SU624571A3 - Способ получени производных бис-(трииодизофталева кислота амидов моноаминокислоты) - Google Patents
Способ получени производных бис-(трииодизофталева кислота амидов моноаминокислоты)Info
- Publication number
- SU624571A3 SU624571A3 SU762318654A SU2318654A SU624571A3 SU 624571 A3 SU624571 A3 SU 624571A3 SU 762318654 A SU762318654 A SU 762318654A SU 2318654 A SU2318654 A SU 2318654A SU 624571 A3 SU624571 A3 SU 624571A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- decomposition
- methyl
- bis
- methylcarbamoyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 31
- 238000000034 method Methods 0.000 title description 2
- 150000001408 amides Chemical class 0.000 title 1
- 238000000354 decomposition reaction Methods 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- -1 2-methoxy-1-methyl-carbamoyl-ethyl Chemical group 0.000 description 20
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 18
- 229940113088 dimethylacetamide Drugs 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- CVZGUJMLZZTPKH-UHFFFAOYSA-N octane-3,6-dione Chemical compound CCC(=O)CCC(=O)CC CVZGUJMLZZTPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 229940078547 methylserine Drugs 0.000 description 5
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229960000250 adipic acid Drugs 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FVUKYCZRWSQGAS-UHFFFAOYSA-N 3-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC(C(O)=O)=C1 FVUKYCZRWSQGAS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940043230 sarcosine Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HJZZQNLKBWJYPD-UHFFFAOYSA-N 2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]acetic acid Chemical compound OC(=O)COCCOCCOCC(O)=O HJZZQNLKBWJYPD-UHFFFAOYSA-N 0.000 description 1
- 229920013663 Acetose Polymers 0.000 description 1
- 101150043532 CISH gene Proteins 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- TWRQCVNFACGORI-UHFFFAOYSA-N hexane;dihydrochloride Chemical compound Cl.Cl.CCCCCC TWRQCVNFACGORI-UHFFFAOYSA-N 0.000 description 1
- LYEKUMJVNIANHM-UHFFFAOYSA-N hexanedioic acid;hydrochloride Chemical compound Cl.OC(=O)CCCCC(O)=O LYEKUMJVNIANHM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DQTOZIJNMYYCJE-UHFFFAOYSA-N methyl 3-carbonochloridoyl-5-nitrobenzoate Chemical compound COC(=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 DQTOZIJNMYYCJE-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000005406 washing Methods 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
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752505320 DE2505320A1 (de) | 1975-02-03 | 1975-02-03 | Dicarbonsaeurederivate von trijod- isophthalsaeuremonoaminosaeureamiden, verfahren zu ihrer herstellung und ihre verwendung als roentgenkontrastmittel |
| DE19752554148 DE2554148A1 (de) | 1975-11-28 | 1975-11-28 | Dicarbonsaeurederivate von trijod- isophthalsaeuremonoaminosaeureamiden, verfahren zu ihrer herstellung und ihre verwendung als roentgenkontrastmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU624571A3 true SU624571A3 (ru) | 1978-09-15 |
Family
ID=25768472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762318654A SU624571A3 (ru) | 1975-02-03 | 1976-02-02 | Способ получени производных бис-(трииодизофталева кислота амидов моноаминокислоты) |
Country Status (17)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52130923A (en) * | 1976-04-27 | 1977-11-02 | Mallinckrodt Chemical Works | Xxray photographic agent |
| JPS5531068A (en) * | 1978-07-04 | 1980-03-05 | Nyegaard & Co As | Manufacture of x ray contrast agent injectable sterilized solution |
| DE2926428A1 (de) * | 1979-06-28 | 1981-01-08 | Schering Ag | Trijodierte 5-aminoisophthalsaeure- derivate |
| IT1207226B (it) * | 1979-08-09 | 1989-05-17 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico, metodo per la loro preparazione e mezzi di contrasto che li contengono. |
| IL94718A (en) * | 1989-07-05 | 1994-10-21 | Schering Ag | Non-ionic carboxamide contrast agent and method of preparation |
-
1976
- 1976-01-13 FI FI760068A patent/FI760068A7/fi not_active Application Discontinuation
- 1976-01-14 DK DK14376*#A patent/DK14376A/da not_active Application Discontinuation
- 1976-01-22 IL IL48893A patent/IL48893A0/xx unknown
- 1976-01-28 AU AU10607/76A patent/AU1060776A/en not_active Expired
- 1976-01-29 GB GB3512/76A patent/GB1538070A/en not_active Expired
- 1976-01-30 DD DD191043A patent/DD123313A5/xx unknown
- 1976-02-02 LU LU74294A patent/LU74294A1/xx unknown
- 1976-02-02 NO NO760327*[A patent/NO760327L/no unknown
- 1976-02-02 AT AT69176A patent/AT344315B/de not_active IP Right Cessation
- 1976-02-02 GR GR49935A patent/GR58172B/el unknown
- 1976-02-02 NL NL7601052A patent/NL7601052A/xx not_active Application Discontinuation
- 1976-02-02 SE SE7601080A patent/SE7601080L/xx unknown
- 1976-02-02 PT PT64764A patent/PT64764B/pt unknown
- 1976-02-02 SU SU762318654A patent/SU624571A3/ru active
- 1976-02-03 ES ES444879A patent/ES444879A1/es not_active Expired
- 1976-02-03 JP JP51010801A patent/JPS51101948A/ja active Pending
- 1976-02-03 FR FR7602878A patent/FR2299020A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ES444879A1 (es) | 1977-08-16 |
| DD123313A5 (enrdf_load_stackoverflow) | 1976-12-12 |
| PT64764B (de) | 1977-06-06 |
| FI760068A7 (enrdf_load_stackoverflow) | 1976-08-04 |
| ATA69176A (de) | 1977-11-15 |
| DK14376A (da) | 1976-08-04 |
| JPS51101948A (enrdf_load_stackoverflow) | 1976-09-08 |
| IL48893A0 (en) | 1976-03-31 |
| AU1060776A (en) | 1977-08-04 |
| GR58172B (en) | 1977-08-22 |
| SE7601080L (sv) | 1976-08-04 |
| NL7601052A (nl) | 1976-08-05 |
| PT64764A (de) | 1976-03-01 |
| LU74294A1 (enrdf_load_stackoverflow) | 1976-06-18 |
| NO760327L (enrdf_load_stackoverflow) | 1976-08-04 |
| GB1538070A (en) | 1979-01-10 |
| AT344315B (de) | 1978-07-10 |
| FR2299020A1 (fr) | 1976-08-27 |
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