IL158121A - 5-membered heterocycles, pharmaceutical compositions comprising them and uses thereof for the manufacture of medicaments - Google Patents

5-membered heterocycles, pharmaceutical compositions comprising them and uses thereof for the manufacture of medicaments

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Publication number
IL158121A
IL158121A IL158121A IL15812103A IL158121A IL 158121 A IL158121 A IL 158121A IL 158121 A IL158121 A IL 158121A IL 15812103 A IL15812103 A IL 15812103A IL 158121 A IL158121 A IL 158121A
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Israel
Prior art keywords
butyl
thiazol
methyl
imidazol
ethylcarbamate
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IL158121A
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Sod Conseils Rech Applic
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Priority claimed from FR0104943A external-priority patent/FR2823208B1/en
Application filed by Sod Conseils Rech Applic filed Critical Sod Conseils Rech Applic
Publication of IL158121A publication Critical patent/IL158121A/en

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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/34—Oxygen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Claims (1)

1. I l l Claims 1. Compound characterized in that it is chosen from the following compounds: - 2,6-di½ri-butyl-4-{ 2-[2-(methylamino)ethyl]-l,3-thiazol-4-yl}phenol; - 2,6-dite/-/-butyl-4-[4-(hydroxymethyl)-l,3-oxazol-2-yl]phenol; - 2-[l -(methylaniino)ethyl]-l ,3-thiazol-4-yl}phenol; - 2,6-diter -butyl-4-[2-(methoxymethyl)-l,3-thiazol-4-yl]phenol; - 2,6-dite/ -butyl-4-{4-[(methylamino)methyl]-l ,3-oxazol-2-yl }phenol; - N-{ [4-(3,5-dir.?rt-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methyl}acetamide; - ethyl [4-(3,5-diter/-butyl-4-hydroxyphenyl)- 1 ,3-thiazol-2-yl]methylcarbamate; - 2,6-di½r butyl-4-[2-(mo holin-4-ylmethyl)-l,3-thiazol-4-yl]phenol; - 2,6-dirert-butyl-4-[2-(thiomorpholin-4-ylmethyl)-l ,3-thiazol-4-yl]phenol; - 4-[2-(anilinomethyl)-l,3-thiazol-4-yl]-2,6-di½rt-butylphenol; - 2,6-dite/ -butyl-4-(2-{ [[2-(dimethylamino)ethyl](methyl)amino]methyl}-l,3-thiazol-4-yl)phenol; - 2,6-di/e -butyl-4-{5-methyl-2-[(methylamino)methyl]-l,3-thiazol-4-yl}phenol; - l -[4-(10H-phenothiazin-2-yl)-l ,3-thiazol-2-yl]methanamine; - N- { [4-(3,5-di/er -butyl-4-hydroxyphenyl)- 1 ,3-thiazol-2-yl]methyl } -N-methyl acetami de ; - l -[4-(3,5-dir 3. Pharmaceutical composition containing, as active ingredient, at least one of the compounds according to claim 2. 4. Use of a compound characterized in that it is chosen from the following compounds: - 2,6-di/err-butyl-4-{2-[2-(methylamino)ethyl]-l ,3-thiazol-4-yl }phenol; - 2,6-di/err-butyl-4-[4-(hydroxymethyl)-l,3-oxazol-2-yl]phenol; - 2,6-difer/-butyl-4- { 2-[ 1 -(methylamino)ethyl]- 1 ,3-thiazol-4-yl }phenol; - 2,6-di/err-butyl-4-[2-(methoxymethyl)-l,3-thiazol-4-yl]phenol; - 2,6-di/m-butyl-4- { 4- [(methylamino)methyl] - 1 ,3-oxazol-2-yl } phenol ; - N-{ [4-(3,5-di/eri-butyl-4-hydroxyphenyl)-l ,3-thiazol-2-yl]methyl}acetamide; - ethyl [4-(3,5-ditert-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methylcarbamate; - 