Patent ID: 6593355
Filing Date: 2003-07-15
Classification: C07D

Abstract:
A compound of the formula wherein Ra denotes a straight-chained C1-3-alkyl group wherein the hydrogen atoms may be wholly or partially replaced by fluorine atoms and which is substituted in the 1 position by: (a) a pyrrolidinocarbonyl or 2,5-dihydropyrrolocarbonyl group optionally substituted by a C1-3-alkyl group and (b) a moiety which is: (1) an ammo group which is monosubstituted by a carboxy-C1-4-alkyl, cyano-C1-4-alkyl or tetrazolyl-C1-4-alkyl group, or (2) a C1-3-alkyl group which is terminally substituted by: (a) an N-(carboxy-C1-3-alkylaminocarbonyl)-amino group optionally substituted by a C1-3-alkyl group at one or both amino nitrogen atoms, (b) carboxy-C1-3-alkoxy, (c) N-(carboxy-C1-3-alkyl) -amino, (d) Nâ€”C1-3-alkyl)-N-(carboxy-C1-3-alkyl)-amino, (e) N-(carboxy-C1-3-alkylsulphonyl)-amino, (f) Nâ€”(C1-3-alkyl)-N-(carboxy-C1-3-alkylsulphonyl)-amino or (g) a tetrazolyl-C1-3-alkyl group, Rb denotes a C1-3-alkyl group and Rc denotes an amidino group, a cyano group or a 1,2,4-oxadiazol-3-yl group substituted in the 5 position by a C1-3-alkyl or phenyl group, while the phenyl substituent may be substituted by a fluorine, chlorine or bromine atom or by a C1-3-alkyl group, wherein any carboxy group mentioned herein before may optionally be replaced by a group which can be converted in vivo into a carboxy group, selected from a hydroxmethyl group, a carboxy group esterified with an alcohol wherein the alcoholic moiety is a C1-6-alkanol, a phenyl-C1-3-alkanol, a C1-9-cycloalkanol, whilst a C5-8-cycloalkanol may additionally be substituted by one or two C1-3-alkyl groups, a C5-8-cycloalkanol, wherein a methylene group in the 3 or 4 position is replaced by an oxygen atom or by an imino group optionally substituted by a C1-3-alkyl, phenyl-C1-3-alkyl, phenyl-C1-3-alkoxycarbonyl or C2-6-alkanoyl group and the cycloalkanol moiety may additionally be substituted by one or two C1-3-alkyl groups, a C4-7-cycloalkenol, a C3-5-alkenol, a phenyl-C3-5-alkenol, a C3-5-alkynol or phenyl-C3-5-alkynol, with the proviso that no bond to the oxygen atom starts from a carbon atom which carries a double or triple bond, a C3-8-cycloalkyl-C1-3-alkanol, a bicycloalkanol having a total of 8 to 10 carbon atoms which may additionally be substituted in the bicycloalkyl moiety by one or two C1-3-alkyl groups, a 1,3 dihydro-3-oxo-1-isobenzofuranol or an alcohol of formula Rdâ€”COâ€”Oâ€”(ReCRf)â€”OH, â€ƒwherein Rd denotes a C1-8-alkyl, C5-7-cycloalkyl, phenyl or phenyl-C1-3-alkyl groups Re denotes a hydrogen atom, a C1-3-alkyl, C5-7-cycloalkyl or phenyl group and Rf denotes a hydrogen atom or a C1-3-alkyl group, or wherein any carboxy group mentioned herein before may optionally be replaced by a group which is negatively charged under physiological conditions, selected from the group consisting of a tetrazol-5-yl, phenylcarbonylaminocarbonyl, trifluoromethylcarbonylaminocarbonyl, C1-6-alkylsulphonylamino, phenylsulphonylamino, benzylsulphonylamino, trifluoromethylsulphonylamino, C1-6-alkylsulphonylaminocarbonyl, phenylsulphonylaminocarbonyl, benzylsulphonylaminocarbonyl and perfluoro-C1-6-alkylsulphonylaminocarbonyl group, and wherein any amino or imino group mentioned herein before may optionally be substituted by a group which can be cleaved in vivo, selected from the group consisting of a hydroxy group, a benzoyl group optionally mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms or by C1-3-alkyl or C1-3-alkoxy groups, whilst the substituents may be identical or different, a pyridinoyl group, a C1-16-alkanoyl group, a 3,3,3-trichloropropionyl or allyloxycarbonyl group, a C1-16-alkoxycarbonyl or C1-16-alkylcarbonyloxy group wherein hydrogen atoms may be wholly or partially replaced by fluorine or chlorine atoms, a phenyl-C1-6-alkoxycarbonyl group, a 3-amino-propionyl group wherein the amino group may be mono- or disubstituted by C1-6-alkyl or C3-7-cycloalkyl groups and the substituents may be identical or different, a C1-3-alkylsulphonyl-C2-4-alkoxycarbonyl, C1-3-alkoxy-C2-4-alkoxy-C2-4-alkoxycarbonyl, Rdâ€”COâ€”Oâ€”(RdCRf)â€”Oâ€”CO, C1-6-alkyl-COâ€”NHâ€”(RgCRh)â€”Oâ€”CO or C1-6-alkyl-COâ€”Oâ€”(RgCRh)â€”(RgCRh)â€”Oâ€”CO group wherein Rd to Rf are as hereinbefore defined, Rg and Rh which may be identical or different, denote hydrogen atoms or C1-3-alkyl groups and wherein the saturated alkyl and alkoxy moieties which contain more than 2 carbon atoms mentioned in the above definitions also include the branched isomers thereof, or a tautomer or a salt thereof.