IL100054A - 1, 3 - Bite -] 3 -) Mono - or Poly - Hydroxy (Asylamino - 5 -) Mono - or Poly - Hydroxy - Alkyl (Aminocrobonyl - 2, 4, 6 - Triodo - Benzville - A - Google Patents
1, 3 - Bite -] 3 -) Mono - or Poly - Hydroxy (Asylamino - 5 -) Mono - or Poly - Hydroxy - Alkyl (Aminocrobonyl - 2, 4, 6 - Triodo - Benzville - AInfo
- Publication number
- IL100054A IL100054A IL10005491A IL10005491A IL100054A IL 100054 A IL100054 A IL 100054A IL 10005491 A IL10005491 A IL 10005491A IL 10005491 A IL10005491 A IL 10005491A IL 100054 A IL100054 A IL 100054A
- Authority
- IL
- Israel
- Prior art keywords
- amino
- hydroxy
- bis
- aminocarbonyl
- triiodo
- Prior art date
Links
- 239000002872 contrast media Substances 0.000 title claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 51
- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229940039231 contrast media Drugs 0.000 title abstract description 10
- -1 2 , 3-dihydroxy-propyl Chemical group 0.000 claims description 103
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 48
- QOFLTGDAZLWRMJ-UHFFFAOYSA-N 2-methylpropane-1,1-diol Chemical compound CC(C)C(O)O QOFLTGDAZLWRMJ-UHFFFAOYSA-N 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 15
- 239000001294 propane Substances 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- SKCKOFZKJLZSFA-KVTDHHQDSA-N (2r,3r,4r,5r)-hexane-1,2,3,4,5-pentol Chemical compound C[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SKCKOFZKJLZSFA-KVTDHHQDSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- XWTSUOQLQNQFMN-RIIWJZGXSA-N 1-N-[2,2-bis(hydroxymethyl)-3-[[3-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodo-5-(1,3,4-trihydroxybutan-2-ylcarbamoyl)benzoyl]amino]propyl]-5-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodo-3-N-(1,3,4-trihydroxybutan-2-yl)benzene-1,3-dicarboxamide Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)C(O)CO)=C(I)C(C(=O)NCC(CO)(CO)CNC(=O)C2=C(I)C(NC(=O)[C@H](C)O)=C(I)C(C(=O)NC(CO)C(O)CO)=C2I)=C1I XWTSUOQLQNQFMN-RIIWJZGXSA-N 0.000 claims description 2
- DLTCLUPPEMEAGB-UHFFFAOYSA-N 3-carbamoyl-2,4,6-triiodobenzoic acid Chemical compound NC(=O)C1=C(I)C=C(I)C(C(O)=O)=C1I DLTCLUPPEMEAGB-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- GRDXPWLPADWYQP-SUKXCGAGSA-N 1-N-[2-hydroxy-3-[[3-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodo-5-(1,3,4-trihydroxybutan-2-ylcarbamoyl)benzoyl]amino]propyl]-5-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodo-3-N-(1,3,4-trihydroxybutan-2-yl)benzene-1,3-dicarboxamide Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)C(O)CO)=C(I)C(C(=O)NCC(O)CNC(=O)C2=C(I)C(NC(=O)[C@H](C)O)=C(I)C(C(=O)NC(CO)C(O)CO)=C2I)=C1I GRDXPWLPADWYQP-SUKXCGAGSA-N 0.000 claims 1
- LNUNMBDGXOLGCP-UHFFFAOYSA-N 1-n-(2,3-dihydroxypropyl)-3-n-[2-[[[3-(2,3-dihydroxypropylcarbamoyl)-5-[(2-hydroxyacetyl)amino]-2,4,6-triiodobenzoyl]amino]methyl]-3-hydroxy-2-(hydroxymethyl)propyl]-5-[(2-hydroxyacetyl)amino]-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(NC(=O)CO)=C(I)C(C(=O)NCC(CO)(CO)CNC(=O)C=2C(=C(C(=O)NCC(O)CO)C(I)=C(NC(=O)CO)C=2I)I)=C1I LNUNMBDGXOLGCP-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- QMTNNWXZZATTEX-UHFFFAOYSA-N 3-n-(2,3-dihydroxypropyl)-1-n-[3-[[3-(2,3-dihydroxypropylcarbamoyl)-5-[(2-hydroxyacetyl)amino]-2,4,6-triiodobenzoyl]amino]-2-hydroxypropyl]-5-[(2-hydroxyacetyl)amino]-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(NC(=O)CO)=C(I)C(C(=O)NCC(O)CNC(=O)C=2C(=C(C(=O)NCC(O)CO)C(I)=C(NC(=O)CO)C=2I)I)=C1I QMTNNWXZZATTEX-UHFFFAOYSA-N 0.000 claims 1
