Amino-benzofuryl-and thienyl-derivatives
First Claim
1. An amino-benzofuryl- or thienyl-derivative of the formula ##STR165## in whichR1 represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms or represents halogen, carboxyl, cyano, nitro, trifluoromethyl or a group of a formula --OR5, --SR6 or --NR7 R8, in whichR5, R6 and R6 are identical or different and denote hydrogen, cycloalkyl having 3 to 6 carbon atoms, benzyl or a 5 to 7-membered saturated or unsaturated heterocycle having up to 4 hetereoatoms selected from the group consisting of N, S or O and to which a phenyl ring can be fused and which is optionally substituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms ordenote straight-chain or branched alkyl or alkenyl each having up to 8 carbon atoms, ordenote phenyl, which is optionally monosubstituted to disubstituted by identical or different substituents selected from the group consisting of nitro, halogen, carboxy or straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms, orR5 denotes a hydroxyl protecting group,R7 denotes hydrogen or a straight-chain or branched alkyl having up to 4 carbon atoms,R2 represents formyl or straight-chain or branched acyl, alkoxy or alkoxycarbonyl each having up to 8 carbon atoms in the alkyl group, or represents benzoyl, which is optionally monosubstituted to trisubstituted by identical or different substituents from the series comprising halogen, cyano, carboxy, straight-chain or branched alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms in the alkyl group, or represents a group of a formula ##STR166## --SO2 R9, --CO--(CH2)a NR10 R11, --CO--(CH2)b --R12, --CO--S--R13 or a residue of the formula ##STR167## in which R9 denotes straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by phenyl, or denotes phenyl, which is optionally substituted by trifluoromethyl, cyano, nitro or straight-chain or branched alkyl having up to 6 carbon atoms,R10 and R11 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or phenyl,R12 denotes straight-chain or branched hydroxyl, oxyacyl, alloxy or alkoxycarbonyl each having up to 6 carbon atoms or carboxy,a denotes a number 0, 1, 2 or 3,b denotes a number 1, 2 or 3,R13 denotes straight-chain or branched alkyl having up to 6 carbon atoms,R3 represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, or has the abovementioned meaning of R2,T represents an oxygen or sulfur atomA represents hydrogen, hydroxyl, cycloalkyl with 3 to 6 carbon atoms, carboxy or straight-chain or branched alkoxycarbonyl or alkoxy each having up to 6 carbon atoms, or straight-chain or branched alkyl or alkenyl each having up 8 carbon atoms and each of which is optionally mono-substituted by cyano or by a 5 to 7-membered saturated or unsaturated heterocycle having up to 4 heteroatoms selected from the group consisting of N, S and O, which is optionally substituted by identical or different substituents selected from the group consisting of hydroxy, halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms, or alkyl or alkenyl are optionally substituted by a group of a formula ##STR168## in which c denotes a number 1 or 2,and in which both rings are optionally monosubstituted by hydroxy, halogen or by straight-chain or branched alkyl having up to 6 carbon atoms,or alkyl or alkenyl are optionally monosubstituted by a group of a formula --CO--R14, --CO--NR15 R16, --CONR17 --SO2 --R18 or --PO(OR19)(OR20), --OR21 or ##STR169## in which R14 denotes hydroxyl, cycloalkyloxy having 3 to 7 carbon atoms or straight-chain or branched alkyl or alkoxy each having up to 8 carbon atoms,R15, R16 and R17 are identical or different and represent hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms, phenyl or benzyl, orR15 denotes hydrogen, andR16 denotes hydroxyl, orR15 and R16 together with the nitrogen atom form a 5- or 6-membered saturated heterocycle,R18 denotes a straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by phenyl or trifluoromethyl, or denotes phenyl, which is optionally substituted by substituents from the series comprising halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms,R19, R20 and R21 are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms,R22 denotes hydrogen, an aminoprotecting group or straight-chain or branched alkyl having up to 6 carbon atoms,R23 and R24 are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, orR23 has the abovementioned meaning, andR24 denotes cycloalkyl having 3 to 6 carbon atoms or aryl having 6 to 10 carbon atoms or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by cyano, methylthio, hydroxy, mercapto, guanidyl or a group of a formula --NR25 R26 or R27 --CO--, whereinR25 and R26 have the meaning shown above for R15, R16 and R17,R27 denotes hydroxyl, benzyloxycarbonyl, straight-chain