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Details for Patent: 5,856,481

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Details for Patent: 5,856,481

Title: 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative
Abstract:The L-monovaline ester derived from 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol and its pharmaceutically acceptable salts are of value as antiviral agents with improved absorption.
Inventor(s): Nestor; John Joseph (Cupertino, CA), Maag; Hans (Menlo Park, CA)
Assignee: Syntex (U.S.A.) Inc. (Palo Alto, CA)
Filing Date:Mar 04, 1997
Application Number:08/812,989
Claims:1. A process for preparing the compound 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propanyl-L-val inate or a pharmaceutically acceptable salt thereof, comprising:

(a) removal of the amino- and hydroxy-protecting groups from a compound of the formula ##STR15## where: P.sup.1 is hydrogen or a hydroxy-protecting group,

P.sup.2 is an amino-protecting group,

P.sup.3 is hydrogen or P.sup.2, and

the asterisk denotes an asymmetric carbon atom; to afford the compound 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)-methoxy-3-hydroxy-1-propanyl-L-va linate; optionally followed by

(b) conversion of the 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)-methoxy-3-hydroxy-1-propanyl-L-va linate into a pharmaceutically acceptable salt thereof.

2. The process of claim 1 where P.sup.1 is hydrogen.

3. The process of claim 2 where P.sup.2 is C.sub.1-4 alkanoyl, trityl, trifluoroacetyl, N-(9-fluorenylmethoxycarbonyl), allyloxycarbonyl, N-benzyloxycarbonyl, t-butyloxycarbonyl, or phthalyl.

4. The process of claim 2, where step (a) is carried out under acidic conditions or by hydrogenolysis.

5. The process of claim 2 where a pharmaceutically acceptable salt of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propanyl-L-val inate is prepared.

6. The process of claim 5 where the pharmaceutically acceptable salt is the hydrochloride.

7. A process for preparing the compound 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propanyl-L-val inate or a pharmaceutically acceptable salt thereof, comprising:

(a) removal of the amino- and hydroxy-protecting groups from a compound of the formula ##STR16## where: P.sup.1 is a hydroxy-protecting group,

P.sup.2 is an amino-protecting group,

P.sup.3 is hydrogen or P.sup.2, and

the asterisk denotes an asymmetric carbon atom; to afford the compound 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)-methoxy-3-hydroxy-1-propanyl-L-va linate; optionally followed by

(b) conversion of the 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)-methoxy-3-hydroxy-1-propanyl-L-va linate into a pharmaceutically acceptable salt thereof.

8. The process of claim 7 where P.sup.2 is C.sub.1-4 alkanoyl, trityl, trifluoroacetyl, N-(9-fluorenylmethoxycarbonyl), allyloxycarbonyl, N-benzyloxycarbonyl, t-butyloxycarbonyl, or phthalyl.

9. The process of claim 7 where step (a) is carried out under acidic conditions or by hydrogenolysis.

10. The process of claim 7 where a pharmaceutically acceptable salt of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propanyl-L-val inate is prepared.

11. The process of claim 10 where the pharmaceutically acceptable salt is the hydrochloride.

12. A process for preparing the compound 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propanyl-L-val inate or a pharmaceutically acceptable salt thereof, comprising:

(a) removal of the amino- and hydroxy-protecting groups from a compound of the formula ##STR17## where: P.sup.1 is a hydroxy-protecting group removable under acidic conditions or by hydrogenolysis,

P.sup.2 is an amino-protecting group,

P.sup.3 is hydrogen or P.sup.2, and

the asterisk denotes an asymmetric carbon atom; to afford the compound 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)-methoxy-3-hydroxy-1-propanyl-L-va linate; optionally followed by

(b) conversion of the 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)-methoxy-3-hydroxy-1-propanyl-L-va linate into a pharmaceutically acceptable salt thereof.

13. The process of claim 12 where P.sup.1 is benzyl, trityl, allyl, tetrahydropyranyl, silyl, or trialkylsilyl.

14. The process of claim 12 where P.sup.2 is C.sub.1-4 alkanoyl, trityl, trifluoroacetyl, N-(9-fluorenylmethoxycarbonyl), allyloxycarbonyl, N-benzyloxycarbonyl, t-butyloxycarbonyl, or phthalyl.

15. The process of claim 14 where P.sup.1 is benzyl, trityl, allyl, tetrahydropyranyl, silyl, or trialkylsilyl.

16. The process of claim 12 where a pharmaceutically acceptable salt of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propanyl-L-val inate is prepared.

17. The process of claim 16 where the pharmaceutically acceptable salt is the hydrochloride.

18. The process of claim 12 were P.sup.1 is benzyl, P.sup.2 is N-benzyloxycarbonyl, and P.sup.3 is hydrogen.

19. The process of claim 18 where a pharmaceutically acceptable salt of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-3-hydroxy-1-propanyl-L-val inate is prepared.

20. The process of claim 19 where the pharmaceutically acceptable salt is the hydrochloride.
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