BE520436A - - Google Patents
Info
- Publication number
- BE520436A BE520436A BE520436DA BE520436A BE 520436 A BE520436 A BE 520436A BE 520436D A BE520436D A BE 520436DA BE 520436 A BE520436 A BE 520436A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- acids
- compound
- amino
- formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000011780 sodium chloride Substances 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 11
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000003000 nontoxic Effects 0.000 claims description 8
- 231100000252 nontoxic Toxicity 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N Meglumine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 2
- 230000002588 toxic Effects 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N iodine atom Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 claims 1
- QGNWXTKXVFUTFK-UHFFFAOYSA-N 2,3-diiodobenzoic acid Chemical compound OC(=O)C1=CC=CC(I)=C1I QGNWXTKXVFUTFK-UHFFFAOYSA-N 0.000 claims 1
- 206010021118 Hypotonia Diseases 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 238000001914 filtration Methods 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000011343 solid material Substances 0.000 description 12
- 230000005591 charge neutralization Effects 0.000 description 11
- -1 isobutyryl Chemical group 0.000 description 11
- 230000001264 neutralization Effects 0.000 description 11
- 238000006386 neutralization reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 239000000908 ammonium hydroxide Substances 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- ZNVHAQRPXAQKRU-UHFFFAOYSA-N 3-Amino-5-nitrobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZNVHAQRPXAQKRU-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000006192 iodination reaction Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- PXAFGNQRBIXGLM-UHFFFAOYSA-N 3-acetamido-5-nitrobenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 PXAFGNQRBIXGLM-UHFFFAOYSA-N 0.000 description 3
- OZRLNHSWJVVZCM-UHFFFAOYSA-N OCC(=O)NC=1C=C(C=C(C(=O)O)C1)[N+](=O)[O-] Chemical compound OCC(=O)NC=1C=C(C=C(C(=O)O)C1)[N+](=O)[O-] OZRLNHSWJVVZCM-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating Effects 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 231100000636 lethal dose Toxicity 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 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 2
- GOQCZMZLABPEME-UHFFFAOYSA-N 3,5-diamino-2,4,6-triiodobenzoic acid Chemical compound NC1=C(I)C(N)=C(I)C(C(O)=O)=C1I GOQCZMZLABPEME-UHFFFAOYSA-N 0.000 description 2
- SETVYNZSWPLKAO-UHFFFAOYSA-N 3-acetamido-5-aminobenzoic acid Chemical compound CC(=O)NC1=CC(N)=CC(C(O)=O)=C1 SETVYNZSWPLKAO-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 210000003734 Kidney Anatomy 0.000 description 2
- OHIDDIWBGAVMRC-UHFFFAOYSA-N NC=1C=C(C(=O)O)C=C(C1)NC(CCC)=O Chemical compound NC=1C=C(C(=O)O)C=C(C1)NC(CCC)=O OHIDDIWBGAVMRC-UHFFFAOYSA-N 0.000 description 2
- BNPWRFOZGWPOBN-UHFFFAOYSA-N NC=1C=C(C(=O)O)C=C(C=1)NC=O Chemical compound NC=1C=C(C(=O)O)C=C(C=1)NC=O BNPWRFOZGWPOBN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 210000003932 Urinary Bladder Anatomy 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium 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
- 239000012265 solid product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LWLHVWSQNTYSSG-UHFFFAOYSA-N 2,4-diiodobenzoic acid Chemical compound OC(=O)C1=CC=C(I)C=C1I LWLHVWSQNTYSSG-UHFFFAOYSA-N 0.000 description 1
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-Iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 1
- IUTSOSUQGPWYBZ-UHFFFAOYSA-N 3,5-diacetamido-2,4-diiodobenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=C(I)C(NC(C)=O)=C1I IUTSOSUQGPWYBZ-UHFFFAOYSA-N 0.000 description 1
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
- PSYVWBBSCKPZNI-UHFFFAOYSA-N 3-(butanoylamino)-5-nitrobenzoic acid Chemical compound CCCC(=O)NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 PSYVWBBSCKPZNI-UHFFFAOYSA-N 0.000 description 1
- OKZGMVXCYARPKZ-UHFFFAOYSA-N 3-amino-5-[(2-hydroxyacetyl)amino]benzoic acid Chemical compound NC1=CC(NC(=O)CO)=CC(C(O)=O)=C1 OKZGMVXCYARPKZ-UHFFFAOYSA-N 0.000 description 1
- CUXQUGJIWQQXNC-UHFFFAOYSA-N 3-formamido-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC(NC=O)=CC([N+]([O-])=O)=C1 CUXQUGJIWQQXNC-UHFFFAOYSA-N 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P Ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- OIGRUUNSOXIHDF-UHFFFAOYSA-N C(C)(=O)NC=1C(=C(C(=C(C(=O)O)C1)I)N)I Chemical compound C(C)(=O)NC=1C(=C(C(=C(C(=O)O)C1)I)N)I OIGRUUNSOXIHDF-UHFFFAOYSA-N 0.000 description 1
- ZZKXOBMSGLCSPW-UHFFFAOYSA-N C(C)(=O)NC=1C(=C(C(=C(C(=O)O)C1)I)NC(CCC)=O)I Chemical compound C(C)(=O)NC=1C(=C(C(=C(C(=O)O)C1)I)NC(CCC)=O)I ZZKXOBMSGLCSPW-UHFFFAOYSA-N 0.000 description 1
- FQHHJOKDRNSNGF-UHFFFAOYSA-N CCC(=O)NC1=CC(=CC(=C1)C(O)=O)[N+]([O-])=O Chemical compound CCC(=O)NC1=CC(=CC(=C1)C(O)=O)[N+]([O-])=O FQHHJOKDRNSNGF-UHFFFAOYSA-N 0.000 description 1
- GOWAEULWYIDIBN-UHFFFAOYSA-N CCC(=O)NC1=CC(=CC(N)=C1)C(O)=O Chemical compound CCC(=O)NC1=CC(=CC(N)=C1)C(O)=O GOWAEULWYIDIBN-UHFFFAOYSA-N 0.000 description 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N Diatrizoic 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
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 231100000601 Intoxication Toxicity 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000020127 ayran Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 230000001665 lethal Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001304 sample melting Methods 0.000 description 1
- ZEYOIOAKZLALAP-UHFFFAOYSA-M sodium amidotrizoate Chemical compound [Na+].CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I ZEYOIOAKZLALAP-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
Classifications
-
- 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
- C07C233/45—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 carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE520436A true BE520436A (xx) |
Family
ID=156314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE520436D BE520436A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE520436A (xx) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2939881A (en) * | 1957-03-20 | 1960-06-07 | Mallinckrodt Chemical Works | Iodo-benzoic acid derivatives |
| FR2176002A1 (xx) * | 1972-03-14 | 1973-10-26 | Bofors Ab |
-
0
- BE BE520436D patent/BE520436A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2939881A (en) * | 1957-03-20 | 1960-06-07 | Mallinckrodt Chemical Works | Iodo-benzoic acid derivatives |
| FR2176002A1 (xx) * | 1972-03-14 | 1973-10-26 | Bofors Ab |
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