Asian Journal of Chemistry

Identification, Synthesis and Characterization of Impurities of Montelukast Sodium

IVS Kumar, VH Bindu

Index: Sunil Kumar; Anjaneyulu; Hima Bindu Asian Journal of Chemistry, 2011 , vol. 23, # 10 p. 4536 - 4546

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Citation Number: 0

Abstract

Abstract Montelukast sodium is a selective leukotriene receptor antagonist which inhibits cysteinyl leukotriene CysLT1 receptor. Various synthesis of Montelukast is published. During laboratory optimization and later in bulk synthesis formation of various impurities was detected. Besides, pharma Europa draft mention nine process related impurities. However, the method of preparation of most of these impurities is not available in literature. Also, ...

 Related Synthetic Route
Methylmagnesium chloride Structure

676-58-4

Methylmagnesium...

Methyl 2-[(3S)-3-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate Structure

181139-72-0

Methyl 2-[(3S)-...

~99%

(1S)-1-{3-[(E)-2-(7-Chloro-2-quinolinyl)vinyl]phenyl}-3-[2-(2-hyd roxy-2-propanyl)phenyl]-1-propanol Structure

287930-77-2

(1S)-1-{3-[(E)-...

1-[2-[(3S)-3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-hydroxypropyl]phenyl]ethanone Structure

184764-13-4

1-[2-[(3S)-3-[3...

Methyl (E)-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoate Structure

149968-11-6

Methyl (E)-2-[3...

~%

(1S)-1-{3-[(E)-2-(7-Chloro-2-quinolinyl)vinyl]phenyl}-3-[2-(2-hyd roxy-2-propanyl)phenyl]-1-propanol Structure

287930-77-2

(1S)-1-{3-[(E)-...

Methyl [S-(E)]-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-methanesulfonyloxy-propyl] benzoate Structure

906107-36-6

Methyl [S-(E)]-...

~%

Montelukast Methyl Ketone Structure

937275-23-5

Montelukast Met...

Methyl (E)-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoate Structure

149968-11-6

Methyl (E)-2-[3...

~%

Montelukast Methyl Ketone Structure

937275-23-5

Montelukast Met...

Methyl 2-[(3S)-3-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate Structure

181139-72-0

Methyl 2-[(3S)-...

~%

Montelukast Methyl Ketone Structure

937275-23-5

Montelukast Met...

2'-Des(1-hydroxy-1-methylethyl)-2'-methycarboxy Montelukast Structure

851755-56-1

2'-Des(1-hydrox...

Methylmagnesium chloride Structure

676-58-4

Methylmagnesium...

~%

Montelukast Methyl Ketone Structure

937275-23-5

Montelukast Met...

Methyl (E)-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoate Structure

149968-11-6

Methyl (E)-2-[3...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

Methyl 2-[(3S)-3-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate Structure

181139-72-0

Methyl 2-[(3S)-...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

(1S)-1-{3-[(E)-2-(7-Chloro-2-quinolinyl)vinyl]phenyl}-3-[2-(2-hyd roxy-2-propanyl)phenyl]-1-propanol Structure

287930-77-2

(1S)-1-{3-[(E)-...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

Montelukast Styrene Structure

918972-54-0

Montelukast Styrene

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

2-(1-((((1R)-1-(3-(1-(((1-(carboxymethyl)cyclopropyl)methyl)thio)-2-(7-chloroquinolin-2-yl)ethyl)phenyl)-3-(2-(prop-1-en-2-yl)phenyl)propyl)thio)methyl)cyclopropyl)acetic acid Structure

1351973-24-4

2-(1-((((1R)-1-...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

N/A Structure

1197374-11-0

N/A

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

N/A Structure

1197374-09-6

N/A

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

N/A Structure

1197374-12-1

N/A

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

(S)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-isopropenylphenyl)propan-1-ol hydrochloride Structure

1197374-10-9

(S)-1-(3-((E)-2...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

(S)-1-(3-((E)-2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl acetate Structure

869066-93-3

(S)-1-(3-((E)-2...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

(S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(prop-1-en-2-yl)phenyl)propan-1-ol Structure

1197414-05-3

(S,E)-1-(3-(2-(...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...

Methyl [1-(sulfanylmethyl)cyclopropyl]acetate Structure

152922-73-1

Methyl [1-(sulf...

2-(3-(S)-(3-(2-(7-chloroquinolinyl)ethenyl)phenyl)-3-methanesulfonyloxypropyl)phenyl-2-propanol Structure

807638-71-7

2-(3-(S)-(3-(2-...

~%

Montelukast Bis-sulfide Structure

1187586-61-3

Montelukast Bis...

1-[[[(1R)-1-[3-[(1S)-1-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid Structure

1187586-58-8

1-[[[(1R)-1-[3-...


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