CA2929084C - Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin b - Google Patents
Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin b Download PDFInfo
- Publication number
- CA2929084C CA2929084C CA2929084A CA2929084A CA2929084C CA 2929084 C CA2929084 C CA 2929084C CA 2929084 A CA2929084 A CA 2929084A CA 2929084 A CA2929084 A CA 2929084A CA 2929084 C CA2929084 C CA 2929084C
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- Prior art keywords
- formula
- compound
- combine
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361899697P | 2013-11-04 | 2013-11-04 | |
| US61/899,697 | 2013-11-04 | ||
| PCT/US2014/063960 WO2015066729A1 (en) | 2013-11-04 | 2014-11-04 | Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2929084A1 CA2929084A1 (en) | 2015-05-07 |
| CA2929084C true CA2929084C (en) | 2022-01-11 |
Family
ID=53005318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2929084A Active CA2929084C (en) | 2013-11-04 | 2014-11-04 | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin b |
Country Status (12)
| Country | Link |
|---|---|
| US (5) | US9783549B2 (https=) |
| EP (2) | EP3689881B1 (https=) |
| JP (3) | JP6625533B2 (https=) |
| CN (3) | CN105683198B (https=) |
| BR (1) | BR112016009452B1 (https=) |
| CA (1) | CA2929084C (https=) |
| ES (1) | ES2787603T3 (https=) |
| HU (1) | HUE049387T2 (https=) |
| IL (4) | IL244694B (https=) |
| RU (1) | RU2710545C2 (https=) |
| SG (1) | SG11201603490TA (https=) |
| WO (1) | WO2015066729A1 (https=) |
Families Citing this family (32)
| 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 |
| 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 |
| 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 |
| 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. |
| US10556910B2 (en) | 2014-06-30 | 2020-02-11 | President And Fellows Of Harvard College | Synthesis of halichondrin analogs and uses thereof |
| 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 |
| WO2017064627A2 (en) * | 2015-10-14 | 2017-04-20 | Dr. Reddy's Laboratories Limited | Process for preparation of eribulin and intermediates thereof |
| 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 |
| 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 |
| 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 |
| ES2931533T3 (es) * | 2017-04-05 | 2022-12-30 | Harvard College | Compuesto macrocíclico y usos del mismo |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| WO2018217894A1 (en) * | 2017-05-24 | 2018-11-29 | Eisai R&D Management Co., Ltd. | Fluorine-labelled halichondrin derivatives and related methods of synthesis |
| 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 |
| CN109694379B (zh) * | 2017-10-24 | 2020-09-11 | 江苏恒瑞医药股份有限公司 | 用于制备艾日布林的中间体及其制备方法 |
| JP6967811B2 (ja) * | 2017-11-09 | 2021-11-17 | ヨンスン ファイン ケミカル カンパニー，リミテッド | エリブリンメシル酸塩の製造中間体及びその製造方法 |
| 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 |
| CN109970822B (zh) * | 2017-12-27 | 2023-03-28 | 上海科胜药物研发有限公司 | 一种合成埃格列净中间体的制备方法 |
| 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 |
| EP3608323B1 (en) * | 2018-03-02 | 2021-11-03 | Beijing Tienyi Lufu Pharmatech Co. Ltd. | Pyran fused ring compound, preparation method therefor and use thereof |
| WO2019211877A1 (en) * | 2018-05-03 | 2019-11-07 | Cipla Limited | Process for the preparation of macrocyclic ketone analogs of halichondrin b |
| JP2021532102A (ja) * | 2018-07-20 | 2021-11-25 | ドクター レディズ ラボラトリーズ リミテッド | エリブリンおよびその中間体の調製のための精製プロセス |
| US11447499B2 (en) * | 2019-06-14 | 2022-09-20 | Rk Pharma Inc. | Process for the preparation of eribulin mesylate intermediate |
| CN110684036B (zh) * | 2019-11-22 | 2022-04-12 | 江苏慧聚药业股份有限公司 | 一条制备甲磺酸艾日布林的方法 |
| WO2023144733A1 (en) * | 2022-01-26 | 2023-08-03 | Simon Fraser University | Compounds and processes for the preparation of eribulin |
| CN119585437A (zh) * | 2022-07-29 | 2025-03-07 | 上海皓元医药股份有限公司 | 一种艾日布林中间体的制备方法 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107206A (en) | 1974-04-08 | 1978-08-15 | Akzona Incorporated | Benzo-bicyclononene- derivatives |
