NO175857B - - Google Patents
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- Publication number
- NO175857B NO175857B NO884127A NO884127A NO175857B NO 175857 B NO175857 B NO 175857B NO 884127 A NO884127 A NO 884127A NO 884127 A NO884127 A NO 884127A NO 175857 B NO175857 B NO 175857B
- Authority
- NO
- Norway
- Prior art keywords
- dihydroxy
- triiodo
- bis
- mmol
- propylcarbamoyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000002872 contrast media Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 claims description 4
- JWTKLOUWVLRHMQ-UHFFFAOYSA-N 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[[3-[3-(2,3-dihydroxypropylcarbamoyl)-5-[2,3-dihydroxypropyl(methyl)carbamoyl]-2,4,6-triiodo-N-methylanilino]-3-oxopropanoyl]-methylamino]-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OC(CN(C(=O)C=1C(=C(N(C(CC(=O)N(C2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(N(C)CC(CO)O)=O)I)C)=O)C)C(=C(C=1I)C(NCC(CO)O)=O)I)I)C)CO JWTKLOUWVLRHMQ-UHFFFAOYSA-N 0.000 claims description 3
- VPOQOMBNJKJYFX-UHFFFAOYSA-N 1-N-(2,3-dihydroxypropyl)-5-[[3-[3-(2,3-dihydroxypropylcarbamoyl)-N-(2-hydroxyethyl)-5-[2-hydroxyethyl(methyl)carbamoyl]-2,4,6-triiodoanilino]-3-oxopropanoyl]-(2-hydroxyethyl)amino]-3-N-(2-hydroxyethyl)-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OCCN(C(=O)C=1C(=C(N(C(CC(=O)N(C2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(N(C)CCO)=O)I)CCO)=O)CCO)C(=C(C=1I)C(NCC(CO)O)=O)I)I)C VPOQOMBNJKJYFX-UHFFFAOYSA-N 0.000 claims description 3
- QRIIIKJEHIXFRK-UHFFFAOYSA-N 3-N-(1,3-dihydroxypropan-2-yl)-5-[[3-[3-(1,3-dihydroxypropan-2-ylcarbamoyl)-5-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodo-N-methylanilino]-2-methoxy-3-oxopropanoyl]-methylamino]-1-N-(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(CO)NC(=O)C=1C(=C(N(C(C(C(=O)N(C2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(NC(CO)CO)=O)I)C)OC)=O)C)C(=C(C=1I)C(NCC(CO)O)=O)I)I QRIIIKJEHIXFRK-UHFFFAOYSA-N 0.000 claims description 3
- LJOWXPVXLSOEFW-UHFFFAOYSA-N 3-N-(2,3-dihydroxypropyl)-5-[[4-[3-(2,3-dihydroxypropylcarbamoyl)-N-(2-hydroxyethyl)-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodoanilino]-2,3-dihydroxy-4-oxobutanoyl]-(2-hydroxyethyl)amino]-1-N-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OC(CNC(=O)C=1C(=C(N(C(C(C(C(=O)N(C2=C(C(=C(C(=C2I)C(NCCO)=O)I)C(NCC(CO)O)=O)I)CCO)O)O)=O)CCO)C(=C(C=1I)C(NCCO)=O)I)I)CO LJOWXPVXLSOEFW-UHFFFAOYSA-N 0.000 claims description 3
- UFRIFFBNKZYPII-UHFFFAOYSA-N 3-N-(2,3-dihydroxypropyl)-5-[[3-[3-[2,3-dihydroxypropyl(methyl)carbamoyl]-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodo-N-methylanilino]-3-oxopropanoyl]-methylamino]-1-N-(2-hydroxyethyl)-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OC(CN(C(=O)C=1C(=C(N(C(CC(=O)N(C2=C(C(=C(C(=C2I)C(NCCO)=O)I)C(N(C)CC(CO)O)=O)I)C)=O)C)C(=C(C=1I)C(NCCO)=O)I)I)C)CO UFRIFFBNKZYPII-UHFFFAOYSA-N 0.000 claims description 2
- GTGSYPNDDOFQAH-UHFFFAOYSA-N 3-n-(2,3-dihydroxypropyl)-5-[2,3-dihydroxypropyl-[3-[n-(2,3-dihydroxypropyl)-3-(2,3-dihydroxypropylcarbamoyl)-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodoanilino]-2-hydroxy-3-oxopropanoyl]amino]-1-n-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(C(=O)NCCO)=C(I)C(N(CC(O)CO)C(=O)C(O)C(=O)N(CC(O)CO)C=2C(=C(C(=O)NCC(O)CO)C(I)=C(C(=O)NCCO)C=2I)I)=C1I GTGSYPNDDOFQAH-UHFFFAOYSA-N 0.000 claims description 2
