JP2011500530A - 造影剤 - Google Patents
造影剤 Download PDFInfo
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- JP2011500530A JP2011500530A JP2010528405A JP2010528405A JP2011500530A JP 2011500530 A JP2011500530 A JP 2011500530A JP 2010528405 A JP2010528405 A JP 2010528405A JP 2010528405 A JP2010528405 A JP 2010528405A JP 2011500530 A JP2011500530 A JP 2011500530A
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- 239000002872 contrast media Substances 0.000 title claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 238000003384 imaging method Methods 0.000 claims abstract description 12
- -1 2,3-dihydroxypropyl moiety Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000000032 diagnostic agent Substances 0.000 claims description 5
- 229940039227 diagnostic agent Drugs 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 238000002405 diagnostic procedure Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- BKQLXOWTSJWKLF-UHFFFAOYSA-N 3-[(2,3-dihydroxypropanoylamino)-[3-[(2,3-dihydroxypropanoylamino)-[3-[2,3-dihydroxypropyl(2-hydroxyethyl)carbamoyl]-2,4,6-triiodobenzoyl]amino]-2-hydroxypropyl]carbamoyl]-n-(2,3-dihydroxypropyl)-n-(2-hydroxyethyl)-2,4,6-triiodobenzamide Chemical compound OCC(O)CN(CCO)C(=O)C1=C(I)C=C(I)C(C(=O)N(CC(O)CN(NC(=O)C(O)CO)C(=O)C=2C(=C(C(=O)N(CCO)CC(O)CO)C(I)=CC=2I)I)NC(=O)C(O)CO)=C1I BKQLXOWTSJWKLF-UHFFFAOYSA-N 0.000 claims description 2
- QSMUCCTTXNYEPS-UHFFFAOYSA-N 3-[[3-[[3-[bis(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodobenzoyl]-[(2-hydroxyacetyl)amino]amino]-2-hydroxypropyl]-[(2-hydroxyacetyl)amino]carbamoyl]-n,n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzamide Chemical compound OCC(O)CN(CC(O)CO)C(=O)C1=C(I)C=C(I)C(C(=O)N(CC(O)CN(NC(=O)CO)C(=O)C=2C(=C(C(=O)N(CC(O)CO)CC(O)CO)C(I)=CC=2I)I)NC(=O)CO)=C1I QSMUCCTTXNYEPS-UHFFFAOYSA-N 0.000 claims description 2
- YXAXYMDPRDFWDU-UHFFFAOYSA-N 3-[[3-[[3-[bis(2-hydroxyethyl)carbamoyl]-2,4,6-triiodobenzoyl]-[(2-hydroxyacetyl)amino]amino]-2-hydroxypropyl]-[(2-hydroxyacetyl)amino]carbamoyl]-n,n-bis(2-hydroxyethyl)-2,4,6-triiodobenzamide Chemical compound OCCN(CCO)C(=O)C1=C(I)C=C(I)C(C(=O)N(CC(O)CN(NC(=O)CO)C(=O)C=2C(=C(C(=O)N(CCO)CCO)C(I)=CC=2I)I)NC(=O)CO)=C1I YXAXYMDPRDFWDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 abstract description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 23
- 239000011630 iodine Substances 0.000 abstract description 23
- 229940039231 contrast media Drugs 0.000 abstract description 18
- 238000002059 diagnostic imaging Methods 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 11
- 239000000539 dimer Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229960004359 iodixanol Drugs 0.000 description 7
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000002708 enhancing effect Effects 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 206010029155 Nephropathy toxic Diseases 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 231100000417 nephrotoxicity Toxicity 0.000 description 4
- 230000007694 nephrotoxicity Effects 0.000 description 4
- 230000003204 osmotic effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 3
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 2
- KOBOTRUWXGCBFD-UHFFFAOYSA-N 2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methylamino]ethanol Chemical compound CC1(C)OCC(CNCCO)O1 KOBOTRUWXGCBFD-UHFFFAOYSA-N 0.000 description 2
- WDMIBBXCJKNKPN-UHFFFAOYSA-N 3-(2-hydroxyethylamino)propane-1,2-diol Chemical compound OCCNCC(O)CO WDMIBBXCJKNKPN-UHFFFAOYSA-N 0.000 description 2
