IP Library › Granted Patent US 8,030,339

Granted Patent B2

US 8,030,339 · App. 12/083,375 · Granted Oct 4, 2011

Imidazole derivatives for the treatment of anxiety and related diseases

Assignee: Neurosearch A/S

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Patent No.: US 8,030,339
App. No.: 12/083,375
Granted: Oct 4, 2011
Kind: B2

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Abstract

This invention relates to novel imidazole derivatives, pharmaceutical compositions containing these compounds, and methods of treatment therewith. The compounds of the invention are useful in the treatment of central nervous system diseases and disorders, which are responsive to modulation of the GABA A receptor complex, and in particular for combating anxiety and related diseases.

Claims (182)

1. A compound of the general formula (I):

any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, wherein

R 1 represents —COR 3 ; wherein R 3 represents —(CH 2 —O) m -aryl or —(CH 2 —O) m -heteroaryl; wherein m is 0 or 1; and which aryl or heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of: halo, hydroxy, R a R b N—, R a R b N-alkyl, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R a —(C═O)—, R a —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl; wherein R a and R b independent of each other are hydrogen or alkyl; and

R 2 represents halo, nitro, aryl or heteroaryl; which aryl or heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of: halo, hydroxy, R d R e N—, R d R e N-alkyl, R d R e N—(C═O)—, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R d —(C═O)—, R d —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl; wherein R d and R e independent of each other are hydrogen or alkyl.

2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 represents —COR 3 ; wherein R 3 represents —(CH 2 —O) m -aryl which aryl group is optionally substituted with one or more substituents independently selected from the group consisting of: halo, hydroxy, R a R b N—, R a R b N-alkyl, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R a —(C═O)—, R a —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl; wherein R a and R b independent of each other are hydrogen or alkyl.

3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 represents —COR 3 ; wherein R 3 represents —(CH 2 —O) m -heteroaryl which heteroaryl group is optionally substituted with one or more substituents independently selected from the group consisting of: halo, hydroxy, R a R b N—, R a R b N-alkyl, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R a —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl; wherein R a and R b independent of each other are hydrogen or alkyl.

4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 represents halo or nitro.

5. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 2 represents aryl, which aryl group is optionally substituted with one or more substituents independently selected from the group consisting of: halo, hydroxy, R d R e N—, R d R e N-alkyl, R d R e N—(C═O)—, cyano, nitro, trifluoromethyl, trifluoromethoxy, alkoxy, cycloalkoxy, R d —(C═O)—, R d —O—(C═O)—, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, and alkynyl; wherein R d and R e independent of each other are hydrogen or alkyl.

6. The compound of claim 1 , which is selected from

1-[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-2-(pyridin-3-yloxy)-ethanone;

[1-(3-Bromo-phenyl)-1H-imidazol-4-yl]-phenyl-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-phenyl-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-pyridin-2-yl-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyridin-2-yl-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methyl-pyridin-2-yl)-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methyl-pyridin-2-yl)-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyrimidin-2-yl-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-(4-fluoro-phenyl)-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-(3-fluoro-phenyl)-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-(4-methoxy-phenyl)-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-(3-methoxy-phenyl)-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-(2-methoxy-phenyl)-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-thiazol-2-yl-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-furan-2-yl-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-thiazol-2-yl-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-furan-2-yl-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(5-methyl-thiazol-2-yl)-methanone;

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(1-methyl-imidazol-2-yl)-methanone;

(1-Ethoxymethyl-1H-imidazol-2-yl)-[1-(5′-fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(1-Ethyl-1H-imidazol-2-yl)-[1-(5′-fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]methanone;

(1-i-Propyl-1H-imidazol-2-yl)-[1-(5′-fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(1-(2-Hydroxyethyl)-1H-imidazol-2-yl)-[1-(5′-fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(1-(2-Methoxyethyl)-1H-imidazol-2-yl)-[1-(5′-fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

[1-(2′-Methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyridin-2-yl-methanone;

[1-(2′-Methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methyl-pyridin-2-yl)-methanone;

[1-(2′-Methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methyl-pyridin-2-yl)-methanone;

[1-(2′-Methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyrimidin-2-yl-methanone;

(4-Fluoro-phenyl)-[1-(2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(3-Fluoro-phenyl)-[1-(2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(4-Methoxy-phenyl)-[1-(2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(3-Methoxy-phenyl)-[1-(2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(2-Methoxy-phenyl)-[1-(2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]methanone;

[1-(2′-Methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-thiazol-2-yl-methanone;

[1-(2′-Methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(5-methyl-thiazol-2-yl)-methanone;

[1-(2′-Methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(1-methyl-imidazol-2-yl)-methanone;

Furan-2-yl-[1-(2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

3′-[4-(Pyridine-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(3-Methyl-pyridine-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(4-Methyl-pyridine-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(Pyrimidine-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3-[4-(4-Fluoro-benzoyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(3-Fluoro-benzoyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(4-Methoxy-benzoyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(3-Methoxy-benzoyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(2-Methoxy-benzoyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(Thiazole-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(5-Methyl-thiazole-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(1-Methyl-1H-imidazole-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

3′-[4-(Furan-2-carbonyl)-imidazol-1-yl]-biphenyl-2-carbonitrile;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-pyridin-2-yl-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methyl-pyridin-2-yl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methyl-pyridin-2-yl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-pyrimidin-2-yl-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-fluoro-phenyl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-fluoro-phenyl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methoxy-phenyl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methoxy-phenyl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(2-methoxy-phenyl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-thiazol-2-yl-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(5-methyl-thiazol-2-yl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H-imidazol-4-yl]-(1-methyl-1H-imidazol-2-yl)-methanone;

[1-(2′-Chloro-biphenyl-3-yl)-1H imidazol-4-yl]-furan-2-yl-methanone;

Pyridin-2-yl-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(3-Methyl-pyridin-2-yl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(4-Methyl-pyridin-2-yl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

Pyrimidin-2-yl-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(4-Fluoro-phenyl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(3-Fluoro-phenyl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(4-Methoxy-phenyl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(3-Methoxy-phenyl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(2-Methoxy-phenyl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

Thiazol-2-yl-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(5-Methyl-thiazol-2-yl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

(1-Methyl-1H-Imidazol-2-yl)-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

Furan-2-yl-[1-(2′-trifluoromethoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyridin-2-yl-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methyl-pyridin-2-yl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methyl-pyridin-2-yl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyrimidin-2-yl-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-fluoro-phenyl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-fluoro-phenyl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methoxy-phenyl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methoxy-phenyl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(2-methoxy-phenyl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-thiazol-2-yl-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(5-methyl-thiazol-2-yl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(1-methyl-1H-imidazol-2-yl)-methanone;

[1-(6′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-furan-2-yl-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyridin-2-yl-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methyl-pyridin-2-yl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methyl-pyridin-2-yl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyrimidin-2-yl-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-fluoro-phenyl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-fluoro-phenyl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(4-methoxy-phenyl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(3-methoxy-phenyl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(2-methoxy-phenyl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-thiazol-2-yl-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(5-methyl-thiazol-2-yl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-(1-methyl-1H-imidazol-2-yl)-methanone;

[1-(3′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-furan-2-yl-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-pyridin-2-yl-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(3-methyl-pyridin-2-yl)-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(4-methyl-pyridin-2-yl)-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-pyrimidin-2-yl-methanone;

(4-Fluoro-phenyl)-{1-[3-(2-fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-methanone;

(3-Fluoro-phenyl)-{1-[3-(2-fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(4-methoxy-phenyl)-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(3-methoxy-phenyl)-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(2-methoxy-phenyl)-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-thiazol-2-yl-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(5-methyl-thiazol-2-yl)-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(1-methyl-1H-imidazol-2-yl)-methanone;

{1-[3-(2-Fluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-furan-2-yl-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-pyridin-2-yl-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(3-methyl-pyridin-2-yl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(4-methyl-pyridin-2-yl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-pyrimidin-2-yl-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(4-fluoro-phenyl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(3-fluoro-phenyl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(4-methoxy-phenyl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(3-methoxy-phenyl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(2-methoxy-phenyl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-thiazol-2-yl-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(5-methyl-thiazol-2-yl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(1-methyl-1H-imidazol-2-yl)-methanone;

