3,4,5-trisubstituted-1,2,4-triazoles and 3,4,5-trisubstituted-3-thio-1,2,4-triazoles and uses thereof
The present disclosure describes novel compounds that are somatostatin receptor type 4 agonists.
1. A compound of Formula (I):
wherein
are independently a single bond or is absent;
A is C(H) or N;
B and C are independently C(H), N, N(H), O, or S, provided that when B or C is C(H) or N, is a single bond, and when B or C is N(H), O, or S, is absent, and further provided that at least one of B and C is N, N(H), O, or S;
R 1 and R 7 are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted C 1 -C 6 alkyl, or substituted or unsubstituted cycloalkyl, or substituted or unsubstituted fused ring system;
R 2 is substituted or unsubstituted C 1 -C 6 alkyl;
R 3 , R 4 , and R 5 are independently hydrogen, F, Cl, Br, I, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amine, thiosulfinate, thiosulfonate, thioamide, sulfimide, sulfoximide, sulfonediimine, or sulfur halide;
R 6 and R 8 are independently substituted or unsubstituted C 1 -C 2 alkyl; and
R 9 is a substituted or unsubstituted C 1 -C 3 alkyl;
with the proviso that when R 9 is C 2 alkyl, R 7 is not a 3,4-dichlorobenzene.
2. The compound of claim 1 , wherein A, B, and C are N.
3. A compound of Formula (I):
wherein
are independently a single bond or is absent;
A is C(H) or N;
B and C are independently C(H), N, N(H), O, or S, provided that when B or C is C(H) or N, is a single bond, and when B or C is N(H), O, or S, is absent, and further provided that at least one of B and C is N, N(H), O, or S;
R 1 and R 7 are independently substituted or unsubstituted aryl or substituted or unsubstituted fused ring system;
R 2 is substituted or unsubstituted C 1 -C 6 alkyl;
R 3 , R 4 , and R 5 are independently hydrogen, F, Cl, Br, I, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amine, thiosulfinate, thiosulfonate, thioamide, sulfimide, sulfoximide, sulfonediimine, or sulfur halide;
R 6 and R 8 are independently hydrogen, F, Cl, Br, I, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted cycloalkyl; and
R 9 is a substituted or unsubstituted C 1 -C 3 alkyl;
with the proviso that when R 9 is C 2 alkyl, R 7 is not a 3,4-dichlorobenzene.
4. The compound of claim 3 , wherein R 1 is substituted or unsubstituted fused ring system.
5. The compound of claim 4 , wherein R 1 is substituted or unsubstituted indole.
6. The compound of claim 3 , wherein R 1 is substituted or unsubstituted aryl.
7. The compound of claim 6 , wherein R 7 is
wherein R 10 , R 11 , R 12 , R 13 , and R 14 is independently hydrogen, F, Cl, Br, I, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted amine, SO 2 CH 3 , thiosulfinate, thiosulfonate, thioamide, sulfimide, sulfoximide, sulfonediimine, or sulfur halide.
8. The compound of claim 7 , wherein R 10 , R 11 , R 12 , R 13 , and R 14 is independently hydrogen, F, Cl, Br, I, CF 3 , OCH 3 , OCH 2 (C 6 H 4 ), SO 2 CH 3 , or OCF 3 .
9. The compound of claim 1 , wherein R 2 is substituted or unsubstituted C 1 -C 3 alkyl.
10. The compound of claim 9 , wherein R 2 is substituted or unsubstituted propyl.
11. The compound of claim 10 , wherein R 2 is unsubstituted propyl.
12. The compound of claim 1 , wherein R 3 , R 4 , and R 5 are independently hydrogen, F, Cl, Br, I, or substituted or unsubstituted alkyl.
13. The compound of claim 12 , wherein R 3 , R 4 , and R 5 are hydrogen.
14. The compound of claim 1 , wherein R 9 is methyl.
15. The compound of claim 1 , wherein R 9 is ethyl.
16. A compound selected from the group consisting of:
17. The compound of claim 3 , wherein A, B, and C are N.
18. The compound of claim 3 , wherein R 2 is substituted or unsubstituted C 1 -C 3 alkyl.
19. The compound of claim 1 , wherein R 1 and R 7 are independently substituted or unsubstituted aryl or substituted or unsubstituted fused ring system.
20. The compound of claim 3 , wherein R 6 and R 8 are independently substituted or unsubstituted C 1 -C 3 alkyl.