CH660183A5 - Diagnostisches mittel. - Google Patents
Diagnostisches mittel. Download PDFInfo
- Publication number
- CH660183A5 CH660183A5 CH266/84A CH26684A CH660183A5 CH 660183 A5 CH660183 A5 CH 660183A5 CH 266/84 A CH266/84 A CH 266/84A CH 26684 A CH26684 A CH 26684A CH 660183 A5 CH660183 A5 CH 660183A5
- Authority
- CH
- Switzerland
- Prior art keywords
- complex
- salt
- iii
- acid
- diagnostic agent
- Prior art date
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- 150000003839 salts Chemical class 0.000 claims description 81
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- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 64
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- 239000000032 diagnostic agent Substances 0.000 claims description 47
- 229940039227 diagnostic agent Drugs 0.000 claims description 47
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 45
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
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- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
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- A61K49/105—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being acyclic, e.g. DTPA the metal complex being Gd-DTPA
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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
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1806—Suspensions, emulsions, colloids, dispersions
- A61K49/1812—Suspensions, emulsions, colloids, dispersions liposomes, polymersomes, e.g. immunoliposomes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Radiology & Medical Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Paper (AREA)
- Heat-Exchange Devices With Radiators And Conduit Assemblies (AREA)
- Forging (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3302410 | 1983-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH660183A5 true CH660183A5 (de) | 1987-03-31 |
Family
ID=6189163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH266/84A CH660183A5 (de) | 1983-01-21 | 1984-01-20 | Diagnostisches mittel. |
Country Status (23)
| Country | Link |
|---|---|
| JP (2) | JPH0772162B2 (fr) |
| AT (1) | AT397465B (fr) |
| AU (2) | AU574658B2 (fr) |
| BE (1) | BE898708A (fr) |
| CA (1) | CA1256249A (fr) |
| CH (1) | CH660183A5 (fr) |
| DE (1) | DE3401052C2 (fr) |
| DK (2) | DK170460B1 (fr) |
| ES (1) | ES529020A0 (fr) |
| FI (1) | FI79026C (fr) |
| FR (2) | FR2539996B1 (fr) |
| GB (3) | GB2137612A (fr) |
| GR (1) | GR81653B (fr) |
| IE (2) | IE56855B1 (fr) |
| IL (2) | IL77761A (fr) |
| IT (1) | IT1213128B (fr) |
| LU (1) | LU85177A1 (fr) |
| NL (2) | NL194579C (fr) |
| NO (1) | NO169103C (fr) |
| NZ (2) | NZ219079A (fr) |
| PT (1) | PT77983B (fr) |
| SE (2) | SE510582C2 (fr) |
| ZA (1) | ZA84472B (fr) |
Families Citing this family (117)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3324235A1 (de) * | 1983-07-01 | 1985-01-10 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue komplexbildner, komplexe und komplexsalze |
| US5720939A (en) * | 1985-08-15 | 1998-02-24 | Nycomed Imaging As | Method of contrast enhanced magnetic resonance imaging using magnetically responsive-particles |
| US5618514A (en) | 1983-12-21 | 1997-04-08 | Nycomed Imaging As | Diagnostic and contrast agent |
| GB8408127D0 (en) * | 1984-03-29 | 1984-05-10 | Nyegaard & Co As | Contrast agents |
| ZA852979B (en) * | 1984-04-27 | 1985-11-27 | Vestar Research Inc | Contrast agents for nmr imaging |
