WO2009078396A1 - 放射性フッ素標識有機化合物の製造方法 - Google Patents

放射性フッ素標識有機化合物の製造方法 Download PDF

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Publication number
WO2009078396A1
WO2009078396A1 PCT/JP2008/072827 JP2008072827W WO2009078396A1 WO 2009078396 A1 WO2009078396 A1 WO 2009078396A1 JP 2008072827 W JP2008072827 W JP 2008072827W WO 2009078396 A1 WO2009078396 A1 WO 2009078396A1
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WO
WIPO (PCT)
Prior art keywords
substituent
radioactive
fluorine
linear
carbon atoms
Prior art date
Application number
PCT/JP2008/072827
Other languages
English (en)
French (fr)
Inventor
Fumie Kurosaki
Masahito Toyama
Akio Hayashi
Original Assignee
Nihon Medi-Physics 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
Priority to CN2008801217441A priority Critical patent/CN101939290B/zh
Priority to ES08863261.7T priority patent/ES2610574T3/es
Application filed by Nihon Medi-Physics Co., Ltd. filed Critical Nihon Medi-Physics Co., Ltd.
Priority to JP2009546266A priority patent/JP5732198B2/ja
Priority to BRPI0821241-4A priority patent/BRPI0821241B1/pt
Priority to NZ586636A priority patent/NZ586636A/en
Priority to SI200831746A priority patent/SI2230229T1/sl
Priority to DK08863261.7T priority patent/DK2230229T3/en
Priority to US12/747,726 priority patent/US8269035B2/en
Priority to CA2709558A priority patent/CA2709558C/en
Priority to EP08863261.7A priority patent/EP2230229B1/en
Priority to MX2010006901A priority patent/MX2010006901A/es
Priority to RU2010129950/04A priority patent/RU2476423C2/ru
Priority to AU2008339435A priority patent/AU2008339435B2/en
Publication of WO2009078396A1 publication Critical patent/WO2009078396A1/ja
Priority to IL206332A priority patent/IL206332A/en
Priority to HK11105401.9A priority patent/HK1151513A1/xx

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Classifications

    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

【課題】放射性フッ素標識有機化合物の製造において、放射性フッ素化収率を向上させ得る方法を提供する。 【解決手段】下記式（１）： 　 （式中、Ｒ１は、直鎖若しくは分岐鎖の炭素数１～１０のアルキル鎖又は芳香族置換基、Ｒ２は、直鎖若しくは分岐鎖の炭素数１～１０のハロアルキルスルホン酸置換基、直鎖若しくは分岐鎖の炭素数１～１０のアルキルスルホン酸置換基、フルオロスルホン酸置換基又は芳香族スルホン酸置換基、Ｒ３は、保護基である）で表される化合物を、不活性有機溶媒中で、相関移動触媒、１８Fイオン及びカリウムイオンの存在下、加熱下にて攪拌して放射性フッ素標識する方法において、加熱温度を４０～９０°Cとし、不活性有機溶媒中における相間移動触媒の濃度を７０ｍｍｏｌ／Ｌ以上とする。相間移動触媒は式（１）の化合物に対してモル比で０．７以上、式（１）の化合物の不活性有機溶媒中の濃度は５０ｍｍｏｌ／Ｌ以上が好ましい。
PCT/JP2008/072827 2007-12-19 2008-12-16 放射性フッ素標識有機化合物の製造方法 WO2009078396A1 (ja)

Priority Applications (15)

Application Number Priority Date Filing Date Title
CA2709558A CA2709558C (en) 2007-12-19 2008-12-16 Process for production of radioactive-fluorine-labeled organic compound
US12/747,726 US8269035B2 (en) 2007-12-19 2008-12-16 Process for production of radioactive-fluorine-labeled organic compound
JP2009546266A JP5732198B2 (ja) 2007-12-19 2008-12-16 放射性フッ素標識有機化合物の製造方法
ES08863261.7T ES2610574T3 (es) 2007-12-19 2008-12-16 Procedimiento para producir un compuesto orgánico marcado con flúor radiactivo
NZ586636A NZ586636A (en) 2007-12-19 2008-12-16 Process for production of radioactive-fluorine-labeled organic compound
SI200831746A SI2230229T1 (sl) 2007-12-19 2008-12-16 Postopek za proizvodnjo z radioaktivnim fluorom markirane organske spojine
EP08863261.7A EP2230229B1 (en) 2007-12-19 2008-12-16 Process for production of radioactive-fluorine-labeled organic compound
CN2008801217441A CN101939290B (zh) 2007-12-19 2008-12-16 放射性氟标记的有机化合物的制备方法
BRPI0821241-4A BRPI0821241B1 (pt) 2007-12-19 2008-12-16 Processo para a produção de um composto orgânico marcado com flúor radioativo
DK08863261.7T DK2230229T3 (en) 2007-12-19 2008-12-16 Process for the preparation of radioactive-fluoro-labeled organic compound
MX2010006901A MX2010006901A (es) 2007-12-19 2008-12-16 Proceso para la produccion del compuesto organico marcado con fluor radioactivo.
RU2010129950/04A RU2476423C2 (ru) 2007-12-19 2008-12-16 Способ получения радиоактивного, меченного фтором органического соединения
AU2008339435A AU2008339435B2 (en) 2007-12-19 2008-12-16 Process for production of radioactive-fluorine-labeled organic compound
IL206332A IL206332A (en) 2007-12-19 2010-06-13 A process for making an organic compound marked with radioactive fluorine
HK11105401.9A HK1151513A1 (en) 2007-12-19 2011-05-31 Process for production of radioactive-fluorine-labeled organic compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-327444 2007-12-19
JP2007327444 2007-12-19

