1,5-anhydrohexitol nucleoside analogues

US5607922A · kind A · utility

Assignee

• STICHTING REGA VZW · BE

Inventors

• Erik De Clercq · Lovenjoel, BE
• Piet Herdewijn · Wezemaal, BE
• Arthur Van Aerschot · Knokke, BE

Key dates

• Filing date: Dec 17, 1993
• Grant date: Mar 4, 1997
• Expiry date: Dec 17, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

1,5-Anhydrohexitol nucleoside analogues represented by the general formula I: ##STR1## wherein the hexitol has the D-configuration and the carbon atom on which the base moiety and the X substituent stand both have the (S)-configuration and further wherein: PA1 B is a heterocyclic ring selected from the group consisting of pyrimidine and purine bases; and PA1 X is hydrogen, azido, F, Cl, Br, I, amino, --NHR.sup.2, --N(R.sup.2).sub.2, --OR.sup.2, --SR.sup.2, or CN; wherein R.sup.1 and R.sup.2 are the same or different and are selected from the group consisting of hydrogen, substituted or unsubstituted C.sub.1 -C.sub.20 alkyl, substituted or unsubstituted C.sub.1 -C.sub.20 alkenyl, aroyl, C.sub.1 -C.sub.20 alkanoyl, and phosphoryl. These nucleoside analogues are useful as antiviral agents against herpes simplex virus, vaccina virus, or varicella zoster virus. The definition of the X group should include --N(R.sup.2).sub.2 instead of --N(N.sup.2).sub.2.