Compounds for the treatment of metabolic disorders
View Patent ↗Agents useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, hyper-lipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis are disclosed. Formula (I) wherein n is 1 or 2; m is 2 or 3; 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 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. Alternatively, when R 1 is hydrogen, the biologically active agent can be a pharmaceutically acceptable salt of the compound of Formula (I)
1. A pharmaceutical composition adapted for oral administration, 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 2 or 3;
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, or alkyl having from 1 to 3 carbon atoms;
A is phenyl, 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; and
R 1 is hydrogen or alkyl having 1 or 2 carbon atoms;
or when R 1 is hydrogen, a pharmaceutically acceptable salt of the compound.
2. The pharmaceutical composition of claim 1 , wherein n is 1; q is 0; t is 0; R 3 is hydrogen; and
A is phenyl, 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 pharmaceutical composition of claim 2 , wherein A is 2,6-dimethylphenyl.
4. The pharmaceutical composition of claim 3 , wherein the biologically active agent is selected from the group consisting of:
5-[3-(2,6-Dimethylbenzyloxy)-phenyl]-pent-4-enoic acid ethyl ester; and
6-[3-(2,6-Dimethylbenzyloxy)-phenyl]-hex-5-enoic acid ethyl ester.
5. The pharmaceutical composition of claim 1 in oral dosage form.