JP2018516885A5 - - Google Patents
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- JP2018516885A5 JP2018516885A5 JP2017558008A JP2017558008A JP2018516885A5 JP 2018516885 A5 JP2018516885 A5 JP 2018516885A5 JP 2017558008 A JP2017558008 A JP 2017558008A JP 2017558008 A JP2017558008 A JP 2017558008A JP 2018516885 A5 JP2018516885 A5 JP 2018516885A5
- Authority
- JP
- Japan
- Prior art keywords
- protecting group
- formula
- hydroxyl protecting
- independently
- compound
- 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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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 82
- 150000001875 compounds Chemical class 0.000 claims 65
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 238000000034 method Methods 0.000 claims 31
- 150000003839 salts Chemical class 0.000 claims 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims 24
- 239000003120 macrolide antibiotic agent Substances 0.000 claims 17
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 16
- 125000004429 atom Chemical group 0.000 claims 14
- 229930195695 Halichondrin Natural products 0.000 claims 13
- 239000000543 intermediate Substances 0.000 claims 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 8
- 239000005977 Ethylene Substances 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000001540 azides Chemical class 0.000 claims 8
- 230000015572 biosynthetic process Effects 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 150000005676 cyclic carbonates Chemical class 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000003106 haloaryl group Chemical group 0.000 claims 8
- 125000002034 haloarylalkyl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 150000002430 hydrocarbons Chemical group 0.000 claims 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 8
- 125000005027 hydroxyaryl group Chemical group 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 8
- 238000005865 alkene metathesis reaction Methods 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- 238000003786 synthesis reaction Methods 0.000 claims 6
- 150000005215 alkyl ethers Chemical class 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000007848 Bronsted acid Substances 0.000 claims 3
- 238000005710 macrocyclization reaction Methods 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 0 *C(*)CCCN Chemical compound *C(*)CCCN 0.000 description 6
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562158506P | 2015-05-07 | 2015-05-07 | |
| US62/158,506 | 2015-05-07 | ||
| US201662291918P | 2016-02-05 | 2016-02-05 | |
| US62/291,918 | 2016-02-05 | ||
| PCT/US2016/031546 WO2016179607A1 (en) | 2015-05-07 | 2016-05-09 | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018516885A JP2018516885A (ja) | 2018-06-28 |
| JP2018516885A5 true JP2018516885A5 (OSRAM) | 2019-06-13 |
| JP6840090B2 JP6840090B2 (ja) | 2021-03-10 |
Family
ID=57218352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017558008A Active JP6840090B2 (ja) | 2015-05-07 | 2016-05-09 | ハリコンドリンマクロライドの合成に有用な大環状化反応および中間体および他のフラグメント |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US10308661B2 (OSRAM) |
| EP (1) | EP3292130B1 (OSRAM) |
| JP (1) | JP6840090B2 (OSRAM) |
| KR (2) | KR102743950B1 (OSRAM) |
| CN (3) | CN117024469A (OSRAM) |
| IL (2) | IL255408B (OSRAM) |
| MX (2) | MX380284B (OSRAM) |
| RU (2) | RU2739034C2 (OSRAM) |
| WO (1) | WO2016179607A1 (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP5800834B2 (ja) | 2010-01-26 | 2015-10-28 | 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類似体の合成において有用なフロ［３，２−ｂ］ピラン誘導体 |
| CN114716453A (zh) | 2013-11-04 | 2022-07-08 | 卫材R&D管理有限公司 | 软海绵素b的类似物合成中有用的大环化反应和中间体 |
| JP6443812B2 (ja) | 2013-12-06 | 2018-12-26 | 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類縁体の合成に有用な方法 |
| 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 |
| WO2016176560A1 (en) | 2015-04-30 | 2016-11-03 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| WO2016179607A1 (en) | 2015-05-07 | 2016-11-10 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides |
| MX377663B (es) | 2016-02-12 | 2025-03-11 | Eisai R&D Man Co Ltd | Intermediarios en la sintesis de eribulina y metodos de sintesis relacionados. |
| MX390072B (es) | 2016-06-30 | 2025-03-20 | Eisai R&D Man Co Ltd | Reaccion de prins e intermediarios utiles en la sintesis de macrolidos de halicondrina y analogos de los mismos. |
| 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 |
| HUE060466T2 (hu) | 2017-04-05 | 2023-03-28 | Harvard College | Makrociklusos vegyület és alkalmazása |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| BR112020000141A2 (pt) | 2017-07-06 | 2020-07-14 | President And Fellows Of Harvard College | síntese de halicondrinas |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