or branched alkoxy having up to 6 carbon atoms or the abovementioned group --NR25 R26,alkyl is optionally substituted by cycloalkyl having 3 to 6 carbon atoms, or by aryl having up 6 to 10 carbon atoms, which is optionally substituted by hydroxyl, halogen, nitro, straight-chain or branched alkoxy having up to 8 carbon atoms or by the abovementioned group of the formula --NR25 R26, or alkyl is optionally substituted by indolyl wherein the --NH-- function is optionally protected by a straight-chain or branched alkyl having up to 6 carbon atoms or by an amino protecting group, or by a 5 to 6 membered unsaturated heterocycle having up to 4 N-atoms wherein all --NH-functions are protected by straight-chain or branched alkyl having up to 6 carbon atoms or by an amino protecting group, andR4 represents phenyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, adamantyl, phenoxy, cycloalkyl having up to 3 to 6 carbon atoms, halogen, nitro, furanyl, thienyl, pyridyl, tetrazolyl, trifluoromethyl, difluoromethyl, cyano, carboxyl, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 11 carbon atoms in the alkyl group or by phenyl, which is optionally monosubstituted to trisubstituted by nitro, halogen, formyl, carbonyl or straight-chain or branched alkoxy, acyl, alkoxycarbonyl or alkyl each having up to 6 carbon atoms, which is optionally substituted by hydroxyl orphenyl is substituted by a group of formula --NR28 R29, --SR30, SO2 R31, --O--SO2 R32 or ##STR170## in which R28 and R29 have the meaning shown above for R10 and R11, orR28 denotes hydrogen, andR29 denotes straight-chain or branched acyl having up to 6 carbon atoms,R30 denotes straight-chain or branched alkyl having up to 6 carbon atoms,R31 and R32 are identical or different and represent straight-chain or branched alkyl having up to 6 carbon atoms, benzyl or phenyl, which are optionally substituted by trifluoromethyl, halogen or straight-chain or branched alkyl having up to 6 carbon atoms, with the proviso that A does not denote methyl orII if A represents a methyl group R1, T and R4 have the meaning described in part I, and in this caseR2 and R3 are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, or represent formyl or straight-chain or branched acyl, alkoxy or alkoxy carbonyl each having up to 8 carbon atoms, or represent benzoyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, carboxy, straight-chain or branched alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms, or represent a group of a formula --SO2 (NH)g R33, SO2 NH2, --CO--(CH2)d NR34 R35, --(CH2)e --CO--R36, --CO--(CH2)f --R37 or --CO--X, in whichR33 has the abovementioned meaning of R9 and is identical or different to the latter,R34 and R35 are identical or different and have the abovementioned meaning of R10 and R11,R36 denotes hydroxyl or straight-chain or branched alkoxy having up to 6 carbon atoms,R37 has the abovementioned meaning of R12 or denotes straight-chain or branched alkoxy or oxyacyl each having up to 6 carbon atoms or hydroxyl,d has the abovementioned meaning of a,e denotes a number 1, 2, 3, 4 or 5,f has the abovementioned meaning of b,g denotes a number 0 or 1,X denotes a 5-membered saturated or unsaturated heterocycle having up to 3 heteroatoms selected from the group consisting of N, S or O, which is optionally monosubstituted to trisubstituted by nitro, methyl or ethyl, orX denotes a residue of the formula ##STR171## orIIIR1, A and T have the abovementioned meaning described in part I orA represents methyl,R2 and R3 have the abovementioned meaning described in part II, and in this caseR4 represents a 5 to 7 membered, saturated or unsaturated hetereocycle, which contains up to three oxygen, sulphur and/or nitrogen atoms as heteroatoms and to which further a benzene ring can be fused and wherein both rings are optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, halogen, nitro, 1H-tetrazolyl, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, cyano, carboxy, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 8 carbon atoms or by a group of formula --NR38 R39, --SR40, SO2 R41 or --O--SO2 R42, in whichR38 and R39 have the meaning shown above for R28 and R29 and are identical to the latter or different from the latter,R40 has the abovementioned meaning of R30,R41 and R42 are identical or different and have the abovementioned meaning of R31 and R32,or a salt thereof,provided that N-[2-(4-ethoxybenzoyl)-3-hydroxy-5-benzofuranyl]-acetamide;
- 6-amino-2-benzoyl-5-cyano-3-methylbenzofuran;
6-amino-2-(4-p-chlorobenzoyl)-5-cyano-3-methylbenzofuran;
N-[2-benzoyl)-3-methyl-5-benzofuranyl]-acetamide;
N-[2-(2,5-dimethylbenzoyl)-3-methyl-5-benzofuranyl]-acetamide; and
5-amino-2-benzoyl-3-methylbenzofuran and salts thereof are excluded.
