2:18-cv-11406
Metuchen Pharma LLC v. Empower Pharma LLC
I. Executive Summary and Procedural Information
- Parties & Counsel:
- Plaintiff: Mitsubishi Tanabe Pharma Corp (Japan) and Metuchen Pharmaceuticals, LLC (Delaware)
- Defendant: Empower Pharmaceuticals LLC (Texas), Empower Clinic Services LLC (Texas), and ARTA SHAUN NOORIAN
- Plaintiff’s Counsel: Pharmaceutical Patent Attorneys, LLC
- Case Identification: 2:18-cv-11406, D.N.J., 09/07/2018
- Venue Allegations: Plaintiffs allege venue is proper in the District of New Jersey because Defendant Empower Clinic Services LLC has maintained a license to practice pharmacy in the state since 2014, which Plaintiffs assert constitutes a "regular and established place of business" in the district.
- Core Dispute: Plaintiffs allege that Defendants' importation, manufacture, and sale of pharmaceutical products containing the active ingredient avanafil infringes a patent covering the chemical compound, its composition, and its use for treating erectile dysfunction.
- Technical Context: The technology concerns a specific chemical compound, avanafil, which is a phosphodiesterase 5 (PDE5) inhibitor used as a prescription treatment for penile erectile dysfunction.
- Key Procedural History: The complaint alleges that on June 1, 2018, Plaintiff Metuchen provided Defendants with a copy of the patent-in-suit and a cease-and-desist letter, to which Defendants allegedly did not respond.
Case Timeline
| Date | Event |
|---|---|
| 1999-09-16 | ’935 Patent Priority Date |
| 2003-12-02 | ’935 Patent Issue Date |
| 2014-05-16 | Defendant Empower maintains a license to practice pharmacy in New Jersey |
| 2018-06-01 | Plaintiff Metuchen sends cease-and-desist letter to Defendants |
| 2018-09-07 | Complaint Filing Date |
II. Technology and Patent(s)-in-Suit Analysis
U.S. Patent No. 6,656,935 - "Aromatic Nitrogen-Containing 6-Membered Cyclic Compounds"
The Invention Explained
- Problem Addressed: The patent's background describes the need for effective treatments for penile erectile dysfunction. It notes that existing phosphodiesterase (PDE) V inhibitors like sildenafil, while useful, have been reported to have side effects such as headache, facial suffusion, and color sense disorder (’935 Patent, col. 1:49-61).
- The Patented Solution: The invention provides a novel class of aromatic nitrogen-containing cyclic compounds that exhibit excellent selective PDE V inhibitory activity, which the patent asserts are useful as a remedy for penile erectile dysfunction with "few side effects" (’935 Patent, Abstract; col. 2:10-15). The core of the invention is the chemical structure of these compounds, which are designed to selectively inhibit the PDE V enzyme responsible for inactivating the second messenger cGMP, thereby facilitating erections (’935 Patent, col. 1:17-26).
- Technical Importance: The invention provided a new chemical entity for the treatment of erectile dysfunction, a significant medical market, purporting to offer an improved side-effect profile over prior-art compounds (’935 Patent, col. 2:13-15).
Key Claims at a Glance
- The complaint asserts infringement of claims 1-16, 19, and 20 (Compl. ¶¶16-18, 24-27). Independent claims 1, 19, and 20 are representative.
- Independent Claim 1 covers a genus of chemical compounds defined by a Markush structure, encompassing:
- An aromatic nitrogen-containing 6-membered cyclic compound of Formula (I)
- Wherein Ring A is a substituted or unsubstituted nitrogen-containing heterocyclic group
- R¹ is a substituted or unsubstituted lower alkyl group, or a group with the formula -NH-Q-R³ or -NH-R⁴
- R² is a substituted or unsubstituted aryl group
- One of Y and Z is =CH- and the other is =N-
- Independent Claim 19 covers a pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.
- Independent Claim 20 covers a method for the treatment of penile erectile dysfunction which comprises administering an effective amount of a compound according to claim 1 to a patient.
- Claim 16, a species claim dependent on claim 1, specifically claims the compound avanafil by its chemical name: "(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidinylmethyl)carbamoyl] pyrimidine."
