CA2065290A1 - Chelates de metal et de composes du type hydroxy-aryle utiles pour l'imagerie rmn diagnostique - Google Patents
Chelates de metal et de composes du type hydroxy-aryle utiles pour l'imagerie rmn diagnostiqueInfo
- Publication number
- CA2065290A1 CA2065290A1 CA2065290A CA2065290A CA2065290A1 CA 2065290 A1 CA2065290 A1 CA 2065290A1 CA 2065290 A CA2065290 A CA 2065290A CA 2065290 A CA2065290 A CA 2065290A CA 2065290 A1 CA2065290 A1 CA 2065290A1
- Authority
- CA
- Canada
- Prior art keywords
- iii
- nitrogens
- hydroxy
- ligand
- nmr
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000003384 imaging method Methods 0.000 title abstract 3
- 125000005027 hydroxyaryl group Chemical group 0.000 title 1
- 239000002184 metal Substances 0.000 title 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 8
- 239000003446 ligand Substances 0.000 abstract 6
- 230000002708 enhancing effect Effects 0.000 abstract 3
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 3
- 229910052693 Europium Inorganic materials 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052692 Dysprosium Inorganic materials 0.000 abstract 1
- 229910052691 Erbium Inorganic materials 0.000 abstract 1
- 229910052688 Gadolinium Inorganic materials 0.000 abstract 1
- 229910052689 Holmium Inorganic materials 0.000 abstract 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052771 Terbium Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000002872 contrast media Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 abstract 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 abstract 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 abstract 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Signal Processing (AREA)
- High Energy & Nuclear Physics (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
Abstract
Une composition d'agents de contraste de résonnance magnétique nucléaire contient un complexe d'un ion métallique sélectionné et d'un ligand sélectionné. L'ion est sélectionné dans le groupe composé de gadolinium (III), fer (III), manganèse (II), manganèse (III), chrome (III), cuivre (II), dysprosium (III), terbium (III), holmium (III), erbium (III), europium (II), et europium (III); et le ligand est un composé linéaire à deux atomes d'azote comportant un groupe 2-hydroxy-aryle au niveau d'un des atomes d'azote; ou le ligand est un composé linéaire à deux atomes d'azote comportant un ou deux groupes 2-hydroxy-aryle à chaque atome d'azote; ou le ligand est un composé linéaire à trois, quatre ou cinq atomes d'azote comportant un ou deux substituants 2-hydroxy-aryle au niveau de chaque atome ou de plusieurs atomes d'azote, ou le ligand est un composé hétérocyclique comportant un anneau contenant trois ou quatre atomes d'azote, et ayant un substituant 2-hydroxy-aryle au niveau d'un ou de plusieurs atomes d'azote; ou bien le ligand est un composé hétérocyclique comportant un anneau contenant quatre atomes d'azote, et ayant un groupe carboxyle au niveau de deux atomes d'azote ainsi qu'un substituant aromatique au niveau des deux autres atomes d'azote. De plus, un procédé d'amélioration du contraste en imagerie RMN chez un patient comprend les étapes consistant à préparer un agent améliorant le contraste de RMN par mélange d'un composé de contraste de RMN de l'invention avec un support pharmaceutiquement acceptable, à introduire l'agent améliorant le contraste de RMN dans le patient, et à soumettre le patient à une imagerie par RMN.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39973789A | 1989-08-28 | 1989-08-28 | |
