CN115806498A - Method for synthesizing 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl chloride - Google Patents
Method for synthesizing 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl chloride Download PDFInfo
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- CN115806498A CN115806498A CN202111112694.4A CN202111112694A CN115806498A CN 115806498 A CN115806498 A CN 115806498A CN 202111112694 A CN202111112694 A CN 202111112694A CN 115806498 A CN115806498 A CN 115806498A
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- chloride
- triiodo
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- chloroacetamide
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 32
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 16
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000008213 purified water Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006482 condensation reaction Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000001035 drying Methods 0.000 claims abstract description 9
- 239000008096 xylene Substances 0.000 claims abstract description 9
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- ZDPKPVZLNQECET-UHFFFAOYSA-N 5-[(2-chloroacetyl)amino]-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClCC(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I ZDPKPVZLNQECET-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 5
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002425 crystallisation Methods 0.000 claims abstract description 4
- 230000008025 crystallization Effects 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 238000001308 synthesis method Methods 0.000 claims description 6
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 5
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000002351 wastewater Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229960004537 ioversol Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- FQAXLTARZOJBPJ-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=C(I)C=C(I)C(C(Cl)=O)=C1I FQAXLTARZOJBPJ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- MFKHKJMRWGOTHL-UHFFFAOYSA-M ethyl(trioctyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CC)(CCCCCCCC)CCCCCCCC MFKHKJMRWGOTHL-UHFFFAOYSA-M 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 5-chloroacetamide-2, 4, 6-triiodo isophthaloyl dichloride, which comprises the following steps: 5-amino-2, 4, 6-triiodo isophthalic acid chloride is used as a raw material, a nonpolar solvent is used as a solvent, and a phase transfer catalyst is used as a catalyst; heating and raising the temperature, and carrying out a condensation reaction on the 5-amino-2, 4, 6-triiodo isophthalic acid chloride and chloroacetyl chloride under the catalytic action of a phase transfer catalyst; after the condensation reaction is finished, cooling to room temperature, adding purified water into the system for crystallization, and filtering and drying to obtain the 5-chloroacetamido-2, 4, 6-triiodo isophthaloyl chloride. The method adopts toluene or xylene as a solvent, the yield of the prepared 5-chloroacetamide-2, 4, 6-triiodo isophthaloyl dichloride is more than 90 percent, the operation is simple, the used solvent of toluene or xylene can be recycled, and the waste water amount is small and easy to treat.
Description
Technical Field
The invention relates to a synthesis method of 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl chloride, belonging to the technical field of chemical synthesis.
Background
5-chloroacetamide-2, 4, 6-triiodoisophthaloyl chloride is an important medical intermediate, and is mainly used for synthesizing a contrast agent ioversol and the like.
2,4, 6-triiodoisophthaloyl chloride is usually condensed with chloroacetyl chloride in solvents of N, N-dimethylformamide and N, N-dimethylacetamide, the reaction solution is viscous in the reaction process, the post-treatment needs to be carried out by adding the reaction solution into purification, and the product is precipitated at low temperature. The product yield after post-treatment is low, the used solvent can not be recovered, the waste water contains a large amount of nitrogen-containing compounds, and the environmental pollution is serious.
Patent CN101654417 reports that 5-amino-2,4,6-triiodo isophthalic acid chloride is used as raw material, N-dimethylacetamide is used as solvent, chloroacetyl chloride is added at low temperature, then the mixture is heated to 30-70 ℃ for reaction, after the reaction is finished, the reaction solution is added into ice water, crystallized at 5 ℃, and filtered to obtain the product, and the method is difficult in waste water treatment. US4396598A, US5648536 and US5075502A report similar and identical processes for the preparation of similar compounds using N, N-dimethylacetamide as solvent.
The ioversol injection is used for large-dose administration, 1ml contains 0.32 g of iodine, and the ioversol injection is sold in the market with the specifications of 20ml and 50ml, and the common dosage is 20-50 ml. Therefore, the consumption of raw materials of ioversol is huge, the preparation demand of the intermediate 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl dichloride is more, and the 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl dichloride prepared by taking N, N-dimethylacetamide as a solvent generates a large amount of nitrogen, thereby causing great pollution to the environment.
Disclosure of Invention
The invention aims to solve the technical problem of the prior art and provides a method for synthesizing 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl dichloride, which takes a nonpolar solvent as a solvent, adds a phase transfer catalyst, heats up, cools down, and then adds purified water for crystallization to obtain the 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl dichloride. The method for preparing the 5-chloroacetamide-2, 4, 6-triiodoisophthaloyl chloride has the advantages of simple operation, recoverable solvent, low cost and small environmental pollution.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for synthesizing 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl chloride comprises the following steps:
5-amino-2, 4, 6-triiodo isophthaloyl chloride is used as a raw material, a nonpolar solvent is used as a solvent, and a phase transfer catalyst is used as a catalyst; heating and raising the temperature, and carrying out a condensation reaction on the 5-amino-2, 4, 6-triiodo isophthalic acid chloride and chloroacetyl chloride under the catalytic action of a phase transfer catalyst; after the condensation reaction is finished, cooling to room temperature, then adding purified water into the system for crystallization, and obtaining the 5-chloroacetamide-2, 4, 6-triiodo isophthaloyl chloride after filtration and drying.
