KR840006337A - Method for preparing azetidinyl sulfonic acid and derivatives thereof - Google Patents

Method for preparing azetidinyl sulfonic acid and derivatives thereof Download PDF

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KR840006337A
KR840006337A KR1019830004744A KR830004744A KR840006337A KR 840006337 A KR840006337 A KR 840006337A KR 1019830004744 A KR1019830004744 A KR 1019830004744A KR 830004744 A KR830004744 A KR 830004744A KR 840006337 A KR840006337 A KR 840006337A
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알렌 슬루사르치크 윌리암
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조오지 제이. 코에서
이이. 아르. 스퀴부. 앤드 산즈 인코오포레이티드
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    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
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    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
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    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Abstract

내용 없음No content

Description

아제티딘일 술폰산 및 그의 유도체의 제조방법Method for preparing azetidinyl sulfonic acid and derivatives thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (15)

다음 일반식(Ⅴ)의 화합물을 환화 반응시켜 다음 일반식(Ⅵ)의 생성물을 얻고, 이 생성물을 할로겐화시약 및 메톡시화 시약처리로 매톡시화시켜서 R2가 메톡시기인 일반식(Ⅵ)의 화합물을 얻은 다음, 이 생성물로 부터 아미노 보호기를 제거하여 R1가 수소인 생성물을 얻고, 이 생성물을 아실화시켜서 R1가 아실기인 생성물을 얻는 것을 특징으로 하는 일반식(Ⅰ)의 β-락탐 또는 이들의 염 또는 에스테르를 제조하는 방법.The compound of formula (V) is then cyclized to obtain the product of formula (VI), which is methoxylated with a halogenated reagent and a methoxylation reagent to give R 2 a methoxy group. And then the amino protecting group is removed from this product to obtain a product wherein R 1 is hydrogen, and the product is acylated to obtain a product wherein R 1 is acyl group, or β-lactam of formula (I) Methods of preparing their salts or esters. 위의 일반식에서 R1는아실기, 수소 또는 아미노 보호기이며, R2는 수소 또는 메톡시이고[일반식(Ⅵ)에서의 R2는 수소임].In the above formula, R 1 is an acyl group, hydrogen or amino protecting group, R 2 is hydrogen or methoxy [R 2 in formula (VI) is hydrogen]. R3및 R4는 서로 동일하거나 상이하며, 각각 수소, 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 페닐기, 치환페닐기 또는 4원, 5원, 6원 또는 7원 헤테로환기이거나, 또는 R3및 R4중의 어느 하나가 수소이면, 다른 하나는 아지도기, 할로메틸기, 디할로메틸기, 트리할로메틸기, 알콕시카르보닐기, 2-페닐에테닐기, 2-페닐에티닐기, 카르복실기, -CH2-X1, -S-X2,또는-NX6X7(여기서, X1은 아지도기, 아미노기, (-NH2), 히드록시기, 알카노일아미노기, 알킬술포닐옥시기, 페닐술포닐옥시기, (치환페닐) 술포닐옥시기, 페닐기, 치환페닐기, 시아노기, -S-X2또는 -O-X2이며 X2는 알킬기, 치환알킬기, 페닐기, 치환페닐기, 페닐알킬기, (치환페닐)알킬기, 알칼노일기, 치환알카노일기, 페닐카르보닐기, (치환페닐)카르보닐기 또는 헤테로아릴카르보닐이고, X3및 X4중의 어느 하나가 수소일 경우에 다른 하나는 수소 또는 알킬기이거나, X3및 X4는 이들이 부착되어 있는 탄소원자와 결합하여 시클로알킬기를 형성하며, X5는 포로밀기, 알칼노일기, 페닐카르보닐기, (치환페닐)카르보닐기, 페닐알킬카르보닐기, (치환페닐)알킬카르보닐기, 카르복실기, 알콜시카르보닐기, 아미노카르보닐기(NH2-OC-), (치환아미노)카르보닐기 또는 시아노기(C=N)이고, A는 -CH=CH-, CH2-CH=CH1, -(CH2)n-, -(CH2)n, -O-, -(CH2)n'-NH- 또는 -(CH2)n'-S-CH2이며, n는 0,1,2 또는 3이고, n'는 1 또는 2이며, X6및 X7은 서로 동일하거나 상이하며 각각 수소 또는 알킬기 이거, , X6은 수소, X7은 아미노기, 치환아미노기, 아실아미노기 또는 알콕시기이다) R5및 R6은 서로 동일하거나 상이하며, 각각 수소, 알킬기 알케닐기, 알키닐기, 페닐기, 치환페닐기, 시클로알킬기, 도는 R7'이거나, R5및 R6가 그들이 부착되어 있는 탄소원자와 결합하여 시클로알킬기 또는 R7'를 형성하거나, R5및 R6중의 어느 하나가 수소이고 나머지 하나가 아지도기, 할로메틸기, 디할로메틸기, 트리할로메틸기, 알톡시카르보닐기, 2-페닐에테닐기, 2-페닐에티닐기, 카르복실기, -CH2X1-, -S-X2, -O-X2또는이다.)R 3 and R 4 are the same as or different from each other, and each is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a phenyl group, a substituted phenyl group or a 4, 5, 6 or 7 membered heterocyclic group, or R 3 and If any one of R 4 is hydrogen, the other is an azido group, a halomethyl group, a dihalomethyl group, a trihalomethyl group, an alkoxycarbonyl group, a 2-phenylethenyl group, a 2-phenylethynyl group, a carboxyl group, -CH 2- X 1 , -SX 2 , or -NX 6 X 7 (wherein X 1 is an azido group, amino group, (-NH 2 ), hydroxy group, alkanoylamino group, alkylsulfonyloxy group, phenylsulfonyloxy group, (substituted phenyl) sulfonyloxy group, phenyl group, substituted phenyl group , Cyano group, -SX 2 or -OX 2 and X 2 is an alkyl group, substituted alkyl group, phenyl