Patent EP-0129509-B1 (EP)
IPC: C07D403/12
Filed: 1984-05-29
Granted: 1989-08-23
Abstract: 1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE Compounds of the formula  see diagramm : EP0129509,P18,F1 wherein R1 is hydrogen, C1 -C4 alkylthio, amino, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, C1 -C4 monoalkyl-, or di-C1 -C4 alkyl-carbamoyl- or -sulfamoyl-, halosulfonyl-, phenyl-C1 -C2 alkoxy-carbonyl-, C1 -C4 alkyl- or di-C1 -C4 alkyl-)amino, C1 -C4 alkoxy, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, mono-C1 -C4 alkyl- or di-C1 -C4 alkyl-carbamoyl- or -sulfamoyl-, halosulfonyl- or phenyl-C1 -C2 alkoxycarbonyl-) oxy, C1 -C4 alkyl, acetyl, propionyl, hydroxy, halogen, trifluoromethyl, cyano, carboxy, methoxy- or ethoxy-carbonyl, carbamoyl, mono- or di-methyl- or -ethyl-carbamoyl, hydroxy-C1 -C4 alkyl or di-C1 -C4 alkylamino-C1 -C4 alkyl ; Cn H2n is C2 -C4 alkylene separating the two nitrogen atoms by 2 or 3 carbon atoms ; R2 is hydrogen, C1 -C7 alkyl, allyl, propargyl, acetyl, propionyl, phenyl-C1 -C3 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, methoxy- or ethoxy-carbonyl, phenylmethoxycarbonyl, phenylethoxycarbonyl, 2-hydroxy-(ethyl or propyl), 3-hydroxy-(propyl or butyl), 4-hydroxybutyl, C2 -C4 alkanoyl-oxy-C2 -C4 alkyl, phenoxy-C2 -C4 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, or C1 -C4 alkoxy-C2 -C4 alkyl ; R3 and R4 independently represent hydrogen, C1 -C7 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, halogen, trifluoromethyl, hydroxy, acetoxy, propionyloxy, sulfamoyl, mono- or di-C1 -C4 alkylsulfamoyl, and R5 and R6 represent hydrogen or C1 -C4 alkyl ; and N-oxides and salts thereof. 1. Claims for the Contracting State : AT A process for the manufacture of compounds of the formula  see diagramm : EP0129509,P20,F2  wherein R1 is hydrogen, C1 -C4 alkylthio, amino, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, C1 -C4 monoalkyl-, or di-C1 -C4 alkyl-carbamoyl- or -sulfamoyl-, halosulfonyl-, phenyl-C1 -C2 alkoxy-carbonyl-, C1 -C4 alkyl- or di-C1 -C4 alkyl-)amino, C1 -C4 alkoxy, (C1 -C4 alkanoyl-, C1 -C4 alkoxycarbonyl-, carbamoyl-, sulfamoyl-, mono-C1 -C4 alkyl- or di- C1 -C4 alkyl-carbamoyl-or -sulfamoyl-, halosulfonyl- or phenyl-C1 -C2 alkoxycarbonyl-)oxy, acyloxy, C1 -C4 alkyl, acetyl, propionyl, hydroxy, halogen, trifluoromethyl, cyano, carboxy, methoxy- or ethoxy-carbonyl, carbamoyl, mono- or di-methyl- or -ethyl-carbamoyl, hydroxy- C1 -C4 alkyl or di-C1 -C4 alkylamino-C1 -C4 alkyl ; Cn H2n is C2 -C4 alkylene separating the two nitrogen atoms by 2 or 3 carbon atoms ; R2 is hydrogen, C1 -C7 alkyl, allyl, propargyl, acetyl, propionyl, phenyl-C1 -C3 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, methoxy- or ethoxy-carbonyl, phenylmethoxycarbonyl, phenylethoxycarbonyl, 2-hydroxy-(ethyl or propyl), 3-hydroxy-(propyl or butyl), 4-hydroxybutyl, C2 -C4 alkanoyloxy-C2 -C4 alkyl, phenoxy-C2 -C4 alkyl which can be substituted at the phenyl ring by halogen, C1 -C4 alkoxy or by C1 -C4 alkyl, or C1 -C4 alkoxy-C2 -C4 alkyl ; R3 and R4 independently represent hydrogen, C1 -C7 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, halogen, trifluoromethyl, hydroxy, acetoxy, propionyloxy, sulfamoyl, mono- or di- C1 -C4 alkylsulfamoyl, and R5 and R6 represent hydrogen or C1 -C4 alkyl ; and N-oxides and salts thereof, characterized in that a) a compound of the formula III  see diagramm : EP0129509,P20,F3  wherein X is a group detachable together with hydrogen or with an alkali metal, and the other symbols are as defined under the formula I, is condensed with a compound of formula IV  see diagramm : EP0129509,P21,F1  or with an alkali metal derivative thereof in which R2 is as defined under the formula I, or b) a compound of the formula VI  see diagramm : EP0129509,P21,F2 wherein Z is oxygen, sulfur or NH, and the other symbols are as defined above, is cyclized under dehydrating, dehydrosulfurating or deaminating conditions, and, if desired, a resulting free compound is converted into a salt or a resulting salt is converted into the free compound or into another salt, and/or, if desired, a resulting mixture of isomers or racemates is resolved into the single isomers or racemates, and/or, if desired, resulting racemates are resolved into the optical antipodes.