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Preparation method of silodosin intermediate

A compound and reaction technology, applied in the field of medicine, can solve the problems of complex synthesis process, high cost and low yield, and achieve the effects of high industrial application value, low purchase cost and high reaction yield

Active Publication Date: 2015-10-14
JIANGSU HECHENG ADVANCED MATERIALS
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The main shortcoming of this route has: when a, bromination will use more expensive tribromopyrrolidone; B, two-step hydrogenation reduction reaction all will use expensive catalyst platinum oxide; Low, use column chromatography to separate and purify
[0026] When synthesizing silodosin based on the prior art, the preparation of the key intermediate usually complicates the synthesis process and the cost is high, so the present invention is proposed

Method used

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  • Preparation method of silodosin intermediate
  • Preparation method of silodosin intermediate
  • Preparation method of silodosin intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0103] 1) Preparation of Compound 9-1

[0104]

[0105] Weigh 140g of benzoyl chloride (commercially available) into a 1L single-necked bottle, add 600mL of dichloromethane and 70g of triethylamine, cool to 0°C, slowly add 94g of 3-chloropropanol dropwise, and keep the temperature below 10°C. After the dropwise addition, the reaction was continued for 1 h.

[0106] After the completion of the reaction was monitored by TLC, the organic layer was washed with 300 mL*3 water, dried over anhydrous sodium sulfate, and the solvent was concentrated to obtain 188 g of a colorless liquid (compound 9-1) with a purity of 99%. MS m / z: 198 (M + ), yield: 95%.

[0107] For the MS diagram of compound 9-1, see figure 1 .

[0108] 2) Preparation of compound 2

[0109]

[0110] Weigh 132g of compound 1 (commercially available) into a 2L three-neck flask, then add 1L of dichloromethane and 167g of triethylamine into it, cool to 0°C, slowly add acetyl chloride (130g, 1.5eq) dropwise, an...

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Abstract

The invention discloses a preparation method of a silodosin intermediate, wherein the structure of the silodosin intermediate is represented as the formula A. The preparation method, wherein indoline is employed as a start raw material, includes the reactions of Friedel-Crafts acylation, carbonyl reduction, Gabriel reaction and chiral resolution and the like. The preparation method is simple in operation, is low in cost, is high in yield, allows the product to purify easily and is stable in processes, and is suitable for industrial production. The invention also discloses a new intermediate compound which is related in the method.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for preparing silodosin intermediates and novel intermediate compounds involved in the method. Background technique [0002] Benign prostatic hyperplasia (BPH) is a common and frequently-occurring disease in middle-aged and elderly men. Currently, the drugs used clinically for the treatment of BPH are mainly divided into two categories: α1-adrenoceptor (α-AR) antagonists and 5α-reductase inhibitors. Among them, the α-AR antagonist has the characteristics of rapidity, safety and high efficiency. Silodosin is a BPH α-AR antagonist for the treatment of dysuria caused by benign prostatic hyperplasia. [0003] Silodosin has a selective inhibitory effect on the contraction of urethral smooth muscle, and reduces urethral pressure, but has no great effect on blood pressure, and has few side effects, so it can be used to treat benign prostatic hyperplasia. [0004]...

Claims

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Application Information

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IPC IPC(8): C07D209/08C07C51/41C07C59/255
CPCC07C51/41C07C59/255C07D209/08
Inventor 刘琦徐爽魏小超靳灿辉谭玉东孙仲猛曹林法
Owner JIANGSU HECHENG ADVANCED MATERIALS
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