KR960703398A - 피페리딘 유도체 및 그의 제조 방법(Piperidine Derivatives and Process for Their Production) - Google Patents

피페리딘 유도체 및 그의 제조 방법(Piperidine Derivatives and Process for Their Production)

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KR960703398A
KR960703398A KR1019950705909A KR19950705909A KR960703398A KR 960703398 A KR960703398 A KR 960703398A KR 1019950705909 A KR1019950705909 A KR 1019950705909A KR 19950705909 A KR19950705909 A KR 19950705909A KR 960703398 A KR960703398 A KR 960703398A
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substantially pure
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piperidine derivative
regioisomers
hydrogen
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토마스 이. 담브라
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토마스 이. 담브라
알바니 몰레큘러 리써취, 인크.
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    • 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
    • C07D211/06—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
    • 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
    • C07D211/20—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
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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
    • C07D211/06—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
    • 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
    • C07D211/20—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—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
    • 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
    • C07D211/30—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 with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—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 with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

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  • Ophthalmology & Optometry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

본 발명은 일반식(I) 또는 (Ⅱ)의 실질적으로 순수한 피페리딘 유도체 화합물에 관한 것이다.
상기 식에서, R1은 수소 또는 히드록시이고; R2는 수소이거나; 또는 R1및 R2가 함께 R1및 R2를 갖는 탄소원자 사이의 제2결합을 형성하고; R3은 -C0OH 또는 -COOR4이며; R4는 1내지 6개의 탄소 원자를 가지며; A,B 및 D는 그들 고리의 치환체로서, 이들 각각은 상이하거나 동일할 수 있고, 수소, 할로겐, 알킬, 히드록시, 알콕시 또는 기타의 치환체로 구성되는 군으로부터 선택된다. 이와 같은 피페리딘 유도체 화합물을 실질적으로 순수한 형태로 제조하는 방법 또한 개시되어 있다.

Description

피페리딘 유도체 및 그의 제조 방법 (Piperidine Derivatives and Process for Their Production)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (31)

