PROCESS FOR OBTAINING NEW ANTHRACENE-9,10-BIS-CARBONYL-HYDRAZONE

There are disclosed anthracene-9, 10- bis- carbonyllydrazones and derivatives thereof useful for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers. The compounds can be represented by the formula: wherein Z is a trivalent moiety selected from the group consisting of those of the formulae: -(CH2)n-@= and -@H-CH= wherein n is 0, 1, 2 or 3 and R is hydrogen, lower alkyl, cycloalkyl, phenyl or benzyl; R1 is of hydrogen or lower alkyl; R2 is selected from the group consisting of monovalent moieties of the formulae: wherein p is 1, 2 or 3, q is 0, 1 or 2, R min is hydrogen or lower alkyl, R sec is lower alkyl R7 is a moiety of the formula: wherein m is 2, 3, 4 or 5, R1, R min and R sec are as hereinbefore defined and the moiety -NR min R sec may be pyrrolidino, piperidino, morpholino or N-methylpiperazino, X is oxo (O =), thioxo (S =) or imino (R min -N =) wherein R min is as hereinbefore defined), and R3, R4, R5 and R6 are each individually selected from the group consisting of hydrogen, halogen, hydroxy, nitro, amino, sulfonamido, lower alkyl; and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof. These compunds can be prepared by reaction of 9,10-anthracenedialdehyde with a hydrazine. The dialdehyde is obtained from the reaction of anthracene with paraformaldehyde and hydrochloric acid, giving the 9,10-bis-(chloromethyl)anthracene derivative, which then is treated with sodium in ethanol. Or anthracene can be reacted with vinylene carbonate, to give a cyclic carbonate which is hydrolised to the diol, which in turn is treated with lead tetraacetate in acetic acid to give the 9,10-anthracenedicarboxaldehyde. Or 9,10-anthracenediacetonitrile, a substituted hydrazine hyrochloride, sodium acetate and Raney nickel is reduced with hydrogen to give the anthracene bis-hydrazone.