IE61263B1 - Iodinated esters - Google Patents
Iodinated estersInfo
- Publication number
- IE61263B1 IE61263B1 IE224788A IE224788A IE61263B1 IE 61263 B1 IE61263 B1 IE 61263B1 IE 224788 A IE224788 A IE 224788A IE 224788 A IE224788 A IE 224788A IE 61263 B1 IE61263 B1 IE 61263B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- mmol
- water
- solution
- groups
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 18
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 210000001124 body fluid Anatomy 0.000 claims abstract description 3
- 239000010839 body fluid Substances 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 49
- 239000002245 particle Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000002872 contrast media Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 241001595582 Octolasmis cor Species 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims 1
- -1 araliphatic Chemical group 0.000 abstract description 14
- 238000002604 ultrasonography Methods 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 33
- 238000003756 stirring Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 210000004185 liver Anatomy 0.000 description 14
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 14
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 14
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 14
- 239000011630 iodine Substances 0.000 description 13
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 239000002953 phosphate buffered saline Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 239000008194 pharmaceutical composition Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 235000009518 sodium iodide Nutrition 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000008354 sodium chloride injection Substances 0.000 description 9
- 239000008215 water for injection Substances 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 210000000952 spleen Anatomy 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000002502 liposome Substances 0.000 description 5
- JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- GGGDNPWHMNJRFN-UHFFFAOYSA-N metrizoic acid Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I GGGDNPWHMNJRFN-UHFFFAOYSA-N 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001493 electron microscopy Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 238000004619 light microscopy Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 239000011859 microparticle Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- VQEZDLXEVJCRMO-UHFFFAOYSA-N 1-chloroethyl 2,2-dimethylpropanoate Chemical compound CC(Cl)OC(=O)C(C)(C)C VQEZDLXEVJCRMO-UHFFFAOYSA-N 0.000 description 2
- VVPUIKNICYCXJZ-UHFFFAOYSA-N 4-iodobutyl benzoate Chemical compound ICCCCOC(=O)C1=CC=CC=C1 VVPUIKNICYCXJZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 2
- KFYXXCWHKINEIC-UHFFFAOYSA-N chloromethyl 2-phenylacetate Chemical compound ClCOC(=O)CC1=CC=CC=C1 KFYXXCWHKINEIC-UHFFFAOYSA-N 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- MZXRBRZQONZAJP-UHFFFAOYSA-N chloromethyl thiophene-2-carboxylate Chemical compound ClCOC(=O)C1=CC=CS1 MZXRBRZQONZAJP-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- 239000013029 homogenous suspension Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 210000003712 lysosome Anatomy 0.000 description 2
- 230000001868 lysosomic effect Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 239000010491 poppyseed oil Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 238000012800 visualization Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 1
- CGKKDGMMKSOGLM-UHFFFAOYSA-N 1-chloroethyl acetate Chemical compound CC(Cl)OC(C)=O CGKKDGMMKSOGLM-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DNMUMZLKDOZMEY-UHFFFAOYSA-N 4-methoxy-3-methylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C DNMUMZLKDOZMEY-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100006370 Arabidopsis thaliana CHX2 gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DBVKZLOIZYVUPX-UHFFFAOYSA-L C([O-])([O-])=O.[Cs+].S1C(=CC=C1)C(=O)OCSC1=CC=CC=C1.[Cs+] Chemical compound C([O-])([O-])=O.[Cs+].S1C(=CC=C1)C(=O)OCSC1=CC=CC=C1.[Cs+] DBVKZLOIZYVUPX-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 229910006024 SO2Cl2 Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- FFINMCNLQNTKLU-UHFFFAOYSA-N adipiodone Chemical compound OC(=O)C1=C(I)C=C(I)C(NC(=O)CCCCC(=O)NC=2C(=C(C(O)=O)C(I)=CC=2I)I)=C1I FFINMCNLQNTKLU-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- GANOALGPACWCPJ-UHFFFAOYSA-N chloromethyl 4-methoxy-3-methylbenzoate Chemical compound COC1=CC=C(C(=O)OCCl)C=C1C GANOALGPACWCPJ-UHFFFAOYSA-N 0.000 description 1
- SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- LPYRCDIRADFIAG-UHFFFAOYSA-L dicesium phenylsulfanylmethyl 2-phenylacetate carbonate Chemical compound C([O-])([O-])=O.[Cs+].C1(=CC=CC=C1)CC(=O)OCSC1=CC=CC=C1.[Cs+] LPYRCDIRADFIAG-UHFFFAOYSA-L 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229940029355 iodipamide Drugs 0.000 description 1
