Ortho-substituted benzoic acid derivatives for the treatment of insulin resistance
AssigneeAstraZeneca AB
InventorLanna Li
Life of this patent
Estimating the term…
Abstract
The present invention provides a compound of formula (I), wherein n is 0, 1 or 2; R1 represents halo, a C1-4alkyl group which is optionally substituted by one or more fluoro, a C1-4alkoxy group which is optionally substituted by one or more fluoro and wherein when n is 2 the substituents R1 may be the same or different; R2 represents an unbranched C2-7alkyl group; R3 represents H or OCH3; and W represents O or S and pharmaceutically acceptable salts and prodrugs thereof, to processes for preparing such compounds, to their utility in treating clinical conditions associated with insulin resistance, to methods for their therapeutic use and to pharmaceutical compositions containing them.
Claims7
A compound of formula I:
- or a pharmaceutically acceptable salt, or an in vivo cleavable ester thereof, wherein:
- n is 0, 1 or 2;
- R1 represents halo, a C1-4alkyl group which is optionally substituted by one or more fluoro, a C1-4alkoxy group which is optionally substituted by one or more fluoro and wherein when n is 2, each R1 may be the same or different;
- R2 represents an unbranched C2-7alkyl group;
- R3 represents H or OCH3;
- and
- W represents O or S.
A compound selected from
- 2-[2-(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid;
- 2-[2-(4-{2-[(2,4-difluorobenzyl)(heptyl)amino]-2-oxoethoxy}-3-methoxyphenyl)ethoxy]benzoic acid;
- 2-[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethylthio]benzoic acid;
- 2-[2-(4-{2-[(4-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid;
- 2-[2-(4-{2-[ethyl(4-trifluoromethylbenzyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid;
- 2-[2-(4-{2-[ethyl(4-trifluoromethylbenzyl)amino]-2-oxoethoxy}phenyl)ethylthio]benzoic acid;
- 2-{2-[4-(2-{butyl[2-fluoro-4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]-ethoxy}benzoic acid;
- 2-[2-(4-{2-[(2,4-difluorobenzyl)(propyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid;
- 2-[2-(4-{2-[benzyl(ethyl)amino]-2-oxoethoxyl}phenyl)ethoxy]benzoic acid;
- 2-{[2-(4-{2-[benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acid;
- 2-[2-(4-{2-[(4-tert-butylbenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid;
- 2-[2-(4-{2-[ethyl(4-fluorobenzyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid;
- 2-{[2-(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acid;
- and
- 2-{[2-(4-{2-[(2-chlorobenzyl)(ethyl)amino]-2-oxoethoxy}phenyl)ethyl]thio}benzoic acid, or a pharmaceutically acceptable salt thereof.
A compound of formula II:
- wherein:
- n is 0, 1 or 2;
- R1 represents halo, a C1-4alkyl group which is optionally substituted by one or more fluoro, a C1-4alkoxy group which is optionally substituted by one or more fluoro and wherein when n is 2, each R1 may be the same or different;
- R2 represents an unbranched C2-7alkyl group;
- R3 represents H or OCH3;
- W represents O or S;
- and
- PG represents a protecting group for a carboxylic hydroxy group.
Dependencies are inferred from the claim text.