Process for the preparation of 2'-deoxy-2'-halocoformycins or st

Details Process for the preparation of 2'-deoxy-2'-halocoformycins or st Process for the preparation of 2'-deoxy-2'-halocoformycins or st

1997-03-04

1998-11-03

Kight, John

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

Organic compounds

Carbohydrates or derivatives

536 2712, 536 276, 536 278, 536 288, 514 45, 514 46, C07H 1923

Patent

active

058310720

ABSTRACT:
An object of this invention is to provide a novel process for the synthesis of a 2'-deoxy-2'-halocoformycin having an inhibitory activity against adenosine deaminase in a practically high yield. Thus, there is provided a process comprising multi-stage reactions with using as the starting intermediate a tert-butyl 1-(3,5-di-O-acyl-2-deoxy-2-halo-.beta.-D-ribofuranosyl or arabinofuranosyl)-5-aminoimidazole-4-carboxylate of formula (II) ##STR1## whereby there are produced a 2'-deoxy-2'-halocoformycin or a 2'-deoxy-2'-epi-2'-halocoformycin of formula (I-a) ##STR2## and also a 2'-deoxy-8-epi-2'-halocoformycin or a 2'-deoxy-8,2'-diepi-2'-halocoformycin of formula (I-b) ##STR3## It is expectable that a 2'-deoxy-2'-halocoformycin and epimers thereof are useful as a drug for lymphocytic leukemias and as drugs for various diseases attributable to the actions of adenosine deaminase.

REFERENCES:
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patent: 4713372 (1987-12-01), Schaumber et al.
Isshiki et al., "Synthesis of Azepinomycin and .beta.-D-ribofuranoside," J. Antibiotics, 40(10), 1461-1463 (1987); Chem. Abstr., 109(5), p. 652, Abstr. No. 38163n (Aug. 1, 1988); only abstract provided.
Omura et al., "Adechlorin, A New Adenosine Deaminase Inhibitor Containing Chlorine. Production, Isolation and Properties," J. Antibiotics, 38(8), 1008-1015 (1985); Chem. Abstr., 103(19), p. 380, Abstr. No. 156967b (Nov. 11, 1985); only abstract provided.
Schaumberg et al., "2'-Chloropentostatin, A New Inhibitor of Adenosine Aminase," J. Organic Chem., 50(10), 1651-1656 (May 17, 1985).
Suhadolnik et al., "Stereospecific 2'-Amination and 2'Chlorination of Adenosine by Actinomadura in the Biosynthesis of 2'-Amino-2'-dexyadenosine and 2'-Chloro-2'-deoxycoformycin," Arch. Biochem. Biophys., 270(1), 347-382 (Apr. 1989). and Potent Adenosine Deaminase Inhibitor," J. Labelled Compounds Radiopharmaceuticals, 28(4), 445-454 (Apr. 1990).

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