KR890012658A - 신규의 링커를 갖는 안트라사이클린 면역결합체 및 그의 제조방법 - Google Patents

신규의 링커를 갖는 안트라사이클린 면역결합체 및 그의 제조방법 Download PDF

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KR890012658A
KR890012658A KR1019890001517A KR890001517A KR890012658A KR 890012658 A KR890012658 A KR 890012658A KR 1019890001517 A KR1019890001517 A KR 1019890001517A KR 890001517 A KR890001517 A KR 890001517A KR 890012658 A KR890012658 A KR 890012658A
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anthracycline
antibody
hydrogen
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에스.그린필드 로버트
알.브라슬라브스키 게리
제이.올레크 리
가네꼬 다꾸시
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로버트 디.오브라이언
브리스톨-마이어즈 컴페니
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Abstract

내용 없음.

Description

신규의 링커를 갖는 안트라사이클린 면역결합체 및 그의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명의 면역결합체 제조에 사용되는 신규의 ADM-HZn 유도체의 합성을 반응식으로 나타낸 도면.
제2도는 SPDP(N-숙신이미딜-3-(2-피리딜디티오)프로피오네이트)나 혹은 2-IT(2-이미노티올란)을 이용하여 모노클로날 항체(MAB)를 우선 티올화시킨 다음 이 티올화된 항체를 ADM-HZN과 반응시켜 ADM의 13-케토 위치에 히드라존 결합을 가지며 링커암(linker arm)에 디술라이드결합을 갖는 본 발명의 면역결합체를 형성시키는 단계로된 본 발명의 한 구체예의 면역결합체의 합성을 도식적으로 나타낸 도면.
제3도는 모노클로날 항체에서 대치된 반응성 티올기의 수(SH/MAB 비율)를 SPDP-티올화 5EP 및 3A1 모노클로날 항체를 ADM-HZN과 축합시켜 생산한 면역결합체에서 얻어진 최종 ADM/MAB 몰비율과 분산도(scatter gram).

Claims (27)

