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US 6,653,346 B1Granted
Cytoprotective benzofuran derivatives
AssigneeGalileo Pharmaceuticals, Inc.
InventorsBing Wang, Jian Chen
Life of this patent
Estimating the term…
Abstract
Cytoprotective compounds, many of which are benzofuran derivatives are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders characterized by inflammation or oxidative damage. They are also useful in the manufacture of pharmaceutical and cosmetic formulations for the treatment of such conditions.
Claims28
A compound represented by Formula I
- wherein:
- R1 is:
- hydrogen, optionally substituted (C1-C6)-alkyl, optionally substituted (C2-C10)-alkenyl, optionally substituted aryl, (optionally substituted (C1-C6)-alkoxy)carbonyl, or halogen;
- R2 and R3 are independently selected from optionally substituted (C1-C6)-alkyl, optionally substituted (C2-C10)-alkenyl, or optionally substituted (C3-C8)-cycloalkyl;
- R4 is:
- hydrogen, optionally substituted aryl, (optionally substituted(C1-C6)-alkyl)carbonyl, (optionally substituted aryl)carbonyl, (optionally substituted heterocyclyl)carbonyl, (optionally substituted heterocyclylalkyl)carbonyl, (optionally substituted (C1-C6)-alkoxy)carbonyl, (optionally substituted (C2-C10)-alkenyloxy)carbonyl, (optionally substituted amino)carbonyl, carboxy, formyl, or hydroxy(optionally substituted)(C1-C6)-alkyl;
- R5 is:
- hydrogen, (C1-C6)-alkyl, (C2-C10)-alkenyl, (optionally substituted alkoxy)carbonyl, carboxy, (optionally substituted amino)carbonyl, or optionally substituted aryl;
- provided that one of R4 or R5 is hydrogen, and that when R4 is hydrogen R5 is not hydrogen, and when R5 is hydrogen R4 is not hydrogen;
- R is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkylcarbonyl, phosphoryl, or polyalkoxy;
- or
- R and R1 with the atoms to which they are attached form an optionally substituted ring;
- single stereoisomers, mixtures of stereoisomers, and the pharmaceutically acceptable salts thereof.
10 more elements
The compound of selected from the group:
- (5-Hydroxy-3,6,7-trimethyl-benzofuran-2-yl)-phenyl-methanone;
- (5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-morpholin-4-yl-methanone;
- 1-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-ethanone;
- Acetic acid 2-(2-bromo-acetyl)-6,7-dimethyl-benzofuran-5-yl ester;
- 2-(i-Hydroxy-2-morpholin-4-yl-ethyl)-6,7-dimethyl-benzofuran-5-ol;
- Acetic acid 6,7-dimethyl-2-(2-morpholin-1-yl-acetyl)-benzofuran-5-yl ester;
- Acetic acid 2-(6-hydroxy-3-methyl-[1,3]oxazinan-6-yl)-6,7-dimethyl-benzofuran-5-yl ester;
- 1-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone;
- 1-(4-Bromo-5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-ethanone;
- 2-Hydroxymethyl-6,7-dimethyl-benzofuran-5-ol;
- 6,7-Dimethyl-3-phenyl-benzofuran-5-ol;
- 6,7-Dimethyl-2-(4-nitro-phenyl)-benzofuran-5-ol;
- 5-Hydroxy-6,7-dimethyl-benzofuran-2-carbaldehyde;
- 4-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-benzonitrile;
- 5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid;
- 5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid methyl ester;
- 5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid 3,7-dimethyl-octa-2,6-dienyl ester;
- 5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid bis-(2-hydroxy-ethyl)-amide;
- 5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester;
- 5-Hydroxy-6,7-dimethyl-benzofuran-2-carboxylic acid (2-hydroxy-ethyl)-amide;
- 3-(4-Methoxy-phenyl)-6,7-dimethyl-benzofuran-5-ol;
- 3-(4-Chloro-phenyl)-6,7-dimethyl-benzofuran-5-ol;
- 3-(4-Fluoro-phenyl)-6,7-dimethyl-benzofuran-5-ol;
- 4,5-Dimethyl-1,8-diphenyl-benzo[1,2-b;4,3-b′]difuran;
- 1,8-Bis-(4-fluoro-phenyl)-4,5-dimethyl-benzo[1,2-b;4,3-b′]difuran;
- and
- 1,8-Bis-(4-methoxy-phenyl)-4,5-dimethyl-benzo[1,2-b;4,3-b′]difuran.
24 more elements
Dependencies are inferred from the claim text.