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KR950700241A - 신규한 아미딘 유도체, 이의 제조방법 및 LTB_4 길항작용을 하는 약제로서의 이의 용도(Novel amidine derivatives, their preparation and their use as medicaments with LTB_4 antagonistic effect) - Google Patents

신규한 아미딘 유도체, 이의 제조방법 및 LTB_4 길항작용을 하는 약제로서의 이의 용도(Novel amidine derivatives, their preparation and their use as medicaments with LTB_4 antagonistic effect)

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KR950700241A
KR950700241A KR1019940702669A KR19940702669A KR950700241A KR 950700241 A KR950700241 A KR 950700241A KR 1019940702669 A KR1019940702669 A KR 1019940702669A KR 19940702669 A KR19940702669 A KR 19940702669A KR 950700241 A KR950700241 A KR 950700241A
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alkyl
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formula
halogen
acyl
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KR0163222B1 (ko
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안더스케비츠 랄프
슈롬 쿠르트
렌트 에른스트-옷토
함멜스바흐 프랑크
비르게 프란츠
퓌그너 아르민
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디터 라우딘, 루돌프 호프만
베링거 인겔하임 카게
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Priority claimed from DE4203201A external-priority patent/DE4203201A1/de
Priority claimed from DE4224289A external-priority patent/DE4224289A1/de
Priority claimed from DE4244241A external-priority patent/DE4244241A1/de
Application filed by 디터 라우딘, 루돌프 호프만, 베링거 인겔하임 카게 filed Critical 디터 라우딘, 루돌프 호프만
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Abstract

본 발명은 통상적인 방법으로 제조될 수 있고 통상적인 생약 제조로서 치료용으로 사용되는 다음 일반식(Ⅰ)의 화합물에 관한 것이다.

Description

신규한 아미딘 유도체, 이의 제조방법 및 LTB4길항작용을 하는 약제로서의 이의 용도(Novel amidine derivatives, their preparation and their use as medicaments with LTB4antagonistic effect)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (15)

