Process for the preparation of D-ribavirin

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S055300, C536S124000

Reexamination Certificate

active

10485335

ABSTRACT:
A process for the preparation of ribavirin on an industrial scale is described which comprises the reaction of glycosylation of 3-substituted triazoles in the presence of a Lewis acid. Said process comprises:a) the reaction of a triazole of the formula with a protected ribofuranose of the formulab) the removal of the Pg groups and, optionally, the conversion into a carboxyamide group of the R2group of the compound obtained of the formula DD/mac—01.07.02.

REFERENCES:
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patent: 6130326 (2000-10-01), Ramasamy et al.
patent: 55 160793 (1980-12-01), None
patent: 55160793 (1980-12-01), None
Revue Roumaine de Chimie, 1987, 32, 329-333.
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B. Shimizu and A. Saito, “The Synthesis of Ara-C Via β-D-Xylofuranosyl-cytosine Derivatives and of ‘Virazole’ by the Trimethylsilyl Ether ‘Solution’ Method”, Nucl. Acid. Chem. (1978), 1, pp. 255-260.
H. Vorbrüggen, et al., “Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts”, Chemische Berichte, Verlag Chemie GmbH, vol. 114, pp. 1234-1255, (1981).
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J. A. Marins, et al., “synthesis of Nucleosides Using Trimethylsilyl Perfluoroethoxyethanesulphonate as Catalyst”, Nucleosides Nucleotides (1991), 10, pp. 619-620.
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K.S. Ramasamy, et al., “Monocyclic L-Nucleosides with Type 1 Cytokine-Inducing Activity”,J. Med. Chem., (2000), 43, pp. 1019-1028.

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