ES2621950T3 - Disolución de eluyente - Google Patents
Disolución de eluyente Download PDFInfo
- Publication number
- ES2621950T3 ES2621950T3 ES11808853.3T ES11808853T ES2621950T3 ES 2621950 T3 ES2621950 T3 ES 2621950T3 ES 11808853 T ES11808853 T ES 11808853T ES 2621950 T3 ES2621950 T3 ES 2621950T3
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- Spain
- Prior art keywords
- eluent
- reaction
- facbc
- exchange column
- solution
- Prior art date
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- 239000003480 eluent Substances 0.000 title claims abstract description 73
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000000243 solution Substances 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- 125000002091 cationic group Chemical group 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000005349 anion exchange Methods 0.000 claims abstract description 9
- 238000005342 ion exchange Methods 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 229940027541 fluciclovine f-18 Drugs 0.000 claims description 36
- 238000002600 positron emission tomography Methods 0.000 claims description 22
- 239000000523 sample Substances 0.000 claims description 19
- 239000002243 precursor Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 6
- 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 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound 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
- 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 2
- 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 2
- 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 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
- 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
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- SMYALUSCZJXWHG-UHFFFAOYSA-N Altanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=S)=O)CC1 SMYALUSCZJXWHG-UHFFFAOYSA-N 0.000 claims 1
- 229960002748 norepinephrine Drugs 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 description 37
- NTEDWGYJNHZKQW-DGMDOPGDSA-N fluciclovine ((18)F) Chemical compound OC(=O)[C@]1(N)C[C@H]([18F])C1 NTEDWGYJNHZKQW-DGMDOPGDSA-N 0.000 description 34
- 230000015572 biosynthetic process Effects 0.000 description 33
- 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 18
- 238000003860 storage Methods 0.000 description 17
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical group [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 7
- 238000002372 labelling Methods 0.000 description 7
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 7
- 238000007080 aromatic substitution reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 238000011194 good manufacturing practice Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 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 3
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic cyclic sulfone Chemical class 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012217 radiopharmaceutical Substances 0.000 description 3
- 229940121896 radiopharmaceutical Drugs 0.000 description 3
- 230000002799 radiopharmaceutical effect Effects 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000012879 PET imaging Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000005323 carbonate salts Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000009206 nuclear medicine Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 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
- 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
- IJPVCOQVFLNLAP-SQOUGZDYSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoyl fluoride Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(F)=O IJPVCOQVFLNLAP-SQOUGZDYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-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
- 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 description 1
- 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 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QYHYQHPUNPVNDV-UHFFFAOYSA-N aluminane Chemical compound C1CC[AlH]CC1 QYHYQHPUNPVNDV-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 238000005102 attenuated total reflection Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000005292 fiolax Substances 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PBVFROWIWWGIFK-KWCOIAHCSA-N fluoromethylcholine (18F) Chemical compound [18F]C[N+](C)(C)CCO PBVFROWIWWGIFK-KWCOIAHCSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000007141 radiochemical reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- JGFYQVQAXANWJU-UHFFFAOYSA-M sodium fluoroacetate Chemical compound [Na+].[O-]C(=O)CF JGFYQVQAXANWJU-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-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
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
-
- 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
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- 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)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Optics & Photonics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
