DE2926428A1 - Trijodierte 5-aminoisophthalsaeure- derivate - Google Patents
Trijodierte 5-aminoisophthalsaeure- derivateInfo
- Publication number
- DE2926428A1 DE2926428A1 DE19792926428 DE2926428A DE2926428A1 DE 2926428 A1 DE2926428 A1 DE 2926428A1 DE 19792926428 DE19792926428 DE 19792926428 DE 2926428 A DE2926428 A DE 2926428A DE 2926428 A1 DE2926428 A1 DE 2926428A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- acid
- mmol
- methyl
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000002872 contrast media Substances 0.000 title claims abstract description 29
- 150000001408 amides Chemical class 0.000 title 1
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003748 selenium group Chemical group *[Se]* 0.000 claims abstract description 5
- -1 2,3-dihydroxypropyl-N-methyl-carbamoyl Chemical group 0.000 claims description 53
- 229940039231 contrast media Drugs 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical class NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- FBFVJAHHUXHNGC-UHFFFAOYSA-N 5-[[2-[2-[2-[3,5-bis[2,3-dihydroxypropyl(methyl)carbamoyl]-2,4,6-triiodoanilino]-2-oxoethyl]sulfanylethylsulfanyl]acetyl]amino]-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1-N,3-N-dimethylbenzene-1,3-dicarboxamide Chemical compound OC(CN(C(=O)C=1C(=C(NC(CSCCSCC(=O)NC2=C(C(=C(C(=C2I)C(N(C)CC(CO)O)=O)I)C(N(C)CC(CO)O)=O)I)=O)C(=C(C=1I)C(N(C)CC(CO)O)=O)I)I)C)CO FBFVJAHHUXHNGC-UHFFFAOYSA-N 0.000 claims 1
- WJXXCTSBMNYHHS-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarbonyl chloride Chemical class NC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 WJXXCTSBMNYHHS-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 239000005864 Sulphur Substances 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 230000003073 embolic effect Effects 0.000 abstract 1
- 230000029142 excretion Effects 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 238000000354 decomposition reaction Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001450 anions Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000001226 reprecipitation Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 210000001165 lymph node Anatomy 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 210000004324 lymphatic system Anatomy 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- 238000002583 angiography Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000003204 osmotic effect Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003490 Thiodipropionic acid Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 210000002751 lymph Anatomy 0.000 description 3
- 229960000554 metrizamide Drugs 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 235000019303 thiodipropionic acid Nutrition 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- 238000007487 urography Methods 0.000 description 3
- JEUVUETXSDIHIE-UHFFFAOYSA-N 2,4,6-triiodo-5-(2-methyl-3,5-dioxothiomorpholin-4-yl)benzene-1,3-dicarbonyl chloride Chemical compound O=C1C(C)SCC(=O)N1C1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I JEUVUETXSDIHIE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000005189 Embolism Diseases 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000010102 embolization Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 230000001926 lymphatic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 210000001635 urinary tract Anatomy 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- INPWHIBRMNBPDX-UHFFFAOYSA-N 2,3,5,6-tetraiodoterephthalic acid Chemical class OC(=O)C1=C(I)C(I)=C(C(O)=O)C(I)=C1I INPWHIBRMNBPDX-UHFFFAOYSA-N 0.000 description 1
- TZEBLZRSPJJCOS-UHFFFAOYSA-N 2,4,6-triiodo-5-(methylamino)benzene-1,3-dicarbonyl chloride Chemical compound CNC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I TZEBLZRSPJJCOS-UHFFFAOYSA-N 0.000 description 1
- FQAXLTARZOJBPJ-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=C(I)C=C(I)C(C(Cl)=O)=C1I FQAXLTARZOJBPJ-UHFFFAOYSA-N 0.000 description 1
