JPWO2020132014A5 - - Google Patents
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- Publication number
- JPWO2020132014A5 JPWO2020132014A5 JP2021535539A JP2021535539A JPWO2020132014A5 JP WO2020132014 A5 JPWO2020132014 A5 JP WO2020132014A5 JP 2021535539 A JP2021535539 A JP 2021535539A JP 2021535539 A JP2021535539 A JP 2021535539A JP WO2020132014 A5 JPWO2020132014 A5 JP WO2020132014A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- ethyl
- dioxopiperidin
- oxo
- trifluoromethyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 206010060862 Prostate cancer Diseases 0.000 claims 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- YUVGVJYLOFTILT-NHYGQJMQSA-N 2-[(2R)-4-[2-[4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-ethylphenoxy]ethyl]-2-methylpiperazin-1-yl]-N-[3-[(2,6-dioxopiperidin-3-yl)amino]phenyl]acetamide Chemical compound C(#N)C1=C(C=C(C=C1)N1C(N(C(C1=O)(C)C)C1=CC(=C(OCCN2C[C@H](N(CC2)CC(=O)NC2=CC(=CC=C2)NC2C(NC(CC2)=O)=O)C)C=C1)CC)=S)C(F)(F)F YUVGVJYLOFTILT-NHYGQJMQSA-N 0.000 claims 3
- YUVGVJYLOFTILT-CPMFFWQLSA-N 2-[(2S)-4-[2-[4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-ethylphenoxy]ethyl]-2-methylpiperazin-1-yl]-N-[3-[(2,6-dioxopiperidin-3-yl)amino]phenyl]acetamide Chemical compound C(#N)C1=C(C=C(C=C1)N1C(N(C(C1=O)(C)C)C1=CC(=C(OCCN2C[C@@H](N(CC2)CC(=O)NC2=CC(=CC=C2)NC2C(NC(CC2)=O)=O)C)C=C1)CC)=S)C(F)(F)F YUVGVJYLOFTILT-CPMFFWQLSA-N 0.000 claims 3
- XJQGVJYVEKFXBT-CPMFFWQLSA-N 2-[(3S)-4-[2-[4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-ethylphenoxy]ethyl]-3-methylpiperazin-1-yl]-N-[3-[(2,6-dioxopiperidin-3-yl)amino]phenyl]acetamide Chemical compound C(#N)C1=C(C=C(C=C1)N1C(N(C(C1=O)(C)C)C1=CC(=C(OCCN2[C@H](CN(CC2)CC(=O)NC2=CC(=CC=C2)NC2C(NC(CC2)=O)=O)C)C=C1)CC)=S)C(F)(F)F XJQGVJYVEKFXBT-CPMFFWQLSA-N 0.000 claims 3
- RVVZDTSLXUHQIZ-YTTGMZPUSA-N C(#N)C1=C(C=C(C=C1)N1C(N(C(C1=O)(C)C)C1=CC(=C(OCCN2CCN(CC2)CC(=O)NC2=CC(=CC=C2)N[C@@H]2C(NC(CC2)=O)=O)C=C1)CC)=S)C(F)(F)F Chemical compound C(#N)C1=C(C=C(C=C1)N1C(N(C(C1=O)(C)C)C1=CC(=C(OCCN2CCN(CC2)CC(=O)NC2=CC(=CC=C2)N[C@@H]2C(NC(CC2)=O)=O)C=C1)CC)=S)C(F)(F)F RVVZDTSLXUHQIZ-YTTGMZPUSA-N 0.000 claims 3
- 239000003098 androgen Substances 0.000 claims 2
- 102000001307 androgen receptors Human genes 0.000 claims 2
- 108010080146 androgen receptors Proteins 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 239000003981 vehicle Substances 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- -1 (2,6-dioxopiperidin-3-yl)amino Chemical group 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- IRJRGQDMZQWBTL-GOSISDBHSA-N tert-butyl (2R)-4-[2-[2-(2,2-difluoroethyl)-4-[(1-ethoxy-2-methyl-1-oxopropan-2-yl)amino]phenoxy]ethyl]-2-methylpiperazine-1-carboxylate Chemical compound FC(CC1=C(OCCN2C[C@H](N(CC2)C(=O)OC(C)(C)C)C)C=CC(=C1)NC(C(=O)OCC)(C)C)F IRJRGQDMZQWBTL-GOSISDBHSA-N 0.000 description 1
