DE69626392T2 - Stabile reagenzien zur herstellung von radiopharmazeutika - Google Patents
Stabile reagenzien zur herstellung von radiopharmazeutika Download PDFInfo
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- DE69626392T2 DE69626392T2 DE69626392T DE69626392T DE69626392T2 DE 69626392 T2 DE69626392 T2 DE 69626392T2 DE 69626392 T DE69626392 T DE 69626392T DE 69626392 T DE69626392 T DE 69626392T DE 69626392 T2 DE69626392 T2 DE 69626392T2
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- Prior art keywords
- hydrazone
- radiopharmaceutical
- ligands
- radiopharmaceuticals
- reagents
- Prior art date
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
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- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
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- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 1
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- PDTWJRMTMGZTTG-UHFFFAOYSA-N methyl 2-hydrazinylidenecyclopentane-1-carboxylate Chemical compound COC(=O)C1CCCC1=NN PDTWJRMTMGZTTG-UHFFFAOYSA-N 0.000 description 1
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- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N p-hydroxybenzoic acid propyl ester Natural products CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- IKZWQDXMCQQSLL-UHFFFAOYSA-N propylidenehydrazine Chemical compound CCC=NN IKZWQDXMCQQSLL-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- BLEQFIQOCMNEBW-UHFFFAOYSA-N pyridin-4-ylmethylidenehydrazine Chemical compound NN=CC1=CC=NC=C1 BLEQFIQOCMNEBW-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
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- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- WUAPFZMCVAUBPE-IGMARMGPSA-N rhenium-186 Chemical compound [186Re] WUAPFZMCVAUBPE-IGMARMGPSA-N 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- KFLRWGSAMLBHBV-UHFFFAOYSA-M sodium;pyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CN=C1 KFLRWGSAMLBHBV-UHFFFAOYSA-M 0.000 description 1
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
- 229940075620 somatostatin analogue Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- QQWYQAQQADNEIC-RVDMUPIBSA-N tert-butyl [(z)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(/C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-RVDMUPIBSA-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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- MYAJTCUQMQREFZ-UHFFFAOYSA-K tppts Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 MYAJTCUQMQREFZ-UHFFFAOYSA-K 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
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003667 tyrosine derivatives Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
-
- 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
- C07B59/008—Peptides; Proteins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Veterinary Medicine (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US476296 | 1983-03-17 | ||
| US08/476,296 US5750088A (en) | 1993-03-30 | 1995-06-07 | Stable hydrazones linked to a peptide moiety as reagents for the preparation of radiopharmaceuticals |
| PCT/US1996/009766 WO1996040637A1 (en) | 1995-06-07 | 1996-06-07 | Stable reagents for the preparation of radiopharmaceuticals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69626392D1 DE69626392D1 (de) | 2003-04-03 |
| DE69626392T2 true DE69626392T2 (de) | 2004-04-22 |
Family
ID=23891282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69626392T Expired - Fee Related DE69626392T2 (de) | 1995-06-07 | 1996-06-07 | Stabile reagenzien zur herstellung von radiopharmazeutika |
Country Status (29)
| Country | Link |
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| US (2) | US5750088A (enExample) |
| EP (1) | EP0832068B1 (enExample) |
| JP (1) | JPH11507364A (enExample) |
| KR (1) | KR19990022573A (enExample) |
| CN (1) | CN1192733A (enExample) |
| AR (1) | AR003959A1 (enExample) |
| AT (1) | ATE233241T1 (enExample) |
| AU (1) | AU718683B2 (enExample) |
| BR (1) | BR9609003A (enExample) |
| CA (1) | CA2222183A1 (enExample) |
| CZ (1) | CZ380197A3 (enExample) |
| DE (1) | DE69626392T2 (enExample) |
| EA (1) | EA000742B1 (enExample) |
| EE (1) | EE9700313A (enExample) |
| ES (1) | ES2193245T3 (enExample) |
| HR (1) | HRP960250A2 (enExample) |
| HU (1) | HUP9901469A3 (enExample) |
| IL (1) | IL118468A0 (enExample) |
| LT (1) | LT4380B (enExample) |
| LV (1) | LV12044B (enExample) |
| MX (1) | MX9709126A (enExample) |
| MY (1) | MY133974A (enExample) |
| NO (1) | NO975678L (enExample) |
| NZ (1) | NZ310799A (enExample) |
| PL (1) | PL323995A1 (enExample) |
| SI (1) | SI9620076B (enExample) |
| SK (1) | SK163497A3 (enExample) |
| WO (1) | WO1996040637A1 (enExample) |
| ZA (1) | ZA964854B (enExample) |
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| CA2249025A1 (en) * | 1996-03-13 | 1997-09-18 | Du Pont Pharmaceuticals Company | New ternary radiopharmaceutical complexes |
| ATE240123T1 (de) * | 1996-10-07 | 2003-05-15 | Bristol Myers Squibb Pharma Co | Radiopharmazeutische mittel zur bildgebung von infektionen und entzündungen |
| 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 |
| US6524553B2 (en) | 1998-03-31 | 2003-02-25 | Bristol-Myers Squibb Pharma Company | Quinolone vitronectin receptor antagonist pharmaceuticals |
| US6537520B1 (en) * | 1998-03-31 | 2003-03-25 | Bristol-Myers Squibb Pharma Company | Pharmaceuticals for the imaging of angiogenic disorders |
| WO1999051628A1 (en) * | 1998-04-03 | 1999-10-14 | Du Pont Pharmaceuticals Company | Radiopharmaceuticals for imaging infection and inflammation and for imaging and treatment of cancer |
| HRP990317A2 (en) * | 1998-10-13 | 2000-06-30 | Du Pont Pharm Co | A process for the preparation of a thrombus imaging agent |
| US6794518B1 (en) * | 1998-12-18 | 2004-09-21 | Bristol-Myers Squibb Pharma Company | Vitronectin receptor antagonist pharmaceuticals |
| CA2349333A1 (en) * | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | Vitronectin receptor antagonist pharmaceuticals |
| CA2727746A1 (en) | 1998-12-18 | 2000-06-22 | Bristol-Myers Squibb Pharma Company | Quinolone vitronectin receptor antagonist pharmaceuticals |
| US6511649B1 (en) | 1998-12-18 | 2003-01-28 | Thomas D. Harris | Vitronectin receptor antagonist pharmaceuticals |
| 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 |
| US6808698B1 (en) | 1999-03-26 | 2004-10-26 | Bristol-Myers Squibb Pharma Company | Method for localization of blood clots |
| US6656448B1 (en) * | 2000-02-15 | 2003-12-02 | Bristol-Myers Squibb Pharma Company | Matrix metalloproteinase inhibitors |
| US20030220646A1 (en) * | 2002-05-23 | 2003-11-27 | Thelen Sarah L. | Method and apparatus for reducing femoral fractures |
| US6534038B2 (en) | 2000-04-07 | 2003-03-18 | Bristol-Myers Squibb Pharma Company | Ternary ligand complexes useful as radiopharmaceuticals |
| JP2004512382A (ja) | 2000-11-03 | 2004-04-22 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | 心臓灌流および心臓炎症の２核種同時イメージング |
