Compounds for the treatment of metabolic disorders
View Patent ↗Agents useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, polycystic ovary syndrome, hyperlipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis are disclosed, wherein n is 1 or 2; m is 0, 1, 2, 3 or 4; q is 0 or 1; t is 0 or 1; R 1 is alkyl having from 1 to 3 carbon atoms; R 2 is hydrogen, halo, alkyl having from 1 to 3 carbon atoms, or alkoxy having from 1 to 3 carbon atoms; A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from: halo, hydroxy, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy; or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl; or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula (I) by a ring carbon. Alternatively, the agent can be a pharmaceutically acceptable salt of the compound of formula (I).
1. A compound of the formula:
wherein
n is 1 or 2;
m is 0, 1, 2, 3 or 4;
q is 0 or 1;
t is 0 or 1;
R 1 is alkyl having from 1 to 3 carbon atoms;
R 2 is hydrogen, halo, alkyl having from 1 to 3 carbon atoms, or alkoxy having from 1 to 3 carbon atoms;
A is 2,6-dimethylphenyl; or
a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula I by a ring carbon;
or a pharmaceutically acceptable salt of the compound.
2. The compound or salt of claim 1 , wherein n is 1; q is 0; t is 0; R 2 is hydrogen; m is 0 or 2; and A is 2,6-dimethylphenyl.
3. The compound or salt of claim 2 , wherein the compound is 2-(3-(2,6-Dimethylbenzyloxy)phenyl)-2-hydroxy-acetic acid.alpha-lactone.
4. The compound or salt of claim 2 , wherein the compound is 4-(3-(2,6-Dimethylbenzyloxy)phenyl)-4-hydroxy-butyric acid.gamma-lactone.
5. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and from one milligram to four hundred milligrams of a biologically active agent,
wherein the agent is a compound of the formula:
wherein
n is 1 or 2;
m is 1, 2, 3 or 4;
q is 0 or 1;
t is 0 or 1;
R 1 is alkyl having from 1 to 3 carbon atoms;
R 2 is hydrogen, halo, alkyl having from 1 to 3 carbon atoms, or alkoxy having from 1 to 3 carbon atoms;
A is 2,6-dimethylphenyl; or
a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula I by a ring carbon;
or a pharmaceutically acceptable salt of the compound.
6. The pharmaceutical composition of claim 5 , wherein n is 1; q is 0; t is 0; R 2 is hydrogen; m is 0 or 2; and A is 2,6-dimethylphenyl.
7. The composition of claim 6 , wherein the compound is 4-(3-(2,6-Dimethylbenzyloxy)phenyl)-4-hydroxy-butyric acid.gamma-lactone.
8. The pharmaceutical composition of claim 5 in oral dosage form.