Patent GB-896652-A (GB)
Title: Bis-amino compounds
IPC: C07D471/20
Filed: 1960-08-04
Abstract: The invention comprises compounds of the formula Pi-Alk-Pi1, wherein Alk is an alkylene radical separating Pi from Pi1 by 4 to 20 carbon atoms, and each of the groups Pi and Pi1 represents a piperidino group substituted in the 3- or 4-position by a free, monoalkyl- or dialkyl-amino group, an alkylene imino group, which may be substituted by a hydroxyl or alkanoyloxy group, or an N-alkanoylamino group, the alkanoyl radical of which may contain at least one halogen atom, and which piperidino group may be further substituted by at least one alkyl group; and salts and quaternary ammonium compounds thereof.  They may be prepared by reducing the corresponding bis-pyridinium alkanes, and, if desired, converting a primary or secondary amino group in a resulting compound into a secondary, tertiary or acylated amino group, and/or, if desired, hydrolysing an acyl compound.  For example, primary amino compounds may be treated with an aldehyde or ketone and the resulting Schiff bases reduced to form secondary amino compounds; primary or secondary amino compounds may be treated with hydrogen and a catalyst in presence of an aldehyde or ketone to form secondary or tertiary amino compounds; N-acylated primary or secondary amino groups may be reduced to form secondary or tertiary amino groups; primary and secondary amino groups may be alkylated, e.g. with alkyl halides; primary and secondary amino compounds may be N-acylated by treatment with a reactive functional derivative of the appropriate acid; N-acylated derivatives may be hydrolysed, those compounds wherein the acyl group is derived from an O-alkyl-carbonic acid or a polyhalogenoalkane carboxylic acid being particularly susceptible to hydrolysis; benzyloxycarbonyloxyamino groups may be subjected to hydrogenolysis; acid-addition salts and free bases may be interconverted by standard procedures; quaternary ammonium compounds, including hydroxides, may be prepared and interconverted by standard procedures; and racemates may be resolved through their salts with optically active acids or by biochemical methods.  Examples are given and detailed lists of salt-forming organic and inorganic acids and quaternizing agents are provided.  Bis-amino-pyridinium-alkanes are prepared by reacting 2 moles of an amino-pyridine with one mole of an ester formed from a dihydroxy-alkane and a strong inorganic acid or a strong organic sulphonic acid.ALSO:Pharmaceutical compositions comprise substituted bis-piperidino-alkanes of the formula Pi-Alk-Pi1, wherein Alk is an alkylene radical separating Pi from Pi1 by 4 to 20 carbon atoms, and each of the groups Pi and Pi1 represents a piperidino group substituted in the 3- or 4-position by a free, monoalkyl- or dialkyl-amino group, an alkyleneimino group which may be substituted by a hydroxyl or alkanoyloxy group, or an N-alkanoylamino group, the alkanol radical of which may contain at least one halogen atom, and which piperidino group may be further substituted by at least one alkyl group, or salts or quaternary ammonium derivatives thereof, and suitable carriers.  The piperidino compounds, which are stated to be bacteriocides, may be formulated as tablets, capsules, dragees, solutions, suspensions, emulsions, ointments, powders or creams which may contain stabilizing, wetting or emulsifying agents, salts for varying the osmotic pressure or buffers.  They may also be used, either alone or as mixtures, for disinfecting instruments, bandages or linen. Salts with organic and inorganic acids and quaternary derivatives with alkyl halides and alkyl alkane sulphonates acids are referred to.