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Synthesis method of ketoconazole metabolite

A synthesis method and metabolite technology, applied in organic chemistry and other directions, to achieve the effect of reasonable process design, easy availability of raw materials and simple operation

Inactive Publication Date: 2021-06-25
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on the research on ketoconazole metabolites. The successful synthesis of our ketoconazole metabolites provides guidance for the synthesis of similar metabolites in the future.

Method used

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  • Synthesis method of ketoconazole metabolite
  • Synthesis method of ketoconazole metabolite
  • Synthesis method of ketoconazole metabolite

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A kind of synthetic method of ketoconazole metabolite, comprises the following steps:

[0046] (1) Dissolve 34.00g of 1-benzyloxy-4-iodobenzene (compound I) in N,N-dimethylformamide, add 11.21g of ethylenediamine, 6.12g of sodium hydroxide and 0.51g of bromine Cuprous chloride was stirred and reacted at room temperature for 5 hours. After the reaction was complete, a brownish-black turbid liquid was obtained, which was diluted with water and extracted with ethyl acetate to obtain 26.00 g of gray solid compound II with a yield of 97.87%.

[0047] (2) Dissolve 26.00 g of compound II in tetrahydrofuran, add 15.30 g of acetic anhydride, and stir at room temperature for 1 hour. After the reaction is complete, a gray cloudy liquid is obtained. After concentration, 26.55 g of gray solid compound III is purified by column chromatography, with a yield of 87.02%. .

[0048] (3) Dissolve 5.00 g of compound III in 1,4-dioxane, add 5.21 g of di-tert-butyl dicarbonate and 3.12 g of ...

Embodiment 2

[0053] A kind of synthetic research of ketoconazole metabolite, comprises the following steps:

[0054] (1) Dissolve 20.00g of 1-benzyloxy-4-iodobenzene (compound I) in tetrahydrofuran, add 11.48g of ethylenediamine, 5.06g of sodium hydroxide and 0.82g of ferrous chloride, and stir at room temperature for 5 After 1 hour, the reaction was complete to obtain a brown-black turbid liquid, which was diluted with water and extracted with ethyl acetate to obtain 15.12 g of gray solid compound II, with a yield of 96.76%.

[0055] (2) Dissolve 15.12g of Compound II in tetrahydrofuran, add 4.76g of acetyl chloride, and stir at room temperature for 1 hour. After the reaction is complete, a gray cloudy liquid is obtained. After concentration, 17.34g of gray solid Compound III is purified by column chromatography, with a yield of 97.73%. .

[0056] (3) Dissolve 5.00 g of compound III in dichloromethane, add 4.22 g of di-tert-butyl dicarbonate and 1.62 g of sodium bicarbonate, stir and rea...

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Abstract

The invention discloses a synthesis method of a ketoconazole metabolite; 1-benzyloxy-4-iodobenzene and cis-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl methyl)-1,3-dioxolan-4-yl]methanol p-toluenesulfonate are used as raw materials, and the ketoconazole metabolite is synthesized through six steps of reaction. The method is reasonable in process design, high in operability, mild in reaction condition, high in yield and capable of achieving industrial production; the prepared ketoconazole metabolite is high in purity, and a basis is provided for quality control and safety and efficiency evaluation of ketoconazole.

Description

technical field [0001] The invention belongs to medicine synthesis technology, in particular to a synthesis method of ketoconazole metabolites. Background technique [0002] Ketoconazole is an imidazole broad-spectrum antifungal drug, which inhibits the biosynthesis of ergosterol on the fungal cell membrane by highly selectively interfering with the activity of fungal cytochrome P-450. It is effective for both superficial and deep fungal infections. It can not only inhibit the growth of fungi, but also inhibit the transformation of spores into mycelium and prevent further infection. It is clinically applicable to the treatment of tinea manuum, tinea pedis, tinea dermatitis, tinea corporis, jock itch, thrush, tinea versicolor and skin candidiasis. [0003] Pharmacology Ketoconazole is an azole antifungal drug, which has antibacterial effects on deep infection fungi such as Candida, Chromomycetes, Coccidioides, Histoplasma, Sporothrix, etc., and has antibacterial effects on T...

Claims

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Application Information

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IPC IPC(8): C07D405/06
CPCC07D405/06
Inventor 何旭毕海峰杨石张池刘春徐一鸣崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
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