RU2016151208A - Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор-пиридин-3-ил]-пиразоло[1, 5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы - Google Patents
Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор-пиридин-3-ил]-пиразоло[1, 5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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Claims (58)
1. Соединение формулы I-A:
или его фармацевтически приемлемая соль или производное, где:
каждый из Y1, Y2, Y3, Y4, Y5, Y6 и Y7 независимо означает водород или дейтерий; при условии, что, по меньшей мере, один из Y1, Y2, Y3, Y4, Y5, Y6 и Y7 означает дейтерий;
каждый из Х1, Х2 и Х4 независимо выбирают из 12С или 13С; и
Х3 независимо выбирают из -12С(О)- или -13С(О)-.
2. Соединение по п.1, где Y1, Y2, Y3 и Y4 независимо выбирают из дейтерия или водорода; и Y5, Y6 и Y7 означают дейтерий.
3. Соединение по п.1, где Y1 и Y2 независимо выбирают из дейтерия или водорода; и Y3, Y4, Y5, Y6 и Y7 означают дейтерий.
4. Соединение по п.1, где Y1, Y2, Y5, Y6 и Y7 независимо выбирают из дейтерия или водорода; и Y3 и Y4 означают дейтерий.
5. Соединение по п.1, где Y1, Y3 и Y4 независимо выбирают из дейтерия или водорода; и Y2, Y5, Y6 и Y7 означают дейтерий.
6. Соединение по п.1, где Y1, Y2, Y3, Y4, Y5, Y6 и Y7 означают водород; и Х4 означает 13С.
7. Соединение по п.1, где Y1, Y2, Y3, Y4, Y5, Y6 и Y7 означают водород; и Х1 и Х4 означают 13С.
8. Соединение по п.1, где Y1, Y2, Y3, Y4, Y5, Y6 и Y7 означают водород; и Х3 означает -13С(О)-.
9. Соединение по п.1, где Y1, Y3, Y4, Y5, Y6 и Y7 означают водород; Y2 означает дейтерий; и Х4 означает 13С.
10. Соединение по п.1, где Y1, Y2, Y3 и Y4 означают водород; Y5, Y6 и Y7 означают дейтерий; и Х1 означает 13С.
11. Соединение по п.1, где Y1, Y3, Y4, Y5, Y6 и Y7 означают водород; Y2 означает дейтерий; и Х1 означает 13С.
12. Соединение по п.1, где Y1, Y2, Y3, Y5, Y6 и Y7 означают водород; Y4 означает дейтерий; и Х1 означает 13С.
13. Соединение по п.1, где Y1 означает водород; Y2, Y3, Y4, Y5, Y6 и Y7 означают дейтерий; Х2 означает 13С; и Х3 означает -13С(О)-.
14. Способ получения соединения формулы I-1:
включающий стадию взаимодействия соединения формулы 6b:
с соединением формулы 11:
в подходящих условиях для образования амидной связи.
15. Способ по п.14, дополнительно включающий стадию получения соединения формулы 11:
путем взаимодействия соединения формулы 9:
с соединением формулы 10:
в подходящих условиях для катализируемой металлом реакции кросс-сочетания с образованием аддукта, содержащего защищенную аминогруппу; после чего
полученный аддукт подвергают воздействию подходящих условий для снятия защиты.
16. Способ по п.15, дополнительно включающий стадию получения соединения формулы 9:
путем взаимодействия соединения формулы 8:
в подходящих условиях для галогенирования.
17. Способ по п.16, дополнительно включающий стадию получения соединения формулы 8:
путем взаимодействия соединения формулы 7:
в подходящих условиях для получения защищенной аминогруппы.
18. Твердая форма соединения формулы I-1:
где эту форму выбирают из группы, состоящей из соединения I-1 в виде безводного свободного основания, соединения I-1 в виде гидрата или соединения I-1 в виде аддукта с винной кислотой.
19. Твердая форма по п.18, где форма представляет собой кристаллическое соединение I-1 в виде безводного свободного основания.
20. Твердая форма по п.19, характеризующаяся одним или более пиками, выраженными значениями 2-тета ± 0,2, равными примерно 9,9, 12,8, 15,4, 17,0, 23,1, 27,8, 29,0 и 30,1 градусов, на порошковой рентгеновской дифрактограмме, полученной с использованием излучения Cu-K-альфа.
