885340-13-6

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-7-carbonitrile, 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]aMino]propyl]is used as an impurity in the synthesis of Silodosin (S465000) for the treatment of benign prostatic hyperplasia. It plays a role in the development and production of this medication, which helps alleviate symptoms associated with an enlarged prostate.

Upstream product

• 115661-82-0 7-cyanoindoline 
• 1269801-73-1 [2-(2,2,2-trifluoroethoxy)phenoxy]acetaldehyde 
• 1269801-74-2 2-[2-(2,2,2-trifluoroethoxy)phenoxy-ethyl]-[1,3]dioxalane 
• 160969-02-8 2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethanol 
• 160968-99-0 2-O-(2,2,2-trifluoroethyl)catechol 
• 106854-74-4 2-methoxy-1-(2,2,2-trifluoroethoxy)benzene 
• 885340-11-4 2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile 
• 120-80-9 benzene-1,2-diol 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 160970-54-7 silodosin 

Relevant academic research and scientific papers

Preparation method of silodosin intermediate

The invention relates to a preparation method of a silodosin intermediate. The preparation method is characterized in that: the intermediate is 1-(3- hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2,2-trifluoroethoxyl] phenoxyl] ethylamino] propyl]-7-nitrile-1H-indoline. The preparation method is shown in the description. The raw materials used in the method are sold on the market, are cheap, and are low in cost. The yield in various step is relatively high, and the post-processing is simple. The preparation method does not use poisonous or hazardous agent, and is convenient for industrialization. The product quality is high, and the optical purity is high.

Preparation method of silodosin

The invention discloses a preparation method of silodosin. The preparation method comprises the following steps: S1, carrying out an asymmetric Henry condensation reaction on a substance 1 and nitroethane under the action of a copper salt and a chiral catalyst 2 to obtain a substance 3; S2, carrying out a reduction reaction on the substance 3 and hydrogen under the action of a catalyst 4 to obtaina substance 5; and S3, enabling the substance 5 to react with 2-(2-trifluoroethoxyphenoxy)ethyl methanesulfonate and an alkali to obtain a substance 6, and hydrolyzing the substance 6 to obtain silodosin. The method is novel in route, short in synthetic route, mild in reaction condition and convenient and controllable to operate, the chiral center is directly synthesized by the chiral catalyst without chiral resolution, and the prepared silodosin is good in chiral purity, high in yield, obvious in cost advantage and suitable for industrial production.

NOVEL SULFONAMIDE INTERMEDIATE AND METHOD FOR PRODUCING SILODOSIN BY USING THE SAME

PROBLEM TO BE SOLVED: To provide a method for producing silodosin by using a novel sulfonamide intermediate. SOLUTION: The method for producing silodosin or a pharmaceutically acceptable salt thereof includes reacting a compound of the formula as given below and a thiol group-containing Meisenheimer complex forming agent in the presence of an alkali metal carbonate or an alkali metal alkoxide. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

A silodosin intermediate and its preparation method, and the intermediate for method of preparation of the silodosin

The invention relates to the field of compound synthesis and especially relates to a silodosin intermediate, a preparation method of the silodosin intermediate, and a method for preparing silodosin from the silodosin intermediate. The method for preparing silodosin from the silodosin intermediate has the characteristics of economy, safety, high purity and high yield and is suitable for large-scale industrial production.

THE PROCESS OF PREPARING INDOLINE COMPOUNDS AND A NOVEL INDOLINE SALT

The present invention provides an industrial method for production of silodosin, which is useful for a therapeutic agent for dysuria associated with benign prostatic hyperplasia. The production of silodosin is characterized by mixing (R)-l-(3-hydroxypropyl)-5-(2-(2- (2-(2, 2, 2-trifluoroethoxy) phenoxy) ethyl amino) propyl) indoline-7-carbonitrile (V) and N-acetyl-L-glutamic acid to yield the N-acetyl-L-glutamate salt, subsequently neutralising the N-acetyl-L-glutamate salt and hydrolyzing the same, and manufacturing intermediates used therefore. The invention also provides an industrial production method of silodosin alpha, beta and gamma crystalline forms.

Method for preparing silodosin

The invention relates to a method for preparing silodosin, especially to an industrial preparation method of a silodosin compound, and belongs to the field of pharmaceutical chemical synthesis. The method includes: carrying out salt hydrolysis on 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-nitrile tartrate to obtain 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-nitrile, preparing benzoic acid-R-3-[7-cyano-5-(2-{2-[2-(2,2,2-trifluoro-ethoxy)-phenoxyl]-ethylamino}-propyl)-2,3-dihydro-indole-1-yl]-propylester which is an intermediate, and finally performing a hydrolysis reaction to produce silodosin. According to the provided industrial production method of silodosin, the yield is high, purification becomes easy and the impurity content is low.

METHOD FOR PRODUCING INDOLINE COMPOUND

Provided is a method for producing a compound represented by a formula (6), the method comprising: a step of mixing a compound represented by a formula (4) and a compound represented by a formula (5) to form a salt consisting of the compound represented by the formula (4) and the compound represented by the formula (5); and a step of removing a protecting group P1 of the salt. In the following formulae, P1 is a protecting group and P2 is a protecting group.

Process for preparing silodosin

The present invention provides a method for producing silodosin through a novel synthesis pathway, wherein the silodosin is a therapeutic agent of urinary disturbances by benign prostatic hyperplasia. In addition, the present invention provides a method for producing a beta crystal form and/or a gamma crystal form of the silodosin using a crystallization solvent with excellent stability.COPYRIGHT KIPO 2016

NOVEL INTERMEDIATE USED FOR THE PREPARATION OF SILODOSIN, METHOD FOR PREPARING SAME, AND METHOD FOR PREPARING SILODOSIN USING SAME

The present invention relates to a 3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoro-ethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indol-1-yl}propyl benzoate 2-oxoglutaric acid salt of chemical formula 5b as a novel intermediate used in preparation of silodosin, a method for preparing the same, and a method for preparing silodosin using the same. The intermediate has excellent filterability of crystals. A process for preparing silodosin uses the intermediate, so that the reaction time is short, and the amount of an unreacted starting material and a dialkylated byproduct is low. Therefore, the novel intermediate according to the present invention can be useful for preparing of silodosin which is a treating agent for prostatism.COPYRIGHT KIPO 2015