Synthesis method of drug intermediate flutamide

A technology of a body flutamide and a synthesis method, which is applied in the field of synthesis of a pharmaceutical intermediate flutamide, can solve problems such as decreased curative effect, and achieve the effects of sufficient exposure, high catalytic efficiency and stable catalytic activity.

Inactive Publication Date: 2018-05-08
徐州诺克非医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of flutamide is that while competitively inhibiting the stimulating effect of dihydrotestosterone on the prostate, it also inhibits the negative feedback effect of androgen on the hypothalamus, which can eventually increase the secretion of testicular T, thereby reducing the curative effect

Method used

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  • Synthesis method of drug intermediate flutamide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] A kind of synthetic method of medicine intermediate flutamide, this method comprises the following steps:

[0019] Step 1. After adding 20ml of n-hexane into a 100ml three-necked flask, add 2.0g of catalyst and 3.22g of m-trifluoromethylaniline, start magnetic stirring, heat to 45°C, and drop 6.32g of isobutyric anhydride within 30min. Incubate for 1 hour, sample and analyze;

[0020] Step 2. Add 10ml of water to the reaction solution. After the addition, the temperature drops. Then add 10ml of 30% NaOH solution again. The temperature rises to above 50°C, then rises to 70°C, keeps warm for 15min, puts it in an ice machine, and cools down to 10°C. Filter and dry under vacuum at 60°C to obtain a white solid;

[0021] Step 3. Put the 100ml three-necked bottle equipped with mechanical stirring and a thermometer into the ice machine, add 23ml of concentrated sulfuric acid, stir, add 10.75g of m-isobutyramide trifluorotoluene, after the solid is dissolved, keep the temperatu...

Embodiment 2

[0031] Step 1. After adding 20ml of n-hexane into a 100ml three-necked flask, add 2.0g of catalyst and 1.61 m-trifluoromethylaniline, start magnetic stirring, heat to 45°C, add 6.32g of isobutyric anhydride dropwise within 30min, and keep warm 1h, sampling analysis; the rest of the steps are the same as in Example 1.

Embodiment 3

[0033] Step 1. After adding 20ml of n-hexane into a 100ml three-necked flask, add 2.0g of catalyst and 0.81 m-trifluoromethylaniline, start magnetic stirring, heat to 45°C, add 6.32g of isobutyric anhydride dropwise within 30min, and keep warm 1h, sampling analysis; the rest of the steps are the same as in Example 1.

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Abstract

The invention discloses a synthesis method of a drug intermediate flutamide. N-hexane, m-trifluoromethylaniline, isobutyric anhydride, NaOH, m-isobutyramidobenzotrifluoride, sodium hydrogen carbonateand ethyl orthosilicate are used as main raw materials; a method of combining a sol-gel method with calcination is utilized; SiO2 is used as a carrier; a perfluorosulfonic resin solution is directly dispersed on a porous SiO2 colloid serving as a skeleton; a mixing-ratio relation among raw materials is strictly explored; a catalyst for preparing the flutamide from the isobutyric anhydride, which has certain crystal form, grain size, pore structure and specific area and high mechanical strength is developed; the raw materials used by the synthesis method are according to the following mixing ratios in which a mass ratio of the isobutyric anhydride to the m-trifluoromethylaniline is 2 to 1, a volume ratio of the n-hexane to the NaOH is 2 to 1, and the volume ratio of concentrated sulfuric acid to concentrated nitric acid is 10 to 1; a preparation method of the flutamide has the characteristics of simpleness, easiness, feasibleness, short preparation period and the like, and the raw materials and the catalyst which are used in a technical process have high efficiency, wide application ranges and an excellent catalytic effect on the preparation of the flutamide from the isobutyric anhydride, are simple, convenient, quick and extremely environment-friendly, moreover, are easily recovered and can be regenerated.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate flutamide, which belongs to the technical field of pharmaceutical synthesis. Background technique [0002] Flutamide can be metabolized in the human body to metabolite, which has biological activity and can prevent the action of androgen in target cells, thereby exerting efficacy on prostate cancer. The disadvantage of flutamide is that while competitively inhibiting the stimulating effect of dihydrotestosterone on the prostate, it also inhibits the negative feedback effect of androgen on the hypothalamus, which can eventually increase the secretion of testicular T, thereby reducing the curative effect. Compared with antiandrogen prostatic drugs with similar structure, flutamide has the advantages of less side effects, simple synthesis and the like. Recently, chelated flutamide analogues have been reported as radiopharmaceuticals for single photon emission computed tomogr...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C231/12C07C233/15B01J27/02
CPCB01J27/02C07C231/02C07C231/12C07C233/15
Inventor 赵青玲李伟新
Owner 徐州诺克非医药科技有限公司
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