- XOYUURPLLKWWHE-UHFFFAOYSA-N 5-[[3-[3-[bis(2-hydroxyethyl)carbamoyl]-5-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodo-N-methylanilino]-3-oxopropanoyl]-methylamino]-1-N-(2,3-dihydroxypropyl)-3-N,3-N-bis(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OC(CNC(=O)C=1C(=C(N(C(CC(=O)N(C2=C(C(=C(C(=C2I)C(N(CCO)CCO)=O)I)C(NCC(CO)O)=O)I)C)=O)C)C(=C(C=1I)C(N(CCO)CCO)=O)I)I)CO XOYUURPLLKWWHE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims description 2
- BPSHBFGQFFHFBZ-UHFFFAOYSA-N 3-N-(1,3-dihydroxypropan-2-yl)-5-[[3-[3-(1,3-dihydroxypropan-2-ylcarbamoyl)-5-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodo-N-methylanilino]-2-hydroxy-3-oxopropanoyl]-methylamino]-1-N-(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(CO)NC(=O)C=1C(=C(N(C(C(C(=O)N(C2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(NC(CO)CO)=O)I)C)O)=O)C)C(=C(C=1I)C(NCC(CO)O)=O)I)I BPSHBFGQFFHFBZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- -1 alkyl radical Chemical class 0.000 description 34
- 239000002244 precipitate Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- 150000002500 ions Chemical class 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000725 suspension Substances 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZSCYHXJRVJWNPF-UHFFFAOYSA-N [2-acetyloxy-3-[[3-carbonochloridoyl-5-[[3-[3-carbonochloridoyl-5-(2,3-diacetyloxypropylcarbamoyl)-2,4,6-triiodoanilino]-3-oxopropanoyl]amino]-2,4,6-triiodobenzoyl]amino]propyl] acetate Chemical compound ClC(=O)C1=C(I)C(C(=O)NCC(COC(=O)C)OC(C)=O)=C(I)C(NC(=O)CC(=O)NC=2C(=C(C(=O)NCC(COC(C)=O)OC(C)=O)C(I)=C(C(Cl)=O)C=2I)I)=C1I ZSCYHXJRVJWNPF-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000007306 turnover Effects 0.000 description 5
- FCKXGFANXSHGAW-DTXPUJKBSA-N (2s)-n,n'-bis[(2s)-1-(2-chloro-4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]-2-hydroxybutanediamide Chemical compound C([C@H](NC(=O)C[C@H](O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)Cl)C(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)Cl)C1=CC=CC=C1 FCKXGFANXSHGAW-DTXPUJKBSA-N 0.000 description 4
- BYNKULISCUABSP-UHFFFAOYSA-N 3-amino-5-(2,3-diacetyloxypropylcarbamoyl)-2,4,6-triiodobenzoic acid hydrochloride Chemical compound Cl.CC(=O)OCC(OC(C)=O)CNC(=O)C1=C(I)C(N)=C(I)C(C(O)=O)=C1I BYNKULISCUABSP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VYSSMAHBUCJDSC-UHFFFAOYSA-N 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[[3-[3-(2,3-dihydroxypropylcarbamoyl)-5-[2,3-dihydroxypropyl(methyl)carbamoyl]-2,4,6-triiodo-N-methylanilino]-2-hydroxy-3-oxopropanoyl]-methylamino]-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OC(CN(C(=O)C=1C(=C(N(C(C(C(=O)N(C2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(N(C)CC(CO)O)=O)I)C)O)=O)C)C(=C(C=1I)C(NCC(CO)O)=O)I)I)C)CO VYSSMAHBUCJDSC-UHFFFAOYSA-N 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000002583 angiography Methods 0.000 description 3
