UA61890C2 - Cascade polymeric complexes, pharmaceutical agents containing them, and original compounds - Google Patents
Cascade polymeric complexes, pharmaceutical agents containing them, and original compounds Download PDFInfo
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- UA61890C2 UA61890C2 UA98020587A UA98020587A UA61890C2 UA 61890 C2 UA61890 C2 UA 61890C2 UA 98020587 A UA98020587 A UA 98020587A UA 98020587 A UA98020587 A UA 98020587A UA 61890 C2 UA61890 C2 UA 61890C2
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- group
- necessary
- cascade
- groups
- carboxy
- Prior art date
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
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- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 210000002966 serum Anatomy 0.000 description 1
- 239000003579 shift reagent Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 101150047903 vapA gene Proteins 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
- ORZHVTYKPFFVMG-UHFFFAOYSA-N xylenol orange Chemical compound OC(=O)CN(CC(O)=O)CC1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(CN(CC(O)=O)CC(O)=O)C(O)=C(C)C=2)=C1 ORZHVTYKPFFVMG-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
-
- 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
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/085—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier conjugated systems
-
- 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
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/12—Macromolecular compounds
- A61K49/124—Macromolecular compounds dendrimers, dendrons, hyperbranched compounds
-
- 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
- A61K51/06—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules
- A61K51/065—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules conjugates with carriers being macromolecules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/76—Metal complexes of amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/16—Dendrimers and dendritic polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19525924A DE19525924A1 (de) | 1995-07-04 | 1995-07-04 | Kaskaden-Polymer-Komplexe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| PCT/EP1996/002671 WO1997002051A2 (de) | 1995-07-04 | 1996-06-20 | Kaskaden-polymer-komplexe, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA61890C2 true UA61890C2 (en) | 2003-12-15 |
Family
ID=7766984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA98020587A UA61890C2 (en) | 1995-07-04 | 1996-06-20 | Cascade polymeric complexes, pharmaceutical agents containing them, and original compounds |
Country Status (27)
| Country | Link |
|---|---|
| US (6) | US5820849A (bg) |
| EP (1) | EP0836485B1 (bg) |
| JP (1) | JP3723219B2 (bg) |
| KR (1) | KR100428272B1 (bg) |
| CN (2) | CN1079679C (bg) |
| AT (1) | ATE220924T1 (bg) |
| BG (1) | BG62600B1 (bg) |
| BR (1) | BR9609478A (bg) |
| CA (1) | CA2225959A1 (bg) |
| CL (1) | CL2004001126A1 (bg) |
| CZ (1) | CZ294951B6 (bg) |
| DE (2) | DE19525924A1 (bg) |
| DK (1) | DK0836485T3 (bg) |
| ES (1) | ES2177792T3 (bg) |
| HK (2) | HK1013915A1 (bg) |
| IL (2) | IL122554A (bg) |
| MX (1) | MX9800023A (bg) |
| NO (1) | NO324560B1 (bg) |
| NZ (1) | NZ312127A (bg) |
| PL (1) | PL187712B1 (bg) |
| PT (1) | PT836485E (bg) |
| RU (1) | RU2166501C2 (bg) |
| SK (1) | SK283838B6 (bg) |
| TW (2) | TW579380B (bg) |
| UA (1) | UA61890C2 (bg) |
| WO (1) | WO1997002051A2 (bg) |
| ZA (1) | ZA965686B (bg) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4425857A1 (de) * | 1994-07-07 | 1996-01-11 | Schering Ag | Kaskaden-Polymer-Komplexe, Verfahren zur ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| DE19525924A1 (de) * | 1995-07-04 | 1997-01-09 | Schering Ag | Kaskaden-Polymer-Komplexe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| DE19652387A1 (de) * | 1996-12-04 | 1998-06-10 | Schering Ag | Macrocyclische Metallkomplexcarbonsäuren, ihre Verwendung sowie Verfahren zu ihrer Herstellung |
| DE19728954C1 (de) * | 1997-06-30 | 1999-04-22 | Schering Ag | Saccharid-Konjugate, diese enthaltende pharmazeutische Mittel, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19729013A1 (de) * | 1997-07-03 | 1999-02-04 | Schering Ag | Oligomere, perfluoralkylhaltige Verbindungen, Verfahren zu deren Herstellung und ihre Verwendung in der NMR-Diagnostik |
