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Claims for Patent: 6,667,314

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Claims for Patent: 6,667,314

Title: Tropane derivatives useful in therapy
Abstract:The present invention provides compounds of the formula: ##STR1## wherein R.sup.1 is C.sub.3-6 cycloalkyl optionally substituted by one or more fluorine atoms, or C.sub.1-6 alkyl optionally substituted by one or more fluorine atoms, or C.sub.3-6 cycloalkylmethyl optionally ring-substituted by one or more fluorine atoms; and R.sup.2 is phenyl optionally substituted by one or more fluorine atoms, to pharmaceutically acceptable salts and solvates thereof, and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such compounds.
Inventor(s): Perros; Manoussos (County of Kent, GB), Price; David Anthony (County of Kent, GB), Stammen; Blanda Luzia Christa (County of Kent, GB), Wood; Anthony (County of Kent, GB)
Assignee: Pfizer, Inc. (New York, NY)
Application Number:09/865,950
Patent Claims: 1. A compound of the formula: ##STR46## or a pharmaceutically acceptable salt or solvate thereof, wherein: R.sup.1 is C.sub.3-6 cycloalkyl optionally substituted by one or more fluorine atoms, or C.sub.1-6 alkyl optionally substituted by one or more fluorine atoms, or C.sub.3-6 cycloalkylmethyl optionally ring-substituted by one or more fluorine atoms; and R.sup.2 is phenyl optionally substituted by one or more fluorine atoms.

2. The compound of claim 1 of the formula: ##STR47## or a pharmaceutically acceptable salt or solvate thereof, wherein: R.sup.1 is either C.sub.3-4 cycloalkyl optionally substituted by one or more fluorine atoms, or C.sub.1-6 alkyl optionally substituted by one or more fluorine atoms.

3. The compound of claim 1, wherein R.sup.1 is either C.sub.4-6 cycloalkyl optionally substituted by one or two fluorine atoms, or C.sub.1-4 alkyl optionally substituted by from one to three fluorine atoms.

4. The compound of claim 3, wherein R.sup.1 is either cyclobutyl, cyclopentyl, 4,4-difluorocyclohexyl or 3,3,3-trifluoropropyl.

5. The compound of claim 1, wherein R.sup.2 is phenyl optionally substituted by 1 or 2 fluorine atoms.

6. The compound of claim 5, wherein R.sup.2 is phenyl or monofluorophenyl.

7. The compound of claim 6, wherein R.sup.2 is phenyl or 3-fluorophenyl.

8. The compound of claim 1 which is selected from the group consisting of: N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2.1]oct-8-yl]-1-phenylpropyl}cyclobutanecarboxamide; N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2.1]oct-8-yl]-1-phenylpropyl}cyclopentanecarboxamide; N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2.1]oct-8-yl]-1-phenylpropyl}-4,4,4-trifluorobutanamide; N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicycio[ 3.2.1]oct-8-yl]-1-phenylpropyl}-4,4-difluorocyclohexanecarboxamide; and N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2. 1]oct-8-yl]-1-(3-fluorophenyl)propyl}-4,4-difluorocyclohexanecarboxamide; or a pharmaceutically acceptable salt or solvate of any thereof.

9. A pharmaceutical composition comprising a compound of claim 1 and one of a pharmaceutically acceptable excipient, a pharmaceutically acceptable diluent or a pharmaceutically acceptable carrier.

10. A method of antagonizing a CCR5 receptor in a mammal comprising administering to said mammal in need thereof an effective amount of a compound of claim 1 to antagonize the CCR5 receptor-associated responses in said mammal.

11. A method of treating an inflammatory disease in a mammal comprising administering to said mammal an effective amount of a compound of claim 1.

12. A compound of the formula: ##STR48## wherein R.sup.2 is phenyl optionally substituted by one or more fluorine atoms.

13. The compound of claim 12, wherein R.sup.2 is phenyl.

14. The compound of claim 12 of the formula: ##STR49##

15. The compound of claim 14, wherein R.sup.2 is phenyl.

16. A compound of the formula: ##STR50## wherein R.sup.2 is phenyl optionally substituted by one or more fluorine atoms; and P is a protecting group.

17. The compound of claim 16, wherein R.sup.2 is phenyl.

18. The compound of claim 16, wherein P is t-butyloxycarbonyl or benzyloxycarbonyl.

19. A compound of the formula: ##STR51## wherein P.sup.1 is hydrogen or a protecting group.

20. The compound of claim 19, wherein P.sup.1 is benzyl.

21. The compound of claim 19, or a salt thereof, having the formula: ##STR52##

22. The p-toluenesulphonate salt of the compound of claim 21.

23. A compound of the formula: ##STR53## wherein R.sup.1 is C.sub.3-6 cycloalkyl optionally substituted by one or more fluorine atoms, or C.sub.1-6 alkyl optionally substituted by one or more fluorine atoms, or C.sub.3-6 cycloalkylmethyl optionally ring-substituted by one or more fluorine atoms; and R.sup.2 is phenyl optionally substituted by one or more fluorine atoms.

24. The compound of claim 23, wherein R.sup.2 is phenyl.

25. A compound of the formula: ##STR54## where R.sup.2 is phenyl optionally substituted by one or more fluorine atoms.

26. The compound of claim 25, wherein R.sup.2 is phenyl.

27. A compound of the formula: ##STR55## wherein R.sup.1 is C.sub.3-6 cycloalkyl optionally substituted by one or more fluorine atoms, or C.sub.1-6 alkyl optionally substituted by one or more fluorine atoms, or C.sub.3-6 cycloalkylmethyl optionally ring-substituted by one or more fluorine atoms; and R.sup.2 is phenyl optionally substituted by one or more fluorine atoms.

28. The compound of claim 27, wherein R.sup.2 is phenyl.

29. A compound selected from the group consisting of: ##STR56##

30. A process for the preparation of a compound of claim 1 selected from a process which comprises: (a) coupling a compound of the formula: ##STR57## with a compound of formula:

31. A compound of claim 1 which is N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2.1]oct-8-yl]-1-phenylpropyl}cyclobutanecarboxamide or a pharmaceutically acceptable salt or solvate thereof.

32. A compound of claim 1 which is N-{(1S)-3-[3-(3-Isopropyl-3-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2.1]oct-8-yl]-1-phenylpropyl}cyclopentanecarboxamide or a pharmaceutically acceptable salt or solvate thereof.

33. A compound of claim 1 which is N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2.1]oct-8-yl]-1-phenylpropyl}-4,4,4-trifluorobutanamide or a pharmaceutically acceptable salt or solvate thereof.

34. A compound of claim 1 which is N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo [3.2.1]oct-8-yl]-1-phenylpropyl}-4,4-difluorocyclohexanecarboxamide or a pharmaceutically acceptable salt or solvate thereof.

35. A compound of claim 1 which is N-{(1S)-3-[3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[ 3.2. 1]oct-8-yl]-1-(3-fluorophenyl)propyl}-4,4-difluorocyclohexanecarboxamide or a pharmaceutically acceptable salt or solvate thereof.
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