JP2013518116A5 - - Google Patents
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- Publication number
- JP2013518116A5 JP2013518116A5 JP2012551271A JP2012551271A JP2013518116A5 JP 2013518116 A5 JP2013518116 A5 JP 2013518116A5 JP 2012551271 A JP2012551271 A JP 2012551271A JP 2012551271 A JP2012551271 A JP 2012551271A JP 2013518116 A5 JP2013518116 A5 JP 2013518116A5
- Authority
- JP
- Japan
- Prior art keywords
- protecting group
- hydroxyl protecting
- alkyl
- silyl
- oxygen atom
- 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 description 69
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 29
- -1 p-methoxybenzoyl Chemical group 0.000 claims description 22
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 10
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims description 10
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 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 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000006266 etherification reaction Methods 0.000 claims description 3
- 238000013467 fragmentation Methods 0.000 claims description 3
- 238000006062 fragmentation reaction Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- HNDXKIMMSFCCFW-UHFFFAOYSA-M propane-2-sulfonate Chemical compound CC(C)S([O-])(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-M 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 6
- UFNVPOGXISZXJD-JBQZKEIOSA-N eribulin Chemical compound C([C@H]1CC[C@@H]2O[C@@H]3[C@H]4O[C@@H]5C[C@](O[C@H]4[C@H]2O1)(O[C@@H]53)CC[C@@H]1O[C@H](C(C1)=C)CC1)C(=O)C[C@@H]2[C@@H](OC)[C@@H](C[C@H](O)CN)O[C@H]2C[C@@H]2C(=C)[C@H](C)C[C@H]1O2 UFNVPOGXISZXJD-JBQZKEIOSA-N 0.000 claims 5
- 229960003649 eribulin Drugs 0.000 claims 4
- 150000001241 acetals Chemical class 0.000 claims 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 229960000439 eribulin mesylate Drugs 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 description 7
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29833710P | 2010-01-26 | 2010-01-26 | |
| US61/298,337 | 2010-01-26 | ||
| PCT/US2011/022611 WO2011094339A1 (en) | 2010-01-26 | 2011-01-26 | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013518116A JP2013518116A (ja) | 2013-05-20 |
| JP2013518116A5 true JP2013518116A5 (enExample) | 2014-03-13 |
| JP5800834B2 JP5800834B2 (ja) | 2015-10-28 |
Family
ID=43726543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012551271A Active JP5800834B2 (ja) | 2010-01-26 | 2011-01-26 | ハリコンドリンｂ類似体の合成において有用なフロ［３，２−ｂ］ピラン誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (6) | US8203010B2 (enExample) |
| EP (1) | EP2528914B1 (enExample) |
| JP (1) | JP5800834B2 (enExample) |
| CN (1) | CN102803254B (enExample) |
| BR (1) | BR112012018232B8 (enExample) |
| CA (1) | CA2787919C (enExample) |
| IL (1) | IL220913A (enExample) |
| MX (1) | MX2012008510A (enExample) |
| RU (1) | RU2579511C2 (enExample) |
| SG (2) | SG182612A1 (enExample) |
| WO (1) | WO2011094339A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2755266C (en) * | 1998-06-17 | 2014-08-12 | Eisai R&D Management Co., Ltd. | Intermediates for preparing macrocyclic analogs |
| AU2005250487B2 (en) | 2004-06-03 | 2012-03-29 | Eisai R&D Management Co., Ltd | Intermediates for the preparation of analogs of halichondrin B |
| EP2200992B1 (en) | 2007-10-03 | 2014-02-26 | Eisai R&D Management Co., Ltd. | Intermediates and methods for the synthesis of halichondrin b analogs |
| JP6001857B2 (ja) * | 2008-04-04 | 2016-10-05 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂ類似体 |
| AU2010232347A1 (en) | 2009-03-30 | 2011-09-29 | Eisai R&D Management Co., Ltd. | Liposome composition |
| BR112012018232B8 (pt) | 2010-01-26 | 2023-01-10 | Eisai R&D Man Co Ltd | Compostos derivados de furo [3,2-b] pirano úteis na síntese de análogos de halicondrina b e métodos de sintetização de er-80402 e de eribulina |
| CN110097416B (zh) | 2011-09-18 | 2022-05-10 | 踏途音乐公司 | 具有卡拉ok和照相亭功能的数字点播设备及相关方法 |
| CA2892780A1 (en) | 2012-12-04 | 2014-06-12 | Eisai R&D Management Co., Ltd. | Use of eribulin in the treatment of breast cancer |
