Patent CA-1175824-A (CA)
Inventor: HERMECZ ISTVAN
IPC: C07D471/04
Filed: 1979-08-15
Granted: 1984-10-09
Abstract: ABSTRACT OF THE DISCLOSURE            The invention is compounds of the general formula:       optically active antipodes and pharmaceutically acceptable salts thereof wherein R stands for hydrogen or C1-4 alkyl, R1 stands for hydrogen of C1-4 alkyl or R and R1 together with the carbon atoms at the 6- and 7-position may form a benzene ring, R2 stands for hydrogen, C1-4 alkyl, R3 stands for hydrogen, C1-4 alkyl, phenyl, carboxy or alkali metal salt thereof, alkoxycarbonyl containing C1-6 alkoxy, carbamoyl, cyano, -CO-NH-CO-SO2-C6H4p-CH3 or -(CH2)s-COOR14-wherein s = 1-3 and R14 stands for hydrogen or C1-4 alkyl, n stands for 0 or 1, a) if R13 stands for hydrogen and R12 and R11 and R9 and R10 together form a chemical bond each, then Y is a stripped oxygen or sulfur atom, in this case R7 and R8 stand for a lone electron-pair or Y stands for a stripped nitrogen atom, R7 stands for C1-4 alkyl, optionally substituted C6-10 aryl or C7-12 aralkyl, R8 is a lone electron-pair or C1-4 alkyl and in this latter case a halide ion forms a salt with the positive nitrogen atom, X (R4, R5, R6) stands for halogen or X is a stripped oxygen or sulfur atom, R4 stands for hydrogen or C1-4 alkyl, R5 and R6 represent an unshared electron-pair or X stands for chloroacetyl, C1-4 alkyl, optionally substituted C6-10 aryl or optionally substituted heteroaryl, R5 stands for hydrogen or alkyl and R6 is a lone electron-pair or b)     if R12 and R15 together form a chemical bond and R11 stands for R4, R5, R6, R7, R8, X and Y are as defined in item a) and c)     if R10 and R11 and R12 and R13 each together form a chemical bond, then Y represents a stripped oxygen or sulphur and if R7, R8, R9 stand for an unshared electron-pair, then a positive cation forms a salt with the thus formed anion or R8 and R9 stand for an unshared electron-pair, R7 stands for hydrogen or C1-4 alkyl or Y stands for a stripped nitrogen atom, R7 stands for hydrogen, C1-4 alkyl, optionally substituted C6-10 aryl, R6 is a C1-4 alkyl, R9 stands for a lone electron-pair, X (R5, R6, R7) stands for halogen or X represents a stripped oxygen or sulfur atom and if R4, R5 and R6 stand for a lone electron-pair, then a positive cation forms a salt with the thus formed anion or R4 stands for hydrogen or C1-4 alkyl, R5 and R6 stands for an unshared electron-pair or X stands for a stripped nitrogen atom and R4 stands for chloroacetyl, C1-4 alkyl, optionally substituted C?-10 aryl or optionally substituted heteroaryl, R5 stands for hydrogen or C1-4 alkyl and R6 stands for an unshared electron-pair and if Y and X stand for a stripped oxygen or sulfur atom and R5, R6, R7, R8 and R9 represent a lone electron-pair or Y and X stand for a stripped nitrogen atom and R6 and R9 stand for a lone electron-pair, R5 and R8 stand for hydrogen or C1-4 alkyl, then R4 and R7 form an optionally substituted -(CH2)s - wherein s stands for 1,2,3 or 4.  The compounds of the invention are useful intermediates in the preparation of compounds having pharmaceutical utility and in particular they may be converted to 9-hydrazono-substituted pyride-[1,2-a]pyrimidine compounds by reacting them with aryl diazonium salts.  These compounds display anti-allergic activity.