KR940006993A - 아미디노페놀 유도체, 이의 제조방법 및 이를 함유하는 제약학적 조성물 - Google Patents

아미디노페놀 유도체, 이의 제조방법 및 이를 함유하는 제약학적 조성물 Download PDF

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KR940006993A
KR940006993A KR1019930019019A KR930019019A KR940006993A KR 940006993 A KR940006993 A KR 940006993A KR 1019930019019 A KR1019930019019 A KR 1019930019019A KR 930019019 A KR930019019 A KR 930019019A KR 940006993 A KR940006993 A KR 940006993A
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alkyl
compound
sulfur
amidinophenoxycarbonyl
phenylalkyl
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히사오 나카이
마사노리 카와무라
츠모루 미야모토
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사노 카즈오
오노 화아마슈티칼 캄파니 리미팃드
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Abstract

하기 일반식(Ⅰ)의 아미디노폐물 유도체:
식에서 R1및R2는 (ⅰ)H, (ⅱ)C1-4알킬, (ⅲ)C1-4알콕시, (ⅳ)C2-5아실, (ⅴ)할로겐, (ⅵ)N02, (ⅶ)벤조일, (ⅷ)COR4(이때 R5및 R6H 또는 C1-4알킬이다)이고; A는 결합, C1-4알킬렌, C(R5)=C(R6)-(이때 R5및 R6H 또는 C1-4알킬이다)이고; R3는 (ⅰ)CON(R7)(R8), (ⅱ)CON(R9)-CH(R7)(R8)또는(ⅲ)CONR10(이때 R7및 R8은 (1)H, (2)페닐, (3)C7-10페닐알킬, (4) 1또는 2개의 C1-4알킬, 할로겐 또는 R11-COOR12(이때 R11은 결합, C1-8알킬렌, C2-8알케닐렌, C2-8알키닐렌이고, R12는 H, C1-4알킬, C7-C10페닐알킬, 페닐, 알릴, 프로파르기이다)에 의해 치환된 페닐 또는 C7-C10페닐알킬, (5)C1-10알킬, (6)1내지 3개의 이중 결합을 갖는 C2-10알케닐, (7)1또는 2개의 삼중 결합을 갖는 C2-10알키닐, (8)R11a-COXR12(이때 R11a는 (a)결합, (b)C1-8알킬렌, (c)주쇄내 1또는 2개의 탄소 원자가 황, 또는 황 및 페닐렌으로 치환되는 C2-8알킬렌, (d)C2-8알케닐렌, (e)주쇄내 1또는 2개의 탄소 원자가 황, 또는 황 및 페닐렌으로 치환되는 C4-8알케닐렌, (f)C2-8알키닐렌, (g)주쇄내 1또는 2개의 탄소 원자가 황, 또는 황 및 페닐렌으로 치환되는 C4-8알키닐렌이고; X는 -O-또는 -NH-이다), (9)1개의 N원자를 함유하는 7-14원, 비-또는 트리-시클릭 헤테로 고리를 치환된 C1-4알킬, (10)C3-7시킬로알킬이다)이고; R9은 (1)H, (2)C1-8알킬, (3)C7-C10페닐알킬, (4)1내지 3개의 이중 결합을 갖는 C2-10알케닐, (5) 1 또는 2개의 삼중 결합을 갖는 C2-10알케닐, (6)R11-COOR12,(7)C3-7시클로알킬이고; N⊃은 1또는 2개의 N 원자를 함유하는 4-7원, 모노-시클릭 헤테로 고리이고; R18은 H, C7-10 페닐알킬 또는 COOR13(이때 R13은 H, C1-4알킬 또는 C7-10페닐알킬이다)이다)이나; 단 (1)R7및 R8둘 다 동시에 수소를 나타내지는 않고, (ⅱ)R7,R8및 R9내 적어도 1개의 기가 t-부틸 에스테르를 함유하는 기를 나타내면, 다른 기들은 카르복시를 함유하는 기를 나타내지 않는다; 또는 이의 산 부가염은 PLA2, 및 트립신, 플라즈민, 트롬빈, 칼리크레인, 특히 트립신과 같은 다양한 프로테아제에 저해 활성을 가지며, 다양한 염증성 질병, 알레르기성 질병, 전염된 매과 내 응혈, 췌장염, 심한 췌장염 및 다중 손상의 예방 및/또는 치료에 유용하다.

