DK147734B - Dicykliske trijodbenzoylforbindelser til anvendelse som roentgenkontrastm dler og roentgenkontrastmidler indeholdende disse forbindelser - Google Patents
Dicykliske trijodbenzoylforbindelser til anvendelse som roentgenkontrastm dler og roentgenkontrastmidler indeholdende disse forbindelser Download PDFInfo
- Publication number
- DK147734B DK147734B DK241876AA DK241876A DK147734B DK 147734 B DK147734 B DK 147734B DK 241876A A DK241876A A DK 241876AA DK 241876 A DK241876 A DK 241876A DK 147734 B DK147734 B DK 147734B
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- DK
- Denmark
- Prior art keywords
- water
- formula
- compounds
- amino
- product
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 28
- -1 BENZOYL COMPOUNDS Chemical class 0.000 title description 12
- 239000000243 solution Substances 0.000 claims description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 20
- 229910052740 iodine Inorganic materials 0.000 claims description 20
- 239000011630 iodine Substances 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000002872 contrast media Substances 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000009608 myelography Methods 0.000 claims description 2
- 241000700159 Rattus Species 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 231100000053 low toxicity Toxicity 0.000 claims 2
- 241000699666 Mus <mouse, genus> Species 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 claims 1
- 238000002583 angiography Methods 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 50
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000003756 stirring Methods 0.000 description 28
- 238000004809 thin layer chromatography Methods 0.000 description 27
- 239000003480 eluent Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 238000004448 titration Methods 0.000 description 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 15
- 235000019253 formic acid Nutrition 0.000 description 15
- 239000007859 condensation product Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 11
- 238000009833 condensation Methods 0.000 description 11
- 230000005494 condensation Effects 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 229960004050 aminobenzoic acid Drugs 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 238000007127 saponification reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- 229940113088 dimethylacetamide Drugs 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- SAGQGRMEBBBUCA-IXCHPVQKSA-N (2S,3S,4R,5R)-2,3,4,5-tetraacetyl-2,3,4,5,6-pentahydroxy-7-oxooctanoyl chloride Chemical compound C(C)(=O)C([C@]([C@]([C@@]([C@](C(=O)Cl)(O)C(C)=O)(O)C(C)=O)(O)C(C)=O)(O)C(C)=O)O SAGQGRMEBBBUCA-IXCHPVQKSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 239000002178 crystalline material Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 150000008040 ionic compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- FQALEPDUVKVXLD-UHFFFAOYSA-N 3-(2-aminoethylcarbamoyl)-5-nitrobenzoic acid Chemical compound NCCNC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 FQALEPDUVKVXLD-UHFFFAOYSA-N 0.000 description 3
- BFUPTGZQMFYMEN-UHFFFAOYSA-N 3-amino-5-(2-aminoethylcarbamoyl)benzoic acid Chemical compound NCCNC(=O)C1=CC(N)=CC(C(O)=O)=C1 BFUPTGZQMFYMEN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- 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 3
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 150000002497 iodine compounds Chemical class 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PYGKVALZAQNJFC-UHFFFAOYSA-N 3-amino-5-(2-aminoethylcarbamoyl)-2,4,6-triiodobenzoic acid Chemical compound NCCNC(=O)C1=C(I)C(N)=C(I)C(C(O)=O)=C1I PYGKVALZAQNJFC-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- JLIWGMLTAVBPHJ-UHFFFAOYSA-N 2-carbamoyl-3-ethylbenzoic acid Chemical compound CCC1=CC=CC(C(O)=O)=C1C(N)=O JLIWGMLTAVBPHJ-UHFFFAOYSA-N 0.000 description 1
- CAHWDGJDQYAFHM-UHFFFAOYSA-N 2-nitroisophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1[N+]([O-])=O CAHWDGJDQYAFHM-UHFFFAOYSA-N 0.000 description 1
