KR840006625A - 3,4-디하이드로-3-r₁-4-r₂-5-q-6-r-2-(1h)-피리디논류의 제법 - Google Patents

3,4-디하이드로-3-r₁-4-r₂-5-q-6-r-2-(1h)-피리디논류의 제법 Download PDF

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KR840006625A
KR840006625A KR1019830005463A KR830005463A KR840006625A KR 840006625 A KR840006625 A KR 840006625A KR 1019830005463 A KR1019830005463 A KR 1019830005463A KR 830005463 A KR830005463 A KR 830005463A KR 840006625 A KR840006625 A KR 840006625A
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formula
compound
lower alkyl
dihydro
pyridinyl
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KR1019830005463A
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요이 레셔어(외2) 죠오지
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원본미기재
스터어링 드럭그 인코포레이팃드
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Publication of KR840006625A publication Critical patent/KR840006625A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D211/86—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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

Abstract

내용 없음.

Description

3,4-디하이드로-3-R1-4-R2-5-Q-6-R-2-(1H)-피리디논류의 제법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (17)

  1. a)구조식의 2-R1-3-R2-4-Q-4-(RCO)부탄니트릴을 강산과 반응시켜 구조식(I)의 3,4-디하이드로화합물을 생성하거나,
  2. b)구조식의 저급-알킬 2-R1-3-R2-4-Q-4-(RCO)부타노에이트를 암모니아 또는 R3가 저급알킬인 경우엔 암모니아 공급원과 반응시켜 구조식(I)의 3,4-디하이드로 화합물을 생성하거나,
  3. c) 구조식 R2-CH=C(R1)-CONH2의 α-R1-β-R2-아크릴아미드를 불활성용매중에서 강염기존재하에 반응시켜 구조식(I)의 3,4-디하이드로 화합물을 생성하거나,
  4. d) 구조식 Q-CH2-C(=O)R의 1-Q-2-알카논과 아세토-아세트아미드의 혼합물을 다가인산과 함께 가열하여 R1이 수소이고 R2가 메틸이며 3-과 4-위치에 이중결합이 있는 구조식(I)의 화합물을 생성함을 특징으로 하며 상기에서 R,R1,R2및 Q는 R1과 R2가 상기(d)에서와 같이 한정된 것이며 Q가 4(또는 3)-하이드록시페닐을 함유하지 않는 경우를 제외하곤 하기 구조식(I)에서 정의한 바와 같으며 소망에 따라, 상기 a)-c) 중 하나에 따라 제조된 구조식(I)의 3,4-디하이드로화합물을 유황존재하기 적당한 불활성용매 중에서 가열하여 3-과 4-위치에 이중결합이 있는 구조식(I)의 상응하는 화합물을 얻고, 소망에 따라 Q가 4(또는 3)-메톡시페닐인 구조식(I)의 화합물을 Q가 4(또는 3)-하이드록시페닐인 상응하는 화합물로 전환시키고, 소망에 따라 Q가 하기 언급한 피리디닐 라디킬중 하나인 염기성 화합물을 그의 산부가염으로 전환시키는 것으로 구성된I하기 구조식(I)의 화합물 또는 그의 산부가염(Q가 하기 언급된 피리디닐라디칼중 하나인 경우)을 제조하는 방법.
  6. 상기식에서, 피리디논환의 3-과 4-위치는 상기 위치에 수소원자를 갖고 있는 단일결합이거나(3,4-디하이드로)또는 상기 위치사이에 이중 결합이 있으며 Q는 4(또는 3)-하이드록시페닐, 4(또는 3)-메톡시페닐, 4(또는 3)-피리디닐 또는 1-2개의 저급알킬 치환분을 갖는 4(또는 3)-피리디닐이며, R1과 R2는 각기 소소이거나 메틸이며, 단 3-4과 4-위치사이에 이중결합이 있는 경우 R1과 R2중 적어도 하나는 메틸이며, R은 저급 알킬이다.
  7. 2. 제1항에 있어서, 방법 a)에서 구조식 Q-CH2-C(=0) R의 1-Q-2-알카논을 경염기존재하에 구조식 R2-CH-C(R1) CN=α-R1-β-R2아크릴로니트릴과 반응시켜 2-R1-3-R2-4-Q-4(RCO)부탄 니트릴을 제조함을 특징으로 하는 방법.
  8. 제2항에 있어서 첫단계에서 강염기가 알칼리수소화물 또는 메톡사이드이며 두 번째 단계에서 강산이 강한 무기산임을 특징으로 하는 방법.
  9. 제1항에 있어서, 방법 b)에서 구조식 Q-CH2-C(=O) R의 1-Q-2-알카논을 구조식 R2-CH=CH(R1) COOR3의 저급알킬 α-R1-β-R2-아크릴레이트와 반응시켜 저급알킬 2-R1-3-R2-4-Q-4-(RCO)부타노에이트를 제조함을 특징으로 하는 방법.
  10. 제4항에 있어서 첫단계에서 R3가 메틸 또는 에틸이며, 둘째 단계에서 암모니아 공급원으로 초산암모늄이 사용됨을 특징으로 하는 방법.
  11. 제1항에 있어서 방법 c)에서 디옥산과 칼륨 또는 나트륨 3급-부톡사이드를 사용함을 특징으로 하는 방법.
  12. 제1항에 있어서 방법 d)에서 메탄설폰산과 다가인산을 함께 사용하여 반응을 수행함을 특징으로 하는 방법.
  13. 제1항 내지 제7항중 어느 하나에서 3,4-디하이드로 화합물을 3-과 4-위치에 이중결합을 갖고 있는 구조식(I)의 화합물로 전환시키는데 사용되는 불활성 용매가 디페닐과 디페닐 에테르의 공융혼합물임을 특징으로 하는 방법.
  14. 하기구조식(IA)의 3,4-디하이드로-3-R1-4-R2-5-Q-6-R-2(1H)-피리디논을 유황존재하에 적당한 불황성 용매중에서 가열한후 소망에 따라 Q가 4(또느 3)-메톡시페닐인 3-R1-4-R2-5-Q-6-R-2(1H)-피리디논을 Q가 4(또는 3)-하이드록시페닐인 상응하는 화합물로 전환시키는 것으로 구성된 하기구조식(1B)의 3-R1-4-R2-5-Q-6-R-2(1H)피리디논을 제조하는 방법.
  16. 상기 구조식(1B)에서 R1과 R2는 각기 수소 또는 메틸이며 R은저급알킬이며 Q는 4(또는 3)-하이드록시페닐, 4(또는 3)-메톡시페닐, 4(또는 3)-피리디닐, 또는 1-2개의 저급알킬치환분을 갖는 4(또는 3)-피리디닐이며, 상기 구조식(IA)에서, R1,R2,R 및 Q는 상기한바와 같으나 단 Q에 (4 또는 3) -하이드록시페닐이 포함되지 않는다.
  17. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019830005463A 1982-11-18 1983-11-17 3,4-디하이드로-3-r₁-4-r₂-5-q-6-r-2-(1h)-피리디논류의 제법 KR840006625A (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US06/442,623 US4431651A (en) 1982-11-18 1982-11-18 2-Pyridinones and their use as cardiotonic agents
US44324982A 1982-11-22 1982-11-22
US443249 1982-11-22
US442623 1995-05-17

