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

• US 10,696,683 B2
• Filed: 05/30/2018
• Issued: 06/30/2020
• 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): Anderson, James D.
• Application Number:
  US15/992,287
• Publication Number:
  US 20180273542A1
• Time in Patent Office: 762 Days
• CPC Class Codes: A61P 25/36 Opioid-abuse
• CPC Class Codes: C07D 489/08 Oxygen atom

Abstract

The invention describes pharmaceutical compounds and compositions comprised of a ligand attached to the opioid oxycodone, 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 oxycodone prodrug of the following formula where the prodrug moiety X is attached covalently to the oxycodone molecule via the 6 position ketone enolate oxygen as the enolate ester,

2. The oxycodone prodrug according to claim 1 wherein the amino acids of compounds (b)(ii) are selected from naturally occurring proteinogenic amino acids, non-natural amino acids, naturally occurring (L)-isomers, non-natural (D)-isomers, mixtures of the (L) and (D) isomers, racemates and mixtures of diastereomers.

3. The oxycodone prodrug according to claim 2 wherein the amino acids of compounds (b)(ii) are selected from the group consisting of any of the 22 naturally occurring proteinogenic amino acids.

4. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable excipient.

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

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