Opioid ketal compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-11731979-B2
Application number	US-202117407222-A
Country	US
Kind code	B2
Filing date	Aug 20, 2021
Priority date	May 24, 2013
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

This invention relates to opioid ketal compounds of Formula (I), Formula (II), or Formula (III): or a pharmaceutically acceptable salts thereof, wherein R1 is H or CH3, R2 is H or OH, n is 0, 1, 2 or 3, R3 and R4 are independently H or optionally substituted C1-C4 alkyl, or when n is 0, then R3 and R4 and the carbon atoms to which they are attached together form six, or seven membered ring, which is optionally mono or disubstituted by C1-C4 alkyl. The invention also relates to oxycodone ketal compounds of Formula (IV) or (V): or a pharmaceutically acceptable salts thereof. The invention also relates to the use of such compounds for the treatment, prevention, or amelioration of pain.

First claim

What is claimed is:

1. A method of treating or ameliorating pain in a mammal identified as in need thereof through an oxycodone therapy, comprising orally administering to the mammal an effective amount of one or more compounds of Formula II, III, or V:

or a pharmaceutically acceptable salt thereof, wherein the carbon atom labeled * or ** is in R or S configuration, and
wherein the method provides the mammal an extended release of the oxycodone, as compared to an oral administration of the oxycodone or a pharmaceutically acceptable salt thereof in an immediate release form to the mammal.

2. The method of claim 1 , wherein the pain is acute pain or chronic pain.

3. The method of claim 1 , wherein the method comprises the administration of an effective amount of a compound of Formula V selected from the group consisting of

or a pharmaceutically acceptable salt thereof.

4. The method of claim 3 , wherein the method comprises administering to the mammal a mixture of two or more compounds of Formula V or pharmaceutically acceptable salts thereof.

5. The method of claim 3 , wherein the method comprises administering to the mammal a mixture comprising compounds VA, VB, VC, and VD, or pharmaceutically acceptable salts thereof.

6. The method of claim 1 , wherein the method comprises the administration of an effective amount of one or more compounds of Formula II or Formula III:

or a pharmaceutically acceptable salt thereof.

7. The method of claim 6 , wherein the method comprises the administration of a mixture comprising two or more stereoisomers of a compound of Formula III, or pharmaceutically acceptable salts thereof.

8. The method of claim 1 , wherein the method reduces an abuse or misuse potential of the oxycodone therapy.

9. The method of claim 1 , wherein the method reduces euphoric effects of the oxycodone therapy.

10. The method of claim 1 , wherein the compound of Formula II, III, or V is administered at a dose of from 0.1 to 5 mg/kg, or a molar equivalent amount of a pharmaceutically acceptable salt thereof, based on the body weight of the mammal.

11. The method of claim 1 , wherein the compound of Formula II, III, or V, or a pharmaceutically acceptable salt thereof, is administered as part of a pharmaceutical composition comprising between 5 mg and 320 mg of the compound of Formula II, III, or V or a molar equivalent of the pharmaceutically acceptable salt thereof.

Assignees

• Rhodes Tech

Inventors

• Kupper Robert J
• Glowaky Raymond C

Classifications

• C07D489/08 Primary

  Oxygen atom · CPC title

• A61K9/0053

  Mouth and digestive tract, i.e. intraoral and peroral administration · CPC title

• A61K31/485

  Morphinan derivatives, e.g. morphine, codeine · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• C07D489/02

  with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone · CPC title