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KR850006403A - 축합 디아제핀온의 제조방법 - Google Patents

축합 디아제핀온의 제조방법 Download PDF

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KR850006403A
KR850006403A KR1019850001629A KR850001629A KR850006403A KR 850006403 A KR850006403 A KR 850006403A KR 1019850001629 A KR1019850001629 A KR 1019850001629A KR 850001629 A KR850001629 A KR 850001629A KR 850006403 A KR850006403 A KR 850006403A
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엥겔 볼프하르트 (외 6)
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베쩰, 좀머
닥터 칼토메 게젤샤프트 미트 베슈랭크터 하프퉁
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Abstract

내용 없음

Description

축합 디아제피온의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (11)

  1. a) 일반식(Ib)의 염기-치환된 축합디아제핀온을 제조하기 위해서, 일반식(Ⅱ)의 할로아실 화합물을 일반식(Ⅲ)의 2급아민과 반응시키거나, b) 일반식(Ib)의 화합물을 제조하기 위해서, 일반식(Iv)의 트리사이클릭 화합물을 일반식(V)의 카복실산 유도체와 아실화시키거나, c) 일반식(Ic)의 피롤로벤조디아제핀온을 제조하기 위해서, R3가 염소원자인 일반식(Ic)의 화합물을 가수소분해시키고, 필요시, 수득된 일반식(I)의 화합물을 이의 NR1R2-N-옥사이드로 산화시키고/시키거나 이의 디아스테레오아이스머 및/또는 에난티오머로 분할시키고/시키거나 무기산 또는 유기산과의 생리학적으로 허용되는 이의 산부가염으로 전환시킴을 특징으로 하여, 일반식(I)의 축합디아제핀은 NR1R2이의 디아스테레오아이소머와 에난티오머, 이의 NR1R2-N-옥사이드, 및 생리학적으로 허용되는 이의 산부가염을 제조하는 방법.
    상기식에서, ]는 2가 그룹인중의 하나이고, X는 =CH그룹이거나, ]가 오르토-페닐렌 그룹일 경우 질소원자이고, A1은 탄소수 1 또는 2의 알킬렌그룹이고, A2는 포화헤테로사이클릭 환의 질소원자에 대해 2-위치에 있을 경우 탄소수 1 또는 2의 알킬렌 그룹이거나, 3 또는 4-위치에 있을 경우 단일 결합 또는 메틸렌그룹을 나타내고, R1은 탄소수 1 내지 3의 측쇄 또는 비측쇄알킬 그룹이고, R2는 2 내지 7번탄소원자상에 하이드록시 그룹에 의해 임의 치환될 수 있는 탄소수 1 내지 7의 측쇄 또는 비측쇄 알킬 그룹이거나, 환탄소수 3 내지 7의 사이클로알킬 또는 사이클로알킬메틸 그룹(여기서 사이클로알킬 환은 하이드록시 그룹에 의해 임의 치환될 수 있다)이거나, R1및 R2는 이들이 결합되어 있는 질소원자와 함께, 산소원자 또는 N-CH3그룹이 임의 삽입될 수 있는 4-내지 7-원 포화모노 사이클릭, 헤테로사이클록 환일 수도 있고, R3는 수소 또는 염소 원자이거나 메틸그룹이고, R4는 수소 원자 또는 탄소수 1 내지 4의 알킬그룹이고, R5는 수소 또는 염소원자이거나 탄소수 1 내지 4의 알킬그룹이고, Z는 단일결합이거나, 산소원자, 메틸렌그룹 또는 1,2-에틸렌그룹이고, ]는 2가 그룹인(여기서, R4및 R5는 상기한 바와 같고 R3´는 메틸그룹 또는 염소이다)중의 하나이고, Hal은 염소, 브롬 요오드 원자이고, Nu는 이핵성 또는 이탈 그룹이고, 단, 일반식(Ic)에서 R는 수소원자이다.
