AU2016360886B2 - Method for synthesizing iodo- or astatoarenes using diaryliodonium salts - Google Patents

Method for synthesizing iodo- or astatoarenes using diaryliodonium salts Download PDF

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AU2016360886B2
AU2016360886B2 AU2016360886A AU2016360886A AU2016360886B2 AU 2016360886 B2 AU2016360886 B2 AU 2016360886B2 AU 2016360886 A AU2016360886 A AU 2016360886A AU 2016360886 A AU2016360886 A AU 2016360886A AU 2016360886 B2 AU2016360886 B2 AU 2016360886B2
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alkylene
alkyl
astatoarene
formula
group
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AU2016360886A1 (en
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Martin W BRECHBIEL
Jean-François GESTIN
François GUERARD
Yong-Sok Lee
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Centre National de la Recherche Scientifique
University of Angers
Institut National de la Santé et de la Recherche Médicale
Nantes Université
United States Department of Health and Human Services
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Centre National de la Recherche Scientifique
University of Angers
Universite de Nantes
Institut National de la Santé et de la Recherche Médicale
Government of the United States of America
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Assigned to CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM), THE GOVERNMENT OF THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, UNIVERSITE D'ANGERS, NANTES UNIVERSITE reassignment CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE Request to Amend Deed and Register Assignors: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM), THE GOVERNMENT OF THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, UNIVERSITE D'ANGERS, UNIVERSITE DE NANTES
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001—Acyclic or carbocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/008—Peptides; Proteins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C247/08—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated
    • C07C247/10—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated and containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/16—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/58—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of halogen, e.g. by hydrogenolysis, splitting-off
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
AU2016360886A 2015-11-24 2016-11-24 Method for synthesizing iodo- or astatoarenes using diaryliodonium salts Active AU2016360886B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP15306862.2 2015-11-24
EP15306862 2015-11-24
PCT/EP2016/078729 WO2017089492A1 (en) 2015-11-24 2016-11-24 Method for synthesizing iodo- or astatoarenes using diaryliodonium salts

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AU2016360886A1 AU2016360886A1 (en) 2018-06-07
AU2016360886B2 true AU2016360886B2 (en) 2021-04-15

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EP (1) EP3380447B1 (cg-RX-API-DMAC10.html)
JP (1) JP6968809B2 (cg-RX-API-DMAC10.html)
AU (1) AU2016360886B2 (cg-RX-API-DMAC10.html)
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Publication number Priority date Publication date Assignee Title
WO2019131998A1 (ja) * 2017-12-29 2019-07-04 国立大学法人大阪大学 アスタチン溶液及びその製造方法
US20230098031A1 (en) * 2019-12-11 2023-03-30 The General Hospital Corporation Methods for cell imaging
US20220356205A1 (en) * 2020-02-21 2022-11-10 National University Corporation Hokkaido University Method for producing aromatic astatine compound
WO2021225147A1 (ja) * 2020-05-07 2021-11-11 国立大学法人東京工業大学 アスタチンの簡便な濃縮法
CN112778089B (zh) * 2021-01-04 2023-09-05 万知科技股份有限公司 一种4,4,4-三氟-1-丁醇及其同系物的新合成方法
WO2023222909A1 (en) * 2022-05-20 2023-11-23 Institut National de la Santé et de la Recherche Médicale Method for synthesizing iodo- or astatoaryl compounds using arylsulfonium salts
JP2025520445A (ja) * 2022-06-16 2025-07-03 ザ ジェネラル ホスピタル コーポレイション 細胞イメージング用のビシクロノニン試薬
CN119552051A (zh) * 2024-11-15 2025-03-04 中国船舶集团有限公司第七一八研究所 一种阳离子光引发剂4-异丁基苯基-4'-甲基苯基碘鎓六氟磷酸盐的制备方法

Citations (3)

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Publication number Priority date Publication date Assignee Title
WO2005021472A2 (en) * 2003-08-29 2005-03-10 Ic Innovations Limited Fluoridation of electron rich aromatic systems
WO2005097713A1 (en) * 2004-04-08 2005-10-20 Ge Healthcare Limited Fluoridation method
WO2011095517A1 (en) * 2010-02-03 2011-08-11 Institut National De La Sante Et De La Recherche Medicale (Inserm) Hypervalent radioactive astatine or iodine compounds, and preparation methods thereof

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US3863010A (en) 1973-09-28 1975-01-28 American Cyanamid Co Compositions of matter and method of use of phenyl and substituted phenyl tetrazines
AU5194798A (en) 1996-10-29 1998-05-22 Guilford Pharmaceuticals Inc. Process for the preparation of radiopharmaceuticals
JP2005508951A (ja) * 2001-10-12 2005-04-07 スミスクライン・ビーチャム・コーポレイション 化合物および方法
GB0921573D0 (en) * 2009-12-10 2010-01-27 Ge Healthcare Ltd Iodine radiolabelling method
JP2016503401A (ja) * 2012-10-27 2016-02-04 グランド・フルーア・ファーマスーティカルズ・インコーポレイテッド ジアリールヨードニウム塩を製造するための方法及び試薬
WO2015147950A2 (en) * 2014-01-03 2015-10-01 Nutech Ventures Radioiodinated compounds
CN106458960B (zh) * 2014-03-07 2020-10-23 通用医疗公司 碘(iii)-介导的放射性氟化
US20170001957A1 (en) * 2015-06-12 2017-01-05 Nutech Ventures Radioiodinated bioconjugation reagents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005021472A2 (en) * 2003-08-29 2005-03-10 Ic Innovations Limited Fluoridation of electron rich aromatic systems
WO2005097713A1 (en) * 2004-04-08 2005-10-20 Ge Healthcare Limited Fluoridation method
WO2011095517A1 (en) * 2010-02-03 2011-08-11 Institut National De La Sante Et De La Recherche Medicale (Inserm) Hypervalent radioactive astatine or iodine compounds, and preparation methods thereof

Non-Patent Citations (1)

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Title
HU, B. ET AL., Chem. Eur. J., 2015, Vol. 21, pages 6394-6398 *

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EP3380447B1 (en) 2025-09-03
US20200239404A1 (en) 2020-07-30
US10858306B2 (en) 2020-12-08
EP3380447C0 (en) 2025-09-03
US10703708B2 (en) 2020-07-07
EP3380447A1 (en) 2018-10-03
JP2018536031A (ja) 2018-12-06
US20190023646A1 (en) 2019-01-24
AU2016360886A1 (en) 2018-06-07
JP6968809B2 (ja) 2021-11-17
WO2017089492A1 (en) 2017-06-01

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