4-demethoxy-4-amino-anthracyclines

Details 4-demethoxy-4-amino-anthracyclines 4-demethoxy-4-amino-anthracyclines

1989-11-01

1990-10-23

Griffin, Ronald W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C07H 1524, A01N 4304

Patent

active

049653512

ABSTRACT:
Anthracycline glycosides of the general formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom or a hydroxyl group, one of R.sub.2 and R.sub.3 represents a hydrogen atom and the other of R.sub.2 and R.sub.3 represents a hydrogen atom or a hydroxyl group; and pharmaceutically acceptable acid addition salts thereof are antitumor agents. These glycosides may be prepared from a daunomycinone derivative of formula (II): ##STR2## in which the 4-amino group is protected. 4-Demethoxy-4-amino-daunomycinone (II) and an earlier intermediate in its preparation, 4-demethoxy-4-amino-7-deoxy-daunomycinone (IX), can be diazotized followed by mild reduction to form 4-demethoxy-daunomycinone or 4-demethoxy-7-deoxy-daunomycinone respectively. 4-Demethoxy-daunomycinone can be converted into another antitumor anthracycline glycoside, 4-demethoxy-daunorubicin.

REFERENCES:
patent: 4021457 (1977-05-01), Kende et al.
patent: 4109076 (1978-08-01), Henry
patent: 4348388 (1982-09-01), Garland
patent: 4448724 (1984-05-01), Cava et al.
I. L. Finar: "Organic Chemistry", 1954, Longmans, Green and Co., London, GB.

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