Glucopyranosyl-substituted phenyl derivates, medicaments containing such compounds, their use and process for their manufacture

Abstract

Glucopyranosyl-substituted benzene derivatives of general formula I where the groups R 1 to R 6 as well as R 7a , R 7b , R 7c are defined herein and the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.

1 .- 28 . (canceled) 
   
   
       29 . Glucopyranosyl-substituted benzene derivatives of general formula I.2c 
     
       
         
         
             
             
         
       
       wherein 
       R 1  is selected from hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, ethynyl, hydroxy, methoxy, ethoxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, and 
       R 2  is hydrogen, fluorine, hydroxy, methoxy, ethoxy or methyl, and 
       R 3  is selected from trimethylsilylethyl, ethynyl, 2-hydroxyprop-2-ylethynyl, 2-methoxyprop-2-ylethynyl, 3-hydroxy-1-propyn-1-yl, 3-methoxy-1-propyn-1-yl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuran-3-yloxy, tetrahydropyran-4-yloxy, piperidin-4-yloxy, N-methylpiperidin-4-yloxy and N-acetylpiperidin-4-yloxy, and 
       R 4 , R 5  independently of one another is hydrogen or fluorine, and 
       R 6  is hydrogen, (C 1-6 -alkyl)carbonyl or (C 1-6 -alkyl)oxycarbonyl, and 
       R 7a , R 7b  and R 7c  are hydrogen, 
     
     while, unless otherwise stated, the above-mentioned alkyl groups may be straight-chain or branched, the stereoisomers thereof, the mixtures thereof and the salts thereof. 
   
   
       30 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 1  is methyl or chlorine. 
   
   
       31 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 3  is ethynyl. 
   
   
       32 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 3  is trimethylsilylethyl. 
   
   
       33 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 3  is cyclobutyloxy. 
   
   
       34 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 3  is cyclopentyloxy. 
   
   
       35 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 3  is cyclohexyloxy. 
   
   
       36 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 3  is tetrahydrofuran-3-yloxy. 
   
   
       37 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 3  is tetrahydropyran-4-yloxy. 
   
   
       38 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 2  is hydrogen or methyl. 
   
   
       39 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 2  is hydrogen. 
   
   
       40 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 4  and R 5  are hydrogen. 
   
   
       41 . Glucopyranosyl-substituted benzene derivatives according to  claim 29 , wherein R 6  is hydrogen. 
   
   
       42 . 1-Chloro-2-(4-cyclopentyloxybenzyl)-4-(β-D-glucopyranos-1-yl)-benzene. 
   
   
       43 . 1-Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene. 
   
   
       44 . 1-Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene. 
   
   
       45 . 1-Chloro-4-(β-D-glucopyranos-1-yl)-2-(4-cyclobutyloxy-benzyl)-benzene. 
   
   
       46 . 1-Chloro-4-(β-D-glucopyranos-1-yl)-2-(4-cyclohexyloxy-benzyl)-benzene. 
   
   
       47 . 1-Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(tetrahydropyran-4-yloxy)-benzyl]-benzene. 
   
   
       48 . 1-Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(1-acetyl-piperidin-4-yloxy)-benzyl]-benzene. 
   
   
       49 . 1-(β-D-Glucopyranos-1-yl)-4-methyl-3-[4-(2-trimethylsilyl-ethyl)-benzyl]-benzene. 
   
   
       50 . 1-Chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene. 
   
   
       51 . 1-Fluoro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene. 
   
   
       52 . 1-(β-D-Glucopyranos-1-yl)-3-(4-ethynyl-benzyl)-benzene. 
   
   
       53 . 1-Methoxy-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene.