DK1633703T3 - Isotopmærkede kemisk stabile reagenser og fremgangsmåder til syntese deraf - Google Patents

Isotopmærkede kemisk stabile reagenser og fremgangsmåder til syntese deraf Download PDF

Info

Publication number
DK1633703T3
DK1633703T3 DK04753682.6T DK04753682T DK1633703T3 DK 1633703 T3 DK1633703 T3 DK 1633703T3 DK 04753682 T DK04753682 T DK 04753682T DK 1633703 T3 DK1633703 T3 DK 1633703T3
Authority
DK
Denmark
Prior art keywords
alkyl
aryl
cycloalkyl
compound
hydrogen
Prior art date
Application number
DK04753682.6T
Other languages
English (en)
Inventor
Jerry Scot Pounds
Original Assignee
Perkinelmer Las Inc
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
Application filed by Perkinelmer Las Inc filed Critical Perkinelmer Las Inc
Application granted granted Critical
Publication of DK1633703T3 publication Critical patent/DK1633703T3/da

Links

Classifications

    • 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
    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • 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
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (15)

1. Isotopmærket reagens omfattende: en forbindelse med formlen
hvor a i hver forekomst uafhængigt er et carbonatom-massetal på mellem 11 og 14, og hvor forbindelsen er isotopisk beriget med mindst ét carbon, hvor a er 11, 13 eller 14, hvor b i hver forekomst uafhængigt er et hydrogenatom-masse-tal på mellem 1 og 3, hvor L er en fraspaltelig gruppe R1S02-0-, hvor n er 0, hvor R1 er aryl, C1-C20 alkyl, C2-C20 alkenyl og C2-C20 alkynyl, hvilken aryl, C1-C20 alkyl, C2-C20 alkenyl og C2-C20 alkynyl valgfrit kan modificeres ved at erstatte et hydrogen, som er bundet til et carbonatom, med en substituent, der uafhængigt er valgt blandt alkyl, amino, cykloalkyl, halogen, nitro, cyano, -OR2, acyl og -COOR3, hvor nævnte aryl er et monovalent, monocyklisk eller bicyklisk aromatisk carbon-hydridradikal med 6 til 10 ringatomer, nævnte alkyl betegner C1-C6 alkyl, nævnte amino betegner NH2, NHR4 eller NR4R5, hvor R4 og R5 uafhængigt er valgt blandt C1-C6 alkyl, en aryl defineret som et monocyklisk eller bicyklisk aromatisk carbonhydridradikal med 6 til 10 ringatomer, C1-C6 alkoxy eller Ce phenoxy, nævnte cykloalkyl betegner cyklopentyl eller cyklohexyl, nævnte halogen betegner fluor, chlor, brom eller iod, nævnte R2 betegner hydrogen, C1-C6 alkyl, C5 eller Ce cykloalkyl, en hetero-cykloalkyl valgt blandt furanyl, tetrahydrofuranyl, epoxy, tetrahydropyranyl, di-oxynyl, thiacyklopentyl, azeridyl pyrolidyl, piperadyl, morpholyl og C1-C6 alkyl-substituerede former deraf og en phenyl, som er blevet modificeret ved at erstatte en hydrogen bundet til et carbonatom med hver substituent, der uaf-
hængigt er valgt blandt alkyl, amino, cykloalkyl, halogen, nitro, cyano, -OR2, acyl og -COOR3, og nævnte R3 betegner hydrogen eller C1-C6 alkyl.
2. Reagens ifølge krav 1, hvor R1 er aryl.
3. Reagens ifølge krav 1, hvor R1 er aryl, som er blevet modificeret ved at erstatte et hydrogen bundet til et carbonatom med hver substituent, der uafhængigt er valgt blandt alkyl, amino, cykloalkyl, halogen, nitro, cyano, -OR2, acyl og -COOR3, hvor alkyl, amino, cykloalkyl, halogen, R2 og R3 er som defineret i krav 1.
4. Reagens ifølge krav 3, hvor R1 er para-CH3C6H5.
5. Reagens ifølge krav 3, hvor R1 er para-N02-C6H5.
6. Fremgangsmåde til fremstilling af en forbindelse ifølge krav 1 omfattende et trin, hvor aCbH3(aCbH2)nX reageres med [l]:'~m2+ hvor a i hver forekomst uafhængigt er et carbonatom-massetal på mellem 11 og 14, og hvor forbindelsen er isotopisk beriget med mindst ét carbon, hvor a er 11,13 eller 14; b i hver forekomst uafhængigt er et hydrogenatom-massetal på mellem 1 og 3; L er en fraspaltelig gruppe R1S020-; n er 0; R1 er aryl, C1-C20 alkyl, C2-C20 alkenyl og C2-C20 alkynyl, hvilken aryl, C1-C20 alkyl, C2-C20 alkenyl og C2-C20 alkynyl valgfrit kan modificeres ved at erstatte et hydrogen bundet til et carbonatom med en substituent, der uafhængigt er valgt blandt alkyl, amino, cykloalkyl, halogen, nitro, cyano, -OR2, acyl og -COOR3, hvor nævnte aryl er et monovalent, monocyklisk eller bicyklisk aromatisk carbon-hydridradikal med 6 til 10 ringatomer, nævnte alkyl betegner C1-C6 alkyl, nævnte amino betegner NH2, NHR4 eller NR4R5, hvor R4 og R5 uafhængigt er valgt blandt C1-C6 alkyl, en aryl defineret som et monocyklisk eller bicyklisk aromatisk carbonhydridradikal med 6 til 10 ringatomer, C1-C6 alkoxy eller C6 phenoxy, nævnte cykloalkyl betegner cyklopentyl eller cyklohexyl, nævnte halogen betegner fluor, chlor, brom eller iod, nævnte R2 betegner hydrogen, CrCe alkyl, C5 eller Ce cykloalkyl, en hetero-cykloalkyl valgt blandt furanyl, tetrahydrofuranyl, epoxy, tetrahydropyranyl, di-oxynyl, thiacyklopentyl, azeridyl pyrolidyl, piperadyl, morpholyl og Ci-Ce alkyl-substituerede former deraf og en phenyl, som er blevet modificeret ved at erstatte en hydrogen bundet til et carbonatom med hver substituent, der uafhængigt er valgt blandt alkyl, amino, cykloalkyl, halogen, nitro, cyano, -OR2, acyl og -COOR3, og nævnte R3 betegner hydrogen eller C1-C6 alkyl; X er et chlorid, bromid eller iodid; M er en metalion eller oniumion; Z+ er en kationisk valens af M; Y- er en anionisk valens af L; P er den absolutte værdi af den ioniske valens divideret med den kationiske valens; og hvor reaktionen sker under vandfrie betingelser i et aprotisk opløsningsmiddel.
7. Fremgangsmåde ifølge krav 6, hvor reaktionstrinnet sker ved opvarmning til en temperatur, der er mindre end eller lig med en kogetemperatur for det aprotiske opløsningsmiddel.
8. Fremgangsmåde ifølge krav 6, hvor aCbH3(aCbH2)nX er 12C3H3I.
9. Fremgangsmåde til isotopisk alkylering af et målmolekyle, hvilken fremgangsmåde omfatter, at målmolekylet blandes med en forbindelse med formel I ifølge et hvilket som helst af kravene 1 eller 2.
10. Fremgangsmåde ifølge krav 9, hvor målmolekylet er en nukleofil.
11. Fremgangsmåde ifølge krav 9, hvor målmolekylet er et metalsalt af en organisk anion.
12. Fremgangsmåde ifølge krav 9, hvor målmolekylet er en tertiær amin.
13. Anvendelse af en forbindelse med formel I ifølge et hvilket som helst af kravene 1 eller 2 til isotopisk mærkning af et målmolekyle.
14. Forbindelse ifølge krav 1, som er opnået ved fremgangsmåden ifølge krav 6.
15. Kommerciel pakke omfattende en forbindelse med formlen I ifølge krav 1 sammen med instruktioner til anvendelse deraf som et isotopmærket alkyleringsreagens.
DK04753682.6T 2003-05-30 2004-05-28 Isotopmærkede kemisk stabile reagenser og fremgangsmåder til syntese deraf DK1633703T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US32023803P 2003-05-30 2003-05-30
PCT/US2004/016898 WO2004108636A2 (en) 2003-05-30 2004-05-28 Isotopically labeled chemically stable reagents and process for the synthesis thereof

