DE2118219C3 - Neues Röntgenkontrastmittel - Google Patents
Neues RöntgenkontrastmittelInfo
- Publication number
- DE2118219C3 DE2118219C3 DE2118219A DE2118219A DE2118219C3 DE 2118219 C3 DE2118219 C3 DE 2118219C3 DE 2118219 A DE2118219 A DE 2118219A DE 2118219 A DE2118219 A DE 2118219A DE 2118219 C3 DE2118219 C3 DE 2118219C3
- Authority
- DE
- Germany
- Prior art keywords
- acetamido
- ray contrast
- compound
- contrast medium
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002872 contrast media Substances 0.000 title claims description 5
- 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 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- KISFRFNQZTVXGT-UHFFFAOYSA-N 3-acetamido-5-[(2-hydroxyacetyl)amino]-2,4,6-triiodobenzoic acid Chemical compound CC(=O)NC1=C(I)C(NC(=O)CO)=C(I)C(C(O)=O)=C1I KISFRFNQZTVXGT-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 150000002169 ethanolamines Chemical class 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- -1 methoxy compound Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound 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
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 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
- PTSMDXFVHORSNF-UHFFFAOYSA-N O.C(C)(=O)NC=1C(=C(C(=O)O)C(=C(C1I)N)I)I Chemical compound O.C(C)(=O)NC=1C(=C(C(=O)O)C(=C(C1I)N)I)I PTSMDXFVHORSNF-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940039231 contrast media Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000036581 peripheral resistance Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical compound CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CUGDYSSBTWBKII-UHFFFAOYSA-N 6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)CC(O)C(O)C(O)C(O)CO CUGDYSSBTWBKII-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- MJIFTQLKFAMPKF-UHFFFAOYSA-N O.O.C(C)(=O)NC=1C(=C(C(=O)O)C(=C(C1I)NC(CO)=O)I)I Chemical compound O.O.C(C)(=O)NC=1C(=C(C(=O)O)C(=C(C1I)NC(CO)=O)I)I MJIFTQLKFAMPKF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 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
- 150000003863 ammonium salts Chemical class 0.000 description 1
- ALMQNZNREIHKET-UHFFFAOYSA-N benzoic acid;dihydrate Chemical compound O.O.OC(=O)C1=CC=CC=C1 ALMQNZNREIHKET-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver 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
- 238000005259 measurement Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000002700 urine Anatomy 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)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2118219A DE2118219C3 (de) | 1971-04-10 | 1971-04-10 | Neues Röntgenkontrastmittel |
| IT22619/72A IT1048929B (it) | 1971-04-10 | 1972-03-30 | Mezzi di contrasto per raggi x |
| AU40633/72A AU463194B2 (en) | 1971-04-10 | 1972-03-30 | New xray shading agents |
| CH503472A CH574740A5 (enrdf_load_stackoverflow) | 1971-04-10 | 1972-04-06 | |
| AT459173A AT318801B (de) | 1971-04-10 | 1972-04-07 | Röntgenkontrastmittel |
| HUSCHE385*1A HU163446B (enrdf_load_stackoverflow) | 1971-04-10 | 1972-04-07 | |
| DD162148A DD95265A5 (enrdf_load_stackoverflow) | 1971-04-10 | 1972-04-07 | |
| AT304472A AT316523B (de) | 1971-04-10 | 1972-04-07 | Verfahren zur Herstellung von 3-Acetamido-5-hydroxyacetamido-2,4,6-trijodbenzoesäure und deren Salzen |
| ES401603A ES401603A1 (es) | 1971-04-10 | 1972-04-08 | Procedimiento para la preparacion de agentes de contraste de rayos x. |
| CA139,316A CA987339A (en) | 1971-04-10 | 1972-04-10 | X-ray contrast medium |
