JP2010540658A5 - - Google Patents
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- JP2010540658A5 JP2010540658A5 JP2010528165A JP2010528165A JP2010540658A5 JP 2010540658 A5 JP2010540658 A5 JP 2010540658A5 JP 2010528165 A JP2010528165 A JP 2010528165A JP 2010528165 A JP2010528165 A JP 2010528165A JP 2010540658 A5 JP2010540658 A5 JP 2010540658A5
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- Japan
- Prior art keywords
- compound
- alkyl
- formula
- protecting group
- group
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 67
- 238000000034 method Methods 0.000 claims 49
- 125000006239 protecting group Chemical group 0.000 claims 39
- 125000000217 alkyl group Chemical group 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- -1 triethylsilyl Chemical group 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 9
- 150000001241 acetals Chemical class 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 8
- 150000005676 cyclic carbonates Chemical class 0.000 claims 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims 6
- 150000004820 halides Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000005907 alkyl ester group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 4
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 4
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- DBASDGQROJIJMT-UHFFFAOYSA-N 2-benzylidenepyran Chemical compound O1C=CC=CC1=CC1=CC=CC=C1 DBASDGQROJIJMT-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 239000012296 anti-solvent Substances 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims 2
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 claims 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99762507P | 2007-10-03 | 2007-10-03 | |
| US60/997,625 | 2007-10-03 | ||
| PCT/US2008/078762 WO2009046308A1 (en) | 2007-10-03 | 2008-10-03 | Intermediates and methods for the synthesis of halichondrin b analogs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010540658A JP2010540658A (ja) | 2010-12-24 |
| JP2010540658A5 true JP2010540658A5 (https=) | 2011-12-15 |
| JP5735277B2 JP5735277B2 (ja) | 2015-06-17 |
Family
ID=40019255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010528165A Active JP5735277B2 (ja) | 2007-10-03 | 2008-10-03 | ハリコンドリンｂ類似体の合成のための中間体および方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (6) | US8093410B2 (https=) |
| EP (2) | EP2578576B9 (https=) |
| JP (1) | JP5735277B2 (https=) |
| CN (3) | CN101883763B (https=) |
| BR (1) | BRPI0817909B1 (https=) |
| CA (1) | CA2701534C (https=) |
| IL (1) | IL204791A (https=) |
| MX (1) | MX2010003599A (https=) |
| RU (1) | RU2489437C2 (https=) |
| SG (1) | SG10201811715YA (https=) |
| WO (1) | WO2009046308A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2682878B2 (ja) | 1989-11-27 | 1997-11-26 | 上村工業株式会社 | シールド付き電気めっき装置 |
| US6214865B1 (en) * | 1998-06-17 | 2001-04-10 | Eisai Co., Ltd. | Macrocyclic analogs and methods of their use and preparation |
| EP2522663B1 (en) | 2004-06-03 | 2015-04-01 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of halichondrin B |
| RU2489437C2 (ru) | 2007-10-03 | 2013-08-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Промежуточные соединения и способы синтеза аналогов галихондрина в |
| CN105801599A (zh) | 2008-04-04 | 2016-07-27 | 卫材R&D管理有限公司 | 软海绵素b类似物 |
| DE102009012660A1 (de) * | 2009-03-13 | 2010-09-16 | H.C. Starck Clevios Gmbh | Polymerbeschichtungen mit verbesserter Temperaturstabilität |
| ES2593027T3 (es) | 2009-03-30 | 2016-12-05 | Eisai R&D Management Co., Ltd. | Composición liposomal |
| WO2011094339A1 (en) | 2010-01-26 | 2011-08-04 | Eisai R&D Management Co., Ltd. | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
| CN102225921B (zh) * | 2011-04-26 | 2013-04-24 | 中国人民解放军第二军医大学 | 一种环戊烷聚酮类化合物simplextone A及其用途 |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| MX2015007185A (es) | 2012-12-04 | 2017-09-05 | Eisai R&D Man Co Ltd | Uso de eribulina en el tratamiento de cancer de pecho. |
| KR102265952B1 (ko) | 2013-06-26 | 2021-06-16 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 암 치료 병용요법으로서 에리불린 및 렌바티닙의 용도 |
| EP3689881B1 (en) | 2013-11-04 | 2022-01-12 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b |
| MX384292B (es) | 2013-12-06 | 2025-03-14 | Eisai R&D Man Co Ltd | Metodos utiles en la sintesis de analogos de halicondrina b. |
| RU2699545C2 (ru) | 2014-05-28 | 2019-09-06 | ЭЙСАЙ Ар ЭНД Ди МЕНЕДЖМЕНТ КО., ЛТД | Применение эрибулина в лечении рака |
| US10556910B2 (en) | 2014-06-30 | 2020-02-11 | President And Fellows Of Harvard College | Synthesis of halichondrin analogs and uses thereof |
| WO2016038624A1 (en) * | 2014-09-09 | 2016-03-17 | Cipla Limited | "process for the preparation of macrocyclic ketone analogs of halichondrin b or pharmaceutically acceptable salts and intermediates thereof" |