- FFGNDBUOGQDUDG-UHFFFAOYSA-N 5-[(2-hydroxyacetyl)amino]-1-n-[2-hydroxy-3-[[3-[(2-hydroxyacetyl)amino]-2,4,6-triiodo-5-(1,3,4-trihydroxybutan-2-ylcarbamoyl)benzoyl]amino]propyl]-2,4,6-triiodo-3-n-(1,3,4-trihydroxybutan-2-yl)benzene-1,3-dicarboxamide Chemical compound OCC(O)C(CO)NC(=O)C1=C(I)C(NC(=O)CO)=C(I)C(C(=O)NCC(O)CNC(=O)C=2C(=C(C(=O)NC(CO)C(O)CO)C(I)=C(NC(=O)CO)C=2I)I)=C1I FFGNDBUOGQDUDG-UHFFFAOYSA-N 0.000 claims 1
- GTCRRSLSCCYZCX-UHFFFAOYSA-N 5-[(2-hydroxyacetyl)amino]-3-n-[2-hydroxy-3-[[3-[(2-hydroxyacetyl)amino]-2,4,6-triiodo-5-(1,3,4-trihydroxybutan-2-ylcarbamoyl)benzoyl]-methylamino]propyl]-2,4,6-triiodo-3-n-methyl-1-n-(1,3,4-trihydroxybutan-2-yl)benzene-1,3-dicarboxamide Chemical compound IC=1C(NC(=O)CO)=C(I)C(C(=O)NC(CO)C(O)CO)=C(I)C=1C(=O)N(C)CC(O)CN(C)C(=O)C1=C(I)C(NC(=O)CO)=C(I)C(C(=O)NC(CO)C(O)CO)=C1I GTCRRSLSCCYZCX-UHFFFAOYSA-N 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 135
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- 238000000921 elemental analysis Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003480 eluent Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 11
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- DWQBWQNQEGJFKV-UHFFFAOYSA-N 3-carbamoyl-2,4,6-triiodobenzoyl chloride Chemical compound NC(=O)C1=C(I)C=C(I)C(C(Cl)=O)=C1I DWQBWQNQEGJFKV-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 6
- SJNHRPFNCJRRPT-UHFFFAOYSA-N 1,3-bis(methylamino)propan-2-ol Chemical compound CNCC(O)CNC SJNHRPFNCJRRPT-UHFFFAOYSA-N 0.000 description 5
- 229910017974 NH40H Inorganic materials 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 238000007069 methylation reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- GYVXJNQPQQGGCZ-UHFFFAOYSA-N 2,2-bis(aminomethyl)propane-1,3-diol Chemical compound NCC(CN)(CO)CO GYVXJNQPQQGGCZ-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 3
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 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 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 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 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000002583 angiography Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229960004359 iodixanol Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 238000009608 myelography Methods 0.000 description 2
- 239000003690 nonionic contrast media Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- AOLBMIGVOLSSNI-UHFFFAOYSA-N 1,3-dioxan-5-amine Chemical compound NC1COCOC1 AOLBMIGVOLSSNI-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- YFUIVPOLDRRCFL-UHFFFAOYSA-N 2,2-bis(methylaminomethyl)propane-1,3-diol Chemical compound CNCC(CO)(CO)CNC YFUIVPOLDRRCFL-UHFFFAOYSA-N 0.000 description 1
- ADLFBRNPQMLXTQ-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxan-5-amine Chemical compound CC1(C)OCC(N)CO1 ADLFBRNPQMLXTQ-UHFFFAOYSA-N 0.000 description 1
- CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical class OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- PMLGQXIKBPFHJZ-UHFFFAOYSA-N 3-aminobutane-1,2,4-triol Chemical compound OCC(N)C(O)CO PMLGQXIKBPFHJZ-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- SLOOQCDTPVGZOA-UHFFFAOYSA-N 6-amino-2-ethyl-2-methyl-1,3-dioxepan-5-ol Chemical compound CCC1(C)OCC(N)C(O)CO1 SLOOQCDTPVGZOA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000212977 Andira Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VLWYRBRAKTVFSI-UHFFFAOYSA-N C(C)(=O)OCC(=O)NC=1C(C(C(=O)Cl)(C(=C(C1I)C(CO)C(CO)O)I)C(=O)N)I Chemical compound C(C)(=O)OCC(=O)NC=1C(C(C(=O)Cl)(C(=C(C1I)C(CO)C(CO)O)I)C(=O)N)I VLWYRBRAKTVFSI-UHFFFAOYSA-N 0.000 description 1
- ZCECNHJZOSUYBT-ABYUVQEBSA-N C(C)(=O)O[C@H](C(=O)C=1C(C(C(=O)Cl)(C(=C(C1I)C(CO)C(CO)O)I)C(=O)NN)I)C Chemical compound C(C)(=O)O[C@H](C(=O)C=1C(C(C(=O)Cl)(C(=C(C1I)C(CO)C(CO)O)I)C(=O)NN)I)C ZCECNHJZOSUYBT-ABYUVQEBSA-N 0.000 description 1
- VRLMFVPUXTZHPS-ZJSCCJKCSA-N C(C)(=O)O[C@H](C(=O)C=1C(C(C(=O)Cl)(C(=C(C1I)C1COC(OC1)(C)C)I)C(=O)NN)I)C Chemical compound C(C)(=O)O[C@H](C(=O)C=1C(C(C(=O)Cl)(C(=C(C1I)C1COC(OC1)(C)C)I)C(=O)NN)I)C VRLMFVPUXTZHPS-ZJSCCJKCSA-N 0.000 description 1
- UAVVJJWZNADUJY-SVEQMNJCSA-N C(C)(=O)O[C@H](C(=O)C=1C(C(C(=O)Cl)(C(=C(C1I)CC(CO)O)I)C(=O)NN)I)C Chemical compound C(C)(=O)O[C@H](C(=O)C=1C(C(C(=O)Cl)(C(=C(C1I)CC(CO)O)I)C(=O)NN)I)C UAVVJJWZNADUJY-SVEQMNJCSA-N 0.000 description 1
- FNTOBXKNGCHZTA-UHFFFAOYSA-N CC(=O)OCC(=O)NC1=C(C(=C(C(C1I)(C(=O)N)C(=O)Cl)I)CC(CO)O)I Chemical compound CC(=O)OCC(=O)NC1=C(C(=C(C(C1I)(C(=O)N)C(=O)Cl)I)CC(CO)O)I FNTOBXKNGCHZTA-UHFFFAOYSA-N 0.000 description 1
- XIIOQYMHTPWSBM-PXNBWNBXSA-N C[C@@H](C(=O)C1=C(C(=C(C(C1I)(C(=O)NN)C(=O)Cl)I)CCO)I)OC(=O)C Chemical compound C[C@@H](C(=O)C1=C(C(=C(C(C1I)(C(=O)NN)C(=O)Cl)I)CCO)I)OC(=O)C XIIOQYMHTPWSBM-PXNBWNBXSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 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
- 241000699670 Mus sp. Species 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940127090 anticoagulant agent Drugs 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 206010003074 arachnoiditis Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 230000001037 epileptic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 125000004997 halocarbonyl group Chemical group 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000000815 hypotonic solution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- MNRGFUBMMILKAL-UHFFFAOYSA-N methyl phenylmethanesulfonate Chemical compound COS(=O)(=O)CC1=CC=CC=C1 MNRGFUBMMILKAL-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- CVWADQNDGJRHQF-UHFFFAOYSA-N n-(3-amino-2-hydroxypropyl)-2,2,2-trifluoroacetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCC(O)CNC(=O)C(F)(F)F CVWADQNDGJRHQF-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 102220043690 rs1049562 Human genes 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000007487 urography Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000010626 work up procedure 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
-
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02208890A IT1245853B (it) | 1990-11-16 | 1990-11-16 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL100054A0 IL100054A0 (en) | 1992-08-18 |
