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Triiodobenzene compound and contrast medium with same

A technology of compound and contrast agent, which is applied in the field of 5--N-methyl-N--N'--2, triiodobenzene compound and the contrast agent containing the compound, which can solve the problem of toxicity, hyperosmosis, high viscosity, etc. question

Active Publication Date: 2011-07-20
ZHEJIANG STARRY PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Clinical studies have found that the above-mentioned three types of iodine contrast agents all have one or another disadvantage, such as toxicity, hyperosmolarity, or high viscosity [Journal of West China Pharmaceutical Sciences, 2000, 15(1): 53-54]

Method used

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  • Triiodobenzene compound and contrast medium with same
  • Triiodobenzene compound and contrast medium with same
  • Triiodobenzene compound and contrast medium with same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 3-Acetoxyacetamido-5-(2,3-diacetoxy-n-propylcarbamoyl)-2,4,6-triiodobenzoic acid (III)

[0031]

[0032] Under ice-water bath cooling and mechanical stirring, to 3-amino-5-(2,3-diacetoxy n-propylcarbamoyl)-2,4,6-triiodobenzoic acid (II, 150g, 0.21mol) Acetoxyacetyl chloride (68.2 g, 0.50 mol) was added dropwise to the tetrahydrofuran (450 ml) solution, and the drop was completed (4 h), then stirred at room temperature, followed by TLC, and the reaction was completed after 28 h. Concentration under reduced pressure gave viscous material III (136.8 g, 80%). The next reaction (acyl chloride) was carried out without purification. 1 HNMR (CDCl 3 , 400MHz): δ: 2.01(s, 3H), 2.07(s, 3H), 2.13(s, 3H), 3.06-4.27(m, 4H), 4.93(s, 2H), 5.11(m, 1H), 8.51 (brs, 1H), 9.95-10.05 (m, 1H), 12.81 (brs, 1H); MS (ESI, m / z): 817 (M+H) + .

Embodiment 2

[0033] Example 2 3-Acetoxyacetamido-5-(2,3-diacetoxy-n-propylcarbamoyl)-2,4,6-triiodobenzoyl chloride (IV)

[0034]

[0035] 3-Acetoxyacetamido-5-(2,3-diacetoxy-n-propylcarbamoyl)-2,4,6-triiodobenzoic acid (III, 136.8g, 0.17mol) obtained in Example 1 , a mixture of chloroform (400ml) and triethylamine (6.8ml) was heated to reflux, and a solution of bis(trichloromethyl)carbonate (32.7g, 0.11mol) in chloroform (100ml) was added dropwise under stirring, and the dropwise completion (6h) , Stir the reaction at the same temperature for 8h. After concentration under reduced pressure, the resulting residue was recrystallized from THF (300ml) to obtain IV as an off-white solid (102.1g, 73%). 1 HNMR (CDCl 3 , 400MHz): δ2.05(s, 3H), 2.11(s, 3H), 2.17(s, 3H), 3.09-4.23(m, 4H), 4.96(s, 2H), 5.23(m, 1H), 8.58 (brs, 1H), 10.05-10.25 (brs, 1H); MS (ESI, m / z): 835 (M+H) + .

Embodiment 3

[0036] Example 3 5-Acetoxyacetamido-N-methyl-N-(2-hydroxyethyl)-N'-(2,3-diacetoxy-n-propyl)-2,4,6- Triiodoisophthalamide (V)

[0037]

[0038] The obtained 3-acetoxyacetamido-5-(2,3-diacetoxy-n-propylcarbamoyl)-2,4,6-triiodobenzoyl chloride (IV, 174.8g, 0.21mol ), chloroform (700ml) and anhydrous sodium carbonate (6g, 0.059mol) were cooled to -5°C with an ice-salt bath, nitrogen methyl ethanolamine (19.7g, 0.26mol) was added dropwise under stirring, and the dropwise (3.5h ). The ice-salt bath was removed, and the reaction was stirred at room temperature for 12h. The reaction mixture was then cooled to -5°C with an ice-salt bath, and nitrogenmethylethanolamine (19.7 g, 0.26 mol) was added dropwise within 3.5 h with stirring. The ice-salt bath was removed, the reaction was stirred at room temperature, and the reaction progress was tracked by TLC, and the reaction was completed within 26 hours. The insoluble matter was filtered off, and the filtrate was concentrated under ...

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Abstract

The invention relates to a triiodobenzene compound and a contrast medium with same and also provides a preparation method of the compound. The compound in the invention is 5-(2-hydroxylacetamido)-N-methyl-N-(2-hydroxyethyl)-N'-(2,3-dihydroxyl-n-propyl)-2,4,6-triiodoisophthalamide (I). Compared with the existing clinical nonionic contrast medium monomers such as Iohexol and Iomeprol, the contrast medium in the invention has lower osmotic pressure and viscosity.

Description

technical field [0001] The invention belongs to the field of non-ionic X-ray contrast agents, and relates to a triiodobenzene compound with excellent physical and chemical properties and a contrast agent containing the compound. More specifically, the compound of the present invention is 5-(2-hydroxyacetamido)-N-methyl-N-(2-hydroxyethyl)-N'-(2,3-dihydroxy-n-propyl)- 2,4,6-Triiodoisophthalamide. Background technique [0002] Since the advent of diatrizoic acid (the first iodine contrast agent) in the 1950s, more than ten kinds of iodine contrast agents have been widely used in clinic as diagnostic reagents. It is reported that there are about 50 million patients who use contrast medium every year in the world [Curr. Opin. Allergy Clin Immunol, 2002(2): 333-339]. According to the permeability, this type of contrast agent can be divided into the following three categories: the first category is hypertonic iodine contrast agent, such as diatrizoic acid, diatrizoate meglumine, ...

Claims

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Application Information

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IPC IPC(8): C07C237/46C07C231/12A61K49/04
Inventor 王哲徐静静张婷婷张鹏王金凤
Owner ZHEJIANG STARRY PHARMA
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