FI67078C - Nya roentgenkontrastmedel och foerfarande foer deras framstaellning - Google Patents
Nya roentgenkontrastmedel och foerfarande foer deras framstaellning Download PDFInfo
- Publication number
- FI67078C FI67078C FI771092A FI771092A FI67078C FI 67078 C FI67078 C FI 67078C FI 771092 A FI771092 A FI 771092A FI 771092 A FI771092 A FI 771092A FI 67078 C FI67078 C FI 67078C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- acid
- hydrogen
- triiodo
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 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 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002872 contrast media Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 150000008424 iodobenzenes Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 20
- 229910052740 iodine Inorganic materials 0.000 description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 239000011630 iodine Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000004448 titration Methods 0.000 description 12
- 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 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- -1 alkali metal salts Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- 239000007864 aqueous solution Substances 0.000 description 2
- PPVMXDNLHFGYJU-UHFFFAOYSA-N azane;ethyl acetate;propan-2-ol Chemical compound N.CC(C)O.CCOC(C)=O PPVMXDNLHFGYJU-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- MQIYRIJWGVZFBK-UHFFFAOYSA-N benzene;butan-2-one;formic acid Chemical compound OC=O.CCC(C)=O.C1=CC=CC=C1 MQIYRIJWGVZFBK-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HEZIBWFSRUEOAR-UHFFFAOYSA-N 3-[(2-aminoacetyl)amino]-2,4,6-triiodo-5-(methylcarbamoyl)benzoic acid Chemical compound CNC(=O)C1=C(I)C(NC(=O)CN)=C(I)C(C(O)=O)=C1I HEZIBWFSRUEOAR-UHFFFAOYSA-N 0.000 description 1
- TWHXKTBRMLBBKZ-UHFFFAOYSA-N 3-[(2-aminoacetyl)amino]-2,4,6-triiodobenzoic acid Chemical compound NCC(=O)NC1=C(I)C=C(I)C(C(O)=O)=C1I TWHXKTBRMLBBKZ-UHFFFAOYSA-N 0.000 description 1
- PUYZMAVZWDONSU-UHFFFAOYSA-N 3-acetamido-5-[(2-aminoacetyl)amino]-2,4,6-triiodobenzoic acid Chemical compound CC(=O)NC1=C(I)C(NC(=O)CN)=C(I)C(C(O)=O)=C1I PUYZMAVZWDONSU-UHFFFAOYSA-N 0.000 description 1
- HYGGDKPPAGGKNN-UHFFFAOYSA-N 5-acetamido-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound CC(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I HYGGDKPPAGGKNN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- PBWKJYMBTSONLV-UHFFFAOYSA-N CNC(=O)C(C(C(CI)N)I)C(C(=O)NC1=CC=CC=C1C(=O)O)I Chemical compound CNC(=O)C(C(C(CI)N)I)C(C(=O)NC1=CC=CC=C1C(=O)O)I PBWKJYMBTSONLV-UHFFFAOYSA-N 0.000 description 1
- 101150047265 COR2 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UXIGWFXRQKWHHA-UHFFFAOYSA-N Iotalamic acid Chemical compound CNC(=O)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I UXIGWFXRQKWHHA-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 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
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 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
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960005223 diatrizoic acid Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000007790 scraping Methods 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
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect 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
- C07C233/12—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 halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14343/76A GB1539791A (en) | 1976-04-08 | 1976-04-08 | X-ray contrast media |
| GB1434376 | 1976-04-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771092A7 FI771092A7 (cs) | 1977-10-09 |
| FI67078B FI67078B (fi) | 1984-09-28 |
| FI67078C true FI67078C (fi) | 1985-01-10 |
Family
ID=10039482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771092A FI67078C (fi) | 1976-04-08 | 1977-04-06 | Nya roentgenkontrastmedel och foerfarande foer deras framstaellning |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4107286A (cs) |
| JP (1) | JPS6023669B2 (cs) |
| AR (1) | AR215624A1 (cs) |
| AT (1) | AT348989B (cs) |
| AU (1) | AU505744B2 (cs) |
| BE (1) | BE853333A (cs) |
