Preparation method of 17β-androst-4-en-3-one-17-carboxylic acid

A technology of androstenedione and androstene, which is applied in the field of preparation of steroid hormone drug intermediates, can solve the problems of complicated process operation, difficult environmental protection treatment, expensive synthetic raw materials, etc., and achieves cheap and easy-to-obtain raw materials and good product quality , the effect of short synthetic route
CN107629101BActive Publication Date: 2020-06-26HUNAN KEREY BIOTECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
HUNAN KEREY BIOTECH
Publication Date
2020-06-26

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Abstract

The invention discloses a preparation method of 17 beta-androst-4-ene-3-one-17-carboxylic acid. The preparation method comprises that 4-androstenedione (called as 4AD for short) as a raw material andtriethyl orthoformate undergo a reaction in an organic solvent under acid catalysis, the reaction product is after-treated to form an etherate, the etherate is dissolved in an organic solvent and undergoes a reaction with trimethylsulfonium iodide under strong base catalysis, the product is after-treated to form an epoxide, the epoxide is dissolved in an organic solvent and then is subjected to rearrangement under acid catalysis to form an aldehyde, and aldehyde is dissolved in an organic solvent and undergoes a catalytic oxidation reaction with hydrogen peroxide acid to produce 17 beta-androst-4-ene-3-one-17-carboxylic acid. The 17 beta-androst-4-ene-3-one-17-carboxylic acid has a melting point of 244-246 DEG C, HPLC content of 99.0% or more and a reaction weight total yield of 70-72%. Compared with the traditional method, the preparation method utilizes cheap and easily available raw materials, has simple and environmental friendly processes and a high synthesis yield, produces highquality products, reduces a cost by 30-40% and is conducive to industrial production.
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Description

technical field

[0001] The invention relates to the preparation technology of steroid hormone drug intermediates, in particular to the preparation method of finasteride intermediate 17β-androst-4-en-3-one-17-carboxylic acid. Background technique

[0002] Finasteride is currently the first-line clinical drug for the treatment of benign prostatic hypertrophy and benign prostatic hyperplasia in elderly men, and it is also used to treat early-stage prostate cancer. Because finasteride can selectively inhibit the activity of 5α-reductase in the human body, thereby blocking the conversion of testosterone into dihydrotestosterone in the body, so that the proliferated prostate shrinks due to the lack of dihydrotestosterone. Indeed, the market potential is huge. The production of finasteride is made from the intermediate 17β-androst-4-en-3-one-17-carboxylic acid through five steps of ring opening, ring closing, hydrogenation, amidation and dehydrogenation.

[0003] The traditional ...

Claims

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