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filingDate 1980-01-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1981-03-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_4f8599a12a3c481436829260b582ad49
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publicationDate 1981-03-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-4254110-A
titleOfInvention Pentofuranosyl anthracyclines, intermediates in and method for their preparation and compositions and use thereof
abstract Antitumor anthracycline glycosides of the formula: <IMAGE> wherein one of R1 and R2 is hydrogen and the other is formyl, hydroxymethyl or aminomethyl, and R3 is hydrogen, hydroxy or an acyloxy group; and pharmaceutically acceptable acid addition salts of said compounds in which one of R1 and R 2 is aminomethyl are prepared from daunorubicin, doxorubicin or 14-O-acyl derivatives of doxorubicin by deamination and C-3' epimerization effected with NaNO2 in a cold aqueous acidic medium, such as 1N aqueous acetic acid at 0 DEG C., to give compounds wherein one of R1 and R2 is formyl and the optional further steps of selective reduction, e.g., with NaCNBH3 in 4:1 dioxan:aqueous acetate buffer at pH 4.6 or with Na(CH3COO)3BH in benzene under reflux, to form compounds in which one of R1 and R2 hydroxymethyl, or selective reductive amination, e.g., with NaCNBH3 in the presence of methanolic CH3COONH4 and a dehydrating agent, to form compounds in which one of R1 and R2 is aminomethyl.
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