PA, for Defendants.


KEELEY, District Judge.

This is an action for the infringement of a chemical invention protected by U.S. Patent No. 5,053,407 (issued Oct. 1, 1991) ("the '407 patent"). The patent, entitled "Optically Active Pyridobenzoxazine Derivatives and Anti-Microbial Use," claims a compound named levofloxacin. The plaintiffs in this suit are Daiichi Pharmaceutical Co., Ltd. ("Daiichi"), levofloxacin's inventor and patent-holder, and Johnson & Johnson, the parent company of Ortho-McNeil Pharmaceutical, Inc. and Johnson & Johnson Pharmaceutical Research & Development, LLC (collectively "Ortho")1, which holds a license to distribute levofloxacin in the United States. The defendants are Mylan Laboratories, Inc. and Mylan Pharmaceuticals, Inc. (collectively "Mylan").

Mylan committed an act of infringement by filing two Abbreviated New Drug Applications ("ANDAs") (Nos. 76-276 & 77-097) with the Food and Drug Administration ("FDA"), seeking permission to manufacture and distribute a generic version of levofloxacin before the '407 patent expires. 35 U.S.C. § 271(e)(2). The ANDAs included a so-called "Paragraph IV" certification, which asserted that the '407 patent is invalid. See 21 U.S.C. § 355(j)(2)(A)(vii)(IV). As statutorily required, Mylan notified Daiichi of its ANDA filing. See id. §§ 355(j)(2)(B)(i)-(ii). In response, Daiichi and Ortho (collectively "Daiichi/Ortho") filed a timely suit for infringement on February 22, 2002. Id. § 355(j)(5)(B)(iii).

Mylan essentially concedes infringement of the '407 patent, but contends that the patent is invalid on a number of grounds. Between November 4, 2003 and December 22, 2003, the Court held a bench trial on four of these invalidity defenses — prior invention, indefiniteness, inequitable conduct and obviousness. On December 5, 2003, the Court entered judgment as a matter of law against Mylan's prior invention and indefiniteness defenses pursuant to Rule 52(c) of Federal Rules of Civil Procedure. The Court then heard evidence on inherent anticipation, the final invalidity issue, from May 24-26, 2004. In lieu of closing arguments, the parties submitted lengthy post-trial briefs. All briefing concluded on July 12, 2004.

Pursuant to Rule 52(a) of the Federal Rules of Civil Procedure, the Court now states its findings of fact and conclusions of law.2 As discussed below, the Court concludes that Mylan has failed to meet its burden to prove the invalidity of the '407 patent.


Only claims 2 and 5 of the '407 patent are in dispute in this case.3 Generally speaking, claim 2 is a compound claim covering levofloxacin, and claim 5 is a method claim covering the administration of "an antimicrobially effective amount" of levofloxacin to a patient.

The invention at issue in both claims is levofloxacin, which is an enantiomeric compound. An enantiomer is one of a pair of isomers4 that are non-superimposeable mirror images of each other. This mirror image structure is often likened to the relative structures of a person's right and left hands, and chemists normally refer to each enantiomer as either the dextro (Latin dexter, or right-handed) or levo (Latin laevus, or left-handed) enantiomer.

The right/left nomenclature also stems from the fact that enantiomers are inherently "optically active." That is, an enantiomer will rotate a plane of polarized light5 clockwise (dextrorotatory) or counterclockwise (levorotatory). Moreover, a given pair of enantiomers will always rotate polarized light in equal and opposite directions. For example, if the dextrorotatory enantiomer rotates polarized light 90 to the right (clockwise), then the levorotatory enantiomer will rotate the polarized light 90 to the left (counterclockwise).

Because enantiomers have identical chemical formulae, chemists distinguish between the chemical names of enantiomeric pairs by preceding each with a symbol that reflects the direction the enantiomer rotates polarized light: "(+)" for dextrorotatory enantiomers, and "(-)" for levorotatory enantiomers.

Chemists also distinguish between enantiomers by designating an enantiomer as either "R" or "S" based upon the arrangement of certain atoms at the enantiomer's "chiral center."6 Where one enantiomer is an "R," the other will be an "S."

When chemists first find or synthesize a given enantiomeric pair, the enantiomers always occur in a perfect 1:1 ratio. This solution of equal amounts of dextrorotatory and levorotatory enantiomers is known as a "racemic compound."7 A racemic compound is optically inactive because, for every dextrorotatory enantiomer rotating polarized light to the right, there exists a levorotatory enantiomer rotating light to the left, resulting in a net rotation of zero. Chemists also have a specific nomenclature for racemic compounds — the chemical name is preceded by either "(±)" or "RS" (or both).

In this case, ofloxacin is a racemic compound comprised of one dextrorotatory enantiomer with an "R" configuration and one levorotatory enantiomer with an "S" configuration. Racemic ofloxacin is disclosed in U.S. Patent No. 4,382,892 ("the '892 patent"). Levofloxacin, the subject of the '407 patent, is the levorotatory isomer of ofloxacin with the "S" configuration.

A. Original Claim Construction

The Court has previously construed the claims in the case at bar. See Ortho-McNeil Pharms., Inc. v. Mylan Labs., Inc., 267 F.Supp.2d 533 (N.D.W.Va.2003). Specifically, the Court held:

An examination of the plain meaning of the claim language as understood by persons skilled in the art at the time of invention, the specification and the prosecution history indicate that "An S(-)-pyridobenzoxazine compound" and "S (-)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de] [1,4]benzoxazine-6-carboxylic acid" refer to the levorotatory enantiomer of racemic ofloxacin, levofloxacin. These terms do not refer to racemic ofloxacin. Furthermore, as demonstrated by the specification's resolution methodology, as well as the specification and prosecution history's repeated emphasis on levofloxacin's unique pharmacological properties, the disputed language refers more specifically to a pharmaceutical preparation comprised principally of levofloxacin.

Id. at 544. (emphasis added).

The Court now recognizes that its prior construction suffered from several infirmities that need to be corrected. First, although that construction relies heavily on the specification and prosecution history, it does not explain what considerations justified their use as a source for claim limitations. Further, the Court failed to differentiate between the multiple claims at issue. Finally, the Court's perspective on the claims has been sharpened by Mylan's injection of new defenses. Accordingly, the Court finds it necessary to amend its claim construction.

B. Standard of Law

When construing patent claims, the Court must look first to the intrinsic evidence in the record: "The claims, the specification, and the prosecution history." Markman v. Westview Instruments, Inc., 52 F.3d 967, 979 (Fed.Cir.1995) (en banc). The court does not look to each of these three sources equally; rather, they are a "hierarchy of analytical tools." Digital Biometrics, Inc. v. Identix, Inc., 149 F.3d 1335, 1344 (Fed.Cir.1998). With these varying sources of information, the Court must be careful to always focus on interpreting the claim language as written. See Eastman Kodak Co. v. Goodyear Tire & Rubber Co., 114 F.3d 1547, 1552 (Fed.Cir.1997) ("... a construing court does not accord the specification, prosecution history, and other relevant evidence the same weight as the claims themselves, but consults these sources to give the necessary context to the claim language.")

Thus, the most important part of the court's analysis is the claim language itself. See Digital Biometrics, 149 F.3d at 1344. ("The...

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