| GB0031592D0 (en) * | 2000-12-28 | 2001-02-07 | Nycomed Amersham Plc | Stabilised radiopharmaceutical compositions |
| HUP0401904A3 (en) * | 2001-08-08 | 2009-01-28 | Bristol Myers Squibb Pharma Co | 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 |
| US7297709B2 (en) | 2003-05-22 | 2007-11-20 | Abbott Laboratories | Indazole, benzisoxazole, and benzisothiazole kinase inhibitors |
| US7317104B2 (en) | 2003-06-13 | 2008-01-08 | Bristol-Myers Squibb Pharma Company | Chelants and macrocyclic metal complex radiopharmaceuticals thereof |
| US7319149B2 (en) * | 2003-06-13 | 2008-01-15 | Bristol-Myers Squibb Pharma Company | Chelants and macrocyclic metal complex radiopharmaceuticals thereof |
| BRPI0412824A (pt) * | 2003-07-24 | 2006-09-26 | Bracco Imaging Spa | composições radiofarmacêuticas estáveis e métodos para suas preparações |
| US20050106100A1 (en) * | 2003-09-03 | 2005-05-19 | Harris Thomas D. | Compounds containing matrix metalloproteinase substrates and methods of their use |
| EP1896086A1 (en) * | 2005-06-30 | 2008-03-12 | Bristol-Myers Squibb Pharma Company | Hydrazide conjugates as imaging agents |
| EP1950205A4 (en) * | 2005-10-19 | 2010-07-07 | Dainippon Sumitomo Pharma Co | METHOD FOR STABILIZING AN ISOXAZOLE COMPOUND |
| US7465795B2 (en) * | 2005-12-20 | 2008-12-16 | Astrazeneca Ab | Compounds and uses thereof |
| RU2008122405A (ru) * | 2005-12-20 | 2010-01-27 | Астразенека Аб (Se) | Замещенные производные циннолина в качестве модуляторов гамма-рецепторов и способ их синтеза |
| US8034815B2 (en) | 2007-01-11 | 2011-10-11 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| TW200911760A (en) * | 2007-06-19 | 2009-03-16 | Astrazeneca Ab | Compounds and uses thereof |
| CA2710039C (en) | 2007-12-26 | 2018-07-03 | Critical Outcome Technologies, Inc. | Semicarbazones, thiosemicarbazones and related compounds and methods for treatment of cancer |
| EP2318406B1 (en) | 2008-07-17 | 2016-01-27 | Critical Outcome Technologies, Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| ES2481042T3 (es) | 2008-12-29 | 2014-07-29 | Sanofi | Derivados de 2-piridin-2-il-pirazol-3(2H)-ona, su preparación y uso terapéutico como activadores de HIF |
| FR2949468B1 (fr) * | 2009-08-28 | 2011-09-30 | Sanofi Aventis | Derives de 2-pyridin-2-yl-pyrazol-3(2h)-one, leur preparation et leur application en therapeutique |
| AU2009334570B2 (en) * | 2008-12-29 | 2016-06-09 | Sanofi | Derivatives of 2-pyridin-2-yl-pyrazol-3(2h)-one, preparation and therapeutic use thereof |
| FR2940652B1 (fr) * | 2008-12-29 | 2011-02-11 | Sanofi Aventis | Derives de 2-pyridin-2-yl-pyrazol-3(2h)-one,leur preparation et leur application en therapeutique |
| CA2999435A1 (en) | 2010-04-01 | 2011-10-06 | Critical Outcome Technologies Inc. | Compounds and method for treatment of hiv |
| FR2967671A1 (fr) * | 2010-11-24 | 2012-05-25 | Pf Medicament | Complexe de technetium 99m en tant qu'outil de diagnostic in vivo des tumeurs cancereuses |
| CN110818624B (zh) * | 2019-11-22 | 2022-11-22 | 华东理工大学 | 吡啶季铵盐腙类化合物及制备方法与在抗菌或香料缓释中的应用 |
| CN112999369B (zh) * | 2021-03-03 | 2022-02-25 | 江苏元本生物科技有限公司 | 一种her2亲合体放射性核素标记物组合物及其应用 |
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| US4427646A (en) | 1981-04-02 | 1984-01-24 | Research Corporation | Use of radiolabeled peptide derived from crosslinked fibrin to locate thrombi in vivo |
| US4792525A (en) | 1982-08-04 | 1988-12-20 | La Jolla Cancer Research Foundation | Tetrapeptide |
| US4578079A (en) | 1982-08-04 | 1986-03-25 | La Jolla Cancer Research Foundation | Tetrapeptide |