- BRXFTKZBVNOXML-CQSZACIVSA-N tert-butyl (2R)-4-[2-[4-amino-2-(2,2-difluoroethyl)phenoxy]ethyl]-2-methylpiperazine-1-carboxylate Chemical compound NC1=CC(=C(OCCN2C[C@H](N(CC2)C(=O)OC(C)(C)C)C)C=C1)CC(F)F BRXFTKZBVNOXML-CQSZACIVSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024083009A JP7724911B2 (ja) | 2018-12-19 | 2024-05-22 | 置換３－（（３－アミノフェニル）アミノ）ピペリジン－２，６－ジオン化合物、その組成物、及びそれを用いた治療方法 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862782298P | 2018-12-19 | 2018-12-19 | |
| US62/782,298 | 2018-12-19 | ||
| US201962879900P | 2019-07-29 | 2019-07-29 | |
| US62/879,900 | 2019-07-29 | ||
| PCT/US2019/067088 WO2020132014A1 (en) | 2018-12-19 | 2019-12-18 | Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024083009A Division JP7724911B2 (ja) | 2018-12-19 | 2024-05-22 | 置換３－（（３－アミノフェニル）アミノ）ピペリジン－２，６－ジオン化合物、その組成物、及びそれを用いた治療方法 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2022514344A JP2022514344A (ja) | 2022-02-10 |
| JPWO2020132014A5 true JPWO2020132014A5 (https=) | 2023-01-20 |
| JP2022514344A5 JP2022514344A5 (https=) | 2023-01-20 |
| JP7494181B2 JP7494181B2 (ja) | 2024-06-03 |
Family
ID=71098067
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021535539A Active JP7494181B2 (ja) | 2018-12-19 | 2019-12-18 | 置換３－（（３－アミノフェニル）アミノ）ピペリジン－２，６－ジオン化合物、その組成物、及びそれを用いた治療方法 |
| JP2024083009A Active JP7724911B2 (ja) | 2018-12-19 | 2024-05-22 | 置換３－（（３－アミノフェニル）アミノ）ピペリジン－２，６－ジオン化合物、その組成物、及びそれを用いた治療方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024083009A Active JP7724911B2 (ja) | 2018-12-19 | 2024-05-22 | 置換３－（（３－アミノフェニル）アミノ）ピペリジン－２，６－ジオン化合物、その組成物、及びそれを用いた治療方法 |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US11149007B2 (https=) |
| EP (2) | EP4494711A3 (https=) |
| JP (2) | JP7494181B2 (https=) |
| KR (2) | KR20250144505A (https=) |
| CN (2) | CN113453681B (https=) |
| AU (1) | AU2019403207B2 (https=) |
| BR (1) | BR112021011968A2 (https=) |
| CA (1) | CA3124130A1 (https=) |
| CL (1) | CL2021001665A1 (https=) |
| CO (1) | CO2021007973A2 (https=) |
| DK (1) | DK3897636T3 (https=) |
| ES (1) | ES3009308T3 (https=) |
| FI (1) | FI3897636T3 (https=) |
| HR (1) | HRP20250095T1 (https=) |
| HU (1) | HUE070506T2 (https=) |
| IL (1) | IL284223B2 (https=) |
| LT (1) | LT3897636T (https=) |
| MX (1) | MX2021007473A (https=) |
| MY (1) | MY205718A (https=) |
| PE (1) | PE20212247A1 (https=) |
| PL (1) | PL3897636T3 (https=) |
| PT (1) | PT3897636T (https=) |
| RS (1) | RS66556B1 (https=) |
| SG (1) | SG11202106507RA (https=) |
| SI (1) | SI3897636T1 (https=) |
| SM (1) | SMT202500111T1 (https=) |
| TW (1) | TWI820276B (https=) |
