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US 2004/0006245 A1Published application
N-(4-substituted phenyl)-anthranilic acid hydroxamate esters
AssigneeWarner-Lambert Company
InventorsGordon William Rewcastle, Julie Ann Spicer, Stephen Douglas Barrett, Michael David Kaufman, Jared Bruce John Milbank, Haile Tecle
Life of this patent
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Abstract
The present invention relates to oxygenated esters of 4-substituted-phenylamino benzhydroxamic acid derivatives, pharmaceutical compositions and methods of use thereof.
Claims39
A compound of formula
- 108
- R2 is hydrogen, methyl, fluorine, or chlorine;
- R3 is hydrogen or fluorine;
- R4 is C1-6 alkyl, C2-4 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, —(CH2)—C3-6 cycloalkyl, —O—(C1-4 alkyl), —S—(C1-2 alkyl), —SO2CH3, —SO2NR6R7, —C≡C—(CH2)nNH2, —C═C(CH2)nOH, —C═C—(CH2)nNH2, —(CH2)mNH2, —(CH2)mNHCH3, —(CH2)mN(CH3)2, —(CH2)mOR8, —(CH2)qCF3, —C≡CCF3, —CH═CHCF3, —CH2CHCF2, or —CH═CF2,
- wherein the C1-6 alkyl and C2-6 alkynyl are optionally substituted with between 1 and 3 substituents selected from hydroxy and alkyl;
- m is 1 to 4;
- n is 1 to 2;
- q is 0 to 2;
- R5 is hydrogen or chlorine;
- R6 and R7 are each independently hydrogen, methyl, or ethyl;
- R8 is independently methyl or ethyl;
- and pharmaceutically acceptable salts thereof.
9 more elements
A compound of formula
- 113
- R2 is hydrogen, fluorine, or chlorine;
- R3 is hydrogen or fluorine;
- R4 is C1-6 alkyl, C2-4 alkenyl, C2-6 alkynyl, —S—(C1-2 alkyl), —SO2CH3, —C═C—(CH2)nNH2, —(CH2)mNH2, —(CH2)mNHCH3, —(CH2)mN(CH3)2, or —(CH2)mOR8, wherein the C1-6 alkyl and C2-6 alkynyl are optionally substituted with between 1 and 3 substituents selected from hydroxy and alkyl;
- m is 1 to 4;
- n is 1 to 2;
- q is 0 to 2;
- R5 is hydrogen or chlorine;
- R6 and R7 are each independently hydrogen, methyl, or ethyl;
- R8 is independently methyl or ethyl;
- and pharmaceutically acceptable salts thereof.
8 more elements
A compound of formula
- 114
- R2 is fluorine, or chlorine;
- R3 is hydrogen or fluorine;
- R4 is C1-4 alkyl, C2-3 alkenyl, C2-4 alkynyl, —S—(C1-2 alkyl), —SO2CH3, —C≡C—(CH2)nNH2, or —(CH2)mOR8, wherein the C1-4 alkyl and
- C2-4 alkynyl are optionally substituted with between 1 and 3 substituents selected from hydroxy and alkyl;
- m is 1 to 4;
- n is 1 to 2;
- q is 0 to 2;
- R5 is hydrogen or chlorine;
- R6 and R7 are each independently hydrogen, methyl, or ethyl;
- R8 is independently methyl or ethyl;
- and pharmaceutically acceptable salts thereof.
9 more elements
A compound which is selected from the group consisting of
- 2-[(4-Ethyl-2-fluorophenyl)amino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 2-(2-Chloro-4-ethyl-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide;
- 3,4-Difluoro-2-[(2-fluoro-4-vinylphenyl)amino]-N-(2-hydroxyethoxy)benzamide;
- 2-(2-Chloro-4-vinyl-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide;
- 2-[(4-Ethynyl-2-fluorophenyl)amino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-N-(2-hydroxyethoxy)-2-[[4-(hydroxymethyl)phenyl]amino] benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(3-methoxypropyl)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(methylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(methylsulfonyl)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- N-[(R-)2,3-Dihydroxy-propoxy]-2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-benzamide;
- and
- 2-(4-Ethyl-2-fluoro-phenylamino)-3,4-difluoro-N-(2-hydroxy-1-hydroxymethyl-ethoxy)-benzamide.
10 more elements
A compound which is selected from the group consisting of:
- 2-[(4-Ethyl-2-fluorophenyl)amino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 2-(2-Chloro-4-ethyl-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide;
- 3,4-Difluoro-2-[(2-fluoro-4-vinylphenyl)amino]-N-(2-hydroxyethoxy)benzamide;
- 2-(2-Chloro-4-vinyl-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide;
- 2-[(4-Ethynyl-2-fluorophenyl)amino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-N-(2-hydroxyethoxy)-2-[[4-(hydroxymethyl)phenyl]amino] benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(3-methoxypropyl)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(methylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[[2-fluoro-4-(methyl sulfonyl)phenyl]amino]-N-(2-hydroxyethoxy)benzamide;
- N-[(R-)2,3-Dihydroxy-propoxy]-2-(4-ethyl -2-fluoro-phenylamino) -3,4-difluoro-benzamide;
- 2-(4-Ethyl-2-fluoro-phenylamino)-3,4-difluoro-N-(2-hydroxy-1-hydroxymethyl-ethoxy)-benzamide;
- 3,4-Difluoro-2-(2-fluoro-4-methylanilino)-N-(2-hydroxyethoxy)benzamide;
- 2-(4-Allyl-2-fluoroanilino)-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 2-(2-Chloro-4-ethynyl-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide;
- 2-[4-(3-Amino-1-propynyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(4-hydroxy-1-butynyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(3-hydroxy-3-methyl-1-butynyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(3-hydroxy-3-methyl-1-pentynyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 2-[4-(3-Aminopropyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 2-{4-[3-(Dimethylamino)propyl]-2-fluoroanilino}-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-{2-fluoro-4-[3-(methylamino)propyl]anilino}-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(hydroxymethyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(3-hydroxypropyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(4-hydroxybutyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 2-[4-(2,3-Dihydroxypropyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(3-hydroxy-3-methylbutyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-[2-fluoro-4-(3-hydroxy-3-methylpentyl)anilino]-N-(2-hydroxyethoxy)benzamide;
- 3,4-Difluoro-2-(2-fluoro-4-propylanilino)-N-(2-hydroxyethoxy)benzamide;
- and
- 2-(4-Butyl-2-fluoroanilino)-3,4-difluoro-N-(2-hydroxyethoxy)benzamide.
30 more elements
Dependencies are inferred from the claim text.