IP Library › Granted Patent US 7,045,522
Granted Patent B2
US 7,045,522 · App. 10/726,680 · Granted May 16, 2006

8-Azabicyclo[3.2.1]oct-2-ene and -octane derivatives technical field

Assignee: Neurosearch A/S
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Quick Facts
Patent No.
US 7,045,522
App. No.
10/726,680
Granted
May 16, 2006
Kind
B2
Abstract

The present invention relates to novel 8-azabicyclo[3.2.1]oct-2-ene and -octane derivatives which are found to be cholinergic ligands at the nicotinic Acetyl Choline Receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neurodegeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

Claims (38)

1. A chemical compound having the formula

in labelled or unlabelled form, or any of its enantiomers or any mixture thereof, or a pharmaceutically acceptable salt thereof;

R represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, a mono- or polycyclic aryl group, or aralkyl; and

R 1 represents a bi-cyclic heterocyclic group selected from the group consisting of 5- or 6-benzimidazolyl, 5- or 6-benzofuranyl, 5- or 6-benzothiazolyl, 5- or 6-benzothienyl, 5- or 6-Benzotriazolyl, 6- or 7-cinnolinyl, 5- or 6-indazolyl, 5- or 6-indolizinyl, 5- or 6-indolyl, 5- or 6- isoindolyl, 6- or 7-isoquinolinyl, 6-phthalazinyl, 6- or 7-quinolinyl, 6- or 7-quinolizinyl, and 6- or 7-quinoxalinyl; which heterocyclic groups may be substituted one or more times with substituents selected from the group consisting halogen, amino, hydroxy, alkoxy, alkoxy-alkyl, alkoxy-alkoxy, sulfanyl, alkylsulfanyl, alkylsulfanyl-alkoxy, alkoxy-alkylsulfanyl, and alkylsulfanyl-alkylsulfanyl.

2. The chemical compound of claim 1 , wherein R 1 represents a bi-cyclic heterocyclic group selected from the group consisting of 5- or 6-benzimidazolyl, 5- or 6-benzofuranyl, 5- or 6-benzothiazolyl, 5- or 6-benzothienyl, 5- or 6-Benzotriazolyl, 6- or 7-cinnolinyl, 5- or 6-indazolyl, 5- or 6-indolizinyl, 5- or 6-indolyl, 5- or 6-isoindolyl, 6- or 7-isoquinolinyl, 6-phthalazinyl, 6- or 7-quinolinyl, 6- or 7-quinolizinyl, and 6- or 7-quinoxalinyl; which heterocyclic groups may be substituted one or more times with substituents selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkoxy-alkyl, alkoxy-alkoxy, sulfanyl, alkylsulfanyl, alkylsulfanyl-alkoxy, alkoxy-alkylsulfanyl, and alkylsulfanyl-alkylsulfanyl.

3. A compound selected from the group consisting of:

(±)-3-[6-Isoquinolinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Quinolinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[7-Isoquinolinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[7-Quinolinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-H-5-Benzimidazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-H-6-Benzimidazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-H-5-Benzotriazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-H-6-Benzotriazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[2-Amino-1-H-5-benzimidazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[2-Amino-1-H-6-benzimidazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-phthalazinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[5-Benzofuranyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Benzofuranyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[5-Benzothienyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Benzothienyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[5-Benzothiazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Benzothiazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-Methyl-5-indolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-Methyl-6-indolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[5-Indolizinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Indolizinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[2-Methyl-5-isoindolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[2-Methyl-6-isoindolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-Methyl-5-indazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[1-Methyl-6-indazolyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Quinolizinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[7-Quinolizinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Cinnolinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[7-Cinnolinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

(±)-3-[6-Quinoxalinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene; or

(±)-3-[7-Quinoxalinyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene;

or a pharmaceutically acceptable addition salt thereof.

Priority Claims (1)
DK 1998 01570 · Nov 27, 1998 · national
Continuity (3)
Division 0986436700 · May 25, 2001
Continuation PCTDK990066100 · Nov 26, 1999
Related Publication 20040116703A1 · Jun 17, 2004