DCT

2:22-cv-00750

Momenta Pharma Inc v. Mylan Pharma Inc

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I. Executive Summary and Procedural Information

  • Parties & Counsel:
  • Case Identification: 2:22-cv-00750, W.D. Pa., 05/20/2022
  • Venue Allegations: Venue is alleged to be proper in the Western District of Pennsylvania because Defendants Viatris, Mylan Inc., and Mylan Pharmaceuticals, Inc. reside in the district and maintain regular and established places of business there. Venue over the foreign defendants is alleged to be proper as they may be sued in any judicial district.
  • Core Dispute: Plaintiff alleges that Defendants’ manufacture, importation, and sale of generic glatiramer acetate products infringes two patents covering methods for manufacturing and analyzing such products.
  • Technical Context: The technology concerns manufacturing and quality control methods for glatiramer acetate, a complex heterogeneous mixture of peptides used to treat multiple sclerosis, where achieving batch-to-batch consistency is a significant technical challenge.
  • Key Procedural History: The complaint alleges that Defendants had pre-suit knowledge of the patents-in-suit and their families through Mylan’s participation in European patent opposition proceedings related to the same technology. The infringement allegations are primarily based on the inference that to gain FDA approval for their generic products, Defendants had to demonstrate "sameness" to the innovator drug, which allegedly required using the patented methods.

Case Timeline

Date Event
2008-04-16 U.S. Patent 9,395,374 Priority Date
2009-04-03 U.S. Patent 8,859,489 Priority Date
2009-06-29 Mylan files Abbreviated New Drug Application (ANDA) for 20 mg/mL product
2014-02-12 Mylan's ANDA for 40 mg/mL product accepted for FDA review
2014-10-14 U.S. Patent 8,859,489 Issued
2016-07-19 U.S. Patent 9,395,374 Issued
2017-10-03 Mylan's ANDAs for both product strengths receive FDA approval
2017-10-04 Mylan begins commercial shipment of accused products in the U.S.
2022-05-20 Complaint Filed

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

U.S. Patent No. 8,859,489 - "Water-Mediated Control of Depolymerization Step of Glatiramer Acetate Synthesis"

  • Patent Identification: U.S. Patent No. 8859489, "Water-Mediated Control of Depolymerization Step of Glatiramer Acetate Synthesis," issued October 14, 2014. (Compl. ¶15).

The Invention Explained

  • Problem Addressed: The patent addresses the difficulty in controlling the manufacturing process for glatiramer acetate (GA) to achieve consistent product quality. Specifically, it was challenging to control the formation of an N-terminal pyro-glutamate (pyro-Glu), a structural feature, and the product's molecular weight during synthesis. (’489 Patent, col. 4:9-17).
  • The Patented Solution: The invention is a method that introduces a controlled amount of water during a key chemical step called depolymerization. By controlling the water content, manufacturers can more precisely steer the reaction to produce a final GA product that has both a desired pyro-Glu concentration and a desired peak molecular weight (Mp). (’489 Patent, Abstract; col. 4:21-45). The patent’s Figure 2 graphically illustrates how adding water (reaction B) versus not adding water (reaction A) allows the process to simultaneously achieve the target molecular weight and target pyro-Glu level, whereas the process without added water does not. (’489 Patent, Fig. 2).
  • Technical Importance: This method provided a way to reliably produce a generic version of GA that was structurally equivalent to the innovator drug, Copaxone®, a critical step in satisfying the FDA's heightened "sameness" criteria for complex generic drugs. (Compl. ¶¶31-33, 40).

