CA2222183A1 - Stable reagents for the preparation of radiopharmaceuticals - Google Patents
Stable reagents for the preparation of radiopharmaceuticals Download PDFInfo
- Publication number
- CA2222183A1 CA2222183A1 CA002222183A CA2222183A CA2222183A1 CA 2222183 A1 CA2222183 A1 CA 2222183A1 CA 002222183 A CA002222183 A CA 002222183A CA 2222183 A CA2222183 A CA 2222183A CA 2222183 A1 CA2222183 A1 CA 2222183A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- substituted
- independently selected
- occurrence
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000012217 radiopharmaceutical Substances 0.000 title claims abstract description 117
- 229940121896 radiopharmaceutical Drugs 0.000 title claims abstract description 117
- 230000002799 radiopharmaceutical effect Effects 0.000 title claims abstract description 115
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 114
- 238000002360 preparation method Methods 0.000 title abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 150000007857 hydrazones Chemical class 0.000 claims abstract description 52
- 239000003446 ligand Substances 0.000 claims description 103
- -1 hydrazone compound Chemical class 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 230000015572 biosynthetic process Effects 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 238000003786 synthesis reaction Methods 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000027455 binding Effects 0.000 claims description 29
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000003638 chemical reducing agent Substances 0.000 claims description 20
- 102000005962 receptors Human genes 0.000 claims description 20
- 108020003175 receptors Proteins 0.000 claims description 20
- 125000005597 hydrazone group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000012546 transfer Methods 0.000 claims description 12
- 229910006069 SO3H Inorganic materials 0.000 claims description 11
- 150000001723 carbon free-radicals Chemical class 0.000 claims description 11
- 238000004108 freeze drying Methods 0.000 claims description 10
- 239000002464 receptor antagonist Substances 0.000 claims description 10
- 229940044551 receptor antagonist Drugs 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 239000000872 buffer Substances 0.000 claims description 9
- 230000006641 stabilisation Effects 0.000 claims description 9
- 238000011105 stabilization Methods 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 101100516569 Caenorhabditis elegans nhr-85 gene Proteins 0.000 claims description 8
- 230000007928 solubilization Effects 0.000 claims description 7
- 238000005063 solubilization Methods 0.000 claims description 7
- 101100294118 Caenorhabditis elegans nhr-53 gene Proteins 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- ZOUTYVWHWSUKPL-RNCFNFMXSA-N C[C@H](CS)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O Chemical compound C[C@H](CS)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O ZOUTYVWHWSUKPL-RNCFNFMXSA-N 0.000 claims description 5
- 101710091342 Chemotactic peptide Proteins 0.000 claims description 5
- 102000009123 Fibrin Human genes 0.000 claims description 5
- 108010073385 Fibrin Proteins 0.000 claims description 5
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229950003499 fibrin Drugs 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 210000000265 leukocyte Anatomy 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 102000003800 Selectins Human genes 0.000 claims description 3
- 108090000184 Selectins Proteins 0.000 claims description 3
- 150000008065 acid anhydrides Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 2
- GZYXAJKEYLROPJ-UHFFFAOYSA-N N=C=S.O=C1NC(=O)C=C1 Chemical compound N=C=S.O=C1NC(=O)C=C1 GZYXAJKEYLROPJ-UHFFFAOYSA-N 0.000 claims 1
- 238000009007 Diagnostic Kit Methods 0.000 abstract description 21
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- 239000012216 imaging agent Substances 0.000 abstract description 6
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- 239000002738 chelating agent Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 22
- 235000001968 nicotinic acid Nutrition 0.000 description 21
- 239000011664 nicotinic acid Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000306 component Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 description 18
- 125000004429 atom Chemical group 0.000 description 18
- 235000018102 proteins Nutrition 0.000 description 17
- 102000004169 proteins and genes Human genes 0.000 description 17
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- 238000004519 manufacturing process Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- 229910052713 technetium Inorganic materials 0.000 description 14
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 238000003384 imaging method Methods 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- UZMAPBJVXOGOFT-UHFFFAOYSA-N Syringetin Natural products COC1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UZMAPBJVXOGOFT-UHFFFAOYSA-N 0.000 description 9
- 239000007997 Tricine buffer Substances 0.000 description 9
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000004007 reversed phase HPLC Methods 0.000 description 9
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- 208000007536 Thrombosis Diseases 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
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- 238000005859 coupling reaction Methods 0.000 description 7
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 229910001882 dioxygen Inorganic materials 0.000 description 6
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 5
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
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- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
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- YSWCBAKPAOEYGF-UHFFFAOYSA-N 2-aminoacetic acid;2,2,2-trifluoroacetic acid Chemical compound NCC(O)=O.OC(=O)C(F)(F)F YSWCBAKPAOEYGF-UHFFFAOYSA-N 0.000 description 2
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- BWLBGMIXKSTLSX-UHFFFAOYSA-M 2-hydroxyisobutyrate Chemical compound CC(C)(O)C([O-])=O BWLBGMIXKSTLSX-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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)
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- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| US08/476,296 | 1995-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2222183A1 true CA2222183A1 (en) | 1996-12-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002222183A Abandoned CA2222183A1 (en) | 1995-06-07 | 1996-06-07 | Stable reagents for the preparation of radiopharmaceuticals |
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| JP (1) | JPH11507364A (enExample) |
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| 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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1995
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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
-
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
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| FZDE | Discontinued |