RU2019134399A - Конъюгат анти-trop2 антитело-лекарственное средство - Google Patents

Конъюгат анти-trop2 антитело-лекарственное средство Download PDF

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RU2019134399A
RU2019134399A RU2019134399A RU2019134399A RU2019134399A RU 2019134399 A RU2019134399 A RU 2019134399A RU 2019134399 A RU2019134399 A RU 2019134399A RU 2019134399 A RU2019134399 A RU 2019134399A RU 2019134399 A RU2019134399 A RU 2019134399A
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RU2019134399A
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RU2743077C2 (ru
RU2019134399A3 (ru
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Тосинори АГАЦУМА
Су ТАКАХАСИ
Дзун ХАСЕГАВА
Даисуке ОКАДЗИМА
Хирофуми ХАМАДА
Микио ЯМАГУТИ
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Дайити Санкио Компани, Лимитед
Саппоро Медикал Юниверсити
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    • C07—ORGANIC CHEMISTRY
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Claims (81)

1. Способ получения конъюгата антитело-лекарственное средство, включающий взаимодействие соединения, представленного следующей формулой:
(малеимид-N-ил)-(CH2)n3-C(=O)-L2-LP-NH-(CH2)n1-La-(CH2)n2-C(=O)-(NH-DX)
с анти-TROP2 антителом или его реакционноспособным производным и конъюгирование фрагмента лекарственное средство-линкер с антителом с помощью способа образования тиоэфирной связи на участке дисульфидной связи, присутствующей в шарнирной части антитела,
где
n1 представляет собой целое число, имеющее значение от 0 до 6,
n2 представляет собой целое число, имеющее значение от 0 до 5,
n3 представляет собой целое число, имеющее значение от 2 до 8,
L2 представляет собой -NH-(CH2CH2-O)n4-CH2CH2-C(=O)- или простую связь,
где где n4 представляет собой целое число, имеющее значение от 1 до 6,
LP представляет собой пептидный остаток, состоящий из 2-7 аминокислот, выбранных из фенилаланина, глицина, валина, лизина, цитруллина, серина, глутаминовой кислоты и аспарагиновой кислоты,
La представляет собой -O- или простую связь, и
(малеимид-N-ил)- представляет собой группу, представленную следующей формулой:
Figure 00000001
где атом азота представляет собой положение связывания, и
-(NH-DX) представляет собой группу, представленную следующей формулой:
Figure 00000002
,
где атом азота амино группы в положении 1 представляет собой положение связывания.
2. Способ по п.1, в котором где LP представляет собой тетрапептидный остаток -GGFG-.
3. Способ по п.1, в котором соединение представляет собой соединение, выбранное из следующей группы:
(малеимид-N-ил)-CH2CH2-C(=O)-GGFG-NH-CH2CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2CH2CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2-O-CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2CH2-O-CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2-C(=O)-NH-CH2CH2-O-CH2CH2-O-CH2CH2-C(=O)-GGFG-NH-CH2CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2-C(=O)-NH-CH2CH2-O-CH2CH2-O-CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2-C(=O)-NH-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-C(=O)-GGFG-NH-CH2CH2-C(=O)-(NH-DX), и
(малеимид-N-ил)-CH2CH2-C(=O)-NH-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2-C(=O)-(NH-DX).
4. Способ по п.3, в котором соединение представлет собой соединение, выбранное из следующей группы:
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2-O-CH2-C(=O)-(NH-DX),
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2CH2-O-CH2-C(=O)-(NH-DX), and
(малеимид-N-ил)-CH2CH2-C(=O)-NH-CH2CH2-O-CH2CH2-O-CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2-C(=O)-(NH-DX).
5. Способ по п.4, в котором соединением является:
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2-O-CH2-C(=O)-(NH-DX).
6. Способ по п.4, в котором структурным фрагментом лекарственное средство-линкер является:
(малеимид-N-ил)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2CH2-O-CH2-C(=O)-(NH-DX).
