DCT
1:18-cv-00052
Purdue Pharma LP v. Kashiv Pharma LLC
I. Executive Summary and Procedural Information
- Parties & Counsel:
- Plaintiff: Purdue Pharma L.P. and Purdue Pharmaceuticals L.P. (Delaware)
- Defendant: Kashiv Pharma, LLC (Delaware)
- Plaintiff’s Counsel: Morris, Nichols, Arsht & Tunnell LLP
- Case Identification: 1:18-cv-00052, D. Del., 01/03/2018
- Venue Allegations: Venue is alleged to be proper in the District of Delaware because the defendant, Kashiv Pharma, LLC, is a Delaware limited liability company that resides in the district and has allegedly committed acts of infringement there.
- Core Dispute: Plaintiff alleges that Defendant’s submission of an Abbreviated New Drug Application (ANDA) to market a generic version of the opioid analgesic OxyContin® constitutes an act of infringement of three patents related to tamper-resistant pharmaceutical formulations.
- Technical Context: The technology concerns extended-release opioid formulations designed with specific physical and chemical properties to deter abuse, such as crushing for inhalation or extraction with solvents for injection.
- Key Procedural History: This action was initiated under the Hatch-Waxman Act following Plaintiff’s receipt of a Notice Letter with a Paragraph IV certification, dated November 21, 2017, regarding Defendant’s ANDA. The complaint notes extensive prior litigation involving the same ANDA (filed by Amneal Pharmaceuticals) and other Purdue patents covering OxyContin®. This suit was filed against Kashiv "out of an abundance of caution" due to uncertainty over whether Amneal or Kashiv is the proper owner of the ANDA.
Case Timeline
| Date | Event |
|---|---|
| 2006-08-25 | Earliest Priority Date for all Patents-in-Suit |
| 2011-09-27 | Alleged filing of Amneal's original ANDA No. 203235 |
| 2015-10-30 | Alleged filing of Amneal's Amended ANDA |
| 2017-09-19 | U.S. Patent No. 9,763,933 Issues |
| 2017-09-26 | U.S. Patent No. 9,770,416 Issues |
| 2017-10-03 | U.S. Patent No. 9,775,808 Issues |
| 2017-11-21 | Date of Kashiv's Paragraph IV Notice Letter |
| 2018-01-03 | Complaint Filed |
II. Technology and Patent(s)-in-Suit Analysis
U.S. Patent No. 9,770,416 - "TAMPER RESISTANT DOSAGE FORMS"
The Invention Explained
- Problem Addressed: The patent addresses the problem of prescription drug abuse, specifically the methods by which individuals circumvent the extended-release properties of opioid analgesics to achieve a rapid, high-dose effect (’416 Patent, col. 1:26-34). This includes physical manipulation like crushing or chewing, and chemical manipulation like extraction using common solvents such as ethanol (’416 Patent, col. 1:34-44).
- The Patented Solution: The invention is a solid oral dosage form that is highly resistant to both physical and chemical tampering (’416 Patent, Abstract). This is achieved by creating a matrix formulation with a high molecular weight polyethylene oxide (PEO), which is first shaped by compression and then subjected to a thermal "curing" step using heated air without further compression (’416 Patent, col. 17:3-9). This process causes the PEO to partially melt and then harden upon cooling, resulting in a tablet with significant physical hardness and resistance to dissolution in ethanol, thereby deterring common methods of abuse (’416 Patent, col. 25:12-19).
- Technical Importance: The development of abuse-deterrent formulations was a significant objective in the pharmaceutical industry to mitigate the public health risks associated with opioid abuse while maintaining legitimate patient access to pain medication (’416 Patent, col. 1:26-34).
Key Claims at a Glance
- The complaint asserts one or more claims, including independent claim 1 (Compl. ¶29).
- The essential elements of independent claim 1 include:
- A pharmaceutical composition with an opioid active agent and a high molecular weight polyethylene oxide (PEO) between 1 and 8 million MW.
- A solid oral extended release dosage form that is (i) compression shaped, (ii) air cured with heated air (60-90°C) without compression for 15 minutes to 8 hours, (iii) cooled, and (iv) hardened.
- The PEO is at least partially melted upon curing and comprises at least 50% by weight of the dosage form.
