ES2313117T3 - Trampa de radicales para fluoracion de sales iodonio. - Google Patents
Trampa de radicales para fluoracion de sales iodonio. Download PDFInfo
- Publication number
- ES2313117T3 ES2313117T3 ES04806112T ES04806112T ES2313117T3 ES 2313117 T3 ES2313117 T3 ES 2313117T3 ES 04806112 T ES04806112 T ES 04806112T ES 04806112 T ES04806112 T ES 04806112T ES 2313117 T3 ES2313117 T3 ES 2313117T3
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- ES
- Spain
- Prior art keywords
- procedure
- compound
- fluoride
- labeled
- reaction
- 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.)
- Expired - Lifetime
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 47
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 22
- 150000003254 radicals Chemical class 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011737 fluorine Substances 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 8
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- -1 Nonaflato Chemical compound 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical group [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 18
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000011698 potassium fluoride Substances 0.000 claims description 9
- 235000003270 potassium fluoride Nutrition 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 6
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001450 anions Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 4
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 235000013734 beta-carotene Nutrition 0.000 claims description 2
- 239000011648 beta-carotene Substances 0.000 claims description 2
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 claims description 2
- 229960002747 betacarotene Drugs 0.000 claims description 2
- 229960003638 dopamine Drugs 0.000 claims description 2
- 229960005219 gentisic acid Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229950002475 mesilate Drugs 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 claims description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 2
- 229940087168 alpha tocopherol Drugs 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 229960004337 hydroquinone Drugs 0.000 claims 1
- 238000004255 ion exchange chromatography Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 230000001012 protector Effects 0.000 claims 1
- 229960000984 tocofersolan Drugs 0.000 claims 1
- 229940035893 uracil Drugs 0.000 claims 1
- 235000004835 α-tocopherol Nutrition 0.000 claims 1
- 239000002076 α-tocopherol Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 62
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 26
- 229920005989 resin Polymers 0.000 description 24
- 239000011347 resin Substances 0.000 description 24
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 23
- 239000004793 Polystyrene Substances 0.000 description 17
- 229920002223 polystyrene Polymers 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 15
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- SYUVAXDZVWPKSI-UHFFFAOYSA-N tributyl(phenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=C1 SYUVAXDZVWPKSI-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 6
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229920005990 polystyrene resin Polymers 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WWYURIBMRGOHSH-UHFFFAOYSA-N 11-(4-iodophenoxy)undecanoic acid Chemical compound OC(=O)CCCCCCCCCCOC1=CC=C(I)C=C1 WWYURIBMRGOHSH-UHFFFAOYSA-N 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000004334 fluoridation Methods 0.000 description 4
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 4
- ZPIPFGZIDSWGSR-UHFFFAOYSA-N 6-(4-iodophenoxy)hexanoic acid Chemical compound OC(=O)CCCCCOC1=CC=C(I)C=C1 ZPIPFGZIDSWGSR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 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
- 150000001501 aryl fluorides Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 238000012565 NMR experiment Methods 0.000 description 2
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 2
- 150000001503 aryl iodides Chemical class 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229960004502 levodopa Drugs 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- XPQPWPZFBULGKT-UHFFFAOYSA-N undecanoic acid methyl ester Natural products CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 description 2
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- GHASVSINZRGABV-SFIIULIVSA-N 5-fluoranyl-1h-pyrimidine-2,4-dione Chemical compound [18F]C1=CNC(=O)NC1=O GHASVSINZRGABV-SFIIULIVSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- IHBJLWSFVHJZSI-UHFFFAOYSA-N COC1=CC=CC=C1I.CON1N=CC=C1.OC(C(F)(F)F)=O Chemical compound COC1=CC=CC=C1I.CON1N=CC=C1.OC(C(F)(F)F)=O IHBJLWSFVHJZSI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GBAASOXMZAYXCZ-UHFFFAOYSA-N FC(C(=O)O)(F)F.NCN Chemical compound FC(C(=O)O)(F)F.NCN GBAASOXMZAYXCZ-UHFFFAOYSA-N 0.000 description 1
- 238000012879 PET imaging Methods 0.000 description 1
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- 241000656145 Thyrsites atun Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- WVKZOKSPFSSWRY-UHFFFAOYSA-N aminomethyl 2,2,2-trifluoroacetate Chemical class NCOC(=O)C(F)(F)F WVKZOKSPFSSWRY-UHFFFAOYSA-N 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- CAVCVQXTTLJZNF-UHFFFAOYSA-N ethyl 6-(4-iodophenoxy)hexanoate Chemical compound CCOC(=O)CCCCCOC1=CC=C(I)C=C1 CAVCVQXTTLJZNF-UHFFFAOYSA-N 0.000 description 1
- DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- JCZSQOVZJXDMTK-UHFFFAOYSA-N iodo trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OI JCZSQOVZJXDMTK-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- HFNPVFKUZYCDIB-UHFFFAOYSA-N methyl 11-bromoundecanoate Chemical compound COC(=O)CCCCCCCCCCBr HFNPVFKUZYCDIB-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DVCMYAIUSOSIQP-UHFFFAOYSA-N phenyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OC1=CC=CC=C1 DVCMYAIUSOSIQP-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000010414 supernatant solution Substances 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
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Liquid Crystal (AREA)
- Saccharide Compounds (AREA)
- Seasonings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0329716 | 2003-12-23 | ||
| GBGB0329716.5A GB0329716D0 (en) | 2003-12-23 | 2003-12-23 | Radical trap |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2313117T3 true ES2313117T3 (es) | 2009-03-01 |
Family
ID=30776291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04806112T Expired - Lifetime ES2313117T3 (es) | 2003-12-23 | 2004-12-17 | Trampa de radicales para fluoracion de sales iodonio. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7642373B2 (https=) |
| EP (1) | EP1697279B1 (https=) |
| JP (1) | JP4809244B2 (https=) |
| CN (1) | CN100415696C (https=) |
| AT (1) | ATE409173T1 (https=) |
| DE (1) | DE602004016771D1 (https=) |
| ES (1) | ES2313117T3 (https=) |
| GB (1) | GB0329716D0 (https=) |
| WO (1) | WO2005061415A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0407952D0 (en) * | 2004-04-08 | 2004-05-12 | Amersham Plc | Fluoridation method |
| GB0525949D0 (en) | 2005-12-21 | 2006-02-01 | Hammersmith Imanet Ltd | Pet radiotracers |
| EP2192928A4 (en) * | 2007-10-03 | 2011-04-06 | Ge Healthcare Ltd | PERFLUOR ARYLIODONIUM SALTS IN A NUCLEOPHILIC AROMATIC 18F FLUORATION |
| EP2238074A2 (en) * | 2008-01-03 | 2010-10-13 | GE Healthcare UK Limited | Fluoride processing method |
| GB0808986D0 (en) | 2008-05-16 | 2008-06-25 | Univ Newcastle | Formation of 18F and 19F fluoroarenes bearing reactive functionalities |
| WO2010015340A1 (en) * | 2008-08-06 | 2010-02-11 | Bayer Schering Pharma Aktiengesellschaft | Daa-pyridine as peripheral benzodiazepine receptor ligand for diagnostic imaging and pharmaceutical treatment |
| GB0814893D0 (en) * | 2008-08-14 | 2008-09-17 | Ge Healthcare Ltd | Improved fluoridation of iodonium salts |
| US9302990B2 (en) | 2008-10-21 | 2016-04-05 | Nutech Ventures | Fluorination of aromatic ring systems |
| EP2537826B1 (en) | 2008-10-21 | 2017-03-08 | Nutech Ventures, Inc. | Fluorination of aromatic ring systems |
| GB0905438D0 (en) | 2009-03-30 | 2009-05-13 | Ge Healthcare Ltd | Radiolabelling reagents and methods |