Key Claims at a Glance

  • The complaint asserts at least independent claim 1. (Compl. ¶137).
  • The essential elements of claim 1 are:
    • A method for preparing purified glatiramer acetate having a pyro-Glu concentration of 2000–7000 ppm and a peak molecular weight (Mp) of 5000–9000 Da.
    • The method comprises a multi-step chemical synthesis including: (1) polymerizing protected amino acids to generate a protected copolymer; (2) treating the copolymer with HBr and acetic acid for partial depolymerization and deprotection; (3) treating with piperidine to deprotect further; and (4) purifying the final product.
    • The key inventive step requires that "water is present during the entirety of the depolymerization step in an amount that yields" the target pyro-Glu concentration and Mp.
  • The complaint reserves the right to assert other claims. (Compl. ¶137).

U.S. Patent No. 9,395,374 - "Analysis of Amino Acid Copolymer Compositions"

  • Patent Identification: U.S. Patent No. 9395374, "Analysis of Amino Acid Copolymer Compositions," issued July 19, 2016. (Compl. ¶16).

The Invention Explained

  • Problem Addressed: The patent addresses the need for a reliable method to analyze and qualify batches of a complex copolymer like GA to ensure they meet quality standards. Standard analyses like average molecular weight were insufficient to capture critical structural variations that affect product quality and consistency. (’374 Patent, col. 9:30-44).
  • The Patented Solution: The invention is a manufacturing method that integrates specific analytical quality control gates. The method requires measuring the pyro-glutamate content (a key structural signature, depicted in Figure 3) and the peak average molecular weight of a manufactured copolymer batch. Crucially, the batch is processed into a final pharmaceutical product only if the measured pyro-Glu content falls within a specified range (2000-7000 ppm). This serves as a critical go/no-go decision point in the manufacturing process. (’374 Patent, Abstract; col. 10:37-47; Fig. 3).
  • Technical Importance: By identifying pyro-Glu as a key process signature and incorporating its measurement as a release criterion, the invention provides a method to ensure batch-to-batch consistency and demonstrate "sameness" to a reference drug, a major hurdle for generic manufacturers of complex drugs. (Compl. ¶¶19, 41).

Key Claims at a Glance

  • The complaint asserts at least independent claim 1. (Compl. ¶157).
  • The essential elements of claim 1 are:
    • A method for manufacturing a pharmaceutical composition of glatiramer acetate.
    • The method comprises a multi-step chemical synthesis process similar to that described in the ’489 patent.
    • The method then requires three distinct quality control steps: (1) "measuring pyro-glutamate content" of the copolymer; (2) "measuring the peak average molecular weight (Mp)" of the copolymer; and (3) "processing the copolymer to produce a pharmaceutical composition... only if the measured pyro-glutamate content... is within 2000–7000 parts per million (ppm)".
  • The complaint reserves the right to assert other claims. (Compl. ¶157).

III. The Accused Instrumentality

Product Identification

  • "Glatiramer Acetate Injection 20 mg/mL" and "Glatiramer Acetate Injection 40 mg/mL," referred to as the "Mylan Glatiramer Acetate Products." (Compl. ¶1).

Functionality and Market Context

  • The accused instrumentalities are the processes used to manufacture generic versions of Copaxone®, an injectable drug for treating multiple sclerosis. (Compl. ¶¶22, 44). The complaint alleges that to obtain FDA approval, Defendants were required to demonstrate that their products were "the same as" the active ingredient in Copaxone®. (Compl. ¶¶37-38). This demonstration of "sameness" allegedly required Mylan to characterize and control for certain "structural signatures," including pyro-glutamate concentration and molecular weight distribution. (Compl. ¶¶41, 145). The complaint points to the approved label for Mylan's products, which allegedly states an average molecular weight of "5,000 to 9,000 daltons," matching a parameter in the asserted claims. (Compl. ¶146). The product is manufactured outside the U.S. by Defendants Natco, Gland, and Mylan Teoranta and then imported for sale in the U.S. by Defendants MPI, Mylan Inc., and Viatris. (Compl. ¶¶137, 142).

