RU2608932C2 - Раствор элюента - Google Patents
Раствор элюента Download PDFInfo
- Publication number
- RU2608932C2 RU2608932C2 RU2013126979A RU2013126979A RU2608932C2 RU 2608932 C2 RU2608932 C2 RU 2608932C2 RU 2013126979 A RU2013126979 A RU 2013126979A RU 2013126979 A RU2013126979 A RU 2013126979A RU 2608932 C2 RU2608932 C2 RU 2608932C2
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- RU
- Russia
- Prior art keywords
- eluent
- solution
- synthesis
- exchange column
- reaction
- Prior art date
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- 239000003480 eluent Substances 0.000 title claims abstract description 75
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000000243 solution Substances 0.000 claims abstract description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 238000002600 positron emission tomography Methods 0.000 claims abstract description 22
- 238000003860 storage Methods 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 125000002091 cationic group Chemical group 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 238000005349 anion exchange Methods 0.000 claims abstract description 9
- 238000005342 ion exchange Methods 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000011049 filling Methods 0.000 claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 46
- 238000003786 synthesis reaction Methods 0.000 claims description 46
- 239000002243 precursor Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002739 cryptand Substances 0.000 claims description 9
- -1 cryptand metal complex Chemical class 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- NTEDWGYJNHZKQW-KWCOIAHCSA-N 1-amino-3-fluoranylcyclobutane-1-carboxylic acid Chemical compound OC(=O)C1(N)CC([18F])C1 NTEDWGYJNHZKQW-KWCOIAHCSA-N 0.000 claims description 4
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229960004502 levodopa Drugs 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- ZCXUVYAZINUVJD-AHXZWLDOSA-N 2-deoxy-2-((18)F)fluoro-alpha-D-glucose Chemical group OC[C@H]1O[C@H](O)[C@H]([18F])[C@@H](O)[C@@H]1O ZCXUVYAZINUVJD-AHXZWLDOSA-N 0.000 claims description 3
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical group C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 claims description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical group [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims description 3
- KDLLNMRYZGUVMA-ZYMZXAKXSA-N (8r,9s,13s,14s,16r,17r)-16-fluoranyl-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H]([18F])C4)O)[C@@H]4[C@@H]3CCC2=C1 KDLLNMRYZGUVMA-ZYMZXAKXSA-N 0.000 claims description 2
- UXCAQJAQSWSNPQ-KXMUYVCJSA-N 1-[4-fluoranyl-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1OC(CO)C([18F])C1 UXCAQJAQSWSNPQ-KXMUYVCJSA-N 0.000 claims description 2
- SMYALUSCZJXWHG-VNRZBHCFSA-N 3-[2-[4-(4-fluoranylbenzoyl)piperidin-1-yl]ethyl]-2-sulfanylidene-1h-quinazolin-4-one Chemical compound C1=CC([18F])=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=S)=O)CC1 SMYALUSCZJXWHG-VNRZBHCFSA-N 0.000 claims description 2
- FOTRTWXNJQSQJS-LURJTMIESA-N 4-[(1r)-2-amino-1-hydroxyethyl]-3-fluorobenzene-1,2-diol Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1F FOTRTWXNJQSQJS-LURJTMIESA-N 0.000 claims description 2
- XIDVXDKBUJEBSC-NUTRPMROSA-N 5-(18F)fluoranyl-2-nitro-1H-imidazole Chemical compound [18F]C=1N=C(NC=1)[N+](=O)[O-] XIDVXDKBUJEBSC-NUTRPMROSA-N 0.000 claims description 2
- QHJLPOSPWKZACG-UHFFFAOYSA-N N-Methylspiperone Chemical compound C1CN(CCCC(=O)C=2C=CC(F)=CC=2)CCC21C(=O)N(C)CN2C1=CC=CC=C1 QHJLPOSPWKZACG-UHFFFAOYSA-N 0.000 claims description 2
- XBJBPGROQZJDOJ-UHFFFAOYSA-N fleroxacin Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(CCF)C2=C1F XBJBPGROQZJDOJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960003306 fleroxacin Drugs 0.000 claims description 2
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 claims description 2
- 229960004884 fluconazole Drugs 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- RBGAHDDQSRBDOG-KVTPGWOSSA-N 6-[2-[4-(4-fluoranylbenzoyl)piperidin-1-yl]ethyl]-7-methyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC=1N=C2SCCN2C(=O)C=1CCN(CC1)CCC1C(=O)C1=CC=C([18F])C=C1 RBGAHDDQSRBDOG-KVTPGWOSSA-N 0.000 claims 1