1 Assignment
0 Petitions
Accused Products
Abstract
6-Amino-benzofuryl- and thienyl-derivatives can be prepared by reacting appropriate amino-substituted benzoyl phenols with appropriate substituted acetophenones and subsequent modification of the substituents. The compounds are useful for the treatment of actual and chronic inflammatory diseases, particularly of the airways and the gastro-intestinal tract.
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Citations
14 Claims
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1. An amino-benzofuryl- or thienyl-derivative of the formula ##STR165## in which
R1 represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms or represents halogen, carboxyl, cyano, nitro, trifluoromethyl or a group of a formula --OR5, --SR6 or --NR7 R8, in which R5, R6 and R6 are identical or different and denote hydrogen, cycloalkyl having 3 to 6 carbon atoms, benzyl or a 5 to 7-membered saturated or unsaturated heterocycle having up to 4 hetereoatoms selected from the group consisting of N, S or O and to which a phenyl ring can be fused and which is optionally substituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms or denote straight-chain or branched alkyl or alkenyl each having up to 8 carbon atoms, or denote phenyl, which is optionally monosubstituted to disubstituted by identical or different substituents selected from the group consisting of nitro, halogen, carboxy or straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms, or R5 denotes a hydroxyl protecting group, R7 denotes hydrogen or a straight-chain or branched alkyl having up to 4 carbon atoms, R2 represents formyl or straight-chain or branched acyl, alkoxy or alkoxycarbonyl each having up to 8 carbon atoms in the alkyl group, or represents benzoyl, which is optionally monosubstituted to trisubstituted by identical or different substituents from the series comprising halogen, cyano, carboxy, straight-chain or branched alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms in the alkyl group, or represents a group of a formula ##STR166## --SO2 R9, --CO--(CH2)a NR10 R11, --CO--(CH2)b --R12, --CO--S--R13 or a residue of the formula ##STR167## in which R9 denotes straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by phenyl, or denotes phenyl, which is optionally substituted by trifluoromethyl, cyano, nitro or straight-chain or branched alkyl having up to 6 carbon atoms, R10 and R11 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or phenyl, R12 denotes straight-chain or branched hydroxyl, oxyacyl, alloxy or alkoxycarbonyl each having up to 6 carbon atoms or carboxy, a denotes a number 0, 1, 2 or 3, b denotes a number 1, 2 or 3, R13 denotes straight-chain or branched alkyl having up to 6 carbon atoms, R3 represents hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, or has the abovementioned meaning of R2, T represents an oxygen or sulfur atom A represents hydrogen, hydroxyl, cycloalkyl with 3 to 6 carbon atoms, carboxy or straight-chain or branched alkoxycarbonyl or alkoxy each having up to 6 carbon atoms, or straight-chain or branched alkyl or alkenyl each having up 8 carbon atoms and each of which is optionally mono-substituted by cyano or by a 5 to 7-membered saturated or unsaturated heterocycle having up to 4 heteroatoms selected from the group consisting of N, S and O, which is optionally substituted by identical or different substituents selected from the group consisting of hydroxy, halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms, or alkyl or alkenyl are optionally substituted by a group of a formula ##STR168## in which c denotes a number 1 or 2, and in which both rings are optionally monosubstituted by hydroxy, halogen or by straight-chain or branched alkyl having up to 6 carbon atoms, or alkyl or alkenyl are optionally monosubstituted by a group of a formula --CO--R14, --CO--NR15 R16, --CONR17 --SO2 --R18 or --PO(OR19)(OR20), --OR21 or ##STR169## in which R14 denotes hydroxyl, cycloalkyloxy having 3 to 7 carbon atoms or straight-chain or branched alkyl or alkoxy each having up to 8 carbon atoms, R15, R16 and R17 are identical or different and represent hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms, phenyl or benzyl, or R15 