94749-08-3

Basic information

• Product Name: Salmeterol xinafoate
• Synonyms: (+/-) 4-HYDROXY-A1-[[[6-(4-PHENYLBUTOXY)HEXYL]AMINO]M-ETHYL]-1,3-BENZENEDIMETHANOL XINAFOATE;GR 33343X XINAFOATE;SALMETEROL XINAFOATE;SALMETEROL XINAFONATE;Arial;GR-33343G;Salmetedur;Salmeterol, 1-Hydroxy-2-naphthoate
• CAS NO: 94749-08-3
• Molecular Formula: C36H45NO7
• Molecular Weight: 603.74
• Product Categories: Active Pharmaceutical Ingredients;API;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor;Amines;Aromatics;Stable Isotopes;Inhibitors
• Mol File: 94749-08-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 137-138°C
• Boiling Point: 603 °C at 760 mmHg
• Flash Point: 318.5 °C
• Appearance: white/solid
• Density: 1.112g/cm3
• Vapor Pressure: 2.16E-15mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: -20°C Freezer
• Solubility: H2O: slightly soluble
• Merck: 14,8337
• CAS DataBase Reference: Salmeterol xinafoate(CAS DataBase Reference)
• NIST Chemistry Reference: Salmeterol xinafoate(94749-08-3)
• EPA Substance Registry System: Salmeterol xinafoate(94749-08-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: QJ1970500
• Hazardous Substances Data: 94749-08-3(Hazardous Substances Data)

Usage

Description

Salmeterol xinafoate, also known as Salmeterol hydroxynaphthoate, is a long-acting β2-selective adrenoceptor agonist. It is a structural analog of albuterol and is used as a bronchodilator for the treatment of reversible airway obstruction in asthma and chronic bronchitis. Salmeterol xinafoate has bronchodilatory activity that is as intense as, and four times longer-lasting than, equivalent doses of salbutamol. It is also reported to be the first bronchodilator with significant anti-inflammatory activity, making it a potential complement to prophylactic corticosteroid therapy.

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

• 934842-69-0 4-hydroxy-1-[[[6-(4-phenylbutoxy)hexyl](phenylmethyl)amino]methyl]-1,3-benzenedimethanol 
• 163923-19-1 2-hydroxy-5-<<<6,6-(4-phenylbutoxy)hexylbenzyl>amino>acetyl>benzaldehyde 
• 115787-50-3 5-(2-bromoacetyl)-2-hydroxybenzaldehyde 
• 97664-55-6 N-[6-(4-phenylbutoxy)hexyl]benzenemethanamine 
• 1351281-52-1 methyl 5-(2-(benzyl(6-(4-phenylbutoxy)hexyl)amino)acetyl)-2-(benzyloxy)benzoate 

Relevant articles and documents

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 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).

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