CN114716453A - 软海绵素b的类似物合成中有用的大环化反应和中间体 - Google Patents

软海绵素b的类似物合成中有用的大环化反应和中间体 Download PDF

Info

Publication number
CN114716453A
CN114716453A CN202210377346.8A CN202210377346A CN114716453A CN 114716453 A CN114716453 A CN 114716453A CN 202210377346 A CN202210377346 A CN 202210377346A CN 114716453 A CN114716453 A CN 114716453A
Authority
CN
China
Prior art keywords
formula
compound
protecting group
salt
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.)
Pending
Application number
CN202210377346.8A
Other languages
English (en)
Chinese (zh)
Inventor
F.G.方
D-S.金
H-W.蔡
C.E.查斯
J.李
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanitary Material R&d Management Co ltd
Original Assignee
Sanitary Material R&d Management Co ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sanitary Material R&d Management Co ltd filed Critical Sanitary Material R&d Management Co ltd
Publication of CN114716453A publication Critical patent/CN114716453A/zh
Pending legal-status Critical Current

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/22Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26Heterocyclic 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
    • C07D307/28Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic 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
    • C07D407/02Heterocyclic 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
    • C07D407/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic 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
    • C07D407/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/14Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558Heterocyclic 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
    • C07F9/65586Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561Heterocyclic 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)
CN202210377346.8A 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体 Pending CN114716453A (zh)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201361899697P 2013-11-04 2013-11-04
US61/899697 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
CN201480059909.2A CN105683198B (zh) 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN201480059909.2A Division CN105683198B (zh) 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体

Publications (1)

Publication Number Publication Date
CN114716453A true CN114716453A (zh) 2022-07-08

Family

ID=53005318

Family Applications (3)

Application Number Title Priority Date Filing Date
CN202210377346.8A Pending CN114716453A (zh) 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体
CN201480059909.2A Active CN105683198B (zh) 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体
CN201910122043.XA Active CN109942560B (zh) 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体

Family Applications After (2)

Application Number Title Priority Date Filing Date
CN201480059909.2A Active CN105683198B (zh) 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体
CN201910122043.XA Active CN109942560B (zh) 2013-11-04 2014-11-04 软海绵素b的类似物合成中有用的大环化反应和中间体

Country Status (12)

Country Link
US (5) US9783549B2 (enExample)
EP (2) EP3689881B1 (enExample)
JP (3) JP6625533B2 (enExample)
CN (3) CN114716453A (enExample)
BR (1) BR112016009452B1 (enExample)
CA (1) CA2929084C (enExample)
ES (1) ES2787603T3 (enExample)
HU (1) HUE049387T2 (enExample)
IL (4) IL244694B (enExample)
RU (1) RU2710545C2 (enExample)
SG (1) SG11201603490TA (enExample)
WO (1) WO2015066729A1 (enExample)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
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
US8598373B2 (en) 2008-04-04 2013-12-03 Eisai R&D Management Co., Ltd. Halichondrin B analogs
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
WO2017064627A2 (en) * 2015-10-14 2017-04-20 Dr. Reddy's Laboratories Limited Process for preparation of eribulin and intermediates thereof
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.
EP3423105B1 (en) 2016-03-02 2021-05-05 Eisai R&D Management Co., Ltd. Eribulin-based antibody-drug conjugates and methods of use
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
US9938288B1 (en) 2017-04-05 2018-04-10 President And Fellows Of Harvard College Macrocyclic compound and uses thereof
HUE060466T2 (hu) 2017-04-05 2023-03-28 Harvard College Makrociklusos vegyület és alkalmazása
WO2018217894A1 (en) * 2017-05-24 2018-11-29 Eisai R&D Management Co., Ltd. Fluorine-labelled halichondrin derivatives and related methods of synthesis
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
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
KR102177992B1 (ko) * 2017-11-09 2020-11-12 연성정밀화학(주) 에리불린 메실산염의 제조 중간체 및 그의 제조방법
ES2974243T3 (es) 2017-11-15 2024-06-26 Harvard College Compuestos macrocíclicos y usos de los mismos
WO2019097073A1 (en) 2017-11-20 2019-05-23 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
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
JP7063487B2 (ja) * 2018-03-02 2022-05-09 北京天一緑甫医葯科技有限公司 ピラン縮合環系化合物、その製造方法及び使用
WO2019211877A1 (en) * 2018-05-03 2019-11-07 Cipla Limited Process for the preparation of macrocyclic ketone analogs of halichondrin b
CN112437775A (zh) * 2018-07-20 2021-03-02 雷迪博士实验室有限公司 用于制备艾日布林及其中间体的纯化方法
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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110184190A1 (en) * 2010-01-26 2011-07-28 Eisai R&D Management Co., Ltd. Compounds useful in the synthesis of halichondrin b analogs
US20120029213A1 (en) * 2004-06-03 2012-02-02 Eisai R&D Management Co., Ltd. Intermediates for the preparation of analogs of halichondrin b
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