US399,737 | 1989-08-28 | ||
PCT/US1990/004887 WO1991003200A1 (fr) | 1989-08-28 | 1990-08-28 | Chelates metalliques d'hydroxy-aryle d'imagerie par resonnance magnetique nucleaire de diagnostic |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2065290A1 true CA2065290A1 (fr) | 1991-03-01 |
CA2065290C CA2065290C (fr) | 2000-12-12 |
Family
ID=23580762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002065290A Expired - Fee Related CA2065290C (fr) | 1989-08-28 | 1990-08-28 | Chelates de metal et de composes du type hydroxy-aryle utiles pour l'imagerie rmn diagnostique |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0489869B1 (fr) |
JP (1) | JPH05503072A (fr) |
AT (1) | ATE173336T1 (fr) |
CA (1) | CA2065290C (fr) |
DE (1) | DE69032761T2 (fr) |
HK (1) | HK1012707A1 (fr) |
WO (1) | WO1991003200A1 (fr) |
Families Citing this family (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5250285A (en) * | 1985-05-08 | 1993-10-05 | The General Hospital Corporation | Hydroxy-aryl metal chelates for diagnostic NMR imaging |
US5562894A (en) * | 1991-08-09 | 1996-10-08 | Regents Of The University Of California | Amino-acyl-type and catecholamine-type contrast agents for MRI |
DE4136489A1 (de) * | 1991-11-06 | 1993-05-13 | Bayer Ag | Neue diethylentriamin-derivate und deren verwendung zu diagnostischen und therapeutischen zwecken |
US5532006A (en) * | 1993-04-23 | 1996-07-02 | The Board Of Trustees Of The University Of Illinois | Magnetic gels which change volume in response to voltage changes for MRI |
US5480970A (en) * | 1993-12-22 | 1996-01-02 | Resolution Pharmaceuticals | Metal chelators |
US5569745A (en) * | 1994-02-25 | 1996-10-29 | Resolution Pharmaceuticals Inc. | Peptide-Chelator conjugates |
US5582814A (en) * | 1994-04-15 | 1996-12-10 | Metasyn, Inc. | 1-(p-n-butylbenzyl) DTPA for magnetic resonance imaging |
TW319763B (fr) | 1995-02-01 | 1997-11-11 | Epix Medical Inc | |
ES2217408T3 (es) | 1996-04-01 | 2004-11-01 | Epix Medical, Inc. | Agentes diagnosticos de contraste para formacion de imagenes bioactivados. |
US6875419B2 (en) | 2000-11-20 | 2005-04-05 | Board Of Regents The University Of Texas System | Paramagnetic metal ion-based macrocyclic magnetization transfer contrast agents and method of use |
ES2398393T3 (es) | 2002-03-01 | 2013-03-15 | Dyax Corp. | Péptidos de unión a KDR y a VEGF/KDR y su uso en diagnóstico y terapia |
US8623822B2 (en) | 2002-03-01 | 2014-01-07 | Bracco Suisse Sa | KDR and VEGF/KDR binding peptides and their use in diagnosis and therapy |
US7261876B2 (en) | 2002-03-01 | 2007-08-28 | Bracco International Bv | Multivalent constructs for therapeutic and diagnostic applications |
EP1587944A4 (fr) | 2002-03-01 | 2007-03-21 | Dyax Corp | Peptides de liaison kdr et vegf/kdr et leur utilisation a des fins diagnostiques et therapeutiques |
US7794693B2 (en) | 2002-03-01 | 2010-09-14 | Bracco International B.V. | Targeting vector-phospholipid conjugates |
US7226577B2 (en) | 2003-01-13 | 2007-06-05 | Bracco Imaging, S. P. A. | Gastrin releasing peptide compounds |
DK2949658T3 (en) | 2003-03-03 | 2018-10-01 | Dyax Corp | Peptides that specifically bind HGF receptor (cMet) and uses thereof |
US20120045393A1 (en) | 2009-03-17 | 2012-02-23 | Linder Karen E | Lhrh-ii peptide analogs |
MX2011009716A (es) | 2009-03-19 | 2011-10-17 | Wyeth Llc | Metodos para la preparacion de acido [2-(8,9-dioxo)-2,6-diazabicic lo[5.2.0]non-1(7)-en-2-il)etil]fosfonico y precursores de este. |