  1. 하기 일반식
    의 실질적으로 순수한 레지오이성질체(regioisomer)를 제공하고, 하기 일반식
    의 피페리딘을 사용하여 상기 실질적으로 순수한 레지오이성질체를 피페리딘 유도체 화합물로 전환시키는 것으로 이루어진, 하기 일반식의 피페리딘 유도체 화합물의 제조 방법.
    상기 식에서, R1은 수소 또는 히드록시이고; R2는 수소이거나; 또는 R1및 R2가 함께 R1및 R2를 갖는 탄소원자 사이의 제2결합을 형성하고; R3은 -C0OH 또는 -COOR4이며; R4는 1내지 6개의 탄소 원자를 가지며; A,B 및 D는 그들 고리의 치환체로서, 이들 각각은 상이하거나 동일할 수 있고, 수소, 할로겐, 알킬, 히드록시, 알콕시 또는 기타의 치환체로 구성되는 군으로부터 선택된다.
  2. 제1항에 있어서, 상기 제공 방법이 하기 일반식
    (여기서, R5는 -OR6, -N(R6)2또는 -SR6이고; R6은 탄소수 1내지 6개의 알킬이다)의 출발 화합물을 일반식
    (여기서 X는 할로겐이다)의 화합물로 하기 일반식
    의 레지오이성질체의 제1혼합물을 생성시키기에 효과적인 조건하에 아실화시키고; 상기 레지오이성질체의 제1혼합물을 하기 일반식
    의 레지오이성질체의 제2혼합물을 생성시키기에 효과적인 조건하에 가수분해하고; 상기 레지오이성질체의 제2혼합물로부터 하기 일반식
    의 실질적으로 순수한 레지오이성질체를 회수하는 것으로 이루어진 제조 방법.
  3. 제2항에 있어서, 상기 회수 방법이 상기 레지오이성질체의 제2혼합물로부터 하기 일반식
    (여기서 X+는 루이스산이다)의 실질적으로 순수한 레지오이성질체 염을 결정화시키고, 상기 실질적으로 순수한 레지오이성질체 염을 단리하고, 상기 실질적으로 순수한 레지오이성질체 염을 하기 일반식
    의 실질적으로 순수한 레지오이성질체로 전환시키는 것으로 이루어진 방법.
  4. 제3항에 있어서, X+가 알칼리 금속염 또는 NR7R8R9형태의 암모늄염(여기서, R7,R8및 R9는 독립적으로 수소 또는 탄소수 1내지 6개의 직쇄 또는 분지쇄 알킬이거나, 또는 임의의 위치에서 페닐환 또는 치환된 페닐환으로 치환된 알킬이다)인 방법.
  5. 제4항에 있어서, X+가 신코니딘(cinchonidine)이고 A가 수소인 방법.
  6. 제2항에 있어서, 상기 아실화 반응이 AICI3촉매를 사용하는 프리델-크래프트(Friedel-Craft) 반응에 의해 수행되는 것인 방법.
  7. 제1항에 있어서, 상기 제공 방법이 하기 일반식
    의 출발 화합물을 구조식
    (여기서, X는 할로겐, 트리알킬 주석, 트리플레이트 또는 유기금속 커플링 반응에 유용한 치환체이다)의 화합물로 하기 일반식
    의 실질적으로 순수한 레지오이성질체를 생성시키기에 효과적인 조건하에 아실화하는 것으로 이루어진 방법.
  8. 제1항에 있어서, 상기 제공 방법이 하기 일반식
    (여기서, R5는 -OR6, -N(R6)2및 -SR6이고; R6은 탄소수 1내지 6개의 알킬이다)의 출발 화합물을 구조식
    의 화합물로 하기 일반식
    의 레지오이성질체의 제1혼합물을 생성시키기에 효과적인 조건하게 아실화시키고; 상기 레지오이성질체의 제1 혼합물을 하기 일반식
    의 레지오이성질체의 제2혼합물을 생성시키기에 효과적인 조건하에 가수분해하고; 상기 레지오이성질체의 제2혼합물로부터 하기 일반식
    의 실질적으로 순수한 레지오이성질체를 회수하는 것으로 이루어진 방법.
  9. 제8항에 있어서, 상기 회수 방법이 하기 일반식
    (여기서 X+는 루이스산이다)의 실질적으로 순수한 레지오이성질체 염을 레지오이성질체의 제2혼합물로부터 결정화시키고; 실질적으로 순수한 레지오이성질체 염을 단리하고; 상기 실질적으로 순수한 레지오이성질체 염을 하기 일반식
    의 실질적으로 순수한 레지오이성질체로 전환시키는 것으로 이루어진 방법.
  10. 제9항에 있어서, X+가 알칼리 금속염 또는 NR7R8R9형태의 암모늄염(여기서, R7, R8및 R9는 독립적으로 수소 또는 탄소수 1 내지 6개의 직쇄 또는 분지쇄 알킬이거나, 또는 임의의 위치에서 페닐환 또는 치환된 페닐환으로 치환된 알킬이다)인 방법.
  11. 제10항에 있어서, X+가 신코니딘(cinchonidine)이고 A가 수소인 방법.
  12. 제8항에 있어서, 상기 아실화 반응이 팔라듐, 니켈 또는 그의 혼합물을 사용하여 수행되는 것인 방법.
  13. 제1항에 있어서, 추가로 하기 일반식
    의 히드록실화된 피페리딘 유도체를 생성시키기에 효과적인 조건하에 피페리딘 유도체를 환원하는 것으로 이루어진 방법.
  14. 제13항에 있어서, 히드록실화된 피페리딘 유도체가 하기 구조식을 갖는 방법.
  15. 제13항에 있어서, 히드록실화된 피페리딘 유도체가 하기 구조식을 갖는 방법.
  16. 제1항에 있어서, 상기 전환 방법이 하기 일반식
    의 실질적으로 순수한 레지오이성질체를 하기 일반식
    (여기서, X는 할로겐이다)의 제1중간체 화합물을 생성시키기에 효과적인 조건하에 할로겐화시키고; 상기 제1중간체 화합물을 하기 일반식
    의 피페리딘 유도체와, 하기 일반식
    의 피페리딘 유도체 화합물을 생성시키기에 효과적인 조건하에 반응시키는 것으로 이루어진 방법.
  17. 제1항에 있어서, 상기 전환 방법이 하기 일반식
    의 실절적으로 순수한 레지오이성질체를 하기 일반식
    의 피페리딘 화합물과, 하기 일반식
    의 피페리딘 유도체를 생성시키기에 효과적인 조건하에 반응시키는 것으로 이루어진 방법.
  18. 제1항에 있어서, 피페리딘 유도체가 하기 구조식을 갖는 것인 방법.
  19. 제1항에 있어서, 피페리딘 유도체가 하기 구조식을 갖는 것인 방법.
  20. 하기 일반식의 실질적으로 순수한 피페리딘 유도체 화합물 또는 그의 염.
    상기 식에서 R1은 수소 또는 히드록시이고; R2는 수소이거나; 또는 R1및 R2가 함께 R1및 R2를 갖는 탄소원자 사이의 제2결합을 형성하고; R3은 -COOH 또는 -COOR4이며; R4는 탄소수 1 내지 6개의 알킬이고; A, B 및 D는 그들 고리의 하나 이상의 상이한 치환체일 수 있으며, 독립적으로 수소, 할로겐, 알킬, 히드록시, 알콕시 또는 기타의 치환체이다.
  21. 제20항에 있어서, 하기 일반식을 갖는 실질적으로 순수한 피페리딘 유도체 화합물.
  22. 제20항에 있어서, 하기 일반식을 갖는 실질적으로 순수한 피페리딘 유도체 화합물.
  23. 제20항에 있어서, 하기 일반식을 갖는 실질적으로 순수한 피페리딘 유도체 화합물.
  24. 제20항에 있어서, 하기 구조식을 갖는 실질적으로 순수한 피페리딘 유도체 화합물.
  25. 제20항에 있어서, 하기 일반식을 갖는 실질적으로 순수한 피페리딘 유도체 화합물.
  26. 제25항에 있어서, 하기 일반식을 갖는 실질적으로 순수한 피페리딘 유도체 화합물.
  27. 약제학적 담체와 제20항에 따른 실질적으로 순수한 피페리딘 유도체 화합물로 이루어진 약제학적 조성물.
  28. 제27항에 있어서, 상기 실질적으로 순수한 피페리딘 유도체 화합물이 항알레르기 유효량으로 존재하는 약제학적 조성물.
  29. 제27항에 있어서, 상기 조성물이 상기 실질적으로 순수한 피페리딘 유도체 화합물을 주성분으로 하는 약제학적 조성물.
  30. 제27항에 따른 상기 약제학적 조성물 유효량을 환자에게 투여하는 것으로 이루어진, 환자의 알레르기 반응의 치료 방법.
  31. 하기 일반식의 화합물.
    상기 식에서, R3은 -COOH 또는 -COOR4이며; R4는 탄소수 1 내지 6개의 알킬이고; A는 그들 고리의 치환체이며, 각각은 상이하거나 동일할 수 있고, 수소, 할로겐, 알킬, 히드록시, 알콕시 또는 기타의 치환체로 구성되는 군으로부터 선택된다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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