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Iopromide preparation method

A technology of iopromide and amidation, which is applied in the field of medicine and can solve the problems of low yield and the like

Active Publication Date: 2015-10-28
白银京宇新药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This patent adopts the method of recrystallization, can remove the bismer by-product in the preparation process of iopromide, but the yield is very low

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: Preparation of 5-methoxyacetyl-2,4,6-triiodoisophthaloyl chloride (3)

[0036] Dissolve 38g (0.35mol) of methoxyacetyl chloride in 20mL of N,N-dimethylacetamide, and drop into 60g (0.1mol) of N,N-dimethylacetamide in an ice bath Acetamide solution (100 mL), after dropping, stirred at room temperature for 20 h. After the reaction was completed, the reaction solution was poured into ice water, and a white solid was precipitated, which was filtered by suction. The solid was dissolved in dichloromethane, washed with water (200mL×3), saturated sodium bicarbonate solution (400mL×2), saturated sodium chloride solution (200mL×2), dried over anhydrous sodium sulfate, and evaporated to dryness , a white solid was obtained. Yield 86%. HPLC purity 98%. mp: 199-201°C.

[0037] MS: 667.2 [M-H] -

[0038] 1 H-NMR (300MHz, DMSO) δ4.02(s, 2H), 3.49(s, 3H).

Embodiment 2

[0039] Example 2: Preparation of 3-methoxyacetyl-5-(2,3-dihydroxy-N-methyl n-propylcarbamoyl)-2,4,6-triiodobenzoic acid (4)

[0040] Dissolve 8.3g (0.079mol) of 3-methylamino-1,2-propanediol and 15.6g (0.084mol) of tri-n-butylamine in 40mL of N,N-dimethylacetamide, drop Put 75g (0.11mol) of intermediate (3) in N,N-dimethylacetamide (150mL) solution, dropwise, react at room temperature for 3h. After the reaction, evaporate the solvent to dryness, add water at 0°C, stir in an ice bath for 0.5 h, filter with suction, wash the filter cake with a small amount of cold water, adjust the pH of the aqueous solution to 9, and separate and purify the resulting aqueous solution with an anion exchange resin to obtain a light white solid. Yield 46%. HPLC purity 99%. mp: 163-165°C.

[0041] MS: 719.4[M+H] + , 740.5[M+Na] + , 716.5[M-H] - , 754[M+Cl] -

[0042] 1 H-NMR (300MHz, DMSO) δ9.79(s, 1H), 4.76(s, 1H), 4.59(s, 1H), 3.96(s, 2H), 3.88(s, 1H), 3.66(d, J =15.6Hz, 1H), 3.45(s, 5H...

Embodiment 3

[0043] Example 3: Preparation of 3-methoxyacetyl-5-(2,3-diacetoxy-N-methyl n-propylcarbamoyl)-2,4,6-triiodobenzoic acid (5)

[0044] Add 25g (0.035mol) of intermediate (4) to 125mL of acetic anhydride and 50mL of glacial acetic acid, add 0.3g (0.0017mol) of p-toluenesulfonic acid at 0-5°C, and stir at room temperature for 10h. After the reaction, the solvent was evaporated to dryness, and an appropriate amount of absolute ethanol was added to the residue, and rotary evaporation was continued to obtain a light white solid. Yield 80%. mp: 108-110°C.

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Abstract

The present invention relates to an X-ray contrast agent iopromide preparation method. According to the method, 3-methoxy acetyl-5-(2,3-dihydroxy-N-methyl-n-propyl-carbamoyl)-2,4,6-triiodobenzoic acid (4) is introduced as an intermediate, the used raw material is cheap and easy to obtain, the experiment operation is relatively simple, the reaction condition is mild, and the product purity is qualified.

Description

technical field [0001] The invention belongs to the technical field of medicine and provides a method for preparing an X-ray contrast agent iopromide. Background technique [0002] Iopromide, a new type of non-ionic hypotonic contrast agent with five hydroxyl groups in the molecule developed by Schering AG in 1982, with a trade name of Ultravist, was officially launched in 1985. It is a contrast agent widely used in China at present. It is used for angiography, renal arteriography, urography, CT contrast-enhanced examination, and body cavity display (arthrography, hysterosalpingography, fistulography). The products on the market are mainly imported from Germany Schering Deut-schland Gmbh. [0003] [0004] iopromide [0005] At present, the references on the preparation method of iopromide include: GB1548594, US4364921, CN102351735, CN102964269, WO2009134030 and so on. [0006] Three methods for preparing iopromide are disclosed in the patent GB1548594. [0007] Rout...

Claims

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Application Information

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IPC IPC(8): C07C237/46C07C231/12
Inventor 何镭任利翔王丽君郭飞
Owner 白银京宇新药业有限公司
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