7. Способ по п.4, в котором структурным фрагментом лекарственное средство-линкер является:
(малеимид-N-ил)-CH2CH2-C(=O)-NH-CH2CH2-O-CH2CH2-O-CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2-C(=O)-(NH-DX).
8. Способ по п.1, в котором конъюгат антитело-лекарственное средство имеет структуру лекарственное средство-линкер, представленное следующей формулой:
-(Сукцинимид-3-ил-N)-(CH2)n3-C(=O)-L2-LP-NH-(CH2)n1-La-(CH2)n2-C(=O)-(NH-DX),
который конъюгирован с анти-TROP2-антителом через тиоэфирную связь, образованную на участке дисульфидной связи, присутствующей в шарнирной части анти-TROP2-антитела.
9. Способ по п.5, в котором конъюгат антитело-лекарственное средство имеет структуру лекарственное средство-линкер, представленную следующей формулой:
-(Сукцинимид-3-ил-N)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2-O-CH2-C(=O)-(NH-DX),
который конъюгирован с анти-TROP2-антителом через тиоэфирную связь, образованную на участке дисульфидной связи, присутствующей в шарнирной части анти-TROP2-антитела.
10. Способ по п.6, в котором конъюгат антитело-лекарственное средство имеет структуру лекарственное средство-линкер, представленную следующей формулой:
-(Сукцинимид-3-ил-N)-CH2CH2CH2CH2CH2-C(=O)-GGFG-NH-CH2CH2-O-CH2-C(=O)-(NH-DX),
который конъюгирован с анти-TROP2-антителом через тиоэфирную связь, образованную на участке дисульфидной связи, присутствующей в шарнирной части анти-TROP2-антитела.
11. Способ по п.7, в котором конъюгат антитело-лекарственное средство имеет структуру лекарственное средство-линкер, представленную следующей формулой:
-(Сукцинимид-3-ил-N)-CH2CH2-C(=O)-NH-CH2CH2-O-CH2CH2-O-CH2CH2-C(=O)-GGFG-NH-CH2CH2CH2-C(=O)-(NH-DX),
который конъюгирован с анти-TROP2-антителом через тиоэфирную связь, образованную на участке дисульфидной связи, присутствующей в шарнирной части анти-TROP2-антитела.
12. Способ по любому из пп.1-11, где анти-TROP2-антитело включает CDRH1, состоящую из аминокислотной последовательности SEQ ID NO: 23, CDRH2, состоящую из аминокислотной последовательности SEQ ID NO: 24, и CDRH3, состоящую из аминокислотной последовательности SEQ ID NO: 25 в ее вариабельной области тяжелой цепи и CDRL1, состоящую из аминокислотной последовательности SEQ ID NO: 26, CDRL2, состоящую из аминокислотной последовательности SEQ ID NO: 27, и CDRL3, состоящую из аминокислотной последовательности SEQ ID NO: 28 в ее вариабельной области легкой цепи.
13. Способ по любому из пп.1-11, в котором анти-TROP2-антитело содержит тяжелую цепь и легкую цепь, выбранные из группы:
вариабельная область тяжелой цепи, состоящая из аминокислотной последовательности, представленной положениями с 20 по 140 SEQ ID NO: 12, и вариабельная область легкой цепи, состоящая из аминокислотной последовательности, представленной положениями с 21 по 129 SEQ ID NO: 18,
вариабельная область тяжелой цепи, состоящая из аминокислотной последовательности, представленной положениями с 20 по 140 SEQ ID NO: 14, и вариабельная область легкой цепи, состоящая из аминокислотной последовательности, представленной положениями с 21 по 129 SEQ ID NO: 18,
вариабельная область тяжелой цепи, состоящая из аминокислотной последовательности, представленной положениями с 20 по 140 SEQ ID NO: 14, и вариабельная область легкой цепи, состоящая из аминокислотной последовательности, представленной положениями с 21 по 129 SEQ ID NO: 20, и
вариабельная область тяжелой цепи, состоящая из аминокислотной последовательности, представленной положениями с 20 по 140 SEQ ID NO: 16, и вариабельная область легкой цепи, состоящая из аминокислотной последовательности, представленной положениями с 21 по 129 SEQ ID NO: 22.
14. Способ по любому из пп.1-11, в котором анти-TROP2-антитело содержит тяжелую цепь и легкую цепь, выбранные из группы:
тяжелая цепь, состоящая из аминокислотной последовательности, представленной положениями с 20 по 470 SEQ ID NO: 12, и легкая цепь, состоящая из аминокислотной последовательности, представленной положениями с 21 по 234 SEQ ID NO: 18,
тяжелая цепь, состоящая из аминокислотной последовательности, представленной положениями с 20 по 470 SEQ ID NO: 14, и легкая цепь, состоящая из аминокислотной последовательности, представленной положениями с 21 по 234 SEQ ID NO: 18,
тяжелую цепь, состоящую из аминокислотной последовательности, представленной положениями с 20 по 470 SEQ ID NO: 14, и легкую цепь, состоящую из аминокислотной последовательности, представленной положениями с 21 по 234 SEQ ID NO: 20, и
тяжелая цепь, состоящая из аминокислотной последовательности, представленной положениями с 20 по 470 SEQ ID NO: 16, и легкая цепь, состоящая из аминокислотной последовательности, представленной положениями с 21 по 234 SEQ ID NO: 22.
15. Способ по любому из пп.1-11, в котором анти-TROP2-антитело содержит вариабельную область тяжелой цепи, состоящую из аминокислотной последовательности, представленной положениями от 20 по 140 SEQ ID NO: 12, и вариабельную область легкой цепи, состоящую из аминокислотной последовательности, представленной положениями с 21 по 129 SEQ ID NO: 18.
16. Способ по любому из пп.1-11, в котором анти-TROP2-антитело содержит тяжелую цепь, состоящую из аминокислотной последовательности, представленной положениями с 20 по 470 SEQ ID NO: 12, и легкую цепь, состоящую из аминокислотной последовательности, представленной положениями с 21 по 234 SEQ ID NO: 18.
17. Способ по п.14, в котором анти-TROP2-антитело не имеет остатка лизина на карбоксильном конце тяжелой цепи.
18. Способ по п.16, в котором анти-TROP2-антитело не имеет остатка лизина на карбоксильном конце тяжелой цепи.
19. Способ по любому из пп.1-11, в котором среднее количество единиц выбранной структуры лекарственное средство-линкер, конъюгированной на антитело, находится в диапазоне от 2 до 8.
20. Способ по любому из пп.1-11, в котором среднее количество единиц выбранной структуры лекарственное средство-линкер, конъюгированной на антитело, находится в диапазоне от 3 до 8.
21. Способ получения конъюгата антитело-лекарственное средство, представленного следующей формулой:
Figure 00000003
где n представляет собой среднее количество звеньев структуры лекарственное средство-линкер, конъюгированных на антитело против TROP2,
где анти-TROP2 антитело содержит:
тяжелую цепь, состоящую из аминокислотной последовательности, представленной положениями с 20 по 470 SEQ ID NO: 12, и легкую цепь, состоящую из аминокислотной последовательности, представленной положениями с 21 по 234 SEQ ID NO: 18,
и, где способ включает стадию
обработки анти-TROP2 антитела в восстановительном состоянии и затем
взаимодействя анти-TROP2 антитела с соединением, представленным следующей формулой:
Figure 00000004
22. Способ по п.21, в котором анти-TROP2 антитело не имеет остатка лизина на карбоксильном конце тяжелой цепи.
23. Способ по п.21 или 22, в котором n имеет значение в диапазоне от 2 до 8.
24. Способ по п.21 или 22, в котором n имеет значение в диапазоне от 3 до 8.
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