KR870003981A - 클라우센아미드의 제조 방법 - Google Patents

클라우센아미드의 제조 방법 Download PDF

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Publication number
KR870003981A
KR870003981A KR1019860008708A KR860008708A KR870003981A KR 870003981 A KR870003981 A KR 870003981A KR 1019860008708 A KR1019860008708 A KR 1019860008708A KR 860008708 A KR860008708 A KR 860008708A KR 870003981 A KR870003981 A KR 870003981A
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KR
South Korea
Prior art keywords
methyl
phenylpyrrolidin
structural formula
hydroxybenzyl
clausenamide
Prior art date
Application number
KR1019860008708A
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English (en)
Inventor
하르트비히 볼프강
Original Assignee
요아힘 그렘,루디마이어
바이엘 악티엔게젤샤프트
구팡 초우
차이니즈 아카데미 오브 메디칼 사이언시즈
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by 요아힘 그렘,루디마이어, 바이엘 악티엔게젤샤프트, 구팡 초우, 차이니즈 아카데미 오브 메디칼 사이언시즈 filed Critical 요아힘 그렘,루디마이어
Publication of KR870003981A publication Critical patent/KR870003981A/ko

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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
    • C07D207/22—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
    • 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
    • C07D207/22—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • 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
    • C07D207/22—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • 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
    • C07D207/22—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Machine Translation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

내용 없음

Description

클라우센아미드의 제조 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(Ⅰ)
    의 (±)4(R*), 5(R*), 7(S*)-5-α-히드록시벤질-1-메틸-4-페닐피롤리딘-2-온을 염기 존재하에서, 필요에 따라서 보조제 존재하에서, 불활성 유기 용매 중에서 산화시키는 것을 특징으로 하는 (±)3(S*), 4(R*), 5(R*), 7(S*)-3-히드록시-5-α-히드록시벤질-1-메틸-4-페닐피롤리딘-2-온(Ⅰ)의 제조방법.
  2. 제1항에 있어서, 산화제로서 무기 또는 유기 퍼옥소 화합물, 산소, 오존 또는 산소 전이제를 사용하는 것을 특징으로 하는 방법.
  3. 제1항에 있어서, 엔올테이트 형성에 적합한 염기 또는 3급 아민을 염기로서 사용하는 것을 특징으로 하는 방법.
  4. 제1항에 있어서, 아인산염을 보조제로서 사용하는 것을 특징으로 하는 방법.
  5. 제1항에 있어서, 산화를 아인산 트리에틸 존재하에서, 테트라 히드로푸란 또는 헥사메틸인산 트리아미드, 또는 이를 용매의 혼합물 증에서 행하는 것을 특징으로 하는 방법.
  6. 제1항에 있어서, 산화 반응을 -100℃ 내지 +20℃, 적합하기로는 -78℃ 내지 0℃에서 행하는 것을 특징으로 하는 방법.
  7. 하기 구조식(Ⅱ)
    의 (±)4(R*), 5(R*), 7(S*)-5-α-히드록시벤질-1-메틸-페닐피롤리딘-2-온.
  8. 하기 구조식(Ⅲ)
    의 (±)4(R*), 5(R*)-5-포르밀-1-메틸-4-페닐-피롤리딘-2-온.
  9. 하기 구조식(Ⅳ)
    의 (±)4(R*), 5(R*)-5-벤조일-l-메틸-4-페닐피롤리딘-2-온.
  10. 하기 구조식(Ⅷ)
    의 (±)4(R*), 5(R*)-5-히드록시메틸-1-메틸-4-페닐-피롤리딘-2-온.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019860008708A 1985-10-18 1986-10-17 클라우센아미드의 제조 방법 KR870003981A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853537075 DE3537075A1 (de) 1985-10-18 1985-10-18 Verfahren zur herstellung von clausenamid
DE3537075.0 1985-10-18

Publications (1)

Publication Number Publication Date
KR870003981A true KR870003981A (ko) 1987-05-06