2,6-di½rr-butyl-4-[2-(morpholin-4-ylmethyl)-l,3-thiazol-4-yl]phenol; - 2,6-di/ert-butyl-4-[2-(thiomo holin-4-ylmethyl)-l,3-thiazol-4-yl]phenol; - 4-[2-(anilinomethyl)-l,3-thiazol-4-yl]-2,6-di½rt-butylphenol; - 2,6-dir -butyl-4-(2-{ [[2-(dimethylarruno)ethyl](methyl)amino]methyl}-l,3-thiazol-4-yl)phenol; - 2,6-direrr-butyl-4-{ 5-methyl-2-[(methylamino)methyl]-l,3-thiazol-4-yl}phenol; - 1 -[4-( 10H-phenothiazin-2-yl)- 1 ,3-thiazol-2-yl]methanamine; - N- { [4-(3,5-direrf-butyl-4-hydroxyphenyl)- 1 ,3-thiazol-2-yl]methyl } -N-methylacetamide; - 1 -[4-(3,5-diterr-butyl-4-methoxyphenyl)- l,3-thiazol-2-yl]-N-methylmethanamine; - 2,6-di/err-butyl-4-{2-[(ethylamino)methyl]-l,3-thiazol-4-yl}phenol; - 2,6-dirm-butyl-4-{ 2-[(4-phenylpiperazin-l -yl)methyl]-l,3-thiazol-4-yl }phenol; - 2,6-dirm-butyl-4- { 2-[(4-methyl- 1 ,4 -diazepan- 1 -yl)methyl]- 1 ,3-thiazol-4-yl Jphenol; - N- { 1 -[4-(4-anilinophenyl)- 1 ,3-thiazol-2-yl]ethyl } -N-methylamine; - 2,6-di½r/-butyl-4-{ 2-[(isopropylamino)methyl]-l,3-thiazol-4-yl}phenol; - 2,6-ditert-butyl-4-{2-[(cyclohexylamino)methyl]-l ,3-thiazol-4-yl}phenol; - 2,6-direrr-butyl-4-{2-[(4-isopropylpiperazin-l-yl)methyl]-l,3-thiazol-4-yl }phenol; - N-methyl-1 -[4-(10H-phenothiazin-2-yl)-l,3-thiazol-2-yl]ethanamine; - 2,6-diri?r/-butyl-4-{2-[(4-ethylpiperazin-l-yl)methyl]-l,3-thiazol-4-yl }phenol; - N-{ [4-(4-anilinophenyl)-l ,3-thiazol-2-yl]methyl}-N-ethylamine; - N-{ [4-(10H-phenothiazin-2-yl)-l ,3-thiazol-2-yl]methyl }ethanamine; - 2,6-direr/-butyl-4-(2- { [4-(dimethylamino)piperidin- 1 -yl]methyl } - 1 ,3-thiazol-4-yl)phenol; - 1 - { [4-(3,5-di½rr-butyl-4-hydroxyphenyl)- 1 ,3-thiazol-2-yl]methyl } piped din-4-ol; - 4-methylpentyl 2-[4-(l,l '-biphenyl-4-yl)-lH-iniidazol-2-yl]ethylcarbamate; - 3,3-dimethylbutyl 2-[4-(4-pyrrolidin-l-ylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - isopentyl 2-[4-(l, -biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - hexyl 2-[4-(4'-bromo-l, r-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - benzyl 2-[4-(4-rerr-butylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - 3,3-dimethylbutyl 2-[4-( l,r-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - hexyl 2-[4-(4-pyrrolidin-l-ylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - hexyl 2-[4-(3,5-di½rt-butyl-4-hydroxyphenyl)-lH-imidazol-2-yl]ethylcarbamate; - 3,3-dimethylbutyl 2-[4-(3,5-di/m-butyl-4-hydroxyphenyl)-lH-imidazol-2-yl]ethylcarbamate; - 3,3-dimethylbutyl 2-[4-(4-methoxyphenyl)-lH-imidazol-2-yl]ethylcarbamate; - benzyl 2-[4-(3,5-dit 6. Use of one of the following compounds: - 2,6-di½rr-butyl-4-{ 2-[2-(methylamino)ethyl]-l,3-thiazol-4-yl}phenol; - 2,6-difm-butyl-4-[4-(hydroxymethyl)-l ,3-oxazol-2-yl]phenol; - 2,6-di ert-butyl-4- { 2-[ 1 -(methylamino)ethyl]- 1 ,3-thiazol-4-yl Jphenol; - 2,6-di/err-butyl-4-[2-(methoxymethyl)-l ,3-thiazol-4-yl]phenol; - 2,6-di/err-butyl-4- { 4-[(methylamino)methyl]- 1 ,3-oxazol-2-yl Jphenol; - N-{ [4-(3,5-dire/V-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methyl }acetamide; - ethyl [4-(3,5-di er/-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methylcarbamate; - 2,6-di/er butyl-4-[2-(mo holin-4-ylmethyl)-l ,3-thiazol-4-yl]phenol; - 2,6-di½rr-butyl-4-[2-(thiomo holin-4-ylmethyl)-l,3-thiazol-4-yl]phenol; - 4-[2-(anilinomethyl)-l ,3-thiazol-4-yl]-2,6-diterf-butylphenol; - 2,6-dirm-butyl-4-(2-{ [[2-(dimethylamino)ethyl](methyl)amino]methyl }-l ,3-thiazol-4-yl)phenol; - 2,6-ditert-butyl-4-{5-methyl-2-[(methylamino)methyl]-l ,3-thiazol-4-yl }phenol; - 1 -[4-( 10H-phenothiazin-2-yl)- 1 ,3-thiazol-2-yl]methanamine; - N-{ [4-(3,5-direr/-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methyl }-N-methy lacetami de ; - l -[4-(3,5-di½^butyl-4-methoxyphenyl)-l,3-thiazol-2-yl]-N-methylmethanamine; - 2,6-dirm-butyl-4-{ 2-[(ethylamino)methyl]-l ,3-thiazol-4-yl Jphenol; - 2,6-di½r/-butyl-4-{ 2-[(4-phenylpiperazin-l-yl)methyl]-l,3-thiazol-4-yl}phenol; - 2,6-di½rt-butyl-4-{2-[(4-methyl-l,4 -diazepan-l-yl)methyl]-l ,3-thiazol-4-yl Jphenol; - N- { 1 -[4-(4-anilinophenyl)- 1 ,3-thiazol-2-yl]ethyl } -N-methylamine; - 2,6-di/ 7. Use according to claim 6, characterized in that the compound used is chosen from one of the following compounds: - 2,6-di½/Y-butyl-4- { 2-[ 1 -(methylamino)ethyl] - 1 ,3-thiazol-4-yl }phenol ; - l -[4-(3,5-ditert-butyl-4-methoxyphenyl)-l,3-thiazol-2-yl]-N-methylmethanamine; - 2,6-di½r/-butyl-4-{ 2-[(ethylamino)methyl]-l,3-thiazol-4-yl Jphenol; - l-{ [4-(3,5-ditert-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methyl }piperidin-4-ol; - l-{ [4-(3,5-di-ier/-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methyl }pyrrolidin-3-ol; - l-{ [4-(3,5-di-reri-butyl-4-hydroxyphenyl)-l,3-thiazol-2-yl]methyl}azetidin-3-ol; - (3R)-l-{ [4-(3,5-di-tert-butyl-4-hydroxyphenyl)-l ,3-thiazol-2-yl]methyl}pyrrolidin-3-ol; - (35)-l-{ [4-(3,5-di-tert-butyl-4-hydroxyphenyl)-l ,3-thiazol-2-yl]methyl}pyrrolidin- 3- ol; - N, 2-dimethyl- 1 -[4-( 10H-phenothiazin-2-yl)- 1 ,3-thiazol-2-yl]propan- 1 -amine; and the pharmaceutically acceptable salts of the latter. 8. Use according to claim 6 or 7, characterized in that the medicament prepared is intended to treat one of the following disorders or diseases: Parkinson's disease, senile dementia, Alzheimer's disease, Huntington's chorea, amyotrophic lateral sclerosis, schizophrenia, depression and psychoses. 9. Use of one of the following compounds - 2,6-di rr-butyl-4- { 2-[2-(methylamino)ethyl]- 1 ,3-thiazol-4-yl Jphenol; - 2,6-dirm-butyl-4- { 2-[ 1 -(methylamino)ethyl]- 1 ,3-thiazol-4-yl Jphenol; - 2,6-direrr-butyl-4-{4-[(methylamino)methyl]-l,3-oxazol-2-yl}phenol; - 2,6-diiert-butyl-4-{5-methyl-2-[(methylamino)methyl]-l,3-thiazol-4-yl Jphenol; - l-[4-(3,5-diie^butyl-4-methoxyphenyl)-l,3-thiazol-2-yl]-N-methylmethanamine; - 2,6-ditm-butyl-4-{ 2-[(ethylamino)methyl]-l,3-thiazol-4-yl Jphenol; - 4-methylpentyl 2-[4-( 1 , 1 '-biphenyl-4-yl)- 1 H-imidazol-2-yl]ethylcarbamate; - 3,3-dimethylbutyl 2-[4-(4-pyrrolidin- 1 -ylphenyl)- 1 H-imidazol-2-yl]ethylcarbamate; - isopentyl 2-[4-(l , -biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - hexyl 2-[4-(4'-bromo-l, -biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbarnate; - benzyl 2-[4-(4-tert-butylphenyl)- lH-imidazol-2-yl]ethylcarbamate; - 3,3-dimethylbutyl 2-[4-( 1 , 1 -biphenyl-4-yl)- lH-imidazol-2-yl]ethylcarbamate; - hexyl 