CS213388B2 - Method of making the derivatives of 2,4,6-triiodbenzonitrile - Google Patents
Method of making the derivatives of 2,4,6-triiodbenzonitrile Download PDFInfo
- Publication number
- CS213388B2 CS213388B2 CS794930A CS493079A CS213388B2 CS 213388 B2 CS213388 B2 CS 213388B2 CS 794930 A CS794930 A CS 794930A CS 493079 A CS493079 A CS 493079A CS 213388 B2 CS213388 B2 CS 213388B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- water
- solution
- acid
- group
- cooh
- Prior art date
Links
- UGOFDMIBHFPSJF-UHFFFAOYSA-N 2,4,6-triiodobenzonitrile Chemical class IC1=CC(I)=C(C#N)C(I)=C1 UGOFDMIBHFPSJF-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000002872 contrast media Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract description 2
- GNOYQZRQXNVAKE-UHFFFAOYSA-N 2,4,6-triiodoaniline Chemical class NC1=C(I)C=C(I)C=C1I GNOYQZRQXNVAKE-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- 239000000243 solution Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 229910001868 water Inorganic materials 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- -1 acyl radical Chemical class 0.000 description 13
- 239000002253 acid Substances 0.000 description 11
- 235000010288 sodium nitrite Nutrition 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229940039231 contrast media Drugs 0.000 description 5
- 150000001879 copper Chemical class 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- DAMMTPUDAGMEIL-UHFFFAOYSA-N 5-cyano-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=C(I)C(C#N)=C(I)C(C(O)=O)=C1I DAMMTPUDAGMEIL-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JDDAFHUEOVUDFJ-UHFFFAOYSA-N 2-iodobenzonitrile Chemical class IC1=CC=CC=C1C#N JDDAFHUEOVUDFJ-UHFFFAOYSA-N 0.000 description 1
- KDEVSMFUAKNOJC-UHFFFAOYSA-N 3-acetamido-5-(aminomethyl)-2,4,6-triiodobenzoic acid Chemical compound CC(=O)NC1=C(I)C(CN)=C(I)C(C(O)=O)=C1I KDEVSMFUAKNOJC-UHFFFAOYSA-N 0.000 description 1
- AKXKBAWZIVNNJR-UHFFFAOYSA-N 3-amino-2,4,6-triiodo-5-(methylcarbamoyl)benzoic acid Chemical compound CNC(=O)C1=C(I)C(N)=C(I)C(C(O)=O)=C1I AKXKBAWZIVNNJR-UHFFFAOYSA-N 0.000 description 1
- BWKWJRRDHNBJTI-UHFFFAOYSA-N 3-amino-5-carbamoyl-2,4,6-triiodobenzoic acid Chemical compound NC(=O)C1=C(I)C(N)=C(I)C(C(O)=O)=C1I BWKWJRRDHNBJTI-UHFFFAOYSA-N 0.000 description 1
- JKVAHSYHFPASPQ-UHFFFAOYSA-N 3-cyano-2,4,6-triiodobenzoic acid Chemical compound OC(=O)C1=C(I)C=C(I)C(C#N)=C1I JKVAHSYHFPASPQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 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
- 229960004901 iodamide Drugs 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000009608 myelography Methods 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000007487 urography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782831496 DE2831496A1 (de) | 1978-07-14 | 1978-07-14 | Neue roentgenkontrastmittel |
| DE19792902456 DE2902456A1 (de) | 1979-01-19 | 1979-01-19 | Neue roentgenkontrastmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS213388B2 true CS213388B2 (en) | 1982-04-09 |
Family
ID=25775051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS794930A CS213388B2 (en) | 1978-07-14 | 1979-07-13 | Method of making the derivatives of 2,4,6-triiodbenzonitrile |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4269819A (no) |
| AT (1) | AT361906B (no) |
| CH (1) | CH641766A5 (no) |
| CS (1) | CS213388B2 (no) |
| FR (1) | FR2430937A1 (no) |
| GB (1) | GB2027696B (no) |
| IT (1) | IT1165150B (no) |
| LU (1) | LU81492A1 (no) |
| NL (1) | NL7905354A (no) |
| NO (1) | NO150680C (no) |
| SE (1) | SE446630B (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5344638A (en) * | 1993-03-11 | 1994-09-06 | Sterling Winthrop Inc. | Compositions of iodobenzoic acid derivatives for visualization of the gastrointestinal tract |
| US5312616A (en) * | 1993-03-11 | 1994-05-17 | Sterling Winthrop Inc. | Compositions of iodobenzoic acid derivatives in film-forming materials for visualization of the gastrointestinal tract |
| US7166740B2 (en) * | 2003-07-14 | 2007-01-23 | Schering Ag | Process for the production of triiodotrimesic acid |
| US7083516B2 (en) * | 2003-07-14 | 2006-08-01 | Schering Ag | Process for the production of triiodotrimesic acid |
| JP2005037464A (ja) * | 2003-07-16 | 2005-02-10 | Matsushita Electric Ind Co Ltd | 光導波路とその製造方法 |
| WO2012136813A2 (en) | 2011-04-07 | 2012-10-11 | Universitetet I Oslo | Agents for medical radar diagnosis |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1467994A1 (de) * | 1965-03-31 | 1969-02-13 | Lentia Gmbh | Roentgenkontrastmittel |
-
1979
- 1979-07-09 NL NL7905354A patent/NL7905354A/nl not_active Application Discontinuation
- 1979-07-12 LU LU81492A patent/LU81492A1/de unknown
- 1979-07-12 FR FR7918103A patent/FR2430937A1/fr active Granted
- 1979-07-12 IT IT24311/79A patent/IT1165150B/it active
- 1979-07-12 AT AT487379A patent/AT361906B/de not_active IP Right Cessation
- 1979-07-12 US US06/057,243 patent/US4269819A/en not_active Expired - Lifetime
- 1979-07-13 CH CH658179A patent/CH641766A5/de not_active IP Right Cessation
- 1979-07-13 NO NO792341A patent/NO150680C/no unknown
- 1979-07-13 CS CS794930A patent/CS213388B2/cs unknown
- 1979-07-13 GB GB7924516A patent/GB2027696B/en not_active Expired
- 1979-07-13 SE SE7906103A patent/SE446630B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2430937B1 (no) | 1981-11-13 |
| IT7924311A0 (it) | 1979-07-12 |
| SE446630B (sv) | 1986-09-29 |
| US4269819A (en) | 1981-05-26 |
| NO792341L (no) | 1980-01-15 |
| NO150680B (no) | 1984-08-20 |
| ATA487379A (de) | 1980-09-15 |
| GB2027696A (en) | 1980-02-27 |
| AT361906B (de) | 1981-04-10 |
| IT1165150B (it) | 1987-04-22 |
| GB2027696B (en) | 1982-11-24 |
| NL7905354A (nl) | 1980-01-16 |
| CH641766A5 (de) | 1984-03-15 |
| FR2430937A1 (fr) | 1980-02-08 |
| SE7906103L (sv) | 1980-01-15 |
| LU81492A1 (de) | 1979-10-31 |
| NO150680C (no) | 1984-11-28 |
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