| BR (1) | BR7702215A (cs) |
| CA (1) | CA1105481A (cs) |
| CH (1) | CH620422A5 (cs) |
| CS (1) | CS204000B2 (cs) |
| DD (1) | DD129979A5 (cs) |
| DE (1) | DE2715382A1 (cs) |
| DK (1) | DK147917B (cs) |
| EG (1) | EG12702A (cs) |
| ES (1) | ES457405A1 (cs) |
| FI (1) | FI67078C (cs) |
| FR (1) | FR2347339A1 (cs) |
| GB (1) | GB1539791A (cs) |
| GR (1) | GR63091B (cs) |
| HU (1) | HU173333B (cs) |
| IL (1) | IL51774A (cs) |
| MX (1) | MX4238E (cs) |
| NL (1) | NL7703675A (cs) |
| NO (1) | NO146862C (cs) |
| SE (1) | SE436872B (cs) |
| SU (1) | SU793387A3 (cs) |
| YU (1) | YU85377A (cs) |
| ZA (1) | ZA771945B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2427326A2 (fr) * | 1978-05-31 | 1979-12-28 | Guerbet Sa | Nouveaux derives ioniques polyiodes du benzene, utilisables comme produits opacifiants pour la radiographie |
| DE2909439A1 (de) * | 1979-03-08 | 1980-09-18 | Schering Ag | Neue nichtionische roentgenkontrastmittel |
| DE3001293A1 (de) * | 1980-01-11 | 1981-07-16 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Ionische 5-c-substitiuerte 2,4,6-trijod-isophtalsaeure-derivete |
| FR2511870A1 (fr) * | 1981-08-28 | 1983-03-04 | Guerbet Sa | Procede pour augmenter la tolerance des produits opacifiants, composes utilisables a cet effet et produits opacifiants les contenant |
| JPH04350468A (ja) * | 1991-04-23 | 1992-12-04 | Asahi Breweries Ltd | 液体の冷却装置 |
| US10918742B2 (en) | 2016-03-25 | 2021-02-16 | Nanoprobes, Inc. | Iodine-based particles |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787669A (fr) * | 1971-08-17 | 1973-02-19 | Schering Ag | Anilides d'acide n-methyl-dicarboxylique triiodes, et leur procede de preparation |
| CH576256A5 (cs) * | 1973-07-17 | 1976-06-15 | Bracco Ind Chimica Spa | |
| CH583562A5 (cs) * | 1973-07-17 | 1977-01-14 | Bracco Ind Chimica Spa | |
| AR207465A1 (es) * | 1974-05-31 | 1976-10-08 | Guerbet Lab Andre | Procedimiento de preparacion de derivados de acido triiodoi2,4,6-(triiodo-2,4,6-benzoil)-amino-alcanoilaminobenzoico de acido triiodo-2,4,6-(triiodo-2,4,6-(triiodo-2,4,6-benzoil)-aminoalcanoilaminobenzoil)-amino-alcanoil-aminobenzoico y de acido triiodo-2,4,6-bis((triiodo-2,4,6-fenil)-carbamoil-metil)-aminoalcanoil-aminobenzoico |
-
1976
- 1976-04-08 GB GB14343/76A patent/GB1539791A/en not_active Expired
-
1977
- 1977-03-25 CH CH380077A patent/CH620422A5/fr not_active IP Right Cessation
- 1977-03-29 IL IL51774A patent/IL51774A/xx unknown
- 1977-03-29 US US05/782,413 patent/US4107286A/en not_active Expired - Lifetime
- 1977-03-30 ZA ZA00771945A patent/ZA771945B/xx unknown
- 1977-03-31 YU YU00853/77A patent/YU85377A/xx unknown
- 1977-03-31 FR FR7709735A patent/FR2347339A1/fr active Granted
- 1977-03-31 ES ES457405A patent/ES457405A1/es not_active Expired
- 1977-04-04 CA CA275,511A patent/CA1105481A/en not_active Expired
- 1977-04-04 NL NL7703675A patent/NL7703675A/xx not_active Application Discontinuation
- 1977-04-05 EG EG192/77A patent/EG12702A/xx active
- 1977-04-05 SE SE7703958A patent/SE436872B/xx unknown
- 1977-04-05 NO NO771209A patent/NO146862C/no unknown
- 1977-04-06 MX MX775615U patent/MX4238E/es unknown
- 1977-04-06 BR BR7702215A patent/BR7702215A/pt unknown
- 1977-04-06 DD DD7700198274A patent/DD129979A5/xx unknown
- 1977-04-06 AR AR267151A patent/AR215624A1/es active
- 1977-04-06 DK DK158277AA patent/DK147917B/da not_active IP Right Cessation
- 1977-04-06 DE DE19772715382 patent/DE2715382A1/de not_active Withdrawn
- 1977-04-06 GR GR53180A patent/GR63091B/el unknown
- 1977-04-06 FI FI771092A patent/FI67078C/fi not_active IP Right Cessation
- 1977-04-07 BE BE176489A patent/BE853333A/xx not_active IP Right Cessation
- 1977-04-07 AU AU24124/77A patent/AU505744B2/en not_active Expired
- 1977-04-07 CS CS772331A patent/CS204000B2/cs unknown
- 1977-04-07 JP JP52039928A patent/JPS6023669B2/ja not_active Expired
- 1977-04-07 AT AT246077A patent/AT348989B/de not_active IP Right Cessation
- 1977-04-08 SU SU772469149A patent/SU793387A3/ru active
- 1977-04-08 HU HU77GU322A patent/HU173333B/hu unknown
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| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: GUERBET S.A. |