{1-[3-(2,4-Difluoro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-furan-2-yl-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-pyridin-2-yl-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-(3-methyl-pyridin-2-yl)-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-(4-methyl-pyridin-2-yl)-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-pyrimidin-2-yl-methanone;

(4-Fluoro-phenyl)-{1-[3-(3-fluoro-pyridin-4-ye-phenyl]-1H-imidazol-4-yl}-methanone;

(3-Fluoro-phenyl)-{1-[3-(3-fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-(4-methoxy-phenyl)-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-(3-methoxy-phenyl)-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-(2-methoxy-phenyl)-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-thiazol-2-yl-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-(5-methyl-thiazol-2-yl)-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-(1-methyl-1H-imidazol-2-yl)-methanone;

{1-[3-(3-Fluoro-pyridin-4-yl)-phenyl]-1H-imidazol-4-yl}-furan-2-yl-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-pyridin-2-yl-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(3-methyl-pyridin-2-yl)-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(4-methyl-pyridin-2-yl)-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-pyrimidin-2-yl-methanone;

(4-Fluoro-phenyl)-{1-[3-(2-chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-methanone;

(3-Fluoro-phenyl)-{1-[3-(2-chloro-pyridin-3-yl)phenyl]-1H-imidazol-4-yl}-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(4-methoxy-phenyl)-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(3-methoxy-phenyl)-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(2-methoxy-phenyl)-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-thiazol-2-yl-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(5-methyl-thiazol-2-yl)-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-(1-methyl-1H-imidazol-2-yl)-methanone;

{1-[3-(2-Chloro-pyridin-3-yl)-phenyl]-1H-imidazol-4-yl}-furan-2-yl-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-pyridin-2-yl-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(3-methyl-pyridin-2-yl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(4-methyl-pyridin-2-yl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-pyrimidin-2-yl-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(4-fluoro-phenyl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(3-fluoro-phenyl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(4-methoxy-phenyl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(3-methoxy-phenyl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(2-methoxy-phenyl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-thiazol-2-yl-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(5-methyl-thiazol-2-yl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-(1-methyl-1H-imidazol-2-yl)-methanone;

{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-imidazol-4-yl}-furan-2-yl-methanone;

(1-Biphenyl-3-yl-1H-imidazol-4-yl)-pyrazol-1-yl-methanone (178);

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyrazol-1-yl-methanone; and

[1-(5′-Fluoro-2′-methoxy-biphenyl-3-yl)-1H-imidazol-4-yl]-pyrrol-1-yl-methanone; or

any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof.

7. A pharmaceutical composition, comprising a therapeutically effective amount of a compound of claim 1 , any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof, together with at least one pharmaceutically acceptable carrier, excipient or diluent.

8. The compound of claim 6 , which is [1-(5′-fluoro-2′-methoxybiphenyl-3-yl)-1H-imidazol-4-yl]-(1-methylimidazol-2-yl)-methanone, or any of its stereoisomers or any mixture of its stereoisomers, or a pharmaceutically acceptable salt thereof.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2013

From: NEUROSEARCH A/S

To: ANIONA APS

Reel/Frame 030049/0894 →

CORRECTIVE ASSIGNMENT TO CORRECT THE SERIAL NUMBER PREVIOUSLY RECORDED ON REEL 021355 FRAME 0802. ASSIGNOR(S) HEREBY CONFIRMS THE CORRECT NUMBER AS 12083375. Recorded Sep 11, 2008

From: BROWN, WILLIAM DALBY; LARSEN, JANUS S.; TEUBER, LENE; BROWN, DAVID TRISTRAM; AHRING, PHILIP K.; MIRZA, NAHEED; NIELSEN, ELSEBET OSTERGAARD

To: NEUROSEARCH A/S

Reel/Frame 021514/0499 →

Priority Claims (1)

DK 2005 01445 · Oct 14, 2005 · national

Continuity (2)

Provisional Application 60726677 · Oct 17, 2005

Related Publication 20090233929A1 · Sep 17, 2009