94749-08-3

Usage

Uses

Used in Pharmaceutical Industry:
Salmeterol xinafoate is used as a bronchodilator for the treatment of reversible airway obstruction in asthma and chronic bronchitis. It is effective in managing symptoms and improving lung function due to its long-lasting bronchodilatory activity.
Used in Respiratory Therapy:
Salmeterol xinafoate is used as a β2-adrenergic agonist to relax smooth muscles in the airways, providing relief from wheezing and other respiratory symptoms associated with asthma and chronic obstructive pulmonary disease (COPD).
Used in Anti-inflammatory Therapy:
Salmeterol xinafoate is used as an anti-inflammatory agent, with significant anti-inflammatory activity that can complement prophylactic corticosteroid therapy. This makes it a valuable component in the management of respiratory conditions characterized by inflammation.
Used in Exercise-induced Asthma Management:
Salmeterol xinafoate is used as a preventive measure for exercise-induced asthma, helping to reduce the risk of bronchoconstriction during physical activity.
Chemical Properties:
Salmeterol xinafoate is a white to off-white solid.
Brand Name:
Serevent (GlaxoSmithKline).

Biochem/physiol Actions

β2-adrenoceptor agonist.

InChI:InChI=1/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2/t25-/m0/s1

Upstream product

• 89365-50-4 salmeterol 
• 86-48-6 1-hydroxy-2-naphthoic acid 
• 97664-55-6 N-[6-(4-phenylbutoxy)hexyl]benzenemethanamine 
• 115787-50-3 5-(2-bromoacetyl)-2-hydroxybenzaldehyde 
• 163923-19-1 2-hydroxy-5-<<<6,6-(4-phenylbutoxy)hexylbenzyl>amino>acetyl>benzaldehyde 

Relevant academic research and scientific papers

Preparation method of Salmeterol Xinafoate

The invention discloses a preparation method of Salmeterol Xinafoate. The method comprises the following steps: condensation reaction of a compound 2 and a compound 3 under alkaline conditions to obtain an intermediate 4; acidic hydrolysis to obtain an intermediate 5, and reduction reaction of the intermediate 5 to obtain an intermediate 6; debenzylation of the intermediate 6 by use of palladium carbon (Pd / C) to obtain a salmeterol basic group; and salification from the salmeterol basic group and 1-hydroxy-2-naphthoic acid to obtain the Salmeterol Xinafoate. The preparation method has the advantages of mild reaction condition, simple post-treatment, low cost, high yield, high product purity and easy industrialization.

PROCESS FOR THE PREPARATION OF SALMETEROL XINAFOATE

The present invention relates to an improved process for the preparation of Salmeterol Xinafoate of Formula (I).

PROCESS FOR THE PREPARATION OF SALMETEROL AND ITS INTERMEDIATES

The present invention discloses a process for the preparation of methyl 2-(benzyloxy)- 5-(2-bromoacetyl)benzoate (V), comprising: (d) benzylating methyl-5-acetyl-2-hydroxybenzoate (VIII) with benzyl chloride in the presence of a base and a catalyst in a suitable polar solvent to obtain 5-acetyl-2- benzyloxy benzoate (VII); (e) brominating methyl 5-acetyl-2-(benzyloxy)benzoate (VII) with a suitable brominating agent in one or more suitable' solvents in the presence of an acid catalyst to obtain methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate V; (c) optionally, purifying the methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate (V) in a suitable solvent; and (f) isolating the methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate (V).

SUBSTITUTED ETHANOLAMINES

The present invention relates to new substituted ethanolamine adrenergic receptor modulators, pharmaceutical compositions thereof, and methods of use thereof.

Novel process for preparing salmeterol

Accordingly, the present invention provides a process for the preparation of a compound of formula (I) or a single enantiomer thereof, or a salt or a solvate thereof, wherein W is a chiral auxiliary or hydrogen and P1 and P2 are each

Control of the physical form of salmeterol xinafoate

Two approaches to the generation of particles of the phenethanolamine, salmeterol xinafoate, are discussed. To produce particles with good flow properties a fast cooling crystallisation process was developed which delivered salmeterol xinafoate as spherical agglomerates of microcrystals which had good powder flow characteristics and could be micronised efficiently in a fluid energy mill. In a radically different approach, salmeterol xinafoate was crystallised using supercritical carbon dioxide in the SEDS (solution enhanced dispersion by supercritical fluids) process. By means of this technique the solid state form, crystal habit, and particle size of salmeterol xinafoate could be effectively controlled.

PHENETHANOLAMINE DERIVATIVES

Phenethanolamine derivatives are disclosed of formula STR1 wherein m is 2 to 8; n is 1 to 7 provided that m+n is 4 to 12; Ar is phenyl or phenyl substituted by one or two halogen atoms, alkyl or alkoxy groups or by an alkylenedioxy group;R. sup.1 and R 2 are hydrogen or alkyl provided that the sum total of carbon atoms in R 1 and R 2 is not more than 4; and the physiologically acceptable salts and solvates thereof. The compounds have a selective stimulant action at β 2-adrenoreceptors and may be used inter alia in the treatment of diseases associated with reversible airways obstructions such as asthma and chronic bronchitis. The compounds may be formulated in conventional manner as pharmaceutical compositions with physiologically acceptable carriers or excipients.The compounds may be prepared, for example by alkylation of an amine: STR2 where R 3, R 5 and R 6 is hydrogen or a protecting group, followed by removal of any protecting group.