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Details for Patent: 4,323,573

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Details for Patent: 4,323,573

Title: Adenine derivatives
Abstract:Novel 2-amino substituted adenine compounds and their use as antiviral compounds are disclosed. In particular the compound 2-amino-9-(2-hydroxyethoxymethyl) adenine is particularly advantageous as an antiviral in that it has high oral absorption and that upon metabolism in mammals, it has the property of being converted to 9-(2-hydroxyethoxymethyl) guanine which is also a highly active antiviral.
Inventor(s): Schaeffer; Howard J. (Raleigh, NC)
Assignee: Burroughs Wellcome Co. (Research Triangle Park, NC)
Filing Date:Feb 01, 1978
Application Number:05/874,130
Claims:1. A compound of the formula (I) ##STR12## wherein R.sup.1 is amino, R.sup.2 is amino

X is oxygen or sulphur

R.sup.3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl;

R.sup.4 is hydrogen, hydroxy or alkyl;

R.sup.5 is hydroxy, amino, alkyl, hydroxyalkyl, benzyloxy, benzoyloxymethyl, sulphamoyloxy, phosphate, or acyloxy having 1 to 8 carbon atoms, R.sup.6 is hydrogen or alkyl; or a pharmaceutically acceptable salt thereof.

2. A pharmaceutical composition for use as an antiviral which comprises an effective antiviral amount of the compound or salt of claim 1.

3. A method of treating a susceptible virus infection in a mammal which comprises the administration to the infected mammal of an effective, non-toxic antiviral amount of the compound or salt of claim 1.

4. The compound or salt of claim 1 in which X is oxygen.

5. The composition of claim 2 in which X is oxygen.

6. The method of claim 3 in which X is oxygen.

7. The compound or salt of claim 1 in which R.sup.5 is acetoxy.

8. The method of claim 3 in which the virus infection is a herpes virus infection.

9. The compound or salt of claim 1 in which the salt is an acid addition salt.

10. The compound or salt of claim 1 in which R.sup.5 is hydroxy or phosphate.

11. The composition of claim 2 in which R.sup.5 is hydroxy or phosphate.

12. The method of claim 3 in which R.sup.5 is hydroxy or phosphate.

13. 2-amino-9-(2-hydroxyethoxymethyl)adenine.

14. A pharmaceutically acceptable salt of 2-amino-9-(2-hydroxyethoxymethyl)adenine.

15. The salt of claim 14 in which the salt is an acid addition salt.

16. The method of treating a susceptible viral infection in a mammal having said viral infection which comprises the administration to said mammal of an effective antiviral non-toxic amount of 2-amino-9-(2-hydroxyethoxymethyl)adenine or a pharmaceutically acceptable salt thereof.

17. The method of claim 16 in which the administration is oral, parenteral or topical.

18. The method of claim 16 in which the viral infection is a herpes virus infection.

19. A pharmaceutical composition comprising an effective antiviral amount of 2-amino-9-(2-hydroxyethoxymethyl)adenine or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier therefore.

20. A pharmaceutical composition of claim 19 in a form for oral, parenteral or topical administration.

21. A pharmaceutical composition for treating a susceptible viral infection comprising an effective antiviral treatment amount of 2-amino-9(2-hydroxyethoxymethyl)adenine together with a pharmacuetically acceptable carrier therefore.

22. A method of treating a herpes virus infection in a human which comprises administering to said human an effective anti herpes treatment amount of the compound 2-amino-9-(2-hydroxyethoxymethyl)adenine.

23. The method of claim 22 in which the compound is administered in a pharmacuetically acceptable carrier.

24. The method of claim 18 in which the viral infection is a herpes simplex or herpes zoster infection.

25. The method of claim 22 in which the herpes virus infection is a herpes simplex or herpes zoster infection.
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