CN110003038A - Ioforminol的中间体化合物的制备 - Google Patents
Ioforminol的中间体化合物的制备 Download PDFInfo
- Publication number
- CN110003038A CN110003038A CN201910145184.3A CN201910145184A CN110003038A CN 110003038 A CN110003038 A CN 110003038A CN 201910145184 A CN201910145184 A CN 201910145184A CN 110003038 A CN110003038 A CN 110003038A
- Authority
- CN
- China
- Prior art keywords
- compound
- ioforminol
- bis
- prepare
- mixture
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 67
- BFVVDRUCXCIALU-UHFFFAOYSA-N 5-[[3-[3,5-bis(2,3-dihydroxypropylcarbamoyl)-n-formyl-2,4,6-triiodoanilino]-2-hydroxypropyl]-formylamino]-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(N(CC(O)CN(C=O)C=2C(=C(C(=O)NCC(O)CO)C(I)=C(C(=O)NCC(O)CO)C=2I)I)C=O)=C1I BFVVDRUCXCIALU-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 229950004332 ioforminol Drugs 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 claims abstract description 31
- -1 formamido group Chemical group 0.000 claims abstract description 19
- 238000012805 post-processing Methods 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000843 powder Substances 0.000 claims description 9
- 239000012296 anti-solvent Substances 0.000 claims description 5
- 125000002346 iodo group Chemical group I* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 229940126214 compound 3 Drugs 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 40
- 239000002872 contrast media Substances 0.000 abstract description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 7
- 238000003384 imaging method Methods 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 4
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 abstract description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 28
- 235000019441 ethanol Nutrition 0.000 description 16
- 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 14
- 235000019253 formic acid Nutrition 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 150000008064 anhydrides Chemical class 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006471 dimerization reaction Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229960004359 iodixanol Drugs 0.000 description 5
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000013590 bulk material Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000193 iodinated contrast media Substances 0.000 description 2
- 229960001025 iohexol Drugs 0.000 description 2
- 229960000780 iomeprol Drugs 0.000 description 2
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 description 2
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 208000003663 ventricular fibrillation Diseases 0.000 description 2
- WEGOLYBUWCMMMY-UHFFFAOYSA-N 1-bromo-2-propanol Chemical class CC(O)CBr WEGOLYBUWCMMMY-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- QMADWSQEVHUFFJ-UHFFFAOYSA-N 2,4,5-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(I)=C(I)C(C(O)=O)=C1I QMADWSQEVHUFFJ-UHFFFAOYSA-N 0.000 description 1
- DUYOHDPGXMPOKD-UHFFFAOYSA-N 2-formyloxypropyl formate Chemical compound O=COC(C)COC=O DUYOHDPGXMPOKD-UHFFFAOYSA-N 0.000 description 1
- HUHDYASLFWQVOL-WZTVWXICSA-N 3-[[2-[[3-[acetyl(methyl)amino]-2,4,6-triiodo-5-(methylcarbamoyl)benzoyl]amino]acetyl]amino]-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I HUHDYASLFWQVOL-WZTVWXICSA-N 0.000 description 1
- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 150000004075 acetic anhydrides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000002586 coronary angiography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960005423 diatrizoate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229960004647 iopamidol Drugs 0.000 description 1
- TYYBFXNZMFNZJT-UHFFFAOYSA-N ioxaglic acid Chemical class CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I TYYBFXNZMFNZJT-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20121102 | 2012-09-27 | ||
| NO20121102 | 2012-09-27 | ||
| CN201380050455.8A CN104661996A (zh) | 2012-09-27 | 2013-09-17 | Ioforminol的中间体化合物的制备 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380050455.8A Division CN104661996A (zh) | 2012-09-27 | 2013-09-17 | Ioforminol的中间体化合物的制备 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110003038A true CN110003038A (zh) | 2019-07-12 |
