Antitumor anthracycline antibiotics
AssigneeZaidan Hojin Biseibutsu Kagaku Kenkyu Kai
InventorsHamao Umezawa, Tomio Takeuchi, Hiroshi Naganawa, Kuniaki Tatsuta
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Abstract
New anthracycline derivatives of adriamycin and daunomycin prepared by the etherification of the C-4' and/or C-14 hydroxyl groups of the starting material glycosides are found to be useful antimicrobial and antitumor agents.
Claims60
An anthracycline glycoside of the formula ##STR35## wherein R.sup.1 represents hydrogen, hydroxyl, tetrahydropyranyloxy, C.sub.2 -C.sub.7 alkanoyloxy or phenylacetyloxy and R.sup.2 represents hydrogen, C.sub.1 -C.sub.8 alkyloxyethyl, cyclohexyloxyethyl, tetrahydrofuranyl, tetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, with the provisos that (1) when R.sup.1 is hydrogen or hydroxyl, R.sup.2 is not hydrogen and (2) when R.sup.1 is tetrahydropyranyloxy, R.sup.2 is hydrogen or tetrahydropyranyl, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR36## wherein R.sup.1 represents a hydrogen atom, a hydroxyl group or a tetrahydropyranyloxy group and R.sup.2 represents a hydrogen atom or a tetrahydropyranyl group, providing that when R.sup.1 is a hydrogen atom or a hydroxyl group, R.sup.2 is a tetrahydropyranyl group, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR37## wherein R.sup.2 is a tetrahydropyranyl group, or a nontoxic acid addition salt thereof.
The anthracycline glycoside of the formula ##STR38## wherein R.sup.1 is a tetrahydropyranyloxy group and R.sup.2 is hydrogen, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR39## wherein R.sup.1 is tetrahydropyranyloxy and R.sup.2 is tetrahydropyranyl, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR40## wherein R.sup.2 is a tetrahydropyranyl group, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR41## wherein R.sup.1 is a hydrogen atom, a hydroxyl group, an alkoanoyloxy group having from 2 to 7 carbon atoms inclusive or a phenylacetyloxy group and R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, tetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, with the proviso that when R.sup.1 is hydrogen or hydroxyl, R.sup.2 is not tetrahydropyranyl, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR42## wherein R.sup.3 is phenylacetyloxy or alkanoyloxy having from 2 to 7 carbon atoms inclusive and R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, tetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR43## wherein R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, 6-methoxytetrahydropyranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, or a nontoxic acid addition salt thereof.
An anthracycline glycoside of the formula ##STR44## wherein R.sup.2 is alkyloxyethyl in which the alkyl portion has from 1 to 8 carbon atoms inclusive, cyclohexyloxyethyl, tetrahydrofuranyl, 6-methoxytetrahydropyranyl, 6-carbomethoxytetrahydropyranyl or 6-acetoxymethyltetrahydropyranyl, or a nontoxic acid addition salt thereof.
Dependencies are inferred from the claim text.