Patent ID: 6043254
Filing Date: 2000-03-28
Classification: A61K,C07D

Abstract:
A compound of the formula ##STR9## wherein R.sub.1 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, a nitro, amino, C.sub.1-4 -alkanoylamino, (C.sub.1-5 -alkoxy)carbonylamino or benzyloxycarbonylamino group,R.sub.2 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, a C.sub.1-5 -alkyl, trifluoromethyl, cyano, aminocarbonyl, nitro or amino group,a C.sub.1-5 -alkyl group, which is substituted by an amino, phthalimido, C.sub.1-5 -alkylamino, C.sub.3-7 -cycloalkylamino, C.sub.3-4 -alkenylamino, benzylamino, di-(C.sub.1-5 -alkyl)-amino, C.sub.2-6 -alkyleneimino, di-(C.sub.3-4 -alkenyl)-amino, N-(C.sub.1-5 -alkyl)-N-(C.sub.3-4 -alkenyl)-amino, N-(C.sub.1-5 -alkyl)-N-benzylamino, C.sub.1-4 -alkanoylamino, (C.sub.1-5 -alkoxy)carbonylamino, benzyloxycarbonylamino, N-(C.sub.1-4 -alkanoyl)-N-(C.sub.1-5 -alkyl)-amino, .alpha.-oxo-C.sub.3-6 -alkyleneimino, N-((C.sub.1-5 -alkoxy)carbonyl)-N-(C.sub.1-5 -alkyl)-amino, N-benzyloxycarbonyl-N-(C.sub.1-5 -alkyl)-amino, N-(C.sub.1-4 -alkanoyl)-N-(C.sub.2-4 -alkenyl)-amino, N-((C.sub.1-5 -alkoxy)carbonyl)-N-(C.sub.2-4 -alkenyl)-amino, N-benzyloxycarbonyl-N-(C.sub.2-4 -alkenyl)-amino, N-(C.sub.1-4 -alkanoyl)-N-benzylamino, N-((C.sub.1-5 -alkoxy)carbonyl)-N-benzylamino, N-benzyloxycarbonyl-N-benzylamino, (C.sub.1-5 -alkoxy)carbonyl, benzyloxycarbonyl, carboxy, cyano, amidinocarbonyl or imidazolyl group,a C.sub.2-5 -alkenyl group, which is substituted by a phthalimido, C.sub.1-4 -alkanoylamino, (C.sub.1-5 -alkoxy)carbonylamino, benzyloxycarbonylamino, N-(C.sub.1-4 -alkanoyl)-N-(C.sub.1-5 -alkyl)-amino, .alpha.-oxo-C.sub.3-6 -alkyleneimino, N-((C.sub.1-5 -alkoxy)carbonyl)-N-(C.sub.1-5 -alkyl)-amino, N-benzyloxycarbonyl-N-(C.sub.1-5 -alkyl)-amino, N-(C.sub.1-4 -alkanoyl)-N-(C.sub.2-4 -alkenyl)-amino, N-((C.sub.1-5 -alkoxy)carbonyl)-N-(C.sub.2-4 -alkenyl)-amino, N-benzyloxycarbonyl-N-(C.sub.2-4 -alkenyl)-amino, N-(C.sub.1-4 -alkanoyl)-N-benzylamino, N-((C.sub.1-5 -alkoxy)-carbonyl)-N-benzylamino, N-benzyloxycarbonyl-N-benzylamino, (C.sub.1-5 -alkoxy)carbonyl, benzyloxycarbonyl, carboxy, cyano or aminocarbonyl group, oran allyl group which is substituted in the 3-position by an amino, C.sub.1-5 -alkylamino, C.sub.3-7 -cycloalkylamino, C.sub.3-4 -alkenylamino, benzylamino, di-(C.sub.1-5 -alkyl)-amino, C.sub.2-6 -alkyleneimino, di-(C.sub.3-4 -alkenyl)-amino, N-(C.sub.1-5 -alkyl)-N-(C.sub.3-4 -alkenyl)-amino or N-(C.sub.1-5 -alkyl)-N-benzylamino group, andR.sub.3 denotes a group of the formulae ##STR10## wherein A denotes a bond, a C.sub.1-4 -alkylene, C.sub.1-4 -alkylidene, C.sub.2-4 -alkenylene or C.sub.2-4 -alkenylidene group, whilst a hydrogen atom which is bound to the carbon atom of the binding site in the group Het, together with a hydrogen atom of the group A in the .alpha.