The Ohio State University

The United States of America As Represented by the Department of Health

Waldemar A Priebe

Derek Horton

Gary W Morrow

John S Swenton

Richard L Wolgemuth

Compounds of the formula (I) and pharmaceutical preparations containing the same are disclosed ##STR1## wherein R.sup.1 is --OOCR.sup.3 or --OOC(CH.sub.2).sub.n COOR.sup.4 ; R.sup.2 is hydrogen, hydroxy or methoxy; one of X and X' is a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine and the other is hydrogen; one of Y and Y' is hydrogen and the other is selected from the group consisting of hydrogen, hydroxy and acyloxy; one of Z and Z' is hydrogen and the other is selected from the group consisting of hydrogen, hydroxy and acyloxy; R.sup.3 is an alkyl group containing 1 to 8 carbon atoms; R.sup.4 is a hydrogen atom, a metal atom, or an alkyl group containing 1 to 4 carbon atoms; and n is an integer of 0 to 6. These compounds are active in the inhibition of malignant diseases.

14-Acyloxy-2'-halo-anthracycline anti-cancer antibiotics

14-acyloxy-2'-halo-anthracycline anti-cancer antibiotics

Compounds represented by the formula (I) ##STR1## wherein R is hydrogen or hydroxyl, one of X and Y is fluorine and the other is hydrogen or both X and Y are fluorine, and Su is a hydrogen atom or a sugar moiety; where Su is a sugar moiety, the compounds are useful anticancer antibiotics; pharmaceutical preparations containing the antibiotics and a method for inhibiting the growth of mammalian tumors are also disclosed.

1-fluoro, 4-fluoro, and 1,4-difluoro anthracycline anticancer antibiotics

Anthracycline antibiotics represented by the formula (I) ##STR1## wherein R is hydrogen or hydroxyl, one of X and Y is fluorine and the other is hydrogen or both X and Y are fluorine, and S is a 2-halo sugar moiety; pharmaceutical preparations containing the same; and a method for inhibiting the growth of mammalian tumors are disclosed.

1-fluoro, 4-fluoro, and 1,4-difluoro-2'-halo anthracycline antibiotics

Compounds of the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a hydroxyl group; R.sup.2 is a hydrogen atom or a hydroxyl or methoxyl group; X is a fluorine, chlorine, bromine or iodine atom; one of Y and Y' is a hydrogen atom and the other is a hydrogen atom or a hydroxyl or acyloxy group; R.sup.3 and R.sup.4 are each independently a hydrogen atom, an alkyl group, a halo- or phenyl-substituted alkyl group, an acyl group or a halo- or phenyl-substituted acyl group or R.sup.3 and R.sup.4 together form a polymethylene chain having 4 to 6 carbon atoms, are useful as anti-tumor agents, especially for treating leukemia; in particular these compounds exhibit high antileukemic activity against P388 murine leukemia.

3'-Amino-2' halo-anthracycline antibiotics

Compounds of the formula (I), acid addition salts thereof, and pharmaceutical preparations containing the same are disclosed ##STR1## wherein R.sup.1 is hydroxy; one of X and X' is hydrogen and the other is a halogen atom selected from the group consisting of fluorine, chlorine, bromine, and iodine; one of Y and Y' is hydrogen and the other is selected from the group consisting of hydrogen, hydroxy and --OCOR; one of Z and Z' is hydrogen and the other is hydrogen, hydroxy or --OCOR; and R is a lower alkyl group.

4-Demethoxy-3'-desamino-2'-halo-anthracycline and pharmaceutical

The compounds are derived from aglycons which may be daunomycin, desmethoxy daunomycin, adriamycin and carminomycin. A preferred compound is ##STR1## (1) R'=H; R.sup.2 =OMe; X; Y (2) R'=OH; R.sup.2 =OMe; X; Y

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Columbus, OH, United States of America

Waldemar A Priebe