Patent ID: 6013662
Filing Date: 2000-01-11
Classification: C07D

Abstract:
A compound of formula (I): ##STR39## in which: Ar representsa phenyl radical substituted by one or more atoms or radicals, which are identical or different and are selected from halogen atoms and the radicals: alkyl, alkenyl containing 2 to 4 carbon atoms, hydroxyl, mercapto, alkylthio, alkylsulphonyl, alkylsulphinyl, amino, alkylamino, dialkylamino, formyl, alkylcarbonyl, carboxyl, alkyloxycarbonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, cyano, and alkyloxy, the alkyl portions and radicals being optionally perhalogenated, ora phenyl radical condensed with a 4- to 7-membered nonaromatic heterocycle containing one or more heteroatoms selected from oxygen, nitrogen and sulphur atoms, ora polycyclic aromatic radical, wherein said polycylic aromatic radical can contain at least one cycle that is saturated or only partially unsaturated but at least one cycle thereof must be aromatic, ora monocyclic 5- to 12-membered heterocyclic aromatic radical incorporating one or more heteroatoms selected from oxygen, nitrogen and sulphur atoms, said heterocyclic aromatic radical being bonded to the condensed ring via a carbon-carbon bond and optionally being substituted by one or more atoms or radicals, which are identical or different and are selected from halogen atoms and the radicals: alkyl, alkenyl containing 2 to 4 carbon atoms, hydroxyl, alkyloxy, mercapto, alkylthio, alkylsulphonyl, alkylsulphinyl, amino, alkylamino, dialkylamino, formyl, alkylcarbonyl, carboxyl, alkyloxycarbonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, cyano, and trifluoromethyl,wherein each of the alkyl portions and radicals in the definition of Ar contains 1 to 4 carbon atoms;R representsa radical of formula:--(CH.sub.2).sub.m --X.sub.1 --(CH.sub.2).sub.n --Zin whichX.sub.1 represents a single bond or an oxygen or sulphur atom,m represents an integer equal to 0 or 1, andn represents an integer equal to 0, 1 or 2;wherein one or more methylene radicals in said R radical can be substituted by a carboxyl, alkyloxycarbonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, amino, alkylamino or dialkylamino radical, wherein each of the alkyl portions and radicals in the definition of R contains 1 to 4 carbon atoms;Z representsa carboxyl radical, ora COOR.sub.6 radical, in which R.sub.6 represents a straight or branched alkyl radical containing 1 to 3 carbon atoms, ora radical of formula CON(R.sub.7)(R.sub.8) in whichR.sub.7 represents a hydrogen atom or a straight or branched alkyl radical containing 1 to 6 carbon atoms, andR.sub.8 representsa hydrogen atom, ora hydroxyl radical, oran arylsulphonyl radical, optionally substituted by one or more atoms or radicals, which are identical or different and are selected from halogen atoms and alkyl and alkyloxy radicals, ora 5- to 7-membered heterocycle incorporating one or more heteroatoms selected from nitrogen, oxygen and sulphur atoms, it being possible for said heterocycle to be bonded to the N in said CON(R.sub.7)(R.sub.8) radical via a heteroatom, oran amino radical optionally substituted by one or two radicals, which are identical or different and are selected from the radicals:alkyl,carbocyclic aryl, optionally substituted by one or more radicals, which are identical or different and are selected from alkyl and alkyloxy radicals,5- to 7-membered heterocyclyl containing one or more heteroatoms selected from nitrogen, oxygen and sulphur atoms,arylcarbonyl, optionally substituted by one or more radicals, which are identical or different and are selected from alkyl and alkyloxy radicals,or R.sub.8 represents an alkyloxy radical containing 1 to 6 straight- or branched-chain carbon atoms optionally substituted by a phenyl radical, ora straight or branched alkyl radical containing 1 to 6 carbon atoms, optionally substituted by at least one radical selected from amino, alkylamino, dialkylamino, hydroxyl, alkyloxy, mercapto, alkylthio, alkyloxycarbonyl, carboxyl, cyano, and optionally substituted mono- and polycyclic aromatic having from 5 to 12 ring members which may or may not incorporate one or more heteroatoms selected from oxygen, nitrogen and sulphur atoms, it being possible for said mono- and polycyclic aromatic radicals incorporating one or more nitrogen heteroatoms to be in the form of the N-oxide,or Z representsa PO(OR.sub.9).sub.2 radical in which R.sub.9 represents a hydrogen atom or a straight or branched alkyl radical containing 1 to 6 carbon atoms, oran --NH--CO--T radical in which T represents a hydrogen atom or a straight or branched alkyl radical containing 1 to 6 carbon atoms, optionally substituted by an amino, carboxyl, alkyloxycarbonyl, hydroxyl, alkyloxy, mercapto, or alkylthio radical,wherein each of the alkyl portions and radicals provided in the definition of Z that is not of a specifically defined carbon length contains 1 to 4 carbon atoms;R.sub.1 and R.sub.2, which are identical or different, are selected from a hydrogen atom, a halogen atom, an alkyl radical, and an alkyloxy radical, wherein each of said radicals may optionally be substituted by a dialkylamino radical, wherein the two alkyl portions of said dialkylamino radical may form, together with the nitrogen atom to which they are attached, a saturated heterocycle containing 5 or 6 ring members, and from an alkylthio radical and an alkyloxycarbonyl radical; or alternatively, situated at the ortho position with respect to one another, R.sub.1 and R.sub.2, together with the ring carbon atoms to which they are attached, form a saturated or unsaturated heterocycle containing 1 or 2 heteroatoms selected from nitrogen and oxygen, optionally substituted by a halogen atom or by an alkyl or alkyloxy radical,wherein the alkyl portions and radicals in the definition of R.sub.1 and R.sub.2 contain 1 to 4 carbon atoms;R.sub.3 and R.sub.4, which are identical or different, are selected from a hydrogen atom, a halogen atom and a radical selected from alkyl, hydroxyl, alkyloxy, alkylcarbonyloxy, mercapto, alkylthio, alkylsulphonyl, alkylsulphinyl, amino, alkylamino, dialkylamino, alkyloxycarbonylamino, carboxyl, alkyloxycarbonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, formyl, alkylcarbonyl, cyano, and trifluoromethyl,wherein the alkyl portions and radicals in the definition of R.sub.3 and R.sub.4 contain 1 to 4 carbon atoms;R.sub.5 represents a hydrogen atom or an alkyl or alkylthio radical, wherein for the definition of R.sub.5, the alkyl portions and radicals contain 1 to 4 carbon atoms;X represents an oxygen or sulphur atom or one of the groups: --NH--, --CO--, methylene, alkene-1,1-diyl, or cycloalkane-1,1-diyl containing 3 to 6 carbon atoms;and Y represents an oxygen or sulphur atom;or a pharmaceutically acceptable salt of a compound of formula (I).