| 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 (https=) | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| WO1998009942A1 (en) | 1996-09-06 | 1998-03-12 | Eli Lilly And Company | Catalytic selective sulfonylation process |
| 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 |
| US6214865B1 (en) | 1998-06-17 | 2001-04-10 | Eisai Co., Ltd. | Macrocyclic analogs and methods of their use and preparation |
| 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 |
| DE10106647A1 (de) | 2001-02-12 | 2002-08-22 | Univ Hannover | Ratjadon-Derivate zum Hemmen des Zellwachstums |
| CA2822994C (en) * | 2004-06-03 | 2016-09-27 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of analogs of halichondrin b |
| 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 | SEARCH FOR TUBULINISOTYPES IN CANCER THERAPY USING HALICHONDRIN B ANALOG |
| WO2007039342A1 (en) | 2005-09-26 | 2007-04-12 | 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 |
| RU2010118063A (ru) | 2007-11-16 | 2011-12-27 | ЭЙСАЙ Ар энд Ди МЕНЕДЖМЕНТ КО., ЛТД. (JP) | Новое промежуточное соединение для синтеза аналога галихондрина в и новая реакция десульфонилирования, применяемая для получения промежуточного соединения |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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" |
| 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 |
| 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 |
| US20180009825A1 (en) * | 2016-07-06 | 2018-01-11 | Apicore Us Llc | Methods of making eribulin mesylate |
| 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 |
-
2014
- 2014-11-04 EP EP20156829.2A patent/EP3689881B1/en active Active
- 2014-11-04 CN CN201480059909.2A patent/CN105683198B/zh active Active
- 2014-11-04 SG SG11201603490TA patent/SG11201603490TA/en unknown
- 2014-11-04 EP EP14858240.6A patent/EP3066102B1/en active Active
- 2014-11-04 RU RU2016121648A patent/RU2710545C2/ru active
- 2014-11-04 JP JP2016527449A patent/JP6625533B2/ja active Active
- 2014-11-04 HU HUE14858240A patent/HUE049387T2/hu unknown
- 2014-11-04 US US15/033,970 patent/US9783549B2/en active Active
- 2014-11-04 CN CN202210377346.8A patent/CN114716453A/zh active Pending
- 2014-11-04 CA CA2929084A patent/CA2929084C/en active Active
- 2014-11-04 WO PCT/US2014/063960 patent/WO2015066729A1/en not_active Ceased
- 2014-11-04 ES ES14858240T patent/ES2787603T3/es active Active
- 2014-11-04 BR BR112016009452-2A patent/BR112016009452B1/pt active IP Right Grant
- 2014-11-04 CN CN201910122043.XA patent/CN109942560B/zh active Active
-
2016
- 2016-03-21 IL IL244694A patent/IL244694B/en active IP Right Grant
-
2017
- 2017-09-18 US US15/707,412 patent/US10221189B2/en active Active
-
2019
- 2019-01-14 US US16/246,999 patent/US10611773B2/en active Active
- 2019-07-09 IL IL267936A patent/IL267936B/en active IP Right Grant
- 2019-10-02 JP JP2019181798A patent/JP6909840B2/ja not_active Expired - Fee Related
- 2019-11-27 JP JP2019213906A patent/JP6889232B2/ja active Active
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2020
- 2020-03-30 US US16/833,923 patent/US10934307B2/en active Active
- 2020-06-09 IL IL275240A patent/IL275240B/en unknown
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2021
- 2021-03-01 US US17/188,819 patent/US11643418B2/en active Active
- 2021-11-28 IL IL288468A patent/IL288468B2/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
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| CA2929084C (en) | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of analogs of halichondrin b | |
| JP7440563B2 (ja) | ハリコンドリンマクロライドおよびその類縁体の合成に有用なプリンス反応および中間体 | |
| EP3292130B1 (en) | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides | |
| RU2777913C2 (ru) | Реакция принса и промежуточные продукты, применимые при синтезе макролидов галихондринового ряда и их аналогов |
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Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT Effective date: 20251217 |