III. The Accused Instrumentality
Product Identification
The accused instrumentalities are "avanafil orally disintegrating tablets ('ODTs')" and "troches" manufactured, offered for sale, and sold by Defendants (Compl. ¶24). An attached exhibit to the complaint shows a hard-copy product catalog from Empower listing "Avanafil" for sale in troche form (Compl. Ex. J).
Functionality and Market Context
The accused products contain the active pharmaceutical ingredient avanafil and are promoted as an "Anti-erectile dysfunction agent" (Compl. ¶27; Compl. Ex. H). The complaint alleges Defendants covertly import bulk avanafil active pharmaceutical ingredient and compound it into the accused finished dosage forms (Compl. ¶25).
IV. Analysis of Infringement Allegations
’935 Patent Infringement Allegations
The complaint’s infringement theory for claim 16 is one of literal identity. The complaint includes a chemical structure diagram of avanafil, alleging it is the compound claimed by the patent and sold by the Defendants (Compl. ¶14).
| Claim Element (from Independent Claim 1, as embodied in species Claim 16) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| An aromatic nitrogen-containing 6-membered cyclic compound, namely, (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidinylmethyl)carbamoyl] pyrimidine. | Defendants manufacture, import, offer for sale, and sell orally disintegrating tablets and troches containing the active pharmaceutical ingredient avanafil, which is the specific chemical compound recited in claim 16. | ¶14, ¶16, ¶24 | col. 60:50-65 |
Identified Points of Contention
- Technical Questions: The central question appears to be a factual one of chemical identity. What is the precise chemical composition, including stereochemistry, of the active pharmaceutical ingredient in Defendants' accused ODTs and troches? The complaint alleges, on information and belief, that it is the patented compound avanafil (Compl. ¶25).
- Scope Questions: Should chemical analysis reveal that the accused product is a salt, ester, or pro-drug form of avanafil, a dispute could arise as to whether such forms fall within the literal scope of the asserted claims, which claim the specific compound itself.
V. Key Claim Terms for Construction
The Term
"(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidinylmethyl)carbamoyl] pyrimidine" (from Claim 16).
Context and Importance
In a chemical patent case such as this, the "term" for construction is often the chemical name or structure itself. The entire infringement case hinges on whether the compound sold by Empower is identical to the one defined by this claim. The "(S)" stereochemical designation is a critical limitation, meaning that only one specific stereoisomer of the molecule is claimed.
Intrinsic Evidence for Interpretation
- Evidence for a Broader Interpretation: The complaint does not present a basis for a broader interpretation of this specific species claim. The plain language of the claim recites a single, specific chemical entity.
- Evidence for a Narrower Interpretation: The patent specification provides an explicit recipe for synthesizing the exact compound of claim 16, solidifying its precise chemical identity ('935 Patent, col. 27:66–col. 28:68, Example 1(5)). The inclusion of the "(S)" prefix in the chemical name explicitly limits the claim to a specific stereoisomer, excluding other isomers like the (R) enantiomer or a racemic mixture.
VI. Other Allegations
Indirect Infringement
The complaint alleges that "Empower promotes its products as an 'Anti-erectile dysfunction agent'" (Compl. ¶27). This allegation may support a claim for induced infringement of method claim 20, which covers the use of avanafil to treat penile erectile dysfunction.
Willful Infringement
The complaint alleges willfulness based on both pre-suit and post-suit knowledge. It asserts pre-suit knowledge from Defendants' alleged obligation to possess the FDA Orange Book, which lists the '935 patent, and from Defendants' alleged copying of the STENDRA® package insert, which contains a patent marking notice (Compl. ¶¶21, 23, 28). Post-suit willfulness is alleged based on Defendants' continued infringement after receiving a cease-and-desist letter on June 1, 2018 (Compl. ¶29).
VII. Analyst’s Conclusion: Key Questions for the Case
- A core issue will be one of chemical identity: will laboratory analysis confirm that the active ingredient in Defendants’ avanafil products is the specific (S)-stereoisomer compound recited in claim 16 of the ’935 Patent, or is it a different compound, isomer, or formulation that may fall outside the claim's scope?
- A key legal question will be one of willfulness: do the complaint’s allegations—constructive knowledge from the FDA Orange Book, actual notice from a patent-marked package insert, and continued sales after receipt of a cease-and-desist letter—collectively amount to the "wanton and malicious" conduct required to support a finding of willful infringement and potential enhanced damages?