- 125000006303 iodophenyl group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000001865 kupffer cell Anatomy 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000012285 ultrasound imaging Methods 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878717625A GB8717625D0 (en) | 1987-07-24 | 1987-07-24 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE882247L IE882247L (en) | 1989-01-24 |
| IE61263B1 true IE61263B1 (en) | 1994-10-19 |
Family
ID=10621281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE224788A IE61263B1 (en) | 1987-07-24 | 1988-07-22 | Iodinated esters |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0300828B1 (enExample) |
| JP (1) | JP2563555B2 (enExample) |
| AT (1) | ATE73763T1 (enExample) |
| AU (1) | AU609858B2 (enExample) |
| DE (1) | DE3869256D1 (enExample) |
| DK (1) | DK14490A (enExample) |
| ES (1) | ES2030170T3 (enExample) |
| FI (1) | FI94095C (enExample) |
| GB (1) | GB8717625D0 (enExample) |
| GR (1) | GR3004614T3 (enExample) |
| HU (1) | HU210550B (enExample) |
| IE (1) | IE61263B1 (enExample) |
| NO (1) | NO180747C (enExample) |
| NZ (1) | NZ225551A (enExample) |
| RU (1) | RU1829940C (enExample) |
| WO (1) | WO1989000988A1 (enExample) |
| ZA (1) | ZA885411B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826689A (en) * | 1984-05-21 | 1989-05-02 | University Of Rochester | Method for making uniformly sized particles from water-insoluble organic compounds |
| US4863714A (en) * | 1987-02-05 | 1989-09-05 | Cook Imaging Corporation | Sterilization of compositions of limited stability |
| US5354549A (en) * | 1987-07-24 | 1994-10-11 | Nycomed Imaging As | Iodinated esters |
| US5580600A (en) * | 1991-06-14 | 1996-12-03 | Associated Food Technology Pty, Ltd. | Monounsaturated dairy products |
| US5330739A (en) * | 1992-12-04 | 1994-07-19 | Sterling Winthrop Inc. | Iodinated benzoyl acetals and ketals for x-ray imaging |
| EP1866155A2 (en) | 2005-04-05 | 2007-12-19 | Bar-Ilan University | New core and core-shell nanoparticles containing iodine for x-ray imaging |
| DE102018212966A1 (de) * | 2018-08-02 | 2020-02-06 | Siemens Mobility GmbH | Verkleidungselement |
| CN119564969B (zh) * | 2025-01-24 | 2025-04-04 | 四川大学华西医院 | 一种荧光显影剂合成注射控制系统、注射泵及存储介质 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1459772A (en) * | 1973-06-28 | 1976-12-31 | Beecham Group Ltd | X-ray contrast agents |
| AU473168B2 (en) * | 1971-04-15 | 1973-10-18 | Nippon Steel Corporation | Magnetic conveyor |
| AT325762B (de) * | 1972-04-12 | 1975-11-10 | Beecham Group Ltd | Rontgenkontrastmittel |
| GB2157283B (en) * | 1984-03-30 | 1987-07-08 | Squibb & Sons Inc | Esters of 3,5-diacetylamino-2,4,6-triiodobenzoic acid as x-ray contrast agents |
| IE63232B1 (en) * | 1987-05-22 | 1995-04-05 | Bracco Int Bv | A process for the preparation of 5-acylamino-2,4,6-triiodo- or tribromo-benzoic acid derivatives and corresponding novel 5-acylamino-2,4,6-triiodo or tribromo-benzoic acid derivatives obtained by said process |
-
1987
- 1987-07-24 GB GB878717625A patent/GB8717625D0/en active Pending
-
1988
- 1988-07-22 HU HU884573A patent/HU210550B/hu not_active IP Right Cessation
- 1988-07-22 AU AU20870/88A patent/AU609858B2/en not_active Ceased
- 1988-07-22 AT AT88306792T patent/ATE73763T1/de not_active IP Right Cessation
- 1988-07-22 JP JP63506227A patent/JP2563555B2/ja not_active Expired - Fee Related
- 1988-07-22 EP EP88306792A patent/EP0300828B1/en not_active Expired - Lifetime
- 1988-07-22 ES ES198888306792T patent/ES2030170T3/es not_active Expired - Lifetime
- 1988-07-22 IE IE224788A patent/IE61263B1/en not_active IP Right Cessation
- 1988-07-22 DE DE8888306792T patent/DE3869256D1/de not_active Expired - Lifetime
- 1988-07-22 WO PCT/GB1988/000604 patent/WO1989000988A1/en not_active Ceased
- 1988-07-25 NZ NZ225551A patent/NZ225551A/en unknown
- 1988-07-25 ZA ZA885411A patent/ZA885411B/xx unknown
-
1990
- 1990-01-18 DK DK014490A patent/DK14490A/da not_active Application Discontinuation
- 1990-01-19 NO NO900269A patent/NO180747C/no unknown
- 1990-01-23 FI FI900347A patent/FI94095C/fi not_active IP Right Cessation
- 1990-01-23 RU SU904742976A patent/RU1829940C/ru active
-
1992
- 1992-05-18 GR GR920400938T patent/GR3004614T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK14490D0 (da) | 1990-01-18 |
| ZA885411B (en) | 1989-04-26 |
| GB8717625D0 (en) | 1987-09-03 |
| NO900269D0 (no) | 1990-01-19 |
| NO900269L (no) | 1990-01-19 |
| ES2030170T3 (es) | 1992-10-16 |
| EP0300828A1 (en) | 1989-01-25 |
| JP2563555B2 (ja) | 1996-12-11 |
| FI94095C (fi) | 1995-07-25 |
| AU2087088A (en) | 1989-03-01 |
| DK14490A (da) | 1990-01-18 |
| RU1829940C (ru) | 1993-07-23 |
| FI900347A0 (fi) | 1990-01-23 |
| NZ225551A (en) | 1991-06-25 |
| IE882247L (en) | 1989-01-24 |
| HU210550B (en) | 1995-05-29 |
| NO180747B (no) | 1997-03-03 |
| EP0300828B1 (en) | 1992-03-18 |
| WO1989000988A1 (en) | 1989-02-09 |
| FI94095B (fi) | 1995-04-13 |
| ATE73763T1 (de) | 1992-04-15 |
| NO180747C (no) | 1997-06-11 |
| DE3869256D1 (de) | 1992-04-23 |
| HUT53585A (en) | 1990-11-28 |
| HU884573D0 (en) | 1990-09-28 |
| JPH02504270A (ja) | 1990-12-06 |
| GR3004614T3 (enExample) | 1993-04-28 |
| AU609858B2 (en) | 1991-05-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |