KR930016398A - Method for preparing 1,4-dihydropyridine derivative - Google Patents

Method for preparing 1,4-dihydropyridine derivative Download PDF

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Publication number
KR930016398A
KR930016398A KR1019920000622A KR920000622A KR930016398A KR 930016398 A KR930016398 A KR 930016398A KR 1019920000622 A KR1019920000622 A KR 1019920000622A KR 920000622 A KR920000622 A KR 920000622A KR 930016398 A KR930016398 A KR 930016398A
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South Korea
Prior art keywords
general formula
acid
following general
hydrogen atom
preparing
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KR1019920000622A
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Korean (ko)
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KR950000215B1 (en
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백우현
김지한
이재형
이재승
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김승호
보령제약 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4422—1,4-Dihydropyridines, e.g. nifedipine, nicardipine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

본 발명은 혈관 확장작용과 항 고혈압성을 나타내는 다음일반식(I)로 표시되는 비대칭 1,4-디하이드로 피리딘 유도체의 새로운 제조방법에 관한 것이다.The present invention relates to a novel method for preparing an asymmetric 1,4-dihydropyridine derivative represented by the following general formula (I) showing vasodilation and antihypertensive properties.

상기식에서, R1은 니트로기에 의해서 임의로 일 치환된 페닐기를 나타내며, R2와 R3는 서로 상이하며 각각 수소원자이거나, 탄소원자가 1내지 4인 저급알킬기 또는 알콕시 에틸기를 나타내고, R4와 R5는 서로 같거나 다른 것으로서 각각 수소원자이거나, 탄소원자가 1 내지 4인 저급알킬기를 나타낸다.Wherein, R 1 represents an phenyl group substituted arbitrarily by groups nitro, R 2 and R 3 are different and are each a hydrogen atom, carbon atom represents a 1 to 4 lower alkyl group or an alkoxy group, R 4 and R 5 Are the same as or different from each other, and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms.

Description

1,4-디하이드로 피리딘 유도체의 제조방법Method for preparing 1,4-dihydropyridine derivative

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

Claims (3)

다음 일반식(Ⅱ)로 표시되는 알데히드화합물을 유기용매, 알콜수용액 또는 수용성 알콜용매중에서 아민을 포함하는 촉매 존재하에 다음 일반식(Ⅲ)으로 표시되는 케토카르복실산과 반응시켜서 중간체인 다음일반식(Ⅳ)로 표시되는 일리덴-β-케토카르복실산 에스테르를 제조하고, 이를 다음 일반식(Ⅴ)의 엔아미노 카르복실산 에스테르와 반응시켜서 상기 일반식(I)의 비대칭 1,4-디하이드로 피리딘을 제조함에 있어서, 상기 중간체 제조시 사용되는 촉매로서 아민과 다음 일반식(A)로 표시되는 디카르복실산을 사용하여 반응시켜서 됨을 특징으로 하는 1,4-디하이드록시 피리딘 유도체의 제조방법.The aldehyde compound represented by the following general formula (II) is reacted with a ketocarboxylic acid represented by the following general formula (III) in the presence of a catalyst containing an amine in an organic solvent, an aqueous alcoholic solution, or an aqueous alcoholic solvent. Ilidene-β-ketocarboxylic acid ester represented by IV) is prepared, and reacted with the enamino carboxylic acid ester of the following general formula (V) to give an asymmetric 1,4-dihydro of general formula (I) In preparing pyridine, a method for preparing 1,4-dihydroxy pyridine derivative, characterized in that the reaction is carried out using an amine and a dicarboxylic acid represented by the following general formula (A) as a catalyst used in the preparation of the intermediate. . 상기식들중에서, R1은 니트로기에 의해서 임의로 일 치환된 페닐기를 나타내며, R2와 R3는 서로 상이하며 각각 수소원자이거나, 탄소원자수가 1내지 4인 저급알킬기 또는 알콕시 에틸기를 나타내고, R4와 R5는 서로 같거나 다른 것으로서 각각 수소원자이거나, 탄소원자가 1내지 4인 저급알킬기를 나태나고, Z는 수소원자 또는 히드록시기이고, m은 0또는 1 이며, n은 0 또는 1 내지 4의 정수이다.In the above formula, R 1 represents a phenyl group optionally substituted by a nitro group, R 2 and R 3 are different from each other and each represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alkoxy ethyl group, and R 4 And R 5 are the same as or different from each other, and each represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, Z is a hydrogen atom or a hydroxyl group, m is 0 or 1, n is 0 or an integer of 1 to 4 to be. 제1항에 있어서, 상기 일반식(A)의 디카르복실산은 숙신산, 아디프산, 말론산, (D,L)-밀린산 중에서 선택된 것임을 특징으로 하는 제조방법.The method according to claim 1, wherein the dicarboxylic acid of general formula (A) is selected from succinic acid, adipic acid, malonic acid, and (D, L) -millic acid. 제1항에 있어서, 상기 촉매는 상기 일반식(Ⅱ)의 알데히드화합물 몰당 0.01 내지 0.2몰의 비율로 사용하는 것을 특징으로 하는 1.4-디하이드로 피리딘 유도체의 제조방법.The method of claim 1, wherein the catalyst is used in a ratio of 0.01 to 0.2 moles per mole of the aldehyde compound of Formula (II). ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019920000622A 1992-01-17 1992-01-17 Process for preparing 1,4-dihydro pyridin derivatives KR950000215B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019920000622A KR950000215B1 (en) 1992-01-17 1992-01-17 Process for preparing 1,4-dihydro pyridin derivatives

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Application Number Priority Date Filing Date Title
KR1019920000622A KR950000215B1 (en) 1992-01-17 1992-01-17 Process for preparing 1,4-dihydro pyridin derivatives

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KR930016398A true KR930016398A (en) 1993-08-26
KR950000215B1 KR950000215B1 (en) 1995-01-12

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US5851966A (en) * 1997-06-05 1998-12-22 The Lubrizol Corporation Reaction products of substituted carboxylic acylating agents and carboxylic reactants for use in fuels and lubricants

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