| US4728575A (en) * | 1984-04-27 | 1988-03-01 | Vestar, Inc. | Contrast agents for NMR imaging |
| DE3577550D1 (de) * | 1984-09-21 | 1990-06-13 | Dow Chemical Co | Aminocarbonsaeurekomplexe zur behandlung von knochentumoren. |
| US4859451A (en) * | 1984-10-04 | 1989-08-22 | Salutar, Inc. | Paramagnetic contrast agents for MR imaging |
| US4687659A (en) * | 1984-11-13 | 1987-08-18 | Salutar, Inc. | Diamide-DTPA-paramagnetic contrast agents for MR imaging |
| US5362476A (en) * | 1984-10-18 | 1994-11-08 | Board Of Regents, The University Of Texas System | Alkyl phosphonate polyazamacrocyclic cheates for MRI |
| US5342606A (en) * | 1984-10-18 | 1994-08-30 | Board Of Regents, The University Of Texas System | Polyazamacrocyclic compounds for complexation of metal ions |
| CA1317937C (fr) * | 1984-10-18 | 1993-05-18 | A. Dean Sherry | Chelates de gadolinium et de derives carboxymethyles de polyazamacrocycles servant d'agents contrastants en rmn |
| US5188816A (en) * | 1984-10-18 | 1993-02-23 | Board Of Regents, The University Of Texas System | Using polyazamacrocyclic compounds for intracellular measurement of metal ions using MRS |
| US5316757A (en) * | 1984-10-18 | 1994-05-31 | Board Of Regents, The University Of Texas System | Synthesis of polyazamacrocycles with more than one type of side-chain chelating groups |
| US4639365A (en) * | 1984-10-18 | 1987-01-27 | The Board Of Regents, The University Of Texas System | Gadolinium chelates as NMR contrast agents |
| DE3577185D1 (de) * | 1984-11-01 | 1990-05-23 | Nycomed As | Paramagnetische kontrastmittel fuer die anwendung in "in vivo" nmr-diagnostischen methoden und die herstellung davon. |
| SE465907B (sv) * | 1984-11-01 | 1991-11-18 | Nyegaard & Co As | Diagnosticeringsmedel innehaallande en paramagnetisk metall |
| DE3443252A1 (de) * | 1984-11-23 | 1986-05-28 | Schering AG, 1000 Berlin und 4709 Bergkamen | Dextran-magnetit-komplexe fuer die nmr-diagnostik |
| DE3443251C2 (de) * | 1984-11-23 | 1998-03-12 | Schering Ag | Eisenoxid-Komplexe für die NMR-Diagnostik, diese Verbindungen enthaltende diagnostische Mittel, ihre Verwendung und Verfahren zu deren Herstellung |
| DE3508000A1 (de) * | 1985-03-04 | 1986-09-04 | Schering AG, Berlin und Bergkamen, 1000 Berlin | Ferromagnetische partikel fuer die nmr-diagnostik |
| US4758422A (en) * | 1985-01-04 | 1988-07-19 | Salutar Inc. | Ferrioxamine paramagnetic contrast agents for MR imaging |
| US4980148A (en) * | 1985-02-06 | 1990-12-25 | Mallinckrodt, Inc. | Methods for enhancing magnetic resonance imaging |
| US4675173A (en) * | 1985-05-08 | 1987-06-23 | Molecular Biosystems, Inc. | Method of magnetic resonance imaging of the liver and spleen |
| GB8518300D0 (en) * | 1985-07-19 | 1985-08-29 | Amersham Int Plc | Contrast agent |
| US5336762A (en) * | 1985-11-18 | 1994-08-09 | Access Pharmaceuticals, Inc. | Polychelating agents for image and spectral enhancement (and spectral shift) |
| JPH07110815B2 (ja) * | 1985-11-18 | 1995-11-29 | ボ−ド・オブ・リ−ジェンツ、ザ・ユニバ−シティ−・オブ・テキサス・システム | 画像及びスペクトル向上（およびスペクトルシフト）のためのポリキレ−ト剤 |
| 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 |
| MX174467B (es) * | 1986-01-23 | 1994-05-17 | Squibb & Sons Inc | 1,4,7-triscarboximetil-1,4,7,10-tetraazaciclodo decano substituido en 1 y compuestos analogos |
| AU605461B2 (en) * | 1986-04-07 | 1991-01-17 | Francois Dietlin | New compositions usable in tomo-densitometry |
