NO317177B1 - Radiofarmasoytikum, radiofarmasoytisk preparat samt kit for fremstilling av et radiofarmasoytikum - Google Patents
Radiofarmasoytikum, radiofarmasoytisk preparat samt kit for fremstilling av et radiofarmasoytikum Download PDFInfo
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- NO317177B1 NO317177B1 NO19974549A NO974549A NO317177B1 NO 317177 B1 NO317177 B1 NO 317177B1 NO 19974549 A NO19974549 A NO 19974549A NO 974549 A NO974549 A NO 974549A NO 317177 B1 NO317177 B1 NO 317177B1
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- independent basis
- group
- carbon atom
- radiopharmaceutical
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- 108010071584 oxidized low density lipoprotein Proteins 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
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- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/745—Blood coagulation or fibrinolysis factors
- C07K14/75—Fibrinogen
-
- 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
-
- 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
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0476—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from monodendate ligands, e.g. sestamibi
-
- 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
- A61K51/0497—Organic compounds conjugates with a carrier being an organic 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
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/082—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being a RGD-containing peptide
-
- 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
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/008—Peptides; Proteins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Hematology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/415,908 US5744120A (en) | 1993-03-30 | 1995-04-03 | Ternary radiopharmaceutical complexes |
| PCT/US1996/004567 WO1996031243A1 (en) | 1995-04-03 | 1996-04-03 | Ternary radiopharmaceutical complexes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO974549D0 NO974549D0 (no) | 1997-10-02 |
| NO974549L NO974549L (no) | 1997-12-02 |
| NO317177B1 true NO317177B1 (no) | 2004-09-06 |
Family
ID=23647726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19974549A NO317177B1 (no) | 1995-04-03 | 1997-10-02 | Radiofarmasoytikum, radiofarmasoytisk preparat samt kit for fremstilling av et radiofarmasoytikum |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US5744120A (de) |
| EP (2) | EP0820312B1 (de) |
| JP (1) | JPH11503166A (de) |
| KR (1) | KR100417558B1 (de) |
| CN (1) | CN1080127C (de) |
| AR (1) | AR006077A1 (de) |
| AT (1) | ATE220335T1 (de) |
| AU (1) | AU719529B2 (de) |
| BR (1) | BR9608065A (de) |
| CA (1) | CA2216423C (de) |
| CZ (1) | CZ291658B6 (de) |
| DE (1) | DE69622267T2 (de) |
| DK (1) | DK0820312T3 (de) |
| EA (1) | EA000636B1 (de) |
| EE (1) | EE9700250A (de) |
| ES (1) | ES2179196T3 (de) |
| HR (1) | HRP960148A2 (de) |
| HU (1) | HU225674B1 (de) |
| IL (1) | IL117642A (de) |
| LT (1) | LT4391B (de) |
| LV (1) | LV12039B (de) |
| MX (1) | MX9707430A (de) |
| NO (1) | NO317177B1 (de) |
| NZ (2) | NZ333276A (de) |
| PL (1) | PL185325B1 (de) |
| PT (1) | PT820312E (de) |
| SI (1) | SI9620044B (de) |
| SK (1) | SK283276B6 (de) |
| TW (1) | TW503110B (de) |
| UA (1) | UA56127C2 (de) |
| WO (1) | WO1996031243A1 (de) |
| ZA (1) | ZA962672B (de) |
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| US5968476A (en) * | 1992-05-21 | 1999-10-19 | Diatide, Inc. | Technetium-99m labeled peptides for thrombus imaging |
