Preparation method for contrast medium intermediate for medical diagnosis

A technology for medical diagnosis and intermediates, applied in the field of chemical drug synthesis, can solve the problems of low yield, high cost, difficulty in synthesizing macrocyclic compounds, etc., and achieve the effects of low cost, stable quality and environmental friendliness

Inactive Publication Date: 2018-11-13
XUCHANG HENGSHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Therefore, it can be seen from the above three commonly used methods that the synthesis of macrocyclic compounds is very difficult, often accompanied by more side reaction

Method used

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  • Preparation method for contrast medium intermediate for medical diagnosis
  • Preparation method for contrast medium intermediate for medical diagnosis
  • Preparation method for contrast medium intermediate for medical diagnosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Put (100.0g, 0.66mol) benzyl ethanolamine and 400g toluene in a 1L three-necked flask, stir evenly, add 100g of concentrated sulfuric acid, and heat up to reflux, heat and reflux for 8 hours, cool to room temperature, add sodium hydroxide Adjust the pH to 10, separate the liquid, and recycle the toluene;

[0027] The resulting aqueous phase was heated to reflux, kept at reflux for 8 hours, cooled to room temperature, and allowed to stand for liquid separation to obtain (66.5 g, 0.50 mol) of an oily intermediate;

[0028] Put the obtained (66.5g, 0.5mol) oil into a reaction flask, add 400g of methanol and 13.3g of concentrated sulfuric acid, heat up to reflux, and keep the temperature for 12 hours. Filter and dry the filter cake to obtain (0.088mol, 47.0g) tetrabenzylcyclene product with a yield of 70.6% and a purity of 99.5%.

Embodiment 2

[0030] Put (100.0g, 0.66mol) benzyl ethanolamine and 500g toluene in a 1L three-neck flask, stir evenly, add 150g of concentrated sulfuric acid, and heat up to reflux, heat and reflux for 12 hours, cool to room temperature, add sodium hydroxide Adjust the pH to 9, separate the liquid, and recycle the toluene;

[0031] The resulting aqueous phase was heated to reflux, kept at reflux for 14 hours, cooled to room temperature, and allowed to stand for liquid separation to obtain (61.8 g, 0.46 mol) of an oily intermediate;

[0032] Put the obtained (61.8g, 0.46mol) oil into a reaction flask, add 800g of methanol and 15.0g of methanesulfonic acid, heat up to reflux, keep the temperature for reaction for 12 hours, after the reaction is completed, cool down to below 0°C, keep warm and crystallize for 8 hours, Suction filtration and drying of the filter cake yielded (0.085 mol, 47.0 g) tetrabenzcyclene product with a yield of 70.6% and a purity of 99.5%.

Embodiment 3

[0034] Put (100.0g, 0.66mol) benzyl ethanolamine and 400g toluene in a 1L three-necked flask, stir evenly, add 100g of concentrated sulfuric acid, and heat up to reflux, heat and reflux for 8 hours, cool to room temperature, add sodium hydroxide Adjust the pH to 8-10, separate the liquid, and recover and reuse the toluene;

[0035] The resulting aqueous phase was heated to reflux, kept at reflux for 8 hours, cooled to room temperature, and allowed to stand for liquid separation to obtain (66.5 g, 0.5 mol) of an oily intermediate;

[0036] Put the obtained (66.5g, 0.5mol) oil into a reaction flask, add 400g of methanol and 20.0g of benzenesulfonic acid, heat up to reflux, and keep the temperature for 16 hours. Suction filtration and drying of the filter cake yielded (0.080 mol, 42.6 g) tetrabenzylcyclene product with a yield of 64.0% and a purity of 99.5%.

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Abstract

The invention discloses a preparation method for a contrast medium intermediate for medical diagnosis, and the intermediate is a key intermediate for macromolecule gadolinium chelate contrast medium.According to the method, benzylethanolamine is adopted as a starting raw material, and the product N',N'',N''',N''''-tetraazacyclododecane is obtained through backflow water diversion, sulfonation andpolymerization reaction. According to the method, methylbenzene, water and methyl alcohol are all recycled, resource saving and the environmental-friendly function are realized, the cost is saved, the product is stable in quality and high in yield, and the method is suitable for large-scale industrial stable production.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and in particular relates to a preparation method of a contrast agent intermediate for medical diagnosis. Background technique [0002] Interventional radiology is a marginal subject that developed rapidly in the late 1970s. Under the guidance of medical imaging equipment, it is based on imaging diagnostics and clinical diagnostics, combined with the principles of clinical therapeutics, and uses catheters, guide wires and other equipment to diagnose and treat various diseases. [0003] In recent years, with the improvement of medical imaging diagnosis technology and the continuous improvement of imaging equipment technology in domestic large and medium-sized hospitals, under the promotion of interventional radiology, contrast agents have developed rapidly from variety to market, and at the same time have driven this The replacement of a class of drugs. Although contrast agent is...

Claims

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Application Information

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IPC IPC(8): C07D257/02
CPCC07D257/02
Inventor 蚩晓娜郭培谷志勇
Owner XUCHANG HENGSHENG PHARMA
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