| FR2596992B1 (fr) * | 1986-04-11 | 1988-12-16 | Guerbet Sa | Sel de lysine du complexe gadolinium-dota et ses applications au diagnostic |
| EP0250358A3 (fr) * | 1986-06-20 | 1988-10-05 | Schering Aktiengesellschaft | Composés complexes |
| US4951675A (en) * | 1986-07-03 | 1990-08-28 | Advanced Magnetics, Incorporated | Biodegradable superparamagnetic metal oxides as contrast agents for MR imaging |
| DE3625417C2 (de) * | 1986-07-28 | 1998-10-08 | Schering Ag | Tetraazacyclododecan-Derivate |
| AU608759B2 (en) * | 1986-08-04 | 1991-04-18 | Amersham Health Salutar Inc | NMR imaging with paramagnetic polyvalents metal salts of poly-(acid-alkylene-amido)-alkanes |
| IL83966A (en) * | 1986-09-26 | 1992-03-29 | Schering Ag | Amides of aminopolycarboxylic acids and pharmaceutical compositions containing them |
| US5135737A (en) * | 1986-11-10 | 1992-08-04 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Amplifier molecules for enhancement of diagnosis and therapy |
| US5567411A (en) * | 1986-11-10 | 1996-10-22 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Dendritic amplifier molecules having multiple terminal active groups stemming from a benzyl core group |
| US4863717A (en) * | 1986-11-10 | 1989-09-05 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Methods for circumventing the problem of free radial reduction associated with the use of stable nitroxide free radicals as contrast agents for magnetic reasonance imaging |
| US5252317A (en) * | 1986-11-10 | 1993-10-12 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Amplifier molecules for diagnosis and therapy derived from 3,5-bis[1-(3-amino-2,2-bis (aminomethyl)-propyl) oxymethyl] benzoic acid |
| US5707604A (en) * | 1986-11-18 | 1998-01-13 | Access Pharmaceuticals, Inc. | Vivo agents comprising metal-ion chelates with acidic saccharides and glycosaminoglycans, giving improved site-selective localization, uptake mechanism, sensitivity and kinetic-spatial profiles |
| DE3640708C2 (de) * | 1986-11-28 | 1995-05-18 | Schering Ag | Verbesserte metallhaltige Pharmazeutika |
| IT1224416B (it) * | 1987-12-24 | 1990-10-04 | Bracco Ind Chimica Spa | Chelanti macrociclici e loro chelati |
| FI80801C (fi) * | 1987-01-14 | 1990-07-10 | Innofarm Oy | Konjugat av en monoklonal antikropp och anvaendning. eller ett fragment daerav och ett kelaterande aemne, dess framstaellning |
| GB8701054D0 (en) * | 1987-01-16 | 1987-02-18 | Amersham Int Plc | Contrast agent for nmr scanning |
| FR2612400A1 (fr) * | 1987-03-16 | 1988-09-23 | Centre Nat Rech Scient | Microcapsules contenant un marqueur radioactif et/ou paramagnetique sous forme de chelate, et leur utilisation dans le domaine de l'imagerie medicale |
| DE3709851A1 (de) * | 1987-03-24 | 1988-10-06 | Silica Gel Gmbh Adsorptions Te | Nmr-diagnostische fluessigkeitszusammensetzungen |
| US5482700A (en) * | 1987-03-31 | 1996-01-09 | Schering Aktiengesellschaft | Substituted polyamino, polycarboxy complexing agent dimers for MRI and X-ray contrast |
| US5693309A (en) * | 1987-03-31 | 1997-12-02 | Schering Aktiengesellschaft | Substituted complexing agents, complexes, and complex salts, processes for their production, and pharmaceuticals containing same |
| US5223538A (en) * | 1987-03-31 | 1993-06-29 | Duke University | Superoxide dismutase mimic |
