JPWO2020243379A5 - - Google Patents
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- Publication number
- JPWO2020243379A5 JPWO2020243379A5 JP2021570866A JP2021570866A JPWO2020243379A5 JP WO2020243379 A5 JPWO2020243379 A5 JP WO2020243379A5 JP 2021570866 A JP2021570866 A JP 2021570866A JP 2021570866 A JP2021570866 A JP 2021570866A JP WO2020243379 A5 JPWO2020243379 A5 JP WO2020243379A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- dioxopiperidin
- oxo
- isoindoline
- trifluoro
- 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 67
- DZACPFIVEGYGNL-UHFFFAOYSA-N 2,3-dihydro-1h-isoindole-5-carboxamide Chemical compound NC(=O)C1=CC=C2CNCC2=C1 DZACPFIVEGYGNL-UHFFFAOYSA-N 0.000 claims 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 40
- 150000003839 salts Chemical class 0.000 claims 33
- 238000000034 method Methods 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 19
- -1 CH2CHF2 Chemical group 0.000 claims 17
- 239000002904 solvent Substances 0.000 claims 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 229910052794 bromium Inorganic materials 0.000 claims 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052740 iodine Inorganic materials 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 5
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 3
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- NPWMTBZSRRLQNJ-UHFFFAOYSA-N pyroglutamine Chemical compound NC1CCC(=O)NC1=O NPWMTBZSRRLQNJ-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 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 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000005936 piperidyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical group C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- LOLDZHDQFVBJTM-PQJIZZRHSA-N C(#N)C([C@H](C(F)(F)F)NC(=O)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(C)C Chemical compound C(#N)C([C@H](C(F)(F)F)NC(=O)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(C)C LOLDZHDQFVBJTM-PQJIZZRHSA-N 0.000 claims 1
- PMDYMDRUXRCPFG-BSOCMFCZSA-N C(#N)C1=C(C=CC=C1)[C@@H](C)NC(=O)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O Chemical compound C(#N)C1=C(C=CC=C1)[C@@H](C)NC(=O)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O PMDYMDRUXRCPFG-BSOCMFCZSA-N 0.000 claims 1
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- ALSLTCWJZQZJBM-FBLFFUNLSA-N C1(CC1)OC1=C(C=CC=C1)[C@H](C(F)(F)F)NC(=O)C=1C(=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)F Chemical compound C1(CC1)OC1=C(C=CC=C1)[C@H](C(F)(F)F)NC(=O)C=1C(=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)F ALSLTCWJZQZJBM-FBLFFUNLSA-N 0.000 claims 1
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- ZCGJWKRNCCRNCC-BDPMCISCSA-N C1(CC1)OC1=CC=C(C=C1)[C@H](C(F)(F)F)NC(=O)C=1C(=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)F Chemical compound C1(CC1)OC1=CC=C(C=C1)[C@H](C(F)(F)F)NC(=O)C=1C(=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)F ZCGJWKRNCCRNCC-BDPMCISCSA-N 0.000 claims 1
- KTDRIAWNJDERGM-VGAJERRHSA-N C1(CC1)OC1=CC=C(C=C1)[C@H](C(F)(F)F)NC(=O)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O Chemical compound C1(CC1)OC1=CC=C(C=C1)[C@H](C(F)(F)F)NC(=O)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KTDRIAWNJDERGM-VGAJERRHSA-N 0.000 claims 1
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| WO2020243379A1 (en) | 2019-05-31 | 2020-12-03 | Celgene Corporation | Substituted 1-oxo-isoindoline-5-carboxamide compounds, compositions thereof, and methods of treatment therewith |
