IP Library › Granted Patent US 7,585,974
Granted Patent B2
US 7,585,974 · App. 11/696,993 · Granted Sep 8, 2009

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

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Quick Facts
Patent No.
US 7,585,974
App. No.
11/696,993
Granted
Sep 8, 2009
Kind
B2
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 (C 1 -C 6 )alkyl, (C 1 -C 6 )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 (C 1 -C 6 )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.

Claims (74)

1. 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).

2. A compound selected from the group consisting of:

5-(2-phenylpyridin-5-yl)-1-azabicyclo[3.2.1]oct-3-ene hydrobromide (2:1);

5-(2-phenylpyridin-5-yl)-1-azabicyclo[3.2.1]octane hydrobromide (2:1);

5-(2-phenylpyridin-5-yl)-1-azabicyclo[3.2.1]oct-2-ene hydrobromide (2:1).

Assignments (1)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →