Abstract: Anthracycline glycosides of the formula I ##STR1## wherein R is hydrogen or hydroxy, one of R.sub.1 and R.sub.2 is methyl and the other of R.sub.1 and R.sub.2 is hydroxy, and pharmaceutically acceptable acid addition salts thereof, which are useful in treating certain mammalian tumors, are prepared by condensing daunomycinone with certain novel sugars in an inert organic solvent and in the presence of a soluble silver salt and a dehydrating agent to form the corresponding protected glycosides from which the protecting groups are removed. This gives the compounds wherein R is hydrogen. The former are converted to the corresponding hydroxyl compounds by treatment with bromine and sodium formate.

Abstract: Anthracycline glycosides of the formula I ##STR1## wherein R is hydrogen or hydroxyl and the hydrochlorides thereof, and which are useful in treating certain mammalian tumors, are prepared by condensing daunomycinone with the novel sugar, 4-O-methyl-2,3,6-trideoxy-3trifluoroacetamidoribohexopyranosyl chloride in an inert organic solvent and in the presence of a soluble silver salt and a dehydrating agent to form 3', 4' -diepi-4'-O-methyl-N-trifluoroacetyl daunorubicin, and removing the N-trifluoroacetyl group therefrom. This gives the compound wherein R is hydrogen. The former is converted to the corresponding hydroxyl compound by conventional means.

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.

Abstract: Disclosed is a new class of antitumor glycoside antibiotics of the formula (IA): ##STR1## wherein R is hydrogen or hydroxy; and X is ##STR2## These compounds are prepared, using novel intermediates, by condensing the appropriate aglycone and amino-deoxy sugar to form the .alpha.-glycosidic linkage.

Abstract: Disclosed is a class of novel daunosaminyl anthracyclinones which are useful in treating Sarcoma 180 ascites.

Abstract: Disclosed is a process for preparing glycoside antitumor antibiotics, including the known compounds daunomycin, adriamycin, 4'-epi-daunomycin and 4'-epi-adriamycin and the novel antibiotics, 3',4'-epi-6'-hydroxydaunomycin, 3',4'-epi-6'-hydroxyadriamycin. 3',4'-epi-daunomycin, 3',4'-epi-adriamycin, 4-demethoxy-4'-epi-daunomycin and 4-demethoxy-4'-epi-adriamycin. Process involves reacting daunomycinone or 4-demethoxy-daunomycinone with a protected 1-halo derivative of 3,4-epi-6-hydroxydaunosamine, 3,4-epi-daunosamine or 4-epi-daunosamine in an inert solvent in the presence of a soluble silver salt catalyst to form a protected derivative of the glycoside antibiotic and removing the protecting groups.

Abstract: The known antibiotics adriamycin and its .beta.-anomer, and the novel compounds, 4'-epiadriamycin (both .alpha.- and .beta.-anomers) are prepared by condensing a novel, reactive protected derivative of adriamycinone with reactive intermediates which are 1-halo-2,3,6-trideoxy-3-trifluoroacetamido-4-trifluoroacetoxy-.alpha.-L-ly xo (or arabino) hexopyranoses.

Abstract: The antitumor efficacy of the known antibiotics daunomycin (daunorubicin) and adriamycin (doxorubicin) is synergized by the use of said antibiotics together with a daunosamine nucleoside. The latter compounds are prepared by condensing a reactive protected daunosamine with a reactive protected heterocyclic base.

Abstract: The novel compounds, 4'-deoxy-daunomycin and 4'-deoxy-adriamycin, as well as derivatives thereof are useful as anti-tumor antibiotics. These compounds are prepared by condensing the corresponding aglycone with a novel trifluoracetyl protected reactive halo sugar which is 2,3,4,6-tetradeoxy-3-trifluoroacetamido-L-threo-hexopyranosyl chloride.

Abstract: The known antitumor antibiotic adriamycin and its .beta.-anomer, and the novel compounds, 4'-epiadriamycin (both .alpha.- and .beta.-anomers) are prepared by condensing a novel, reactive protected derivative of adriamycinone with reactive intermediates which are 1-halo-2,3,6-trideoxy-3-trifluoroacetamido-4-trifluoroacetoxy-.alpha.-L-ly xo (or arabino) hexopyranoses.

Abstract: Daunomycin analogues of the formula: ##STR1## wherein when each R.sub.1 is hydrogen, each R is hydrogen, chlorine, bromine, methyl or methoxy and when each R.sub.1 is chlorine, bromine or methyl, each R is hydrogen, are useful in treating various mammalian tumors and are prepared by reacting a daunomycinone derivative of the formula: ##STR2## wherein R and R.sub.1 are as defined above with 1-chloro-2,3,6-trideoxy-3-trifluoroacetamido-4-trifluoroacetoxy-.alpha.-L- lyxopyranose in an inert anhydrous organic solvent in the presence of a catalyst and a hydrogen chloride acceptor.

Abstract: The known antibiotic daunomycin, and the novel compounds daunomycin-.beta.-anomer and 4'-epidaunomycin (both .alpha.- and .beta.-anomers) are prepared by condensing daunomycinone with reactive novel intermediates which are 1-chloro-2,3,6-trideoxy-3-trifluoroacetamido-4-trifluoroacetoxy-.alpha.-L- lyxo (or arabino) hexopyranoses.

Abstract: Disclosed are novel C-14 adriamycin esters which are useful in the treatment of certain tumors.

Abstract: 14-Aminodaunomycins, which are prepared by reacting 14-bromodaunomycin with an amine in a solvent at about 20.degree.-60.degree. C. are useful in treating certain tumors such as ascites Sarcoma 180 and solid Sarcoma 180.

Abstract: 1. A process for the preparation of a new antibiotic F.I. 1762, which comprises cultivating the Streptomyces 1762 under aerobic conditions in a liquid nutrient medium containing a carbon source, a nitrogen source and mineral salts, at a temperature between 25.degree. and 37.degree. C, over a period of time from 3 to 7 days, and extracting the formed antibiotic from the fermentation broth at a pH between 8 and 9 by means of a water-immiscible solvent, isolating and purifying the antibiotic F.I. 1762.