DK2579902T3 - Fremgangsmåde til fremstilling af f-18-mærkede amyloid-beta-ligander - Google Patents

Fremgangsmåde til fremstilling af f-18-mærkede amyloid-beta-ligander Download PDF

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DK2579902T3
DK2579902T3 DK11723431.0T DK11723431T DK2579902T3 DK 2579902 T3 DK2579902 T3 DK 2579902T3 DK 11723431 T DK11723431 T DK 11723431T DK 2579902 T3 DK2579902 T3 DK 2579902T3
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ethoxy
compound
formula
hplc
vinyl
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DK11723431.0T
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DK2579902T4 (da
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Mathias Berndt
Matthias Friebe
Fabrice Samson
Rainer Braun
Gunnar Garke
Marianne Patt
Andreas Schildan
Christoph Smuda
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Piramal Imaging Sa
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/041—Heterocyclic compounds
    • A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K51/0453—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/041—Heterocyclic compounds
    • A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K51/0455—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
    • A61K51/121—Solutions, i.e. homogeneous liquid formulation
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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

Claims (10)

1. Fremgangsmåde til fremstilling af en forbindelse med formel I
I omfattende trinnene: Trin 1: Radiomærkning af en forbindelse med formel II med et F-18 fluoreret middel til opnåelse af en forbindelse med formel I, hvis R = H, eller til opnåelse af en forbindelse med formel III, hvis R = PG
Trin 2: Hvis R = PG, spaltning af den beskyttende gruppe PG til opnåelse af en forbindelse med formel I Trin 3: Oprensning og formulering af en forbindelse med formel I hvor: n = 1-6, X er udvalgt fra gruppen bestående af a) CH, b) N, R er udvalgt fra gruppen bestående af a) H, b) PG, PG er en "amin-beskyttende gruppe", LG er en fraspaltelig enhed, hvor der, i trin 3, anvendes en HPLC-fremgangsmåde, hvor HPLC-opløsningsmidlet eller opløsningsmiddelblandingen er en del af en injicerbar formulering af forbindelse I, som er egnet til injektion i mennesker, hvor HPLC-opløsningsmidlet er udvalgt fra gruppen bestående af ethanol, en vandig buffer eller en ethanol/vandig buffer-blanding.
2. Fremgangsmåde ifølge krav 1, hvor PG er udvalgt fra gruppen bestående af: a) Boc, b) trityl og c) 4-methoxytrityl.
3. Fremgangsmåde ifølge krav 1 eller 2, hvor LG er udvalgt fra gruppen bestående af: a) halogen og b) sulfonyloxy, halogen er chlor, brom eller iodo.
4. Fremgangsmåde ifølge krav 3, hvor sulfonyloxy er udvalgt fra gruppen omfattende: a) methansulfonyloxy, b) p-toluensulfonyloxy, c) (4-nitrophenyl)sulfonyloxy, d) (4-bromphenyl)sulfonyloxy.
5. Fremgangsmåde ifølge krav 1, hvor n = 3 og X = CH.
6. Fremgangsmåde ifølge krav 1, hvor n = 3, X = CH, R = Boc, og LG = methansulfonyloxy.
7. Fremgangsmåde ifølge krav 1-6, hvor den vandige buffer er udvalgt fra gruppen af opløsninger af natriumchlorid, natriumphosphat-buffer, ascorbin-syre, ascorbat-buffer eller blandinger deraf.
8. Fremgangsmåde ifølge krav 1 - 7, hvor HPLC-opløsningsmidlet er en blanding af ethanol og en vandig buffer omfattende ascorbinsyre eller ascor-binsyresalte.
9. Fremgangsmåde ifølge krav 1 - 8, hvor der anvendes 10-50 pmol af en forbindelse med formel II.
10. Fremgangsmåde ifølge krav 1 - 9, hvor fremgangsmåden udføres som en fuldautomatisk proces.
DK11723431.0T 2010-06-04 2011-05-30 Fremgangsmåde til fremstilling af f-18-mærkede amyloid-beta-ligander DK2579902T4 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10164949 2010-06-04
PCT/EP2011/058820 WO2011151283A1 (en) 2010-06-04 2011-05-30 Method for production of f-18 labeled amyloid beta ligands

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DK2579902T3 true DK2579902T3 (da) 2017-08-28
DK2579902T4 DK2579902T4 (da) 2019-10-21

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DK11723431.0T DK2579902T4 (da) 2010-06-04 2011-05-30 Fremgangsmåde til fremstilling af f-18-mærkede amyloid-beta-ligander

