SU514566A3 - Способ получени производных трийодированных аминобензолкарбоновых кислот, или их низких алкиловых сложных эфиров, или солей - Google Patents
Способ получени производных трийодированных аминобензолкарбоновых кислот, или их низких алкиловых сложных эфиров, или солейInfo
- Publication number
- SU514566A3 SU514566A3 SU1948994A SU1948994A SU514566A3 SU 514566 A3 SU514566 A3 SU 514566A3 SU 1948994 A SU1948994 A SU 1948994A SU 1948994 A SU1948994 A SU 1948994A SU 514566 A3 SU514566 A3 SU 514566A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- residue
- acid
- carbon atoms
- lower alkyl
- hydrogen
- Prior art date
Links
- 125000005907 alkyl ester group Chemical group 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 aliphatic alcohols Chemical class 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- VZLKQEPNZIWSFF-UHFFFAOYSA-N 1-pyrrolidin-1-ylpiperidine Chemical compound C1CCCN1N1CCCCC1 VZLKQEPNZIWSFF-UHFFFAOYSA-N 0.000 claims 1
- KQTGCJMBUBYSLL-UHFFFAOYSA-N 4-piperidin-1-ylmorpholine Chemical compound C1CCCCN1N1CCOCC1 KQTGCJMBUBYSLL-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229910019213 POCl3 Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VVODXPFIWOSTQB-UHFFFAOYSA-N 3-amino-2,4,6-triiodobenzoyl chloride Chemical compound NC1=C(I)C=C(I)C(C(Cl)=O)=C1I VVODXPFIWOSTQB-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2235935A DE2235935C3 (de) | 1972-07-21 | 1972-07-21 | Neue Derivate von trijodierten Aminobenzolcarbonsäuren, ein Verfahren zu deren Herstellung und diese Verbindungen enthaltende Röntgenkontrastmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU514566A3 true SU514566A3 (ru) | 1976-05-15 |
Family
ID=5851343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1948994A SU514566A3 (ru) | 1972-07-21 | 1973-07-20 | Способ получени производных трийодированных аминобензолкарбоновых кислот, или их низких алкиловых сложных эфиров, или солей |
Country Status (8)
| Country | Link |
|---|---|
| ES (1) | ES417136A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2193621A1 (enrdf_load_stackoverflow) |
| HU (1) | HU166753B (enrdf_load_stackoverflow) |
| IT (1) | IT991822B (enrdf_load_stackoverflow) |
| PL (1) | PL85383B1 (enrdf_load_stackoverflow) |
| RO (3) | RO63770A2 (enrdf_load_stackoverflow) |
| SU (1) | SU514566A3 (enrdf_load_stackoverflow) |
| YU (3) | YU36488B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH480070A (de) * | 1967-03-01 | 1969-10-31 | Eprova Ag | Röntgenkontrastmittel |
-
1973
- 1973-07-11 YU YU187573A patent/YU36488B/xx unknown
- 1973-07-13 HU HUOE000205 patent/HU166753B/hu unknown
- 1973-07-18 FR FR7326277A patent/FR2193621A1/fr active Granted
- 1973-07-20 RO RO83230A patent/RO63770A2/ro unknown
- 1973-07-20 SU SU1948994A patent/SU514566A3/ru active
- 1973-07-20 PL PL16419673A patent/PL85383B1/pl unknown
- 1973-07-20 IT IT6918773A patent/IT991822B/it active
- 1973-07-20 RO RO8322673A patent/RO64154A/ro unknown
- 1973-07-20 RO RO7554573A patent/RO62908A/ro unknown
- 1973-07-21 ES ES417136A patent/ES417136A1/es not_active Expired
-
1979
- 1979-11-14 YU YU279279A patent/YU36489B/xx unknown
- 1979-11-15 YU YU280679A patent/YU36490B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO62908A (fr) | 1978-02-15 |
| FR2193621B1 (enrdf_load_stackoverflow) | 1977-01-28 |
| YU36490B (en) | 1984-02-29 |
| PL85383B1 (enrdf_load_stackoverflow) | 1976-04-30 |
| IT991822B (it) | 1975-08-30 |
| HU166753B (enrdf_load_stackoverflow) | 1975-05-28 |
| RO64154A (fr) | 1979-01-15 |
| YU36488B (en) | 1984-02-29 |
| YU187573A (en) | 1982-02-25 |
| YU279279A (en) | 1982-02-25 |
| ES417136A1 (es) | 1976-03-16 |
| FR2193621A1 (en) | 1974-02-22 |
| RO63770A2 (ro) | 1978-09-15 |
| YU280679A (en) | 1982-02-25 |
| YU36489B (en) | 1984-02-29 |
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