  2. 제1항에 있어서, R1내지 R3및 X가 제1항에서의 정의한 동일하고, Z가 단일 결합 또는 메틸렌 그룹이고, A1및 A2가 각기 메틸렌그룹이고, R4가 수소원자 또는 메틸그룹이고, R5가 수소 또는 염소 원자 이거나 메틸그룹인, 일반식(I)축합디아제핀은, 이의 디아스테레오아이소머와 에난티오머, 이의 NR1R2-N-옥사이드, 및 무기산 또는 유기산과의 생리학적으로 허용되는 이의 산부가염을 제조하는 방법.
  3. 제1항에 있어서, X가 제1항에서의 정의와 동일하고, Z가 단일결합 또는 메틸렌그룹이고, ]가 오르토-페닐렌그룹 또는 3,4-결합된 티에노 그룹이고, A1이 메틸렌그룹이고, A2가 포화 헤테로사이클릭환의 N-원자에 대해 2-위치에 있는 메틸렌 그룹이고, R1이 메틸 또는 에틸그룹이고, R2가 메틸, 에틸 또는 4-하이드록시 사이클로헥실그룹인, 일반식(I)의 축합 디에제핀온, 이의 디아스 테로오아이소머와 에난티오머, 이의 NR1R2-N-옥사이드, 및 무기산 또는 유기산과의 생리학적으로 허용되는 이의 산부가 염을 제조하는 방법.
  4. 제1항에 있아서, 11-[[2-[(-디에틸아미노)메틸]-1-피페리디닐]아세틸]-5,11-디하이드록-6H-피리도[2,3-b][1,4]벤조디아제핀-6-온을 제조하는 방법.
  5. 제1항에 있어서, 트란스-5,11-디하이드로-11-[[2-[[(4-하이드록시사이클로헥실)(메틸)아미노]메틸]-1-피페리디닐]아세틸]-6H-피리도-[2,3-b][1,4]벤조디아제핀-6-온을 제조하는 방법.
  6. 제1항에 있어서, 5,11-디하이드로-11-[[2-(디메틸 아미노)메틸]-1-피페리디닐]아세틸]-6H-피리도[2,3-b][1,4]벤조디아제핀-6-온을 제조하는 방법.
  7. 제1항에 있어서, (s)-11-[[2-[[(디에틸아미노)메틸]-1-피롤리디닐]아세틸]-5,11-디하이드로-6H-피리도[2,3-b][1,4]벤조디아제핀-6-온을 제조하는 방법.
  8. 일반식(Ⅵ)의 화합물을 폐환시킨 후, 필요시, 수득된 일반식(Ia)의 트리사이클릭 화합물(R=H)을 할로아실화시킴을 특징으로 하여, 일반식(Ia)의중간체 생성물을 제조하는 방법.
    상기식에서, R은 수소원자 또는 총 탄소수 2 또는 3의 할로아실 그룹(바람직하게는 클로로아실 그룹)이고, Nu1은 적절한 이핵성그룹이다.
  9. 제1 a)항에 있어서, 일반식(Ⅱ)의 할로아실화합물을 일반식(Ⅲ)의 2급아민과, 불활성용매중에서 -10℃ 내지 용매 비점의 온도에서, 임의로 보조염기 또는 과량의 일반식(Ⅲ)의 아민 존재하에 반응시키되 임의로 우선 염기를 사용하여 일반식(Ⅱ)의 할로아실 화합물로부터 분자 H-Hal을 분해시킨 후 형성된 아크릴로일 화합물을 일반식(Ⅲ)의 아민과 반응시킴을 특징으로 하는 방법.
  10. 제1 b)항에 있어서, 일반식(Ⅳ)의 트리사이클릭 화합물을 일반식(V)의 카복실산 유도체와 바람직하게는 카복실산 유도체가 근거한, 이들 카복실산의 N-2-알킬아실옥시피리-디늄염, 산할라이드, 에스테르, 무수물 또는 혼합무수물과, 불활성 용매중에서 -25℃ 내지 130℃의 온도로, 임의로 산결합제 존재하에 반응시킴을 특징으로 하는 방법.
  11. 제1 c)항에 있어서, 일반식(Ic)의 화합물의 가수소분해를, 주기율표상의 Ⅷ족 아그룹금속의 촉매 존재하에 1 내지 300바의 수소압 및 0 내지 130℃의 온도에서 용매존재시 수행함을 특징으로 하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850001629A 1984-03-14 1985-03-14 축합 디아제핀온의 제조방법 Expired KR920003980B1 (ko)