Publications (1)

Publication Number Publication Date
WO2009078396A1 true WO2009078396A1 (ja) 2009-06-25

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Family Applications (1)

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PCT/JP2008/072827 WO2009078396A1 (ja) 2007-12-19 2008-12-16 放射性フッ素標識有機化合物の製造方法

Country Status (19)

Country Link
US (1) US8269035B2 (ja)
EP (1) EP2230229B1 (ja)
JP (1) JP5732198B2 (ja)
KR (1) KR101583544B1 (ja)
CN (1) CN101939290B (ja)
AU (1) AU2008339435B2 (ja)
BR (1) BRPI0821241B1 (ja)
CA (1) CA2709558C (ja)
DK (1) DK2230229T3 (ja)
ES (1) ES2610574T3 (ja)
HK (1) HK1151513A1 (ja)
IL (1) IL206332A (ja)
MX (1) MX2010006901A (ja)
NZ (1) NZ586636A (ja)
PL (1) PL2230229T3 (ja)
RU (1) RU2476423C2 (ja)
SI (1) SI2230229T1 (ja)
TW (1) TWI458494B (ja)
WO (1) WO2009078396A1 (ja)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014508731A (ja) * 2010-12-29 2014-04-10 ジーイー・ヘルスケア・リミテッド 溶出溶液
JP2014509303A (ja) * 2010-12-20 2014-04-17 ジーイー・ヘルスケア・リミテッド 結晶化による前駆体化合物の精製
JP2015530985A (ja) * 2012-08-09 2015-10-29 ジーイー・ヘルスケア・リミテッド １８ｆ−フルシクロビンの製造
JP2017214389A (ja) * 2010-12-20 2017-12-07 ジーイー・ヘルスケア・リミテッド 結晶化による前駆体化合物の精製
JPWO2016194586A1 (ja) * 2015-06-05 2018-03-22 日本メジフィジックス株式会社 放射性標識化合物の製造装置及び製造方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2006319987B2 (en) 2005-11-29 2012-09-06 Nihon Medi-Physics Co., Ltd. Precursor compound of radioactive halogen labeled organic compound
GB201021523D0 (en) * 2010-12-20 2011-02-02 Ge Healthcare Ltd Process simplification for precursor compound
GB201305687D0 (en) 2013-03-28 2013-05-15 Ge Healthcare Ltd Radiolabelling process
GB201411571D0 (en) * 2014-06-30 2014-08-13 Ge Healthcare Ltd Radiolabelling method
KR101842989B1 (ko) * 2018-01-02 2018-03-28 (주)퓨쳐켐 카보닐기를 갖는 알코올 용매를 이용한 플루오르화 화합물의 제조방법
KR20210093802A (ko) 2021-07-08 2021-07-28 서정철 펄스파를 이용한 직류 접지회선 추적 방법과 접지 전류의 위상분석을 통한 접지 극성 판단 장치

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11295494A (ja) * 1998-04-08 1999-10-29 Nippon Meji Physics Kk ［ｆ−１８］−フッ化物イオンの製造方法
JP2000500442A (ja) 1995-11-09 2000-01-18 エモリー ユニバーシティ 腫瘍画像化のためのアミノ酸アナログ
JP2004529989A (ja) * 2001-06-05 2004-09-30 フォルシュングスツェントルム ユーリッヒ ゲーエムベーハー 保護されたチロシン誘導体、その製造方法、及びｏ−（２−〔１８ｆ〕−フルオロエチル）−ｌ−チロシン製造のためのその使用
WO2007063940A1 (ja) * 2005-12-02 2007-06-07 Nihon Medi-Physics Co., Ltd. 放射性フッ素標識化合物の製造方法
WO2007132689A1 (ja) * 2006-05-11 2007-11-22 Nihon Medi-Physics Co., Ltd. 放射性フッ素標識有機化合物の製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0229695D0 (en) 2002-12-20 2003-01-29 Amersham Plc Solid-phase preparation of 18F-labelled amino acids
WO2007001958A2 (en) 2005-06-23 2007-01-04 Emory University Stereoselective synthesis of amino acid analogs for tumor imaging

