KR960705869A - 수용성의 활성 술폰을 갖는 폴리 (에틸렌글리콜) (water soluble active sulfones of poly(ethylene glycol) - Google Patents

수용성의 활성 술폰을 갖는 폴리 (에틸렌글리콜) (water soluble active sulfones of poly(ethylene glycol)

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KR960705869A
KR960705869A KR1019960702507A KR19960702507A KR960705869A KR 960705869 A KR960705869 A KR 960705869A KR 1019960702507 A KR1019960702507 A KR 1019960702507A KR 19960702507 A KR19960702507 A KR 19960702507A KR 960705869 A KR960705869 A KR 960705869A
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sulfone
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밀톤 하리스 제이.
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밀톤 하리스 제이.
쉬워워터 폴리머 인코퍼레이티드
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Abstract

폴리(에틸렌글리콜) 유도체는 분자 및 표면상의 티올 부분에 대한 선택적 부착을 위한 술폰 부분으로 활성화된다고 개시된다. 활성 PEG는 수용성이고 장기간 동안 가수분해적으로 안정하며, 티올 부분과 가수분해적으로 안정한 결합을 형성한다. 결합은 일반적으로 환원 분위기에서 가역적이지 않다. PEG 유도체는 생물학적 활성 분자 및 표면을 생체적합성을 갖도록 변형시키는 것을 포함하는 물질 특성의 변형에 유용하다. 활성 PEG의 합성방법과 활성 PEG와 생물학적 합성물질을 포함하는 다른 물질의 콘쥬게이트의 제조방법도 또한 개시된다.

Description

수용성의 활성 술폰을 갖는 폴리(에틸렌글리콜)(WATER SOLUBLE ACTIVE SULFONES OF POLY(ETHYLENE GLYCOL)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (66)

  1. 가수분해에 대해 안정한 수용성 활성 폴리머에 있어서, 상기 폴리머는 폴리(알킬렌옥시드), 폴리(옥시에틸화폴리올) 및 폴리(올레핀알코올)로 구성된 군으로부터 선택되고 적어도 한개의 활성 술폰 부분을 가지는 활성 폴리머.
  2. 제1항에 있어서, 상기 적어도 한개의 활성 술폰 부분은 적어도 두개의 탄소 원자를 가지고 술폰기로부터의 제2탄소에 위치한 반응 부위를 가지는 술폰기로 이루어진 것을 특징으로 하는 활성 폴리머.
  3. 제2항에 있어서, 상기 적어도 한개의 활성 술폰 부분은 비닐술폰, 활성 에틸술폰, 비닐술폰 및 에틸술폰의 활성 유도체와 그것들의 조합으로 구성된 군으로부터 선택되는 것을 특징으로 하는 활성 폴리머.
  4. 제3항에 있어서, 상기 폴리머는 폴리(에틸렌글리콜)이고, 상기 적어도 한개의 활성 술폰 부분은 비닐술폰 및 할로에틸술폰으로 구성된 군으로부터 선택되는 것을 특징으로 하는 활성 폴리머.
  5. 제1항에 있어서, 상기 폴리머는 폴리(에틸렌글리콜) 비닐술폰인 것을 특징으로 하는 활성 폴리머.
  6. 제1항에 있어서, 상기 폴리머는 폴리(에틸렌글리콜), 폴리(프로필렌글리콜), 폴리(옥시에틸화글리콜), 폴리(옥시에틸화소르비톨), 폴리(옥시에틸화글루코스) 및 폴리(비닐알코올)로 구성된 군으로부터 선택되는 것을 특징으로 하는 활성 폴리머.
  7. 제1항에 있어서, 상기 폴리머는 폴리(에틸렌글리콜)인 것을 특징으로 하는 활성 폴리머.
  8. 제1항에 있어서, 상기 폴리머는 생물공학적 용도에 적합한 실질적 직쇄형 폴리머인 것을 특징으로 하는 활성 폴리머.
  9. 제8항에 있어서, 상기 실질적 직쇄형 폴리머는 활성 술폰 부분이외에는 실질적으로 치환되지 않은 것을 특징으로 하는 활성 폴리머.
  10. 제10항에 있어서, 상기 폴리머는 랜덤 또는 블록 코폴리머 또는 터폴리머인 것을 특징으로 하는 활성 폴리머.
  11. 제1항에 있어서, 상기 폴리머는 폴리머 골격의 적어도 한 말단에 상기 활성 부분을 가지고 폴리머 골격의 반대편 말단에 상기 활성 부분과 동일하거나 다를 수 있는 활성 부분을 가지는 아령형 구조인 것을 특징으로 하는 활성 폴리머.
