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US 7,745,414 B2Granted
Glucopyranosyl-substituted benzonitrile derivatives, pharmaceutical compositions containing such compounds, their use and process for their manufacture
AssigneeBoehringer Ingelheim International GmbH
InventorsMatthias Eckhardt, Frank Himmelsbach, Peter Eickelmann, Achim Sauer, Leo Thomas
Life of this patent
Estimating the term…
Abstract
Glucopyranosyl-substituted benzonitrile derivatives as defined herein, including 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.
Claims11
A glucopyranosyl-substituted benzonitrile derivative selected from the list according to formula II, III, or i.2,
- wherein
- R3 is cyclopentyloxy, cyclobutyloxy, cyclohexyloxy, tetrahydropyran-4-yloxy, 1-acetyl-piperidin-4-yloxy or C1-3-alkyloxy, and
- R′ denotes H, C1-4-alkyl, (C1-18-alkyl)carbonyl, (C1-18-alkyl)oxycarbonyl, arylcarbonyl or aryl-(C1-3-alkyl)-carbonyl, wherein the alkyl or aryl groups may be mono- or polysubstituted by halogen;
- R8a, R8b, R8c, R8d independently of one another denote hydrogen or an allyl group, a benzyl group, a (C1-4-alkyl)carbonyl, (C1-4-alkyl)oxycarbonyl, arylcarbonyl, aryl-(C1-3-alkyl)-carbonyl and aryl-(C1-3-alkyl)-oxycarbonyl or a RaRbRcSi group or a ketal or acetal group, particularly an alkylidene or arylalkylidene ketal or acetal group, while in each case two adjacent groups R8a, R8b, R8c, R8d may form a cyclic ketal or acetal group or a 1,2-di(C1-3-alkoxy)-1,2-di(C1-3-alkyl)-ethylene bridge, while the above-mentioned ethylene bridge forms, together with two oxygen atoms and the two associated carbon atoms of the pyranose ring, a substituted dioxane ring, particularly a 2,3-dimethyl-2,3-di(C1-3-alkoxy)- 1,4-dioxane ring, and while alkyl, allyl, aryl and/or benzyl groups may be mono- or polysubstituted by halogen or C1-3-alkoxy, and while benzyl groups may also be substituted by a di-(C1-3-alkyl)amino group;
- and
- Ra, Rb, Rc independently of one another denote C1-4-alkyl, aryl or aryl-C1-3-alkyl, wherein the aryl or alkyl groups may be mono- or polysubstituted by halogen;
- while by the aryl groups mentioned in the definition of the above groups are meant phenyl or naphthyl groups;
- and
- Alk denotes C1-4-alkyl.
6 more elements
A glucopyranosyl-substituted benzonitrile derivative selected from the group consisting of:
- (1) 2-(4-Cyclopentyloxy-benzyl)-4-(β-D-glucopyranos- 1-yl)-benzonitrile,
- (2) 2-(4-Cyclobutyloxy-benzyl)-4-(β-D-glucopyranos- 1-yl)-benzonitrile,
- (3) 2-(4-Cyclohexyloxy-benzyl)-4-(β-D-glucopyranos- 1-yl)-benzonitrile,
- (4) 2-[4-(Tetrahydropyran-4-yloxy)-benzyl]-4-(β-D-glucopyranos-1-yl)-benzonitrile,
- (5) 2-[4-(1-Acetyl-piperidin-4-yloxy)-benzyl]-4-(β-D-glucopyranos-1-yl)-benzonitrile,
- (6) 2-(4-Methoxy-benzyl)-4-(β-D-glucopyranos- 1-yl)-benzonitrile,
- (7) 2-(4-Ethoxy-benzyl)-4-(β-D-glucopyranos- 1-yl)-benzonitrile,
- (8) 4-(β-D-glucopyranos-1-yl)-2-(4-isopropoxy-benzyl)-benzonitrile,
- or a derivative thereof wherein one or more hydroxyl groups of the β-D-glucopyranosyl group are acylated with groups selected from (C1-18-alkyl)carbonyl, (C1-18-alkyl)oxycarbonyl, phenylcarbonyl and phenyl-(C1-3-alkyl)-carbonyl.
6 more elements
Dependencies are inferred from the claim text.