| IL100054A true IL100054A (en) | 1996-05-14 |
Family
ID=11191331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10005491A IL100054A (en) | 1990-11-16 | 1991-11-14 | 1, 3 - Bite -] 3 -) Mono - or Poly - Hydroxy (Asylamino - 5 -) Mono - or Poly - Hydroxy - Alkyl (Aminocrobonyl - 2, 4, 6 - Triodo - Benzville - A |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0557345B1 (ja) |
| JP (1) | JP2977613B2 (ja) |
| KR (1) | KR930702281A (ja) |
| AT (1) | ATE111441T1 (ja) |
| AU (1) | AU646119B2 (ja) |
| CA (1) | CA2096136A1 (ja) |
| DE (2) | DE69104059T2 (ja) |
| DK (1) | DK0557345T3 (ja) |
| ES (1) | ES2060415T3 (ja) |
| GR (1) | GR930300134T1 (ja) |
| HU (1) | HUT65652A (ja) |
| IE (1) | IE66460B1 (ja) |
| IL (1) | IL100054A (ja) |
| IS (1) | IS3781A7 (ja) |
| IT (1) | IT1245853B (ja) |
| MX (1) | MX9102103A (ja) |
| NZ (1) | NZ240566A (ja) |
| WO (1) | WO1992008691A1 (ja) |
| ZA (1) | ZA919065B (ja) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2717799B1 (fr) * | 1994-03-22 | 1996-07-19 | Guerbet Sa | Composés polyiodes : procédé de préparation ; composition de diagnostic. |
| ES2341296T3 (es) | 2001-12-20 | 2010-06-17 | Bone Support Ab | Un nuevo sustituto mineral de hueso. |
| ATE429933T1 (de) * | 2004-07-02 | 2009-05-15 | Bracco Imaging Spa | 1,4-bis(carboxymethyl)-6- |
| US7407647B2 (en) * | 2005-12-07 | 2008-08-05 | Cordis Corporation | Organic radiographic contrasting agents for medical devices |
| US20070134163A1 (en) * | 2005-12-13 | 2007-06-14 | Zhao Jonathon Z | Radiographic contrasting agents and radio-opaque polymeric materials for medical devices |
| JP5248329B2 (ja) * | 2006-02-14 | 2013-07-31 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| KR20100033405A (ko) | 2007-07-12 | 2010-03-29 | 지이 헬스케어 에이에스 | 조영제 |
| JP2011500531A (ja) * | 2007-10-12 | 2011-01-06 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| JP2011500532A (ja) * | 2007-10-12 | 2011-01-06 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| GB2453654A (en) * | 2007-10-12 | 2009-04-15 | Ge Healthcare As | A compound for use in X-ray contrast examinations |
| WO2009047319A1 (en) | 2007-10-12 | 2009-04-16 | Ge Healthcare As | Contrast agents |
| CN101820924A (zh) * | 2007-10-12 | 2010-09-01 | 通用电气医疗集团股份有限公司 | 造影剂 |
| WO2009056555A1 (en) * | 2007-10-30 | 2009-05-07 | Ge Healthcare As | Contrast agents |
| JP2011506286A (ja) * | 2007-12-05 | 2011-03-03 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| EP2247314A4 (en) * | 2008-02-01 | 2013-11-27 | Univ Boston | CATIONIC CONTRASTING AGENTS AND METHOD FOR THEIR USE |
| US20110021824A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | Adsorptive purification method for iodixanol |
| EP3220887A1 (en) | 2014-11-21 | 2017-09-27 | Technical University of Denmark | Gel formulations for local drug release |
| US10610366B2 (en) | 2015-01-29 | 2020-04-07 | Theracell, Inc. | Demineralized bone fiber composition for use in minimally invasive surgery |
| CN109475491B (zh) | 2016-05-20 | 2022-06-24 | 丹麦技术大学 | 可触诊的标记物组合物 |
| US10639157B2 (en) | 2017-03-14 | 2020-05-05 | Theracell, Inc. | Demineralized bone fiber composition for use in minimally invasive surgery |
| US20220339285A1 (en) | 2019-06-12 | 2022-10-27 | Technical University Of Denmark | Dissacharide formulations for controlled drug release |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1491129A (en) * | 1975-06-04 | 1977-11-09 | Guerbet Sa | Iodo-benzene derivatives and an x-ray contrast medium containing them |
| CH626873A5 (ja) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa | |
| US4584401A (en) * | 1983-10-20 | 1986-04-22 | Biophysica Foundation | Methods and compositions involving polyhydroxylated polyiodo non-ionic contrast media |
| DE3731542A1 (de) * | 1987-09-17 | 1989-03-30 | Schering Ag | Neue dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6-triiod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
-
1990
- 1990-11-16 IT IT02208890A patent/IT1245853B/it active IP Right Grant
-
1991
- 1991-11-11 IS IS3781A patent/IS3781A7/is unknown
- 1991-11-12 NZ NZ240566A patent/NZ240566A/en unknown
- 1991-11-14 IL IL10005491A patent/IL100054A/en not_active IP Right Cessation
- 1991-11-15 EP EP91919864A patent/EP0557345B1/en not_active Expired - Lifetime
- 1991-11-15 AT AT91919864T patent/ATE111441T1/de not_active IP Right Cessation
- 1991-11-15 DE DE69104059T patent/DE69104059T2/de not_active Expired - Fee Related
- 1991-11-15 DK DK91919864.8T patent/DK0557345T3/da active
- 1991-11-15 AU AU89253/91A patent/AU646119B2/en not_active Ceased
- 1991-11-15 DE DE0557345T patent/DE557345T1/de active Pending
- 1991-11-15 WO PCT/EP1991/002151 patent/WO1992008691A1/en active IP Right Grant
- 1991-11-15 MX MX9102103A patent/MX9102103A/es not_active IP Right Cessation
- 1991-11-15 CA CA002096136A patent/CA2096136A1/en not_active Abandoned
- 1991-11-15 HU HU9301375A patent/HUT65652A/hu unknown
- 1991-11-15 ES ES91919864T patent/ES2060415T3/es not_active Expired - Lifetime
- 1991-11-15 JP JP3517985A patent/JP2977613B2/ja not_active Expired - Fee Related
- 1991-11-15 IE IE398691A patent/IE66460B1/en not_active IP Right Cessation
- 1991-11-15 ZA ZA919065A patent/ZA919065B/xx unknown
-
1993
- 1993-05-12 KR KR1019930701423A patent/KR930702281A/ko not_active Application Discontinuation
-
1994
- 1994-02-28 GR GR930300134T patent/GR930300134T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR930300134T1 (en) | 1994-02-28 |
| MX9102103A (es) | 1992-06-01 |
| ZA919065B (en) | 1992-08-26 |
| HUT65652A (en) | 1994-07-28 |
| IE66460B1 (en) | 1995-12-27 |
| DE69104059D1 (de) | 1994-10-20 |
| CA2096136A1 (en) | 1992-05-17 |
| IT9022088A1 (it) | 1992-05-17 |
| ES2060415T3 (es) | 1994-11-16 |
| DE557345T1 (de) | 1994-07-28 |
| IS3781A7 (is) | 1992-05-17 |
| IT1245853B (it) | 1994-10-25 |
| DE69104059T2 (de) | 1995-02-02 |
| WO1992008691A1 (en) | 1992-05-29 |
| AU8925391A (en) | 1992-06-11 |
| AU646119B2 (en) | 1994-02-10 |
| JP2977613B2 (ja) | 1999-11-15 |
| KR930702281A (ko) | 1993-09-08 |
| IL100054A0 (en) | 1992-08-18 |
| EP0557345A1 (en) | 1993-09-01 |
| JPH06504268A (ja) | 1994-05-19 |
| IT9022088A0 (it) | 1990-11-16 |
| NZ240566A (en) | 1994-02-25 |
| EP0557345B1 (en) | 1994-09-14 |
| ATE111441T1 (de) | 1994-09-15 |
| HU9301375D0 (en) | 1993-09-28 |
| DK0557345T3 (da) | 1995-03-06 |
| IE913986A1 (en) | 1992-05-20 |
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