Bicyclic compounds
Disclosed herein are compounds of Formulae (I) and (II), methods of synthesizing compounds of Formulae (I) and (II), and methods of using compounds of Formulae (I) and (II) as an analgesic.
1. A method for reducing pain or fever comprising administering to a subject an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, in a subject in need thereof, wherein Formula (I) has the structure:
wherein:
R 1 is selected from the group consisting of H, D, a substituted or unsubstituted C 1-6 alkyl and a substituted or unsubstituted C 1-6 haloalkyl;
R 2 is H;
R 3 is selected from the group consisting of D, halo, hydroxy, a substituted or unsubstituted C 1-8 alkyl, a substituted or unsubstituted C 2-8 alkenyl, a substituted or unsubstituted C 2-8 alkynyl, a substituted or unsubstituted C 3-20 cycloalkyl, a substituted or unsubstituted C 3-20 cycloalkenyl, a substituted or unsubstituted C 8-20 cycloalkynyl, a substituted or unsubstituted C 6-20 aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl(C 1-6 alkyl), a substituted or unsubstituted heteroaryl(C 1-6 alkyl), a substituted or unsubstituted heterocyclyl(C 1-6 alkyl), a substituted or unsubstituted C 1-8 haloalkyl and a substituted or unsubstituted sulfonyl;
m is 0; and
provided that when R 1 is H, then R 3 is not t-butyl; and provided that a compound of Formula (I), or a pharmaceutically salt thereof, is not
2. A compound of Formula (I), or a pharmaceutically acceptable salt thereof,
wherein:
R 1 is selected from the group consisting of H, D, a substituted or unsubstituted C 1-6 alkyl and a substituted or unsubstituted C 1-6 haloalkyl;
R 2 is H;
R 3 is selected from the group consisting of D, hydroxy, an unsubstituted C 1-8 alkyl, a substituted or unsubstituted C 2-8 alkenyl, a substituted or unsubstituted C 2-8 alkynyl, a substituted or unsubstituted C 3-20 cycloalkenyl, a substituted or unsubstituted C 8-20 cycloalkynyl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl(C 1-6 alkyl), a substituted or unsubstituted heteroaryl(C 1-6 alkyl), a substituted or unsubstituted heterocyclyl(C 1-6 alkyl), CHF 2 , CH 2 F, CF 2 CH 3 and a substituted or unsubstituted sulfonyl; and
m is 0; and
provided that when R 1 is H then R 3 is not selected from the group consisting of CH 3 , hydroxy and an unsubstituted t-butyl; and provided that a compound of Formula (I), or a pharmaceutically salt thereof, cannot be N,N-diethyl-alpha-methyl-bicyclo[1.1.1]pentane-1-methanamine or
3. A pharmaceutical composition comprising an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, as recited in claim 2 , and a pharmaceutically acceptable carrier, diluent, excipient or combination thereof.
4. The compound of claim 2 , wherein R 1 is H.
5. The compound of claim 2 , wherein R 3 is an unsubstituted C 1-8 alkyl.
6. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted sulfonyl.
7. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted C 2-8 alkenyl, a substituted or unsubstituted C 2-8 alkynyl, a substituted or unsubstituted C 3-20 cycloalkenyl, a substituted or unsubstituted C 8-20 cycloalkynyl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl(C 1-6 alkyl), a substituted or unsubstituted heteroaryl(C 1-6 alkyl) or a substituted or unsubstituted heterocyclyl(C 1-6 alkyl).
8. The compound of claim 2 , wherein the compound is selected from
or a pharmaceutically acceptable salt of any of the foregoing.
9. The compound of claim 2 , wherein R 1 is an unsubstituted C 1-6 alkyl.
10. The compound of claim 2 , wherein R 1 is H; and R 3 is CHF 2 , CH 2 F or CF 2 CH 3 .
11. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted C 3-20 cycloalkenyl.
12. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted C 8-20 cycloalkynyl.
13. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted heteroaryl.
14. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted heterocyclyl.
15. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted aryl(C 1-6 alkyl).
16. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted heteroaryl(C 1-6 alkyl).
17. The compound of claim 2 , wherein R 3 is a substituted or unsubstituted heterocyclyl(C 1-6 alkyl).
18. The method of claim 1 , wherein the compound is selected from
or a pharmaceutically acceptable salt of any of the foregoing.
19. The method of claim 1 , wherein the compound is
or a pharmaceutically acceptable salt thereof.
20. The compound of claim 2 , wherein R 3 is CHF 2 , CH 2 F or CF 2 CH 3 .
21. The method of claim 1 , wherein R 3 is CHF 2 , CH 2 F or CF 2 CH 3 .
22. The method of claim 21 , wherein R 1 is H.