IV. Analysis of Infringement Allegations

8,859,489 Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A method for preparing a composition comprising purified glatiramer acetate having a pyro-Glu concentration of 2000–7000 ppm and a Mp of 5000–9000 Da... Defendants' process allegedly produces glatiramer acetate with these properties because FDA approval required showing "sameness" to Copaxone®, which has these characteristics. Mylan's product label allegedly states an Mp of 5,000-9,000 daltons. ¶¶145, 146 col. 7:15-20
...polymerizing N-carboxy anhydrides...to generate a protected copolymer... Defendants' manufacturing process is alleged to follow the fundamental synthetic scheme for glatiramer acetate identified by the FDA, which includes this polymerization step. ¶147 col. 7:21-25
...treating the protected copolymer with HBr and acetic acid to partially depolymerize the protected copolymer... Defendants' process allegedly includes this depolymerization and deprotection step, as it is part of the required fundamental synthetic scheme. ¶148 col. 7:25-30
...treating the partially depolymerized product with piperidine to deprotect TFA-protected lysines... Defendants' process allegedly includes this deprotection step, as it is also part of the required fundamental synthetic scheme. ¶149 col. 7:30-33
...purifying the glatiramer acetate to create purified glatiramer acetate... Defendants' commercial process is alleged to include a final purification step to produce the finished drug substance. ¶150 col. 7:33-38
...wherein water is present during the entirety of the depolymerization step in an amount that yields glatiramer acetate having a pyro-Glu concentration of 2000–7000 ppm and a Mp of 5000–9000 Da. The complaint alleges, upon information and belief, that Defendants control the presence of water during this step to control the final product characteristics, based on FDA guidance and the known chemical relationship between water, pyro-Glu, and molecular weight. ¶151 col. 7:38-43
  • Identified Points of Contention:
    • Scope Questions: A central issue may be whether meeting the FDA's regulatory standard of "sameness" necessarily requires practicing every limitation of the patented method. Defendants may argue that alternative, non-infringing processes could also achieve a product with the required characteristics.
    • Technical Questions: The infringement allegation for the "wherein water is present" clause is based on information and belief, inferred from regulatory guidance. (Compl. ¶151). A key question for the court will be what factual evidence demonstrates that Defendants' process actually controls water "during the entirety of the depolymerization step" and in an "amount that yields" the claimed result, as opposed to water being an uncontrolled or incidental component.

9,395,374 Infringement Allegations

Claim Element (from Independent Claim 1) Alleged Infringing Functionality Complaint Citation Patent Citation
A method for manufacturing a pharmaceutical composition comprising glatiramer acetate, the method comprising: preparing an amino acid copolymer... Defendants' process is alleged to use the fundamental multi-step synthesis for glatiramer acetate required by the FDA for generic approval. ¶¶166-169 col. 10:15-36
measuring pyro-glutamate content of the copolymer in a sample of the copolymer; The complaint alleges that because pyro-glutamate is a critical process signature for ensuring batch-to-batch consistency and "sameness," Defendants must, as a quality control measure, measure its content. ¶170 col. 10:37-39
measuring the peak average molecular weight (Mp) of the copolymer; The complaint alleges that because the product's approved label specifies a molecular weight range, Defendants must measure this parameter as part of their commercial manufacturing and quality control process. ¶171 col. 10:40-41
processing the copolymer to produce a pharmaceutical composition comprising glatiramer acetate only if the measured pyro-glutamate content of the copolymer in the sample is within 2000–7000 parts per million (ppm)... It is alleged that because FDA authorized Defendants to commercialize only products that are the "same" as Copaxone®, Defendants' process must include a selection step to ensure that only batches with the correct pyro-glutamate content are processed into the final drug product. ¶173 col. 10:42-47
  • Identified Points of Contention:
    • Scope Questions: The core of the dispute for this patent will likely be the "processing... only if" limitation. A question for the court will be whether a highly controlled manufacturing process that consistently yields an in-specification product—without necessarily performing a discrete "measure-and-select" action for each batch—falls within the scope of this claim language.
    • Technical Questions: The allegations for the "measuring" and "processing only if" steps are inferred from regulatory requirements and quality control necessities. (Compl. ¶¶170, 173). An evidentiary question will be whether discovery reveals that Defendants' process includes these specific, discrete analytical and conditional processing steps, or if their quality control is achieved through other means.