Family

ID=6283835

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019860008708A KR870003981A (ko) 1985-10-18 1986-10-17 클라우센아미드의 제조 방법

Country Status (9)

Country Link
US (2) US4731456A (ko)
EP (1) EP0219055B1 (ko)
JP (1) JPH0794430B2 (ko)
KR (1) KR870003981A (ko)
CN (1) CN1015710B (ko)
AT (1) ATE43836T1 (ko)
CA (1) CA1280427C (ko)
DE (2) DE3537075A1 (ko)
ES (1) ES2009758B3 (ko)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3717394A1 (de) * 1987-05-23 1988-12-01 Basf Ag 3-phenyl-2-styryl-pyrrolidine, ihre herstellung und verwendung
DE3717395A1 (de) * 1987-05-23 1988-12-08 Basf Ag 5-phenyl-1,2,3a,4,5,9b-hexahydro-3h-benz(e) indole, ihre herstellung und verwendung als arzneimittel
DE3927367A1 (de) * 1989-08-19 1991-02-21 Bayer Ag Verfahren zur herstellung von dehydrocycloclausenamid und dessen derivate in der racemischen form und als optisch aktive (+) oder (-)-enantiomere
DE3927370A1 (de) * 1989-08-19 1991-02-21 Bayer Ag Verfahren zur herstellung von clausenamid und neoclausenamid und deren derivate
US5049578A (en) * 1990-03-09 1991-09-17 E. R. Squibb & Sons, Inc. 1-aroyl or 1-acyl-2-2pyrrolidinyl-3,5-dihydroxy alkanoic and alkenoic acids, salts, esters and lactones
US6486169B1 (en) * 2002-02-19 2002-11-26 Yaguang Liu Botanical drug for treatment and prevention of alzhimer's disease
US6787564B2 (en) * 2002-03-26 2004-09-07 Institute Of Materia Medica, Chinese Academy Of Medical Sciences Optically active clausenamides, process of the preparation thereof, pharmaceutical composition containing the same and their medical use
CN102249976B (zh) * 2011-06-10 2012-11-14 中国科学院化学研究所 一种光学纯的（-）-黄皮酰胺类化合物的制备方法
CN103285123B (zh) * 2013-06-20 2015-04-22 广东医学院 黄皮果提取物在防治药源性肝炎药物中的应用
CN105017124A (zh) * 2015-07-10 2015-11-04 广西师范大学 一种合成黄皮酰胺的新方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4119637A (en) * 1975-09-23 1978-10-10 A. H. Robins Company, Inc. 4-Hydroxymethyl-2-pyrrolidinones
AT374457B (de) * 1977-08-18 1984-04-25 Hoechst Ag Verfahren zur herstellung von neuen benzolsulfonamidderivaten
CH646149A5 (de) * 1981-02-05 1984-11-15 Hoffmann La Roche Pyrrolidin-derivat.
DE3346623A1 (de) * 1983-12-14 1985-07-04 Bayer Ag, 5090 Leverkusen N-glycosylierte harnstoffe, carbamate und thiocarbamate, verfahren zu ihrer herstellung sowie ihre verwendung
DE3508025A1 (de) * 1985-03-07 1986-09-11 Bayer Ag, 5090 Leverkusen Substituierte o-sulfonyl-glycosylamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
JPS61245607A (ja) * 1985-04-24 1986-10-31 Hitachi Ltd 周波数復調回路

Also Published As

Publication number Publication date
US4751315A (en) 1988-06-14
JPH0794430B2 (ja) 1995-10-11
CA1280427C (en) 1991-02-19
JPS62187450A (ja) 1987-08-15
CN1015710B (zh) 1992-03-04
US4731456A (en) 1988-03-15
EP0219055B1 (de) 1989-06-07
DE3537075A1 (de) 1987-04-23
ES2009758B3 (es) 1989-10-16
EP0219055A1 (de) 1987-04-22
CN86107090A (zh) 1987-04-22
ATE43836T1 (de) 1989-06-15
DE3663809D1 (en) 1989-07-13

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