503068-34-6

Basic information

• Product Name: Vilanterol
• Synonyms: Vilanterol;GW 642444X;Vilanterol API;GW 642444;GW642444;GW-642444;4-[(R)-2-[[6-[2-(2,6-Dichlorobenzyloxy)ethoxy]hexyl]amino]-1-hydroxyethyl]-2-hydroxymethylphenol;Vilanterol(GW642444)
• CAS NO: 503068-34-6
• Molecular Formula: C₂₄H₃₃Cl₂NO₅
• Molecular Weight: 486.42852
• EINECS: 690-631-3
• Product Categories: Inhibitors
• Mol File: 503068-34-6.mol

Chemical Properties

• Boiling Point: 646.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• Solubility: Soluble in DMSO
• PKA: 9.99±0.20(Predicted)
• CAS DataBase Reference: Vilanterol(CAS DataBase Reference)
• NIST Chemistry Reference: Vilanterol(503068-34-6)
• EPA Substance Registry System: Vilanterol(503068-34-6)

Safety Data

• Hazardous Substances Data: 503068-34-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Vilanterol is used as a bronchodilator for the treatment of chronic obstructive pulmonary disease (COPD). It works by relaxing the muscles in the airways, which helps to improve lung function and reduce symptoms such as shortness of breath and wheezing in patients with this condition.

Biological Activity

vilanterol is a novel and selective agonist of β2-ar with a pec50 value of 10.37±0.05 [1].vilanterol is a novel long-acting β2-ar agonist (laba) with 24h activity in development for inhaled once daily treatment. in the radioligand binding studies, vilanterol has shown the binding affinity in the one-affinity site model with pkd values of 9.44±0.07 and 10.82±0.12 in the presence gpp(nh)p and absence gpp(nh)p, respectively. in dissociation studies, vilanterol has been reported to bind from the β2-ar with a dissociation t1/2 value of 3.5 min in the presence of gpp(nh)p. vilanterol has been found to have a good selectivity for β2-ar over the other β-ar receptor subtypes(β1and β3) with pec50 values of 10.37±0.05, 6.98±0.03 and 7.36±0.03, respectively. vilanterol has exhibited at least 1000-fold selectivity over both β1-and β3-ar subtypes [1].

references

[1] slack rj1, barrett vj, morrison vs, sturton rg, emmons aj, ford aj, knowles rg.in vitro pharmacological characterization of vilanterol, a novel long-acting β2-adrenoceptor agonist with 24-hour duration of action.j pharmacol exp ther. 2013 jan; 344(1):218-30.

Upstream product

• 54030-34-1 1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanone 
• 102293-80-1 2-bromo-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethanone 
• 452339-70-7 di-(tert-butyl) 2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxoethyliminodicarbonate 
• 452339-71-8 tert-butyl 2-(2,2-dimethyl-4H-1,3-benzodioxane-6-yl)-2-carbonylethylcarbamate 
• 452339-72-9 tert-butyl (2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethylcarbamate 
• 452339-73-0 (5R)-5-(2,2-dimethyl- 4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one 
• 20443-98-5 2,6-Dichlorobenzyl bromide 
• 503070-57-3 2-((2-((6-bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzene 
• 52113-69-6 6-bromo-2,2-dimethyl-4H-benzo[1,3]dioxine 
• 503068-36-8 (5R)-3-{6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one 
• 503068-37-9 (2R)-hydroxy-2-(2,2-dimethyl-4Η-1,3-benzodioxole-6-yl)-N-3-[6-[2-[(2,6-dichlorophenyl)methoxy]ethoxy]hexyl]-ethylamine 
• 2316-64-5 5-bromo-2-hydroxybenzyl alcohol 
• 743460-69-7 (R)-(2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethoxy)(tert-butyl)dimethylsilane 
• 72189-44-7 3-hydroxymethyl-4-hydroxymandelic acid 

Downstream Products

• 503070-59-5 4-[(1R)-2-({6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol α-phenylcinnamate 
• 503070-58-4 4‐{(1R)‐2‐[(6‐{2‐[(2,6‐dichlorobenzyl)oxy]ethoxy}hexyl)amino]‐1‐hydroxyethyl}‐2‐(hydroxymethyl)phenol triphenylacetate 

Relevant articles and documents

METHOD FOR THE PURIFICATION OF VILANTEROL TRIFENATATE

Method for the purification of vilanterol trifenatate It is provided a method for the purification of vilanterol trifenatate of formula (I) comprising crystallizing vilanterol trifenatate from a ketone solvent selected from the group consisting of methyl ethyl ketone (MEK), methyl isobutyl ketone (MIK), ethyl isopropyl ketone, methyl isopropyl ketone, 3-methyl-2-pentanone, and a mixture thereof.

