Compositions and processes for preparing...

Details Compositions and processes for preparing... Compositions and processes for preparing...

2007-07-17

2007-07-17

Peselev, Elli (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C552S201000, C552S202000

Reexamination Certificate

active

10982873

ABSTRACT:
13-benzenesulfonylhydrazone anthracyclines useful in producing improved yields in the synthesis 13-deoxyanthrcyclines, and an improved method of reducing 13-benzene-sulfonylhydrazone anthracyclines to 13-deoxyanthrcyclines wherein the reduction reaction is maintained at temperatures of about 55° C. to 64° C. without stirring or agitation. The reaction is completed with the addition of aqueous bicarbonate which forms the 13-deoxyanthracycline and precipitates. The precipitates are filtered and the precipitate and filtrate are extracted separately with organic solvents. The crude 13-deoxy anthracycline can be converted to 5-imino-13-deoxy anthracycline by reaction with methanolic ammonia. The reaction can also be performed with an acidic pyridinium salt instead of a strong acid so that neutralization of the reaction or extraction of the product is not necessary, thereby facilitating purification.

REFERENCES:
patent: 5942605 (1999-08-01), Zhang et al.
patent: 5948896 (1999-09-01), Zhang
Adriamycin Analogues. 2 Synthesis of 13-Deoxyanthracyclines by Thomas Smith et al.,Journal of Medicinal Chemistry, 1978, vol. 21, No. 3.

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