KR840000494A - 디하이드로피리딘의 제조방법 - Google Patents

디하이드로피리딘의 제조방법 Download PDF

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KR840000494A
KR840000494A KR1019820003412A KR820003412A KR840000494A KR 840000494 A KR840000494 A KR 840000494A KR 1019820003412 A KR1019820003412 A KR 1019820003412A KR 820003412 A KR820003412 A KR 820003412A KR 840000494 A KR840000494 A KR 840000494A
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프랭코 비아크 게르하르트 (외 9)
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바이엘 아크티엔 게젤샤프트
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Abstract

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Description

디하이드로피리딘의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (5)

  1. a) 다음 일반식(Ⅱ)의 카보닐 화합물을 다음 일반식(Ⅲ) 및 (Ⅳ)의 케톤 및 다음 일반식(Ⅴ)의 1급아민과 반응시키거나, b) 일반식(Ⅱ)의 카보닐화합물을 다음 일반식(Ⅵ)의 엔아민 및 일반식(Ⅳ)의 케톤과 반응시키거나, c) 일반식(Ⅵ)의 엔아민을 다음 일반식(Ⅶ)의 일리덴 화합물과 반응시키거나, d) 상기 a), b) 또는 c)에 의해 얻어진 화합물 또는 디하이드로피리딘의 작용기하나이상을 적합한 시약으로 산-촉매화 또는 염기-촉매화 가수분해, 에스테르화, 트랜스-에스테르화, 락톤화, 축합, 아실화, 환원 또는 환화시키거나, 분자내 반응시키고; 바람직하게는 0-알킬화 또는 0-아실화된 2-(하이드록시알킬)-1,4-디하이드로피리딘-3-카복실산에스테르를 산 또는 염기처리하여 탈자단시키고 생성된 2-(하이드록시알킬)-1,4-디하이드로 피리딘-3-카복실에스테르 또는-카복실레이트를 일반식(Ⅰ)의 락톤을 형성시키는데 사용된 반응조건하에 자발적 환화시킴)시키고, 필요한 경우, 개개의 이성체 또는 광학 대장체로 분리시킴을 특징으로 하여 다음 일반식(Ⅰ)의 화합물 및 이의 약학적으로 무독한 염을 제조하는 방법.
    상기 일반식에서, n은 0,1 또는 2이고, R1은 a) 수소; 0, CO, SOm(여기서, m은 0,1 또는 2이다), =N-, NRI및 SiRIIRIII중에서 선택된, 1내지 3개의 같거나 다른 헤테로 쇄원(hetero chain member)을 임의로 함유하는 직쇄, 측쇄, 환상, 포화 또는 불포화 지방족탄화수소기(여기서 탄화수소기는 할로겐, NO2, CN,N3, 하이드록실, 아릴 또는 헤테로 아릴로 임의로 치환된다)이거나, b) 아릴, 알킬, 알케닐, 알키닐, 알켄옥시, 알켄옥시, 아르알킬, 아실, 알킬렌, 디옥시알킬렌, 할로겐, CF3,OCF3,SCF3,NO2,NO,CN,N3,CORIVCOOR|V, ORVI, NRI및 NRVIIRVIII중에서 선택된, 1내지 5개의 같거나 다른 치환체를 임의로 함유하는 아릴 또는 헤테로아릴기(여기서 상술한 치환체중 알킬, 알콕시 및 아릴기는 할로겐, CORV또는 NRVIIRVIII로 치환될 수 있다)이거나, c) 일반식 NRVIIRPI의 기이고, R2는 a) R1에서 정의한 기와 같으나 R1과는 독립적이고, b) 일반식 NHRI또는의 기이거나, R1및 R2는 함께 O,S,NRI및 CO중에서 선택된, 1내지 3개의 같거나 다른 환형(ring member)을 임의로 함유하며 할로겐, 하이드록실, 알킬, 알콕시 아릴 및 아르알킬 중에서 선택된, 1내지 3개의 같거나 다른 치환체를 임의로 함유하는 5-원 내지 8-원의 포화 또는 불포화환을 형성하고
