KR102256410B1 - 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 - Google Patents
트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 Download PDFInfo
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- KR102256410B1 KR102256410B1 KR1020207006108A KR20207006108A KR102256410B1 KR 102256410 B1 KR102256410 B1 KR 102256410B1 KR 1020207006108 A KR1020207006108 A KR 1020207006108A KR 20207006108 A KR20207006108 A KR 20207006108A KR 102256410 B1 KR102256410 B1 KR 102256410B1
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Abstract
Description
도 1b는 QS-21-Api 및 QS-21-Xyl의 화학 구조를 도시한다. 백분율(%)은 QS-21의 단리된 추출물 중 각 이성질체의 천연 존재량에 상응한다.
도 2a 내지 도 2c는 아주반트 NQS-21, SQS-21-Mix, SQS-21-Api 또는 SQS-21-Xyl를 각각 20 ㎍ 용량으로 사용하고 GD3-KLH 접합체 (10 ㎍)로 백신접종한 후의 항-GD3 및 항-KLH 항체 역가를 보여준다. 각각의 값은 5 마리 마우스 (3차 및 4차 백신접종 7일 후에 시험한 혈청)의 중앙 값을 나타낸다. NQS-21 = 천연 유도된 QS-21, SQS-21-Mix = 합성 QS-21.
도 3은 20 ㎍ 용량의 다양한 SQS-아주반트를 사용한 백신접종 사이에서 세포주 SK-Mel-28에 대한 세포 표면 반응성의 비교를 보여준다.
도 4는 GD3-KLH (10 ㎍) 및 SQS-21-Mix, SQS-21-Api 또는 SQS-21-Xyl (각각 20 ㎍씩)를 주사한 C57BL/6J 암컷 마우스에서의 독성 연구를 아주반트가 없거나 천연 NQS-21 (20 ㎍)을 사용한 경우와 비교하여 도시한다.
도 5는 GD3-KLH 항원을 사용한 합성 SQS-유사체의 아주반트 활성에 대한 결과를 보여준다. 항체-역가는 5 마리 마우스 군의 중앙 값이며, 아주반트 용량은 10 ㎍이다. SQS-7 = 합성 QS-7-Api, SQS-0101 = 화합물 I-9, SQS-0102 = 화합물 I-10, SQS-0103 = 화합물 I-8.
도 6 내지 도 14는 본원에 기재된 화합물의 1H-NMR 스펙트럼을 보여준다.
도 15a 및 도 15b는 천연 및 반합성 QS-7-Api의 1:1 혼합물의 고성능 액체 크로마토그래피 추적도이다.
Claims (40)
- 하기 화학식 II-b의 화합물 또는 그의 제약상 허용가능한 염:
<화학식 II-b>
상기 식에서,
는 단일 또는 이중 결합이고,
W는 Me, -CHO 또는 -CH2OH이고,
V는 -OH이고,
각 경우의 Rx는 수소이고,
Ry는 -OH이거나, 또는 에스테르, 아미드 및 히드라지드로 구성된 군에서 선택된 카르복실 보호기이고,
Rs는 이고,
각 경우의 R1은 수소이거나, 또는 하기 구조를 갖는 탄수화물 도메인이고:
여기서,
a는 0이고,
b, c 및 d의 각각은 1이고,
R0은 수소이고,
Ra는 -OH이고,
Rb는 -OH이고,
Rc는 수소이고,
Rd는 치환되지 않은 C1-10 알킬이거나, 또는
R1은
, , 또는 의 구조를 갖는 기이고, 여기서 R5는 치환되지 않은 C1-10 알킬이고,
R3은 -CH2OH이고,
R4는 이거나, 또는
R4는 -(CH2)10-Me이거나, 또는
R4는 이지만,
단, 상기 화합물은 하기의 것 중 하나는 아니다:
. - 제1항에 따른 화합물 및 제약상 허용가능한 부형제를 포함하는, 암 또는 감염성 질환을 치료하거나 예방하기 위한 백신으로 사용하기 위한 제약 조성물.
- 제3항에 있어서, 면역 유효량의 항원을 추가로 포함하는 제약 조성물.
- 제1항에 있어서, Ry가 -OH인 화합물.
- 제2항에 따른 화합물 및 제약상 허용가능한 부형제를 포함하는, 암 또는 감염성 질환을 치료하거나 예방하기 위한 백신으로 사용하기 위한 제약 조성물.
- 제6항에 있어서, 면역 유효량의 항원을 추가로 포함하는 제약 조성물.
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