Compounds useful as modulators of TRPM8

Patent metadata

Field	Value
Publication number	US-9840471-B2
Application number	US-201414768146-A
Country	US
Kind code	B2
Filing date	Feb 19, 2014
Priority date	Feb 19, 2013
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

The present invention includes compounds useful as modulators of TRPM8, such as compounds of Formulae (Ia), (Ib) and (Ic), and the subgenus and species thereof; personal products containing those compounds; and the use of those compounds and the personal products, particularly the use of increasing or inducing chemesthetic sensations, such as cooling or cold sensations.

First claim

What is claimed is:

1. A compound having structural Formula (Ia):

or a salt or solvate thereof;
wherein
R 1 is optionally substituted phenyl;
R 2 and R 3 are independently selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted carbocyclyl, optionally substituted heteroaryl, and optionally substituted heterocyclyl; and
R 4 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted carbocyclyl, optionally substituted heteroaryl, or optionally substituted heterocyclyl.

2. The compound of claim 1 , a:
wherein
R 4 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted carbocyclyl, optionally substituted heteroaryl, or substituted heterocyclyl.

3. The compound of claim 2 , wherein R 1 is phenyl.

4. The compound of claim 2 , wherein R 2 is optionally substituted aryl, optionally substituted carbocyclyl, optionally substituted heteroaryl, or optionally substituted heterocyclyl.

5. The compound of claim 2 , wherein R 3 is optionally substituted alkyl or optionally substituted alkenyl.

6. The compound of claim 5 , wherein R 3 is optionally substituted C 1 -C 4 alkyl.

7. The compound of claim 2 ;
R 2 is optionally substituted carbocyclyl; and
R 3 is optionally substituted alkyl.

8. The compound of claim 2 , wherein R 4 is optionally substituted alkyl.

9. The compound of claim 8 , wherein R 4 is optionally substituted C 1 -C 4 alkyl.

10. The compound of claim 1 , which is selected from the group consisting of

and a salt or solvate thereof.

11. A composition comprising a compound of claim 1 , or a salt or solvate thereof; and at least one carrier.

12. The composition of claim 11 , which is an ingestible composition or personal care composition.

13. The composition of claim 12 , wherein the ingestible composition is a food or beverage.

14. The composition of claim 11 , wherein the compound in the composition is in a concentration ranging from about 1 ppm to 500 ppm.

15. The composition of claim 11 , which is a textile product or a packaging material.

16. A compound having structural Formula (Ia):

or a salt or solvate thereof;
wherein
R 1 is selected from the group consisting of pyrrolyl, thienyl, and pyridyl, each of which is optionally substituted;
R 2 and R 3 are independently selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted carbocyclyl, optionally substituted heteroaryl, and optionally substituted heterocyclyl; and
R 4 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted carbocyclyl, optionally substituted heteroaryl, or optionally substituted heterocyclyl.

17. The compound of claim 16 , wherein R 2 is optionally substituted aryl, optionally substituted carbocyclyl, optionally substituted heteroaryl, or optionally substituted heterocyclyl.

18. The compound of claim 16 , wherein R 3 is optionally substituted alkyl or optionally substituted alkenyl.

19. The compound of claim 18 , wherein R 3 is optionally substituted C 1 -C 4 alkyl.

20. The compound of claim 16 ;
R 2 is optionally substituted carbocyclyl; and
R 3 is optionally substituted alkyl.

21. The compound of claim 16 , wherein R 4 is optionally substituted alkyl.

22. The compound of claim 21 , wherein R 4 is optionally substituted C 1 -C 4 alkyl.

23. The compound of claim 16 , which is selected from the group consisting of

and a salt or solvate thereof.

Assignees

• Senomyx Inc

Inventors

• Chumakova Lyudmyla
• Patron Andrew
• Priest Chad
• Karanewsky Donald
• Kimmich Rachel
• Boren Brant Clayton
• Hammaker Jeffrey Robert
• Chumakov Volodymyr
• Zhao Wen
• Noncovich Alain
• Ung Jane

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• C07D233/78

  Radicals substituted by oxygen atoms · CPC title

• C07D401/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D239/22

  with hetero atoms directly attached to ring carbon atoms · CPC title

• C07D207/333

  Radicals substituted by oxygen or sulfur atoms · CPC title