- The active agent comprises at least 1.3% by weight of the dosage form.
- The PEO molecular weight is based on rheological measurements.
- The total weight of the dosage form excludes film coatings.
- The dosage form expands upon curing (density decreases by at least 1.5%) and provides a hardness of at least 439 N.
- The complaint reserves the right to assert other claims (Compl. ¶29).
U.S. Patent No. 9,775,808 - "TAMPER RESISTANT DOSAGE FORMS"
The Invention Explained
- Problem Addressed: The '808 Patent addresses the same technical problem as the ’416 Patent: the abuse of controlled-release opioid dosage forms through tampering (’808 Patent, col. 1:26-44).
- The Patented Solution: The solution is again a tamper-resistant extended-release formulation based on a high molecular weight PEO matrix. The '808 Patent claims a composition specifically comprising oxycodone and a PEO with a molecular weight of 1 to 15 million (’808 Patent, claim 1). The manufacturing process similarly involves compression followed by thermal curing with heated air for at least 5 minutes at a temperature above the PEO's softening point, which hardens the tablet and imparts abuse-deterrent properties (’808 Patent, col. 17:3-9, claim 1).
- Technical Importance: This invention provides another specific embodiment of an abuse-deterrent formulation for oxycodone, a widely used but also widely abused opioid analgesic (’808 Patent, col. 1:26-34).
Key Claims at a Glance
- The complaint asserts one or more claims, including independent claim 1 (Compl. ¶36).
- The essential elements of independent claim 1 include:
- A pharmaceutical composition with an oxycodone active agent, a high molecular weight PEO (1-15 million MW), and an additive or film coating.
- A solid oral extended release dosage form that is (i) compression shaped, (ii) air cured with heated air without compression for at least 5 minutes at a temperature above the PEO's softening temperature, (iii) cooled, and (iv) hardened.
- The high molecular weight PEO comprises at least 30% by weight of the dosage form.
- The molecular weight of each PEO is based on rheological measurements.
- The total weight of the dosage form is calculated excluding the weight of film coatings.
- The complaint reserves the right to assert other claims (Compl. ¶36).
U.S. Patent No. 9,763,933 - "TAMPER RESISTANT DOSAGE FORMS" (Multi-Patent Capsule)
- Patent Identification: U.S. Patent No. 9763933, titled “TAMPER RESISTANT DOSAGE FORMS,” issued on September 19, 2017 (the “’933 Patent”) (Compl. ¶19).
- Technology Synopsis: The ’933 Patent is part of the same patent family and is directed to the same core technology of abuse-deterrent opioid formulations (’933 Patent, Abstract). It claims pharmaceutical compositions comprising an active agent and a high molecular weight PEO, which are made into hardened, tamper-resistant tablets through a process of compression followed by thermal curing at a temperature above the PEO’s softening temperature (’933 Patent, col. 1:49-56, claim 1).
- Asserted Claims: The complaint asserts independent claim 1 (Compl. ¶43).
- Accused Features: The complaint alleges that the formulation and manufacturing process of the Amneal Amended ANDA Products, which are generic versions of OxyContin®, meet the limitations of the ’933 Patent’s claims (Compl. ¶43).
III. The Accused Instrumentality
Product Identification
The accused instrumentalities are the "Amneal's Amended ANDA Products," which are generic versions of OxyContin® (oxycodone hydrochloride extended-release tablets) described in Abbreviated New Drug Application (ANDA) No. 203235 (Compl. ¶1, 22). The act of infringement is the submission of the ANDA to the FDA seeking approval to market these products (Compl. ¶28, 35, 42).
Functionality and Market Context
The products are solid oral pharmaceutical dosage forms designed for extended release of oxycodone to treat severe pain (Compl. ¶1, 7). The complaint alleges that these generic products are formulated with a high molecular weight PEO and manufactured using a process that includes a thermal curing step, mirroring the technology claimed in the patents-in-suit (Compl. ¶29, 36, 43). As generic equivalents to OxyContin®, they are intended to compete directly in the large commercial market for long-term opioid pain treatment (Compl. ¶1, 22).
No probative visual evidence provided in complaint.
