Case 1:14-cv-03962-JBS-KMW Document 1 Filed 06/20/14 Page 1 of 12 PageID: 1
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`IN THE UNITED STATES DISTRICT COURT
`FOR THE DISTRICT OF NEW JERSEY
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`Civil Action No.:
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`SENJU PHARMACEUTICAL CO., LTD.,
`BAUSCH & LOMB, INC. and BAUSCH &
`LOMB PHARMA HOLDINGS CORP.
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`Plaintiffs,
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`v.
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`METRICS, INC., COASTAL
`PHARMACEUTICALS, INC., MAYNE
`PHARMA GROUP LIMITED, and MAYNE
`PHARMA (USA), INC.,
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`Defendants.
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`COMPLAINT FOR PATENT INFRINGEMENT
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`Plaintiffs Senju Pharmaceutical Co., Ltd., Bausch & Lomb Incorporated and Bausch &
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`Lomb Pharma Holdings Corp. (collectively, “Plaintiffs”) by way of Complaint against
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`Defendants Metrics, Inc. (“Metrics”), Coastal Pharmaceuticals, Inc. (“Coastal”), Mayne Pharma
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`Group Limited (“Mayne Pharma”), and Mayne Pharma (USA), Inc. (“Mayne Pharma USA”)
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`(collectively, “Defendants”) allege as follows:
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`THE PARTIES
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`1.
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`Plaintiff Senju Pharmaceutical Co., Ltd. (“Senju”) is a corporation organized and
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`existing under the laws of Japan, with a principal place of business at 2-5-8, Hirano-machi,
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`Chuo-ku, Osaka 541-0046, Japan.
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`2.
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`Plaintiff Bausch & Lomb Incorporated (“B+L”) is a corporation organized and
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`existing under the laws of New York, with a place of business at 1400 North Goodman St.,
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`Rochester, New York 14609. B+L is the registered holder of approved New Drug Application
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`No. 203168, which covers Prolensa®.
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`Page 1 of 46
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`SENJU EXHIBIT 2017
`METRICS v. SENJU
`IPR2014-01043
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`3.
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`Plaintiff Bausch & Lomb Pharma Holdings Corp. (“B+L Pharma Holdings”) is a
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`corporation organized and existing under the laws of Delaware, with a principal place of
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`business at 700 Route 202/206, Bridgewater, New Jersey 08807. B+L Pharma Holdings is a
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`wholly-owned subsidiary of B+L.
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`4.
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`Upon information and belief, defendant Metrics is a corporation organized and
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`existing under the laws of North Carolina, having a place of business at 1240 Sugg Parkway,
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`Greenville, NC 27834. Upon information and belief, defendant Metrics, Inc. is a wholly-owned
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`subsidiary of defendant Mayne Pharma.
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`5.
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`Upon information and belief, defendant Coastal is a corporation organized and
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`existing under the laws of North Carolina, having a place of business at 1240 Sugg Parkway,
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`Greenville, NC 27834. Upon information and belief, defendant Coastal is a wholly-owned
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`subsidiary of defendant Mayne Pharma.
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`6.
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`Upon information and belief, defendant Mayne Pharma is a corporation organized
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`and existing under the laws of Australia, having a place of business at Level 14, 474 Flinders
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`Street, Melbourne VIC 3000, Australia.
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`7.
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`Upon information and belief, defendant Mayne Pharma USA is a corporation
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`organized and existing under the laws of New Jersey, having a place of business at 650 From
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`Road, 2nd Floor, Mack Cali Centre, Paramus, NJ 07652. Upon information and belief, defendant
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`Mayne Pharma USA is a wholly-owned subsidiary of defendant Mayne Pharma.
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`NATURE OF THE ACTION
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`8.
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`This is an action for infringement of United States Patent Nos. 8,129,431 (“the
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`’431 patent”), 8,669,290 (“the ’290 patent”), and 8,754,131 patent (“the ’131 patent”) arising
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`under the United States patent laws, Title 35, United States Code, § 100 et seq., including 35
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`U.S.C. §§ 271 and 281, and for declaratory judgment of infringement of the ’431 patent, the ’290
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`patent, and the ’131 patent under 28 U.S.C. §§ 2201 and 2202. This action relates to Metrics’
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`filing of an Abbreviated New Drug Application (“ANDA”) under Section 505(j) of the Federal
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`Food, Drug, and Cosmetic Act (“the Act”), 21 U.S.C. § 355(j), seeking U.S. Food and Drug
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`Administration (“FDA”) approval to market generic Bromfenac Ophthalmic Solution 0.07%
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`(“Metrics’ generic bromfenac ophthalmic solution”).