| 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 |
| US5217705A (en) | 1987-09-25 | 1993-06-08 | Neorx Corporation | Method of diagnosing blood clots using fibrin-binding proteins |
| WO1989005150A1 (en) | 1987-12-10 | 1989-06-15 | La Jolla Cancer Research Foundation | Conformationally stabilized cell adhesion peptides |
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| US5002754A (en) * | 1988-06-15 | 1991-03-26 | University Of Cincinnati | Technetium (III/II) imaging agents |
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| 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 |
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| 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. |
| IL99537A (en) | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical compositions containing them |
| AU8730691A (en) * | 1990-09-28 | 1992-04-28 | Neorx Corporation | Polymeric carriers for release of covalently linked agents |
| US5112594A (en) * | 1991-04-04 | 1992-05-12 | Mallinckrodt Medical, Inc. | Kit for preparing a technetium-99m myocardial imaging agent |
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-
1995
- 1995-06-07 US US08/476,296 patent/US5750088A/en not_active Expired - Fee Related
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1996
- 1996-05-30 IL IL11846896A patent/IL118468A0/xx unknown
- 1996-06-04 HR HR08/476,296A patent/HRP960250A2/hr not_active Application Discontinuation
- 1996-06-06 MY MYPI96002227A patent/MY133974A/en unknown
- 1996-06-07 WO PCT/US1996/009766 patent/WO1996040637A1/en not_active Ceased
- 1996-06-07 SI SI9620076A patent/SI9620076B/sl unknown
- 1996-06-07 CN CN96196141A patent/CN1192733A/zh active Pending
- 1996-06-07 MX MX9709126A patent/MX9709126A/es unknown
- 1996-06-07 JP JP9501990A patent/JPH11507364A/ja not_active Ceased
- 1996-06-07 AT AT96919289T patent/ATE233241T1/de not_active IP Right Cessation
- 1996-06-07 CA CA002222183A patent/CA2222183A1/en not_active Abandoned
- 1996-06-07 CZ CZ973801A patent/CZ380197A3/cs unknown
- 1996-06-07 EP EP96919289A patent/EP0832068B1/en not_active Expired - Lifetime
- 1996-06-07 KR KR1019970709054A patent/KR19990022573A/ko not_active Ceased
- 1996-06-07 ZA ZA9604854A patent/ZA964854B/xx unknown
- 1996-06-07 DE DE69626392T patent/DE69626392T2/de not_active Expired - Fee Related
- 1996-06-07 NZ NZ310799A patent/NZ310799A/xx unknown
- 1996-06-07 AR ARP960103028A patent/AR003959A1/es not_active Application Discontinuation
- 1996-06-07 BR BR9609003-0A patent/BR9609003A/pt not_active Application Discontinuation
- 1996-06-07 SK SK1634-97A patent/SK163497A3/sk unknown
- 1996-06-07 ES ES96919289T patent/ES2193245T3/es not_active Expired - Lifetime
- 1996-06-07 EA EA199800025A patent/EA000742B1/ru not_active IP Right Cessation
- 1996-06-07 EE EE9700313A patent/EE9700313A/xx unknown
- 1996-06-07 AU AU61661/96A patent/AU718683B2/en not_active Ceased
- 1996-06-07 PL PL96323995A patent/PL323995A1/xx unknown
- 1996-06-07 HU HU9901469A patent/HUP9901469A3/hu unknown
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1997
- 1997-10-23 US US08/956,313 patent/US6015904A/en not_active Expired - Fee Related
- 1997-12-05 NO NO975678A patent/NO975678L/no not_active Application Discontinuation
- 1997-12-05 LT LT97-191A patent/LT4380B/lt not_active IP Right Cessation
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1998
- 1998-01-28 LV LVP-97-247A patent/LV12044B/en unknown
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| 8339 | Ceased/non-payment of the annual fee |