- 238000004334 fluoridation Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 238000003682 fluorination reaction Methods 0.000 abstract description 5
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- 230000002799 radiopharmaceutical effect Effects 0.000 abstract description 4
- 238000000354 decomposition reaction Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 229940027541 fluciclovine f-18 Drugs 0.000 description 40
- NTEDWGYJNHZKQW-DGMDOPGDSA-N fluciclovine ((18)F) Chemical compound OC(=O)[C@]1(N)C[C@H]([18F])C1 NTEDWGYJNHZKQW-DGMDOPGDSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical class [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
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- 239000000203 mixture Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000011194 good manufacturing practice Methods 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HIIJZYSUEJYLMX-UHFFFAOYSA-N 1-fluoro-3-(2-nitroimidazol-1-yl)propan-2-ol Chemical compound FCC(O)CN1C=CN=C1[N+]([O-])=O HIIJZYSUEJYLMX-UHFFFAOYSA-N 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 2
- 238000012879 PET imaging Methods 0.000 description 2
- 238000007080 aromatic substitution reaction Methods 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- 150000005323 carbonate salts Chemical class 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
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- 238000001308 synthesis method Methods 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- 238000006257 total synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- CKEOSLXCJBTWQG-AWDFDDCISA-N (1,4-dioxonaphthalen-2-yl)methyl 4-fluoranylbenzoate Chemical compound C1=CC([18F])=CC=C1C(=O)OCC1=CC(=O)C2=CC=CC=C2C1=O CKEOSLXCJBTWQG-AWDFDDCISA-N 0.000 description 1
- HIIJZYSUEJYLMX-JZRMKITLSA-N 1-fluoranyl-3-(2-nitroimidazol-1-yl)propan-2-ol Chemical compound [18F]CC(O)CN1C=CN=C1[N+]([O-])=O HIIJZYSUEJYLMX-JZRMKITLSA-N 0.000 description 1
- AOYNUTHNTBLRMT-MXWOLSILSA-N 2-Deoxy-2(F-18)fluoro-2-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H]([18F])C=O AOYNUTHNTBLRMT-MXWOLSILSA-N 0.000 description 1
- WPKXGJXEAGYSBQ-RVRFMXCPSA-N 4-(2-aminoethyl)-5-fluoranylbenzene-1,2-diol Chemical compound NCCC1=CC(O)=C(O)C=C1[18F] WPKXGJXEAGYSBQ-RVRFMXCPSA-N 0.000 description 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 101100208721 Mus musculus Usp5 gene Proteins 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
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- OIBDVHSTOUGZTJ-PEBLQZBPSA-N [(2r,3r,4s,5s,6s)-3,4,6-triacetyloxy-5-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@@H](OS(=O)(=O)C(F)(F)F)[C@@H](OC(C)=O)[C@@H]1OC(C)=O OIBDVHSTOUGZTJ-PEBLQZBPSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- QYHYQHPUNPVNDV-UHFFFAOYSA-N aluminane Chemical compound C1CC[AlH]CC1 QYHYQHPUNPVNDV-UHFFFAOYSA-N 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
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- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
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- JGFYQVQAXANWJU-UHFFFAOYSA-M sodium fluoroacetate Chemical compound [Na+].[O-]C(=O)CF JGFYQVQAXANWJU-UHFFFAOYSA-M 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- GZXOHHPYODFEGO-UHFFFAOYSA-N triglycine sulfate Chemical class NCC(O)=O.NCC(O)=O.NCC(O)=O.OS(O)(=O)=O GZXOHHPYODFEGO-UHFFFAOYSA-N 0.000 description 1
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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
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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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
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B9/00—General methods of preparing halides
- C01B9/08—Fluorides
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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
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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
- C07B59/001—Acyclic or carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- A—HUMAN NECESSITIES
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- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| PCT/EP2011/073670 WO2012089594A1 (en) | 2010-12-29 | 2011-12-21 | Eluent solution |
