JP2012522052A - 放射性標識試薬及び方法 - Google Patents
放射性標識試薬及び方法 Download PDFInfo
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- JP2012522052A JP2012522052A JP2012503484A JP2012503484A JP2012522052A JP 2012522052 A JP2012522052 A JP 2012522052A JP 2012503484 A JP2012503484 A JP 2012503484A JP 2012503484 A JP2012503484 A JP 2012503484A JP 2012522052 A JP2012522052 A JP 2012522052A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
【選択図】なし
Description
2−トリメチルアンモニウムニコチン酸のN−ヒドロキシスクシンイミド(NHS)エステルを6−クロロニコチン酸から合成し、上記の方法と同様にして19Fで標識した。
両エステルは良好な収率(6−クロロニコチン酸から出発して>30%)で合成され、室温のアセトニトリル中においてフッ化物と容易に反応した。NHSエステルはTfpエステルより加水分解を受けやすく、したがってそれ以上は評価しなかった。Tfpエステルの反応を30分間にわたり1H−NMRによって調べたところ、室温でフッ化物の迅速な取込みが示され、2.5分後には32%の出発原料が所望のフッ素化生成物に転化された。1組の実験では、70%のフッ素化生成物が20分未満で得られた。所望の生成物と共に、2種のニコチン酸誘導体が副生物として同定された。
アセトニトリル/0.1Mリン酸ナトリウム(pH9)の1:1溶液(全量3mL)中において、実施例1のフッ素化生成物(1mg)と適宜に官能化されたRGDペプチド(5mg、国際公開第01/77415号及び同第03/006491号に記載されているようにして製造された)とを反応させることで、LC−MSにより分析して所望の生成物が得られた。LC−MS条件:Phenomenex Luna C18(2) 3μ 2×50mm、移動相A:水/0.1%トリフルオロ酢酸(TFA)、移動相B:アセトニトリル/0.1%TFA、流量:0.6mL/分、5分で10〜30%B。保持時間(Rt)=3.42分、M+H+(期待値1381.5、実測値1381.6)。
2mLのアセトニトリル中に[18F]フルオロニコチン酸2,3,5,6−テトラフルオロフェニルエステルを含む粗反応混合物を蒸留水で30%アセトニトリルまで希釈した。水溶液を(製造者の推奨条件に従ってコンディショニングした)カートリッジ付きのOasis MCXに通した。次いで、カートリッジを5mLの蒸留水で洗った。次いで、精製された生成物を100%アセトニトリルによって90%を超える放射化学純度でカラムから溶出した。未反応前駆体トリメチル−[5−(2,3,5,6−テトラフルオロ−フェノキシカルボニル)ピリジン−2−イル]アンモニウムメタンスルホネートはすべてカートリッジ上に残留した。
Claims (10)
- 次の式(I)の化合物。
- 次の式(Ia)を有する、請求項1記載の化合物。
- 次の式(II)の化合物又はその塩。
- Lがトリ(C1-6アルキル)アンモニウム(好適にはトリメチルアンモニウム)である、請求項3記載の式(II)の化合物又はその塩。
- 次式の化合物である、請求項3又は請求項4記載の式(II)の化合物。
- 請求項1又は請求項2で定義された式(I)又は式(Ia)の化合物を次の式(III)の化合物と反応させて次の式(IV)の18F−生成物を得ることを含んでなる18F−フッ素化方法。
- 生体分子がペプチドである、請求項6記載の方法。
- 生体分子が、オクトレオチドのようなソマトスタチン類似体、ボンベシン、血管作用性小腸ペプチド、走化性ペプチド類似体、α−メラノサイト刺激ホルモン、ニューロテンシン、Arg−Gly−Aspペプチド及びその類似体、ヒトプロインスリン結合ペプチド、エンドセリン、アンギオテンシン並びにホルミル−ノルロイシル−ロイシル−フェニルアラニル−ノルロイシル−チロシル−リシンから選択されるペプチドである、請求項6又は請求項7記載の方法。
- 生体分子が次式のフラグメントを含む、請求項6乃至請求項8のいずれか1項記載の方法。
- 生体分子が次の式(A)のペプチドである、請求項6乃至請求項9のいずれか1項記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US16449409P | 2009-03-30 | 2009-03-30 | |
GB0905438.8 | 2009-03-30 | ||
US61/164,494 | 2009-03-30 | ||
GBGB0905438.8A GB0905438D0 (en) | 2009-03-30 | 2009-03-30 | Radiolabelling reagents and methods |
PCT/US2010/028078 WO2010114723A1 (en) | 2009-03-30 | 2010-03-22 | Radiolabelling reagents and methods |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2012522052A true JP2012522052A (ja) | 2012-09-20 |
Family
ID=40671939
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012503484A Ceased JP2012522052A (ja) | 2009-03-30 | 2010-03-22 | 放射性標識試薬及び方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US8530620B2 (ja) |
EP (1) | EP2414333B1 (ja) |
JP (1) | JP2012522052A (ja) |
KR (1) | KR20110133038A (ja) |
CN (2) | CN102356069B (ja) |
AU (1) | AU2010232828A1 (ja) |
BR (1) | BRPI1011531A2 (ja) |
CA (1) | CA2757016A1 (ja) |
ES (1) | ES2404346T3 (ja) |
GB (1) | GB0905438D0 (ja) |
MX (1) | MX2011010295A (ja) |
PL (1) | PL2414333T3 (ja) |
PT (1) | PT2414333E (ja) |
RU (1) | RU2524284C2 (ja) |