- JUVHQPRUPDZMOJ-UHFFFAOYSA-N 2-(2-chloro-2-oxoethyl)sulfanylpropanoyl chloride Chemical compound ClC(=O)C(C)SCC(Cl)=O JUVHQPRUPDZMOJ-UHFFFAOYSA-N 0.000 description 1
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 1
- LKTLLQVZWBEGQH-UHFFFAOYSA-N 2-[(2-chloro-2-oxoethyl)sulfanylmethylsulfanyl]acetyl chloride Chemical compound ClC(=O)CSCSCC(Cl)=O LKTLLQVZWBEGQH-UHFFFAOYSA-N 0.000 description 1
- ALVKRCAHYQOHKD-UHFFFAOYSA-N 2-[2-(2-chloro-2-oxoethyl)sulfanylethylsulfanyl]acetyl chloride Chemical compound ClC(=O)CSCCSCC(Cl)=O ALVKRCAHYQOHKD-UHFFFAOYSA-N 0.000 description 1
- CCQMORVULNZXIA-UHFFFAOYSA-N 2-[2-(carboxymethylsulfanyl)ethylsulfanyl]acetic acid Chemical compound OC(=O)CSCCSCC(O)=O CCQMORVULNZXIA-UHFFFAOYSA-N 0.000 description 1
- ZOVYZYRQVHMFMP-UHFFFAOYSA-N 2-[4-(2-chloro-2-oxoethyl)sulfanylbutylsulfanyl]acetyl chloride Chemical compound ClC(=O)CSCCCCSCC(Cl)=O ZOVYZYRQVHMFMP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LCPDKKGCRNTHHR-UHFFFAOYSA-N 3-(3-chloro-3-oxopropyl)selanylpropanoyl chloride Chemical compound ClC(=O)CC[Se]CCC(Cl)=O LCPDKKGCRNTHHR-UHFFFAOYSA-N 0.000 description 1
- VURCJRMYKFUQSW-UHFFFAOYSA-N 3-[(3-chloro-3-oxopropyl)disulfanyl]propanoyl chloride Chemical compound ClC(=O)CCSSCCC(Cl)=O VURCJRMYKFUQSW-UHFFFAOYSA-N 0.000 description 1
- UPZCIAVCFJRASZ-UHFFFAOYSA-N 3-[(3-chloro-3-oxopropyl)sulfanylmethylsulfanyl]propanoyl chloride Chemical compound ClC(=O)CCSCSCCC(Cl)=O UPZCIAVCFJRASZ-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- BUXKMDZAXXJMPA-UHFFFAOYSA-N 5-[[2-[4-[2-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-2-oxoethyl]sulfanylbutylsulfanyl]acetyl]amino]-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C=1C(=C(NC(CSCCCCSCC(=O)NC2=C(C(=C(C(=C2I)C(=O)Cl)I)C(=O)Cl)I)=O)C(=C(C=1I)C(=O)Cl)I)I BUXKMDZAXXJMPA-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- SHWNNYZBHZIQQV-UHFFFAOYSA-J EDTA monocalcium diisodium salt Chemical compound [Na+].[Na+].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O SHWNNYZBHZIQQV-UHFFFAOYSA-J 0.000 description 1
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- CDDRKQSSJLYBCQ-UHFFFAOYSA-N NC1=C(C(Cl)=O)C=CC=C1C(Cl)=O Chemical compound NC1=C(C(Cl)=O)C=CC=C1C(Cl)=O CDDRKQSSJLYBCQ-UHFFFAOYSA-N 0.000 description 1
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- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- VVDGWALACJEJKG-UHFFFAOYSA-N iodamide Chemical compound CC(=O)NCC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I VVDGWALACJEJKG-UHFFFAOYSA-N 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 238000009608 myelography Methods 0.000 description 1
- JNJACCPWFNVVOX-UHFFFAOYSA-N n-[bis(dimethylamino)phosphoryl]-n-methylmethanamine;n,n-dimethylacetamide Chemical compound CN(C)C(C)=O.CN(C)P(=O)(N(C)C)N(C)C JNJACCPWFNVVOX-UHFFFAOYSA-N 0.000 description 1
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 1
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- 229940037001 sodium edetate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
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)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792926428 DE2926428A1 (de) | 1979-06-28 | 1979-06-28 | Trijodierte 5-aminoisophthalsaeure- derivate |
| SU802934454A SU969156A3 (ru) | 1979-06-28 | 1980-06-23 | Способ получени трийодированных производных 5-аминоизофталевой кислоты |
| DK273280A DK273280A (da) | 1979-06-28 | 1980-06-25 | Trijoderede 5-aminoisophthalsyrederivater |
| YU01676/80A YU167680A (en) | 1979-06-28 | 1980-06-26 | Process for obtaining triiodated 5-amino-isophthalic acid derivatives |
| DD80222179A DD151748A5 (de) | 1979-06-28 | 1980-06-26 | Verfahren zur herstellung von trijodierten 5-aminoisophtalsaeure-derivaten |
| GR62306A GR69655B (enrdf_load_stackoverflow) | 1979-06-28 | 1980-06-26 | |
| NO801916A NO151005C (no) | 1979-06-28 | 1980-06-26 | Trijoderte 5-aminoisofthalsyrederivater og anvendelse av disse som skyggegivende komponent i roentgenkontrastmidler |
| PT71462A PT71462A (en) | 1979-06-28 | 1980-06-26 | Trijodierte 5-aminoisophtalsaure-derivate |
