DK1805186T3 - Radikaler og deres anvendelse som paramagnetiske midler i en dynamisk kernepolariseringsproces - Google Patents
Radikaler og deres anvendelse som paramagnetiske midler i en dynamisk kernepolariseringsproces Download PDFInfo
- Publication number
- DK1805186T3 DK1805186T3 DK05771195.4T DK05771195T DK1805186T3 DK 1805186 T3 DK1805186 T3 DK 1805186T3 DK 05771195 T DK05771195 T DK 05771195T DK 1805186 T3 DK1805186 T3 DK 1805186T3
- Authority
- DK
- Denmark
- Prior art keywords
- acid
- compound
- radical
- carboxyl groups
- formula
- Prior art date
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B5/00—Measuring for diagnostic purposes; Identification of persons
- A61B5/05—Detecting, measuring or recording for diagnosis by means of electric currents or magnetic fields; Measuring using microwaves or radio waves
- A61B5/055—Detecting, measuring or recording for diagnosis by means of electric currents or magnetic fields; Measuring using microwaves or radio waves involving electronic [EMR] or nuclear [NMR] magnetic resonance, e.g. magnetic resonance imaging
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/20—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations containing free radicals, e.g. trityl radical for overhauser
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
- G01R33/44—Arrangements or instruments for measuring magnetic variables involving magnetic resonance using nuclear magnetic resonance [NMR]
- G01R33/48—NMR imaging systems
- G01R33/54—Signal processing systems, e.g. using pulse sequences ; Generation or control of pulse sequences; Operator console
- G01R33/56—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution
- G01R33/5601—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution involving use of a contrast agent for contrast manipulation, e.g. a paramagnetic, super-paramagnetic, ferromagnetic or hyperpolarised contrast agent
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
- G01R33/62—Arrangements or instruments for measuring magnetic variables involving magnetic resonance using double resonance
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- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Radiology & Medical Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- High Energy & Nuclear Physics (AREA)
- Epidemiology (AREA)
- Signal Processing (AREA)
- Biomedical Technology (AREA)
- Pathology (AREA)
- Biophysics (AREA)
- Heart & Thoracic Surgery (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Surgery (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
Claims (19)
1. Fremgangsmåde til dynamisk kernepolarisering (DNP) af en forbindelse omfattende en eller flere carboxylgrupper, kendetegnet ved, at et radikal med formlen (I)
hvor M betegner hydrogen eller en ækvivalent afen kation; og R1, som er ens eller forskellig, betegner en ligekædet eller forgrenet C1-C6- alkylgruppe eller en -(CH2)n-X-R2-gruppe, hvor n er 1,2 eller 3; X er O eller S og R2 er en ligekædet eller forgrenet CrC4-alkylgruppe anvendes som det paramagnetiske middel i DNP-processen.
2. Fremgangsmåde ifølge krav 1, kendetegnet ved, at der anvendes et radikal med formel (I), hvor M betegner hydrogen eller en ækvivalent af en fysiologisk acceptabel kation.
3. Fremgangsmåde ifølge krav 1 eller 2, kendetegnet ved, at der anvendes et radikal med formel (I), hvor M betegner hydrogen, en alkalisk kation, fortrinsvis natrium, en ammoniumion eller organisk aminion.
4. Fremgangsmåde ifølge krav 1 til 3, kendetegnet ved, at der anvendes et radikal med formel (I), hvor R1 er den samme.
5. Fremgangsmåde ifølge krav 1 til 4, kendetegnet ved, at der anvendes et radikal med formel (I), hvor R1 er den samme og betegner en ligekædet eller forgrenet Ci-C4-alkylgruppe, fortrinsvis methyl, ethyl eller isopropyl.
6. Fremgangsmåde ifølge krav 1 til 5, kendetegnet ved, at der anvendes et radikal med formel (I), hvor R1 er den samme og betegner -CFI2-OCFI3, -CH2-OC2H5, -CH2-CH2-OCH3, -CH2-SCH3, -CH2-SC2H5 eller -CH2-CH2-SCH3, fortrinsvis -CFI2-CFI2-OCFI3.