- 229940039231 contrast media Drugs 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- JQLWYHOWDBLTRN-UHFFFAOYSA-N 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[[3-[3-(2,3-dihydroxypropylcarbamoyl)-5-[2,3-dihydroxypropyl(methyl)carbamoyl]-2,4,6-triiodoanilino]-3-oxopropanoyl]amino]-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OC(CN(C(=O)C=1C(=C(NC(CC(=O)NC2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(N(C)CC(CO)O)=O)I)=O)C(=C(C=1I)C(NCC(CO)O)=O)I)I)C)CO JQLWYHOWDBLTRN-UHFFFAOYSA-N 0.000 description 2
- WRDSUKPVTFSFOR-UHFFFAOYSA-N 1-N-(2,3-dihydroxypropyl)-5-[[3-[3-(2,3-dihydroxypropylcarbamoyl)-5-[2-hydroxyethyl(methyl)carbamoyl]-2,4,6-triiodoanilino]-3-oxopropanoyl]amino]-3-N-(2-hydroxyethyl)-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OCCN(C(=O)C=1C(=C(NC(CC(=O)NC2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(N(C)CCO)=O)I)=O)C(=C(C=1I)C(NCC(CO)O)=O)I)I)C WRDSUKPVTFSFOR-UHFFFAOYSA-N 0.000 description 2
- ZOBCRLXOSDRIHM-UHFFFAOYSA-N 1-N-(2,3-dihydroxypropyl)-5-[[3-[3-(2,3-dihydroxypropylcarbamoyl)-N-(2-hydroxyethyl)-5-[2-hydroxyethyl(methyl)carbamoyl]-2,4,6-triiodoanilino]-2-hydroxy-3-oxopropanoyl]-(2-hydroxyethyl)amino]-3-N-(2-hydroxyethyl)-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OCCN(C(=O)C=1C(=C(N(C(C(C(=O)N(C2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(N(C)CCO)=O)I)CCO)O)=O)CCO)C(=C(C=1I)C(NCC(CO)O)=O)I)I)C ZOBCRLXOSDRIHM-UHFFFAOYSA-N 0.000 description 2
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 2
- RSVSHBISQDLBEZ-UHFFFAOYSA-N 3-(2,3-dihydroxypropylcarbamoyl)-5-nitrobenzoic acid Chemical compound OCC(O)CNC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 RSVSHBISQDLBEZ-UHFFFAOYSA-N 0.000 description 2
- CIFCCZCMZVSQEC-UHFFFAOYSA-N 3-N-(1,3-dihydroxypropan-2-yl)-5-[[3-[3-(1,3-dihydroxypropan-2-ylcarbamoyl)-5-(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodoanilino]-2-methoxy-3-oxopropanoyl]amino]-1-N-(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(CO)NC(=O)C=1C(=C(NC(C(C(=O)NC2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(NC(CO)CO)=O)I)OC)=O)C(=C(C=1I)C(NCC(CO)O)=O)I)I CIFCCZCMZVSQEC-UHFFFAOYSA-N 0.000 description 2
- UZZHWFMZODTGKD-UHFFFAOYSA-N 3-N-(2,3-dihydroxypropyl)-5-[2,3-dihydroxypropyl-[3-[N-(2,3-dihydroxypropyl)-3-(2,3-dihydroxypropylcarbamoyl)-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodoanilino]-3-oxopropanoyl]amino]-1-N-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OC(CNC(=O)C=1C(=C(N(C(CC(=O)N(C2=C(C(=C(C(=C2I)C(NCCO)=O)I)C(NCC(CO)O)=O)I)CC(CO)O)=O)CC(CO)O)C(=C(C=1I)C(NCCO)=O)I)I)CO UZZHWFMZODTGKD-UHFFFAOYSA-N 0.000 description 2
- AJJQFEXUWFFGQD-UHFFFAOYSA-N 3-N-(2,3-dihydroxypropyl)-5-[[3-[3-(2,3-dihydroxypropylcarbamoyl)-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodoanilino]-2-hydroxy-3-oxopropanoyl]amino]-1-N-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OC(CNC(=O)C=1C(=C(NC(C(C(=O)NC2=C(C(=C(C(=C2I)C(NCCO)=O)I)C(NCC(CO)O)=O)I)O)=O)C(=C(C=1I)C(NCCO)=O)I)I)CO AJJQFEXUWFFGQD-UHFFFAOYSA-N 0.000 description 2
- LNYKMWWAEDEVJQ-UHFFFAOYSA-N 3-N-(2,3-dihydroxypropyl)-5-[[3-[3-[2,3-dihydroxypropyl(methyl)carbamoyl]-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodoanilino]-3-oxopropanoyl]amino]-1-N-(2-hydroxyethyl)-2,4,6-triiodo-3-N-methylbenzene-1,3-dicarboxamide Chemical compound OC(CN(C(=O)C=1C(=C(NC(CC(=O)NC2=C(C(=C(C(=C2I)C(NCCO)=O)I)C(N(C)CC(CO)O)=O)I)=O)C(=C(C=1I)C(NCCO)=O)I)I)C)CO LNYKMWWAEDEVJQ-UHFFFAOYSA-N 0.000 description 2
- SKBGREWGHYZJAC-UHFFFAOYSA-N 3-N-(2,3-dihydroxypropyl)-5-[[4-[3-(2,3-dihydroxypropylcarbamoyl)-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodoanilino]-2,3-dihydroxy-4-oxobutanoyl]amino]-1-N-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OC(CNC(=O)C=1C(=C(NC(C(C(C(=O)NC2=C(C(=C(C(=C2I)C(NCCO)=O)I)C(NCC(CO)O)=O)I)O)O)=O)C(=C(C=1I)C(NCCO)=O)I)I)CO SKBGREWGHYZJAC-UHFFFAOYSA-N 0.000 description 2
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 230000036772 blood pressure Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 150000004691 decahydrates Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 238000009608 myelography Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000029219 regulation of pH Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940037001 sodium edetate Drugs 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 238000007487 urography Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyesters Or Polycarbonates (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873731542 DE3731542A1 (de) | 1987-09-17 | 1987-09-17 | Neue dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6-triiod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
Publications (4)
Publication Number | Publication Date |
---|---|
NO884127D0 NO884127D0 (no) | 1988-09-16 |
NO884127L NO884127L (no) | 1989-03-20 |
NO175857B true NO175857B (fr) | 1994-09-12 |
NO175857C NO175857C (no) | 1994-12-21 |
Family
ID=6336386
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO884127A NO175857C (no) | 1987-09-17 | 1988-09-16 | Nye dicarboxylsyre-bis(3,5-dicarbamoyl-2,4,6-trijodanilider), og röntgenkontrastmidler inneholdende disse |
Country Status (15)
Country | Link |
---|---|
US (1) | US5073362A (fr) |
EP (1) | EP0308364B1 (fr) |
JP (1) | JP2569144B2 (fr) |
KR (1) | KR0139061B1 (fr) |
AT (1) | ATE97126T1 (fr) |
AU (1) | AU616203B2 (fr) |
CA (1) | CA1333911C (fr) |
DE (2) | DE3731542A1 (fr) |
DK (1) | DK514788A (fr) |
ES (1) | ES2059557T3 (fr) |
FI (1) | FI93208C (fr) |
IE (1) | IE62460B1 (fr) |
NO (1) | NO175857C (fr) |
PT (1) | PT88537B (fr) |
ZA (1) | ZA886939B (fr) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3739098A1 (de) * | 1987-11-16 | 1989-05-24 | Schering Ag | Neue substituierte dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6- trijod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
EP0410974A4 (en) * | 1988-03-01 | 1991-09-11 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
IL94718A (en) * | 1989-07-05 | 1994-10-21 | Schering Ag | Non-ionic carboxamide contrast agent and method of preparation |
US5191120A (en) * | 1989-12-13 | 1993-03-02 | Mallinckrodt Medical, Inc. | Process for preparing nonionic X-ray contrast agents |
US5075502A (en) * | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
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 |
FR2673180B1 (fr) * | 1991-02-25 | 1994-03-04 | Guerbet Sa | Nouveaux composes non ioniques poly-iodes, procede de preparation, produit de contraste les contenant. |
