NO323772B1 - Motsatt fasekromatografisk prosess - Google Patents
Motsatt fasekromatografisk prosess Download PDFInfo
- Publication number
- NO323772B1 NO323772B1 NO19985542A NO985542A NO323772B1 NO 323772 B1 NO323772 B1 NO 323772B1 NO 19985542 A NO19985542 A NO 19985542A NO 985542 A NO985542 A NO 985542A NO 323772 B1 NO323772 B1 NO 323772B1
- Authority
- NO
- Norway
- Prior art keywords
- column
- contrast agent
- agent compound
- solvent
- ionic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 53
- 230000008569 process Effects 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 69
- 239000002904 solvent Substances 0.000 claims abstract description 35
- 239000012535 impurity Substances 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 22
- 238000012856 packing Methods 0.000 claims abstract description 19
- 238000000746 purification Methods 0.000 claims abstract description 13
- 238000004042 decolorization Methods 0.000 claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 239000002872 contrast media Substances 0.000 claims description 58
- 238000011084 recovery Methods 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 27
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000000356 contaminant Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 2
- 239000003690 nonionic contrast media Substances 0.000 abstract description 11
- 239000000047 product Substances 0.000 description 20
- AMDBBAQNWSUWGN-UHFFFAOYSA-N Ioversol Chemical compound OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I AMDBBAQNWSUWGN-UHFFFAOYSA-N 0.000 description 10
- 229960004537 ioversol Drugs 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000002242 deionisation method Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000011097 chromatography purification Methods 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000002595 magnetic resonance imaging Methods 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- -1 2-hydroxytrimethylene Chemical group 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- DGAIEPBNLOQYER-UHFFFAOYSA-N iopromide Chemical compound COCC(=O)NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I DGAIEPBNLOQYER-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- KZYHGCLDUQBASN-UHFFFAOYSA-N 1-n,1-n,3-n,3-n,5-n,5-n-hexakis(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3,5-tricarboxamide Chemical compound OCCN(CCO)C(=O)C1=C(I)C(C(=O)N(CCO)CCO)=C(I)C(C(=O)N(CCO)CCO)=C1I KZYHGCLDUQBASN-UHFFFAOYSA-N 0.000 description 1
- DFDJVFYYDGMDTB-BIYVAJLZSA-N 1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[[(3s,4r,5s)-3,4,5,6-tetrahydroxy-2-oxohexanoyl]amino]benzene-1,3-dicarboxamide Chemical compound OCC(O)CNC(=O)C1=C(I)C(NC(=O)C(=O)[C@@H](O)[C@H](O)[C@@H](O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I DFDJVFYYDGMDTB-BIYVAJLZSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- MKMHLTWTZQIVCH-SFNQMWQSSA-N 3-[acetyl(2-hydroxyethyl)amino]-2,4,6-triiodo-n-methyl-5-[[(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoyl]amino]benzamide Chemical compound CNC(=O)C1=C(I)C(NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)=C(I)C(N(CCO)C(C)=O)=C1I MKMHLTWTZQIVCH-SFNQMWQSSA-N 0.000 description 1
- OQHLOKBHRXMXLD-UHFFFAOYSA-N 5-[3-[3-[3,5-bis[2,3-dihydroxypropyl(methyl)carbamoyl]-2,4,6-triiodoanilino]-3-oxopropyl]sulfanylpropanoylamino]-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1-n,3-n-dimethylbenzene-1,3-dicarboxamide Chemical compound OCC(O)CN(C)C(=O)C1=C(I)C(C(=O)N(CC(O)CO)C)=C(I)C(NC(=O)CCSCCC(=O)NC=2C(=C(C(=O)N(C)CC(O)CO)C(I)=C(C(=O)N(C)CC(O)CO)C=2I)I)=C1I OQHLOKBHRXMXLD-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 125000003713 acetylimino group Chemical group [H]C([H])([H])C(=O)N=[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229960004359 iodixanol Drugs 0.000 description 1