- HUHDYASLFWQVOL-WZTVWXICSA-N 3-[[2-[[3-[acetyl(methyl)amino]-2,4,6-triiodo-5-(methylcarbamoyl)benzoyl]amino]acetyl]amino]-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I HUHDYASLFWQVOL-WZTVWXICSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PQZLQOGLMSANKA-UHFFFAOYSA-N [2-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I PQZLQOGLMSANKA-UHFFFAOYSA-N 0.000 description 2
- SHYMHRFJAFRKKD-UHFFFAOYSA-N [2-[3-[bis(prop-2-enyl)carbamoyl]-5-carbonochloridoyl-2,4,6-triiodoanilino]-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(=O)N(CC=C)CC=C)=C1I SHYMHRFJAFRKKD-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 210000000746 body region Anatomy 0.000 description 2
- 231100000045 chemical toxicity Toxicity 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000815 hypotonic solution Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000000193 iodinated contrast media Substances 0.000 description 2
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 2
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002601 radiography Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 206010020852 Hypertonia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LLWMNRMHBHLGRC-UHFFFAOYSA-N [2-acetyloxy-3-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-3-oxopropyl] acetate Chemical compound CC(=O)OCC(OC(C)=O)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I LLWMNRMHBHLGRC-UHFFFAOYSA-N 0.000 description 1
- ZBLCSMWNTDSUQT-UHFFFAOYSA-N [2-acetyloxy-3-[3-carbonochloridoyl-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl-(2-hydroxyethyl)carbamoyl]-2,4,6-triiodoanilino]-3-oxopropyl] acetate Chemical compound CC(=O)OCC(OC(C)=O)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(=O)N(CCO)CC2OC(C)(C)OC2)=C1I ZBLCSMWNTDSUQT-UHFFFAOYSA-N 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000007321 biological mechanism Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002586 coronary angiography Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229960005423 diatrizoate Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 231100000268 induced nephrotoxicity Toxicity 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 229960001025 iohexol Drugs 0.000 description 1
- 229960000780 iomeprol Drugs 0.000 description 1
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 description 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 229960001707 ioxaglic acid Drugs 0.000 description 1
- TYYBFXNZMFNZJT-UHFFFAOYSA-N ioxaglic acid Chemical compound CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I TYYBFXNZMFNZJT-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002595 magnetic resonance imaging Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003690 nonionic contrast media Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0438—Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20075241 | 2007-10-12 | ||
| PCT/EP2008/063584 WO2009047315A1 (en) | 2007-10-12 | 2008-10-10 | Contrast agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011500530A true JP2011500530A (ja) | 2011-01-06 |
| JP2011500530A5 JP2011500530A5 (https=) | 2011-11-24 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2010528405A Pending JP2011500530A (ja) | 2007-10-12 | 2008-10-10 | 造影剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100221191A1 (https=) |
| EP (1) | EP2203189B1 (https=) |
| JP (1) | JP2011500530A (https=) |
| CN (1) | CN101820924A (https=) |
| ES (1) | ES2389974T3 (https=) |
| WO (1) | WO2009047315A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101209633B1 (ko) * | 2009-09-09 | 2012-12-06 | 주식회사 휴메딕스 | 페길레이션된 삼요오드화 아릴 화합물 및 그를 포함하는 ｘ-선 조영제 |
