DK175089B1 - Estersubstituerede diamindithioler eller farmaceutisek egnede salte deraf, især i steril, farmaceutisk acceptabel form, samt deres anvendelse i forbindelse med radionuclidkomplekser - Google Patents
Estersubstituerede diamindithioler eller farmaceutisek egnede salte deraf, især i steril, farmaceutisk acceptabel form, samt deres anvendelse i forbindelse med radionuclidkomplekser Download PDFInfo
- Publication number
- DK175089B1 DK175089B1 DK198800816A DK81688A DK175089B1 DK 175089 B1 DK175089 B1 DK 175089B1 DK 198800816 A DK198800816 A DK 198800816A DK 81688 A DK81688 A DK 81688A DK 175089 B1 DK175089 B1 DK 175089B1
- Authority
- DK
- Denmark
- Prior art keywords
- carbon atoms
- ester
- alkyl
- sterile
- diamine dithiol
- Prior art date
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- -1 diamine dithiols Chemical class 0.000 title claims description 63
- 150000003839 salts Chemical class 0.000 title claims description 13
- 239000012217 radiopharmaceutical Substances 0.000 claims abstract description 41
- 229940121896 radiopharmaceutical Drugs 0.000 claims abstract description 41
- 230000002799 radiopharmaceutical effect Effects 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 40
- 239000003446 ligand Substances 0.000 claims abstract description 23
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 claims abstract description 17
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 229940056501 technetium 99m Drugs 0.000 claims abstract description 11
- 230000001698 pyrogenic effect Effects 0.000 claims abstract description 7
- 125000004185 ester group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 239000004201 L-cysteine Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 229910052713 technetium Inorganic materials 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000002285 radioactive effect Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- NRDHIACOBGNXHY-UHFFFAOYSA-N ethoxyethane;dihydrochloride Chemical compound Cl.Cl.CCOCC NRDHIACOBGNXHY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000003573 thiols Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 2
- 235000013878 L-cysteine Nutrition 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 210000004556 brain Anatomy 0.000 abstract description 27
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- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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- 150000001875 compounds Chemical class 0.000 description 10
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- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 8
- 230000003727 cerebral blood flow Effects 0.000 description 7
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- 230000014759 maintenance of location Effects 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 238000000605 extraction Methods 0.000 description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
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- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent 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 4
- 229930195725 Mannitol Natural products 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
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- 238000004108 freeze drying Methods 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
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- 235000011150 stannous chloride Nutrition 0.000 description 4
- 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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- 241000124008 Mammalia Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 239000011780 sodium chloride Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
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- 150000003548 thiazolidines Chemical class 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
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- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- ITHGGMSDPOKFOA-WCCKRBBISA-N methyl (2s)-2-amino-3-methyl-3-sulfanylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](N)C(C)(C)S ITHGGMSDPOKFOA-WCCKRBBISA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001936 parietal effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- YWLXEQKAKDKVBQ-DFWYDOINSA-M sodium;(4r)-1,3-thiazolidine-4-carboxylate Chemical compound [Na+].[O-]C(=O)[C@@H]1CSCN1 YWLXEQKAKDKVBQ-DFWYDOINSA-M 0.000 description 1
- TWAKIVGCPLPQLC-UHFFFAOYSA-N sodium;1,3-thiazolidine Chemical compound [Na].C1CSCN1 TWAKIVGCPLPQLC-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003495 technetium Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/29—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1698287A | 1987-02-18 | 1987-02-18 | |
| US1698287 | 1987-02-18 | ||
| US14356188 | 1988-01-26 | ||
| US07/143,561 US5279811A (en) | 1987-02-18 | 1988-01-26 | Ester-substituted diaminedithiols and radiolabeled complexes thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK81688D0 DK81688D0 (da) | 1988-02-17 |
| DK81688A DK81688A (da) | 1988-08-19 |
| DK175089B1 true DK175089B1 (da) | 2004-05-24 |
Family
ID=26689304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198800816A DK175089B1 (da) | 1987-02-18 | 1988-02-17 | Estersubstituerede diamindithioler eller farmaceutisek egnede salte deraf, især i steril, farmaceutisk acceptabel form, samt deres anvendelse i forbindelse med radionuclidkomplekser |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5279811A (es) |
| EP (1) | EP0279417B1 (es) |
| JP (1) | JPH0764802B2 (es) |
| KR (1) | KR910006978B1 (es) |
| AT (1) | ATE76401T1 (es) |
| AU (1) | AU614276B2 (es) |
| CA (1) | CA1271195A (es) |
| DE (2) | DE19475010I2 (es) |
| DK (1) | DK175089B1 (es) |
| ES (1) | ES2042609T3 (es) |
| GR (1) | GR3004986T3 (es) |
| HK (1) | HK66292A (es) |
| IE (1) | IE61254B1 (es) |
| IL (1) | IL85445A (es) |
| NL (1) | NL940008I2 (es) |
| NZ (1) | NZ223552A (es) |
| PT (1) | PT86787B (es) |
| SG (1) | SG71192G (es) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5279811A (en) * | 1987-02-18 | 1994-01-18 | The Du Pont Merck Pharmaceutical Company | Ester-substituted diaminedithiols and radiolabeled complexes thereof |
| US5071965A (en) * | 1988-07-19 | 1991-12-10 | Mallinckrodt Medical, Inc. | Novel tc-99m complexes |
| US4925650A (en) * | 1988-11-16 | 1990-05-15 | Mallinckrodt, Inc. | Technetium -99m complex for examining the renal function |
| DE69023616T2 (de) * | 1989-06-16 | 1996-04-18 | Neorx Corp | Radionukleid-chelatverbindungen zur radiomarkierung von proteinen. |
| 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. |
| US5443815A (en) * | 1991-11-27 | 1995-08-22 | Diatech, Inc. | Technetium-99m labeled peptides for imaging |
| US7238340B1 (en) | 1991-11-27 | 2007-07-03 | Cis Bio International | Monoamine, diamide, thiol-containing metal chelating agents |
| US5997844A (en) * | 1991-02-08 | 1999-12-07 | Diatide, Inc. | Technetium-99m labeled peptides for imaging |
| US5965107A (en) * | 1992-03-13 | 1999-10-12 | Diatide, Inc. | Technetium-99m labeled peptides for imaging |
| US5192655A (en) * | 1991-07-05 | 1993-03-09 | E. I. Du Pont De Nemours And Company | Silver halide elements with improved speed and low fog |
| 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. |
| DE4128183C1 (en) * | 1991-08-24 | 1993-01-14 | Forschungszentrum Juelich Gmbh, 5170 Juelich, De | New technetium complexes and corresp. complexing agents - useful for measurement of cerebral perfusion, diagnosis of Alzheimer's disease or epilepsy and localisation of tumours |
| EP0542216A1 (de) * | 1991-11-13 | 1993-05-19 | Hoechst Aktiengesellschaft | Diaminomercapto (thio)ether als Komplexbildner für in der Nuklearmedizin einsetzbare Nuklide, Verfahren zur Herstellung der Komplexe, sowie Markierungskits, enthaltend diese Komplexe |
| US5783170A (en) * | 1991-11-27 | 1998-07-21 | Diatide, Inc. | Peptide-metal chelate conjugates |
| US5807535A (en) * | 1992-07-31 | 1998-09-15 | Australian Nuclear Science & Technology Organisation | Metal complexes of hydroxyaryl containing aminocarboxylic acid chelating agents |
| US5688485A (en) * | 1992-12-31 | 1997-11-18 | The Dupont Merck Pharmaceutical Company | Radiolabelled complexes of ester-substituted diaminethiols |
| 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 |
| US5690904A (en) * | 1993-07-12 | 1997-11-25 | Amersham International Plc | Diagnostic radiopharmaceutical compounds (That) |
| US20030220233A1 (en) | 1994-01-24 | 2003-11-27 | Neorx Corporation | Radiolabeled annexins |