| DE3710730A1 (de) * | 1987-03-31 | 1988-10-20 | Schering Ag | Substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| FR2614020B1 (fr) * | 1987-04-14 | 1989-07-28 | Guerbet Sa | Nouveaux ligands cycliques azotes, complexes metalliques formes par ces ligands, compositions de diagnostic contenant ces complexes et procede de preparation des ligands. |
| DE3713842A1 (de) * | 1987-04-22 | 1988-11-17 | Schering Ag | Substituierte cyclische komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| ES2026257T3 (es) * | 1987-06-23 | 1992-04-16 | Hafslund Nycomed Innovation Ab | Mejoras introducidas en la presentacion de imagenes por resonancia magnetica nuclear. |
| AU617338B2 (en) * | 1987-07-16 | 1991-11-28 | Nycomed As | Aminopolycarboxylic acids and derivatives thereof |
| US5198208A (en) * | 1987-07-16 | 1993-03-30 | Nycomed Imaging As | Aminopolycarboxylic acids and derivatives thereof |
| US5531978A (en) * | 1987-07-16 | 1996-07-02 | Nycomed Imaging As | Aminopolycarboxylic acids and derivatives thereof |
| JP2520262B2 (ja) * | 1987-08-21 | 1996-07-31 | 春幸 川原 | パツチテスト材料 |
| DE3728525A1 (de) * | 1987-08-24 | 1989-03-16 | Schering Ag | Mehrkernige substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| DE3927444A1 (de) * | 1989-08-16 | 1991-02-28 | Schering Ag | Verwendung von amid-komplexverbindungen |
| GB8801646D0 (en) * | 1988-01-26 | 1988-02-24 | Nycomed As | Chemical compounds |
| DE3806795A1 (de) * | 1988-02-29 | 1989-09-07 | Schering Ag | Polymer-gebundene komplexbildner, deren komplexe und konjugate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE3809671A1 (de) * | 1988-03-18 | 1989-09-28 | Schering Ag | Porphyrin-komplexverbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE4001655A1 (de) | 1990-01-18 | 1991-07-25 | Schering Ag | 6-ring enthaltende makrocyclische tetraaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE3825040A1 (de) | 1988-07-20 | 1990-01-25 | Schering Ag, 13353 Berlin | 5- oder 6-ring- enthaltende makrocyclische polyaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| JPH02140286A (ja) * | 1988-08-08 | 1990-05-29 | Biomira Inc | キレート化グループ置換ポリ（アミノ）酸化合物、キレート化合物グループの生体分子への光化学的付加用組成物および付加方法 |
| JP2854905B2 (ja) * | 1988-09-27 | 1999-02-10 | サリユーター・インコーポレイテツド | キレート組成物 |
| US4889931A (en) * | 1988-09-27 | 1989-12-26 | Salutar, Inc. | Manganese (II) chelate manufacture |
| US5260050A (en) * | 1988-09-29 | 1993-11-09 | Ranney David F | Methods and compositions for magnetic resonance imaging comprising superparamagnetic ferromagnetically coupled chromium complexes |
| US5213788A (en) * | 1988-09-29 | 1993-05-25 | Ranney David F | Physically and chemically stabilized polyatomic clusters for magnetic resonance image and spectral enhancement |
| GB8900719D0 (en) * | 1989-01-13 | 1989-03-08 | Nycomed As | Compounds |
| US6139603A (en) * | 1989-02-22 | 2000-10-31 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Process for recovering oxygen |
| US5011925A (en) * | 1989-03-09 | 1991-04-30 | Mallinckrodt, Inc. | Morpholinoamido EDTA derivatives |
| US5364613A (en) * | 1989-04-07 | 1994-11-15 | Sieving Paul F | Polychelants containing macrocyclic chelant moieties |
| US5384108A (en) * | 1989-04-24 | 1995-01-24 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| DE3922005A1 (de) * | 1989-06-30 | 1991-01-10 | Schering Ag | Derivatisierte dtpa-komplexe, diese verbindungen enthaltende pharmazeutische mittel, ihre verwendung und verfahren zu deren herstellung |
| US5087440A (en) * | 1989-07-31 | 1992-02-11 | Salutar, Inc. | Heterocyclic derivatives of DTPA used for magnetic resonance imaging |
