DK2646411T3 - Preparation of pet precursor - Google Patents

Preparation of pet precursor Download PDF

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Publication number
DK2646411T3
DK2646411T3 DK11801996.7T DK11801996T DK2646411T3 DK 2646411 T3 DK2646411 T3 DK 2646411T3 DK 11801996 T DK11801996 T DK 11801996T DK 2646411 T3 DK2646411 T3 DK 2646411T3
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DK
Denmark
Prior art keywords
compound
formula
carbamate
acid substituent
acid
Prior art date
Application number
DK11801996.7T
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English (en)
Inventor
Tom Christian Berg
Anne Nilsen
Original Assignee
Blue Earth Diagnostics Ltd
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Publication of DK2646411T3 publication Critical patent/DK2646411T3/da

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    • 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
    • C07C269/04—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 from amines with formation of carbamate 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38—Separation; Purification; Stabilisation; Use of additives
    • C07C227/40—Separation; Purification
    • 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
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
    • 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
    • C07C269/08—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (15)

1. Fremgangsmåde til fremstilling af en forbindelse med formlen Illa:
hvor: R betegner en alkylgruppe med 1 til 5 carbonatomer udvalgt fra methyl, ethyl, 1- propyl eller isopropyl; X betegner en beskyttelsesgruppe for en alkohol udvalgt fra benzyl (Bn), methoxymethyl (MOM), 2-methoxyethoxymethyl (MEM), methylthiomethyl (MTM), tetrahydropyranyl (THP), benzyloxymethyl (BOM), p-methoxyphenyl, /;-mcthoxybcnzyl (MPM), p-methoxybenzyloxymethyl (PMBM), triisopropylsilyl (TIPS), tert-butyldimethylsilyl (TBDMS), 2-(trimethylsilyl)ethoxymethyl (SEM) og (phenyldimethylsilyl)methoxymethyl (SMOM); Y betegner en beskyttelsesgruppe for en amin udvalgt fra tert-h utyl c arb a m at (Boc), 9-fluorenylmethylcarbamat (Fmoc), methylcarbamat, ethylcarbamat, 2-chlor-3-indenylmethylcarbamat (Climoc), benz[f]inden-3-ylmethylcarbamat (Bimoc), 2,2,2-trichlorethylcarbamat (Troc), 2-chlorethylcarbamat, l,l-dimethyl-2,2-dibromethylcarbamat (DB-z-BOC), l,l-dimethyl-2,2,2-trichlorethylcarbamat (TCBOC), benzylcarbamat (Cbz) og diphenylmethylcarbamat, og hvor fremgangsmåden omfatter en oparbejdningsproces, der omfatter følgende trin: i) tilvejebringelse af et råt reaktionsprodukt, der omfatter forbindelsen med formlen Illa; ii) tilsætning af ethylacetat til det rå reaktionsprodukt fra trin i) for at fremstille en suspension; iii) tilsætning af vand til suspensionen fra trin ii) for at danne et tofasesystem, der omfatter en vandig fase og en organisk fase, og kassering af den vandige fase; iv) tilsætning af en syre til den organiske fase fra trin iii) for at danne et tofasesystem, der omfatter en sur, vandig fase og en organisk fase, og kassering af den sure, vandige fase; v) vask af den organiske fase fra trin iv) med vand.
2. Fremgangsmåde ifølge krav 1, hvor X er benzyl.
3. Fremgangsmåde ifølge enten krav 1 eller krav 2, hvor R er ethyl.
4. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 3, hvor Y er tert-butylcarbamat (Boc).
5. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 4, hvor i trin ii) mængden af tilsat ethylacetat sammenlignet med mængden af et udgangsmateriale, der omfatter en forbindelse med formlen Ila:
hvor X og R er defineret som i krav 1; er mellem 15:1 og 25:1 i volumen/vægt-%.
6. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5, hvor i trin iii) mængden af tilsat vand er ca. det halve af mængden af ethylacetat tilsat i trin ii).
7. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 6, hvor i trin iv) den tilsatte syre er HC1.
8. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 7, hvor i trin iv) vask indbefatter vask med rent vand, med en vandig opløsning af natriumhydrogencarbonat og med saltopløsning.
9. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 8, der endvidere indbefatter trinnene med opkoncentrering af sammensætningen fra trin iv) under reduceret tryk, tørring og oprensning.
10. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 9, hvor det rå reaktionsprodukt indbefatter en blanding af syn- og anti-enantiomeme af forbindelsen med formlen Illa.
11. Fremgangsmåde til fremstilling af forbindelsen med formlen Va:
hvor Y er som defineret i enten krav 1 eller krav 4 og R er som defineret i enten krav 1 eller krav 3, og LG er en fraspaltelig gruppe; hvor fremgangsmåden omfatter fremstilling af forbindelsen med formlen Illa ifølge fremgangsmåden ifølge et hvilket som helst af kravene 1-10 og omdannelse af -O-X til -LG.
12. Fremgangsmåde som defineret i krav 11 hvor den fraspaltelige gruppe er en halogensubstituent eller en gruppe repræsenteret ved -OR2, hvor R2 enten er en fluorsulfonsyresubstituent eller en aromatisk sulfonsyresubstituent.
13. Fremgangsmåde som defineret i krav 12 hvor den fraspaltelige gruppe er udvalgt fra en toluensulfonsyresubstituent, en nitrobenzensulfonsyresubstituent, en benzensulfonsyresubstituent, en trifluormethansulfonsyresubstituent, en fluorsulfonsyresubstituent eller en perfluoralkylsulfonsyresubstituent.
14. Fremgangsmåde som defineret i enten krav 11 eller krav 12, hvor forbindelsen med formlen Va er en forbindelse med formlen V:
15. Fremgangsmåde til fremstilling af en forbindelse med formlen VI:
hvor fremgangsmåden omfatter fremstilling af forbindelsen med formlen Va ifølge fremgangsmåden som defineret i et hvilket som helst af kravene 11-14 efterfulgt af nukleofil fortrængning af LG med formlen Va med [18F]fluorid.
DK11801996.7T 2010-11-29 2011-11-28 Preparation of pet precursor DK2646411T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41749010P 2010-11-29 2010-11-29
PCT/EP2011/071145 WO2012072567A1 (en) 2010-11-29 2011-11-28 Preparation of pet precursor

