NO791772L - Polyjodbenzen-roentgenkontrastmidler. - Google Patents
Polyjodbenzen-roentgenkontrastmidler.Info
- Publication number
- NO791772L NO791772L NO791772A NO791772A NO791772L NO 791772 L NO791772 L NO 791772L NO 791772 A NO791772 A NO 791772A NO 791772 A NO791772 A NO 791772A NO 791772 L NO791772 L NO 791772L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen atom
- triiodo
- group
- product
- Prior art date
Links
- 239000002872 contrast media Substances 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 4
- 239000000047 product Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HZYCLELWSFMAFD-UHFFFAOYSA-N 2-[(2-aminoacetyl)amino]benzoic acid Chemical compound NCC(=O)NC1=CC=CC=C1C(O)=O HZYCLELWSFMAFD-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VGEZCDZTFHVHTC-UHFFFAOYSA-N 3-amino-5-(hydroxymethyl)-2,4,6-triiodobenzoic acid Chemical compound NC1=C(I)C(CO)=C(I)C(C(O)=O)=C1I VGEZCDZTFHVHTC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RIWAPWDHHMWTRA-UHFFFAOYSA-N 1,2,3-triiodobenzene Chemical compound IC1=CC=CC(I)=C1I RIWAPWDHHMWTRA-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- OZWUITKBAWTEAQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)propanoic acid Chemical compound C1=CC=C2C(=O)N(C(C)C(O)=O)C(=O)C2=C1 OZWUITKBAWTEAQ-UHFFFAOYSA-N 0.000 description 1
- NJYFBFNECKCDSB-UHFFFAOYSA-N 3-(2-aminoacetyl)-2-(methylamino)benzoic acid Chemical compound NCC(=O)C=1C(=C(C(=O)O)C=CC=1)NC NJYFBFNECKCDSB-UHFFFAOYSA-N 0.000 description 1
- JYBVKPOTTPXOCO-UHFFFAOYSA-N 3-[(2-aminoacetyl)amino]-5-(hydroxymethyl)-2,4,6-triiodobenzoic acid Chemical compound NCC(=O)NC1=C(I)C(CO)=C(I)C(C(O)=O)=C1I JYBVKPOTTPXOCO-UHFFFAOYSA-N 0.000 description 1
- VROWKQWFMZLPKY-UHFFFAOYSA-N 3-amino-5-(hydroxymethyl)-2,4-diiodo-6-[(2-iodoacetyl)amino]benzoic acid Chemical compound ICC(=O)NC1=C(C(=O)O)C(=C(C(=C1CO)I)N)I VROWKQWFMZLPKY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2482878 | 1978-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791772L true NO791772L (no) | 1979-12-03 |
Family
ID=10217860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791772A NO791772L (no) | 1978-05-31 | 1979-05-29 | Polyjodbenzen-roentgenkontrastmidler. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4225577A (de) |
| JP (1) | JPS54163542A (de) |
| BE (1) | BE876640R (de) |
| CA (1) | CA1137995A (de) |
| CH (1) | CH637918A5 (de) |
| DE (1) | DE2921467A1 (de) |
| DK (1) | DK224279A (de) |
| ES (1) | ES480979A0 (de) |
| FR (1) | FR2427326A2 (de) |
| NL (1) | NL7904076A (de) |
| NO (1) | NO791772L (de) |
| SE (1) | SE7904543L (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3044814A1 (de) * | 1980-11-25 | 1982-07-08 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Unsymmetrisch substituierte dicarbonsaeure-bis-(2,4,6-trijod-anilide), deren herstellung und diese enthaltende roentgenkontrastmittel |
| US4634551A (en) * | 1985-06-03 | 1987-01-06 | Procter & Gamble Company | Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain |
| GB8415909D0 (en) * | 1984-06-21 | 1984-07-25 | Procter & Gamble Ltd | Peracid compounds |
| US4852989A (en) * | 1987-05-08 | 1989-08-01 | The Procter & Gamble Company | Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain |
| US5668196A (en) * | 1995-08-10 | 1997-09-16 | Nanosystems Llc | 3-amido-triiodophenyl esters as x-ray contrast agents |
| US6265610B1 (en) | 1999-01-12 | 2001-07-24 | The University Of North Carolina At Chapel Hill | Contrast media for angiography |
| WO2017165841A1 (en) | 2016-03-25 | 2017-09-28 | Nanoprobes, Inc. | Iodine-based particles |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732293A (en) * | 1968-03-15 | 1973-05-08 | Sterling Drug Inc | Iodinated bis(aminobenzoic acids) and esters thereof |
| US3803221A (en) * | 1969-07-14 | 1974-04-09 | Sterling Drug Inc | Anilic acids of 3-substituted 2,4,6-triiodoanilines |
| DD104193A5 (de) * | 1972-12-22 | 1974-03-05 | ||
| AR207465A1 (es) * | 1974-05-31 | 1976-10-08 | Guerbet Lab Andre | Procedimiento de preparacion de derivados de acido triiodoi2,4,6-(triiodo-2,4,6-benzoil)-amino-alcanoilaminobenzoico de acido triiodo-2,4,6-(triiodo-2,4,6-(triiodo-2,4,6-benzoil)-aminoalcanoilaminobenzoil)-amino-alcanoil-aminobenzoico y de acido triiodo-2,4,6-bis((triiodo-2,4,6-fenil)-carbamoil-metil)-aminoalcanoil-aminobenzoico |
| GB1539791A (en) * | 1976-04-08 | 1979-02-07 | Guerbet Sa | X-ray contrast media |
-
1979
- 1979-05-21 FR FR7912901A patent/FR2427326A2/fr active Granted
- 1979-05-23 NL NL7904076A patent/NL7904076A/xx not_active Application Discontinuation
- 1979-05-23 SE SE7904543A patent/SE7904543L/xx not_active Application Discontinuation
- 1979-05-26 DE DE19792921467 patent/DE2921467A1/de not_active Withdrawn
- 1979-05-28 ES ES1979480979A patent/ES480979A0/es active Granted
- 1979-05-28 CH CH493279A patent/CH637918A5/fr not_active IP Right Cessation
- 1979-05-29 NO NO791772A patent/NO791772L/no unknown
- 1979-05-29 US US06/043,046 patent/US4225577A/en not_active Expired - Lifetime
- 1979-05-30 BE BE0/195464A patent/BE876640R/xx not_active IP Right Cessation
- 1979-05-30 DK DK224279A patent/DK224279A/da not_active Application Discontinuation
- 1979-05-31 CA CA000328771A patent/CA1137995A/en not_active Expired
- 1979-05-31 JP JP6808379A patent/JPS54163542A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE7904543L (sv) | 1979-12-01 |
| BE876640R (fr) | 1979-11-30 |
| NL7904076A (nl) | 1979-12-04 |
| CA1137995A (en) | 1982-12-21 |
| FR2427326B2 (de) | 1983-08-12 |
| DE2921467A1 (de) | 1979-12-06 |
| ES8200648A2 (es) | 1981-12-01 |
| US4225577A (en) | 1980-09-30 |
| ES480979A0 (es) | 1981-12-01 |
| JPS54163542A (en) | 1979-12-26 |
| CH637918A5 (fr) | 1983-08-31 |
| FR2427326A2 (fr) | 1979-12-28 |
| DK224279A (da) | 1979-12-01 |
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