DCT

1:25-cv-01201

Orion Corp v. MSN Laboratories Pvt Ltd

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I. Executive Summary and Procedural Information

  • Parties & Counsel:
  • Case Identification: 1:25-cv-01201, D. Del., 09/26/2025
  • Venue Allegations: Venue is alleged to be proper in the District of Delaware because Defendant MSN Pharmaceuticals Inc. is a Delaware corporation, and Defendant MSN Laboratories Private Limited is subject to personal jurisdiction in the district.
  • Core Dispute: Plaintiffs allege that Defendants' filing of an Abbreviated New Drug Application (ANDA) to market a generic version of the prostate cancer drug Nubeqa® (darolutamide) constitutes an act of infringement of four patents covering specific crystalline forms, pharmaceutical formulations, and particle characteristics of the active ingredient.
  • Technical Context: The patents relate to the solid-state chemistry and formulation of the androgen receptor inhibitor darolutamide, focusing on stable and pure crystalline forms with specific physical properties intended to ensure manufacturing consistency and bioavailability.
  • Key Procedural History: The litigation was initiated under the Hatch-Waxman Act following Defendants' submission of ANDA No. 220822 to the FDA and subsequent notification to Plaintiffs via a Paragraph IV certification letter. The complaint notes that Defendants' notification letter did not contest that their proposed generic product would infringe certain claims of the asserted patents.

Case Timeline

Date Event
2015-01-30 Earliest Priority Date (’530, ’853, ’515 Patents)
2017-03-07 Priority Date (’058 Patent)
2018-07-03 U.S. Patent No. 10,010,530 Issues
2019-08-20 U.S. Patent No. 10,383,853 Issues
2020-11-17 U.S. Patent No. 10,835,515 Issues
2021-11-09 U.S. Patent No. 11,168,058 Issues
2025-08-26 Date of MSN's Notice Letter to Plaintiffs
2025-09-26 Complaint Filing Date

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

U.S. Patent No. 10,010,530 - "Carboxamide Derivative and Its Diastereomers in Stable Crystalline Form"

Issued July 3, 2018

The Invention Explained

  • Problem Addressed: The patent addresses the need to obtain the pharmaceutical compound darolutamide in a stable and substantially pure crystalline form, which is critical for consistent manufacturing and performance in a final drug product (’530 Patent, col. 2:40-44).
  • The Patented Solution: The invention is a specific solid crystalline form of darolutamide, designated "Crystalline Form I." This form is defined by its unique X-ray powder diffraction (XRPD) pattern, which serves as a fingerprint for its crystal structure (’530 Patent, Abstract; col. 3:28-33). The specification details a method for preparing this form by crystallization from an acetonitrile and water mixture under specific heating and cooling conditions (’530 Patent, col. 8:38-63).
  • Technical Importance: Obtaining a specific, stable crystalline form (polymorph) is a critical step in drug development, as different forms can have different properties affecting solubility, stability, and bioavailability, thereby impacting a drug's safety and efficacy (’530 Patent, col. 3:6-10).

Key Claims at a Glance

  • The complaint asserts infringement of at least independent claim 1 (Compl. ¶55).
  • Claim 1 requires:
    • Crystalline form I of the compound N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl) propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide (I)
    • having an X-ray powder diffraction pattern comprising characteristic peaks at about 8.5, 10.4, 16.6, 16.9, and 24.3 degrees 2-theta.
  • The complaint does not explicitly reserve the right to assert dependent claims.

U.S. Patent No. 10,383,853 - "Carboxamide Derivative and Its Diastereomers in Stable Crystalline Form"

Issued August 20, 2019

The Invention Explained

  • Problem Addressed: Similar to the ’530 Patent, this patent addresses the need for a stable and pure crystalline form of darolutamide suitable for pharmaceutical use (’853 Patent, col. 2:40-44).
  • The Patented Solution: The invention is also directed to "Crystalline Form I" of darolutamide, identified by the same characteristic XRPD peaks as in the ’530 Patent. However, the claims in this patent add a specific purity limitation, requiring that the Crystalline Form I be "substantially free of any other crystalline form" of the compound (’853 Patent, Abstract; col. 2:60-63).
  • Technical Importance: This patent emphasizes the importance of polymorph purity, as the presence of other, less stable crystalline forms could compromise the long-term stability and performance of the final drug product (’853 Patent, col. 3:6-10).