| JPH04507401A (ja) * | 1989-09-05 | 1992-12-24 | マリンクロッド・インコーポレイテッド | 新規磁気共鳴造影剤 |
| US5516503A (en) * | 1989-11-16 | 1996-05-14 | Guerbet S.A. | Diagnostic composition comprising a binuclear complex, its method of preparation and its use in magnetic resonance imaging |
| FR2654344B1 (fr) * | 1989-11-16 | 1994-09-23 | Cis Bio Int | Complexe paramagnetique de gadolinium, son procede de preparation et son utilisation pour le diagnostic par irm. |
| DE3938992A1 (de) | 1989-11-21 | 1991-05-23 | Schering Ag | Kaskadenpolymer-gebundene komplexbildner, deren komplexe und konjugate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| EP0511275A1 (fr) * | 1990-01-19 | 1992-11-04 | Nycomed Imaging As | Composes de chelation |
| BR9102490A (pt) * | 1990-06-18 | 1992-01-21 | Dow Chemical Co | Metodo para uso diagnostico na formacao de imagens e composicao |
| US5310539A (en) * | 1991-04-15 | 1994-05-10 | Board Of Regents, The University Of Texas System | Melanin-based agents for image enhancement |
| CA2115275A1 (fr) * | 1991-08-09 | 1993-02-18 | David L. White | Agents contrastants a base d'acide amine, d'ester et (ou) de catechol pour irm |
| US5464696A (en) * | 1992-08-13 | 1995-11-07 | Bracco International B.V. | Particles for NMR imaging |
| DE4317588C2 (de) * | 1993-05-24 | 1998-04-16 | Schering Ag | Fluorhaltige makrocyclische Metallkomplexe, Verfahren zu ihrer Herstellung, sowie ihre Verwendung |
| DE4318369C1 (de) * | 1993-05-28 | 1995-02-09 | Schering Ag | Verwendung von makrocyclischen Metallkomplexen als Temperatursonden |
| US5405601A (en) * | 1993-07-02 | 1995-04-11 | Mallinckrodt Medical Inc. | Functionalized tripodal ligands for imaging applications |
| DE4340809C2 (de) * | 1993-11-24 | 2000-08-03 | Schering Ag | 1.4,7,10-Tetraazacyclododecan-Derivate, diese enthaltende pharmazeutische Mittel und Verfahren zu deren Herstellung |
| US5582814A (en) * | 1994-04-15 | 1996-12-10 | Metasyn, Inc. | 1-(p-n-butylbenzyl) DTPA for magnetic resonance imaging |
| DE19500665A1 (de) * | 1995-01-12 | 1996-07-18 | Axel Prof Dr Haase | Verfahren zur ortsauflösenden Abbildung eines Bereiches eines biologischen Objektes mit Hilfe elektromagnetischer Strahlen unter Applikation von Kontrastmittel |
| TW319763B (fr) | 1995-02-01 | 1997-11-11 | Epix Medical Inc | |
| DE19507820A1 (de) * | 1995-02-21 | 1996-08-22 | Schering Ag | Neuartig substituierte DTPA-Derivate, deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik, sowie Verfahren zur Herstellung der Komplexe und Mittel |
| DE19505960A1 (de) * | 1995-02-21 | 1996-08-22 | Deutsches Krebsforsch | Konjugat zur individuellen Dosierung von Arzneimitteln |
| DE19507819A1 (de) * | 1995-02-21 | 1996-08-22 | Schering Ag | DTPA-Monoamide der zentralen Carbonsäure und deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik und Therapie sowie Verfahren zur Herstellung der Komplexe und Mittel |
| DE19507822B4 (de) * | 1995-02-21 | 2006-07-20 | Schering Ag | Substituierte DTPA-Monoamide der zentralen Carbonsäure und deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik und Therapie sowie Verfahren zur Herstellung der Komplexe und Mittel |
| US6106866A (en) * | 1995-07-31 | 2000-08-22 | Access Pharmaceuticals, Inc. | In vivo agents comprising cationic drugs, peptides and metal chelators with acidic saccharides and glycosaminoglycans, giving improved site-selective localization, uptake mechanism, sensitivity and kinetic-spatial profiles, including tumor sites |
