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Alfuzosin hydrochloride intermediate compound

A technology of alfuzosin hydrochloride and intermediates, which is applied in the field of pharmaceutical synthesis, can solve the problems of unsuitable industrial production, high risk, and high equipment requirements, and achieve the effects of avoiding high temperature and high pressure reactions, low cost, and high purity

Pending Publication Date: 2021-12-17
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process uses alfuzosin as raw material, but in the process of synthesizing alfuzosin, there is still a step of reducing cyano group to amino group, and at the same time, a flammable Raney nickel catalyst is used, and it is carried out under high temperature and high pressure conditions. , so the equipment requirements are high, the risk is high, and it is not suitable for industrial production

Method used

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  • Alfuzosin hydrochloride intermediate compound
  • Alfuzosin hydrochloride intermediate compound
  • Alfuzosin hydrochloride intermediate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Add N,N-dimethyl In methyl formamide (120ml), the temperature was raised to 100°C for reaction, TLC detected that the reaction was complete, cooled to room temperature, and suction filtered to obtain the solid intermediate compound I hydrochloride; then the intermediate compound I hydrochloride was transferred to the reaction flask , add purified water (100ml), heat up to 70-80°C, keep stirring until the solids are completely dissolved, then add NaOH solution with a concentration of 30% dropwise, adjust the pH value to 12-14, gradually turn off the heating after solids are precipitated, and cool down to Stir and crystallize at 20-30°C for 3 hours, start suction filtration, rinse the filter cake with purified water until the pH value of the filtrate is equal to 7, and dry the filter cake to obtain 26.60 g of white solid intermediate compound Ⅰ with a yield of 95.91 %, purity 99.63%.

Embodiment 2

[0060] Add 2-chloro-4-amino-6,7-dimethoxyquinazoline (24.00g, 0.10mol) and 1,3-propanediamine (8.15g, 0.11mol) to isopropanol (120ml) in sequence During the reaction, the temperature was raised to 80°C for reaction, TLC detected that the reaction was complete, and the reaction was completed after cooling down to room temperature and suction filtration to obtain the solid intermediate compound I hydrochloride; then the intermediate compound I hydrochloride was transferred to the reaction bottle, and purified water (100ml ), heat up to 70-80°C, heat and stir until all the solids are dissolved, then add NaOH solution with a concentration of 30% dropwise, adjust the pH value to 12-14, gradually turn off the heating after solids are precipitated, cool down to 20-30°C, and stir After crystallization for 3 hours, suction filtration was started, and the filter cake was rinsed with purified water to pH 7. After suction filtration, the filter cake was dried to obtain 25.72 g of white sol...

Embodiment 3

[0062] Add 2-chloro-4-amino-6,7-dimethoxyquinazoline (24.00g, 0.10mol) and 1,3-propylenediamine (11.12g, 0.15mol) to diglyme in sequence (120ml), heat up to 120°C for reaction, TLC detects that the reaction is complete, cool down to room temperature, and filter with suction to obtain a solid intermediate compound I hydrochloride; then transfer the intermediate compound I hydrochloride into the reaction flask, add purification Water (100ml), heat up to 70-80°C, heat and stir until the solids are completely dissolved, then add NaOH solution with a concentration of 30% dropwise, adjust the pH value to 12-14, turn off the heating after solids are gradually precipitated, and cool down to 20-30 ℃, stirred and crystallized for 3 hours, started suction filtration, rinsed the filter cake with purified water to a pH value of 7, completed the suction filtration, and dried the filter cake to obtain 25.49 g of white solid intermediate compound Ⅰ with a yield of 91.91% and a purity of 99.12%...

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to an alfuzosin hydrochloride intermediate compound I and a preparation method thereof. 3-methylaminopropionitrile commonly used in the alfuzosin hydrochloride synthesis process is replaced with 1, 3-propane diamine. As the activities of two amino groups are consistent, the selectivity problem does not exist, and side reactions are few. Meanwhile, a high-temperature and high-pressure cyano reduction reaction is avoided. A method for preparing alfuzosin hydrochloride by using the intermediate is simple and convenient to operate, low in cost, high in yield and purity and suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and in particular relates to an alfuzosin hydrochloride intermediate compound. Background technique [0002] Alfuzosin hydrochloride (alfuzosinhydrochloride), that is, N-[3-(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl-tetrahydro-2-furamide Hydrochloride, a quinazoline derivative, is an α1-adrenergic receptor antagonist, which can selectively combine with the α1-receptors of the prostate and prostatic capsule, and affect the α1-receptor mediation The contraction of smooth muscle induced by it can reduce the voiding disorder in patients with benign prostatic hyperplasia and improve the quality of life of patients. Alfuzosin hydrochloride was researched and developed by Sanofi Sandela Fort, France, and was first launched in France in 1988. It has been widely used in the treatment of benign prostatic hyperplasia and high blood pressure all over the world. Its structural...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/95C07D405/12
CPCC07D239/95C07D405/12
Inventor 张贵民汪慧岩翟立海黄超马超刘忠
Owner LUNAN PHARMA GROUP CORPORATION
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