C-5 Substituted cytosine nucleosides

• US 4,267,171 A
• Filed: 07/02/1979
• Issued: 05/12/1981
• Est. Priority Date: 07/02/1979
• Status: Expired due to Term

• Current Assignee: Regents of the University of California (University of California)
• Original Assignee: Regents of the University of California (University of California)
• Inventors: Bergstrom, Donald E., Ruth, Jerry L.
• Primary Examiner(s): Brown, Johnnie R.
• Assistant Examiner(s): Hazel, Blondel
• Application Number:
  US06/053,943
• Time in Patent Office: 680 Days
• Field of Search: 536/23, 424/180
• US Class Current: 514/49
• CPC Class Codes: C07H 19/06 Pyrimidine radicals

Abstract

C-5 Substituted cytosine nucleosides wherein the C-5 substituent is substituted alkyl, alkenyl or substituted alkenyl; and the pharmaceutically acceptable acid addition salts thereof, are useful as antiviral agents. A novel process for the preparation of the subject compounds is also disclosed.

Claims

1. A compound of the formula ##STR9## wherein R_o is β

-D-ribofuranosyl, β

-D-2-deoxyribofuranosyl or β

-D-arabinofuranosyl and R is selected from the group consisting of ##STR10## wherein R₁ is hydrogen;

R₃ is hydrogen or methyl;

R₄ is C_1-4 lower alkyl;

R₆ is hydrogen; and

the pharmaceutically acceptable acid addition salts thereof.

2. A compound according to claim 1 wherein R_o is β

-D-2-deoxyribofuranosyl.

3. A compound according to claim 2 wherein R₃ is hydrogen.

4. The compound of claim 2 which is 5-(ethenyl)-2'"'"'-deoxycytidine.

5. A compound according to claim 2, wherein R is allyl.

6. A compound according to claim 2, wherein R is 1-methoxyethyl.

7. A method of treating herpes simplex virus 1 in a host mammal afflicted with such infection which comprises administering to said host an effective amount of a compound according to claims 2, 3, 4, 5 or 5.