| US6019959A (en) * | 1997-07-31 | 2000-02-01 | Schering Aktiengesellschaft | Oligomeric compounds that contain perfluoroalkyl, process for their production, and their use in NMR diagnosis |
| US7745142B2 (en) | 1997-09-15 | 2010-06-29 | Molecular Devices Corporation | Molecular modification assays |
| US6297018B1 (en) | 1998-04-17 | 2001-10-02 | Ljl Biosystems, Inc. | Methods and apparatus for detecting nucleic acid polymorphisms |
| DE19758105A1 (de) * | 1997-12-18 | 1999-06-24 | Schering Ag | Dendritische Polymer-Saccharid-Konjugate, diese enthaltende pharmazeutische Mittel, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US7405320B2 (en) * | 1998-06-22 | 2008-07-29 | Immunomedics, Inc. | Therapeutic and diagnostic conjugates for use with multispecific antibodies |
| US6515113B2 (en) | 1999-02-18 | 2003-02-04 | The Regents Of The University Of California | Phthalamide lanthanide complexes for use as luminescent markers |
| AU762754B2 (en) | 1999-02-18 | 2003-07-03 | Regents Of The University Of California, The | Salicylamide-lanthanide complexes for use as luminescent markers |
| HUP0202635A3 (en) * | 1999-07-29 | 2006-03-28 | Epix Medical Inc Cambridge | Targeting multimeric imaging agents through multilocus binding |
| US6549798B2 (en) * | 2001-02-07 | 2003-04-15 | Epix Medical, Inc. | Magnetic resonance angiography data |
| AU2002350991A1 (en) * | 2001-06-25 | 2003-01-08 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of | Macromolecular imaging agents for liver imaging |
| DE10135356C1 (de) * | 2001-07-20 | 2003-04-17 | Schering Ag | Makrocyclische Metallkomplexe und deren Verwendung zur Herstellung von Konjugaten mit Biomolekülen |
| TWI221406B (en) | 2001-07-30 | 2004-10-01 | Epix Medical Inc | Systems and methods for targeted magnetic resonance imaging of the vascular system |
| GB0122049D0 (en) * | 2001-09-12 | 2001-10-31 | Nycomed Imaging As | Method |
| US7648678B2 (en) | 2002-12-20 | 2010-01-19 | Dako Denmark A/S | Method and system for pretreatment of tissue slides |
| AR047692A1 (es) * | 2003-07-10 | 2006-02-08 | Epix Medical Inc | Imagenes de blancos estacionarios |
| EP1541568A1 (de) * | 2003-12-09 | 2005-06-15 | Deutsches Wollforschungsinstitut an der Rheinisch-Westfälischen Technischen Hochschule Aachen e.V. | Reaktive cyclische Carbonate und Harnstoffe zur Modifizierung von Biomolekülen, Polymeren und Oberflächen |
| US7199268B2 (en) | 2003-12-16 | 2007-04-03 | Schering Aktiengesellschaft | Process for the production of dendritic trimesic acid triamides |
| DE10361140B4 (de) * | 2003-12-16 | 2006-11-09 | Schering Ag | Verfahren zur Herstellung von dendritischen Trimesinsäuretriamiden, dabei verwendete Diethylentriaminderivate und Verwendung der Diethylentriaminderivate |
| WO2006001835A2 (en) * | 2003-12-30 | 2006-01-05 | The Regents Of The University Of California | Aromatic triamide-lanthanide complexes |
| US20050171424A1 (en) * | 2004-01-13 | 2005-08-04 | The Gov. Of The Usa As Rep. By The Secretary Of The Dept. Of Health And Human Services | Methods for imaging the lymphatic system using dendrimer-based contrast agents |
| DE102004062258B3 (de) * | 2004-12-23 | 2006-01-05 | Schering Ag | Hydroxypyridinon-Derivate, deren Metallkomplexe und deren Verwendung zur Herstellung von Konjugaten mit Biomolekülen |
| US20060204443A1 (en) * | 2005-03-11 | 2006-09-14 | The Government Of The Usa As Represented By The Secretary Of The Dept. Of Health & Human Services | Methods for tumor treatment using dendrimer conjugates |
| AU2007272604B2 (en) | 2006-07-10 | 2013-08-01 | The Regents Of The University Of California | Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides |
| CA2660800C (en) * | 2006-08-15 | 2016-03-01 | The Regents Of The University Of California | Luminescent macrocyclic lanthanide complexes |
| CA2660717A1 (en) * | 2006-08-17 | 2008-02-21 | Epix Pharmaceuticals, Inc. | Methods for lymph system imaging |
| 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 |
| EP2114905B1 (en) * | 2007-01-25 | 2015-04-15 | Lumiphore, Inc. | Multi-color time resolved fluorophores based on macrocyclic lanthanide complexes |
| DE102007058220A1 (de) | 2007-12-03 | 2009-06-04 | Bayer Schering Pharma Aktiengesellschaft | Dimere macrocyclisch substituierte Benzolderivate |
