DCT
3:18-cv-14693
Patheon Softgels Inc v. Puracap Pharmaceutical LLC
I. Executive Summary and Procedural Information
- Parties & Counsel:
- Plaintiff: Patheon Softgels Inc. (Delaware) and Bionpharma Inc. (Delaware)
- Defendant: PuraCap Pharmaceutical LLC (New Jersey)
- Plaintiff’s Counsel: Walsh Pizzi O'Reilly Falanga LLP
- Case Identification: 3:18-cv-14693, D.N.J., 10/05/2018
- Venue Allegations: Venue is alleged to be proper in the District of New Jersey because the defendant, PuraCap, resides in New Jersey and maintains a regular and established place of business in Piscataway.
- Core Dispute: Plaintiffs allege that Defendant’s generic naproxen sodium softgel capsules, marketed under an Abbreviated New Drug Application (ANDA), infringe four patents related to pharmaceutical solvent systems and liquid dosage formulations.
- Technical Context: The technology at issue involves formulations designed to create stable, liquid-filled softgel capsules for the pain reliever naproxen sodium, a drug that can be difficult to dissolve in high concentrations.
- Key Procedural History: The asserted patents are listed in the FDA's "Orange Book" for Plaintiffs' 220 mg Naproxen Sodium OTC capsules. The complaint alleges this suit was triggered by Defendant PuraCap submitting ANDA No. 208363 to the FDA seeking approval to market a generic version of Plaintiffs' product. The complaint also notes prior, consolidated litigation involving the same patent family against other generic manufacturers.
Case Timeline
| Date | Event |
|---|---|
| 2005-03-08 | Priority Date for '978, '979, '344, and '925 Patents |
| 2017-07-04 | U.S. Patent No. 9,693,978 Issues |
| 2017-07-04 | U.S. Patent No. 9,693,979 Issues |
| 2017-11-13 | '978 and '979 Patents Allegedly Listed in Orange Book |
| 2018-03-15 | FDA Approves Defendant's ANDA No. 208363 |
| 2018-07-17 | U.S. Patent No. 10,022,344 Issues |
| 2018-07-24 | U.S. Patent No. 10,028,925 Issues |
| 2018-07-25 | '344 and '925 Patents Allegedly Listed in Orange Book |
| 2018-10-05 | Complaint Filed |
II. Technology and Patent(s)-in-Suit Analysis
U.S. Patent No. 9,693,978 - “Solvent System for Enhancing the Solubility of Pharmaceutical Agents”
Issued July 4, 2017
The Invention Explained
- Problem Addressed: The patent background describes challenges in creating stable liquid formulations for softgel capsules. When a drug is in its salt form (like naproxen sodium), it can react with common solvents like polyethylene glycol (PEG), forming unwanted esters and reducing the amount of available active drug ('344 Patent, col. 2:25-32). Additionally, the pH of the liquid fill must be controlled to avoid damaging the gelatin shell ('344 Patent, col. 1:37-42).
- The Patented Solution: The invention uses a "de-ionizing agent," such as lactic acid, to partially convert the drug salt back to its free acid form within the solvent system ('344 Patent, col. 2:46-53). This partial neutralization is claimed to minimize the formation of PEG esters and enhance the drug's bioavailability, while maintaining a pH level (2.5-7.5) that does not compromise the softgel capsule's integrity ('344 Patent, col. 2:49-53).
- Technical Importance: This approach enables the creation of a concentrated, stable liquid drug solution within a softgel, which can offer faster and more uniform absorption compared to suspensions or solid dosage forms ('344 Patent, col. 1:43-50).
Key Claims at a Glance
- The complaint asserts independent claims 1 and 18, among others (Compl. ¶24).
- Independent Claim 1 requires a pharmaceutical composition in a softgel capsule comprising a fill material with:
- (a) a naproxen salt;
- (b) about 5% lactic acid by weight of the fill material; and
- (c) polyethylene glycol.
(’978 Patent, col. 10:62-67).
- The complaint reserves the right to assert other claims, including dependent claims (Compl. ¶24).