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아미디노페놀 유도체, 이의 제조방법 및 이를 함유하는 제약학적 조성물
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Claims (18)

  1. 하기 일반식(Ⅰ)의 화합물, 또는 이의 산-부가염:
    식에서 R1및 R2는 각각 독립적으로; (ⅰ)수소, (ⅱ)C1-4알킬, (ⅲ)C1-4알콕시, (ⅳ)C2-5아실, (ⅴ)할로겐, (ⅵ)니트로, (ⅶ)벤조일 또는 (ⅷ)COOR4( 이때 R4는 C1-3알킬이다)이고; A는 결합, C1-4알킬렌 또는
    (이때 R5및 R6는 각각 독립적으로 수소 또는 C1-4알킬이다)이고; R3는또는(이때, R7및 R8은 (1)수소, (2)페닐, (3)C7-10페닐알킬, (4) C1-4알킬, 할로겐 또는 R11-COOR12(이때 R11은 (a)결합, (b)C1-8알킬렌, (c)C2-8알케닐렌 또는 (d)C2-8알키닐렌이고, R12는 (a) 수소, (b)C1-4알킬, (c)C7-C10페닐알킬, (d)페닐, (e)알릴 또는 (f)프로파르길이다)에 로부터 선택된 1또는 2개의 치환체로 가각 치환되는 페닐 또는 C7-C10페닐알킬, (5)C1-10알킬, (6)1내지 3개의 이중 결합을 갖는 C2-10알케닐, (7)1내지 2개의 삼중 결합을 갖는 C2-10알키닐, (8)R11a-COXR12(이때 R11a-COXR12는 (a)결합, (b)C1-8알킬렌, (c)주쇄내 1또는 2개의 탄소 원자가 황, 또는 황 및 페닐렌으로 치환되는 C2-8알킬렌, (d)C2-8알케닐렌, (e)주쇄내 1또는 2개의 탄소 원자가 황, 또는 황 및 페닐렌으로 치환되는 C4-8알케닐렌, (f)C2-8알키닐렌, (g)주쇄내 1또는 2개의 탄소 원자가 황, 또는 황 및 페닐렌으로 치환되는 C4-8알키닐렌이고; X는 산소 또는 -NH-이며, R12는 상기 정의된 바와 같은 의미이다) (9)질소원자 1개를 함유하는 7-14원, 비-또는 트리-시클릭 헤테로 고리에 의해 치환되는 C1-4알킬, 또는 (10)C3-7시킬로알킬이다)이고; R9은 (1)수소, (2)C1-8알킬, (3)C7-C10페닐알킬, (4)1내지 3개의 이중 결합을 갖는 C2-10알케닐, (5) 1또는 2개의 삼중 결합을 갖는 C2-10알키닐, (6)R11-COOR12(이때 R11및R12는 상기 정의된 바와 같은 의미이다), 또는 (7)C3-7시클로알킬이고; N⊃은 1또는 2개의 질소를 함유하는 4-7원, 모노-시클릭 헤테로 고리이고; R10은 (1)수소, (2)C7-10페닐알킬 또는 (3)COOR13(이때 R13은 수소, C1-4알킬 또는 C7-10페닐알킬이다)이다); 단 (i)R7및 R8둘 다 동시에 수소를 나타내지는 않고, (ⅱ)R7,R8및 R9내 적어도 1개의 기가 t-부틸 에스테르를 함유하는 기를 나타내면, 다른 기들은 카르복시를 함유하는 기를 나타내지 않는다.
  2. 제1항에 있어서, R3는 (ⅰ)또는 (ⅱ)(식에서 다양한 부호는 제1항에 정의된 바와 같다)인 화합물.
  3. 제1항에 있어서, R3는 (ⅲ)CON⊃ -R10(식에서 다양한 부호는 제1항에 정의된 바와 같다)인 화합물.
  4. 제1항에 있어서, N⊃은 1개의 질소를 함유하는 4-7원, 모노-시클릭 헤테로 고리인 화합물.
  5. 제1항에 있어서, N⊃은 1개의 질소를 함유하는 4-7원, 모노-시클릭 헤테로 고리인 화합물.
  6. 제2항에 있어서, R7및 R8중 하나는 (9)1개의 질소원자 함유하는 7-14원, 비-또는 트리-시클릭 헤테로 고리에 의해 치환되는 C1-4알킬인 화합물.
  7. 제2항에 있어서, R7및 R8은 (2)페닐, (3)C7-10페닐알킬, 94) C1-4알킬, 할로겐, 및 R11-COR12(식에서 R11및R12는 제1항에 정의된 바와 같다)로 부터 임의로 선택된 1또는 2개의 치환제로 치환되는 페닐 또는 C7-10페닐알킬, (8)R11a-COXR12(이때 R11a는 (C)주쇄내 2개의 탄소 원자가 황 및 페닐렌에 의해 치환되는 C2-8알킬렌, (e)주쇄내 2개의 탄소원자가 황 및 페닐렌에 의해 치환되는 C2-8알킬렌(e)주쇄내 2개의 탄소원자가 황 및 페닐렌에 의해 치환되는 C4-8알킬렌, (g)주쇄내 2개의 탄소 원자가 황 및 페닐렌으로 치환되는 C4-8알키닐렌이고 X및 R12는 제2항에 정의된 바와같다)또는 (10)C3-7시클로알킬인 화합물.
  8. 제2항에 있어서, R7및 R8은 (5)C1-10알킬, (6)1내지 3개의 이중 결합을 갖는 C2-10알케닐, (7)1또는 2개의 삼중 결합을 갖는 C2-10알키닐, 또는 (8)R11a-COXR12(식에서 R11a는(a)결합, (b)C1-8알킬렌, (c)주쇄내탄소 원자가 황에 의해 치환되는 C2-8알킬렌, (d)C2-8알케닐렌, (e)주쇄 내 탄소 원자가 황에 의해 치환되는 C4-8알케닐렌, (f)C2-8알키닐렌, 또는 (g)주쇄 내 탄소 원자가 황으로 치환되는 C4-8알키닐렌이고 X및 R12는 제1항에 정의된 바와 같다)인 화합물.
