Patent ID: 6169106
Filing Date: 2001-01-02
Classification: C07D

Abstract:
A compound of the formula I ##STR6## wherein: X is an oxygen atom, R.sub.1 is a hydrogen atom or a C.sub.1-4 -alkoxycarbonyl group; R.sub.2 is a carboxy, C.sub.1-4 -alkoxycarbonyl, or aminocarbonyl group wherein the amino moiety may be substituted by one or two C.sub.1-3 -alkyl groups and the substituents may be identical or different; R.sub.3 is a phenyl group unsubstituted or substituted by a fluorine, chlorine, or bromine atom, or by a methyl, cyano, or aminomethyl group; R.sub.4 is a hydrogen atom or a C.sub.1-4 -alkyl group; and R.sub.5 is a hydrogen atom, a C.sub.1-5 -alkyl group unsubstituted or substituted by a carboxy or C.sub.1-3 -alkoxycarbonyl group, or a benzyl group, a C.sub.3-7 -cycloalkyl group unsubstituted or substituted by a methyl group, an indanyl, pyridyl, oxazolyl, thiazolyl, or imidazolyl group unsubstituted or substituted by a methyl group, to which a phenyl ring may additionally be fused via two adjacent carbon atoms, a methylphenyl group unsubstituted or substituted by a fluorine, chlorine, or bromine atom, or by a methoxy, carboxy, C.sub.1-3 -alkyloxycarbonyl, nitro, or aminosulphonyl group, or a dimethoxyphenyl group, a pyrrolidinyl or piperidinyl group linked via a carbon atom, which may be substituted at the nitrogen atom by a C.sub.1-3 -alkyl group, a phenyl group which is substituted by a trifluoromethoxy group, by a fluorine, chlorine, bromine, or iodine atom, by a C.sub.1-3 -alkoxy group which may be substituted in the 2- or 3-position by an amino, C.sub.1-3 -alkylamino, di-(C.sub.1-3 -alkyl)amino, phenyl-C.sub.1-3 -alkylamino, N-(C.sub.1-3 -alkyl)-phenyl-C.sub.1-3 -alkylamino, pyrrolidino, or piperidino group, by a phenyl-C.sub.1-3 -alkylamino-C.sub.1-3 -alkyl group which may be in the phenyl nucleus by a fluorine, chlorine, bromine, or iodine atom, by a C.sub.1-5 -alkyl, C.sub.1-3 -alkoxy, or trifluoromethyl group and additionally at the amine nitrogen atom by a C.sub.1-3 -alkyl group wherein the hydrogen atoms from the 2-position may be wholly or partially replaced by fluorine atoms, by a C.sub.1-5 -alkyl, phenyl, imidazolyl, C.sub.3-7 -cycloalkyl, C.sub.1-3 -alkoxy-C-.sub.1-3 -alkoxy, phenyl-C.sub.1-3 -alkoxy, carboxy-C.sub.1-3 -alkyl, C.sub.1-3 -alkoxycarbonyl-C.sub.1-3 -alkyl, carboxy, C.sub.1-3 -alkoxycarbonyl, aminocarbonyl, C.sub.1-3 -alkylaminocarbonyl, di-(C.sub.1-3 -alkyl)-aminocarbonyl, phenyl-C.sub.1-3 -alkylaminocarbonyl, N-(C.sub.1-3 -alkyl)-phenyl-C.sub.1-3 -alkylaminocarbonyl, piperazinocarbonyl, N-(C.sub.1-3 -alkyl)-piperazinocarbonyl, nitro, amino, C.sub.1-3 -alkylamino, di-(C.sub.1-3 -alkyl)-amino, pyrrolidino, piperidino, morpholino, C.sub.2-4 -alkanoyl-amino, N-(C.sub.1-3 -alkyl)-C.sub.2-4 -alkanoylamino, benzoylamino, or N-(C.sub.1-3 -alkyl)-benzoylamino group, by an N-(C.sub.1-3 -alkyl)-C.sub.2-4 -alkanoylamino group which is additionally substituted in the alkyl moiety by a carboxy or C.sub.1-3 -alkoxycarbonyl group, by a C.sub.1-3 -alkylaminocarbonyl or di-(C.sub.1-3 -alkyl)-aminocarbonyl group wherein an alkyl moiety is additionally substituted by a di-(C.sub.1-3 -alkyl)-amino group, or by an N-(C.sub.1-3 -alkyl)-C.sub.1-3 -alkylsulphonylamino or N-(C.sub.1-3 -alkyl)-phenylsulphonylamino group wherein the alkyl moiety may additionally be substituted by a cyano, carboxy, C.sub.1-3 -alkoxycarbonyl, C.sub.1-3 -alkylamino, di-(C.sub.1-3 -alkyl)-amino group, aminocarbonyl, C.sub.1-3 -alkylaminocarbonyl, di-(C.sub.1-3 -alkyl)-aminocarbonyl, piperidinocarbonyl, or 2-ethylaminocarbonyl group, a phenyl group unsubstituted or substituted by a C.sub.1-3 -alkyl group wherein the alkyl moiety is substituted by a hydroxy, C.sub.1-3 -alkoxy, carboxy, C.sub.1-3 -alkoxy-carbonyl, amino, C.sub.1-5 -alkylamino, di-(C.sub.1-5 -alkyl)-amino, C.sub.2-4 -alkanoylamino, N-(C.sub.1-3 -alkyl)-C.sub.2-4 -alkanoylamino, pyrrolidino, dehydropyrrolidino, piperidino, dehydropiperidino, 3-hydroxypiperidino, 4-hydroxypiperidino, hexamethyleneimino, morpholino, thiomorpholino, piperazino, 4-(C.sub.1-3 -alkyl)-piperazino, 4-phenyl-piperazino, 4-(C.sub.2-4 -alkanoyl)-piperazino, 4-benzoyl-piperazino, or imidazolyl group, wherein the abovementioned saturated cycloalkyleneimino rings, C.sub.1-5 -alkylamino or di-(C.sub.1-5 -alkyl)-amino groups may additionally be substituted by one or two C,-.sub.5 -alkyl groups, by a C.sub.3-7 -cycloalkyl, hydroxy, C.sub.1-3 -alkoxy, carboxy, C.sub.1-3 -alkoxycarbonyl, aminocarbonyl, C.sub.1-3 -alkylaminocarbonyl, or di-(C.sub.1-3 -alkyl)-aminocarbonyl group, by a phenyl-C.sub.1-3 -alkyl or phenyl group optionally mono- or disubstituted in the phenyl nucleus by fluorine, chlorine, bromine, or iodine atoms or by C.sub.1-3 -alkyl or cyano groups, wherein the substituents may be identical or different, or a methylene group adjacent to the nitrogen atom in the abovementioned cycloalkyleneimino rings may be replaced by a carbonyl or sulphonyl group, and the abovementioned monosubstituted phenyl groups may additionally be substituted by a fluorine, chlorine, or bromine atom or by a methyl, amino, C.sub.1-3 -alkylamino, or di-(C.sub.1-3 -alkyl)-amino group, or a phenyl ring unsubstituted or substituted by one or two C.sub.1-3 -alkoxy groups may be fused to one of the abovementioned unsubstituted cycloalkyleneimino rings via two adjacent carbon atoms, or a salt thereof.