  12. 제11항에 있어서, 상기 폴리머 골격의 반대편 말단에 아미노 부분과 반응성인 다른 활성 부분으로 이루어진 것을 특징으로 하는 활성 폴리머.
  13. 제1항에 있어서, 상기 폴리머는 적어도 한개 가지의 분지형 분자구조로 이루어진 것을 특징으로 하는 활성 폴리머.
  14. 제13항에 있어서, 상기 분지형 분자 구조는 수지상인 것을 특징으로 하는 활성 폴리머.
  15. 제1항에 있어서, 상기 적어도 한개의 활성 술폰 부분은 표면상 또는 분자내에서 반응성 부분과 결합을 형성하는 것을 특징으로 하는 활성 폴리머.
  16. 제15항에 있어서, 상기 반응성 부분은 티올 부분인 것을 특징으로 하는 활성 폴리머.
  17. 제1항에 있어서, 상기 활성 술폰 부분은 링커 부분을 포함하는 결합에 의해 상기 폴리머에 연결되고, 상기 폴리머는 상기 링커 부분에 연결하기 위한 상기 활성 술폰 부분 이외의 활성 부분을 포함하는 것을 특징으로 하는 활성 폴리머.
  18. 제17항에 있어서, 상기 다른 활성 부분은 아민-특이적이고 상기 링커 부분은 활성 아미노 부분을 포함하는 것을 특징으로 하는 활성 폴리머.
  19. 제17항에 있어서, 상기 활성 폴리머는 폴리(에틸렌글리콜)이고, 상기 다른 활성 부분은 아미노 부분이고, 상기 링커 구조는 구조식 NHS-O2C-CH2-CH2-SO2-CH=CH2를 가지고, 상기 활성 폴리머는 구조식 PEG-NH-CO-CH2-CH2-SO2-CH=CH2를 가지는 것을 특징으로 하는 활성 폴리머.
  20. 제1항에 있어서, 상기 활성 폴리머는 약 11 이하의 pH의 수성 분위기에서 안정한 것을 특징으로 하는 활성 폴리머.
  21. 제1항에 있어서, 상기 활성 폴리머는 약 9 이하의 pH 조건에서 티올 부분과의 반응에 대해 선택적인 것을 특징으로 하는 활성 폴리머.
  22. 제1항에 있어서, 상기 활성 폴리머는 환원 분위기에서 안정한 것을 특징으로 하는 활성 폴리머.
  23. 제1항에 있어서, 상기 활성 폴리머는 무한하게 수용성인 것을 특징으로 하는 활성 폴리머.
  24. 구조식 R-(OCH2CH2)n-Y를 갖는 활성 폴리(에틸렌글리콜) 유도체(상기 식에서 n은 5 내지 3,000이고, Y는 -SO2-CH=CH2, -SO2-CH2-CH2-X(여기서 X는 할로겐) 및 그것의 유도체로 구성된 군으로부터 선택되고, R은 Y와 동일하거나 다르다).
  25. 제24항에 있어서, n은 약 5 내지 2200인 것을 특징으로 하는 활성 폴리(에틸렌글리콜) 유도체.
  26. 제24항에 있어서, n은 약 34 내지 1100인 것을 특징으로 하는 활성 폴리(에틸렌글리콜) 유도체.
  27. 제24항에 있어서, n은 약 45 내지 110인 것을 특징으로 하는 활성 폴리(에틸렌글리콜) 유도체.
  28. 제24항에 있어서, R은 H-,H3C-, CH2=-CH-SO2, -X-CH2-CH2-SO2- 및 그것의 유도체로 구성된 군으로부터 선택되거나 CH2=-CH-SO2- 또는 X-CH2-CH2-SO2- 및 그것의 유도체 이외의 폴리((에틸렌글리콜) 활성 부분인 것을 특징으로 하는 활성 폴리(에틸렌글리콜) 유도체.
  29. 반응성 티올 부분을 갖는 생물학적 활성 분자와 상기 티올 부분과 결합을 형성하는 활성 술폰 부분을 갖는 수용성 폴리머 유도체로 이루어진 가수분해적으로 안정한 생물학적 활성 콘쥬게이트.
  30. 제29항에 있어서, 상기 생물학적 활성 분자는 단백질이고, 상기 반응성 티올 부분은 상기 단백질의 시스테인 부분내에 함유되는 것을 특징으로 하는 콘쥬게이트.
