KR890014516A - 피페라진 유도체 또는 이의 염, 이의 제조방법 및 활성 성분으로서 이를 함유하는 약제학적 조성물 - Google Patents

피페라진 유도체 또는 이의 염, 이의 제조방법 및 활성 성분으로서 이를 함유하는 약제학적 조성물 Download PDF

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KR890014516A
KR890014516A KR1019890002601A KR890002601A KR890014516A KR 890014516 A KR890014516 A KR 890014516A KR 1019890002601 A KR1019890002601 A KR 1019890002601A KR 890002601 A KR890002601 A KR 890002601A KR 890014516 A KR890014516 A KR 890014516A
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South Korea
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group
compound
pyridine
hydrogen atom
piperazin
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KR1019890002601A
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KR910002583B1 (ko
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도루 히라이와
겐지 다께다
조지 나까노
미네이찌 수다니
구니까쭈 후루하따
마꼬또 다까따
히로요 가와후찌
이사오 와따나베
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원본미기재
도야마 가가꾸 고교 가부시끼가이샤
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Publication of KR890014516A publication Critical patent/KR890014516A/ko
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Abstract

내용 없음.

Description

피페라진 유도체 또는 이의 염, 이의 제조방법 및 활성 성분으로서 이를 함유하는 약제학적 조성물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (83)

  1. 하기 일반식(I)의 피페라진 유도체 또는 이의 염.
    상기식에서, A 및 A가 결합하는 2개의 탄소원자는 피리딘환, 또는 니트로 그룹에 의해 치환된 벤젠환을 형성하고, X는 수소원자, 할로겐원자, 저급 알킬 그룹, 보호되거나 보호되지 않은 하이드록실 그룹, 저급 알콕시 그룹, 보호되거나 보호되지 않은 하이드록실 그룹, 저급 알콕시 그룹, 보호되거나 보호되지 않은 아미노 그룹 또는 니트로 그룹이며, B는 구조식 -CH2CH2- 또는 -CH=CH-의 그룹, 또는 구조식 -CH2O- 또는 -CH2S-의 그룹(여기서, 이들은 어떤 배향으로도 존재할 수 있다)이고, R1은 수소원자, 할로겐원자, 니트로 그룹 또는 저급 알킬 그룹이며, R2는 수소원자, 할로겐원자 또는 저급 알킬 그룹이고, R은 하나이상의 치환체[여기서, 치환체는 할로겐원자, 보호되거나 보호되지 않은 하이드록실 그룹, 니트로 그룹, 보호되거나 보호되지 않은 아미노 그룹, 디-(저급 알킬)아미노 그룹, 보호되거나 보호되지 않은 카복실 그룹, 시아노 그룹, 저급 알케닐 그룹, 저급 아실 그룹, 아릴 그룹, 저급 알케닐 옥시 그룹, 아릴옥시 그룹, 헤테로사이클릭 그룹, 헤테로사이클릭옥시 그룹, 저급 알콕시 그룹, 저급 알킬티오 그룹, 저급 알킬설피닐 그룹, 저급 알킬설포닐 그룹, 저급 알킬설포닐아미노 그룹, 저급 아킬렌디옥시 그룹, 및 치환되거나 치환되지 않은 카바모일, 설파모일 또는 저급 알킬 그룹으로 이루어진 그룹중에서 선택된다]에 의해 치환될 수 있는 아릴 또는 헤테로사이클릭 그룹이다.
  2. 제1항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하는 피페라진 유도체 또는 이의 염.
  3. 제1항 또는 2항에 있어서, X가 수소원자인 피페라진 유도체 또는 이의 염.
  4. 제1항 내지 3항중 어느 한 항에 있어서, B가 구조식 -CH2CH2- 그룹인 피페라진 유도체 또는 이의 염.
  5. 제1항 내지 4항중 어느 한 항에 있어서, R1이 수소원자인 피페라진 유도체 또는 이의 염.
  6. 제1항 내지 5항중 어느 한 항에 있어서, R2가 수소원자인 피페라진 유도체 또는 이의 염.
  7. 제1항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하고, X가 수소원자, 할로겐원자, 저급 알킬 그룹, 하이드록실 그룹, 저급 알콕시 그룹, 아미노 그룹 또는 니트로 그룹이며, B가 구조식 -CH2CH2-의 그룹이고, R1이 수소원자, 할로겐원자, 니트로 그룹 또는 저급 알킬 그룹이며, R2가 수소원자 또는 저급 알킬 그룹이고, R이 하나이상의 치환체(여기서, 치환체는 할로겐원자, 하이드록실 그룹, 니트로 그룹, 아미노 그룹, 카복실 그룹, 시아노 그룹, 저급 알케닐 그룹, 저급 아실 그룹, 아릴 그룹, 아릴옥시 그룹, 헤테로사이클릭 그룹, 헤테로사이클릭옥시 그룹, 저급 알콕시 그룹, 저급 알콕시카보닐 그룹, 저급 알킬티오 그룹, 저급 알킬설피닐 그룹, 저급 알킬설포닐 그룹, 저급 알킬설포닐아미노 그룹, 저급 알킬렌디옥시 그룹, 카바모일 그룹 및 치환되거나 치환되지 않은 저급 알킬 그룹으로 이루어진 그룹중에서 선택된다)에 의해 치환될 수 있는 페닐 그룹인 피페라진 유도체 또는 이의 염.
  8. 제7항에 있어서, X가 수소원자인 피페라진 유도체 또는 이의 염.
  9. 제7항 또는 8항에 있어서, R1이 수소원자인 피페라진 유도체 또는 이의 염.
  10. 제7항 내지 9항중 어느 한 항에 있어서, R2가 수소원자인 피페라진 유도체 또는 이의 염.
  11. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디클로로페닐)아릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  12. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(2,3-디클로로페닐)아릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  13. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(4-메톡시-3-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  14. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(3-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  15. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디메톡시페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  16. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(5-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  17. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(5-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  18. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(7-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  19. 제1항에 있어서, 화합물이 5-[4-{(E)-3-(8-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 피페라진 유도체 또는 이의 염.
  20. 일반식(II)의 화합물을 일반식(III)의 화합물과 반응시킴을 특징으로 하여, 일반식(I)의 피페라진 유도체 또는 이의 염을 제조하는 방법.
    상기식에서, A, X, B, R1, R2및 R은 1은 제1항에서 정의된 바와 같고, Y는 제거 가능한 그룹이다.
  21. 제20항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하는 방법.
  22. 제20항 또는 21항에 있어서, X가 수소원자인 방법.
  23. 제20항 내지 항중 어느 한 항에 있어서, B가 구조식 -CH1CH2-의 그룹인 방법.
  24. 제20항 내지 23항중 어느 한 항에 있어서, R1이 수소원자인 방법.
  25. 제20항 내지 24항중 어느 한 항에 있어서, R2가 수소원자인 방법.
  26. 제20항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하고, X가 수소원자, 할로겐원자, 저급 알킬 그룹, 하이드록실 그룹, 저급 알콕시 그룹, 아미노 그룹 또는 니트로 그룹이며, B가 구조식 -CH2CH2-의 그룹이고, R1이 수소원자, 할로겐원자, 니트로 그룹 또는 저급 알킬 그룹이며, R2가 수소원자 또는 저급 알킬 그룹이고, R이 하나이상의 치환체(여기서, 치환체는 할로겐원자, 하이드록실 그룹, 니트로 그룹, 아미노 그룹, 카복실 그룹, 시아노 그룹, 저급 알케닐 그룹, 저급 아실 그룹, 아릴 그룹, 아릴옥시 그룹, 헤테로사이클릭 그룹, 헤테로사이클릭옥시 그룹, 저급 알콕시 그룹, 저급 알콕시카보닐 그룹, 저급 알킬티오그룹, 저급 알킬설피닐 그룹, 저급 알킬설포닐 그룹, 저급 알킬설포닐아미노 그룹, 저급 알킬렌디옥시 그룹, 카바모일 그룹 및 치환되거나 치환되지 않은 저급 알킬 그룹으로 이루어진 그룹중에서 선택된다)에 의해 치환될 수 있는 페닐 그룹인 방법.
  27. 제26항에 있어서, X가 수소원자인 방법.
  28. 제26항 또는 27항에 있어서, R1이 수소원자인 방법.
  29. 제26항 내지 28항중 어느 한 항에 있어서, R2가 수소원자인 방법.
  30. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디클로로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  31. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(2,3-디클로로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  32. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(4-메톡시-3-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  33. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(3-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  34. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디메톡시페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  35. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(5-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  36. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(5-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  37. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(7-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  38. 제20항에 있어서, 화합물이 5-[4-{(E)-3-(8-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  39. 일반식(IV)의 화합물을 일반식(V)의 화합물과 반응시킴을 특징으로 하여, 일반식(I)의 피페라진 유도체 또는 이의 염을 제조하는 방법.
