Endo Pharmaceuticals Inc. v. Amneal Pharmaceuticals, LLC

224 F. Supp. 3d 368, 2016 WL 5869946
CourtDistrict Court, D. Delaware
DecidedOctober 7, 2016
DocketCivil Action No. 14-1382-RGA, Civil Action No. 14-1389-RGA
StatusPublished

This text of 224 F. Supp. 3d 368 (Endo Pharmaceuticals Inc. v. Amneal Pharmaceuticals, LLC) is published on Counsel Stack Legal Research, covering District Court, D. Delaware primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Endo Pharmaceuticals Inc. v. Amneal Pharmaceuticals, LLC, 224 F. Supp. 3d 368, 2016 WL 5869946 (D. Del. 2016).

Opinion

TRIAL OPINION

ANDREWS, UNITED STATES DISTRICT JUDGE:

Plaintiffs brought these patent infringement actions against Amneal Pharmaceuticals, LLC, Amneal Pharmaceuticals of New York, LLC (collectively, “Amneal”), Teva Pharmaceuticals USA, Inc., and Barr Laboratories, Inc. (collectively, “Teva”) in 2014. (D.I. 1).1 On April 3, 2012, Amneal filed an Abbreviated New Drug Application (“ANDA”), seeking to engage in the commercial manufacture, use, and sale of generic versions of Endo’s Opana ER CRF product.2 (D.I. 130, Ex. ¶ 14). Teva filed an ANDA on April 17, 2012, with amendments on May 4, 2012 and September 20, 2012, seeking to do the same. (Id. ¶ 16). Plaintiffs allege that these ANDAs infringe U.S. Patent No. 8,871,779 (“the ’779 patent”).

These cases concern two molecules. The first is 14-hydroxydihydromorphinone, also referred to as “oxymorphone” or “oxy-morphone HC1.”3 The other is 14-hydrox-ymorphinone, also referred to as “oxymor-phone ABUK.” ABUK stands for alpha, beta-unsaturated ketone, an organic compound having a double bond between the ketone’s alpha and beta carbons.

Oxymorphone HC1 was first patented in 1955 and first approved by the FDA in 1959. (Trial Transcript (“Tr.”) at 86:1-5, 11-14). Prior to 2002, manufacturers of oxymorphone HC1 were aware of the presence of the impurity now known as oxy-morphone ABUK. (Tr. at 229:9-230:4; see also JTX-23). During the period before 2002, manufacturers regularly sold oxymorphone HC1 with oxymorphone ABUK levels in the range of hundreds of parts per million (“ppm”). (Tr. at 229:9-230:4). In 2002, the FDA informed Mallinckrodt and several other manufacturers that it was concerned about the levels of ABUK in certain products. (Tr. 217:9-218:22). The FDA informed Mallinckrodt that it intended to impose limits on the levels of ABUK, and that it might require limits as low as 0.001 percent (or 10 ppm) ABUK. (Tr. 110:19-111:21, 218:7-18). In 2004, the FDA mandated that opioid manufacturers lower the levels of ABUK in opioid pharmaceuticals to less than 10 ppm. (Tr. 199:10-201:20, 218:7-18). In these cases, oxymor-phone HC1 which contains less than 10 ppm of oxymorphone ABUK—and thus complies with FDA’s mandate—is called “low-ABUK oxymorphone.”

In 2005, Mallinckrodt succeeded in reaching the low ABUK levels mandated by the FDA for oxymorphone HC1. Mallinckrodt applied for a patent on its new low-ABUK oxymorphone product. The application ultimately issued as the ’779 patent. The asserted claims of the ’779 patent 4 are all composition claims directed to low-ABUK oxymorphone. (Tr. 88:22-89:8, 111:13-21; DTX-17 at 37:58-38:61).

[373]*373Independent claim 1 of the ’779 patent reads:

A hydrochloride salt of oxymorphone comprising less than 0.001% of 14-hy-droxymorphinone.

