CN114805322B - 可用于合成软海绵素大环内酯类及其类似物的普林斯反应和中间体 - Google Patents

可用于合成软海绵素大环内酯类及其类似物的普林斯反应和中间体 Download PDF

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CN114805322B
CN114805322B CN202210653392.6A CN202210653392A CN114805322B CN 114805322 B CN114805322 B CN 114805322B CN 202210653392 A CN202210653392 A CN 202210653392A CN 114805322 B CN114805322 B CN 114805322B
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alkyl
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CN114805322A (zh
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C.E.蔡斯
H-W.蔡
A.恩多
F.G.方
D-S.金
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Sanitary Material R&d Management Co ltd
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • 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
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    • 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
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    • 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
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    • 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
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    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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    • C07D493/16—Peri-condensed systems
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    • 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
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    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CN202210653392.6A 2016-06-30 2017-06-30 可用于合成软海绵素大环内酯类及其类似物的普林斯反应和中间体 Active CN114805322B (zh)

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US201662357031P 2016-06-30 2016-06-30
US62/357031 2016-06-30
CN201780052964.2A CN109641917B (zh) 2016-06-30 2017-06-30 可用于合成软海绵素大环内酯类及其类似物的普林斯反应和中间体
PCT/US2017/040401 WO2018006031A1 (en) 2016-06-30 2017-06-30 Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof

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US (1) US11136335B2 (https=)
EP (1) EP3478691A4 (https=)
JP (3) JP7068204B2 (https=)
KR (1) KR102404629B1 (https=)
CN (2) CN114805322B (https=)
IL (2) IL263845B (https=)
MX (1) MX390072B (https=)
SG (1) SG11201811671XA (https=)
WO (1) WO2018006031A1 (https=)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI2522663T1 (sl) 2004-06-03 2015-08-31 Eisai R&D Management Co., Ltd. Vmesne spojine za pripravo halihondrina B
BRPI0817909B1 (pt) 2007-10-03 2022-06-21 Eisai R&D Management Co., Ltd Métodos de obtenção e de preparação de uma composição diastereomericamente pura, compostos, e método para produzir os referidos compostos
RU2579511C2 (ru) 2010-01-26 2016-04-10 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Производные фуро[3,2-в]пирана, применимые в синтезе аналогов
BR112016009452B1 (pt) 2013-11-04 2022-06-07 Eisai R&D Management Co., Ltd Métodos de preparar intermediários na síntese de eribulina, métodos de preparar eribulina e mesilato de eribulina, e compostos intermediários
EP3077399B1 (en) 2013-12-06 2019-02-20 Eisai R&D Management Co., Ltd. Methods useful in the synthesis of halichondrin b analogs
MX392296B (es) 2015-05-07 2025-03-24 Eisai R&D Man Co Ltd Reacciones de macrociclizacion e intermediarios y otros fragmentos utiles en la sintesis de macrolidos de halicondrina.
CN108601760A (zh) 2016-02-12 2018-09-28 卫材R&D管理有限公司 艾日布林的合成中的中间体及相关的合成方法
IL275729B2 (en) 2018-01-03 2023-09-01 Eisai R&D Man Co Ltd Prins reaction and compounds useful in the synthesis of helicondrin macrolides and their analogs
WO2019166019A1 (zh) * 2018-03-02 2019-09-06 北京天一绿甫医药科技有限公司 吡喃稠环类化合物、其制备方法和用途

Family Cites Families (33)

