NO853953L - R¯ntgenkontrastmidler. - Google Patents
R¯ntgenkontrastmidler.Info
- Publication number
- NO853953L NO853953L NO853953A NO853953A NO853953L NO 853953 L NO853953 L NO 853953L NO 853953 A NO853953 A NO 853953A NO 853953 A NO853953 A NO 853953A NO 853953 L NO853953 L NO 853953L
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- formula
- sup
- triiodo
- acetamido
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 79
- 238000002360 preparation method Methods 0.000 claims description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- -1 hydroxy- Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000002872 contrast media Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229940054066 benzamide antipsychotics Drugs 0.000 claims description 7
- 150000003936 benzamides Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- SUTLSOBQYUMBQQ-UHFFFAOYSA-N IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O Chemical compound IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O SUTLSOBQYUMBQQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000006462 rearrangement reaction Methods 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- NTUGHKBFDCJJIQ-UHFFFAOYSA-N IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)NC(COC)=O Chemical compound IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)NC(COC)=O NTUGHKBFDCJJIQ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 239000003480 eluent Substances 0.000 description 61
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 53
- 229910001868 water Inorganic materials 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 37
- 229910052740 iodine Inorganic materials 0.000 description 30
- 239000011630 iodine Substances 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- KMIRYMVKGREVFO-UHFFFAOYSA-N n-(3,5-diacetamido-2,4,6-triiodophenyl)acetamide Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(NC(C)=O)=C1I KMIRYMVKGREVFO-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 230000010933 acylation Effects 0.000 description 6
- 238000005917 acylation reaction Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000026045 iodination Effects 0.000 description 4
- 238000006192 iodination reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BZOWQNVPWVLNKD-UHFFFAOYSA-N 2-methoxy-n-[2,4,6-triiodo-3,5-bis[(2-methoxyacetyl)amino]phenyl]acetamide Chemical compound COCC(=O)NC1=C(I)C(NC(=O)COC)=C(I)C(NC(=O)COC)=C1I BZOWQNVPWVLNKD-UHFFFAOYSA-N 0.000 description 3
- YEUAPBRQESJLLW-UHFFFAOYSA-N 3,5-diacetamido-2,4,6-triiodobenzamide Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(N)=O)=C1I YEUAPBRQESJLLW-UHFFFAOYSA-N 0.000 description 3
- DFWXYHZQNLIBLY-UHFFFAOYSA-N 5-nitrobenzene-1,3-diamine Chemical compound NC1=CC(N)=CC([N+]([O-])=O)=C1 DFWXYHZQNLIBLY-UHFFFAOYSA-N 0.000 description 3
- SDQJTJLJXCWVQR-UHFFFAOYSA-N 5-nitrobenzene-1,3-dicarboxamide Chemical compound NC(=O)C1=CC(C(N)=O)=CC([N+]([O-])=O)=C1 SDQJTJLJXCWVQR-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VTUDWKBFGHYLQD-UHFFFAOYSA-N N-(3-acetamido-5-amino-2,4,6-triiodophenyl)acetamide Chemical compound C(C)(=O)NC=1C(=C(N)C(=C(C=1I)NC(C)=O)I)I VTUDWKBFGHYLQD-UHFFFAOYSA-N 0.000 description 3
- CUGLQJNZJZUBHQ-UHFFFAOYSA-N N-[3-amino-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]phenyl]-2-methoxyacetamide Chemical compound IC1=C(N)C(=C(C(=C1NC(COC)=O)I)NC(COC)=O)I CUGLQJNZJZUBHQ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- FZKCAEWEKNKSNI-UHFFFAOYSA-N n-(3,5-diamino-2,4,6-triiodophenyl)acetamide Chemical compound CC(=O)NC1=C(I)C(N)=C(I)C(N)=C1I FZKCAEWEKNKSNI-UHFFFAOYSA-N 0.000 description 3
- UIHKUEVMCAOIFV-UHFFFAOYSA-N n-[3-[acetyl(2,3-dihydroxypropyl)amino]-5-amino-2,4,6-triiodophenyl]-n-(2,3-dihydroxypropyl)acetamide Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(N)=C(I)C(N(CC(O)CO)C(C)=O)=C1I UIHKUEVMCAOIFV-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 3
- HGVUWQBXZZWUGD-REOHCLBHSA-N (2s)-2-hydroxypropanoyl chloride Chemical compound C[C@H](O)C(Cl)=O HGVUWQBXZZWUGD-REOHCLBHSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- NQFCGZOGSBSBOU-UHFFFAOYSA-N 2-hydroxy-n-[2,4,6-triiodo-3,5-bis[(2-methoxyacetyl)amino]phenyl]propanamide Chemical compound COCC(=O)NC1=C(I)C(NC(=O)COC)=C(I)C(NC(=O)C(C)O)=C1I NQFCGZOGSBSBOU-UHFFFAOYSA-N 0.000 description 2
