Patent ID: 6248770
Filing Date: 2001-06-19
Classification: C07D

Abstract:
A compound of the formula (I) ##STR12##whereinAr is a phenylene or naphthylene group optionally substituted by a fluorine, chlorine, or bromine atom or by a trifloromethyl, C.sub.1-3 -alkyl, or C.sub.1-3 -alkoxy group,a thienylene, thiazolylene, pyridinylene, pyrimidinylene, pyrazinylene, or pyridazinylene group optionally substituted in the carbon skeleton by a C.sub.1-3 -alkyl group;A is a C.sub.1-3 -alkylene group;B is an oxygen or sulfuir atom, or a methylene, carbonyl, sulfinyl, or sulfonyl group, or an imino group optionally substituted by a C.sub.1-3 -alkyl group wherein the alkyl moiety may be mono- or disubstituted by a carboxy group;R.sub.a is an R.sub.1 -CO-C.sub.3-5 -cycloalkyl group, whereinR.sub.1 is a C.sub.1-3 -alkoxy, amino, C.sub.1-4 -alkylamino, or di-(C.sub.1-4 -alkyl)-amino group wherein each alkyl moiety may be substituted by a carboxy group,a 4- to 7-membered cycloalkyleneimino or cycloalkenyleneimino group which may be substituted by a hydroxy group or by one or two C.sub.1-3 -alkyl groups, wherein an alkyl substituent may simultaneously be substituted by a hydroxy, C.sub.1-3 -alkoxy, carboxy, carboxy-C.sub.1-3 -alkoxy, carboxy-C.sub.1-3 -alkylamino, N-(C.sub.1-3 -alkyl)-N-(carboxy-C.sub.1-3 -alkyl)-amino, carboxy-C.sub.1-3 -alkylaminocarbonyl, N-(C.sub.1-3 -alkyl)-N-(carboxy-C.sub.1-3 -alkyl)-aminocarbonyl, carboxy-C.sub.1-3 -alkylaminocarbonylamino, 1-(C.sub.1-3 -alkyl)-3-(carboxy-C.sub.1-3 -alkyl)-aminocarbonylamino, 3-(C.sub.1-3 -alkyl)-3-(carboxy-C.sub.1-3 -alkyl)-aminocarbonylamino, or 1,3-di-(C.sub.1-3 -alkyl)-3-(carboxy-C.sub.1-3 -alkyl)-aminocarbonylamino group,a 4- to 7-membered cycloalkenyleneimino group substituted by a hydroxy group,a 5- to 7-membered cycloalkyleneimino group to which a phenyl ring is fused via two adjacent carbon atoms, wherein the cycloalkyleneimino moiety is optionally substituted by a C.sub.1-3 -alkyl group,a morpholino, piperazino, N-(C.sub.1-3 -alkyl)-piperazino, pyrrolino, 3,4-dehydropiperidino, or pyrrol-1-yl group,an R.sub.2 -CX- C.sub.3-5 -cycloalkyl group, whereinR.sub.2 is a phenyl, naphthyl or monocyclic 5- or 6-membered heteroaryl group optionally substituted by a C.sub.1-3 -alkyl group, wherein the 6-membered heteroaryl group contains one, two, or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted by a C.sub.1-3 -alkyl group, an oxygen or sulfur atom, or an imino group optionally substituted by a C.sub.1-3 -alkyl group and an oxygen or sulfur atom or one or two nitrogen atoms and the abovementioned alkyl substituent may be substituted by a carboxy, carboxy-C.sub.1-3 -alkoxy, carboxy-C.sub.1-3 -alkylamino, or N-(C.sub.1-3 -alkyl)-carboxy-C.sub.1-3 -alkylamino group, andX is an oxygen atom, a C.sub.1-3 -alkylimino, C.sub.1-3 -alkoxyimino, C.sub.1-3 -alkylhydrazino, di-(C.sub.1-3 -alkyl)-hydrazino, C.sub.2-4 -alkanoylhydrazino, N-(C.sub.1-3 -alkyl)-C.sub.2-4 -alkanoylhydrazino or C.sub.1-3 -alkylidene group each of which may be substituted in the alkyl or alkanoyl rnoiety or in the alkyl and alkanoyl moieties by a carboxy group,a C.sub.1-3 -alkyl or C.sub.3-5 -cycloalkyl group substituted by an imidazole or irnidazolone group, whereinthe imidazole ring may be substituted by a phenyl or carboxy group and by one or two C.sub.1-3 -alkyl groups or by one, two, or three C.sub.1-3 -alkyl groups, wherein the substituents may be identical or different and one of the abovementioned alkyl substituents may simultaneously be substituted by a carboxy group or may be substituted in the 2 or 3 position by an amino, C.sub.2-4 -alkanoylamino, C.sub.1-3 -alkylamino, N-(C.sub.2-4 -alkanoyl)-C.sub.1-3 -alkylamino or di-(C.sub.1-3 -alkyl)-amino