  31. 제29항에 있어서, 상기 폴리머 유도체는 가수분해적으로 안정하고 폴리(알킬렌옥시드), 폴리(옥시에틸화폴리올) 및 폴리(올레핀알코올)로 구성된 군으로부터 선택되는 것을 특징으로 하는 콘쥬게이트.
  32. 제29항에 있어서, 상기 콘쥬게이트는 다음 구조식 PEG-SO2-CH2-CH2-S-W(여기서 W는 생물학적 활성 분자)를 가지는 것을 특징으로 하는 콘쥬게이트.
  33. 동일하거나 다를 수 있고 적어도 한개는 반응성 티올 부분을 갖는 두개의 생물학적 활성 부분과 그것의 각 말단에 반응성 부분을 갖는 수용성 아령형 폴리머 유도체로 이루어진 가수분해적으로 안정한 생물학적 활성 콘쥬게이트로서, 상기 폴리머상에서 상기 반응성 부분중 적어도 한개는 활성 술폰 부분이고 적어도 한개의 상기 생물학적 활성 부분의 상기 티올 부분과 결합을 형성하며 다른 한개의 상기 생물학적 활성 부분은 상기 반응성 부분중 다른 한개와 결합을 형성하는 콘쥬게이트.
  34. 제33항에 있어서, 상기 생물학적 활성 부분은 단백질, 약제, 세포, 비타민 및 그것들의 조합으로 구성된 군으로부터 선택되는 것을 특징으로 하는 콘쥬게이트.
  35. 제33항에 있어서, 상기 활성 술폰 부분은 비닐술폰 또는 할로에틸술폰이고, 상기 폴리머 유도체상의 상기 다른 반응성 부분은 아미노기와의 반응에 대해 선택적인 것을 특징으로 하는 콘쥬게이트.
  36. 티올 부분과의 반응에 대해 선택적인 적어도 한개의 활성 술폰 부분과 아미노 부분과의 반응에 대해 선택적인 적어도 한개의 다른 부분을 갖는 활성 수용성 폴리머, 티올 부분이 상기 폴리머상의 상기 술폰 부분과 가수분해적으로 안정한 결합을 형성하는 상기 티올 부분을 갖는 제1단백질과 아미노 부분이 상기 폴리머상의 상기 다른 부분과 결합을 형성하는 상기 아미노 부분을 갖는 제2단백질로 이루어진 생물학적 활성 콘쥬게이트.
  37. 제36항에 있어서, 상기 제1단백질은 시스테인 단위체를 함유하고, 상기 제2단백질은 리신 단위체를 함유하는 것을 특징으로 하는 콘쥬게이트.
  38. 표면과 상기 표면에 연결된 적어도 한개의 수용성 폴리머 유도체로 이루어진 생재료로서, 상기 폴리머 유도체는 폴리(알킬렌옥시드), 폴리(옥시에틸화폴리올) 및 폴리(올레핀알코올)로 구성된 군으로부터 선택되고 적어도 한개의 활성 술폰 부분을 가지는 생재료.
  39. 제38항에 있어서, 상기 표면은 표면상에 적어도 한개의 반응성 부분을 가지고, 상기 폴리머 유도체는 한 말단에 상기 표면상의 상기 반응성 부분에 연결된 부분을 갖고 반대편 말단에 위치한 활성 술폰 부분을 갖는 헤테로이작용성 아령형 구조인 것을 특징으로 하는 생재료.
  40. 제39항에 있어서, 상기 반응성 부분은 아민이고, 상기 아민 부분과 상기 폴리머 유도체의 상기 부분은 아민-선택적 부분인 것을 특징으로 하는 생재료.
  41. 제38항에 있어서, 상기 활성 술폰 부분은 비닐술폰, 활성 에틸술폰 및 그것의 유도체로 구성된 군으로부터 선택되는 것을 특징으로 하는 생재료.
  42. 제38항에 있어서, 상기 폴리머 유도체는 PEG 폴리머로 이루어지는 것을 특징으로 하는 생재료.
  43. 폴리머 및 술폰 부분 사이의 결합이 가수분해에 대해 안정한 활성 술폰 부분을 갖는 수용성 활성 유기폴리머의 합성 방법으로서, 황함유 부분을 폴리머의 탄소원자에 직접 연결시키는 단계 다음에 황함유 부분을 활성 술폰 부분으로 전환시키는 단계로 이루어지는 합성 방법.
  44. 제42항에 있어서, 활성 술폰 부분을 갖는 활성 폴리머를 단리시키는 단계를 더 포함하는 것을 특징으로 하는 합성 방법.
