Analogs of xanomeline
Disclosed herein are xanomeline analogs, as well as methods for making and using the analogs to, for example, treat neuropsychiatric disorders.
1. A compound according to the following formula:
wherein:
R 1 and R 2 are independently selected from hydrogen and C 1-6 alkyl;
R 3 is —C(O)R 5 ;
R 5 is C 1-14 alkyl; and
X − is a pharmaceutically acceptable counterion.
2. The compound of claim 1 , wherein R 1 is H.
3. The compound of claim 1 , wherein R 2 is C 1-2 alkyl.
4. The compound of claim 1 , wherein:
(i) R 1 is H, and R 2 is C 1-2 alkyl; or
(ii) R 1 is H, and R 2 is H.
5. The compound of claim 1 , wherein R 5 is C 4-12 alkyl.
6. The compound of claim 1 , wherein R 5 is C 4 alkyl, C 7 alkyl, or C 12 alkyl.
7. The compound of claim 1 , wherein:
(i) R 1 is H, R 2 is H, and R 5 is C 7 alkyl or C 12 alkyl; or
(ii) R 1 is H, R 2 is C 1-2 alkyl, and R 5 is C 4 alkyl.
8. The compound of claim 1 , wherein the compound
9. A pharmaceutical composition comprising the compound of claim 8 and a pharmaceutically acceptable excipient.
10. The compound of claim 1 , wherein the compound is
11. A pharmaceutical composition comprising the compound of claim 3 and a pharmaceutically acceptable excipient.
12. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the compound of claim 10 to the subject.
13. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the pharmaceutical composition of claim 11 to the subject.
14. The compound of claim 10 , wherein the compound is
15. The compound of claim 14 , wherein the compound is:
16. A pharmaceutical composition comprising the compound of claim 15 and a pharmaceutically acceptable excipient.
17. A method for treating a neuropsychiatric disease, in a subject in need thereof, comprising administering an effective amount of the compound of claim 15 to the subject.
18. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the pharmaceutical composition of claim 16 to the subject.
19. The compound of claim 14 , wherein the compound is:
20. A pharmaceutical composition comprising the compound of claim 19 and a pharmaceutically acceptable excipient.
21. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the compound of claim 19 to the subject.
22. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the pharmaceutical composition of claim 20 to the subject.
23. The compound of claim 1 , wherein the compound is
24. A pharmaceutical composition comprising the compound of claim 23 and a pharmaceutically acceptable excipient.
25. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the compound of claim 23 to the subject.
26. The compound of claim 1 , wherein R 5 is C 1 -C 5 alkyl.
27. The compound of claim 26 , wherein R 1 is H and R 2 is H.
28. The compound of claim 23 , wherein the compound is
29. The compound of claim 28 , wherein the compound is
30. A pharmaceutical composition comprising the compound of claim 28 and a pharmaceutically acceptable excipient.
31. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the compound of claim 28 to the subject.
32. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the pharmaceutical composition of claim 30 to the subject.
33. The compound of claim 23 , wherein the compound is
34. The compound of claim 33 , wherein the compound is
35. A pharmaceutical composition comprising the compound of claim 33 and a pharmaceutically acceptable excipient.
36. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the compound of claim 33 to the subject.
37. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the pharmaceutical composition of claim 35 to the subject.
38. The compound of claim 23 , wherein the compound is
39. The compound of claim 38 , wherein the compound is
40. A pharmaceutical composition comprising the compound of claim 38 and a pharmaceutically acceptable excipient.
41. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the compound of claim 38 to the subject.
42. A method for treating a neuropsychiatric disease in a subject in need thereof, comprising administering an effective amount of the pharmaceutical composition of claim 40 to the subject.