Process for the preparation of 5-(2-bromovinyl)-uridine

Details Process for the preparation of 5-(2-bromovinyl)-uridine Process for the preparation of 5-(2-bromovinyl)-uridine

1982-09-07

1985-10-01

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536122, C07H 1908

Patent

active

045447403

ABSTRACT:
The invention relates to (E)-5-(2-bromovinyl)-uridine and its derivatives of general formula VI, ##STR1## wherein R.sup.1 stands for a hydrogen atom, C.sub.1-8 alkanoyl group, benzoyl group or a benzoyl group substituted in para position either with a C.sub.1-4 alkyl group or a halogen atom, and a process for preparing them by brominating 2',3',5'-tri-O-acyl-5-ethyl-uridine of general formula IV, ##STR2## wherein R is identical with R.sup.1, except where R.sup.1 stands for a hydrogen atom, dehydrohalogenating the resulting dibromo compound of general formula V ##STR3## and optionally deacylating it. The resulting compounds of general formula VI are exhibiting significant potency against Herpes simplex virus species and are of remarkably low acute toxicity.

REFERENCES:
patent: 4247544 (1981-01-01), Bergstrom et al.
patent: 4382925 (1983-05-01), de Clercq et al.
patent: 4386076 (1983-05-01), Machida et al.
Kulikowski et al., "Jour. of Medicinal Chem.", vol. 17, No. 3, 1974, pp. 269-273.
de Clercq, "Meth. and Find. Exptl. Clin. Pharmacol.", vol. 2, No. 5, pp. 253-267, 1980.
Jones et al., Tetrahedron Letters, No. 45, pp. 4415-4418, 1979.

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