135271-49-7

Basic information

• Product Name: (R)-Salmeterol 1-hydroxy-2-naphthoic acid salt
• Synonyms: (R)-Salmeterol 1-hydroxy-2-naphthoic acid salt;1,3-Benzenedimethanol, 4-hydroxy-a1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-, (a1R)-, 1-hydroxy-2-naphthalenecarboxylate (salt) (9CI);2-Naphthalenecarboxylic acid, 1-hydroxy-, compd. with (a1R)-4-hydroxy-a1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol (1:1) (9CI)
• CAS NO: 135271-49-7
• Molecular Formula: C36H45NO7
• Molecular Weight: 603.76
• Mol File: 135271-49-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-Salmeterol 1-hydroxy-2-naphthoic acid salt(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Salmeterol 1-hydroxy-2-naphthoic acid salt(135271-49-7)
• EPA Substance Registry System: (R)-Salmeterol 1-hydroxy-2-naphthoic acid salt(135271-49-7)

Safety Data

• Hazardous Substances Data: 135271-49-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-Salmeterol 1-hydroxy-2-naphthoic acid salt is used as a therapeutic agent for the treatment of asthma and chronic obstructive pulmonary disease (COPD). It functions by relaxing the smooth muscles in the airways, facilitating easier breathing and alleviating the symptoms associated with these respiratory conditions.
Additionally, the 1-hydroxy-2-naphthoic acid salt form of (R)-salmeterol may offer improved pharmacokinetic properties and stability compared to the free base form, potentially making it a more effective and convenient treatment option for patients with respiratory conditions.

Upstream product

• 89365-50-4 salmeterol 
• 86-48-6 1-hydroxy-2-naphthoic acid 
• 94749-73-2 6-bromohexyl 4-phenylbutyl ether 
• 629-03-8 1 ,6-dibromohexane 
• 3360-41-6 4-phenyl-butan-1-ol 
• 27475-14-5 2-benzyloxy-5-(2-bromoacetyl)benzoic acid methyl ester 
• 27475-09-8 5-acetyl-2-benzyloxybenzoic acid methyl ester 
• 16475-90-4 estere metilico dell'acido 5-acetilsalicilico 
• 163923-18-0 N-[6-(4-phenylbutoxy)hexyl] benzenemethanamine hydrochloride 
• 1351281-52-1 methyl 5-(2-(benzyl(6-(4-phenylbutoxy)hexyl)amino)acetyl)-2-(benzyloxy)benzoate 
• 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 articles and documents

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.

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

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.