Key Claims at a Glance

  • The complaint asserts infringement of at least independent claim 1 (Compl. ¶64).
  • Claim 1 requires:
    • Crystalline form I of the compound N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide (I)
    • having an X-ray powder diffraction pattern comprising characteristic peaks at about 8.5, 10.4, 16.6, and 24.3 degrees 2-theta
    • wherein the crystalline form I is substantially free of any other crystalline form of the compound.
  • The complaint does not explicitly reserve the right to assert dependent claims.

U.S. Patent No. 10,835,515 - "Carboxamide Derivative and Its Diastereomers in Stable Crystalline Form"

Issued November 17, 2020

  • Technology Synopsis: This patent claims a finished pharmaceutical product rather than just the active ingredient. It specifically covers an oral dosage form, such as a tablet or capsule, that comprises the Crystalline Form I of darolutamide (as defined by its XRPD pattern) combined with a "pharmaceutical excipient" (’515 Patent, Abstract; col. 1:4-10).
  • Asserted Claims: At least independent claim 1 (Compl. ¶73).
  • Accused Features: The accused feature is Defendants' entire proposed generic tablet, which is alleged to be a pharmaceutical dosage form containing Crystalline Form I of darolutamide and one or more excipients (Compl. ¶¶48, 73).

U.S. Patent No. 11,168,058 - "Manufacture of a Crystalline Pharmaceutical Product"

Issued November 9, 2021

  • Technology Synopsis: This patent focuses on the physical characteristics of the darolutamide particles themselves, which are important for manufacturing and drug delivery. The claims are directed to crystalline particles of the compound having specific physical properties, including a defined specific surface area (SSA) range, a large volume median diameter, and a "rounded particle shape" (’058 Patent, col. 2:8-16; Abstract). These properties are alleged to provide better flowability and processing characteristics compared to small, irregular particles with sharp edges (’058 Patent, col. 2:1-4).
  • Asserted Claims: At least independent claims 1 and 10 (Compl. ¶82).
  • Accused Features: The accused features are the physical properties of the crystalline darolutamide particles within Defendants' proposed generic product, which are alleged to meet the claimed SSA, particle size, and shape limitations (Compl. ¶82).

III. The Accused Instrumentality

Product Identification

The accused instrumentality is "MSN's ANDA Product," identified as a generic version of Plaintiffs' Nubeqa® (darolutamide) tablets, with a proposed dosage strength of 300 mg (Compl. ¶¶1, 47, 49).

Functionality and Market Context

The accused product is a pharmaceutical tablet intended for oral administration as a generic equivalent to the branded Nubeqa® drug (Compl. ¶47). The complaint alleges that MSN filed ANDA No. 220822 with the FDA to obtain approval to manufacture and sell this product in the United States before the expiration of the patents-in-suit (Compl. ¶1, 45). The filing of the ANDA itself is the statutory act of infringement under the Hatch-Waxman Act (Compl. ¶54). No probative visual evidence provided in complaint.

IV. Analysis of Infringement Allegations

U.S. Patent No. 10,010,530 Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
Crystalline form I of N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl) propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide (I) The complaint alleges on information and belief that MSN's ANDA Product contains this specific compound in the claimed crystalline form. It further states that MSN’s Notice Letter did not contest infringement of this claim. ¶55 col. 1:23-33
having an X-ray powder diffraction pattern comprising characteristic peaks at about 8.5, 10.4, 16.6, 16.9, and 24.3 degrees 2-theta. The complaint alleges on information and belief that the crystalline form of darolutamide in MSN's ANDA Product exhibits an XRPD pattern with these characteristic peaks. ¶¶27, 55 col. 3:28-33

U.S. Patent No. 10,383,853 Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
Crystalline form I of N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide (I) having an X-ray powder diffraction pattern comprising characteristic peaks at about 8.5, 10.4, 16.6, and 24.3 degrees 2-theta The complaint alleges on information and belief that MSN's ANDA Product contains the compound in this specific crystalline form. It further states that MSN’s Notice Letter did not contest infringement of this claim. ¶¶32, 64, 66 col. 3:25-30
wherein the crystalline form I is substantially free of any other crystalline form of N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide (I). The complaint alleges on information and belief that the Crystalline Form I in MSN's ANDA Product meets this purity requirement. ¶¶32, 64 col. 2:60-65

