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Novel synthesis method for iopromide

A technology of iopromide and a new method, applied in the field of organic preparation, can solve the problems of unfavorable large-scale industrial production, high production cost, expensive raw materials, etc., and achieve the effects of easy control of product quality, few by-products, and cheap reagents

Active Publication Date: 2014-08-06
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The technical problem to be solved by the present invention is to overcome the defects of expensive raw materials, easy to produce uncontrollable impurities, high production cost, complicated operation and unfavorable industrialized large-scale production in the existing technology for preparing iopromide, and provide an effective preparation The method of iopromide, the raw material of this method is easy to get, difficult to produce impurity that is difficult to control, reaction condition is gentle, step is simple, production cost is low, is suitable for suitability for industrialized production

Method used

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  • Novel synthesis method for iopromide
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  • Novel synthesis method for iopromide

Examples

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Effect test

Embodiment 1

[0025] Embodiment 1 The preparation of formula (II) compound 5-[(2-methoxy)acetamido]-2,4,6-triiodoisophthaloyl chloride

[0026] Add 300mmol of methoxyacetic acid, 110mmol of triphosgene and 300mL of dichloromethane into the reaction flask, stir under reflux for 3h, evaporate the solvent under reduced pressure, cool the reaction flask to 15-20°C and add 200mmol of 5-amino-2,4 , 6-triiodoisophthaloyl chloride and 150mL DMAC were added, and stirring was continued at this temperature for 5h. 700 mL of dichloromethane and 400 mL of water were added and stirred for 0.5 h. Separate the organic layer, wash the organic layer with saturated aqueous sodium bicarbonate solution and distilled water, dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and obtain a solid. Yield 90%.

Embodiment 2

[0027] Example 2 Formula (III) compound 5-[(2-methoxy)acetamido]-3-(2,3-dihydroxy-N-methylpropylcarbamoyl)-2,4,6-tri Preparation of iodobenzoyl chloride

[0028] With 100mmol formula (II) compound, 100mmol solid base catalyst ZrO 2 -Cr 2 o 3 and 200mL DMAC were added to the reaction flask, the temperature of the reaction system was lowered to 10-15°C, 90mmol N-methyl-2,3-dihydroxypropylamine was slowly added dropwise, and the reaction was stirred at this temperature for 5h after the drop was completed. The reaction temperature is raised to room temperature, the catalyst is filtered, and the catalyst can be reused after drying. The solvent was evaporated under reduced pressure, 400 mL of dichloromethane was added to the residue, and stirred for 0.5 h. Filter and collect the precipitated solid, add 300mL tetrahydrofuran to the solid, and stir at room temperature for 0.5h. The precipitated solid was filtered and dried to obtain the compound of formula (III) with a yield of 8...

Embodiment 3

[0029] The preparation of embodiment 3 formula (I) compound iopromide

[0030] Add 100mmol of the compound of formula (III), 120mmol of sodium carbonate, 100mmol of 2,3-dihydroxypropylamine and 150mL of DMAC into the reaction flask, stir at room temperature for 2h, evaporate the solvent under reduced pressure, add 400mL of water to the residue, and wash with saturated sodium hydroxide solution After adjusting to weak alkalinity, it was eluted with a cation exchange column and an anion exchange column in sequence. The eluate from the anion exchange column was collected, and the water was distilled off under reduced pressure to obtain a white solid, which was dried under reduced pressure at 70°C to obtain the compound of formula (I) with a yield of 92% and a purity of 99.7% as measured by high pressure liquid chromatography.

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Abstract

The invention discloses a novel synthesis method for iopromide. The novel synthesis method comprises the following steps of 1, enabling methoxyacetic acid to react with triphosgene to obtain a reaction product, and then, enabling the reaction production to be directly subjected to one-pot reaction with 5-amino-2, 4, 6-triiodo-isophthalicacyl chloride to prepare a compound 5-[(2-methoxyl) acetamido]-2, 4, 6-triiodo-isophthalicacyl chloride as shown in the formula (II); 2, condensing the compound as shown in the formula (II) and N-methyl-2, 3-dihydroxyl propylamine under the action of a solid catalyst ZrO2-Cr2O3 to obtain a compound 5-[(2-methoxyl) acetamido]-3-(2, 3-dihydroxyl-N-methylpropylaminoformoxyl)-2, 4, 6-triiodo-benzoyl chloride as shown in the formula (III); 3, condensing the compound as shown in the formula (III) and 2, 3-dihydroxylpropylamine under the action of a catalyst to prepare a compound iopromide as shown in the formula (I). The synthesis method for iopromide, disclosed by the invention, is few in byproduct, easy to control the product quality, high in product purity, cheap and easily-obtained in used reagent, few in step, simple in operation, relatively high in total yield and suitable for industrial production, and provides a novel approach for preparing iopromide.

Description

technical field [0001] The invention belongs to the technical field of organic preparation, and in particular relates to a new method for synthesizing iopromide. Background technique [0002] Iopromide, the chemical name is N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxy)acetamido]-N- Methyl-1,3-phthalamide is a non-ionic iodine contrast agent developed by Schering-Plough of Germany. It was first launched in Germany in 1985 and is clinically used as an X-ray contrast agent. Iopromide is a non-ionic iodine contrast agent, and its Chinese trade name is Youweixian or iopromide, which has good safety and imaging effect. At present, the drug is widely used in angiography, renal arteriography, urography, CT contrast-enhanced examination, body cavity display and other X-ray contrast agents. As a water-soluble contrast agent, it has high water solubility, low viscosity, good tolerance, and low intravenous toxicity. It is an ideal contrast agent for CT enhanced scanning. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/46C07C231/02C07C231/12
Inventor 王启发王静文沈梦瑶程青芳
Owner HUAIHAI INST OF TECH
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