    R3는 R2에서 정의한 기와 같으나 R2와는 독립적이며, 단 각 경우 R2또는 R3치환체중 하나만이 알콕시, 알킬티오 또는 NHRI을 나타낼 수 있고, R4및 R5는 같거나 다르며, 각각 a) 수소, NO2,NO,CN,SOm-RXI(여기서 m은 0,1 또는 2이다), 할로겐,, 또는이거나 b) 할로겐, OH,CN,알콕시, 알킬티오, 아릴옥시, COORV또는로 임의로 치환된 직쇄 또는 측쇄, 환상, 포화 또는 불포화 지방족 탄화수소기이거나, c) 방향족 탄화수소기, 또는 O,S,-N= 및 NRI중에서 선택된, 1내지 4개의 같거나 다른 헤테로원(hetero member)을 함유하는 5-원 내지 7-원 포화 또는 불포화 헤테로환(여기서 헤테로환은 탄소원자 또는 질소원자를 통해 디하이드로피리딘 환과 결합되며, 방향족 탄화수소기 및 헤테로환은 할로겐, OH,CN,CF3,OCF3,SCF3,NO2, 알킬, 알콕시, 아릴 및중에서 선택된, 1내지 3개의 같거나 다른 치환체를 임의로 함유할 수 있다)이거나, d) 일반식의 기(여기서 X는 산소, 황 또는 NRI이고 Y는 단일결합, O, S 또는 NRI이고 R8은 R1에서 정의한 기와 같으나 R1과는 독립적이다)이거나 e) 다음 일반식의 기
    (상기식에서, n',R1',R2',R3',R5',R6'및 R7'는 n,R1,R2,R3,R5,R6및 R7에서 정의한 기와 같으나 n,R1,R2,R3,R5,R6및 R7과는 독립적이고 R4*및 R4**는 같거나 다르며, 각각 상기 a)-d)의 R4정의에서 주어진 치환체를 나타내며 수소로 환원된 기이다), 또는 R2및 R4, 및/또는 R3및 R5는 독립적으로, O,CO,CS,C=NRI, =N-, NRI, SOm(여기서 m은 0,1 또는 2이다) 및 SiRIIRIII중에서 선택된, 1내지 3개의 같거나 다른 환원을 임의로 함유하며 할로겐, 하이드록실, 알콕시, 아릴, 아르알킬 또는로 임의로 치환되거나 탄소수 3내지 8의 직쇄, 또는 측쇄 알킬렌쇄로 이치환된 5-원내지 8-원의직쇄, 측쇄, 포화 또는 불포화 환을 형성하며, 또한 R2및 R4의 공동환(common ring)은 R1및 R2의 공동환과 직접 융합될 수 있고
    R6는 수소 또는 알킬 또는 할로게노알킬기이고, R7은 a) 할로겐, 아릴 또는 헤테로아릴로 임의로 치환된 포화 또는 불포화, 환상, 직쇄 또는 측쇄 지방족 탄화수소기이거나, b) NO2,CN,N3,NO,CF3, 할로겐, CORIV, COORV,, SOmRXI(여기서 m은 0,1 또는 2이다),, 알킬, 아릴, 알케닐, 알키닐, 알켄옥시, 알킨옥시, 아르알킬, 아실, 알킬렌 및 디옥시알킬렌중에서 선택된, 1내지 5개의 같거나 다른 치환체를 임의로 함유하는 아릴 또는 헤테로아릴기)여기서 상술한 치환체중 알킬 및 아릴 치환체는 할로겐, COORV또는로 치환될 수 있다)이고, RI은 수소, 알킬, 아릴, 아르알킬, 헤테로아릴 또는 아실기이고, RII및 RIII는 같거나 다르며, 각각 알킬, 아릴, 아르알킬 또는 헤테로아릴기이고, RIV, RV및 RVI는 같거나 다르며, 각각 수소, 알킬아릴, 아르알킬 또는 헤테로아릴기이고, RVII및 RVIII은 같거나 다르며, 각각 수소, 아릴 또는 아르알킬기 또는 O, S 또는 NRI으로 임의로 삽입된 알킬기이거나, RVII및 RVIII는 질소원자와 함께, O, S 및 NRI중에서 선택된, 1 또는 2개의 같거나 다른 헤테로 환원을 함유할 수 있는 5-원 내지 7-원 환을 형성하거나 RVII또는 RVIII중 하나는 탄소수 6이하의 지방족 아실기를 나타내고, RIX, RX, RXI, RXII및 RXIII는 같거나 다르며, 각각 알킬, 아릴 또는 아르알킬기이고, R1-R8및 RI-RXIII의 정의에서 기술된 알킬, 아릴, 아르알킬, 헤테로아릴 및 아실기와 RVII및 RVIII에 의해 형성된 헤테로 환은 OH,CF3,OCF3,CN,NO2, 할로겐, 탄소수 1내지 6의 티오알킬, 탄소수 1내지 6의 알콕시, 아릴 및 아르알킬 및 추가로 알킬(단 알킬의 경우는 제외)중에서 선택된 치환체(들)로, 임의로 치환된다.
  2. 제1(a),1(b) 또는 1(c)항에 있어서, 반응을 불활성 용매하에 수행하는 방법.
  3. 제 1(d) 또는 2항에 있어서, 상기 1(a),1(b) 또는 1(c)항의 방법으로 얻어진, R2및 R4및/또는 R3및 R5가 유리 및/또는 보호그룹에 의해 자단된 카복실기 및 하이드록시를 함유하는 화합물을 염기-촉매화 또는 산-촉매화 반응 조건하에 환화시키고, 필요한 경우 보호그룹을 완전히 또는 부분적으로 분리, 제거시켜 일반식(Ⅰ)의 락톤을 제조하는 방법.
  4. 제1항에 있어서, 실시예 46내지 254중 하나에 기술되어 있는 방법.
  5. 제1항에 있어서, 실시예 1내지 10,19내지 23,26,28,29,30,31,32,35내지 38,41,42 및 45중 하나에 기술되어 있는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8203412A 1981-07-30 1982-07-30 디하이드로 피리딘의 제조방법 KR890001566B1 (ko)

