577953-88-9

Usage

Uses

Used in Pharmaceutical Industry:
Montelukast Dicyclohexylamine Salt is used as an antiasthmatic agent for the treatment of asthma and other respiratory conditions. It works by blocking the action of leukotriene D4, a substance that can cause inflammation and narrowing of the airways, thereby helping to alleviate asthma symptoms and improve lung function.

InChI:InChI=1/C35H36ClNO3S.C12H23N/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39);11-13H,1-10H2/b15-10+;/t32-;/m1./s1

Upstream product

• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 158966-92-8 montelukast 
• 169954-93-2 2-(2-(3(S)-(3-(2-(7-chloroquinolin-2-yl)ethyl)phenyl)-3-(methanesulfonyl-1-oxy)methylethyl)phenyl)-2-propanol 
• 866923-62-8 2-(1-((((R)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)sulfanyl)methyl)cyclopropyl)acetonitrile 
• 855473-51-7 1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid methyl ester 
• 920739-17-9 (S)-benzenepropanol α-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methyl ethyl)-α-methane sulfonate 
• 162515-68-6 1-(sulfanylmethyl)cyclopropaneacetic acid 
• 807638-71-7 2-[2-[3(S)-[3-[(1E)-2-(7-chloroquinoline-2-yl)ethenyl]phenyl]-3-methanesulfonyloxypropyl]phenyl]-2-propanol 
• 287930-77-2 (S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol 
• 1359172-44-3 1-{3-[(E)-2-(7-chloroquinolin-2-yl)vinyl]phenyl}-3-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]propan-1-one 
• 1359172-74-9 7-chloro-2-[(E)-2-(3-{(S)-3-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]-1-trimethylsilanyloxypropyl}phenyl)vinyl]quinoline 
• 1359172-33-0 C₃₃H₃₈ClNO₄SSi 
• 1359172-40-9 C₇H₁₁O₂S^(1-)*Cs⁽¹⁺⁾ 
• 1359172-54-5 (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-methyl-1-trimethylsilanyloxy-ethyl)-phenyl]-propan-1-ol 

Downstream Products

• 151767-02-1 Montelukast sodium 
• 158966-92-8 montelukast 

Relevant academic research and scientific papers

A synthesis process of montelukast sodium (by machine translation)

A synthesis process of montelukast sodium, relates to the field of drug synthesis, adopts a double hydroxy precursor of a sulfonyl derivative, and mercapto carboxylic acid compound, b cyclohexylamine in the reaction under the action of a catalyst, to obtain the ammonium salt, the quaternary ammonium salt is converted into the montelukast sodium. Compared with the direct synthesis of montelukast sodium, synthetic ammonium salt reaction not only conversion is higher, but also easy to separate, high purity, thus being beneficial to obtain high-purity of montelukast sodium. The synthesizing process of the synthetic route is simple, easy to operate, low requirements on equipment, can realize the large-scale production of montelukast sodium. (by machine translation)

METHOD FOR PRODUCING CRYSTAL OF MONTELUKAST FREE ACID

PROBLEM TO BE SOLVED: To provide a method for producing high-purity 1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid (montelukast free acid) efficiently in high yield. SOLUTION: The method for producing high-purity montelukast free acid, in which acid salt of organic amine salt does not remain, efficiently in high yield comprises a step of continuously performing such a reaction that montelukast organic amine salt is led to the montelukast free acid by using an acid in a mixture of a water-soluble organic solvent with water and continuously crystallizing the montelukast free acid from the obtained reaction solution. COPYRIGHT: (C)2015,JPO&INPIT

NOVEL MONTELUKAST 4-HALOBENZYLAMINE SALT AND METHOD FOR PREPARING MONTELUKAST SODIUM SALT BY USING THE SAME

Disclosed are a novel montelukast 4-halobenzylamine salt, and a method for preparing a montelukast sodium salt by using the same. In the disclosed method, a montelukast 4-halobenzylamine salt represented by Formula 2 or a montelukast sodium salt represented by Formula 1 is prepared by obtaining a compound represented by Formula 3 from a compound represented by Formula 5, in the same reactor, without an additional obtaining process. In Formula 2, X represents F, Cl, Br or I.

NOVEL MONTELUKAST 4-HALOBENZYLAMINE SALT AND METHOD FOR PREPARING MONTELUKAST SODIUM SALT BY USING THE SAME

Disclosed are a novel montelukast 4-halobenzylamine salt, and a method for preparing a montelukast sodium salt by using the same. In the disclosed method, a montelukast 4-halobenzylamine salt represented by Formula 2 or a montelukast sodium salt represented by Formula 1 is prepared by obtaining a compound represented by Formula 3 from a compound represented by Formula 5, in the same reactor, without an additional obtaining process. (Formular I and II should be inserted here) In Formula 2, X represents F, CI, Br or I.

PROCESS FOR THE PREPARATION OF MONTELUKAST SODIUM

The present invention relates to a process for the synthesis of Montelukast sodium of formula I the chemical name of which is [(R)-(E)]-1-[[[1-[3-[2-(7-chloro-2- quinolinyl)ethenyl]phenyl] -3 - [2-( 1 -hydroxy- 1 -methylethyl)phenyl]propyl] thio]methyl] - -cyclopropaneacetic acid sodium salt. The present invention further provides compounds of general formulae V, VI, VIb and VIII as new intermediates.

PREPARATION OF MONTELUKAST

Processes for the preparation of montelukast and its salts.

METHOD FOR ISOLATION AND PURIFICATION OF MONTELUKAST

A method of isolation of Montelukast of formula I from reaction mixtures, comprising conversion of the crude sub-stance to well-crystallizing salts with primary amines in the environment of at least one organic solvent and acetonitrile, followed by re-crystallization of these salts with simultaneous removal of chemical impurities and use of the chemically pure salts of Montelukast with primary amines for direct transformation to the pharmaceutically useful amorphous form of Montelukast sodium of formula II.

Process for the Preparation of Montelukast and its Salts

The present invention relates to an improved process for the preparation of 1-[[[(1R)-1-[3[(1E)-2-(7chloro-2-quinolinyl) ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl) phenyl] propyl] thio] methyl] cyclopropaneacetic acid (Formula-1) and its salts using Methyl 2-[(3S)-[3-[(2E)-(7-chloro quinolin-2-yl) ethenyl] phenyl]-3-halopropyl] benzoate (Formula-2)

Process for the Preparation of Montelukast and Its Pharmaceutically Acceptable Salts

An improved process for the preparation of Montelukast and its pharmaceutically acceptable salts comprises of reacting (S) Benzenepropanol α-[3-[2-(7-chloro2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methyl ethyl)-α-methane sulfonate compound of formula (II) with 1-(mercapto methyl)cyclo propane acetic acid or its ester or nitrile in presence of alkali or alkaline carbonates and/or alkali or alkaline earth metal alkoxide in a suitable polar aprotic solvent with or without combination of C1-C4 alcoholic solvents and then treating with organic amine in a suitable ester and/or acetone and/or aliphatic or aromatic hydrocarbon solvents, and converting the corresponding amine salt compound of montelukast into its sodium salt compound of formula (I) using sodium ion source in methanol, without converting into montelukast free acid.