KR950014105A - Method for preparing azole derivatives - Google Patents

Method for preparing azole derivatives Download PDF

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KR950014105A
KR950014105A KR1019930024780A KR930024780A KR950014105A KR 950014105 A KR950014105 A KR 950014105A KR 1019930024780 A KR1019930024780 A KR 1019930024780A KR 930024780 A KR930024780 A KR 930024780A KR 950014105 A KR950014105 A KR 950014105A
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South Korea
Prior art keywords
formula
alkali metal
hydrogen
group
catalyst
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KR1019930024780A
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Korean (ko)
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김기성
김덕규
김문성
윤영구
조종환
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유충식
동아제약 주식회사
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Priority to KR1019930024780A priority Critical patent/KR950014105A/en
Publication of KR950014105A publication Critical patent/KR950014105A/en

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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 항진균제로 유용한 다음 일반식( I )로 표시되는 트리아졸 유도체, 그의 입체 이성질체 및 그의 약제학적으로 허용되는 산부가염을 제조하는 방법에 관한 것으로, 불활성 유기용매와 알칼리금속 염기 존재하, 다음 일반식(Ⅲ)로 표시되는 트리아졸 페닐 피페라진 페놀 유도체를 일반식(V)로 표시되는 18-크라운-6과 같은 크라운 에테르(Crownether)를 촉매로 사용하여 일반식(Ⅱ)로 표시되는 아졸 유도체와 반응시켜서 목적화합물을 제조한다.The present invention relates to a process for preparing triazole derivatives represented by the following general formula (I), useful as antifungal agents, stereoisomers thereof and pharmaceutically acceptable acid addition salts thereof, in the presence of an inert organic solvent and an alkali metal base, Azole represented by formula (II) using a triazole phenyl piperazine phenol derivative represented by formula (III) as a catalyst using a crown ether such as 18-crown-6 represented by formula (V) as a catalyst Reaction with a derivative yields the desired compound.

상기 식에서, B는 CH또는 N이며, Ar은 할로겐 및 메톡시기로 구성된 군에서 독립적으로 선택된 1개 또는 2개의 라디칼로 임의로 치환된 페닐기이며, R1은 수소, C1-4의 저급알킬 또는 아릴알킬이며, X는 할로겐, 메탈설포닐옥시 또는 4-메틸벤젠설포닐옥시 등의 설폰산기 같은 반응성 에스테르잔기이며, Y는 수소 또는 알칼리금속 즉, 소디움, 칼륨, 바륨 또는 세슘 등이며, M은 소디움, 칼륨, 바륨 또는 세슘등의 알칼리 금속이고, Z는 하이드록시기, 탄산영, 메톡시, 에톡시, t-부톡시 또는 수소 등이고, R2는 및 R3는 서로 같거나 다를 수 있으며, 알킬, 헥실, 페닐 또는 벤조일기이고, n은 4-8의 정수로 폴리에테르환을 이룬다.Wherein B is CH or N, Ar is a phenyl group optionally substituted with one or two radicals independently selected from the group consisting of halogen and methoxy groups, R 1 is hydrogen, lower alkyl or aryl of C 1-4 Alkyl, X is a reactive ester residue such as a sulfonic acid group such as halogen, metalsulfonyloxy or 4-methylbenzenesulfonyloxy, Y is hydrogen or an alkali metal such as sodium, potassium, barium or cesium, and M is sodium , An alkali metal such as potassium, barium or cesium, Z is a hydroxy group, carbonate, methoxy, ethoxy, t-butoxy or hydrogen, etc., R 2 and R 3 may be the same or different from each other, alkyl , Hexyl, phenyl or benzoyl group, n forms a polyether ring with an integer of 4-8.

본 발명은 새로운 방법에 의해 개발된 카폴링(coupling)효과가 우수한 촉매로 크라운 에테르를 이용함으로써 현재 가동중인 공정을 살릴 수 있을 뿐만 아니라, 종래의 기술에 비해 온화한 반응온도, 짧은 시간, 높은 수율로 목적화합물을 제조할 수 있다.The present invention not only saves the current process by using the crown ether as a catalyst having excellent coupling effect developed by the new method, but also has a mild reaction temperature, short time, and high yield compared to the prior art. The desired compound can be prepared.

