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Shire Orphan Therapies LLC v. Fresenius Kabi USA, LLC

United States District Court, D. Delaware

June 5, 2018

SHIRE ORPHAN THERAPIES LLC and SANOFI-AVENTIS DEUTSCHLAND GMBH Plaintiffs,
v.
FRESENIUS KABI USA, LLC, Defendant.

          MEMORANDUM

         I. INTRODUCTION

         In this patent infringement action, Shire Orphan Therapies, LLC, and Sanofi-Aventis Deutschland GMBH, (collectively, "Plaintiffs") allege that Fresenius Kabi USA, LLC, ("Defendant") filed an Abbreviated New Drug Application ("ANDA") with the U.S. Food and Drug Administration ("FDA") to manufacture and sell a generic version of FIRAZYR® prior to the expiration of U.S. Patent No. 5, 648, 333 ("the '333 Patent"). The court held a four-day bench trial in this matter beginning on January 29, 2018. Presently before the court are the parties' post-trial proposed findings of fact and conclusions of law concerning the validity of the patent-in-suit, specifically whether the asserted claims are invalid under the doctrine of obviousness-type double patenting ("OTDP") in light of the prior art and whether prosecution laches bars recovery. (D.I. 111.); (D.I. 112 at 35.)

         Pursuant to Federal Rule of Civil Procedure 52(a), having considered the entire record in this case and the applicable law, the court concludes that the asserted claims of the patents-in-suit are not invalid due to obviousness-type double patenting and that the doctrine of prosecution laches does not bar recovery because there was no unreasonable or unexplained delay in prosecution. These findings of fact and conclusions of law are set forth in further detail below.

         II. FINDINGS OF FACT[1]

         A. The Parties

         1. Plaintiff Shire Orphan Therapies, LLC ("Shire") is a limited-liability company organized and existing under the laws of the State of Delaware, with its principal place of business located at 300 Shire Way, Lexington, Massachusetts 02421. Shire Orphan Therapies, LLC was formerly known as Shire Orphan Therapies, Inc.

         2. Plaintiff Sanofi-Aventis Deutschland GmbH ("Sanofi") is a company organized and existing under the laws of Germany, with its principal place of business located at Briiningstrasse 50, D-65926, Frankfurt am Main, Germany.

         3. Defendant Fresenius Kabi USA, LLC ("Fresenius") is a limited-liability company organized and existing under the laws of the State of Delaware, with its principal place of business located at Three Corporate Drive, Lake Zurich, Illinois 60047.

         4. The court has subject matter jurisdiction and personal jurisdiction over all parties.

         B. Background[2]

         5. This is a civil action for patent infringement arising under the patent laws, 35 U.S.C. § 100 et seq., and the Hatch-Waxman Act, codified as amended at 21 U.S.C. § 355(j) and 35 U.S.C. § 271(e). (D.I. 94 at 2.)

         6. Shire is the holder of New Drug Application ("NDA") No. 022150, which provides for the use of FIRAZYR® (icatibant) Injection for the treatment of acute attacks of hereditary angioedema ("HAE") in adults 18 years of age and older. (D.I. 94 at 2.)

         7. FIRAZYR® (icatibant acetate) is supplied as a single-use, prefilled syringe for subcutaneous administration, each prefilled syringe delivering 3 mL of a solution equivalent to a 30 mg icatibant (free base) dose. (D.I. 94 at 2.)

         8. The '333 Patent is listed in the FDA's publication "Approved Drug Products with Therapeutic Equvalence Evaluations" (commonly known as the "Orange Book") as covering FIRAZYR®. (D.I. 94 at 2.)

         9. The '333 patent, entitled "Peptides Having Bradykinin Antagonist Action, " was issued on July 15, 1997. Sanofi currently owns the '333 Patent, and Shire is the current exclusive licensee of the '333 patent.

         10. By letter dated October 27, 2015, Fresenius provided notice to Plaintiffs that it had filed ANDA No. 208317 with a certification under 21 U.S.C. § 355(j)(2)(A)(vii)(IV) ("Paragraph IV Certification") to obtain FDA approval to engage in the commercial manufacture, use, or sale of icatibant prior to the expiration of the '333 Patent.

         11. On November 30, 2015, Plaintiffs filed suit against Fresenius, asserting infringement of the '333 patent by Fresenius's submission of ANDA No. 208317 and proposed commercial manufacture, use, sale, offer for sale, and/or importation of icatibant thereunder. (D.I. 1.)

         12. Fresenius answered Plaintiffs' Complaint on January 13, 2016, asserting counterclaims for declaratory judgment of invalidity of the '333 Patent under 35 U.S.C. §§101, 102, 103, and/or 112 and non-infringement of the '333 Patent. (D.I. 11.) Plaintiffs answered Fresenius's counterclaims on February 8, 2016. (D.I. 14.)

         13. On August 12, 2016, Fresenius filed an Amended Answer and Counterclaim, which added a counterclaim for declaratory judgment of unenforceability of the '333 Patent under the doctrine of prosecution laches. (D.I. 41.) Plaintiffs answered Fresenius's amended counterclaims on September 6, 2016. (D.I. 43.)