Publications (1)

Publication Number Publication Date
DK1633703T3 true DK1633703T3 (da) 2019-04-15

Family

ID=33510232

Family Applications (1)

Application Number Title Priority Date Filing Date
DK04753682.6T DK1633703T3 (da) 2003-05-30 2004-05-28 Isotopmærkede kemisk stabile reagenser og fremgangsmåder til syntese deraf

Country Status (8)

Country Link
US (3) US8058464B2 (da)
EP (1) EP1633703B1 (da)
JP (1) JP5204401B2 (da)
CA (1) CA2527809C (da)
DK (1) DK1633703T3 (da)
ES (1) ES2714780T3 (da)
HU (1) HUE044033T2 (da)
WO (1) WO2004108636A2 (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK1633703T3 (da) * 2003-05-30 2019-04-15 Perkinelmer Las Inc Isotopmærkede kemisk stabile reagenser og fremgangsmåder til syntese deraf
US8299258B2 (en) 2008-11-04 2012-10-30 Cambrex Charles City Method of making piperidine derivatives
WO2012033374A2 (ko) * 2010-09-09 2012-03-15 서강대학교 산학협력단 1,2,3-트리아졸륨 염을 갖는 설포네이트 전구체, 그 제조방법 및 이를 사용하는 분자내 친핵성 플루오르화반응