| WO2009127715A1 (en) * | 2008-04-18 | 2009-10-22 | Ge Healthcare As | Compounds comprising paramagnetic chelates arranged around a central core and their use in magneto resonance imaging and spectroscopy |
| US20100008864A1 (en) * | 2008-07-10 | 2010-01-14 | Andreas Meijer | Aromatic multimers |
| US20100151591A1 (en) * | 2008-10-31 | 2010-06-17 | Butlin Nathaniel G | Rapid homogeneous diagnostic testing platform based on lanthanide fluorescent resonance energy transfer |
| EP2816038B8 (en) | 2009-08-24 | 2019-12-25 | Lumiphore, Inc. | Hopo chelators |
| WO2011079291A1 (en) * | 2009-12-24 | 2011-06-30 | Lumiphore, Inc. | Radiopharmaceutical complexes |
| KR101334780B1 (ko) | 2010-08-13 | 2013-12-02 | 한국생명공학연구원 | 요오드를 함유한 방사형상의 고분자 화합물, 이의 제조방법 및 이를 포함하는 ｃｔ용 조영제 조성물 |
| US9439984B2 (en) * | 2012-05-31 | 2016-09-13 | The Regents Of The University Of California | Macrocycles |
| CA2891593C (en) | 2012-11-16 | 2021-09-14 | Lumiphore, Inc. | Di-macrocycles |
| US11453652B2 (en) | 2013-03-15 | 2022-09-27 | Lumiphore, Inc. | Di-macrocycles |
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| CN110035996B (zh) | 2016-11-28 | 2022-08-09 | 拜耳医药股份公司 | 用于磁共振成像的新型高弛豫性钆螯合物 |
| CN109503770B (zh) * | 2018-10-18 | 2021-03-09 | 合肥工业大学 | 一种具有高弛豫率的水溶性交联纳米聚合物及其合成方法和用途 |
| KR20210095168A (ko) | 2018-11-23 | 2021-07-30 | 바이엘 악티엔게젤샤프트 | 조영 매체의 제형 및 그의 제조 방법 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4587329A (en) * | 1984-08-17 | 1986-05-06 | The Dow Chemical Company | Dense star polymers having two dimensional molecular diameter |
| US5527524A (en) * | 1986-08-18 | 1996-06-18 | The Dow Chemical Company | Dense star polymer conjugates |
| 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 |
| 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 |
| US5364613A (en) * | 1989-04-07 | 1994-11-15 | Sieving Paul F | Polychelants containing macrocyclic chelant moieties |
| GB8923843D0 (en) * | 1989-10-23 | 1989-12-13 | Salutar Inc | Compounds |
| US5446145A (en) * | 1990-01-19 | 1995-08-29 | Nycomed Salutar, Inc. | Polychelant compounds |
| 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 |
| US5162109A (en) * | 1990-09-13 | 1992-11-10 | Mallinckrodt Medical, Inc. | Magnetic resonance imaging agents |
| GB9024208D0 (en) * | 1990-11-07 | 1990-12-19 | Salutar Inc | Compounds |
| US5385719A (en) * | 1991-09-24 | 1995-01-31 | Unger; Evan C. | Copolymers and their use as contrast agents in magnetic resonance imaging and in other applications |
| US5405601A (en) * | 1993-07-02 | 1995-04-11 | Mallinckrodt Medical Inc. | Functionalized tripodal ligands for imaging applications |
| US5534241A (en) * | 1993-07-23 | 1996-07-09 | Torchilin; Vladimir P. | Amphipathic polychelating compounds and methods of use |
| US5449761A (en) * | 1993-09-28 | 1995-09-12 | Cytogen Corporation | Metal-binding targeted polypeptide constructs |
| DE4344464A1 (de) * | 1993-12-22 | 1995-06-29 | Schering Ag | Kaskadenpolymere mit Iodaromaten |
| DE4344460A1 (de) * | 1993-12-22 | 1995-06-29 | Schering Ag | Metallkomplexe von dendrimeren Makromolekülen, diese enthaltende diagnostische Mittel sowie Verfahren zur Herstellung der Komplexe und Mittel |
| GB9404208D0 (en) * | 1994-03-04 | 1994-04-20 | Nycomed Salutar Inc | Chelants |
| GB9407812D0 (en) * | 1994-04-20 | 1994-06-15 | Nycomed Salutar Inc | Compounds |
| DE4425857A1 (de) * | 1994-07-07 | 1996-01-11 | Schering Ag | Kaskaden-Polymer-Komplexe, Verfahren zur ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| US5634613A (en) * | 1994-07-18 | 1997-06-03 | Mccarthy; Peter T. | Tip vortex generation technology for creating a lift enhancing and drag reducing upwash effect |
| US5573750A (en) * | 1995-05-22 | 1996-11-12 | Nanosystems L.L.C. | Diagnostic imaging x-ray contrast agents |
| DE19525924A1 (de) * | 1995-07-04 | 1997-01-09 | Schering Ag | Kaskaden-Polymer-Komplexe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel |
| US5874061A (en) * | 1995-12-22 | 1999-02-23 | Schering Aktiengesellschaft | Cascade polymer complexes, process for their production and pharmaceutical agents containing said complexes |
| GB9624822D0 (en) | 1996-11-28 | 1997-01-15 | Nycomed Imaging As | Method |
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