| WO2010117435A2 (en) * | 2009-04-08 | 2010-10-14 | The Regents Of The University Of California | No-carrier-added nucleophilic [f-18] fluorination of aromatic compounds |
| US8377704B2 (en) | 2009-10-20 | 2013-02-19 | Nutech Ventures | Detection and quantification of anions |
| US8546578B2 (en) * | 2010-02-04 | 2013-10-01 | Nutech Ventures | Iodonium Cyclophanes for SECURE arene functionalization |
| WO2011141515A1 (en) | 2010-05-14 | 2011-11-17 | Bayer Pharma Aktiengesellschaft | Diagnostic agents for amyloid beta imaging |
| KR101441406B1 (ko) * | 2011-05-25 | 2014-11-04 | 주식회사 바이오이미징코리아 | 디아릴이오도늄 염 전구체를 이용한 플로오린-18이 표지된 플루마제닐의 제조 방법 |
| EP2912011A4 (en) * | 2012-10-27 | 2016-11-09 | Ground Fluor Pharmaceuticals Inc | METHODS AND REAGENTS FOR MANUFACTURING DIARYLIODONIUM SALTS |
| EP2821383B1 (en) * | 2013-07-02 | 2017-08-30 | Trasis S.A. | Stabilization of radiosynthetic intermediates |
| WO2015157597A1 (en) * | 2014-04-11 | 2015-10-15 | The Regents Of The University Of Michigan | Copper catalyzed [18f]fluorination of iodonium salts |
| CN105237483B (zh) * | 2015-11-10 | 2018-04-20 | 东华大学 | 一种对称型嘧啶基碘鎓盐及其制备方法 |
| FR3054445B1 (fr) * | 2016-07-26 | 2019-07-05 | Laboratoires Cyclopharma | Synthese d'une composition d'agent radioactif |
| US10695450B2 (en) | 2016-07-26 | 2020-06-30 | Laboratoires Cyclopharma | Synthesis of a radioactive agent composition |
| RU2020116649A (ru) | 2017-10-24 | 2021-11-30 | Лунелла Байотек, Инк. | Митофлавосцины: нацеливание на флавин-содержащие ферменты устраняет злокачественные стволовые клетки (cscs) посредством ингибирования митохондриального дыхания |
| GB201805253D0 (en) * | 2018-03-29 | 2018-05-16 | Ge Healthcare Ltd Ip | Solid phase extraction |
| JP7556709B2 (ja) * | 2019-07-01 | 2024-09-26 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7627551B2 (ja) * | 2019-07-01 | 2025-02-06 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP7558694B2 (ja) * | 2019-07-01 | 2024-10-01 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| JP2021008455A (ja) * | 2019-07-01 | 2021-01-28 | 住友化学株式会社 | カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| GB201915206D0 (en) | 2019-10-21 | 2019-12-04 | Ge Healthcare Ltd | Use of cyclodextrins as a radiostabilizer |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52133994A (en) * | 1976-04-29 | 1977-11-09 | Daikin Ind Ltd | Method of fluorination |
| JP3165775B2 (ja) * | 1994-08-31 | 2001-05-14 | 日本鋼管株式会社 | フッ素放射性同位元素標識ｌ−ドーパの製造方法 |
| JP3171036B2 (ja) * | 1994-11-16 | 2001-05-28 | 日本鋼管株式会社 | フッ素放射性同位元素標識ドーパミンの製造方法 |
| GB0115927D0 (en) * | 2001-06-29 | 2001-08-22 | Nycomed Amersham Plc | Solid-phase nucleophilic fluorination |
| GB0206750D0 (en) * | 2002-03-22 | 2002-05-01 | Amersham Plc | Radiofluorination methods |
| DE10346228B4 (de) * | 2003-09-25 | 2009-04-09 | Eberhard-Karls-Universität Tübingen Universitätsklinikum | Herstellung von [18F]fluormarkierten aromatischen L-Aminosäuren |
| GB0407952D0 (en) * | 2004-04-08 | 2004-05-12 | Amersham Plc | Fluoridation method |
-
2003
- 2003-12-23 GB GBGB0329716.5A patent/GB0329716D0/en not_active Ceased
-
2004
- 2004-12-17 EP EP04806112A patent/EP1697279B1/en not_active Expired - Lifetime
- 2004-12-17 ES ES04806112T patent/ES2313117T3/es not_active Expired - Lifetime
- 2004-12-17 US US10/559,879 patent/US7642373B2/en not_active Expired - Fee Related
- 2004-12-17 JP JP2006546303A patent/JP4809244B2/ja not_active Expired - Fee Related
- 2004-12-17 DE DE602004016771T patent/DE602004016771D1/de not_active Expired - Lifetime
- 2004-12-17 WO PCT/GB2004/005304 patent/WO2005061415A1/en not_active Ceased
- 2004-12-17 AT AT04806112T patent/ATE409173T1/de not_active IP Right Cessation
- 2004-12-17 CN CNB2004800384699A patent/CN100415696C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1697279B1 (en) | 2008-09-24 |
| DE602004016771D1 (de) | 2008-11-06 |
| EP1697279A1 (en) | 2006-09-06 |
| WO2005061415A1 (en) | 2005-07-07 |
| JP2007515465A (ja) | 2007-06-14 |
| US7642373B2 (en) | 2010-01-05 |
| US20060292060A1 (en) | 2006-12-28 |
| GB0329716D0 (en) | 2004-01-28 |
| CN100415696C (zh) | 2008-09-03 |
| JP4809244B2 (ja) | 2011-11-09 |
| ATE409173T1 (de) | 2008-10-15 |
| CN1898184A (zh) | 2007-01-17 |
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