L-2',3'-dideoxy nucleoside analogs as anti-Hepatitis B (HBV) agents

• US 5,631,239 A
• Filed: 10/18/1995
• Issued: 05/20/1997
• Est. Priority Date: 05/25/1993
• Status: Expired due to Fees

• Current Assignee: Yale University
• Original Assignee: Yale University
• Inventors: Cheng, Yung-Chi, Lin, Tai-Shun
• Primary Examiner(s): Wilson, James O.
• Application Number:
  US08/544,650
• Time in Patent Office: 580 Days
• Field of Search: 536/28.2, 536/28.52, 514/50, 514/893, 514/894
• US Class Current: 514/49
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/16 Purine radicals

Abstract

The present invention relates to the surprising discovery that certain dideoxynucleoside analogs which contain a dideoxy ribofuranosyl moiety having an L-configuration (as opposed to the naturally occurring D- configuration) exhibit unexpected activity against Hepatitis B virus (HBV). In particular, the compounds according to the present invention show potent inhibition of the replication of the virus in combination with very low toxicity to the host cells (i.e., animal or human tissue). Compounds according to the present invention exhibit primary utility as agents for inhibiting the growth or replication of HBV, HIV and other retroviruses, most preferably HBV.

Claims

1. The compound 1-(2,3-Dideoxy-beta-L-ribofuranosyl)-5-fluorocytosine.

2. A pharmaceutical composition comprising a therapeutically effective amount of the compound 1-(2,3-Dideoxy-beta-L-ribofuranosyl)-5-fluorocytosine in combination with a pharmaceutically acceptable additive, carrier or excipient.

3. A method of treating an HBV infection in a patient comprising administering to said patient a therapeutically effective amount of the compound 1-(2,3-Dideoxy-beta-L-ribofuranosyl)-5-fluorocytosine.