         14. On December 15, 2017, Fresenius filed a Second Amended Answer and Counterclaim (D.I. 93), which amended its counterclaim for declaratory judgment of invalidity of the '333 Patent by adding an assertion of obviousness-type double patenting.

         15. On January 22, 2018, the parties agreed to dismiss the 35 U.S.C. § 103 challenge to the '333 Patent. (D.I. 99.)

         C. The Patents-in-Suit

         16. The '333 Patent may be referred to as the "Patent-in-suit."

         17. The '333 Patent entitled, "Peptides Having Bradykinin Antagonist Action, " was issued on July 15, 1997 to inventors Stephan Henke, Hiristo Anagnostopulos, Gerhard Breipohl, Jochen Knolle, Jens Stechl, Bernward Scholkens, Hans-Wolfram Fehlhaber, Hermann Gerhards, and Franz Hock.

         18. The application resulting in the '333 Patent, U.S. Application No. 08/487, 442, filed June 7, 1995, is a continuation of U.S. Application No. 08/236, 018, filed May 2, 1994, which is a continuation of U.S. Application No. 08/012, 849, filed February 3, 1993, which is a continuation-in-part of U.S. Application No. 07/982, 052, filed November 25, 1992, U.S. Application No. 07/837, 090, filed February 18, 1992, and U.S. Application No. 07/969, 523, filed Oct. 30, 1992, which is a continuation of U.S. Application No. 07/841, 766, filed March 2, 1992, which is a continuation of U.S. Application No. 07/690, 297, filed April 24, 1991, which is a continuation-in-part of U.S. Application No. 07/374, 162, filed June 30, 1989 and U.S. Application No. 07/565, 270, filed August 10, 1990, which is a continuation-in-part of U.S. Application No. 07/374, 162, said U.S. Application No. 07/982, 052, is a continuation of U.S. Application No. 07/746, 149, filed August 14, 1991, which is a continuation-in-part of U.S. Application No. 07/374, 162, said U.S. Application No. 07/837, 090, is a continuation-in-part of U.S. Application No. 07/565, 270, and U.S. Application No. 07/746, 149.

         19. The rights to the invention claimed in the '333 Patent were originally assigned from the inventors to Hoechst Aktiengesellschaft ("Hoechst"), then from Hoechst to Hoechst GmbH, and then from Hoechst GmbH to Sanofi. Sanofi is the current owner of the '333 Patent.

         20. Including a five-year patent term extension, the '333 Patent will expire on July 15, 2019.

         21. The '333 Patent is listed in the FDA publication entitled "Approved Drug Products with Therapeutic Equivalence Evaluations'" (commonly known as the "Orange Book") as covering FIRAZYR®.

         1. The Asserted Claim

         22. Plaintiffs have asserted Claim 14 of the '333 Patent.

         23. Claim 14 of the '333 Patent claims:

         A peptide of the formula H-D-Arg-Arg-Pro-Hyp-Gly-Thia-Ser-D-Tic-Oic-Arg-OH or a physiologically tolerable salt of said peptide.

         2. The Accused Products

         i. Firazyr®

         24. Shire is the holder of New Drug Application ("NDA") No. 022150.

         25. NDA No. 022150 was approved by the United States Food and Drug Administration ("FDA") on August 25, 2011.

         26. NDA No. 022150 provides for the use of FIRAZYR® (icatibant) Injection for the treatment of acute attacks of hereditary angioedema in adults 18 years of age and older.

         27. FIRAZYR® was subject to five-year New Chemical Entity Exclusivity, which expired on August 25, 2016.

         28. FIRAZYR® is supplied in a single-use, prefilled syringe for subcutaneous administration, each syringe delivering 3 mL of a sterile solution of icatibant 30 mg (as icatibant acetate).

         29. Icatibant acetate is the active pharmaceutical ingredient contained in FIRAZYR®.

         30. The chemical name of icatibant is D-Arginyl-L-arginyl-L-prolyl-L[(4R)-4-hydroxyprolyl]-glycyl-L[3-(2-thienyl)alanyl]-L-seryl-D-(1, 2, 3, 4-tetrahydroisoquinolin-3-ylcarbonyl)-L[(3aS, 7aS)-octahydroindol-2-ylcarbonyl]-L-arginine.

         31. A chemical abbreviation for icatibant is H-D-Arg-Arg-Pro-Hyp-Gly-Thia-Ser-DTic-Oic-Arg-OH.

         32. A chemical structure of icatibant acetate is presented below:

         (Image Omitted)

         33. Fresenius prepared, submitted, and filed Abbreviated New Drug Application ("ANDA") No. 208317 under § 505Q) of the Federal Food, Drag, and Cosmetic Act ("FDCA") (codified at 21 U.S.C. § 3550)) for the purpose of obtaining FDA approval to engage in the commercial manufacture, use, or sale of its Icatibant Injection, 30 mg/3 mL prefilled syringe (the "ANDA Product") before the expiration of the '333 Patent.

