NO742584L - - Google Patents
Info
- Publication number
- NO742584L NO742584L NO742584A NO742584A NO742584L NO 742584 L NO742584 L NO 742584L NO 742584 A NO742584 A NO 742584A NO 742584 A NO742584 A NO 742584A NO 742584 L NO742584 L NO 742584L
- Authority
- NO
- Norway
- Prior art keywords
- triiodo
- acid
- denotes
- hydroxy
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- PIXCADDWHUNZGA-UHFFFAOYSA-N 3-[(2-hydroxyacetyl)amino]-5-[[(2-hydroxyacetyl)amino]methyl]-2,4,6-triiodobenzoic acid Chemical group OCC(=O)NCC=1C(=C(C(=O)O)C(=C(C1I)NC(CO)=O)I)I PIXCADDWHUNZGA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 4
- 239000002872 contrast media Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 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 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- JBJLEUTWAFDYOV-UHFFFAOYSA-N 3-amino-5-(aminomethyl)-2,4,6-triiodobenzoic acid Chemical compound NCC=1C(=C(C(=O)O)C(=C(C1I)N)I)I JBJLEUTWAFDYOV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000012266 salt solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- -1 hydroxyacetylaminomethyl group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 2
- CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical compound OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 description 2
- GTFQFVVSKKXTMM-UHFFFAOYSA-N 3-acetamido-5-[(2-hydroxypropanoylamino)methyl]-2,4,6-triiodobenzoic acid Chemical compound OC(C(=O)NCC=1C(=C(C(=O)O)C(=C(C=1I)NC(C)=O)I)I)C GTFQFVVSKKXTMM-UHFFFAOYSA-N 0.000 description 2
- RJCHCFQTUKAYAA-UHFFFAOYSA-N 5-[[2-amino-5-[(4-methoxyphenyl)methyl]-3-methylimidazol-4-yl]methyl]-2-methoxybenzene-1,3-diol Chemical compound C1=CC(OC)=CC=C1CC1=C(CC=2C=C(O)C(OC)=C(O)C=2)N(C)C(=N)N1 RJCHCFQTUKAYAA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000007487 urography Methods 0.000 description 2
- ALHZEIINTQJLOT-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) acetate Chemical compound ClC(=O)C(C)OC(C)=O ALHZEIINTQJLOT-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- AZXYWIRQFXFELJ-UHFFFAOYSA-N 3-(acetamidomethyl)-5-[(2-hydroxyacetyl)amino]-2,4,6-triiodobenzoic acid Chemical compound C(C)(=O)NCC=1C(=C(C(=O)O)C(=C(C1I)NC(CO)=O)I)I AZXYWIRQFXFELJ-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
- QMQFFHSJUJDRPG-UHFFFAOYSA-N 3-amino-2,4,6-triiodobenzoic acid Chemical compound NC1=C(I)C=C(I)C(C(O)=O)=C1I QMQFFHSJUJDRPG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WOMTYMDHLQTCHY-UHFFFAOYSA-N 3-methylamino-1,2-propanediol Chemical compound CNCC(O)CO WOMTYMDHLQTCHY-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 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
- 239000000571 coke Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HXLVCCRPDYIRRX-UHFFFAOYSA-N iodoamine Chemical compound IN HXLVCCRPDYIRRX-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 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
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GKODZWOPPOTFGA-UHFFFAOYSA-N tris(hydroxyethyl)aminomethane Chemical compound OCCC(N)(CCO)CCO GKODZWOPPOTFGA-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- 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
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1044973A CH576256A5 (en, 2012) | 1973-07-17 | 1973-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO742584L true NO742584L (en, 2012) | 1975-02-10 |
Family
ID=4363336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742584A NO742584L (en, 2012) | 1973-07-17 | 1974-07-16 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3886203A (en, 2012) |
| JP (1) | JPS5534793B2 (en, 2012) |
| AT (2) | AT336580B (en, 2012) |
| BE (1) | BE816452A (en, 2012) |
| CA (1) | CA1013366A (en, 2012) |