| FR7212450A FR2132810B1 (enrdf_load_stackoverflow) | 1971-04-10 | 1972-04-10 | |
| NL7204789A NL7204789A (enrdf_load_stackoverflow) | 1971-04-10 | 1972-04-10 | |
| ZA722396A ZA722396B (en) | 1971-04-10 | 1972-04-10 | New x-ray shading agents |
| GB1634672A GB1391843A (en) | 1971-04-10 | 1972-04-10 | X-ray contrast agents |
| BE781889A BE781889A (fr) | 1971-04-10 | 1972-04-10 | Produits de contraste aux rayons x, et leur preparation |
| IL39167A IL39167A (en) | 1971-04-10 | 1972-04-10 | X-ray shading agents containing a water soluble salt of 3-acetamido-5-hydroxy-acetamido-2,4,6-triiodobenzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2118219A DE2118219C3 (de) | 1971-04-10 | 1971-04-10 | Neues Röntgenkontrastmittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2118219A1 DE2118219A1 (de) | 1972-10-26 |
| DE2118219B2 DE2118219B2 (de) | 1980-07-03 |
| DE2118219C3 true DE2118219C3 (de) | 1981-07-16 |
Family
ID=5804754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2118219A Expired DE2118219C3 (de) | 1971-04-10 | 1971-04-10 | Neues Röntgenkontrastmittel |
Country Status (15)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH641682A5 (en) * | 1978-10-05 | 1984-03-15 | Daeniker Felix | X-ray contrast medium |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3076024A (en) * | 1954-02-19 | 1963-01-29 | Sterling Drug Inc | Acylated 3, 5-diaminopolyhalobenzoic acids |
| DE1129260B (de) * | 1961-05-12 | 1962-05-10 | Schering Ag | Roentgenkontrastmittel |
-
1971
- 1971-04-10 DE DE2118219A patent/DE2118219C3/de not_active Expired
-
1972
- 1972-03-30 IT IT22619/72A patent/IT1048929B/it active
- 1972-03-30 AU AU40633/72A patent/AU463194B2/en not_active Expired
- 1972-04-06 CH CH503472A patent/CH574740A5/xx not_active IP Right Cessation
- 1972-04-07 AT AT304472A patent/AT316523B/de not_active IP Right Cessation
- 1972-04-07 DD DD162148A patent/DD95265A5/xx unknown
- 1972-04-07 HU HUSCHE385*1A patent/HU163446B/hu unknown
- 1972-04-07 AT AT459173A patent/AT318801B/de not_active IP Right Cessation
- 1972-04-08 ES ES401603A patent/ES401603A1/es not_active Expired
- 1972-04-10 IL IL39167A patent/IL39167A/en unknown
- 1972-04-10 ZA ZA722396A patent/ZA722396B/xx unknown
- 1972-04-10 CA CA139,316A patent/CA987339A/en not_active Expired
- 1972-04-10 FR FR7212450A patent/FR2132810B1/fr not_active Expired
- 1972-04-10 BE BE781889A patent/BE781889A/xx unknown
- 1972-04-10 NL NL7204789A patent/NL7204789A/xx not_active Application Discontinuation
- 1972-04-10 GB GB1634672A patent/GB1391843A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1048929B (it) | 1980-12-20 |
| IL39167A0 (en) | 1972-06-28 |
| CH574740A5 (enrdf_load_stackoverflow) | 1976-04-30 |
| FR2132810A1 (enrdf_load_stackoverflow) | 1972-11-24 |
| IL39167A (en) | 1976-01-30 |
| DE2118219B2 (de) | 1980-07-03 |
| FR2132810B1 (enrdf_load_stackoverflow) | 1975-03-14 |
| ZA722396B (en) | 1972-12-27 |
| NL7204789A (enrdf_load_stackoverflow) | 1972-10-12 |
| AT316523B (de) | 1974-07-10 |
| BE781889A (fr) | 1972-10-10 |
| AT318801B (de) | 1974-11-25 |
| AU463194B2 (en) | 1975-07-02 |
| ES401603A1 (es) | 1975-02-16 |
| DD95265A5 (enrdf_load_stackoverflow) | 1973-01-20 |
| AU4063372A (en) | 1973-10-04 |
| HU163446B (enrdf_load_stackoverflow) | 1973-08-28 |
| DE2118219A1 (de) | 1972-10-26 |
| GB1391843A (en) | 1975-04-23 |
| CA987339A (en) | 1976-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ZOELLNER, GEORG, DR., 1000 BERLIN, DE |
|
| 8339 | Ceased/non-payment of the annual fee |