Preparing brivaracetam used for treating partial-onset seizure, involves reducing (S)-2-(2-oxo-4-propyl-2,5-dihydro-1H-pyrrol-1-yl) butanamide in presence of catalyst, hydrogen, organic acid followed by resolution of mixture of isomers via chiral reagent, desalification of chiral salt in base
	MEENAKSHISUNDERAM S; ALI N A S; DUSSA N; KHAN M U; UMMADI R R; SINGH A K; KONDURU R R
	2023-08-04
专利权人	AUROBINDO PHARMA LTD (AUMA-C)
申请日期	2023-08-04
专利号	IN202341052597-A
成果简介	NOVELTY - Preparing brivaracetam of (I), involves: (a) performing reduction of (S)-2-(2-oxo-4-propyl-2,5-dihydro-1H-pyrrol-1-yl) butanamide (II) using a catalyst in the presence of hydrogen and an organic acid to give a diastereomeric mixture of (2S)-2-((4R)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide of (III) and (2S)-2-((4S)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide of (IV); (b) performing resolution of mixture of isomers, i.e. (2S)-2-((4R)-2-oxo-4-N-propyl-1- pyrrolidinyl) butanamide and (2S)-2-((4S)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide using a chiral reagent to give brivaracetam chiral salt of (V); and (c) performing de-salification of brivaracetam chiral salt using a suitable base to give brivaracetam. USE - Process for preparing brivaracetam used for treating partial-onset seizures in patients 1 month of age and older. ADVANTAGE - The process provides good yield and purity, without the use of preparative column chromatography. DETAILED DESCRIPTION - Preparing brivaracetam of formula (I), involves: (a) performing reduction of (S)-2-(2-oxo-4-propyl-2,5-dihydro-1H-pyrrol-1-yl) butanamide of formula (II) using a catalyst in the presence of hydrogen and an organic acid to give a diastereomeric mixture of (2S)-2-((4R)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide of formula (III) and (2S)-2-((4S)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide of formula (IV); (b) performing resolution of mixture of isomers, i.e. (2S)-2-((4R)-2-oxo-4-N-propyl-1- pyrrolidinyl) butanamide and (2S)-2-((4S)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide using a chiral reagent to give brivaracetam chiral salt of formula (V); and (c) performing de-salification of brivaracetam chiral salt using a suitable base to give brivaracetam. An INDEPENDENT CLAIM is included for a process for the resolution of mixture of brivaracetam isomers, i.e., (2S)-2- ((4R)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide and (2S)-2-((4S)-2-oxo-4-N-propyl-1-pyrrolidinyl) butanamide, which involves: using a chiral reagent comprising R-mandelic acid, D-tartaric acid or D5 malic acid.
IPC 分类号	A61K-031/4015 ; B01J-023/44 ; C07D-207/27
国家	印度
专业领域	医药卫生
语种	英语
成果类型	专利
文献类型	科技成果
条目标识符	http://119.78.100.226:8889/handle/3KE4DYBR/20966
专题	中国科学院新疆生态与地理研究所
作者单位	AUROBINDO PHARMA LTD (AUMA-C)
推荐引用方式 GB/T 7714	MEENAKSHISUNDERAM S,ALI N A S,DUSSA N,et al. Preparing brivaracetam used for treating partial-onset seizure, involves reducing (S)-2-(2-oxo-4-propyl-2,5-dihydro-1H-pyrrol-1-yl) butanamide in presence of catalyst, hydrogen, organic acid followed by resolution of mixture of isomers via chiral reagent, desalification of chiral salt in base. IN202341052597-A[P]. 2023.

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