Patent ID: 6040289
Filing Date: 2000-03-21
Classification: A61P,C07C,C07D

Abstract:
A compound of the formula whereinR denotes a phenyl, 1-naphthyl or 2-naphthyl, a 5-membered heteroaromatic ring linked via a carbon atom and containing a nitrogen, oxygen or sulphur atom or a nitrogen atom and an oxygen, a sulphur or further nitrogen atom, wherein a nitrogen atom of an imino group of said 5-membered heteroaromatic ring is optionally substituted by an alkyl, alkoxycarbonylalkyl, carboxyalkyl,. dialkylaminoalkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or alkoxycarbonyl, or a 6-membered heteroaromatic ring linked via a carbon atom, containing 1, 2 or 3 nitrogen atoms, wherein a 1,4-butadienylene group is optionally attached both to the 5-membered or to the 6-membered heteroaromatic rings via two adjacent carbon atoms to form bicyclic heteroaromatic rings which are optionally bound via a carbon atom of the 1,4-butadienylene group,wherein the groups mentioned for R hereinbefore, including the mono- and bicyclic heteroaromatic rings in their carbon skeleton, are optionally mono-, di- or at most trisubstituted by fluorine, chlorine,bromine, alkyl, cycloalkyl groups with 3 to 8 carbon atoms, alkoxy, phenyl, phenylalkoxy, trifluoromethyl, alkoxycarbonylalkyl, carboxyalkyl, dialkylaminoalkyl, hydroxy, amino, acetylamino, propionylamino, benzoyl, benzoylamino, benzoylmethylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkanoyl, cyano, trifluoromethoxy, trifluoromethylthio, trifluoromet hylsulphynyl or trifluoromethylsulphonyl, wherein the substituents are identical or different and the ab)ovementioned benzoyl, benzoylamino and benzoylmethylamino groups are optionally substituted in the phenyl moiety by fluorine, chlorine, bromine, alkyl, trifluoromethyl, amino or acetylamino,or R is a diphenylmethyl group, whereinthe phenyl groups independently of one another are optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, methoxy, hydroxycarbonylmethoxy, alkoxycarbonylmethoxy, hydroxy or trifluoromethyl, wherein the substituents in each case are identical or different;n denotes the numbers 0, 1 or 2,U denotes a single bond, a oxygen atom or an --NH-- group,R.sup.1 denotes a branched or unbranched aliphatic alkylcarbonyl containing 2 to 5 carbon atoms optionally substituted in the alkyl moiety by an alkoxycarbonyl, phenylalkoxycarbonyl, phenyl or by a 5- or 6-membered heteroaromatic ring linked via a carbon atom or a benzoyl group wherein the phenyl moiety is optionally replaced by a 5- or 6-membered heteroaromatic ring linked via a carbon atom,wherein the 5-membered heteroaromatic rings mentioned hereinbefore contain a nitrogen, an oxygen or sulphur atom or a nitrogen atom and an additional oxygen, sulphur or further nitrogen atom and are optionally substituted by an alkyl group at a nitrogen atom, the 6-membered heteroaromatic rings contain 1, 2 or 3 nitrogen atoms; wherein phenyl groups and 5- or 6-membered heteroaromatic rings in their carbon skeleton mentioned hereinbefore are optionally mono-, di- or tri- substituted by fluorine, chlorine, bromine, alkyl, cycloalkyl groups with 3 to 8 carbon atoms, alkoxy, trifluoromethyl, alkoxycarbonylalkyl, carboxyalkyl, hydroxy, amino, acetylamino, propionylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkanoyl, cyano, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphynyl or trifluoromethylsulphonyl, wherein the substituents are identical or different, the aminocarbonyl group in this subparagraph is optionally mono- or disubstituted at the nitrogen atom by alkyl, phenylalkyl, (1-naphthyl)alkyl, (2-naphthyl)alkyl, alkoxycarbonylalkyl, phenylalkoxycarbonylalkyl, phenoxycarbonylalkyl, carboxyalkyl, diphenylalkyl, phenyl, cycloalkyl or cycloalkylalkyl groups with 3 to 8 carbon atoms in the ring in each case, the substituents are identical or different and the abovementioned phenyl groups are optionally independently mono- or disubstituted by fluorine, chlorine, bromine, methyl, methoxy, hydroxycarbonylmethoxy, alkoxycarbonylmethoxy, hydroxy or trifluoromethyl;or R.sup.1 is an alkoxycarbonyl or phenylalkoxycarbonyl, wherein the phenyl moiety is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, methoxy, hydroxycarbonylmethoxy, alkoxycarbonylmethoxy, hydroxy or trifluoromethyl wherein the substituents in each case are identical or different,or R.sup.1 is phenyl, a five-membered heteroaromatic ring bound via a carbon atom which contains a nitrogen, oxygen or sulphur atom or a nitrogen atom and an oxygen, sulphur or further