    상기식에서, A, X, B, R1, R2및 R은 제1항에서 정의된 바와 같고, Y는 제거가능한 그룹이다.
  40. 제39항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하는 방법.
  41. 제39항에 내지 40항에 있어서, X가 수소원자인 방법
  42. 제39항에 내지 41항중 어느 한 항에 있어서, B가 구조식 -CH2CH2-의 그룹인 방법.
  43. 제39항에 내지 42항중 어느 한 항에 있어서, R1이 수소원자인 방법.
  44. 제39항에 내지 43항중 어느 한 항에 있어서, R2가 수소원자인 방법.
  45. 제39항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하고, X가 수소원자, 할로겐원자, 저급 알킬 그룹, 하이드록실 그룹, 저급 알콕시 그룹, 아미노 그룹 또는 니트릴 그룹이며, B가 구조식 -CH2CH2-의 그룹이고, R1이 수소원자, 할로겐원자, 니트로 그룹 또는 저급 알킬 그룹이며, R2가 수소원자 또는 저급 알킬 그룹이고, R이 하나이상의 치환체(여기서, 치환체는 할로겐원자, 하이드록실 그룹, 니트로 그룹, 아미노 그룹, 카복실 그룹, 시아노 그룹, 저급 알케닐 그룹, 저급 아실 그룹, 아릴 그룹, 아릴옥시 그룹, 헤테로사이클릭 그룹, 헤테로사이클록옥시 그룹, 저급 알콕시 그룹, 저급 알콕시카보닐 그룹, 저급 알킬티오 그룹, 저급 알킬설피닐 그룹, 저급 알킬설포닐 그룹, 저급 알킬설포닐아미노 그룹, 저급 알킬렌디옥시 그룹, 카바모일 그룹 및 치환되거나 치환되지 않은 저급 알킬 그룹으로 이루어진 그룹중에서 선택된다)에 의해 치환될 수 있는 페닐 그룹인 방법.
  46. 제45항에 있어서, X가 수소원자인 방법.
  47. 제45항 또는 46항에 있어서, R1이 수소원자인 방법.
  48. 제45항 내지 47항중 어느 한 항에 있어서, R2가 수소원자인 방법.
  49. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디클로로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  50. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(2,3-디클로로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  51. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(4-메톡시-3-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  52. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(3-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  53. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디메톡시페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  54. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(5-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  55. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(5-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  56. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(7-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  57. 제39항에 있어서, 화합물이 5-[4-{(E)-3-(8-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  58. 일반식(VI)의 화합물을 환원시킴을 특징으로 하여, 일반식(I)의 피페라진 유도체 또는 이의 염을 제조하는 방법.
    상기식에서, A, X, B, R1, R2및 R은 제1항에서 정의된 바와 같다.
  59. 제58항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하는 방법.
  60. 제58항 또는 59항에 있어서, X가 수소원자인 방법.
  61. 제58항 내지 60항중 어느 한 항에 있어서, B가 구조식 -CH2CH2-의 그룹인 방법.
  62. 제58항 내지 61항중 어느 한 항에 있어서, R1이 수소원자인 방법.
  63. 제58항 내지 62항중 어느 한 항에 있어서, R2가 수소원자인 방법.
  64. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디클로로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  65. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(2,3-디클로로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  66. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(4-메톡시-3-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  67. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-니트로페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  68. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(3,4-디메톡시페닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  69. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(5-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  70. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(5-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  71. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(7-벤조티에닐)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  72. 제58항에 있어서, 화합물이 5-[4-{(E)-3-(8-니트로-1-나프틸)알릴}피페라진-1-일]-10,11-디하이드로-5H-벤조[4,5]사이클로헵타[1,2-b]-피리딘인 방법.
  73. 하기 일반식(I)의 피페라진 유도체 또는 이의 염의 유효량을 함유함을 특징으로 하는 약제학적 조성물.
    상기식에서, A, X, B, R1, R2및 R은 제1항에서 정의된 바와 같다.
  74. 제73항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하는 약제학적 조성물.
  75. 제73항 또는 74항에 있어서, X가 수소원자인 약제학적 조성물.
  76. 제73항 내지 75항중 어느 한 항에 있어서, B가 구조식 -CH2CH2-의 그룹인 약제학적 조성물.
  77. 제73항 내지 76항중 어느 한 항에 있어서, R1이 수소원자인 약제학적 조성물.
  78. 제73항 내지 77항중 어느 한 항에 있어서, R2가 수소원자인 약제학적 조성물.
  79. 제73항에 있어서, A 및 A가 결합하는 2개의 탄소원자가 피리딘환을 형성하고, X가 수소원자, 할로겐원자, 저급 알킬 그룹, 하이드록실 그룹, 저급 알콕시 그룹, 아미노 그룹, 또는 니트릴 그룹이며, B가 구조식 -CH2CH2-의 그룹이고, R1이 수소원자, 할로겐원자, 니트로 그룹 또는 저급 알킬 그룹이며, R2가 수소원자 또는 저급 알킬 그룹이고, R이 하나 이상의 치환체(여기서, 치환체는 할로겐원자, 하이드록실 그룹, 니트로 그룹, 아미노 그룹, 카복실 그룹, 시아노 그룹, 저급 알케닐 그룹, 저급 아실 그룹, 아릴 그룹, 아릴옥시 그룹, 헤테로사이클릭 그룹, 헤테로사이클릭옥시 그룹, 저급 알콕시 그룹, 저급 알콕시카보닐 그룹, 저급 알킬티오 그룹, 저급 알킬설피닐 그룹, 저급 알킬설포닐 그룹, 저급 알킬설포닐아미노 그룹, 저급 알킬렌디옥시 그룹,카바모일 그룹 및 치환되거나 치환되지 않은 저급 알킬 그룹으로 이루어진 그룹중에서 선택된다)에 의해 치환될 수 있는 페닐 그룹인 약제학적 조성물.
  80. 제79항에 있어서, X가 수소원자인 약제학적 조성물.
  81. 제79항에 또는 80항에 있어서, R1이 수소원자인 약제학적 조성물.
  82. 제79항에 내지 81항중 어느 한 항에 있어서, R2가 수소원자인 약제학적 조성물.
  83. 뇌 혈관성 질병 또는 후-뇌 혈관성 질병의 치료제를 제조하기 위한 제1항에 따른 피페라진 유도체 또는 이의 염의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890002601A 1988-03-03 1989-03-03 피페라진 유도체 또는 이의 염, 이의 제조방법 및 활성 성분으로서 이를 함유하는 약제학적 조성물 KR910002583B1 (ko)

