WO2014052091A1 - Preparation of an intermediate compound of ioforminol - Google Patents
Preparation of an intermediate compound of ioforminol Download PDFInfo
- Publication number
- WO2014052091A1 WO2014052091A1 PCT/US2013/060081 US2013060081W WO2014052091A1 WO 2014052091 A1 WO2014052091 A1 WO 2014052091A1 US 2013060081 W US2013060081 W US 2013060081W WO 2014052091 A1 WO2014052091 A1 WO 2014052091A1
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- WO
- WIPO (PCT)
- Prior art keywords
- compound
- compound mixture
- preparation
- mixture
- bis
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 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 abstract description 8
- 229950004332 ioforminol Drugs 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 37
- 238000010626 work up procedure Methods 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000000843 powder Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- KAEGSAWWVYMWIQ-UHFFFAOYSA-N 5-amino-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I KAEGSAWWVYMWIQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 229960004592 isopropanol Drugs 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000002872 contrast media Substances 0.000 abstract description 24
- 239000000543 intermediate Substances 0.000 abstract description 5
- 238000003384 imaging method Methods 0.000 abstract description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 150000008064 anhydrides Chemical class 0.000 description 13
- 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 10
- 235000019253 formic acid Nutrition 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 229940039231 contrast media Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006170 formylation reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 239000012296 anti-solvent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- -1 isophthalamide compound Chemical class 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
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000022244 formylation Effects 0.000 description 3
- 229960004359 iodixanol Drugs 0.000 description 3
- 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 3
- 239000000463 material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-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
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940126214 compound 3 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
- 239000012535 impurity Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229960001025 iohexol Drugs 0.000 description 2
- 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 2
- 239000000178 monomer Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012066 reaction slurry Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- KIHQZLPHVZKELA-UHFFFAOYSA-N 1,3-dibromopropan-2-ol Chemical compound BrCC(O)CBr KIHQZLPHVZKELA-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- TVCINXHQUODERO-UHFFFAOYSA-N 1-n,3-n-bis(2,3-dihydroxypropyl)-5-formamido-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(NC=O)=C(I)C(C(=O)NCC(O)CO)=C1I TVCINXHQUODERO-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-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
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 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
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 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
- 125000003277 amino group Chemical group 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
- 239000002585 base Substances 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 229960005423 diatrizoate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical group O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 231100000268 induced nephrotoxicity Toxicity 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000193 iodinated contrast media Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960000780 iomeprol Drugs 0.000 description 1
- 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 1
- 150000002500 ions Chemical class 0.000 description 1
- 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 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 229940029407 ioxaglate Drugs 0.000 description 1
- TYYBFXNZMFNZJT-UHFFFAOYSA-N ioxaglic acid Chemical compound 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
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 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
Definitions
- the process comprises the steps of:
- the amount of alcohol used in the washing may be about the same amount as used in the precipitation, divided on the number of portions. It has been found that it is beneficially for the further synthesis that some alcohol is left in the compound mixture (3) after the work-up procedure has finished, hence the drying should be adjusted accordingly. Preparation of compound mixture (3) with a rest alcohol content of 0-7 % has been found appropriate.
- the compounds prepared according to the invention may be used as contrast agents and may be formulated with conventional carriers and excipients to produce diagnostic contrast media.
- the invention provides a diagnostic composition comprising loforminol prepared according to the process of the invention, together with at least one physiologically tolerable carrier or excipient, e.g. in aqueous solution for injection optionally together with added plasma ions or dissolved oxygen.
- the contrast agent composition of the invention may be in a ready to use concentration or may be a concentrate form for dilution prior to administration.
- the invention further embraces use of loforminol prepared according to the process of preparation, and a diagnostic composition containing such, in X-ray contrast examinations.
- the invention is illustrated with reference to the following non-limiting examples.
