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US 7,732,618 B2Granted
Benzimidazole acetic acids exhibiting CRTH2 receptor antagonism and uses thereof
AssigneeWyeth
InventorsYoussef L. Bennani, Lawrence Nathan Tumey, Elizabeth Ann Gleason, Michael Joseph Robarge
Life of this patent
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Abstract
The invention relates to benzimidazole acetic acid compounds which function as antagonists of the Chemoattractant Receptor-homologous molecule expressed on T-Helper type 2 cells (CRTH2) receptor. The invention also relates to the use of these compounds to inhibit the binding of prostaglandin D2 and its metabolites or certain thromboxane metabolites to the CRTH2 receptor and to treat disorders responsive to such inhibition.
Claims6
A compound selected from:
- {5-[benzyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluoro-benzenesulfonyl)-(4-fluoro-benzyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluoro-benzenesulfonyl)-(3-methyl-butyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluoro-benzenesulfonyl)-isopropyl-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(2-chloro-benzyl)-(4fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid:
- {5-[(3-chloro-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-chloro-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(2,3-dichloro-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[[2-(4-chloro-phenoxy)-ethyl]-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluoro-benzenesulfonyl)-(3-phenyl-propyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluorobenzenesulfonyl)-(3-phenoxy-propyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-cyano-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-trifluoromethoxybenzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[benzothiazol-2-ylmethyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- and
- {5-[but-2-enyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- or a pharmaceutically acceptable salt thereof.
15 more elements
A compound selected from:
- [2(1,5-dimethyl-hex-4-enyl)-5-(4-fluoro-benzenesulfonylamino)-benzoimidazol-1-yl]-acetic acid;
- [2(1-ethyl-pentyl)-5-(4-fluoro-benzenesulfonylamino)-benzoimidazol-1-yl]-acetic acid;
- [2(2-allyloxycarbonylamino-enyl)-5-(4-fluoro-benzenesulfonylamino)-benzoimidazol-1-yl]-acetic acid;
- [2-but-1-enyl-5-(4-fluoro-benzenesulfonylamino)-benzoimidazol-1-yl]-acetic acid;
- [2-butyl-5- (4-fluoro-benzenesulfonylamino)-benzoimidazol-1-yl]-acetic acid;
- [2-ethyl-5- (4-fluoro-benzenesulfonylamino)-benzoimidazol-1-yl]-acetic acid;
- [2-propyl-5- (1,1,3-trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-benzoimidazol-1-yl]-acetic acid;
- [5-(4-fluoro-benzenesulfonylamino)-2-(2-methylsulfanyl-ethyl)-benzoimidazol-1-yl]-acetic acid;
- [5-(4-fluoro-benzenesulfonylamino)-2-(1-methyl-butyl)-benzoimidazol-1-yl]-acetic acid;
- [5-(4-fluoro-benzenesulfonylamino)-2-(2,4,4-trimethyl-pentyl)-benzoimidazol-1-yl]-acetic acid;
- [5-(4-fluoro-benzenesulfonylamino)-2-isobutyl-benzoimidazol-1-yl]-acetic acid;
- [5-(4-fluoro-benzenesulfonylamino)-2-isopropyl-benzoimidazol-1-yl]-acetic acid;
- [5-(4-fluoro-benzenesulfonylamino)-2-pentyl-benzoimidazol-1-yl]-acetic acid;
- [5-(4-fluoro-benzenesulfonylamino)-2-propyl-benzoimidazol-1-yl]-acetic acid;
- {2-butyl-5-[(4-fluoro-benzenesulfonylamino)-methyl-amino]-benzoimidazol-1-yl}-acetic acid;
- {4-[benzyl-(4-fluoro-phenylmethanesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {4-[(3-fluoro-benzenesulfonyl)-(4-fluoro-benzyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {4-[(3-fluoro-benzenesulfonyl)-(2-methoxy-ethyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {4-[(3-fluoro-benzenesulfonyl)-(3-methyl-butyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {4-[(3-fluoro-benzenesulfonyl)-isopropyl-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {4-[benzyl-(3-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(2-cyano-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid
- {5-[(2-fluoro-benzenesulfonyl)-(4-fluoro-benzyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(2-trifluoromethyl-benzyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(3,5-dimethyl-isoxazol-4-ylmethyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(3-fluoro-benzenesulfonyl)-(4-fluoro-benzyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluoro-benzenesulfonyl)-(2-methyl-thiazol-4-ylmethyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluoro-benzenesulfonyl)-(3-fluoro-benzyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(4-fluoro-benzenesulfonyl)-(3-trifluoromethyl-benzyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[(cyclohexyl)-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[benzyl-(4-fluoro-benzenesulfonyl)-amino]-2-butyl-benzoimidazol-1-yl}-acetic acid;
- {5-[benzyl-(4-fluoro-benzenesulfonyl)-amino]-2-isopropyl-benzoimidazol-1-yl}-acetic acid;
- {5-[ethanesulfonyl-(4-fluoro-benzyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- {5-[ethoxycarbonylmethyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- and
- {7-[benzyl-(4-fluoro-benzenesulfonyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid;
- or a pharmaceutically acceptable salt thereof.
34 more elements
Dependencies are inferred from the claim text.