Compounds for the treatment of metabolic disorders

1. A biologically active agent, wherein the agent is 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 2 is alkyl having from 1 to 3 carbon atoms;

R 3 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, 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; and

R 1 is hydrogen or alkyl having 1 or 2 carbon atoms, provided that when m is 0 or 1, R 1 is not hydrogen;

or when R 1 is hydrogen, a pharmaceutically acceptable salt of the compound, wherein the agent is substantilly pure.

2. The biologically active agent of claim 1 , wherein n is 1; q is 0; t is 0; R 3 is hydrogen; and

A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from: halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy.

3. The biologically active agent of claim 2 , wherein wherein A is 2,6-dimethylphenyl.

4. The biologically active agent of claim 3 , 4-(3-(2,6-Dimethylbenzyloxy)-phenyl)-4-hydroxybutanoic acid.

5. A biologically active agent, wherein the agent is a compound of the formula:

wherein

n is 1 or2;

m is 0,1,2,3 or 4;

q is 0 or 1;

t is 0 or 1;

R 2 is alkyl having from 1 to 3 carbon atoms;

R 3 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, 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 0 and the heteroaromatic ring is covalently bound to the remainder of the compound of formula I by a ring carbon; and

R 1 is hydrogen or alkyl having 1 or 2 carbon atoms, provided that when m is 0 or 1, R 1 is not hydrogen;

or when R 1 is hydrogen, a pharmaceutically acceptable salt of the compound, wherein the agent is present in a mammal other than a mouse.

6. The biologically active agent of claim 5 , wherein n is 1; q is 0; t is 0; R 3 is hydrogen; and

A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from: halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy.

7. The biologically active agent of claim 6 , wherein A is 2,6-dimethylphenyl.

8. The biologically active agent of claim 7 , 4-(3-(2,6-Dimethylbenzyloxy)-phenyl)-4-hydroxybutanoic acid.

9. The biologically active agent of claim 8 , wherein the mammal is a human.

10. The biologically active agent of claim 5 , wherein the mammal is a human.

11. 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 0,1,2,3 or 4;

q is 0 or 1;

t is 0 or 1;

R 2 is alkyl having from 1 to 3 carbon atoms;

R 3 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, 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; and

R 1 is hydrogen or alkyl having 1 or 2 carbon atoms, provided that when m is 0 or 1, R 1 is not hydrogen;

or when R 1 is hydrogen, a pharmaceutically acceptable salt of the compound.

12. The pharmaceutical composition of claim 11 , wherein n is 1; q is 0; t is 0;R 3 is hydrogen; and

A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from: halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy.

13. The pharmaceutical composition of claim 12 , wherein A is 2,6-dimethylphenyl.

14. The pharmaceutical composition of claim 13 , wherein the biologically active agent is 4-(3-(2,6-Dimethylbenzyloxy)-phenyl)-4-hydroxybutanoic acid.

15. The pharmaceutical composition of claim 11 in oral dosage form.

16. A method for treating a mammalian subject with a condition selected from the group consisting of insulin resistance syndrome,and Type II Diabetes, comprising administering to the subject an amount of a biologically active agent,

wherein the agent is 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 2 is alkyl having from 1 to 3 carbon atoms;

R 3 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, 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; and

R 1 is hydrogen or alkyl having 1 or 2 carbon atoms, provided that when m is 0 or 1, R 1 is not hydrogen;

or when R 1 is hydrogen, a pharmaceutically acceptable salt of the compound.

17. The method of claim 16 , wherein n is 1; q is 0; t is 0; R 3 is hydrogen; and

A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from: halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy.

18. The method of claim 17 , wherein A is 2,6-dimethylphenyl.

19. The method of claim 18 , wherein the biologically active agent is 4-(3-(2,6-Dimethylbenzyloxy)-phenyl)-4-hydroxybutanoic acid.

20. The method of any one of claims 16 to 19 , wherein the subject is a human.

21. The method of claim 20 , wherein the agent is administered orally in an amount from one milligram to four hundred milligrams per day.

22. The method of claim 16 , wherein the treatment reduces a symptom of diabetes or the chances of developing a symptom of diabetes, wherein the symptom is selected from the group consisting of: atherosclerosis, obesity, hypertension, hyperlipidemia, fatty liver disease, nephropathy, neuropathy, retinopathy, foot ulceration and cataracts, associated with diabetes.