DCT

1:15-cv-01057

AstraZeneca LP v. Prinston Pharmaceutical Inc

Log In
Key Events
Complaint

I. Executive Summary and Procedural Information

  • Parties & Counsel:
  • Case Identification: 1:15-cv-01057, D. Del., 11/16/2015
  • Venue Allegations: Venue is alleged to be proper in the District of Delaware because Defendant is incorporated in Delaware and, upon information and belief, will market and sell the accused product in the district.
  • Core Dispute: Plaintiff alleges that Defendant's filing of an Abbreviated New Drug Application (ANDA) seeking to market a generic version of Plaintiff's BRILINTA® (ticagrelor) tablets constitutes an act of infringement of five U.S. patents listed in the FDA's Orange Book.
  • Technical Context: The technology relates to the anti-platelet drug ticagrelor, a P2T receptor antagonist used to reduce the risk of cardiovascular death, myocardial infarction, and stroke.
  • Key Procedural History: This action was initiated under the Hatch-Waxman Act following Defendant's submission of ANDA No. 208599 to the FDA. The ANDA included a "Paragraph IV certification" asserting that Plaintiff's listed patents are invalid, unenforceable, or will not be infringed. Defendant notified Plaintiff of its ANDA filing via a Notice Letter dated October 3, 2015, which precipitated this lawsuit.

Case Timeline

Date Event
1997-07-22 ’910 Patent Priority Date
1998-12-04 ’060 Patent Priority Date
1999-12-02 ’419 Patent Priority Date
2000-06-02 ’124 Patent Priority Date
2001-06-26 ’910 Patent Issue Date
2003-02-25 ’060 Patent Issue Date
2006-08-21 ’934 Patent Priority Date
2007-07-31 ’419 Patent Issue Date
2007-09-04 ’124 Patent Issue Date
2013-04-23 ’934 Patent Issue Date
2015-10-03 Date of Defendant's Notice Letter
2015-11-16 Complaint Filing Date

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

No probative visual evidence provided in complaint.

U.S. Patent No. 6,251,910 - “1,2,3-triazolo[4,5-d]pyrimidines as P2T receptor antagonists”

  • Issued: June 26, 2001

The Invention Explained

  • Problem Addressed: The patent addresses arterial thrombosis, where platelet aggregation can lead to acute events like myocardial infarction and unstable angina. The specification notes that existing anti-thrombotic agents carried risks of excessive bleeding, while the widely used aspirin had limited efficacy because it only blocks one pathway for ADP, a key mediator of thrombosis. (’910 Patent, col. 1:11-59).
  • The Patented Solution: The invention provides a new class of chemical compounds, triazolo[4,5-d]pyrimidines, that act as P2T-receptor antagonists. By targeting this receptor on the platelet membrane, the compounds inhibit ADP-induced platelet aggregation, a central mechanism in thrombosis. (’910 Patent, col. 1:59-68; Abstract).
  • Technical Importance: The patent asserts that antagonists at the P2T-receptor offer "significant improvements over other anti-thrombotic agents." (’910 Patent, col. 1:61-63).

Key Claims at a Glance

  • The complaint does not identify specific claims asserted against the Defendant, stating only that the ANDA product will infringe "at least one claim of the '910 patent" (Compl. ¶36). Independent claim 1 is a composition-of-matter claim directed to a genus of chemical compounds.
  • Independent Claim 1 Elements:
    • A compound of formula (I)
    • Wherein R¹ is a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl or a phenyl group, with optional substitutions
    • Wherein R² is a C1-8 alkyl or C3-8 cycloalkyl group, with optional substitutions
    • Wherein one of R³ and R⁴ is hydroxy and the other is hydrogen, hydroxy or NR⁹R¹⁰
    • Wherein R is a group (CR⁵R⁶)mOR⁷ or a substituted C1-4 alkyl or C2-4 alkenyl group

U.S. Patent No. 6,525,060 - “Triazolo(4,5-d)pyrimidine compounds”

  • Issued: February 25, 2003

The Invention Explained

  • Problem Addressed: The patent addresses the same technical problem as the ’910 Patent: the need for effective P2T-receptor antagonists to serve as anti-thrombotic agents without the limitations of prior therapies. (’060 Patent, col. 1:12-49).
  • The Patented Solution: The patent discloses a class of triazolo[4,5-d]pyrimidine compounds, defined by a general formula (I), that act as P2T receptor antagonists to inhibit platelet aggregation. The structural definitions in the ’060 Patent differ from those in the ’910 Patent, suggesting a focus on a different or refined set of compounds within the broader chemical class. (’060 Patent, col. 1:50-55; Abstract).
  • Technical Importance: The patent notes that antagonists at the P2T receptor were recently shown to offer "significant improvements over other anti-thrombotic agents." (’060 Patent, col. 2:1-3).

Key Claims at a Glance

  • The complaint does not identify specific claims asserted against the Defendant (Compl. ¶40). Independent claim 1 is a composition-of-matter claim.
  • Independent Claim 1 Elements:
    • A compound of formula (I) with a specified stereochemistry
    • Wherein R¹ is a C3-5 alkyl optionally substituted by one or more halogen atoms
    • Wherein R² is a phenyl group, optionally substituted by one or more fluorine atoms
    • Wherein R³ and R⁴ are both hydroxy
    • Wherein R is XOH, where X is CH₂, OCH₂CH₂ or a bond

U.S. Patent No. 7,250,419 - “Trisubstituted triazolopyrimidines for use in platelet aggregation inhibition”

  • Issued: July 31, 2007
  • Technology Synopsis: This patent claims methods of using certain triazolopyrimidine compounds to inhibit platelet aggregation. This is a method-of-use patent, distinct from the compound patents.
  • Asserted Claims: The complaint does not identify specific asserted claims (Compl. ¶44).
  • Accused Features: The accused feature is the intended use of Prinston's generic ticagrelor product to treat the same conditions as BRILINTA®, which would allegedly be described in the product's labeling upon FDA approval (Compl. ¶44).