Identified Points of Contention

  • Scope Questions: The dispute may center on the scope of "about" as it modifies the claimed XRPD peak locations. The definition of "substantially free" in the ’853 Patent will also be a key issue, as it dictates the level of polymorph purity required to infringe.
  • Technical Questions: A primary technical question is factual: does the active pharmaceutical ingredient in MSN's ANDA product actually exist as Crystalline Form I, and does it meet the purity requirements of the ’853 Patent? As the complaint is based on "information and belief," this raises an evidentiary question that will be addressed through discovery and expert analytical testing of the accused product.

V. Key Claim Terms for Construction

The Term: "about"

(from '530 Patent, Claim 1 and '853 Patent, Claim 1)

  • Context and Importance: This term modifies the numerical values of the XRPD peaks that define the patented crystalline form. The construction of "about" is critical because if MSN's product exhibits peaks that are numerically close but not identical to the claimed values, the breadth of this term could determine the outcome of infringement.
  • Intrinsic Evidence for Interpretation:
    • Evidence for a Broader Interpretation: The patent specification explicitly states that "X-ray powder diffraction pattern peak positions referred to herein can be subject to variations of +/-0.15 degrees 2-theta according to various factors" (’530 Patent, col. 4:21-24). This language may support a construction that gives the term a specific numerical range.
    • Evidence for a Narrower Interpretation: A party could argue that the term should be limited by the precision of the instrument used in the patent's examples or that the provided +/- 0.15 degree range represents the maximum allowable variance.

The Term: "substantially free of any other crystalline form"

(from '853 Patent, Claim 1)

  • Context and Importance: This purity limitation is a key distinguishing feature of the ’853 Patent. Infringement hinges on whether MSN's product contains a level of other crystalline forms that falls outside what is considered "substantially free."
  • Intrinsic Evidence for Interpretation:
    • Evidence for a Broader Interpretation: The specification does not provide a specific percentage (e.g., less than 5% impurities) to define "substantially free." The absence of a precise numerical boundary could support an argument for a less stringent standard of purity.
    • Evidence for a Narrower Interpretation: The patent's stated goal of providing a stable form for "pharmaceutical processing and storage" may suggest that the term implies a high degree of purity common in the pharmaceutical industry to ensure product consistency and safety (’853 Patent, col. 3:6-10).

VI. Other Allegations

Indirect Infringement

The complaint alleges that upon approval of its ANDA, MSN will actively induce infringement by marketing its product with labeling that directs physicians and patients to use it in an infringing manner (Compl. ¶¶57-58, 66-67). It also alleges contributory infringement, asserting that MSN's product and labeling are "especially made or adapted for use in infringing" the patents and are not suitable for substantial non-infringing uses (Compl. ¶¶59, 68).

Willful Infringement

The complaint does not contain a specific count for willful infringement. However, it alleges that MSN has knowledge of the patents-in-suit, at minimum through the Paragraph IV notice process (Compl. ¶¶90, 101, 112, 123). The prayer for relief requests a declaration that the case is "exceptional" and an award of attorneys' fees under 35 U.S.C. § 285, which is often associated with findings of willful infringement or other litigation misconduct (Compl. p. 24, ¶(g)).

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

  • A central issue will be one of factual proof: Will discovery and expert analysis of samples from MSN's ANDA submission confirm that the darolutamide active ingredient is, in fact, the patented "Crystalline Form I" as defined by the specific XRPD peaks, purity levels, and particle characteristics claimed across the four patents-in-suit?
  • A key legal question will be one of definitional scope: How will the court construe the claim terms "about" and "substantially free"? The precise boundaries given to these terms during claim construction will likely be dispositive for infringement of the core patents covering the crystalline form.
  • A significant strategic question relates to estoppel and admissions: What legal effect, if any, will result from the complaint's allegation that MSN's Paragraph IV notice letter "did not contest" infringement of certain claims? This could potentially narrow the issues for trial or be used by Plaintiffs to argue against certain non-infringement positions.