106138-88-9

Basic information

• Product Name: (+)-Tamsulosin
• Synonyms: Benzenesulfonamide, 5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-, (S)- (9CI)
• CAS NO: 106138-88-9
• Molecular Formula: C20H28 N2 O5 S
• Molecular Weight: 408.51
• Mol File: 106138-88-9.mol

Chemical Properties

• Boiling Point: 595.5°Cat760mmHg
• Flash Point: 313.9°C
• Appearance: /
• Density: 1.191g/cm³
• Vapor Pressure: 3.79E-14mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: (+)-Tamsulosin(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Tamsulosin(106138-88-9)
• EPA Substance Registry System: (+)-Tamsulosin(106138-88-9)

Safety Data

• Hazardous Substances Data: 106138-88-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Tamsulosin is used as a medication for treating symptoms of benign prostatic hyperplasia (BPH). It is prescribed to improve symptoms such as difficulty urinating, weak stream, and the need to urinate frequently or urgently. The medication is typically taken orally and is available in both immediate-release and extended-release formulations.
Common side effects of (+)-Tamsulosin include dizziness, headache, and nasal congestion.

InChI:InChI=1/C20H28N2O5S/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)/t15-/m0/s1

Upstream product

• 86225-65-2 (R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride 
• 3259-03-8 2-(o-ethoxyphenoxy)-ethyl bromide 
• 852619-17-1 C₂₀H₂₆N₂O₅S 
• 3250-73-5 2-(2-ethoxyphenoxy)ethanol 
• 169506-15-4 2-(2-ethyloxyphenoxy)ethyl methanesulfonate 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 104-01-8 4-Methoxyphenylacetic acid 
• 80223-79-6 2-methoxy-5-(2-oxopropyl)benzenesulfonyl chloride 
• 94-71-3 2-Ethoxyphenol 
• 131029-02-2 (S)-1-(4-methoxyphenyl)propan-2-yl acetate 
• 131029-01-1 (S)-(+)-1-(4-methoxyphenyl)propan-2-ol 
• 1666-74-6 1-allyloxy-2-ethoxybenzene 
• 937018-21-8 (S)-1-(3-(chlorosulfonyl)-4-methoxyphenyl)propan-2-yl acetate 
• 937018-23-0 (S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl acetate 

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.

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)

Novel Pharmaceutical Forms, and Methods of Making and Using the Same

Crystalline salts, polymorphs, solvates, and hydrates of bicalutamide, 5-fluorouracil, donepezil, anastrozole, nelfinavir, mirtazapine, lansoprazole, and tamsulosin, or derivatives thereof are provided by the subject invention. Methods of making and using the same are also provided.

METHOD FOR PRODUCING OPTICALLY ACTIVE AMINE

The present invention provides a method for producing chiral amines, comprising asymmetric transfer hydrogenation of imine compounds in the presence of a hydrogen donor compound and an iridium(III) complex having a chiral prolinamide compound as a ligand. The present invention is useful for production of chiral amines in an efficient manner in terms of their optical and chemical yields.

THERAPY FOR COMPLICATIONS OF DIABETES

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

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 AND RELATED COMPOUNDS

The invention relates, in general, to the preparation of tamsulosin free base. More particularly, the invention relates to a process for preparing pure solid crystalline tamsulosin in its free base form as a precursor for the production of tamsulosin hydrochloride.