         34. Included in ANDA No. 208317 is Fresenius's certification pursuant to § 505(j)(2)(A)(vii)(iV) of the FDCA and 21 U.S.C. § 355Q)(2)(A)(vii)(IV) that the '333 Patent is either invalid, unenforceable, or will not be infringed by the manufacture, use, or sale of Fresenius' ANDA Product.

         35. ANDA No. 208317 was submitted to the FDA on August 25, 2015.

         36. By letter dated October 27, 2015 to Shire and Sanofi, Fresenius provided notice under § 505G)(2)(B) of the FDCA and 21 U.S.C. § 355Q)(2)(B) that it had submitted ANDA No. 208317 with a Paragraph IV Certification to obtain approval to engage in the commercial manufacture, use, or sale of its ANDA Product before the expiration of the '333 Patent.

         37. Included in ANDA No. 208317 is Fresenius's request under 21 C.F.R. § 320.22(a) for a waiver of in vivo bioavailability/bioequivalence requirements, based on 21 C.F.R. § 320.22(b), which states that for certain drug products, the in vivo bioavailability or bioequivalence of the drug product may be self-evident.

         38. The active pharmaceutical ingredient, route of administration, dosage form, and strength of the Fresenius ANDA Product are the same as that of FIRAZYR®, as required by law.

         39. The Fresenius ANDA No. 208317 seeks FDA approval of its ANDA Product for the same indication as FIRAZYR®.

         4. Obviousness-Type Double Patenting

         40. U.S. Patent No. 5, 597, 803 ("the '7, 803 Patent"), entitled "Bradykinin Peptides Having Modifications At the N-Terminus, " issued on January 28, 1997 to inventors Gerhard Breipohl, Stephan Henke, Jochen Knolle, Bernward Scholkens, Hans-Georg Alpermann, Hermann Gerhards, Klaus Wirth.

         41. Claim 1 of the '7, 803 Patent claims:

"A peptide of the formula I
Z-P-A-B-C-E-F-K-(D)Q-G-M-F'-I
in which
Z is Fmoc, dibenzylacetyl, cyclohexylcarbonyl, N, N-dibenzyl-glycyl, 2-(4- isobutylphenyl)propionyl, (2-R-(tert butylsulfonylmethyl)-3-(1-naphthyl) propionyl, indole-3-yl-acetyl, 6-(4-benzoyl-benzoylamino)hexanoyl, 1, 8-naphthalimidoacetyl, 7- theophyllineacetyl, or N-benzoyl; P is a direct linkage, Aoc, e-aminohexanoyl, D-Aoc, Aeg(Fmoc), 4- aminocyclohexylcarbonyl or Oic;
A is (D)- or (L)-Arg, (D)- or (L)-Lys, or is a bond;
B is Arg;
C is Pro-Hyp-Gly;
E is Thia;
F is Ser;
K is a direct linkage;
Q is Tic;
M is a direct linkage;
G is cis-endo-, cis-exo-, trans-octahydroindole-2-carboxylic acid;
F' is Arg; and
I is OH."

         5. Prosecution Laches

         42. GATT Legislation:

         43. On December 8, 1994, the Uruguay Round of the General Agreement on Tariffs and Trade, P.L. 103-465 ("GATT") was signed into law. The changes went into effect on June 8, 1995.

         44. The GATT legislation changed the term of U.S. patents issued for an application filed on or after June 8, 1995, to 20 years from the filing date of the original application. Applications filed before June 8, 1995, continued to have a seventeen-year term from the date of issuance or 20 years from the filing date of the original application, whichever was longer.

         45. Continuation applications and continuation-in-part ("OP") applications are two types of continuing applications authorized by statute.

         46. The '333 Patent issued from U.S. Patent Application 08/487, 442 ("the '442 Application"), which was filed on June 7, 1995. The '442 Application claims priority to five German patent applications and ten U.S. patent applications.

         47. German Patent Applications Include: (1)DE 38 39 581.9 was filed on November 24, 1988; (2) DE 39 16 291.5 was filed on May 19, 1989; (3) DE 39 18 225.8 was filed on June 3, 1989; (4) DE 39 26 822.5 was filed on August 14, 1989; and (5) DE 40 13 270.6 was filed on April 26, 1990.

         48. United States Patent Applications:

         i. The '162 Application

         49. The ' 162 Application, entitled "Peptides Having Bradykinin Antagonist Action, " was filed on June 30, 1989.

         50. The '162 Application claimed priority to German patent applications DE 38 39 581.9, DE 39 16 291.5, and DE 39 18 225.8.

         51. The '162 Application contained 6 claims, 164 examples, and in vitro IC50 data for 25 of those examples.

         52. Example 59 is the peptide icatibant.

         53. The '162 Application contained in vitro IC50 data for Example 59.

         ii. The '149 CIP Application

         54. The '149 CIP Application, entitled "Peptides Having Bradykinin Antagonist Action, " was filed on August 14, 1991, as a CIP of the '162 Application.

         iii. The ...


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