Granted Patent B2

US 7,884,219 · App. 12/046,872 · Granted Feb 8, 2011

Abstract

Claims (22)

1. A polymorph of [3-(4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine, having a solid state 13 C NMR spectrum comprising peaks at 153.6, 140.1 and 119.9 ppm, when the upfield resonance of crystalline adamantane is set to 29.5 ppm.

2. The polymorph of claim 1 , having a solid state 13 C NMR spectrum comprising peaks at 153.6, 149.0, 140.1, 119.9, and 28.6 ppm, when the upfield resonance of crystalline adamantane is set to 29.5 ppm.

3. The polymorph of claim 2 , having a solid state 13 C NMR spectrum comprising peaks at 153.6, 149.0, 140.1, 123.2, 121.6, 119.9, and 28.6 ppm, when the upfield resonance of crystalline adamantane is set to 29.5 ppm.

4. The polymorph of claim 1 , having IR absorption maxima at 816, 1046 and 1178 cm −1 .

5. The polymorph of claim 4 , having IR absorption maxima at 660, 707, 735, 816, 969, 1024, 1046, 1135 and 1178 cm −1 .

6. The polymorph of claim 1 , having a Raman spectrum comprising Raman shifts of 300 and 1180 cm −1 .

7. The polymorph of claim 6 , having a Raman spectrum comprising Raman shifts of 257, 300, 326, 590, 646, 1180, 1348 and 1370 cm −1 .

8. A polymorph of [3-(4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine, having an X-ray powder diffraction comprising the following 2θ values, measured using CuKα radiation having a wavelength of 1.54056 Å: 18.8 and 20.1 degrees.

9. The polymorph of claim 8 , having IR absorption maxima at 816, 1046 and 1178 cm −1 .

10. The polymorph of claim 9 , having IR absorption maxima at 660, 707, 735, 816, 969, 1024, 1046, 1135 and 1178 cm −1 .

11. The polymorph of claim 8 , having a Raman spectrum comprising Raman shifts of 300 and 1180 cm −1 .

12. The polymorph of claim 11 , having a Raman spectrum comprising Raman shifts of 257, 300, 326, 590, 646, 1180, 1348 and 1370 cm −1 .

13. A polymorph of [3-(4-{2-butyl-1[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine, having a Raman spectrum comprising Raman shifts of 300 and 1180 cm −1 .

14. The polymorph of claim 13 , having a Raman spectrum comprising Raman shifts of 257, 300, 326, 590, 646, 1180, 1348 and 1370 cm −1 .

15. The polymorph of claim 1 , 8 , or 13 , where the polymorph exists in a form that is substantially free of Form I of [3-(4-{2-butyl-1[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine.

16. A method of producing a polymorph of [3-(4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine comprising:

(a) dissolving [3-(4-{2-butyl-1[ 4 4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine in a solvent system comprising an alcoholic solvent;

(b) adding a precipitating solvent to the solvent system such that [3-(4-{2-butyl-1[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine precipitates from the solvent system; and

(c) recovering the precipitate from the solvent system.

17. The method of claim 16 , wherein the alcoholic solvent is selected from the group consisting of methanol, ethanol, isopropanol, and mixtures thereof.

18. The method of claim 16 , wherein the precipitating solvent is water.

19. The method of claim 16 , wherein the polymorph of [3-(4-{2-butyl-[1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine comprises Form II.

Assignments (12)