JP2011500770A - 造影剤 - Google Patents
造影剤 Download PDFInfo
- Publication number
- JP2011500770A JP2011500770A JP2010530487A JP2010530487A JP2011500770A JP 2011500770 A JP2011500770 A JP 2011500770A JP 2010530487 A JP2010530487 A JP 2010530487A JP 2010530487 A JP2010530487 A JP 2010530487A JP 2011500770 A JP2011500770 A JP 2011500770A
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- JP
- Japan
- Prior art keywords
- bis
- group
- compound
- formula
- dihydroxypropyl
- 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.)
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- 239000002872 contrast media Substances 0.000 title claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 238000003384 imaging method Methods 0.000 claims abstract description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 66
- -1 N-substituted urea group Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- KGENISXXKJIIGQ-UHFFFAOYSA-N [3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodophenyl]carbamic acid Chemical compound OCC(O)CNC(=O)C1=C(I)C(NC(O)=O)=C(I)C(C(=O)NCC(O)CO)=C1I KGENISXXKJIIGQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 5
- 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
- 241001465754 Metazoa Species 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 238000002405 diagnostic procedure Methods 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- KJFCRDWRVOFQHN-UHFFFAOYSA-N [3-[bis(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodophenyl]carbamic acid Chemical compound OCC(O)CN(CC(O)CO)C(=O)C1=C(I)C=C(I)C(NC(O)=O)=C1I KJFCRDWRVOFQHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004437 phosphorous atom Chemical class 0.000 claims description 2
- 150000003463 sulfur Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 abstract description 22
- 239000011630 iodine Substances 0.000 abstract description 22
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 21
- 229940039231 contrast media Drugs 0.000 abstract description 18
- 238000002059 diagnostic imaging Methods 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000002953 preparative HPLC Methods 0.000 description 10
- 239000000539 dimer Substances 0.000 description 9
- 238000004108 freeze drying Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- 238000005833 cis-dihydroxylation reaction Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 206010029155 Nephropathy toxic Diseases 0.000 description 4
- DUSXUYXPDYMORM-UHFFFAOYSA-N [2-acetyloxy-3-[[3-(2,3-diacetyloxypropylcarbamoyl)-2,4,6-triiodo-5-isocyanatobenzoyl]amino]propyl] acetate Chemical compound CC(=O)OCC(OC(C)=O)CNC(=O)C1=C(I)C(N=C=O)=C(I)C(C(=O)NCC(COC(C)=O)OC(C)=O)=C1I DUSXUYXPDYMORM-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000002708 enhancing effect Effects 0.000 description 4
- 238000009472 formulation Methods 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- 239000000815 hypotonic solution 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
- 239000002243 precursor Substances 0.000 description 2
- 238000002601 radiography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 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
- 0 OCC(CN(CC(CO)O)C(c(c(I)c(c(I)c1C(N(CC(CO)O)CC(CO)O)=O)NC(NCC(CNC(Nc(c(I)c(C2=*C(CO)CN2CC(CO)O)c(I)c2C(N(CC(CO)O)CC(CO)O)=O)c2I)=O)O)=O)c1I)=O)O Chemical compound OCC(CN(CC(CO)O)C(c(c(I)c(c(I)c1C(N(CC(CO)O)CC(CO)O)=O)NC(NCC(CNC(Nc(c(I)c(C2=*C(CO)CN2CC(CO)O)c(I)c2C(N(CC(CO)O)CC(CO)O)=O)c2I)=O)O)=O)c1I)=O)O 0.000 description 1
- PEWGLCHLAYAOGA-UHFFFAOYSA-N OCC(CN(CC(CO)O)C(c(c(I)c(c(I)c1C(N(CC(CO)O)CC(CO)O)=O)NC(OCCCOC(Nc(c(I)c(C(N(CC(CO)O)CC(CO)O)=O)c(I)c2C(N(CC(CO)O)CC(CO)O)=O)c2I)=O)=O)c1I)=O)O Chemical compound OCC(CN(CC(CO)O)C(c(c(I)c(c(I)c1C(N(CC(CO)O)CC(CO)O)=O)NC(OCCCOC(Nc(c(I)c(C(N(CC(CO)O)CC(CO)O)=O)c(I)c2C(N(CC(CO)O)CC(CO)O)=O)c2I)=O)=O)c1I)=O)O PEWGLCHLAYAOGA-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- SHUOZUDQONPJGS-UHFFFAOYSA-N [2-acetyloxy-3-[[3-amino-5-(2,3-diacetyloxypropylcarbamoyl)-2,4,6-triiodobenzoyl]amino]propyl] acetate Chemical compound CC(=O)OCC(OC(C)=O)CNC(=O)C1=C(I)C(N)=C(I)C(C(=O)NCC(COC(C)=O)OC(C)=O)=C1I SHUOZUDQONPJGS-UHFFFAOYSA-N 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 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
