US 2007/0185137 A1Published application

Derivatives of 5-(pyridin-3-yl)-1-azabicyclo[3.2.1]octane, their preparation and their therapeutic application

AssigneeSanofi-Aventis

InventorsFrederic GALLI, Odile LECLERC, Alistair LOCHEAD, Alain NEDELEC

Life of this patent

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Abstract

Compounds complying with the general formula in which R either represents a halogen atom or a phenyl group substituted by one or more groups chosen from halogen atoms and (C1-C6)alkyl, (C1-C6)alkoxy, nitro, amino, trifluoromethyl, cyano, hydroxy, acetyl or methylenedioxy groups, or represents a pyridinyl group, a thienyl group, an indolyl group, or a pyrimidinyl group optionally substituted by one or more (C1-C6)alkoxy groups, where, of the two carbon-carbon bonds represented by one is single and the other may be single or double. The compounds of this invention are useful as therapeutic agents.

Claims2

Dependent claims

A compound selected from the group consisting of:

5-[2-(2,4-dimethoxy-5-pyrimidinyl)-pyridin-5-yl]-1-azabicyclo[3.2.1]oct-2-ene hydrobromide (2:1);
5-[2-(3,4-dimethoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3,4-dimethoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1)
5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-nitrophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-trifluoromethylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(1,3-benzodioxol-5-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-chlorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
1-{3-[5-(1-azabicyclo[3.2.1]oct-3-en-5-yl)pyridin-2-yl]phenyl}ethanone ethanedioate (1:1);
5-[2-(3-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(5-indolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3,5-dimethylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3,5-dimethylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(1,3-benzodioxol-5-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-nitrophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-trifluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-bromopyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-bromopyridin-5-yl]-1-azabicyclo[3.2.1]oct-2-ene hydrobromide (2:1);
5-[2-(4-piperidinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-piperidinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
(+)-5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
(−)-5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
(+)-5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
(−)-5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
5-[2-(2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(5-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(5-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(5-chloro-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(5-chloro-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(5-indolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1);
5-[2-(2-benzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene;
5-[2-(2-benzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-pyrrolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2-pyrrolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1);
5-[2-(2-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene;
5-[2-(2-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-hydroxy-3-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
5-[2-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2,4-dimethoxypyrimidin-5-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1);
5-[2-(4-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(1-dibenzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(1-dibenzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(1-phenoxatiinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(1-phenoxatiinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(8-quinoleinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(8-quinoleinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1).

66 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/696,993Filed 5 Apr 2007
Priority: FR 02001097 Jan 2002
Published: 9 Aug 2007
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 471/08
In which the condensed system contains two hetero rings: bridged systems
A61P 25/00
Drugs for disorders of the nervous system
A61P 25/14
Drugs for disorders of the nervous system: for treating abnormal movements, e.g. chorea, dyskinesia
A61P 25/16
For treating abnormal movements, e.g. chorea, dyskinesia: anti-Parkinson drugs

Family

Application10/500,015Continuation · filed 23 Jun 2004
Application11/696,993Continuation · filed 5 Apr 2007
US 2005/0020568 A1Published application
US 7,223,750 B2Related patent
US 7,585,974 B2Related patent
US 2007/0185137 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound selected from the group consisting of:

5-[2-(2,4-dimethoxy-5-pyrimidinyl)-pyridin-5-yl]-1-azabicyclo[3.2.1]oct-2-ene hydrobromide (2:1);
5-[2-(3,4-dimethoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3,4-dimethoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1)
5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-nitrophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-trifluoromethylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(1,3-benzodioxol-5-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-chlorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
1-{3-[5-(1-azabicyclo[3.2.1]oct-3-en-5-yl)pyridin-2-yl]phenyl}ethanone ethanedioate (1:1);
5-[2-(3-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(5-indolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(3,5-dimethylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene ethanedioate (1:1);
5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-methylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3,5-dimethylphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(1,3-benzodioxol-5-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-nitrophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-trifluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-bromopyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-bromopyridin-5-yl]-1-azabicyclo[3.2.1]oct-2-ene hydrobromide (2:1);
5-[2-(4-piperidinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-piperidinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
(+)-5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
(−)-5-[2-(4-methoxyphenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
(+)-5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
(−)-5-[2-(3-fluorophenyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
5-[2-(2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(5-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(5-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(5-chloro-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(5-chloro-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(5-indolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1);
5-[2-(2-benzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene;
5-[2-(2-benzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(2-pyrrolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2-pyrrolyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1);
5-[2-(2-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene;
5-[2-(2-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3-furyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-hydroxy-3-pyridinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane;
5-[2-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(2,4-dimethoxypyrimidin-5-yl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1);
5-[2-(4-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(4-methyl-2-thienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(1-dibenzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(1-dibenzofuryl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(1-phenoxatiinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(1-phenoxatiinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(8-quinoleinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane hydrobromide (2:1);
5-[2-(8-quinoleinyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);
5-[2-(3-benzothienyl)pyridin-5-yl]-1-azabicyclo[3.2.1]octane ethanedioate (1:1).

66 more elements

Facts

Application

11/696,993Filed 5 Apr 2007

Priority

FR 02001097 Jan 2002

Published

9 Aug 2007

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 471/08
In which the condensed system contains two hetero rings: bridged systems
A61P 25/00
Drugs for disorders of the nervous system
A61P 25/14
Drugs for disorders of the nervous system: for treating abnormal movements, e.g. chorea, dyskinesia
A61P 25/16
For treating abnormal movements, e.g. chorea, dyskinesia: anti-Parkinson drugs

Family

Application10/500,015Continuation · filed 23 Jun 2004

Application11/696,993Continuation · filed 5 Apr 2007

US 2005/0020568 A1Published application

US 7,223,750 B2Related patent

US 7,585,974 B2Related patent

US 2007/0185137 A1This patent

From the US filing history. Foreign family members aren’t listed.