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EP (1) EP0109628A1 (ko)
KR (1) KR840006625A (ko)
AU (1) AU2141383A (ko)
DK (1) DK527383A (ko)
ES (1) ES527344A0 (ko)
FI (1) FI834215A (ko)
GR (1) GR79123B (ko)
IL (1) IL70169A0 (ko)
NO (1) NO834227L (ko)
NZ (1) NZ206215A (ko)
PT (1) PT77670B (ko)

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Publication number Priority date Publication date Assignee Title
DE3427146A1 (de) * 1984-07-24 1986-02-06 Dynamit Nobel Ag, 5210 Troisdorf Neue pyridon-derivate
DE3433953A1 (de) * 1984-09-15 1986-03-27 A. Nattermann & Cie GmbH, 5000 Köln Neue, eine imidazol-gruppe enthaltende 3,4-dihydro-2(1h)-pyridone und2(1h)-pyridone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
PE20060285A1 (es) 2004-03-30 2006-05-08 Aventis Pharma Inc Piridonas sustituidas como inhibidores de pol(adp-ribosa)-polimerasa (parp)
DE102004050196A1 (de) * 2004-10-15 2006-04-20 Sanofi-Aventis Deutschland Gmbh Substituierte 2-Pyridon-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikament
WO2008133660A2 (en) 2006-11-21 2008-11-06 Qd Vision, Inc. Nanocrystals including a group iiia element and a group va element, method, composition, device and other prodcucts
WO2013028253A1 (en) 2011-08-19 2013-02-28 Qd Vision, Inc. Semiconductor nanocrystals and methods
WO2013173409A1 (en) 2012-05-15 2013-11-21 Qd Vision, Inc. Semiconductor nanocrystals and methods of preparation

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Publication number Priority date Publication date Assignee Title
US3718743A (en) * 1970-11-19 1973-02-27 Merck & Co Inc 5-phenyl-2-piperidones and 5-phenyl-2-thiopiperidones in compositions and methods for treating pain, fever and inflammation
IL61501A (en) * 1979-11-26 1984-06-29 Sterling Drug Inc 5-(pyridinyl)-2(1h)-pyridinones,their preparation and pharmaceutical compositions containing them
FI820573L (fi) * 1981-03-03 1982-09-04 Lilly Co Eli 1-bentsoyl-3-(arylpyridyl)ureafoereningar beroerande eller till dessa hoerande foerbaettringar
US4465686A (en) * 1981-09-08 1984-08-14 Sterling Drug Inc. 5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones, their cardiotonic use and preparation

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FI834215A (fi) 1984-05-19
DK527383D0 (da) 1983-11-17
DK527383A (da) 1984-05-19
GR79123B (ko) 1984-10-02
IL70169A0 (en) 1984-02-29
PT77670A (en) 1983-12-01
AU2141383A (en) 1984-05-24
NZ206215A (en) 1986-01-24
ES8601138A1 (es) 1985-10-01
EP0109628A1 (en) 1984-05-30
ES527344A0 (es) 1985-10-01
PT77670B (en) 1986-03-27
NO834227L (no) 1984-05-21

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