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`JURISDICTION AND VENUE
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`9.
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`This Court has subject matter jurisdiction under 28 U.S.C. §§ 1331 and 1338(a).
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`10.
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`Upon information and belief, this Court has jurisdiction over Metrics. Upon
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`information and belief, Metrics is in the business of manufacturing, marketing, importing and
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`selling pharmaceutical drug products, including generic drug products. Upon information and
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`belief, Metrics directly manufactures, markets and sells generic drug products throughout the
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`United States and in this judicial district, and this judicial district is a likely destination for
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`Metrics’ generic bromfenac ophthalmic solution. Upon information and belief, Metrics
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`purposefully has conducted and continues to conduct business in this judicial district.
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`11.
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`Upon information and belief, this court has jurisdiction over Coastal. Upon
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`information and belief, Coastal directly, or indirectly, manufactures, markets and sells generic
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`drug products, including generic drug products manufactured by Metrics, throughout the United
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`States and in this judicial district. Upon information and belief, Coastal purposefully has
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`conducted and continues to conduct business in this judicial district.
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`12.
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`Upon information and belief, this court has jurisdiction over Mayne Pharma.
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`Upon information and belief, Mayne Pharma directly, or indirectly, manufactures, markets and
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`sells generic drug products, including generic drug products manufactured by Metrics,
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`throughout the United States and in this judicial district. Upon information and belief, Mayne
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`Pharma purposefully has conducted and continues to conduct business in this judicial district.
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`13.
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`Upon information and belief, this court has jurisdiction over Mayne Pharma USA.
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`Upon information and belief, Mayne Pharma USA directly, or indirectly, manufactures, markets
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`and sells generic drug products, including generic drug products manufactured by Metrics,
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`throughout the United States and in this judicial district. Upon information and belief, Mayne
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`Pharma USA purposefully has conducted and continues to conduct business in this judicial
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`district.
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`14.
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`Upon information and belief, venue is proper in this judicial district under 28
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`U.S.C. §§ 1391(c) and (d), and § 1400(b).
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`THE PATENTS IN SUIT
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`15.
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`The U.S. Patent and Trademark Office (“PTO”) issued the ’431 patent on March
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`6, 2012. The ’431 patent claims, inter alia, formulations of bromfenac for ophthalmic
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`administration. Plaintiffs holds all substantial rights in the ’431 patent and have the right to sue
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`for infringement thereof. Senju is the assignee of the ’431 patent. A copy of the ’431 patent is
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`attached hereto as Exhibit A.
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`16.
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`The U.S. Patent and Trademark Office (“PTO”) issued the ’290 patent on March
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`1, 2014. The ’290 patent claims, inter alia, formulations of bromfenac for ophthalmic
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`administration. Plaintiffs holds all substantial rights in the ’290 patent and have the right to sue
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`for infringement thereof. Senju is the assignee of the ’290 patent. A copy of the ’290 patent is
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`attached hereto as Exhibit B.
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`17.
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`The U.S. Patent and Trademark Office (“PTO”) issued the ’131 patent on June 17,
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`2014. The ’131 patent claims, inter alia, formulations of bromfenac for ophthalmic
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`administration. Plaintiffs holds all substantial rights in the ’131 patent and have the right to sue
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`for infringement thereof. Senju is the assignee of the ’131 patent. A copy of the ’131 patent is
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`attached hereto as Exhibit C.
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`18.
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`B+L is the holder of New Drug Application (“NDA”) No. 203168 for Prolensa®,
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`which the FDA approved on April 5, 2013. In conjunction with NDA No. 203168, the ’431 and
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`’290 patents are listed in the FDA’s Approved Drug Products with Therapeutic Equivalence
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`Evaluations (“the Orange Book”).
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`19.
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`Bromfenac Ophthalmic Solution 0.07% is sold in the United States under the
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`trademark Prolensa®.
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`METRICS’ INFRINGING ANDA SUBMISSION
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`20.
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`Upon information and belief, Metrics filed with the FDA an ANDA for a generic
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`version of Prolensa® under Section 505(j) of the Act and 21 U.S.C. § 355(j) containing a
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`Paragraph IV certification to the ’431 patent.
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`21.
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`Upon information and belief, Metrics’ ANDA seeks FDA approval to sell in the
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`United States Metrics’ generic bromfenac ophthalmic solution, intended to be a generic version
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`of Prolensa®.
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`22.
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`Upon information and belief, Metrics’ actions relating to the ANDA complained
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`of herein were done with the cooperation, the participation, the assistance of, and at least in part
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`for the benefit of Coastal, Mayne Pharma, and Mayne Pharma USA.
