Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Methods for preparing n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and polymorphic form c

A kind of fluorophenylmethyl, methyl propoxy technology, applied in the field of medicine and chemistry

Active Publication Date: 2018-03-27
ACADIA PHARMA INC
View PDF7 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While the pathway described is sufficient to produce pimavanserin, there may be other pathways that offer other opportunities

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Methods for preparing n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and polymorphic form c
  • Methods for preparing n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and polymorphic form c
  • Methods for preparing n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and polymorphic form c

Examples

Experimental program
Comparison scheme
Effect test

example

[0250] Experimental Procedures and Instruments

[0251] Examples of devices and methods useful in assisting in the preparation of the compounds described herein are:

[0252] NMR equipment: VARIAN INOVA 400mhz.

[0253] GC-MS equipment: TRACE GC THERMO FINNIGAN (method: column: ZB-5MS, 30x 0.25mm, 0.25μm. Temperature gradient: 50°C for 2min, then rise to 320°C at 20°C / min. Hold time: 15min. Flow rate : 1.0ml / min, split: 1:50, injection temperature: 200°C. injection volume: 1μL. diluent: acetonitrile).

[0254] LC-MS equipment: AGILENT 6530ACCURATE-MASS Q-TOF (Method: Column: ACQUITYUPLC BEHC18, 100x 2.1mm, 1.7μm. Eluent A: 0.1% HFo in acetonitrile. Eluent B: 0.1% HFo in h 2 O middle. Gradient: 10% A 90% B at 0 min, 95% A 5% B at 15 min, 95% A 5% B at 20 min. Flow rate: 0.25ml / min, temperature: 40°C. Injection volume: 1 μL. Diluent: Acetonitrile. ); or LCQ ADVANTAGE THERMO FINNIGAN (Method: Column: Symmetry Shield RP18, 150 x 3.0 mm, 3.5 μm, Eluent A: 0.05% TFA in Ace...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Disclosed herein are methods for obtaining N-(4-fluorobenzyl)-N-(l-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl) carbamide (pimavanserin) comprising the step of contacting an intermediate according to Formula (A) or a salt thereof, with an intermediate Formula B, or a salt thereof, to produce pimavanserin or a salt thereof wherein Y is -ORi or -NR2aR2b; R3 is hydrogen or substitutedor unsubstituted heteroalicyclyl, R4 is substituted or unsubstituted aralkyl; X is -OR22 or -NR23R24; (wherein R22 is hydrogen or substituted or unsubstituted C1-6alkyl and one of R23 and R24 is hydrogen and the other is hydrogen or N- methylpiperidin-4-yl); and R21 is -OCH2CH(CH3)2 or F; Also disclosed herein is the tartrate salt of N-(4-fluorobenzyl)-N-(l-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl) carbamide and methods for obtaining the salt.

Description

[0001] background technical field [0002] This disclosure relates to the fields of medicine and chemistry. More specifically, the present disclosure relates to one or more methods for obtaining N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methyl Propoxy)-phenylmethyl)urea, its tartrate salts and polymorphs, methods of intermediates, and their synthesis and use. Background technique [0003] N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropoxy)-phenylmethyl)urea (also known as pimavanserin) is described in WO 2004 / 064738, WO 2006 / 037043, WO 2007 / 124136 and WO 2008 / 144326, each of which is incorporated herein by reference in its entirety. These publications describe routes to the preparation of pimavanserin. While the pathway described is sufficient to produce pimavanserin, there may be other pathways that offer other opportunities. Contents of the invention [0004] Disclosed herein include methods of preparing pimavanserin. [0005] Also dis...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58
CPCC07D211/58C07B2200/13A61K31/4468C07C233/00C07D211/98
Inventor 马龙·卡洛斯萨冈·坦德尔R·奥尔森米卡尔·希尔格伦马修·J·弗莱明安德烈亚斯·菲利普·布迪耶贝亚特·T·韦伯
Owner ACADIA PHARMA INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com