KR860003220A - 1-(아미노알킬)-α,α-디아릴 피롤리딘-, 피페리딘-및 호모피페리딘-아세트아미드 및 아세토니트릴의 제조방법 - Google Patents

1-(아미노알킬)-α,α-디아릴 피롤리딘-, 피페리딘-및 호모피페리딘-아세트아미드 및 아세토니트릴의 제조방법 Download PDF

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KR860003220A
KR860003220A KR1019850007677A KR850007677A KR860003220A KR 860003220 A KR860003220 A KR 860003220A KR 1019850007677 A KR1019850007677 A KR 1019850007677A KR 850007677 A KR850007677 A KR 850007677A KR 860003220 A KR860003220 A KR 860003220A
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존 웰스 테드 쥬니어 윌리엄
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존 칼머스 고돈
에이. 에이치. 로빈스 캄파니, 인코포레이티드
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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    • C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract

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Description

1-(아미노알킬)-α,α-디아릴 피롤리딘-, 피페리딘- 및 호모 피페리딘-아세트아미드 및 아세토니트릴의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. 일반식(Ⅱ)의 화합물을 염기의 존재하에서 일반식(Ⅲ)의 화합물과 반응시켜 일반식(Ⅰ)의 화합물을 유리 염기의 형태로 또는 산과 반응시킨 후에 염의 형태로 수득하거나; 일반식(Ⅳ)의 화합물을 일반식(Ⅴ)의 화합물 및 일반식(Ⅵ)의 화합물과 연속적으로 반응시켜 일반식(Ⅰ-A)의 화합물을 유리 염기의 형태로 또는 산과 반응시킨 후에 염의 형태로 수득하거나; Y가 CN인 일반식(Ⅰ)의 화합물, 즉 일반식(Ⅰ-A)의 화합물을 뜨거운 진한 강산으로 가수분해시켜 Y가 아미노카보닐인 일반식(Ⅰ)의 화합물, 즉 일반식(Ⅰ-B)의 화합물을 수득하거나; 일반식(Ⅰ-C)의 화합물을 하이드라진 수화물과 반응시켜 일반식(Ⅰ-D)의 1급 아민 화합물을 수득하거나; 일반식(Ⅰ-D)의 화합물을, 메탄이미드산 에스테르를 형성시키기에 충분한 시간 동안 환류 트리에틸오르토포르메이트와 반응시킨후 나트륨 보로하이드라이드와 반응시켜 R1이 메틸이고 R2가 수소인 일반식(Ⅰ)의 화합물을 수득하거나; 일반식(Ⅰ-D)의 화합물을 에틸클로로포르메이트와 반응시킨 후 리튬 알루미늄 하이드라이드로 환원시켜 R1이 메틸이고 R2가 수소인 일반식(Ⅰ)의 화합물을 수득하거나; 일반식 (Ⅰ-E)의 화합물을 수성염기로 가수분해시켜 일반식(Ⅰ-F)의 화합물을 수득하거나; 일반식(Ⅰ-D)의 화합물을, 포름산 및 포름알데히드와 반응시켜 R1및 R2가 모두 메틸인 일반식(Ⅰ)의 화합물을 수득하거나, NaBH3CN 및 메탄올의 존재하에서 알킬디할라이드 또는와 반응시켜 R1및 R2가 인접한 질소원자와 함께 헤테로사이클릭 잔기를 형성하는 일반식(Ⅰ)의 화합물을 수득하거나, 메탄올중에서 1몰의 알데히드 또는 케톤 및 1몰의 NaBH3CN과 반응시켜 R2가 수소인 일반식(Ⅰ)의 화합물을 수득하거나, 메탄올중에서 2몰의 알데히드 또는 케톤 및 2몰의 NaBH3CN과 반응시켜 일반식(Ⅰ)의 화합물을 수득하거나, 적절한 용매중에서 트리플루오로아세틸 클로라이드, 아킬 또는 페닐알킬할라이드, KH, 및 금순히드록시드와 연속적으로 반응시켜 R2가 수소인 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 허용되는 산부가 염 및 부분입체이성체를 제조하는 방법.
