GB1001665A - Triazine derivatives and process for their preparation - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:1001665/C2/1> (wherein R is a lower alkyl, C3-7 cycloalkyl, hydroxy-lower alkyl, phenyl-lower alkyl, lower alkenyl or propargyl group, R1 is hydrogen or R, and X and Y are identical or different and are hydrogen or halogen atoms or lower alkyl, trihalomethyl, phenyl-lower alkyl, lower alkoxy, lower alkylmercapto, phenyl, lower alkoxyalkoxy, lower alkoxyalkyl, mercapto, hydroxy, phenoxy, phenylthio or amino groups, or mono-or di-substituted amino groups, viz.-NRR1, piperidino, lower alkyl-piperidino, piperazino, 4-R-piperazino, morpholino or pyrrolidino, or <FORM:1001665/C2/2> any phenyl radical optionally bearing halogen, trifluoromethyl, lower alkyl or lower alkoxy substituents, and the term "lower" denoting a maximum of 6 carbon atoms) and their pharmaceutically acceptable salts, and the preparation thereof by condensing a compound of the general formula <FORM:1001665/C2/3> (wherein Z is a halogen atom and Xa and Ya are Z or are X and Y) with an oxyamine of the general formula <FORM:1001665/C2/4> (wherein R11 is hydrogen or R), and, if necessary, converting Xa and/or Ya into X and/or Y by a displacement reaction and/or replacing R11, when hydrogen, by R, and, if desired, replacing R1, when hydrogen, by R, and in all cases, if desired, converting the product into a pharmaceutically acceptable salt thereof, or by the following alternative processes illustrated in examples: (a) using, in place of a compound of the general formula above, a corresponding compound containing one or more mercapto groups in place of one or more halogen atoms; (b) <FORM:1001665/C2/5> trimerizing a cyanamide RON(R1)CN by the action of a strong acid, or heating a pseudourea RON(R1)C(:NH)-O-alkyl with acid; (c) (when X = Y) condensing 2 mols of a nitrile XCN with 1 mol of a cyanamide RON(R1)CN, or 2 mols of an imidate RC(:NH)-O-alkyl with 1 mol of a pseudourea RON(R1)C(:NH)-O-alkyl; (d) (when X = Y = NH2) condensing 2 mols of biguanide with 1 mol of a carbamate RON(R1)-COO-alkyl, or 2 mols of dicyandiamide with 1 mol of a cyanamide RON(R1)CN; (e) (when Y = NH2) condensing 1 mol of an alkoxybiguanide RON(R1)C(: NH)NHC(: NH)NH2 with 1 mol of an ester X-COO-alkyl; (f) for 2,4 - bis - (N - methyl - N - methoxyamino)-s-triazine, condensing 2 mols of N-methyl-N-methoxy-O-methylpseudourea with 1 mol of formamidine. Pharmaceutical preparations comprise the compounds of the invention in pharmaceutically acceptable carriers. They possess a tranquillizing activity and may take the form of tablets, dragees, capsules, suppositories, drops, emulsions, suspensions, syrups, chocolate, candy and chewing gum.