WO2010121133A2 (fr) | 2009-04-17 | 2010-10-21 | The General Hospital Corporation | Imagerie multimodale de fibrine |
US20110077396A1 (en) * | 2009-09-30 | 2011-03-31 | General Electric Company | Intermediates for hydroxylated contrast enhancement agents |
US8378134B2 (en) | 2009-09-30 | 2013-02-19 | General Electric Company | Hydroxylated contrast enhancement agents |
US8722020B2 (en) * | 2010-03-31 | 2014-05-13 | General Electric Company | Hydroxylated contrast enhancement agents |
JP6297440B2 (ja) * | 2013-07-31 | 2018-03-20 | キヤノンメディカルシステムズ株式会社 | 造影剤 |
WO2015038968A1 (fr) | 2013-09-13 | 2015-03-19 | The General Hospital Corporation | Sondes de liaison à la fibrine activables |
US20150344523A1 (en) | 2014-05-05 | 2015-12-03 | California Institute Of Technology | Mutant akt-specific capture agents, compositions, and methods of using and making |
US10471162B2 (en) | 2014-06-20 | 2019-11-12 | The General Hospital Corporation | Collagen targeted imaging probes |
EP3270951B1 (fr) | 2015-03-16 | 2020-09-09 | California Institute of Technology | Agents de capture spécifiques de la neurotoxine botulique, compositions et méthodes d'utilisation et de préparation associées |
CN104910030B (zh) * | 2015-05-14 | 2018-03-23 | 石家庄杰克化工有限公司 | 一种高纯度乙醇胺类氨羧螯合剂的合成工艺 |
EP3101012A1 (fr) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | Nouveaux composés de chélate de gadolinium pour une utilisation dans l'imagerie par résonance magnétique |
US10598671B2 (en) | 2015-07-15 | 2020-03-24 | Indi Molecular, Inc. | IL-17F-specific capture agents, compositions, and methods of using and making |
US9829474B2 (en) * | 2015-10-16 | 2017-11-28 | General Electric Company | Acetate complexes and methods for acetate quantification |
US20170319722A1 (en) | 2016-04-04 | 2017-11-09 | Indi Molecular, Inc. | Cd8-specific capture agents, compositions, and methods of using and making |
EP3519425B1 (fr) | 2016-09-29 | 2024-02-28 | Indi Molecular, Inc. | Compositions pour la détection, l'inhibition et l'imagerie de l'indoléamine 2,3-dioxygénase 1 (ido1) et leurs méthodes de production et d'utilisation |
EP3535278A4 (fr) | 2016-11-01 | 2020-06-24 | Ohio State Innovation Foundation | Procédés d'iodation de biomolécules |
JP7034160B2 (ja) | 2016-11-28 | 2022-03-11 | バイエル・ファルマ・アクティエンゲゼルシャフト | 磁気共鳴画像法に使用するための高緩和度ガドリニウムキレート化合物 |
EP3638687A1 (fr) | 2017-06-15 | 2020-04-22 | Indi Molecular, Inc. | Agents de capture spécifiques d'il-17f et il-17a, compositions et procédés d'utilisation et de production |
US11919972B2 (en) | 2018-11-02 | 2024-03-05 | Regeneron Pharmaceuticals, Inc. | Peptide libraries with non-canonical amino acids |
US11638764B2 (en) | 2018-11-08 | 2023-05-02 | Indi Molecular, Inc. | Theranostic capture agents, compositions, and methods of using and making |
PE20211471A1 (es) | 2018-11-23 | 2021-08-05 | Bayer Ag | Formulacion de medios de contraste y proceso para prepararlos |
WO2020186091A1 (fr) | 2019-03-12 | 2020-09-17 | Indi Molecular, Inc. | Épitopes réticulés et leurs méthodes d'utilisation |
WO2020236969A1 (fr) | 2019-05-20 | 2020-11-26 | Indi Molecular, Inc. | Compositions et procédés se rapportant à la détection, à l'inhibition et à l'imagerie de l'indoléamine 2,3-dioxygénase 1 (ido1) |
WO2020236952A1 (fr) | 2019-05-20 | 2020-11-26 | Ohio State Innovation Foundation | Complexes d'apohémoglobine-haptoglobine et leurs procédés d'utilisation |
US11414460B2 (en) | 2019-07-19 | 2022-08-16 | Institute For Systems Biology | KRAS-specific capture agents, compositions, and methods of making and using |