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`COUNT I
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`Infringement of the ’431 Patent Under 35 U.S.C. § 271(e)(2)
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`Paragraphs 1-22 are incorporated herein as set forth above.
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`Under 35 U.S.C. § 271(e)(2), Metrics has infringed at least one claim of the ’431
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`23.
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`24.
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`patent by submitting, or causing to be submitted to the FDA, an ANDA seeking approval for the
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`commercial marketing of Metrics’ generic bromfenac ophthalmic solution before the expiration
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`date of the ’431 patent.
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`25.
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`Upon information and belief, Metrics’ generic bromfenac ophthalmic solution
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`will, if approved and marketed, infringe at least one claim of the ’431 patent.
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`26.
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`Upon information and belief, Metrics will, through the manufacture, use import,
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`offer for sale and/or sale of Metrics’ generic bromfenac ophthalmic solution, directly infringe,
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`contributorily infringe and/or induce infringement of at least one claim of the ’431 patent.
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`COUNT II
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`Declaratory Judgment of Infringement of the ’431 Patent
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`Paragraphs 1-26 are incorporated herein as set forth above.
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`These claims arise under the Declaratory Judgment Act, 28 U.S.C. §§ 2201 and
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`27.
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`28.
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`2201.
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`29.
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` There is an actual case or controversy such that the Court may entertain
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`Plaintiffs’ request for declaratory relief consistent with Article III of the United States
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`Constitution, and this actual case or controversy requires a declaration of rights by this Court.
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`30. Metrics has made, and will continue to make, substantial preparation in the United
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`States to manufacture, use, offer to sell, sell and/or import Metrics’ generic bromfenac
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`ophthalmic solution before the expiration date of the ’431 patent, including Metrics’ filing of an
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`ANDA.
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`31.
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`Upon information and belief, any commercial manufacture, use, offer for sale,
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`sale, and/or importation of Metrics’ generic bromfenac ophthalmic solution will directly infringe,
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`contributorily infringe and/or induce infringement of at least one claim of the ’431 patent.
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`32.
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`Plaintiffs are entitled to a declaratory judgment that future commercial
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`manufacture, use, offer for sale, sale, and/or importation of Metrics’ generic bromfenac
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`ophthalmic solution will constitute infringement of at least one claim of the ’431 patent.
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`COUNT III
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`Infringement of the ’290 Patent Under 35 U.S.C. § 271(e)(2)
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`Paragraphs 1-32 are incorporated herein as set forth above.
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`Under 35 U.S.C. § 271(e)(2), Metrics has infringed at least one claim of the ’290
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`33.
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`34.
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`patent by submitting, or causing to be submitted to the FDA, an ANDA seeking approval for the
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`commercial marketing of Metrics’ generic bromfenac ophthalmic solution before the expiration
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`date of the ’290 patent.
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`35.
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`Upon information and belief, Metrics’ generic bromfenac ophthalmic solution
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`will, if approved and marketed, infringe at least one claim of the ’290 patent.
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`36.
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`Upon information and belief, Metrics will, through the manufacture, use import,
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`offer for sale and/or sale of Metrics’ generic bromfenac ophthalmic solution, directly infringe,
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`contributorily infringe and/or induce infringement of at least one claim of the ’290 patent.
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`COUNT IV
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`Declaratory Judgment of Infringement of the ’290 Patent
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`Paragraphs 1-36 are incorporated herein as set forth above.
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`These claims arise under the Declaratory Judgment Act, 28 U.S.C. §§ 2201 and
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`37.
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`38.
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`2201.
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`39.
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` There is an actual case or controversy such that the Court may entertain
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`Plaintiffs’ request for declaratory relief consistent with Article III of the United States
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`Constitution, and this actual case or controversy requires a declaration of rights by this Court.
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`40. Metrics has made, and will continue to make, substantial preparation in the United
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`States to manufacture, use, offer to sell, sell and/or import Metrics’ generic bromfenac
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`ophthalmic solution before the expiration date of the ’290 patent, including Metrics’ filing of an
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`ANDA.
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`41.
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`Upon information and belief, any commercial manufacture, use, offer for sale,
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`sale, and/or importation of Metrics’ generic bromfenac ophthalmic solution will directly infringe,
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`contributorily infringe and/or induce infringement of at least one claim of the ’290 patent.
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`42.
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`Plaintiffs are entitled to a declaratory judgment that future commercial
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`manufacture, use, offer for sale, sale, and/or importation of Metrics’ generic bromfenac
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`ophthalmic solution will constitute infringement of at least one claim of the ’290 patent.
