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Generated: September 19, 2017

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Title: 2-Substituted-4-substituted-1,3-dioxolanes and use thereof
Abstract:Nucleoside analogues containing a 1,3-dioxolane structure are suitable antiviral agents, particulary for the treatment of the HIV infections in mammals, especially humans. Examples of the nucleoside analogues include: cis-2-acetoxymethyl-4-(thymin-1'-yl)-1,3,-dioxolane, cis-2-hydroxymethyl-4-(thymin-1'-yl)-1,3-dioxolane, cis-2-benzoyloxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane, and cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane. These compounds can be in the form of their racemates or their separate enantiomers.
Inventor(s): Belleau; Bernard (late of Westmount, CA), Dixit; Dilip M. (Roxboro, CA), Nguyen-Ba; Paul (La Prairie, CA)
Assignee: Biochem Pharma Inc. (Quebec, CA)
Filing Date:Sep 30, 1998
Application Number:09/163,374
Claims:1. A compound selected from the group consisting of:

cis-2-acetoxymethyl-4-(thymin-1'-yl)-1,3,-dioxolane;

cis-2-hydroxymethyl-4-(thymin-1'-yl)-1,3-dioxolane;

cis-2-benzoyloxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane; and

cis-2-hydroxymethyl-4-(cytosin-1'yl)-1,3-dioxolane.

2. A compound according to claim 1, wherein said compound is in the form of a single optical isomer or a mixture of optical isomers.

3. A compound according to claim 1, wherein said compound is

cis-2-acetoxymethyl-4-(thymin-1'-yl)-1,3-dioxolane.

4. A compound according to claim 1, wherein said compound is:

cis-2-hydroxymethyl-4-(thymin-1'-yl)-1,3-dioxolane.

5. A compound according to claim 1, wherein said compound is

cis-2-benzoyloxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane.

6. A compound according to claim 1, wherein said compound is

cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane.

7. A compound according to claim 2, wherein said compound is

cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane.

8. A compound according to claim 7, wherein said compound is in the form of the racemic mixture.

9. A compound according to claim 7, wherein said compound is in the form of a single optical isomer.

10. A compound according to claim 6, wherein said compound is:

(d)-cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane.

11. A compound according to claim 6, wherein said compound is

(l)-cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3dioxolane.

12. A compound according to claim 2, wherein said compound is

cis-2-hydroxymethyl-4-(thymin-1'-yl)-1,3-dioxolane.

13. A compound according to claim 12, wherein said compound is in the form of the racemic mixture.

14. A compound according to claim 12, wherein said compound is in the form of a single optical isomer.

15. A compound according to claim 14, wherein said compound is

(d)-cis-2-hydroxymethyl-4-(thymin-1'-yl)-1,3-dioxolane.

16. A compound according to claim 14, wherein said compound is

(l)-cis-2-hydroxymethyl-4-(thymin-1-yl)-1,3-dioxolane.

17. A method for the treatment of an HIV infection, in a mammal, comprising administering an effective amount of a compound according to claim 9 to a mammal in need of such treatment.

18. A method for the treatment of an HIV infection, in a mammal, comprising administering an effective amount of a compound according to claim 10 to a mammal in need of such treatment.

19. A method for the treatment of an HIV infection, in a mammal, comprising C administering an effective amount of a compound according to claim 10 to a mammal in need of such treatment.

20. A method for the treatment of an HIV infection, in a mammal, comprising administering an effective amount of a compound according to claim 11 to a mammal in need of such treatment.

21. A method according to claim 17, wherein said mammal is a human.

22. A method according to claim 10, wherein said mammal is a human.

23. A method according to claim 19, wherein said mammal is a human.

24. A method according to claim 20, wherein said mammal is a human.

25. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 1.

26. A composition according to claim 25, wherein the amount of said compound is 10-1500 mg.

27. A pharmaceutical composition according to claim 26, wherein said compound is

cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane.

28. A pharmaceutical composition according to claim 27, wherein said compound is:

(d)-cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-dioxolane.

29. A pharmaceutical composition according to claim 27, wherein said compound is

(l)-cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3 dioxolane.

30. A pharmaceutical composition of claim 26, wherein the amount of said compound is 20-1000 mg.

31. A pharmaceutical composition of claim 27, wherein the amount of said compound is 20-1000 mg.

32. A pharmaceutical composition of claim 28, wherein the amount of said compound is 20-1000 mg.

33. A pharmaceutical composition of claim 28, wherein the amount of said compound is 20-1000 mg.

34. A pharmaceutical composition of claim 30, wherein the amount of the compound is 50-700 mg.

35. A pharmaceutical composition of claim 31, wherein the amount of the compound is 50-700 mg.

36. A pharmaceutical composition of claim 32, wherein the amount of the compound is 50-700 mg.

37. A pharmaceutical composition of claim 33, wherein the amount of the compound is 50-700 mg.

38. A compound selected from the group consisting of:

cis-2-benzoyloxymethyl-4-(cytosin-1'-yl),-1,3 dioxolane;

cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3 dioxolane;

and pharmaceutically acceptable salts, pharmaceutically acceptable esters, and pharmaceutically acceptable salts of esters thereof.

39. A compound according to claim 38, wherein said compound is cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3 dioxolane or a pharmaceutically acceptable salt, pharmaceutically acceptable ester, or pharmaceutically acceptable salt of an ester thereof, in the form of a racemic mixture or a single optical isomer.
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