Therapeutic compounds
View Patent ↗A (−)-stereoisomer of formula (I): (formula I), wherein X is H or F; or a pharmaceutically acceptable salt or pro drug thereof, is useful as an anesthetic.
1. A (+)-stereoisomer of formula (I):
wherein X is H or F; or a salt or prodrug thereof.
2. The compound of claim 1 , wherein X is H.
3. The compound of claim 1 , which is a (+)-stereoisomer of formula (I) or a pharmaceutically acceptable salt or prodrug thereof.
4. The compound of claim 3 , wherein X is H.
5. A pharmaceutical composition comprising the compound of claim 3 , and a pharmaceutically acceptable carrier.
6. The pharmaceutical composition of claim 5 , wherein X is H.
7. The pharmaceutical composition of claim 5 , which is formulated for intravenous administration.
8. The pharmaceutical composition of claim 7 , wherein X is H.
9. The pharmaceutical composition of claim 7 , which is formulated as a lipid emulsion.
10. The pharmaceutical composition of claim 9 , wherein X is H.
11. The compound of claim 3 , which is a (+)-stereoisomer of formula (I) or a pharmaceutically acceptable salt thereof.
12. The compound of claim 11 , wherein X is H.
13. A pharmaceutical composition comprising a compound of formula (I):
wherein the compound is a (+)-stereoisomer of formula (I) and wherein X is H or F; or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
14. The pharmaceutical composition of claim 13 , wherein X is H.
15. The pharmaceutical composition of claim 13 , which is formulated for intravenous administration.
16. The pharmaceutical composition of claim 15 , wherein X is H.
17. The pharmaceutical composition of claim 15 , which is formulated as a lipid emulsion.
18. The pharmaceutical composition of claim 17 , wherein X is H.
19. A method for inducing or maintaining general anesthesia in an animal comprising administering to the animal an effective amount of a (+)-stereoisomer of formula (I):
wherein X is H or F; or a pharmaceutically acceptable salt or prodrug thereof.
20. The method of claim 19 , wherein X is H.
21. The method of claim 19 , wherein the compound is a (+)-stereoisomer of formula (I) or a pharmaceutically acceptable salt thereof.
22. The method of claim 19 , comprising administering to the animal an effective amount of a (+)-stereoisomer of formula (I) in which X is H, or a pharmaceutically acceptable salt thereof.
23. A method for inducing or maintaining general anesthesia in an animal comprising administering to the animal an effective amount of the pharmaceutical composition of claim 15 .
24. The method of claim 23 , wherein X is H.
25. A method for promoting sedation in an animal comprising administering to the animal an effective amount of a (+)-stereoisomer of formula (I):
wherein X is H or F; or a pharmaceutically acceptable salt or prodrug thereof.
26. The method of claim 25 , wherein X is H.
27. The method of claim 25 , wherein the compound is a (+)-stereoisomer of formula (I) or a pharmaceutically acceptable salt thereof.
28. The method of claim 25 , comprising administering to the animal an effective amount of a (+)-stereoisomer of formula (I) in which X is H, or a pharmaceutically acceptable salt thereof.
29. A method for promoting sedation in an animal comprising administering to the animal an effective amount of the pharmaceutical composition of claim 15 .
30. The method of claim 29 , wherein X is H.
31. A process for preparing a (+)-stereoisomer of formula (I)
wherein X is H or F; or a salt or prodrug thereof, which comprises
(a) hydrolysing a carbamic acid (+)-2-sec-butyl-6-isopropylphenyl ester diastereomer of formula:
in which R 1 represents a chiral amino group;
(b) diazotizing a corresponding (+)-2-sec-butyl-6-isopropyl aniline of formula
or
(c) reducing a corresponding 2-(1-methylallyl)-6-isopropylphenol of formula
followed if required by forming the free phenol or salt or pro-drug thereof.
32. The process of claim 31 , wherein the salt is a pharmaceutically acceptable salt.
33. The process of claim 31 , wherein X is H.
34. The process of claim 31 , wherein the method comprises forming the free phenol or salt or pro-drug thereof.
35. The process of claim 34 , wherein X is H.
36. The process of claim 34 , wherein the method comprises forming the free phenol or pharmaceutically acceptable salt or pro-drug thereof.
37. The process of claim 36 , wherein X is H.
38. The process of claim 36 , wherein the method comprises forming the free phenol or pharmaceutically acceptable salt.
39. The process of claim 38 , wherein X is H.
40. A carbamic acid (+)-2-sec-butyl-6-isopropylphenyl ester diastereoisomer of formula
in which R 1 represents a chiral amino group, and in which X is H or F.
41. A diastereoisomer of claim 40 , wherein R 1 represents an (S)-1-arylethylamino group.