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`COUNT V
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`Infringement of the ’131 Patent Under 35 U.S.C. § 271(e)(2)
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`Paragraphs 1-42 are incorporated herein as set forth above.
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`Under 35 U.S.C. § 271(e)(2), Metrics has infringed at least one claim of the ’131
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`43.
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`44.
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`patent by submitting, or causing to be submitted to the FDA, an ANDA seeking approval for the
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`commercial marketing of Metrics’ generic bromfenac ophthalmic solution before the expiration
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`date of the ’131 patent.
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`45.
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`Upon information and belief, Metrics’ generic bromfenac ophthalmic solution
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`will, if approved and marketed, infringe at least one claim of the ’131 patent.
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`46.
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`Upon information and belief, Metrics will, through the manufacture, use import,
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`offer for sale and/or sale of Metrics’ generic bromfenac ophthalmic solution, directly infringe,
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`contributorily infringe and/or induce infringement of at least one claim of the ’131 patent.
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`COUNT VI
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`Declaratory Judgment of Infringement of the ’131 Patent
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`Paragraphs 1-46 are incorporated herein as set forth above.
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`These claims arise under the Declaratory Judgment Act, 28 U.S.C. §§ 2201 and
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`47.
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`48.
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`2201.
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`49.
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` There is an actual case or controversy such that the Court may entertain
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`Plaintiffs’ request for declaratory relief consistent with Article III of the United States
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`Constitution, and this actual case or controversy requires a declaration of rights by this Court.
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`50. Metrics has made, and will continue to make, substantial preparation in the United
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`States to manufacture, use, offer to sell, sell and/or import Metrics’ generic bromfenac
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`ophthalmic solution before the expiration date of the ’131 patent, including Metrics’ filing of an
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`ANDA.
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`51.
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`Upon information and belief, any commercial manufacture, use, offer for sale,
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`sale, and/or importation of Metrics’ generic bromfenac ophthalmic solution will directly infringe,
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`contributorily infringe and/or induce infringement of at least one claim of the ’131 patent.
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`52.
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`Plaintiffs are entitled to a declaratory judgment that future commercial
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`manufacture, use, offer for sale, sale, and/or importation of Metrics’ generic bromfenac
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`ophthalmic solution will constitute infringement of at least one claim of the ’131 patent.
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`PRAYER FOR RELIEF
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`WHEREFORE, Plaintiffs respectfully request that the Court enter judgment in their
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`favor and against Defendants on the patent infringement claim set forth above and respectfully
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`request that this Court:
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`1.
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`enter judgment that, under 35 U.S.C. § 271(e)(2), Defendants have infringed at
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`least one claim of the ’431 patent through Metrics’ submission of an ANDA to the FDA to
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`obtain approval for the commercial manufacture, use, import, offer for sale and/or sale in the
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`United States of Metrics’ generic bromfenac ophthalmic solution before the expiration of the
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`’431 patent;
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`2.
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`enter judgment that, under 35 U.S.C. § 271(e)(2), Defendants have infringed at
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`least one claim of the ’290 patent through Metrics’ submission of an ANDA to the FDA to
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`obtain approval for the commercial manufacture, use, import, offer for sale and/or sale in the
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`United States of Metrics’ generic bromfenac ophthalmic solution before the expiration of the
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`’290 patent;
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`3.
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`enter judgment that, under 35 U.S.C. § 271(e)(2), Defendants have infringed at
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`least one claim of the ’131 patent through Metrics’ submission of an ANDA to the FDA to
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`obtain approval for the commercial manufacture, use, import, offer for sale and/or sale in the
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`United States of Metrics’ generic bromfenac ophthalmic solution before the expiration of the
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`’131 patent;
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`4.
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`declare under 28 U.S.C. § 2201 that if Metrics or any person acting or attempting
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`to act in concert with Metrics engages in the manufacture, use, offer for sale, sale and/or
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`importation of Metrics’ generic bromfenac ophthalmic solution, it will infringe at least one claim
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`of the ’431 patent.
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`5.
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`declare under 28 U.S.C. § 2201 that if Metrics or any person acting or attempting
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`to act in concert with Metrics engages in the manufacture, use, offer for sale, sale and/or
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`importation of Metrics’ generic bromfenac ophthalmic solution, it will infringe at least one claim
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`of the ’290 patent.
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`6.
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`declare under 28 U.S.C. § 2201 that if Metrics or any person acting or attempting
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`to act in concert with Metrics engages in the manufacture, use, offer for sale, sale and/or
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`importation of Metrics’ generic bromfenac ophthalmic solution, it will infringe at least one claim
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`of the ’131 patent.
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`7.