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KR910002583B1 (ko) 1991-04-27
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GB8904163D0 (en) 1989-04-05
SE8900727L (sv) 1989-09-04
JP2852659B2 (ja) 1999-02-03
DK101489D0 (da) 1989-03-02
JPH01316363A (ja) 1989-12-21
BE1002334A5 (fr) 1990-12-18
HU201923B (en) 1991-01-28
CA1336429C (en) 1995-07-25
NL8900517A (nl) 1989-10-02
AU3091489A (en) 1989-09-07
HU211567A9 (en) 1995-12-28
GB2216517A (en) 1989-10-11
AU612469B2 (en) 1991-07-11
IT1231942B (it) 1992-01-16
NL193024B (nl) 1998-04-01
GB2216517B (en) 1991-11-06
DE3906920C2 (de) 1998-07-02
DE3906920A1 (de) 1989-09-14
IT8947701A0 (it) 1989-03-02
CH678427A5 (ko) 1991-09-13
FR2628108B1 (ko) 1994-04-22
HUT49601A (en) 1989-10-30
DK171436B1 (da) 1996-10-28
DK101489A (da) 1989-09-04
SE508347C2 (sv) 1998-09-28
US4948796A (en) 1990-08-14
SE8900727D0 (sv) 1989-03-02
FR2628108A1 (fr) 1989-09-08

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