KR20230175222A - Nek7 억제제 - Google Patents
Nek7 억제제 Download PDFInfo
- Publication number
- KR20230175222A KR20230175222A KR1020237037931A KR20237037931A KR20230175222A KR 20230175222 A KR20230175222 A KR 20230175222A KR 1020237037931 A KR1020237037931 A KR 1020237037931A KR 20237037931 A KR20237037931 A KR 20237037931A KR 20230175222 A KR20230175222 A KR 20230175222A
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- KR
- South Korea
- Prior art keywords
- compound
- mmol
- methyl
- pyrimidin
- trifluoromethyl
- Prior art date
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A—HUMAN NECESSITIES
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- 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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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
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- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US63/170,708 | 2021-04-05 | ||
| US202163185282P | 2021-05-06 | 2021-05-06 | |
| US63/185,282 | 2021-05-06 | ||
| PCT/US2022/023443 WO2022216680A1 (en) | 2021-04-05 | 2022-04-05 | Nek7 inhibitors |
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| MX (1) | MX2023011464A (https=) |
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| JP7729000B2 (ja) * | 2023-02-24 | 2025-08-25 | 日本たばこ産業株式会社 | ６－アルコキシピラゾロピリミジン化合物及びその医薬用途 |
| CN121368589A (zh) * | 2023-03-17 | 2026-01-20 | 万特斯治疗美国公司 | 用于抑制nlrp3的脲衍生物及其用途 |
| WO2025067411A1 (zh) * | 2023-09-28 | 2025-04-03 | 北京普祺医药科技股份有限公司 | 一种nek7抑制剂、药物组合物及其用途 |
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| BR112014030284B1 (pt) | 2012-07-18 | 2021-11-30 | Sunshine Lake Pharma Co., Ltd | Composto, composição farmacêutica, e, uso de um composto ou de uma composição farmacêutica |
| US8859553B2 (en) | 2012-07-30 | 2014-10-14 | Astar Biotech Llc | Protein kinase inhibitors |
| ES2755772T3 (es) | 2012-11-07 | 2020-04-23 | Nerviano Medical Sciences Srl | Pirimidinil y piridinilpirrolopiridinonas sustituidas, proceso para su preparación y su uso como inhibidores de cinasas |
| EP2997030B1 (en) | 2013-05-14 | 2017-08-09 | Nerviano Medical Sciences S.R.L. | Pyrrolo[2,3-d]pyrimidine derivatives, process for their preparation and their use as kinase inhibitors |
| EA029412B1 (ru) | 2013-06-28 | 2018-03-30 | Бейджин, Лтд. | Конденсированные трициклические соединения мочевины в качестве ингибиторов киназы raf и/или димера киназы raf |
| WO2015117147A1 (en) | 2014-02-03 | 2015-08-06 | Quadriga Biosciences, Inc. | Beta-substituted beta-amino acids and analogs as chemotherapeutic agents |
| JP2017525727A (ja) | 2014-08-26 | 2017-09-07 | アスター バイオテック リミテッド ライアビリティ カンパニー | プロテインキナーゼ阻害剤 |
| CN105837575B (zh) | 2015-01-13 | 2019-01-15 | 四川大学 | 3-乙炔基吡唑并嘧啶衍生物及其制备方法和用途 |
| EA038421B1 (ru) | 2015-12-30 | 2021-08-26 | ВиПиЭс-3, ИНК. | Соединения, ингибирующие металлоферменты |
| CN107513068A (zh) | 2016-06-16 | 2017-12-26 | 中国科学院上海药物研究所 | 一种具有fgfr抑制活性的新型化合物及其制备和应用 |
| JP6570776B2 (ja) | 2016-06-20 | 2019-09-04 | テグ−キョンプク メディカル イノベーション ファウンデーション | 新規のイミダゾピリジン誘導体、その製造方法及びこれを有効成分として含有する癌の予防又は治療用医薬組成物 |
| JP6867417B2 (ja) | 2016-06-21 | 2021-04-28 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | キナーゼ阻害剤としてのｎ−（置換フェニル）−スルホンアミド誘導体 |
| EP3296297A1 (en) | 2016-09-15 | 2018-03-21 | Centre National De La Recherche Scientifique | Benzimidazol derivatives for treating filovirus infection |
| EP3548476A4 (en) | 2016-12-02 | 2020-05-20 | Quentis Therapeutics, Inc. | SMALL MOLECULAR IRE1 INHIBITORS |
| AU2018272986A1 (en) | 2017-05-26 | 2019-12-12 | Ichnos Sciences SA | Novel inhibitors of MAP4K1 |
| WO2018222917A1 (en) | 2017-06-01 | 2018-12-06 | Quentis Therapeutics, Inc. | Ire1 small molecule inhibitors |
| CA3074208C (en) | 2017-08-31 | 2023-10-03 | Daiichi Sankyo Company, Limited | Novel method for producing antibody-drug conjugate |
| IL277408B2 (en) * | 2018-04-05 | 2024-08-01 | Merck Patent Gmbh | Heteroaryl compounds as IRAK type II inhibitors and their use |
| WO2019196812A1 (zh) | 2018-04-09 | 2019-10-17 | 上海科技大学 | 蛋白降解靶向化合物、其抗肿瘤应用、其中间体及中间体应用 |
| US20210139484A1 (en) | 2018-04-11 | 2021-05-13 | Gossamer Bio Services, Inc. | Dihydroisoquinoline-2(1h)-carboxamide and related compounds and their use in treating medical conditions |
| CN112243439A (zh) | 2018-06-13 | 2021-01-19 | 百济神州有限公司 | 作为hpk1抑制剂的吡咯并[2,3-b]吡啶或吡咯并[2,3-b]吡嗪及其用途 |
| WO2020135507A1 (zh) | 2018-12-26 | 2020-07-02 | 杭州百新生物医药科技有限公司 | 一种多取代苯氨基嘧啶衍生物及其制备方法和用途 |
| CN111646995B (zh) * | 2019-03-04 | 2023-03-21 | 四川大学 | 4-氨基-嘧啶并氮杂环-苯基脲类衍生物及其制备方法和用途 |
| WO2020206583A1 (en) | 2019-04-08 | 2020-10-15 | Qilu Regor Therapeutics Inc. | Kinase inhibitors and uses thereof |
| CA3152508A1 (en) * | 2019-08-29 | 2021-03-04 | Hibercell, Inc. | Perk inhibiting pyrrolopyrimidine compounds |
| WO2021057877A1 (zh) * | 2019-09-26 | 2021-04-01 | 深圳市塔吉瑞生物医药有限公司 | 取代的芳香稠合环衍生物及其组合物及用途 |
| US20220389009A1 (en) | 2019-10-01 | 2022-12-08 | Goldfinch Bio, Inc. | Substituted 1,6-naphthyridine inhibitors of cdk5 |
| US12565481B2 (en) | 2020-02-20 | 2026-03-03 | Guangzhou Baiyunshan Pharmaceutical Holdings Co., Ltd. Baiyunshan Pharmaceutical General Factory | 6,7-dimethoxy-3-(pyridin-2-yl)quinoline compounds for inhibiting RET |
| WO2021226547A2 (en) | 2020-05-08 | 2021-11-11 | Halia Therapeutics, Inc. | Targeted nek7 inhibition for modulation of the nlrp3 inflammasome |
| CN113717156B (zh) | 2020-05-25 | 2023-05-09 | 南京红云生物科技有限公司 | Egfr抑制剂、其制备方法及用途 |
| GB202010464D0 (en) | 2020-07-08 | 2020-08-19 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of diseases |
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