Patent EP-0190563-A1 (EP)
Inventor: LOSEL WALTER DR
IPC: C07D471/00
Filed: 1986-01-10
Abstract: 1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE 12-Amino-pyridazino[4',5':3,4]pyrrolo[2,1-a]isoquinolines of general formula I  see diagramm : EP0190563,P15,F1  wherein R1 and R2 , which may be identical or different, each represent hydrogen, C3-7 cycloalkyl, C2-5 alkenyl, phenyl (optionally mono- or disubstituted by halogen atoms or methoxy groups), propargyl, a straight-chained or branched, saturated or unsaturated alkyl group with 1 to 5 carbon atoms which may be substituted by hydroxy, alkoxy with 1 to 4 carbon atoms, halogen, NH2 , NH-alkyl with 1 to 2 carbon atoms, N,N-dialkyl with 1 to 2 carbon atoms, NH-acyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, phenyl (optionally substituted by halogen, alkyl with 1 to 2 carbon atoms, alkoxy with 1 to 2 carbon atoms, NH-alkyl with 1 to 2 carbon atoms, N,N-dialkyl with 1 to 2 carbon atoms, NH2 , N-acyl with 2 to 3 carbon atoms), furyl, thienyl, a nitrogen-containing heterocyclic 5- or 6-membered ring which may optionally contain as a further heteroatom an oxygen or sulphur atom (and the ring may optionally be substituted by alkyl with 1 to 4 carbon atoms), or R1 and R2 together with the nitrogen atom represent a 3- to 7-membered ring which may optionally contain as a further heteroatom an oxygen or nitrogen atom [the ring may be optionally substituted by phenyl (C1-4 ) alkyl (this phenyl ring in turn being mono- or disubstituted by halogen atoms or methoxy groups)], or R2 , if R1 represents hydrogen, represents -NH2 , di(C1-2 ) alkylamino, acetonylamino, -NH(C2-3 ) acyl, alkylsulphonyl or alkyloxycarbonyl group with 1 to 3 carbon atoms in the alkyl chain, a isopropylideneimino group  see diagramm : EP0190563,P15,F2 or a heterocyclic 5- or 6-membered ring containing a nitrogen atom and optionally containing as a further heteroatom an oxygen, nitrogen or sulphur atom, R3 , R4 and R5 , which may be identical or different, represent hydrogen or alkyl groups with 1 to 4 carbon atoms, R7 and R8 , which may be identical or different, represent hydroxy, alkoxy with 1 to 4 carbon atoms or alkylthio groups with 1 to 4 carbon atoms, and R6 and R9 , which may be identical or different, represent hydrogen, hydroxy, alkoxy with 1 to 4 carbon atoms or alkylthio groups with 1 to 4 carbon atoms or a group  see diagramm : EP0190563,P16,F1  wherein R10 represents hydrogen or alkyl with 1 to 4 carbon atoms and R11 represents alkyl with 1 to 4 carbon atoms any such alkyl group being optionally substituted by a hydroxy, methoxy or furfuryl group and physiologically acceptable acid addition salts thereof. 1. Claims for the Contracting State : AT Process for preparing a 12-amino-pyridazino[4',5':3,4]pyrrolo[2,1-a]isoquinoline of general formula  see diagramm : EP0190563,P17,F1  wherein R1 and R2 , which may be identical or different, each represent hydrogen, C3-7 cycloalkyl, C2-5 alkenyl, phenyl (optionally mono- or disubstituted by halogen atoms or methoxy groups), propargyl, a straight-chained or branched, saturated or unsaturated alkyl group with 1 to 5 carbon atoms which may be substituted by hydroxy, alkoxy with 1 to 4 carbon atoms, halogen, NH2 , NH-alkyl with 1 to 2 carbon atoms, N,N-dialkyl with 1 to 2 carbon atoms, NH-acyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, phenyl (optionally substituted by halogen, alkyl with 1 to 2 carbon atoms, alkoxy with 1 to 2 carbon atoms, NH-alkyl with 1 to 2 carbon atoms, N,N-dialkyl with 1 to 2 carbon atoms, NH2 , N-acyl with 2 to 3 carbon atoms), furyl, thienyl, a nitrogen-containing heterocyclic 5- or 6-membered ring which may optionally contain as a further heteroatom an oxygen or sulphur atom (and the ring may optionally be substituted by alkyl with 1 to 4 carbon atoms), or R1 and R2 together with the nitrogen atom represent a 3- to 7-membered ring which may optionally contain as a further heteroatom an oxygen or nitrogen atom [the ring may optionally be substituted by phenyl (C1-4 ) alkyl (this phenyl ring in turn being mono- or disubstituted by halogen atoms or methoxy groups)], or R2 , if R1 represents hydrogen, represents -NH2 , di(C1-2 ) alkylamino, acetonylamino, -NH(C2-3 ) acyl, alkylsulphonyl or alkyloxycarbonyl group with 1 to a carbon atoms in the alkyl chain, a isopropylideneimino group  see diagramm : EP0190563,P17,F2  or a heterocyclic 5- or 6-membered ring containing a nitrogen atom and optionally containing as a further heteroatom an oxygen, nitrogen or sulphur atom, R3 , R4 and R5 , which may be identical or different, represent hydrogen or alkyl groups with 1 to 4 carbon atoms, R7 and R8 , which may be identical or different, represent hydroxy, alkoxy with 1 to 4 carbon atoms or alkylthio groups with 1 to 4 carbon atoms, and R6 and R9 , which may be identical or different, represent hydrogen, hydroxy, alkoxy with 1 to 4 carbon atoms or alkylthio groups with 1 to 4 carbon atoms or a group  see diagramm : EP0190563,P17,F3  wherein R10 represents hydrogen or alkyl with 1 to 4 carbon atoms and R11 represents alkyl with 1 to 4 carbon atoms any such alkyl group being optionally substituted by a hydroxy, methoxy or furfuryl group or a physiologically acceptable acid addition salt thereof, characterised in that a 3,4-dihydro-12-methyl-mercapto- pyridazino[4',5':3,4]pyrrolo[2,1-a]isoquinoline of general formula II see diagramm : EP0190563,P18,F1  wherein the groups R3 , R4 , R5 , R6 , R7 , R8 and R9 are as hereinbefore defined, is reacted with a compound of general formula III  see diagramm : EP0190563,P18,F2 wherein R1 and R2 are as hereinbefore defined, and in that a compound thus obtained is optionally converted, in a manner known per se, into a physiologically acceptable acid addition salt.