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Generated: September 26, 2017

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Title:Salts of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-y1)-N'-(4-(2-methylprop- yloxy)phenylmethyl)carbamide and their preparation
Abstract: Disclosed herein are salts of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy) phenylmethyl)carbamide including the citrate, fumarate, maleate, malate, phosphate, succinate, sulphate, and edisylate salts.
Inventor(s): Thygesen; Mikkel Boas (Copenhagen East, DK), Schlienger; Nathalie (Frederiksberg, DK), Tolf; Bo-Ragnar (Malmo, SE), Blatter; Fritz (Reinach, CH), Berghausen; Jorg (Lorrach, DE)
Assignee: ACADIA Pharmaceuticals, Inc. (San Diego, CA)
Filing Date:Sep 26, 2005
Application Number:11/235,381
Claims:1. An isolated and purified crystalline salt of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)ph- enylmethyl)carbamide of formula I, ##STR00032## wherein the salt is the citrate or edisylate salt.

2. The salt of claim 1, wherein the salt is a citrate.

3. The salt of claim 2 that exhibits a X-ray powder diffraction pattern comprising peaks having d-values in angstroms of about 31.8, about 15.9, about 7.9, about 6.3, about 5.96, about 5.23, and about 4.68.

4. The salt of claim 1, wherein the salt is an edisylate (ethanedisulfonate).

5. The salt of claim 4 that exhibits a X-ray powder diffraction pattern comprising peaks having d-values in angstroms of about 10.0, about 6.05, about 5.31, about 4.97, about 4.26, and about 4.12.

6. A crystalline salt of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)ph- enylmethyl)carbamide of formula I, ##STR00033## produced by a process comprising: a) forming a solution of the compound of formula I in an organic solvent; b) adding citric acid or 1,2-ethane disulfonic acid to said solution; and c) isolating the salt.

7. A pharmaceutical composition comprising one or more salts of claim 1 and a pharmaceutically acceptable carrier.

8. The phatinaceutical composition of claim 7, wherein the composition is in a solid dosage form.

9. The pharmaceutical composition of claim 8, wherein the solid dosage form is suitable for oral administration.

10. The pharmaceutical composition of claim 9, wherein the amount of the salt of formula IV is from about 1 to 100 mg.

11. The salt of claim 2 that exhibits a X-ray powder diffraction pattern comprising peaks having d-values in angstroms of about 15.9, about 7.9, about 6.3, and about 4.68.

12. The salt of claim 4 that exhibits a X-ray powder diffraction pattern comprising peaks having d-values in angstroms of about 10.0, about 6.05, and about 4.97.

13. The citrate salt of claim 2, wherein the salt is of formula IV: ##STR00034##

14. The edisylate salt of claim 4, wherein the salt is of formula XI: ##STR00035##

15. The citrate salt of claim 2, wherein the salt has a water solubility of about 14 mg/mL.

16. The edisylate salt of claim 4, wherein the salt has a water solubility of about 4 mg/mL.
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