Novel intermediate for synthesizing silodosin as well as preparation method and purpose of novel intermediate

A technology of intermediates and compounds, which is applied in the field of preparation of intermediate compounds, can solve problems such as high cost and complicated preparation process, and achieve the effects of reduced production costs, controllable optical purity, and mild reaction conditions

Active Publication Date: 2012-10-03
北京联本医药化学技术有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] When preparing silodosin based on the prior art, due to the key intermediate, i.e. 5-[(2R)-2-(amino)propyl]-1-[3-(benzoyloxy)propyl]- The prepa

Method used

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  • Novel intermediate for synthesizing silodosin as well as preparation method and purpose of novel intermediate
  • Novel intermediate for synthesizing silodosin as well as preparation method and purpose of novel intermediate
  • Novel intermediate for synthesizing silodosin as well as preparation method and purpose of novel intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation of 5-[2-(amino)propyl]-1-[3-(benzoyloxy)propyl]-7-cyanindoline L-tartrate

[0033] Add 3 kg of methanol into the hydrogenation kettle, then add 152.4 g of glacial acetic acid, 500 g of 5-[2-(nitro)propyl]-1-[3-(benzoyloxy)propyl]-7-cyanoindol Indoline, 50g of 10% palladium on carbon, after nitrogen replacement, heat to 60-65°C, feed hydrogen to 4-5 atmospheric pressure, react for 12 hours, monitor the reaction by TLC, after the reaction is completed, cool to room temperature, filter to remove palladium on carbon, a little methanol Rinse the palladium carbon, and the filtrate is concentrated under reduced pressure to remove the solvent. With stirring, it is added to the potassium carbonate solution prepared by 525.7 g of potassium carbonate and 2 kg of water, and then 1500 ml of tetrahydrofuran is added, and the organic phase is added by 209.7 g The solution prepared by L-tartaric acid and 1258 grams of water was cooled to about zero degree, kept fo...

Embodiment 2 6

[0037] The preparation of embodiment two to six 5-[2-(amino)propyl]-1-[3-(benzoyloxy)propyl]-7-cyanoindoline L-tartrate

[0038] Add methanol to the hydrogenation kettle, then add glacial acetic acid, 5-[2-(nitro)propyl]-1-[3-(benzoyloxy)propyl]-7-cyanindoline, 10 % palladium on carbon, after nitrogen replacement, heat to 60-65°C, feed hydrogen to 4-5 atmospheric pressure, react for 12 hours, monitor the reaction by TLC, after the reaction is completed, cool to room temperature, remove palladium carbon by filtration, rinse palladium carbon with a little methanol , the filtrate was concentrated under reduced pressure and evaporated to remove the solvent. Under stirring, it was added to the prepared aqueous potassium carbonate solution, then extracted with tetrahydrofuran, separated, the organic phase was added to the pre-prepared L-tartaric acid aqueous solution, cooled to about zero, and kept for 3 Hours, the solid was filtered and weighed after drying.

[0039] The specific ...

Embodiment 2 6

[0040] Table 1 embodiment two to six preparation 5-[2-(amino) propyl]-1-[3-(benzoyloxy) propyl]-7-cyanoindoline L-tartrate feed amount and results

[0041]

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PUM

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Abstract

The invention provides a novel optical active compound 5-[(2R)-2-(benzyl amino) propyl]-1-[3-( benzoyloxy) propyl]-7-cyanogroup indoline and a preparation method of the novel optical active compound. The compound can be used as an intermediate for synthesizing silodosin.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a new intermediate compound 5-[(2R)-2-(benzylamino)propyl]-1 for the synthesis of silodosin, a drug for treating benign prostatic hyperplasia -[3-(benzoyloxy)propyl]-7-cyanoindoline, and the preparation method and application of the new intermediate compound. Background technique [0002] 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 little side effects. It is used for the treatment of benign prostatic hyperplasia. At present, there are many synthetic methods related to the synthesis of silodosin, but there is a lack of methods with high yield and suitable for industrialized large-scale production. [0003] JP2001199956 reported the preparation of 5-[(2R)-2-aminopropyl[-1-[3-(benzoyloxy)propyl]--7-cyanindole by multi-step reaction using benzoic acid as ...

Claims

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Application Information

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IPC IPC(8): C07D209/08
Inventor 郭荣耀吕关锋刘贵斌
Owner 北京联本医药化学技术有限公司
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