IE35388B1 - Nitrofuryl- and nitrothienyl- amidine derivatives - Google Patents

Abstract

1309727 Nitrofuran and nitrothiophene derivatives BOEHRINGER MANNHEIM GmbH 16 June 1971 [20 June 1970] 28217/71 Heading C2C Novel compounds of Formula I (in which Het is a naphthyridine or s-triazolo- [4,3-b]pyridazine ring system which is optionally substituted by hydroxy, amino or C 1-3 alkyl groups, X is an oxygen or sulphur atom, and each of R 1 , R 2 and R 3 is a hydrogen atom or a C 1-3 alkyl or alkoxyalkyl radical, or two of R 1 , R 2 and R 3 , together with the atoms to which they are attached, can form a 5- or 6-membered ring which optionally contains 1 or 2 additional N, O or S atoms) and pharmacologically acceptable acid addition salts thereof, are prepared by (a) condensing a compound of the Formula II with a compound of the Formulµ III, VIII, IX or X (in which R 4 is alkyl ) or with a nitrile of Formula R 3 CN, or (b) reacting a compound of the Formula IV (in which Y is an alkoxy or alkylthio group and R 4 is H or C 1-3 alkyl) with an amine of Formula HNR 1 R 2 , or (c) reacting a compound of Formula V with 5-nitrofurfural or 5-nitrothiophene-2-aldehyde or a reactive derivative thereof, or (d) nitrating a compound of Formula VI and optionally converting the resulting compounds into their pharmacologically acceptable acid addition salts. 3 - Methyl - 6 - (dimethylaminomethyleneamino) - s - triazolo[4,3-b]pyridazine is prepared by reacting 3 - methyl - 6 - amino - s - triazolo- [4,3-b]pyridazine with N,N-dimethylformamide diethyl acetal and dimethylformamide. Pharmaceutical compositions having antibacterial activity, for oral, parenteral or topical administration, comprise one of the above novel compounds together with a pharmaceutical carrier or diluent. [GB1309727A]