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Merck Sharp & Dohme Corp. v. Amneal Pharmaceuticals LLC

United States District Court, D. Delaware

January 30, 2017


          Jack B. Blumenfeld, Esquire and Derek J. Fahnestock, Esquire of Morris, Nichols, Arsht & Tunnell LLP, Wilmington, Delaware. Counsel for Plaintiffs. Of Counsel: Nicolas Barzoukas, Esquire, Joshua Davis, Esquire, Kevin E. Cadwell, Esquire, and Lisa M. Thomas, Esquire of Reed Smith LLP.

          Anne Shea Gaza, Esquire, Robert M. Vrana, Esquire, and Samantha G. Wilson, Esquire of Young Conaway Stargatt & Taylor, LLP, Wilmington, Delaware. Counsel for Defendant. Of Counsel: Constance S. Huttner, Esquire, Michael H. Imbacuan, Esquire, Stephanie J. Kamerow, Esquire, Caroline Sun, Esquire of Budd Larner, P.C.


          ROBINSON District Judge


         This action arises out of the filing of Abbreviated New Drug Application ("ANDA") No. 207989 by defendant Amneal Pharmaceuticals LLC ("Amneal") seeking to produce and market a generic mometasone furoate nasal spray. (D.I. 56) On March 20, 2015, plaintiff Merck Sharp & Dohme Corp. ("Merck") brought this action alleging infringement of U.S. Patent No. 6,127,353 ("the '353 patent").[1] (D.I. 1) Merck filed an amended complaint on September 4, 2015,[2] which Amneal answered on September 18, 2015. (D.I. 56; D.I. 59) The court held a Markman hearing on July 31, 2015 and issued a claim construction order on September 3, 2015, construing certain disputed limitations. (D.I. 107[3]) The court held a final pretrial conference on June 7, 2016, and a two-day bench trial on June 21 and 22, 2016 on the infringement issue. The parties have since completed post-trial briefing. The 30-month stay of FDA final approval on Amneal's ANDA expires on August 4, 2017. (D.I. 142, ex. 1 at ¶46) The court has jurisdiction over this matter pursuant to 28 U.S.C. §§ 1331, 1338(a), and 1400(b). Having considered the documentary evidence and testimony, the court makes the following findings of fact and conclusions of law pursuant to Federal Rule of Civil Procedure 52(a).


         A. Technology at Issue

         1. Development of MFM

         Anhydrous mometasone furoate ("MFA") was first synthesized and patented by a Merck chemist, Dr. Elliot Shapiro, in the early 1980s. (D.I. 163 at 4) After MFA was discovered, its unique physical properties that prevented it from dissolving in water or known pharmaceutically acceptable compounds kept it on the "backbumer" for further research. (Id.) Years later, scientists found that MFA dissolved in a new pharmaceutical solvent and developed MFA for the treatment of psoriasis, a skin condition. (Id.)

         In the late 1980s, a formulator at Merck, Dr. Yuen, led a project seeking to develop mometasone furoate for nasal applications. As a result of this project, mometasone furoate monohydrate ("MFM") was developed. MFM has the chemical name, 9a,21 -dichloro-16a-methyl-1,4-pregnadiene-1113,17a-diol-3,20-dione-17-(2'-furoate) monohydrate and the following chemical structure:

         Image Omitted

         (D.I. 163 at 46; '353 patent)

         MFA and MFM are polymorphs. MFM differs from MFA in that every molecule of MFM is associated with a molecule of water, whereas no water is present in the crystal lattice structure of MFA. The difference between the molecular structures of MFM and MFA causes changes to the solid structure of the two crystalline forms. (D.I. 163 at 5; PTX18[4])

         2. Development of Nasonex

          Upon discovering MFM, Dr. Yuen determined that using MFM as a suspension in water with other excipients provided a stable formulation. (D.I. 163 at 6) The formation was further developed and ultimately was approved as Nasonex. The formulation is protected by the '353 patent. (Id.)

         Nasonex is indicated for the treatment of perennial allergenic rhinitis, seasonal allergic rhinitis, nasal polyps, and congestion associated with the nasal symptoms of allergic rhinitis (D.I. 142, ex. 1 at ¶ 26) The product insert for Nasonex states: "[Nasonex] Nasal Spray 50 meg is a corticosteroid demonstrating potent antiinflammatory properties." (Id. at ¶ 35) It further states: "The precise mechanism of corticosteroid action on allergic rhinitis is not known. Corticosteroids have been shown to have a wide range of effects on multiple cell types . . . and mediators . . . involved in inflammation." (Id.) Nasonex contains MFM as its active pharmaceutical ingredient ("API"). (Id. at ¶ 34)

         3. The '353 patent

          The '353 patent, titled "Mometasone furoate monohydrate, process for making same and pharmaceutical compositions," issued on October 3, 2000. (JTX 1) Merck alleges infringement of independent claims 1 and 6 and dependent claims 9-12. (D.I. 142, ex. 1 at ¶ 15) The patent claims MFM, a process for preparing MFM by crystallization from a saturated aqueous water miscible organic solution, and aqueous stable pharmaceutical compositions of MFM. ('353 patent, 1:31-48) Independent claim 1 recites "9a,21 -dichloro-16a-methyl-1,4-pregnadiene-11 (3,17a-diol-3,20-dione-17-(2'-furoate) monohydrate" and independent claim 6 recites "[a] pharmaceutical composition comprising mometasone furoate monohydrate in a carrier consisting essentially of water."