- SVZMDJJCFHWLRI-UHFFFAOYSA-N 3,5-diamino-2,4,6-triiodobenzamide Chemical compound NC(=O)C1=C(I)C(N)=C(I)C(N)=C1I SVZMDJJCFHWLRI-UHFFFAOYSA-N 0.000 description 2
- UUKWKUSGGZNXGA-UHFFFAOYSA-N 3,5-dinitrobenzamide Chemical compound NC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UUKWKUSGGZNXGA-UHFFFAOYSA-N 0.000 description 2
- ZCRNIIJXDRYWDU-UHFFFAOYSA-N 3-(methoxycarbonyl)-5-nitrobenzoic acid Chemical compound COC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZCRNIIJXDRYWDU-UHFFFAOYSA-N 0.000 description 2
- IBUKQAXCRVJPHF-UHFFFAOYSA-N 5-acetamido-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound CC(=O)NC1=C(I)C(C(N)=O)=C(I)C(C(N)=O)=C1I IBUKQAXCRVJPHF-UHFFFAOYSA-N 0.000 description 2
- GBUPGCQLNMNZPA-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound NC(=O)C1=C(I)C(N)=C(I)C(C(N)=O)=C1I GBUPGCQLNMNZPA-UHFFFAOYSA-N 0.000 description 2
- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- RAIVLFPWSORAOZ-UHFFFAOYSA-N [1-[3-(2-acetyloxypropanoylamino)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]anilino]-1-oxopropan-2-yl] acetate Chemical compound COCC(=O)NC1=C(I)C(NC(=O)C(C)OC(C)=O)=C(I)C(NC(=O)C(C)OC(C)=O)=C1I RAIVLFPWSORAOZ-UHFFFAOYSA-N 0.000 description 2
- MBVDTIMAKWGWBU-UHFFFAOYSA-N [1-oxo-1-[2,4,6-triiodo-3,5-bis[(2-methoxyacetyl)amino]anilino]propan-2-yl] acetate Chemical compound COCC(=O)NC1=C(I)C(NC(=O)COC)=C(I)C(NC(=O)C(C)OC(C)=O)=C1I MBVDTIMAKWGWBU-UHFFFAOYSA-N 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002242 deionisation method Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002496 iodine Chemical class 0.000 description 2
- 150000008424 iodobenzenes Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- POGCCFLNFPIIGW-UHFFFAOYSA-N methyl 3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 POGCCFLNFPIIGW-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- 238000005406 washing Methods 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
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- PSYQXTDKRKLJQC-UHFFFAOYSA-N 1-chloropropane-1,3-diol Chemical compound OCCC(O)Cl PSYQXTDKRKLJQC-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- FHNBMJLRCHDUQX-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]-n-(2,3-dihydroxypropyl)-n-(2,4,6-triiodo-3-methylphenyl)acetamide;hydrochloride Chemical compound Cl.CC1=C(I)C=C(I)C(N(CC(O)CO)C(=O)CN(CCO)CCO)=C1I FHNBMJLRCHDUQX-UHFFFAOYSA-N 0.000 description 1
- HGVUWQBXZZWUGD-UHFFFAOYSA-N 2-hydroxypropanoyl chloride Chemical compound CC(O)C(Cl)=O HGVUWQBXZZWUGD-UHFFFAOYSA-N 0.000 description 1
- YEOYYWCXWUDVCX-UHFFFAOYSA-N 2-iodobenzamide Chemical class NC(=O)C1=CC=CC=C1I YEOYYWCXWUDVCX-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MPBZUKLDHPOCLS-UHFFFAOYSA-N 3,5-dinitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 MPBZUKLDHPOCLS-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UXPIWHPHEGRYLB-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxamide Chemical compound NC(=O)C1=CC(N)=CC(C(N)=O)=C1 UXPIWHPHEGRYLB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-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
- 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
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- OEZZSLPHYRNCQP-UHFFFAOYSA-N N-[3,5-bis[acetyl(2,3-dihydroxypropyl)amino]-2,4,6-triiodophenyl]-2-hydroxypropanamide Chemical compound IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)NC(C(C)O)=O OEZZSLPHYRNCQP-UHFFFAOYSA-N 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Chemical class CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HXLVCCRPDYIRRX-UHFFFAOYSA-N iodoamine Chemical class IN HXLVCCRPDYIRRX-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229960000554 metrizamide Drugs 0.000 description 1
- YDCVMRKHEGIECM-UHFFFAOYSA-N n,n-dimethylacetamide;1,4-dioxane Chemical compound CN(C)C(C)=O.C1COCCO1 YDCVMRKHEGIECM-UHFFFAOYSA-N 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002243 precursor Substances 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002330 subarachnoid space Anatomy 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- 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