ES2037605B1 (es) * | 1991-11-18 | 1994-02-01 | Invest Justesa Imagen S A Cent | Metodo para preparar nuevos agentes yodados no ionicos de constraste a los rayos x. |
FR2695125B1 (fr) * | 1992-08-25 | 1994-12-23 | Guerbet Sa | Nouveaux composés poly-iodés, procédé de préparation, produit de contraste les contenant. |
WO1994022810A1 (fr) * | 1993-04-01 | 1994-10-13 | Centro Investigacion Justesa Imagen, S.A. | Nouveaux dimeres iodes non-ioniques utiles comme agents de contraste aux rayons x, procede de preparation de ces nouveaux dimeres, et compositions galeniques les contenant |
US5611342A (en) * | 1994-02-15 | 1997-03-18 | Molecular Biosystems, Inc. | Method of computer tomography imaging the gastrointestinal tract and surrounding upper abdominal tissues and organs using an orally administered low density contrast medium |
WO1995026331A1 (fr) * | 1994-03-25 | 1995-10-05 | Centro Investigacion Justesa Imagen, S.A. | Nouveaux dimeres iodes non-ioniques, utiles en tant qu'agents de contraste aux rayons x, procede de preparation, et compositions pharmaceutiques les contenant |
SE520688C2 (sv) | 2000-04-11 | 2003-08-12 | Bone Support Ab | Ett injicerbart ersättningsmaterial för benmineral |
SE517168C2 (sv) | 2000-07-17 | 2002-04-23 | Bone Support Ab | En komposition för ett injicerbart ersättningsmaterial för benmineral |
SE522098C2 (sv) | 2001-12-20 | 2004-01-13 | Bone Support Ab | Ett nytt benmineralsubstitut |
DE60220949T2 (de) | 2001-12-20 | 2008-03-06 | Bone Support Ab | Neuer knochenmineralien-ersatzstoff |
KR100442293B1 (ko) | 2001-12-27 | 2004-07-30 | 엘지.필립스 엘시디 주식회사 | 패턴 형성방법 |
SE0300620D0 (sv) | 2003-03-05 | 2003-03-05 | Bone Support Ab | A new bone substitute composition |
SE0302983D0 (sv) | 2003-11-11 | 2003-11-11 | Bone Support Ab | Anordning för att förse spongiöst ben med benersättnings- och/eller benförstärkningsmaterial och förfarande i samband därmed |
SE527528C2 (sv) | 2004-06-22 | 2006-04-04 | Bone Support Ab | Anordning för framställning av härdbar massa samt användning av anordningen |
WO2006055959A2 (fr) * | 2004-11-19 | 2006-05-26 | Bioquanta Corp. | Pharmacophores pf4 et leurs utilisations |
AU2007297012B2 (en) * | 2006-09-13 | 2011-12-22 | Sanofi-Aventis | Tartrate derivatives for use as coagulation factor IXa inhibitors |
US9180137B2 (en) | 2010-02-09 | 2015-11-10 | Bone Support Ab | Preparation of bone cement compositions |
KR101012646B1 (ko) * | 2010-04-01 | 2011-02-09 | 대우조선해양 주식회사 | 공기 공동 선박 |
WO2012136813A2 (fr) | 2011-04-07 | 2012-10-11 | Universitetet I Oslo | Agents pour un diagnostic par radar médical |
PL2958603T3 (pl) | 2013-02-20 | 2018-10-31 | Bone Support Ab | Ulepszone zestalanie utwardzalnego materiału zastępczego kości |
US10610366B2 (en) | 2015-01-29 | 2020-04-07 | Theracell, Inc. | Demineralized bone fiber composition for use in minimally invasive surgery |
US10639157B2 (en) | 2017-03-14 | 2020-05-05 | Theracell, Inc. | Demineralized bone fiber composition for use in minimally invasive surgery |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
CH626873A5 (fr) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa | |
DE2909439A1 (de) * | 1979-03-08 | 1980-09-18 | Schering Ag | Neue nichtionische roentgenkontrastmittel |
DK273280A (da) * | 1979-06-28 | 1980-12-29 | Schering Ag | Trijoderede 5-aminoisophthalsyrederivater |
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. |
US4341756A (en) * | 1980-01-31 | 1982-07-27 | The Regents Of The University Of California | Novel amino-dioxepane intermediates for the synthesis of new non-ionic contrast media |
NO161560C (no) * | 1980-04-17 | 1989-09-06 | Univ California | Symmetriske trijodisoftaldiamid-derivater og roentgenkontrastmidler inneholdende disse. |
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) |
EP0108638B1 (fr) * | 1982-11-08 | 1986-07-16 | NYEGAARD & CO. A/S | Agents de contraste pour rayons X |
DE3739098A1 (de) * | 1987-11-16 | 1989-05-24 | Schering Ag | Neue substituierte dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6- trijod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
-
1987
- 1987-09-17 DE DE19873731542 patent/DE3731542A1/de not_active Withdrawn
-
1988
- 1988-09-14 CA CA000577366A patent/CA1333911C/fr not_active Expired - Fee Related
- 1988-09-14 JP JP63228903A patent/JP2569144B2/ja not_active Expired - Lifetime
- 1988-09-15 ES ES88730215T patent/ES2059557T3/es not_active Expired - Lifetime
- 1988-09-15 EP EP88730215A patent/EP0308364B1/fr not_active Expired - Lifetime
- 1988-09-15 AT AT88730215T patent/ATE97126T1/de not_active IP Right Cessation
- 1988-09-15 DK DK514788A patent/DK514788A/da not_active Application Discontinuation
- 1988-09-15 DE DE88730215T patent/DE3885557D1/de not_active Expired - Lifetime
- 1988-09-16 AU AU22251/88A patent/AU616203B2/en not_active Ceased
- 1988-09-16 FI FI884271A patent/FI93208C/fi not_active IP Right Cessation
- 1988-09-16 ZA ZA886939A patent/ZA886939B/xx unknown
- 1988-09-16 KR KR1019880011967A patent/KR0139061B1/ko not_active IP Right Cessation
- 1988-09-16 NO NO884127A patent/NO175857C/no unknown
- 1988-09-16 IE IE280888A patent/IE62460B1/en not_active IP Right Cessation
- 1988-09-16 PT PT88537A patent/PT88537B/pt not_active IP Right Cessation
-
1990
- 1990-07-16 US US07/554,948 patent/US5073362A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US5073362A (en) | 1991-12-17 |
CA1333911C (fr) | 1995-01-10 |
IE882808L (en) | 1989-03-17 |
ZA886939B (en) | 1989-06-28 |
NO175857C (no) | 1994-12-21 |
AU616203B2 (en) | 1991-10-24 |
DE3885557D1 (de) | 1993-12-16 |
DK514788D0 (da) | 1988-09-15 |
DE3731542A1 (de) | 1989-03-30 |
EP0308364B1 (fr) | 1993-11-10 |
NO884127D0 (no) | 1988-09-16 |
JP2569144B2 (ja) | 1997-01-08 |
NO884127L (no) | 1989-03-20 |
AU2225188A (en) | 1989-04-13 |
FI884271A (fi) | 1989-03-18 |
JPH0196160A (ja) | 1989-04-14 |
IE62460B1 (en) | 1995-02-08 |
ATE97126T1 (de) | 1993-11-15 |
EP0308364A3 (fr) | 1991-01-30 |
PT88537B (pt) | 1992-11-30 |
PT88537A (pt) | 1988-10-01 |
ES2059557T3 (es) | 1994-11-16 |
DK514788A (da) | 1989-03-18 |
FI884271A0 (fi) | 1988-09-16 |
EP0308364A2 (fr) | 1989-03-22 |
FI93208B (fi) | 1994-11-30 |
FI93208C (fi) | 1995-03-10 |
KR0139061B1 (ko) | 1998-05-01 |
KR890005034A (ko) | 1989-05-11 |
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