Analgesic compounds and methods of use

Patent metadata

Field	Value
Publication number	US-10167295-B2
Application number	US-201514851248-A
Country	US
Kind code	B2
Filing date	Sep 11, 2015
Priority date	Mar 15, 2013
Publication date	Jan 1, 2019
Grant date	Jan 1, 2019

Abstract

Provided herein, inter alia, are methods and compositions for achieving an analgesic effect in subjects in need thereof.

First claim

What is claimed is:

1. A method of producing sexually dimorphic analgesia in a male subject in need thereof, the method comprising administering to the male subject a therapeutically effective amount of a compound having the formula:

or a pharmaceutically acceptable salt thereof; wherein R 4 is hydrogen or methyl; R 5 is —C(O)-L 1 -R 3 ; L 1 is a bond, —CH 2 —, —CH 2 CH 2 —, or —CH 2 CH 2 CH 2 —; and R 3 is (i) an unsubstituted 5-membered heterocyloalkyl; (ii) an unsubstituted 6-membered heterocycloalkyl; (iii) a 5-membered heterocyloalkyl substituted with one or two substituents selected from the group consisting of ═O, halogen, —OH, —NH 2 , —SH, —C(O)OH, —C(O)NH 2 , —CF 3 , —CCl 3 , —CN, —N 3 , an unsubstituted C 1 -C 8 alkyl, and benzyl; or (iv) a 6-membered heterocycloalkyl.

2. The method of claim 1 , wherein R 3 is (i) an unsubstituted 5-membered heterocyloalkyl containing one nitrogen heteroatom; (ii) an unsubstituted 6-membered heterocycloalkyl containing one nitrogen heteroatom; (iii) a 5-membered heterocyloalkyl containing one nitrogen heteroatom and one or two substituents selected from the group consisting of ═O, halogen, —OH, —NH 2 , —SH, —C(O)OH, —C(O)NH 2 , —CF 3 , —CCl 3 , —CN, —N 3 , an unsubstituted C 1 -C 8 alkyl, and a benzyl; or (iv) a 6-membered heterocycloalkyl containing one nitrogen heteroatom and one or two substituents selected from the group consisting of ═O, halogen, —OH, —NH 2 , —SH, —C(O)OH, —C(O)NH 2 , —CF 3 , —CCl 3 , —CN, —N 3 , an unsubstituted C 1 -C 8 alkyl, a benzyl, and an indene moiety.

3. The method of claim 1 , wherein R 3 is a 5-membered heterocyloalkyl containing one nitrogen heteroatom and one or two substituents selected from the group consisting of ═O, —OH, —NH 2 , benzyl, methyl, and ethyl; or a 6-membered heterocycloalkyl containing one nitrogen heteroatom and one or two substituents selected from the group consisting of ═O, —OH, —NH 2 , methyl, ethyl, benzyl, and an indene moiety.

4. The method of claim 1 , wherein the compound is of the formula:

5. The method of claim 4 , wherein the compound is of the formula:

6. The method of claim 5 , wherein the compound is of the formula:

Assignees

• Univ California

Inventors

• Levine Jon D
• Gallardo-Godoy Alejandra

Classifications

• C07D491/107 Primary

  with only one oxygen atom as ring hetero atom in the oxygen-containing ring · CPC title

• C07D489/02

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

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title