- 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 1
- 229950008828 ioglucol Drugs 0.000 description 1
- 229960001025 iohexol 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
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229960004647 iopamidol Drugs 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
- 229960000824 iopentol Drugs 0.000 description 1
- IUNJANQVIJDFTQ-UHFFFAOYSA-N iopentol Chemical compound COCC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I IUNJANQVIJDFTQ-UHFFFAOYSA-N 0.000 description 1
- 229960002603 iopromide Drugs 0.000 description 1
- 229950011065 iosimide Drugs 0.000 description 1
- 229950011097 iotasul Drugs 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/32—Bonded phase chromatography
- B01D15/325—Reversed phase
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE960412 | 1996-06-05 | ||
| PCT/IE1997/000040 WO1997046299A1 (en) | 1996-06-05 | 1997-06-04 | Reversed phase chromatographic process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO985542D0 NO985542D0 (no) | 1998-11-27 |
| NO985542L NO985542L (no) | 1999-01-18 |
| NO323772B1 true NO323772B1 (no) | 2007-07-02 |
Family
ID=11041183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19985542A NO323772B1 (no) | 1996-06-05 | 1998-11-27 | Motsatt fasekromatografisk prosess |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0907395B1 (es) |
| AT (1) | ATE208223T1 (es) |
| AU (1) | AU3187197A (es) |
| DE (1) | DE69708090T2 (es) |
| ES (1) | ES2163170T3 (es) |
| GB (1) | GB2328385B (es) |
| NO (1) | NO323772B1 (es) |
| WO (1) | WO1997046299A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101961564B (zh) * | 2010-08-13 | 2012-07-04 | 浙江大学宁波理工学院 | 五区模拟移动床色谱分离系统 |
| FR3084668A1 (fr) | 2018-08-02 | 2020-02-07 | Guerbet | Procede de preparation monotope de composes organo-iodes intermediaires a la synthese du ioversol |
| CN112724035A (zh) * | 2021-03-01 | 2021-04-30 | 江苏汉邦科技有限公司 | 一种纯化制备碘佛醇水解物的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5204005A (en) * | 1990-02-26 | 1993-04-20 | Mallinckrodt, Inc. | Reversed phase chromatographic process |
| WO1997020609A1 (en) * | 1995-12-01 | 1997-06-12 | Mallinckrodt Medical Imaging-Ireland | Reversed phase chromatographic process |
| WO1997020610A1 (en) * | 1995-12-01 | 1997-06-12 | Mallinckrodt Medical Imaging-Ireland | Reversed phase chromatographic process |
-
1997
- 1997-06-04 AT AT97927343T patent/ATE208223T1/de not_active IP Right Cessation
- 1997-06-04 ES ES97927343T patent/ES2163170T3/es not_active Expired - Lifetime
- 1997-06-04 EP EP97927343A patent/EP0907395B1/en not_active Expired - Lifetime
- 1997-06-04 GB GB9824512A patent/GB2328385B/en not_active Expired - Fee Related
- 1997-06-04 DE DE69708090T patent/DE69708090T2/de not_active Expired - Fee Related
- 1997-06-04 AU AU31871/97A patent/AU3187197A/en not_active Abandoned
- 1997-06-04 WO PCT/IE1997/000040 patent/WO1997046299A1/en active IP Right Grant
-
1998
- 1998-11-27 NO NO19985542A patent/NO323772B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB9824512D0 (en) | 1999-01-06 |
| AU3187197A (en) | 1998-01-05 |
| DE69708090T2 (de) | 2002-07-18 |
| ES2163170T3 (es) | 2002-01-16 |
| NO985542L (no) | 1999-01-18 |
| IE970412A1 (en) | 1997-12-17 |
| GB2328385B (en) | 2000-10-25 |
| EP0907395A1 (en) | 1999-04-14 |
| WO1997046299A1 (en) | 1997-12-11 |
| ATE208223T1 (de) | 2001-11-15 |
| NO985542D0 (no) | 1998-11-27 |
| DE69708090D1 (de) | 2001-12-13 |
| EP0907395B1 (en) | 2001-11-07 |
| GB2328385A (en) | 1999-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |