DCT

1:18-cv-02051

AstraZeneca Ab v. MSN Pharma Inc

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I. Executive Summary and Procedural Information

  • Parties & Counsel:
  • Case Identification: 1:18-cv-02051, D. Del., 12/26/2018
  • Venue Allegations: Venue is alleged to be proper in Delaware for MSN Pharmaceuticals as it is a Delaware corporation. Venue is alleged for MSN Laboratories (India) based on its purposeful availment through its U.S. subsidiary, its regular engagement in patent litigation in the district, and the expectation of being sued in Delaware after sending a notice letter to a Delaware-based entity.
  • Core Dispute: Plaintiffs allege that Defendants’ filing of an Abbreviated New Drug Application (ANDA) to market a generic version of Plaintiffs' Movantik® (naloxegol) product constitutes an act of infringement of a patent covering a crystalline form of the active ingredient.
  • Technical Context: The technology relates to peripherally acting opioid antagonists used to treat opioid-induced constipation, a common side effect of chronic pain therapy, without interfering with the central pain-relieving effects of opioids.
  • Key Procedural History: This case was initiated under the Hatch-Waxman Act following a November 14, 2018 notice letter from MSN informing Plaintiffs of its ANDA filing. The complaint notes that MSN’s notice letter asserted the patent-in-suit is invalid and/or not infringed, but also alleges that the letter did not contest infringement of at least one specific claim. The complaint also cites several other recent patent litigations involving MSN in the District of Delaware to support personal jurisdiction.

Case Timeline

Date Event
2010-09-30 Earliest Priority Date for ’469 Patent
2015-04-21 U.S. Patent No. 9,012,469 Issues
2018-11-14 MSN Laboratories Sends Notice Letter of ANDA Filing
2018-12-26 Complaint for Patent Infringement Filed

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

No probative visual evidence provided in complaint.

U.S. Patent No. 9,012,469 - “Crystalline Naloxol-PEG Conjugate”

  • Patent Identification: U.S. Patent No. 9,012,469, “Crystalline Naloxol-PEG Conjugate,” issued April 21, 2015.

The Invention Explained

  • Problem Addressed: The patent’s background section describes the challenge of developing the drug candidate mPEG₇-O-naloxol into a viable pharmaceutical product. The free base form of the drug existed as an unstable oil, which could undergo oxidative degradation and was difficult to formulate for large-scale production, transportation, and storage (ʼ469 Patent, col. 1:41-60).
  • The Patented Solution: The invention is a solid, crystalline salt form of the mPEG₇-O-naloxol conjugate, specifically an oxalate salt. The patent discloses that creating this stable, solid crystalline form solves the problems associated with the oily free base, making it suitable for use in a pharmaceutical drug product (ʼ469 Patent, col. 2:35-44; Abstract). The patent describes specific crystalline forms, designated Form A and Form B, and methods for producing them (ʼ469 Patent, col. 2:45-52).
  • Technical Importance: The development of a stable, solid, and crystalline form of a drug substance is a critical step in pharmaceutical manufacturing, as it enables consistent dosing, improved stability, and practical formulation into tablets or capsules (ʼ469 Patent, col. 1:45-48).

Key Claims at a Glance

  • The complaint identifies independent claim 5 as a claim infringed by the defendants (Compl. ¶40).
  • Claim 5 (Independent): A composition of matter claim covering:
    • A naloxol-polyethylene glycol conjugate oxalate salt
    • Wherein the naloxol-polyethylene glycol conjugate has a specific chemical structure depicted in the claim.
  • The complaint reserves the right to assert other claims (Compl. ¶45).

III. The Accused Instrumentality

Product Identification

The accused instrumentality is the generic "naloxegol oxalate tablets" described in MSN Laboratories' Abbreviated New Drug Application (ANDA) No. 212625 (Compl. ¶3).

Functionality and Market Context

  • The ANDA Product is a generic version of Plaintiffs' branded drug, Movantik®, and is intended for the treatment of opioid-induced constipation in adult patients with chronic non-cancer pain (Compl. ¶1-¶2).
  • The complaint alleges that the ANDA Product contains the "same or equivalent ingredients in the same or equivalent amounts" as Movantik® (Compl. ¶6). The product is designed to be manufactured and sold in 12.5 mg and 25 mg tablet form for oral use (Compl. ¶3).