denotes hydrogen, and R16 denotes hydroxyl, or R15 and R16 together with the nitrogen atom form a 5- or 6-membered saturated heterocycle, R18 denotes a straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by phenyl or trifluoromethyl, or denotes phenyl, which is optionally substituted by substituents from the series comprising halogen, cyano, nitro or by a straight-chain or branched alkyl having up to 6 carbon atoms, R19, R20 and R21 are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, R22 denotes hydrogen, an aminoprotecting group or straight-chain or branched alkyl having up to 6 carbon atoms, R23 and R24 are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, or R23 has the abovementioned meaning, and R24 denotes cycloalkyl having 3 to 6 carbon atoms or aryl having 6 to 10 carbon atoms or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by cyano, methylthio, hydroxy, mercapto, guanidyl or a group of a formula --NR25 R26 or R27 --CO--, wherein R25 and R26 have the meaning shown above for R15, R16 and R17, R27 denotes hydroxyl, benzyloxycarbonyl, straight-chain or branched alkoxy having up to 6 carbon atoms or the abovementioned group --NR25 R26, alkyl is optionally substituted by cycloalkyl having 3 to 6 carbon atoms, or by aryl having up 6 to 10 carbon atoms, which is optionally substituted by hydroxyl, halogen, nitro, straight-chain or branched alkoxy having up to 8 carbon atoms or by the abovementioned group of the formula --NR25 R26, or alkyl is optionally substituted by indolyl wherein the --NH-- function is optionally protected by a straight-chain or branched alkyl having up to 6 carbon atoms or by an amino protecting group, or by a 5 to 6 membered unsaturated heterocycle having up to 4 N-atoms wherein all --NH-functions are protected by straight-chain or branched alkyl having up to 6 carbon atoms or by an amino protecting group, and R4 represents phenyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, adamantyl, phenoxy, cycloalkyl having up to 3 to 6 carbon atoms, halogen, nitro, furanyl, thienyl, pyridyl, tetrazolyl, trifluoromethyl, difluoromethyl, cyano, carboxyl, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 11 carbon atoms in the alkyl group or by phenyl, which is optionally monosubstituted to trisubstituted by nitro, halogen, formyl, carbonyl or straight-chain or branched alkoxy, acyl, alkoxycarbonyl or alkyl each having up to 6 carbon atoms, which is optionally substituted by hydroxyl or phenyl is substituted by a group of formula --NR28 R29, --SR30, SO2 R31, --O--SO2 R32 or ##STR170## in which R28 and R29 have the meaning shown above for R10 and R11, or R28 denotes hydrogen, and R29 denotes straight-chain or branched acyl having up to 6 carbon atoms, R30 denotes straight-chain or branched alkyl having up to 6 carbon atoms, R31 and R32 are identical or different and represent straight-chain or branched alkyl having up to 6 carbon atoms, benzyl or phenyl, which are optionally substituted by trifluoromethyl, halogen or straight-chain or branched alkyl having up to 6 carbon atoms, with the proviso that A does not denote methyl or II if A represents a methyl group R1, T and R4 have the meaning described in part I, and in this case R2 and R3 are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, or represent formyl or straight-chain or branched acyl, alkoxy or alkoxy carbonyl each having up to 8 carbon atoms, or represent benzoyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, carboxy, straight-chain or branched alkoxy, alkoxycarbonyl or acyl each having up to 6 carbon atoms, or represent a group of a formula --SO2 (NH)g R33, SO2 NH2, --CO--(CH2)d NR34 R35, --(CH2)e --CO--R36, --CO--(CH2)f --R37 or --CO--X, in which R33 has the abovementioned meaning of R9 and is identical or different to the latter, R34 and R35 are identical or different and have the abovementioned meaning of R10 and R11, R36 denotes hydroxyl or straight-chain or branched alkoxy having up to 6 carbon atoms, R37 has the abovementioned meaning of R12 or denotes straight-chain or branched alkoxy or oxyacyl each having up to 6 carbon atoms or hydroxyl, d has the abovementioned meaning of a, e denotes a number 1, 2, 3, 4 or 5, f has the abovementioned meaning of b, g