- 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
- C07C233/30—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 doubly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Led Devices (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8415494A FR2571367B1 (fr) | 1984-10-09 | 1984-10-09 | Composes triaminobenzeniques iodes et/ou bromes, leur procede de preparation et leur application dans des produits de contraste |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO853953L true NO853953L (no) | 1986-04-10 |
Family
ID=9308495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO853953A NO853953L (no) | 1984-10-09 | 1985-10-07 | R¯ntgenkontrastmidler. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0177414A1 (it) |
| JP (1) | JPS6191161A (it) |
| KR (1) | KR860003202A (it) |
| CN (1) | CN85107303A (it) |
| AU (1) | AU4720085A (it) |
| DD (1) | DD238970A5 (it) |
| DK (1) | DK459585A (it) |
| ES (1) | ES8604858A1 (it) |
| FI (1) | FI853854L (it) |
| FR (1) | FR2571367B1 (it) |
| GR (1) | GR852421B (it) |
| HU (1) | HUT39718A (it) |
| IL (1) | IL76354A0 (it) |
| NO (1) | NO853953L (it) |
| ZA (1) | ZA857277B (it) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863714A (en) * | 1987-02-05 | 1989-09-05 | Cook Imaging Corporation | Sterilization of compositions of limited stability |
| ES2021944A6 (es) * | 1990-02-14 | 1991-11-16 | Rhone Poulenc Farma Sa | Procedimiento para preparar nuevos derivados de 1,3,5,-triamino-2,4,6-triyodobenceno. |
| ES2341296T3 (es) | 2001-12-20 | 2010-06-17 | Bone Support Ab | Un nuevo sustituto mineral de hueso. |
| CN101190888B (zh) * | 2006-11-24 | 2011-01-19 | 浙江尖峰海洲制药有限公司 | 5-乙酰氨基-2,4,6-三碘-1,3-苯二甲酰胺的制备方法 |
| WO2009106552A2 (en) * | 2008-02-27 | 2009-09-03 | Ge Healthcare As | Contrast agents |
| EP2245004A2 (en) * | 2008-02-27 | 2010-11-03 | GE Healthcare AS | Contrast agents |
| WO2010060941A2 (en) * | 2008-11-27 | 2010-06-03 | Ge Healthcare As | Contrast agents |
| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2313917A1 (fr) * | 1975-06-10 | 1977-01-07 | Cortial | Nouveaux agents de contraste radiographique constitues par les derives de l'acide n-acetyl n-(diamino-3,5 triiodo-2,4,6 phenyl) b-aminopropionique, leurs intermediaires de synthese et leur preparation |
-
1984
- 1984-10-09 FR FR8415494A patent/FR2571367B1/fr not_active Expired
-
1985
- 1985-09-10 AU AU47200/85A patent/AU4720085A/en not_active Abandoned
- 1985-09-10 IL IL76354A patent/IL76354A0/xx unknown
- 1985-09-19 KR KR1019850006871A patent/KR860003202A/ko not_active IP Right Cessation
- 1985-09-23 ZA ZA857277A patent/ZA857277B/xx unknown
- 1985-09-25 EP EP85401878A patent/EP0177414A1/fr not_active Withdrawn
- 1985-09-30 ES ES547411A patent/ES8604858A1/es not_active Expired
- 1985-10-04 FI FI853854A patent/FI853854L/fi not_active Application Discontinuation
- 1985-10-07 CN CN198585107303A patent/CN85107303A/zh active Pending
- 1985-10-07 GR GR852421A patent/GR852421B/el unknown
- 1985-10-07 NO NO853953A patent/NO853953L/no unknown
- 1985-10-08 JP JP60224613A patent/JPS6191161A/ja active Pending
- 1985-10-08 HU HU853909A patent/HUT39718A/hu unknown
- 1985-10-08 DK DK459585A patent/DK459585A/da not_active Application Discontinuation
- 1985-10-09 DD DD85281566A patent/DD238970A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2571367A1 (fr) | 1986-04-11 |
| DK459585D0 (da) | 1985-10-08 |
| KR860003202A (ko) | 1986-05-21 |
| FI853854L (fi) | 1986-04-10 |
| ZA857277B (en) | 1986-05-28 |
| DK459585A (da) | 1986-04-10 |
| ES547411A0 (es) | 1986-03-16 |
| HUT39718A (en) | 1986-10-29 |
| CN85107303A (zh) | 1986-03-10 |
| GR852421B (it) | 1986-02-10 |
| IL76354A0 (en) | 1986-01-31 |
| EP0177414A1 (fr) | 1986-04-09 |
| FR2571367B1 (fr) | 1987-02-13 |
| JPS6191161A (ja) | 1986-05-09 |
| AU4720085A (en) | 1986-04-17 |
| DD238970A5 (de) | 1986-09-10 |
| ES8604858A1 (es) | 1986-03-16 |
| FI853854A0 (fi) | 1985-10-04 |
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