Substituted pyridyl amide compounds as modulators of the histamine H3 receptor

Patent metadata

Field	Value
Publication number	US-9321729-B2
Application number	US-201414561156-A
Country	US
Kind code	B2
Filing date	Dec 4, 2014
Priority date	May 30, 2006
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

Certain substituted pyridyl amide compounds are histamine H 3 receptor modulators useful in the treatment of histamine H 3 receptor-mediated diseases.

First claim

What is claimed is:

1. A compound of Formula (I):

wherein
R 1 is —C 1-4 alkyl or saturated monocyclic cycloalkyl;
m is 1 or 2;
X is CH;
Y is N;
R a is —H, —Z—Ar, —CH 2 NR b R c , —CN, —CO 2 C 1-4 alkyl, —CO 2 H, or —CONR b R c ;
where R b and R c are each independently —H or —C 1-4 alkyl; and

R 2 is Z—Ar;
where Z is O or S; and
Ar is a phenyl or monocyclic heteroaryl group unsubstituted or substituted with one, two, or three R 3 substituents;
where each R 3 substituent is independently selected from the group consisting of:
halo, —C 1-4 alkyl, —OH, —OC 1-4 alkyl, —SC 1-4 alkyl, —CN, —CONR d R e , and —NO 2 ;
where R d and R e are each independently —H or —C 1-4 alkyl;

or a pharmaceutically acceptable salt thereof.

2. A compound as defined in claim 1 , wherein R 1 is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, or tert-butyl.

3. A compound as defined in claim 1 , wherein R 1 is methyl or isopropyl.

4. A compound as defined in claim 1 , wherein R 1 is cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

5. A compound as defined in claim 1 , wherein m is 1.

6. A compound as defined in claim 1 , wherein m is 2.

7. A compound as defined in claim 1 , wherein R a is —CN, —CONH 2 , or —CH 2 NH 2 .

8. A compound as defined in claim 1 , wherein R a is —H.

9. A compound as defined in claim 1 , wherein Z is O.

10. A compound as defined in claim 1 , wherein Z is S.

11. A compound as defined in claim 1 , wherein Ar is a phenyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyrimidinyl, or pyrazinyl group, each unsubstituted or substituted with one, two, or three R 3 substituents.

12. A compound as defined in claim 1 , wherein Ar is a phenyl group unsubstituted or substituted with one, two, or three R 3 substituents.

13. A compound as defined in claim 1 , wherein Ar is a 4-halophenyl group.

14. A compound as defined in claim 1 , wherein Ar is phenyl, 3,4-dichlorophenyl, 4-methylsulfanylphenyl, 3-chlorophenyl, 3-fluorophenyl, 4-chloro-3-methylphenyl, 3-cyanophenyl, 4-chlorophenyl, 4-fluorophenyl, 3,4-difluorophenyl, 2-fluorophenyl, 3-chlorophenyl, 2,4-difluorophenyl, 3,5-dichlorophenyl, 2,5-difluorophenyl, 3,5-difluorophenyl, 3-methyl-4-methylsulfanylphenyl, or 3-pyridyl.

Assignees

• Janssen Pharmaceutica Nv

Inventors

• Keith John M
• Letavic Michael A
• Ly Kiev S
• Mani Neelakandha S
• Mills John E
• Pandit Chennagiri R
• Villani Frank J
• Zhong Hua

Classifications

• A61P43/00

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

• A61P25/18

  Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia · CPC title

• A61P25/20

  Hypnotics; Sedatives · CPC title

• A61P25/06

  Antimigraine agents · CPC title

• A61P25/30

  for treating abuse or dependence · CPC title