Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy) phenylmethyl)carbamide and its tartrate salt and crystalline forms

US8236960B2 · kind B2 · utility

Assignee

• ACADIA Pharmaceuticals Inc. · US

Inventors

• Mikkel Boas Thygesen · Copenhagen, DK
• Nathalie Schlienger · Copenhagen, DK
• Bo-Ragnar Tolf · Malmö, SE
• Carl-Magnus A. Andersson · Hjo, SE
• Fritz Blatter · Reinach, CH
• Jörg Berghausen · Bad Kötzting, DE

Key dates

• Filing date: Apr 6, 2011
• Grant date: Aug 7, 2012
• Expiry date: Apr 6, 2031

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P43/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

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)-phenylmethyl)carbamide and its hemi-tartrate salt including various polymorphs and solvates.