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Low-osmotic-pressure triiodo-benzene compound contrast agent

A kind of compound and contrast agent technology, applied in the field of non-ionic triiodobenzene compound contrast agent

Active Publication Date: 2013-11-13
ZHEJIANG STARRY PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the viscosity of the non-ionic monomer contrast agent is already low, but its osmotic pressure is between the hypertonic iodine contrast agent and the non-ionic dimer contrast agent, how to maintain the existing non-ionic monomer contrast agent Based on the viscosity of the contrast agent, reducing its osmotic pressure is the biggest problem faced by this type of contrast agent

Method used

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  • Low-osmotic-pressure triiodo-benzene compound contrast agent
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  • Low-osmotic-pressure triiodo-benzene compound contrast agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Formula (3) compound N, N-dimethyl-N'-(2,3-dihydroxy n-propyl)-5-acetamido-2,4,6-triiodo-1,3- Synthesis of Isophthalamide

[0032]

[0033]Formula (2) compound 3-acetamido-5-(2,3-diacetoxy n-propylcarbamoyl)-2,4,6-triiodobenzoyl chloride (70g, 0.09mol), tetrahydrofuran ( 210ml) into a 1L three-necked bottle. After cooling to 0°C in an ice-water bath, an aqueous solution of dimethylamine (86.2 g, 0.63 mol, 33%) was added dropwise. After dropping (1 h), the ice-water bath was removed, and the reaction was allowed to rise to room temperature naturally, and the reaction was stirred for 48 h (the completion of the reaction was tracked by HPLC). Adjust the pH to 7 with concentrated hydrochloric acid, and concentrate under reduced pressure to obtain a yellow viscous substance. The viscous obtained was separated and purified through LX18 macroporous adsorption resin, the main component eluate was collected, treated with activated carbon, and filtered. The filtr...

Embodiment 2

[0034] Example 2 Compound 1N, N-dimethyl-N'-(2,3-dihydroxy-n-propyl)-5-(N-methylacetamido)-2,4,6-triiodo-1, Synthesis of 3-isophthalamide

[0035]

[0036] Formula (3) compound N,N-dimethyl-N'-(2,3-dihydroxy n-propyl)-5-acetamido-2,4,6-triiodo-1,3-m-benzene Diformamide (42.3g, 0.06mol), sodium hydroxide (3.1g, 0.08mol), water (40ml), ethylene glycol monomethyl ether (160ml) were added to a 0.5L three-necked bottle, and stirred thoroughly for 30min (dissolving clear). To the reaction mixture was slowly added iodomethane (10.9 g, 0.08 mol) dropwise at room temperature. After dripping (1h). The reaction was stirred at room temperature 25°C for 21h. At room temperature, iodomethane (11 g, 0.08 mol) was continuously added dropwise to the reaction mixture slowly, and the drop was completed (1 h). Sodium hydroxide (3.1 g, 0.08 mol) was added, and the reaction was continued at room temperature (HPLC detection end point), and the reaction was completed (8h). Adjust the pH of t...

Embodiment 3

[0038] Example 3 Injection 1

[0039] Prescription 1 (300mgI / ml)

[0040]

[0041] Prescription 2 (350mgI / ml)

[0042]

[0043] Preparation:

[0044] Take the prescribed amount of compound 1, 10.0 mg of disodium calcium salt of ethylenediamine tetracarboxylic acid, and 120.0 mg of trishydroxymethylaminomethane in a 100ml volumetric flask, add water for injection to dissolve, adjust the pH to neutral, dilute to 100ml, and use a microporous Filter through a filter membrane, seal in a 10ml bottle, sterilize at 120°C for 20 minutes, take it out and cool it down to room temperature to obtain injections with different iodine contents.

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Abstract

The invention belongs to the field of nonionic monomer X-ray contrast agents, and relates to a triiodo-benzene compound contrast agent with excellent physicochemical properties and a preparation method of the compound. The compound is N,N-dimethyl-N'-(2,3-dihydroxy-n-propyl)-5-(N-methylacetamido)-2,4,6-triiodo-1,3-isophthalamide.

Description

technical field [0001] The invention belongs to the field of nonionic X-ray contrast agent, and relates to a nonionic triiodobenzene compound contrast agent with low osmotic pressure. More specifically, the compound of the invention is N,N-dimethyl-N'-(2,3-dihydroxy-n-propyl)-5-(N-methylacetamido)-2,4,6 - Triiodo-1,3-isophthalamide. Background technique [0002] Contrast agent is a substance that is introduced into the body through a certain way, so as to make an organ or tissue contrast with its surrounding structure or tissue, and plays an important role in the diagnosis and treatment of medical imaging. The X-ray absorption performance of a substance is approximately proportional to the cube of its atomic number, and any substance with a high atomic number that exists in a biocompatible form can become an X-ray contrast agent. Iodine with a large atomic number is opaque to X-rays, so iodine-containing compounds (including inorganic iodine compounds and organic iodine co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/46C07C231/12A61K49/04
Inventor 王哲张婷婷徐静静陈仕洪李灵巧罗盈营
Owner ZHEJIANG STARRY PHARMA
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