| KR102662228B1 (ko) | 2015-03-04 | 2024-05-02 | 머크 샤프 앤드 돔 코포레이션 | 암을 치료하기 위한 pd-1 길항제 및 vegfr/fgfr/ret 티로신 키나제 억제제의 조합 |
| CA2978311A1 (en) | 2015-03-04 | 2016-09-09 | Merck Sharp & Dohme Corp. | Combination of a pd-1 antagonist and eribulin for treating cancer |
| US10344038B2 (en) | 2015-04-30 | 2019-07-09 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| KR102743950B1 (ko) | 2015-05-07 | 2024-12-18 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 할리콘드린 마크롤라이드의 합성에 유용한 마크로고리화 반응 및 중간체 및 기타 단편 |
| EP3413887B1 (en) * | 2016-02-12 | 2021-04-07 | Eisai R&D Management Co., Ltd. | Intermediates in the synthesis of eribulin and related methods of synthesis |
| EP3423105B1 (en) | 2016-03-02 | 2021-05-05 | Eisai R&D Management Co., Ltd. | Eribulin-based antibody-drug conjugates and methods of use |
| US12029724B2 (en) | 2016-04-28 | 2024-07-09 | Eisai R&D Management Co., Ltd. | Method for inhibiting tumor growth |
| US11136335B2 (en) * | 2016-06-30 | 2021-10-05 | Eisai R&D Management Co., Ltd. | Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof |
| BR112019007145A2 (pt) | 2016-10-14 | 2019-07-02 | Eisai R&D Man Co Ltd | combinação de um antagonista de pd-1 e eribulina para o tratamento de câncer urotelial |
| JP6978758B2 (ja) | 2016-11-11 | 2021-12-08 | プレジデント アンド フェローズ オブ ハーバード カレッジ | パラジウム媒介ケトール化 |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| ES2931533T3 (es) | 2017-04-05 | 2022-12-30 | Harvard College | Compuesto macrocíclico y usos del mismo |
| HUE061306T2 (hu) * | 2017-07-06 | 2023-06-28 | Harvard College | Halikondrinok szintézise |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
| US20190046513A1 (en) | 2017-08-10 | 2019-02-14 | Huya Bioscience International, Llc | Combination therapies of hdac inhibitors and tubulin inhibitors |
| CN111566113B (zh) | 2017-11-15 | 2024-01-09 | 哈佛大学的校长及成员们 | 大环化合物及其用途 |
| US11419856B2 (en) | 2017-11-20 | 2022-08-23 | Basilea Pharmaceutica International AG | Pharmaceutical combinations for use in the treatment of neoplastic diseases |
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| US11447499B2 (en) | 2019-06-14 | 2022-09-20 | Rk Pharma Inc. | Process for the preparation of eribulin mesylate intermediate |
| JP7574232B2 (ja) | 2019-06-21 | 2024-10-28 | カウンスィル オブ サイエンティフィック アンド インダストリアル リサーチ | ホモプロパルギルアルコールを調製するための化学酵素的プロセス |
| US11083705B2 (en) | 2019-07-26 | 2021-08-10 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
| US12036204B2 (en) | 2019-07-26 | 2024-07-16 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
| CN110981903A (zh) * | 2019-11-28 | 2020-04-10 | 南京正济医药研究有限公司 | 一种艾日布林中间体化合物提高光学纯度的精制方法 |
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| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
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| EP3689881B1 (en) | 2013-11-04 | 2022-01-12 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b |
| MX384292B (es) | 2013-12-06 | 2025-03-14 | Eisai R&D Man Co Ltd | Metodos utiles en la sintesis de analogos de halicondrina b. |
| WO2016038624A1 (en) | 2014-09-09 | 2016-03-17 | Cipla Limited | "process for the preparation of macrocyclic ketone analogs of halichondrin b or pharmaceutically acceptable salts and intermediates thereof" |
| KR102743950B1 (ko) | 2015-05-07 | 2024-12-18 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 할리콘드린 마크롤라이드의 합성에 유용한 마크로고리화 반응 및 중간체 및 기타 단편 |
| EP3413887B1 (en) | 2016-02-12 | 2021-04-07 | Eisai R&D Management Co., Ltd. | Intermediates in the synthesis of eribulin and related methods of synthesis |
| US11136335B2 (en) | 2016-06-30 | 2021-10-05 | Eisai R&D Management Co., Ltd. | Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof |
| WO2018217894A1 (en) | 2017-05-24 | 2018-11-29 | Eisai R&D Management Co., Ltd. | Fluorine-labelled halichondrin derivatives and related methods of synthesis |
| SG11202005548WA (en) | 2018-01-03 | 2020-07-29 | Eisai R&D Man Co Ltd | Prins reaction and compounds useful in the synthesis of halichondrin macrolides and analogs thereof |
-
2008
- 2008-10-03 RU RU2010117520/04A patent/RU2489437C2/ru active
- 2008-10-03 CN CN200880119686.9A patent/CN101883763B/zh active Active
- 2008-10-03 CA CA2701534A patent/CA2701534C/en active Active
- 2008-10-03 SG SG10201811715YA patent/SG10201811715YA/en unknown
- 2008-10-03 EP EP12191294.3A patent/EP2578576B9/en active Active
- 2008-10-03 WO PCT/US2008/078762 patent/WO2009046308A1/en not_active Ceased
- 2008-10-03 MX MX2010003599A patent/MX2010003599A/es unknown
- 2008-10-03 CN CN201410421907.5A patent/CN104311571B/zh active Active
- 2008-10-03 CN CN201810736587.0A patent/CN108948039B/zh active Active
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