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KR940005614A - 디페닐 옥사졸 티아졸 및 이미다졸의 아데노신 재흡수 억제 유도체 - Google Patents

디페닐 옥사졸 티아졸 및 이미다졸의 아데노신 재흡수 억제 유도체 Download PDF

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KR940005614A
KR940005614A KR1019930014660A KR930014660A KR940005614A KR 940005614 A KR940005614 A KR 940005614A KR 1019930014660 A KR1019930014660 A KR 1019930014660A KR 930014660 A KR930014660 A KR 930014660A KR 940005614 A KR940005614 A KR 940005614A
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methyl
oxazolyl
diphenyl
dimethylphenyl
piperazinacetamide
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발라수브라마니언 닐아칸탄
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데이비드 엠.몰스
브리스톨-마이어스 스퀴브 캄파니
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Abstract

신규한 아데노신 수송 억제제인 4, 5-디페닐-옥사졸, 티아졸, 및 이미다졸의 1-피페라지닐-N-페닐아세타미드 유도체 계열이 CNS조직, 특히 신경에 유효한 허혈 치료효과를 제공하는 것으로 밝혀져 왔다. 회상, 졸중, 또는 그밖의 허혈상태로부터 발생되는 것과 같은 CNS허혈로부터 보호하기 위한 치료방법은 이를 필요로 하는 대상에게 이들 신교한 화합물을 투여하는 것을 포함한다.