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)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2881852A CA2881852A1 (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol |
RU2015107016A RU2654461C2 (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol synthesis |
US14/430,155 US9884808B2 (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol |
MX2015003912A MX354604B (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol. |
AU2013323981A AU2013323981B2 (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of Ioforminol |
KR1020157007427A KR20150061635A (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol |
BR112015004591A BR112015004591A2 (en) | 2012-09-27 | 2013-09-17 | processes for preparing a mixture of a compound and preparing ioforminol, and mixing a compound in powder form |
JP2015534549A JP6431842B2 (en) | 2012-09-27 | 2013-09-17 | Preparation of intermediate compound of ioforminol |
CN201380050455.8A CN104661996A (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol |
EP13771008.3A EP2900632B1 (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol |
IN1185DEN2015 IN2015DN01185A (en) | 2012-09-27 | 2015-02-13 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO20121102 | 2012-09-27 | ||
NO20121102 | 2012-09-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014052091A1 true WO2014052091A1 (en) | 2014-04-03 |
Family
ID=49274871
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2013/060081 WO2014052091A1 (en) | 2012-09-27 | 2013-09-17 | Preparation of an intermediate compound of ioforminol |
Country Status (12)
Country | Link |
---|---|
US (1) | US9884808B2 (en) |
EP (1) | EP2900632B1 (en) |
JP (1) | JP6431842B2 (en) |
KR (1) | KR20150061635A (en) |
CN (2) | CN110003038A (en) |
AU (1) | AU2013323981B2 (en) |
BR (1) | BR112015004591A2 (en) |
CA (1) | CA2881852A1 (en) |
IN (1) | IN2015DN01185A (en) |
MX (1) | MX354604B (en) |
RU (1) | RU2654461C2 (en) |
WO (1) | WO2014052091A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9884808B2 (en) | 2012-09-27 | 2018-02-06 | Ge Healthcare As | Preparation of an intermediate compound of ioforminol |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0108638A1 (en) | 1982-11-08 | 1984-05-16 | NYEGAARD & CO. A/S | X-ray contrast agents |
WO1998023296A1 (en) | 1996-11-26 | 1998-06-04 | Nycomed Imaging As | Process for the production of iodinated organic x-ray contrast agents |
WO2000047549A1 (en) * | 1999-02-11 | 2000-08-17 | Nycomed Imaging As | Preparation of iodixanol |
WO2006016815A1 (en) | 2004-08-09 | 2006-02-16 | Ge Healthcare As | Preparation of iodixanol |
WO2009008734A2 (en) | 2007-07-12 | 2009-01-15 | Ge Healthcare As | Contrast agents |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0855997A4 (en) | 1995-06-16 | 1998-10-07 | Biophysica Inc | Formyl derivatives as nonionic contrast media |
NO20053687D0 (en) | 2005-07-29 | 2005-07-29 | Amersham Health As | Crystallization Process. |
US20110021822A1 (en) * | 2009-07-21 | 2011-01-27 | Ge Healthcare As | continuous deacetylation and purification process in synthesis of non-ionic x-ray contrast agents |
JP6431842B2 (en) | 2012-09-27 | 2018-11-28 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | Preparation of intermediate compound of ioforminol |
WO2014052092A1 (en) * | 2012-09-27 | 2014-04-03 | Ge Healthcare As | Preparation of ioforminol, an x-ray contrast agent |
-
2013
- 2013-09-17 JP JP2015534549A patent/JP6431842B2/en not_active Expired - Fee Related
- 2013-09-17 US US14/430,155 patent/US9884808B2/en not_active Expired - Fee Related
- 2013-09-17 CN CN201910145184.3A patent/CN110003038A/en active Pending
- 2013-09-17 MX MX2015003912A patent/MX354604B/en active IP Right Grant
- 2013-09-17 WO PCT/US2013/060081 patent/WO2014052091A1/en active Application Filing
- 2013-09-17 CN CN201380050455.8A patent/CN104661996A/en active Pending
- 2013-09-17 BR BR112015004591A patent/BR112015004591A2/en not_active Application Discontinuation
- 2013-09-17 AU AU2013323981A patent/AU2013323981B2/en not_active Ceased
- 2013-09-17 EP EP13771008.3A patent/EP2900632B1/en active Active
- 2013-09-17 KR KR1020157007427A patent/KR20150061635A/en not_active Application Discontinuation
- 2013-09-17 RU RU2015107016A patent/RU2654461C2/en not_active IP Right Cessation
- 2013-09-17 CA CA2881852A patent/CA2881852A1/en not_active Abandoned
-
2015
- 2015-02-13 IN IN1185DEN2015 patent/IN2015DN01185A/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0108638A1 (en) | 1982-11-08 | 1984-05-16 | NYEGAARD & CO. A/S | X-ray contrast agents |
WO1998023296A1 (en) | 1996-11-26 | 1998-06-04 | Nycomed Imaging As | Process for the production of iodinated organic x-ray contrast agents |
WO2000047549A1 (en) * | 1999-02-11 | 2000-08-17 | Nycomed Imaging As | Preparation of iodixanol |
WO2006016815A1 (en) | 2004-08-09 | 2006-02-16 | Ge Healthcare As | Preparation of iodixanol |
WO2009008734A2 (en) | 2007-07-12 | 2009-01-15 | Ge Healthcare As | Contrast agents |
Non-Patent Citations (3)
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US9884808B2 (en) | 2012-09-27 | 2018-02-06 | Ge Healthcare As | Preparation of an intermediate compound of ioforminol |
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CN110003038A (en) | 2019-07-12 |
EP2900632B1 (en) | 2019-10-30 |
BR112015004591A2 (en) | 2017-07-04 |
RU2654461C2 (en) | 2018-05-18 |
JP6431842B2 (en) | 2018-11-28 |
AU2013323981B2 (en) | 2017-09-14 |
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RU2015107016A (en) | 2016-11-20 |
AU2013323981A1 (en) | 2015-03-05 |
US20150246871A1 (en) | 2015-09-03 |
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JP2015532280A (en) | 2015-11-09 |
CN104661996A (en) | 2015-05-27 |
US9884808B2 (en) | 2018-02-06 |
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MX2015003912A (en) | 2015-08-05 |
EP2900632A1 (en) | 2015-08-05 |
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