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Novel method for synthesizing finasteroid

A technology of finasteride and a synthesis method, applied in the field of drug synthesis, can solve the problems of many reaction steps, high price, complicated operation and the like, and achieves the effects of good product yield, simple operation and prolonged reaction time

Inactive Publication Date: 2009-07-22
ZHEJIANG XIANJU JUNYE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The method uses expensive and difficult-to-obtain synthetic reagents such as lithium bistrimethylsilylamide, di-tert-butyl carbonate, and diphenyl disulfide compound. The reaction steps are many, the operation is complicated, the energy consumption is high, and the yield is low. Low, the two-step total yield is only 60.2%

Method used

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  • Novel method for synthesizing finasteroid
  • Novel method for synthesizing finasteroid
  • Novel method for synthesizing finasteroid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Step a: the synthesis of dihydrofinasteride iodide (F9-I)

[0053] In a clean and dry 500ml reaction bottle, 200ml toluene, 20.00g dihydrofinasteride (F 9 ), 25ml triethylamine, blow nitrogen, freeze to 0-5°C, add 13.5ml trimethylchlorosilane, add 20.5g iodine in portions at about 0-5°C, keep warm for 4 hours, monitor by TLC end. After the completion of the reaction, add 100 ml of 20% sodium thiosulfate aqueous solution to quench the reaction; add 100 ml of isopropanol and stir for 2 hours, and separate the liquids; the organic phase is washed once with 100 ml of 20% sodium thiosulfate aqueous solution; phase, back-extract once with a mixture of 20ml isopropanol and 30ml toluene, and discard the water phase; combine the organic phases, wash once with 100ml of 2% aqueous sodium hydroxide solution, and then wash three times with tap water to separate the flocs; Evaporate most of the solvent under reduced pressure, lower to room temperature, slowly add 100ml of petroleum...

Embodiment 2

[0062] Step a: the synthesis of dihydrofinasteride iodide (F9-I)

[0063] In a clean and dry 500ml reaction bottle, 200ml benzene, 20.00g dihydrofinasteride (F 9 ), 30ml of tetramethylethylenediamine, blown nitrogen, freeze to -5°C ~ 0°C, add 16.5ml of iodotrimethylsilane, keep warm at -5°C ~ 0°C, add 25.00g of iodine in stages, after the addition, Continue to incubate the reaction for 6 hours, and monitor the end point by TLC. After the reaction was completed, add 150 ml of a 15% sodium metabisulfite aqueous solution dropwise to quench the reaction; add 100 ml of isopropanol and stir for 2 hours, then separate the liquids; the organic phase was washed once with 150 ml of a 15% sodium metabisulfite aqueous solution; the combined aqueous phase was washed with 20 ml The mixed solution of isopropanol and 30ml of benzene was back extracted once, and the water phase was discarded; the organic phase was combined, washed once with 100ml of 2% aqueous sodium hydroxide solution, and w...

Embodiment 3

[0067] Step a: the synthesis of dihydrofinasteride iodide (F9-I)

[0068] In a clean and dry 500ml reaction bottle, drop 200ml xylene and 20.00g dihydrofinasteride (F 9), 40ml diisopropylethylamine, blow nitrogen, freeze to 0°C~5°C, add 14.5ml trimethylchlorosilane, keep warm at 0°C~5°C, add 18.05g iodine in portions, after the addition is complete, continue the heat preservation reaction 8 hours, TLC monitors the endpoint. After completion of the reaction, add 100ml of 30% sodium sulfite aqueous solution dropwise to quench the reaction; add 100ml of isopropanol and stir for 2 hours, and separate the liquids; the organic phase is washed once with 100ml of 30% sodium sulfite aqueous solution; The mixed solution of alcohol and 30ml xylene was back-extracted once, and the water phase was discarded; the organic phase was combined, washed once with 100ml of 2% aqueous sodium hydroxide solution, and then washed three times with tap water, and the flocs were separated; the organic p...

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Abstract

The invention provides a new synthetic method of finasteride, belonging to the technical field of drug synthesis. The method comprises the following steps of: a. synthesis of dihydro finasteride iodo complex; and b. synthesis of finasteride; the synthesis method can transform dihydrotestosterone finasteride (F9) into the finasteride with a theoretic volume, avoids the use of harmful and toxic chemicals which are sensitive to the environment, has the advantages of total two-step reaction yield of more than 90%, purity of over 99.0%, good product yield, high purity, easy refining, simple operation, low cost, and less three-waste, conforms with the requirements of green chemical synthesis, and can achieve the requirements of high yield, high purity, green cleaning and industrial production of the finasteride.

Description

technical field [0001] The invention relates to a method for synthesizing drugs for treating prostate diseases, in particular to a new method for synthesizing finasteride for treating prostate diseases; it belongs to the technical field of drug synthesis. Background technique [0002] Finasteride (finasteride) scientific name N-tert-butyl-3-oxo-4-aza-5α-androst-1-ene-17β-amide, it is a common disease of elderly men benign prostatic hyperplasia ( BPH) drug, trade name Proscar (Proscar). The drug has been widely used at home and abroad, and the market demand is large. Recently, it has also been found that it has significant curative effects on the prevention and treatment of prostate cancer, male hair loss and women's hirsutism, which shows that the drug has excellent application prospects and development potential. [0003] Dihydrofinasteride (Dihydrofinasteride) scientific name N-tert-butyl-3-oxo-4-aza-5α-androst-17β-amide (Finasteride European Pharmacopoeia EP6.0 impurity...

Claims

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Application Information

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IPC IPC(8): C07J73/00A61P13/08
Inventor 尹金玉张汝金刘龙成
Owner ZHEJIANG XIANJU JUNYE PHARM CO LTD
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