U.S. Patent No. 9,693,979 - “Liquid Dosage Forms of Sodium Naproxen”
Issued July 4, 2017
The Invention Explained
- Problem Addressed: The '979 Patent addresses the same technical challenges as the '978 Patent: creating a stable, high-concentration liquid form of sodium naproxen suitable for a softgel capsule ('344 Patent, col. 1:26-50).
- The Patented Solution: The patented solution is a specific liquid matrix formulation for a softgel capsule. The core concept remains the partial de-ionization of naproxen sodium using lactic acid in a PEG-based solvent, but the claims add a "solubilizer" element to the required composition ('979 Patent, col. 11:25-32). This solubilizer is intended to further enhance the drug's solubility in the fill material ('344 Patent, col. 4:13-20).
- Technical Importance: As with the '978 Patent, the invention provides a method for producing a stable, liquid-filled naproxen sodium softgel that facilitates rapid and consistent drug delivery.
Key Claims at a Glance
- The complaint asserts independent claim 1, among others (Compl. ¶24).
- Independent Claim 1 requires a soft gelatin capsule comprising a fill material with:
- (a) naproxen sodium;
- (b) about 5% of a deionizing agent comprising acetic acid, propionic acid, pyruvic acid, or lactic acid;
- (c) polyethylene glycol; and
- (d) a solubilizer comprising glycerin, polyvinylpyrrolidone, propylene glycol, or combinations thereof.
(’979 Patent, col. 11:25-32).
- The complaint reserves the right to assert other claims, including dependent claims (Compl. ¶24).
U.S. Patent No. 10,022,344 - “Liquid Dosage Forms of Sodium Naproxen”
Issued July 17, 2018
- Technology Synopsis: This patent describes a stable liquid dosage form of sodium naproxen for softgel capsules. The claimed solution is a fill material comprising sodium naproxen, a de-ionizing agent (such as lactic acid), polyethylene glycol, a solubilizer, and water, which together create a stable liquid matrix suitable for encapsulation (’344 Patent, col. 11:13-25).
- Asserted Claims: Independent claims 1 and 13 (Compl. ¶24).
- Accused Features: The complaint alleges that the PuraCap Generic Product, which is alleged to contain naproxen sodium, lactic acid, polyethylene glycol, povidone, and propylene glycol, infringes these claims (Compl. ¶19, ¶20, ¶24).
U.S. Patent No. 10,028,925 - “Liquid Dosage Forms of Sodium Naproxen”
Issued July 24, 2018
- Technology Synopsis: This patent covers pharmaceutical compositions in softgel capsules with a specific liquid matrix. The matrix requires naproxen sodium, about 5% lactic acid by weight, polyethylene glycols, and one or more solubilizers, a combination intended to ensure product stability and bioavailability (’925 Patent, col. 11:1-8).
- Asserted Claims: Independent claims 1, 9, and 19 (Compl. ¶24).
- Accused Features: The formulation of the PuraCap Generic Product is alleged to embody the composition claimed in the patent (Compl. ¶19, ¶20, ¶24).
III. The Accused Instrumentality
- Product Identification: The accused instrumentality is the "PuraCap Generic Product," a generic version of a 220 mg Naproxen Sodium over-the-counter (OTC) drug product, for which PuraCap received FDA approval via ANDA No. 208363 (Compl. ¶15).
- Functionality and Market Context: The product is a liquid-filled softgel capsule marketed as a "pain reliever/fever reducer (NSAID)" (Compl. ¶21). The complaint alleges, upon information and belief, that the product's liquid fill material contains naproxen sodium, lactic acid, polyethylene glycol, povidone (polyvinylpyrrolidone), and propylene glycol, among other inactive ingredients (Compl. ¶19). Exhibit G, a photograph of the PuraCap Generic Product's packaging, lists ingredients including povidone and propylene glycol (Compl., Ex. G). The product is allegedly manufactured in China, imported into the U.S., and sold by major retailers such as Target, CVS, and Walgreens (Compl. ¶18, ¶22).
