NO133665B - - Google Patents
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- Publication number
- NO133665B NO133665B NO1688/72A NO168872A NO133665B NO 133665 B NO133665 B NO 133665B NO 1688/72 A NO1688/72 A NO 1688/72A NO 168872 A NO168872 A NO 168872A NO 133665 B NO133665 B NO 133665B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- triiodobenzoic
- triiodobenzoic acid
- acetamidomethyl
- salts
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000002872 contrast media Substances 0.000 claims description 4
- HBPFBHDBLVTAQV-UHFFFAOYSA-N 3-(acetamidomethyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]benzoic acid Chemical compound C(C)(=O)NCC=1C(=C(C(=O)O)C(=C(C1I)NC(COC)=O)I)I HBPFBHDBLVTAQV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 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 2
- 150000001875 compounds Chemical class 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 acetoxyacetyl Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000002583 angiography Methods 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000007487 urography Methods 0.000 description 2
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 description 1
- VDYXCTNJHWITDQ-UHFFFAOYSA-N 2-butoxyacetyl chloride Chemical compound CCCCOCC(Cl)=O VDYXCTNJHWITDQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 244000182067 Fraxinus ornus Species 0.000 description 1
- 206010021703 Indifference Diseases 0.000 description 1
- 206010051602 Laziness Diseases 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002349 favourable effect Effects 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000002792 vascular Effects 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
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
- A61K49/0452—Solutions, e.g. for injection
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2124904A DE2124904C3 (de) | 1971-05-15 | 1971-05-15 | Hydroxy- und Alkoxyacetamido-trijodbenzoesäuren, deren Salze mit physiologisch verträglichen Basen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Röntgenkontrastmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133665B true NO133665B (fr) | 1976-03-01 |
| NO133665C NO133665C (fr) | 1976-06-09 |
Family
ID=5808368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1688/72A NO133665C (fr) | 1971-05-15 | 1972-05-12 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3912776A (fr) |
| AR (1) | AR192247A1 (fr) |
| AT (2) | AT324313B (fr) |
| AU (1) | AU458136B2 (fr) |
| BE (1) | BE783483A (fr) |
| CA (1) | CA959070A (fr) |
| CH (1) | CH583180A5 (fr) |
| DD (1) | DD100155A5 (fr) |
| DE (1) | DE2124904C3 (fr) |
| DK (1) | DK129986B (fr) |
| ES (2) | ES402711A1 (fr) |
| FR (1) | FR2137807B1 (fr) |
| GB (1) | GB1388863A (fr) |
| HU (1) | HU162903B (fr) |
| IL (1) | IL39407A (fr) |
| IT (1) | IT1006032B (fr) |
| NL (1) | NL7206552A (fr) |
| NO (1) | NO133665C (fr) |
| PL (2) | PL83419B1 (fr) |
| SU (1) | SU515446A3 (fr) |
| ZA (1) | ZA723271B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281967A (en) * | 1964-03-30 | 1966-11-01 | Gen Electric | Measurement tool |
| CH576256A5 (fr) * | 1973-07-17 | 1976-06-15 | Bracco Ind Chimica Spa | |
| CH608189A5 (fr) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3076024A (en) * | 1954-02-19 | 1963-01-29 | Sterling Drug Inc | Acylated 3, 5-diaminopolyhalobenzoic acids |
| CH414063A (de) * | 1962-11-23 | 1966-05-31 | Eprova Ag | Röntgenkontrastmittel |
| BE667886A (fr) * | 1965-04-23 |
-
1971
- 1971-05-15 DE DE2124904A patent/DE2124904C3/de not_active Expired
-
1972
- 1972-04-30 SU SU1779677A patent/SU515446A3/ru active
- 1972-05-02 DD DD162683A patent/DD100155A5/xx unknown
- 1972-05-08 GB GB2129172A patent/GB1388863A/en not_active Expired
- 1972-05-09 IT IT24087/72A patent/IT1006032B/it active
- 1972-05-10 CA CA141,815A patent/CA959070A/en not_active Expired
- 1972-05-10 IL IL39407A patent/IL39407A/xx unknown
- 1972-05-12 FR FR7216989A patent/FR2137807B1/fr not_active Expired
- 1972-05-12 NO NO1688/72A patent/NO133665C/no unknown
- 1972-05-12 AT AT359473A patent/AT324313B/de not_active IP Right Cessation
- 1972-05-12 PL PL1972155350A patent/PL83419B1/pl unknown
- 1972-05-12 DK DK239072AA patent/DK129986B/da unknown
- 1972-05-12 HU HUSC391A patent/HU162903B/hu unknown
- 1972-05-12 PL PL1972172232A patent/PL90766B1/pl unknown
- 1972-05-12 AT AT416672A patent/AT314078B/de active
- 1972-05-13 ES ES402711A patent/ES402711A1/es not_active Expired
- 1972-05-13 ES ES402710A patent/ES402710A1/es not_active Expired
- 1972-05-15 AR AR242003A patent/AR192247A1/es active
- 1972-05-15 US US253026A patent/US3912776A/en not_active Expired - Lifetime
- 1972-05-15 NL NL7206552A patent/NL7206552A/xx unknown
- 1972-05-15 BE BE783483A patent/BE783483A/fr unknown
- 1972-05-15 CH CH715872A patent/CH583180A5/xx not_active IP Right Cessation
- 1972-05-15 AU AU42303/72A patent/AU458136B2/en not_active Expired
- 1972-05-15 ZA ZA723271A patent/ZA723271B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK129986C (fr) | 1975-05-20 |
| AU458136B2 (en) | 1975-02-20 |
| IT1006032B (it) | 1976-09-30 |
| CH583180A5 (fr) | 1976-12-31 |
| DK129986B (da) | 1974-12-09 |
| DD100155A5 (fr) | 1973-09-12 |
| IL39407A0 (en) | 1972-07-26 |
| CA959070A (en) | 1974-12-10 |
| HU162903B (fr) | 1973-04-28 |
| AT324313B (de) | 1975-08-25 |
| ES402710A1 (es) | 1975-04-01 |
| SU515446A3 (ru) | 1976-05-25 |
| AU4230372A (en) | 1973-11-22 |
| PL83419B1 (fr) | 1975-12-31 |
| IL39407A (en) | 1975-04-25 |
| NO133665C (fr) | 1976-06-09 |
| PL90766B1 (fr) | 1977-01-31 |
| NL7206552A (fr) | 1972-11-17 |
| FR2137807B1 (fr) | 1975-03-14 |
| AR192247A1 (es) | 1973-02-08 |
| BE783483A (fr) | 1972-11-16 |
| US3912776A (en) | 1975-10-14 |
| ES402711A1 (es) | 1975-04-01 |
| DE2124904A1 (de) | 1972-12-07 |
| ZA723271B (en) | 1973-03-28 |
| GB1388863A (en) | 1975-03-26 |
| DE2124904C3 (de) | 1980-09-18 |
| DE2124904B2 (de) | 1980-01-17 |
| AT314078B (de) | 1974-03-25 |
| FR2137807A1 (fr) | 1972-12-29 |
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