  1. 사멸시키고자 하는 선택된 세포집단과 반응성인 항체와 이에 결합된 약 4-10개의 안트라사이클린 분자로 이루어지며, 여기서 각 안트라사이클린은 C-13 위치에 케토기를 가지고 링커 암을 통해 항체에 부착되어 있으며, 이때 링커 암은 안트라사이클린의 13-케토 위치에서 아실히드라존 결합에 의해 안트라사이클린에 고유결합되어 있는 것이 특징인 면역결합체.
  2. 제1항에 있어서, 링커 암이 디술파이드 결합 또는 티오에테르 결합을 추가로 포함하는 것이 특징인 면역결합체.
  3. 사멸시키고자 하는 선택된 세포집단과 반응성인 항체에 링커 암을 통해 부착되어 있으면서 C-13위치에 케토기를 갖는 안트라사이클린 분자를 적어도 하나 포함하고, 여기서 링커 암은 안트라사이클린의 13-케토 위치에서 아실히드라존 결합에 의해 안트라사이클린에 공유결합되고 디술파이드 또는 티오에테르 결합을 추가로 포함하는 것이 특징인 면역결합체.
  4. 제1항에 있어서, 안트라사이클린을 아드리아마이신, 다우노마이신, 데토루비신, 카르미노마이신, 이다루비신, 에피루비신, 에소루비신, 4′-THP-아드리아마이신, AD-32 및 3′-데아미노-3′-(3-시아노-4-모르폴리닐)-독소루비신으로 이루어진 군중에서 선택함을 특징으로하는 면역결합체.
  5. 제1항 또는 제3항에 있어서, 안트라사이클린이 아드리아마이신 또는 다우노마이신인 것이 특징인 면역결합체.
  6. 제1항 또는 제3항에 있어서, 항체가 종양세포와 반응성인 것이 특징인 면역결합체.
  7. 제6항에 있어서, 항체가 암종, 흑색종, 임파종, 뼈 또는 연조직 육종과 관련된 항원과 반응성인 것이 특징인 면역결합체.
  8. 제1항 또는 제3항에 있어서, 항체가 B 세포 임파종에서 발견되는 CD37 항원과 반응성인 것이 특징인 면역결합체.
  9. 제1항에 있어서, 항체가 모노클로날 항체인 것이 특징인 면역결합체.
  10. 제1항 또는 제3항에 있어서, 항체가 모노클로날 항체 5E9, 3Al, L6,G28.1 또는 G28.5이고 안트라사이클린은 아드리아마이신인 것이 특징인 면역결합체.
  11. 다음의 일반식을 갖는 화합물:
    상기 일반식중, R1은 CH3, CH2OH, CH2OCO(CH2) CH3또는 CH2OCOCH(OC2H5)2이고: R2는또는이고 이때 X는 H,NO2, 또는 할로겐이며; R3은 OCH3, OH 또는 수소이고; R4은 NH2, NHCOCF3, 4-모르폴리닐, 3-시아노-4-모르폴리닐, 1-피페리디닐, 4-메톡시-1-피피레디닐, 벤질, 아민, 디벤질 아민, 사이노메틸 아민 또는 1-시아노-2-메톡시에틸아민이고; R5은 OH, O-THP 또는 수소이며; R6은 OH 또는 R5가 OH 또는 O-THP인 경우 R6이 OH가 아니라면 수소이며; n은 1에서 10까지의 정수임.
  12. 다음의 일반식을 갖는 화합물
    상기 일반식중, R1은 CH3, CH2OH, CH2OCH(CH2)3또는 CH2OCOCH(OC2H5)2이고; R3은 OCH1, OH 또는 수소이며; R4는 NH2, NHCOCF2, 4-모르폴리닐, 3-시아노-4-모르폴리닐, 1-피페리디닐, 4-메톡시-1-피페리디닐, 벤질아민, 디벤질아민, 시아노메틸 아민 또는 1-시아노-2-메톡시에틸 아민이고; R5는 OH, O-THP 또는 수소이며, R6은 OH 또는 R5가 OH 또는 O-THP인 경우 R6이 OH가 아니라면 수소이고; n은 1에서 10까지의 정수임.
  13. 다음의 일반식을 갖는 화합물.
    상기 일반식중, R1은 CH3, CH2OH, CH2OCO(CH2)3CH3또는 CH2OCOCH(OC2H5)2이고; R2는또는이고 이때 X는 H, NO2또는 할로겐이며; R3는 OCH3, OH 또는 수소이고, R4및 R7은 각각 수소, 알킬, 치환알킬, 시클로알킬, 치환 시클로알킬, 아릴, 치환아릴, 아르알킬 또는 치환 아르알킬이거나; 또는 R4,R7및 N은 함께 4 내지 7원고리를 형성하며, 여기서 상기 고리는 임의로 치환될 수 있고; R5는 OH,O-THP 또는 수소이고; R6은 OH 또는 R5가 OH 또는 O-THP인 경우 R6이 OH가 아니라면 수소이고, n은 1에서 10까지의 정수임.
  14. 아드리아마이신 13-{3-(2-피리딜디티오)프로피오닐}-히드라존 염산염(ADM-HZN).
  15. 13-{3-메르캅토프로피오닐)}아드리아마이신 히드라존.
  16. a) ω-(R2디티오)카르복실산의 N-히드록시숙신이미도 에스테르를 히드라진과 반응시켜, ω-(R2디티오)카르복실산 히드라지를 생성시키고(여기서 R2는 상기 정의한 바와같음); b) 상기 히드라지드를 다음의 일반식을 갖는 안트라사이클린
