KR920702349A - N-치환 복소환식 유도체, 그의 제조방법 및 그를 함유하는 약학 조성물 - Google Patents

N-치환 복소환식 유도체, 그의 제조방법 및 그를 함유하는 약학 조성물

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KR920702349A
KR920702349A KR1019910701647A KR910701647A KR920702349A KR 920702349 A KR920702349 A KR 920702349A KR 1019910701647 A KR1019910701647 A KR 1019910701647A KR 910701647 A KR910701647 A KR 910701647A KR 920702349 A KR920702349 A KR 920702349A
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phenyl
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베르나르 끌로드
브레리에르 쟝-끌로드
끌레망 쟈크
니사토 디노
뻬레오 삐에르
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사노피
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Priority claimed from FR9003563A external-priority patent/FR2659967B1/fr
Priority claimed from FR9010144A external-priority patent/FR2665702B1/fr
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Abstract

내용 없음

Description

N-치환 복소환식 유도체, 그의 제조방법 및 그를 함유하는 약학 조성물
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Claims (21)

  1. 하기식(Ⅰ)의 화합물 및 그의 염.
    [상기 식중, R1및 R2는 유사하거나 상이하며, 각각은 수소 또는 C1~C6알킬, C1~C4알콕시, 아미노, 아미노 메틸, 카르복실, 알콕시 부분이 C1~C4인 알콕시카르보닐, 시아노, 테트라졸릴, 메틸테트라졸릴, 메틸술포닐아미노, 트리플루오로메틸술포닐아미노, 트리플루오로메틸술포닐아미노메틸, N-시아노아세트아미드, N-히드록시아세트아미드, N-(4-카르복시-1,3-티아졸-2-일)아세트아미드, 우레이도, 2-시아노구아니디노카르보닐, 2-시아노구아디노메틸, 이미다졸-1-일카르보닐 및 3-시아노-2-메틸이소티오우레이도메틸에서 선택된 기이고, 단, 적어도 하나의 치환기 R1또는 R2는 수소 이외의 것이며, R3는 수소, 비치환되었거나 1개 이상의 할로겐원자로 치환된 C1~C6알킬, C2~C6알케닐, C3~C7시클로알킬, 페닐, 알킬 부분이 C1~C3인 페닐알킬, 또는 알케닐 부분이 C2~C3인 페닐알케닐이며, 이들 페닐기는 비치환되거나 할로겐원자, C1~C4알킬, C1~C4할로겐노알킬, C1~C|4폴리할로게노알킬, 히드록실 또는 C1~C4알콕시로 단일 치환 또는 다중치환되고, R4및 R5는 각각 C1~C6알키, 페닐, 또는 알킬 부분이 C1~C3인 페닐알킬이며, 이들 알킬, 페닐 및 페닐알킬기는 비치환되거나 1개 이상의 할로겐원자 또는 C1~C4퍼플루오로알킬, 히드록실 및 C1~C|4알콕시에서 선택된 기로 치환되거나, 또는 R4및 R5는 함께 식=CR7R8(식중, R7는 수소, C1~C4알킬 또는 페닐이고, R8는 C1~C4알킬 또는 페닐이다)의 기를 형성하거나, 또는 R4및 R5는 모두 식(CH2)n(식중, n는 2~11의 정수이다)의 기 또는 식(CH2)|pY(CH2)q(식중, Y는 산소원자, 또는 황원자, 또는 C1~C4알킬기, 페닐기 또는 알킬 부분이 C1~C|3인 페닐알킬기로 치환된 탄소원자이고, p+q=m이며, m은 2~5의 정수이다)의 기, 또는 식 N-R6(식중, R6는 수소, C1~C4알킬, 알킬부분이 C1~C3인 페닐알킬, C1~C4알킬카르보닐, C1~C4할로게노알킬 카르보닐, C1~C4폴리할로게노알킬카르보닐, 벤조일, α-아미노아실 또는 N-보호기이다)의 기이거나, 또는 R4및 R5는 이들이 결합된 탄소원자와 함께 인단 또는 아다만탄을 형성하며, X는 산소원자 또는 황원자이고, z및 t는 0이거나, 이들중 하나는 0이고 다른 하나는 1이다)
