JPWO2020038415A5 - - Google Patents
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- Publication number
- JPWO2020038415A5 JPWO2020038415A5 JP2021509151A JP2021509151A JPWO2020038415A5 JP WO2020038415 A5 JPWO2020038415 A5 JP WO2020038415A5 JP 2021509151 A JP2021509151 A JP 2021509151A JP 2021509151 A JP2021509151 A JP 2021509151A JP WO2020038415 A5 JPWO2020038415 A5 JP WO2020038415A5
- Authority
- JP
- Japan
- Prior art keywords
- piperazin
- pyrrolidin
- pyridazin
- imidazo
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000005647 linker group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 4
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- GSAFGEITCNSCAJ-YTKQHNFLSA-N 2-(2,6-dioxopiperidin-3-yl)-5-[3-[[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]methyl]pyrrolidin-1-yl]isoindole-1,3-dione Chemical compound C1C[C@@H](N(C1)C2=NN3C(=NC=C3C4=NC(=CC=C4)N5CCN(CC5)CC6CCN(C6)C7=CC8=C(C=C7)C(=O)N(C8=O)C9CCC(=O)NC9=O)C=C2)C1=CC(=CC=C1)F GSAFGEITCNSCAJ-YTKQHNFLSA-N 0.000 claims 2
- GUXGUSYUJZREHG-KWRHIPAJSA-N 3-[5-[3-[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]-3-oxoprop-1-ynyl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(C=CC=1)[C@@H]1N(CCC1)C=1C=CC=2N(N=1)C(=CN=2)C1=CC=CC(=N1)N1CCN(CC1)C(C#CC1=CC=C2CN(C(C2=C1)=O)C1C(NC(CC1)=O)=O)=O GUXGUSYUJZREHG-KWRHIPAJSA-N 0.000 claims 2
- KORPLFDBDVBAFK-KWRHIPAJSA-N 3-[6-[3-[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]-3-oxoprop-1-ynyl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(C=CC=1)[C@@H]1N(CCC1)C=1C=CC=2N(N=1)C(=CN=2)C1=CC=CC(=N1)N1CCN(CC1)C(C#CC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O KORPLFDBDVBAFK-KWRHIPAJSA-N 0.000 claims 2
- RIYXRIJSDXMVNL-PBBFAOSKSA-N N-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl]-2-[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]acetamide Chemical compound C1N(C2=NC(=CC=C2)C=2N3C(=NC=2)C=CC(N2[C@H](CCC2)C2=CC(F)=CC=C2)=N3)CCN(C1)CC(=O)NC1=CC=2C(=O)N(C(=O)C=2C=C1)C1C(=O)NC(=O)CC1 RIYXRIJSDXMVNL-PBBFAOSKSA-N 0.000 claims 2
- JIGZJNQMIOEJSM-UHFFFAOYSA-N N-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-[4-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl]amino]ethyl]piperazin-1-yl]-2-(oxan-4-ylamino)benzamide Chemical compound C1C(NC2=C(C(=O)NC=3C4=CC(CC5=CC(F)=CC(F)=C5)=CC=C4NN=3)C=CC(N3CCN(CC3)CCNC3=CC=C4C(=C3)C(=O)N(C4=O)C3C(=O)NC(=O)CC3)=C2)CCOC1 JIGZJNQMIOEJSM-UHFFFAOYSA-N 0.000 claims 2
- HMQGMDOSEOPTJW-UHFFFAOYSA-N N-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-[4-[[1-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl]azetidin-3-yl]methyl]piperazin-1-yl]-2-(oxan-4-ylamino)benzamide Chemical compound O=C1C(N2C(=O)C3=CC(N4CC(CN5CCN(CC5)C5=CC=C(C(=O)NC=6C7=CC(=CC=C7NN=6)CC6=CC(=CC(=C6)F)F)C(NC6CCOCC6)=C5)C4)=CC=C3C2=O)CCC(=O)N1 HMQGMDOSEOPTJW-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 108091005682 Receptor kinases Proteins 0.000 claims 2
- 102000005937 Tropomyosin Human genes 0.000 claims 2
- 108010030743 Tropomyosin Proteins 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000015556 catabolic process Effects 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 238000006731 degradation reaction Methods 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 1
- APRUIDKBAJQJRN-XGDNGBMYSA-N 2-(2,6-dioxopiperidin-3-yl)-5-[2-[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]ethylamino]isoindole-1,3-dione Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1=O)NCCN1CCN(CC1)C1=NC(=CC=C1)C1=CN=C2N1N=C(C=C2)N1[C@H](CCC1)C1=CC(=CC=C1)F)=O)=O APRUIDKBAJQJRN-XGDNGBMYSA-N 0.000 claims 1
- GATVUHGZGNWIHZ-PBBFAOSKSA-N 2-(2,6-dioxopiperidin-3-yl)-5-[[2-[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]-2-oxoethyl]amino]isoindole-1,3-dione Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1=O)NCC(=O)N1CCN(CC1)C1=NC(=CC=C1)C1=CN=C2N1N=C(C=C2)N1[C@H](CCC1)C1=CC(=CC=C1)F)=O)=O GATVUHGZGNWIHZ-PBBFAOSKSA-N 0.000 claims 1
- HAOMASYZSUGNTB-BONSOQDYSA-N 3-[5-[3-[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]propyl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(C=CC=1)[C@@H]1N(CCC1)C=1C=CC=2N(N=1)C(=CN=2)C1=CC=CC(=N1)N1CCN(CC1)CCCC1=CC=C2CN(C(C2=C1)=O)C1C(NC(CC1)=O)=O HAOMASYZSUGNTB-BONSOQDYSA-N 0.000 claims 1
- MDRMKDKRQWVBFF-BONSOQDYSA-N 3-[6-[3-[4-[6-[6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]piperazin-1-yl]propyl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(C=CC=1)[C@@H]1N(CCC1)C=1C=CC=2N(N=1)C(=CN=2)C1=CC=CC(=N1)N1CCN(CC1)CCCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O MDRMKDKRQWVBFF-BONSOQDYSA-N 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 206010012305 Demyelination Diseases 0.000 claims 1
- 206010067601 Dysmyelination Diseases 0.000 claims 1
- FKUUPOKOGMWVTB-BONSOQDYSA-N O=C1NC(CCC1N1C(C2=CC=C(C=C2C1=O)N1CC(C1)CN1CCN(CC1)C1=NC(=CC=C1)C1=CN=C2N1N=C(C=C2)N1[C@H](CCC1)C1=CC(=CC=C1)F)=O)=O Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1=O)N1CC(C1)CN1CCN(CC1)C1=NC(=CC=C1)C1=CN=C2N1N=C(C=C2)N1[C@H](CCC1)C1=CC(=CC=C1)F)=O)=O FKUUPOKOGMWVTB-BONSOQDYSA-N 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 230000014509 gene expression Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000035772 mutation Effects 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000002018 overexpression Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2018101715 | 2018-08-22 | ||
| CNPCT/CN2018/101715 | 2018-08-22 | ||
| CNPCT/CN2019/086894 | 2019-05-14 | ||
| CN2019086894 | 2019-05-14 | ||
| PCT/CN2019/101850 WO2020038415A1 (en) | 2018-08-22 | 2019-08-21 | Tropomyosin receptor kinase (trk) degradation compounds and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021535104A JP2021535104A (ja) | 2021-12-16 |
| JPWO2020038415A5 true JPWO2020038415A5 (ru) | 2022-08-29 |
| JP7472103B2 JP7472103B2 (ja) | 2024-04-22 |