WO (1) | WO2010114723A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016531851A (ja) * | 2013-09-26 | 2016-10-13 | イーライ リリー アンド カンパニー | タウ画像化剤の調製のための新規化合物および使用、ならびにタウ画像化製剤 |
JP2018531243A (ja) * | 2015-09-30 | 2018-10-25 | ドイチェス クレブスフォルシュンクスツェントルム | 前立腺特異的膜抗原(psma)の18f−タグ付加インヒビターおよび前立腺癌についての画像化剤としてのその使用 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107382846B (zh) | 2008-08-01 | 2021-07-06 | 约翰.霍普金斯大学 | Psma-结合剂及其用途 |
US9180213B2 (en) | 2010-12-09 | 2015-11-10 | Ge Healthcare Limited | Radiotracer compositions |
WO2013048811A1 (en) | 2011-09-30 | 2013-04-04 | Ge Healthcare Limited | Imaging and radiotherapy methods for tumour stem cells |
ES2912753T3 (es) * | 2014-08-24 | 2022-05-27 | Max Planck Gesellschaft Zur Foerderung Der Wss | Método para la producción de ésteres activos marcados con 18F y su aplicación ejemplificada por la preparación de un marcador de PET específico de PSMA |
GB201518918D0 (en) * | 2015-10-26 | 2015-12-09 | Norsk Medisinsk Syklotronsenter As And Uni I Oslo | Method |
WO2018022603A1 (en) * | 2016-07-25 | 2018-02-01 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods of making 18f-labeled precursors and peptides, labeled c-met binding peptides, and methods of use thereof |
WO2018169942A1 (en) * | 2017-03-13 | 2018-09-20 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Method of synthesizing 18f radiolabeled biomolecular agents |
GB202019006D0 (en) | 2020-12-02 | 2021-01-13 | Vestlandets Innovasjonsselskap As | GFR targeting compounds |
Citations (3)
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WO2004002984A2 (fr) * | 2002-07-01 | 2004-01-08 | Commissariat A L'energie Atomique | Composes de maleimides marques, leur procede de preparation et leur utilisation pour le marquage de macromolecules |
WO2009035959A2 (en) * | 2007-09-10 | 2009-03-19 | Ge Healthcare Limited | Radiofluorination methods |
FR2926079A1 (fr) * | 2008-01-03 | 2009-07-10 | Commissariat Energie Atomique | Procede de preparation d'un derive de purine marque, ledit derive et ses utilisations |
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US5346686A (en) * | 1992-10-05 | 1994-09-13 | Mallinckrodt Medical, Inc. | Labelled interleukin-8 and medical uses thereof |
EP0850320B1 (en) * | 1996-01-23 | 1999-12-08 | Rapigene, Inc. | Methods for detecting binding of ligand pair with enhanced sensitivity |
DE69719529T2 (de) * | 1996-10-17 | 2003-12-11 | Immunomedics, Inc. | Nichtantigenes toxinkonjugat und fusionsprotein eines internalisierendes rezeptorsystems |
AU9375698A (en) * | 1997-09-03 | 1999-03-22 | Immunomedics Inc. | Fluorination of proteins and peptides for f-18 positron emission tomography |
US6350360B1 (en) | 2000-04-07 | 2002-02-26 | Sandia Coroporation | Method of fabricating a 3-dimensional tool master |
GB0115927D0 (en) * | 2001-06-29 | 2001-08-22 | Nycomed Amersham Plc | Solid-phase nucleophilic fluorination |
RU2303042C2 (ru) | 2001-07-10 | 2007-07-20 | Джи-И Хелткер АС | Соединения на основе пептидов для направленной доставки к рецепторам интегринов |
GB0305704D0 (en) | 2003-03-13 | 2003-04-16 | Amersham Plc | Radiofluorination methods |