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4269777A (en) * 1979-05-21 1981-05-26 Wisconsin Alumni Research Foundation Isotopically labeled vitamin D derivatives and processes for preparing same
JPS56123938A (en) * 1980-03-06 1981-09-29 Yuki Gosei Yakuhin Kogyo Kk Preparation of 3,4,5-trimethoxybenzoic acid
DE4012792A1 (de) * 1990-04-21 1991-10-24 Bayer Ag Verfahren zur herstellung von 1-alkoxyhexatrien-2-carbonsaeureestern
JP2641363B2 (ja) * 1992-04-22 1997-08-13 三共株式会社 新規なフェネチルアルコール及びその製法
FR2725982B1 (fr) * 1994-10-24 1996-12-20 Rhone Poulenc Chimie Procede de preparation d'isovanilline
DE19643592A1 (de) * 1996-10-22 1998-04-23 Bayer Ag Verfahren zur Herstellung von alpha-Alkoxy-alpha-trifluormethyl-arylessigsäureestern und -arylessigsäuren
WO1999012902A1 (fr) * 1997-09-11 1999-03-18 Kureha Kagaku Kogyo Kabushiki Kaisha Derives de methylpropylamines n-heterocycliques, procede de productions de ces derives et germicides
US6713044B2 (en) * 2002-02-13 2004-03-30 The Regents Of The University Of California Synthesis of [2H1, 13C], [2H2, 13C] and [2H3, 13C]methyl aryl sulfides
DK1633703T3 (da) * 2003-05-30 2019-04-15 Perkinelmer Las Inc Isotopmærkede kemisk stabile reagenser og fremgangsmåder til syntese deraf

Also Published As

Publication number Publication date
EP1633703A4 (en) 2006-11-15
US20130030184A1 (en) 2013-01-31
US20060205953A1 (en) 2006-09-14
US8987501B2 (en) 2015-03-24
WO2004108636A2 (en) 2004-12-16
WO2004108636A3 (en) 2005-09-09
EP1633703B1 (en) 2018-12-26
US8329934B2 (en) 2012-12-11
ES2714780T3 (es) 2019-05-30
EP1633703A2 (en) 2006-03-15
US20120004413A1 (en) 2012-01-05
HUE044033T2 (hu) 2019-09-30
JP5204401B2 (ja) 2013-06-05
JP2006526645A (ja) 2006-11-24
CA2527809A1 (en) 2004-12-16
US8058464B2 (en) 2011-11-15
CA2527809C (en) 2012-07-10

Similar Documents

Publication Publication Date Title
Kim et al. Tetrabutylammonium tetra (tert-butyl alcohol)-coordinated fluoride as a facile fluoride source
CN101094824B (zh) 在醇溶剂中制备有机氟化物的方法
AU2008315950B2 (en) Compounds for use in imaging, diagnosing, and/or treatment of diseases of the central nervous system or of tumors
JP2020117507A (ja) ヨウ素（ｉｉｉ）を媒介とする放射性フッ素化
US8987501B2 (en) Isotopically labeled chemically stable reagents and process for the synthesis thereof
JP2018536031A (ja) ジアリールヨードニウム塩を使用してヨード−又はアスタトアレーンを合成するための方法
Krasikova et al. Phase Transfer catalysts and role of reaction environment in nucleophilc radiofluorinations in automated synthesizers
BR112013008404B1 (pt) Processo para a preparação de (3s,3s) 4,4-dissulfanodiilbis (ácido 3-aminobutano 1- sulfônico)
JP2011530572A (ja) ヨードニウム塩のフッ素化の改良
KR101842989B1 (ko) 카보닐기를 갖는 알코올 용매를 이용한 플루오르화 화합물의 제조방법
JP2020037545A (ja) 酸素同位体標識カルボン酸塩化合物、酸素同位体標識用試薬、酸素同位体標識カルボン酸塩化合物の製造方法、及び酸素同位体標識アルコールの製造方法
Gu et al. Labeling strategies with F-18 for positron emission tomography imaging
US20110184159A1 (en) Process for production of radiopharmaceuticals
US20150367005A1 (en) Method of synthesizing fluorine-18 labeled radiopharmaceuticals in ethanol and water
EP1960324B1 (en) Method for the preparation of [18f]fluoroalkylhalides
US6979431B2 (en) Method for labelling technetium or rhenium using borohydride exchange resin
EP3842405A1 (en) Method for preparing fluorine-18-labeled fluoromethyl-substituted radiopharmaceuticals using selective azide substitution reaction and precursor scavenging
US6888019B1 (en) Method of preparing rhenium complex using borohydride exchange resin
KR101229929B1 (ko) 1,2,3-트리아졸기를 갖는 새로운 말레이미드 화합물, 이의 제조방법 및 이를 보결그룹으로 하는 생체화합물의 ｆ­18 표지방법
KR20170076933A (ko) 불소-18 동위원소를 함유하는 방사성 화합물의 제조방법
JP2006526645A5 (da)
KR930003753B1 (ko) 방사성동위원소 표지화합물로서의 글리세롤(2-14c)의 제조방법
JP2016074605A (ja) アミノ酸の製造方法およびアミノ酸合成キット
CN117777011A (zh) 一种烷氧基取代的吡啶类化合物的制备方法
AU2012298458A1 (en) Simplified radiosynthesis of [18F]fluoromethyl bromide