KR890009940A - Silyl cephalosporin compound and preparation method thereof - Google Patents

Silyl cephalosporin compound and preparation method thereof Download PDF

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Publication number
KR890009940A
KR890009940A KR870014208A KR870014208A KR890009940A KR 890009940 A KR890009940 A KR 890009940A KR 870014208 A KR870014208 A KR 870014208A KR 870014208 A KR870014208 A KR 870014208A KR 890009940 A KR890009940 A KR 890009940A
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South Korea
Prior art keywords
acid
general formula
silyl
group
producing
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KR870014208A
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Korean (ko)
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KR900003562B1 (en
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장문호
고훈영
최경일
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이정오
한국과학 기술원
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

내용 없음No content

Description

실릴세팔로스포린 화합물 및 그 제조방법Silyl cephalosporin compound and preparation method thereof

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

Claims (9)

히기식 (Ⅰ)로 표시되는 실릴세팔로스포린 화합물.The silyl cephalosporin compound represented by the formula (I). 일반식 (Ⅰ)에 있어서 R₁은 수소 또는 트리틸기를 표시하며, R₂는 아세토메틸(1-메틸-1H-테트라졸-5-일) 티오메틸또는 비닐기를 표시한다. 그리고 R₃는 수소 또는 나트륨을 표시하며 n은 1이며, X,Y 및 Z는 각각 메틸기를 표시한다.In general formula (I), R 'represents hydrogen or a trityl group, and R2 represents acetomethyl. (1-methyl-1H-tetrazol-5-yl) thiomethyl Or a vinyl group. And R₃ represents hydrogen or sodium, n is 1, and X, Y and Z each represent a methyl group. 하기 일반식(Ⅱ)의 실릴화합물과 하기 일반식(Ⅲ)의 셀팔로 스포린을 유기용매와 산 또는 염기 존재하에 반응시키는 것을 특징으로 하는 하기 일반식(Ⅰ)로 표시되는 실릴팔로스포린 화합물의 제조방법.Preparation of the silyl palosporin compound represented by the following general formula (I) characterized by reacting the silyl compound of the following general formula (II) and the celphalosporin of the general formula (III) in the presence of an organic solvent and an acid or a base. Way. 일반식(Ⅰ)에 있어서, R₁은 수소 또는 트리틸기를 표시하며, R₂는 아세톡시메틸(-CH₁-O-CO-CH₃), 1-메틸-1H-테트라졸-5-일 티오메틸 또는 비닐기를 표시하고 R₃는 수소 또는 나트륨을 표시하며 n은 1이다. 그리고 X,Y 및 X는 각각 메틸기를 표시한다. 일반식(Ⅱ)에 있어서, R₁은 수소 또는 트리틸기를 표시하며, R₂는 카르복실산 또는 메틸카르복실산기를 표시하고, n은 1이다. 그리고 X,Y 및 Z는 각각 메틸기를 표시한다. 일반식(Ⅲ)에 있어서, R₂는 아세톡시메틸, (1-메틸-1H-테틀라졸-5-일)티오메틸 또는 비닐기를 표시하고 R₃는 수소 또는 나트륨을 표시한다.In general formula (I), R 'represents hydrogen or a trityl group, and R2 represents acetoxymethyl (-CHO-O-CO-CH₃), 1-methyl-1H-tetrazol-5-yl thiomethyl or vinyl And R₃ represents hydrogen or sodium and n is 1. And X, Y and X each represent a methyl group. In general formula (II), R 'represents a hydrogen or a trityl group, R2 represents a carboxylic acid or a methylcarboxylic acid group, n is 1. And X, Y and Z each represent a methyl group. In general formula (III), R2 represents acetoxymethyl, (1-methyl-1H-tetrazol-5-yl) thiomethyl or a vinyl group and R3 represents hydrogen or sodium. 