885340-11-4

Usage

Uses

Used in Pharmaceutical Industry:
1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-Indole-7-carbonitrile is used as a potential pharmaceutical agent for its possible biological activity, which may be attributed to its diverse functional groups and structural complexity.
Used in Chemical Industry:
In the chemical industry, 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-Indole-7-carbonitrile may serve as a building block for the synthesis of other complex molecules, given its unique structural features and functional groups. This could be particularly useful in the development of new materials or compounds with specific properties.

Upstream product

• 239463-85-5 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt 
• 239463-72-0 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile 
• 160969-03-9 1-(2-methanesulfonyloxyethoxy)-2-(2,2,2-trifluoroethoxy)benzene 
• 942-95-0 3-chloropropyl benzoate 
• 115661-82-0 7-cyanoindoline 
• 87-69-4 L-Tartaric acid 
• 350797-52-3 1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole 
• 350797-51-2 1-(3-benzoyloxypropyl)-2,3-dihydroindole hydrochloride 
• 1338365-54-0 5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole 

Downstream Products

• 885340-13-6 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile 
• 160970-54-7 silodosin 
• 885340-12-5 (2R)-3-(7-cyano-5-(2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)-2,3-dihydro-1H-indol-1-yl)propyl benzoate oxalate 

Relevant academic research and scientific papers

5-substituted indoline derivative or salt thereof, preparation method and application of 5-substituted indoline derivative or salt thereof, and preparation method of silodosin

The invention relates to the technical field of medicines, in particular to a 5-substituted indoline derivative or a salt thereof, a preparation method and application of the 5-substituted indoline derivative or the salt thereof, and a preparation method of silodosin. Silodosin can be prepared by taking the 5-substituted indoline derivative provided by the invention as an intermediate through first N-alkylation, bromination, cyano substitution, deprotection, second N-alkylation and hydrolysis. The reaction route is short, and the total yield of the silodosin is high. The 5-substituted indoline derivative salt provided by the invention has good stability. According to the method, phthalic anhydride or substituted phthalic anhydride and D-alanine are taken as starting materials, the 5-substituted indoline derivative can be obtained through condensation, acylating chlorination, Friedel-Crafts reaction, reduction and hydrolysis, the reaction route is short, chiral construction does not need resolution, the atom utilization rate is high, the total yield is larger than 57.5%, and the yield is high; and the raw materials are cheap and easily available, and the production cost is low.

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.

Preparation method of silodosin intermediate

The present invention relates to a method for preparing a silodosin intermediate represented by a formula III. The method comprises: reacting a compound represented by a formula I or a salt thereof with a compound represented by a formula II to generate a compound represented by a formula III, wherein X is a leaving group, PG is a protecting group of hydroxyl, and the reaction system used in the reaction comprises alkali metal phosphate and/or alkali metal halide.

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

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.

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.

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

Process for preparing an intermediate useful for the synthesis of silodosin

The present invention provides an improved producing method of 3-{7-cyano-5[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl)-2,3-dihydro-1H-indole-1-yl}propylene benzoate, as an essential intermediate product used in synthesizing silodosin which is a therapeutic agent of urinary disturbances by benign prostatic hyperplasia. In addition, the present invention provides: a novel acid addition salt of the essential intermediate product; and a producing method of silodosin using the improved producing method.COPYRIGHT KIPO 2016