IP Library › Patent Application 13584043
Patent Application
App. No. 13/584,043

3-AMINO-PYRIDINE DERIVATIVES FOR THE TREATMENT OF METABOLIC DISORDERS

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Patent No.
US None
App. No.
13/584,043
Abstract

Compounds represented by the general formula (1): pharmaceutically acceptable salts or solvates thereof, a process for their manufacture; pharmaceutical compositions containing them; and use of the compounds in the treatment of metabolic disorders related to insulin resistance or hyperglycemia are described.

Claims (49)

1 . A method for the treatment of a metabolic disorder related to insulin resistance or hyperglycemia, comprising:

administering to a mammal in need thereof a therapeutically effective amount of a compound of formula (I), or a pharmaceutically acceptable salt thereof, the formula (I) being represented by:

where:

Ar is isoquinolin-3-yl;

B is —O—;

R 1 is H;

R 2 is —S(O) 2 R 4 ;

R 3 is chlorine; and

R 4 is 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 3-chloro-4-methylphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 3,4-dimethoxyphenyl, 4-trifluoromethoxyphenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2-chloro-4-fluorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 4-chlorophenyl, 2-chloro-4-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-fluoro-4-chlorophenyl; 4-cyanophenyl, phenyl-3-carboxylic acid [phenyl-3-COOH], or 4-acetamidophenyl [CH 3 CONH-phenyl].

2 . The method according to claim 1 ;

wherein the compound of formula (I) is selected from:

2,4-Dichloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)benzenesulfonamide;

3-(N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)sulfamoyl)benzoic acid;

3-Chloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-methylbenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-2,4,6-trimethyl benzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-1-cyanobenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-3,5-dimethylbenzenesulfonamide;

3,5-Dichloro-N (5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)benzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-2-methylbenzenesulfonamide;

N-(5-Chloro-6 (isoquinolin-3-yloxy)pyridin-3-yl)-3-methylbenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-3-(trifluoromethyl)benzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-(trifluoromethyl)benzenesulfonamide;

4-Chloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)benzenesulfonamide;

4-Chloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-2-fluorobenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-2,4-difluorobenzenesulfonamide;

2-Chloro-N-(5 chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-fluorobenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-methylbenzenesulfonamide;

3,4-Dichloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)benzenesulfonamide;

N-(5-Chloro-6 (isoquinolin-3-yloxy)pyridin-3-yl)-4-(trifluoromethoxy)benzene-sulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-2,5-dimethoxybenzenesulfonamide;

2-Chloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4(trifluoromethyl)benzene sulfonamide;

N-(4-(N-(5 Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)sulfamoyl)phenyl)acetamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-3,4-dimethoxybenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-2,4-dimethoxybenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-methoxybenzenesulfonamide; and

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-fluorobenzenesulfonamide.

3 . The method according to claim 1 ;

wherein the compound of formula (I) is selected from:

2,4-Dichloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-Yl)benzenesulfonamide;

2-Chloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-fluorobenzenesulfonamide;

N-(5-Chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)-4-methylbenzenesulfonamide; and

3,4-Dichloro-N-(5-chloro-6-(isoquinolin-3-yloxy)pyridin-3-yl)benzenesulfonamide.

4 . The method according to claim 1 ;

wherein the metabolic disorder related to insulin resistance or hyperglycemia is selected from:

type 2 diabetes, obesity, glucose intolerance, dyslipidemia, hyperinsulinemia, atherosclerotic disease, polycystic ovary syndrome, coronary artery disease, hypertension, or non alcoholic fatty liver disease.

5 . The method according to claim 4 ;

wherein the metabolic disorder related to insulin resistance or hyperglycemia is type 2 diabetes.

6 . The method according to claims 4 ;

wherein the metabolic disorder related to insulin resistance or hyperglycemia is dyslipidemia.

Assignments (1)
CHANGE OF NAME Recorded Dec 19, 2012
From: PIRAMAL HEALTHCARE LIMITED
To: PIRAMAL ENTERPRISES LIMITED
Reel/Frame 029501/0861 →