Process of preparing ziprasidone mesylate

• US 20060258679A1
• Filed: 02/13/2006
• Published: 11/16/2006
• Est. Priority Date: 02/11/2005
• Status: Abandoned Application

• Current Assignee: Teva Pharmaceuticals USA, Inc. (Teva Pharmaceutical Industries Limited)
• Original Assignee: Teva Pharmaceuticals USA, Inc. (Teva Pharmaceutical Industries Limited)
• Inventors: Gold, Amir, Mendelovici, Marioara, Mainfeld, Alex
• Application Number:
  US11/353,304
• Publication Number:
  US 20060258679A1
• Time in Patent Office: Days
• US Class Current: 514/254.40
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/14 containing three or more hetero rings

Abstract

The invention provides a process of preparing ziprasidone mesylate.

Claims

1. A process for preparing amorphous ziprasidone mesylate comprising the step of spray-drying a solution of ziprasidone mesylate at an outlet temperature of above 90°

C. in a solvent selected from a group consisting of;

C₁-C₅ alcohols, C₂-C₈ ethers, glacial acetic acid, optionally in mixture with water.

2. The process of claim 1, wherein the inlet temperature is higher the outlet temperature.

3. The process of claim 1, wherein the solution is formed by dissolving dihydrate needle crystals of ziprasidone mesylate in a solvent.

4. The process of claim 1, wherein the solvent is selected from the group consisting of:

diethyl ether, tetrahydrofuran, methyl t-butyl ether, glacial acetic acid, ethanol and mixtures thereof with water.

5. The process of claim 4, wherein the solvent is an ethanol/water mixture.

6. The process of claim 5, wherein the ethanol/water ratio is from about 50:

50 to about 95;

5 ethanol to water by volume.

7. The process of claim 1, wherein the outlet temperature is about 90°

C.

8. The process of claim 7, wherein the inlet temperature is above 90°

C.

9. The process of claim 8, wherein the inlet temperature is about 150°

C.

10. The process of claim 1, wherein the amorphous ziprasidone mesylate contains less than about 10% of crystalline material as percentage area XRD.

11. The process of claim 10, wherein the amorphous ziprasidone mesylate contains less than about 5% of crystalline material as percentage area XRD.

12. The process of claim 11, wherein the amorphous ziprasidone mesylate contains less than about 1% of crystalline material as percentage area XRD.

13. A process for preparing ziprasidone mesylate crystal form characterized by X-ray powder diffraction peaks at 11.7, 17.3, 23.5, 24.2, and 25.2 degrees two-theta, ±

0.2 degrees two-theta (herein defined as Form I) comprising the step of spray-drying a solution of ziprasidone mesylate an outlet temperature of above 70°

C. in a solvent selected from a group consisting of;

glacial acetic acid, optionally in mixture with C₂-C₈ ethers, and collecting the obtained Form I.

14. The process of claim 13, wherein the inlet temperature is higher than the outlet temperature.

15. The process of claim 13, wherein dihydrate needle crystals of ziprasidone mesylate are used to form the solution.

16. The process of claim 13, wherein the solvent is glacial acetic acid.

17. The process of claim 13, wherein the outlet temperature is from about 70°

C. to about 100°

C.

18. The process of claim 13, wherein Form I is collected from the upper side of the apparatus.

19. The process of claim 18, wherein Form I is collected from the upper side of the cyclone.

20. A process for preparing ziprasidone mesylate crystal form characterized by X-ray powder diffraction peaks at 17.1, 18.7, 23.8, and 24.4 degrees two-theta, +0.2 degrees two-theta (herein defined as Form VIII) comprising the step of spray-drying a solution of ziprasidone mesylate at an outlet temperature of from about above 45°

C. to about 70°

C. in a solvent selected from the group consisting of;

C₁-C₅ alcohols, optionally in mixture with water.

21. The process of claim 20, wherein the inlet temperature is higher than the outlet temperature.

22. The process of claim 20, wherein the solution is formed by dissolving dihydrate needle crystals of ziprasidone mesylate in a solvent.

23. The process of claim 20, wherein the solvent is a mixture of ethanol and water.

24. The process of claim 23, wherein the ethanol/water ratio is from about 50:

50 to about 95;

5 ethanol to water by volume.

25. The process of claim 20, wherein the outlet temperature is about 55°

C.

26. The process of claim 20, wherein the inlet temperature is above 55°

C.

27. The process of claim 26, wherein the inlet temperature is about 80°

C.