IT1277950B1 - Prepn. of crystalline, anhydrous Iopamidol - by crystallisation from deionised water, useful as X=ray contrast agent - Google Patents
Prepn. of crystalline, anhydrous Iopamidol - by crystallisation from deionised water, useful as X=ray contrast agentInfo
- Publication number
- IT1277950B1 IT1277950B1 ITRM950831A IT1277950B1 IT 1277950 B1 IT1277950 B1 IT 1277950B1 IT RM950831 A ITRM950831 A IT RM950831A IT 1277950 B1 IT1277950 B1 IT 1277950B1
- Authority
- IT
- Italy
- Prior art keywords
- solution
- crystallisation
- crystalline
- deionised water
- prepn
- Prior art date
Links
- 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 title abstract 3
- 238000002425 crystallisation Methods 0.000 title abstract 2
- 239000008367 deionised water Substances 0.000 title abstract 2
- 229960004647 iopamidol Drugs 0.000 title abstract 2
- 239000002872 contrast media Substances 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000013078 crystal Substances 0.000 abstract 3
- 239000007810 chemical reaction solvent Substances 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000003226 decolorizating effect Effects 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000010899 nucleation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Process (I) for the crystallisation of Iopamidol ((S)-N,N'-bis(2-hydroxy-1- (hydroxymethyl)ethyl)-5- ((2-hydroxy-1-oxopropyl)amino)- 2,4,6-triiodo-1,3-benzenedicarboxamide) (II) from water to afford a crystalline anhydrous form of pharmacopoeia standard involves: (a) dissolving (II) in deionised water by heating; (b) decolourising the solution with active carbon; (c) concn. of the aq. solution in vacuo at 60[deg]C; (d) seeding the hot solution with anhydrous (II); (e) crystallising at 60[deg]C; (f) filtering the ppte; and (g) drying the wet product in vacuo. The use of a 1-4C alcohol to reduce the residual content of reaction solvents in the crystals is also claimed. The aq. solution in step (a) is pref. satd. i.e. contg. > 78.6 g (II)/ml of solution and the amt. of seed crystals added in step (d) is 1-10% of the crude (II). To reduce the content of reaction solvents esp. dimethylacetamide deriving from the previous synthetic steps, the filtered crystals are washed with pref. EtOH.
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITRM950831 IT1277950B1 (en) | 1995-12-19 | 1995-12-19 | Prepn. of crystalline, anhydrous Iopamidol - by crystallisation from deionised water, useful as X=ray contrast agent |
EP96928403A EP0790979B1 (en) | 1995-09-08 | 1996-08-02 | Process for the crystallization from water of (s)-n,n'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide |
DE69605528T DE69605528T2 (en) | 1995-09-08 | 1996-08-02 | METHOD FOR CRYSTALLIZING FROM WATER OF (S) -N, N'-BIS [2-HYDROXY-1- (HYDROXYMETHIEL) ETHYL] -5 - [(2-HYDROXY-1-OXOPROPYL) AMINO] -2,4,6- TRIIODO-1,3-BENZOLDICARBOXAMIDE |
PCT/EP1996/003399 WO1997009300A1 (en) | 1995-09-08 | 1996-08-02 | Process for the crystallization from water of (s)-n,n'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide |
AU67888/96A AU708195B2 (en) | 1995-09-08 | 1996-08-02 | Process for the crystallization from water of (S)-N,N'-bis{2-hydroxy-1-(hydroxymethyl)ethyl}-5-{(2-hydroxy -1-oxopropyl)amino}-2,4,6-triiodo-1,3-benzendicarboxamide |
KR1019970702994A KR100270411B1 (en) | 1995-09-08 | 1996-08-02 | Process for the Crystallization from Water of (S)-N,N'-Bis[2-Hydroxy-1-(Hydroxymethyl)Ethyl]-5-[(2-Hydroxy-1-Oxopropyl)Amino]-2,4,6-Triiodo-1,3-Benzendicarboxamide |