| US5744120A (en) * | 1993-03-30 | 1998-04-28 | The Dupont Merick Pharmaceutical Company | Ternary radiopharmaceutical complexes |
| JP2954355B2 (ja) * | 1993-04-08 | 1999-09-27 | ダイアテク，インコーポレイテッド | 血栓イメージング用の放射性同位体標識化合物 |
| US5855867A (en) * | 1995-03-29 | 1999-01-05 | The Curators Of The University Of Missouri | Hydroxymethyl phosphine compounds for use as diagnostic and therapeutic pharmaceuticals and method of making same |
| US5739313A (en) | 1995-11-13 | 1998-04-14 | Regents Of The University Of Minnesota | Radionuclide labeling of vitamin B12 and coenzymes thereof |
| EP0888130B1 (de) * | 1996-03-13 | 2003-07-02 | Bristol-Myers Squibb Pharma Company | Ternäre radiopharmazeutische komplexe |
| US6416733B1 (en) * | 1996-10-07 | 2002-07-09 | Bristol-Myers Squibb Pharma Company | Radiopharmaceuticals for imaging infection and inflammation |
| US20030124053A1 (en) * | 1996-10-07 | 2003-07-03 | Barrett John Andrew | Radiopharmaceuticals for imaging infection and inflammation |
| US6403054B1 (en) * | 1997-05-28 | 2002-06-11 | Bristol-Myers Squibb Pharma Company | Ternary ligand complexes useful as radiopharmaceuticals |
| US7060251B1 (en) * | 1997-09-08 | 2006-06-13 | The General Hospital Corporation | Imaging agents for early detection and monitoring of cardiovascular plaque |
| AU9307498A (en) * | 1997-09-08 | 1999-03-29 | General Hospital Corporation, The | Imaging agents for early detection and monitoring of cardiovascular plaque |
| US6537520B1 (en) | 1998-03-31 | 2003-03-25 | Bristol-Myers Squibb Pharma Company | Pharmaceuticals for the imaging of angiogenic disorders |
| US6548663B1 (en) | 1998-03-31 | 2003-04-15 | Bristol-Myers Squibb Pharma Company | Benzodiazepine vitronectin receptor antagonist pharmaceuticals |
| US6524553B2 (en) | 1998-03-31 | 2003-02-25 | Bristol-Myers Squibb Pharma Company | Quinolone vitronectin receptor antagonist pharmaceuticals |
| SK13952000A3 (sk) | 1998-03-31 | 2001-12-03 | Dupont Pharmaceuticals Company | Farmaceutické zlúčeniny na zobrazovanie porúch angiogenézy |
| EP1068222A1 (de) * | 1998-04-03 | 2001-01-17 | Du Pont Pharmaceuticals Company | Radiopharmazeutika zur darstellung einer infektion, einer entzündung sowie der darstellung und behandlung von krebs |
| US6569402B1 (en) | 1998-12-18 | 2003-05-27 | Bristol-Myers Squibb Pharma Company | Vitronectin receptor antagonist pharmaceuticals |
| US6794518B1 (en) * | 1998-12-18 | 2004-09-21 | Bristol-Myers Squibb Pharma Company | Vitronectin receptor antagonist pharmaceuticals |
| US6511649B1 (en) * | 1998-12-18 | 2003-01-28 | Thomas D. Harris | Vitronectin receptor antagonist pharmaceuticals |
| BR9917079A (pt) | 1998-12-18 | 2001-10-30 | Du Pont Pharm Co | Compostos antagonistas de receptor devitronectina, kit, composição metalofarmacêuticade diagnóstico ou terapêutica, composição deagente de contraste para ultra-som, composiçãoradiofarmacêutica terapêutica, composiçãofarmacêutica de diagnóstico, método detratamento da artrite reumatóide, do cancêr e darestenose em um paciente, método de formação deimagem da angiogênese terapêutica, do câncer, denovos vasos sanguìneos, da arteriosclerose, darestenose, da isquemia e da lesão por reperfusãodo miocárdio em um paciente |
| CA2349333A1 (en) | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | Vitronectin receptor antagonist pharmaceuticals |
| US6346547B1 (en) | 1999-02-08 | 2002-02-12 | Checkpoint, Genetics, Inc. | N-substituted amino acids, antioxidant pharmaceutical compositions containing n-substituted amino acids and methods for preventing cardiovascular diseases and/or preventing and/or treating antioxidant responsive diseases therewith |