- 150000001412 amines Chemical group 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
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 239000012141 concentrate Substances 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
- 229960005423 diatrizoate Drugs 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 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
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 231100000268 induced nephrotoxicity Toxicity 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 125000006303 iodophenyl group Chemical group 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
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 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
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- 125000004355 nitrogen functional group Chemical group 0.000 description 1
- 239000003690 nonionic contrast media Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003826 tablet Substances 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
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| NO20075474 | 2007-10-30 | ||
| PCT/EP2008/064632 WO2009056555A1 (en) | 2007-10-30 | 2008-10-29 | Contrast agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011500770A true JP2011500770A (ja) | 2011-01-06 |
| JP2011500770A5 JP2011500770A5 (https=) | 2012-12-06 |
Family
ID=40201831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010530487A Pending JP2011500770A (ja) | 2007-10-30 | 2008-10-29 | 造影剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8551449B2 (https=) |
| EP (1) | EP2203190A1 (https=) |
| JP (1) | JP2011500770A (https=) |
| CN (1) | CN101842120A (https=) |
| WO (1) | WO2009056555A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017063B (zh) * | 2014-04-18 | 2018-11-20 | 沈阳中海生物技术开发有限公司 | 5-氨基-2,4,6-三碘间苯二甲酸衍生物及其盐、水合物或溶剂化物 |
| CN105001114B (zh) * | 2014-04-18 | 2018-11-20 | 沈阳中海生物技术开发有限公司 | 制备碘普罗胺的新方法 |
| EP3548531B1 (en) * | 2016-12-02 | 2023-06-28 | The Texas A&M University System | Chemically modified shape memory polymer embolic foams with increased x-ray visualization |
| CN116813495A (zh) * | 2023-06-16 | 2023-09-29 | 上海慧聚药业有限公司 | 合成碘克沙醇 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS537637A (en) * | 1976-06-23 | 1978-01-24 | Schering Ag | Production of novel dicarboxylic aciddbis*3*55dicarbamoyll2*4*66 triiodo anilide* and xxray contrast medium containing same * production of tetraacarboxylic acid tetrachloride |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1245853B (it) * | 1990-11-16 | 1994-10-25 | Bracco Spa | 1,3-bis(3-(mono o poliidrossi)acilamino-5-(mono o poliidrossi-alchil) aminocarbonil-2,4,6-triiodo-benzoil-amino)-idrossi- o idrossi-alchil- propani, loro metodo di preparazione e mezzi di contrasto roentgenografici che li contengono |
| GB9419206D0 (en) * | 1994-09-23 | 1994-11-09 | Nycomed Innovation Ab | Contrast media |
| PT1435935E (pt) * | 2001-10-12 | 2009-12-29 | Lasser Family Partnership L P | Meios de contraste de raios-x concentrados podem actuar como antigénios universais e podem inibir ou prevenir reacções alérgicas |
-
2008
- 2008-10-29 EP EP08844863A patent/EP2203190A1/en not_active Withdrawn
- 2008-10-29 WO PCT/EP2008/064632 patent/WO2009056555A1/en not_active Ceased
- 2008-10-29 CN CN200880114820A patent/CN101842120A/zh active Pending
- 2008-10-29 US US12/739,977 patent/US8551449B2/en not_active Expired - Fee Related
- 2008-10-29 JP JP2010530487A patent/JP2011500770A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS537637A (en) * | 1976-06-23 | 1978-01-24 | Schering Ag | Production of novel dicarboxylic aciddbis*3*55dicarbamoyll2*4*66 triiodo anilide* and xxray contrast medium containing same * production of tetraacarboxylic acid tetrachloride |
Non-Patent Citations (1)
| Title |
|---|
| JPN5010014560; ＪＯＨＮＳＯＮ， ＪＯＨＮ Ｄ．Ａ．: ＪＯＵＲＮＡＬ ＯＦ ＴＨＥ ＣＨＥＭＩＣＡＬ ＳＯＣＩＥＴＹ , 1955, Ｐ３３２２-３３２４ * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2203190A1 (en) | 2010-07-07 |
| US8551449B2 (en) | 2013-10-08 |
| US20100260685A1 (en) | 2010-10-14 |
| WO2009056555A1 (en) | 2009-05-07 |
| CN101842120A (zh) | 2010-09-22 |
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