  1. 라세미체로서, 순수하거나 집중적인 형태를 이룬 거울상 이성체, 가능하게는 부분입체이성체의 쌍으로서, 시스- 또는 트랜스 형태로서, 및 유리 염기 또는 염, 바람직하게는 약리학적으로 허용되는 산과의 염으로서의 다음 일반식(Ⅰ)의 화합물.
    상기식에서, R1및 R2는 동일하거나 상이하며, CF3, 할로겐, R5, OR5, COR6, SR6, SOR6, S02R6, S02NR5R7또는 C(OH)R5R7이거나, 벤젠 환의 인접한 탄소 원자와 결합하여, 각각 C1-4알킬에 의해 치환될 수 있는 -CR8=CR9-CH=CH-, -CH=CR8-CR9=CH-, -CR8=CH-CR9=CH-, -0-CHR10-CH12-, 0-CH2-0-, -0-CH|2-CH2-0-, -(CH2)3-4, -NH-CO-0-, -NH-CO-CH2-0-, -CO-CH2-0- 또는 -CO-CH2CH2-0의 이중결합된 그룹을 나타낼 수 있고, R3은 할로겐, OH, CF3, R5, OR6, COR6, CONH5R7, CH2OH, CH2-0(C1-4-알킬), SR6, SOR6, SO2R6, S02NR5R7, NH-CO-(C1-4-알킬), NH-S02-(C1-4-알킬), NR5R7또는 C(OH)R5R7[여기서, R3이 R5와 동일한 경우, 치환체 R1및 R2중의 적어도 하나가 H가 아니라면 R5는 반드시 H이다]이거나, 1 내지 3개의 헤테로 원자를 갖는 일반식
    헤테로사이클릭 5원환[여기서, D, E 및 G는 동일하거나 상이하며, CH, N, C-(C1-4-알킬) 또는 C-페닐이고, L은 0 또는 S이다]이며, R4는 할로겐, NH2, NH-(C1-4-알킬); N(C1-4-알킬)2, OH 또는 C1-4-알콕시이고, R5는 H, C1-12-알킬 또는 페닐이거나, 할로겐, C1-4-알킬, C1-4-알콕시 또는 C2-5-아실에 의해 임의로 치환된 페닐이거나, 또는 페닐-(C1-4-알킬)이며, R6은 C1-12-알킬 또는 페닐이거나, 할로겐, C1-4-알킬, C1-4-알콕시 또는 C2-C5-아실에 의해 임의로 치환된 페닐이고, R7은 H 또는 C1-12-알킬이며, R8및 R9는 동일하거나 상이하고, H, OH, C1-4-알킬, C1-4-알콕시 또는 C2-5-아실이며, R10은 H 또는 C1-4-알킬이고, R11및 R12는 동일하거나 상이하며, H, OH, 할로겐, CF3, C1-4-알킬 또는 C1-4-알콕시이고, A는 그룹
    X1-A1-X2(Ⅱ)
    X2-A2-X3(Ⅲ)
    X4-A2-X2(Ⅳ)
    (CH2)1-2-NH-CO-(CH2)1-3-X2(Ⅴ)
    -CH=CH-A2-X2(Ⅵ)
    중의 하나이며, B는 CH=CH, CH=N, S 또는이고, A1은 C2-4-알킬렌, 시스- 또는 트랜스 -CH2-CH=CH-CH2,
    CH2-CC-CH2,
    또는이며, A는 C1-5-알킬렌이고, X1은 O, NH, S, SO, SO2, CO, CH2또는이며, X2는 O, NH, S 또는이고, X3은 NH-CO, CO-NH, SO2-NH 또는이며, X4는 NH-CO, CO-NH, NH-S02, S02-NH 또는 NH-CO-NH이다.
  2. 다음 일반식(Ⅰ')의 화합물.
    상기식에서, R1및 R2는 동일하거나 상이하며, R7, OR7, COR6또는 할로겐이거나, 벤젠 환의 인접한 탄소원자와 결합하여, -CR8=R9-CH=CH-, -CH=CR8-CR9=CH-, -0-CHR10-CH2- 또는 -CO-CH2-CH2-0-의 이중결합된 그룹을 나타낼 수 있고, R3은 할로겐, CF3, R7, OR7, C0-(C1-4-알킬), NH-CO-(C1-4-알킬), NHS02-(C1-4-알킬) 또는 N(R10)2[여기서, 치환체 R1및 R2중의 적어도 하나가 H가 아닌 경우, R7은 반드시 H이다]이거나, 일반식
    헤테로사이클릭 5원 환이며, R6및 R7은 위에서 정의한 바와 같고, A는 그룹(Ⅱ)이다.
  3. 제1항 또는 제2항에 있어서, R1/R2/R3이 C2-5-아실/H/H, C6H5CO/H/H, C1-4-알킬/OH/H, C2-5-아실/C1-4-알킬/H, C2-5-아실/OH/C1-4-알킬 또는 OH/C2-5-아실/C1-4-알킬인 화합물.
  4. 제1항 내지 제3항 중의 어느 한 항에 있어서, A가 0-(CH2)2-0, 0-(CH2)4-0 또는인 화합물.
  5. 제1항 내지 제4항 중의 어느 한 항에 있어서, 그룹(Ⅱ)가 아세틸페닐렌 화합물.
  6. 제1항 내지 제5항 중의 어느 한 항에 있어서, 그룹이인 화합물.
  7. 유리 염기 또는 산 부가염 형태인 다음 일반식의 화합물.
    상기식에서, a는 0 또는 1이고, b는 1 또는 2이며, R은 C1-4-알킬이고, 단 a가 0 또는 1이고 b가 1인 경우와 a가 1이고, b가 2인 경우에는, R이 수소일 수도 있다.
  8. 제7항에 있어서, 유리 염기로서 또는 산 부가염으로서, a가 0 또는 1이고 b가 1이거나 a가 0이고 b가 2인 화합물.
  9. 제8항에 있어서, 유리 염기로서 또는 산 부가염으로서, R이 H, CH3또는 C2H5이고 a가 0 또는 1이며, b가 1인 화합물.
  10. 제8항에 있어서, 유리 염기로서 또는 산 부가염으로서, a가 0이고 b가 2이며 R이 CH3인 화합물.
  11. 제1항 내지 제10항 중의 어느 한 항에 따른 화합물을 함유함을 특징으로 하는 약제학적 조성물.
  12. 염증성 및/또는 알레르기성 증상이 관련된 질환, 특히 천식, 궤양성 대장염 및 건선의 치료와 비스테로이드성 소염제에 의해 유도된 위장질환의 치료를 목적으로 하는 약제학적 조성물을 제조하기 위한, 제1항 내지 제10항 중의 어느 한 항에 따른 화합물의 용도.
  13. LTB4길항성 화합물이 사용될 수 있는 질환을 치료하기 위한, 제1항 내지 제10항 중의 어느 한 항에 따른 유효 복용량의 화합물의 용도.
  14. 염증성 및/또는 알레르기성 증상이 관련된 질환, 특히 천식, 궤양성 대장염 및 건선을 치료하고 비스테로이드성 소염제에 의해 유도된 위장 질환을 치료하기 위한, 제1항 내지 제10항 중의 어느 한 항에 따른 유효 복용량의 화합물의 용도.
  15. (a) 일반식(X)의 이미도에스테르를 암모니아와 반응시키거나, (b1) 일반식(XI)의 페놀 또는 티오페놀을 일반식(XII) 또는 (XIII)의 화합물과 반응시키거나, (b2) 일반식(XIV)의 페놀 또는 티오페놀을 일반식(XV), (XVI), (XVII) 또는 (XVIII)의 화합물과 반응시키거나, (c) 일반식(XIX)의 아미드옥심을 상응하는 아미딘이 형성되도록 환원시킴을 특징으로 하는, 제1항 내지 제10항 중의 어느 한 항에 따른 화합물의 제조방법.
    상기식에서, R1내지 R4, A, B, A1, A2, X2및 X3은 제1항에서 정의한 바와 같고, R은 바람직하게는 C1-6알킬 그룹 또는 벤질이며, Z는 OH 또는 SH이고, L은 이핵성 이탈 그룹이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940702669A 1992-02-05 1993-01-14 아미딘 유도체, 이의 제조방법 및 이를 함유하는 ltd4 길항작용을 갖는 약제 Expired - Fee Related KR0163222B1 (ko)

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DEP4203201.6 1992-02-05
DE4203201A DE4203201A1 (de) 1992-02-05 1992-02-05 Neue amidinderivate, ihre herstellung und verwendung
DE4224289A DE4224289A1 (de) 1992-07-23 1992-07-23 Neue Amidinderivate, ihre Herstellung und Verwendung
DEP4224289.4 1992-07-23
DE4244241A DE4244241A1 (de) 1992-12-24 1992-12-24 Neue Verbindungen, ihre Herstellung und ihre Verwendung
DEP4244241.9 1992-12-24
PCT/EP1993/000070 WO1993016036A1 (de) 1992-02-05 1993-01-14 Neue amidinderivate, ihre herstellung und verwendung als arzneimittel mit ltb4-antagonischer wirkung

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