         4. The accused ANDA product

         Amneal's ANDA product is a generic mometasone furoate nasal spray, 50 meg, using MFA as the active pharmaceutical ingredient. Amneal's ANDA product has a proposed shelf-life of two years. Merck does not allege that the pre-formulation active pharmaceutical ingredient used in Amneal's ANDA product contains MFM or otherwise infringes the '353 patent. (D.I. 142, ex. 1 at ¶¶ 43-47; D.I. 163 at 3; PTX 23)

         B. Infringement Standard

         A patent is infringed when a person "without authority makes, uses or sells any patented invention, within the United States . . . during the term of the patent." 35 U.S.C. § 271(a). To prove direct infringement, the patentee must establish that one or more claims of the patent read on the accused device literally or under the doctrine of equivalents. See Advanced Cardiovascular Sys., Inc. v. Scimed Life Sys., Inc., 261 F.3d 1329, 1336 (Fed. Cir. 2001). A two-step analysis is employed in making an infringement determination. See Markman v. Westview Instruments, Inc., 52 F.3d 967, 976 (Fed. Cir. 1995), aff'd, 517 U.S. 370 (1996). First, the court must construe the asserted claims to ascertain their meaning and scope, a question of law. See Id. at 976-77; see also Teva Pharms. USA, Inc. v. Sandoz, Inc., __ U.S. __, 135 S. Ct. 831, 837 (2015). The trier of fact must then compare the properly construed claims with the accused infringing product. See Markman, 52 F.3d at 976. This second step is a question of fact. Spectrum Pharm., Inc. v. Sandoz Inc., 802 F.3d 1326, 1337 (Fed. Cir. 2015) (citing Bai v. L & L Wings, Inc., 160 F.3d 1350, 1353 (Fed. Cir. 1998)). "Direct infringement requires a party to perform each and every step or element of a claimed method or product." Exergen Corp. v. Wal-Mart Stores, Inc., 575 F.3d 1312, 1320 (Fed. Cir. 2009) (quoting BMC Res., Inc. v. Paymentech, LP., 498 F.3d 1373, 1378 (Fed. Cir. 2007)). "If any claim limitation is absent. . ., there is no literal infringement as a matter of law." Bayer AG v. Elan Pharm. Research Corp., 212 F.3d 1241, 1247 (Fed. Cir. 2000). If an accused product does not infringe an independent claim, it also does not infringe any claim depending thereon. Ferring B.V. v. Watson Labs., Inc.-Florida, 764 F.3d 1401, 1411 (Fed. Cir. 2014) (citing Wahpeton Canvas Co., Inc. v. Frontier, Inc., 870 F.2d 1546, 1552 (Fed. Cir. 1989) ("One who does not infringe an independent claim cannot infringe a claim dependent on (and thus containing all the limitations of) that claim.")). However, "[o]ne may infringe an independent claim and not infringe a claim dependent on that claim." Monsanto Co. v. Syngenta Seeds, Inc., 503 F.3d 1352, 1359 (Fed. Cir. 2007) (quoting Wahpeton Canvas, 870 F.2d at 1552) (internal quotations omitted). The patent owner has the burden of proving literal infringement by a preponderance of the evidence. Octane Fitness, LLC v. ICON Health & Fitness, Inc., __ U.S. __, 134 S. Ct. 1749, 1758 (2014).

         C. Analysis

          The question for infringement is whether Amneal's ANDA product (an aqueous suspension made with prior art MFA) contains any patented MFM during the product's two-year shelf life.[5]

         1. Samples

         Amneal produced samples of Batch Nos. BB-ST-13003A (manufactured October 28, 2013), 13005A (manufactured November 22, 2013), and 13006A (manufactured December 9, 2013) (collectively "the Exhibit Batches") and samples of Batch No. RD-3965-162 ("the R&D Batch") to Merck.[6] (JTX 8-10, 14-16) The samples were packaged in nasal spray bottles, Amneal's finished product form. (D.I. 176 at 55:17-23, 110:23-111:5) Amneal produced samples from Batch No. RD-3965-157 ("the Commercial Batch"), after which Amneal changed its manufacturing process. The court ruled that evidence of MFM in such samples could not be used to show infringement.[7] (D.I. 89, 98, 154) Amneal produced samples of another commercial-sized batch, Batch No. BB-ST-16001 ("Batch 16001") in glass bottles. (D.I. 130; D.I. 176 at 110:20-111:5; JTX 5, 13) The samples produced were drawn after manufacture on January 11, 2016 ("Batch 16001 Day 1"). Three days later, on January 14, 2016, the batch was mixed and a certain portion was removed and packaged in nasal spray bottles ("Batch 16001 A"). The next day, the batch was mixed, samples were drawn ("Batch 16001 Day 4"), and the remainder was packaged in nasal spray bottles ("Batch 16001A").[8] (JTX 11-12) Amneal stipulated that the Batch 16001 Day 1 samples produced to Merck are representative of its ANDA product. (D.I. 130)

         2. Merck's ...

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