PL96320027A PL184937B1 (en) | 1995-09-08 | 1996-08-02 | Method of crystallising s)-n,n'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[2-hydroxy-1-oxypropyl)amino]2,4,6-triiodine-1,3-benzenodicarboxyamide from aquepus solution |
ES96928403T ES2140887T3 (en) | 1995-09-08 | 1996-08-02 | PROCEDURE FOR CRYSTALLIZING IN WATER (S) -N-N'-BIS (2-HIDROXI-1- (HIDROXIMETIL) ETIL) -5 - ((2-HIDROXI-1-OXOPROPIL) AMINO) -2,4,6-TRIYODO -1,3-BENZENODICARBOXAMIDE. |
CZ19971385A CZ288645B6 (en) | 1995-09-08 | 1996-08-02 | Crystallization process of Iopamidol |
CN96191028A CN1070843C (en) | 1995-09-08 | 1996-08-02 | Process for crystallization from water of (S)-N,N'-bis[2-hydroxy-1-(hydroxymethyl) ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide |
CA002204734A CA2204734C (en) | 1995-09-08 | 1996-08-02 | Process for the crystallization from water of (s)-n,n'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide |
JP50604597A JP4070235B2 (en) | 1995-09-08 | 1996-08-02 | (S) -N, N′-bis [2-hydroxy-1- (hydroxymethyl) ethyl] -5-[(2-hydroxy-1-oxopropyl) amino] -2,4,6-triiodo-1, Method for crystallizing 3-benzenedicarboxamide from water |
BR9606624A BR9606624A (en) | 1995-09-08 | 1996-08-02 | Process for the crystallization of (s) -n, n'-bisÚ2-hydroxy-1- (hydroxymethyl) ethyl¾-5-Ú (2-hydroxy-1-oxopropyl) amino¾-2,4,6-triiodo-1,3 -benzonodicar-boxamide from water |
AT96928403T ATE187437T1 (en) | 1995-09-08 | 1996-08-02 | METHOD FOR CRYSTALLIZATION FROM WATER OF (S)-N,N'-BIS(2-HYDROXY-1-(HYDROXYMETHIEL)ETHYL>5-((2-HYDROXY-1-OXOPROPYL)AMINO>-2,4,6-TRIIODO - ,3- BENZOLDICARBOXAMIDE |
HU9801837A HU220965B1 (en) | 1995-09-08 | 1996-08-02 | Process for the crystallization from water of (s)-n,n'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide |
US08/708,668 US5689002A (en) | 1995-09-08 | 1996-09-05 | Process for the crystallization from water of (S)-N,N'-bis 2-hydroxy-1-(hydroxymethyl)ethyl!-5- 2-hydroxy-1-oxopropyl)amino!-2,4,6-triiodo-1,3-benzendicarboxamide |
NO971863A NO308841B1 (en) | 1995-09-08 | 1997-04-23 | Process for the crystallization of (S) -N, N'-bis [2-hydroxy-1- (hydroxymethyl) ethyl] -5 [(2-hydroxy-1-oxopropyl) amino] -2,4,6-triiodo-1 , 3-benzenedicarboxamide from water, and uses of (C1-C4 alcohols) |
MXPA/A/1997/003341A MXPA97003341A (en) | 1995-09-08 | 1997-05-07 | Process for the crystallization of (s) -n, n'-bis [2-hydroxy-1- (hydroxymethyl) ethyl] -5 - [(2-hydroxy-1-oxopropyl) amino] -2,4,6-triyodo -1,3-bencendicarboxamide from a |
HK98100990A HK1001861A1 (en) | 1995-09-08 | 1998-02-10 | Process for the crystallization from water of (s)-n,n'-bis(2-hydroxy-1-(hydroxymethyl)ethyl)-5-((2-hydroxy-1-oxopropyl)amino)-2,4,6-triiodo-1,3-benzendicarboxamide |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITRM950831 IT1277950B1 (en) | 1995-12-19 | 1995-12-19 | Prepn. of crystalline, anhydrous Iopamidol - by crystallisation from deionised water, useful as X=ray contrast agent |
Publications (3)
Publication Number | Publication Date |
---|---|
ITRM950831A0 ITRM950831A0 (en) | 1995-12-19 |
ITRM950831A1 ITRM950831A1 (en) | 1997-06-19 |
IT1277950B1 true IT1277950B1 (en) | 1997-11-12 |
Family
ID=11403721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ITRM950831 IT1277950B1 (en) | 1995-09-08 | 1995-12-19 | Prepn. of crystalline, anhydrous Iopamidol - by crystallisation from deionised water, useful as X=ray contrast agent |
Country Status (1)
Country | Link |
---|---|
IT (1) | IT1277950B1 (en) |
-
1995
- 1995-12-19 IT ITRM950831 patent/IT1277950B1/en active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
ITRM950831A1 (en) | 1997-06-19 |
ITRM950831A0 (en) | 1995-12-19 |
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