Patent ID: 6218385
Filing Date: 2001-04-17
Classification: A61P,C07D

Abstract:
A compounds of the formula ##STR28##whereinR.sup.1 signifies hydrogen, hydroxy, lower alkyl, oxygen, halogen, or--OR, --O(C.sub.3 -C.sub.6)cycloalkyl, --O(CHR).sub.n --(C.sub.3 -C.sub.6)cycloalkyl, --O(CHR).sub.n CN, --O(CHR).sub.n CF.sub.3, --O(CHR)(CHR).sub.n,NR.sub.2, --O(CHR)(CHR).sub.n OR, --O(CHR).sub.n -lower alkenyl, --OCF.sub.3, --OCF.sub.2 --R, --OCF.sub.2 -lower alkenyl, --OCHRF, --OCHF-lower alkenyl, --OCF.sub.2 CRF.sub.2, --OCF.sub.2 Br, --O(CHR).sub.n CF.sub.2 Br, --O(CHR).sub.n -phenyl, wherein the phenyl group may be optionally substituted independently from each other by one to three lower alkyl, lower alkoxy, halogen, nitro or cyano groups,--O(CHR)(CHR).sub.n -morpholino, --O(CHR)(CHR).sub.n -pyrrolidino, --O(CHR)(CHR).sub.n -piperidino, --O(CHR)(CHR).sub.n -imidazolo, --O(CHR)(CHR).sub.n -triazolo, --O(CHR).sub.n -pyridino, --O(CHR)(CHR).sub.n --OSi-lower alkyl, --O(CHR)(CHR).sub.n OS(O).sub.2 -lower alkyl, --O(CH.sub.2).sub.n CH.dbd.CF.sub.2, --O(CHR).sub.n -2,2-dimethyl-[1.3]dioxolane, --O(CHR).sub.n --CHOR--CH.sub.2 OR, --O(CHR).sub.n,CHOR--(CHR).sub.n --CH.sub.2 OR or--SR or --S(CHR).sub.n COOR, or--NR.sub.2, --N(R)(CHR)(CHR).sub.n OR, --N(R)(CHR).sub.n CF.sub.3, --N(R)(CHR)(CHR).sub.n -morpholino, --N(R)(CHR)(CHR).sub.n -imidazolo, --N(R)(CHR)(CHR).sub.n -pyrrolidino, --N(R)(CHR)(CHR).sub.n -pyrrolidin-2-one, --N(R)(CHR)(CHR).sub.n -piperidino, --N(R)(CHR)(CHR).sub.n -triazolo, --N(R)(CHR).sub.n -pyridino, orR.sup.1 and R.sup.4 are interconnected to the groups --(CH.sub.2).sub.3-5 --, --(CH.sub.2).sub.2 --N.dbd., --CH.dbd.N--N.dbd.--, --CH.dbd.CH--N.dbd., --NH--CH.dbd.CH-- or --NR--CH.sub.2 -CH.sub.2 -- and form together with any N or C atoms to which they are attached an additional ring;n is 1-6;R signifies hydrogen, lower alkyl or lower alkenyl, independently from each other, if more than one R is present;R.sup.2 signifies nitro or cyano;R.sup.3 signifies hydrogen, lower alkyl, .dbd.O, .dbd.S, --SR, --S(O).sub.2 -lower alkyl, --(C.sub.3 -C.sub.6)cycloalky or piperazino, optionally substituted by lower alkyl, or--CONR.sub.2, --(CHR).sub.n CONR.sub.2, --(CHR).sub.n OR, --(CH.sub.2).sub.n --CF.sub.3, --CF.sub.3, --(CHR).sub.n OC(O)CF.sub.3, --(CHR).sub.n COOR, --(CHR).sub.n SC.sub.6 H.sub.5, wherein the phenyl group may be optionally substituted independently from each other by one to three lower alkyl, lower alkoxy, halogen, nitro or cyano groups,--(CHR).sub.n -1,3-dioxo-1,3-dihydro-isoindol, --(CHR).sub.n -tetrahydro-pyran-2-yloxy or --(CHR).sub.n --S-lower alkyl, or--NR.sub.2, --NRCO-lower alkyl, --NRCHO, --N(R)(CHR).sub.n CN, --N(R)(CHR).sub.n CF.sub.3, --N(R)(CHR)(CHR).sub.n --OR, --N(R)C(O)(CHR).sub.n O-lower alkyl, --NR(CHR).sub.n -lower alkyl, --NR(CHR)(CHR).sub.n --OR, --N(R)(CHR)(CHR).sub.n --O-phenyl, wherein the phenyl group maybe optionally substituted independently from each other by one to three lower alkyl, lower alkoxy, halogen, nitro or cyano groups,--N(R)(CHR).sub.n -lower alkenyl, --N(R)(CHR)(CHR).sub.n --O--(CHR).sub.n OR, --N(R)(CHR).sub.n C(O)O-lower alkyl, --N(R)(CHR).sub.n C(O)NR-lower alkyl, --N(R)(CH.sub.2).sub.n -2,2-dimethyl-[1.3]dioxolane, --N(R)(CHR)(CHR).sub.n morpholino, --N(R)(CHR).sub.n -pyridino, --N(R)(CHR)(CHR).sub.n -piperidino, --N(R)(CHR)(CHR).sub.n -pyrrolidino, --N(R)(CHR)(CHR).sub.n --O-pyridino, --N(R)(CHR)(CHR).sub.n imidazolo, --N(R)(CHR).sub.n --CR.sub.2 --(CHR).sub.n --OR, --N(R)(CHR).sub.n --CR.sub.2 --OR, --N(R)(CHR).sub.n --CHOR--CH.sub.2 OR, --N(R)(CHR).sub.n --CHOR--(CHR).sub.n --CH.sub.2 OR, or--OR, --O(CHR).sub.n CF.sub.3, --OCF.sub.3, --O(CHR)(CHR).sub.n --O-phenyl, wherein the phenyl group may be optionally substituted independently from each other by one to three lower alkyl, lower alkoxy, halogen, nitro or cyano groups, --O(CHR)(CHR) --O-lower alkyl, --O(CHR).sub.n -pyridino or--O(CHR)(CHR).sub.n -morpholino;or R.sup.3 and R.sup.4 are interconnected to the groups --(CH.sub.2).sub.3-5 --, --(CH.sub.2).sub.2 --N.dbd., --CH.dbd.N--N.dbd.--, --CH.dbd.CH--N.dbd., --NH--CH.dbd.CH-- or--NR--CH.sub.2 -CH.sub.2 -- and form together with any N or C atoms to which they are attached an additional ring; andR.sup.4 signifies hydrogen, lower alkyl, lower alkenyl or nitro, or--OR, --OCF.sub.3, --OCF.sub.2 --R, --OCF.sub.2 -lower alkenyl, --OCHRF, --OCHP-lower alkenyl, --O(CHR).sub.n CF.sub.3, or--(CHR).sub.n CHRF, --(CHR).sub.n CF.sub.2 R, --(CHR).sub.n CF.sub.3, --(C.sub.3 -C.sub.6)cycloalkyl, --(CHR).sub.n (C.sub.3 -C.sub.6)cycloalkyl, --(CHR).sub.n CN, --(CHR).sub.n -phenyl, wherein the phenyl group may be optionally substituted independently from each other by one to three lower alkyl, lower alkoxy, halogen, nitro or cyano groups,--(CHR)(CHR).sub.n OR, --(CHR).sub.n CHORCH.sub.2 OR, --(CHR)(CHR).sub.n NR.sub.2, --(CHR).sub.n COOR, --(CHR)(CHR).sub.n OSi-lower alkyl, --(CHR)(CHR).sub.n --OS(O).sub.2 -lower alkyl, --(CH.sub.2).sub.n --CH.dbd.CF.sub.2, --CF.sub.3, --CF.sub.2 --R, --CF.sub.2 -lower alkenyl, --CHRF, --CHF-lower alkenyl, --(CHR).sub.n -2,2-dimethyl-[1.3]dioxolane, --(CH.sub.2).sub.n -2-oxo-azepan-1-yl, --(CHR)(CHR).sub.n -morpholino, --(CHR).sub.n -pyridino, --(CHR)(CHR).sub.n -imidazolo, --(CHR)(CHR).sub.n -triazolo, --(CHR)(CHR).sub.n -pyrrolidino, optionally substituted by --(CH.sub.2).sub.n OH, --(CHR)(CHR).sub.n -3-hydroxy-pyrrolidino or --(CHR)(CHR).sub.n -piperidino, or--NR.sub.2, --N(R)(CHR).sub.n -pyridino, --N(R)C(O)O-lower alkyl, --N(CH.sub.2 CF.sub.3)C(O)O-lower alkyl, --N[C(O)O-lower alkyl].sub.2, --NR--NR--C(O)O-lower alkyl or --N(R)(CHR).sub.n CF.sub.3, --NRCF.sub.3, --NRCF.sub.2 --R, --NRCF.sub.2 -lower alkenyl, --NRCHRF, --NRCHF-lower alkenyl;or is absent if X is --N.dbd. or .dbd.N--;R.sup.5, R.sup.6 signify hydrogen, lower alkyl, lower alkoxy, amino, nitro, --SO.sub.2 NH.sub.2, or halogen; orR.sup.5 and R.sup.6 are interconnected to the group --O--CH.sub.2 --O-- and form together with the C atoms to which they are attached an additional 5-membered ring;R.sup.7, R.sub.8 signify hydrogen, lower alkyl, lower alkoxy, amino, nitro or halogen;R.sup.9, R.sup.10 signify hydrogen or lower alkyl;R.sup.11, R.sup.12 signifies hydrogen, lower alkyl, hydroxy, lower alkoxy, lower alkoxycarbonyloxy or lower alkanoyloxy;R.sup.13, R.sup.14 signify hydrogen, tritium or lower alkyl;R.sup.15, R.sup.16 signifies hydrogen, tritium, lower alkyl, hydroxy, lower alkoxy or are together an oxo group; orX signifies --N.dbd., .dbd.N--, --N<, >C.dbd. or .dbd.C<;Y signifies --N.dbd., .dbd.N--, --NH--, --CH.dbd. or .dbd.CH--; andthe dotted line maybe a bond when R.sup.1, R.sup.3 or R.sup.4 represent a bivalent atom,or a pharmaceutically acceptable salt thereof or their racemic or optically active form.