Preparing gemigliptin for treating type 2 diabetes by reacting amine compound with difluoro compound, deprotecting tert-butyl (S)-(4-(2,4-bis(trifluoromethyl)-dihydropyrido[3,4-d]pyrimidin-7(6H)-yl)-1-(5,5-difluoro-2-oxopiperidin-1-yl)-4- oxobutan-2-yl)carbamate to obtain gemigliptin
	SOMISETTI N R; NANDEPU H; NANDEPU V R
	2023-09-05
专利权人	METROCHEM API PVT LTD (METR-Non-standard)
申请日期	2023-09-05
专利号	IN202341059510-A
成果简介	NOVELTY - Preparing gemigliptin of formula (I) or its salts comprises: (a) reacting amine based compound of formula (II) with 5-amino-4,4-difluoro compound (III) or its salt to provide tert-butyl (S)-3-((tert-butoxycarbonyl)amino)-4-(5,5-difluoro-2-oxopiperidin-1-yl)butanoate compound (IV); (b) optionally converting the compound (IV) into (S)-3-((tert-butoxycarbonyl)amino)-4-(5,5-difluoro-2-oxopiperidin-1-yl)butanoic acid compound (IVa); (c) reacting the compound (IV) or (IVa) with a 2,4-bis(trifluoromethyl)-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine compound (V) or its salts, in the presence of a base and/or a condensing agent to provide tert-butyl (S)-(4-(2,4-bis(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidin-7(6H)-yl)-1-(5,5-difluoro-2-oxopiperidin-1-yl)-4- oxobutan-2-yl)carbamate compound (VI); (d) deprotecting the compound (VI) to provide gemigliptin; and (e) optionally converting the gemigliptin into its salts. USE - Process for preparing gemigliptin using intermediates that is used for treating type 2 diabetes. No biological data given. ADVANTAGE - The process is cost effective, shorter process. DETAILED DESCRIPTION - Preparing gemigliptin of formula (I) or its salts comprises: (a) reacting amine based compound of formula (II) with 5-amino-4,4-difluoro compound of formula (III) or its salt to provide tert-butyl (S)-3-((tert-butoxycarbonyl)amino)-4-(5,5-difluoro-2-oxopiperidin-1-yl)butanoate compound of formula (IV); (b) optionally converting the compound (IV) into (S)-3-((tert-butoxycarbonyl)amino)-4-(5,5-difluoro-2- oxopiperidin-1-yl)butanoic acid compound of formula (IVa); (c) reacting the compound (IV) or (IVa) with a 2,4-bis(trifluoromethyl)-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine compound of formula (V) or its salts, in the presence of a base and/or a condensing agent to provide tert-butyl (S)-(4-(2,4-bis(trifluoromethyl)-5,8-dihydropyrido[3,4-d]pyrimidin-7(6H)-yl)-1-(5,5-difluoro-2-oxopiperidin-1-yl)-4- oxobutan-2-yl)carbamate compound of formula (VI); (d) deprotecting the compound (VI) to provide gemigliptin; and (e) optionally converting the gemigliptin into its salts. R1=1-6C alkyl; P=amine protecting group; and R2=1-6C alkyl. INDEPENDENT CLAIMS are included for: 1. a process for the preparation of a compound (IV) comprising: reacting a compound (II) with a compound (III) or its salt, in the presence of a suitable reducing agent to provide a compound (IV); 2. a process for preparation of a compound (III) or its salts comprising: converting a compound of formula (VII), into ethyl 4,4-difluoro-5-(((trifluoromethyl)sulfonyl)oxy) pentanoate compound of formula (VIII); converting the compound (VIII) into ethyl 5-azido-4,4-difluoropentanoate compound of formula (IX); converting the compound (IX) into a compound (III); and optionally the compound (III) further converted into its organic acid addition salts; 3. a compound of formulae (II, III`, IIIa, III`a) which are used as an intermediate for the preparation of Gemigliptin and its intermediates. R3=optionally substituted 1-6C alkyl, or aryl.
IPC 分类号	C07C-013/615 ; C07C-229/36 ; C07C-025/13 ; C07D-207/22 ; C07D-209/52 ; C07D-213/63 ; C07D-471/04
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/20496
专题	中国科学院新疆生态与地理研究所
作者单位	METROCHEM API PVT LTD (METR-Non-standard)
推荐引用方式 GB/T 7714	SOMISETTI N R,NANDEPU H,NANDEPU V R. Preparing gemigliptin for treating type 2 diabetes by reacting amine compound with difluoro compound, deprotecting tert-butyl (S)-(4-(2,4-bis(trifluoromethyl)-dihydropyrido[3,4-d]pyrimidin-7(6H)-yl)-1-(5,5-difluoro-2-oxopiperidin-1-yl)-4- oxobutan-2-yl)carbamate to obtain gemigliptin. IN202341059510-A[P]. 2023.

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