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`order that the effective date of any approval by the FDA of Metrics’ generic
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`bromfenac ophthalmic solution be a date that is not earlier than the expiration of the ’431 patent,
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`’290 patent, and ’131 patent or such later date as the Court may determine;
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`8.
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`enjoin Defendants from the commercial manufacture, use, import, offer for sale
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`and/or sale of Metrics’ generic bromfenac ophthalmic solution until expiration of the ’431 patent,
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`’290 patent, and ’131 patent or such later date as the Court may determine;
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`9.
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`enjoin Metrics and all persons acting in concert with Metrics from seeking,
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`obtaining or maintaining approval of Metrics’ ANDA until expiration of the ’431 patent, ’290
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`patent, and ’131 patent;
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`10.
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`declare this to be an exceptional case under 35 U.S.C. §§ 285 and 271(e)(4) and
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`award Plaintiffs costs, expenses and disbursements in this action, including reasonable attorneys
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`fees;
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`11.
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`award Plaintiff such further and additional relief as this Court deems just and
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`proper.
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`Dated: June 20, 2014
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`-11-
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` Respectfully submitted,
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`s/ John F. Brenner
`John F. Brenner
`PEPPER HAMILTON, LLP
`Suite 400
`301 Carnegie Center
`Princeton, New Jersey, 08543-5276
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`(609) 951-4193
`brennerj@pepperlaw.com
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`Attorneys for Plaintiffs
`SENJU PHARMACEUTICAL CO., LTD.,
`BAUSCH & LOMB, INC. and BAUSCH & LOMB
`PHARMA HOLDINGS CORP.
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`Of Counsel:
`Bryan C. Diner
`Justin J. Hasford
`FINNEGAN, HENDERSON,
`FARABOW, GARRETT & DUNNER, LLP
`901 New York Avenue, NW
`Washington, DC 20001-4413
`(202) 408-4000
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`EXHIBIT C
`
`Page 33 of 46
`
`

`

`Case 1:14-cv-03962-JBS-KMW Document 1-3 Filed 06/20/14 Page 2 of 11 PageID: 34
`1111111111111111111 llllllllllllllllllllllllllllllllllllllll~ 11111111
`
`US008754!31B2
`
`i! 2i United States Patent
`Sawa et al.
`
`(!OJ I'alent No.:
`1·151 Date of I'alent:
`
`US 8,754,131 H2
`*.Jun. 17,2014
`
`i:'\4)
`
`-\QOEOl!S IJ<)tJII) PREPARATJO"
`('()'•ffAl:"o'IN<;
`l-A"ll :X0-3-1 4-l!RO:\ciOilE'\iZOYL )I'll E'WI.A( 'ETI <'
`ACill
`
`·)5'J7,SfA)
`
`\
`\
`\
`\
`A
`~.9'JXA6S
`h,l62,3<J3 A
`6)74,S92 Bl
`(),274,609 Ill
`tdl9.SJJ Ill
`0,369,1!2 Ill
`6,_;X.'I,..J7 I Bl
`6,l9i.746 Ill
`20U!-OO"i6U')l\ \I
`2007 (J{))(!X"7 A!
`
`I !')')7
`fkrgamini d a!
`?. l 'N7
`Dcs;ti d I!]
`:·< 1997 D.:s!H d a!
`K! 'N') Saw;1
`l Jd!berg Cl al
`L'-1949
`IJ<C Brwju d al
`12'.!000
`K/001 S;1W!l
`l\:?OUl Yac:w.::d;t et :ll
`1!:2()01 J)obr(i/si
`4-2002 Xia
`\2002 ( -h;;n d
`;)]
`S: 2002
`( 'ap.k et al
`]]_, ?001 Sawn
`4::?007 Sawa
`
`( 7! J
`
`/\pplicant: Senju Pharmaceuth:aJ ( 'o., l_td .. ()sakt
`{JP)
`
`('72J
`
`lnvcnhm; Shinm Sawa, \lyogp (JP): Shuhei
`Fujita, I IycJgn ( J!>)
`
`(71,)
`
`f\ssrgn.__>e Senju Pharmal·euticaJ ( 'o .. I ,hk ()saka
`(JPJ
`
`( +) N<lti .. ·e-
`
`Subject !(J <lilY disd<lim~·r. the term of!hh
`patent is exknded ur :tdjuslell 11nder 1:"
`llS(' JS4(b)hy0day;;
`
`J'his p:llent is: subject [(l a knninal dis~
`claimer
`
`(21 i
`
`·\ppl. No 14/165,976
`
`(22)
`
`riled:
`
`Jan. 28,2014
`
`(hS)
`
`Prior Puhlication Data
`
`US 20l4!0142JK1,/\l
`
`May 22. 2014
`
`FORFI()N PA\"FN'J' !)OC!JMENJ'S
`
`707 !!9
`) OJ \ l)<k
`() '\()(, 9:\4
`62-!261}4
`I- 10402.1
`020ST123
`2-!24S!9
`"·22J0"2
`'j-S(),l7') 1
`! I ~22X404
`:wo2~3ox764
`96'14S29
`oo .. S'J475
`OJ- !S677
`02 UX04
`
`9 I'N"
`9 J<)')(J
`j,J')l{')
`6 19k7
`4 J9N0
`;, !990
`5 19<)0
`
`' [<)IF)
`
`4- !')'}7
`K 199~J
`J(J-2:002
`),J 996
`JO 2000
`_L!OOI
`2 200::
`
`-\l'
`
`CA rP
`
`II'
`II'
`JP
`JP
`II'
`Jl'
`JP
`JP
`wo
`wo
`wo
`wo
`
`l~dakd lJ.S. Application nata
`
`( (12)
`
`!)ivision uf <lpplic~ll ion Nt\. I .116X7 242. llled on Nov
`2K 2012. nuw l':lL Nn. S.MJ9.200. which is a division
`l!( app!icu!ion Nn_ 11;(~51.651, J\kd on J~ul. ]9, 2012,
`nuw P<ll. N\l_ i(4'J7 ,104, which is a divisam nl
`application No. J0/525,006. lik'-d as app!icatinn No.
`P('T!JP2004/0f}(X'50 on Jan. J(J, 2004, !l<lW !)at. N,,
`X.I29A1l.
`
`(30)
`
`Foreign Application Prioriiy l>ata
`
`OIIIJ!R l'l!ill.ll 'AllONS
`
`'\nv Dlllgs ill .bpan. 2001, 200 I Fditi,)n. Published by Yakuii '\ipiXl
`JJd, \-1ay 11,2001, pp .. ?7-29. and 1ts Lng!ish lr;mslat1on of the
`makria! por1i<lllS
`!ST\ l'h!Uma.:cuti<.:ak '"'iev..· Dn1g, Appli~·;tlions- Xibrom". http
`vvv.w_,iJugsxom:nth·xibmm 040525.htmt, ;}<.:cesscd online Scp
`! 1J, 2007
`~<llan C"l a!..· The Topical Anti-lnilammawry and Am1lgesic Proper·
`tics ofBJ\)mJCnic in Rodents", Agents ll1ld A<.:tions, vol. 2S, No. l-2,
`pp 17-k\ Aug. 19XX:
`
`JaiL 21, 2003
`
`(JP)
`
`(51)
`
`(52)
`
`(20<h01)
`(21Xl6.01!
`(21X)(i,()J)
`(2006.01)
`(_20<)(i_()J)
`(2001i.Ol)
`
`Int. Cl.
`AfJJN JY/8
`A6!K 3!/165
`AfJJ/V 37/44
`A6!K 31124
`AO!N ./7/f()
`A6/K 31//fJ
`lJ.S. CJ.
`IJSI\'
`514/619·. 51-j./5_15·, .'114/570: 514/(dS
`Field of ( "las:sification Search
`514!619, 535,570
`tJSI~'
`Se._• application tile f0:1r complete senrch histury.
`
`(56)
`
`References Cited
`
`IJS 1'.\TI 'NT DOI'llMFNTS
`
`4.()4<;.)76 A
`4.6X3.247 A
`4.1!10.:;::.'-
`-"-110.491
`\
`".47~.014 .\
`
`'
`'-,540,93() ,,
`
`-~--~SX.X76 A
`
`\Vdstead. J1 d a!
`K 1977
`7 1<JS7 Post:!
`.J Jl)t)() Ogawa d (I]
`( 'herng...( 'hyi d al
`"-1992
`p 1995 Yann1 d a!
`7 1996 Uuy
`9 !996 Desai o::t a!
`
`((\mtinucd)
`
`I.ayla Soroush
`Primary Examiner
`Wcndcroth [ .ind & !\mack,
`(74) Attorney. Agent. or Firm
`LI .. P.
