(R)- AND (S)-ISOMERS OF 3-METHYLSPERMIDINE Russian patent published in 2015 - IPC C07C211/14 C07C209/08 C07C209/16 C07C209/62 A61P35/00 A61P43/00 

FIELD: chemistry.

SUBSTANCE: invention relates to novel trihydrochlorides of (R)- and (S)-isomers of 1,8-diamino-3-methyl-4-azaoctane (3-methylspermidine), corresponding to structural formulae given below and to a method for production thereof. Said compounds can be used in vitro and in vivo to investigate individual cell functions of easily interconvertible and partially interchangeable spermine and spermidine, which are vital for tumour cells and pathogenic trypanosomatids. The (R)-isomer of 3-methylspermidine trihydrochloride is the first metabolically stable functionally active spermidine mimetic.

. A method of producing said isomers includes alkylating salts of (R)- and (S)-isomers of N¹-protected 1,3-diaminobutane sulphamide with N-protected 1-amino-4-butylhalides, followed by successive removal of protective groups and treatment of the obtained residue with hydrochloric acid solution. The alkylating agent used can be N-(phthaloyl)-1-amino-4-butylhalides in aprotic polar solvents or N-(4-iodobutyl)phthalimide in dimethyl formamide in the presence of calcium carbonate. Removal of the phthalyl protection is normally carried out with hydrazine hydrate in alcohol. Removal of benzyloxycarbonyl groups is normally carried out by catalytic hydrogenation over Pd-black at atmospheric pressure in a mixture of methanol and acetic acid.

EFFECT: converting the obtained triacetates of R)- and (S)-isomers of 1,8-diamino-3-methyl-4-azaoctane into tetrahydrochlorides is carried out with aqueous hydrochloric acid solution.

7 cl, 5 dwg, 5 ex