CN105683198B - 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

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CN105683198B
CN105683198B CN201480059909.2A CN201480059909A CN105683198B CN 105683198 B CN105683198 B CN 105683198B CN 201480059909 A CN201480059909 A CN 201480059909A CN 105683198 B CN105683198 B CN 105683198B
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formula
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CN105683198A (zh
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F.G.方
D-S.金
H-W.蔡
C.E.查斯
J.李
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Sanitary Material R&d Management Co ltd
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    • 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
    • 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
    • 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

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  • 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)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Steroid Compounds (AREA)
CN201480059909.2A 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 Active CN105683198B (zh)

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CN201910122043.XA 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
CN202210377346.8A 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

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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

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CN201910122043.XA Division 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

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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

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Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2522663T3 (pl) 2004-06-03 2015-08-31 Eisai R&D Man Co Ltd Produkty pośrednie do otrzymywania halichondryny B
CN108948039B (zh) 2007-10-03 2021-12-31 卫材R&D管理有限公司 用于合成软海绵素b类似物的中间体和方法
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
CN102803254B (zh) 2010-01-26 2016-09-14 卫材R&D管理有限公司 用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物
CN105683198B (zh) 2013-11-04 2019-03-12 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
HUE043088T2 (hu) 2013-12-06 2019-08-28 Eisai R&D Man Co Ltd Halikondrin B analógok szintézisében alkalmazható eljárások
EP3160970A4 (en) 2014-06-30 2017-12-27 President and Fellows of Harvard College Synthesis of halichondrin analogs and uses 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
RU2020141025A (ru) 2015-05-07 2020-12-28 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Реакции макроциклизации и промежуточные соединения и другие фрагменты, полезные в синтезе макролидов галихондринов
WO2017064627A2 (en) * 2015-10-14 2017-04-20 Dr. Reddy's Laboratories Limited Process for preparation of eribulin and intermediates thereof
US10676481B2 (en) 2016-02-12 2020-06-09 Eisai R&D Management Co., Ltd. Intermediates in the synthesis of eribulin and related methods of synthesis
MA45280B1 (fr) 2016-03-02 2021-08-31 Eisai R&D Man Co Ltd Conjugués anticorps-médicament à base d'éribuline et leurs procédés d'utilisation
SG11201811671XA (en) * 2016-06-30 2019-01-30 Eisai R&D Man 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
KR102836514B1 (ko) 2017-04-05 2025-07-22 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 마크로시클릭 화합물 및 그의 용도
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
US11142509B2 (en) * 2017-11-09 2021-10-12 Yonsung Fine Chemical Co., Ltd. Intermediate for preparing eribulin mesylate and process for preparing the same
ES2974243T3 (es) 2017-11-15 2024-06-26 Harvard College Compuestos macrocíclicos y usos de los mismos
EP3713565A1 (en) 2017-11-20 2020-09-30 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
KR20250057138A (ko) 2018-01-03 2025-04-28 에자이 알앤드디 매니지먼트 가부시키가이샤 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 화합물
US11396515B2 (en) * 2018-03-02 2022-07-26 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

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060045846A1 (en) * 2004-08-30 2006-03-02 Horstmann Thomas E Reagents and methods for labeling terminal olefins
CN1993342A (zh) * 2004-06-03 2007-07-04 卫材株式会社 用于制备软海绵素b的中间体
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
US20110184190A1 (en) * 2010-01-26 2011-07-28 Eisai R&D Management Co., Ltd. Compounds useful in the synthesis of halichondrin b analogs
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 (33)