Publications (1)

Publication Number Publication Date
DK2646411T3 true DK2646411T3 (da) 2017-10-16

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Application Number Title Priority Date Filing Date
DK11801996.7T DK2646411T3 (da) 2010-11-29 2011-11-28 Preparation of pet precursor

Country Status (13)

Country Link
US (1) US9278916B2 (da)
EP (1) EP2646411B1 (da)
JP (1) JP6018578B2 (da)
KR (1) KR20130140041A (da)
CN (1) CN103221382B (da)
AU (1) AU2011335084B2 (da)
CA (1) CA2820363A1 (da)
DK (1) DK2646411T3 (da)
ES (1) ES2643500T3 (da)
MX (1) MX2013006050A (da)
NO (1) NO2646411T3 (da)
RU (1) RU2587308C2 (da)
WO (1) WO2012072567A1 (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201214220D0 (en) * 2012-08-09 2012-09-19 Ge Healthcare Ltd Radiosynthesis
CN114767929A (zh) * 2022-03-14 2022-07-22 上海理工大学 一种连通多孔PHBHHx骨填充微球材料及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3325225B2 (ja) 1998-04-20 2002-09-17 株式会社トクヤマ Ｎ−炭化水素オキシカルボニルアミノ酸エステルの製造方法
ES2663496T3 (es) * 2005-11-29 2018-04-13 Nihon Medi-Physics Co., Ltd. Compuesto precursor de compuesto orgánico marcado con halógeno radiactivo
BRPI0711144B1 (pt) 2006-05-11 2017-03-28 Nihon Mediphysics Co Ltd processo para produção de um composto orgânico marcado com flúor radioativo
NO345488B1 (no) * 2006-12-27 2021-03-01 Nihon Mediphysics Co Ltd Fremgangsmåte for fremstilling av forløperforbindelse for radioaktiv fluormerket organisk forbindelse

Also Published As

Publication number Publication date
RU2013122655A (ru) 2015-01-10
JP6018578B2 (ja) 2016-11-02
CN103221382A (zh) 2013-07-24
CN103221382B (zh) 2016-06-01
AU2011335084A1 (en) 2013-07-04
US20130245307A1 (en) 2013-09-19
ES2643500T3 (es) 2017-11-23
RU2587308C2 (ru) 2016-06-20
AU2011335084B2 (en) 2015-08-20
US9278916B2 (en) 2016-03-08
WO2012072567A1 (en) 2012-06-07
KR20130140041A (ko) 2013-12-23
CA2820363A1 (en) 2012-06-07
EP2646411A1 (en) 2013-10-09
EP2646411B1 (en) 2017-08-16
JP2014506236A (ja) 2014-03-13
MX2013006050A (es) 2013-06-28
NO2646411T3 (da) 2018-01-13

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