- ODYPLCHSCOJEIZ-GMYJMXFCSA-N 3-[acetyl(methyl)amino]-n-(2-hydroxyethyl)-2,4,6-triiodo-5-[[(2s,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoyl]amino]benzamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)=C(I)C(C(=O)NCCO)=C1I ODYPLCHSCOJEIZ-GMYJMXFCSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 229920001875 Ebonite Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- SMQYOVYWPWASGU-UHFFFAOYSA-N Iocarmic acid Chemical compound OC(=O)C1=C(I)C(C(=O)NC)=C(I)C(NC(=O)CCCCC(=O)NC=2C(=C(C(=O)NC)C(I)=C(C(O)=O)C=2I)I)=C1I SMQYOVYWPWASGU-UHFFFAOYSA-N 0.000 description 1
- BAQCROVBDNBEEB-UBYUBLNFSA-N Metrizamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H]2[C@H]([C@H](O)[C@@H](CO)OC2O)O)=C1I BAQCROVBDNBEEB-UBYUBLNFSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 229950006335 ioglunide Drugs 0.000 description 1
- DQTOZIJNMYYCJE-UHFFFAOYSA-N methyl 3-carbonochloridoyl-5-nitrobenzoate Chemical compound COC(=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 DQTOZIJNMYYCJE-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229960000554 metrizamide Drugs 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 229940023486 oral product Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2411875 | 1975-06-04 | ||
| GB24118/75A GB1491129A (en) | 1975-06-04 | 1975-06-04 | Iodo-benzene derivatives and an x-ray contrast medium containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK241876A DK241876A (da) | 1976-12-05 |
| DK147734B true DK147734B (da) | 1984-11-26 |
Family
ID=10206681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK241876AA DK147734B (da) | 1975-06-04 | 1976-06-02 | Dicykliske trijodbenzoylforbindelser til anvendelse som roentgenkontrastm dler og roentgenkontrastmidler indeholdende disse forbindelser |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4062934A (Direct) |
| JP (1) | JPS6023108B2 (Direct) |
| BE (1) | BE842374A (Direct) |
| BR (1) | BR7603602A (Direct) |
| CA (1) | CA1075712A (Direct) |
| CH (1) | CH614700A5 (Direct) |
| DE (1) | DE2624153C2 (Direct) |
| DK (1) | DK147734B (Direct) |
| ES (1) | ES448475A1 (Direct) |
| FR (1) | FR2313018A1 (Direct) |
| GB (1) | GB1491129A (Direct) |
| NL (1) | NL7605980A (Direct) |
| NO (1) | NO146907C (Direct) |
| SE (1) | SE428921B (Direct) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH626873A5 (Direct) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa | |
| DE3001292A1 (de) * | 1980-01-11 | 1981-07-16 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Nichtionische 5-c-substituierte 2,4,6-trijod-isophthalsaeure-derivate |
| 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) |
| FR2511870A1 (fr) * | 1981-08-28 | 1983-03-04 | Guerbet Sa | Procede pour augmenter la tolerance des produits opacifiants, composes utilisables a cet effet et produits opacifiants les contenant |
| US4584401A (en) * | 1983-10-20 | 1986-04-22 | Biophysica Foundation | Methods and compositions involving polyhydroxylated polyiodo non-ionic contrast media |
| DE3447970C1 (en) * | 1984-02-29 | 1988-06-30 | Dr. Franz Koehler Chemie Gmbh, 6146 Alsbach, De | N-(3,5-Diacetamido-2,4,6-triiodobenzoyl)amino acid esters, process for their preparation and their use |
| US5117057A (en) * | 1985-10-21 | 1992-05-26 | Rohm And Haas Company | Insecticidal N' substituted-N-N'-disubstituted-hydrazines |
| US4985461A (en) * | 1985-10-21 | 1991-01-15 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-diacylhydrazines |
| US5354762A (en) * | 1986-07-14 | 1994-10-11 | Rohm And Haas Company | Six-membered heterocyclic derivatives of N'-substituted N,N'-diacylhydrazines |
| US5225443A (en) * | 1986-05-01 | 1993-07-06 | Rohm And Haas Company | Insecticidal N'-substituted-N'-substituted N,N'-diacylhydrazines |
| CA1281716C (en) * | 1986-05-01 | 1991-03-19 | Raymond August Murphy | Insecticidal n-substituted-n'-substituted-n,n'- diacylhydrazines |
| DE4009119A1 (de) * | 1990-03-19 | 1991-09-26 | Schering Ag | 1,4,7,10-tetraazacyclododecan-butyltriole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| 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 |
| US6013836A (en) * | 1992-02-28 | 2000-01-11 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-disubstitutedhydrazines |