* 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
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
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
HU227912B1 (en) 1998-06-17 2012-05-29 Eisai R & D Man Co Halichondrin analogs and methods of their use and preparation
US8097648B2 (en) 1998-06-17 2012-01-17 Eisai R&D Management Co., Ltd. Methods and compositions for use in treating cancer
US6653341B1 (en) 1998-06-17 2003-11-25 Eisai 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
PL2522663T3 (pl) 2004-06-03 2015-08-31 Eisai R&D Man Co Ltd Produkty pośrednie do otrzymywania halichondryny B
EP1831697A4 (en) 2004-12-09 2011-01-26 Eisai R&D Man Co Ltd SEARCH FOR TUBULINISOTYPES IN CANCER THERAPY USING HALICHONDRIN B ANALOG
JP2009510005A (ja) 2005-09-26 2009-03-12 シムライズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツト・ゲゼルシヤフト 分子内プリンス反応および該反応に適する触媒
US8119839B2 (en) 2007-07-20 2012-02-21 Yamada Apiculture Center, Inc. Carboxylic acid and antidepressant composition containing the same as active ingredient
CN108948039B (zh) 2007-10-03 2021-12-31 卫材R&D管理有限公司 用于合成软海绵素b类似物的中间体和方法
US20090203771A1 (en) 2007-11-16 2009-08-13 Eisai R&D Management Co., Ltd. Novel intermediate for halichondrin b analog synthesis and novel desulfonylation reaction used for the intermediate
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
WO2012147900A1 (en) 2011-04-28 2012-11-01 Eisai R&D Management Co., Ltd. Microreactor process for halichondrin b analog synthesis
CA2857385A1 (en) * 2011-11-30 2013-06-06 Alphora Research Inc. Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene
US9850254B2 (en) 2013-07-03 2017-12-26 Sandoz Ag Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein including intermediates containing-SO2-(p-tolyl) groups
CN105683198B (zh) 2013-11-04 2019-03-12 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
HUE043088T2 (hu) 2013-12-06 2019-08-28 Eisai R&D Man Co Ltd Halikondrin B analógok szintézisében alkalmazható eljárások
EP3191479B1 (en) 2014-09-09 2020-04-08 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
RU2020141025A (ru) * 2015-05-07 2020-12-28 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Реакции макроциклизации и промежуточные соединения и другие фрагменты, полезные в синтезе макролидов галихондринов
US10676481B2 (en) 2016-02-12 2020-06-09 Eisai R&D Management Co., Ltd. Intermediates in the synthesis of eribulin and related methods of synthesis
SG11201811671XA (en) 2016-06-30 2019-01-30 Eisai R&D Man 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
KR20250057138A (ko) * 2018-01-03 2025-04-28 에자이 알앤드디 매니지먼트 가부시키가이샤 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 화합물

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1993342A (zh) * 2004-06-03 2007-07-04 卫材株式会社 用于制备软海绵素b的中间体
US20060045846A1 (en) * 2004-08-30 2006-03-02 Horstmann Thomas E Reagents and methods for labeling terminal olefins
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
US20110184190A1 (en) * 2010-01-26 2011-07-28 Eisai R&D Management Co., Ltd. Compounds useful in the synthesis of halichondrin b analogs
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 (1)

* Cited by examiner, † Cited by third party
Title
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》.2013,第135卷第10986-10989页,尤其Scheme 4,10988页左栏第1段. *

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IL244694B (en) 2019-07-31
US10221189B2 (en) 2019-03-05
EP3689881B1 (en) 2022-01-12
US20180002342A1 (en) 2018-01-04
US10611773B2 (en) 2020-04-07
BR112016009452B1 (pt) 2022-06-07
EP3066102A4 (en) 2017-04-26
IL267936A (en) 2019-09-26
RU2016121648A (ru) 2017-12-08
RU2710545C2 (ru) 2019-12-27
IL288468B (en) 2022-10-01
CA2929084A1 (en) 2015-05-07
CN109942560A (zh) 2019-06-28
JP6889232B2 (ja) 2021-06-18
ES2787603T3 (es) 2020-10-16
BR112016009452A8 (pt) 2020-03-24
WO2015066729A1 (en) 2015-05-07
CN105683198A (zh) 2016-06-15
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