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Sumitomo Dainippon Pharma Co., Ltd. v. Emcure Pharmaceuticals Ltd.

United States Court of Appeals, Federal Circuit

April 16, 2018

SUMITOMO DAINIPPON PHARMA CO., LTD., SUNOVION PHARMACEUTICALS INC., Plaintiffs-Appellees
v.
EMCURE PHARMACEUTICALS LIMITED, HERITAGE PHARMA LABS INC., FKA EMCURE PHARMACEUTICALS USA INC., INVAGEN PHARMACEUTICALS, INC., TEVA PHARMACEUTICALS USA, INC., TEVA PHARMACEUTICAL INDUSTRIES, LTD., Defendants-Appellants

          Appeals from the United States District Court for the District of New Jersey in Nos. 2:15-cv-00280-SRC-CLW, 2:15-cv-00281-SRC-CLW, 2:15-cv-06401-SRC-CLW, Judge Stanley R. Chesler.

          Preston K. Ratliff, II, Paul Hastings LLP, New York, NY, argued for plaintiffs-appellees. Also represented by Joseph M. O'Malley, Jr.; Stephen Blake Kinnaird, Washington, DC; William Charles Baton, Charles M. Lizza, Saul Ewing Arnstein & Lehr LLP, Newark, NJ.

          Christopher K. Hu, Blank Rome LLP, New York, NY, argued for all defendants-appellants. Defendants-appellants Emcure Pharmaceuticals Limited, Heritage Pharma Labs Inc. also represented by Jay Philip Lessler; David C. Kistler, Princeton, NJ.

          Robert S. Silver, Caesar, Rivise, Bernstein, Cohen & Pokotilow, Ltd., Philadelphia, PA, for defendant-appellant Invagen Pharmaceuticals, Inc. Also represented by Salvatore Guerriero, Pei-Ru Wey.

          Ira J. Levy, Goodwin Procter LLP, New York, NY, for defendants-appellants Teva Pharmaceuticals USA, Inc., Teva Pharmaceutical Industries, Ltd. Also represented by Linnea P. Cipriano, Cynthia Lambert Hardman; William M. Jay, Washington, DC; David Zimmer, Boston, MA; Brian Joseph Prew, Greenberg Traurig, LLP, New York, NY.

          Before Moore, Mayer, and Stoll, Circuit Judges.

          Stoll, Circuit Judge.

         This Hatch-Waxman appeal requires us to construe the scope of a claim depicting a compound's chemical structure. Although the compound can exist in two different three-dimensional orientations that are mirror images of each other, only one is portrayed in the claim. The district court construed the claim to cover the two three-dimensional orientations in isolation-both the one shown in the claim and its mirror image-as well as mixtures of the two in any ratio. The parties then stipulated to infringement and the entry of an injunction. We agree that, at a minimum, the claim encompasses the specific orientation depicted. Because this orientation is the active pharmaceutical ingredient in each party's commercial product, we need not determine what else falls within the claim's ambit to resolve the present dispute. We affirm.

         I

         Stereochemistry is the study of a molecule's three-dimensional structure. Stereoisomers are molecules with the same chemical formula and structure but different three-dimensional configurations. If two stereoisomers are non-superimposable mirror images of one another, they are called enantiomers. Compounds with chiral centers-a carbon atom bonded to four non-identical atoms or groups of atoms-provide common examples of compounds with enantiomers. Although enantiomers often have identical physical properties, such as density and boiling point, they can exhibit different pharmacological properties in the human body.

         When drawing enantiomers, chemists use wedges and dashes to indicate the three-dimensional structure. A wedge designates a bond coming out of the plane of the paper towards the reader, a dashed line represents a bond extending behind the plane of the paper, and normal lines signify bonds in the same plane as the paper. A simple example of two enantiomers is shown below:

         (Image Omitted)

         J.A. 1010. The two molecules are enantiomers because they cannot be made identical to one another without breaking and rearranging the chemical bonds. If the molecule on the right is rotated to align atoms "1" and "2" with the molecule on the left, atoms "3" and "4" are in the reverse position.

         Chemists often characterize enantiomers as "()" or "(-)" based on their optical activity-the ability of a solution containing one enantiomer to rotate polarized light. A solution of the ()-enantiomer rotates the plane of polarized light in a clockwise direction, and a solution of the (-)-enantiomer ...


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