α-(Trifluoromethyl-substituted aryloxy, arylamino, arylthio or arylmethyl)-trifluoromethyl-substituted phenylacetic acids and derivatives as antidiabetic agents

1. A compound having the formula

and all pharmaceutically acceptable salts and prodrugs thereof, wherein

X is a member selected from the group consisting of O, and NR, wherein R is H,

Y is a member selected from the group consisting of CH 2 OR c and CO 2 R c , wherein R c is a member selected from the group consisting of H, (C 1 -C 8 )alkyl, and (C 1 -C 8 )alkylene-Z, wherein Z is selected from the group consisting of COR d , COOR d , NR d R e , NR d CONR c R f , NR d COR c , NR d COOR c and CONR d R e wherein R d , R e and R f are each independently selected from the group consisting of H, (C 1 -C 8 )alkyl and phenyl;

each R 1 and R 3 is a member independently selected from the group consisting of halogen, (C 1 -C 8 )alkyl, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkyl, O(C 1 -C 8 )haloalkyl, and nitro;

R 2 is a member selected from the group consisting of H and CH 3 ;

Q is C

the subscript m is an integer of from 0 to 2; and

the subscript p is an integer of from 0 to 1.

2. A compound of claim 1 , wherein Y is CO 2 R c .

3. A compound of claim 1 , wherein each R 1 is selected from the group consisting of halogen, nitro, (C 1 -C 8 ) alkyl and (C 1 -C 8 ) alkoxy; and each R 3 is selected from the group consisting of halogen, nitro, (C 1 -C 8 ) alkyl and (C 1 -C 8 ) alkoxy.

4. A compound of claim 3 , wherein X is O and Y is CO 2 R c .

5. A compound of claim 3 , wherein X is O and Y is CH 2 OR c .

6. A compound of claim 3 , wherein X is NH and Y is CO 2 R c .

7. A compound of claim 3 , wherein X is NH and Y is CH 2 OR c .

8. A composition comprising a pharmaceutically acceptable excipient and a compound having a formula:

and all pharmaceutically acceptable salts and prodrugs thereof, wherein

X is a member selected from the group consisting of O, and NR, wherein R is H,

Y is a member selected from the group consisting of CH 2 OR c and CO 2 R c , wherein R c is a member selected from the group consisting of H, (C 1 -C 8 )alkyl, and (C 1 -C 8 )alkylene-Z, wherein Z is selected from the group consisting of COR d , COOR d , NR d R e , NR d CONR e R f , NR d COR e , NR d COOR e and CONR d R e wherein R d , R e and R f are each independently selected from the group consisting of H, (C 1 -C 8 )alkyl and phenyl;

each R 1 and R 3 is a member independently selected from the group consisting of halogen, (C 1 -C 8 )alkyl, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkyl, O(C 1 -C 8 )haloalkyl, and nitro,

R 2 is a member selected from the group consisting of H and CH 3 ;

Q is C

the subscript m is an integer of from 0 to 2; and

the subscript p is an integer of from 0 to 1.

9. A compound selected from the group consisting of:

(4-Trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid;

(2-Trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid;

(4-Trifluoromethyl-phenoxy)-(4-trifluoromethyl-phenyl)-acetic acid;

(3,5-Bis-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid;

(2-Chloro-4-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid;

(3-Trifluoromethyl-phenoxy)-(4-trifluoromethyl-phenyl)-acetic acid;

(2-Trifluoromethyl-phenoxy)-(4-trifluoromethyl-phenyl)-acetic acid;

(2-Chloro-4-trifluoromethyl-phenoxy)-(4-trifluoromethyl-phenyl)-acetic acid;

(2-Fluoro-5-trifluoromethyl-phenoxy)-(4-trifluoromethyl-phenyl)-acetic acid;

(3-Fluoro-5-trifluoromethyl-phenyl)-(5-methoxy-2-trifluoromethyl-phenoxy)-acetic acid;

(2,4-Bis-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid ethyl ester;

(3-Trifluoromethyl-phenyl)-(2-trifluoromethyl-phenylamino)-acetic acid;

(3-Trifluoromethyl-phenyl)-(3-trifluoromethyl-phenylamino)-acetic acid;

(3,5-Bis-trifluoromethyl-phenylamino)-(3-trifluoromethyl-phenyl)-acetic acid;

(3-Trifluoromethyl-phenyl)-(4-trifluoromethyl-phenylamino)-acetic acid;

(4-Isopropyl-2-trifluoromethyl-phenylamino)-(3-trifluoromethyl-phenyl)-acetic acid;

(4-Trifluoromethyl-phenyl)-(2-trifluoromethyl-phenylamino)-acetic acid;

2-(4-Trifluoromethyl-phenoxy)-2-(3-trifluoromethyl-phenyl)-propionic acid;

2-(4-Trifluoromethyl-phenoxy)-2-(4-trifluoromethyl-phenyl)-propionic acid;

2-(2-Trifluoromethyl-phenoxy)-2-(3-trifluoromethyl-phenyl)-propionic acid;

2-(4-trifluoromethyl-phenoxy)-2-(3-trifluoromethyl-phenyl)-ethanol;

(4-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid 2-acetylamino-ethyl ester;

(4-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid sodium salt;

(+)-(4-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid; and

(−)-(4-trifluoromethyl-phenoxy)-(3-trifluoromethyl-phenyl)-acetic acid.

10. A compound selected from the group consisting of: