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Details for Patent: 4,360,522

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Details for Patent: 4,360,522

Title: Purine derivatives
Abstract:9-Hydroxyethoxymethyl (and related) derivatives of certain 6-, and 2,6-substituted purines have been discovered to have potent anti-viral activities. Novel compounds and their pharmaceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-hydroxyethoxymethyl) guanine and 2-amino-9-(2-hydroxyethoxymethyl)adenine are examples of especially active compounds of this invention.
Inventor(s): Schaeffer; Howard J. (Raleigh, NC)
Assignee: Burroughs Wellcome Co. (Research Triangle Park, NC)
Filing Date:Feb 01, 1978
Application Number:05/874,067
Claims:1. A substituted purine of formula ##STR12## wherein X is sulphur or oxygen; R.sup.1 is halogen, hydrogen, thio,alkylthio, alkoxy or azide; R.sup.2 is hydrogen, halogen, amino or azide; R.sup.3 is nitrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl; R.sup.4 is hydrogen, hydroxy, or lower alkyl; R.sup.5 is hydrogen, hydroxy, amino, alkyl, hydroxyalkyl, benzoyloxy, benzoyloxymethyl, benzyloxy, sulphamoyloxy, phosphate, carboxypropionyloxy, or acetoxy; and R.sup.6 is hydrogen alkyl, hydroxyalkyl or a pharmaceutically acceptable salt thereof.

2. A substituted purine of formula (I) according to claim 1 wherein X is an oxygen atom.

3. A method of treating a susceptible viral infection in a mammal which comprises administering an effective non-toxic amount of the compound or a pharmaceutically acceptable salt of claim 1.

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

5. The method of claim 4 in which R.sup.1 is chlorine, R.sup.2 is amino, R.sup.5 is benzoyloxy and R.sup.3, R.sup.4 and R.sup.6 are hydrogen.

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

7. The method of claim 5 in which the viral infection is a herpes virus infection.

8. A pharmaceutical composition comprising an effective anti-viral amount of the compound or salt of claim 1 and a pharmaceutically acceptable carrier therefore.

9. The composition of claim 8 in which X is oxygen.

10. The composition of claim 8 in which the amount is an effective anti-herpes amount.

11. The composition of claim 8 in a form for oral or topical administration.

12. A compound of formula (I) ##STR13## wherein R.sup.1 is chlorine, R.sup.2 is amino, R.sup.5 is benzoyloxy and R.sup.3, R.sup.4 and R.sup.6 are each hydrogen or a pharmaceutically acceptable salt thereof, wherein X is oxygen.

13. A method of treating a susceptible viral infection in a mammal which comprises administering an effective non-toxic amount of the compound or salt of claim 12.

14. A pharmaceutical composition comprising an effective anti-viral amount of the compound or salt of claim 12 and a pharmaceutically acceptable carrier therefor.

15. The compound of the formula I ##STR14## wherein X is sulphur or oxygen; R.sup.1 is hydrogen, halogen, hydroxy, alkoxy, azide, thio, or alkylthio; R.sup.2 is hydrogen, halogen, alkylthio, amino or azide, provided R.sup.2 is not amino when R.sup.1 is hydroxy; 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 hydrogen hydroxy, amino, alkyl, hydroxyalkyl, benzyloxy, benzoyloxy, benzoyloxymethyl, sulphamoyloxy, phosphate, or straight or branched chain or cyclic acyloxy having from 1 to 8 carbon atoms; R.sup.6 is hydrogen or alkyl; or a pharmaceutically acceptable salt thereof.

16. The compound or salt of claim 15 wherein R.sup.5 is straight or branched chain or cyclic acyloxy having from 1 to 8 carbon atoms.
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