IV. Analysis of Infringement Allegations
’416 Patent Infringement Allegations
| Claim Element (from Independent Claim 1) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| a pharmaceutical composition comprising: at least active agent comprising an opioid or a pharmaceutically acceptable salt thereof, and at least one high molecular weight polyethylene oxide (PEO), having an approximate molecular weight of from 1 million to 8 million; | The complaint alleges that Amneal's Amended ANDA Products are pharmaceutical compositions containing an opioid and high molecular weight PEO as claimed. | ¶29 | col. 167:38-45 |
| wherein (a) the active agent and high molecular weight PEO are combined in a solid oral extended release dosage form that is (i) compression shaped, (ii) air cured by heated air, without compression, for a curing time of about 15 minutes to about 8 hours at a curing temperature of about 60 C to about 90 C, (iii) cooled, and (iv) hardened; | The complaint alleges the ANDA Products are solid oral dosage forms manufactured using the claimed shaping, curing, cooling, and hardening process. | ¶29 | col. 167:46-53 |
| (b) the high molecular weight PEO is at least partially melted upon curing and comprises at least about 50% (by weight) of the dosage form; | The complaint alleges the PEO in the ANDA Products is at least partially melted upon curing and meets the claimed weight percentage. | ¶29 | col. 167:54-57 |
| (c) the active agent comprises at least about 1.3% (by weight) of the dosage form; | The complaint alleges the active agent in the ANDA Products meets the claimed weight percentage. | ¶29 | col. 167:58-60 |
| (d) the molecular weight of each PEO is based on rheological measurements; | The complaint alleges the PEO molecular weight in the ANDA Products is based on rheological measurements. | ¶29 | col. 167:61-62 |
| (e) the total weight of the dosage form is calculated by excluding the combined weight of said film coatings; | The complaint alleges the total weight of the ANDA Products is calculated by excluding film coatings. | ¶29 | col. 167:63-65 |
| and (f) the dosage form is expanded upon curing, as measured by a decrease in density of at least about 1.5%, and the dosage form provides a hardness of at least about 439 N. | The complaint alleges the ANDA Products expand upon curing, decrease in density, and achieve the claimed hardness as specified. | ¶29 | col. 168:1-5 |
’808 Patent Infringement Allegations
| Claim Element (from Independent Claim 1) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| A pharmaceutical composition comprising: at least one active agent comprising oxycodone or a pharmaceutically acceptable salt thereof; and at least one high molecular weight polyethylene oxide (PEO), having an approximate molecular weight of from 1 million to 15 million; at least one of an additive and a film coating; | The complaint alleges that Amneal's Amended ANDA Products are compositions containing oxycodone, high molecular weight PEO, and an additive/coating. | ¶36 | col. 159:36-44 |
| wherein (a) the active agent and high molecular weight PEO are combined in a solid oral extended release dosage form that is (i) compression shaped, (ii) air cured by heated air, without compression, for at least about 5 minutes at a temperature above the softening temperature of the high molecular weight PEO, (iii) cooled, and (iv) hardened; | The complaint alleges the ANDA Products are solid oral dosage forms made using the claimed shaping, curing, cooling, and hardening process. | ¶36 | col. 159:45-53 |
| (b) the high molecular weight PEO comprises at least about 30% (by weight) of the dosage form; | The complaint alleges the PEO in the ANDA Products meets the claimed weight percentage. | ¶36 | col. 159:54-56 |
| (c) the molecular weight of each PEO is based on rheological measurements; | The complaint alleges the PEO molecular weight in the ANDA Products is based on rheological measurements. | ¶36 | col. 159:57-59 |
| and (d) the total weight of the dosage form is calculated by excluding the combined weight of said film coatings. | The complaint alleges the total weight of the ANDA Products is calculated by excluding film coatings. | ¶36 | col. 159:60-62 |
Identified Points of Contention
- Technical Questions: The complaint makes conclusory allegations of infringement by reciting claim language. The central dispute will depend on the technical evidence contained within the confidential ANDA. Key factual questions will include: Does the ANDA specify a manufacturing process that includes a thermal curing step meeting the patents' time and temperature parameters? Does the ANDA provide data showing the final product exhibits the claimed physical properties, such as the specific hardness (439 N for the ’416 Patent), PEO concentration, and density decrease upon curing?
