RU2021125455A - Твердые формы { [5-(3-хлорфенил)-3-гидроксипиридин-2-карбонил]амино} уксусной кислоты, их композиции и применения - Google Patents

Твердые формы { [5-(3-хлорфенил)-3-гидроксипиридин-2-карбонил]амино} уксусной кислоты, их композиции и применения Download PDF

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RU2021125455A
RU2021125455A RU2021125455A RU2021125455A RU2021125455A RU 2021125455 A RU2021125455 A RU 2021125455A RU 2021125455 A RU2021125455 A RU 2021125455A RU 2021125455 A RU2021125455 A RU 2021125455A RU 2021125455 A RU2021125455 A RU 2021125455A
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Джеймс Денсмор КОПП
Энн У. НЬЮМАН
Энн ЛУОНГ
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Экебиа Терапьютикс, Инк.
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Claims (63)

1. Кристаллическое соединение (I):
Figure 00000001
которое имеет порошковую рентгеновскую дифрактограмму, содержащую пики при 18,1, 20,3, 22,9, 24,0 и 26,3° ±0,2 2θ; и
где указанное кристаллическое соединение (I):
является безводным и несольватированным;
содержит менее чем 5% по массе любого другого кристаллического соединения (I);
содержит менее чем 5% по массе аморфного соединения (I);
содержит менее чем 100 частей на миллион соединения формулы (II):
Figure 00000002
как определено с помощью ГХ/МС; и
является чистым по меньшей мере на 99,5%, как измерено с помощью ВЭЖХ; и
где указанное кристаллическое соединение (I) получают способом, включающим
a) приготовление раствора соединения (I) в органическом растворителе, где органический растворитель представляет собой ацетон;
b) доведение раствора до перенасыщения, чтобы вызвать образование кристаллического соединения (I).
2. Кристаллическое соединение (I) по п.1, где ацетоновый раствор соединения (I) фильтруют через угольный фильтр.
3. Кристаллическое соединение (I) по п.1, образованное способом, в котором стадия (b) включает добавление антирастворителя, охлаждение раствора, уменьшение объема раствора, замену растворителя, или любую их комбинацию,
где уменьшение объема производится путем испарения,
антирастворитель представляет собой воду,
доведение раствора до перенасыщения включает охлаждение раствора и добавление антирастворителя, где антирастворитель представляет собой воду,
доведение раствора до перенасыщения включает замену растворителя и охлаждение раствора, где замена растворителя включает замену растворителя отгонкой при пониженном давлении, где ацетон заменяют на метилизобутилкетон,
и/или
раствор охлаждают до температуры от 19°C до 25°C, где раствор охлаждают также до температуры от 0°C до 5°C.
4. Кристаллическое соединение (I) по любому из пп.1-3, образованное способом, дополнительно включающем введение затравки в ацетоновый раствор, и/или промывку кристаллов, и
где промывка включает промывку с использованием жидкости, выбранной из ацетона, метилизобутилкетона, н-гептана и воды, или любой их комбинации.
5. Кристаллическое соединение (I) по п.4, где промывка включает промывку с использованием комбинации ацетона и воды, или метилизобутилкетона.
6. Кристаллическое соединение (I) по любому из пп.1-5, где выделение кристаллов соединения (I) на стадии (с) включает фильтрацию.
7. Кристаллическое соединение (I) по любому из пп.1-6, где кристаллическое соединение (I) сушат при пониженном давлении, необязательно при повышенной температуре, и где сушку проводят при температуре 50°C.
8. Кристаллическое соединение (I) по любому из пп.1-7, где кристаллическое соединение (I) имеет точку плавления температуре около 175,8°C±5°C.
9. Кристаллическое соединение (I) по любому из пп.1-8, где кристаллическое соединение (I) содержит менее чем 50 частей на миллион соединения формулы (II), как определено с помощью ГХ/МС.
10. Кристаллическое соединение (I) по любому из пп.1-8, где кристаллическое соединение содержит менее 10 частей на миллион соединения формулы (II), как определено с помощью ГХ/МС.
11. Кристаллическое соединение (I) по любому из пп.1-8, где кристаллическое соединение содержит менее 1 части на миллион соединения формулы (II), как определено с помощью ГХ/МС.
12. Кристаллическое соединение (I) по любому из пп.1-11, где кристаллическое соединение (I) является чистым по меньшей мере на 99,6%, как измерено с помощью ВЭЖХ.
13. Кристаллическое соединение (I) по любому из пп.1-11, где кристаллическое соединение (I) является чистым по меньшей мере на 99,7%, как измерено с помощью ВЭЖХ.
14. Кристаллическое соединение (I) по любому из пп.1-11, где кристаллическое соединение (I) является чистым по меньшей мере на 99,8%, как измерено с помощью ВЭЖХ.
15. Кристаллическое соединение (I) по любому из пп.1-11, где кристаллическое соединение (I) является чистым по меньшей мере на 99,9%, как измерено с помощью ВЭЖХ.
16. Фармацевтическая композиция, содержащая кристаллическое соединение (I) по любому из пп.1-15.
17. Пероральная дозированная форма, содержащая кристаллическое соединение по любому из пп.1-15.
18. Кристаллическое соединение (I) по любому из пп.1-15, или фармацевтическая композиция по п.16, или пероральная дозированная форма по п.17, для применения в способе лечения анемии, где анемия представляет собой анемию, вызванную хроническим заболеванием почек.
19. Способ получения кристаллического соединения (I), включающий:
Figure 00000001
a) приготовление раствора соединения (I) в органическом растворителе, представляющем собой ацетон;
b) доведение раствора до перенасыщения, чтобы вызвать образование кристаллов; и
c) выделение кристаллов.
20. Способ по п.19, где кристаллическое соединение (I) имеет порошковую рентгеновскую дифрактограмму, содержащую пики при 18,1, 20,3, 22,9, 24,0 и 26,3±2° 2θ.
21. Способ по п.19, где кристаллическое соединение (I) содержит менее чем 10% по массе любого другого кристаллического соединения (I).
22. Способ по п.22, где кристаллическое соединение (I) содержит менее чем 5% по массе любого другого кристаллического соединения (I).
23. Способ по п.19, где кристаллическое соединение содержит менее чем 10% по массе аморфного соединения (I).
24. Способ по п.23, где кристаллическое соединение содержит менее чем 5% по массе аморфного соединения (I).
25. Способ по п.19, где кристаллическое соединение (I) имеет пик в термограмме ДСК около 175,8°С.
26. Способ по п.19, где кристаллическое соединение (I) содержит менее чем 100 частей на миллион соединения формулы (II):
Figure 00000002
как определено с помощью ГХ/МС.
27. Способ по п.26, где кристаллическое соединение (I) содержит менее чем 50 частей на миллион соединения формулы (II).
28. Способ по п.27, где кристаллическое соединение (I) содержит менее чем 10 частей на миллион соединения формулы (II).
29. Способ по п.28, где кристаллическое соединение (I) является чистым по меньшей мере на 99,5%, как измерено с помощью ВЭЖХ.
30. Способ по п.19, дополнительно включающий фильтрование раствора через угольный фильтр.
31. Способ по п.19, где доведение раствора до перенасыщения включает добавление антирастворителя, представляющего собой воду, охлаждение раствора, и уменьшение объема раствора путем выпаривания, замену растворителя, или любую их комбинацию.
32. Способ по п.19, дополнительно включающий промывку кристаллов.
33. Способ по п.32, где промывка включает промывку с использованием ацетона или воды, или любой их комбинации.
34. Способ по п.32, где промывка включает промывку с использованием комбинации ацетона и воды.
35. Способ по п.19, где выделение кристаллов включает фильтрацию кристаллов.
36. Способ по п.19, дополнительно включающий сушку кристаллов при пониженном давлении, необязательно при повышенной температуре.
37. Способ по п.36, где сушку проводят при температуре около 50°C.
RU2021125455A 2013-11-15 2014-11-14 Твердые формы { [5-(3-хлорфенил)-3-гидроксипиридин-2-карбонил]амино} уксусной кислоты, их композиции и применения RU2021125455A (ru)

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