IP Library Granted Patent US 7,402,602
Granted Patent B2
US 7,402,602 · App. 11/281,864 · Granted Jul 22, 2008

Imidazole derivatives modulating the sodium channels

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Quick Facts
Patent No.
US 7,402,602
App. No.
11/281,864
Granted
Jul 22, 2008
Kind
B2
Abstract

A method of treating cardiac rhythm disorders linked with neurodegenerating depression, bipolar disorders and irritable bowel disorders in warm-blooded animals in need thereof by administering a compound of the formula wherein the substituents are defined as in the specification.

Claims (41)

1. A method of treating depression, bipolar disorder, and irritable bowel syndrome in warm blooded animals comprising administering to warm-blooded animals in need thereof an amount of a compound of the formula

wherein

R 1 is alkyl of 3 to 16 carbon atoms or a cycloalkylalkyl, the cycloalkyl of which contains 3 to 7 carbon atoms and the alkyl of which is 1 to 6 carbon atoms,

or R 1 is aralkyl optionally substituted 1 to 3 times on the aryl with at least one member selected from the group consisting of halogen, alkyl and alkoxy of 1 to 6 carbon atoms;

R 2 is phenyl optionally substituted 1 to 3 times by at least one member selected from the group consisting of halogen, alkyl and alkoxy of 1 to 6 carbon atoms,

or R 2 is biphenyl optionally substituted 1 to 4 times by at least one member of the group consisting of halogen, and alkyl and alkoxy of 1 to 6 carbon atoms;

R 3 is hydrogen or alkyl of 1 to 6 carbon atoms; and its pharmaceutically acceptable salts.

2. The method of claim 1 wherein the compound is selected from the group consisting of:

4-(1,1′-biphenyl-4-yl)-2-(4-isobutylbenzyl)-1H-imidazole;

2-hexyl-4-(4-isobutylphenyl)-1H-imidazole;

4-phenyl-2-(3-phenylpropyl)-1H-imidazole;

2-(1-pentylhexyl)-4-phenyl- 1H-imidazole;

4-(4-fluorophenyl)-2-(1-pentylhexyl)-1H-imidazole;

2-(cyclohexylmethyl)-4-(4-fluorophenyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(1-pentylhexyl)-1H-imidazole;

4-(4-tert-butylphenyl)-2-(1-propylbutyl)-1H-imidazole;

4-(4-fluorophenyl)-2-(1-propylbutyl)-1H-imidazole;

4-(4′-bromo-1,1′-biphenyl-4-yl)-2-(1-propylbutyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(2-cyclohexylethyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-hexyl-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-[1-(4-isobutylphenyl)ethyl]-1H-imidazole;

4-(4-fluorophenyl)-2-[1-(4-isobutylphenyl)ethyl]-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(1-phenylethyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(1-propylbutyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(cyclohexylmethyl)-1H-imidazole; and

4-(1,1′-biphenyl-4-yl)-2-(3-cyclohexylpropyl)-1H-imidazole;

and a pharmaceutically acceptable salt thereof.

3. The method of claim 1 , wherein the compound is selected from the group consisting of:

4-(1,1′-biphenyl-4-yl)-2-(4-isobutylbenzyl)-1H-imidazole;

2-hexyl-4-(4-isobutylphenyl)-1H-imidazole;

2-(1-pentylhexyl)-4-phenyl-1H-imidazole;

4-(4-fluorophenyl)-2-(1-pentylhexyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(1-pentylhexyl)-1H-imidazole;

4-(4-tert-butylphenyl)-2-(1-propylbutyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(2-cyclohexylethyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-hexyl-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-[1-(4-isobutylphenyl)ethyl]-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(1-propylbutyl)-1H-imidazole;

4-(1,1′-biphenyl-4-yl)-2-(cyclohexylmethyl)-1H-imidazole; and

4-(1,1′-biphenyl-4-yl)-2-(3-cyclohexylpropyl)-1H-imidazole;

and a pharmaceutically acceptable salt thereof.

Assignments (1)
CHANGE OF NAME Recorded Feb 11, 2009
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES
To: IPSEN PHARMA S.A.S.
Reel/Frame 022240/0147 →