Description

아졸 유도체의 제조 방법Process for preparing azole derivatives

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

Claims (5)

다음 일반식(Ⅲ)의 화합물을 일반식(Ⅳ)의 알칼리금속 염기 존재하, 일반식(V)의 크라운에테르화합물을 촉매로 하여 일반식(Ⅱ)의 반응성 에스테르와 가온 상태에서 반응시킴을 특징으로 하는 일반 식( I )로 표시되는 아졸 화합물 및 이의 약학적으로 허용되는 산부가염의 제조방법.The following compounds of formula (III) are reacted in the presence of alkali metal bases of formula (IV) with a reactive ester of formula (II) in a warmed state with a crown ether compound of formula (V) as a catalyst. A method for producing an azole compound represented by the general formula (I) and pharmaceutically acceptable acid addition salts thereof. 상기 식에서, B는 CH또는 N이며, Ar은 할로겐 및 메륵시기로 구성된 군에서 독립적으로 선택된 1개 또는 2개의 라디칼로 임의로 치환된 페닐기이며, R1은 수소, C1-C4일 저급알킬 또는 아릴알킬이며, X는 할로겐 또는, 메탄설포닐옥시 또는 4-메틸벤젠설포닐옥시 등의 설폰산기 갈은 반응성 에스테르잔기이며, Y는 수소 또는 알칼리금속이며, M은 알칼리 금속이고, Z는 하이드록시기, 탄산염, 메톡시, 에톡시,t-부톡시 또는 수소이고, R2및 R3는 서로 같거나 다를 수 있으며, 저급알킬, 헥실, 페닐 또는 벤조일기이고,n은 4-8의 정수로 폴리에테르환을 이룬다.Wherein B is CH or N, Ar is a phenyl group optionally substituted with one or two radicals independently selected from the group consisting of halogen and mesoxy groups, R 1 is hydrogen, C 1 -C 4 day lower alkyl or Arylalkyl, X is halogen or a sulfonic acid group ground reactive ester residue such as methanesulfonyloxy or 4-methylbenzenesulfonyloxy, Y is hydrogen or an alkali metal, M is an alkali metal, and Z is hydroxide Timing, carbonate, methoxy, ethoxy, t-butoxy or hydrogen, R 2 and R 3 may be the same or different from each other, a lower alkyl, hexyl, phenyl or benzoyl group, n is an integer of 4-8 It forms a polyether ring. 제1항에 있어서,0-알킬화반응시 50-90℃에서, 2-7시간 동안 행함을 특징으로 하는 제조방법The method according to claim 1, wherein the process is performed at 50-90 ° C. for 2-7 hours during the 0-alkylation reaction. 제1항에 있어서, 촉매로 18-크라운-6-을 사응함을 특징으로 하는 제조방법.The process according to claim 1, characterized in that 18-crown-6- is reacted with a catalyst. 제1항에 있어서, 불활성 유기용매로 디메틸설폭사이드 또는 디메틸포름아미드를 사용함을 특징으로 하는 제조방법.The method according to claim 1, wherein dimethyl sulfoxide or dimethylformamide is used as the inert organic solvent. 제1항에 있어서, 알칼리금속의 염기로 수산화나트륨 또는 수산화칼륨을 사용함을 특징으로 하는 제조방법.The method according to claim 1, wherein sodium hydroxide or potassium hydroxide is used as the base of the alkali metal. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930024780A 1993-11-19 1993-11-19 Method for preparing azole derivatives KR950014105A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160145237A (en) * 2015-06-09 2016-12-20 한국기계연구원 Wear Resistance High Strength Brass Alloy and Method for Manufacturing the Same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160145237A (en) * 2015-06-09 2016-12-20 한국기계연구원 Wear Resistance High Strength Brass Alloy and Method for Manufacturing the Same

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