`
`(57)
`
`AilS TRACT
`
`An aqw .. •-nus liquid preparation of the presem invent ion cun(cid:173)
`tuining 2-amino-:\-( 4-bmmobenzoyl)pheuylaccti~; acid or its
`plwmwcu!ogically acceptable salt or a hydrutl' therc"of. an
`alkyl aryl poly ether ;lknhnl type polymer <>uch as tyloxilpol,
`or a polyethylene glycol httfy acid ester such as polyt'!hylene
`glycol mono stearate is stable. Since even in the cast: where a
`prescrvativ.: is incorporated into said aqueous liquid prepa(cid:173)
`ration. the preservative exhibits a sutiicient prescrv<Jtive
`dft..'Ct f(Jr a lung time. s~lid aqueous liquid pn:pllration in the
`form of an eye drl)p is uscti.ll fix the treatment of blepharitis,
`conjunctivitis. scleritis, and postoperative inlhmunation.
`Also. the uquL·ous liquid preparation nfthc present inwmiun
`in the fllml of a nasal drop is useful fur the trcatmelll of
`Jllcrj.!_k rhinitis and inlbmmatory rhinitis (e.g. dmmic rhini(cid:173)
`tis, hypertrophic rhinitis, n<lsa! polyp, etc).
`
`JO Claims, ~o I>rawings
`
`Page 34 of 46
`
`

`

`Case 1:14-cv-03962-JBS-KMW Document 1-3 Filed 06/20/14 Page 3 of 11 PageID: 35
`
`lJS 8, 754,131 B2
`2
`
`Couccted fMJi:al Fng:!Jsh ILtrHin!wn of "ic\\- I )!ug,; m Iapan, .JOO I.
`:1\Xl! !:di1wn, f'ubhshcd by Yaklqi "SipJki l Jd., :Vi.1y ! I, !UOI. pp
`Y!~2'!. ptc¥1ou~!y whmllli:d <'Jl Apr- I!, 200)
`(',JJnpletc Ftig_l!~h lf;wslllliun of "--ew lJnJg:; 10 Japan, !OOL 200!
`hillnn. Pub!Jshed by YakUJ! Nipfl(l Lid., \1ay I L .'JlO L pp Tf<!•J
`
`:\oli.:e of0pp11SI1ion dated h:h. I 9, 2009 1%Ued hy !]\) m n'nne,>
`Uvn Wilh I he ,_;,,n,;:;ponding rurope:m jllliCIII :tpplinHion itlld l)ppo-
`SIOOil
`http. mcdKitl·dJc! !\JII;Hy.th.:frcedic:lwn;u)' com prophylad :.:
`;JC((:SM:d J)e..:. ]'\. 20(Jij
`fl. Stoll d al . "( 'ompMing I he Surl!Kc ( 'hcnw .. ·a! J>roperlics and !he
`Ulcc1 of Salts un the ('loud P,Jin1 uf a (·onventwnal '\onionic
`Ot:WXYII<)I 9 (rrilon X-100), and <)f !IS Olig:.>nwr.
`Surli:!uanl,
`I mon WR-! )39)"', J,nnnal of Co!lo!d and lnkrfa~;c Sn(cid:173)
`lyhxapol
`pp 4<)6· so~. ! 'J9k
`cncc, vol
`
`Page 35 of 46
`
`

`

`Case 1:14-cv-03962-JBS-KMW Document 1-3 Filed 06/20/14 Page 4 of 11 PageID: 36
`
`US 8, 754,131 B2
`
`2
`ln these prior Jrt relhences. there i,; no dlsck,sure th~ll <llky!
`~nyl polyetlkT :1k•>hoJ type polym\.~rs or pulyethykne glycol
`bl1y <Kid e;;ters ;m: :1hk' ttr st:.~bilizc wl. uquc'<.)US liquid prepa(cid:173)
`mtion of .2-mniuu-1-{.4-hrornob-enzuyl) phenylacetic add or
`its ph;wmacnh)gicdly :wu.'PLll-,k salt, and inhihit dccr(·ase in
`pre~'f1/ntiw cilt..'Ctofhenialkonium vhluridc and o1her gua(cid:173)
`temary anunoninm compounds
`I >lS( 'I J )Sl JRf~ tJF -n ll: JN\"1-'NTH }N
`
`A()lii':OUS LH)I!IJ) PREPARATIO'i
`('0:"\TAJNJ:'\(;
`z,AyiiN<H'{HIRO.VIO!ll<iV:OYI.)I'IU:'iYI A<'ET!(.
`.\CIIJ
`
`IH 'liN I( ·.\1 I 111.1 l
`
`!lw prcgcnt ,lflh'Oiinn tebteS !o an aq!lC<.'itlS liquid prcpa(cid:173)
`rwinll cuHtaining 2<uuino"_)-( 4~hromohcnzoyl )phcnylac .. ~tic
`acid or n pharmacnln&ical!y e~cc<.·pt~lhle ~al! thereof llr ;1
`hydrate tbcrcor Mnrc particularly, the present invcn!iun
`rdatcs h'J an aqueous liquid prcpanltion C<ll1ldining 2-amino-
`:\-( 4-bromobcnmyl'iphcoyb.:etic :~cid or <l phnrnwculugi(cid:173)
`c;dly :Ktcpl:lblc s;1lt !hlTcnf or a hydntk tlk'fC~ll-and an ;dky! 1,
`aryl pnlydhcr alcohnl1ypc polymer or a polyethylene gl].-col
`fairy ucid ester.
