ES379873A1 - 2,4,6-trisubstituted-s-triazines - Google Patents

Abstract

Procedure for obtaining 2,4,6-trisubstituted S-triasines, of formula: **(See formula)** and the pharmaceutically acceptable acid addition salts thereof, wherein R1 is unsubstituted- or methyl-substituted adamantyl or bicyclo [2.2,1] heptyl or is tertiary alkyl of 4 to 11 carbon atoms, R2 and R3 are the same or different and are secondary alkyl of 4 to 8 carbon atoms, tertiary alkyl of 4 to 11 carbon atoms, unsubstituted- or methyl-substituted cycloalkyl of 3 to 8 carbon atoms, unsubstituted- or methyl-substituted bicyclo [2.2,1] heptyl or adamantyl when R4 and R5 are hydrogen, and may additionally be 3-8-carbon lower cycloalkyl, methyl substituted or unsubstituted lower alkyl when R4 and/or R5 are n- or sec-lower alkyl or hydrogen, and when R2 and R4 and/or R3 and R5, when taken together with the nitrogen atom to which they are attached, in each case, form a polymethylonimino ring of 4 to 6 carbon atoms containing 0 to 4 methyl groups, with the condition of than when R4 and R5. are hydrogen R1, R2 and R3 are not all tertiary butyl or 2,4,4-triaethyl-2-pentyl by reacting a compound of the formula: **(See formula)** where n = 1, 2 or 3, Z is the same or different and is chlorine, bromine, fluorine, iodine, hydrozyl, -O-alkyl, -O-phenyl, -SH, S-alkyl, -SO-alkyl, - SO2-alkyl, -N3 -CN, N + (CH3) 3, -NH2, trichloroalkyl, trifluoroalkyl, guanidino, R-substituted guanidino, NH-R1, NR2 R4 or where R is R1, R2, R3, R4, or R5, and R1, R2, R3, R4 or R5 are as defined above; A and B are chemical valences which, when taken together, form a single bond, or may be linked to other atoms in a symmetrically or asymmetrically substituted symmetrically or asymmetrically substituted trimeric or dimeric open chain; with a compound of the formula: R - X wherein R is normal, secondary or tertiary alkyl, unsubstituted or methyl-substituted bicyclo [2.2.1] heptyl, cycloalkyl or adamantyl, X is NH2, (see formula), -CHO, CR = CR2 or NHY where Y is CN, NH2, OH, acyl, sulfonyl, Si (CH3) 3 or a negative charge; C1, Br, F, I, -OH, O-alkyl, O-phenyl, -SH, -S-alkyl, -SO-alkyl, -SO2-alkyl, -N3 -CN, -N + (CH3) 3, - NH2, -NH-R1, -NHR2, -NHR3, -NHR4, and -NHR5, where R1, R2, R3, R4 and R5 are as defined above, where when R2-5 and R are taken together with nitrogen atom to which they are attached form a polyinethylenimyal ring of 4 to 6 carbon atoms and contain 0 to 4 methyl groups; with the proviso that when X is equal to Z, X and Z can only be -NH2, -NHR1, -NHR2, -NHR3, -NHR4 or -NHR5 as defined above; in the presence or absence of a Lewis acid catalyst, in a stepwise manner when the substituents on the s-triazine product are different, or in stages and/or concurrently when the substituents on the s-triazine are the same; and when X is **(See formula)** the resulting compound is reduced to give a compound of formula I and when the resulting compound is in the RNH-C = H monomeric form, the tris (substituted amino) -s-triazine is trimerized by heat treatment with alkali; and when the resulting compound is in the form of an isomelamine, I can isomerize into an s-triazine of formula I by treatment with a base, said reaction being carried out in an inert solvent for a period of time between 3 and 24 hours at a temperature between 25ºC and 200ºC. (Machine-translation by Google Translate, not legally binding)