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Details for Patent: 5,061,708

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Details for Patent: 5,061,708

Title: Therapeutic guanine esters
Abstract:The present invention relates to certain amino acid esters of the purine nucleoside acyclovir, pharmaceutically acceptable salts thereof and their use in the treatment and prophylaxis of herpes virus infections. The invention also includes pharmaceutical formulations and processes for the preparation of such compounds.
Inventor(s): Krenitsky; Thomas A. (Chapel Hill, NC)
Assignee: Burroughs Wellcome Co. (Research Triangle Park, NC)
Filing Date:Nov 21, 1989
Application Number:07/442,415
Claims:1. The L form of a compound of formula (I) ##STR6## wherein R.sub.1 represents a group of formula --CH[CH.sub.3 ]CH.sub.2 CH.sub.3 or a pharmaceutically acceptable salt thereof.

2. 2-(2-Amino-1,6-dihydro-6-oxo-9H(purin-9-yl)methoxy)ethyl L-isoleucinate.

3. A compound according to claim 1 which is 2-(2-amino-1,6-dihydro-6-oxo-9H(purin-9-yl)methoxy)ethyl L-isoleucinate.

4. A compound according to claim 1 which is 2-(2-amino-1,6-dihydro-6-oxo-9H(purin-9-yl)methoxy)ethyl L-isoleucinate hydrochloride.

5. A compound according to claim 1 which is in the form of a pharmaceutically acceptable salt.

6. A compound according to claim 5 wherein said salt is the hydrochloride salt.

7. A pharmaceutical composition comprising as active ingredient a compound of formula (I) as defined in claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.

8. A method of treating a susceptible viral infection in a mammal which comprises the administration to said mammal of an effective antiviral amount of a compound of formula (I) as defined in claim 1 or a pharmaceutically acceptable salt thereof.

9. The method of claim 8 wherein said viral infection is caused by a herpes virus.

10. A method of treating a herpes virus infection in a human having said infection which comprises orally or parenterally administering an effective herpes simplex virus infection treatment amount of 2-(2-amino-1,6-dihydro-6-oxo-9H(purin-9-yl)methoxy) ethyl-L-isoleucinate or a pharmaceutically acceptable salt thereof to said human.

11. The method of claim 10 in which the virus infection is a herpes simplex infection.

12. The method of claim 10 in which the virus infection is a herpes zoster infection.

13. The method of claim 10 in which the virus infection is a cytomegalovirus infection.

14. A tablet or capsule containing the compound 2-(2-amino-1,6-dihydro-6-oxo-9H(purin-9-yl)methoxy) ethyl-L-isoleucinate or a pharmaceutically acceptable salt thereof.

15. A method of generating acyclovir in the plasma of a mammal, which comprises orally administering the compound 2-(2-amino-1,6-dihydro-6-oxo-9H(purin-9-yl)methoxy) ethyl-L-isoleucinate or a pharmaceutically acceptable salt thereof.

16. The method of claim 15, in which the salt is an acid addition salt, which is orally administered.

17. The method of claim 16, in which the salt is the hydrochloride salt.

18. The method of claim 15, in which the compound is orally administered.
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