denotes a number 0 or 1, X denotes a 5-membered saturated or unsaturated heterocycle having up to 3 heteroatoms selected from the group consisting of N, S or O, which is optionally monosubstituted to trisubstituted by nitro, methyl or ethyl, or X denotes a residue of the formula ##STR171## or III R1, A and T have the abovementioned meaning described in part I or A represents methyl, R2 and R3 have the abovementioned meaning described in part II, and in this case R4 represents a 5 to 7 membered, saturated or unsaturated hetereocycle, which contains up to three oxygen, sulphur and/or nitrogen atoms as heteroatoms and to which further a benzene ring can be fused and wherein both rings are optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, halogen, nitro, 1H-tetrazolyl, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, cyano, carboxy, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 8 carbon atoms or by a group of formula --NR38 R39, --SR40, SO2 R41 or --O--SO2 R42, in which R38 and R39 have the meaning shown above for R28 and R29 and are identical to the latter or different from the latter, R40 has the abovementioned meaning of R30, R41 and R42 are identical or different and have the abovementioned meaning of R31 and R32, or a salt thereof, provided that N-[2-(4-ethoxybenzoyl)-3-hydroxy-5-benzofuranyl]-acetamide; - 6-amino-2-benzoyl-5-cyano-3-methylbenzofuran;
6-amino-2-(4-p-chlorobenzoyl)-5-cyano-3-methylbenzofuran;
N-[2-benzoyl)-3-methyl-5-benzofuranyl]-acetamide;
N-[2-(2,5-dimethylbenzoyl)-3-methyl-5-benzofuranyl]-acetamide; and
5-amino-2-benzoyl-3-methylbenzofuran and salts thereof are excluded. - View Dependent Claims (2, 3, 4, 6, 7, 9, 10, 11, 12)
- 6-amino-2-benzoyl-5-cyano-3-methylbenzofuran;
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5. An amino-benzofuryl or thienyl-derivative of the formula ##STR183## wherein
I R1 represents hydrogen, R2 represents formyl or methyl or represents benzoyl, which is optionally substituted by substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, carboxy, straight-chain or branched alkoxy, alkoxycarbonyl or acyl, each having up to 3 carbon atoms in the alkyl group, or represents a group of a formula ##STR184## --SO2 R9, --CO--(CH2)a NR10 R11, --CO--(CH2)b --R12, --CO--S--R13 or a residue of the formula ##STR185## in which R9 denotes straight-chain or branched alkyl having up to 4 carbon atoms, R10 and R11 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 3 carbon atoms or phenyl, R12 denotes straight-chain or branched alkoxycarbonyl having up to 3 carbon atoms or carboxy, a denotes a number 0, 1, 2 or 3, b denotes a number 1, 2 or 3, R13 denotes straight-chain or branched alkyl having up to 3 carbon atoms, R3 represents hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, or has the abovementioned meaning of R2, T represents an oxygen or a sulfur atom, A represents hydrogen, cyclopropyl, cyclobutyl, cyclopentyl, carboxyl, or straight-chain or a branched alkoxycarbonyl or alkoxy each having up to 3 carbon atoms, or straight-chain or branched alkyl having up to 5 carbon atoms which is optionally monosubstituted by cyano or by a group of a formula --CO--R14, --CO--NR15 R16, in which R14 denotes hydroxyl, cyclopropyloxy, cyclopentyloxy, cyclohexyloxy or straight-chain or branched alkyl or alkoxy having up to 5 carbon atoms, R15 and R16 are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 3 carbon atoms or phenyl, and R4 represents phenyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, adamantyl, phenoxy, N-methyl-pyrrolyl, cyclopropyl, cyclopentyl, cyclohexyl, fluorine, chlorine, bromine, furanyl, thienyl, pyridyl, nitro, trifluoromethyl, difluoromethyl, cyano, carboxyl, methylthio, straight-chain or branched alkyl, alkoxy, acyl or alkoxycarbonyl each having up to 9 carbon atoms, or by phenyl, which is optionally monosubstituted to trisubstituted by fluorine formyl or straight-chain or branched-alkyl having up to 3 carbon atoms, which is optionally substituted by hydroxyl, with the proviso that A does not denote methyl, or when A represents hydroxyl R4 represents phenyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, adamantyl, phenoxy, N-methyl-pyrrolyl, cyclopropyl, cyclohexyl, fluorine, chlorine, bromine, furanyl, thienyl, pyridyl, nitro, trifluoromethyl, difluoromethyl, cyano, carboxyl, methylthio, straight-chain