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Claims for Patent: 7,893,097

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Claims for Patent: 7,893,097

Title:Methods and compositions for increasing solubility of azole drug compounds that are poorly soluble in water
Abstract: The combination of any two of a polyol, a polyol ether, and a low carbon organic alcohol provides a synergistic effect on the solubility of azole compounds, such as metronidazole, in aqueous fluid.
Inventor(s): Yang; Meidong (Richmond, CA), Chen; Haigang (Petaluma, CA)
Assignee: Dow Pharmaceutical Sciences, Inc. (Petaluma, CA)
Application Number:12/012,413
Patent Claims: 1. An aqueous solution comprising water at a concentration of about 55% w/w or higher, a poorly water-soluble imidazole or triazole chemical compound, and at least two of a polyol, a polyol ether, and a low carbon organic alcohol, wherein the at least two of a polyol, a polyol ether, and a low carbon organic alcohol are present in the aqueous solution in amounts sufficient to provide a synergistic effect on the solubility of the chemical compound in the aqueous solution.

2. The aqueous solution of claim 1 wherein the imidazole or triazole chemical compound is selected from the group consisting of metronidazole, ketoconazole, itraconazole, miconazole, dimetridazole, secnidazole, omidazole, tinidazole, carnidazole, and panidazole.

3. The aqueous solution of claim 2 wherein the chemical compound is metronidazole.

4. The aqueous solution of claim 1 which comprises a polyol and a polyol ether.

5. The aqueous solution of claim 1 which comprises a polyol and a low carbon organic alcohol.

6. The aqueous solution of claim 1 which comprises a polyol ether and a low carbon organic alcohol.

7. The aqueous solution of claim 1 which comprises a polyol, a polyol ether, and a low carbon organic alcohol.

8. The aqueous solution of claim 7 wherein the polyol is propylene glycol, the polyol ether is diethylene glycol monoethyl ether, and the low carbon organic alcohol is benzyl alcohol.

9. The aqueous solution of claim 1 wherein the polyol is selected from the group consisting of polyether glycol, propylene glycol, hexylene glycol, and sugar alcohol.

10. The aqueous solution of claim 9 wherein the polyol is propylene glycol.

11. The aqueous solution of claim 1 wherein the polyol ether is selected from the group consisting of diethylene glycol monoethyl ether, ethers of pentaerythritol, ethers of alkylene glycol, ethers of a fatty alcohol, and ethers of a sugar.

12. The aqueous solution of claim 11 wherein the polyol ether is diethylene glycol monoethyl ether.

13. The aqueous solution of claim 1 wherein the low carbon organic alcohols is selected from the group consisting of ethyl alcohol, propyl alcohol, phenol, and benzyl alcohol.

14. The aqueous solution of claim 1 wherein the polyol is propylene glycol, the polyol ether is diethylene glycol monoethyl ether, and the low carbon organic alcohol is benzyl alcohol.

15. The aqueous solution of claim 1 which is stable when stored for a period of two weeks at room temperature or for a period of one week or more at a temperature of 5.degree. C.

16. A method for making an aqueous solution of a poorly water-soluble imidazole or triazole chemical compound comprising combining in an aqueous fluid the chemical compound and at least two of a polyol, a polyol ether, and a low carbon organic alcohol, wherein the at least two of a polyol, a polyol ether, and a low carbon organic alcohol are combined in the aqueous fluid in amounts sufficient to provide a synergistic effect on the solubility of the chemical compound in the aqueous fluid, and wherein the concentration of water in the aqueous fluid is about 55% w/w or higher.

17. The method of claim 16 wherein the imidazole or triazole chemical compound is selected from the group consisting of metronidazole, ketoconazole, itraconazole, miconazole, dimetridazole, secnidazole, ornidazole, tinidazole, carnidazole, and panidazole.

18. The method of claim 17 wherein the chemical compound is metronidazole.

19. The method of claim 16 wherein a polyol and a polyol ether are combined in the aqueous fluid.

20. The method of claim 16 wherein a polyol and a low carbon organic alcohol are combined in the aqueous fluid.

21. The method of claim 16 wherein a polyol ether and a low carbon organic alcohol are combined in the aqueous fluid.

22. The method of claim 16 wherein a polyol, a polyol ether, and a low carbon organic alcohol are combined in the aqueous fluid.

23. The method of claim 22 wherein the polyol is propylene glycol, the polyol ether is diethylene glycol monoethyl ether, and the low carbon organic alcohol is benzyl alcohol.

24. The method of claim 16 wherein the polyol is selected from the group consisting of polyether glycol, propylene glycol, and sugar alcohol.

25. The method of claim 24 wherein the polyol is propylene glycol.

26. The method of claim 16 wherein the polyol ether is selected from the group consisting of diethylene glycol monoethyl ether, ethers of pentaerythritol, ethers of alkylene glycol, ethers of a fatty alcohol, and ethers of a sugar.

27. The method of claim 26 wherein the polyol ether is diethylene glycol monoethyl ether.

28. The method of claim 16 wherein the low carbon organic alcohol is selected from the group consisting of ethyl alcohol, propyl alcohol, phenol, and benzyl alcohol.

29. The method of claim 16 wherein the polyol is propylene glycol, the polyol ether is diethylene glycol monoethyl ether, and the low carbon organic alcohol is benzyl alcohol.
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