Difluro antivirals and intermediate therefor

• US 5,118,820 A
• Filed: 02/07/1991
• Issued: 06/02/1992
• Est. Priority Date: 03/10/1983
• Status: Expired due to Term

• Current Assignee: Eli Lilly and Company
• Original Assignee: Eli Lilly and Company
• Inventors: Hertel, Larry W.
• Primary Examiner(s): GRIFFIN, RONALD
• Application Number:
  US07/652,349
• Time in Patent Office: 481 Days
• Field of Search: 549/313, 536/1.1, 536/18.4
• US Class Current: 549/313
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: C07D 307/33 in position 2, the oxygen atom being in its keto or unsubstituted enol form
• CPC Class Codes: C07D 317/30 Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07H 11/00 Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof halo-sugars C07H5/02; thio-, seleno-, or telluro-sugars C07H5/08
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 5/02 to halogen
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

A 2,2-difluoro-2-desoxycarbohydrate is used to prepare antiviral nucleosides.

Claims

1. A difluoro-desoxy carbohydrate of the formula ##STR11## wherein X is hydroxy or a leaving group;

and the Y groups independently are hydrogen or hydroxy-protecting groups.

2. A carbohydrate of claim 1 which is in the ribose form.

3. A carbohydrate of claim 2 wherein X is hydroxy.

4. A carbohydrate of claim 1 wherein X is hydroxy.

5. A carbohydrate of claim 3 wherein Y is hydrogen.

6. A carbohydrate of claim 4 wherein Y is hydrogen.

7. A carbohydrate of claim 1 wherein X is a sulfonate leaving group.

8. A carbohydrate of claim 2 wherein X is a sulfonate leaving group.

9. A carbohydrate of claim 7 wherein Y is a silyl hydroxy-protecting group.

10. A carbohydrate of claim 8 wherein Y is a silyl hydroxy-protecting group.