4'-Epi-6'-hydroxyadriamycin and method of use

Details 4'-Epi-6'-hydroxyadriamycin and method of use 4'-Epi-6'-hydroxyadriamycin and method of use

1975-10-10

1977-05-24

Brown, Johnnie R.

Drug, bio-affecting and body treating compositions

Conjugate or complex of monoclonal or polyclonal antibody,...

Conjugated via claimed linking group, bond, chelating agent,...

536 4, 536 17, 536 18, A61K 3171

Patent

active

040256235

ABSTRACT:
The novel glycoside antibiotic: 4'-epi-6'-hydroxydaunomycin is prepared by condensing daunomycin with a novel protected, reactive derivative, which is 1,2,3-trideoxy-4,6-di-O-(p-nitrobenzoyl)-3-trifluoroacetamido-L-arabino -hex-1-enepyranose and thereafter removing the protecting groups. A further novel glycoside antibiotic: 4'-epi-6'-hydroxyadriamycin is prepared by reacting 4'-epi-6'-hydroxydaunomycin with bromine to form an intermediate bromo derivative which is then mildly hydrolyzed to form 4'-epi-6'-hydroxyadriamycin. These novel glycoside antibiotics, while not as effective as the parent compounds daunomycin and adriamycin in the treatment of tumors, are considerably less toxic than the parent compounds.

REFERENCES:
patent: 3784541 (1974-01-01), Culbertson et al.
patent: 3803124 (1974-04-01), Arcamone et al.
Pigman "The Carbohydrates," Academic Press Inc., New York, N.Y., pp. 208-213.

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