`
`J·•
`
`11 is an nhjL'"\:Juf1he pre-sent invelltiDoto provide :m aque(cid:173)
`,,us liquid prepannion t(lmprising 2-amino-~-( 4~brumtJbcn­
`tuyl)pbel1YLK-ctic :l(id <lr:l p!wrfll<H..-l:.lltlg_ically ac~.,'c-ptable -;all
`thereofnr a hydrate thereof, whlch is $!able within a pll range
`givi!ljl.lW irritation to eyes and in which, when a prcserv<ltive
`such as henn1lkonium chloride i~ incurpor:.~ted therein, pre-
`sl:.'rvative dTCct of the preservative docs not substantially
`dctcri(Jf:lle.
`Another nlzject nf the invention i;; to provide ~l method for
`.->tnbi!i?ing an lKjuenus liquid prepM<ilion nf 2-amino<'+.t-(cid:173)
`hromobenzoy!)plwnylacc!it: add or a phannat:ologically
`acceptable salt thereof or a hydrate thereof.
`Further nbjcct of the invcn!i\ln is tu provide an aqueous
`liquid preparation comprising 2·amioo-:1--(4-bromobenzoyl)
`_, ~ pheny bcetic add or a pharmncnlogic;dly acceplah!c ~-mlt
`thereof or a hydra!(.: thert:d' und il pn;servative wherein, when
`sfX:t .. 'itlc~tl!y a lf!laternary ammonium salt such as benz:llko(cid:173)
`nium chloride is incorpnrcl!c-d as a preservative, dL'Crease in
`prest:rv;Jtivc eJl(_'Ct of said preserv<Jtive is inhibited.
`As a resuh ofv;:lrious studies, the inventors of the present
`invention have t{mnd that. by addinp.. fur r.:xample, :.~n alkyl
`aryl polyethcr alcohol type polymer such as ty!oxapo!, or a
`polyethylene glycol !i!lty ~1cid eskr such as polyethylene
`glycul mono;;tcamte to <ln aqueous liquid preparation of
`~~ 2-amimJ-5~( 4-bnJrnobennlyl)phcnylacetic acid or a phanna(cid:173)
`colug.ic;.dly atxcptab!e salt thereof or a hydrate thereoL the
`aqueous solution becomes stable v.:ithin a pi I range giving no
`irritation to cyt:s, nnd change ufthe 2-muino-5-( 4-bmmubcn(cid:173)
`;_()yl)phenylacetic acid over time c;m be inhihitl:.'d. and fw-
`thenw.lre, when the 3queous solution contains a prcserwJtivt:.
`deterioration in the preservative efit-:t:T of :;aid preservative
`can be inhibitc>d f()fa long. period of time. ·nw invenTors pftht·
`present invention have h1rther studied extensively and cnm-
`pictcd the present invention.
`Namely. the present invention relates to:
`( 1) An aqueous liquid preparation comprising_ 2-mnino-3-( 4-
`bromobenzoyl)phcnybcetic acid or a phannacolngically
`acCL'fllable snlt thereof or a hydrate thereof, and an alkyl aryl
`polyether alcohol type polymer or a polyethylene glycol ti.1tty
`5n acid ester.
`(2) 'fhe nqueous liquid prcparati\lll according tu the aht1ve ( l ),
`wherein the alkyl aryl pulyether alcohol Type polymer Jws a
`polymerization degree of 1 to I 0. the nlkyl contaim I to 1 X
`carbon atoms, the af)'l is ;:1 phenyl residue, ;md the polycther
`~' alcohol i$ represented hy the fonnula O(CI 12C! /_z())) I in
`\'1.-·hich X is an integer of 5 tn 100.
`(3) The uqueuus liquid prepamtion according to the above ( 1)
`or (2), wlKreinthe nlkyl aryl poly ether alcohul type polymer
`is tyluxapnl.
`(>~; (4) "l11e <lqw.:ous liquid preparation according to the above ( i ).
`"'-'herein the c;.trbon munber of the illny acid in the polyethyl(cid:173)
`ene glycol fi.ltty acid ester is J 2 to 1 S,
`(5) The aqueous liquid prepa