887 F.3d 1153 (Fed. Cir. 2018), 2017-1798, Sumitomo Dainippon Pharma Co., Ltd. v. Emcure Pharmaceuticals Limited

Docket Nº:2017-1798, 2017-1799, 2017-1800
Citation:887 F.3d 1153, 126 U.S.P.Q.2d 1389
Opinion Judge:Stoll, Circuit Judge.
Party Name: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
Attorney: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, Ne...
Judge Panel:Before Moore, Mayer, and Stoll, Circuit Judges.
Case Date:April 16, 2018
Court:United States Courts of Appeals, Court of Appeals for the Federal Circuit

Page 1153

887 F.3d 1153 (Fed. Cir. 2018)

126 U.S.P.Q.2d 1389

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

Nos. 2017-1798, 2017-1799, 2017-1800

United States Court of Appeals, Federal Circuit

April 16, 2018

Page 1154

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.

OPINION

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

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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 rotates the plane of polarized light in a counter-clockwise direction.

Mixtures can contain enantiomers in any ratio. A mixture with 50% of the (+)-enantiomer and 50% of the (-)-enantiomer is known as a " racemate" or " racemic mixture." Racemic mixtures do not rotate the plane of polarized light because the clockwise rotation caused by the (+)-enantiomer cancels out the equal but opposite counter-clockwise rotation of the (-)-enantiomer.

Having summarized the relevant organic chemistry principles, we now turn to the merits of this appeal. Sumitomo Dainippon Pharma Co. and Sunovion Pharmaceuticals Inc. own U.S. Patent No. 5,532,372. The ’372 patent relates generally to " novel imide compounds and their acid addition

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salts" that are useful as antipsychotic agents. ’372 patent col. 1 ll. 8-12. The ’372 patent dis-closes and claims more than one billion compounds, some of which have stereo and optical isomers. Id. at col. 4 ll. 51-53. Lurasidone, the (-)-enantiomer of an imide compound covered by the ’372 patent, is the active ingredient in Sunovion’s schizophrenia and bipolar depression drug LATUDA® .

The ’372 patent specification teaches several preferred embodiments in Examples 1(a) through 1(e). Example 1(a) describes the synthesis of Compound No. 101, which the specification portrays as follows:

(Image Omitted)

Id. at col. 30 ll. 40-65. Compound No. 101 is a chiral molecule because it contains a cyclohexyl linker— the region between the imide group on the left and the arylpiperazine group on the right— with two chiral centers.

The subsequent examples, 1(b) through 1(e), describe methods for separating Compound No. 101 into its constituent enantiomers in various salt forms. Examples 1(b) and 1(c) detail the process for obtaining the (+)-enantiomer (Compound No. 102) and (-)-enantiomer (Compound No. 103), respectively, in the tartrate salt form. See id. at col. 31 ll. 10-54. Examples 1(d) and 1(e) then convert Compound Nos. 102 and 103 from the tartrate salt form to the hydrochloride salt form. Example 1(d) produces the (+)-enantiomer (Compound No. 104), and Example 1(e) creates the (-)-enantiomer (Compound No. 105), which is lurasidone. See id. at col. 32 ll. 1-22.

After Emcure Pharmaceuticals Ltd., Heritage Pharma Labs Inc., InvaGen Pharmaceuticals, Inc., Teva Pharmaceuticals USA, Inc., and Teva Pharmaceutical Industries, Ltd. (collectively, " Appellants" ) filed Abbreviated New Drug Applications with the U.S. Food and Drug Administration seeking approval to market generic versions of LATUDA® , Sumitomo and Sunovion sued the Appellants for infringing claim 14 of the ’372 patent. Claim 14 recites: 14. The imide compound of the formula:

(Image Omitted)

or an acid addition salt thereof.

Just like depicted Compound No. 101, the claimed molecule is chiral because of the two carbons in the cyclohexyl linker. Both parties agree that the specific three-dimensional structure depicted in claim 14 is lurasidone, the (-)-enantiomer.

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The claim construction question for the district court centered on what combination of enantiomers claim 14 encompassed. Appellants sought to limit claim 14 to " a racemic mixture of two enantiomers of which the structural formula is representative." Sumitomo Dainippon Pharma Co. v. Emcure Pharm. Ltd., No. CV 15-280, 2016 WL 6803077, at *2 (D.N.J. Nov. 15, 2016). For support, Appellants relied on the claimed structure’s similarities to Compound No. 101, which Appellants contend is a racemic mixture, organic chemistry textbooks suggesting that ordinarily skilled artisans draw a single enantiomer as a shorthand representation for a racemic mixture, and the ’372 patent’s prosecution history.

The district court rejected Appellants’ narrow construction, which would have excluded the specific enantiomer depicted in claim 14. According to the court, even if Compound No. 101 is a racemic mixture, its resemblance to claim 14 did not justify importing that limitation from the specification into the claim. The court also concluded that the cited extrinsic evidence and prosecution history were at best irrelevant and at worst contradictory to Appellants’ construction. Therefore, the court adopted Sunovion’s proposal to construe claim 14 as covering " lurasidone, lurasidone’s enantiomer, as well as mixtures of these enantiomers." Id. at *8.

Following the district court’s claim construction order, Appellants stipulated to infringement of claim 14 and the entry of permanent injunctions....

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