RU2019113160A - Соединения пригодные для использования в качестве ингибиторов atr киназы - Google Patents
Соединения пригодные для использования в качестве ингибиторов atr киназы Download PDFInfo
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- RU2019113160A RU2019113160A RU2019113160A RU2019113160A RU2019113160A RU 2019113160 A RU2019113160 A RU 2019113160A RU 2019113160 A RU2019113160 A RU 2019113160A RU 2019113160 A RU2019113160 A RU 2019113160A RU 2019113160 A RU2019113160 A RU 2019113160A
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- formula
- compound
- amide bond
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- 150000001875 compounds Chemical class 0.000 title claims 28
- 239000003112 inhibitor Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims 18
- 230000015572 biosynthetic process Effects 0.000 claims 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 239000000010 aprotic solvent Substances 0.000 claims 6
- 230000003993 interaction Effects 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 239000002738 chelating agent Substances 0.000 claims 3
- 238000010511 deprotection reaction Methods 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- VORIUEAZEKLUSJ-UHFFFAOYSA-M [(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylidene]-dimethylazanium;trifluoroborane;fluoride Chemical compound [F-].FB(F)F.C1=C(Cl)C=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 VORIUEAZEKLUSJ-UHFFFAOYSA-M 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims 1
- 239000012317 TBTU Substances 0.000 claims 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- BFZXXCSKNHQBEF-UHFFFAOYSA-N ethane-1,2-diamine;propane-1,3-diamine Chemical compound NCCN.NCCCN BFZXXCSKNHQBEF-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (49)
1. Способ получения соединения формулы I-1
включающий стадию
a) взаимодействия соединения формулы 6a*
с соединением формулы 27:
при соответствующих условиях образования амидной связи с образованием соединения формулы 28
b) очистку соединения формулы 28 с использованием соответствующего хелатирующего агента для палладия;
c) взаимодействия соединения формулы 28 при соответствующих условиях снятия защиты с образованием соединения формулы 30
d) взаимодействия соединения формулы 30 с соединением формулы 25:
при соответствующих условиях образования амидной связи с образованием соединения формулы I-1.
2. Способ по п.1, в котором соответствующие условия для образования амидной связи включают взаимодействие соединения формулы 30 с соединением формулы 25 в присутствии партнера для образования амидной связи, апротонного растворителя и основания.
3. Соединение по п.2, где апротонный растворитель независимо выбирают из NMP, DMF или тетрагидрофурана.
4. Способ по п.3, в котором апротонный растворитель представляет собой тетрагидрофуран.
5. Способ по п.2, в котором основание представляет собой алифатический амин.
6. Способ по п.5, в котором основание представляет собой DIPEA.
7. Способ по любому из пп.2-6, в котором партнер для образования амидной связи независимо выбирают из CDI, TBTU, или TCTU.
8. Способ по п.7, в котором партнер для образования амидной связи представляет собой TCTU.
9. Способ по п.7, в котором партнер для образования амидной связи представляет собой CDI.
10. Способ по п.1, в котором соответствующие условия снятия защиты включают взаимодействие соединения формулы 28 с кислотой в присутствии растворителя.
11. Способ по п.10, в котором кислота представляет собой HCl.
12. Способ по п.10, в котором растворитель представляет собой 1,4-диоксан.
13. Способ по п.1, в котором соответствующие условия для образования амидной связи включают взаимодействие соединения формулы 6a* с соединением формулы 27 в апротонном растворителе при нагреве.
14. Способ по п.13, в котором апротонный растворитель независимо выбирается из NMP, пиридин или DMF.
15. Способ по п.14, в котором апротонный растворитель представляет собой пиридин.
16. Способ по п.15, в котором реакцию осуществляют при температуре, по меньшей мере, 80°C.
17. Способ по п.1, в котором хелатирующий агент для палладия независимо выбирается из пропан-1,2-диамина; этан-1,2-диамина; этан-1,2-диамина; пропан-1,3-диамина; тетраметилэтилендиамина; этиленгликоля; 1,3-бис(дифенилфосфанил)пропана; 1,4-бис(дифенилфосфанил)бутана; и 1,2-бис(дифенилфосфанил)этан/Pr-1,2-диамина.
18. Способ по п.17, в котором хелатирующий агент для палладия представляет собой пропан-1,2-диамин.
19. Способ получения соединения формулы I-1
включающий стадии
a) взаимодействия соединения формулы 5a
при соответствующих условиях галогенирования с образованием соединения формулы 34
где X представляет собой галоген;
b) взаимодействия соединения формулы 34 с соединением формулы 27
при соответствующих условиях образования амидной связи с образованием соединения формулы 28.