| AU2014299699B2 (en) | 2013-06-26 | 2019-10-10 | Eisai R&D Management Co., Ltd. | Use of eribulin and lenvatinib as combination therapy for treatment of cancer |
| WO2015000070A1 (en) | 2013-07-03 | 2015-01-08 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein including intermediates containing -so2-(p-tolyl) groups |
| CN103483352A (zh) * | 2013-10-18 | 2014-01-01 | 李友香 | 抗肿瘤的药用原料药 |
| RU2710545C2 (ru) | 2013-11-04 | 2019-12-27 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Реакции макроциклизации и промежуточные соединения и другие фрагменты, пригодные в получении аналогов халихондрина 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. |
| EP3148526B1 (en) | 2014-05-28 | 2021-01-06 | Eisai R&D Management Co., Ltd. | Use of eribulin in the treatment of cancer |
| JP2017520586A (ja) | 2014-06-30 | 2017-07-27 | 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 | ハリコンドリン類似体の合成およびその使用 |
| AU2015384801B2 (en) | 2015-03-04 | 2022-01-06 | Eisai R&D Management Co., Ltd. | Combination of a PD-1 antagonist and a VEGFR/FGFR/RET tyrosine kinase inhibitor for treating cancer |
| KR20170122810A (ko) | 2015-03-04 | 2017-11-06 | 머크 샤프 앤드 돔 코포레이션 | 암을 치료하기 위한 pd-1 길항제 및 에리불린의 조합 |
| US10344038B2 (en) | 2015-04-30 | 2019-07-09 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| RU2739034C2 (ru) * | 2015-05-07 | 2020-12-21 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Реакции макроциклизации и промежуточное соединение и другие фрагменты, полезные в синтезе макролидов галихондринов |
| KR20180107243A (ko) | 2016-02-12 | 2018-10-01 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 에리불린의 합성에서의 중간체 및 관련된 합성 방법 |
| RS62108B1 (sr) | 2016-03-02 | 2021-08-31 | Eisai R&D Man Co Ltd | Antitelo-lek konjugati na bazi eribulina i postupci primene |
| EP3449921B1 (en) | 2016-04-28 | 2023-05-31 | Eisai R&D Management Co., Ltd. | Eribulin 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 |
| MX2019003994A (es) | 2016-10-14 | 2019-09-19 | Merck Sharp & Dohme | Combinacion de un antagonista de proteina de muerte programada-1 (pd-1) y eribulina para el tratamiento de cancer 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 |
| CN108658956B (zh) * | 2017-03-28 | 2021-02-02 | 上海时莱生物技术有限公司 | 艾日布林中间体及其制备方法 |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| TWI863657B (zh) | 2017-04-05 | 2024-11-21 | 哈佛大學校長及研究員協會 | 巨環化合物及其用途 |
| CN108948064B (zh) * | 2017-05-17 | 2021-02-02 | 上海时莱生物技术有限公司 | 一种艾日布林中间体及其制备方法 |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
| CN118515685A (zh) | 2017-07-06 | 2024-08-20 | 哈佛大学的校长及成员们 | 软海绵素的合成 |
| US20190046513A1 (en) | 2017-08-10 | 2019-02-14 | Huya Bioscience International, Llc | Combination therapies of hdac inhibitors and tubulin inhibitors |
| EP4403560A3 (en) | 2017-11-15 | 2024-10-23 | President And Fellows Of Harvard College | Macrocyclic compounds and uses thereof |
| US11419856B2 (en) | 2017-11-20 | 2022-08-23 | Basilea Pharmaceutica International AG | Pharmaceutical combinations for use in the treatment of neoplastic diseases |
| EP3737673B1 (en) | 2018-01-03 | 2024-03-06 | Eisai R&D Management Co., Ltd. | Process for preparing halichondrin macrolides and analogs thereof by a prins reaction, and intermediates of this process |
| US12036204B2 (en) | 2019-07-26 | 2024-07-16 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
| US11083705B2 (en) | 2019-07-26 | 2021-08-10 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU652180A1 (ru) * | 1975-12-16 | 1979-03-15 | Краснодарский политехнический институт | 1(Фурил-2,)-2-(2-,, формилфурил-5,, ) этилен или его метильное производное как промежуточный продукт дл синтеза фуран-2,5-дикарбоновой кислоты и способ его получени |
| US5338865A (en) * | 1992-03-12 | 1994-08-16 | President And Fellows Of Harvard College | Synthesis of halichondrin B and norhalichondrin B |
| US5436238A (en) * | 1992-03-12 | 1995-07-25 | President And Fellows Of Harvard College | Halichondrins and related compounds |
| GB9206244D0 (en) | 1992-03-23 | 1992-05-06 | Pharma Mar Sa | Cytotoxic compound from a marine sponge |
