Claims
- 1. A compound of formula I:
- 2. A compound according to claim 1 comprising a hydrate.
- 3. A compound according to claim 1 or 2 having the stereochemistry in formula (IA):
- 4. A compound according to any one of claims 1-3, wherein X is a linear C2-4 alkylene moiety unsubstituted or substituted by one or more fluorine atoms.
- 5. A compound according to claim 4, wherein X is propylene.
- 6. A compound according to any one of claims 1-5, wherein R is C3-8 cycloalkyl unsubstituted or substituted by one or more fluorine atoms.
- 7. A compound according to claim 6, wherein R is cyclobutyl or cyclohexyl unsubstituted or substituted by one or more fluorine atoms.
- 8. A compound according to any one of claims 1-7, wherein W is N, CH or CCH3.
- 9. A compound according to any one of claims 1-8, wherein Y1 is:
C1-C4 alkyl, unsubstituted or substituted by phenyl or by one or more halogen atoms; phenyl, unsubstituted or substituted by one or more substituents independently selected from halogen, C1-C4 alkoxy, and C1-C4 alkyl unsubstituted or substituted with one or more halogen, wherein said phenyl ring is optionally pyrido-fused; or a 5- or 6- membered heterocyclic ring with one or two ring heteroatoms selected from N, O and S, which heterocyclic ring is unsubstituted or substituted by one or more substituents independently selected from halogen, C1-C4 alkoxy, and C1-C4 alkyl unsubstituted or substituted with one or more halogen.
- 10. A compound according to claim 9, wherein Y1 is selected from phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-isopropylphenyl, 3,4-dimethoxyphenyl, 8-quinolinyl, 3,5-dimethyl-4-isoxazolyl, isopropyl, methyl, benzyl and 3-pyridyl.
- 11. A compound according to any one of claims 1-10, wherein X1 is H or methyl.
- 12. A compound according to claim 1 which is selected from:
(3R)-6-Cyclohexyl-N-hydroxy-3-(3 -{[(phenylsulfonyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanamide; (3R)-6-Cyclohexyl-N-hydroxy-3-[3-({[(4-methylphenyl)sulfonyl]amino}carbonyl)-1,2,4-oxadiazol-5-yl]hexanamide; (3R)-6-Cyclohexyl-N-hydroxy-3-[3-({[(4-methoxyphenyl)sulfonyl]amino}carbonyl)-1,2,4-oxadiazol-5-yl]hexanamide; (3R)-6-Cyclohexyl-3-[3-({[(4-fluorophenyl)sulfonyl]amino}carbonyl)-1,2,4-oxadiazol-5-yl]-N-hydroxyhexanamide; (3R)-6-Cyclohexyl-N-hydroxy-3-[3-({[(4-isopropylphenyl)sulfonyl]amino}carbonyl)-1,2,4-oxadiazol-5-yl]hexanamide; (3R)-6-Cyclohexyl-3-[3-({[(3,4-dimethoxyphenyl)sulfonyl]amino}carbonyl)-1,2,4-oxadiazol-5-yl]-N-hydroxyhexanamide; (3R)-6-Cyclohexyl-N-hydroxy-3-(3-{[(8-quinolinylsulfonyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanamide; (3R)-6-Cyclohexyl-3-[3-({[(3,5-dimethyl-4-isoxazolyl)sulfonyl]amino}carbonyl)-1,2,4-oxadiazol-5-yl]-N-hydroxyhexanamide; (3R)-6-Cyclohexyl-N-hydroxy-3-(3{[(isopropylsulfonyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanamide; (3R)-6-Cyclohexyl-N-hydroxy-3-(3-{[methyl(methylsulfonyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl]hexanamide; (3R)-6-Cyclohexyl-N-hydroxy-3-(3-{[(phenylmethyl)sulfonyl]amino}carbonyl)-1,2,4-oxadiazol-5-yl)hexanamide; and (3R)-6-Cyclohexyl-N-hydroxy-3-(3-{[(3-pyridylsulfonyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanamide; and the salts, solvates and prodrugs thereof.
- 13. A compound according to claim 12 comprising a hydrate.
- 14. A method of treating a PCP mediated condition or disease comprising administering a compound according to any one of claims 1 to 13.
- 15. A pharmaceutical composition comprising a compound of formula (I):
- 16. A method of treating a condition mediated by PCP comprising administering a therapeutically effective amount of a compound according to any one of claims 1 to 13.
- 17. A process for making a compound according to claim 1, wherein W=CZ, comprising one or more of steps (a) to (d):
(a) reacting a compound of formula (V), deprotonated if necessary with a base, with a reagent of formula X2SO2Y1, where x2 is a suitable leaving group, to make a compound of formula (IV); 62(b) deprotecting a compound of formula (IV) to make a compound of formula (III); 63(c) reacting a compound of formula (III) with a coupling agent to form a compound of formula (II) where L1 is a suitable leaving group; 64and (d) reacting a compound of formula (II) with hydroxylamine or a protected derivative thereof to form the hydroxamic acid of formula (I) 65
- 18. A process for making a compound of claim 1, wherein W=N, comprising one or more of steps (a) to (d):
(a) reacting a compound of formula (XII), deprotonated if necessary with a base, with a reagent of formula X2SO2Y1, where X2 is a suitable leaving group, to make a compound of formula (XI); 66(b) deprotecting a compound of formula (XI) to make a compound of formula X); 67(c) reacting a compound of formula (X) with a coupling agent, to form a compound of formula (IX), where L1 is a suitable leaving group; 68and (d) reacting a compound of formula (IX) with hydroxylamine or a protected derivative thereof to form a hydroxamic acid of formula (I): 69
- 19. A process according to claim 18, wherein said coupling agent comprises an alkylhaloformate or carbonyldiimidazole.
- 20. A compound of formula (II), (III) or (IV):
- 21. A compound of formula (IX), (X) or (XI):
Priority Claims (1)
Number |
Date |
Country |
Kind |
GB 0108097.7 |
Mar 2001 |
GB |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This non-provisional patent application claims priority to United Kingdom Patent Application No. GB 0108097.7, filed Mar. 30, 2001, and to U.S. Patent Application No. 60/293,419, filed May 24, 2001, each is which is hereby incorporated by reference in its entirety.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60293419 |
May 2001 |
US |