Description

디페닐옥사졸, 티아졸 및 이미다졸의 아데노신 재-흡수억제 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(Ⅰ) 화합물 또는 이의 약제학적으로 허용되는 산구가염 및 수화물:
    상기식에서, R1및 R2는 수소, C1-4알킬, C1-4알콕시, 할로겐 및 트리플루오로메틸중에서 독립적으로 선택되고, R3은 수소, 할로겐, C1-4알콕시, 니트로 또는 -NR9R10이고, R4는 수소 또는 C1-4알킬이고, R5및 R6은 수소, -CO2R11, -CONR9R10및 옥소중에서 독립적으로 선택되거나, R5및 R6은 함께 결합되어 메틸렌 또는 에틸렌 다리를 형성할 있고, R7및 R8은 부틸렌 다리로서 함게 결합되거나, R7및 R8은 각각이고, R9및 R10은 수소, C1-4알킬, 알카노일 및중에서 독립적으로 선택되고, R11은 C1-4알킬이고, R12는 수소, 할로겐, 트리플루오로메틸, C1-4알킬 또는 C2-4알킬 -N(R4)2이고, N은 0 또는 정수 1 내지 4이고, X는 S, O 또는 NH이다.
  2. 제1항에 있어서, R1및 R2가 메틸 및 클로로중에서 선택되고, R5는 아미노카르보닐이고, R7및 R8는 페닐이고, n은 1인 화합물.
  3. 제1항에 있어서, n-(2, 6-디메틸페닐)-4-[(4, 5-띠페닐-2-옥사졸릴)메틸]-1-피페라진아세트아미드, N-(2, 6-디클로로페닐)-4[(4, 5-디페닐-2-옥사졸릴)메틸]-1-피페라진아세트아미드, 4-[[4, 5-비스(4-에틸페닐)-2-옥사졸릴]메틸]-N-(2, 6-디메틸페닐)-1-피페라진아세트아미드, 4-[[4, 5-비스(4-플루오로페닐)-2-옥사졸릴]메틸]-N-(2, 6-디메틸페닐)-1-피페라진아세트아미드, 4-[[4, 5-비스[4-(트리플루오로메틸)-페닐]-2-옥사졸릴]메틸]-N-(2, 6-디메틸페닐)-1-피페라진아세트아미드, 4-[[4, 5- 비스(3-클로로페닐)-2-옥사졸릴]메틸]-N-(2, 6-디메틸페닐)-1-피페라진아세트아미드, 4-[[4, 5-디페닐-2-옥사졸릴]에틸]-N-(2, 6-디메틸페닐)-1-피페라진아세트아미드, N-(2, 6-디메틸페닐)-4-[4-(4, 5-디페닐-2-옥사졸릴)-부틸]-1-피페라진아세트아미드, N-(4-아미노-2, 6-디클로로페닐)-4-[(4, 5-디페닐옥사졸릴)메틸]-1-피페라진아세트아미드, 4-[(4, 5-디페닐-2-옥사졸릴)메틸]-N-페닐-1-피페라진아세트아미드, N-(4-클로로페닐)-4-[(4, 5-디페닐-2-옥사졸릴)메틸]-1-피페라진아세트아미드, 4-[(4, 5-디페닐-2-옥사졸릴)메틸]-N-(4-플루오로페닐)-1-피페라진아세트아미드, 4-[(4, 5-띠페닐-2-옥사졸릴]메틸]-N-(4-메톡시페닐)-1-피페라진아세트아미드, 4-[(4, 5-디페닐-2-옥사졸릴)메틸]-N-(4-메틸페닐)-1-피페라진아세트아미드, N-(2, 6-디클로로페닐)-4-[4-(4, 5-디페닐-2-옥사졸릴)메틸]-1-피페라진아세트아미드, 및 2, 6-디메틸페닐-4-[[4, 5-(4-메톡시페닐)-2-옥사졸릴]메틸]-1-피페라진아세트아미드로 이루어진 그룹ㅂ중에서 선택된 화합물.
  4. 제1항에 있어서, 4-[[4, 5-비스(4-에틸페닐)-2-이미다졸릴]메틸]-N-(2, 6-디메틸페닐)-1-피페라진아세트아미드, N-(2, 6-디메틸페닐)-4-[[4, 5-디페닐-2-이미다졸릴)메틸]-1-피페라진아세트아미드, N-(2, 6-디메틸페닐)-4-[4-(4, 5-디페닐-2-티아졸릴)부타닐]-1-피페라진아세트아미드, N-(2, 6-디메틸페닐)-4-[[(4, 5-디페닐-2-티아졸릴)메틸]-1-피페라진아세트아미드, 및 N-(2, 6-디메티레핀ㄹ)-4[[5-[4[(디메틸아미노)페닐]]-[5-페닐-2-이미다졸릴)메틸]-1-피페라진아세트아미드로 이루어진 그룹중에서 선택된 화합물.
  5. 제1항에 있어서, 에틸-4-[[[(2, 6-디메티레닐)아미노]카르복시메틸]-1-[(4, 5-디페닐-옥사졸릴)메틸)-2-피페라진카르복시레이트, 2-아미노카르보닐-4-[[4, 5-디페닐-2-옥사졸릴]메틸]-N-(2, 6-디메틸페닐)-1-피페라진아세트아미드. (1S, 4S) N-(2, 6-디메틸페닐)-5-[[4, 5-디페닐-2-옥사졸릴)메틸]-2, 5-디아자바이사이클로[2, 2, 1]헵탄-2-아세트아미드, 2-아미노카르보닐-N-(2, 6-디메틸페닐)-4-[[4, 5-디페닐-2-옥사졸리)메틸]-1-피페라진아세트아미드, 3-(아미노카르보닐)-N-(4-아미노-2, 6-디클로로페닐)-4-[[(4, 5-디페닐-2-옥사졸리)메틸-1-피페라진아세트아미드, 2-아미노카르보닐-N-(4-아미노-2, 6-디클로로페닐-4-[[(4, 5-디페닐옥사졸릴)메틸-1-피페라진아세트아미드, 2-아미노카르보닐-4-[(4, 5-디페닐-2-옥사졸릴)메틸]-N-(4-아미노-2, 6-디클로로페닐)-1-피페라진아세트아미드. 5-[[3, 5-디클로로-4-[[[4-[2-(아미노카르보닐)-4-[(4, 5-디페닐-2-옥사졸릴)메틸]-1-피페라지닐]아세틸]아미노]페닐]아미노]-S-옥소 펜탄산 메틸에스테르, 2-(아미노카르보닐)-4-[(4, 5-디페닐-2-옥사졸릴)메틸]-N-(2, 6-디클로로페닐)-1-피페라진아세트아미드, 메틸 1-[[[(2 6-디메틸페닐)아미노]카르보닐]메틸]-4-[(4, 5-디페닐-2-옥사졸릴)메틸]-2-피페라진카르복실레트, 2-(아미노카르보닐)-N-(4-아미노-2, 6-디클로로페닐)-4-[[4, 5-비스(4-플루오로페닐)-2-옥사졸릴]메틸]-1-피페라진아세트아미드, 및 2-(아미노카르보닐)-N-(2, 6-디클로로-4-니트로페닐)-4-[(4, 5-디페닐-2-옥사졸릴)메틸]-1-페페라진아세트아미드로 이루어진 그룹중에서 선택된 화합물.
  6. 제5항에 있어서, 2-아미노카르보닐-4-[(4, 5-디페닐-2-옥사졸릴)메틸]-N-(4-아미노-2, 6-디클로로페닐)-1-피페라진아세트아미드인 화합물.
  7. 제1항 내지 제6항중 어느 한 항에 있어서, 허혈치료제로서 사용하기 위한 화합물.
  8. 활성성분으로서 제1항 내지 제6항중 어느 한 항에 따른 화합물과 함게 이의 약제학적으로 허용되는 담체, 부형제 또는 희석제를 함유한 약제.
  9. 제8항에 있어서, 단위용량형인 약제.
  10. 일반식(Ⅱ)의 화합물을 a)일반식 (X)의 화합물과 반응시켜 X 가 O 또는 S 인 일반식(Ⅰ)생성물을 수득하거나 b)일반식(Ⅶ)의 화합물 즉 Eto2C-(CH2)n-LG와 반응시킨 후 일반식(Ⅸ)의 화합물 즉
    과 반응시켜 중간체 일반식(Ⅵ)를 얻은 다음 NH4OAc/HOAc와 반응시켜 X가 O또는 NH인 일반식(Ⅰ)생성물을 수득하거나, c) 일반식(Ⅶ)의 화합물과 반응시켜 중간체(Ⅵ)를 수득하고 NH4OAc/HOAc와 반응시켜 X가 O 또는 NH인 일반식(Ⅰ)생성물 수득함을 포함하며, 제1항 내지 제6항중 어느 한 항에 따른 화합물을 제조하는 방법:
    상기식에서, R1및 R2는 수소, C1-4알킬, C1-4알콕시, 할로겐 및 트리플루오로메틸중에서 독립적으로 선택되고, R3은 수소, 할로겐, C1-4알콕시, 니트로 또는 -NR9R10이고, R4는 수소 또는 C1-4알킬이고, R5및 R6은 수소, -CO2R11, -CONR9R10및 옥소중에서 독립적으로 선택되거나, R5및 R6은 함께 결합되어 메틸렌 또는 에틸렌 다리를 형성할 있고, R7및 R8은 부틸렌 다리로서 함께 결합되거나, R7및 R8은 각각이고, R9및 R10은 수소, C1-4알킬, 알카노일 및중에서 독립적으로 선택되고, R11은 C1-4알킬이고, n은 0 또는 1 내지 4이고, R12는 수소, 할로겐, 트리플루오로메틸, C1-4알킬 또는 C2-4알킬 -N(R4)2이고, LG는 이탈그룹이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930014660A 1992-07-31 1993-07-29 디페닐 옥사졸 티아졸 및 이미다졸의 아데노신 재흡수 억제 유도체 KR940005614A (ko)

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