Chemical compounds
Compounds of Formula I and methods for treating metabolic disorders are disclosed.
1. A compound of Formula I
wherein R 1 is H, Cl, Br, N(CH 3 ) 2 , or methoxy;
R 2 is H or OH;
each R 3 is independently C 1-6 alkyl;
X is CH 2 , C(O), or CH═CH;
Q is C 0-6 alkyl;
R 4 is OH, SO 3 H, CO 2 H, PO 3 H 2 , CONR 5 R 5 , NR 5 R 5 ; or NHC(O)CH 2 NR 5 R 5 ;
each R 5 is independently H, OH, C 1-6 alkyl, C 0-6 alkylCO 2 H, C 0-6 alkylSO 3 H, C 0-6 alkylPO 3 H 2 , C(O)C 0-6 alkylCO 2 H, C(O)C 0-6 alkylSO 3 H, C(O)C 0-6 alkylPO 3 H 2 , or CH(R 7 )C 0-6 alkyCO 2 H; and
R 7 is C 0-6 alkylCO 2 H, C 0-6 alkylOH, C 0-6 alkylSO 3 H, or C 0-6 alkylPO 3 H 2 .
2. A compound according to claim 1 wherein R 1 is methoxy.
3. A compound according to claim 2 wherein R 2 is H.
4. A compound according to claim 3 wherein X is CH 2 .
5. A compound according to claim 1 wherein X is C(O).
6. A compound according to claim 1 wherein Q is C 0-2 alkyl.
7. A compound according to claim 4 wherein Q is absent.
8. A compound according to claim 7 wherein each R 3 is independently C 2-4 alkyl.
9. A compound according to claim 8 wherein each R 3 is independently ethyl or n-butyl.
10. A compound according to claim 1 wherein R 4 is PO 3 H 2 .
11. A compound according to claim 9 wherein R 4 is NR 5 R 5 .
12. A compound according to claim 11 wherein one R 5 is H and the other is OH, methyl, C 1-4 alkylCO 2 H, C 0-2 alkylSO 3 H, C 1-2 alkylPO 3 H 2 , C(O)CO 2 H, C(O)C 1-2 alkylSO 3 H, C(O)C 1-2 alkylPO 3 H 2 , or CH(R 7 )C 0-1 alkyCO 2 H.
13. A compound according to claim 12 wherein one R 5 is H and the other is CH 2 CO 2 H, CH 2 SO 3 H, CH 2 CH 2 SO 3 H, or CH(R 7 )C 0-1 alkyCO 2 H.
14. A compound according to claim 13 wherein R 7 is C 0-1 alkylCO 2 H or C 0-2 alkylSO 3 H.
15. The compound
16. The compound
17. The compound of claim 16 wherein said compound is crystalline.
18. A pharmaceutically acceptable salt of a compound according to claim 1 .
19. A pharmaceutical composition comprising a compound according to claim 16 .
20. A method for treating diabetes mellitus (Type I or Type II) or obesity, in a human comprising administration of a composition according to claim 19 .
21. The method of claim 20 wherein said method is for treating Type II diabetes mellitus.
22. The method of claim 21 wherein said method further comprises administration of metformin.