-position, may also be replaced by another carbon-carbon bond,D denotes a --CH.dbd.CH--NR.sub.a, --CH.dbd.N--NR.sub.a, --N.dbd.CH--NR.sub.a, --NR.sub.a --CO--NR.sub.b, --CH.sub.2 --CO--NR.sub.a, --CO--NR.sub.c --CO, --CH.sub.2 --NR.sub.a --CH.sub.2, --CH.sub.2 --CH.sub.2 --NR.sub.a, --CH.dbd.CH--CH.dbd.N, --CH.sub.2 --CH.sub.2 --CH.sub.2 --NR.sub.d, --CH.dbd.CH--N.dbd.CH, --CH.sub.2 --CH.sub.2 --NR.sub.d --CH.sub.2, --CH.sub.2 --CH.sub.2 --CO--NH, --CH.dbd.CH--CO--NH, --NR.sub.a --CO--CH.dbd.N or --(R.sub.a CR.sub.b)--CO--NR.sub.a --CO bridge, whilstR.sub.a and R.sub.b, which may be identical or different, each denote a hydrogen atom or a methyl group,R.sub.c denotes a hydrogen atom, a (C.sub.1-5 -alkoxy)carbonyl-C.sub.1-5 -alkyl or benzyloxycarbonyl-C.sub.1-5 -alkyl group,R.sub.d denotes a hydrogen atom, a C.sub.1-5 -alkyl, C.sub.1-4 -alkanoyl, (C.sub.1-5 -alkoxy)carbonyl or benzyloxycarbonyl group, andHet denotes a 5-membered heteroaromatic ring which contains a nitrogen atom or a nitrogen atom and an oxygen, sulphur or nitrogen atom, whilst the abovementioned ring may also be substituted by a C.sub.1-5 -alkyl, C.sub.5-7 -cycloalkyl, phenyl, phenyl-C.sub.1-3 -alkyl, amino, C.sub.1-4 -alkanoylamino, (C.sub.1-5 -alkoxy)carbonylamino or benzyloxycarbonylamino group and also by a further C.sub.1-5 -alkyl group,a 5-membered dihydrogenated heteroaromatic ring which contains a nitrogen atom or a nitrogen atom and an oxygen, sulphur or nitrogen atom, whilst the abovementioned ring may also be substituted by one or two C.sub.1-5 -alkyl groups and may contain a carbonyl group and additionally may be substituted at a cyclic nitrogen atom by a (C.sub.1-5 -alkoxy)carbonyl or benzyloxycarbonyl group,a 5-membered tetrahydrogenated heteroaromatic ring, which contains a nitrogen atom, whilst the abovementioned ring may additionally be substituted by one or two C.sub.1-5 -alkyl groups, by a hydroxy, carboxy, (C.sub.1-5 -alkoxy)carbonyl or aminocarbonyl group and may also contain one or two carbonyl groups,a 5-membered tetrahydrogenated heteroaromatic ring which contains a nitrogen atom and an oxygen, sulphur or nitrogen atom, whilst the abovementioned ring may additionally be substituted by one or two C.sub.1-5 -alkyl groups and may contain one or two carbonyl groups, ora tetrazolyl or imidazo[1,2-a]pyrimidin-2-yl group,or a pharmaceutically acceptable salt thereof.