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Details for Patent: 8,236,960

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Details for Patent: 8,236,960

Title:Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy) phenylmethyl)carbamide and its tartrate salt and crystalline forms
Abstract: Disclosed herein are methods for synthesizing N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl) -N'-(4-(2-methylpropyloxy)-phenylmethyl)carbamide. Also disclosed herein is the hemi-tartrate salt of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2 -methylpropyloxy)-phenylmethyl)carbamide and methods for obtaining the salt. Further disclosed are various crystalline forms of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)-p- henylmethyl)carbamide and its hemi-tartrate salt including various polymorphs and solvates.
Inventor(s): Thygesen; Mikkel Boas (Copenhagen East, DK), Schlienger; Nathalie (Frederiksberg, DK), Tolf; Bo-Ragnar (Malmo, SE), Andersson; Carl-Magnus A. (Hjarup, SE), Blatter; Fritz (Reinach, SE), Berghausen; Jorg (Lorrach, DE)
Assignee: ACADIA Pharmaceuticals Inc. (San Diego, CA)
Filing Date:Apr 06, 2011
Application Number:13/081,427
Claims:1. Crystalline form B of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)ph- enylmethyl)carbamide tartrate of formula IV, ##STR00032## which shows an endothermic signal at 131.degree. C. as measured by differential scanning calorimetry.

2. The crystalline form of claim 1, wherein the endothermic signal at 131.degree. C. has an enthalpy of fusion of about 63 J/g.

3. The crystalline form of claim 1, wherein the crystalline form is a mono-hydrate.

4. The crystalline form of claim 1, wherein the crystalline form is about 3.4% by weight water.

5. The crystalline form of claim 4, wherein the crystalline form is about 3.4% by weight water at a relative humidity of greater than or equal to 20%.

6. Crystalline form B of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)ph- enylmethyl)carbamide tartrate of formula IV, ##STR00033## which shows an endothermic signal at 129.degree. C. as measured by differential scanning calorimetry.

7. The crystalline form of claim 6, wherein the endothermic signal at 129.degree. C. has an enthalpy of fusion of about 71 J/g.

8. The crystalline form of claim 6, wherein the crystalline form is a mono-hydrate.

9. The crystalline form of claim 6, wherein the crystalline form is about 3.4% by weight water.

10. The crystalline form of claim 9, wherein the crystalline form is about 3.4% by weight water at a relative humidity of greater than or equal to 20%.
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