7. Fremgangsmåde ifølge krav 1 til 6, hvor forbindelsen omfattende en eller flere carboxylgruppper er en endogen forbindelse, fortrinsvis en endogen forbindelse, som spiller en rolle i en metabolsk proces i den menneskelige eller ikke menneskelige dyrekrop.
8. Fremgangsmåde ifølge krav 1 til 7, hvor forbindelsen omfattende en eller flere carboxylgrupper er en forbindelse udvalgt fra gruppen bestående af sy-reholdige aminosyrer, eddikesyre, aceteddikesyre, hydroxybutansyre, mælkesyre, pyrodruesyre, fumarsyre, ravsyre, citronsyre, æblesyre, ascorbinsyre og fedtsyrer.
9. Fremgangsmåde ifølge krav 1 til 8, hvor forbindelsen omfattende en eller flere carboxylgrupper er pyrodruesyre.
10. Fremgangsmåde ifølge krav 1 til 9, hvor forbindelsen omfattende en eller flere carboxylgrupper er beriget isotopisk med en non-nul kernespin, fortrinsvis med 15N og/eller 13C.
11. Radikaler med formlen (I)
hvor M betegner hydrogen eller en ækvivalent afen kation; og R1, som er ens eller forskellig, betegner -(CH2)n-X-R2, hvor n er 1,2 eller 3; X er O eller S; og R2 er en ligekædet eller forgrenet Ci-C4-alkylgruppe.
12. Radikaler ifølge krav 11, hvor M betegner hydrogen eller en ækvivalent af en fysiologisk acceptabel kation, fortrinsvis en alkalisk kation, en ammoniumion eller en organisk aminion.
13. Radikaler ifølge krav 11 og 12, hvor R1 er den samme og betegner -CH2-OCH3, -CH2-OC2H5, -CH2-CH2-OCH3, -CH2-SCH3, -CH2-SO2H5 eller -CH2-CH2-SCH3, mest fortrinsvis -CH2-CH2-OCH3.
14. Radikal ifølge krav 11 til 13, hvor M betegner hydrogen eller en ækvivalent af en fysiologisk acceptabel kation, fortrinsvis natrium, og R1 er den samme og betegner -CH2-CH2-OCH3.
15. Anvendelse af radikaler ifølge krav 11 til 14 som paramagnetiske midler i en DNP-proces.
16. Anvendelse af radikaler ifølge krav 15, hvor den forbindelse, der skal polariseres i DNP-processen, er en forbindelse omfattende en eller flere carbo-xylgrupper.
17. Sammensætning omfattende et radikal ifølge krav 11 til 14 og en forbindelse omfattende en eller flere carboxylgrupper.
18. Sammensætning ifølge krav 17, hvor forbindelsen omfattende en eller flere carboxylgrupper er en endogen forbindelse, fortrinsvis en endogen forbindelse, som spiller en rolle i en metabolsk proces i den menneskelige eller ikke menneskelige dyrekrop.
