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(R,E)-2-(2-(3-((1-(aminomethyl)cyclopropyl)methylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)phenyl)propan-2-ol, an impurity of Montelukast sodium

IP.com Disclosure Number: IPCOM000191568D
Publication Date: 2010-Jan-07
Document File: 2 page(s) / 46K

Publishing Venue

The IP.com Prior Art Database

Abstract

The disclosure relates to an impurity of Montelukast sodium, and a process for its preparation

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The present disclosure relates to (R,E)-2-(2-(3-((1-(aminomethyl)cyclopropyl)methylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)phenyl)propan-2-ol of formula (I), which is an impurity in Montelukast sodium, and a process for its preparation:

The (R,E)-2-(2-(3-((1-(aminomethyl)cyclopropyl)-methylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)phenyl)-propan-2-ol of formula (I) can be used as reference marker to analyze the purity of Montelukast sodium or as reference standard  to quantify its amount in a sample of Montelukast sodium by using appropriate analytical assays, in particular HPLC.

Using processes known in the prior art Montelukast can be obtained with an amount of this impurity below 0.1%. Known Montelukast salts containing this impurity may be further purified by conventional crystallization methods.

 

Example 1: Preparation of (R,E)-2-(2-(3-((1-(aminomethyl)cyclopropyl)

methylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)phenyl)-

propan-2-ol

2.60g of NaN3 (39.99 mmol) were added to a solution of (R,E)-(1-((1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propylthio)methyl)cyclopropyl)methyl methanesulfonate in DMF (8.95g, 12.80 mmol, in 130 ml of DMF). The mixture was heated to 50 ºC and stirred for 3 hours. Next, it was cooled down to room temperature and poured to...