CH494576A - Verfahren zur Herstellung von neuen Röntgenkontrastmitteln - Google Patents
Verfahren zur Herstellung von neuen RöntgenkontrastmittelnInfo
- Publication number
- CH494576A CH494576A CH1533669A CH1533669A CH494576A CH 494576 A CH494576 A CH 494576A CH 1533669 A CH1533669 A CH 1533669A CH 1533669 A CH1533669 A CH 1533669A CH 494576 A CH494576 A CH 494576A
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- ray contrast
- alkylene
- carbon atoms
- alkyl
- Prior art date
Links
- 239000002872 contrast media Substances 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229940039231 contrast media Drugs 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- -1 amine salts Chemical class 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 241000283973 Oryctolagus cuniculus Species 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 210000000232 gallbladder Anatomy 0.000 abstract 1
- 210000002700 urine Anatomy 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OQZKUFFJJZRJIG-UHFFFAOYSA-N N-(3-hydroxy-2,4,6-triiodophenyl)butanamide Chemical compound C(CCC)(=O)NC=1C(=C(C(=CC1I)I)O)I OQZKUFFJJZRJIG-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- XGZGQQDTACZODX-UHFFFAOYSA-N n-(3-hydroxyphenyl)-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC=CC(O)=C1 XGZGQQDTACZODX-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KLLOEOPUXBJSOW-UHFFFAOYSA-N 3-(methylamino)phenol Chemical compound CNC1=CC=CC(O)=C1 KLLOEOPUXBJSOW-UHFFFAOYSA-N 0.000 description 1
- NMOVGKYYUYVCKE-UHFFFAOYSA-N C(C)N(C=1C(=C(C(=CC=1I)I)O)I)C(C)=O Chemical compound C(C)N(C=1C(=C(C(=CC=1I)I)O)I)C(C)=O NMOVGKYYUYVCKE-UHFFFAOYSA-N 0.000 description 1
- IVMOJRDEDKWZQW-UHFFFAOYSA-N CC(N(C)C(C(I)=C(C(I)=C1)OCCOC2=C(CC(O)=O)C=CC=C2)=C1I)=O Chemical compound CC(N(C)C(C(I)=C(C(I)=C1)OCCOC2=C(CC(O)=O)C=CC=C2)=C1I)=O IVMOJRDEDKWZQW-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009606 cholecystography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- LPICKVRTXDYZBC-UHFFFAOYSA-N ethyl 2-(2-chloroethoxy)propanoate Chemical compound CCOC(=O)C(C)OCCCl LPICKVRTXDYZBC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 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
-
- 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
- A61K49/0495—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 intended for oral administration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1533669A CH494576A (de) | 1967-05-29 | 1967-05-29 | Verfahren zur Herstellung von neuen Röntgenkontrastmitteln |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1533669A CH494576A (de) | 1967-05-29 | 1967-05-29 | Verfahren zur Herstellung von neuen Röntgenkontrastmitteln |
| CH748267A CH483262A (de) | 1967-05-29 | 1967-05-29 | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH494576A true CH494576A (de) | 1970-08-15 |
Family
ID=4325807
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1533669A CH494576A (de) | 1967-05-29 | 1967-05-29 | Verfahren zur Herstellung von neuen Röntgenkontrastmitteln |
| CH748267A CH483262A (de) | 1967-05-29 | 1967-05-29 | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH748267A CH483262A (de) | 1967-05-29 | 1967-05-29 | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314055A (en) * | 1975-09-29 | 1982-02-02 | Mallinckrodt, Inc. | 3,5-Disubstituted-2,4,6-triiodoanilides of polyhydroxy-monobasic acids |
| US5348727A (en) * | 1993-03-11 | 1994-09-20 | Sterling Winthrop Inc. | Compositions of iodophenoxy alkylene ethers for visualization of the gastrointestinal tract |
| US5310538A (en) * | 1993-03-11 | 1994-05-10 | Sterling Winthrop Inc. | Compositions of iodophenoxy alkylene ethers in film-forming materials for visualization of the gastrointestinal tract |
-
1967
- 1967-05-29 CH CH1533669A patent/CH494576A/de unknown
- 1967-05-29 CH CH748267A patent/CH483262A/de not_active IP Right Cessation
-
1968
- 1968-05-02 SE SE05927/68A patent/SE352340B/xx unknown
- 1968-05-07 GB GB1228851D patent/GB1228851A/en not_active Expired
- 1968-05-14 DK DK223568AA patent/DK123762B/da unknown
- 1968-05-14 US US728894A patent/US3553259A/en not_active Expired - Lifetime
- 1968-05-16 NO NO1936/68A patent/NO121611B/no unknown
- 1968-05-24 NL NL6807381A patent/NL6807381A/xx unknown
- 1968-05-25 DE DE19681768553 patent/DE1768553B1/de not_active Withdrawn
- 1968-05-27 AT AT60669A patent/AT284825B/de not_active IP Right Cessation
- 1968-05-27 AT AT506668A patent/AT277452B/de not_active IP Right Cessation
- 1968-05-28 FR FR1596453D patent/FR1596453A/fr not_active Expired
- 1968-05-28 ES ES354410A patent/ES354410A1/es not_active Expired
- 1968-05-28 BE BE715799D patent/BE715799A/xx unknown
- 1968-05-28 FR FR153106A patent/FR7769M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3553259A (en) | 1971-01-05 |
| DK123762B (da) | 1972-07-31 |
| FR7769M (enrdf_load_stackoverflow) | 1970-03-23 |
| FR1596453A (enrdf_load_stackoverflow) | 1970-06-22 |
| AT277452B (de) | 1969-12-29 |
| NL6807381A (enrdf_load_stackoverflow) | 1968-12-02 |
| DE1768553B1 (de) | 1970-09-16 |
| ES354410A1 (es) | 1969-11-01 |
| SE352340B (enrdf_load_stackoverflow) | 1972-12-27 |
| GB1228851A (enrdf_load_stackoverflow) | 1971-04-21 |
| BE715799A (enrdf_load_stackoverflow) | 1968-11-28 |
| CH483262A (de) | 1969-12-31 |
| NO121611B (enrdf_load_stackoverflow) | 1971-03-22 |
| AT284825B (de) | 1970-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PLZ | Patent of addition ceased |