Process for preparing spirocyclic cyclohexane compounds, compositions containing such compounds and method of using such compounds

1. A method of treating pain, said method comprising administering to a patient in need thereof an effective amount of a spirocyclic cyclohexane compound selected from the group consisting of:

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano [3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-2-thia-9-azafluorene,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-2-oxa-9-thiafluorene,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-3,4-dihydro-1H-2-oxa-9-thiafluorene,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-2,9-dioxafluorene,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methoxy-1,3,4,9-tetrahydropyrano[3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole,

6-bromo-1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-6-nitro-1,3,4,9-tetrahydropyrano[3,4-b]indole,

6-chloro-1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole,

3,9-dimethyl-1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[3,4-b]indole,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetra-hydro-pyrano[3,4-b]indole,

1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetra-hydro-pyrano[3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano [3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-methyl-1,3,4,9-tetrahydropyrano [3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-9-phenyl-1,3,4,9-tetrahydropyrano [3,4-b]indole,

1,1-(3-methylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano-[3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-3-methyl-1,3,4,9-tetrahydro-pyrano-[3,4-b]indole,

3,6-dimethyl-1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetra-hydro-pyrano-[3,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3-methyl-9-phenyl-1,3,4,9-tetrahydropyrano[3,4-b]indole,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-1,3,4,9-tetra-hydro-2-thia-9-azafluorene,

1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetra-hydro-2-thia-9-azafluorene,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-9-oxa-2-thiafluorene,

6,6-(3-dimethylamino-3-phenylpentamethylene)-1,2,3,4,4a,6,7,11c-octahydro-5-oxa-7-azabenzo [c]fluorene,

1,1-(3-dimethylamino-3-phenylpentamethylene)-6-bromo- 1,3,4,9-tetrahydropyrano [3 ,4-b]indole,

1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydro-pyrano [3,4-b]indol-6-ol,

1,1-(3-methylamino-3-phenylpentamethylene)-6-fluoro- 1,3,4,9-tetrahydropyrano [3,4-b]indole,

1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-3,4-dihydro- 1H-2,9-dithiafluorene,

1,1-(3-dimethylamino-3-phenylpentamethylene)-3,4-dihydro-1H-2,9-dithiafluorene, and

1,1-(3-dimethylamino-3-phenylpentamethylene)-2-oxo-1,3,4,9-tetrahydro-2-thia-9-aza-fluorene and 1,1-(3-dimethylamino-3-(4-fluorophenyl)pentamethylene)-2-oxo-3,4-dihydro-1H-2-thia-9-thiafluorene,

or a salt of any of the foregoing with a physiologically acceptable acid.

2. A method according to claim 1 , wherein said pain is selected from the group consisting of acute pain, neuropathic pain, and chronic pain.

3. A method according to claim 1 , wherein said spirocyclic cyclohexane compound corresponds to a formula selected from the group consisting of:

or a salt of any of the foregoing with a physiologically acceptable acid selected from the group consisting of hydrochloric acid, citric acid, tartaric acid, methane sulfonic acid, and trifluoromethane sulfonic acid.

4. A method according to claim 1 , wherein said spirocyclic cyclohexane compound is 1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole or a salt thereof with a physiologically acceptable acid.

5. A method according to claim 4 , wherein said spirocyclic cyclohexane compound is the more polar diastereomer.

6. A method according to claim 4 , wherein said spirocyclic cyclohexane compound is the more non-polar diastereomer.

7. A method according to claim 1 , wherein said spirocyclic cyclohexane compound corresponds to the formula:

or a salt thereof with a physiologically acceptable acid selected from the group consisting of hydrochloric acid, citric acid, tartaric acid, methane sulfonic acid, and trifluoromethane sulfonic acid.

8. A method according to claim 1 , wherein said spirocyclic cyclohexane compound is 1,1-(3-methylamino-3-phenylpentamethylene)-6-fluoro-1,3,4,9-tetrahydropyrano[3,4-b]indole or a salt thereof with a physiologically acceptable acid.

9. A method according to claim 1 , wherein said spirocyclic cyclohexane compound corresponds to the formula:

or a salt thereof with a physiologically acceptable acid selected from the group consisting of hydrochloric acid, citric acid, tartaric acid, methane sulfonic acid, and trifluoromethane sulfonic acid.

10. A method according to claim 8 , wherein said spirocyclic cyclohexane compound is in the form of an enantiomer or diastereomer.

11. A method according to claim 10 , wherein the spirocyclic cyclohexane compound is administered orally.

12. A method according to claim 4 , wherein said pain is selected from the group consisting of acute pain, visceral pain, neuropathic pain, chronic pain, and chronic neuropathic pain.

13. A method according to claim 4 , wherein the spirocyclic cyclohexane compound is administered orally.

14. A method according to claim 1 , wherein said spirocyclic cyclohexane compound is in the form of a racemate.

15. A method according to claim 1 , wherein said spirocyclic cyclohexane compound is in the form of an enantiomer or diastereomer.

16. A method according to claim 1 , wherein said spirocyclic cyclohexane compound is in the form of a mixture of enantiomers or diastereomers.

17. A method according to claim 8 , wherein said spirocyclic cyclohexane compound is in the form of a racemate.

18. A method according to claim 10 , wherein said pain is selected from the group consisting of acute pain, visceral pain, neuropathic pain, chronic pain, and chronic neuropathic pain.

19. A method according to claim 8 , wherein said spirocyclic cyclohexane compound is in the form of a mixture of enantiomers or diastereomers.