Family Cites Families (34)

* Cited by examiner, † Cited by third party
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
US5436238A (en) 1992-03-12 1995-07-25 President And Fellows Of Harvard College Halichondrins and related compounds
US5338865A (en) 1992-03-12 1994-08-16 President And Fellows Of Harvard College Synthesis of halichondrin B and norhalichondrin B
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
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
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
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
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
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
WO2012147900A1 (en) 2011-04-28 2012-11-01 Eisai R&D Management Co., Ltd. Microreactor process for halichondrin b analog synthesis
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
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.
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
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

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120029213A1 (en) * 2004-06-03 2012-02-02 Eisai R&D Management Co., Ltd. Intermediates for the preparation of analogs of halichondrin b
US20120309988A1 (en) * 2004-06-03 2012-12-06 Eisai R&D Management Co., Ltd. Intermediates for the preparation of analogs of halichondrin b
US20110184190A1 (en) * 2010-01-26 2011-07-28 Eisai R&D Management Co., Ltd. Compounds useful in the synthesis of halichondrin b analogs
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

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
AKIHIKO YAMAMOTO等: "Total Synthesis of Halichondrin C", 《J. AM. CHEM.SOC.》, vol. 134, 20 November 2011 (2011-11-20), pages 893 - 896, XP055341148, DOI: 10.1021/ja2108307 *
DAVID J. DEL VALLE等: "Total Synthesis of (+)-Trienomycins A and F via C-C Bond-Forming Hydrogenation and Transfer Hydrogenation", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》, vol. 135, 17 July 2013 (2013-07-17), pages 10986 - 10989, XP055341147, DOI: 10.1021/ja4061273 *
MICHAEL R. GESINSKI等: "Symmetric Macrocycles by a Prins Dimerization and Macrocyclization Strategy", 《ORG. LETT.》, vol. 11, no. 22, 29 October 2009 (2009-10-29), pages 5342 - 5345, XP055341149, DOI: 10.1021/ol9022062 *

Also Published As

Publication number Publication date
RU2710545C2 (ru) 2019-12-27
EP3066102A1 (en) 2016-09-14
RU2016121648A (ru) 2017-12-08
EP3066102A4 (en) 2017-04-26
EP3689881A1 (en) 2020-08-05
CN105683198A (zh) 2016-06-15
ES2787603T3 (es) 2020-10-16
JP2020023521A (ja) 2020-02-13
US20210188867A1 (en) 2021-06-24
BR112016009452A8 (pt) 2020-03-24
EP3689881B1 (en) 2022-01-12
IL244694B (en) 2019-07-31
CN109942560B (zh) 2022-06-17
IL288468A (en) 2022-01-01
RU2016121648A3 (enExample) 2018-08-06
US20180002342A1 (en) 2018-01-04
IL275240B (en) 2022-01-01
CN109942560A (zh) 2019-06-28
US10934307B2 (en) 2021-03-02
CN105683198B (zh) 2019-03-12
HUE049387T2 (hu) 2020-09-28
IL267936A (en) 2019-09-26
WO2015066729A1 (en) 2015-05-07
US10611773B2 (en) 2020-04-07
SG11201603490TA (en) 2016-05-30
US9783549B2 (en) 2017-10-10
JP6625533B2 (ja) 2019-12-25
US10221189B2 (en) 2019-03-05
IL288468B2 (en) 2023-02-01
JP6909840B2 (ja) 2021-07-28
EP3066102B1 (en) 2020-02-26
IL275240A (en) 2020-07-30
US20200223864A1 (en) 2020-07-16
US20190144463A1 (en) 2019-05-16
JP6889232B2 (ja) 2021-06-18
CA2929084A1 (en) 2015-05-07
IL244694A0 (en) 2016-04-21
JP2020059728A (ja) 2020-04-16
US11643418B2 (en) 2023-05-09
BR112016009452B1 (pt) 2022-06-07
JP2016536316A (ja) 2016-11-24
CA2929084C (en) 2022-01-11
IL288468B (en) 2022-10-01
US20160264594A1 (en) 2016-09-15
IL267936B (en) 2020-06-30

Similar Documents

Publication Publication Date Title
CN109942560B (zh) 软海绵素b的类似物合成中有用的大环化反应和中间体
CN107849057B (zh) 用于合成软海绵素大环内酯的大环化反应及中间体和其他片段
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
IL275729B2 (en) Prins reaction and compounds useful in the synthesis of helicondrin macrolides and their analogs

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
AD01 Patent right deemed abandoned

Effective date of abandoning: 20251121

AD01 Patent right deemed abandoned