IV. Analysis of Infringement Allegations
’978 Patent Infringement Allegations
| Claim Element (from Independent Claim 1) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| (a) a naproxen salt | The accused product contains "naproxen sodium." | ¶19 | col. 10:64 |
| (b) about 5% lactic acid by weight of the fill material | The amount of lactic acid in the product is alleged to be "about 5% by weight of the capsule fill material." | ¶20 | col. 10:65 |
| (c) polyethylene glycol | The accused product contains "polyethylene glycol." | ¶19 | col. 10:66 |
’979 Patent Infringement Allegations
| Claim Element (from Independent Claim 1) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| (a) naproxen sodium | The accused product contains "naproxen sodium." | ¶19 | col. 11:27 |
| (b) about 5% of a deionizing agent comprising... lactic acid | The product allegedly contains "about 5% by weight" of lactic acid. | ¶20 | col. 11:28-29 |
| (c) polyethylene glycol | The accused product contains "polyethylene glycol." | ¶19 | col. 11:30 |
| (d) a solubilizer comprising... polyvinylpyrrolidone, propylene glycol, or combinations thereof | The product's ingredients allegedly include "povidone" (polyvinylpyrrolidone) and "propylene glycol." | ¶19 | col. 11:31-32 |
- Identified Points of Contention:
- Factual Question: The complaint's central allegation that the accused product contains "about 5%" lactic acid is made "on information and belief" (Compl. ¶20). A primary point of contention will be whether discovery and chemical analysis confirm that the actual concentration of lactic acid in the PuraCap product falls within the scope of this limitation.
- Scope Questions: The term "about 5%" will be a focus. The parties may dispute the permissible range of deviation from 5.0% that the term "about" allows. The interpretation will be critical, as a narrow construction could allow a product with a slightly different concentration to fall outside the claim's scope.
V. Key Claim Terms for Construction
- The Term: "about 5%"
- Context and Importance: This quantitative limitation appears in the independent claims of all four asserted patents. The infringement analysis for each patent hinges on whether the accused product's formulation meets this specific percentage requirement. Practitioners may focus on this term because its construction will likely be dispositive of infringement.
- Intrinsic Evidence for Interpretation:
- Evidence for a Broader Interpretation: Plaintiffs may argue that the term "about" should be interpreted functionally, encompassing any percentage of lactic acid that achieves the claimed technical benefits of partial de-ionization and stability described in the specification, consistent with normal manufacturing tolerances. The specification does not define the term, potentially leaving its scope open to a broader, ordinary meaning.
- Evidence for a Narrower Interpretation: Defendant may argue that the explicit recitation of "5%" in the claims, as opposed to a broader range, was a deliberate choice to distinguish the invention from the prior art. The prosecution history (not provided with the complaint) may contain statements that limit the scope of "about." The specificity of this term across multiple patents suggests it may be treated as a critical, rather than merely exemplary, parameter of the invention.
VI. Other Allegations
- Indirect Infringement: The complaint alleges induced infringement, stating that PuraCap's product packaging and labels instruct patients, doctors, and pharmacists on how to use the product in an infringing manner (Compl. ¶25, ¶26).
- Willful Infringement: The willfulness allegation is based on PuraCap's alleged knowledge of the patents. The complaint claims PuraCap was aware of the '978 and '979 patents at least since their listing in the FDA's Orange Book on or about November 13, 2017, and the '344 and '925 patents since their listing on or about July 25, 2018, both dates preceding the filing of the complaint (Compl. ¶25).
VII. Analyst’s Conclusion: Key Questions for the Case
- A primary issue will be one of evidentiary proof: can Plaintiffs prove through discovery and testing that the accused generic product's formulation, as manufactured and sold, actually contains "about 5% lactic acid by weight," as alleged on information and belief?
- The case will also turn on a question of claim construction: how will the court define the scope of the term "about 5%"? The outcome of this legal determination will set the numerical boundaries for the factual infringement analysis.
- A likely, though unstated, question will be one of validity: is the claimed invention—a specific formulation using known pharmaceutical excipients at a specific percentage—non-obvious over the prior art? The defense will probably assert that combining naproxen sodium with common ingredients like lactic acid and PEG was obvious to a person of ordinary skill in the art.