IP Library Granted Patent US 7,951,948
Granted Patent B2
US 7,951,948 · App. 12/762,719 · Granted May 31, 2011

Spirocyclic cyclohexane compounds

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Quick Facts
Patent No.
US 7,951,948
App. No.
12/762,719
Granted
May 31, 2011
Kind
B2
Abstract

Spirocyclic cyclohexane compounds corresponding to formula I a method for producing them, pharmaceutical compositions containing them, and methods of using them.

Claims (52)

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.

Assignments (2)
CHANGE OF NAME Recorded May 21, 2025
From: PARK THERAPEUTICS, INC.
To: ADNEURIS THERAPEUTICS, INC.
Reel/Frame 071349/0825 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2021
From: GRÜNENTHAL GMBH
To: PARK THERAPEUTICS, INC.
Reel/Frame 057212/0157 →