KR940014327A - Method for producing proline derivative - Google Patents

Method for producing proline derivative Download PDF

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Publication number
KR940014327A
KR940014327A KR1019920023798A KR920023798A KR940014327A KR 940014327 A KR940014327 A KR 940014327A KR 1019920023798 A KR1019920023798 A KR 1019920023798A KR 920023798 A KR920023798 A KR 920023798A KR 940014327 A KR940014327 A KR 940014327A
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South Korea
Prior art keywords
proline derivative
general formula
producing
following general
formula
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KR1019920023798A
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Korean (ko)
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KR960009267B1 (en
Inventor
김만근
이관호
이기홍
김동수
류일환
조영우
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장기하
주식회사 진로
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Priority to KR1019920023798A priority Critical patent/KR960009267B1/en
Publication of KR940014327A publication Critical patent/KR940014327A/en
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Publication of KR960009267B1 publication Critical patent/KR960009267B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 프롤린유도체의 제조방법에 관한 것으로서, 더욱 상세하게는 항고혈압제로 유용한 다음 일반식(Ⅰ)로 표시되는 프롤린유도체 및 그의 약리학적으로 허용가능한 염의 신규한 제조방법에 관한 것이다.The present invention relates to a method for producing a proline derivative, and more particularly, to a novel method for producing a proline derivative represented by the following general formula (I) and a pharmacologically acceptable salt thereof useful as an antihypertensive agent.

Description

프롤린유도체의 제조방법Method for producing proline derivative

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

Claims (7)

다음 일반식(Ⅱ)로 표시되는 L-알라닌유도체와 다음 일반식(Ⅲ)으로 표시되는 프롤린유도체를 사용하여서 아실화반응에 의해 다음 일반식(Ⅰ)로 표시되는 프롤린유도체를 제조하는 방법에 있어서, 상기 일반식(Ⅱ)의 L-알라닌유도체를 염기를 사용하여 축합체인 다음 일반식(Ⅳ)로 표시되는 알킬포스클로리데이트와 반응시키고, 이를 상기 일반식(Ⅲ)의 프롤린유도체와 유기용매하에서 아실화반응시켜서 다음 일반식(Ⅴ)로 표시되는 포스포아미테이트를 제조한 다음, 이 화합물을 가수분해하여 제조하는 것을 특징으로 하는 프롤린유도체의 제조방법.In the method for producing the proline derivative represented by the following general formula (I) by acylation reaction using the L-alanine derivative represented by the following general formula (II) and the proline derivative represented by the following general formula (III) And reacting the L-alanine derivative of Formula (II) with an alkylphospholidate represented by the following Formula (IV) as a condensate using a base, which is the proline derivative of Formula (III) and an organic solvent. A method for producing a proline derivative, characterized in that the acylation reaction is carried out to produce a phosphoramitate represented by the following general formula (V), and then the compound is hydrolyzed to prepare it. 상기 식들중에서, R1은 나트륨,칼륨 또는 트리메실릴기이고, R2는 R1이 나트륨 또는 칼륨일때는 수소이고 R1이 트리메실릴기일때는 트리메실릴기이며, R3는 메틸,에틸 또는 부틸의 저급알킬기이다.In the above formula, R 1 is sodium, potassium or trimesylyl group, R 2 is hydrogen when R 1 is sodium or potassium, trimesylyl when R 1 is trimesylyl group, R 3 is methyl, ethyl Or a lower alkyl group of butyl. 제 1 항에 있어서, 상기의 염료로는 트리메틸아민 또는 피리딘을 사용하는 것을 특징을 하는 프롤린유도체의 제조방법.The method for producing a proline derivative according to claim 1, wherein trimethylamine or pyridine is used as the dye. 제 1 항에 있어서, 상기 아실화반응시의 유기용매로는 디클로로메탄, 클로로포름, 아세토니트릴, 디메틸포름아미드 중에서 단독 또는 2가지 이상을 혼합하여 사용하는 것을 특징으로 하는 프롤린유도체의 제조방법.The method of claim 1, wherein the organic solvent used in the acylation reaction is a dichloromethane, chloroform, acetonitrile, dimethylformamide, or a mixture of two or more thereof. 제 1 항에 있어서, 상기 축합제인 일반식(Ⅳ)의 화합물은 -20℃~0℃의 온도에서 적가하여 반응시키는 것을 특징으로 하는 프롤린유도체의 제조방법.The method for producing a proline derivative according to claim 1, wherein the compound of the general formula (IV) which is the condensing agent is added dropwise at a temperature of -20 deg. 제 1 항에 있어서, 상기 아실화반응은 -30℃~0℃에서 시행하는 것을 특징으로 하는 프롤린유도체의 제조방법.The method according to claim 1, wherein the acylation reaction is carried out at -30 ° C to 0 ° C. 제 1 항에 있어서, 상기 가수분해는 물과 메탄올을 혼합한 혼합용매중에서 반응온도는 20~60℃로 시행하는 것을 특징으로 하는 프롤린유도체의 제조방법.The method for preparing a proline derivative according to claim 1, wherein the hydrolysis is performed at a reaction temperature of 20 to 60 ° C in a mixed solvent of water and methanol. 다음 일반식(Ⅰ)로 표시되는 프롤린유도체에 말레인산을 1:1의 몰비로 첨가하고, 여기에 아세토니트릴 또는 아세톤중에서 선택된 것을 용해시켜서 프롤린유도체의 말레인산염을 제조하는 방법.Maleic acid is added to the proline derivative represented by the following general formula (I) in a molar ratio of 1: 1, and a solution selected from acetonitrile or acetone is dissolved therein to prepare maleate of the proline derivative. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019920023798A 1992-12-10 1992-12-10 Preparation process of proline derivatives KR960009267B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019920023798A KR960009267B1 (en) 1992-12-10 1992-12-10 Preparation process of proline derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019920023798A KR960009267B1 (en) 1992-12-10 1992-12-10 Preparation process of proline derivatives

Publications (2)

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KR940014327A true KR940014327A (en) 1994-07-18
KR960009267B1 KR960009267B1 (en) 1996-07-16

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KR960009267B1 (en) 1996-07-16

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