  2. 제1항에 있어서, R1가 오르토 위치이며 카르복실 또는 테트라 졸릴기이고, R2가 수소인 화합물.
  3. 제1항 또는 제2항에 있어서, R4및 R5가 이들이 결합된 탄소와 함께 시클로펜탄 또는 시클로헥산을 형성하는 화합물.
  4. 제1항 내지 제3항중 어느 한 항에 있어서, R3가 직쇄 C1~C6알킬기인 화합물.
  5. 제1항 내지 제4항중 어느 한 항에 있어서, X가 산소인 화합물.
  6. 제1항 내지 제5항중 어느 한 항에 있어서, z=t=0인 화합물.
  7. 제1항에 있어서, 2-n-부틸-4-스피로시클로펜탄-1-[(2'-테트라졸-5-일)비페닐-4-일)메틸]-2-이미다졸릴-5-온 또는 그의 산 또는 염기와의 염.
  8. a1)하기식(2)의 복소환식 유도체를 하기식(3)의 (비페닐-4-일) 메틸 유도체와 반응시키고, b1)필요에 따라, 하기식(4)의 생성 화합물을 라웨손 시약 2,4-비스(4-메톡시페닐)-1,3-디티아-2,4-디포스페탄 2,4-디술피드]으로 처리하고, c1) 상기 a1) 또는 b1)에서 수득된 하기식(5)의 화합물을 기 R'1및/또는 R'2을 각각 기 R1및/또는 R2로 전환하는 처리를 수행시켜 화합물(Ⅰ)을 수득함을 특징으로 하는 제1항 내지 제7항중 어느 한 항에 따른 화합물(Ⅰ)의 제조방법.
    [상기 식중, z, t, R3, R4및 R5는 상기 제1항에서 화합물(Ⅰ)에 대해 정의한 바와 동일하고, Hal는 할로겐 원자이며, R'1및 R'2는 각각 R1및 R2또는 R1및 R2의 전구체 기이다]
  9. a2)하기식 (7)의 아미노산을 하기식(8)의 (비페닐-4-일)메틸아민 유도체와 반응시키고, b2)아민의 탈보호후, 하기식(9)의 생성화합물을 하기식(10)의 알킬 오르토-에스테르로 처리하고, c2)필요에 따라, 하기식(4)의 생성 화합물을 라웨손 시약[2,4-비스-(4-메톡시페닐)-1,3-디티아-2,4-디포스페탄 2,4-디술피드]으로 처리하고, d2)상기 b2) 또는 c2)에서 수득된 하기식(5)의 화합물을 기 R'2및/또는 R'1을 각각 기 R2및/또는 R1로 전환하는 화합물(Ⅰ)의 제조에 적합한 조건하에 처리함을 특징으로 하는, 제1항 내지 제7항중 어느 한 항에 따른 화합물(Ⅰ)의 제조방법.
    [상기 식중, z, t, R3, R4및 R5는 상기 제1항에서 화합물(Ⅰ)에 대해 정의한 바와 동일하고, 식(7)의 아민기는 Pr기로 보호되며, R'1및 R'2는 각각 R1및 R2의 전구체 기이고, R는 C1~C4알킬이다]
  10. a3)하기식 (3)의 (비페닐-4-일)메틸 유도체를 산소 및 UN조사 존재하에 염기성 매질에서 하기식(11)의 이미다졸 유도체와 반응시키고, b3)의 필요에 따라, 하기식(4')의 생성 화합물을 라웨손 시약[2,4-비스-(4-메톡시페닐)-1,3-디티아-2,4-디포스페탄 2,4-디술피드]으로 처리하고, c3)상기 b3 또는 c3에서 수득한 하기식(5')의 화합물을 기 R'1및/또는 R'2을 각각 기 R1및/또는 R2로 전환하는 화합물(Ⅰ)을 제조하는데 적합한 조건하에 처리함을 특징으로 하는 제6항에 따른 화합물(Ⅰ)의 제조방법.
    [상기 식중, Hal은 할로겐 원자이고, R'1및 R'2는 R1및 R2의 전구체 기이며, R3, R4및 R5는 상기 제1항에서 화합물(Ⅰ)에 대해 정의한 바와 동일하다]
  11. 하기식(Ⅱ)의 화합물.