or branched alkyl, alkoxy, acyl or alkoxycarbonyl each having up to 9 carbon atoms, or by phenyl, which is optionally monosubstituted to trisubstituted by fluorine, formyl or straight-chain or branched alkyl having up to 3 carbon atoms, which is optionally substituted by hydroxyl, II if A represents a methyl group, R1 and T have the meaning described in part I, and in this case R2 and R3 are identical or different and represent hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, or represent formyl or straight-chain or branched acyl or alkoxycarbonyl each having up to 4 carbon atoms or represent benzoyl, which is optionally substituted by substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, straight-chain or branched alkoxy or alkoxycarbonyl each having up to 3 carbon atoms, or represents a group of a formula --CO--NH2, SO2 NH2, --(CH2)e --CO--R36, --CO--(CH2)f --R37 or --CO--X, in which R37 has the abovementioned meaning of R12 or denotes hydroxyl or straight-chain or branched alkoxy or oxacyl each having up to 4 carbon atoms, R36 denotes hydroxyl or straight-chain or branched alkoxy having up to 3 carbon atoms, e denotes a number 1, 2, 3 or 4, f has the abovementioned meaning of b, X denotes pyrrolyl, N-methyl-pyrrolyl, furyl or isoxacolyl, which are optionally monosubstituted to trisubstituted by nitro, methyl or ethyl, or X denotes a residue of the formula ##STR186## b denotes a number 1 or 2, and R4 represents phenyl, which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of hydroxyl, adamantyl, phenoxy, N-methyl-pyrrolyl, cyclopropyl, cyclopentyl, cyclohexyl, fluorine, chlorine, bromine, furanyl, thienyl, pyridyl, nitro, trifluoromethyl, difluoromethyl, cyano, carboxyl, methylthio, straight-chain or branched acyl or alkoxycarbonyl each having up to 9 carbon atoms, or by phenyl, which is optionally monosubstituted to trisubstituted by fluorine, formyl or straight-chain or branched-alkyl having up to 3 carbon atoms, which is optionally substituted by hydroxyl, III if A represents methyl, R1, A and T have the abovementioned meaning described in part I, R2 and R3 have the meaning described in part II, and in this case R4 represents pyridyl, which optionally is optionally substituted to trisubstituted by identical or different substituents from the group consisting of hydroxyl, fluorine, chlorine, bromine, nitro, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, cyano, carboxy, straight-chain or branched alkyl, alkoxy, alkoxycarbonyl or acyl each having up to 5 carbon atoms, or a salt thereof.
- 8. A compound wherein such compount is [3-methyl-2-(4-methyl-benzoyl)-benzofuran-6-ylamino]-acetic acid ethyl ester of the formula ##STR189## or a salt thereof.
Specification
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- Resources
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Current AssigneeBayer AG
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Original AssigneeBayer AG
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InventorsFitzgerald, Mary F., Tudhope, Stephen, McDonald-Gibson, Wendy J., Abram, Trevor, Fischer, R udiger, Br aunlich, Gabriele, Es-Sayed, Mazen, Hanko, Rudolf, Sturton, Graham
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Primary Examiner(s)DENTZ, BERNARD I
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Application NumberUS08/449,402Time in Patent Office700 DaysField of Search549/468, 549/466, 546/281.7, 548/248, 514/469, 514/470US Class Current514/469CPC Class CodesA61P 1/00 Drugs for disorders of the ...A61P 11/00 Drugs for disorders of the ...A61P 11/08 BronchodilatorsA61P 29/00 Non-central analgesic, anti...A61P 43/00 Drugs for specific purposes...A61P 9/00 Drugs for disorders of the ...A61P 9/10 for treating ischaemic or a...C07D 307/80 Radicals substituted by oxy...C07D 307/83 Oxygen atomsC07D 307/84 Carbon atoms having three b...C07D 405/06 linked by a carbon chain co...C07D 405/10 linked by a carbon chain co...C07D 405/12 linked by a chain containin...C07D 409/10 linked by a carbon chain co...C07D 409/12 linked by a chain containin...C07D 413/12 linked by a chain containin...