| US6844425B1 (en) * | 1999-02-24 | 2005-01-18 | Mallinckrodt Inc. | Combination of intercalating organometallic complexes and tumor seeking biomolecules for DNA cleavage and radiotherapy |
| US6808698B1 (en) | 1999-03-26 | 2004-10-26 | Bristol-Myers Squibb Pharma Company | Method for localization of blood clots |
| BR0010517A (pt) * | 1999-03-26 | 2002-01-08 | Du Pont Pharm Co | Métodos de formação de imagem de um trombo, de um êmbolo pulmonar, de um trombo arterial e de um trombo coronariano |
| US6806363B1 (en) | 1999-04-16 | 2004-10-19 | Mayo Foundation For Medical Education & Research | Cobalamin conjugates useful as antitumor agents |
| EP1239887A1 (de) | 1999-10-15 | 2002-09-18 | Mayo Foundation For Medical Education And Research | Cobalamin-konjugate geeignet zur verwendung wie bilderzeugungs- oder therapeutische mitteln |
| US7591995B2 (en) | 1999-10-15 | 2009-09-22 | Mayo Foundation For Medical Education And Research | Cobalamin conjugates useful as imaging and therapeutic agents |
| US6534038B2 (en) * | 2000-04-07 | 2003-03-18 | Bristol-Myers Squibb Pharma Company | Ternary ligand complexes useful as radiopharmaceuticals |
| AU2001261728A1 (en) | 2000-05-17 | 2001-11-26 | Bristol-Myers Squibb Pharma Company | Use of small molecule radioligands for diagnostic imaging |
| EP1268450A1 (de) | 2000-06-01 | 2003-01-02 | Bristol-Myers Squibb Pharma Company | Durch bernsteinsäurediamid substituierte lactamverbindungen als a-beta-protein-produktionsinhibitoren |
| HUP0400758A3 (en) * | 2000-11-03 | 2005-02-28 | Bristol Myers Squibb Pharma Co | Simultaneous dual isotope imaging of cardiac perfusion and cardiac inflammation |
| WO2002055111A2 (en) * | 2000-11-27 | 2002-07-18 | Bristol Myers Squibb Medical I | Simultaneous imaging of cardiac perfusion and a vitronectin receptor targeted imaging agent |
| US6776977B2 (en) | 2001-01-09 | 2004-08-17 | Bristol-Myers Squibb Pharma Company | Polypodal chelants for metallopharmaceuticals |
| US20020094316A1 (en) * | 2001-01-09 | 2002-07-18 | Shuang Liu | Polypodal chelants for metallopharmaceuticals |
| US6517814B2 (en) | 2001-01-09 | 2003-02-11 | Bristol-Myers Squibb Pharma Company | Macrocyclic chelants useful for metallopharmaceuticals |
| WO2002067761A2 (en) | 2001-02-23 | 2002-09-06 | Bristol-Myers Squibb Pharma Company | Labeled macrophage scavenger receptor antagonists for imaging atherosclerosis and vulnerable plaque |
| AU2002331042B2 (en) * | 2001-08-08 | 2007-10-25 | Bristol-Myers Squibb Pharma Company | Simultaneous imaging of cardiac perfusion and a vitronectin receptor targeted imaging agent |
| US6838074B2 (en) | 2001-08-08 | 2005-01-04 | Bristol-Myers Squibb Company | Simultaneous imaging of cardiac perfusion and a vitronectin receptor targeted imaging agent |
| US7319149B2 (en) * | 2003-06-13 | 2008-01-15 | Bristol-Myers Squibb Pharma Company | Chelants and macrocyclic metal complex radiopharmaceuticals thereof |
| US7317104B2 (en) | 2003-06-13 | 2008-01-08 | Bristol-Myers Squibb Pharma Company | Chelants and macrocyclic metal complex radiopharmaceuticals thereof |
| US20050106100A1 (en) * | 2003-09-03 | 2005-05-19 | Harris Thomas D. | Compounds containing matrix metalloproteinase substrates and methods of their use |
| KR20080022588A (ko) * | 2005-06-30 | 2008-03-11 | 브리스톨-마이어스 스퀴브 파마 컴퍼니 | 영상화제로서의 히드라지드 컨쥬게이트 |
| US8668900B2 (en) | 2011-02-15 | 2014-03-11 | Kuwait University | Cancer-imaging agent and method of radioimaging using the same |
