FIELD: chemistry.
SUBSTANCE: invention relates to improved method of obtaining 4-R-substituted anthracyclines of formula (I) , and their corresponding salts from 4-demethyldaunorubicin. Steps of treating 4-demethyldaunorubicin with a sulfonylating agent to form 4-demethyl-4-sulfonyl-R3-daunorubicin. 4-Demethyl-4-R3-sulfonyl-daunorubicin are performed, then it is processed with reducing agent in the presence of a transition metal catalyst in a temperature range from 30°C to 100°C in polar aprotic solvent in an inert atmosphere. Protected 4-demethoxy-4-R-daunomycin then undergoes hydrolysis in a basic solution to form the 4-R-substituted anthracyclines. Application of novel method makes it possible to avoid stage of forming stereospecific glycoside bond between aglycone and aminoglycoside. The method also increases the yield of final product up to 30-40%.
EFFECT: elaboration of efficient method of obtaining 4-R-substituted demethyldaunorubicin.
13 cl, 10 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD OF OBTAINING 4-DEMETHOXYDAUNORUBICINE | 2012 |
|
RU2540968C2 |
ANTHRACYCLINE GLYCOSIDE AND METHOD OF ITS SYNTHESIS | 1990 |
|
RU2073681C1 |
PROCESS FOR PREPARING ANTHRACYCLINE GLYCOZIDES | 0 |
|
SU1014477A3 |
PROCESS FOR PREPARING 4-SUBSTITUTED ANTHRACYCLINONES | 1989 |
|
RU2071463C1 |
ANTHRACYCLINE GLYCOSIDE AND METHOD OF ITS SYNTHESIS | 1992 |
|
RU2081878C1 |
4-SUBSTITUTED ANTHRACYCLINONES AND ANTHRACYCLINE GLYCOSIDE | 1991 |
|
RU2024483C1 |
METHOD OF ARALKYLATION OF 4'-HYDROXYL GROUP OF ANTHRACYCLINES | 2008 |
|
RU2563453C2 |
METHOD OF OBTAINING HYDROCHLORIDE OF OPTICALLY ACTIVE DOWN-SAMINYL-DERIVATIVES OF ANTHRACYCLINONS | 0 |
|
SU724087A3 |
ANTRACYCLINIC DISACCHARIDES, METHOD OF PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEREOF | 1994 |
|
RU2144540C1 |
8-FLUOROANTHRACYCLINES, METHODS OF THEIR SYNTHESIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEREOF | 1995 |
|
RU2146261C1 |
Authors
Dates
2008-10-20—Published
2004-05-20—Filed