| ES2974243T3 (es) | 2017-11-15 | 2024-06-26 | Harvard College | Compuestos macrocíclicos y usos de los mismos |
| CN111868044B (zh) * | 2018-01-03 | 2024-07-19 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯及其类似物的普林斯反应和化合物 |
| CN115583875B (zh) * | 2022-09-28 | 2023-12-01 | 联化科技（台州）有限公司 | 在连续流反应器中将烯丙型醇氧化为α,β-不饱和醛酮的方法 |
Family Cites Families (34)
| 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 (OSRAM) | 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 |
| US6870058B2 (en) | 1996-12-03 | 2005-03-22 | The Trustees Of The University Of Pennsylvania | Compounds which mimic the chemical and biological properties of discodermolide |
| US6653341B1 (en) | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| CN1216051C (zh) * | 1998-06-17 | 2005-08-24 | 卫材株式会社 | 大环类似物及其使用和制备的方法 |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| DE10106647A1 (de) | 2001-02-12 | 2002-08-22 | Univ Hannover | Ratjadon-Derivate zum Hemmen des Zellwachstums |
| EP2522663B1 (en) | 2004-06-03 | 2015-04-01 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of halichondrin B |
| US20060045846A1 (en) | 2004-08-30 | 2006-03-02 | Horstmann Thomas E | Reagents and methods for labeling terminal olefins |
| EP1831697A4 (en) | 2004-12-09 | 2011-01-26 | Eisai R&D Man Co Ltd | SCREENING OF TUBULIN ISOTYPE IN CANCER THERAPY USING ANALOGUES OF HALICHONDRIN B |
| US7915457B2 (en) | 2005-09-26 | 2011-03-29 | Symrise Gmbh & Co. Kg | Intramolecular Prins reaction and catalysts suitable therefor |
| 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 |
| JPWO2009014105A1 (ja) | 2007-07-20 | 2010-10-07 | 株式会社山田養蜂場本社 | 新規カルボン酸およびそれを有効成分とする抗うつ用組成物 |
| RU2489437C2 (ru) | 2007-10-03 | 2013-08-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Промежуточные соединения и способы синтеза аналогов галихондрина в |
| 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 |
| US8598373B2 (en) * | 2008-04-04 | 2013-12-03 | Eisai R&D Management Co., Ltd. | Halichondrin B analogs |
| JP5371091B2 (ja) | 2009-01-23 | 2013-12-18 | 三菱レイヨン株式会社 | モノスルホン酸エステルの製造方法 |
| JP5800834B2 (ja) | 2010-01-26 | 2015-10-28 | 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類似体の合成において有用なフロ［３，２−ｂ］ピラン誘導体 |
| WO2012147900A1 (en) * | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| EP2785687B1 (en) | 2011-11-30 | 2019-02-20 | Sandoz AG | Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene |
| EP2831082B1 (en) | 2012-03-30 | 2019-02-20 | Sandoz AG | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein |
| CA2916537C (en) * | 2013-07-03 | 2021-07-27 | 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 |
| CN114716453A (zh) | 2013-11-04 | 2022-07-08 | 卫材R&D管理有限公司 | 软海绵素b的类似物合成中有用的大环化反应和中间体 |
| JP6443812B2 (ja) | 2013-12-06 | 2018-12-26 | 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類縁体の合成に有用な方法 |
| US10208058B2 (en) | 2014-09-09 | 2019-02-19 | Cipla Limited | Process for the preparation of macrocyclic ketone analogs of halichondrin B or pharmaceutically acceptable salts and intermediates thereof |
| WO2016179607A1 (en) | 2015-05-07 | 2016-11-10 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides |
| MX377663B (es) | 2016-02-12 | 2025-03-11 | Eisai R&D Man Co Ltd | Intermediarios en la sintesis de eribulina y metodos de sintesis relacionados. |
| MX390072B (es) | 2016-06-30 | 2025-03-20 | Eisai R&D Man Co Ltd | Reaccion de prins e intermediarios utiles en la sintesis de macrolidos de halicondrina y analogos de los mismos. |
| WO2018217894A1 (en) | 2017-05-24 | 2018-11-29 | Eisai R&D Management Co., Ltd. | Fluorine-labelled halichondrin derivatives and related methods of synthesis |
| CN111868044B (zh) | 2018-01-03 | 2024-07-19 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯及其类似物的普林斯反应和化合物 |
-
2016
- 2016-05-09 WO PCT/US2016/031546 patent/WO2016179607A1/en not_active Ceased
- 2016-05-09 EP EP16790247.7A patent/EP3292130B1/en active Active
- 2016-05-09 CN CN202310983219.7A patent/CN117024469A/zh active Pending
- 2016-05-09 MX MX2017014237A patent/MX380284B/es unknown
- 2016-05-09 JP JP2017558008A patent/JP6840090B2/ja active Active
- 2016-05-09 RU RU2017142100A patent/RU2739034C2/ru active
- 2016-05-09 KR KR1020177034639A patent/KR102743950B1/ko active Active
- 2016-05-09 CN CN202011142074.0A patent/CN112250692B/zh active Active
- 2016-05-09 CN CN201680040015.8A patent/CN107849057B/zh active Active
- 2016-05-09 MX MX2021002629A patent/MX392296B/es unknown
- 2016-05-09 RU RU2020141025A patent/RU2020141025A/ru unknown
- 2016-05-09 KR KR1020247041347A patent/KR20250012090A/ko active Pending
- 2016-05-09 US US15/571,921 patent/US10308661B2/en active Active
-
2017
- 2017-11-02 IL IL255408A patent/IL255408B/en active IP Right Grant
-
2019
- 2019-04-18 US US16/387,820 patent/US10913749B2/en active Active
-
2020
- 2020-07-29 IL IL276376A patent/IL276376B/en unknown
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