| WO (1) | WO2020132014A1 (https=) |
| ZA (1) | ZA202104200B (https=) |
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| PL3897636T3 (pl) * | 2018-12-19 | 2025-04-28 | Celgene Corporation | Podstawione związki 3-((3-aminofenylo)amino)piperydyno-2,6-dionu, ich kompozycje i sposoby leczenia nimi |
| US11325889B2 (en) * | 2018-12-19 | 2022-05-10 | Celgene Corporation | Substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds, compositions thereof, and methods of treatment therewith |
| CA3165168A1 (en) | 2019-12-19 | 2021-06-24 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| CN115996918A (zh) | 2020-05-09 | 2023-04-21 | 阿尔维纳斯运营股份有限公司 | 制造双官能团化合物的方法、双官能团化合物的超纯形式以及包括所述双官能团化合物的剂型 |
| JP7778095B2 (ja) | 2020-06-24 | 2025-12-01 | セルジーン コーポレーション | セレブロン結合化合物、その組成物及びそれによる治療方法 |
| PE20231746A1 (es) * | 2020-06-24 | 2023-11-06 | Celgene Corp | Compuestos de union a cereblon, composiciones de estos y metodos de tratamiento con estos |
| KR20230027214A (ko) | 2020-06-24 | 2023-02-27 | 셀진 코포레이션 | 세레블론 결합 화합물, 이의 조성물, 및 이에 의한 치료 방법 |
| WO2022019597A1 (ko) * | 2020-07-21 | 2022-01-27 | 주식회사 유빅스테라퓨틱스 | 안드로겐 수용체 분해용 화합물 및 이들의 의약 용도 |
| WO2022061348A1 (en) | 2020-09-16 | 2022-03-24 | Biotheryx, Inc. | Sos1 protein degraders, pharmaceutical compositions thereof, and their therapeutic applications |
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| TW202237580A (zh) | 2020-12-14 | 2022-10-01 | 美商拜歐斯瑞克斯公司 | Pde4降解劑、醫藥組合物及治療應用 |
| TWI807697B (zh) * | 2021-03-17 | 2023-07-01 | 大陸商南京明德新藥研發有限公司 | 呋喃稠環取代的戊二醯亞胺類化合物 |
| EP4359407A4 (en) * | 2021-06-25 | 2025-04-30 | Celgene Corporation | CEREBLON-BINDING COMPOUNDS, COMPOSITIONS THEREOF AND METHODS OF TREATMENT USING THEM |
| EP4359404A4 (en) * | 2021-06-25 | 2025-06-04 | Celgene Corporation | Cereblon-binding compounds, compositions thereof and methods of treatment therewith |
| JP2024526192A (ja) * | 2021-06-25 | 2024-07-17 | セルジーン コーポレーション | セレブロン結合化合物、その組成物及びそれによる治療方法 |
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| WO2024102706A1 (en) * | 2022-11-09 | 2024-05-16 | Bristol-Myers Squibb Company | Combination therapy with substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds |
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| US20250346577A1 (en) * | 2024-05-07 | 2025-11-13 | Bristol-Myers Squibb Company | Processes for the preparation of substituted 3-((3-aminophenyl)amino)piperidine-2,6-dione compounds |
| WO2025235577A1 (en) * | 2024-05-09 | 2025-11-13 | Bristol-Myers Squibb Company | Forms and formulations of substituted 3-((3-amino)piperidine-2,6-dione compounds |
| CN118993935B (zh) * | 2024-10-23 | 2025-02-14 | 江苏恒瑞医药股份有限公司 | 咪唑啉衍生物或其盐的制备方法 |
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