    상기식에서, n은 0,1 및 2중에서 선택되고; Ar1및 Ar2는 같거나 다를 수 있으며, 2,3 또는 4-피리도, 페닐, 및 저급알킬, 저급알콕시, 할로겐 및 트로플루오로메틸 중에서 선택된 같거나 다른 1 내지 3개의 라디칼로 치환된 페닐로 구성된 그룹중에서 선택되며; Y는 아미노카보닐 및 시아노 중에서 선택되고; X는 2 내지 5중에서 선택되며; R은 수소 및 저급알킬중에서 선택되고; R1및 R2는 서로 같거나 다를 수 있으며 수소; 저급알킬; 페닐; 할로겐, 저급알킬 또는 저급알콕시에 의해 치환된 페닐; 및 페닐이 할로겐 저급알킬 또는 저급알콕시에 의해 치환될 수 있는 페닐-저급알킬로 이루어진 그룹 중에서 선택되거나, R1및 R2가 인접한 질소원자와 함께는 피롤리디노, 피페라디노, 4-페닐피페리디노, 2,6-디저급알킬-피페리디노, 4-하이드록시-4-페닐피페리디노, 4-시아노-4-페닐피페리디노, 4-페닐-1,2,3,6-테트라하이드로피페리디노, 피페라지노, 4-저급알킬 피페라지노, 4-페닐 피페라지노, (4-페닐저급알킬)-피페라지노 및 4-모르폴리노 라디칼로 부터 선택된 헤테로사이클릭 잔기를 형성할 수 있으며; W는 저급알킬, 페닐, 또는 비간섭 라디칼로 치환된 페닐이고;은 알칼리-금속 이온이며; 단, 일반식(Ⅲ) 및 (I-A)에서, R1및/또는 R2는 수소 또는 비보호된 피페라진일 수는 없으며 그외에, R1및 R2는 상기에서 언급한 정의를 포함하고 또한 할로이거나, 인접한 질소와 함께는 1-프탈이미도, 4-치환된 피페라진, 또는저급알킬을 형성할 수 있으며; 일반식(I-B)에서, R1및 R2는 4-치환된 피페라지닐이 피페라진-1-이로 전환되고저급알킬이 -NH-저급알킬로 저급알킬전환되는 것을 제외하고는 일반식(Ⅲ) 및 (I-A)에서 정의 한 바와 같고; 일반식(Ⅳ)에서, 하이드록시 그룹은 피롤리딘 및 그 유도체의 3-위치 또는 피페리딘 및 호모피페리딘 유도체의 4-위치에만 존재할 수 있고 피페리딘 및 호모피페리딘의 3-위치에는 존재할 수 없다.
  2. 제1항에 있어서, 1-[2-(디메틸아미노)에틸]-α,α-디페닐-3-피롤리딘아세토니트릴 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
  3. 제1항에 있어서, 1-[2-(디메틸아미노)에틸]-α,α-디페닐-3-피롤리딘아세트아미드 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
  4. 제1항에 있어서, 1-[3-(디메틸아미노)프로필]-α,α-디페닐-3-피롤리딘아세트아미드 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
  5. 제1항에 있어서, 1-[2-(디에틸아미노)에틸]-α,α-디페닐-3-피롤리딘아세트아미드 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
  6. 제1항에 있어서, α,α-디페닐-1-[2-(1-피롤리디닐)에틸]-3-피롤리딘아세트아미드 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
  7. 제1항에 있어서, 1-[2-(디메틸아미노)에틸]-α,α-디페닐-3-피페리딘아세트아미드 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
  8. 제1항에 있어서, 1-[2-(디메틸아미노)에틸]-α,α-디페닐-4-피페리딘아세트아미드 또는 그의 약제학적으로 허용되는 산부가염을 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850007677A 1984-10-19 1985-10-18 1-(아미노알킬)-α, α-디아릴 피롤리딘-, 피페리딘- 및 호모피페리딘-아세트아미드 및 아세토니트릴, 및 이의 제조방법 KR900005022B1 (ko)

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CA1246564A (en) 1988-12-13
EP0178946A3 (en) 1988-06-22
JPS61100562A (ja) 1986-05-19
IL76583A0 (en) 1986-02-28
PH23368A (en) 1989-07-14
KR900005022B1 (ko) 1990-07-18
EP0178946A2 (en) 1986-04-23
AU4890685A (en) 1986-04-24
AU584930B2 (en) 1989-06-08

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