GB1141949A — 7-azaindole derivatives

USPTO Abstract

1,141,949. 7-Azaindole derivatives. STERLING DRUG Inc. 2 Feb., 1967 [23 Feb., 1966], No. 5200/67. Heading C2C. Novel compounds of the general formula and their salts wherein 1 or 2 of R, R<SP>1</SP> and R<SP>11</SP> is (2-imidazolin-2-yl) lower alkyl and the remainder are H, lower alkyl, phenyl or phenyl lower alkyl and all or any of the rings may be substituted are prepared by reacting a cyanoalkyl-7-azaindole of the general formula wherein 1 or 2 of Y, Y<SP>1</SP> and Y<SP>11</SP> is cyano lower alkyl and the remainder are H, phenyl, lower alkyl or phenyl lower alkyl with a diamine of the general formula wherein the R's, which may be the same or different, are H or lower alkyl in the presence of a small amount of carbon disulphide or by reacting a suitable alkyl (7-azaindolyl)-alkanimidate hydrochloride with a diamine of the above general formula. The cyanoalkyl- 7 -azaindole intermediates of the second general formula above may be prepared by substituting a suitable nucleus with a halo-alkanenitrile, or by reacting acrylonitrile with an aromatic compound having an active hydrogen atom, or by replacing a tertiary amino group of a Mannich base or by introducing the cyano-alkyl side chain through the formation of the aromatic ring to which it is attached. N,N - Dimethyl - 7 - azaindole - 2 - carboxamide is prepared by treating the acid chloride of 7- azaindole-2-carboxylic acid with dimethylamine, the acid being obtained by hydrolysing ethyl-(2- nitro-3-pyridyl)-pyrurate and then ring closing. The pyrurate is prepared by treating 3-methyl- 2-nitropyridine with ethyl oxalate. # (7 - Azaindol - 3 - yl) - α - cyanoacrylic acid is prepared by treating 7-azaindole-3-carboxaldehyde with cyanoacetic acid and pyridine, the aldehyde being prepared by treating 3-dimethylaminomethyl-7-azaindole, prepared from the acid chloride, with hexamine and propionic acid. The alkyl - (7 - azaindolyl) - alkanimidate hydrochloride intermediates are prepared by treating a cyanoalkyl-7-azaindole of the second general formula above with alkanolic hydrochloric acid. Pharmaceutical compositions comprise as active ingredient a compound of the first general formula above and a pharmaceutical excipient, adjuvant, aqueous medium or water. The compositions may be in the form of tablets or capsules, or solutions or suspensions for oral administration, or solutions for use by injection. The compositions are stated to have vasoconstrictor, cardiovascular and hypotensive properties.