Substituted benzimidazole-, benztriazole-, and benzimidazolone-o-glucosides

Abstract

This invention relates to substituted benzimidazole-O-glucosides, benztriazole-O-glucosides, and benzimidazolone-O-glucosides, compositions containing them, and methods of using them, for example, for the treatment or prophylaxis of diabetes and Syndrome X.

1 - 20 . (canceled) 
     
     
         21 . A method for treating diabetes or Syndrome X, or associated symptoms or complications thereof in a mammal, said method comprising administering to a mammal in need of treatment an effective amount of a compound selected from the group consisting of 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-3H-benzoimidazol-4-yloxy}-β-D glucopyranoside; 2-[3-(4-Ethyl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl)-3H-benzotriazol-4-yloxy]-β-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. 
     
     
         22 . The method of  claim 21 , wherein said diabetes is type II diabetes. 
     
     
         23 - 54 . (canceled) 
     
     
         55 . A method for treating diabetes or Syndrome X, or associated symptoms or complications thereof in a mammal, said method comprising administering to a mammal in need of treatment an effective amount of a compound selected from the group consisting of 2-[3-(4-Ethyl-benzyl)-6-methyl-3H-benzoimidazol-4-yloxy]-D-glucopyranoside; 2-{3-[2-(4-Methoxyphenyl)-ethyl]-3H-benzoimidazol-4-yloxy}-β-D-glucopyranoside; 2-{3-[2-(4-methoxy-phenyl)-ethyl]-3H-benzotriazol-4-yloxy}-β-D-glucopyranoside; 2-[3-(2-Naphthalen-2-yl-ethyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl)-1,3-dihydro-benzoimidazol-2-one-4-yloxy]-β-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. 
     
     
         56 . The method of  claim 55 , wherein said diabetes is type II diabetes. 
     
     
         57 . A method for treating diabetes or Syndrome X, or associated symptoms or complications thereof in a mammal, said method comprising administering to a mammal in need of treatment an effective amount of a compound selected from the group consisting of 2-[3-(2-Naphthalen-2-yl-ethyl)-1,3-dihydro-benzoimidazol-2-one-4-yloxy]-β-D-glucopyranoside and 2-[3-(2-(4-Methoxyphenyl)-ethyl)-1,3-dihydro-benzoimidazol-2-one-4-yloxy]-β-D glucopyranoside; or a pharmaceutically acceptable salt thereof. 
     
     
         58 . The method of  claim 57 , wherein said diabetes is type II diabetes. 
     
     
         59 . A method for treating diabetes or Syndrome X, or associated symptoms or complications thereof in a mammal, said method comprising administering to a mammal in need of treatment an effective amount of a compound selected from the group consisting of 2-[3-(5-Ethyl-thiophen-2-ylmethyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Ethoxy-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Ethoxy-benzyl)-3H-benzotriazol-4-yloxy]-β-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-3H-benzoimidazol-4-yloxy}-β-D-glucopyranoside; 2-[3-(4-Thiophen-3-yl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Pyrazol-1-yl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Pyridin-3-yl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Pyrrol-1-yl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Imidazol-1-yl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-(3-Biphenyl-4-ylmethyl-3H-benzoimidazol-4-yloxy)-β-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-6-methoxy-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-6-trifluoromethyl-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-3H-benzoimidazol-4-yloxy]-6-O-ethoxycarbonyl-β-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-3H-benzotriazol-4-yloxy]-6-O-ethoxycarbonyl-β-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl)-6-methyl-3H-benzotriazol-4-yloxy]-β-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. 
     
     
         60 . The method of  claim 59 , wherein said diabetes is type II diabetes. 
     
     
         61 . A method for treating diabetes or Syndrome X, or associated symptoms or complications thereof in a mammal, said method comprising administering to a mammal in need of treatment an effective amount of a compound selected from the group consisting of 2-[3-(4-Ethyl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-3H-benzoimidazol-4-yloxy}-β-D glucopyranoside; 2-[3-(4-Ethyl-benzyl)-3H-benzotriazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-6-methyl-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-{3-[2-(4-methoxy-phenyl)-ethyl]-3H-benzotriazol-4-yloxy}-β-D-glucopyranoside; 2-[3-(5-Ethyl-thiophen-2-ylmethyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-3H-benzoimidazol-4-yloxy}-β-D-glucopyranoside; 2-[3-(4-Thiophen-3-yl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-[3-(4-Pyrrol-1-yl-benzyl)-3H-benzoimidazol-4-yloxy]-β-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-3H-benzoimidazol-4-yloxy}-β-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-3H-benzotriazol-4-yloxy}-β-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-3H-benzotriazol-4-yloxy}-β-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl)-6-methyl-3H-benzotriazol-4-yloxy]-β-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. 
     
     
         62 . The method of  claim 61 , wherein said diabetes is type II diabetes.