Alpha-hydroxy carboxylic acid and derivatives and other GRAS-based prodrugs of oxymorphone and uses thereof

• US 9,987,269 B2
• Filed: 12/01/2015
• Issued: 06/05/2018
• Est. Priority Date: 04/27/2015
• Status: Active Grant

• Current Assignee: 3St Research LLC
• Original Assignee: 3St Research LLC
• Inventors: Thottathil, John K.
• Primary Examiner(s): Sznaidman, Marcos L
• Application Number:
  US14/956,143
• Publication Number:
  US 20170151228A1
• Time in Patent Office: 917 Days
• Field of Search: 514282
• CPC Class Codes: A61K 31/485 Morphinan derivatives, e.g. morphine, codeine
• CPC Class Codes: A61K 47/542 Carboxylic acids, e.g. a fatty acid or an amino acid
• CPC Class Codes: A61K 47/543 Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
• CPC Class Codes: A61K 9/0053 Mouth and digestive tract, i.e. intraoral and peroral administration rectal administration A61K9/0031
• CPC Class Codes: A61P 25/36 Opioid-abuse

Abstract

The invention describes pharmaceutical compounds and compositions comprised of a ligand attached to the opioid oxymorphone, in a manner that substantially decreases or deters the potential for opioid abuse, addiction, illicit and illegal use, and overdose. When delivered at the proper dosage, the pharmaceutical composition provides therapeutic activity similar to that of the parent active agent.

Claims

1. An oxymorphone prodrug of the following formula where the prodrug moiety X is attached covalently to the oxymorphone molecule via the 6 position ketone enolate oxygen as the enolate ester,

4. An oral pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.

5. The pharmaceutical composition of claim 4, wherein the compound is a pharmaceutically acceptable salt form.

6. A method of treating pain comprising orally administering the composition of claim 4 to a patient.

2. An oxymorphone prodrug compound represented by any one of

3. A pharmaceutical composition comprising one or more of the oxymorphone prodrugs according to claim 2 and one or more pharmaceutically acceptable excipients.