The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Nov. 24, 1998

Filed:

Jan. 22, 1997
Applicant:
Inventors:

Leroy B Townsend, Ann Arbor, MI (US);

John C Drach, Ann Arbor, MI (US);

George A Freeman, Raleigh, NC (US);

Assignees:

The Regents of the University of Michigan, Ann Arbor, MI (US);

Glaxo Wellcome Inc., Research Triangle Park, NC (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
A61K / ; C07D / ;
U.S. Cl.
CPC ...
514395 ; 514394 ; 5483047 ;
Abstract

This invention pertains to nucleoside analogs which have antiviral activity and improved metabolic stability. More specifically, this invention pertains to modified sugar benzimidazole nucleosides, as exemplified by compounds such as benzimidazole nucleosides possessing a fluorinated sugar-like moiety (for example, a 2'-fluoro-furanosyl moiety or a 3'-fluoro-furanosyl moiety), and may be represented by the following formula, ##STR1## wherein R.sup.1 is a fluorinated sugar-like moiety; and R.sup.2, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are benzimidazole substituents, such as --H, halogens (e.g., --F, --Cl, --Br, --I), --NO.sub.2, --NR.sub.2 (where R is independently --H or an alkyl group having 1-6 carbon atoms), --OR (where R is --H or an alkyl group having 1-6 carbon atoms), --SR (where R is --H or a hydrocarbyl of 1-10 carbon atoms), and --CF.sub.3. In one embodiment, R.sup.1 is 2'-fluoro-furanosyl or 3'-fluoro-furanosyl; R.sup.2 is --H, --F, --Cl, --Br, --I, or --NR.sub.2, wherein R is independently --H or an alkyl group having 1-6 carbon atoms; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently --H, --F, --Cl, --Br, or --I.


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