KR970042551A - Method for preparing benzodiazepines derivatives - Google Patents

Method for preparing benzodiazepines derivatives Download PDF

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Publication number
KR970042551A
KR970042551A KR1019950051751A KR19950051751A KR970042551A KR 970042551 A KR970042551 A KR 970042551A KR 1019950051751 A KR1019950051751 A KR 1019950051751A KR 19950051751 A KR19950051751 A KR 19950051751A KR 970042551 A KR970042551 A KR 970042551A
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South Korea
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formula
compound
carboxylic acid
esters
addition salts
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KR1019950051751A
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Korean (ko)
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KR0167401B1 (en
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박희석
박진규
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강재헌
동국제약 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

본 발명은 벤조디아제핀-3-카르복시산 알킬 유도체를 제조하는 유용한 방법에 관한 것이다. 더욱 상세하게는 2-아미노-벤조산 유도체로부터 5,6-디히드로-5-메틸-6-옥소-4H-이미다조[1,5-a][1,4]벤조디아제핀-3-카르복시산 알킬 유도체를 제조하는 간편하고, 유용한 방법에 관한 것이다.The present invention relates to a useful method for preparing benzodiazepines-3-carboxylic acid alkyl derivatives. More specifically, 5,6-dihydro-5-methyl-6-oxo-4H-imidazo [1,5-a] [1,4] benzodiazepine-3-carboxylic acid alkyl derivatives are obtained from 2-amino-benzoic acid derivatives. A simple, useful method of manufacturing.

Description

벤조디다제핀 유도체의 제조방법Method for preparing benzodiazepine derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (5)

불활성 용매하에서 일반식(V)의 화합물을 저급 알킬아민으로 처리하여 일반식(VI)의 히드록시알킬아민 화합물을 제조하고,Treating a compound of formula (V) with a lower alkylamine in an inert solvent to prepare a hydroxyalkylamine compound of formula (VI), 일반식(VI)의 화합물을 알코올의 할로겐화 시약 부가에 의해 일반식(VII)의 화합물을 제조하고,Compound of formula (VI) is prepared by addition of a halogenating reagent of alcohol to prepare a compound of formula (VII), 일반식(VII)의 화합물을 염기 존재하에서 폐환시켜 일반식(I)의 벤조디아제핀-3-카르복시산 알킬 유도체 및 그것의 약제학적으로 허용되는 산부가염 또는 에스테르를 제조하는 방법.A method for preparing a benzodiazepine-3-carboxylic acid alkyl derivative of formula (I) and pharmaceutically acceptable acid addition salts or esters thereof by ring closure of the compound of formula (VII) in the presence of a base. 상기 일반식에서, R1은 메틸, 에틸 또는 이소프로필이고,; R2및 R3각각 수소 또는 탄소수 1~6의 저급알킬이며, R4는 수소, 할로겐 또는 트리플루오로메틸이고 ; C로 표시된 탄소원자는 S- 또는 R,S- 배위를 지닌다.In the above formula, R 1 is methyl, ethyl or isopropyl; R 2 and R 3 are each hydrogen or lower alkyl having 1 to 6 carbon atoms, and R 4 is hydrogen, halogen or trifluoromethyl; Carbon atoms represented by C have an S- or R, S- configuration. 제1항에 있어서, 일반식(V)의 화합물은 일반식(II)의 2-아미노-벤조산 유도체를 출발물질로하여The compound of formula (V) according to claim 1, wherein the compound of formula (V) is a starting material of 2-amino-benzoic acid derivative 염기성 조건하에서 고리화시켜, 일반식(III)의 화합물을 제조하고,By cyclization under basic conditions to prepare the compound of formula (III), 일반식(III)의 화합물에 이탈기 X를 부가시켜 일반식(IV)의 화합물을 제조한 후,After adding leaving group X to the compound of formula (III) to prepare a compound of formula (IV), 상기식에서, X는 포스피닐그룹, 할로겐원자, 알킬티오그룹, 아르알킬티오그룹, n-니트로소알킬아미노그룹, 알콕시그룹을 나타낸다. 불활성 용매하에서 이소시아노아세트산알킬을 강염기 존재하에서 반응시켜 일반식(V)에 벤조옥사제핀온 유도체를 제조함을 특징으로 하는 일반식(I)의 벤조디아제핀-3-카르복시산 알킬 유도체 및 그것의 약제학적으로 허용되는 산부가염 또는 에스테르의 제조방법.Wherein X represents a phosphinyl group, a halogen atom, an alkylthio group, an aralkylthio group, an n-nitrosoalkylamino group, an alkoxy group. Benzodiazepine-3-carboxylic acid alkyl derivatives of general formula (I) and pharmaceuticals thereof, characterized in that benzoxazepinone derivatives are prepared in general formula (V) by reacting alkyl isocyanate acetate in the presence of a strong base in an inert solvent. Method for preparing acid addition salts or esters as is acceptable. 제1항 또는 제2항에 있어서, 염기는 알칼리금속알콕사이드, 알칼리금속 수소화물, 알칼리금속 아미드 3급아민 등을 사용함을 특징으로 하는 일반식(I)의 벤조디아제핀-3-카르복시산 알킬 유도체 및 그것의 약제학적으로 허용되는 산 부가염 또는 에스테르의 제조방법.The benzodiazepine-3-carboxylic acid alkyl derivative of general formula (I) according to claim 1 or 2, wherein the base uses an alkali metal alkoxide, an alkali metal hydride, an alkali metal amide tertiary amine or the like. Processes for preparing pharmaceutically acceptable acid addition salts or esters. 제1항 또는 제2항에 있어서, 불활성용매는 아세토니트릴, 피리딘, 디에틸포름아미드, 헥사메틸인산 트리아미드, 디메틸술폭사이드, 테트라히드로푸란 등임을 특징으로 하는 일반식(I)의 벤조디아제핀-3-카르복시산 알킬 유도체 및 그것의 약제학적으로 허용되는 산 부가염 또는 산에스테르의 제조방법.The benzodiazepine of formula (I) according to claim 1 or 2, wherein the inert solvent is acetonitrile, pyridine, diethylformamide, hexamethylphosphate triamide, dimethyl sulfoxide, tetrahydrofuran, or the like. -Carboxylic acid alkyl derivatives and pharmaceutically acceptable acid addition salts or acid esters thereof. 일반식(V)로 표시되는 일반식(I)의 벤조디아제핀-3-카르복시산 알킬 유도체 및 그것의 약제학적으로 허용되는 산 부가염 또는 에스테르의 개조에 사용되는 반응 중간체Reaction intermediates used in the modification of benzodiazepines-3-carboxylic acid alkyl derivatives of general formula (I) represented by general formula (V) and pharmaceutically acceptable acid addition salts or esters thereof 상기식에서, R1은 메틸, 에틸 또는 이소프로필이고 ; R2는 수소 또는 탄소수 1~6의 저급알킬이며, R4는 수소, 할로겐 또는 트리플루오로메틸이고 ; C로 표시된 탄소원자는 S- 또는 R,S- 배위를 지닌다.Wherein R 1 is methyl, ethyl or isopropyl; R 2 is hydrogen or lower alkyl having 1 to 6 carbon atoms, R 4 is hydrogen, halogen or trifluoromethyl; Carbon atoms represented by C have an S- or R, S- configuration.
KR1019950051751A 1995-12-19 1995-12-19 A process for preparing benzodiazepine derivatives KR0167401B1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100283474B1 (en) * 1999-01-18 2001-02-15 박호군 Flumazenil derivative having n2s2ligand and preparation thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100283474B1 (en) * 1999-01-18 2001-02-15 박호군 Flumazenil derivative having n2s2ligand and preparation thereof

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