- Scope Questions: A likely area of dispute will be the interpretation of process limitations. For example, does the accused manufacturing process constitute "air cured by heated air, without compression" as that phrase is understood in light of the patent specification? The defendant may argue its process differs in a way that avoids this limitation, raising a question of claim scope for the court.
V. Key Claim Terms for Construction
The Term: "air cured by heated air, without compression"
- Context and Importance: This process limitation is a cornerstone of the asserted independent claims in both the ’416 and ’808 patents. The definition of this multi-part term—particularly what constitutes "curing" and "without compression"—will be critical to determining whether the manufacturing process detailed in the ANDA infringes. Practitioners may focus on this term because infringement will turn on whether the accused process falls within its scope.
- Intrinsic Evidence for Interpretation:
- Evidence for a Broader Interpretation: The specification suggests that curing can take place in various apparatuses, such as a "convection pan or fluidized bed" (’416 Patent, col. 20:42-45), which may support an interpretation not strictly limited to the specific equipment used in the patent's examples.
- Evidence for a Narrower Interpretation: The patents describe the curing step in detail, including specific temperature profiles (e.g., a "plateau-like form") and durations that result in the desired tamper-resistance (’416 Patent, col. 19:6-8). A defendant could argue that "cured" requires achieving these specific thermal conditions and resultant physical properties, potentially narrowing the term's scope to exclude processes that differ meaningfully.
The Term: "hardened"
- Context and Importance: This term describes the final state of the dosage form after the claimed process. While qualitative, it is tied to the quantitative, objective metrics of tamper resistance, such as the hardness value of 439 N in claim 1 of the ’416 Patent. The construction of "hardened" will be important for establishing whether the accused product achieves the claimed result.
- Intrinsic Evidence for Interpretation:
- Evidence for a Broader Interpretation: The patents do not provide an explicit definition for "hardened," which may support giving the term its plain and ordinary meaning as understood by a person of ordinary skill in the art of pharmaceutical formulation.
- Evidence for a Narrower Interpretation: The specification consistently links the "hardened" state to measurable physical properties, such as resistance to crushing and a specific breaking strength or hardness value (’416 Patent, col. 168:1-5). A party may argue that for a tablet to be considered "hardened" under the claims, it must meet these objective, functional criteria described in the specification.
VI. Other Allegations
Indirect Infringement
The complaint alleges that upon FDA approval, Kashiv's commercial manufacture, use, importation, or sale of its ANDA products will contribute to and/or induce infringement of the patents-in-suit (Compl. ¶30, 37, 44). These allegations are prospective and rely on future commercial activity.
Willful Infringement
Willfulness is alleged based on Kashiv's purported knowledge of the patents-in-suit. The complaint states that Kashiv "has been aware of the existence of" the patents and has "no reasonable basis for believing" its products would not infringe, which it claims renders the case "exceptional" under 35 U.S.C. § 285 (Compl. ¶32, 39, 46). This knowledge is premised on the Orange Book listing of the patents and the sending of the Paragraph IV certification letter (Compl. ¶1, 25).
VII. Analyst’s Conclusion: Key Questions for the Case
- A central evidentiary question will be one of technical proof: as this is a Hatch-Waxman action, the case will depend almost entirely on the contents of the defendant's confidential ANDA. The primary issue will be whether discovery reveals that the accused generic product's formulation (e.g., PEO weight percentage, molecular weight) and manufacturing process (e.g., curing time, temperature, method) map onto the specific quantitative and qualitative limitations of the asserted claims.
- A core legal dispute will be one of claim construction: the outcome will likely hinge on the court's interpretation of key terms defining the patented process and product, such as "air cured by heated air, without compression" and "hardened." Whether these terms are construed broadly based on their plain meaning or more narrowly in light of the specific examples and physical properties described in the specification will be critical to the infringement analysis.
- A threshold procedural issue is one of party liability: the complaint explicitly notes uncertainty about whether Defendant Kashiv or non-party Amneal is the owner of the ANDA at issue (Compl. ¶6, 25). Resolving which entity is the proper defendant responsible for the ANDA submission will be a necessary prerequisite to adjudicating the substantive infringement claims.