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Method for preparing 3-carbonyl-4-aza-5alpha-androstanes

A compound and carbonyl technology, applied in the field of preparation of pharmaceutical intermediates, can solve the problems of high production cost, difficulty in mass production, expensive precious metal reagents, etc., and achieve the effect of low cost and mild reaction

Active Publication Date: 2009-06-17
JIANGSU JIAERKE PHARMA GRP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has certain risks in operation. At the same time, due to the high price of the precious metal reagent 10% Pd / C, the production cost is relatively high, so the production operability of this process is not strong, and it is difficult to industrialize mass production.

Method used

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  • Method for preparing 3-carbonyl-4-aza-5alpha-androstanes
  • Method for preparing 3-carbonyl-4-aza-5alpha-androstanes
  • Method for preparing 3-carbonyl-4-aza-5alpha-androstanes

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Effect test

Embodiment 1

[0024] This embodiment is the preparation method of 3-carbonyl-4-aza-5α-androst-17β-carboxylic acid, the steps are as follows:

[0025] ①Add 10g of 3-carbonyl-4-aza-5-androstene-17β-carboxylic acid, 6g of ammonium formate and 250ml of formic acid into a dry reaction flask, stir and heat up to 60°C for hydrogenation reaction for 24h. Then concentrated under reduced pressure to remove formic acid, washed the reactant into 125ml of ice water to precipitate crystals, filtered and dried to obtain 9.6g of crude product.

[0026] ② Add the crude product to ethyl acetate for refluxing and dissolve, then recrystallize at 0-5°C to obtain 7.3 g of white crystals, and the α-body is determined to be 98.5 wt% by HPLC (high performance liquid chromatography).

Embodiment 2～ Embodiment 8

[0028] The rest are the same as in Example 1, and the differences are shown in Table 1.

[0029] Table 1

[0030] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 3-carbonyl-4-

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Abstract

The invention discloses a preparation method for a 3-carbonyl-4-aza-5alpha-androstane compound. The method comprises the following steps: 1, carrying out the hydrogenation action to a 3-carbonyl-4-aza-5 -androstane alkenyl compound, formic acid and a hydrogen donor agent for 5 to 24hours at 60 to 101 DEG C, then carrying out decompression and concentration to remove the formic acid, flushing the reactants into ice water for separating crystals, and obtaining a crude product after filtration and drying; and 2, adding the crude product into a recrystallization solution for recrystallization and obtaining the product. The hydrogen donor agent can be ammonium formate, potassium formate, sodium formate or triethylammonium formate. The preparation has the moderate reaction and low cost, and is suitable for the industrialized volume production.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of a class of 3-carbonyl-4-aza-5α-androsteroids. Background technique [0002] Benign prostatic hyperplasia (BHP) is a common disease in middle-aged and elderly men, and has been widely concerned by people. The theory of dihydrotestosterone has been used as the pathogenesis of benign prostatic hyperplasia. According to this theory, in the process of finding BPH therapeutic drugs, 5α reductase has become the target of screening drugs, and its inhibitors have also become a hot spot in drug development. 5α-reductase (5e-reductase) is a membrane protease dependent on reduced coenzyme II (NADPH), and its function is to catalyze the conversion of testosterone (T) into dihydrotestosterone (DHT), when DHT accumulates to a high level in the prostate and skin After that, it will cause many pathological changes, such as BPH, acne, male baldness, ...

Claims

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Application Information

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IPC IPC(8): C07J73/00
Inventor 蒋澄宇是东坡顾向忠
Owner JIANGSU JIAERKE PHARMA GRP CORP
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