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EP0213293B1 (de) * 1985-06-27 1992-01-02 Dr. Karl Thomae GmbH In 11-Stellung substituierte 5,11-Dihydro-6H-pyrido-[2,3-b][1,4]benzodiazepin-6-one, Verfahren zur ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3529372A1 (de) * 1985-08-16 1987-02-19 Dompe Farmaceutici Spa Aminoacyl-derivat von 4,9-dihydro-10h-pyrido(3,2-b)-thieno(3,2-e) (1,4)-diazepinon und von 4,9-dihydro-10h-pyrido(3,2-b)thieno(3,4-e) (1,4)diazepinon, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen
DE3531682A1 (de) * 1985-09-05 1987-03-12 Thomae Gmbh Dr K (+)-6-chlor-5,10-dihydro-5-((1-methyl-4- piperidinyl)acetyl)-11h-dibenzo(b,e)(1,4) diazepin-11-on, seine isolierung und verwendung als arzneimittel
JPS62107216A (ja) * 1985-11-05 1987-05-18 Ngk Insulators Ltd バルブシートインサート及びその製造法並びにそれを使用してなるシリンダーヘッド
DE3626095A1 (de) * 1986-07-31 1988-02-11 Thomae Gmbh Dr K Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3643666A1 (de) * 1986-12-20 1988-06-30 Thomae Gmbh Dr K Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3726908A1 (de) * 1987-08-13 1989-02-23 Thomae Gmbh Dr K Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3735895A1 (de) * 1987-10-23 1989-05-03 Thomae Gmbh Dr K Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3802334A1 (de) * 1988-01-27 1989-08-10 Thomae Gmbh Dr K Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
GB8803259D0 (en) * 1988-02-12 1988-03-09 Zambeletti Spa L Compounds
DE3819444A1 (de) * 1988-06-08 1989-12-14 Thomae Gmbh Dr K Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3820347A1 (de) * 1988-06-15 1989-12-21 Thomae Gmbh Dr K Verwendung von in 11-stellung substituierten 5,11-dihydro-6h-pyrido(2,3-b) (1,4)benzodiazepin-6-onen zur behandlung von bradycardien und bradyarrhythmien in der human- und veterinaermedizin
US4931436A (en) * 1988-08-09 1990-06-05 Dr. Karl Thomae Gmbh Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds
DD293582A5 (de) * 1989-07-31 1991-09-05 Arzneimittelwerk Dresden,De Neue 5-(omega-aminoacyl)-5,10-dihydro-11h-dibenzo/b,e//1,4/-diazepin-11-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5179090A (en) * 1989-09-11 1993-01-12 Klaus Rudolf Condensed diazepinones and medicaments containing these compounds
JPH05506650A (ja) * 1990-04-28 1993-09-30 スミスクライン　ビーチャム　ファルマシューティッチ　エッセ　ピ　ア アザ環式誘導体
DE4112014A1 (de) * 1991-04-12 1992-10-15 Thomae Gmbh Dr K Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel zur behandlung von erkrankungen des zentralnervensystems und zur foerderung der cerebralen durchblutung
DE4117123A1 (de) * 1991-05-25 1992-11-26 Dresden Arzneimittel Neue 5-aminoacyl-5,10-dihydro-11h-dibenzo/b,e//1,4/-diazepin-11-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5324832A (en) * 1991-07-03 1994-06-28 The United States Of America As Represented By The Department Of Health And Human Services Muscarinic antagonists
US5716952A (en) * 1992-03-18 1998-02-10 Allergan Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists
TW202402753A (zh) 2022-03-30 2024-01-16 日商參天製藥股份有限公司 高純度化合物之製造方法及純化方法

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DE3028001A1 (de) * 1980-07-24 1982-02-18 Dr. Karl Thomae Gmbh, 7950 Biberach Neue, in 5-stellung substituierte 5,10-dihydro-11h-dibenzo (b,e)(1,4) diazepin-11-one, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel
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US4558132A (en) * 1982-07-02 1985-12-10 A. H. Robins Company, Incorporated Nitro, amino and aroylamino-N-phenylpyridinamines in a process for preparing pyrido[1,4]benzodiazepines
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