Patent ID: 6479524
Filing Date: 2002-11-12
Classification: A61P,C07C,C07D

Abstract:
A compound of the formulaArâ€”Aâ€”(HCR1)â€”Xâ€”Yâ€ƒâ€ƒ(I), wherein:A denotes an ethynylene group, R1 denotes a hydrogen atom or a C1-3-alkyl group, Ar denotes a phenyl group substituted by the groups R2 to R4, whilst R2 denotes a phenyl or phenoxy group, a C1-3-alkyl group which may be substituted by a phenyl, phenylamino, N-(C1-3-alkyl)-phenylamino or N-(C1-3alkanoyl)-phenylamino group, a carboxy or C1-3-alkoxycarbonyl group, a benzoyl or phenylsulphonyl group wherein in each case the phenyl moiety may additionally be substituted by a fluorine, chlorine or bromine atom, by a methyl, methoxy, carboxy or C1--alkoxycarbonyl group, whilst in the above-mentioned benzoyl groups the oxygen atom may additionally be replaced by a carboxy-C1-3-alkoxyimino or C1-3-alk-oxycarbonyl-C1-3-alkoxyimino group, a C1-5-alkylamino group which may be substituted in the alkyl moiety by a phenyl, carboxy, C1-3-alkoxycarbonyl, carboxy-C1-3-alkylaminocarbonyl, C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl, N-(C1-3-alkyl)carboxy-C1-3-alkylaminocarbonyl or N-(C1-3-alkyl)-C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl group, or a C3-7-cycloalkylamino group, whilst the above-mentioned groups may each additionally be substituted at the amino nitrogen atom by a C3-7-cycloalkanoyl, benzoyl or phenylsulphonyl group, by a carboxy-C1-3-alkylcarbonyl or C1-3-alkoxycarbonyl-C1-3-alkylcarbonyl group wherein the alkyl moiety of the alkylcarbonyl group is substituted in each case by an amino or trifluoroacetylamino group, by a C2-4-alkanoyl group, which may be substituted in the alkanoyl moiety by an amino, carboxy, C1-3-alkoxycarbonyl, carboxy-C1-3-alkoxy, C1-3-alkoxycarbonyl-C1-3-alkoxy, carboxy-C1-3-alkylaminocarbonyl, C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl, N-(C1-3-alkyl)-carboxy-C1-3-alkylaminocarbonyl or N-(C1-3-alkyl)-C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl group, by a carboxy-C1-2-alkylaminocarbonyl, C1-3-alkoxycarbonyl-C1-2-alkylaminocarbonyl, carboxy-C1-3-alkylaminocarbonyl-C1-2-alkylaminocarbonyl or C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl-C1-2-alkylaminocarbonyl group, a formyl, pyridylcarbonyl, thienylcarbonyl, imidazolylcarbonyl, 1-methyl-imidazolylcarbonyl, thiazolylcarbonyl or indolylcarbonyl group, a benzimidazol-1-yl, benzimidazol-1-yl-methyl or 5-oxo-4,5-dihydro-pyrazol-3-yl group optionally substituted by 1 or 2 methyl groups, a pyrazol-1-yl group substituted by a phenyl group, by a phenyl group and a C1-4-alkyl group or by one or two C1-4-alkyl groups wherein an alkyl substituent may at the same time be substituted by a carboxy or C1-3-alkoxycarbonyl group, or a carbonyl group which is substituted by a C1-5-alkyl group optionally substituted by a carboxy or C1-3-alkoxycarbonyl group, by a C3-7-cycloalkyl group, by an amino or C1-5-alkylamino group, which are in each case substituted at the amino nitrogen atom by a C1-3-alkyl group which may be substituted by a C3-7-cycloalkyl, phenyl, pyrrolidinyl or pyridinyl group or in the 2 or 3 position by a di-(C1-3-alkyl)-amino group, or by a di-(C1-3-alkyl)-amino group, by a carboxy-C1-3-alkylamino or C1-3-alkoxycarbonyl-C1-3-alkylamino group which is in each case substituted at the amino nitrogen atom by a pyrazolyl group optionally substituted by a C1-3-alkyl group, by a 3- to 7-membered cycloalkyleneimino group which may be substituted by one or two C1-3-alkyl groups, whilst the above-mentioned pyrrolidino groups optionally substituted by a methyl group may additionally be substituted by a hydroxymethyl, carboxy, C1-3-alkoxycarbonyl, carboxy-C1-3-alkyl, C1-3-alkoxycarbonyl-C1-3-alkyl, carboxy-C1-3-alkyloxy-C1-3-alkyl, C1-3-alkoxycarbonyl-C1-3-alkyloxy-C1-3-alkyl, carboxy-C1-3-alkylamino-C1-3-alkyl, N-(C-1-3-alkyl)-carboxy-C1-3-alkylamino-C1-3-alkyl, C1-3-alkoxycarbonyl-C1-3-alkylamino-C1-3-alkyl, N-(C1-3-alkyl)-carboxy-C1-3-alkylamino-C1-3-alkyl or N-(C1-3-alkyl)-C1-3-alkoxycarbonyl-C1-3-alkylamino-C1-3-alkyl group, by a morpholino, piperazino, 4-methyl-piperazino, piperazino-C1-3-alkyl, dihydropyrazolo, tetrahydropyrazolo, tetrahydroisoxazolo or 7-azabicycloheptyl group or by a N-(C1-3-alkyl)phenyl or N-(C1-3-alkyl)-pyridylamino group optionally substituted in the alkyl moiety by a carboxy or C1-3-alkoxycarbonyl group, R3 denotes a hydrogen, fluorine, chlorine or bromine atom, a hydroxy, C1-3-alkoxy, trifluoromethyl, amino or C2-3-alkanoylamino group, a C1-3-alkyl group which may be substituted by a hydroxy, carboxy, C1-3-alkoxycarbonyl, carboxy-C1-3-alkoxy, C1-3-alkoxycarbonyl-C1-3-alkoxy, carboxy-C1-3alkylaminocarbonyl, C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl, N-(C1-3-alkyl)-carboxy-C1-3-alkylaminocarbonyl or N-(C1-3-alkyl)-C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl group, a C1-3-alkyl group which is substituted by a carboxy-C1-3-alkylamino, C1-3-alkoxycarbonyl-C1-3-alkylamino, N-(C1-3-alkyl)-carboxy-C1-3-alkylamino or C1-3-alkoxycarbonyl-C1-3-alkylaminocarbonyl group, a C2-3-alkenyl group substituted by a carboxy or C1-3-alkoxycarbonyl group or a carbimino group optionally substituted at the carbon atom by a C1-3-alkyl group, which is substituted at the imino nitrogen atom by a carboxy-C1-3-alkoxy, C1-3-alkoxycarbonyl-C1-3-alkoxy or aminocarbonylamino group, or R2 and R3 together denote a â€”COâ€”Oâ€”CH2-group and R4 denotes a hydrogen, fluorine, chlorine or bromine atom, a C1-3-alkyl or trifluoromethyl group, X denotes an â€”NH-group optionally substituted by a Cb 1-3-alkyl group and Y denotes a cyclohexyl group substituted by an amino group, a phenylene group substituted by an amidino group, which may be substituted by a benzoyl or C1-8-alkoxycarbonyl group, whilst the above-mentioned phenylene group may be substituted by a methyl or methoxy group, or a tautomer or salt thereof.