C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
167/202, 260/229
C07H 19/04 (2006.01) A61K 31/70 (2006.01) C07H 13/06 (2006.01) C07H 19/06 (2006.01) C07H 19/16 (2006.01)
Patent
CA 2013874
Abstract of the Disclosure Certain 3'-substituted methyl nucleosides are disclosed which are useful in the treatment of viral infections, e.g., infections caused by herpes simplex virus types 1 and 2, and/or are useful as intermediates in the preparation of 3'-substituted methyl nucleosides having antiviral activity. In accordance with one aspect of the invention, there are provided novel 3'-substituted methyl nucleosides represented by Formulas I and II Image Image I II wherein: B indicates that B can be either alpha or beta; B is a member selected from the group consisting of the pyrimidine and purine nucleoside bases connected to the tetrahydrofuran ring through the N1 heterocyclic nitrogen atom of the pyrimidines and the N9 or N7 heterocyclic nitrogen atom of the purines including the naturally occurring nucleoside bases and 5-fluoro, 5-bromo, 5-iodo, 5-chloro, 5-trifluoromethyl, 5-ethyl, 5-(2-bromovinyl)- uracil; triazolecarboxamide; 2-aminopurine; 2,6-diaminopurine; 4-chloropyrimidine; pyrimidine; azapyrimidine; purine; 2,6-dichloropurine; 2-amino-6- chloropurine; and deazapurine; R and Q are either both hydrogen or halogen, especially fluorine, or one is hydrogen and the other one is hydroxy or halogen, especially fluorine; in Formula I at least one of R and Q is halogen; and X and Y can be the same or different and are selected from the group consisting of O-alkyl, O-aryl, O-acyl-, halogen, especially fluorine, azido, amino, acylamido, -SH, S-alkyl and S-aryl, or one of X or Y can be hydroxy, or X may be the group R10 and Y may be the group R20 wherein R1 and R2 are hydrogen or hydroxy-protecting groups. Preferred O-alkyl and S-alkyl groups contain from one to four carbon atoms; preferred O-aryl and S-aryl groups contain from 6 to 10 carbon atoms; and preferred O-acyl groups contain from one to four carbon atoms.
Mansuri Muzammil M.
Martin John C.
Sterzycki Roman
Barrigar & Moss
Bristol-Myers Squibb Company
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