Purinyl and pyrimidinyl tetrahydrofurans

• US 5,272,152 A
• Filed: 06/24/1991
• Issued: 12/21/1993
• Est. Priority Date: 07/02/1990
• Status: Expired due to Term

• Current Assignee: E R Squibb & Sons Incorporated
• Original Assignee: E R Squibb & Sons Incorporated
• Inventors: Goodfellow, Val S., Zahler, Robert
• Primary Examiner(s): Berch, Mark L.
• Application Number:
  US07/719,861
• Time in Patent Office: 911 Days
• Field of Search: 544/255, 544/265, 544/276, 544/277, 514/81, 514/262, 514/266
• US Class Current: 514/45
• CPC Class Codes: C07D 473/00 Heterocyclic compounds containing purine ring systems

Abstract

Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts.

Claims

1. A compound of the formula ##STR50## wherein the sterochemistry is absolute and is derived from the chiral precursors D-sorbitol or 1,4-andro-d-ribitol and a pharmaceutically acceptable salt thereof wherein R₁ is ##STR51## R₄ and R₅ are independently selected from the group consisting of hydrogen, --PO₃ H₂, and ##STR52## and R₆ is hydrogen, alkyl, substituted alkyl or aryl wherein the term "alkyl" refers to straight or branched chain groups of 1 to 10 carbons, the term "substituted alkyl" refers to straight or branched chain alkyl of 1 to 10 carbons wherein said substituent is selected from the group consisting of halogen, amino, azido, hydroxy, cyano, trialkylammonium (wherein each alkyl group has 1 to 6 carbons), aryl, and carboxy, and the term "aryl" refers to phenyl and phenyl having one, two, or three substituents selected from the group consisting of alkyl of 1 to 6 carbons, alkoxy of 1 to 6 carbons, halogen, trifluoromethyl, amino, amido, alkylamino of 1 to 6 carbons, dialkylamino (wherein each alkyl group has 1 to 6 carbons), nitro, cyano, alkanoyloxy of 2 to 11 carbons, carboxy, carbamoyl, and hydroxy.

2. An antiviral pharmaceutical composition comprising as the active component a compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

3. A compound in accordance with claim 1 wherein R₁ is ##STR53##

4. The composition of claim 2 wherein the active component is [3R-(3α

,4β

,5α

)]-2-amino-1,9-dihydro-9-[tetrahydro-4-hydroxy-5-(hydroxymethyl)-3-furanyl]-6-H-purin-6-one.

5. The method of treating a herpes simplex virus type 1 or 2 or a varacella-zoster virus in a mammal which comprises administering an antiviral effective amount of the composition of claim 4.

6. A compound in accordance with claim 1 wherein R₄ and R₅ are independently hydrogen or ##STR54##

7. A compound in accordance with claim 1 wherein R₄ and R₅ are independently hydrogen or --PO₃ H₂.

8. A compound in accordance with claim 1 wherein R₄ and R₅ are hydrogen.

9. A compound in accordance with claim 1, [3R-(3α

,4β

,5α

)]-2-amino-1,9-dihydro-9-tetrahydro-4-hydroxy-5-(hydroxymethyl)-3-furanyl]-6H-purin-6-one.