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US (2) US20130209363A1 (da)
EP (1) EP2579902B2 (da)
JP (2) JP5869562B2 (da)
KR (1) KR101761451B1 (da)
CN (1) CN103269724B (da)
AU (1) AU2011260421B2 (da)
BR (1) BR112012030935B1 (da)
CA (1) CA2801530C (da)
DK (1) DK2579902T4 (da)
EA (1) EA022897B1 (da)
ES (1) ES2642086T5 (da)
HR (1) HRP20171397T4 (da)
HU (1) HUE033237T2 (da)
IL (1) IL223358A (da)
LT (1) LT2579902T (da)
MX (1) MX345069B (da)
PL (1) PL2579902T5 (da)
PT (1) PT2579902T (da)
SG (1) SG185782A1 (da)
SI (1) SI2579902T2 (da)
TW (1) TWI583397B (da)
WO (1) WO2011151283A1 (da)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2012014115A (es) * 2010-06-04 2013-07-03 Piramal Imaging Sa Metodo para la produccion de ligandos beta amiloide marcados con 18f.
ES2642086T5 (es) 2010-06-04 2020-04-13 Life Molecular Imaging Sa Procedimiento para la producción de ligandos de beta amiloide marcados con F-18
WO2012089594A1 (en) * 2010-12-29 2012-07-05 Ge Healthcare Limited Eluent solution
CN105833303A (zh) * 2011-06-21 2016-08-10 皮拉莫尔影像股份公司 适用于pet成像的氟化茋的制剂
CA2852840A1 (en) * 2011-10-19 2013-04-25 Piramal Imaging Sa Improved method for production of f-18 labeled a.beta. ligands
KR101326000B1 (ko) * 2012-01-30 2013-11-07 재단법인 아산사회복지재단 수소이온 농도가 조절된 플루오린-18의 용리액 제조 및 이를 이용한 플루오린-18의 표지방법
GB201318450D0 (en) * 2013-10-18 2013-12-04 Ge Healthcare Ltd Closed evaporation system
DK3538161T3 (da) 2016-11-08 2022-09-05 Univ California Fremgangsmåder til flerdosissyntese af [F-18]FDDNP til kliniske indstillinger
JP7241013B2 (ja) * 2017-03-17 2023-03-16 日本メジフィジックス株式会社 イオフルパンの製造方法
JP2021512064A (ja) * 2018-01-24 2021-05-13 エーシー・イミューン・エス・アー 画像化化合物を調製する新規方法
CN109867591B (zh) * 2019-03-12 2020-11-06 浙江大学 18f标记的aie荧光/pet双模态探针及其制备方法和应用

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US5723103A (en) * 1994-12-09 1998-03-03 Vanderbilt University Substituted benzamides and radioligand analogs and methods of use
EP1560601B1 (en) 2002-11-05 2010-07-07 Ion Beam Applications S.A. Stabilization of aqueous compositions of 18f-isotope labelled 2-fluoro-2-deoxy-d-glucose with ethanol
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PL2213652T3 (pl) * 2004-12-17 2015-04-30 Univ Pennsylvania Pochodne stilbenu i ich zastosowanie do wiązania i obrazowania płytek amyloidowych
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ES2642086T5 (es) 2010-06-04 2020-04-13 Life Molecular Imaging Sa Procedimiento para la producción de ligandos de beta amiloide marcados con F-18

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PL2579902T5 (pl) 2020-08-10
SI2579902T1 (sl) 2017-10-30
SG185782A1 (en) 2013-01-30
EP2579902B2 (en) 2019-08-14
US9592308B2 (en) 2017-03-14
KR20130136423A (ko) 2013-12-12
MX345069B (es) 2017-01-16
HRP20171397T4 (hr) 2019-11-15
HUE033237T2 (hu) 2017-11-28
PL2579902T3 (pl) 2017-12-29
TWI583397B (zh) 2017-05-21
CA2801530A1 (en) 2011-12-08
HRP20171397T1 (hr) 2017-11-03
AU2011260421A1 (en) 2013-01-10
US20130209363A1 (en) 2013-08-15
SI2579902T2 (sl) 2019-10-30
MX2012014117A (es) 2013-07-03
CN103269724B (zh) 2017-06-23
EA022897B1 (ru) 2016-03-31
TW201204395A (en) 2012-02-01
US20160184465A1 (en) 2016-06-30
AU2011260421B2 (en) 2015-06-04
LT2579902T (lt) 2017-09-25
IL223358A (en) 2015-09-24
JP2013532137A (ja) 2013-08-15
EA201201645A1 (ru) 2013-05-30
JP2016047831A (ja) 2016-04-07
ES2642086T5 (es) 2020-04-13
PT2579902T (pt) 2017-08-17
DK2579902T4 (da) 2019-10-21
KR101761451B1 (ko) 2017-07-25
BR112012030935A2 (pt) 2016-11-01
BR112012030935B1 (pt) 2020-11-17
CA2801530C (en) 2017-09-12
WO2011151283A1 (en) 2011-12-08
ES2642086T3 (es) 2017-11-15
EP2579902A1 (en) 2013-04-17
JP5869562B2 (ja) 2016-02-24
EP2579902B1 (en) 2017-07-12
CN103269724A (zh) 2013-08-28

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