GB596975A - Manufacture of pyridoacridines - Google Patents

Abstract

1 : 2 : 31 : 21-Pyridoacridines, suitable for use as parasiticides, optionally bearing a non-acidic substituent in either or both of the 3- and 6-positions and bearing in the 9-position a substituted amino group of the form -NH-A-NRR1 (wherein A is a linking group which is aliphatic or alicyclic or aliphatic-carbocyclic and which may be substituted, e.g. by hydrocarbon radicals, hydroxy or alkoxy groups, or dialkylaminoalkyl groups, and which, when wholly or partly an aliphatic chain, may be interrupted by oxygen, nitrogen or sulphur atoms; and wherein NRR1 is a strongly basic amino or substituted amino group such as alkylamino, dialkylamino or piperidino or other strongly basic nitrogen-containing heterocyclic group) are obtained either by the interaction of a diamine NH2-A-N-RR1, optionally in the form of a salt, e.g. the hydrochloride or acetate, with the corresponding 1 : 2 : 31 : 21-pyridoacridine optionally bearing a non-acidic substituent in either or both of the 3- and 6-positions and bearing in the 9-position a labile substituent such as a halogen atom or an alkoxy, aryloxy or alkyl- or aryl-mercapto group, or by the action, optionally in the presence of a solvent or diluent, of a cyclising agent, viz. the pentachloride, pentabromide, oxychloride or oxybromide of phosphorus, or a mixture of such compounds, e.g. a mixture of phosphorus pentachloride and phosphorus oxychloride, on a 2-(quinolyl-(61)-amino)-benzamide substituted on the amido nitrogen atom by the group -A-NRR1 and optionally bearing a non-acidic substituent in either or both of the 4- and 81-positions. Specified diamines are: ethylene diamine, 2-dimethylaminoethylamine, 2 - diethylaminoethylamine, 3 - dimethylaminopropylamine, 3 - diethylaminopropylamine, 4 - diethylaminobutylamine, 4 - diethylamino - 1 - methylbutylamine, 3 - diethylamino - 1 : 2 - dimethylpropylamine, 3-diethylamino-2-hydroxypropylamine, 2 - methylaminoethylamine, 3 - n - butylaminopropylamine, 3-di-n-butylaminopropylamine, 3 - (b - diethylaminoethoxy) - propylamine, 3 - (b - diethylaminoethylmercapto) - propylamine, 5 - diethylamino - 1 - aminopentane, 2-pyrrolidinoethylamine, 1 : 3 - bis - diethylamino - 2 - aminopropane, N - ethyl - N - b - diethylaminoethylethylenediamine, 2 - piperidinoethylamine, 3 - piperidinopropylamine, p - (b - diethylaminoethylmercapto) - aniline, 3 - diethylamino - 2 : 2 - dimethylpropylamine, N - methyl - N - b - diethylaminoethyltrimethylenediamine and b -piperidino-a -methyl-ethylamine. Numerous examples are given.