| US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| DE69826528T2 (de) * | 1997-12-23 | 2006-02-23 | Amersham Health As | Stickstoffoxid freisetzende chelatbildner und ihre therapeutische verwendung |
| IT1297035B1 (it) | 1997-12-30 | 1999-08-03 | Bracco Spa | Derivati dell'acido 1,4,7,10-tetraazaciclododecan-1,4-diacetico |
| IT1315263B1 (it) | 1999-12-21 | 2003-02-03 | Bracco Spa | Composti chelanti,loro chelati con ioni metallici paramagnetici, loropreparazione ed uso |
| US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
| US7244853B2 (en) | 2001-05-09 | 2007-07-17 | President And Fellows Of Harvard College | Dioxanes and uses thereof |
| WO2006102557A2 (fr) | 2005-03-22 | 2006-09-28 | The President And Fellows Of Harvard College | Traitement de troubles lies a la degradation de proteines |
| WO2006124726A2 (fr) | 2005-05-12 | 2006-11-23 | The General Hospital Corporation | Nouvelles compositions biotinylatees |
| CN101400362B (zh) * | 2006-02-14 | 2016-10-12 | 哈佛大学校长及研究员协会 | 双官能组蛋白去乙酰化酶抑制剂 |
| CA2654540C (fr) | 2006-05-03 | 2017-01-17 | President And Fellows Of Harvard College | Inhibiteurs d'histone desacetylases et de tubuline desacetylases |
| DE102007002726A1 (de) | 2007-01-18 | 2008-07-31 | Bayer Schering Pharma Aktiengesellschaft | Neue Kaskaden-Polymer-Komplexe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| DE102007058220A1 (de) | 2007-12-03 | 2009-06-04 | Bayer Schering Pharma Aktiengesellschaft | Dimere macrocyclisch substituierte Benzolderivate |
| US20090208421A1 (en) | 2008-02-19 | 2009-08-20 | Dominique Meyer | Process for preparing a pharmaceutical formulation of contrast agents |
| JP5397976B2 (ja) * | 2008-05-07 | 2014-01-22 | 公立大学法人大阪府立大学 | 常磁性金属含有ポリアミドアミンデンドロン脂質 |
| CA2731730C (fr) | 2008-07-23 | 2017-06-13 | President And Fellows Of Harvard College | Inhibiteurs de desacetylase et leurs utilisations |
| FR2945448B1 (fr) | 2009-05-13 | 2012-08-31 | Guerbet Sa | Procede de preparation d'une formulation pharmaceutique de chelate de lanthanide sous forme de poudre. |
| WO2011019393A2 (fr) | 2009-08-11 | 2011-02-17 | President And Fellows Of Harvard College | Inhibiteurs de hdac classe- et isoforme-spécifiques et utilisations de ceux-ci |
| EP2338874A1 (fr) * | 2009-12-16 | 2011-06-29 | Bracco Imaging S.p.A | Procédé pour la préparation de composés chélatés |
| PE20141325A1 (es) | 2011-04-21 | 2014-10-08 | Bayer Ip Gmbh | Preparacion de gadobutrol de alta pureza |
| EP3441467A3 (fr) | 2012-08-31 | 2019-04-24 | The General Hospital Corporation | Complexes de biotine pour le traitement et le diagnostic de la maladie d'alzheimer |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1070695A (fr) * | 1975-09-02 | 1980-01-29 | Michael D. Loberg | Produit pharmaceutique a base d'acide iminodiacetique |
| US4176173A (en) * | 1977-07-18 | 1979-11-27 | Medi-Physics, Inc. | Radiographic compositions |
| US4352751A (en) * | 1979-09-10 | 1982-10-05 | Analytical Radiation Corporation | Species-linked diamine triacetic acids and their chelates |
| DE3033651A1 (de) * | 1980-09-06 | 1982-03-25 | Wilhelm Bögle KG, 7410 Reutlingen | Haltevorrichtung fuer stoffbespannbare paneelierte wandungen |
| DE3038853A1 (de) * | 1980-10-10 | 1982-05-27 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue n-hydroxy-alkylierte dicarbonsaeure-bis-(3,5-dicarbamoyl-2,4,6-trijodanilide), deren herstellung und diese enthaltende roentgenkonstrastmittel (ii) |