| IT1264690B1 (it) * | 1993-07-08 | 1996-10-04 | Bracco Spa | Compositi oligomeri iodurati e composizioni diagnostiche contenenti gli stessi |
| US5888481A (en) * | 1995-09-29 | 1999-03-30 | Alliedsignal Inc. | Cinnamamides and their use as stabilizers |
| CN101820923A (zh) | 2007-10-12 | 2010-09-01 | 通用电气医疗集团股份有限公司 | 对比剂 |
| WO2009047317A1 (en) * | 2007-10-12 | 2009-04-16 | Ge Healthcare As | Contrast agents |
| AU2017333698B2 (en) | 2016-09-27 | 2020-12-24 | Bayer Pharma Aktiengesellschaft | Method for producing the crystalline form of modification a of calcobutrol |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178473A (en) * | 1962-03-02 | 1965-04-13 | Nyegaard & Co As | Process for the n-alkylation of acyl anilides halogen substituted in the nucleus |
| US3290366A (en) * | 1963-03-06 | 1966-12-06 | Mallinckrodt Chemical Works | 5-amino-nu-alkyl-2, 4, 6-triiodoisophthalamic acid derivatives |
| US3306927A (en) * | 1963-06-06 | 1967-02-28 | Sterling Drug Inc | N,n'-bis(3-amino-5-carboxy-2,4,6-trhodophenyl)-lower-alkanedioic acid amides and derivatives |
| US3541141A (en) * | 1967-06-29 | 1970-11-17 | Squibb & Sons Inc | Bis-triiodoisophthalamic acid compounds |
| US3732293A (en) * | 1968-03-15 | 1973-05-08 | Sterling Drug Inc | Iodinated bis(aminobenzoic acids) and esters thereof |
| CH502104A (de) * | 1968-05-02 | 1971-01-31 | Bracco Ind Chimica Spa | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
| FR2053037B1 (Direct) * | 1969-06-27 | 1974-08-09 | Nyegaard & Co As | |
| US3660469A (en) * | 1969-08-04 | 1972-05-02 | Squibb & Sons Inc | Bis-triiodoisophthalamic acid compounds |
| DD104193A5 (Direct) * | 1972-12-22 | 1974-03-05 | ||
| GB1436357A (en) * | 1973-12-07 | 1976-05-19 | Laboraoires Andre Guerbet | Tri-iodo benzene derivatives and their use as x-ray contrast |
| AR207465A1 (es) * | 1974-05-31 | 1976-10-08 | Guerbet Lab Andre | Procedimiento de preparacion de derivados de acido triiodoi2,4,6-(triiodo-2,4,6-benzoil)-amino-alcanoilaminobenzoico de acido triiodo-2,4,6-(triiodo-2,4,6-(triiodo-2,4,6-benzoil)-aminoalcanoilaminobenzoil)-amino-alcanoil-aminobenzoico y de acido triiodo-2,4,6-bis((triiodo-2,4,6-fenil)-carbamoil-metil)-aminoalcanoil-aminobenzoico |
| GB1488903A (en) * | 1974-05-31 | 1977-10-19 | Guerbet Sa | X-ray contrast media |
-
1975
- 1975-06-04 GB GB24118/75A patent/GB1491129A/en not_active Expired
-
1976
- 1976-05-17 FR FR7614807A patent/FR2313018A1/fr active Granted
- 1976-05-17 CH CH612376A patent/CH614700A5/xx not_active IP Right Cessation
- 1976-05-25 US US05/689,929 patent/US4062934A/en not_active Expired - Lifetime
- 1976-05-25 CA CA253,277A patent/CA1075712A/en not_active Expired
- 1976-05-29 DE DE2624153A patent/DE2624153C2/de not_active Expired
- 1976-05-31 BE BE167459A patent/BE842374A/xx not_active IP Right Cessation
- 1976-06-02 ES ES448475A patent/ES448475A1/es not_active Expired
- 1976-06-02 SE SE7606203A patent/SE428921B/xx unknown
- 1976-06-02 NL NL7605980A patent/NL7605980A/xx not_active Application Discontinuation
- 1976-06-02 DK DK241876AA patent/DK147734B/da not_active Application Discontinuation
- 1976-06-03 NO NO761880A patent/NO146907C/no unknown
- 1976-06-03 JP JP51065109A patent/JPS6023108B2/ja not_active Expired
- 1976-06-04 BR BR3602/76A patent/BR7603602A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1491129A (en) | 1977-11-09 |
| NO761880L (Direct) | 1976-12-07 |
| JPS6023108B2 (ja) | 1985-06-05 |
| US4062934A (en) | 1977-12-13 |
| SE428921B (sv) | 1983-08-01 |
| DK241876A (da) | 1976-12-05 |
| NO146907B (no) | 1982-09-20 |
| JPS51146431A (en) | 1976-12-16 |
| NO146907C (no) | 1982-12-29 |
| ES448475A1 (es) | 1977-07-01 |
| BE842374A (fr) | 1976-12-01 |
| FR2313018B1 (Direct) | 1979-10-05 |
| CH614700A5 (Direct) | 1979-12-14 |
| DE2624153A1 (de) | 1976-12-23 |
| CA1075712A (en) | 1980-04-15 |
| FR2313018A1 (fr) | 1976-12-31 |
| DE2624153C2 (de) | 1981-10-15 |
| SE7606203L (sv) | 1976-12-05 |
| BR7603602A (pt) | 1977-01-18 |
| NL7605980A (nl) | 1976-12-07 |
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| PHB | Application deemed withdrawn due to non-payment or other reasons |