Claims
- 1. A (2S, 3S, 5R) compound of formula (I) ##STR7## or the (+-)-(2R*,3R*,5S*) racemate thereof wherein
- X is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or a group --CH.sub.2 --X.sup.1 where X.sup.1 is cycloalkyl of 3 to 6 carbon atoms,
- or a pharmaceutically acceptable salt thereof.
- 2. A (2S,3S,5R) compound according to claim 1, or a pharmaceutically acceptable salt thereof, substantially free from the (2R,3R,5S) - enantiomorph.
- 3. A compound according to claim 1 or 2 wherein X is hydrogen or alkyl of 1 to 6 carbon atoms, or a pharmaceutically acceptable salt thereof.
- 4. (2S,3S,5R)-2-(3.5-Difluorophenyl)-3,5-dimethyl-2-morpholinol or a pharmaceutically acceptable salt thereof.
- 5. (+-)-(2R*,3R*,5S*)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol or a pharmaceutically acceptable salt thereof.
- 6. (2S,3S,5R)-2-(3,5-Difluorophenyl)-3,4,5-trimethyl-2-morpholinol or a pharmaceutically acceptable salt thereof.
- 7. (+-)-(2R*,3R*5S*)-2-(3,5-Difluorophenyl-3,4,5-trimethyl-2-morpholinol or a pharmaceutically acceptable salt thereof.
- 8. (2S,3S,5R)-2-(3,5-Difluorophenyl)-4-ethyl-3,5-dimethyl-2-morpholinol or a pharmaceutically acceptable salt thereof.
- 9. A pharmaceutically acceptable salt of a compound according to claims 4, 5, 6, 7 or 8.
- 10. The hydrochloride salt of a compound according to claim 9.
- 11. A pharmaceutical composition comprising a (2S,3S,5R) compound of formula (I) ##STR8## or the (+-)-(2R*,3R*,5S*) racemate thereof wherein
- X is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or a group --CH.sub.2 --X.sup.1 where X.sup.1 is cycloalkyl of 3 to 6 carbon atoms.
- or, a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier therefor.
- 12. A pharmaceutical composition according to claim 11 wherein the compound is selected from
- (2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethyl-2-morpholinol
- (+-)-(2R*,3R*,5S*)-2-(3,5-difluorophenyl)-3,5-dimethyl-2-morpholinol (2S,3S,5R)-2-(3,5-difluorophenyl)-3,4,5-trimethyl-2-morpholinol
- (+-)-(2R*,3R*,5S*)-2-(3,5-difluorophenyl)-3,4,5-trimethyl-2-morpholinol and
- (2S,3S,5R)-2-(3,5-difluorophenyl)-4-ethyl-3,5-dimethyl-2-morpholinol.
- 13. A composition according to claim 12 for oral administration.
- 14. A composition according to claim 13 in the form of a capsule or tablet.
- 15. A method of treating narcolepsy-cataplexy syndrome in a human which comprises administering to said human an effective narcolepsy-cataplexy syndrome treatment amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.
- 16. A method of treating depression in a human identified as being depressed, which comprises administering to said human an effective antidepressant amount of a (2S, 3S, 5R) compound of formula (I) ##STR9## or the (+-)-(2R*,5S*) racemate thereof wherein
- X is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or a group --CH.sub.2 X.sup.1 where X.sup.1 is cycloalkyl of 3 to 6 carbon atoms,
- or a pharmaceutically acceptable salt thereof.
- 17. The method of claim 16, in which the compound (2S, 3S, 5R)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol or a pharmaceutically acceptable salt thereof is administered.
- 18. The method of claim 16, in which a (2S, 3S, 5R) compound according to claim 1, or a pharmaceutically acceptable salt thereof, substantially from the (2S, 3S, 5R)-entantimorph is administered.
- 19. The method of claim 16 or claim 18, in which X is hydrogen or alkyl of 1 to 6 carbon atoms, or a pharmaceutically acceptable salt thereof is administered.
- 20. The method of claim 16, in which the compound (+-) -(2R*,3R*,5S*)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol or a pharmaceutically acceptable salt is administered.
- 21. The method of claim 16, in which the compound (2S,3S,5R) -2-(3,5-Difluorophenyl)-3,4,5-trimethyl-2-morpholinol or a pharmaceutically acceptable salt is administered.
- 22. The method of claim 16, in which the compound (+-) -(2R*,3R*,5S*)-2-(3,5-Difluorophenyl)-3,4,5-trimethyl-2-morpholinol or a pharmaceutically acceptable salt is administered.
- 23. The method of claim 16, in which the compound (2S,3S,5R) -2-(3,5-Difluorophenyl)-4-ethyl-3,5-dimethyl-2-morpholinol or a pharmaceutically acceptable salt is administered.
- 24. A method of treating a human identified as being depressed, comprising administering to said human a pharmaceutically acceptable salt of (2S,3S,5R)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol.
- 25. The method of claim 24, in which the hydrochloride salt is administered.
- 26. The method of claim 24 or claim 25, in which the salt is administered orally or parenterally.
- 27. A pharmaceutically acceptable salt of
- (2S,3S,5R)-2-(3,5-Difluorophenyl)-3,4,5-trimethyl-2-morpholinol.
- 28. The hydrochloride salt of
- (2S,3S,5R)-2-(3,5-Difluorophenyl)-3,4,5-trimethyl-2-morpholinol.
- 29. A method of treating depression in a human identified as being depressed, which comprises administering to said human an effective antidepressant amount of the salt of claim 19 or 20.
- 30. A method of treating narcolepsy--cataplexy syndrome in a human identified as being depressed, which comprises administering to said human an effective narcolepsy-- cataplexy syndrome treatment amount of a compound of claim 19 or 20.
- 31. A tablet or capsule containing the salt of claim 19 or 20.
- 32. The method of claim 21, in which the salt is administered orally.
- 33. The method of claim 22, in which the salt is administered orally.
Priority Claims (1)
Number |
Date |
Country |
Kind |
8924528 |
Oct 1989 |
GBX |
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Parent Case Info
This is a continuation of copending application(s) Ser. No. 07/605,890 filed on Oct. 30, 1990 now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3117967 |
Anderson et al. |
Jan 1964 |
|
4576944 |
Lafon |
Mar 1986 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
0139590A3 |
May 1985 |
EPX |
Non-Patent Literature Citations (1)
Entry |
European Patent Application, 170,430, 2-1986. |
Continuations (1)
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Number |
Date |
Country |
Parent |
605890 |
Oct 1990 |
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