Family
ID=69592803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021509151A Active JP7472103B2 (ja) | 2018-08-22 | 2019-08-21 | トロポミオシン受容体キナーゼ（ｔｒｋ）分解化合物とその使用方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20210363146A1 (ru) |
| EP (1) | EP3841098A4 (ru) |
| JP (1) | JP7472103B2 (ru) |
| KR (1) | KR20210069634A (ru) |
| CN (2) | CN115626927B (ru) |
| AU (1) | AU2019323446A1 (ru) |
| BR (1) | BR112021003098A2 (ru) |
| CA (1) | CA3110267A1 (ru) |
| IL (1) | IL280984A (ru) |
| MX (1) | MX2021001957A (ru) |
| WO (1) | WO2020038415A1 (ru) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11969472B2 (en) | 2018-08-22 | 2024-04-30 | Cullgen (Shanghai), Inc. | Tropomyosin receptor kinase (TRK) degradation compounds and methods of use |
| GB201820165D0 (en) | 2018-12-11 | 2019-01-23 | Ucb Biopharma Sprl | Therapeutic agents |
| EP4076536A4 (en) * | 2019-12-17 | 2024-05-01 | Kymera Therapeutics, Inc. | IRAQ DEGRADATION AGENTS AND THEIR USES |
| JP2023514872A (ja) * | 2020-02-26 | 2023-04-11 | クルゲン（シャンハイ），インク． | トロポミオシン受容体キナーゼ（ｔｒｋ）分解化合物とその使用方法 |
| JP2023518423A (ja) * | 2020-03-19 | 2023-05-01 | カイメラ セラピューティクス， インコーポレイテッド | Ｍｄｍ２分解剤およびそれらの使用 |
| WO2021222542A1 (en) * | 2020-04-30 | 2021-11-04 | President And Fellows Of Harvard College | 5-amino-2-piperidinon-3-yl-1-oxoisoindoline derivatives for degradation of ikzf2 degraders |
| US11739101B2 (en) | 2020-05-06 | 2023-08-29 | Nurix Therapeutics, Inc. | Bifunctional degraders of hematopoietic progenitor kinase and therapeutic uses thereof |
| CN113801062B (zh) * | 2020-06-15 | 2023-05-26 | 沈阳药科大学 | 3-氨基-5-(3,5-二氟苄基)-1h-吲唑的制备方法 |
| CN112125977B (zh) * | 2020-09-29 | 2022-03-08 | 西安交通大学 | 一种tweak-mv1偶联蛋白及其抗银屑病的应用 |
| CN116583509A (zh) * | 2020-10-07 | 2023-08-11 | 上海睿跃生物科技有限公司 | 治疗癌症的化合物和方法 |
| WO2022152821A1 (en) | 2021-01-13 | 2022-07-21 | Monte Rosa Therapeutics Ag | Isoindolinone compounds |
| EP4323353A1 (en) * | 2021-04-12 | 2024-02-21 | Cullgen (Shanghai), Inc. | Tropomyosin receptor kinase (trk) degradation compounds and methods of use |
| CN113402467B (zh) * | 2021-06-18 | 2022-05-13 | 山东汇海医药化工有限公司 | 一种氟班色林的合成方法 |
| CA3223447A1 (en) | 2021-06-25 | 2022-12-29 | Korea Research Institute Of Chemical Technology | Novel bifunctional heterocyclic compound having btk degradation function via ubiquitin proteasome pathway, and use thereof |
| CN113278023B (zh) * | 2021-07-22 | 2021-10-15 | 上海睿跃生物科技有限公司 | 含氮杂环化合物及其制备方法和应用 |
| WO2023066350A1 (zh) * | 2021-10-22 | 2023-04-27 | 标新生物医药科技(上海)有限公司 | Crbn e3连接酶配体化合物、基于该配体化合物开发的蛋白降解剂及它们的应用 |
| EP4180428A1 (en) | 2021-11-12 | 2023-05-17 | Genzyme Corporation | Crystalline imidazo[4,5-b]pyridine compound, pharmaceutical compositions, and their use in treating medical conditions |
| CN114230518A (zh) * | 2021-12-13 | 2022-03-25 | 海南梵圣生物科技有限公司 | 一种5-苄基-1h-吲唑-3-胺类化合物的制备方法 |
| WO2023116835A1 (zh) * | 2021-12-24 | 2023-06-29 | 苏州开拓药业股份有限公司 | 一种具有酰亚胺骨架的多蛋白降解剂 |