| US5968477A (en) | 1994-01-24 | 1999-10-19 | Neorx Corporation | Radiolabeled annexin conjugates with hexose and a chelator |
| CA2190727C (en) * | 1994-05-19 | 2006-07-18 | Sudhakar Kasina | Aromatic amine substituted bridged nitrogen and sulfur donor atom ligands for imaging |
| IL115099A (en) * | 1994-10-14 | 1999-04-11 | Upjohn Co | Lyophilizate of phospholipid complex of water insoluble camptothecins |
| EP0779628A3 (en) * | 1995-12-11 | 1997-07-09 | Institut National des Radioéléments, Nationaal Instituut voor Radio-elementen | Method of stabilizing an aqueous solution of 99Mo molybdate |
| US5961952A (en) * | 1996-01-24 | 1999-10-05 | Dupont Pharmaceuticals Company | 99m Tc-tertiary-butyl isonitrile as breast tumor imaging agents |
| US6005083A (en) * | 1997-03-28 | 1999-12-21 | Neorx Corporation | Bridged aromatic substituted amine ligands with donor atoms |
| DE19741694C2 (de) * | 1997-09-18 | 2002-10-31 | Schering Ag | Verwendung von Komplexen, deren Ligand ein Bis-Amin-Oxim-Derivat oder ein N¶2¶S¶2¶-Derivat und deren Zentralatom ein Radionuklid ist |
| US6436365B2 (en) * | 1997-09-23 | 2002-08-20 | Schering Aktiengesellschaft | Process for therapeutic treatment of proliferative diseases |
| WO1999040882A2 (en) * | 1998-02-06 | 1999-08-19 | Trustees Of The University Of Pennsylvania | STEREOSELECTIVE Tc-99m LIGANDS |
| US6692724B1 (en) * | 1999-10-25 | 2004-02-17 | Board Of Regents, The University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| US7067111B1 (en) * | 1999-10-25 | 2006-06-27 | Board Of Regents, University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| CA2410906C (en) * | 2000-06-02 | 2012-10-02 | Board Of Regents, The University Of Texas System | Ethylenedicysteine (ec)-drug conjugates |
| US7311893B2 (en) * | 2000-07-25 | 2007-12-25 | Neurochem (International) Limited | Amyloid targeting imaging agents and uses thereof |
| CA2444483A1 (en) * | 2001-04-26 | 2002-11-07 | Board Of Regents, The University Of Texas System | Diagnostic imaging compositions, their methods of synthesis and use |
| US7261875B2 (en) * | 2001-12-21 | 2007-08-28 | Board Of Regents, The University Of Texas System | Dendritic poly (amino acid) carriers and methods of use |
| EP2316493A3 (en) * | 2002-11-07 | 2011-08-10 | Board of Regents, The University of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| US9050378B2 (en) * | 2003-12-10 | 2015-06-09 | Board Of Regents, The University Of Texas System | N2S2 chelate-targeting ligand conjugates |
| US7414137B2 (en) * | 2006-03-23 | 2008-08-19 | Inspire Pharmaceuticals, Inc. | Process for the preparation of 3,4-disubstituted-thiazolidin-2-ones |
| WO2007111020A1 (ja) | 2006-03-24 | 2007-10-04 | Fujifilm Ri Pharma Co., Ltd. | 局所脳血流診断用放射性医薬品製造用組成物 |
| US8758723B2 (en) | 2006-04-19 | 2014-06-24 | The Board Of Regents Of The University Of Texas System | Compositions and methods for cellular imaging and therapy |
| US10925977B2 (en) * | 2006-10-05 | 2021-02-23 | Ceil>Point, LLC | Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications |
| KR100891197B1 (ko) * | 2008-09-29 | 2009-04-02 | 설상준 | 쌀 세척기 |
| WO2015200187A1 (en) * | 2014-06-27 | 2015-12-30 | Reiley Pharmaceuticals, Inc. | Conjugates derived from non-steroidal anti-inflammatory drugs and methods of use thereof in imaging |
| WO2016111834A1 (en) | 2015-01-09 | 2016-07-14 | Reiley Pharmaceuticals, Inc. | Cox-2-targeting, platinum-containing conjugates and their use in the treatment of tumors and cancers |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB742996A (en) * | 1953-01-19 | 1956-01-04 | Dow Chemical Co | Di-sulfhydryl alkylene diamine polycarboxylic acids and salts thereof |
| US2810753A (en) * | 1954-05-24 | 1957-10-22 | Dow Chemical Co | Metal ion chelating agents |
| US4284619A (en) * | 1978-11-29 | 1981-08-18 | Medi-Physics, Inc. | Esters useful as brain imaging agents |
| US4444690A (en) * | 1982-02-25 | 1984-04-24 | University Patents, Inc. | Technetium chelates |
| US4434151A (en) * | 1982-11-08 | 1984-02-28 | Medi-Physics, Inc. | Bifunctional chelating agents |
| US4575556A (en) * | 1982-11-08 | 1986-03-11 | Medi-Physics, Inc. | Bifunctional chelating agents |
| US4571430A (en) * | 1982-11-08 | 1986-02-18 | Medi-Physics, Inc. | Homocysteine and homocysteinamide derivatives |
