	US 7,585,974 B2
	Derivatives of 5-(pyridin-3-yl)-1-azabicyclo[3.2.1]octane, their preparation and their therapeutic application
Frederic Galli, Vaucresson (France); Odile LeClerc, Massy (France); Alistair Lochead, Charenton le Pont (France); and Alain Nedelec, Paris (France)
Assigned to Sanofi-Aventis, Paris (France)
Filed on Apr. 05, 2007, as Appl. No. 11/696,993.
Application 11/696993 is a continuation of application No. 10/500015, granted, now 7,223,750, previously published as PCT/FR03/00004, filed on Jan. 03, 2003.
Claims priority of application No. 02 00109 (FR), filed on Jan. 07, 2002.
Prior Publication US 2007/0185137 A1, Aug. 09, 2007
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 237/00 (2006.01); C07D 401/00 (2006.01); C07D 221/99 (2006.01)

U.S. Cl. 544—240 [544/310; 546/112]

2 Claims

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).