| WO2023239629A1 (en) | 2022-06-06 | 2023-12-14 | Plexium, Inc. | Compounds and pharmaceutical compositions that degrade cdk2 |
| WO2023249994A1 (en) * | 2022-06-22 | 2023-12-28 | Mayo Foundation For Medical Education And Research | Methods and materials for treating cancer |
| CN117510504A (zh) * | 2022-08-05 | 2024-02-06 | 深圳市新樾生物科技有限公司 | 蛋白激酶降解剂、药物及应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201605917SA (en) * | 2014-01-24 | 2016-08-30 | Abbvie Inc | 6-phenyl- or 6-(pyridin-3-yl)indazole derivatives and methods of use |
| WO2015143652A1 (en) * | 2014-03-26 | 2015-10-01 | Merck Sharp & Dohme Corp. | TrkA KINASE INHIBITORS,COMPOSITIONS AND METHODS THEREOF |
| AU2015247817C1 (en) | 2014-04-14 | 2022-02-10 | Arvinas Operations, Inc. | Imide-based modulators of proteolysis and associated methods of use |
| EP3233840B1 (en) * | 2014-12-16 | 2018-11-21 | Eudendron S.r.l. | Heterocyclic derivatives modulating activity of certain protein kinases |
| CA2979070A1 (en) | 2015-03-18 | 2016-09-22 | Arvinas, Inc. | Compounds and methods for the enhanced degradation of targeted proteins |
| BR112018008918A8 (pt) * | 2015-11-02 | 2019-02-26 | Univ Yale | compostos de quimera proteólise dirigida e métodos para preparação e uso dos mesmos |
| WO2017197046A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | C3-carbon linked glutarimide degronimers for target protein degradation |
| WO2017197051A1 (en) * | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Amine-linked c3-glutarimide degronimers for target protein degradation |
| WO2017197055A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| KR102538307B1 (ko) * | 2017-12-13 | 2023-05-31 | 상하이테크 유니버시티 | Alk 단백질 분해제 및 암 치료에서의 이의 용도 |
| US11969472B2 (en) * | 2018-08-22 | 2024-04-30 | Cullgen (Shanghai), Inc. | Tropomyosin receptor kinase (TRK) degradation compounds and methods of use |
| JP2023514872A (ja) * | 2020-02-26 | 2023-04-11 | クルゲン（シャンハイ），インク． | トロポミオシン受容体キナーゼ（ｔｒｋ）分解化合物とその使用方法 |
-
2019
- 2019-08-21 CA CA3110267A patent/CA3110267A1/en active Pending
- 2019-08-21 EP EP19852808.5A patent/EP3841098A4/en active Pending
- 2019-08-21 KR KR1020217008232A patent/KR20210069634A/ko unknown
- 2019-08-21 CN CN202210693243.2A patent/CN115626927B/zh active Active
- 2019-08-21 MX MX2021001957A patent/MX2021001957A/es unknown
- 2019-08-21 BR BR112021003098-0A patent/BR112021003098A2/pt unknown
- 2019-08-21 US US17/269,670 patent/US20210363146A1/en active Pending
- 2019-08-21 AU AU2019323446A patent/AU2019323446A1/en active Pending
- 2019-08-21 WO PCT/CN2019/101850 patent/WO2020038415A1/en unknown
- 2019-08-21 CN CN201980067402.4A patent/CN112888681A/zh active Pending
- 2019-08-21 JP JP2021509151A patent/JP7472103B2/ja active Active
-
2021
- 2021-02-21 IL IL280984A patent/IL280984A/en unknown
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