    [상기 식중, R3는 수소, 비치환되었거나 1개 이상의 할로겐원자로 치환된 C1~C6알킬, C2~C6알케닐, C3~C7시클로알킬, 페닐, 알킬 부분이 C1~C3인 페닐알킬, 또는 알케닐 부분이 C2~C3인 페닐알케닐이며, 이들 페닐기는 비치환되거나 할로겐원자, C1~C4알킬, C1~C4할로게노알킬, C1~C4폴리할로게노알킬, 히드록실 또는 C1~C4알콕시이고, R4및 R5는 각각 C1~C6알킬, 페닐, 또는 알킬 부분이 C1~C3인 페닐알킬이며, 이들 알킬, 페닐 및 페닐알킬기는 비치환되거나 1개 이상의 할로겐원자 또는 C1~C4퍼플루오로알킬, 히드록실 및 C1~C4알콕시에서 선택된 기로 치환되거나, 또는 R4및 R5는 함께 식=CR7R8(식중, R7는 수소, C1~C4알킬 또는 페닐이고, R8는 C1~C4알킬 또는 페닐이다)의 기를 형성하거나, 또는 R4및 R5는 모두 식(CH2)n(식중, n는 2~11의 정수이다)의 기 또는 식(CH2)pY(CH2)q(식중, Y는 산소원자, 황원자, 또는 C1~C4알킬기, 페닐기 또는 알킬 부분이 C1~C3인 페닐알킬기이고, p+q=m이며, m은 2~5의 정수이다)의 기, 또는 기 N-R6(식중, R6는 수소, C1~C4알킬, 알킬부분이 C1~C3인 페닐알킬, C1~C4알킬카르보닐, C1~C4할로게노알킬 카르보닐, C1~C4폴리할로게노알킬카르보닐, 벤조일, α-아미노아실 또는 N-보호기이다)이고, X는 산소원자 또는 황원자이며, z및 t는 0이거나, 이들중 하나는 0이고 다른 하나는 1이며, z및 t가 0이고, X가 산소원자일 경우, R4및 R5는 C1~C6알킬, 페닐, 또는 알킬부분이 C1~C3인 페닐알킬이며, 이들 알킬, 페닐 및 페닐알킬기는 비치환되거나 1개이상의 할로겐원자 또는 C1~C4퍼플루오로알킬, 히드록실 및 C1~C4알콕시에서 선택된 기에 의해 치환된 것 이외의 것이나, R4및 R5는 모두 기 N-R6(식중, R5는 수소, C1~C|4알킬 또는 알킬부분이 C1~C3인 페닐알킬이다)이외의 것이며, n은 6이외의 것이고, 또는 R3가 치환페닐기를 나타내는 경우, R4및 R5는 식 (CH2)n(식중, n는 3~5이다)의 기 이외의 것이며, z=1이고 R3가 페닐일 경우, R4및 R5는 각각 메틸 이외의 것이다]
  12. 제11항에 있어서, 하기식(Ⅱ')의 화합물.
    [상기 식중, X는 산소원자 또는 황원자이고, R3는 수소, 비치환되거나 1개 이상의 할로겐원자로 치환된 C1~C6알킬, C2~C6알케닐, C3~C7시클로알킬, 페닐, 알킬 부분이 C1~C4인 페닐알킬, 또는 알케닐 부분이 C2~C3인 페닐알케닐이며, 이들 페닐기는 비치환되거나 할로겐원자, C1~C4알킬, C1~C4할로게노알킬, C1~C4폴리할로게노알킬, 히드록실 또는 C1~C4알콕시이고, 단 X가 산소일 경우 R3는 치환 페닐기 이외의 것이다]
  13. 제11항에 있어서, 하기식(Ⅱ")의 화합물.
    [상기 식중, R3, R4, R5및 X는 상기 제10항에서 화합물 (Ⅱ)에 대해 정의한 바와 동일하다]
  14. 제11항에 있어서, 하기식(Ⅱ"')의 화합물.
    [상기 식중, R3는 수소, 비치환되었거나 1개 이상의 할로겐원자로 치환된 C1~C6알킬, C2~C6알케닐, C3~C7시클로알킬, 페닐, 알킬 부분이 C1~C4인 페닐알킬, 또는 알케닐 부분이 C2~C3인 페닐알케닐이며, 이들 페닐기는 비치환되거나 할로겐원자, C1~C4알킬, C1~C4할로게노알킬, C1~C4폴리할로게노알킬, 히드록실 또는 C1~C4알콕시에 의해 단일 치환 또는 다중치환되고, R4및 R5는 각각 C1~C6알킬, 페닐 또는 알킬 부분이 C1~C3인 페닐알킬이며, 이들 알킬, 페닐 및 페닐알킬기는 비치환되거나 1개 이상의 할로겐원자 또는 C1~C4퍼플루오로알킬, 히드록실 및 C1~C4알콕시에서 선택된 기로 치환되거나, 또는 R4및 R5는 함께 식=CR7R8(식중, R7는 수소, C1~C4알킬 또는 페닐이고, R8는 C1~C4알킬 또는 페닐이다)의 기를 형성하거나, 또는 R4및 R5는 모두 식(CH2)n(식중, n는 2~11의 정수이다)의 기 또는 식(CH2)pY(CH|2)q(식중, Y는 산소원자, 황원자, 또는 C1~C4알킬기, 페닐기 또는 알킬 부분이 C1~C3인 페닐알킬에 의해 치환된 탄소원자이고, p+q=m이며, m은 2~5의 정수이다)의 기, 또는 기 N-R6(식중, R6는 수소, C1~C4알킬, 알킬부분이 C1~C3인 페닐알킬, C1~C4알킬카르보닐, C1~C4할로게노알킬카르보닐, C1~C4폴리할로게노알킬카르보닐, 벤조일, α-아미노아실 또는 N-보호기이다)이거나, 또는 R4및 R5는 이들이 결합된 탄소원자와 함께 인단 또는 아다만탄을 형성하며, X는 산소원자 또는 황원자이고, 단 R4및 R5가 각각 메틸일 경우, R3는 페닐이외의 것이다]