c) взаимодействия соединения формулы 28 при соответствующих условиях снятия защиты с образованием соединения формулы 30
d) взаимодействия соединения формулы 30 с соединением формулы 25
при соответствующих условиях образования амидной связи с образованием соединения формулы I-1.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361912636P | 2013-12-06 | 2013-12-06 | |
| US61/912,636 | 2013-12-06 | ||
| US201462008220P | 2014-06-05 | 2014-06-05 | |
| US62/008,220 | 2014-06-05 | ||
| US201462058819P | 2014-10-02 | 2014-10-02 | |
| US62/058,819 | 2014-10-02 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016126919A Division RU2687276C2 (ru) | 2013-12-06 | 2014-12-05 | Соединения, пригодные для использования в качестве ингибиторов atr киназы |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2020114516A Division RU2750148C1 (ru) | 2013-12-06 | 2020-04-23 | Соединения, пригодные для использования в качестве ингибиторов atr киназы |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2019113160A true RU2019113160A (ru) | 2019-06-17 |
| RU2019113160A3 RU2019113160A3 (ru) | 2019-11-19 |
| RU2720408C2 RU2720408C2 (ru) | 2020-04-29 |
Family
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Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2019113160A RU2720408C2 (ru) | 2013-12-06 | 2014-12-05 | Способ получения ингибиторов atr киназы (варианты) |
| RU2016126919A RU2687276C2 (ru) | 2013-12-06 | 2014-12-05 | Соединения, пригодные для использования в качестве ингибиторов atr киназы |
| RU2020114516A RU2750148C1 (ru) | 2013-12-06 | 2020-04-23 | Соединения, пригодные для использования в качестве ингибиторов atr киназы |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016126919A RU2687276C2 (ru) | 2013-12-06 | 2014-12-05 | Соединения, пригодные для использования в качестве ингибиторов atr киназы |
| RU2020114516A RU2750148C1 (ru) | 2013-12-06 | 2020-04-23 | Соединения, пригодные для использования в качестве ингибиторов atr киназы |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US10160760B2 (ru) |
| EP (1) | EP3077397B1 (ru) |
| JP (1) | JP6543252B2 (ru) |
| KR (1) | KR102153886B1 (ru) |
| CN (1) | CN105934435B (ru) |
| AU (2) | AU2014360380B2 (ru) |
| BR (1) | BR112016012734B1 (ru) |
| CA (1) | CA2932757C (ru) |
| DK (1) | DK3077397T3 (ru) |
| ES (1) | ES2768678T3 (ru) |
| HR (1) | HRP20192183T1 (ru) |
| HU (1) | HUE046727T2 (ru) |
| IL (1) | IL246028B (ru) |
| LT (1) | LT3077397T (ru) |
| MX (1) | MX370390B (ru) |
| PL (1) | PL3077397T3 (ru) |
| PT (1) | PT3077397T (ru) |
| RS (1) | RS59679B1 (ru) |
| RU (3) | RU2720408C2 (ru) |
| SG (2) | SG11201604519PA (ru) |
| SI (1) | SI3077397T1 (ru) |
| WO (1) | WO2015085132A1 (ru) |
| ZA (1) | ZA201603893B (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106518856B (zh) | 2008-12-19 | 2020-04-28 | 沃泰克斯药物股份有限公司 | 用作atr激酶抑制剂的化合物 |
| US9309250B2 (en) | 2011-06-22 | 2016-04-12 | Vertex Pharmaceuticals Incorporated | Substituted pyrrolo[2,3-b]pyrazines as ATR kinase inhibitors |
| CA2850566C (en) | 2011-09-30 | 2022-05-03 | Vertex Pharmaceuticals Incorporated | Process for making 4-[chloro-n-hydroxycarbonimidoyl]phenyl derivative |
| EP3733185B1 (en) | 2011-09-30 | 2022-12-07 | Vertex Pharmaceuticals Incorporated | Treating non-small cell lung cancer with atr inhibitors |
| EP2833973B1 (en) | 2012-04-05 | 2017-09-13 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase and combination therapies thereof |
| DK3418281T3 (da) | 2012-12-07 | 2020-12-07 | Vertex Pharma | Pyrazolo[1,5-a]pyrimidiner, der er anvendelige som inhibitorer af atr-kinase til behandling af cancersygdomme |
| 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 |
| KR102575125B1 (ko) | 2014-06-05 | 2023-09-07 | 버텍스 파마슈티칼스 인코포레이티드 | Atr 키나제의 저해제로서 유용한 2-아미노-6-플루오로-n-[5-플루오로-피리딘-3-일]-피라졸로[1,5-a]피리미딘-3-카복스아미드 화합물의 방사성표지된 유도체, 상기 화합물의 제조 및 이의 다양한 고체 형태 |
| DK3157566T3 (da) | 2014-06-17 | 2019-07-22 | Vertex Pharma | Fremgangsmåde til behandling af cancer under anvendelse af en kombination chk1- og atr-inhibitorer |
| MX395066B (es) | 2015-09-30 | 2025-03-24 | Vertex Pharma | Método para tratar cáncer usando una combinación de agentes que dañan el adn e inhibidores de proteína relacionada con ataxia telangiectasia y rad3 (atr). |
| WO2018077246A1 (zh) * | 2016-10-28 | 2018-05-03 | 正大天晴药业集团股份有限公司 | 用作神经营养因子酪氨酸激酶受体抑制剂的氨基吡唑并嘧啶化合物 |
| 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 |
| WO2018153972A1 (en) | 2017-02-24 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Combination of atr kinase inhibitors and antiandrogens |
| 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 |
| IL271930B (en) | 2017-07-13 | 2022-07-01 | Univ Texas | Heterocyclic inhibitors of atr kinase |
| CA3071760A1 (en) | 2017-08-04 | 2019-02-07 | Bayer Pharma Aktiengesellschaft | Combination of atr kinase inhibitors and pd-1/pd-l1 inhibitors |
| US10800774B2 (en) | 2017-08-17 | 2020-10-13 | Board Of Regents, The University Of Texas System | Heterocyclic inhibitors of ATR kinase |
| EP3461480A1 (en) | 2017-09-27 | 2019-04-03 | Onxeo | Combination of a dna damage response cell cycle checkpoint inhibitors and belinostat for treating cancer |
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