Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1976-01-19
1977-04-26
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
260396R, 424180, 536 4, 536 17, C07H 506
Patent
active
040202704
ABSTRACT:
Anthracyclinone glycoside antibiotics including the known antibiotics daunomycin and adriamycin, as well as other, novel glycoside antibiotics of the formula (VIII): ##STR1## wherein WHEN R.sub.1 is hydrogen, R.sub.2 and R.sub.3 are each independently hydrogen, methyl, methoxy, chloro, or bromo; and when R.sub.2 and R.sub.3 are hydrogen, R.sub.1 is methyl, chloro, or bromo and R.sub.4 and R.sub.5 are each independently hydrogen or hydroxy are prepared by an acid catalyzed addition reaction between (a) an anthracyclinone compound of the formula ##STR2## or a dioxolanyl protected derivative thereof (VI) having the formula: ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above, and R.sub.6, R.sub.7 and R.sub.8 are independently selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl; or R.sub.7 and R.sub.8, together with the carbon atom to which they are bound may form a saturated or unsaturated ring of 3-8 carbon atoms and (b) a novel reactive, protected 1,2-unsaturated pyranoid sugar, preferably, 1,2,3,6-tetradeoxy-3-trifluoroacetamido-4-trifluoroacetoxy-L-lyxo-hex-1-en opyranose which forms protected derivatives of said glycoside antibiotics and then removing the protecting groups from said glycoside antibiotics. These antibiotics are useful in the treatment of various human cancers and leukemia such as sarcomas, breast cancer, bronchogenic carcinoma, malignant lymphomas, neuroblastomas, acute leukemia and bladder cancer.
REFERENCES:
patent: 3803124 (1974-04-01), Arcamone et al.
Noller "Chem. of Organic Compounds" 3rd Ed. 1965, W. B. Saunders Co., Phila., Pa. pp. 123-126, 166 and 168.
Arcamone Federico
Cassinelli Giuseppe
Brown Johnnie R.
Societa Farmaceutici Italia S.p.A.
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