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DEP3130041.3 1981-07-30
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DE19823206671 DE3206671A1 (de) 1982-02-25 1982-02-25 Dihydropyridine mit positiv inotroper wirkung, neue verbindungen, ihre verwendung in arzneimitteln und verfahren zu ihrer herstellung

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FI822643A0 (fi) 1982-07-28
IL66405A0 (en) 1982-11-30
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IL66405A (en) 1987-12-31
EP0071819B1 (de) 1987-04-22
IE821827L (en) 1983-01-30
ES8305716A1 (es) 1983-04-16
AU566502B2 (en) 1987-10-22
CH656530A5 (de) 1986-07-15
FR2511247B1 (fr) 1986-03-07
IE54259B1 (en) 1989-08-02
KR890001567B1 (ko) 1989-05-08
NL8202958A (nl) 1983-02-16
ES514525A0 (es) 1983-04-16
CA1212672A (en) 1986-10-14
IT1190929B (it) 1988-02-24
KR890001566B1 (ko) 1989-05-08
DE3276112D1 (en) 1987-05-27
JPS5826872A (ja) 1983-02-17
PH23086A (en) 1989-04-10
FR2511247A1 (fr) 1983-02-18
JPH05271078A (ja) 1993-10-19
IT8222620A0 (it) 1982-07-28
US4532248A (en) 1985-07-30
AU8594582A (en) 1983-02-03
IT8222620A1 (it) 1984-01-28
FI822643L (fi) 1983-02-01
EP0071819B2 (de) 1992-06-10
EP0071819A1 (de) 1983-02-16
GB2105989A (en) 1983-04-07
HK19389A (en) 1989-03-17
DK339782A (da) 1983-01-31
GB2105989B (en) 1986-01-08
JPH066535B2 (ja) 1994-01-26

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