Glucopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
AssigneeBoehringer Ingelheim International GmbH
InventorsMatthias Eckhardt, Peter Eickelmann, Frank Himmelsbach, Edward Leon Barsoumian, Leo Thomas
Life of this patent
Estimating the term…
Abstract
Glucopyranosyl-substituted benzene derivatives of general formula I where the groups R1 to R6 as well as R7a, R7b, R7c 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.
Claims25
Glucopyranosyl-substituted benzene derivatives of general formula I.2c
- wherein
- R1 is selected from hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, ethynyl, hydroxy, methoxy, ethoxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, and
- R2 is hydrogen, fluorine, hydroxy, methoxy, ethoxy or methyl, and
- R3 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
- R4, R5 independently of one another is hydrogen or fluorine, and
- R6 is hydrogen, (C1-6-alkyl)carbonyl or (C1-6-alkyl)oxycarbonyl, and
- R7a, R7b and R7c 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.
1 -Chloro-2-(4-cyclopentyloxybenzyl)-4-(β-D-glucopyranos- 1-yl)-benzene.
1 -Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene.
1 -Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene.
1 -Chloro-4-(β-D-glucopyranos-1-yl)-2-(4-cyclobutyloxy-benzyl)-benzene.
1 -Chloro-4-(β-D-glucopyranos-1-yl)-2-(4-cyclohexyloxy-benzyl)-benzene.
1 -Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(tetrahydropyran-4-yloxy)-benzyl]-benzene.
1 -Chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(1-acetyl-piperidin-4-yloxy)-benzyl]-benzene.
1-(β-D-Glucopyranos-1-yl)-4-methyl-3-[4-(2-trimethylsilyl-ethyl)-benzyl]-benzene.
1-Chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene.
1-Fluoro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene.
1-(β-D-Glucopyranos-1-yl)-3-(4-ethynyl-benzyl)-benzene.
1-Methoxy-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene.
Dependencies are inferred from the claim text.