group, substituted phenyl group, phenylalkyl group, (substituted phenyl) alkyl group, alkanoyl group, substituted alkanoyl group, phenylcarbonyl group, (substituted phenyl) carbonyl group Or heteroarylcarbonyl, and when one of X 3 and X 4 is hydrogen, the other is hydrogen or an alkyl group, or X 3 and X 4 combine with the carbon atom to which they are attached to form a cycloalkyl group, X 5 is a formomyl group, an alkanoyl group, a phenylcarbonyl group, a (substituted phenyl) carbonyl group, a phenylalkylcarbonyl group, a (substituted phenyl) alkylcarbonyl group, a carboxyl group, an alcoholic carbonyl group, an aminocarbonyl group (NH 2 -OC-), (substituted amino) carbonyl group or Is a cyano group (C = N), A is -CH = CH-, CH 2 -CH = CH 1 ,-(CH 2 ) n -,-(CH 2 ) n , -O-,-(CH 2 ) n '-NH- or-(CH 2 ) n ' -S-CH 2 , n is 0,1,2 or 3, n 'is 1 or 2, X 6 and X 7 are the same as or different from each other Hydrogen or an alkyl group, wherein X 6 is hydrogen, X 7 is an amino group, a substituted amino group, an acylamino group or an alkoxy group) R 5 and R 6 are the same as or different from each other, and each hydrogen, alkyl group alkenyl group, alkynyl group, phenyl group, A substituted phenyl group, a cycloalkyl group, or R 7 ', or R 5 and R 6 combine with the carbon atom to which they are attached to form a cycloalkyl group or R 7 ', or one of R 5 and R 6 is hydrogen and the other an azido group, a halo group, a methyl group to a methyl group, and a trihalomethyl-dihalo, Al-butoxycarbonyl group, a 2-phenylethyl group, Te, Ti in the 2-phenyl group, a carboxyl group, -CH 2 X 1 -, -SX 2, -OX 2 or to be.) 제1항에 있어서, R2가 수소임을 특징으로 하는 제조방법.The process according to claim 1, wherein R 2 is hydrogen. 제2항에 있어서, R3및 R4중의 어느 하나가 기가 수소가 아님을 특징으로 하는 제조방법.The process according to claim 2, wherein any one of R 3 and R 4 is not hydrogen. 제2항에 있어서, R3가 수소이고, R4가 메틸기임을 특징으로 하는 제조방법.The process according to claim 2, wherein R 3 is hydrogen and R 4 is a methyl group. 제2항에 있어서, R3가 메틸기이고 R4가 수소임을 특징으로 하는 제조방법.The process according to claim 2, wherein R 3 is a methyl group and R 4 is hydrogen. 제2항에 있어서, R5및 R6이 각각 수소임을 특징으로 하는 제조방법.The process according to claim 2, wherein R 5 and R 6 are each hydrogen. 제2항에 있어서, R5및 R5이 각각 메틸기임을 특징으로 하는 제조방법.The method according to claim 2, wherein R 5 and R 5 are each a methyl group. 제2항에 있어서, R1가 (Z)-2-아미노-α-[(1-카르복시-1-메틸에톡시)이미노]-4-티아졸아세틸기임을 특징으로 하는 제조방법.The process according to claim 2, wherein R 1 is a (Z) -2-amino-α-[(1-carboxy-1-methylethoxy) imino] -4-thiazoleacetyl group. 제1항에 있어서, R2, R5및 R6이 각각 수소이고 R3및 R4중의 어느 하나가 알킬기이고 나머지 하나는 수소임을 특징으로 하는 제조방법.The process according to claim 1, wherein R 2 , R 5 and R 6 are each hydrogen and one of R 3 and R 4 is an alkyl group and the other is hydrogen. 제3항에 있어서, R2, R3, R5및 R6이 각각 수소이고, R4각 메틸기임을 특징으로 하는 제조방법.The process according to claim 3, wherein R 2 , R 3 , R 5 and R 6 are each hydrogen and each R 4 methyl group. 제3항에 있어서, R2, R4, R5및 R6, 각각 수소이고, R3이 메틸기임을 특징으로 하는 제조방법.4. A process according to claim 3 wherein R 2 , R 4 , R 5 and R 6 are each hydrogen and R 3 is a methyl group. 제1항에 있어서, R1가 수소임을 특징으로 하는 제조방법.The process according to claim 1, wherein R 1 is hydrogen. 제1항에 있어서, R1가 아미노 보호기임을 특징으로 하는 제조방법.A process according to claim 1 wherein R 1 is an amino protecting group. 제1항에 있어서, 생성물이 [3S-[3α(Z), 4β]]-2-[[[1-(2-아미노-4-티아졸릴)-2-[[4-메틸-2-옥소-1-(술포메톡시)-3-아제티디닐]아미노]-2-옥소에틸리덴]아미노]옥시]-2-메틸프로판산임을 특징으로 하는 제조방법.The product of claim 1, wherein the product is [3S- [3α (Z), 4β]]-2-[[[1- (2-amino-4-thiazolyl) -2-[[4-methyl-2-oxo -1- (sulfomethoxy) -3-azetidinyl] amino] -2-oxoethylidene] amino] oxy] -2-methylpropanoic acid. 제1항에 있어서, 생성물이 [3S-(3α,4β)]-1-술포메톡시-3-아미노-4-메틸-2-옥소-1-아제티딘임을 특징으로 하는 제조방법.The process according to claim 1, wherein the product is [3S- (3α, 4β)]-1-sulfomethoxy-3-amino-4-methyl-2-oxo-1-azetidine. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019830004744A 1982-10-06 1983-10-06 Azetidinyl sulfonic acid and their derivatives KR900005132B1 (en)