US20230183354A1 (en) | 2020-04-30 | 2023-06-15 | Sairopa B.V. | Anti-cd103 antibodies |
WO2022098743A1 (fr) | 2020-11-03 | 2022-05-12 | Indi Molecular, Inc. | Compositions, imagerie et procédés thérapeutiques ciblant le récepteur 1 de folate (folr1) |
WO2022098745A1 (fr) | 2020-11-03 | 2022-05-12 | Indi Molecular, Inc. | Compositions, systèmes d'administration et méthodes utiles dans la thérapie antitumorale |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3632637A (en) * | 1968-02-13 | 1972-01-04 | Arthur E Martell | Hydroxyaryl-containing aminocarboxylic chelating agents |
FR2354993A1 (fr) * | 1976-06-16 | 1978-01-13 | Dabeer | Procede pour la preparation de derives phenoliques d'acides hydroxyalcoyl-alcoylene-diaminoacetiques et de leurs sels |
US4687658A (en) * | 1984-10-04 | 1987-08-18 | Salutar, Inc. | Metal chelates of diethylenetriaminepentaacetic acid partial esters for NMR imaging |
US4639365A (en) * | 1984-10-18 | 1987-01-27 | The Board Of Regents, The University Of Texas System | Gadolinium chelates as NMR contrast agents |
US4746507A (en) * | 1985-04-02 | 1988-05-24 | Salutar, Inc. | EDHPA based contrast agents for MR imaging, apparatus and methods |
US4899755A (en) * | 1985-05-08 | 1990-02-13 | The General Hospital Corporation | Hepatobiliary NMR contrast agents |
US4880008A (en) * | 1985-05-08 | 1989-11-14 | The General Hospital Corporation | Vivo enhancement of NMR relaxivity |
DE3772785D1 (de) * | 1986-01-23 | 1991-10-17 | Squibb & Sons Inc | 1-substituiertes-4,7,10-triscarboxymethyl-1,4,7,10-tetraazacyclododecan und analoga. |
US4885363A (en) * | 1987-04-24 | 1989-12-05 | E. R. Squibb & Sons, Inc. | 1-substituted-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs |
GB2205128A (en) * | 1987-05-22 | 1988-11-30 | Daniel Stefanini | Pumps |
GB8719042D0 (en) * | 1987-08-12 | 1987-09-16 | Parker D | Conjugate compounds |
GB8719041D0 (en) * | 1987-08-12 | 1987-09-16 | Parker D | Conjugate compounds |
DE3728600A1 (de) * | 1987-08-27 | 1989-03-09 | Hoechst Ag | Verfahren zur markierung von substanzen mit technetium oder rhenium |
NZ229700A (en) * | 1988-06-24 | 1993-01-27 | Dow Chemical Co | Tetraazacyclododecane derivatives containing a linker/spacer moiety capable of forming antibody conjugates; complexes with radionuclides and conjugates of such compounds and complexes with antibodies or antibody fragments |
JP2930708B2 (ja) * | 1988-12-23 | 1999-08-03 | ザ ダウ ケミカル カンパニー | イソチオシアナト官能化金属錯体の製造方法 |
FR2643370B1 (fr) * | 1989-02-22 | 1991-08-23 | Air Liquide | Derives polyazotes et leurs complexes metalliques utilisables pour la fixation de l'oxygene |
-
1990
- 1990-08-28 AT AT90914613T patent/ATE173336T1/de not_active IP Right Cessation
- 1990-08-28 CA CA002065290A patent/CA2065290C/fr not_active Expired - Fee Related
- 1990-08-28 DE DE69032761T patent/DE69032761T2/de not_active Expired - Fee Related
- 1990-08-28 EP EP90914613A patent/EP0489869B1/fr not_active Expired - Lifetime
- 1990-08-28 JP JP2513710A patent/JPH05503072A/ja active Pending
- 1990-08-28 WO PCT/US1990/004887 patent/WO1991003200A1/fr active IP Right Grant
-
1998
- 1998-12-16 HK HK98113763A patent/HK1012707A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
WO1991003200A1 (fr) | 1991-03-21 |
EP0489869A4 (en) | 1993-03-17 |
HK1012707A1 (en) | 1999-08-06 |
ATE173336T1 (de) | 1998-11-15 |
DE69032761T2 (de) | 1999-04-22 |
EP0489869B1 (fr) | 1998-11-11 |
JPH05503072A (ja) | 1993-05-27 |
CA2065290C (fr) | 2000-12-12 |
EP0489869A1 (fr) | 1992-06-17 |
DE69032761D1 (de) | 1998-12-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |