80223-99-0

Basic information

• Product Name: Tamsulosin hydrochloride
• Synonyms: Tamsulosinehydrochloride;Benzenesulfonamide, 5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-, monohydrochloride (9CI);dl-Tamsulosin hydrochloride;(-)-(R)-5-[2-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide hydrochloride;Tamsulosin hydrochloride;Tamuzosin hydrochloride;EC-617;Racemic Tamsulosin Hydrochloride (50 mg)
• CAS NO: 80223-99-0
• Molecular Formula: C20H29ClN2O5S
• Molecular Weight: 444.97
• Product Categories: Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 80223-99-0.mol

Chemical Properties

• Melting Point: 228-230℃
• Boiling Point: 595.5 °C at 760 mmHg
• Flash Point: 313.9 °C
• Appearance: /
• Vapor Pressure: 3.79E-14mmHg at 25°C
• CAS DataBase Reference: Tamsulosin hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Tamsulosin hydrochloride(80223-99-0)
• EPA Substance Registry System: Tamsulosin hydrochloride(80223-99-0)

Safety Data

• Hazardous Substances Data: 80223-99-0(Hazardous Substances Data)

Usage

Clinical Use

Treatment of benign prostatic hyperplasia

Drug interactions

Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Antidepressants: enhanced hypotensive effect with MAOIs. Antifungals: concentration increased by ketoconazole. Avanafil, vardenafil, sildenafil and tadalafil: enhanced hypotensive effect, avoid concomitant use. Beta-blockers: enhanced hypotensive effect; increased risk of first dose hypotensive effect. Calcium-channel blockers: enhanced hypotensive effect; increased risk of first dose hypotensive effect. Diuretics: enhanced hypotensive effect; increased risk of first dose hypotensive effect. Moxisylyte: possibly severe postural hypotension.

Metabolism

Tamsulosin is metabolised slowly in the liver primarily by the cytochrome P450 isoenzymes CYP2D6 and CYP3A4; it is excreted mainly in the urine as metabolites and some unchanged drug

InChI:InChI=1/C20H28N2O5S.ClH/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24;/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24);1H

Upstream product

• 80223-99-0 (+/-)-Tamsulosin hydrochloride 
• 106463-17-6 (+)-Tamsulosin 
• 521300-99-2 (R)-tamsarocin (-)-camphor-10-sulfonate 
• 3259-03-8 2-(o-ethoxyphenoxy)-ethyl bromide 
• 112101-81-2 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide 
• 94-71-3 2-Ethoxyphenol 
• 80223-79-6 2-methoxy-5-(2-oxopropyl)benzenesulfonyl chloride 
• 104-01-8 4-Methoxyphenylacetic acid 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 94666-07-6 5-[2-[2-(2-ethoxyphenoxy)-ethylamino]-2-methylethyl]-2-methoxybenzenesulfonamide 
• 169506-15-4 2-(2-ethyloxyphenoxy)ethyl methanesulfonate 
• 3250-73-5 2-(2-ethoxyphenoxy)ethanol 
• 106133-20-4 (R)-tamsulosin 
• 6781-17-5 2-(2-ethoxyphenoxy)-ethylamine 

Relevant articles and documents

Continuous-Flow Synthesis of (R)-Tamsulosin Utilizing Sequential Heterogeneous Catalysis

We describe the continuous-flow synthesis of (R)-tamsulosin, a blockbuster therapeutic drug employed for dysuria associated with urinary stones and benign prostatic hyperplasia, by utilizing sequential heterogeneous catalysis. Two heterogeneous catalysts have been developed for the synthesis, and the key step involves reductive amination of nitriles using dimethylpolysilane-modified Pd on activated carbon/calcium phosphate. Overall, (R)-tamsulosin was obtained in 60 % yield and 64 % ee (99 % ee after recrystallization) in a flow stream through four catalytic transformations without the need for the isolation or purification of any intermediates or byproduct.

Preparation method of tamsulosin hydrochloride

The invention belongs to the technical field of chemical synthesis, and relates to a synthesis method of tamsulosin hydrochloride. The preparation method comprises the following steps: firstly reacting benzenesulfonamide as shown in a formula (II) with bromo ether as shown in a formula (III) to obtain a condensation compound intermediate as shown in a formula (IV), carrying out transfer hydrogenation reaction on the intermediate as shown in the formula (IV) in the presence of ammonium formate and a catalyst to obtain R-tamsulosin free alkali as shown in a formula (V), subjecting the R-tamsulosin free alkali and hydrochloric acid to a salt forming reaction in an organic solvent, so that the tamsulosin hydrochloride shown in the formula (I) is obtained. The method is characterized in that the reaction of the formula (II) and the formula (III) is carried out in a solvent containing water. According to the synthesis route disclosed by the invention, in the reaction process of the obtained tamsulosin hydrochloride, no disubstituted by-product generated by reaction of bimolecular bromide and amine exists, the obtained tamsulosin hydrochloride has the advantages of good product purity, stable quality and high yield, and the synthesis method disclosed by the invention is mild in reaction condition and convenient to synthesize.