In the technical scheme, the molar ratio of the chloracetyl chloride to the 5-amino-2, 4, 6-triiodoisophthaloyl dichloride is 1: 1.0-2.0, preferably 1: 1.4-1.7.
In the technical scheme, the nonpolar solvent is any one of toluene and xylene or a mixture of the toluene and the xylene which are mixed in any proportion; preferably, the solvent is either toluene or xylene.
In the technical scheme, the mass ratio of the nonpolar solvent to the 5-amino-2, 4, 6-triiodo isophthaloyl chloride is 1: 1-3, preferably 1: 1.5-2.
In the technical scheme, the phase transfer catalyst is a mixture formed by mixing any one, two or more than two of tetrabutylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium iodide, methyl trioctyl ammonium chloride, propylene glycol, DMF and DMAC in any proportion; preferably, the mixture is prepared by mixing any one, two or more than two of tetrabutylammonium bromide, methyltrioctylammonium chloride, DMF and DMAC in any proportion.
In the technical scheme, the mass ratio of the phase transfer catalyst to the 5-amino-2, 4, 6-triiodo isophthaloyl chloride is 1: 0.01-0.1, preferably 1: 0.02-0.05.
In the technical scheme, the condensation reaction is carried out at the reaction temperature of 60-90 ℃ for 6-12 h; preferably, the reaction temperature is 70-80 ℃, and the reaction time is 7-10 h.
In the technical scheme, the mass ratio of the purified water to the 5-amino-2, 4, 6-triiodo isophthaloyl chloride is 1: 0-2, preferably 1: 0.5-1.5.
In the technical scheme, the drying is carried out at the temperature of 50-60 ℃ for 8-10h.
The technical scheme of the invention has the advantages that: the invention adopts toluene or xylene as solvent, 5-amino-2, 4, 6-triiodo isophthalic acid chloride and chloroacetyl chloride react for condensation reaction under the action of phase transfer catalyst, the yield of 5-chloroacetamide-2, 4, 6-triiodo isophthalic acid chloride is more than 90% by post-treatment, cooling and adding purified water, the operation is simple, the used solvent toluene or xylene can be recovered, the waste water amount is small, and the treatment is easy.
Detailed Description
The following detailed description of the embodiments of the present invention is provided, but the present invention is not limited to the following descriptions:
the invention will now be illustrated with reference to specific examples:
example 1:
a method for synthesizing 5-chloroacetamide-2, 4, 6-triiodoisophthaloyl chloride comprises the following steps:
adding 5-amino-2, 4, 6-triiodoisophthaloyl chloride (200g, 0.34mol) into a 2L three-necked flask, adding 300g of toluene, adding 5g of methyl trioctylmethylammonium chloride, and adding 10g of DMAC; adding chloroacetyl chloride (56.87g, 0.50mol), heating to 70-80 ℃ after adding, keeping the temperature for 8h, monitoring 5-amino-2, 4, 6-triiodo isophthaloyl chloride by TLC for complete reaction, cooling to room temperature, adding 200g of purified water, stirring for 0.5h, filtering, and drying at 50-60 ℃ for 8h to obtain 210.3g of 5-chloroacetamido-2, 4, 6-triiodo isophthaloyl chloride with the yield of 93.2%, and the HPLC purity: 98.2 percent.
Example 2:
a method for synthesizing 5-chloroacetamide-2, 4, 6-triiodoisophthaloyl chloride comprises the following steps:
adding 5-amino-2, 4, 6-triiodoisophthaloyl chloride (200g, 0.34mol), adding 300g of dimethylbenzene, adding 5g of tetrabutylammonium bromide, adding 56.87g,0.50mol of chloroacetyl chloride, heating to 70-80 ℃ after adding, preserving heat for 10h, monitoring 5-amino-2, 4, 6-triiodoisophthaloyl chloride by TLC to react completely, cooling to room temperature, adding 100g of purified water, stirring for 0.5h, filtering, drying at 50-60 ℃ for 9h to obtain 206.5g of 5-chloroacetamido-2, 4, 6-triiodoisophthaloyl chloride, the yield is 91.5%, and the HPLC purity is as follows: 98.3 percent.
Example 3:
a method for synthesizing 5-chloroacetamide-2, 4, 6-triiodoisophthaloyl chloride comprises the following steps:
adding 5-amino-2, 4, 6-triiodo isophthaloyl chloride (300g, 0.504mol) into a 2L three-necked bottle, adding 450g of methylbenzene, adding 7.5g of tetrabutylammonium bromide and adding 15g of DMF; adding chloroacetyl chloride (91g, 0.81mol), heating to 70-80 ℃ after adding, keeping the temperature for 8h, monitoring the 5-amino-2, 4, 6-triiodo isophthaloyl chloride to be reacted completely by TLC, cooling to room temperature, adding 150g of purified water, stirring for 0.5h, filtering, drying at 50-60 ℃ for 10h to obtain 311.4g of 5-chloroacetamido-2, 4, 6-triiodo isophthaloyl chloride, the yield is 92.0 percent, and the HPLC purity is as follows: 97.8 percent.
