Pentofuranosyl anthracyclines, intermediates in and method for t

Drug – bio-affecting and body treating compositions – Conjugate or complex of monoclonal or polyclonal antibody,... – Conjugated via claimed linking group – bond – chelating agent,...

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536 17A, A61K 3171, C07H 1524

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active

042541107

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.

REFERENCES:
patent: 4146616 (1979-03-01), Penco et al.
patent: 4181795 (1980-01-01), Whistler
patent: 4183919 (1980-01-01), Cassinelli et al.
Pigman, "The Carbohydrates", 1957, Academic Press Inc., New York, N.Y., pp. 380-381.
Neller, "Chemistry of Organic Compounds", 3rd Ed., 1965, W. B. Saunders, Co., Philadelphia, Pa., pp. 254-255.
William, "Advances in Carbohydrate Chem. and Biochem.", vol. 31, p. 28, 1975, Academic Press, New York, N.Y.
Gribble et al., J.C.S. Chem. Comm., 1975, p. 535.

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