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| US4248802A (en) * | 1975-06-20 | 1981-02-03 | Rhone-Poulenc Industries | Catalytic hydroformylation of olefins |
| CA1300608C (en) * | 1985-05-10 | 1992-05-12 | Edward A. Deutsch | 99 mtc (iii) myocardial imaging agents which are non-reducable in vivo |
| GB8624272D0 (en) * | 1986-10-09 | 1986-11-12 | Amersham Int Plc | Cationic complexes of tc-99m |
| GB8711496D0 (en) * | 1987-05-15 | 1987-06-17 | Amersham Int Plc | Tc-99m radiopharmaceuticals |
| ATE85619T1 (de) * | 1988-03-09 | 1993-02-15 | Cis Bio Int | Herstellung von als radiopharmazeutische produkte verwendbare nitruroverbindungen. |
| GB8808414D0 (en) * | 1988-04-11 | 1988-05-11 | Amersham Int Plc | Ligands & cationic complexes thereof with technetium-99m |
| US5002754A (en) * | 1988-06-15 | 1991-03-26 | University Of Cincinnati | Technetium (III/II) imaging agents |
| US5066789A (en) * | 1988-09-30 | 1991-11-19 | Neorx Corporation | Targeting substance-diagnostic/therapeutic agent conjugates having Schiff base linkages |
| GB8902362D0 (en) * | 1989-02-03 | 1989-03-22 | Amersham Int Plc | Cationic complexes of technetium-99m |
| US5206370A (en) * | 1989-02-24 | 1993-04-27 | Johnson Matthey, Inc. | Certain pyridyl hydrazines and hydrazides useful for protein labeling |
| US5792444A (en) * | 1989-05-09 | 1998-08-11 | The General Hospital Corporation | Labeled chemotactic peptides to image focal sites of infection or inflammation |
| US4957728A (en) * | 1989-05-19 | 1990-09-18 | University Of Cincinnati | Kit for preparing Tc (III)-99m myocardial imaging agents that are effective in humans |
| US4917879A (en) * | 1989-05-19 | 1990-04-17 | University Of Cincinnati | 99MTC(III) myocardial imaging agents that are effective in humans |
| US5384309A (en) * | 1989-07-17 | 1995-01-24 | Genentech, Inc. | Cyclized peptides and their use as platelet aggregation inhibitors |
| GB8919488D0 (en) * | 1989-08-29 | 1989-10-11 | Amersham Int Plc | New cores for technetium radiopharmaceuticals |
| EP0427360B1 (de) * | 1989-10-30 | 1994-06-15 | Verein für Kernverfahrenstechnik und Analytik Rossendorf e.V. | Kit (nichtradioaktive Vorstufe) zur Herstellung einer enantiomeren Form des Nierenfunktionsdiagnostikums Technetium-99m-Mercaptoacetyltriglycin (99m-Tc-MAG-3) und Verfahren zur Herstellung des Kits |
| FR2664166A1 (fr) * | 1990-07-04 | 1992-01-10 | Cis Bio Int | Procede de preparation de complexes nitruro de metaux de transition utilisables comme produits radiopharmaceutiques ou pour la synthese de nouveaux produits radiopharmaceutiques. |
| US5112594A (en) * | 1991-04-04 | 1992-05-12 | Mallinckrodt Medical, Inc. | Kit for preparing a technetium-99m myocardial imaging agent |
| WO1992017492A1 (en) * | 1991-04-05 | 1992-10-15 | Genentech, Inc. | PLATELET AGGREGATION INHIBITORS HAVING HIGH SPECIFICITY FOR GP IIbIII¿a? |
| FR2679452B1 (fr) * | 1991-07-22 | 1993-11-12 | Cis Bio International | Produit radiopharmaceutique ayant notamment un tropisme cerebral, comportant un complexe nitruro d'un metal de transition, et son procede de preparation. |
| US5336482A (en) * | 1991-12-05 | 1994-08-09 | The Du Pont Merck Pharmaceutical Company | Technetium-99m complexes with N-substituted 3-hydroxy-4-pyridinones |
| US5300280A (en) * | 1992-02-14 | 1994-04-05 | Mallinckrodt Medical, Inc. | Stabilized radiopharmaceutical kits |
| GB9209641D0 (en) * | 1992-05-02 | 1992-06-17 | Johnson Matthey Plc | Improvements in radiolabelling |
