Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1990-01-09
1991-01-15
Lilling, Herbert J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C07H 1500, C07H 1524, A61K 3100
Patent
active
049855484
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 diazotised 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.
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Tetrahedron, vol. 40, No. 22, 1984, Pergamon Press Ltd., GB, K. Tamoto et al.: "Novel Resolution of the Anthracyclinone Intermediate by the Use of (2R,3R)-(+)- and (2S,3S)-(-)-1,4-bis(4-Chlorobenzyloxy)-Butane-2,3-Diol"; A Simple And . . .
Angelucci Francesco
Arcamone Federico
Caruso Michele
Suarato Antonino
Farmitalia Carlo Erba S.r.l.
Lilling Herbert J.
Webber Pamela S.
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