Halogenated sulfonamide derivatives

Abstract

This invention is directed to halogenated sulfonamide derivatives which are ligands at the NPY Y5 receptor. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention also provides a pharmaceutical composition made by admixing a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention further provides a process for making a pharmaceutical composition comprising combining a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention also provides a method of treating a subject suffering from depression which comprises administering to the subject an amount of a compound of the subject invention. This invention also provides a method of treating a subject suffering from anxiety which comprises administering to the subject an amount of a compound of the subject invention. This invention also provides a method of treating a subject suffering from obesity which comprises administering to the subject an amount of a compound of the subject invention. Furthermore, the present invention is directed to use of a compound of the invention for the manufacture of a medicament for treating a subject suffering from depression, anxiety or obesity.

Description

Claims

1. A compound having the structure:

2. The compound of claim 1, wherein R3 is H; wherein m is 0 or 1; and wherein n is 0 or 1.

3. The compound of claim 2, wherein R1 is H or C1-C4 straight chained or branched alkyl.

4. The compound of claim 3, wherein R2 is C1-C4 straight chained or branched alkyl.

5. The compound of claim 4, wherein R1 is H, methyl or ethyl; and wherein R2 is methyl or ethyl.

6. The compound of claim 5, wherein R1 is methyl; R2 is methyl; and R4 is 2-pyridyl or 3-pyridyl, wherein the 2-pyridyl or 3-pyridyl is substituted with F or CF3 and optionally substituted with CH3.

7. The compound of claim 6, wherein n is 1.

8. The compound of claim 6, wherein m is 1.

9. The compound of claim 7, wherein R4 is 3-pyridyl substituted with F; and wherein R5 is H.

10. The compound of claim 8, wherein R4 is 3-pyridyl substituted with F; and wherein R5 is H.

11. The compound of claim 2, wherein R1, R2 and the carbon to which they are attached form C3-C6 cycloalkyl.

12. The compound of claim 11, wherein R4 is 2-pyridyl or 3-pyridyl substituted with F.

13. The compound of claim 12, wherein R1, R2 and the carbon to which they are attached form cyclopropyl or cyclobutyl; wherein R4 is 3-pyridyl substituted with F; wherein R5 is H; and wherein n is 0.

14. The compound of claim 1, wherein the compound is selected from the group consisting of [(methylethyl)sulfonyl](trans-4-{[(4-(6-fluoro-pyridin-2-yl)(1,3-thiazol-2-yl))amino]methyl}cyclohexyl)amine; [(methylethyl)sulfonyl]({trans-4-[(4-(6-fluoro-pyridin-2-yl)(1,3-thiazol-2-yl))amino]cyclohexyl}methyl)amine; [(methylethyl)sulfonyl]({trans-4-[(4-(2-methyl,6-fluoro-pyridin-3-yl)(1,3-thiazol-2-yl))amino]cyclohexyl}methyl)amine; and (methylethyl)sulfonyl](trans-4-{[(4-(2-fluoro-pyridin-3-yl)(1,3-thiazol-2-yl))amino]methyl}cyclohexyl)amine or a pharmaceutically acceptable salt thereof.

15. The compound of claim 1, wherein the compound is selected from the group consisting of [(methylethyl)sulfonyl]({trans-4-[(4-(2-fluoro-pyridin-3-yl)(1,3-thiazol-2-yl))amino]cyclohexyl}methyl)amine; [(methylethyl)sulfonyl]({trans-4-[(4-(6-fluoro-pyridin-3-yl)(5-methyl-1,3-thiazol-2-yl))amino]cyclohexyl}methyl)amine; and (methylethyl)sulfonyl]({trans-4-[(4-(2-fluoro-pyridin-3-yl)(5-methyl-1,3-thiazol-2-yl))amino]cyclohexyl}methyl)amine or a pharmaceutically acceptable salt thereof.

16. The compound of claim 1, wherein the compound is selected from the group consisting of [(methylethyl)sulfonyl]({trans-4-[(4-(6-trifluoromethyl-pyridin-3-yl)(5-methyl-1,3-thiazol-2-yl))amino]cyclohexyl}methyl)amine; and [(methylethyl)sulfonyl](trans-4-{[(4-(6-bromopyridin-2-yl)(1,3-thiazol-2-yl))amino]methyl}cyclohexyl)amine or a pharmaceutically acceptable salt thereof.

17. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.

18. A method of treating a subject suffering from depression comprising administering to the subject a therapeutically effective amount of a compound of claim 1.

19. A method of treating a subject suffering from anxiety comprising administering to the subject a therapeutically effective amount of a compound of claim 1.

20. A method of treating a subject suffering from obesity comprising administering to the subject a therapeutically effective amount of a compound of claim 1.