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| US201061427839P | 2010-12-29 | 2010-12-29 | |
| US201061427839P | 2010-12-29 | ||
| PCT/EP2011/073670 WO2012089594A1 (en) | 2010-12-29 | 2011-12-21 | Eluent solution |
Publications (1)
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|---|---|
| ES2621950T3 true ES2621950T3 (es) | 2017-07-05 |
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| ES20196030T Active ES2917875T3 (es) | 2010-12-29 | 2012-12-21 | Método automatizado para la preparación de composiciones de 18F-fluciclovina |
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| ES20196030T Active ES2917875T3 (es) | 2010-12-29 | 2012-12-21 | Método automatizado para la preparación de composiciones de 18F-fluciclovina |
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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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| US5425063A (en) | 1993-04-05 | 1995-06-13 | Associated Universities, Inc. | Method for selective recovery of PET-usable quantities of [18 F] fluoride and [13 N] nitrate/nitrite from a single irradiation of low-enriched [18 O] water |
| ZA978758B (en) * | 1996-10-02 | 1999-03-30 | Du Pont Merck Pharma | Technetium-99m-labeled chelator incorporated cyclic peptides that bind to the GPIIb/IIIa receptor as imaging agents |
| RU2165266C1 (ru) | 2000-06-28 | 2001-04-20 | Центральный научно-исследовательский рентгенорадиологический институт | Способ получения [2-18f]-2-дезоксиглюкозы |
| EP1356827A1 (en) | 2002-04-24 | 2003-10-29 | Mallinckrodt Inc. | Method for obtaining a 2-18F-fluor-2-deoxy-D-glucose (18F-FDG)-solution |
| DE60236971D1 (de) | 2002-11-05 | 2010-08-19 | Ion Beam Applic Sa | Stabilisierung von wässerigen zusammensetzungen von 18f-markiertem 2-fluoro-2-deoxy-d-glukose mit ethanol |
| GB0422004D0 (en) * | 2004-10-05 | 2004-11-03 | Amersham Plc | Method of deprotection |
| GB0425501D0 (en) * | 2004-11-19 | 2004-12-22 | Amersham Plc | Fluoridation process |
| US7235216B2 (en) * | 2005-05-01 | 2007-06-26 | Iba Molecular North America, Inc. | Apparatus and method for producing radiopharmaceuticals |
| GB0524851D0 (en) * | 2005-12-06 | 2006-01-11 | Ge Healthcare Ltd | Radiolabelling method using polymers |
| WO2007148088A2 (en) * | 2006-06-21 | 2007-12-27 | Ge Healthcare Limited | Radiopharmaceutical products |
| WO2008056481A1 (en) | 2006-11-09 | 2008-05-15 | Nihon Medi-Physics Co., Ltd. | Radioactive diagnostic imaging agent |
| WO2008075522A1 (ja) | 2006-12-21 | 2008-06-26 | Nihon Medi-Physics Co., Ltd. | 放射性画像診断剤 |
| JP5258583B2 (ja) * | 2007-02-13 | 2013-08-07 | 日本メジフィジックス株式会社 | 放射性画像診断剤の製造方法 |
| EP2017359A3 (en) * | 2007-06-11 | 2009-08-05 | Trasis S.A. | Method for the elution of 18F fluoride trapped on an anion-exchange resin in a form suitable for efficient radiolabeling without any evaporation step |
| KR101009712B1 (ko) | 2007-02-22 | 2011-01-19 | 재단법인 아산사회복지재단 | 양성자성 용매와 이에 녹는 염들을 이용한 음이온 교환고분자 지지체로부터의 플루오린-18 플루오라이드 용리와이를 이용한 플루오린-18의 표지방법 |
| US20100150835A1 (en) * | 2007-02-27 | 2010-06-17 | Bengt Langstrom | Synthesis of [18F] Fluoromethyl Benzene Using Benzyl Pentafluorobenzenesulfonate |
| EP1990310A1 (en) * | 2007-04-23 | 2008-11-12 | Trasis S.A. | Method for the preparation of reactive 18F fluoride, and for the labeling of radiotracers, using a modified non-ionic solid support and without any evaporation step |
| WO2009045535A2 (en) * | 2007-10-04 | 2009-04-09 | Sloan-Kettering Institute For Cancer Research | Fluorine-18 derivative of dasatinib and uses thereof |
| BRPI0821241B1 (pt) * | 2007-12-19 | 2021-04-06 | Nihon Medi-Physics Co., Ltd. | Processo para a produção de um composto orgânico marcado com flúor radioativo |
| US20090171272A1 (en) | 2007-12-29 | 2009-07-02 | Tegg Troy T | Deflectable sheath and catheter assembly |
| CN102026913B (zh) * | 2008-01-03 | 2014-10-22 | 通用电气健康护理有限公司 | 氟化物处理方法 |
| EP2110367A1 (en) * | 2008-04-14 | 2009-10-21 | Bayer Schering Pharma Aktiengesellschaft | Purification strategy for direct nucleophilic procedures |
| GB0819293D0 (en) * | 2008-10-21 | 2008-11-26 | Hammersmith Imanet Ltd | Radiofluorination |
| US20110250137A1 (en) * | 2008-12-04 | 2011-10-13 | Bayer Schering Pharma Aktiengesellchaft | Radioisotope-labeled lysine and ornithine derivatives, their use and processes for their preparation |
| TW201033713A (en) | 2009-03-03 | 2010-09-16 | Wintek Corp | Reflective color-changing liquid crystal display |
| PL2579902T5 (pl) * | 2010-06-04 | 2020-08-10 | Life Molecular Imaging Sa | Sposób wytwarzania znakowanych F-18 ligandów amyloidu beta |
| US11504430B2 (en) * | 2010-12-29 | 2022-11-22 | Ge Healthcare Limited | Eluent solution |
| GB201214220D0 (en) * | 2012-08-09 | 2012-09-19 | Ge Healthcare Ltd | Radiosynthesis |
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2011
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- 2011-12-21 CN CN201810077584.0A patent/CN108218650A/zh active Pending
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- 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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2022
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