| US4615876A (en) * | 1983-04-25 | 1986-10-07 | Curators Of The University Of Missouri | Macrocyclic complexes of technetium-99m for use as diagnostic radionuclides |
| US4673562A (en) * | 1983-08-19 | 1987-06-16 | The Children's Medical Center Corporation | Bisamide bisthiol compounds useful for making technetium radiodiagnostic renal agents |
| US4638051A (en) * | 1984-04-30 | 1987-01-20 | The Johns Hopkins University | Brain imaging radiopharmaceuticals |
| US4963688A (en) * | 1984-07-19 | 1990-10-16 | University Of Florida | Compounds for site-enhanced delivery of radionuclides and uses thereof |
| US5175343A (en) * | 1985-01-14 | 1992-12-29 | Neorx Corporation | Metal radionuclide labeled proteins for diagnosis and therapy |
| US4897255A (en) * | 1985-01-14 | 1990-01-30 | Neorx Corporation | Metal radionuclide labeled proteins for diagnosis and therapy |
| US4746505A (en) * | 1985-04-26 | 1988-05-24 | President And Fellows Of Harvard College | Technetium radiodiagnostic fatty acids derived from bisamide bisthiol ligands |
| ZA863205B (en) * | 1985-05-01 | 1987-08-26 | Univ New York State Res Found | Diagnostic radiopharmaceutical compounds |
| DE3772785D1 (de) * | 1986-01-23 | 1991-10-17 | Squibb & Sons Inc | 1-substituiertes-4,7,10-triscarboxymethyl-1,4,7,10-tetraazacyclododecan und analoga. |
| US4693688A (en) * | 1986-07-14 | 1987-09-15 | Amp Incorporated | Grounding connector |
| US5279811A (en) * | 1987-02-18 | 1994-01-18 | The Du Pont Merck Pharmaceutical Company | Ester-substituted diaminedithiols and radiolabeled complexes thereof |
| US5037631A (en) * | 1990-10-29 | 1991-08-06 | Mallinckrodt Medical, Inc. | Technetium-99M complex for examinating the renal function |
-
1988
- 1988-01-26 US US07/143,561 patent/US5279811A/en not_active Expired - Lifetime
- 1988-02-16 AU AU11748/88A patent/AU614276B2/en not_active Expired
- 1988-02-17 IE IE43188A patent/IE61254B1/en not_active IP Right Cessation
- 1988-02-17 IL IL8544588A patent/IL85445A/en not_active IP Right Cessation
- 1988-02-17 ES ES88102252T patent/ES2042609T3/es not_active Expired - Lifetime
- 1988-02-17 AT AT88102252T patent/ATE76401T1/de not_active IP Right Cessation
- 1988-02-17 NZ NZ223552A patent/NZ223552A/en unknown
- 1988-02-17 EP EP88102252A patent/EP0279417B1/en not_active Expired - Lifetime
- 1988-02-17 KR KR1019880001657A patent/KR910006978B1/ko not_active IP Right Cessation
- 1988-02-17 DE DE1994175010 patent/DE19475010I2/de active Active
- 1988-02-17 DK DK198800816A patent/DK175089B1/da not_active IP Right Cessation
- 1988-02-17 DE DE88102252T patent/DE3871173D1/de not_active Expired - Lifetime
- 1988-02-18 PT PT86787A patent/PT86787B/pt not_active IP Right Cessation
- 1988-02-18 JP JP63034137A patent/JPH0764802B2/ja not_active Expired - Lifetime
- 1988-02-18 CA CA000559230A patent/CA1271195A/en not_active Expired - Lifetime
-
1992
- 1992-06-18 GR GR920401321T patent/GR3004986T3/el unknown
- 1992-07-08 SG SG711/92A patent/SG71192G/en unknown
- 1992-09-03 HK HK662/92A patent/HK66292A/xx not_active IP Right Cessation
-
1993
- 1993-10-20 US US08/139,894 patent/US5431900A/en not_active Expired - Lifetime
-
1994
- 1994-05-31 NL NL940008C patent/NL940008I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL940008I1 (nl) | 1994-07-18 |
| JPS63295549A (ja) | 1988-12-01 |
| NL940008I2 (nl) | 1999-07-01 |
| CA1271195A (en) | 1990-07-03 |
| PT86787B (pt) | 1995-03-01 |
| US5279811A (en) | 1994-01-18 |
| KR910006978B1 (ko) | 1991-09-14 |
| AU1174888A (en) | 1988-09-01 |
| DE19475010I2 (de) | 2001-07-19 |
| IL85445A0 (en) | 1988-07-31 |
| ATE76401T1 (de) | 1992-06-15 |
| HK66292A (en) | 1992-09-11 |
| EP0279417A2 (en) | 1988-08-24 |
| ES2042609T3 (es) | 1993-12-16 |
| KR880009917A (ko) | 1988-10-05 |
| GR3004986T3 (es) | 1993-04-28 |
| PT86787A (pt) | 1989-02-28 |
| NZ223552A (en) | 1990-04-26 |
| IL85445A (en) | 1994-01-25 |
| SG71192G (en) | 1992-09-04 |
| US5431900A (en) | 1995-07-11 |
| DK81688D0 (da) | 1988-02-17 |
| AU614276B2 (en) | 1991-08-29 |
| JPH0764802B2 (ja) | 1995-07-12 |
| IE880431L (en) | 1988-08-18 |
| EP0279417A3 (en) | 1989-07-26 |
| EP0279417B1 (en) | 1992-05-20 |
| DE3871173D1 (es) | 1992-06-25 |
| IE61254B1 (en) | 1994-10-19 |
| DK81688A (da) | 1988-08-19 |
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