U.S. Patent No. 7,265,124 - “Cristalline and amorphous form of a triazolo (4,5-D) pyridimine compound”

  • Issued: September 4, 2007
  • Technology Synopsis: This patent claims specific solid-state forms (polymorphs) of a triazolopyrimidine compound. Different crystalline or amorphous forms of a drug can have different physical properties, such as stability and dissolution rate.
  • Asserted Claims: The complaint does not identify specific asserted claims (Compl. ¶48).
  • Accused Features: The accused feature is the specific crystalline or amorphous form of the ticagrelor active pharmaceutical ingredient (API) contained in the generic product described in Prinston's ANDA (Compl. ¶48).

U.S. Patent No. 8,425,934 - “Pharmaceutical compositions”

  • Issued: April 23, 2013
  • Technology Synopsis: This patent claims pharmaceutical compositions, or formulations, containing the triazolopyrimidine compound along with specific excipients. It protects the final drug product tablet, not just the active ingredient.
  • Asserted Claims: The complaint does not identify specific asserted claims (Compl. ¶52).
  • Accused Features: The accused feature is the complete formulation of Prinston's generic ticagrelor tablet, including both the ticagrelor API and the other inactive ingredients, as described in its ANDA (Compl. ¶51).

III. The Accused Instrumentality

Product Identification

  • The accused product is the "generic ticagrelor tablets" for which Defendant Prinston submitted ANDA No. 208599 for approval to the FDA (Compl. ¶1, ¶30).

Functionality and Market Context

  • The product is a generic version of AstraZeneca's BRILINTA® drug product, which contains the active ingredient ticagrelor (Compl. ¶1). BRILINTA® is marketed to "reduce the rate of cardiovascular death, myocardial infarction, and stroke in patients with acute coronary syndrome (ACS) or a history of myocardial infarction (MI)" (Compl. ¶28). The complaint alleges that Prinston intends to commercially manufacture, use, and sell its generic product in the United States upon receiving FDA approval (Compl. ¶31).

IV. Analysis of Infringement Allegations

The complaint does not allege infringement of any specific patent claims or provide a technical basis for its infringement allegations beyond stating that Defendant's submission of its ticagrelor ANDA constitutes an act of infringement. In the context of an ANDA case involving compound patents, the infringement theory is typically that the active pharmaceutical ingredient in the generic product is the same chemical compound covered by the patent claims.

'910 Patent Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A compound of formula (I) having the structure and substituents as defined in the claim The ticagrelor active pharmaceutical ingredient contained in the product described in Defendant's ANDA No. 208599 is alleged to be a compound of formula (I). ¶1, ¶35, ¶36 col. 2:5-40

'060 Patent Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A compound of formula (I) having the stereochemistry, structure, and substituents as defined in the claim The ticagrelor active pharmaceutical ingredient contained in the product described in Defendant's ANDA No. 208599 is alleged to be a compound of formula (I). ¶1, ¶39, ¶40 col. 2:28-44
  • Identified Points of Contention:
    • Scope Questions: A central question will be whether the specific chemical structure of ticagrelor falls within the scope of the genus of compounds claimed in the asserted patents. As this is an ANDA litigation, Prinston’s non-infringement defense may argue that the claims, when properly construed, do not read on the ticagrelor compound.
    • Technical Questions: The complaint does not provide evidence regarding the specific composition, crystalline form, or formulation of the accused generic product. A technical question for the court will be whether the product described in ANDA No. 208599, if and when it is manufactured and sold, will in fact embody the compound, form, formulation, and method of use claimed in the patents-in-suit.

V. Key Claim Terms for Construction

The complaint, by alleging infringement without identifying specific claims or articulating any theory of infringement, does not provide a basis for identifying specific claim terms that are likely to be in dispute for construction. In pharmaceutical compound patent litigation, disputes often center on the definitions of the various substituent groups (e.g., "C1-6 alkyl," "aryl") that define the boundaries of the claimed chemical genus.

VI. Other Allegations

  • Indirect Infringement: The complaint alleges that upon FDA approval, Defendant will infringe under 35 U.S.C. §§ 271(b) and/or 271(c) (Compl. ¶36, ¶40, ¶44, ¶48, ¶52). The basis for this allegation is that Defendant will actively induce and contribute to infringement by physicians and patients through the sale of its generic product with labeling that instructs its use for patented methods.
  • Willful Infringement: The complaint does not contain an explicit allegation of willful infringement. The prayer for relief requests relief deemed proper under 35 U.S.C. § 285, which pertains to attorney's fees in exceptional cases, rather than enhancement of damages for willful infringement under § 284 (Compl. p. 11, ¶E).

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

This litigation is a structurally typical Hatch-Waxman action precipitated by a Paragraph IV certification. The case will likely focus on two central issues for the court's determination:

  • A core issue will be one of claim validity: Can Prinston prove by clear and convincing evidence that the asserted claims of AstraZeneca's patents are invalid, for reasons such as anticipation or obviousness, as it certified to the FDA? This is often the primary battleground in ANDA litigation.
  • A secondary, but fundamental, question is one of infringement and claim scope: Do the asserted claims of the five Orange Book patents—covering the ticagrelor compound itself, its solid-state form, its formulation, and its methods of use—literally cover the product described in Prinston’s ANDA No. 208599?