KR920018021A - New pyrrolidine derivatives and preparation methods thereof - Google Patents

New pyrrolidine derivatives and preparation methods thereof Download PDF

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Publication number
KR920018021A
KR920018021A KR1019910003933A KR910003933A KR920018021A KR 920018021 A KR920018021 A KR 920018021A KR 1019910003933 A KR1019910003933 A KR 1019910003933A KR 910003933 A KR910003933 A KR 910003933A KR 920018021 A KR920018021 A KR 920018021A
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South Korea
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general formula
compound
following general
represented
group
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KR1019910003933A
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KR930008224B1 (en
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김완주
박명환
백경업
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채영복
재단법인 한국화학연구소
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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

Abstract

내용 없음No content

Description

새로운 피롤리딘 유도체와 그 제조방법New pyrrolidine derivatives and preparation methods thereof

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

Claims (6)

다음 일반식(Ⅰ)로 표시되는 새로운 피롤리딘 유도체New pyrrolidine derivatives represented by the following general formula (I) 상기식중에서, R1는 수소원자 또는 탄소수1~4개의 저급알킬기를 나타내며, R2및 R3는 서로 같거나 다른것으로서, 각각 수소원자, 탄소수 1~3개의 저급알킬기, 시클로알킬기 또는 수산기를 나타내며, n은 1 또는 2의 정수를 나타낸다.In the above formula, R 1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and R 2 and R 3 are the same or different from each other, and each represents a hydrogen atom, a lower alkyl group having 1 to 3 carbon atoms, a cycloalkyl group or a hydroxyl group , n represents an integer of 1 or 2. 다음 일반식(Ⅰa)로 표시되는 새로운 피롤리딘 유도체New pyrrolidine derivatives represented by the following general formula (Ia) 상기 식중에서, R1,R2,R3및 n은 상술한 바와 같으며, A는 염산, 황산, 인산 또는 트리플루오로초산을 나타낸다.Wherein R 1, R 2, R 3 and n are as described above and A represents hydrochloric acid, sulfuric acid, phosphoric acid or trifluoroacetic acid. 다음 일반식(Ⅱ)로 표시되는 화합물에다 트리에틸 포스포노아세테이트 또는 에틸브로모아아세테이트 프리페닐포스포염을 강한 염기존재하에 Witting 반응시켜서 엑소이중결합을 갖는 다음 일반식(Ⅲ)의 화합물을 제조하고, 여기에 에틸클로로포르메이트를 가하고 가열하여 질소 보호기를 에톡시카보닐기로 치환한 다음, 디이소프로필알루미늄 하이드라이드(Dabal-H)나 리티움알루미늄하이드라이드로 에스테르를 환원시켜 다음 일반식(Ⅴ)로 표시되는 알콜화합물을 제조한후 다음 일반식(Ⅵ) 의 메탄술포닐 유도체로 전환시킨 다음 NH(R2,R3)인 아민을 치환시켜서 다음 일반식(Ⅶ)의 화합물을 합성하고 이를 가수분해시켜서 다음 일반식(Ⅰ)로 표시되는 새로운 피롤리딘 유도체를 제조하는 방법.To the compound represented by the following general formula (II) to triethyl phosphonoacetate or ethyl bromoacetate prephenylphospho salt in the presence of a strong base Witting reaction to prepare a compound of the following general formula (III) having an exo double bond, Ethylchloroformate was added thereto and heated to replace the nitrogen protecting group with an ethoxycarbonyl group, followed by reduction of the ester with diisopropylaluminum hydride (Dabal-H) or lithium aluminum hydride, followed by the following general formula (V). After preparing an alcoholic compound represented by the following formula (VI) is converted to a methanesulfonyl derivative of the general formula (VI) and then substituted by the amine of NH (R 2, R 3 ) to synthesize a compound of the following general formula (VII) A method of producing a new pyrrolidine derivative represented by the following general formula (I) by decomposition. 상기 식중에서, R1,R2,R3및 n은 각각 상기 정의한 바와 같고, A는 염산, 황산, 인산 또는 트리플루오로초산을 나타낸다.Wherein R 1, R 2, R 3 and n are each as defined above and A represents hydrochloric acid, sulfuric acid, phosphoric acid or trifluoroacetic acid. 제 3 항에 있어서, 상기 일반식(Ⅴ)로 표시되는 화합물중 이중결합늘 중심으로 한 이성체인 시스체와 트란스체를 분리하여 상기 일반(Ⅰ)의 화합물이 시스-이성체, 트린스-이성체 또는 이들 이성체 혼합물을 제조하는 방법.The compound of general formula (I) according to claim 3, wherein the compound of general formula (I) is a cis-isomer, a tris-isomer or Process for preparing these isomeric mixtures. 다음 일반식(Ⅰ)로 표시되는 피롤리딘 유도체를 퀴놀론 화합물 또는 세팔로스포린 화합물의 제조시 중간체로 이용하는 방법.A method of using a pyrrolidine derivative represented by the following general formula (I) as an intermediate in the preparation of a quinolone compound or a cephalosporin compound. 상기 식중에서, R1,R2,R3및 n은 상술한 바와 같다.Wherein R 1, R 2, R 3 and n are as described above. 다음 일반식(Ⅰ)로 표시되는 피롤리딘 유도체 또는 그 염을 도입기로 함유하는 퀴놀론 화합물 또는 세팔로스포린 화합물을 향균 또는 항생활성의 유효성분으로 포함하는 의약조성물.A pharmaceutical composition comprising a quinolone compound or a cephalosporin compound containing a pyrrolidine derivative represented by the following general formula (I) or a salt thereof as an introducing group as an antibacterial or anti-bioactive active ingredient. 상기 식중에서, R1,R2,R3및 n은 상술한 바와 같다.Wherein R 1, R 2, R 3 and n are as described above. ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.※ Note: This is to be disclosed by the original application.
KR1019910003933A 1991-03-12 1991-03-12 Process for the production of pyrrolidine derivatives KR930008224B1 (en)

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Application Number Priority Date Filing Date Title
KR1019910003933A KR930008224B1 (en) 1991-03-12 1991-03-12 Process for the production of pyrrolidine derivatives

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Application Number Priority Date Filing Date Title
KR1019910003933A KR930008224B1 (en) 1991-03-12 1991-03-12 Process for the production of pyrrolidine derivatives

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KR920018021A true KR920018021A (en) 1992-10-21
KR930008224B1 KR930008224B1 (en) 1993-08-27

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