Claims
- 1. A method of preparing a compound of Formula (I) or a pharmaceutically acceptable complex thereof
- 2. The method of claim 1 wherein p is 1 to 2.
- 3. The method of claim 1 wherein q is 1 to 2.
- 4. The method of claim 1 wherein R1 is selected from the group consisting of hydrogen, alkyl, chlorine, and fluorine.
- 5. The method of claim 4 wherein p is 1, and R1 is selected from the group consisting of hydrogen, chlorine, and methyl.
- 6. The method of claim 5 wherein R1 is at the 4-position.
- 7. The method of claim 1 wherein R2 is selected from the group consisting of hydrogen, an alkyl group, an alkoxy group and an alkylthio group.
- 8. The method of claim 7 wherein q is 1, and R2 is selected from the group consisting of ethyl, ethoxy and methylthio.
- 9. The method of claim 8 wherein R2 is at the 4-position.
- 10. The method of claim 1 wherein A is (CH2) located at the 3-position.
- 11. The method of claim 1 wherein the compound of Formula (I) is a compound of Formula (IA):
- 12. The method of claim 11 wherein R1 is hydrogen and R2 is ethyl.
- 13. The method of claim 11 wherein R1 is chlorine and R2 is ethoxy.
- 14. The method of claim 11 wherein R1 is methyl and R2 is methylthio.
- 15. The method of claim 1 further comprising reacting the compound of Formula (I) with at least one amino acid complex forming reagent to yield the pharmaceutically acceptable complex of the compound of Formula (I).
- 16. The method of claim 15 wherein the amino acid is L-phenylalanine.
- 17. A method of forming C-aryl glucoside compounds comprising reacting a compound of Formula (VI)
- 18. The method of claim 17 wherein the reducing reagent is selected from the group consisting of silyl hydrides.
- 19. The method of claim 18 wherein the reducing reagent is an alkylsilyl hydride.
- 20. The method of claim 17 wherein the reaction between the compound of Formula (VI) and the reducing reagent is carried out in the presence of an activating group.
- 21. The method of claim 20 wherein the activating group is selected from the group consisting of Lewis acids.
- 22. The method of claim 17 further comprising reacting a compound of Formula (V)
- 23. The method of claim 22 wherein the acylating reagent is selected from the group consisting of acyl derivatives, acyl halides, acetyl chloride, acid anhydrides, acetic anhydride, propionic anhydride and combinations thereof.
- 24. The method of claim 22 further comprising reacting a compound of Formula (IV)
- 25. The method of claim 24 wherein the acid labile protecting group is selected from the group consisting of methoxymethyl ether, methylthiomethyl ether, 2-methoxyethoxymethyl ether, bis(2-chloroethoxy)methyl ether, tetrahydropyranyl ether, tetrahydrothiopyranyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxytetrahydrothiopyranyl ether, tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 1-ethoxyethyl ether, 1-methyl-1-methoxyethyl ether, 2-(phenylselenyl)ethyl ether, t-butyl ether, allyl ether, triphenylmethyl ether, α-naphthyldiphenylmethyl ether, p-methoxyphenyldiphenyl methyl ether, trialkylsilyl ether, trimethylsilyl ether, triethylsilyl ether, isopropyldimethylsilyl ether, t-butyidimethylsilyl ether, t-butyidiphenylsilyl ether and combinations thereof.
- 26. The method of claim 25 wherein the acid labile protecting group is selected from the group consisting of methoxymethyl ether, 2-methoxyethoxymethyl ether, tetrahydropyranyl ether, trimethylsilyl ether, isopropyldimethylsilyl ether, t-butyldimethylsilyl ether, t-butyldiphenylsilyl ether, and combinations thereof.
- 27. The method of claim 24 further comprising reacting a compound of Formula (II)
- 28. The method of claim 27 wherein Y is selected from the group consisting of alkali metals, and alkaline earth metals.
- 29. The method of claim 27 further comprising reacting D-glucono-1,5-lactone with an acid labile protecting group providing reagent to form the compound of Formula (II).
- 30. The method of claim 29 wherein the acid labile protecting group providing reagent is selected from the group consisting of trimethylsilylchloride, trimethylsilyl trifluoromethanesulfonic acid, methyoxymethylchloride, dihydrofuran, benzyloxymethylchloride, triethylsilylchloride and tetrahydropyran.
- 31. A method of preparing an intermediate compound of Formula (IV)
- 32. A method of preparing an intermediate compound of Formula (V)
- 33. The method of claim 32 further comprising isolating the compound of Formula (V) from the reaction mixture.
- 34. A method of preparing an intermediate compound of Formula (VI)
- 35. A method of preparing an intermediate compound of Formula (VII)
- 36. A compound of Formula (IV)
- 37. A compound of Formula (V)
- 38. A compound of Formula (VI)
- 39. A compound of Formula (VII)
- 40. The method of claim 1 wherein steps (a) through (e) are performed in situ.
Parent Case Info
[0001] This application claims priority from U.S. Provisional Application 60/437,847 filed Jan. 3, 2003 which is incorporated herein by reference.
Provisional Applications (1)
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Number |
Date |
Country |
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60437847 |
Jan 2003 |
US |