Spirocyclic cyclohexane compounds
View Patent ↗Spirocyclic cyclohexane compounds corresponding to formula I a method for producing them, pharmaceutical compositions containing them, and methods of using them.
1. 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-tetrahydropyrano[3,4-b]indole;
1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydropyrano[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-tetrahydropyrano[3,4-b]indole;
1,1-(3-dimethylamino-3-phenylpentamethylene)-6-fluoro-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole;
3,6-dimethyl-1,1-(3-dimethylamino-3-phenylpentamethylene)-1,3,4,9-tetrahydropyrano[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-tetrahydro-2-thia-9-azafluorene;
1,1-(3-dimethylamino-3-(3-fluorophenyl)pentamethylene)-1,3,4,9-tetrahydro-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,
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.
2. A compound as claimed in claim 1 , wherein said compound is the more polar diastereomer.
3. A compound as claimed in claim 1 , wherein said compound is the more non-polar diastereomer.
4. A spirocyclic cyclohexane compound corresponding to a formula selected from the group consisting of:
or a salt of any of the foregoing with a physiologically acceptable acid.
5. A compound as claimed in claim 4 , wherein said compound is the more polar diastereomer.
6. A compound as claimed in claim 4 , wherein said compound is the more non-polar diastereomer.
7. 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 selected from the group consisting of hydrochloric acid, citric acid, tartaric acid, methane sulfonic acid, and trifluoromethane sulfonic acid.
8. A compound as claimed in claim 7 , wherein said compound is the more polar diastereomer.
9. A compound as claimed in claim 7 , wherein said compound is the more non-polar diastereomer.
10. A spirocyclic cyclohexane compound corresponding to the formula:
or a salt thereof with a physiologically acceptable acid.
11. A compound as claimed in claim 10 , wherein said compound is the more polar diastereomer.
12. A compound as claimed in claim 10 , wherein said compound is the more non-polar diastereomer.
13. 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 selected from the group consisting of hydrochloric acid, citric acid, tartaric acid, methane sulfonic acid, and trifluoromethane sulfonic acid.
14. A compound as claimed in claim 13 , wherein said compound is the more polar diastereomer.
15. A compound as claimed in claim 13 , wherein said compound is the more non-polar diastereomer.
16. A spirocyclic cyclohexane compound corresponding to the formula:
or a salt thereof with a physiologically acceptable acid.
17. A compound as claimed in claim 16 , wherein said compound is the more polar diastereomer.
18. A compound as claimed in claim 16 , wherein said compound is the more non-polar diastereomer.