  45. 제42항에 있어서, 황함유 부분을 폴리머의 탄소원자에 직접 연결시키는 상기 단계는 폴리머상의 적어도 한개의 활성가능한 히드록실 부분을 활성화시키는 단계와 결과의 화합물을 티올 부분 함유 알코올과 반응시켜 황이 폴리머의 탄소-탄소 사슬에 직접 연결되도록 만드는 단계로 이루어지는 것을 특징으로 하는 합성 방법.
  46. 제44항에 있어서, 적어도 한개의 활성가능한 히드록실 부분을 활성화시키는 상기 단계는 더 반응성 부분에 의한 히드록실 치환과 히드록실 수소의 대체로 구성된 단계들로부터 선택되는 것을 특징으로 하는 합성 방법.
  47. 제44항에 있어서, 티올 부분 함유 알코올은 메르캅토에탄올인 것을 특징으로 하는 합성 방법.
  48. 제44항에 있어서, 황함유 부분내의 황을 술폰으로 산화시키는 단계와 생성물을 히드록실 활성 또는 치환 부분과 반응시키는 단계에 의해 티올 부분 함유 알코올을 활성 술폰 부분으로 전환시키는 것을 특징으로 하는 합성 방법.
  49. 제47항에 있어서, 술폰은 활성 에틸술폰이고, 방법은 활성 에틸술폰을 감염기와 반응시킴으로써 폴리머상에 비닐술폰 부분을 형성하는 단계를 더 포함하는 것을 특징으로 하는 활성 방법.
  50. 다음 단계들로 이루어진 폴리(에틸렌글리콜) 비닐술폰의 제조방법 : (a) 적어도 한개의 활성 히드록실 부분을 갖는 폴리(에틸렌글리콜)를 화합물과 반응시켜 에스테르 또는 할로겐화물 치환된 폴리(에틸렌글리콜)를 형성하는 단계; (b) 단계(a)의 에스테르 또는 할로겐화물 치환된 폴리(에틸렌글리콜)를 메르캅토에탄올과 반응시켜 에스테르 또는 할로겐화물 부분을 메르캅토에탄올 라디칼로 치환되는 단계; (c) 단계(b)의 메르캅토에탄올 치환된 폴리(에틸렌글리콜)를 산화제와 반응시켜 메르캅토에탄올 부분내의 황을 술폰으로 산화하는 단계; (d) 단계(c)의 술폰을 화합물과 반응시켜 메르캅토에탄올 부분의 히드록실을 에스테르 또는 할로겐화물 부분으로 전환하는 단계; (e) 단계(d)의 에틸술폰을 염기와 반응시켜 폴리(에틸렌글리콜) 비닐술폰을 형성하는 단계.
  51. 제49항에 있어서, 폴리(에틸렌글리콜) 비닐술폰을 단리하는 단계를 더 포함하는 것을 특징으로 하는 제조 방법.
  52. 제49항에 있어서, 단계(d)의 할로겐화물을 클로린이고, 단계(d)의 생성물은 폴리(에틸렌글리콜) 클로로에틸술폰이고, 방법은 디클로로메탄에 클로로에틸술폰을 용해시키고 에틸에테르에서 클로로에틸술폰을 침전시키고 에틸아세테이트로부터 침전물을 재결정화함으로써 폴리(에틸렌글리콜) 클로로에틸슬폰을 단리하는 단계를 더 포함하는 것을 특징으로 하는 제조 방법.
  53. 제51항에 있어서, 유기 용매에 폴리(에틸렌글리콘) 클로로에틸슬폰결정을 용해시킨 후 염기와 반응시켜 폴리(에틸렌글리콜) 비닐술폰을 형성하는 단계와 여과하여 염기를 제거하고 용매를 증발시킴으로써 폴리(에틸렌글리콜) 비닐술폰 생성물을 단리하는 단계를 더 포함하는 것을 특징으로 하는 제조 방법.
  54. 활성술폰부분을 갖는 수용성 활성유기폴리머의 합성방법으로서, 폴리머 및 술폰부분 사이의 결합은 가수분해에 대해 안정하고, 방법은 활성술폰부분 및 또 다른 활성부분을 함유하는 연결부분을 술폰부분 이외의 작용기를 갖고 그 작용기는 상기 링커부분상의 다른 활성부분에 대해 선택적인 폴리(알킬렌옥시드), 폴리(옥시에틸화폴리올) 및 폴리(올레핀알코올)로 구성된 군으로부터 선택된 폴리머유도체에 부착하는 단계로 이루어지는 합성 방법.
  55. 제54항에 있어서, 상기 폴리머 유도체상의 작용기는 아미노부분과의 반응에 대해 선택적이고, 링커부분상의 다른 활성부분은 활성아미노부분을 함유하는 것을 특징으로 하는 합성 방법.
  56. 제54항에 있어서, 폴리머 유도체는 PEG 숙식이미딜 활성 에스테르이고, 링커 부분은 구조식 NH2-CH2-CH2-SO2-CH=CH2를 가지는 것을 특징으로 하는 합성 방법.
  57. 제54항에 있어서, 아미노 부분에 대해 선태적인 작용기를 갖는 폴리(에틸렌글리콜), 폴리(프로필렌글리콜), 폴리(옥시에틸화글리세롤), 폴리(옥시에틸화소르비톨), 폴리(옥시에틸화글루코스) 및 폴리(비닐알코올)로 구성된 군으로부터 선택된 폴리머 유도체를 제조하는 단계, 아미노 부분 및 술폰 부분을 함유하는 링커부분을 제조하는 단계와 링커 부분상의 아미노 부분을 폴리머 유도체상의 아미노 선택적 부분에 연결하는 단계를 더 포함하는 것을 특징으로 하는 합성 방법.
  58. 적어도 한개의 술폰 부분을 갖는 폴리(알킬렌옥시드), 폴리(옥시에틸화폴리올) 및 폴리(올레핀알코올)로 구성된 군으로부터 선택된 수용성 활성 폴리머와 물질의 콘쥬게이트의 제조 방법으로서, 상기 방법은 물질을 활성 술폰 부분을 갖는 활성 폴리머와 반응시키는 단계와 물질 및 폴리머 유도체 사이의 결합을 형성하는 단계로 이루어진 제조 방법.
  59. 제58항에 있어서, 물질은 활성 티올 부분을 포함하고, 결합은 티올부분과 술폰 부분 사이에 있는 것을 특징으로 하는 제조 방법.
  60. 제58항에 있어서, 물질은 활성 아미노 부분을 포함하고, 폴리머 유도체는 아미노 선택적 부분을 포함하고, 결합은 아미노 부분과 아미노 선택적 부분 사이에 형성되는 것을 특징으로 하는 제조 방법.
  61. 제58항에 있어서, 활성 폴리머는 폴리(에틸렌글리콜), 폴리(프로필렌글리콜), 폴리(옥시에틸화글리세롤), 폴리(옥시에틸화소르비톨), 폴리(옥시에틸화글루코스) 및 폴리(비닐알코올)로 구성된 군으로부터 선택되는 것을 특징으로 하는 제조 방법.
  62. 제58항에 있어서, 상기 물질을 합성 생재료, 단백질, 약재, 세포 및 비타민으로 구성된 군으로부터 선택되는 것을 특징으로 하는 제조 방법.
  63. 생물학적 활성분자와 폴리(에틸렌글리콜) 활성유도체의 콘쥬게이드의 제조 방법으로서, 상기 방법은 반응성 티올 부분을 갖는 생물학적 활성분자를 활성 술폰 부분을 갖는 폴리(에틸렌글리콜) 유도체와 반응시키는 단계와 티올 부분 및 활성 술폰 부분 사이에 결합을 형성하는 단계로 이루어진 제조 방법.
  64. 제63항에 있어서, 생물학적 활성분자를 폴리(에틸렌글리콜) 유도체와 반응시키는 상기 단계는 약 11 미만의 pH의 조건에서 수행하는 것을 특징으로 하는 제조 방법.
  65. 제63항에 있어서, 생물학적 활성분자를 폴리(에틸렌글리콜) 유도체와 반응시키는 상기 단계는 약 9 이하의 pH에서 수행하는 것을 특징으로 하는 제조 방법.
  66. 제63항에 있어서, 활성 술폰 부분은 비닐술폰, 활성 에틸술폰 및 그것의 활성 유도체로 구성된 군으로부터 선택되는 것을 특징으로 하는 제조 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960702507A 1993-11-12 1994-11-14 수용성의 활성 술폰을 갖는 폴리 (에틸렌글리콜) KR100225746B1 (ko)

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US151,481 1993-11-12
US08/151,481 US5446090A (en) 1993-11-12 1993-11-12 Isolatable, water soluble, and hydrolytically stable active sulfones of poly(ethylene glycol) and related polymers for modification of surfaces and molecules
US8/151481 1993-11-12
PCT/US1994/013013 WO1995013312A1 (en) 1993-11-12 1994-11-14 Water soluble active sulfones of poly(ethylene glycol)

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