V. Key Claim Terms for Construction

  • Term from the ’489 Patent: "present during the entirety of the depolymerization step"

    • Context and Importance: This temporal and conditional language is at the heart of the infringement allegation for the ’489 patent. Its construction will determine whether incidental moisture is sufficient or if an active, controlled presence of water is required throughout the specific chemical reaction step.
    • Intrinsic Evidence for Interpretation:
      • Evidence for a Broader Interpretation: The specification notes that the depolymerization reaction can "consume and produce water" and that the amount can "change slightly over the course," which may suggest that a fluctuating, but never-absent, presence of water meets the limitation. (’489 Patent, col. 6:58-60).
      • Evidence for a Narrower Interpretation: The patent repeatedly emphasizes controlling and adjusting the water content to achieve a predetermined level, which may support a narrower construction requiring active and intentional maintenance of water within the system, not merely its passive presence. (’489 Patent, col. 4:25-30).

  • Term from the ’374 Patent: "processing the copolymer... only if the measured pyro-glutamate content... is within [the specified range]"

    • Context and Importance: This term defines the active, gate-keeping quality control step. Practitioners may focus on this term because the dispute will likely center on whether Defendants' quality system constitutes an infringing conditional "processing" step or merely a process that is robust enough to not require such a gate.
    • Intrinsic Evidence for Interpretation:
      • Evidence for a Broader Interpretation: The claim is for a "method for manufacturing," and the specification describes the analysis of pyro-Glu as a way to "assess product and process quality." (’374 Patent, col. 9:39-44). This could support an interpretation where any quality system that ensures only compliant batches are released for sale embodies this limitation.
      • Evidence for a Narrower Interpretation: The specific language "only if" implies a specific condition precedent. This may support an interpretation requiring a discrete action: a batch is measured, the measurement is compared to a value, and a decision is made to proceed (or not) based on that comparison. A process that is simply well-controlled and never fails might not be seen as practicing this explicit conditional step.

VI. Other Allegations

  • Indirect Infringement: The complaint alleges infringement under 35 U.S.C. § 271(g) by the U.S.-based Defendants (Mylan Pharmaceuticals, Mylan Inc., Viatris) for importing and selling products made abroad by the allegedly infringing processes of the foreign Defendants (Mylan Teoranta, Natco, Gland). (Compl. ¶¶137-138). It also alleges induced infringement under § 271(b), asserting that Defendants knowingly and intentionally encourage infringement through, for example, the dissemination of promotional materials and instructions for the accused products. (Compl. ¶¶139, 159).
  • Willful Infringement: The complaint alleges that Defendants had knowledge of the patents-in-suit and willfully infringed. This allegation is supported by claims that Mylan participated in European Opposition proceedings against patents in the same family, which allegedly demonstrates pre-suit knowledge of the technology and patents. (Compl. ¶¶68-71, 153, 176).

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

  • A central issue will be one of evidentiary sufficiency: The complaint’s infringement theory is built on the inference that meeting the FDA’s stringent "sameness" requirements for a complex generic drug necessitates the use of the patented methods. A key question for the court will be whether Plaintiff can produce direct evidence of Defendants' actual manufacturing process—specifically the controlled use of water (’489 patent) and the practice of a "measure-and-select" quality control step (’374 patent)—or if infringement can be established based on the strong circumstantial evidence tied to regulatory submissions and approvals.
  • The case will also turn on a question of claim scope and process definition: Does a well-designed, robust manufacturing process that consistently yields a product meeting specific quality parameters (e.g., pyro-Glu content) inherently practice a claim that requires an explicit conditional step, such as "processing... only if" a measurement is within a certain range? The construction of this gate-keeping limitation in the ’374 patent will be critical to the outcome of that infringement claim.