| JP6150179B2 (ja) | 2011-08-19 | 2017-06-21 | パセオン オーストリア ゲーエムベーハー ウント ツェーオー カーゲー | Ｒ−ビフェニルアラニノールの合成 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06504268A (ja) * | 1990-11-16 | 1994-05-19 | ブラッコ エッセ ピ ア | １，３−ビス−［３−（モノ−またはポリ−ヒドロキシ）アシルアミノ−５−（モノ−またはポリ−ヒドロキシアルキル）アミノカルボニル−２，４，６−トリヨ−ド−ベンゾイル−アミノ］−ヒドロキシ−またはヒドロキシアルキル−プロパン類、それらの製造法、およびそれらを含有する造影剤 |
| WO2007094683A1 (en) * | 2006-02-15 | 2007-08-23 | Ge Healthcare As | Contrast agents |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE344166B (https=) | 1966-12-13 | 1972-04-04 | Pharmacia Ab | |
| US3804892A (en) | 1967-12-28 | 1974-04-16 | Pharmacia Ab | Novel 3,5-substituted 2,4,6-triiodobenzoic acids and salts thereof |
| SE315974B (https=) | 1967-12-28 | 1969-10-13 | Pharmacia Ab | |
| US3763227A (en) | 1967-12-28 | 1973-10-02 | Pharmacia Ab | Novel 3,5-substituted 2,4,6-triiodobenzoic acids and salts thereof |
| DE2628517C2 (de) | 1976-06-23 | 1985-02-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | Dicarbonsäure-bis(3,5-dicarbamoyl-2,4,6-trijodanilid)-Verbindungen, Verfahren zu ihrer Herstellung und Röntgenkontrastmittel |
| IT1207226B (it) | 1979-08-09 | 1989-05-17 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico, metodo per la loro preparazione e mezzi di contrasto che li contengono. |
| DE3038853A1 (de) | 1980-10-10 | 1982-05-27 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue n-hydroxy-alkylierte dicarbonsaeure-bis-(3,5-dicarbamoyl-2,4,6-trijodanilide), deren herstellung und diese enthaltende roentgenkonstrastmittel (ii) |
| DK160868C (da) | 1982-11-08 | 1991-10-14 | Nyegaard & Co As | Trijodfenylderivater, fremgangsmaader til fremstilling deraf og radiologisk praeparat indeholdende dem |
| FR2634571B1 (fr) | 1988-07-19 | 1990-10-19 | Kodak Pathe | Procede d'organisation et de lecture d'un support magnetique et support en faisant application |
| GB9020091D0 (en) | 1990-09-14 | 1990-10-24 | Nycomed As | Contrast media |
| GB9303992D0 (en) | 1993-02-26 | 1993-04-14 | Nycomed Imaging As | Contrast agents |
| AU6114396A (en) | 1995-06-16 | 1997-01-15 | Biophysica Foundation | Formyl derivatives as nonionic contrast media |
| US6072069A (en) | 1998-11-04 | 2000-06-06 | Biophysica, Inc. | Biodegradable nonionic contrast media |
| EP1186305A1 (en) | 2000-09-07 | 2002-03-13 | Schering Aktiengesellschaft | New brominated compounds as contrast media for X-ray mammography |
| EP1492776B1 (en) | 2002-03-27 | 2008-10-29 | FUJIFILM Corporation | Iodinated triglyceride analogs |
-
2008
- 2008-10-10 CN CN200880111358A patent/CN101820924A/zh active Pending
- 2008-10-10 US US12/682,063 patent/US20100221191A1/en not_active Abandoned
- 2008-10-10 ES ES08805206T patent/ES2389974T3/es active Active
- 2008-10-10 JP JP2010528405A patent/JP2011500530A/ja active Pending
- 2008-10-10 WO PCT/EP2008/063584 patent/WO2009047315A1/en not_active Ceased
- 2008-10-10 EP EP08805206A patent/EP2203189B1/en not_active Not-in-force
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06504268A (ja) * | 1990-11-16 | 1994-05-19 | ブラッコ エッセ ピ ア | １，３−ビス−［３−（モノ−またはポリ−ヒドロキシ）アシルアミノ−５−（モノ−またはポリ−ヒドロキシアルキル）アミノカルボニル−２，４，６−トリヨ−ド−ベンゾイル−アミノ］−ヒドロキシ−またはヒドロキシアルキル−プロパン類、それらの製造法、およびそれらを含有する造影剤 |
| WO2007094683A1 (en) * | 2006-02-15 | 2007-08-23 | Ge Healthcare As | Contrast agents |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101820924A (zh) | 2010-09-01 |
| EP2203189B1 (en) | 2012-07-18 |
| WO2009047315A1 (en) | 2009-04-16 |
| EP2203189A1 (en) | 2010-07-07 |
| ES2389974T3 (es) | 2012-11-05 |
| US20100221191A1 (en) | 2010-09-02 |
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