19. Sammensætning ifølge krav 17 og 18, hvor forbindelsen omfattende en eller flere carboxylgrupper er en forbindelse udvalgt fra gruppen bestående af syreholdige aminosyrer, eddikesyre, aceteddikesyre, hydroxybutansyre, mælkesyre, pyrodruesyre, fumarsyre, ravsyre, citronsyre, æblesyre, ascor-binsyre og fedtsyrer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20043227 | 2004-07-30 | ||
| PCT/NO2005/000283 WO2006011811A2 (en) | 2004-07-30 | 2005-07-28 | Radicals and their use as paramagnetic agents in a dynamic nuclear polarisation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK1805186T3 true DK1805186T3 (da) | 2015-08-24 |
Family
ID=35502005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK05771195.4T DK1805186T3 (da) | 2004-07-30 | 2005-07-28 | Radikaler og deres anvendelse som paramagnetiske midler i en dynamisk kernepolariseringsproces |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8431723B2 (da) |
| EP (1) | EP1805186B1 (da) |
| JP (1) | JP5535435B2 (da) |
| KR (3) | KR101413934B1 (da) |
| CN (1) | CN101027310B (da) |
| AU (1) | AU2005267670B2 (da) |
| BR (1) | BRPI0513880A (da) |
| CA (1) | CA2575473C (da) |
| DK (1) | DK1805186T3 (da) |
| ES (1) | ES2545377T3 (da) |
| HK (1) | HK1107692A1 (da) |
| IL (1) | IL180895A (da) |
| MX (1) | MX2007001034A (da) |
| NO (1) | NO339934B1 (da) |
| PL (1) | PL1805186T3 (da) |
| RU (1) | RU2374253C2 (da) |
| WO (1) | WO2006011811A2 (da) |
| ZA (1) | ZA200701272B (da) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1797102B1 (en) * | 2004-07-30 | 2015-05-27 | Ge Healthcare As | Composition comprising triarylmethyl radical, useful in mri diagnostics |
| ES2375089T3 (es) * | 2005-12-01 | 2012-02-24 | Ge Healthcare As | Procedimiento de la polarización nuclear dinámica(dnp) que usa un radical tritilo y un ión metálico paramagnético. |
| JP5102221B2 (ja) * | 2005-12-16 | 2012-12-19 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 過分極カルボン酸塩の製造方法 |
| KR101502180B1 (ko) | 2006-08-30 | 2015-03-12 | 지이 헬스케어 에이에스 | 동적 핵 분극화 방법 및 이러한 방법에서 사용되는 화합물 및 조성물 |
| JP2008084485A (ja) * | 2006-09-28 | 2008-04-10 | Toshiba Corp | 不揮発性半導体記憶装置及びデータ読出方法 |
| US20100092391A1 (en) * | 2007-01-11 | 2010-04-15 | Huntington Medical Research Institutes | Imaging agents and methods of use thereof |
| US9227173B2 (en) | 2007-06-22 | 2016-01-05 | General Electric Company | Methods for dynamic filtration of pharmaceutical products |
| EP2072061A1 (en) | 2007-12-19 | 2009-06-24 | GE Healthcare Limited | Composition and method for generating a metabolic profile using 13C-MR detection |
| WO2009129265A1 (en) | 2008-04-14 | 2009-10-22 | Huntington Medical Research Institutes | Methods and apparatus for pasadena hyperpolarization |
| EP2476009A1 (en) | 2009-09-10 | 2012-07-18 | GE Healthcare UK Limited | 13c-mr detection using hyperpolarised 13c-fructose |
| WO2011052760A1 (ja) * | 2009-10-29 | 2011-05-05 | 国立大学法人九州大学 | 生体内因性分子の検出方法 |
| FR2967158A1 (fr) | 2010-11-08 | 2012-05-11 | Phosphoenix Sarl | Nouveaux radicaux triarylmethyle: leur preparation et application |
| EP2640263A1 (en) * | 2010-11-16 | 2013-09-25 | Aspect Magnet Technologies Ltd. | System and method for generating invasively hyperpolarized images |
| GB2498181A (en) | 2011-12-29 | 2013-07-10 | Bruker Biospin Gmbh | Device and method for rapid dynamic nuclear polarisation |
| CN104981256B (zh) * | 2013-01-31 | 2020-02-18 | 伯拉考成像股份公司 | 作为mr中的代谢标记的超极化酯类 |
| US9874622B2 (en) | 2013-09-27 | 2018-01-23 | General Electric Company | Hyperpolarized media transport vessel |