| US5879657A (en) * | 1993-03-30 | 1999-03-09 | The Dupont Merck Pharmaceutical Company | Radiolabeled platelet GPIIb/IIIa receptor antagonists as imaging agents for the diagnosis of thromboembolic disorders |
| US5744120A (en) * | 1993-03-30 | 1998-04-28 | The Dupont Merick Pharmaceutical Company | Ternary radiopharmaceutical complexes |
| HU222574B1 (hu) * | 1993-03-31 | 2003-08-28 | Mallinckrodt Medical Inc. | Redukálószerként foszfinokat tartalmazó radioaktív gyógyászati készítmények és az ezeket tartalmazó készletek |
| IT1261386B (it) * | 1993-12-21 | 1996-05-20 | Sorin Biomedica Spa | Peptidi modificati con gruppo fosfinico per la marcatura con 99m-tc e 186-188-re o agenti paramagnetici. |
| US5521156A (en) * | 1994-02-03 | 1996-05-28 | Merrell Pharmaceuticals Inc. | Cyclic neurokinin A antagonists |
| US8019150B2 (en) | 2007-10-11 | 2011-09-13 | Kwe International, Inc. | Color quantization based on desired upper bound for relative quantization step |
-
1995
- 1995-04-03 US US08/415,908 patent/US5744120A/en not_active Expired - Fee Related
-
1996
- 1996-03-04 UA UA97094591A patent/UA56127C2/uk unknown
- 1996-03-25 IL IL11764296A patent/IL117642A/xx active IP Right Grant
- 1996-04-01 HR HR08/415,908A patent/HRP960148A2/hr not_active Application Discontinuation
- 1996-04-03 ZA ZA9602672A patent/ZA962672B/xx unknown
- 1996-04-03 CN CN96194172A patent/CN1080127C/zh not_active Expired - Fee Related
- 1996-04-03 AU AU57874/96A patent/AU719529B2/en not_active Ceased
- 1996-04-03 DK DK96914548T patent/DK0820312T3/da active
- 1996-04-03 WO PCT/US1996/004567 patent/WO1996031243A1/en active IP Right Grant
- 1996-04-03 CA CA002216423A patent/CA2216423C/en not_active Expired - Fee Related
- 1996-04-03 AT AT96914548T patent/ATE220335T1/de not_active IP Right Cessation
- 1996-04-03 EA EA199700291A patent/EA000636B1/ru not_active IP Right Cessation
- 1996-04-03 EP EP96914548A patent/EP0820312B1/de not_active Expired - Lifetime
- 1996-04-03 BR BR9608065A patent/BR9608065A/pt not_active IP Right Cessation
- 1996-04-03 AR ARP960102071A patent/AR006077A1/es active IP Right Grant
- 1996-04-03 PL PL96322583A patent/PL185325B1/pl unknown
- 1996-04-03 ES ES96914548T patent/ES2179196T3/es not_active Expired - Lifetime
- 1996-04-03 DE DE69622267T patent/DE69622267T2/de not_active Expired - Fee Related
- 1996-04-03 EP EP01123928A patent/EP1195168A3/de not_active Withdrawn
- 1996-04-03 EE EE9700250A patent/EE9700250A/xx unknown
- 1996-04-03 JP JP8530453A patent/JPH11503166A/ja not_active Ceased
- 1996-04-03 HU HU9801949A patent/HU225674B1/hu not_active IP Right Cessation
- 1996-04-03 CZ CZ19973027A patent/CZ291658B6/cs not_active IP Right Cessation
- 1996-04-03 PT PT96914548T patent/PT820312E/pt unknown
- 1996-04-03 SI SI9620044A patent/SI9620044B/sl not_active IP Right Cessation
- 1996-04-03 MX MX9707430A patent/MX9707430A/es not_active IP Right Cessation
- 1996-04-03 NZ NZ333276A patent/NZ333276A/xx unknown
- 1996-04-03 KR KR1019970706964A patent/KR100417558B1/ko not_active IP Right Cessation
- 1996-04-03 SK SK1329-97A patent/SK283276B6/sk unknown
- 1996-04-03 NZ NZ308284A patent/NZ308284A/xx unknown
- 1996-04-05 TW TW085104041A patent/TW503110B/zh not_active IP Right Cessation
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1997
- 1997-10-01 LV LVP-97-185A patent/LV12039B/en unknown
- 1997-10-01 LT LT97-157A patent/LT4391B/lt not_active IP Right Cessation
- 1997-10-02 NO NO19974549A patent/NO317177B1/no unknown
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1998
- 1998-01-26 US US09/013,320 patent/US6010679A/en not_active Expired - Fee Related
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