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EP0135194A1 (en) * 1983-09-16 1985-03-27 Takeda Chemical Industries, Ltd. Azetidinones and their production
WO1985004876A1 (en) * 1984-04-24 1985-11-07 Takeda Chemical Industries, Ltd. 2-azetidinone derivatives and process for their preparation
US4581170A (en) * 1984-08-03 1986-04-08 E. R. Squibb & Sons, Inc. N-hydroxyl protecting groups and process and intermediates for the preparation of 3-acylamino-1-hydroxy-2-azetidinones
JPH0649710B2 (en) * 1984-08-06 1994-06-29 藤沢薬品工業株式会社 Azetidinone derivative and method for producing the same
UY34585A (en) 2012-01-24 2013-09-02 Aicuris Gmbh & Co Kg B-LACTAMIC COMPOUNDS REPLACED WITH AMIDINE, ITS PREPARATION AND USE

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AU1993983A (en) 1984-04-12
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DD222016A5 (en) 1985-05-08
GB2129428A (en) 1984-05-16
BE897883A (en) 1984-03-30
NL8303410A (en) 1984-05-01
CH658858A5 (en) 1986-12-15
PH24175A (en) 1990-03-22
ES8504814A1 (en) 1985-04-16
GB8326626D0 (en) 1983-11-09
IE832354L (en) 1984-04-06
AU568312B2 (en) 1987-12-24
LU85033A1 (en) 1984-05-10
IL69917A (en) 1987-10-20
DK457983A (en) 1984-04-07
IL69917A0 (en) 1984-01-31
NO833626L (en) 1984-04-09
ES526282A0 (en) 1985-04-16
IT1171722B (en) 1987-06-10
FR2534253A1 (en) 1984-04-13
NZ205642A (en) 1986-08-08
IT8323172A0 (en) 1983-10-06
SU1318146A3 (en) 1987-06-15
DK457983D0 (en) 1983-10-04

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