AU2013239290B2 - Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein - Google Patents

Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein Download PDF

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Publication number
AU2013239290B2
AU2013239290B2 AU2013239290A AU2013239290A AU2013239290B2 AU 2013239290 B2 AU2013239290 B2 AU 2013239290B2 AU 2013239290 A AU2013239290 A AU 2013239290A AU 2013239290 A AU2013239290 A AU 2013239290A AU 2013239290 B2 AU2013239290 B2 AU 2013239290B2
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Australia
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group
compound
alcohol protecting
protecting group
formula
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AU2013239290A1 (en
Inventor
Jason A. BEXRUD
Boris Gorin
Teng Ko NGOOI
Ricardo Orprecio
Ming PAN
Huzaifa RANGWALA
Alena Rudolph
Fabio E.S. Souza
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Sandoz AG
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Sandoz AG
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    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
    • 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
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen 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
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Peptides Or Proteins (AREA)
AU2013239290A 2012-03-30 2013-03-28 Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein Ceased AU2013239290B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261618004P 2012-03-30 2012-03-30
US61/618,004 2012-03-30
US201261647127P 2012-05-15 2012-05-15
US61/647,127 2012-05-15
PCT/CA2013/050254 WO2013142999A1 (en) 2012-03-30 2013-03-28 Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein

Publications (2)

Publication Number Publication Date
AU2013239290A1 AU2013239290A1 (en) 2014-10-30
AU2013239290B2 true AU2013239290B2 (en) 2017-08-03

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AU2013239290A Ceased AU2013239290B2 (en) 2012-03-30 2013-03-28 Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein

Country Status (8)

Country Link
US (2) US9278979B2 (OSRAM)
EP (1) EP2831082B1 (OSRAM)
JP (1) JP6531911B2 (OSRAM)
CN (1) CN104334562A (OSRAM)
AU (1) AU2013239290B2 (OSRAM)
CA (1) CA2868627C (OSRAM)
IN (1) IN2014MN02106A (OSRAM)
WO (1) WO2013142999A1 (OSRAM)

Cited By (2)

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US11725015B2 (en) 2017-04-05 2023-08-15 President And Fellows Of Harvard College Macrocyclic compound and uses thereof
US11814398B2 (en) 2017-11-15 2023-11-14 President And Fellows Of Harvard College Macrocyclic compounds and uses thereof

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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
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
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
US9174956B2 (en) 2011-12-16 2015-11-03 Alphora Research Inc. Process for preparation of 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivatives and intermediates useful thereof
JP6300030B2 (ja) 2011-12-29 2018-03-28 サンド アクツィエンゲゼルシャフト ２−（（２ｓ，３ｓ，４ｒ，５ｒ）−５−（（ｓ）−３−アミノ−２−ヒドロキシプロプ−１−イル）−４−メトキシ−３−（フェニルスルホニルメチル）テトラヒドロフラン−２−イル）アセトアルデヒド誘導体およびこれらを調製するためのプロセス
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
CN103483352A (zh) * 2013-10-18 2014-01-01 李友香 抗肿瘤的药用原料药
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
TW201617326A (zh) * 2014-03-06 2016-05-16 Ａｌｐｈｏｒａ研發股份有限公司 （ｓ）－１－（（２ｒ，３ｒ，４ｓ，５ｓ）－５－烯丙－３－甲氧－４－（對甲苯磺醯甲基）四氫呋喃－２－基）－３－氨基丙－２－醇之結晶衍生物
EP3160970A4 (en) 2014-06-30 2017-12-27 President and Fellows of Harvard College Synthesis of halichondrin analogs and uses thereof
CN105713031B (zh) * 2014-12-05 2021-05-07 正大天晴药业集团股份有限公司 一种用于制备艾日布林的中间体及其制备方法
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
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
WO2017203459A1 (en) * 2016-05-26 2017-11-30 Dr. Reddy's Laboratories Limited Process for preparation of eribulin and intermediates thereof
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
WO2018096478A2 (en) 2016-11-23 2018-05-31 Dr. Reddy’S Laboratories Limited Process for preparation of eribulin and intermediates thereof
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
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
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
KR20250057138A (ko) 2018-01-03 2025-04-28 에자이 알앤드디 매니지먼트 가부시키가이샤 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 화합물
IL279168B (en) * 2020-12-02 2022-04-01 Finetech Pharmaceutical Ltd A process for the preparation of eribulin
CN114213429B (zh) * 2021-12-22 2023-06-20 苏州正济药业有限公司 一种甲磺酸艾立布林杂质的制备方法
KR20250133788A (ko) * 2023-01-17 2025-09-08 시스트이뮨, 인코포레이티드 에리불린 약물 접합체

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WO2013097042A1 (en) * 2011-12-29 2013-07-04 Alphora Research Inc. 2-((2s,3s,4r,5r)-5-((s)-3-amino-2-hydroxyprop-1-yl)-4-methoxy-3-(phenylsulfonylmethyl)tetrahydrofuran-2-yl)acetaldehyde derivatives and process for their preparation

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US5436238A (en) 1992-03-12 1995-07-25 President And Fellows Of Harvard College Halichondrins and related compounds
ATE191712T1 (de) 1993-07-09 2000-04-15 Theramex Neue strukturelle vitamin d derivate
HU227912B1 (en) * 1998-06-17 2012-05-29 Eisai R & D Man Co Halichondrin analogs and methods of their use and preparation
US7001982B2 (en) 2003-03-31 2006-02-21 Council Of Scientific And Industrial Research Non-natural C-linked carbo-β-peptides with robust secondary structures
PL2522663T3 (pl) 2004-06-03 2015-08-31 Eisai R&D Man Co Ltd Produkty pośrednie do otrzymywania halichondryny B
US20060045846A1 (en) * 2004-08-30 2006-03-02 Horstmann Thomas E Reagents and methods for labeling terminal olefins
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
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
US9174956B2 (en) 2011-12-16 2015-11-03 Alphora Research Inc. Process for preparation of 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivatives and intermediates useful thereof
AU2014268086A1 (en) 2013-05-15 2015-11-05 Alphora Research Inc. 3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propanol derivatives, their preparation and intermediates useful thereof

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11725015B2 (en) 2017-04-05 2023-08-15 President And Fellows Of Harvard College Macrocyclic compound and uses thereof
US12421248B2 (en) 2017-04-05 2025-09-23 President And Fellows Of Harvard College Macrocyclic compound and uses thereof
US11814398B2 (en) 2017-11-15 2023-11-14 President And Fellows Of Harvard College Macrocyclic compounds and uses thereof

Also Published As

Publication number Publication date
IN2014MN02106A (OSRAM) 2015-09-11
JP6531911B2 (ja) 2019-06-19
US20150065733A1 (en) 2015-03-05
US9695187B2 (en) 2017-07-04
CA2868627C (en) 2021-02-16
US9278979B2 (en) 2016-03-08
WO2013142999A1 (en) 2013-10-03
US20160152631A1 (en) 2016-06-02
JP2015512897A (ja) 2015-04-30
CN104334562A (zh) 2015-02-04
EP2831082B1 (en) 2019-02-20
EP2831082A4 (en) 2016-01-06
AU2013239290A1 (en) 2014-10-30
CA2868627A1 (en) 2013-10-03
EP2831082A1 (en) 2015-02-04

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Owner name: SANDOZ AG

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