Claims
- 1. A compound of Formula I or a pharmaceutically acceptable salt thereof, with Formula I being: ##STR87## wherein R.sub.1 and R.sub.2 are independently selected from H, halogen, CF.sub.3, or C.sub.1-4 alkoxy groups except that R.sub.1 and R.sub.2 cannot both be H simultaneously, or R.sub.1 and R.sub.2, when on adjacent carbon atoms, can be taken together to form a ##STR88## bridge with n being an integer from 1 to 3; R.sub.3 is H or C.sub.1-4 alkyl;
- R.sub.4 and R.sub.5 are each independently selected from H, C.sub.1-4 alkyl or phenyl;
- Y is CH; and
- Ar is an unsubstituted phenyl ring; a substituted phenyl ring of structure II: ##STR89## wherein Xp and Xq may be halogen, nitro, amino, carboxamido, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 alkylthio or Xp and Xq can be taken together to form a ##STR90## (n=1-3); or a heteroaryl group selected from 3-pyridinyl, 4-pyridinyl, 2-thienyl, 2-furanyl, and 1-methyl-2-pyrrolyl moieties.
- 2. The compound of claim 1 wherein R.sub.1 and R.sub.2 taken together form the bridge ##STR91## (n=1-3).
- 3. The compound of claim 2 wherein each of R.sub.3, R.sub.4 and R.sub.5 is H.
- 4. The compound of claim 1, Z-1-(1,3-benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol.
- 5. The compound of claim 1, Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]-cyclohexanol.
- 6. The compound of claim 1, Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperidine.
- 7. The compound of claim 1, Z-1-(4-methoxyphenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol.
- 8. The compound of claim 1 selected from the group consisting of:
- Z-1-1-(1,3-benzodioxol-5-yl)-4-[4(phenylmethyl )-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-[(2,5-difluorophenyl)methyl]-1piperidinyl]cyclohexanol; and
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperidine.
- 9. The compound of claim 1 selected from the group consisting of:
- Z-1-(1,4-benzodioxan-6-yl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperidine;
- Z-1-[4-(1,4-benzodioxan-6-yl)-4-methoxy-1-cyclohexyl]-4-[3-(methoxyphenyl)methyl]piperidine fumarate; and
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl-4-[(2,5-difluorophenyl)methyl]piperidine fumarate.
- 10. The compound of claim I selected from the group consisting of:
- Z-1-(4-fluorophenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol; and
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol.
- 11. The compound according to claim 1 selected from the group consisting of:
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-[4-(methoxy-1-cyclohexyl]-4-(3-methoxyphenyl)methyl]piperidine; and
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol.
- 12. A pharmaceutical composition comprising an effective anxiolytic amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
- 13. The composition of claim 12 wherein the compound is Z-1-(1,3-benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol.
- 14. The composition of claim 12 the compound is selected from the group consisting of:
- Z-1 -(1,3-benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperidine;
- Z-1-(4-fluorophenyl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol; and
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol.
- 15. A method of treating anxiety comprising administering to a patient in need therof an effective amount of a compound of claim 1.
- 16. The method of claim 15 herein the compound is selected from the group consisting of: Z-1-(1,3-benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol; and
- Z-1-(4-methoxyphenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol.
- 17. The method of claim 15 wherein the compound is
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]-cyclohexanol.
- 18. The method of claim 15 wherein the compound is Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperidine.
- 19. The method of claim 15 wherein the compound is selected from the group consisting of:
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]-piperidine; and
- Z-1-(4-fluorophenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol.
- 20. The method of claim 19 wherein the compound is selected from the group consisting of:
- Z-1-(1,4-benzodioxan-6-yl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperidine;
- Z-1-]4-(1,4-benzodioxan-6-yl)-4-methoxy-1-cyclohexyl]-4-[3-(methoxyphenyl)methyl]piperidine fumarate; and
- Z-1-]4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(2,5-difluorophenyl)methyl]piperidine fumarate.
- 21. The method of claim wherein the compound is selected from the group consisting of:
- Z-1-(4-fluorophenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol; and
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol.
- 22. A method for the prophylactic treatment of migraines comprising administering to a patient in need thereof an effective amount of a compound of claim 1.
- 23. The method of claim 22 wherein the compound is selected from the group consisting of: Z-1-(1,3-benzodioxol-5-yl)-4-[(phenylmethyl)-1-piperidinyl]cyclohexanol; and
- Z-1-(4-methoxyphenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol.
- 24. The method of claim 22 wherein the compound is selected from the group consisting of:
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-(phenylmethyl)-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(3-methoxyphenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(4-fluorophenyl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol;
- Z-1-(1,3-benzodioxol-5-yl)-4-[4-[(2,5-difluorophenyl)methyl]-1-piperidinyl]cyclohexanol; and
- Z-1-[4-(1,3-benzodioxol-5-yl)-4-methoxy-1-cyclohexyl]-4-[(3-methoxyphenyl)methyl]piperidine.
Parent Case Info
CROSS REFERENCE TO RELATED PATENT
This application is a continuation-in-part of copending application U.S. Ser. No. 07/952,229, filed Sep. 28, 1992 and now abandoned, which is a continuation-in-part of U.S. Ser. No. 07/806,989, filed Dec. 13, 1991 now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3965180 |
Lednicer |
Jun 1976 |
|
Non-Patent Literature Citations (2)
Entry |
Mattson et al, Chemical Abstracts, vol. 119, No. 180667 (Abstract for EP 546583, Jun. 16, 1993) (1993). |
Mattson et al, Chemical Abstracts, vol. 120, No. 45972 (Abstract for EP 560669, Sep. 15, 1993) (1994). |
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
952229 |
Sep 1992 |
|
Parent |
806989 |
Dec 1991 |
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