DCT

1:17-cv-00302

Pfizer Inc v. Breckenridge Pharmaceutical Inc

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I. Executive Summary and Procedural Information

  • Parties & Counsel:
  • Case Identification: 1:17-cv-00302, D. Del., 03/21/2017
  • Venue Allegations: Venue is alleged to be proper based on general venue statutes. Personal jurisdiction is asserted based on the defendants' filing of an Abbreviated New Drug Application (ANDA) which constitutes a tortious act of patent infringement causing foreseeable harm in Delaware, and based on Breckenridge having previously availed itself of the court by initiating other actions in the district.
  • Core Dispute: Plaintiff alleges that Defendant’s filing of an ANDA to market a generic version of the rheumatoid arthritis drug Xeljanz® constitutes an act of infringement of two patents covering a specific crystalline salt form of the active ingredient, tofacitinib citrate, and the compound itself.
  • Technical Context: The technology concerns specific pharmaceutical compounds and crystalline forms for Janus kinase (JAK) inhibitors, used in the treatment of autoimmune diseases like rheumatoid arthritis.
  • Key Procedural History: The lawsuit was triggered by Breckenridge's filing of ANDA No. 209633 with the U.S. Food and Drug Administration (FDA), which included a "Paragraph IV" certification asserting that Pfizer's patents are invalid, unenforceable, and/or will not be infringed. This certification is the statutory basis for this Hatch-Waxman infringement action.

Case Timeline

Date Event
2001-05-31 U.S. Patent No. 7,301,023 Priority Date
2001-12-06 U.S. Patent No. 6,965,027 Priority Date
2005-11-15 U.S. Patent No. 6,965,027 Issued
2007-11-27 U.S. Patent No. 7,301,023 Issued
2017-02-01 Date of Breckenridge's Notice Letter regarding ANDA filing
2017-03-21 Complaint Filed

II. Technology and Patent(s)-in-Suit Analysis

U.S. Patent No. 6,965,027, "Crystalline 3-{4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile citrate," Issued Nov. 15, 2005

The Invention Explained

  • Problem Addressed: The background of the patent describes the compound tofacitinib as a useful inhibitor of protein kinases like Janus Kinase 3 (JAK3) for immunosuppressive therapy, but does not identify a specific problem with prior forms of the compound (’965 Patent, col. 1:21-52). The invention implies a need for a form of the compound with solid-state properties suitable for pharmaceutical tablet development (’965 Patent, col. 1:52-56).
  • The Patented Solution: The invention is a specific crystalline form of the mono-citrate salt of tofacitinib. The patent provides data from X-ray powder diffraction (XRPD) and differential scanning calorimetry (DSC) to characterize this specific crystalline structure, distinguishing it from other potential solid forms, such as amorphous forms (’965 Patent, col. 2:5-17; Fig. 1-2).
  • Technical Importance: Developing a stable, reproducible crystalline form of an active pharmaceutical ingredient is critical for ensuring consistent bioavailability, manufacturability, and shelf-life in a solid dosage form like a tablet (’965 Patent, col. 1:52-56).

Key Claims at a Glance

  • The complaint asserts infringement of at least Claim 1 (Compl. ¶41).
  • Independent Claim 1:
    • A crystalline form of 3-{(3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile mono citrate salt.

U.S. Patent No. 7,301,023, "Chiral Salt Resolution," Issued Nov. 27, 2007

The Invention Explained

  • Problem Addressed: The patent addresses the challenge of separating mixtures of enantiomers (non-superimposable mirror-image molecules) of chemical compounds (’023 Patent, col. 1:11-19). The background notes that while racemic mixtures are often initially synthesized, individual enantiomers are frequently preferred for drug use, requiring an effective method of resolution (’023 Patent, col. 1:39-44).
  • The Patented Solution: The patent claims the specific (3R,4R) enantiomer of the tofacitinib compound, or a pharmaceutically acceptable salt thereof. This claim covers the specific stereoisomer that is the active ingredient in Xeljanz®, independent of whether it is in a particular crystalline form or is combined with a specific salt, as long as the salt is pharmaceutically acceptable (’023 Patent, Certificate of Correction). The patent describes methods for resolving enantiomers using chiral resolving agents (’023 Patent, col. 5:16-30).

Key Claims at a Glance

  • The complaint asserts infringement of Claim 1 (Compl. ¶45, 47).
  • Independent Claim 1 (as corrected):
    • The compound 3-{(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile or a pharmaceutically acceptable salt thereof.

III. The Accused Instrumentality

Product Identification

  • Breckenridge Generic Tablets, which are the subject of ANDA No. 209633, intended to be a generic version of Pfizer’s Xeljanz® (Compl. ¶12, 30).

Functionality and Market Context

  • The complaint alleges that the Breckenridge Generic Tablets contain tofacitinib citrate as the active ingredient (Compl. ¶32). This is the same active ingredient in Pfizer's Xeljanz®, which is an inhibitor of Janus kinases (JAKs) indicated for treating moderately to severely active rheumatoid arthritis (Compl. ¶19). The filing of the ANDA is an attempt to market and sell these generic tablets prior to the expiration of the patents-in-suit (Compl. ¶2, 33). No probative visual evidence provided in complaint.