GB0317815D0 (en) | 2003-07-30 | 2003-09-03 | Amersham Health As | Imaging agents |
GB0329716D0 (en) | 2003-12-23 | 2004-01-28 | Amersham Plc | Radical trap |
GB0420344D0 (en) * | 2004-09-14 | 2004-10-13 | Amersham Plc | Diagnostic compounds |
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-
2009
- 2009-03-30 GB GBGB0905438.8A patent/GB0905438D0/en not_active Ceased
-
2010
- 2010-03-22 PL PL10710143T patent/PL2414333T3/pl unknown
- 2010-03-22 AU AU2010232828A patent/AU2010232828A1/en not_active Abandoned
- 2010-03-22 ES ES10710143T patent/ES2404346T3/es active Active
- 2010-03-22 KR KR1020117022881A patent/KR20110133038A/ko not_active Application Discontinuation
- 2010-03-22 JP JP2012503484A patent/JP2012522052A/ja not_active Ceased
- 2010-03-22 EP EP10710143A patent/EP2414333B1/en not_active Not-in-force
- 2010-03-22 CN CN201080013540.3A patent/CN102356069B/zh not_active Expired - Fee Related
- 2010-03-22 CN CN201410441411.4A patent/CN104292155A/zh active Pending
- 2010-03-22 RU RU2011139219/04A patent/RU2524284C2/ru not_active IP Right Cessation
- 2010-03-22 CA CA2757016A patent/CA2757016A1/en not_active Abandoned
- 2010-03-22 BR BRPI1011531A patent/BRPI1011531A2/pt not_active IP Right Cessation
- 2010-03-22 MX MX2011010295A patent/MX2011010295A/es active IP Right Grant
- 2010-03-22 WO PCT/US2010/028078 patent/WO2010114723A1/en active Application Filing
- 2010-03-22 PT PT107101438T patent/PT2414333E/pt unknown
- 2010-03-22 US US13/256,511 patent/US8530620B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2004002984A2 (fr) * | 2002-07-01 | 2004-01-08 | Commissariat A L'energie Atomique | Composes de maleimides marques, leur procede de preparation et leur utilisation pour le marquage de macromolecules |
WO2009035959A2 (en) * | 2007-09-10 | 2009-03-19 | Ge Healthcare Limited | Radiofluorination methods |
FR2926079A1 (fr) * | 2008-01-03 | 2009-07-10 | Commissariat Energie Atomique | Procede de preparation d'un derive de purine marque, ledit derive et ses utilisations |
Non-Patent Citations (1)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016531851A (ja) * | 2013-09-26 | 2016-10-13 | イーライ リリー アンド カンパニー | タウ画像化剤の調製のための新規化合物および使用、ならびにタウ画像化製剤 |
JP2018531243A (ja) * | 2015-09-30 | 2018-10-25 | ドイチェス クレブスフォルシュンクスツェントルム | 前立腺特異的膜抗原(psma)の18f−タグ付加インヒビターおよび前立腺癌についての画像化剤としてのその使用 |
Also Published As
Publication number | Publication date |
---|---|
CN102356069B (zh) | 2014-09-24 |
CN102356069A (zh) | 2012-02-15 |
US20120022227A1 (en) | 2012-01-26 |
CN104292155A (zh) | 2015-01-21 |
GB0905438D0 (en) | 2009-05-13 |
EP2414333A1 (en) | 2012-02-08 |
KR20110133038A (ko) | 2011-12-09 |
RU2011139219A (ru) | 2013-05-10 |
PL2414333T3 (pl) | 2013-07-31 |
MX2011010295A (es) | 2012-03-26 |
WO2010114723A1 (en) | 2010-10-07 |
PT2414333E (pt) | 2013-05-07 |
US8530620B2 (en) | 2013-09-10 |
BRPI1011531A2 (pt) | 2016-03-29 |
CA2757016A1 (en) | 2010-10-07 |
ES2404346T3 (es) | 2013-05-27 |
AU2010232828A1 (en) | 2011-10-13 |
EP2414333B1 (en) | 2013-02-13 |
RU2524284C2 (ru) | 2014-07-27 |
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