  9. 제1항에 있어서, p-(p-아미디노페녹시카르보닐)-α-메틸신남산 N-(2-에톡시카르보닐퍼히드로아제피닐)아미드인 화합물.
  10. 제1항에 있어서, p-(p-아미디노페녹시카르보닐)-α-메틸신남산-(2-에톡시카르보닐피페리디노)아미드, 또는 p-(p-아미디노페녹시카르보닐)신남산 N-(2-에톡시카르보닐)아미드인 화합물.
  11. 제1항에 있어서, p-(p-아미디노페녹시카르보닐)-α-메틸신남산N'-페닐메틸피페라지닐아미드인 화합물.
  12. 제1항에 있어서, p-(p-아미디노페녹시카르보닐)벤조산 N-[1-에톡시카르보닐-2-(3-인돌릴)]에틸아미드인 화합물.
  13. 제1항에 있어서, p-(p-아미디노페녹시카르보닐)-α-메틸신남산N-에톡시카르보닐메틸-N-페닐아미드, p-(p-아미디노페녹시카르보닐)-α-메틸신남산 N-(1-에톡시카르보닐-2-페닐)에틸아미드, p-(p-아미디노페녹시카르보닐)-α-메틸신남산 N-3.5-비스(에톡시카르보닐)페닐아미드, p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-(1-에톡시카르보닐-2-(4-에톡시카르보닐페닐메틸티오))에티아미드, p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-시클로프로필-N-에톡시카르보닐메틸아미드 또는 p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-시클로헥실-N-카르복시메틸아미드인 화합물.
  14. 제1항에 있어서, p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-2(-에톡시카르보닐에틸)-N-이소프로필아미드, p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-알릴-N-에톡시카르보닐메틸아미드, p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-카르복시메틸-N-알릴아미드, p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-프로파르길-N-에톡시카르보닐메틸아미드, p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-알릴-N-((1-에톡시카보닐-2-에톡시카르보닐메틸티오)에틸)아미드 또는 p(p-아미디노페녹시카르보닐)-α-메틸신남산 N-(1,1-비스(에톡시카르보닐)메틸-N-에톡시카르보닐메틸아미드인 화합물.
  15. 제1-14항 두 어느 한 항에 있어서, 산 부가염 형태인 화합물.
  16. 하기 (ⅰ)-(ⅲ)을 특징으로 하는 제1항에 청구된 일반식(Ⅰ)화합물의 제조방법; (ⅰ)하기 일반식(Ⅱa)화합물:
    (식에서 R3a는 R3에 대해 상기 정의된 바와 같은 의미이나, 단R3내 모든 R7,R8,R9및R10은 COOH 및 COOt-Bu를 함유하지 않는 기들이며, R2및 A는 제1항에 정의된 바와 같다)을 하기 일반식(Ⅲ)의 화합물:
    (식에서 R1은 제1항에 정의된 바와 같다)로써 에스테르화; (ⅱ)하기 일반식(Ⅱb)의 화합물.
    (식에서 다양한 부호들은 제1항에 정의된 바와 같다)을 하기 일반식(Ⅲb)의 화합물:
    (식에서 R7b,RR9b, R9b및 R10b는 각각 R7R8R9및 R10에 대해 상기 정의된 바와 같은 의미이나, 단 R7b, R9b및R9b중 적어도 1개의 기는 COOt-Bu를 함유하는 기이고, 다른 기들은 COOH를 함유하지 않는 기들이거나, R10bCOOt-Bu이다)로써 아미드화; 또는 (ⅲ)다양한 부호들이 제1항에서 정의된 바와 같은 일반식(Ⅰb) 화합물의 t-부틸 에스테르기의 가수분해.
  17. 부형제 또는 코우팅과, 활성 성분으로서 효과적인 양의 제1항에 표사된 일반식(Ⅰ)화합물, 또는 이의 산 부가염으로 구성되는 제약학적 조성물.
  18. 다양성 염증성 질별, 알레르기성 질병, 전염된 맥관내 응혈, 췌장염, 심한 췌장염 또는 다중 손상의 예방 및/또는 치료를 위한 제약학적 조성물의 제조에 사용하기 위한 일반식(Ⅰ)화합물 또는 이의 산 부가염.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930019019A 1992-09-18 1993-09-18 아미디노페놀 유도체, 이의 제조 방법 및 이를 함유하는 제약학적 조성물 KR100210355B1 (ko)

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