IV. Analysis of Infringement Allegations

The complaint does not provide a detailed claim chart. The infringement allegation is based on the statutory act of filing an ANDA under 35 U.S.C. § 271(e)(2)(A) (Compl. ¶39, 45). The technical basis for infringement is the allegation that the product for which Breckenridge seeks FDA approval contains the patented compounds (Compl. ¶32).

’965 Patent Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A crystalline form of 3-{(3R,4R)-4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile mono citrate salt. The Breckenridge Generic Tablets described in ANDA No. 209633 are alleged to contain tofacitinib citrate as the active ingredient, and upon approval will be manufactured and sold, thereby infringing the claim. (Compl. ¶32, 41). ¶32, 41 col. 1:15-20

’023 Patent Infringement Allegations

Claim Element (from Independent Claim 1, as corrected) Alleged Infringing Functionality Complaint Citation Patent Citation
The compound 3-{(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-3-oxo-propionitrile or a pharmaceutically acceptable salt thereof. The Breckenridge Generic Tablets described in ANDA No. 209633 are alleged to contain tofacitinib citrate as the active ingredient, which is a pharmaceutically acceptable salt of the claimed compound. (Compl. ¶32, 47). ¶32, 47 col. 10:52-61
  • Identified Points of Contention:
    • Factual Question: The primary factual question, which will be resolved through discovery, is whether the generic product described in Breckenridge's ANDA is, in fact, the specific "crystalline form" of tofacitinib citrate claimed in the ’965 patent. The complaint alleges Breckenridge's defense is focused on invalidity rather than non-infringement, suggesting Breckenridge does not contest that its product meets the claim limitations (Compl. ¶35).
    • Scope Question: For the ’023 patent, the analysis will center on whether the tofacitinib citrate in the accused product falls within the scope of a "pharmaceutically acceptable salt thereof" as that term is used in the patent.

V. Key Claim Terms for Construction

For the ’965 Patent:

  • The Term: "crystalline form"
  • Context and Importance: The scope of this term is central to the infringement analysis for the ’965 patent. A narrow construction tied to the specific XRPD and DSC data in the patent could provide the defendant with an avenue for a non-infringement argument if their product exhibits even minor variations in its crystal structure. Practitioners may focus on this term because polymorphism is a common issue in pharmaceutical patent litigation.
  • Intrinsic Evidence for Interpretation:
    • Evidence for a Broader Interpretation: The claim itself does not recite any specific analytical data (e.g., peak locations), which might suggest the term is not limited to a single, exact pattern. The abstract refers to "novel amorphous and crystalline forms," suggesting a distinction between the general state of matter rather than a specific polymorph (’965 Patent, Abstract).
    • Evidence for a Narrower Interpretation: The specification provides highly specific characterization data, including a table of 31 distinct XRPD peaks and a DSC thermogram with a characteristic peak. A court could be persuaded that "crystalline form" refers only to a substance exhibiting these specific properties (’965 Patent, Fig. 1-2, Table 1).

For the ’023 Patent:

  • The Term: "pharmaceutically acceptable salt"
  • Context and Importance: This term's construction is key to the scope of Claim 1 of the ’023 patent. Its definition will determine whether the "tofacitinib citrate" in the accused product qualifies.
  • Intrinsic Evidence for Interpretation:
    • Evidence for a Broader Interpretation: The specification provides a non-exclusive list of acids that can form such salts, including "citrate, acid citrate," which explicitly covers the salt form in the accused product. The list includes numerous other common pharmaceutical salts, suggesting the term is meant to be comprehensive (’023 Patent, col. 4:15-22).
    • Evidence for a Narrower Interpretation: The complaint does not provide sufficient detail for analysis of arguments for a narrower interpretation.

VI. Other Allegations

  • Indirect Infringement: The complaint alleges that Pensa Pharma S.A. and Laboratorios del Dr. Esteve, S.A. induced infringement by "actively and knowingly causing to be submitted, and/or assisting with" the filing of Breckenridge's ANDA, knowing that the submission would constitute direct infringement (Compl. ¶52).
  • Willful Infringement: The complaint does not contain an explicit count for willful infringement, but it does allege that Breckenridge had knowledge of the patents when it submitted its ANDA (Compl. ¶40, 46). It also requests a judgment that the case is exceptional under 35 U.S.C. § 285, which is often associated with findings of willfulness or other litigation misconduct (Compl., Prayer for Relief ¶E).

VII. Analyst’s Conclusion: Key Questions for the Case

  • A central issue will be one of validity: As this is a Hatch-Waxman case where non-infringement is reportedly not being argued by the defendant, the case will likely turn on whether Breckenridge can successfully prove by clear and convincing evidence that the asserted claims of the ’965 and ’023 patents are invalid, for reasons such as anticipation or obviousness.
  • A key evidentiary question will be one of polymorphic identity: Should a dispute over infringement arise, the case for the ’965 patent will hinge on whether Breckenridge's generic product possesses the specific "crystalline form" defined by the patent's specification. This will involve a detailed comparison of the analytical data (e.g., XRPD) of the accused product against the data disclosed and claimed in the patent.
  • A secondary question relates to inducement liability: The court will need to determine whether the alleged actions of the foreign parent and partner companies—assisting with and directing the ANDA submission—are sufficient to establish the specific intent required to prove induced infringement under U.S. patent law.