| CA000355018A CA1160243A (en) | 1979-06-28 | 1980-06-27 | Tri-iodised 5-aminoisophthalic acid derivatives |
| ES492891A ES492891A0 (es) | 1979-06-28 | 1980-06-27 | Procedimiento para la preparacion de derivados triyodados deacido 5-amino- isoftalico |
| FI802054A FI802054A7 (fi) | 1979-06-28 | 1980-06-27 | Trijodattuja 5- aminoisoftaalihappojohdannaisia. |
| DE8080730044T DE3063966D1 (en) | 1979-06-28 | 1980-06-27 | Dimers of tri-iodated isophthalic acid diamides, their preparation, x-ray contrast agent containing them, and dimer of tri-iodated isophthalic acid chloride |
| IL60416A IL60416A (en) | 1979-06-28 | 1980-06-27 | Tri-iodised 5-aminoisophthalic acid derivatives,process for their preparation and x-ray contrast preparations comprising them |
| US06/163,895 US4367216A (en) | 1979-06-28 | 1980-06-27 | Triiodinated 5-aminoisophthalic acid derivatives |
| AT80730044T ATE3975T1 (de) | 1979-06-28 | 1980-06-27 | Dimere trijodierte isophthalsaeurediamide, deren herstellung, diese enthaltendes roentgenkontrastmittel, und dimere trijodierte isophthalsaeure-chloride. |
| JP8667780A JPS5618954A (en) | 1979-06-28 | 1980-06-27 | Iodinated 55aminoisophthalic acid derivative* its manufacture and x ray contrast agent containing it |
| EP80730044A EP0022056B1 (de) | 1979-06-28 | 1980-06-27 | Dimere trijodierte Isophthalsäurediamide, deren Herstellung, diese enthaltendes Röntgenkontrastmittel, und dimere trijodierte Isophthalsäure-chloride |
| ZA00803878A ZA803878B (en) | 1979-06-28 | 1980-06-27 | Tri-iodised 5-aminoisophthalic acid derivatives |
| IE1336/80A IE49948B1 (en) | 1979-06-28 | 1980-06-27 | Tri-iodised 5-aminoisophthalic acid derivatives |
| PH24209A PH15404A (en) | 1979-06-28 | 1980-06-27 | Triiodinated 5-aminoisophthalic acid derivatives |
| AU59769/80A AU532175B2 (en) | 1979-06-28 | 1980-06-30 | Amides of tetracarboxylic acid tetrahalide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792926428 DE2926428A1 (de) | 1979-06-28 | 1979-06-28 | Trijodierte 5-aminoisophthalsaeure- derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2926428A1 true DE2926428A1 (de) | 1981-01-08 |
Family
ID=6074568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792926428 Withdrawn DE2926428A1 (de) | 1979-06-28 | 1979-06-28 | Trijodierte 5-aminoisophthalsaeure- derivate |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5618954A (enrdf_load_stackoverflow) |
| DE (1) | DE2926428A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA803878B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19731591A1 (de) * | 1997-07-17 | 1999-01-21 | Schering Ag | Pharmazeutische Mittel enthaltend perfluoralkylgruppenhaltige Trijodaromaten und ihre Verwendung in der Tumortherapie und interventionellen Radiologie |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5114703A (en) * | 1989-05-30 | 1992-05-19 | Alliance Pharmaceutical Corp. | Percutaneous lymphography using particulate fluorocarbon emulsions |
| JP2742337B2 (ja) * | 1991-05-29 | 1998-04-22 | 富士写真フイルム株式会社 | 電子写真製版装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI760068A7 (enrdf_load_stackoverflow) * | 1975-02-03 | 1976-08-04 | Schering Ag |
-
1979
- 1979-06-28 DE DE19792926428 patent/DE2926428A1/de not_active Withdrawn
-
1980
- 1980-06-27 JP JP8667780A patent/JPS5618954A/ja active Granted
- 1980-06-27 ZA ZA00803878A patent/ZA803878B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19731591A1 (de) * | 1997-07-17 | 1999-01-21 | Schering Ag | Pharmazeutische Mittel enthaltend perfluoralkylgruppenhaltige Trijodaromaten und ihre Verwendung in der Tumortherapie und interventionellen Radiologie |
| DE19731591C2 (de) * | 1997-07-17 | 1999-09-16 | Schering Ag | Pharmazeutische Mittel enthaltend perfluoralkylgruppenhaltige Trijodaromaten und ihre Verwendung in der Tumortherapie und interventionellen Radiologie |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH029584B2 (enrdf_load_stackoverflow) | 1990-03-02 |
| ZA803878B (en) | 1981-06-24 |
| JPS5618954A (en) | 1981-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |