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1. WO2016151464 - AN IMPROVED PROCESS FOR THE PREPARATION OF CLOBAZAM AND ITS INTERMEDIATE

Publication Number WO/2016/151464
Publication Date 29.09.2016
International Application No. PCT/IB2016/051562
International Filing Date 21.03.2016
IPC
C07D 243/12 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
243Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
06having the nitrogen atoms in positions 1 and 4
10condensed with carbocyclic rings or ring systems
121,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
C07C 231/02 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
231Preparation of carboxylic acid amides
02from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
C07C 233/43 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
233Carboxylic acid amides
01having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
34having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
42with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
43having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
C07B 43/06 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
43Formation or introduction of functional groups containing nitrogen
06of amide groups
CPC
C07B 2200/13
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200Indexing scheme relating to specific properties of organic compounds
13Crystalline forms, e.g. polymorphs
C07B 37/10
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
37Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
10Cyclisation
C07C 231/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
231Preparation of carboxylic acid amides
02from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
C07C 233/43
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
233Carboxylic acid amides
01having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
34having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
42with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
43having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
C07D 243/12
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
243Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
06having the nitrogen atoms in positions 1,4
10condensed with carbocyclic rings or ring systems
121,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
Applicants
  • PIRAMAL ENTERPRISES LIMITED [IN]/[IN]
Inventors
  • JAGTAP, Ashutosh
  • GHARPURE, Milind
  • SHINDE, Navnath
  • PATIL, Navnath
  • SHAH, Chirag
  • RAUT, Changdev
  • KRISHNMURTHY, Dhileepkumar
Priority Data
966/MUM/201524.03.2015IN
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) AN IMPROVED PROCESS FOR THE PREPARATION OF CLOBAZAM AND ITS INTERMEDIATE
(FR) PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE CLOBAZAM ET SON INTERMÉDIAIRE
Abstract
(EN)
The present invention provides an improved process for the preparation of 8-chloro-1-phenyl- 1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (hereafter referred to as the compound (IV)), which is useful as a key intermediate for the synthesis of Clobazam (referred to as the compound (I)) 7-chloro-1-methyl-5-phenyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione. The process of the present invention further involves transformation of the compound (IV) into Clobazam (I), comprising (a) reacting the compound (II) (as described herein) with monoalkyl malonate in the presence of a coupling agent to obtain the compound (III) (as described herein); followed by the cyclization using a base; (b) reacting the compound-IV (as described herein) obtained from step (a) with methylating agent. The process of the present invention involves formation of novel intermediates methyl 3-((4- chloro-2-(phenylamino)phenyl)amino)-3-oxopropanoate (IlIa) and 3-((4-chloro-2- (phenylamino)phenyl)amino)-3-oxopropanoic acid (V).
(FR)
La présente invention prévoit un procédé amélioré de préparation de 8-chloro-1-phényl-1H-benzo[b][1,4]diazépine-2,4(3H,5H)-dione (ci-après désigné par le composé (IV)), qui est utile comme intermédiaire clé de synthèse de clobazam (désigné par composé (I)) 7-chloro-1-méthyl-5-phényl-1H-benzo[b][1,4]diazépine-2,4(3H,5H)-dione. Le procédé de la présente invention implique en outre la transformation du composé (IV) en clobazam (I), comprenant (a) la réaction du composé (II) (tel que décrit dans la description) avec du malonate de monoalkyle en présence d'un agent de couplage pour obtenir le composé (III) (tel que décrit dans la description) ; suivi de la cyclisation en utilisant une base ; (b) la réaction du composé IV (tel que décrit dans la description) obtenu à partir de l'étape (a) avec un agent de méthylation. Le procédé de la présente invention implique la formation de nouveaux intermédiaires 3-((4-chloro-2-(phénylamino)phényl)amino)-3-oxopropanoate de méthyle (IIIa) et acide 3-((4-chloro-2-(phénylamino)phényl)amino)-3-oxopropanoïque (V).
Also published as
Latest bibliographic data on file with the International Bureau