2-[4-(4-pyrrolidin-l -ylphenyl)- lH-imidazol-2-yl]ethylcarbamate; - hexyl 2-[4-(3,5-dite;v-butyl-4-hydroxyphenyl)-lH-imidazol-2-yl]ethylcarbamate; - hexyl 2-[4-(3,5-di½rt-butyl-4-hydroxyphenyl)-lH-imidazol-2-yl]ethylcarbamate; - 3,3-dimethylbutyl 2-[4-(4-methoxyphenyl)-lH-imidazol-2-yl]ethylcarbamate; - benzyl 2-[4-(3,5-di/e^butyl-4-hydroxyphenyl)-lH-imidazol-2-yl]ethylcarbamate; - benzyl 2-[4-(4-pyrrolidin-l-ylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - 2-phenylethyl 2-[4-(l , -biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(4'-fluoro- 1 , 1 -biphenyl-4-yl)- lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(l,l '-biphenyl-4-yl)-5-methyl-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(4'-methyl- 1 , 1 '-biphenyl-4-yl)- lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(4'-chloro-l ,r-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(2'-fluoro-l, r-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(2', 4'-difluoro-l , r-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(3'-chloro- 1 , 1 '-biphenyl-4-yl)- 1 H-imidazol-2-yl]ethylcarbamate; - butyl 2- [4-(3'-fluoro- 1 , 1 '-biphenyl-4-yl)- 1 H-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(4-isobutylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - benzyl 2-[4-(4-isobutylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(3'-chloro-4'-fluoro-l, -biphenyl-4-yl)-lH-irrddazol-2-yl]ethylcarbarnate; - butyl 2-[4-(3', 4'-dichloro-l,r-biphenyl-4-yl)-lH-irnidazol-2-yl]ethylcarbamate; - butyl 2-[4-(4-propylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(4-ethylphenyl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(4'-cyano-l,r-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(l, -biphenyl-4-yl)-5-ethyl-lH-imidazol-2-yl]ethylcarbarnate; - butyl 2-[4-(2'-chloro- 1 , 1 -biphenyl-4-yl)- lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(2', 3'-difluoro-l ,l '-biphenyl-4-yl)-lH-irnidazol-2-yl]ethylcarbarnate; - butyl 2-[4-(2'-bromo-l ,1 ,-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(3', 5'-difluoro-l, -biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbarnate; - butyl 2-[4-(2'-methoxy- 1 , 1 '-biphenyl-4-yl)- lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(3'-nitro-l, -biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbarnate; - butyl 2-[4-(2', 5'-difluoro-l,r-biphenyl-4-yl)-lH-imidazol-2-yl]ethylcarbamate; - butyl 2-[4-(3'-methoxy- 1 , 1 '-biphenyl-4-yl)- lH-imidazol-2-yl]ethylcarbamate; or of a pharmaceutically acceptable salt of one of the latter for preparing a medicament intended to modulate the sodium channels. 10. Use according to claim 9, characterized in that the medicament prepared is intended to treat one of the following disorders or diseases: Parkinson's disease, Alzheimer's disease, amyotrophic lateral sclerosis, migraine or pain and in particular neuropathic pain. For ftfae ApplloQR¾o Mmm com moie
IL158121A 2001-04-10 2003-09-25 5-membered heterocycles, pharmaceutical compositions comprising them and uses thereof for the manufacture of medicaments IL158121A (en)

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