Dimethyltryptamine analogues as nitric oxide delivery drugs
Provided herein are compounds of Formula (I), (II), or a pharmaceutically acceptable salt thereof. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I), (II), or pharmaceutically acceptable salt thereof, and methods of using a compound of Formula (I), (II), or a pharmaceutically acceptable salt thereof.
1. A compound of Formula (II):
or a pharmaceutically acceptable salt thereof; wherein,
R 3 , R 4 , and R 5 are independently H, halogen, or C 1 -C 6 alkyl;
R 6 is —(C═O)(CR 7 R 7 ′) n —ONO 2 ,
or —(C═O)(CR 7 R 7 ′) m —CH(NH 2 )CH 2 ONO 2 ;
R 1 and R 2 are independently H or C 1 -C 6 alkyl;
R 7 and R 7 ′ are independently H, halogen, or C 1 -C 6 alkyl;
X, Y, and Z are independently absent or O;
each m is 2, 3, or 4; and
each n is independently 1, 2, 3, 4 or 5.
2. The compound of claim 1 , wherein R 1 is C 1 -C 6 alkyl.
3. The compound of claim 1 , wherein R 1 is methyl.
4. The compound of claim 1 , wherein R 1 is H.
5. The compound of claim 1 , wherein R 2 is C 1 -C 6 alkyl.
6. The compound of claim 1 , wherein R 2 is methyl.
7. The compound of claim 1 , wherein R 2 is H.
8. The compound of claim 1 , wherein R 3 is H and X is absent.
9. The compound of claim 1 , wherein R 3 is halogen and X is absent.
10. The compound of claim 1 , wherein R 3 is H and X is O.
11. The compound of claim 1 , wherein R 3 is C 1 -C 6 alkyl and X is O.
12. The compound of claim 1 , wherein R 4 is H and Y is absent.
13. The compound of claim 1 , wherein R 4 is H and Y is O.
14. The compound of claim 1 , wherein R 4 is halogen and Y is absent.
15. The compound of claim 1 , wherein R 4 is C 1 -C 6 alkyl and Y is O.
16. The compound of claim 1 , wherein R 5 is H and Z is absent.
17. The compound of claim 1 , wherein R 5 is H and Z is O.
18. The compound of claim 1 , wherein R 5 is halogen and Z is absent.
19. The compound of claim 1 , wherein R 5 is C 1 -C 6 alkyl and Z is absent.
20. The compound of claim 1 , wherein R 5 is C 1 -C 6 alkyl and Z is O.
21. The compound of claim 1 , wherein R 6 is —(C═O)(CR 7 R 7 ′) n —ONO 2 .
22. The compound of claim 1 , wherein R 6 is —(C═O)(CR 7 R 7 ′) m —CH(NH 2 )CH 2 ONO 2 .
23. The compound of claim 1 , wherein R 6 is —(C═O)(CH 2 ) n —ONO 2 .
24. The compound of claim 1 , wherein R 6 is —(C═O)(CH 2 ) m —CH(NH 2 )CH 2 ONO 2 .
25. The compound of claim 1 , wherein R 6 is —(C═O)(CH 2 ) 3 —ONO 2 .
26. The compound of claim 1 , having the following chemical formula:
or a pharmaceutically acceptable salt thereof.
27. The compound of claim 26 , having the following chemical formula:
or a pharmaceutically acceptable salt thereof.
28. The compound of claim 26 , having the following chemical formula:
or a pharmaceutically acceptable salt thereof.
29. A pharmaceutical composition, comprising a compound of claim 1 and a pharmaceutically acceptable excipient.
30. A compound of chemical formula
or a pharmaceutically acceptable salt thereof.
31. The compound of claim 26 , having the following chemical formula:
or a pharmaceutically acceptable salt thereof.
32. The compound of claim 26 , having the following chemical formula:
or a pharmaceutically acceptable salt thereof.
33. The compound of claim 26 , having the following chemical formula:
or a pharmaceutically acceptable salt thereof.