nitrogen atom, wherein a nitrogen atom of an imino group of said five-membered heteroaromatic ring is optionally substituted by an alkyl, or a 6-membered heteroaromatic ring linked via a carbon atom, which contains 1, 2 or 3 nitrogen atoms, wherein the phenyl group and 5- and 6-membered heteroaromatic rings in their carbon skeleton are optionally mono-, di- or at most trisubstituted, by fluorine, chlorine, bromine, alkyl, cycloalkyl groups with 3 to 8 carbon atoms, phenylalkyl, alkoxy, trifluoromethyl, alkoxycarbonylalkyl, carboxyalkyl, hydroxy, amino, acetylamino, propionylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkanoyl, cyano, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl and wherein the substituents are identical or different;or, if R.sup.2 denotes a hydrogen atom, R.sup.1 is optionally methyl;R.sup.2 denotes a hydrogen atom, an alkyl or phenylalkyl optionally mono- or disubstituted in the phenyl moiety by fluorine, chlorine, bromine, alkyl, trifluoromethyl, amino or acetylamino, wherein the substltuents are identical or different;R.sup.3 denotes a hydrogen atom or an alkyl;Y denotes an oxygen atom or --NR.sup.4 -- whereinR.sup.4 denotes a hydrogen atom, a branched or unbranched alkyl with 1 to 6 carbon atoms or a phenylmethyl group;m denotes the number 1 or 2 andV denotes a hydrogen atom, fluorine, chlorine, bromine, iodine, cyano, alkyl, hydroxy, alkoxy, phenylalkoxy-, alkylcarbonyl, dialkylamino, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or the group --(CH.sub.2).sub.o --Y.sup.1 --W'Y.sup.2, whereino denotes the number 0, 1 or 2,W denotes the --SO.sub.2 -- group or the group >C.dbd.X whereinX denotes an oxygen atom or one of the divalent groups .dbd.N--CONH.sub.2 or .dbd.N--CN,Y1 denotes a single bond, an oxygen atom or --NR.sup.5 -- whereinR.sup.5 denotes a hydrogen atom or a straight-chained or branched alkyl with 1 to 6 carbon atoms orR.sup.5 together with the group Y.sup.2, the enclosed nitrogen atom and the enclosed group >C.dbd.X forms a saturated heterocyclic ring with 5 to 7 ring members,Y.sup.2 denotes a straight-chained or branched alkyl with 1 to 10 carbon atoms optionally substituted by a hydroxy, alkoxycarbonyl, aminocarbonyl, a cycloalkyl group with 4 to 10 carbon atoms, a straight-chained or branched alkoxy with 1 to 5 carbon atoms, an aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, phenylmethoxy, 2-phenylethoxy, phenyl or phenylalkyl with 1 to 3 carbon atoms in the alkyl moiety optionally mono-, di- or trisubstituted in the phenyl moiety by fluorine, chlorine, bromine, methyl, trifluoromethyl, cyano, amino, hydroxy, methoxy, acetyl, acetylamino, aminocarbonyl, methylaminocarbonyl or dimethylaminocarbonyl, wherein the substituents are identical or different; orY2 is --NR.sup.6 R.sup.7 wherein:R.sup.6 denotes a hydrogen atom, a straight-chained or branched alkyl with 1 to 6 carbon atoms optionally substituted by a hydroxy, carboxy, alkoxycarbonyl or dialkylamino with the proviso that the hydroxy is not bound in the 1-position of the alkyl, a cycloalkyl group with 4 to 8 carbon atoms, or R.sup.6 is phenyl, phenylmethyl, 2-phenylethyl or 3-phenylpropyl optionally mono-, di- or trisubstituted in the phenyl moiety by fluorine, chlorine, bromine, methyl, trifluoromethyl, hydroxy, methoxy, amino, acetylamino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl or cyano, wherein the substituents are identical or different, or R.sup.6 is an alkanoyl, benzoyl, phenylalkanoyl, alkoxycarbonyl or aminocarbonyl; andR.sup.7 has the meanings given for R.sup.6 with the exception of a phenyl, alkanoyl, benzoyl, phenylalkanoyl, alkoxycarbonyl or aminocarbonyl orR.sup.6 and R.sup.7 together denote an n-alkylene group with 4 to 6 carbon atoms orR.sup.7 together with the group R.sup.5 of the group --NR.sup.5 -- mentioned for Y.sup.1 hereinbefore denotes an unbranched alkylene group or oxoalkylene group with 2 to 4 carbon atoms;wherein all the abovementioned alkyl, cycloalkylalkyl, alkoxy, phenoxycarbonylalkyl, phenylalkoxy, phenylalkoxycarbonyl, phenylalkoxycarbonylalkyl, phenylalkanoyl, phenylalkyl, diphenylalkyl, naphthylalkyl, alkoxycarbonylalkyl, alkoxycarbonylmethoxy, carboxyalkyl, aminoalkyl, monoalkylamino, dialkylamino, alkylaminoalkyl, dialkylaminomethyl, dialkylaminoalkyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkanoyl and alkoxycarbonyl, unless otherwise stated, each contain 1 to 5 carbon atoms in the alkyl and alkoxy moieties,or a tautomer, diastereomer, enantiomer or physiologically acceptable salt thereof.