AN IMPROVED PROCESS FOR PREPARATION OF VILANTEROL OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

The invention discloses an improved process for preparation of Vilanterol or a pharmaceutically acceptable salt thereof with good yields and high purity.

Preparation method of vilanterol

The invention provides a preparation method of vilanterol, which comprises the following steps: 1) oxidation reaction: reacting a compound A with an oxidant to obtain a compound B; wherein the oxidantis selenium dioxide; 2) reductive amination reaction: carrying out condensation reaction on the compound B and a compound C to generate an imine intermediate, and carrying out a reaction on the imineintermediate under the action of a reducing agent to obtain a compound D; 3) reduction reaction: carrying out a reaction on the compound D with a chiral catalyst and a reducing agent to obtain a compound E, and 4) ring-opening reaction: performing deprotection ring-opening on the compound E under an acidic condition to obtain vilanterol. The method is advantaged in that the initial raw materialsare easy to obtain, the process is suitable for industrial production, the production yield is high and quality is stable.

Preparation method of vilanterol and salt thereof

The invention relates to a preparation method of vilanterol and a salt thereof. The preparation method comprises the following steps: in a solvent, reacting a mixture containing a compound shown as aformula I with succinic acid to obtain a compound shown as a formula II-1; and subjecting the obtained compound shown as the formula II-1 to reacting and conversion to obtain vilanterol and the salt thereof. The preparation method of the vilanterol and the salt thereof has the advantages of higher yield, high purity, easiness in refining, simplicity and convenience in operation and suitability forindustrialization.

Method for preparing Vilanterol

The invention discloses a method for preparing Vilanterol, and belongs to the field of drug synthesis. The method includes the steps: (1) performing addition reaction on salicyloyl and glyoxylic acidto generate an intermediate 1; (2) performing chiral resolution on the intermediate 1 to obtain a chiral intermediate 2; (3) performing acylation reaction on the intermediate 2 and an intermediate 3 to generate an intermediate 4; (4) reducing the intermediate 4 to obtain the Vilanterol. The intermediate 3 is obtained by performing Darebin reaction on an intermediate 5. Raw materials are easily obtained, a synthetic route is short, production cost is reduced, reaction conditions are mild, and the method is simple in operation and suitable for industrial production.

BIOCATALYTIC PROCESSES FOR THE PREPARATION OF VILANTEROL

A process for preparing Vilanterol includes a biocatalytic conversion of a ketone substrate to its corresponding alcohol, and then converting the obtained alcohol into Vilanterol. Polypeptides may be used for the biocatalytic conversion of the ketone substrate, such as 2-bromo-l-(2,2-dimethyl-4H-l,3-benzodioxin-6-yl)ethanone, to an enantiopure alcohol, (R)-2-bromo-l-(2,2-dimethyl-4H-l,3-benzodioxin-6-yl)ethanol for the preparation of Vilanterol. Also disclosed is vilanterol tartrate and solid state forms thereof for use as medicaments and for the preparation of other vilanterol salts, or of vilanterol, solid state forms and/or formulations thereof. Also disclosed is a process for the preparation of pharmaceutical formulations including vilanterol tartrate and solid state forms thereof, as well as a method of treating a person suffering from COPD and asthma by administering a therapeutically effective amount of any one or a combination of vilanterol tartrate and solid state forms thereof or a pharmaceutical composition and/or formulation comprising vilanterol tartrate and solid state forms thereof.

A new technology of blue Trowsynthesizes Uygur

The present invention discloses a new method for synthesizing vilanterol. The present invention provides a completely-new vilanterol synthesis method, wherein the easily available starting raw material is adopted so as to effectively avoid disadvantages of harsh reaction conditions (such as anhydrous reaction), expensive reagents and the like of the existing process, and the method has characteristics of short route, high yield, and market competitiveness.

PROCESS FOR THE PREPARATION OF VILANTEROL AND INTERMEDIATES THEREOF

An improved process for the preparation of vilanterol and pharmaceutically acceptable salts thereof is disclosed. More specifically the improved process for preparing intermediates for the preparation of vilanterol is disclosed.