IP Library Granted Patent US 7,989,470
Granted Patent B2
US 7,989,470 · App. 12/727,972 · Granted Aug 2, 2011

3,8-substituted 8-aza-bicyclo[3.2.1]octane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors

Assignee: Neurosearch A/S
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Quick Facts
Patent No.
US 7,989,470
App. No.
12/727,972
Granted
Aug 2, 2011
Kind
B2
Abstract

This invention relates to novel 8-aza-bicyclo[3.2.1]octane derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

Claims (45)

1. An 8-aza-bicyclo[3,2,1]octane chemical compound of Formula I:

or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof;

wherein

R a represents —(R c ) n —C(═O)R′, —(R c ) n —C(═O)OR′, —(R c ) n —C(═S)NR′R″ or —(R c ) n —C(═O)NR′R″;

wherein R c represents alkyl;

n is 0 or 1;

R′ and R″ independent of each other represent hydrogen, alkyl, or aryl;

X represents —O—;

R b represents phenyl, pyridyl or naphthyl,

which phenyl, pyridyl or naphthyl is substituted with one or more substituents independently selected from the group consisting of:

chloro, bromo and alkoxy.

2. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R a represents —(R c ) n —C(═O)R′;

wherein R′ represents hydrogen.

3. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R a represents —(R c ) n —C(═O)OR′;

wherein R′ represents alkyl.

4. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R a represents —(R c ) n —C(═S)NR′R″;

wherein R′ and R″ represent hydrogen.

5. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R a represents —(R c ) n —C(═O)NR′R″;

wherein R′ represents hydrogen; and

R″ represents hydrogen or phenyl.

6. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

n is 0.

7. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

n is 1 and R c represents —CH 2 —, —CH 2 —CH 2 — or —C(CH 3 )H—.

8. The chemical compounds of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R b represents phenyl or pyridyl substituted with one or more chloro.

9. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R b represents phenyl substituted with one or more chloro.

10. The chemical compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R b represents pyridyl substituted with one or more chloro.

11. The chemical compound of claim 1 , which is

2-[3-(3,4-Dichloro-phenoxy)-8-aza-bicyclo[3.2.1]oct-8-yl]-acetamide;

3-(3,4-Dichloro-phenoxy)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid phenylamide;

3-(3,4-Dichloro-phenoxy)-8-aza-bicyclo[3.2.1]octane-8-carbaldehyde;

3-(5-Chloro-pyridin-2-yloxy)-8-aza-bicyclo[3.2.1]octane-8-carbaldehyde;

2-[3-(6-Bromo-pyridin-2-yloxy)-8-aza-bicyclo[3.2.1]oct-8-yl]-acetamide;

[3-(3,4-Dichloro-phenoxy)-8-aza-bicyclo[3.2.1]oct-8-yl]-acetic acid ethyl ester;

2-[3-(5-Chloro-pyridin-2-yloxy)-8-aza-bicyclo[3.2.1]oct-8-yl]acetamide; or

2-[3-(3,4-Dichloro-phenoxy)-8-aza-bicyclo[3.2.1]oct-8-yl]-thioacetamide;

or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof.

12. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 1 , or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, together with at least one pharmaceutically acceptable carrier, excipient or diluent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2013
From: NEUROSEARCH A/S
To: ANIONA APS
Reel/Frame 030049/0894 →
Priority Claims (1)
DK 2005 00068 · Jan 13, 2005 · national
Continuity (3)
Division 11794365
Provisional Application 60643590 · Jan 14, 2005
Related Publication 20100190821A1 · Jul 29, 2010