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000500442A (ja) 1995-11-09 2000-01-18 エモリー ユニバーシティ 腫瘍画像化のためのアミノ酸アナログ
JPH11295494A (ja) * 1998-04-08 1999-10-29 Nippon Meji Physics Kk ［ｆ−１８］−フッ化物イオンの製造方法
JP2004529989A (ja) * 2001-06-05 2004-09-30 フォルシュングスツェントルム ユーリッヒ ゲーエムベーハー 保護されたチロシン誘導体、その製造方法、及びｏ−（２−〔１８ｆ〕−フルオロエチル）−ｌ−チロシン製造のためのその使用
WO2007063940A1 (ja) * 2005-12-02 2007-06-07 Nihon Medi-Physics Co., Ltd. 放射性フッ素標識化合物の製造方法
WO2007132689A1 (ja) * 2006-05-11 2007-11-22 Nihon Medi-Physics Co., Ltd. 放射性フッ素標識有機化合物の製造方法

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
APPLIED RADIATION AND ISOTOPES, vol. 58, no. 6, 2003, pages 657 - 666 *
J. MCCONATHY ET AL., APPLIED RADIATION AND ISOTOPES, vol. 58, 2003, pages 657 - 666
JONATHAN MCCONATHY ET AL.: "Improved synthesis of anti-[18F]FACBC: improved preparation of labeling precursor and automated radiosynthesis", APPLIED RADIATION AND ISOTOPES, (NETHERLANDS), vol. 58, 2003, pages 657 - 666, XP055266777, DOI: doi:10.1016/S0969-8043(03)00029-0
See also references of EP2230229A4
THE JOURNAL OF NUCLEAR MEDICINE, vol. 40, no. 2, 1999, pages 331 - 338 *
TIMOTHY M. ET AL., J. NUC. MED., vol. 40, 1999, pages 331 - 338
TIMOTHY M. SHOUP ET AL.: "Synthesis and Evaluation of [18F]1-Amino-3-fluorocyclobutane-1-carboxylic Acid to Image Brain Tumors", THE JOURNAL OF NUCLEAR MEDICINE, vol. 40, 1999, pages 331 - 338

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014509303A (ja) * 2010-12-20 2014-04-17 ジーイー・ヘルスケア・リミテッド 結晶化による前駆体化合物の精製
JP2017214389A (ja) * 2010-12-20 2017-12-07 ジーイー・ヘルスケア・リミテッド 結晶化による前駆体化合物の精製
JP2014508731A (ja) * 2010-12-29 2014-04-10 ジーイー・ヘルスケア・リミテッド 溶出溶液
JP2015530985A (ja) * 2012-08-09 2015-10-29 ジーイー・ヘルスケア・リミテッド １８ｆ−フルシクロビンの製造
US10023525B2 (en) 2012-08-09 2018-07-17 Ge Healthcare Limited Preparation of 18F-fluciclovine
JPWO2016194586A1 (ja) * 2015-06-05 2018-03-22 日本メジフィジックス株式会社 放射性標識化合物の製造装置及び製造方法

Also Published As

Publication number Publication date
NZ586636A (en) 2012-05-25
CA2709558C (en) 2016-08-16
EP2230229A4 (en) 2010-11-24
JPWO2009078396A1 (ja) 2011-04-28
EP2230229B1 (en) 2016-10-12
MX2010006901A (es) 2010-09-30
BRPI0821241A2 (pt) 2015-06-16
EP2230229A1 (en) 2010-09-22
AU2008339435B2 (en) 2012-08-16
JP5732198B2 (ja) 2015-06-10
RU2476423C2 (ru) 2013-02-27
CN101939290A (zh) 2011-01-05
ES2610574T3 (es) 2017-04-28
BRPI0821241B1 (pt) 2021-04-06
KR20100108519A (ko) 2010-10-07
AU2008339435A1 (en) 2009-06-25
HK1151513A1 (en) 2012-02-03
KR101583544B1 (ko) 2016-01-08
IL206332A0 (en) 2010-12-30
RU2010129950A (ru) 2012-01-27
TWI458494B (zh) 2014-11-01
US8269035B2 (en) 2012-09-18
SI2230229T1 (sl) 2017-03-31
DK2230229T3 (en) 2017-01-23
PL2230229T3 (pl) 2017-04-28
TW200930410A (en) 2009-07-16
CN101939290B (zh) 2013-11-06
US20100261931A1 (en) 2010-10-14
IL206332A (en) 2013-10-31
CA2709558A1 (en) 2009-06-25

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