| TW255880B (enExample) | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| US6194586B1 (en) | 1996-09-06 | 2001-02-27 | Eli Lilly And Company | Selective sulphonation of the primary alcohol of a diol containing both primary and secondary alcohols |
| US6653341B1 (en) * | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| CA2755266C (en) * | 1998-06-17 | 2014-08-12 | Eisai R&D Management Co., Ltd. | Intermediates for preparing macrocyclic analogs |
| CN109180615A (zh) * | 2004-06-03 | 2019-01-11 | 卫材R&D管理有限公司 | 用于制备软海绵素b的类似物的中间体 |
| AU2005250487B2 (en) | 2004-06-03 | 2012-03-29 | Eisai R&D Management Co., Ltd | Intermediates for the preparation of analogs of halichondrin B |
| US20060045846A1 (en) | 2004-08-30 | 2006-03-02 | Horstmann Thomas E | Reagents and methods for labeling terminal olefins |
| WO2006076100A2 (en) | 2004-12-09 | 2006-07-20 | Eisai Co. Ltd. | Tubulin isotype screening in cancer therapy using halichondrin b analogs |
| WO2008010776A1 (en) | 2006-07-21 | 2008-01-24 | Agency For Science, Technology And Research | Aigialomycin d and derivatives thereof and their use in treating cancer or malaria or a microbial infection |
| EP2200992B1 (en) | 2007-10-03 | 2014-02-26 | Eisai R&D Management Co., Ltd. | Intermediates and methods for the synthesis of halichondrin b analogs |
| CA2705383A1 (en) | 2007-11-16 | 2009-05-22 | Eisai R&D Management Co., Ltd. | Novel intermediate for halichondrin b analog synthesis and novel desulfonylation reaction used for the intermediate |
| JP6001857B2 (ja) | 2008-04-04 | 2016-10-05 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂ類似体 |
| BR112012018232B8 (pt) | 2010-01-26 | 2023-01-10 | Eisai R&D Man Co Ltd | Compostos derivados de furo [3,2-b] pirano úteis na síntese de análogos de halicondrina b e métodos de sintetização de er-80402 e de eribulina |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| WO2013078559A1 (en) | 2011-11-30 | 2013-06-06 | Alphora Research Inc. | Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene |
| WO2013142999A1 (en) | 2012-03-30 | 2013-10-03 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein |
| WO2015000070A1 (en) | 2013-07-03 | 2015-01-08 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein including intermediates containing -so2-(p-tolyl) groups |
| RU2710545C2 (ru) | 2013-11-04 | 2019-12-27 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Реакции макроциклизации и промежуточные соединения и другие фрагменты, пригодные в получении аналогов халихондрина 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. |
| RU2739034C2 (ru) | 2015-05-07 | 2020-12-21 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Реакции макроциклизации и промежуточное соединение и другие фрагменты, полезные в синтезе макролидов галихондринов |
| KR20180107243A (ko) | 2016-02-12 | 2018-10-01 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 에리불린의 합성에서의 중간체 및 관련된 합성 방법 |
| 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 |
-
2011
- 2011-01-26 BR BR112012018232A patent/BR112012018232B8/pt active IP Right Grant
- 2011-01-26 SG SG2012053468A patent/SG182612A1/en unknown
- 2011-01-26 JP JP2012551271A patent/JP5800834B2/ja active Active
- 2011-01-26 MX MX2012008510A patent/MX2012008510A/es unknown
- 2011-01-26 CA CA2787919A patent/CA2787919C/en active Active
- 2011-01-26 EP EP11702900.9A patent/EP2528914B1/en active Active
- 2011-01-26 SG SG10201500552PA patent/SG10201500552PA/en unknown
- 2011-01-26 RU RU2012136468/04A patent/RU2579511C2/ru active
- 2011-01-26 US US13/014,517 patent/US8203010B2/en active Active
- 2011-01-26 WO PCT/US2011/022611 patent/WO2011094339A1/en not_active Ceased
- 2011-01-26 CN CN201180015757.2A patent/CN102803254B/zh active Active
-
2012
- 2012-05-22 US US13/477,483 patent/US8350067B2/en active Active
- 2012-07-12 IL IL220913A patent/IL220913A/en active IP Right Grant
-
2013
- 2013-01-07 US US13/735,516 patent/US8927597B2/en active Active
-
2014
- 2014-12-19 US US14/577,417 patent/US9382262B2/en active Active
-
2016
- 2016-06-29 US US15/196,600 patent/US9856276B2/en active Active
-
2017
- 2017-12-13 US US15/840,109 patent/US10494388B2/en active Active
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