  15. 하기식 (14)의 화합물을 하기식(13)의 화합물과 반응시키고, 필요에 따라 생성 화합물을 라웨손 시약 (2,4-비스(4-메톡시페닐)-1,3-디티아-2,4-디포스페탄 디술피드)으로 처리함을 특징으로 하는, 제11항 내지 제14항중 어느 한 항에 따른 화합물의 제조방법.
    [상기 식중, R3는 상기 제11항 내지 제14항에 나타낸 정의를 갖고, B는 기 C(OR)3,또는 기 COHal
    (식중, R은 C1~C4알킬이고, Hal는 할로겐원자, 바람직하게는 염소이다)이며, R4및 R5는 상기 제10항에서 화합물(Ⅱ)에 대해 정의한 바와 동일하고, A는 OH기, NO2기 또는 기 OR'(식중, R'는 수소 또는 C1~C4알킬이다)이다]
  16. 제1항 내지 제7항중 어느 한 항에 따른 화합물이 활성소로 존재하는 약학 조성물.
  17. 제1항 내지 제7항중 어느 한 항에 따른 화합물이 β-차단 화합물과 함께 존재하는 약학 조성물.
  18. 제1항 내지 제7항중 어느 한 항에 따른 화합물이 이뇨제와 함께 존재하는 약학 조성물.
  19. 제1항 내지 제7항중 어느 한 항에 따른 화합물이 비스테로이드성 소염제와 함께 존재하는 약학 조성물.
  20. 제1항 내지 제7항중 어느 한 항에 따른 화합물이 칼슘 길항질과 함께 존재하는 약학 조성물.
  21. 제1항 내지 제7항중 어느 한 항에 따른 화합물이 진정제와 함께 존재하는 약학 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910701647A 1990-03-20 1991-03-20 N-치환 복소환식 유도체, 그의 제조방법 및 그를 함유하는 약학 조성물 KR0175310B1 (ko)

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FR9010144A FR2665702B1 (fr) 1990-08-08 1990-08-08 Derives heterocycliques n-substitues, leur preparation, les compositions pharmaceutiques en contenant.
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PT97078B (pt) 1997-07-31
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AU641005B2 (en) 1993-09-09
IL110820A (en) 1995-11-27
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CZ287064B6 (cs) 2000-08-16
CS74591A3 (en) 1991-11-12
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HU223141B1 (hu) 2004-03-29
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ATE167475T1 (de) 1998-07-15
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FI103407B (fi) 1999-06-30
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UA42669A (uk) 2001-11-15
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