* Cited by examiner, † Cited by third party
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
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 (https=) 1992-09-09 1995-09-01 Hoechst Ag
AU4255697A (en) 1996-09-06 1998-03-26 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
US6653341B1 (en) 1998-06-17 2003-11-25 Eisai Co., Ltd. Methods and compositions for use in treating cancer
JP4454151B2 (ja) 1998-06-17 2010-04-21 エーザイ・アール・アンド・ディー・マネジメント株式会社 大環状類似体及びそれらの使用並びに調製方法
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
SI2522663T1 (sl) 2004-06-03 2015-08-31 Eisai R&D Management Co., Ltd. Vmesne spojine za pripravo halihondrina B
US20060045846A1 (en) 2004-08-30 2006-03-02 Horstmann Thomas E Reagents and methods for labeling terminal olefins
US20060154312A1 (en) 2004-12-09 2006-07-13 Sergei Agoulnik Tubulin isotype screening in cancer therapy using halichondrin B analogs
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
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
US8119839B2 (en) 2007-07-20 2012-02-21 Yamada Apiculture Center, Inc. Carboxylic acid and antidepressant composition containing the same as active ingredient
BRPI0817909B1 (pt) 2007-10-03 2022-06-21 Eisai R&D Management Co., Ltd Métodos de obtenção e de preparação de uma composição diastereomericamente pura, compostos, e método para produzir os referidos compostos
CN101910180A (zh) 2007-11-16 2010-12-08 卫材R&D管理有限公司 用于软海绵素b类似物合成的新颖中间体和用于该中间体的新颖脱磺酰化反应
CA2720632C (en) 2008-04-04 2016-12-20 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
RU2579511C2 (ru) 2010-01-26 2016-04-10 Эйсай Ар Энд Ди Менеджмент Ко., Лтд. Производные фуро[3,2-в]пирана, применимые в синтезе аналогов
WO2012147900A1 (en) 2011-04-28 2012-11-01 Eisai R&D Management Co., Ltd. Microreactor process for halichondrin b analog synthesis
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
US9278979B2 (en) 2012-03-30 2016-03-08 Alphora Research Inc. Synthetic process for preparation of macrocyclic C1-keto analogs of halichondrin B and intermediates useful therein
EP3016957A4 (en) 2013-07-03 2016-11-30 Alphora Res Inc SYNTHETIC METHOD FOR THE PRODUCTION OF CYCLIC C1-KETO ANALOGUE OF HALICHONDRIN B AND USEFUL INTERMEDIATE PRODUCTS, INCLUDING INTERMEDIATE PRODUCTS WITH -SO2- (P-TOLYL) GROUPS
BR112016009452B1 (pt) 2013-11-04 2022-06-07 Eisai R&D Management Co., Ltd Métodos de preparar intermediários na síntese de eribulina, métodos de preparar eribulina e mesilato de eribulina, e compostos intermediários
EP3077399B1 (en) 2013-12-06 2019-02-20 Eisai R&D Management Co., Ltd. Methods useful in the synthesis of halichondrin b analogs
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
MX392296B (es) * 2015-05-07 2025-03-24 Eisai R&D Man Co Ltd Reacciones de macrociclizacion e intermediarios y otros fragmentos utiles en la sintesis de macrolidos de halicondrina.
CN108601760A (zh) 2016-02-12 2018-09-28 卫材R&D管理有限公司 艾日布林的合成中的中间体及相关的合成方法
WO2018217894A1 (en) 2017-05-24 2018-11-29 Eisai R&D Management Co., Ltd. Fluorine-labelled halichondrin derivatives and related methods of synthesis
IL275729B2 (en) 2018-01-03 2023-09-01 Eisai R&D Man Co Ltd Prins reaction and compounds useful in the synthesis of helicondrin macrolides and their analogs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PubChem CID 10501910;PubChem;《PubChem》;20061025;第1-6页 *

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JP7068204B2 (ja) 2022-05-16
US20190161495A1 (en) 2019-05-30
EP3478691A4 (en) 2020-07-22
JP2019524674A (ja) 2019-09-05
RU2019102375A3 (https=) 2021-07-05
CN114805322A (zh) 2022-07-29
JP7440563B2 (ja) 2024-02-28
IL263845A (en) 2019-01-31
RU2019102375A (ru) 2020-07-30
IL288460A (en) 2022-01-01
IL263845B (en) 2022-01-01
IL288460B2 (en) 2023-08-01
EP3478691A1 (en) 2019-05-08
MX2018016329A (es) 2019-09-18
CN109641917A (zh) 2019-04-16
CN109641917B (zh) 2022-06-14
JP2022105115A (ja) 2022-07-12
JP2024056892A (ja) 2024-04-23
SG11201811671XA (en) 2019-01-30
IL288460B1 (en) 2023-04-01
KR102404629B1 (ko) 2022-06-02
US11136335B2 (en) 2021-10-05
KR20190039103A (ko) 2019-04-10
MX390072B (es) 2025-03-20
WO2018006031A1 (en) 2018-01-04

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