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| RU2013126979A RU2013126979A (ru) | 2015-03-20 |
| RU2608932C2 true RU2608932C2 (ru) | 2017-01-26 |
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| US11504430B2 (en) * | 2010-12-29 | 2022-11-22 | Ge Healthcare Limited | Eluent solution |
| WO2013093025A1 (en) * | 2011-12-21 | 2013-06-27 | Ge Healthcare Limited | 18f - fluciclovine compositions in citrate buffers |
| AU2012324940A1 (en) * | 2011-10-19 | 2014-04-17 | Piramal Imaging Sa | Improved method for production of F-18 labeled Abeta ligands |
| GB201411569D0 (en) | 2014-06-30 | 2014-08-13 | Ge Healthcare Ltd | Novel formulation and method of synthesis |
| US11534494B2 (en) | 2011-12-21 | 2022-12-27 | Ge Healthcare Limited | Formulation and method of synthesis |
| GB201214220D0 (en) * | 2012-08-09 | 2012-09-19 | Ge Healthcare Ltd | Radiosynthesis |
| GB201221266D0 (en) | 2012-11-27 | 2013-01-09 | Ge Healthcare Ltd | Aldehyde compositions |
| GB201305687D0 (en) * | 2013-03-28 | 2013-05-15 | Ge Healthcare Ltd | Radiolabelling process |
| US10584078B2 (en) * | 2013-11-13 | 2020-03-10 | Ge Healthcare Limited | Dual run cassette for the synthesis of 18F-labelled compounds |
| US9988336B2 (en) * | 2014-03-18 | 2018-06-05 | Mayo Foundation For Medical Education And Research | Gaseous F-18 technologies |
| NL2014828B1 (en) | 2015-05-20 | 2017-01-31 | Out And Out Chemistry S P R L | Method of performing a plurality of synthesis processes of preparing a radiopharmaceutical in series, a device and cassette for performing this method. |
| JP6827709B2 (ja) * | 2016-04-25 | 2021-02-10 | 日本メジフィジックス株式会社 | ２−［１８ｆ］フルオロ−２−デオキシ−ｄ−グルコースの製造方法 |
| US10695450B2 (en) | 2016-07-26 | 2020-06-30 | Laboratoires Cyclopharma | Synthesis of a radioactive agent composition |
| JP7148121B2 (ja) * | 2018-08-31 | 2022-10-05 | 国立大学法人北海道大学 | 放射性核種１８ｆの精製方法 |
| GB202005282D0 (en) | 2020-04-09 | 2020-05-27 | Blue Earth Diagnostics Ltd | Pharmaceutical Formulations |
| JP7127164B2 (ja) * | 2021-01-19 | 2022-08-29 | 日本メジフィジックス株式会社 | ２－［１８ｆ］フルオロ－２－デオキシ－ｄ－グルコースの製造方法 |
| CN113372399A (zh) * | 2021-06-04 | 2021-09-10 | 江苏华益科技有限公司 | 一种氟[18f]脱氧葡糖注射液的合成方法 |
| CN119591463B (zh) * | 2024-11-27 | 2025-12-09 | 遵义医科大学 | 一种 [18f] 三氟甲基末端烯烃的放射性标记方法 |
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2011
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- 2011-12-21 CN CN201810077584.0A patent/CN108218650A/zh active Pending
- 2011-12-21 JP JP2013546670A patent/JP6018581B2/ja active Active
- 2011-12-21 MX MX2013007699A patent/MX363538B/es unknown
- 2011-12-21 ES ES11808853.3T patent/ES2621950T3/es active Active
- 2011-12-21 PL PL11808853T patent/PL2658831T3/pl unknown
- 2011-12-21 CN CN2011800634887A patent/CN103270004A/zh active Pending
- 2011-12-21 KR KR1020197001271A patent/KR102218263B1/ko active Active
- 2011-12-21 CA CA2823063A patent/CA2823063C/en active Active
- 2011-12-21 DK DK11808853.3T patent/DK2658831T3/en active
- 2011-12-21 WO PCT/EP2011/073670 patent/WO2012089594A1/en not_active Ceased
- 2011-12-21 RU RU2013126979A patent/RU2608932C2/ru active
- 2011-12-21 EP EP11808853.3A patent/EP2658831B1/en active Active
- 2011-12-21 BR BR112013015396-2A patent/BR112013015396B1/pt active IP Right Grant
- 2011-12-21 KR KR1020137017012A patent/KR20130132892A/ko not_active Ceased
- 2011-12-21 AU AU2011351550A patent/AU2011351550B2/en active Active
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2012
- 2012-12-21 PL PL20196030T patent/PL3766522T3/pl unknown
- 2012-12-21 DK DK12806500.0T patent/DK2793954T3/da active
- 2012-12-21 KR KR1020197030135A patent/KR102137348B1/ko active Active
- 2012-12-21 DK DK20196030.9T patent/DK3766522T3/da active
- 2012-12-21 SG SG10201805198TA patent/SG10201805198TA/en unknown
- 2012-12-21 PT PT128065000T patent/PT2793954T/pt unknown
- 2012-12-21 EP EP20196030.9A patent/EP3766522B1/en active Active
- 2012-12-21 PT PT201960309T patent/PT3766522T/pt unknown
- 2012-12-21 ES ES20196030T patent/ES2917875T3/es active Active
- 2012-12-21 BR BR112014015042-7A patent/BR112014015042B1/pt active IP Right Grant
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2019
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