Comparative example 1: DMAC as solvent
In a 1L three-necked flask, 5-amino-2, 4, 6-triiodoisophthaloyl chloride (60g, 0.1mol) was added to 125ml of N, N-dimethylacetamide at room temperature, stirred well, and cooled to 10 ℃. Dropping 16.0g (15 mmol) of chloroacetyl chloride for about 30min, heating to 50 ℃ after the addition, stirring for 4 hours, finishing TLC reaction, cooling to room temperature, dropping the reaction solution into 500ml of ice-water mixture, continuously cooling to 0-5 ℃, stirring for 1 hour, filtering, washing with 100ml of purified water, drying at 50-6 ℃ to obtain 57.1g of product, wherein the yield is 89%, and the HPLC purity: 96.1 percent.
The above examples are only for illustrating the technical concept and features of the present invention, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (9)
1. A method for synthesizing 5-chloroacetamide-2, 4, 6-triiodo isophthaloyl chloride is characterized by comprising the following steps:
5-amino-2, 4, 6-triiodo isophthalic acid chloride is used as a raw material, a nonpolar solvent is used as a solvent, and a phase transfer catalyst is used as a catalyst; heating and raising the temperature, and carrying out a condensation reaction on the 5-amino-2, 4, 6-triiodo-isophthaloyl dichloride and chloroacetyl chloride under the catalytic action of a phase transfer catalyst; after the condensation reaction is finished, cooling to room temperature, adding purified water into the system for crystallization, and filtering and drying to obtain the 5-chloroacetamido-2, 4, 6-triiodo isophthaloyl chloride.
2. The synthesis method of claim 1, wherein the molar ratio of chloroacetyl chloride to 5-amino-2, 4, 6-triiodoisophthaloyl chloride is 1: 1.0-2.0.
3. The method according to claim 1, wherein the nonpolar solvent is one of toluene and xylene, or a mixture of toluene and xylene mixed at an arbitrary ratio.
4. The method as set forth in claim 1, wherein the mass ratio of the nonpolar solvent to the 5-amino-2, 4, 6-triiodoisophthaloyl chloride is 1: 1-3.
5. The synthesis method of claim 1, wherein the phase transfer catalyst is a mixture of one, two or more of tetrabutylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium iodide, methyltrioctylammonium chloride, propylene glycol, DMF and DMAC in any proportion.
6. The synthesis method of claim 1, wherein the mass ratio of the phase transfer catalyst to the 5-amino-2, 4, 6-triiodoisophthaloyl chloride is 1: 0.01-0.1.
7. The synthesis method according to claim 1, wherein the condensation reaction is carried out at a temperature of 60-90 ℃ for 6-12 h.
8. The synthesis method according to claim 1, wherein the mass ratio of the purified water to the 5-amino-2, 4, 6-triiodoisophthaloyl chloride is 1: 0-2.
9. The synthesis process as claimed in claim 1, wherein the drying is carried out at 50-60 ℃ for 8-10h.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111112694.4A CN115806498A (en) | 2021-09-15 | 2021-09-15 | Method for synthesizing 5-chloroacetamide-2, 4, 6-triiodo-isophthaloyl chloride |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4283381A (en) * | 1979-07-12 | 1981-08-11 | Schering Aktiengesellschaft | Triiodinated aminoacetamido isophthalamide x-ray contrast agents |
| ES2037605A1 (en) * | 1991-11-18 | 1993-06-16 | Invest Justesa Imagen S A Cent | New iodinated dimers X=ray contrast agent prepn. |
| EP0571593A1 (en) * | 1991-11-18 | 1993-12-01 | Invest Justesa Imagen S A Cent | New non ionic iodized agents for x-ray contrasting, method for preparing them and galenical compositions containing them. |
| CN101654417A (en) * | 2009-09-01 | 2010-02-24 | 江苏省原子医学研究所 | Preparation method of X-ray contrast agent ioversol intermediate |
-
2021
- 2021-09-15 CN CN202111112694.4A patent/CN115806498A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4283381A (en) * | 1979-07-12 | 1981-08-11 | Schering Aktiengesellschaft | Triiodinated aminoacetamido isophthalamide x-ray contrast agents |
| ES2037605A1 (en) * | 1991-11-18 | 1993-06-16 | Invest Justesa Imagen S A Cent | New iodinated dimers X=ray contrast agent prepn. |
| EP0571593A1 (en) * | 1991-11-18 | 1993-12-01 | Invest Justesa Imagen S A Cent | New non ionic iodized agents for x-ray contrasting, method for preparing them and galenical compositions containing them. |
| CN101654417A (en) * | 2009-09-01 | 2010-02-24 | 江苏省原子医学研究所 | Preparation method of X-ray contrast agent ioversol intermediate |
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