    상기 일반식중, R1은 COCH3, COCH2OH, COCH2OCOCH(OC2H5)2또는 COCH2OCO(CH2)3CH3이고; R3은 OCH3, OH 또는 수소이며; R4는 NH2, NHCOCF3, 4-모르폴리닐, 3-시아노-4-모르폴리닐, 1-피페리디닐, 4-메톡시-1-피페리디닐, 벤질아민, 디벤질아민, 시아노메틸아민 또는 1-시아노-2-메톡시에틸 아민이고; R5는 OH, O-THP 또는 수소이며; R6은 OH 또는 R5가 OH 또는 O-THP인 경우 R6이 OH가 아니라면 수소임, 과 반응시키는 단계로 이루어짐을 특징으로 하는 다음의 일반식을 갖는 화합물의 제조방법.
    상기 일반식중, R1은 CH3,CH2OH, CH2OCO(CH2)3CH3또는 CH2OCOCH(OC2H5)2이고; R2는또는이고 이때, X는 H, NO2또는 할로겐이며; R3은 OCH3, OH 또는 수소이며; R4및 R7은 각각 수소, 알킬, 치환알킬, 시클로알킬, 치환시클로알킬, 아릴, 치환아릴, 아르알킬 또는 치환 아르알킬이거나; 또는 R4,R7및 N은 함께 4내지 7원고리를 형성하고 여기서, 상기 고리는 임의 치환될 수 있으며; R5는 OH, O-THP 또는 수소이고; R6은 OH 또는 R5가 OH 또는 O-THP인 경우 R6이 OH가 아니라면 수소이고; n은 1에서 10까지의 정수임.
  17. 제16항에 있어서, 화합물을 환원제로 처리하여 13-{3-(메르캅토프로피오닐)}안트라사이클린 히드라존을 생성시키는 단계를 추가로 포함하는 것이 특징인 제조방법.
  18. a) SPDP를 히드라진과 반응시켜 3-(2-피리딜티오)프로피오닐히드라지드를 생성시키고; b) 아드리아마이신-염산염을 상기 히드라지드와 반응시키는 단계로 이루어짐을 특징으로 하는 ADM-HZN의 제조방법.
  19. a) 항체를 티올화제와 반응시키고, b) 티올화 항체를 청구범위 제11항, 제12항 또는 제13항의 아실히드라존과 반응시키는 단계로 이루어짐을 특징으로 하는 제1항 또는 제3항의 면역결합체의 제조방법.
  20. 제19항에 있어서, 이실히드라존이 ADM-HZN인 것이 특징인 제1항 또는 제3항 면역결합체의 제조방법.
  21. 제19항에 있어서, 티올화제가 SPDP 또는 2-IT인 것이 특징인 제1항 또는 제3항의 면역결합체의 제조방법.
  22. a) SPDP를 히드라진과 반응시켜 3-(2-피리딜티오)프로피오닐히드라지드를 생성시키고; b)아드리아마이신-염산염을 상기 히드라지드와 반응시켜 ADM-HZN을 생성시킨 다음; c) 티올기가 부착되어 있으며 사멸시키고자 하는 선택돈 세포집단과 반응성인 항체와 상기 ADM-HZN을 반응시키는 단계로 이루어짐을 특징으로하는 제1항 또는 제3항의 면역결합체의 제조방법.
  23. a) SPDP를 히드라진과 반응시켜 3-(2-피리딜티오)프로피오닐히드라지드를 생성시키고, b)아드리아마이신-염산염을 상기 히들라지드와 반응시켜 ADM-HZN을 생성시키며; c) 사이 ADM-HZN을 환원제로 처리하여 13-{3-(메르캅토프로피오닐)}아드리아마이신 히드라존을 생성시키고; d) 말레이미드기가 부착되어 있으며 사멸시키고자 하는 선택된 세포집단과 반응성인 항체와 상기 히드라존을 반응시키는 단계로 이루어짐을 특징으로 하는 제1항 또는 제3항의 면역결합체의 제조방법.
  24. 제1항 또는 제3항에 따른 면역결합체중 적어도 한가지 이상을 약리적 유효량으로 투여함을 특징으로 하는 사멸시키고자 하는 선택된 세포집단에 안트라사이클린을 전달하는 방법.
  25. 한가지 이상의 면역결합체의 약리적 유효량을 투여하는 것으로 이루어지고, 상기 면역결합에 있어서, 사멸시키고자 하는 선택된 세포집단과 반응성인 항체는 안트라사이클린의 13-케토 위치에서의 아실히드라존 결합에 의해 안트라사이클린에 부착된 링커 암을 통해 적어도 하나의 안트라사이클린에 연결되어 있으며, 이때 각 결합체의 항체는 상기 세포집단과 관련된 같거나 다른 항원 또는 에피토프와 반응성이고 각 결합체의 안트라사이클린은 같거나 다름을 특징으로 하는, 사멸시키고자 하는 선택된 세포집단에 안트라사이클린의 배합물을 전달하는 방법.
  26. 제1항 또는 제3항에 따른 적어도 한가지의 면역결합체의 약리적 유효량과 약리적으로 허용되는 담체로 이루어짐을 특징으로 하는 질병 치료에 유효한 약리적으로 허용되는 조성물.
  27. 제26항에 있어서, 치료하고자 하는 질명이 암, 비 악성종양, 비 사포사멸성 바이러스 또는 병원채 감염, 및 자가면역 장애로 이루어진 군에서 선택되는 것이 특징인 질병 치료에 유효한 약리적으로 허용되는 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890001517A 1988-02-11 1989-02-10 신규의 링커를 갖는 안트라사이클린 면역결합체 및 그의 제조방법 KR960015398B1 (ko)

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