| CH (1) | CH576256A5 (en, 2012) |
| DD (1) | DD111804A5 (en, 2012) |
| DK (1) | DK345474A (en, 2012) |
| ES (1) | ES427653A1 (en, 2012) |
| FR (1) | FR2237622B1 (en, 2012) |
| GB (1) | GB1412239A (en, 2012) |
| HU (1) | HU168361B (en, 2012) |
| IT (1) | IT1019717B (en, 2012) |
| NL (1) | NL156919B (en, 2012) |
| NO (1) | NO742584L (en, 2012) |
| SE (1) | SE7408014L (en, 2012) |
| ZA (1) | ZA743961B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021481A (en) * | 1969-06-27 | 1977-05-03 | Nyegaard & Co. A/S | Amido derivatives of 2,4,6-triiodobenzoic acids containing at least one N-hydroxyalkyl and at least two hydroxyl groups |
| CH608189A5 (en, 2012) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| GB1539791A (en) * | 1976-04-08 | 1979-02-07 | Guerbet Sa | X-ray contrast media |
| DE2629228C2 (de) * | 1976-06-25 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Jodierte Isophthalamsäure-Derivate Verfahren zu deren Herstellung sowie deren Verwendung |
| JPH02111248U (en, 2012) * | 1989-02-21 | 1990-09-05 | ||
| DE4207944C2 (de) * | 1992-03-12 | 1994-08-25 | Hench Automatik App Masch | Vorrichtung zum Abkühlen und Granulieren von schmelzflüssig aus Düsen austretenden Strängen aus thermoplastischen Kunststoffen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR6777M (en, 2012) * | 1967-07-10 | 1969-03-10 | ||
| DE2124904C3 (de) * | 1971-05-15 | 1980-09-18 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Hydroxy- und Alkoxyacetamido-trijodbenzoesäuren, deren Salze mit physiologisch verträglichen Basen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Röntgenkontrastmittel |
-
1973
- 1973-07-17 CH CH1044973A patent/CH576256A5/xx not_active IP Right Cessation
-
1974
- 1974-06-11 CA CA202,215A patent/CA1013366A/en not_active Expired
- 1974-06-17 BE BE145528A patent/BE816452A/xx unknown
- 1974-06-18 AT AT505574A patent/AT336580B/de not_active IP Right Cessation
- 1974-06-18 AT AT505474A patent/AT331968B/de not_active IP Right Cessation
- 1974-06-18 GB GB2703174A patent/GB1412239A/en not_active Expired
- 1974-06-18 SE SE7408014A patent/SE7408014L/ not_active Application Discontinuation
- 1974-06-20 ZA ZA00743961A patent/ZA743961B/xx unknown
- 1974-06-24 US US482666A patent/US3886203A/en not_active Expired - Lifetime
- 1974-06-25 ES ES427653A patent/ES427653A1/es not_active Expired
- 1974-06-26 HU HUBA3095A patent/HU168361B/hu unknown
- 1974-06-27 DK DK345474A patent/DK345474A/da unknown
- 1974-07-04 NL NL7409056.A patent/NL156919B/xx unknown
- 1974-07-15 DD DD179911A patent/DD111804A5/xx unknown
- 1974-07-15 FR FR7424538A patent/FR2237622B1/fr not_active Expired
- 1974-07-16 NO NO742584A patent/NO742584L/no unknown
- 1974-07-16 IT IT25234/74A patent/IT1019717B/it active
- 1974-07-16 JP JP8080674A patent/JPS5534793B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3886203A (en) | 1975-05-27 |
| JPS5534793B2 (en, 2012) | 1980-09-09 |
| FR2237622A1 (en, 2012) | 1975-02-14 |
| DD111804A5 (en, 2012) | 1975-03-12 |
| ZA743961B (en) | 1975-06-25 |
| CA1013366A (en) | 1977-07-05 |
| SE7408014L (en, 2012) | 1975-01-20 |
| GB1412239A (en) | 1975-10-29 |
| AU7133774A (en) | 1976-01-22 |
| HU168361B (en, 2012) | 1976-04-28 |
| BE816452A (fr) | 1974-12-17 |
| DE2425912B2 (de) | 1977-06-02 |
| JPS5047939A (en, 2012) | 1975-04-28 |
| ATA505474A (de) | 1975-12-15 |
| NL7409056A (nl) | 1975-01-21 |
| CH576256A5 (en, 2012) | 1976-06-15 |
| DE2425912A1 (de) | 1975-03-20 |
| AT331968B (de) | 1976-09-10 |
| NL156919B (nl) | 1978-06-15 |
| FR2237622B1 (en, 2012) | 1977-07-08 |
| ES427653A1 (es) | 1977-02-16 |
| IT1019717B (it) | 1977-11-30 |
| DK345474A (en, 2012) | 1975-03-17 |
| AT336580B (de) | 1977-05-10 |
| ATA505574A (de) | 1976-09-15 |
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