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Preparation method of silodosin intermediate

A technology for organic ligands and compounds, applied in the field of preparing silodosin intermediates and new intermediate compounds, can solve problems such as unsuitable industrial production, and achieve the effects of simple operation, mild reaction conditions and high purity

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

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Problems solved by technology

[0012] JP2006188470 reported the R-compound shown in formula M (R 1 = benzyl), but several steps in the method are purified by column chromatography, which is not suitable for industrial production

Method used

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  • Preparation method of silodosin intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0081] 1) Preparation of compound SLD-8C

[0082]

[0083] Weigh 107g of SLD-9C (commercially available) into a 2L three-necked flask, add 600mL of methanol, stir mechanically and add 131mL of thionyl chloride dropwise in an ice-water bath, and build an exhaust gas absorption device, and then reflux for 5 to 8 hours after dropping.

[0084] After the completion of the reaction monitored by TLC, methanol was directly concentrated and evaporated, washed with 120mL*3 toluene, concentrated and evaporated to remove residual toluene, and pumped for 24 hours to obtain 167g of white solid SLD-8C, yield: 99.6%.

[0085] 1 H-NMR (d 6 -DMSO) δ: 8.71 (s, 1H); 8.52 (s, 2H); 3.71 ~ 4.05 (m, 1H); 3.36 ~ 3.46 (s, 3H); 1.19 ~ 1.62 (d, 3H).

[0086] Compound SLD-8C 1 H NMR chart see figure 1 .

[0087] 3) Preparation of compound SLD-7C

[0088]

[0089] Weigh 167g of SLD-8C, 242g of triethylamine, and 1L of dichloromethane into a 2L three-necked flask, add dropwise 313g of di-tert-b...

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Abstract

A method for preparing silodosin intermediate is disclosed. Said intermediate has the structure of (M), wherein R is benzyl or benzoyl. Said preparation method has the characteristics of short reaction route, simple operation, low cost, high yield, stable process, etc. The method is suitable for industrial production, and has extra-high industrial application value. Intermediate compounds for preparing the intermediate represented by M are also disclosed.

Description

technical field [0001] The invention belongs to the technical field of medicines, 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. There a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 刘琦严加浩徐爽靳灿辉谭玉东孙仲猛曹林法
Owner JIANGSU HECHENG ADVANCED MATERIALS
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