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US 2008/0188561 A1Published application
N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators
AssigneeValeant Pharmaceuticals International
InventorsJean-Michel Vernier, Jianlan Song, Huanming Chen, Zhi Hong
Life of this patent
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Abstract
This invention provides compounds of formula A and formula B which are modulators of potassium ion channels and are useful for the treatment of seizure disorders.
Claims31
A compound of formula A
- where Ar is phenyl, pyridyl, thienyl, furyl, or benzothienyl;
- U═—C(Rm)═ or —N═;
- Ra and R′a are, independently, H, F, Cl, methyl, methoxy, fluoromethyl, difluoromethyl, or trifluoromethyl;
- R′m and Rm are, independently, H, F, Cl, methyl, fluoromethyl, difluoromethyl, trifluoromethyl or methoxy;
- RN is H or C1-C4 alkyl, which may be straight-chain, branched, or cyclic;
- and RO is H, isopropyl, sec-butyl, or straight-chain C1-C8 alkyl, alkenyl, or alkynyl, any of which may be substituted by methyl, fluoro, chloro methoxy, phenyl, or benzoyloxy, where the methyl, methoxy, phenyl, and benzyl groups are optionally substituted with one or two fluorine atoms or one or two chlorine atoms.
3 more elements
A compound which is selected from the following:
- N-(2-amino-4-(4-fluorobenzyloxy)phenyl)-3,3-dimethylbutanamide
- N-(2-amino-4-(3,4-difluorobenzyloxy)phenyl)-3,3-dimethylbutanamide
- N-(2-amino-4-((5-chlorothiophen-2-yl)methoxy)phenyl)-3,3-dimethylbutanamide
- N-(2-amino-4-(4-fluorobenzyloxy)phenyl)butyramide
- N-(2-amino-4-(4-fluorobenzyloxy)phenyl)pivalamide
- N-(2-amino-4-(4-fluorobenzyloxy)phenyl)-2-(4-fluorophenyl)acetamide
- N-(2-amino-4-(4-fluorobenzyloxy)phenyl)-2-phenylacetamide
- N-(2-amino-4-(4-fluorobenzyloxy)phenyl)-2-phenoxyacetamide
5 more elements
A composition comprising a pharmaceutically acceptable carrier and one or more of the following:
- a compound of formula A;
- a salt, solvate, ester, or prodrug thereof.
A method of treating a disease or disorder which is affected by activation of potassium ion channels comprising administering to a patient in need thereof a therapeutically affective amount of a composition comprising one or more of the following:
- a compound of formula A;
- a salt, solvate, ester, or prodrug thereof.
A compound of formula B
- where Ar is phenyl, pyridyl, thienyl, furyl, or benzothienyl;
- U═—C(Rm)═ or —N═;
- Ra and R′a are, independently, H, F, Cl, methyl, methoxy, fluoromethyl, difluoromethyl, or trifluoromethyl;
- R′m and Rm are, independently, H, F, Cl, methyl, fluoromethyl, difluoromethyl, trifluoromethyl or methoxy;
- RN is H or C1-C4 alkyl, which may be straight-chain, branched, or cyclic;
- and RO is isopropyl, sec-butyl, or straight-chain C1-C8 alkyl, alkenyl, or alkynyl, any of which may be substituted by methyl, fluoro, chloro methoxy, phenyl, or benzoyloxy, where the methyl, methoxy, phenyl, and benzyl groups are optionally substituted with one or two fluorine atoms or one or two chlorine atoms.
3 more elements
A compound selected from the following:
- Ethyl 2-amino-4-(2-fluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(2,4-difluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(4-bromo-2-fluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3-fluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3,4-difluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3,5-difluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(2-chloro-5-fluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(2,5-dichlorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-((4-chlorothiophen-2-yl)methoxy)phenylcarbamate
- Ethyl 2-amino-4-((4-(trifluoromethyl)furan-2-yl)methoxy)phenylcarbamate
- Ethyl 2-amino-4-(4-chlorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(4-methylbenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(4-(trifluoromethyl)benzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(4-cyanobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(4-(methylthio)benzyloxy)phenylcarbamate
- Methyl 4-((3-amino-4-(ethoxycarbonylamino)phenoxy)methyl)benzoate
- Ethyl 2-amino-4-(3-fluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3-chlorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3-methylbenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3-(trifluoromethyl)benzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3-cyanobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(3-methoxybenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(naphthalen-2-ylmethoxy)phenylcarbamate
- Ethyl 2-amino-4-(2-fluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(pyridin-3-ylmethoxy)phenylcarbamate
- Ethyl 2-amino-4-(benzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(2-methylbenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(2-(trifluoromethyl)benzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(2-(trifluoromethoxy)benzyloxy)phenylcarbamate
- [2-Amino-4-(4-fluoro-benzyloxy)-phenyl]-carbamic acid propyl ester
- Methyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Ethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Butyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Hexyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate.
- Octyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Isopropyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Isobutyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Allyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- But-3-enyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Cyclopentyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Neopentyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Prop-2-ynyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- But-3-ynyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Fluoroethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- But-2-ynyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Chloroethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Methoxyethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Benzyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Chlorobenzyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Methoxyethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Methoxyethyl 2-amino-4-(3,4-difluorobenzyloxy)phenylcarbamate
- 2-Methoxyethyl 2-amino-4-((5-chlorothiophen-2-yl)methoxy)phenylcarbamate
- Ethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Isopropyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Propyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- Butyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Chloroethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 3-Chloropropyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- 2-Methoxyethyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
- But-2-ynyl 2-amino-4-(4-fluorobenzyloxy)phenylcarbamate
57 more elements
A composition comprising a pharmaceutically acceptable carrier and one or more of the following:
- a compound of formula B;
- a salt, solvate, ester, or prodrug thereof.
A method of treating a disease or disorder which is affected by activation of potassium ion channels comprising administering to a patient in need thereof a therapeutically affective amount of a composition comprising one or more of the following:
- a compound of formula B;
- a salt, solvate, ester, or prodrug thereof.
Dependencies are inferred from the claim text.