Family
ID=49274871
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910145184.3A Pending CN110003038A (zh) | 2012-09-27 | 2013-09-17 | Ioforminol的中间体化合物的制备 |
| CN201380050455.8A Pending CN104661996A (zh) | 2012-09-27 | 2013-09-17 | Ioforminol的中间体化合物的制备 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380050455.8A Pending CN104661996A (zh) | 2012-09-27 | 2013-09-17 | Ioforminol的中间体化合物的制备 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9884808B2 (https=) |
| EP (1) | EP2900632B1 (https=) |
| JP (1) | JP6431842B2 (https=) |
| KR (1) | KR20150061635A (https=) |
| CN (2) | CN110003038A (https=) |
| AU (1) | AU2013323981B2 (https=) |
| BR (1) | BR112015004591A2 (https=) |
| CA (1) | CA2881852A1 (https=) |
| IN (1) | IN2015DN01185A (https=) |
| MX (1) | MX354604B (https=) |
| RU (1) | RU2654461C2 (https=) |
| WO (1) | WO2014052091A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX354604B (es) | 2012-09-27 | 2018-03-07 | Ge Healthcare As | Preparacion de un compuesto intermediario de ioforminol. |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000047549A1 (en) * | 1999-02-11 | 2000-08-17 | Nycomed Imaging As | Preparation of iodixanol |
| CN101233092A (zh) * | 2005-07-29 | 2008-07-30 | 通用电气医疗集团股份有限公司 | 碘化苯基衍生物的连续结晶方法 |
| CN101687051A (zh) * | 2007-07-12 | 2010-03-31 | 通用电气医疗集团股份有限公司 | 造影剂 |
| CN101962342A (zh) * | 2009-07-21 | 2011-02-02 | 通用电气医疗集团股份有限公司 | 非离子x射线造影剂的合成中的连续脱乙酰化和纯化工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE20733T1 (de) | 1982-11-08 | 1986-08-15 | Nyegaard & Co As | Roentgenkontrastmittel. |
| AU6114396A (en) | 1995-06-16 | 1997-01-15 | Biophysica Foundation | Formyl derivatives as nonionic contrast media |
| GB9624612D0 (en) | 1996-11-26 | 1997-01-15 | Nycomed Imaging As | Process |
| NO20043305D0 (no) | 2004-08-09 | 2004-08-09 | Amersham Health As | Preparation of lodixanol |
| MX354604B (es) | 2012-09-27 | 2018-03-07 | Ge Healthcare As | Preparacion de un compuesto intermediario de ioforminol. |
| AU2013323982B2 (en) * | 2012-09-27 | 2017-11-23 | Ge Healthcare As | Preparation of Ioforminol, an X-ray contrast agent |
-
2013
- 2013-09-17 MX MX2015003912A patent/MX354604B/es active IP Right Grant
- 2013-09-17 AU AU2013323981A patent/AU2013323981B2/en not_active Ceased
- 2013-09-17 CA CA2881852A patent/CA2881852A1/en not_active Abandoned
- 2013-09-17 CN CN201910145184.3A patent/CN110003038A/zh active Pending
- 2013-09-17 WO PCT/US2013/060081 patent/WO2014052091A1/en not_active Ceased
- 2013-09-17 RU RU2015107016A patent/RU2654461C2/ru not_active IP Right Cessation
- 2013-09-17 EP EP13771008.3A patent/EP2900632B1/en active Active
- 2013-09-17 US US14/430,155 patent/US9884808B2/en not_active Expired - Fee Related
- 2013-09-17 CN CN201380050455.8A patent/CN104661996A/zh active Pending
- 2013-09-17 JP JP2015534549A patent/JP6431842B2/ja not_active Expired - Fee Related
- 2013-09-17 KR KR1020157007427A patent/KR20150061635A/ko not_active Ceased
- 2013-09-17 BR BR112015004591A patent/BR112015004591A2/pt not_active Application Discontinuation
-
2015
- 2015-02-13 IN IN1185DEN2015 patent/IN2015DN01185A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000047549A1 (en) * | 1999-02-11 | 2000-08-17 | Nycomed Imaging As | Preparation of iodixanol |
| CN101233092A (zh) * | 2005-07-29 | 2008-07-30 | 通用电气医疗集团股份有限公司 | 碘化苯基衍生物的连续结晶方法 |
| CN101687051A (zh) * | 2007-07-12 | 2010-03-31 | 通用电气医疗集团股份有限公司 | 造影剂 |
| CN101962342A (zh) * | 2009-07-21 | 2011-02-02 | 通用电气医疗集团股份有限公司 | 非离子x射线造影剂的合成中的连续脱乙酰化和纯化工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015532280A (ja) | 2015-11-09 |
| CN104661996A (zh) | 2015-05-27 |
| AU2013323981A1 (en) | 2015-03-05 |
| IN2015DN01185A (https=) | 2015-06-26 |
| MX2015003912A (es) | 2015-08-05 |
| US9884808B2 (en) | 2018-02-06 |
| RU2015107016A (ru) | 2016-11-20 |
| WO2014052091A1 (en) | 2014-04-03 |
| US20150246871A1 (en) | 2015-09-03 |
| CA2881852A1 (en) | 2014-04-03 |
| EP2900632A1 (en) | 2015-08-05 |
| JP6431842B2 (ja) | 2018-11-28 |
| KR20150061635A (ko) | 2015-06-04 |
| AU2013323981B2 (en) | 2017-09-14 |
| MX354604B (es) | 2018-03-07 |
| EP2900632B1 (en) | 2019-10-30 |
| RU2654461C2 (ru) | 2018-05-18 |
| BR112015004591A2 (pt) | 2017-07-04 |
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