Pentofuranosyl anthracyclines, intermediates in and method for their preparation and compositions and use thereof
US4254110A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jan 28, 1980 |
| Grant date | Mar 3, 1981 |
| Priority date | — |
| Expiry date | Jan 28, 2000 |
Classification
- Technology area (CPC A)Human Necessities
- CPC primaryA61P35/00
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Antitumor anthracycline glycosides of the formula: ##STR1## wherein one of R.sub.1 and R.sub.2 is hydrogen and the other is formyl, hydroxymethyl or aminomethyl, and R.sub.3 is hydrogen, hydroxy or an acyloxy group; and pharmaceutically acceptable acid addition salts of said compounds in which one of R.sub.1 and R.sub. 2 is aminomethyl are prepared from daunorubicin, doxorubicin or 14-O-acyl derivatives of doxorubicin by deamination and C-3' epimerization effected with NaNO.sub.2 in a cold aqueous acidic medium, such as 1N aqueous acetic acid at 0.degree. C., to give compounds wherein one of R.sub.1 and R.sub.2 is formyl and the optional further steps of selective reduction, e.g., with NaCNBH.sub.3 in 4:1 dioxan:aqueous acetate buffer at pH 4.6 or with Na(CH.sub.3 COO).sub.3 BH in benzene under reflux, to form compounds in which one of R.sub.1 and R.sub.2 hydroxymethyl, or selective reductive amination, e.g., with NaCNBH.sub.3 in the presence of methanolic CH.sub.3 COONH.sub.4 and a dehydrating agent, to form compounds in which one of R.sub.1 and R.sub.2 is aminomethyl.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.