Patent GB-1088942-A (GB)
Title: Improvements in or relating to triazines and the manufacture thereof
IPC: C07D251/20
Filed: 1965-01-11
Abstract: Novel compounds of the Formula I wherein R1 represents a hydrogen atom or a C1- 8 alkyl, C2- 8 alkenyl, C2- 8 alkoxyalkyl, C3- 10 cycloalkyl, phenyl or naphthyl radical optionally substituted by a C1- 8 alkyl, phenyl- or naphthyl-C1- 8\t alkyl, C1- 8 alkyl-(phenyl- or naphthyl-) C1- 8 alkyl, C1- 8 alkoxy - (phenyl or naphthyl - ) C1- 8 alkyl, halophenyl or halonaphthyl radical; R2 represents a di - (C1- 8 alkyl)amino, di - (C2- 8 alkenyl)amino, N-(C1- 8 alkyl)-N-(C2- 8 alkenyl)-amino, aziridinyl, azetidinyl, pyrrolidinyl, piperidino, hexamethyleneimino, heptamethyleneimino, octamethyleneimino or morpholino radical, each of said heterocyclic radicals being optionally substituted on carbon atoms thereof by 1 to 3 C1- 8 alkyl radicals, a nitrogen atom of R2 being the point of attachment of said radical to the triazine ring; R3 represents a hydrogen atom or a C1- 8 alkyl, C2- 8 alkenyl, C3- 10 cycloalkyl, phenyl, naphthyl, phenyl-C1- 8 alkyl or naphthyl-C1- 8 alkyl radical and R4 represents a C1- 8 alkyl, C2- 8 alkenyl, C2- 8 alkenyl, C3- 10 cycloalkyl-(phenyl- or naphthyl-) C1- 8 alkyl, C1- 8 alkyl-(phenyl- or naphthyl-)C1- 8 alkyl, C1- 8 alkoxy-(phenyl- or naphthyl-) C1- 8 alkyl, halophenyl or halonaphthyl radical and wherein cycloalkylradicals may be substituted by C1- 8 alkyl radicals, and acid addition salts thereof, are prepared by mixing a triazine of the Formula II with an organic halide of the Formula R4-X wheren X represents a chlorine, bromine or iodine atom.  <FORM:1088942/C2/1> <FORM:1088942/C2/2> <FORM:1088942/C2/3> 1,2 - Dihydro - 1 - hydroxy - 1,3,5 - triazines of the Formula II may be prepared by oxidizing a triazine of the Formula III with a percarboxylic acid.  Compounds of the Formula II having as substituents alkenyl groups may be converted to the corresponding saturated triazines by hydrogenation. 1,3,5-Triazines of the Formula III may be prepared by reacting a biguanide of the formula R2-C(:NH)NHC(:NH)NHR3 with a carboxylic acid ester, halide, anhydride or nitrile, the above biguanides, where R3 represents a hydrogen atom, being suitably prepared by reacting cyanoguanidine with a secondary amine salt or, where R3 does not represent a hydrogen atom, by reacting the appropriate R3 substituted cyanoguanidine with a secondary amine salt or by reacting a 3,3-disubstituted guanidine with a primary amine salt. 1,3,5-Triazines of the Formula III may also be prepared by reacting cyanuric chloride with a Grignard reagent of the formula R1MgX, where R1 is as defined above but does not represent a hydrogen atom and X represents a halogen atom, to give 2 - (R1-substituted) - 4,6 - dichloro - 1,3,5 - triazines and replacing the chlorine atoms in the latter compounds by primary and secondary amino groups, the replacement being carried out in any order.  In the latter reactions, 2-(R1 - substituted) - 4,6 - di - (trichloromethyl)-1,3,5-triazines may be used in place of the 4,6-dichloro-compounds.  Therapeutic compositions with antihypertensive, vasodilatory, antisecretory and central nervous system depressing properties in forms suitable for oral and parenteral application comprise compounds of the Formula I and acid addition salts thereof together with a suitable carrier therefor.