Antidiabetic Oxazolidinediones and Thiazolidinediones

1 . A compound of formula I:

or a pharmaceutically acceptable salt thereof, wherein:

one of the groups J, K and L is N, and the other two of the groups J, K and L are C(R 5 );

A is O or S;

X is a bond or —C(R 7 ) 2 —;

R 1 is selected from the group consisting of H and C 1 -C 3 alkyl, wherein C 1 -C 3 alkyl is optionally substituted with 1-3 halogens;

each R 2 is independently selected from the group consisting of halogen, C 1 -C 3 alkyl, and —OC 1 -C 3 alkyl, wherein C 1 -C 3 alkyl and —OC 1 -C 3 alkyl are optionally substituted with 1-3 halogens;

R 3 is selected from the group consisting of

Y is selected from the group consisting of ═O and ═N—OH;

D and Z are each independently selected from the group consisting of C(R 7 ) and N;

B is selected from the group consisting of —N(R 7 )—, —O— and —S—;

each R 4 is independently selected from the group consisting of halogen, —OH, C 1 -C 3 alkyl, —OC 1 -C 3 alkyl, —OC(═O)C 1 -C 3 alkyl, and —S(O) q C 1 -C 3 alkyl, wherein C 1 -C 3 alkyl, —OC 1 -C 3 alkyl, —OC(═O)C 1 -C 3 alkyl, and —S(O) q C 1 -C 3 alkyl are optionally substituted with 1-5 halogens;

each R 5 is independently selected from the group consisting of H, halogen, C 1 -C 3 alkyl, and —OC 1 -C 3 alkyl, wherein C 1 -C 3 alkyl and —OC 1 -C 3 alkyl are optionally substituted with 1-3 halogens;

R 6 is selected from the group consisting of C 2 -C 5 alkyl, —CH 2 Cyclopropyl, C 3 -C 6 cycloalkyl, —OC 2 -C 5 alkyl and —C(═O)C 1 -C 3 alkyl, wherein the alkyl, cyclopropyl, and cycloalkyl groups of said R 6 substituent are optionally substituted with 1-3 halogens;

each R 7 is independently selected from the group consisting of H and C 1 -C 3 alkyl, wherein C 1 -C 3 alkyl is optionally substituted with 1-3 F;

m is an integer from 0-4;

n is an integer from 0-5; and

q is an integer from 0-2.

2 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

X is a bond or CH 2 ;

R 1 is selected from the group consisting of H and C 1 -C 3 alkyl, wherein C 1 -C 3 alkyl is optionally substituted with 1-3 F;

each R 2 is independently selected from the group consisting of F, Cl, CH 3 , CF 3 , —OCH 3 , and —OCF 3 ;

each R 4 is independently selected from the group consisting of halogen, —OH, C 1 -C 3 alkyl, —OC 1 -C 3 alkyl, —OC(═O)C 1 -C 3 alkyl, and —S(O) q C 1 -C 3 alkyl, wherein C 1 -C 3 alkyl, —OC 1 -C 3 alkyl, —OC(═O)C 1 -C 3 alkyl, and —S(O) q C 1 -C 3 alkyl are optionally substituted with 1-3 F;

each R 5 is independently selected from the group consisting of H, F, Cl, CH 3 , —OCH 3 , CF 3 , and —OCF 3 ;

R 6 is selected from the group consisting of C 2 -C 5 alkyl, —CH 2 Cyclopropyl, and —C(═O)C 1 -C 3 alkyl, wherein any alkyl or cycloalkyl group of said R 6 substituent is optionally substituted with 1-3 F;

R 7 is selected from the group consisting of H and C 1 -C 3 alkyl;

m is an integer selected from 0 and 1; and

n is an integer from 0-3.

3 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is H or CH 3 .

4 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is CH 3 .

5 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein A is O.

6 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R 4 is independently selected from the group consisting of F, Cl, —OH, CH 3 , CF 3 , —OCH 3 , —OCF 3 , —OCBF 2 , —OC 2 H 5 , —OC(═O)CH 3 , and —S(O) q CH 3 , wherein q is 0, 1 or 2, and n is 0, 1, or 2.

7 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein X is a bond.

8 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein X is CH 2 .

9 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 6 is selected from the group consisting of n-C 3 H 7 , —CH 2 Cyclopropyl, and —C(═O)C 2 H 5 .

10 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 6 is n-C 3 H 7 .

11 . The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein

A is O;

X is a bond or CH 2 ;

R 1 is CH 3 ;

each R 4 is independently selected from the group consisting of F, Cl, —OH, CH 3 , CF 3 , —OCH 3 , —OCF 3 , —OCH 2 CH 3 , —OC(═O)CH 3 , —OCHF 2 , and —S(O) q CH 3 ;

R 5 is H, Cl or F;

R 6 is selected from the group consisting of n-C 3 H 7 , —CH 2 Cyclopropyl, and —C(═O)C 2 H 5 ;

R 7 is selected from H and CH 3 ;

m is 0; and

n is an integer from 0-2.

12 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 5 is H; and

n is 1 or 2.

13 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 3 is

14 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 3 is

15 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 3 is

16 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 3 is

17 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 3 is

18 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 3 is

19 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein R 3 is

20 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein L is N; and J and K are each C(R 5 ).

21 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein J is N; and L and K are each C(R 5 ).

22 . The compound of claim 11 , or a pharmaceutically acceptable salt thereof, wherein K is N; and L and J are each C(R 5 ).

23 . A pharmaceutical composition comprising the compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

24 . A method for treating type 2 diabetes in a patient in need of treatment comprising the administration of a therapeutically effective amount of the compound of claim 1 , or a pharmaceutically acceptable salt thereof.

25 . (canceled)

26 . The compound of claim 20 , selected from the group consisting of the compounds listed below, or a pharmaceutically acceptable salt thereof:

27 . (canceled)