IP Library › Granted Patent US 7,282,494
Granted Patent B2
US 7,282,494 · App. 11/312,574 · Granted Oct 16, 2007

Heteroaryl diazacycloalkanes, their preparation and use

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Quick Facts
Patent No.
US 7,282,494
App. No.
11/312,574
Granted
Oct 16, 2007
Kind
B2
Abstract

The present invention relates to novel heteroaryl diazacycloalkane 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 (103)

1. A diazacycloalkane compound selected from the group consisting of:

5-(1-heptynyl)-3-pyridyl-homopiperazine;

5-(1-hexynyl)-3-pyridyl-homopiperazine;

5-(1-pentynyl)-3-pyridyl-homopiperazine;

5-(1-butynyl)-3-pyridyl-homopiperazine;

5-(1-propynyl)-3-pyridyl-homopiperazine;

5,6-dichloro-3-pyridyl-homopiperazine;

6-fluoro-3-pyridyl-homopiperazine;

6-iodo-3-pyridyl-homopiperazine;

5-chloro-6-fluoro-3-pyridyl-homopiperazine;

5-chloro-6-iodo-3-pyridyl-homopiperazine;

5-bromo-6-fluoro-3-pyridyl-homopiperazine;

5-bromo-6-iodo-3-pyridyl-homopiperazine;

6-fluoro-pyridazine-homopiperazine;

6-iodopyridazine-homopiperazine;

5-(trans-hex-2-en-1-yl-oxy)-3-pyridyl-homopiperazine;

5-ethoxy-3-pyridyl-4-(prop-2-en-1-yl)-homopiperazine;

1-(5-(cyclobutylmethoxy)-3-pyridyl)-homopiperazine;

1-(5-(hex-2-en-oxy)-3-pyridyl)-homopiperazine;

1-(5-(2-methyl-1-prop-1-en-oxy)-3-pyridyl)-homopiperazine;

1,4-Bis-[5-ethoxy-3-pyridyl]-homopiperazine;

1,4-Bis-[5-(1-propyl-1-en-oxy)-3-pyridyl]-homopiperazine;

1-(5-Iodo-3-pyridyl)-homopiperazine;

1,4-Bis-[5-(vinyl-oxy)-3-pyridyl]-homopiperazine;

1-[5-Phenyl-2-eth-1-yl-3-pyridyl]-homopiperazine;

1-[5-Ethyl-3-pyridyl]-homopiperazine;

1-[3-(4-Chloro-1,2,5-thiadiazolyl)]-homopiperazine;

1-(5-Bromo-3-pyridyl)-homopiperazine;

1-(6-Amino-3-pyridyl)-homopiperazine;

1-(6-Nitro-3-pyridyl)-homopiperazine;

1-[3-(1,2,5-thiadiazolyl)]-homopiperazine;

1-(6-Fluoro-5-ethynyl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-ethynyl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-ethynyl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-ethynyl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-propyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-propyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-propyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-propyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-butyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-butyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-butyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-butyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-pentyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-pentyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-pentyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-pentyn-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-ethenyl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-ethenyl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-ethenyl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-ethenyl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-propen-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-propen-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-propen-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-propen-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-buten-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-buten-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-buten-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-penten-1-yl-3-pyridyl-homopiperazine;

1-(6-Chloro-5-penten-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-penten-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-penten-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-ethyl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-ethyl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-ethyl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-ethyl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-prop-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-prop-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-prop-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-prop-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-but-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-but-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-but-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-but-1-yl-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-pent-1-yl-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-pent-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-pent-1-yl-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-pent-1-yl-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-methoxy-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-methoxy-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-methoxy-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-methoxy-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-ethoxy-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-ethoxy-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-ethoxy-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-propyloxy-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-propyloxy-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-propyloxy-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-propyloxy-3-pyridyl)-homopiperazine;

1-(6-Bromo-5-vinyloxy-3-pyridyl)-homopiperazine;

1-(6-Chloro-5-vinyloxy-3-pyridyl)-homopiperazine;

1-(6-Fluoro-5-vinyloxy-3-pyridyl)-homopiperazine;

1-(6-Iodo-5-vinyloxy-3-pyridyl)-homopiperazine;

1-(5-Ethenyl-3-pyridyl)-homopiperazine;

1-(5-Propen-1-yl-3-pyridyl)-homopiperazine;

1-(5-buten-1-yl-3-pyridyl)-homopiperazine;

1-(5-Penten-1-yl-3-pyridyl)-homopiperazine;

1-(5-Prop-1-yl-3-pyridyl)-homopiperazine;

1-(5-But-1-yl-3-pyridyl)-homopiperazine; and

1-(5-Pent-1-yl-3-pyridyl)-homopiperazine; or

an enantiomer or any mixture of its enantiomers or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , which is 1-(6-bromo-5-methoxy-3-pyridyl)-homopiperazine.

3. A pharmaceutical composition comprising a therapeutically-effective amount of a diazacycloalkane compound of claim 1 , or a pharmaceutically-acceptable addition salt thereof, together with at least one pharmaceutically-acceptable carrier or diluent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 14, 2013
From: NEUROSEARCH A/S
To: DANPET AB
Reel/Frame 029811/0215 →