GB1381979A — Amino derivatives of quinoline quinoxaline and quinazoline

USPTO Abstract

1381979 Derivatives of 2-aminoimidazoline PFIZER Ltd 27 Feb 1973 [29 Feb 1972 8 Nov 1972] 9196/72 and 51629/72 Heading C2C The invention comprises compounds of formulae and their pharmaceutically acceptable acid addition salts, wherein the imidazolinamino group is in one of the 5, 6, 7, and 8-positions of the fused ring system, and any of the remaining such positions contain (R<SP>1</SP>) x where x is 0À3 and R<SP>1</SP> is halogen, CF 3 or C 1-6 alkyl or alkoxy; and R<SP>2</SP> which is H or C 1-6 alkyl or alkoxy, is in the heterocyclic portion of the fused ring system. In examples, these compounds are prepared by either (1) reacting an isothiocyanato-quinoline -quinazoline or -quinoxaline with ethylenediamine, and heating the corresponding 2-am noethylthioureido-compound (e.g. with HgO), or (2) reacting a substituted aminoquinoline (or an aminoquinazoline or aminoquinoxaline with PhCONCS to give (e.g.) a benzoylthioureidoquinoline, hydrolysing this to a thioureidoquinoline, and reacting the S-methylthiouranium derivative of the latter with ethylenediamine. Also prepared is 8-bromo-7-nitroquinoline. Therapeutic compositions for oral or parenteral administration comprise compounds of the above formula, which are regulators of the cardiovascular system.