HETEROCYCLIC COMPOUNDS

摘要

1308787 Phenanthrolines and other pyridoquinolines IMPERIAL CHEMICAL INDUSTRIES Ltd 7 Sept 1971 [5 Oct 1970 18 Nov 1970 22 Feb 1971] 47151/70 54868/70 and 5096/71 Heading C2C [Also in Division A5] The invention comprises compounds of formulµ and their non-toxic pharmaceutically acceptable salts, wherein R1 is H or Me; R2 is OH, C 1-6 alkoxy, C 7-10 phenylalkoxy or PhO; ring B optionally bears 1 or 2 substituents selected from C 1-8 alkyl, up to C 6 cycloalkyl, C 1-6 alkoxy, CF 3 , Ph, PhO, halogen or NR3R4 (R3, R4 = C 1-6 alkyl or R4 = Ph, or NR3R4 is up to C 7 N- heterocyclyl), or ring B in the phenanthrolines may bear a C 3-5 alkylene radical, but when R1 is Me, the only optional monovalent substituents on ring B are 5- or 6-C 1-5 alkyl, C 1-4 alkoxy, PhO, piperidines or morpholines, or 5,6-Me 2 or 5-Ph-6-MeO; excluding 2,8-dicarboxy-4,10-dihydroxy-1,7-phenanthroline and its C 1-6 alkyl esters ,and 4,9-dihydroxy-2,7-dimethoxycarbonylpyrido[2,3-g]quinoline. These compounds are prepared by cyclization of the corresponding diimine of formula (where the ring is optionally substituted as described for ring B), which is itself made by reacting the corresponding phenylenediamine with R2COCHR1COCOR2 or R2COC:CCOR2; the diamines, usually characterized as the N,N1- diacetyl derivatives, are prepared by reducing the corresponding dinitrobenzenes. Interconversion of acids and esters may be effected by standard procedures.