| IL302038A (en) * | 2020-10-14 | 2023-06-01 | C4 Therapeutics Inc | Tricyclic ligands for degradation of ikzf2 or ikzf4 |
| CN112679421A (zh) * | 2021-01-04 | 2021-04-20 | 都创(上海)医药科技股份有限公司 | 一种(r)-3-氯吡啶基-2-三氟乙胺盐酸盐的合成方法 |
| JP2024504932A (ja) | 2021-01-13 | 2024-02-02 | モンテ ローザ セラピューティクス， インコーポレイテッド | イソインドリノン化合物 |
| CN118019534A (zh) * | 2021-05-06 | 2024-05-10 | 细胞基因公司 | 使用n-((r)-1-(3-氯吡啶-2-基)-2,2,2-三氟乙基)-2-((s)-2,6-二氧代哌啶-3-基)-1-氧代异吲哚啉-5-甲酰胺的治疗方法 |
| US20240294500A1 (en) * | 2021-06-08 | 2024-09-05 | Hangzhou Glubio Pharmaceutical Co., Ltd. | Isoindolinone compounds, and uses thereof |
| CN115504963A (zh) * | 2021-06-22 | 2022-12-23 | 苏州开拓药业股份有限公司 | 一种c-Myc蛋白降解剂 |
| EP4452415B1 (en) | 2021-12-22 | 2026-02-25 | Gilead Sciences, Inc. | Ikaros zinc finger family degraders and uses thereof |
| CA3253296A1 (en) | 2022-03-17 | 2023-09-21 | Gilead Sciences, Inc. | Zinc Finger Degradation Agents of the Ikaros Family and Their Uses |
| WO2023244815A1 (en) * | 2022-06-16 | 2023-12-21 | Monte Rosa Therapeutics, Inc. | Molecular glue degraders and methods of using the same |
| WO2023244818A1 (en) * | 2022-06-16 | 2023-12-21 | Monte Rosa Therapeutics, Inc. | Molecular glue degraders and methods of using the same |
| US20260055077A1 (en) * | 2022-08-01 | 2026-02-26 | Suzhou Kintor Pharmaceuticals, Inc. | Protein degradation agent |
| WO2024120441A1 (zh) * | 2022-12-07 | 2024-06-13 | 杭州格博生物医药有限公司 | 氧异吲哚-5-甲酰胺类化合物或其盐、溶剂合物的结晶形式或无定形形式 |
| WO2024120438A1 (zh) * | 2022-12-07 | 2024-06-13 | 杭州格博生物医药有限公司 | 一种固体分散体、其制备方法和应用 |
| PL249026B1 (pl) * | 2022-12-09 | 2026-02-23 | Univ Mikolaja Kopernika W Toruniu | Pochodna azetydyno-2,4-dionu, sposób jej otrzymywania i zastosowanie |
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| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US7091353B2 (en) * | 2000-12-27 | 2006-08-15 | Celgene Corporation | Isoindole-imide compounds, compositions, and uses thereof |
| KR20080042158A (ko) * | 2005-08-31 | 2008-05-14 | 셀진 코포레이션 | 이소인돌-이미드 화합물과 이를 포함하는 조성물 및 이를이용한 방법 |
| MX2009001989A (es) | 2006-08-30 | 2009-03-09 | Celgene Corp | Compuestos de isoindolina 5-substituidos. |
| US8877780B2 (en) * | 2006-08-30 | 2014-11-04 | Celgene Corporation | 5-substituted isoindoline compounds |
| ZA200901078B (en) * | 2006-08-30 | 2010-06-30 | Celgene Corp | 5-substituted isoindoline compounds |
| US9499514B2 (en) * | 2014-07-11 | 2016-11-22 | Celgene Corporation | Antiproliferative compounds and methods of use thereof |
| WO2017007612A1 (en) | 2015-07-07 | 2017-01-12 | Dana-Farber Cancer Institute, Inc. | Methods to induce targeted protein degradation through bifunctional molecules |
| WO2017024318A1 (en) * | 2015-08-06 | 2017-02-09 | Dana-Farber Cancer Institute, Inc. | Targeted protein degradation to attenuate adoptive t-cell therapy associated adverse inflammatory responses |
| WO2017024317A2 (en) * | 2015-08-06 | 2017-02-09 | Dana-Farber Cancer Institute, Inc. | Methods to induce targeted protein degradation through bifunctional molecules |
| WO2020243379A1 (en) | 2019-05-31 | 2020-12-03 | Celgene Corporation | Substituted 1-oxo-isoindoline-5-carboxamide compounds, compositions thereof, and methods of treatment therewith |
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2020
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2022
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