| US4385046A (en) * | 1980-12-15 | 1983-05-24 | Minnesota Mining And Manufacturing Company | Diagnostic radio-labeled polysaccharide derivatives |
| DE3129906C3 (de) * | 1981-07-24 | 1996-12-19 | Schering Ag | Paramagnetische Komplexsalze, deren Herstellung und Mittel zur Verwendung bei der NMR-Diagnostik |
| CA1242643A (fr) * | 1983-08-12 | 1988-10-04 | Eric T. Fossel | Imagerie medicale par rmn faisant appel a des reactifs provoquant des deplacements chimiques |
| US4687658A (en) * | 1984-10-04 | 1987-08-18 | Salutar, Inc. | Metal chelates of diethylenetriaminepentaacetic acid partial esters for NMR imaging |
-
1984
- 1984-01-10 NL NL8400079A patent/NL194579C/nl not_active IP Right Cessation
- 1984-01-11 DE DE3401052A patent/DE3401052C2/de not_active Expired - Lifetime
- 1984-01-18 NZ NZ219079A patent/NZ219079A/xx unknown
- 1984-01-18 AU AU23559/84A patent/AU574658B2/en not_active Expired
- 1984-01-18 NZ NZ206868A patent/NZ206868A/xx unknown
- 1984-01-18 IL IL77761A patent/IL77761A/xx not_active IP Right Cessation
- 1984-01-18 IL IL70711A patent/IL70711A/xx not_active IP Right Cessation
- 1984-01-18 JP JP59005849A patent/JPH0772162B2/ja not_active Expired - Lifetime
- 1984-01-19 FR FR8400812A patent/FR2539996B1/fr not_active Expired
- 1984-01-19 ES ES529020A patent/ES529020A0/es active Granted
- 1984-01-19 FI FI840226A patent/FI79026C/fi not_active IP Right Cessation
- 1984-01-19 SE SE8400254A patent/SE510582C2/sv not_active IP Right Cessation
- 1984-01-19 GR GR73552A patent/GR81653B/el unknown
- 1984-01-19 BE BE2/60318A patent/BE898708A/nl not_active IP Right Cessation
- 1984-01-19 IT IT8419241A patent/IT1213128B/it active
- 1984-01-20 GB GB08401486A patent/GB2137612A/en not_active Withdrawn
- 1984-01-20 PT PT77983A patent/PT77983B/pt unknown
- 1984-01-20 CH CH266/84A patent/CH660183A5/de not_active IP Right Cessation
- 1984-01-20 AT AT0019184A patent/AT397465B/de not_active IP Right Cessation
- 1984-01-20 DK DK025484A patent/DK170460B1/da not_active IP Right Cessation
- 1984-01-20 CA CA000445771A patent/CA1256249A/fr not_active Expired
- 1984-01-20 IE IE126/84A patent/IE56855B1/en not_active IP Right Cessation
- 1984-01-20 NO NO840223A patent/NO169103C/no not_active IP Right Cessation
- 1984-01-20 ZA ZA84472A patent/ZA84472B/xx unknown
- 1984-01-20 LU LU85177A patent/LU85177A1/de unknown
- 1984-01-20 IE IE169/89A patent/IE56857B1/en not_active IP Right Cessation
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1985
- 1985-12-04 GB GB08529901A patent/GB2169598B/en not_active Expired
- 1985-12-04 GB GB08529903A patent/GB2169599B/en not_active Expired
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1986
- 1986-08-04 FR FR868611256A patent/FR2590484B1/fr not_active Expired
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1988
- 1988-01-11 AU AU10184/88A patent/AU607456B2/en not_active Expired
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1991
- 1991-03-14 JP JP3073718A patent/JP2556627B2/ja not_active Expired - Lifetime
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1993
- 1993-05-06 SE SE9301557A patent/SE512863C2/sv not_active IP Right Cessation
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1994
- 1994-08-01 DK DK089794A patent/DK170461B1/da not_active IP Right Cessation
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2001
- 2001-12-13 NL NL9900020A patent/NL195071C/nl not_active IP Right Cessation
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