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Endo Pharmaceuticals Inc. v. Actavis LLC

United States Court of Appeals, Federal Circuit

May 3, 2019


          Appeal from the United States District Court for the District of Delaware in No. 1:14-cv-01381-RGA, Judge Richard G. Andrews.

          Martin Jay Black, Dechert LLP, Philadelphia, PA, argued for plaintiffs-appellees. Also represented by Sharon K. Gagliardi; Blake Greene, Austin, TX; Jonathan Loeb, Mountain View, CA; Robert Rhoad, Princeton, NJ.

          Jeffrey J. Toney, Kasowitz, Benson, Torres & Friedman LLP, Atlanta, GA, for plaintiff-appellee Mallinckrodt LLC. Also represented by Rodney R. Miller, Paul Gunter Williams.

          John C. O'Quinn, Kirkland & Ellis LLP, Washington, DC, argued for defendants-appellants. Also represented by William H. Burgess; Charles A. Weiss, Eric H. Yecies, Holland & Knight, LLP, New York, NY.

          Before Wallach, Clevenger, and Stoll, Circuit Judges.


         Appellees Endo Pharmaceuticals Inc. ("Endo Pharmaceuticals") and Mallinckrodt LLC ("Mallinckrodt") (collectively, "Endo") sued Appellants Actavis LLC, Actavis South Atlantic LLC, and Teva Pharmaceuticals USA, Inc. (collectively, "Actavis") in the U.S. District Court for the District of Delaware ("District Court"), alleging that two Abbreviated New Drug Applications filed by Actavis infringed claims 1-6 ("the Asserted Claims") of Mallinckrodt's U.S. Patent No. 8, 871, 779 ("the '779 patent"), which Endo Pharmaceuticals licenses. The District Court held that Actavis failed to "prove[] by clear and convincing evidence that any of the [A]sserted [C]laims . . . were invalid" as obvious or anticipated, Endo Pharm. Inc. v. Actavis Inc., No. 14-1381-RGA, 2017 WL 3731001, at *1 (D. Del. Aug. 30, 2017), and entered final judgment of infringement, based on a stipulation by Actavis, J.A. 1.

         Actavis appeals, challenging the invalidity determination. We have jurisdiction pursuant to 28 U.S.C. § 1295(a)(1) (2012). We affirm.


         I. The '779 Patent

         Entitled "Process for Preparing Morphinan-6-One Products with Low Levels of α, β-Unsaturated Ketone Compounds," the '779 patent generally relates to compounds known as "morphinan alkaloids," such as "oxymorphone," which have "great medical importance" and "are used extensively for pain relief." '779 patent col. 1 ll. 24-30. "Morphinan compounds and analogs thereof typically have a ring structure . . . corresponding to Formula (1)”:

         (Image Omitted)

         Id. col. 1 ll.38-53. "[P]harmaceutically desirable morphinan compounds" often "have a ketone group[1] on the C-ring of Formula (1) and a saturated bond[, i.e., single bond, ] between the two carbon atoms positioned a and p to the ketone on the C-ring." Id. col. 2 ll. 21-24. "[T]hese compounds may be referred to as morphinan-6-one compounds." Id. col. 2 ll. 28-29. "[T]he ketone is present on the C(6) carbon atom, with the α and β carbon atoms being the C(7) and C(8) positions . . . ." Id. col. 2 ll. 25-26.

         In describing the prior art, the '779 patent explains that "[v]arious processes for producing morphinan-6-one compounds are known," and "many . . . involve some form of catalytic hydrogenation[2] of α, β-unsaturated ketone intermediate compounds [('ABUKs')]," i.e., applying catalytic hydrogenation to compounds containing ketone groups with double bonds between the α and β carbon atoms to convert the double bonds to single bonds. Id. col. 2 ll. 29- 32. However, "[ABUKs] may persist as impurities in the final products." Id. col. 2 ll. 43-45. These hydrogenation processes also "may tend to undesirably reduce the ketone[, a key functional part of morphinan-6-one compounds, ] as well as reducing or removing the α, β-unsaturation." Id. col. 2 ll. 47-48.

         The '779 patent discloses "processes for preparing highly pure morphinan-6-one products" having a relatively low concentration of ABUKs present as impurities, which "involve treating a reaction mixture including a morphinan-6-one compound and an [ABUK] with a sulfur-containing compound." Id. col. 5 ll. 6-10. These processes can "effectively reduce[] the concentration of undesirable [ABUKs] to acceptable levels," id. col. 5 ll. 11-13, with the process employing a sulfur-containing compound that can reduce ABUK concentration "from levels of about 0.5% (by weight) or more to levels of not more than about 0.1% . . ., or lower (e.g., about 0.01% . . ., about 0.001% . . ., or lower), with minimal side reactions, ketone reduction, and/or any other undesirable effects," id. col. 5 ll. 17-22.

         The Asserted Claims recite:

1.A hydrochloride salt of oxymorphone comprising less than 0.001% of 14-hydroxymorphinone.[3]
2.The hydrochloride salt of claim 1 comprising less than 0.0005% of 14-hydroxymorphinone.
3. A pharmaceutical acceptable form comprising the oxymorphone hydrochloride according to claim 1.
4.A hydrochloride salt of a morphinan-6-one compound corresponding to Formula (2):
(Image Omitting)
comprising less than 0.001% measured by [high performance liquid chromatography] of an [ABUK] corresponding to Formula (3):
(Image Omitting)
wherein the morphinan-6-one compound is oxymorphone and wherein X is -N(R17)-;
R1 and R2 are hydrogen;
R3 is hydroxy;
R10 is ...

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