ANTHRACYCLINE DERIVATIVES, METHOD OF PRODUCING 13-BENZENIDESULPHONYLHYDRAZINE DERIVATIVES OF ANTHRACYCLINES, METHOD OF PRODUCING 13-DEOXYANTHRACYCLINES, METHOD OF PRODUCING 5-IMINO-13-DEOXYANTHRACYCLINES Russian patent published in 2010 - IPC C07H15/252 C07H1/00 A61K31/704 A61P35/00 

FIELD: chemistry.

SUBSTANCE: invention relates to anthracycline derivatives of general structural formula given below

where R₁, R₂ and R₃ are H or OH; R₄ denotes H, OH, C₁-C₅alkyl, or O-(C₁-C₅)alkyl; R₅ is O or NH; and R₆ is selected from a group comprising H, OH and a sugar residue which is The invention also relates to a method of producing said derivatives by reacting 13-ketoanthracycline or acid salt thereof with benzenidesulphonylhydrazide in an alcohol solvent at temperature of approximately 35-50°C for approximately 10-24 hours. The invention also pertains to a method of producing 13-deoxyanthracyclines, involving preparation of an alcoholic solution of the said 13-benzenidesulphonylhydrazine anthracycline; addition of a reducing agent and acid to the said solution; heating said solution without stirring, agitation or dephlegmation in order to reduce said 13-benzenidesulphonylhydrazine anthracycline; neutralisation of said solution with an aqueous solution of a base to obtain said 13-deoxyanthracycline derivative and precipitation; and, additionally, filtration of said precipitate, extraction of said 13-deoxyanthracycline from said precipitate, as well as extraction of said 13-deoxyanthracycline from the filtrate. The invention also relates to a method of producing 5-imino-13-deoxyanthracyclines involving synthesis of 13-deoxyanthracyclines as described above; dissolution of said 13-deoxyanthracyclines in an alcohol and conversion of said 13-deoxyanthracyclines to the corresponding 5-imino-13-deoxyanthracyclines under the effect of ammonia at temperature lower than approximately 20°C. The invention also relates to a method of producing 13-deoxyanthracyclines involving preparation of an alcoholic solution of 13-benzenidesulphonylhydrazine anthracycline having structural formula given below; addition of a reducing agent and a pyridinium acid salt to the said solution and heating said solution to reduce said 13-benzenidesulphonylhydrazine anthracycline. The invention also relates to a method of producing 5-imino-13-deoxyanthracyclines involving preparation of said 13-deoxyanthracycline and its conversion to the corresponding 5-imino-13-deoxyanthracycline under the effect of ammonia at temperature lower than approximately 20°C.

EFFECT: new compounds have useful biological properties.

21 cl, 4 tbl, 4 ex