group, andthe imidazolone ring may be substituted by a C.sub.1-3 -alkyl group, wherein the alkyl substituent may be substituted by a carboxy group or in the 2 or 3 position by anamino, C.sub.2-4 -alkanoylamino, C.sub.1-3 -alkylamino, N-(C.sub.2-4 -alkanoyl)-C.sub.1-3 -alkylamino, or di-(C.sub.1-3 -alkyl)-amino group, andadditionally a phenyl or pyridine ring may be fused to the abovementioned imidazole or imidazolone rings via two adjacent carbon atoms,an imidazolidine-2,4-dion-5-yl group which may be substituted by one or two C.sub.1-3 -alkyl groups, wherein at the same time an alkyl substituent may be substituted by a carboxy group,a C.sub.1-4 -alkyl group which is substitutedby a C.sub.1-3 -alkyl-Y.sub.1 -C.sub.1-3 -alkyl, HOOC-C.sub.1-3 -alkyl-Y.sub.1 -C.sub.1-3 -alkyl, tetrazolyl-C.sub.1-3 -alkyl-Y.sub.2, R.sub.3 NR.sub.4 --, or R.sub.3 NR.sub.4 -C.sub.1-3 -alkyl group, andby an isoxazolidinylcarboniyl group optionally substituted by a C.sub.1-3 -alkyl group, by a pyrrolino-carbonyl, 3,4-dehydro-piperidinocarbonyl, pyrrol-1-yl-carbonyl, carboxy, aminocarbonyl, C.sub.1-3 -alkylaminocarbonyl, di-(C.sub.1-3 -alkyl)-aminocarbonyl, or 4- to 7-membere,d cycloalkyleneiminocarbonyl group, wherein in the abovementioned groups; the cycloalkyleneimino moiety may be substituted by one or two C.sub.1-3 -alkyl groups and at the same time each alkyl moiety or alkyl substituent in the abovementioned C.sub.1-3 -alkylaminocarbonyl, di-(C.sub.1-3 -alkyl)-aminocarbonyl, or cycloalkyleneiminocarbonyl groups may be substituted by a carboxy group, and the remaining hydrogen atoms of the C.sub.1-4 -alkyl group may be wholly or partially replaced by fluorine atoms, whereinR.sub.3 is a hydrogen atom or a C.sub.1-3 -alkyl group optionally substituted by a carboxy group, andR.sub.4 is a hydrogen atom, a C.sub.1-3 -alkyl-Y.sub.1 -C.sub.1-3 -alkyl-Y.sub.2, carboxy-C.sub.1-3 -alkyl-Y.sub.1 -C.sub.1-3 -alkyl-Y.sub.2, C.sub.1-3 -alkyl-Y.sub.2, or carboxy-C.sub.1-3 -alkyl-Y.sub.2 group, orR.sub.3 and R.sub.4 together with the nitrogen atom between them are an 4- to 7-membered cycloalkyleneimino group optionally substituted by a carboxy, C.sub.1-3 -alkyl, or carboxy-C.sub.1-3 -alkyl group, whereinY.sub.1 is a carbon-carbon bond, an oxygen or sulfur atom, or a sulfinyl, sulfonyl, --NH--, --NH--CO--, or --NH--CO--NH-- group, andY.sub.2 is a carbon--nitrogen bond or a carbonyl, sulfonyl, imino, or --NH--CO-- group, wherein the carbonyl group of the --NH--CO-- group is linked to the nitrogen atom of the R.sub.3 NR.sub.4 -- group, and the imino groups occurring in the definition of the groups Y.sub.1 and Y.sub.2 may each additionally be substituted by a C.sub.1-3 -alkyl or carboxy-C.sub.1-3 -alkyl group,a C.sub.1-3 -alkyl or C.sub.3-5 -cycloalkyl group substituted by a R.sub.5 NR.sub.6 -- group, whereinR.sub.5 is a hydrogen atom, a C.sub.1-3 -alkyl, C.sub.5-7 -cycloalkyl, phenylcarbonyl, phenylsulfonyl, or pyridinyl group, andR.sub.6 is a C.sub.1-3 -alkyl, carboxy-C.sub.1-3 -alkyl, or carboxy-C.sub.1-3 -alkylcarbonyl group,a C.sub.1-3 -alkyl group which is substituted by a C.sub.2-4 -alkanoyl or C.sub.5-7 -cycloalkanoyl group and by a C.sub.1-3 -alkyl group substituted by a chlorine, brouiine, or iodine atom;R.sub.b is a hydrogen atom or a C.sub.1-3 -alkyl group; andR.sub.c is a cyano group or an amidino group optionally substituted by one or two C.sub.1-3 -alkyl groups,wherein the carboxy, amino and imino groups mentioned in the definition of the abovementioned groups may also be substituted by a group which can be cleaved in vivo,or a tautomer thereof, or a compound thereof which contains, instead of a carboxy group, a group which is negatively charged under physiological conditions, or a salt thereof.