제2항에 있어서, 용매로 물, 아세톤, 디옥산, 아세토니트릴, 클로로포름, 메틸렌클로리드, 테트라하이 드로퓨란, 에틸아세테이트, N, N-디메틸호포름아미드 중에서 선택하여 반응시키는 것을 특징으로 하는 일반식(Ⅰ)의 실릴세팔로스포린 화합물의 제조방법.The method of claim 2, wherein the solvent is selected from water, acetone, dioxane, acetonitrile, chloroform, methylene chloride, tetrahydrofuran, ethyl acetate, N, and N-dimethylhoformamide. A process for producing the silyl cephalosporin compound of formula (I). 제2항에 있어서, 염기로 알칼리 금속히드록시드, 알칼리 금속 아세테이드, 트리-저급알킬 아민, 아민피리딘, N-저급-알킬모르포린, N,N-디-(저급)-알킬벤질아민, N,N-디-(저급)-알킬아닐린 중에서 선택하여 반응시키는 것을 특징으로 하는 일반식(Ⅰ)의 실릴세팔로스포린 화합물의 제조방법.3. Alkali metal hydroxide, alkali metal acetate, tri-lower alkyl amine, aminepyridine, N-lower-alkylmorpholine, N, N-di- (lower) -alkylbenzylamine as base And N, N-di- (lower) -alkylaniline. The method for producing a silylcephalosporin compound of formula (I), wherein the reaction is selected from the group consisting of the following compounds. 제2항에 있어서, 반응온도를 0℃내지 25℃에서 반응시키는 것을 특징으로 하는 일반식(Ⅰ)의 실릴세팔로스포린 화합물의 제조방법.The process for producing the silyl cephalosporin compound of formula (I) according to claim 2, wherein the reaction temperature is reacted at 0 ° C to 25 ° C. 제2항에 있어서, 일반식(Ⅰ)의 실릴세팔로스포린 화합물의 2위치의 보호기를 산 존재하에 제거하여 일반식(Ⅰ)의 실릴세팔로스포린 화합물의 제조방법.The process for producing the silyl cephalosporin compound according to claim 2, wherein the protecting group at the 2-position of the silyl cephalosporin compound of the general formula (I) is removed in the presence of an acid. 제2항에 있어서, 일반식(Ⅰ)의 실릴세팔로스포린 화합물의 4위치의 카르복실산을 염기 존재하에 일반식(Ⅰ)의 실릴세팔로스포린의 수용성 염의 제조방법.The process for producing a water-soluble salt of silylcephalosporin of general formula (I) according to claim 2, wherein the carboxylic acid at position 4 of the silylcephalosporin compound of general formula (I) is present in the presence of a base. 제6항에 있어서, 산으로 포름산, 아세트산, 프로피온산, 트리폴루오르아세트산, 염산, 황산, 염화브롬산 중에서 선택하여 반응시키는 것을 특징으로 하는 일반식(Ⅰ)의 실릴세팔로스포린 화합물의 제조방법The method for producing a silyl cephalosporin compound according to claim 6, wherein the acid is selected from formic acid, acetic acid, propionic acid, tripoloric acid, hydrochloric acid, sulfuric acid, and bromic acid. 제7항에 있어서, 염기로 나트륨 2-에틸헥실노에이트를 사용하는 것을 특징으로 하는 일반식(Ⅰ)의 실릴셀로스포린 화합물의 제조방법.8. The process for producing the silylcellosporin compound of formula (I) according to claim 7, wherein sodium 2-ethylhexylnoate is used as the base. ※ 참고사항：최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019870014208A 1987-12-12 1987-12-12 Process for preparing sillyl cephalosproin derivatives KR900003562B1 (en)

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KR1019870014208A KR900003562B1 (en) 1987-12-12 1987-12-12 Process for preparing sillyl cephalosproin derivatives

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Application Number Priority Date Filing Date Title
KR1019870014208A KR900003562B1 (en) 1987-12-12 1987-12-12 Process for preparing sillyl cephalosproin derivatives

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KR890009940A true KR890009940A (en) 1989-08-05
KR900003562B1 KR900003562B1 (en) 1990-05-21

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