21. Твердая форма по п.19, характеризующаяся порошковой рентгеновской дифрактограммой, по существу такой же, как представлена на Фиг.1а.
22. Твердая форма по п.18, где эта форма представляет собой кристаллическое соединение I-1 в виде гидрата.
23. Твердая форма по п.22, где кристаллическое соединение I-1 в виде гидрата имеет соотношение соединения I-1 к воде, составляющее 1:3.
24. Твердая форма по п.22, характеризующаяся потерей массы от примерно 12,6% в диапазоне температуры от примерно 40°С до примерно 100°С.
25. Твердая форма по п.22, характеризующаяся одним или более пиками, выраженными значениями 2-тета ± 0,2, равными примерно 27,5, 20,6 и 9,7 градусов, на порошковой рентгеновской дифрактограмме, полученной с использованием излучения Cu-K-альфа.
26. Твердая форма по п.22, характеризующаяся порошковой рентгеновской дифрактограммой, по существу такой же, как приведена на Фиг.1b.
27. Твердая форма по п.18, где форма представляет собой кристаллическое соединение I-1 в виде аддукта с винной кислотой.
28. Твердая форма по п.27, где кристаллическое соединение I-1в виде аддукта с винной кислотой имеет соотношение соединения I-1 к винной кислоте, составляющее 1:1.
29. Твердая форма по п.27, характеризующаяся одним или более пиками, выраженными значениями 2-тета ± 0,2, равными примерно 7,1, 18,3 и 13,2 градусов, на порошковой рентгенограмме, полученной с использованием излучения Cu-K-альфа.
30. Твердая форма по п.27, характеризующаяся порошковой рентгенограммой, по существу такой же, как представлена на Фиг.1с.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462008277P | 2014-06-05 | 2014-06-05 | |
| US62/008,277 | 2014-06-05 | ||
| PCT/US2015/032879 WO2015187451A1 (en) | 2014-06-05 | 2015-05-28 | Radiolabelled derivatives of a 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]- pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, the preparation of said compound and different solid forms thereof |
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| RU2020110358A Division RU2020110358A (ru) | 2014-06-05 | 2015-05-28 | Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор- пиридин-3-ил]-пиразоло[1,5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы |
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| RU2016151208A true RU2016151208A (ru) | 2018-07-10 |
| RU2016151208A3 RU2016151208A3 (ru) | 2018-11-14 |
| RU2719583C2 RU2719583C2 (ru) | 2020-04-21 |
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| RU2016151208A RU2719583C2 (ru) | 2014-06-05 | 2015-05-28 | Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор-пиридин-3-ил]-пиразоло[1, 5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы |
| RU2020110358A RU2020110358A (ru) | 2014-06-05 | 2015-05-28 | Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор- пиридин-3-ил]-пиразоло[1,5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы |
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| RU2020110358A RU2020110358A (ru) | 2014-06-05 | 2015-05-28 | Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор- пиридин-3-ил]-пиразоло[1,5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы |
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| US (3) | US9670215B2 (ru) |
| EP (1) | EP3152212B9 (ru) |
| JP (2) | JP6568111B2 (ru) |
| KR (1) | KR102575125B1 (ru) |
| CN (2) | CN110590787A (ru) |
| AU (2) | AU2015271030B2 (ru) |
| BR (1) | BR112016028273B1 (ru) |
| CA (1) | CA2950587C (ru) |
| DK (1) | DK3152212T3 (ru) |
| ES (1) | ES2777608T3 (ru) |
| HR (1) | HRP20200186T1 (ru) |
| IL (1) | IL249361B (ru) |
| LT (1) | LT3152212T (ru) |
| MX (2) | MX2016015874A (ru) |
| PL (1) | PL3152212T3 (ru) |
| PT (1) | PT3152212T (ru) |
| RS (1) | RS60013B1 (ru) |
| RU (2) | RU2719583C2 (ru) |
| SG (2) | SG10201902206QA (ru) |
| SI (1) | SI3152212T1 (ru) |
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| SG10201607592PA (en) | 2008-12-19 | 2016-11-29 | Vertex Pharma | Pyrazine derivatives useful as inhibitors of atr kinase |
| WO2013049859A1 (en) | 2011-09-30 | 2013-04-04 | Vertex Pharmaceuticals Incorporated | Treating pancreatic cancer and non-small cell lung cancer with atr inhibitors |
| EP2940017B1 (en) | 2011-09-30 | 2019-08-28 | Vertex Pharmaceuticals Incorporated | Process for making compounds useful as inhibitors of ATR kinase |
| CN108478577A (zh) | 2012-04-05 | 2018-09-04 | 沃泰克斯药物股份有限公司 | 可用作atr激酶抑制剂的化合物及其组合疗法 |
| LT3418281T (lt) | 2012-12-07 | 2021-01-11 | Vertex Pharmaceuticals Inc. | Pirazolo[1,5-a]pirimidinai, naudotini kaip atr kinazės inhibitoriai, skirti vėžinių ligų gydymui |
| JP2016512815A (ja) | 2013-03-15 | 2016-05-09 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ａｔｒキナーゼの阻害剤として有用な縮合ピラゾロピリミジン誘導体 |
| PT3077397T (pt) | 2013-12-06 | 2020-01-22 | Vertex Pharma | Composto de 2-amino-6-fluoro-n-[5-fluoro-piridin-3-il]pirazolo[1,5-a]pirimidin-3-carboxamida útil como inibidor da atr quinase, a sua preparação, diferentes formas sólidas e derivados radiomarcados do mesmo |
| RS60013B1 (sr) | 2014-06-05 | 2020-04-30 | Vertex Pharma | Radioaktivno obeleženi derivati jedinjenja 2-amino-6-fluoro-n-[5-fluoropiridin-3-il]pirazolo[1,5-a]pirimidin-3-karboksamida, korisnog kao inhibitora atr kinaze, dobijanje pomenutog jedinjenja i njegovi različiti čvrsti oblici |
| CA2950780C (en) | 2014-06-17 | 2023-05-16 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of chk1 and atr inhibitors |
| AU2016331955B2 (en) | 2015-09-30 | 2022-07-21 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
| AU2017205101B2 (en) * | 2016-01-08 | 2023-05-04 | Breast Cancer Now | Inhibitors of ataxia-telangiectasia mutated and Rad3-related protein kinase (ATR) for use in methods of treating cancer |
| WO2018153972A1 (en) | 2017-02-24 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Combination of atr kinase inhibitors and antiandrogens |
| WO2018153969A1 (en) | 2017-02-24 | 2018-08-30 | Bayer Aktiengesellschaft | Combination of atr kinase inhibitors with radium-223 salt |
| JOP20190197A1 (ar) | 2017-02-24 | 2019-08-22 | Bayer Pharma AG | مثبط كيناز ايه تي آر للاستخدام في طريقة لعلاج مرض فرط التكاثر |
| WO2018206547A1 (en) | 2017-05-12 | 2018-11-15 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and atr inhibitors |
| EP3630116B1 (en) | 2017-05-26 | 2024-05-01 | The Board Of Regents Of The University Of Texas System | Tetrahydropyrido[4,3-d]pyrimidine inhibitors of atr kinase |
| CN111867590B (zh) | 2017-07-13 | 2023-11-17 | 德州大学系统董事会 | Atr激酶的杂环抑制剂 |
| US11690911B2 (en) | 2017-08-04 | 2023-07-04 | Bayer Aktiengesellschaft | Combination of ATR kinase inhibitors and PD-1/PD-L1 inhibitors |
| JP7290627B2 (ja) | 2017-08-17 | 2023-06-13 | ボード オブ レジェンツ，ザ ユニバーシティ オブ テキサス システム | Ａｔｒキナーゼの複素環式阻害剤 |
| EP3461480A1 (en) | 2017-09-27 | 2019-04-03 | Onxeo | Combination of a dna damage response cell cycle checkpoint inhibitors and belinostat for treating cancer |
| CA3084863A1 (en) | 2017-12-08 | 2019-06-13 | Bayer Aktiengesellschaft | Predictive markers for atr kinase inhibitors |
| CN112218631B (zh) | 2018-03-16 | 2023-12-22 | 德州大学系统董事会 | Atr激酶的杂环抑制剂 |
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