(DTX-17 at 37:58-59). Dependent claim 2 limits the level of 14-hydroxymorphinone to less than 0.0005%. (Id. at 37:60-61). Dependent claim 3 claims a pharmaceutically acceptable form of the hydrochloride salt in claim 1. (Id. at 37:62-63). Independent claim 4 reads:

A hydrochloride salt of a morphinan-6-one compound corresponding to Formula (2):
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comprising less than 0.001% measured by HPLC of an a,(3-unsaturated ketone compound corresponding to Formula (3):
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[374]*374wherein the morphinan-6-one compound is oxymorphone and wherein X is— N(RW)—;
R 1 and R 2 are hydrogen;
R 3 is hydroxy;
R 10 is hydrogen;
R 14 is hydroxy; and
R 17 is methyl.

(Id. at 38:16-57). Dependent claim 5 limits the level of 14-hydroxymorphinone to 0.0005%. (Id. at 38:58-59). Dependent claim 6 claims a pharmaceutical formulation of the oxymorphone chloride in claim 4. (Id. at 38:60-61).

The Court held a bench trial on July 11-13, 2016. Both Amneal and Teva concede that their proposed products meet all the limitations of the ’779 patent. (D.I. 150, Ex. 1 ¶¶ 18-20). Teva contends, however, that because it obtained an implied license from Mallinckrodt, it does not infringe. Both defendants argue that the ’779 patent is invalid as obvious.

I. OBVIOUSNESS

A. Legal Standard

A patent claim is invalid as obvious under 35 U.S.C. § 103 “if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains.” 35 U.S.C. § 103; see also KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 406-07, 127 S.Ct. 1727, 167 L.Ed.2d 705 (2007). The determination of obviousness is a question of law with underlying factual findings. See Kinetic Concepts, Inc. v. Smith & Nephew, Inc., 688 F.3d 1342, 1359-60 (Fed. Cir. 2012). “The underlying factual inquiries include (1) the scope and content of the prior art; (2) the differences between the prior art and the claims at issue; (3) the level of ordinary skill in the art; and (4) any relevant secondary considerations .... ” Western Union Co. v. MoneyGram Payment Sys., Inc., 626 F.3d 1361, 1370 (Fed. Cir. 2010) (citing Graham v. John Deere Co., 383 U.S. 1, 17-18, 86 S.Ct. 684, 15 L.Ed.2d 545 (1966)).

A court is required to consider secondary considerations, or objective indi-cia of nonobviousness, before reaching an obviousness determination, as a “check against hindsight bias.” See In re Cyclobenzaprine Hydrochloride Extended-Release Capsule Patent Litig., 676 F.3d 1063, 1078-79 (Fed. Cir. 2012). Relevant secondary considerations include commercial success, long felt but unsolved needs, failure of others, praise, unexpected results, and copying, among others. Graham, 383 U.S. at 17-18, 86 S.Ct. 684; Ruiz v. A.B. Chance Co., 234 F.3d 654, 662-63 (Fed. Cir. 2000); Tex. Instruments, Inc. v. U.S. Int’l Trade Comm’n, 988 F.2d 1165, 1178 (Fed. Cir. 1993).

A party asserting that a patent is invalid as obvious must “show by clear and convincing evidence that a skilled artisan would have been motivated to combine the teachings of the prior art references to achieve the claimed invention, and that the skilled artisan would have had a reasonable expectation of success in doing so.” Pfizer, Inc. v. Apotex, Inc., 480 F.3d 1348, 1361 (Fed. Cir. 2007). That “expectation of success need only be reasonable, not absolute.” Id. at 1364. “Whether an ordinarily skilled artisan would have reasonably expected success .... is measured as of the date of the invention[ ] .... ” Amgen Inc. v. F.

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Bluebook (online)
224 F. Supp. 3d 368, 2016 WL 5869946, Counsel Stack Legal Research, https://law.counselstack.com/opinion/endo-pharmaceuticals-inc-v-amneal-pharmaceuticals-llc-ded-2016.