Preparation method of tamsulosin hydrochloride crystal form

The invention relates to the technical field of preparation of crystal forms of organic compounds, in particular to a preparation method of a tamsulosin hydrochloride crystal form. The method comprises the following steps: completely dissolving tamsulosin in a solvent at 60-70 DEG C, then dropwise adding acid for reaction for a period of time, conducting cooling to 20-30 DEG C, and conducting filtering, washing and drying to obtain tamsulosin, wherein tamsulosin is a refined product. The method is simple in process, high in yield, high in product purity and suitable for large-scale industrialization.

Preparation method of tamsulosin hydrochloride

The invention provides a preparation method of tamsulosin hydrochloride. Specifically, the preparation method comprises a step of reacting 5-acetonyl-2-methoxybenzenesulfonamide with (R)-1-phenylethylamine under the action of a reducing agent to obtain a compound as shown in a formula (IV) or pharmaceutically acceptable salt thereof, and further comprises a step of preparing tamsulosin hydrochloride from the compound as shown in the formula (IV) or pharmaceutically acceptable salt thereof. The preparation method provided by the invention is high in safety and strong in operability, avoids theuse of a heavy metal catalyst, and has an industrial actual use value.

A high optical purity of tamsulosin preparation method of leach

The invention discloses a preparation method of tamsulosin hydrochloride with high optical purity, and belongs to a medicine technology and a chemical field. A recrystallization method is adopted, crude products of (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl phenyl sulfonamide hydrochloride are refined, so that pure products of the (R)-5-(2-(2-(2-ethoxyphenoxy) ethyl amino) propyl)-2-methoxyl group sulfonamide hydrochloride of which the e.e. value is larger than 99.8% is obtained; a crystallizing solvent adopted by the recrystallization method is a mixed solvent consisting of an organic solvent and water, the organic solvent is selected from one of methanol, ethyl alcohol, acetone, acetonitrile and isopropyl alcohol, and the recrystallization temperature is under 15 DEG C. The preparation method disclosed by the invention is simple to operate, short in period, low in cost and good in repeatability, and can solve the inevitable problem of rework for treatment in the industrial production.

Method of resolving tamsulosin enantiomer

The invention relates to a method of resolving tamsulosin enantiomer, and in particular, relates to a method of resolving tamsulosin, represented as the formula (I), into an R-enantiomer and an S-enantiomer. The method includes the steps of: (a) dissolving a solid mixture of (R)-tamsulosin free alkali and (S)-tamsulosin free alkali in a solvent and performing a reaction to the free alkalis with camphor-10-sulfonic acid to form a solution containing a pair of diastereomeric camphor-10-sulfonates of tamsulosin, and then preferentially precipitating one diastereomeric camphor-10-sulfonate of the tamsulosin from the solution containing a pair of the diastereomeric camphor-10-sulfonates of tamsulosin, thereby forming a precipitate, in which one diastereomer is enriched, and a solute, in which the other one diastereomer is enriched; and (b) from one of the precipitate and the solute, releasing tamsulosin free alkali to obtain optical-rotation-enriched tamsulosin free alkali. The method has excellent technical performance.

PROCESS FOR PREPARATION OF HIGH PURITY TAMSULOSIN OR SALT THEREOF

The present invention refers to of the existing method contain pharmaceutically available plasticizer manufacturing method compared to a simple, low-environmentally friendly, purity contain pharmaceutically available plasticizer or contain pharmaceutically available plasticizer hydrochloride provides manufacturing method. (by machine translation)

Process for Preparing Tamsulosin Hydrochloride

The invention relates to an process for preparing Tamsulosin hydrochloride of Formula (I) which comprises (i) reacting (R)-(?)-5-(2-amino-propyl)-2-methoxybenzenesulfonamide of Formula (II) with substituted phenoxy compound of Formula (III), wherein Z represents a removing group, such as —OSO2CH3, —OSO2C6H4CH3, —F, —Br, —Cl, or —I, in a solvent in the presence of an alkaline earth metal oxide to obtain Tamsulosin base and (ii) converting Tamsulosin base into hydrochloride salt in a solvent by addition of aqueous hydrochloric acid.

AN IMPROVED PROCESS FOR THE PREPARATION OF TAMSULOSIN HYDROCHLORIDE

The invention relates an improved process for preparing the (R)-(-)5-[2-[[2-(2-ethoxyphenoxyethyl]amino]propyl]-2-methoxybenzenesulfonamide of Formula (I): and its pharmaceutically acceptable salts.

PROCESS FOR THE PREPARATION OF TAMSULOSIN

The invention includes an improved process for producing tamsulosin comprising reacting 5-(2-aminopropyl)-2-methoxybenzenesulfonamide with 2-(o-ethoxyphenoxy)ethyl bromide in an organic phosphite solvent to obtain tamsulosin. Optically pure (R)- 5-(2-aminopropyl)-2- methoxybenzenesulfonamide can be employed to produce optically pure (R)-tamsulosin product. The organic phosphite solvent utilized in the reaction can include tri-alkyl phosphites such as triethyl phosphite, trimethyl phosphite, and tributyl phosphite. Additionally, processes for producing tamsulosin having a low concentration of by-product contaminants, such as 5-((R)-2- {Bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide, and the use of such by-products to monitor the chemical purity of tamsulosin, are provided.