| US10918744B2 (en) | 2017-03-01 | 2021-02-16 | Educational foundation Kyushu Bunka Gakuen | Biometric method |
| CN108794510B (zh) * | 2018-07-25 | 2021-08-06 | 天津医科大学 | 一种由三芳基甲基自由基与氮氧自由基组成的双自由基化合物及其盐、其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3175940B2 (ja) | 1990-02-12 | 2001-06-11 | ニコムド イノベーション アーベー | トリアリールメチルラジカルおよび磁気共鳴造影法における不活性炭素フリーラジカルの用途 |
| GB9704669D0 (en) * | 1997-03-06 | 1997-04-23 | Nycomed Imaging As | Free radicals |
| US5728370A (en) * | 1993-04-02 | 1998-03-17 | Nycomed Imaging As | Free Radicals |
| WO1998039277A1 (en) * | 1997-03-06 | 1998-09-11 | Nycomed Imaging As | Triarylmethyl free radicals as image enhancing agents |
| US6278893B1 (en) * | 1998-01-05 | 2001-08-21 | Nycomed Imaging As | Method of magnetic resonance imaging of a sample with ex vivo polarization of an MR imaging agent |
-
2005
- 2005-07-28 KR KR1020137005589A patent/KR101413934B1/ko not_active IP Right Cessation
- 2005-07-28 US US11/572,654 patent/US8431723B2/en active Active
- 2005-07-28 PL PL05771195T patent/PL1805186T3/pl unknown
- 2005-07-28 CA CA2575473A patent/CA2575473C/en active Active
- 2005-07-28 KR KR1020147006039A patent/KR101554832B1/ko active IP Right Grant
- 2005-07-28 WO PCT/NO2005/000283 patent/WO2006011811A2/en active Application Filing
- 2005-07-28 KR KR1020077004778A patent/KR20070061805A/ko not_active Application Discontinuation
- 2005-07-28 MX MX2007001034A patent/MX2007001034A/es active IP Right Grant
- 2005-07-28 DK DK05771195.4T patent/DK1805186T3/da active
- 2005-07-28 CN CN2005800325159A patent/CN101027310B/zh active Active
- 2005-07-28 EP EP05771195.4A patent/EP1805186B1/en active Active
- 2005-07-28 BR BRPI0513880-9A patent/BRPI0513880A/pt not_active Application Discontinuation
- 2005-07-28 ES ES05771195.4T patent/ES2545377T3/es active Active
- 2005-07-28 RU RU2007102844/04A patent/RU2374253C2/ru not_active IP Right Cessation
- 2005-07-28 AU AU2005267670A patent/AU2005267670B2/en not_active Ceased
- 2005-07-28 JP JP2007523506A patent/JP5535435B2/ja active Active
-
2007
- 2007-01-23 IL IL180895A patent/IL180895A/en active IP Right Grant
- 2007-02-13 ZA ZA200701272A patent/ZA200701272B/en unknown
- 2007-02-27 NO NO20071116A patent/NO339934B1/no not_active IP Right Cessation
- 2007-12-05 HK HK07113303.8A patent/HK1107692A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1107692A1 (en) | 2008-04-11 |
| CA2575473C (en) | 2013-02-19 |
| EP1805186A2 (en) | 2007-07-11 |
| US8431723B2 (en) | 2013-04-30 |
| AU2005267670B2 (en) | 2011-03-03 |
| IL180895A0 (en) | 2007-07-04 |
| AU2005267670A1 (en) | 2006-02-02 |
| PL1805186T3 (pl) | 2015-10-30 |
| CN101027310A (zh) | 2007-08-29 |
| KR20140146042A (ko) | 2014-12-24 |
| JP5535435B2 (ja) | 2014-07-02 |
| CA2575473A1 (en) | 2006-02-02 |
| EP1805186B1 (en) | 2015-05-27 |
| WO2006011811A3 (en) | 2006-06-01 |
| ZA200701272B (en) | 2008-04-30 |
| JP2008508267A (ja) | 2008-03-21 |
| KR20070061805A (ko) | 2007-06-14 |
| KR20130045378A (ko) | 2013-05-03 |
| MX2007001034A (es) | 2007-07-25 |
| NO339934B1 (no) | 2017-02-20 |
| RU2007102844A (ru) | 2008-09-10 |
| IL180895A (en) | 2013-03-24 |
| RU2374253C2 (ru) | 2009-11-27 |
| CN101027310B (zh) | 2012-08-22 |
| WO2006011811A2 (en) | 2006-02-02 |
| BRPI0513880A (pt) | 2008-05-20 |
| ES2545377T3 (es) | 2015-09-10 |
| KR101413934B1 (ko) | 2014-06-30 |
| KR101554832B1 (ko) | 2015-09-21 |
| NO20071116L (no) | 2007-04-30 |
| US20090214432A1 (en) | 2009-08-27 |
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