IV. Analysis of Infringement Allegations

’469 Patent Infringement Allegations

Claim Element (from Independent Claim 5) Alleged Infringing Functionality Complaint Citation Patent Citation
A naloxol-polyethylene glycol conjugate oxalate salt, wherein the naloxol-polyethylene glycol conjugate has the formula: [depicted chemical structure] The complaint alleges that MSN filed an ANDA seeking approval to market a generic version of Movantik® consisting of "naloxegol oxalate tablets." Naloxegol is the international nonproprietary name for the chemical structure recited in the claim. The complaint further states that in its notice letter, "MSN did not contest infringement of claim 5." ¶3, ¶6, ¶41 col. 27:1-15

Identified Points of Contention

  • Scope Questions: The complaint's allegation that MSN "did not contest infringement of claim 5" (Compl. ¶41) suggests that the primary dispute may not be over the chemical composition itself. However, a potential issue for the court could be the scope of the claims. For instance, if Plaintiffs assert other claims requiring a specific crystalline form (e.g., Claim 6 or 8), a key question will be whether MSN's ANDA product meets those specific crystalline limitations (e.g., Form A or Form B), as opposed to being an amorphous version or a different polymorph of the same salt.
  • Technical Questions: While the complaint lacks detailed technical analysis of the ANDA product, a central evidentiary question for the court will be to determine if the product described in the ANDA specification possesses the exact chemical structure and, if other claims are asserted, the specific crystalline properties required by the claims. The main challenge for the plaintiff will be to prove infringement of claims that recite specific crystalline forms, such as Form A or Form B.

V. Key Claim Terms for Construction

  • The Term: "crystalline oxalate salt of mPEG₇-O-naloxol" (from Claim 1) and "naloxol-polyethylene glycol conjugate oxalate salt" (from Claim 5).
  • Context and Importance: Practitioners may focus on these terms because the patent’s inventive concept is the creation of a crystalline solid form from a previously unstable oil. Claim 5 recites the chemical salt by name without expressly requiring crystallinity, whereas Claim 1 explicitly requires a "crystalline oxalate salt." The definition of these terms will be critical to determine whether Claim 5 is limited to the crystalline forms described in the specification or if it also covers non-crystalline (amorphous) forms of the same salt, which would significantly impact the scope of infringement.
  • Intrinsic Evidence for Interpretation:
    • Evidence for a Broader Interpretation: An argument for a broader reading of Claim 5 is that the claim language itself does not contain the word "crystalline." Under the doctrine of claim differentiation, the presence of the term "crystalline" in other claims (e.g., Claim 1, Claim 6) suggests its absence in Claim 5 was intentional, meaning Claim 5 was not intended to be limited to crystalline forms.
    • Evidence for a Narrower Interpretation: An argument for a narrower reading is that the patent specification as a whole may limit the claims. The patent is titled “Crystalline Naloxol-PEG Conjugate” and the background exclusively discusses the problem of the non-crystalline oil and the solution of creating a stable, solid, crystalline form (ʼ469 Patent, col. 1:41-60; col. 2:35-37). A defendant may argue that the entire invention is defined by its crystallinity, and therefore all claims should be construed as being limited to crystalline forms.

VI. Other Allegations

  • Indirect Infringement: The complaint alleges that MSN will induce infringement upon ANDA approval. This is based on the allegation that MSN's proposed product labeling will instruct physicians and patients to use the ANDA Product in a manner that directly infringes the ’469 patent (Compl. ¶46-¶47). The complaint also pleads contributory infringement, alleging the ANDA Product is not a staple article of commerce and lacks substantial non-infringing uses (Compl. ¶48).
  • Willful Infringement: Willfulness is alleged based on MSN's knowledge of the ’469 Patent "at least before submitting the ANDA" (Compl. ¶42). The complaint further alleges that MSN acted with "full knowledge of the '469 patent and without a reasonable basis for believing that it would not be liable for infringement" (Compl. ¶51).

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

This litigation will likely center on the following key questions for the court:

  1. Validity of the Patent: Given the allegation that MSN did not contest infringement of Claim 5, the primary legal battle will likely concern the validity of the ’469 Patent. MSN’s defense, as foreshadowed in its notice letter, will likely focus on arguments that the claimed crystalline salt form was obvious or anticipated by the prior art.
  2. Scope of the Claims: A central issue of claim construction will be whether the claims are limited to the specific crystalline forms disclosed in the patent. The resolution of whether Claim 5 covers only crystalline forms or also encompasses amorphous forms of the naloxegol oxalate salt will be a critical determinant of the patent's reach and the extent of MSN's potential infringement.
  3. Proof of Crystalline Structure: Should Plaintiffs press claims that explicitly require a specific crystalline form (e.g., Form A or Form B), a key evidentiary question will be whether the product detailed in MSN’s ANDA will, in fact, embody the specific X-ray powder diffraction patterns and other physical characteristics required by those claims.