1313429-32-1

Usage

Uses

Used in Pharmaceutical Industry:
(αR,βR)-β-ethyl-3-methoxy-α-methylbenzenepropanoic acid is used as an analgesic and anti-inflammatory agent for managing conditions such as arthritis, headache, and menstrual cramps. Its application is based on its ability to inhibit the activity of cyclooxygenase enzymes, which are responsible for the production of inflammatory mediators like prostaglandins.
Used in Pain Management:
Naproxen is utilized as a pain reliever for various types of pain, including musculoskeletal, dental, and postoperative pain. Its effectiveness in pain management is due to its ability to reduce inflammation and alleviate discomfort.
Used in Inflammation Reduction:
(αR,βR)-β-ethyl-3-methoxy-α-methylbenzenepropanoic acid is employed to reduce inflammation associated with various conditions, such as tendinitis, bursitis, and gout. Its anti-inflammatory action helps to decrease swelling, redness, and heat in the affected areas.

Upstream product

• 2972-72-7 2-(3-methoxybenzylidene)malononitrile 
• 591-31-1 3-methoxy-benzaldehyde 
• 24393-44-0 2-cyano-3-(3-methoxyphenyl)acrylic acid ethyl ester 
• 1313429-15-0 2-[1-(3-methoxy-phenyl)-propyl]-malononitrile 
• 1313429-17-2 3-(1-bromopropyl)anisole 
• 1313429-18-3 3-(3-methoxy-phenyl)-2-(toluene-4-sulfonyl)-pentanoic acid ethyl ester 
• 1313429-19-4 3-(3-methoxy-phenyl)-2-(toluene-4-sulfonyl)-pentanenitrile 
• 1313429-21-8 2-[1-(3-methoxy-phenyl)-propyl]-2-methyl-malononitrile 
• 1313429-22-9 3-(3-methoxy-phenyl)-2-methyl-2-(toluene-4-sulfonyl)-pentanoic acid ethyl ester 
• 1313429-23-0 3-(3-methoxy-phenyl)-2-methyl-2-(toluene-4-sulfonyl)-pentanenitrile 
• 1313429-24-1 2-methyl-3-(3-methoxyphenyl)pentanenitrile 
• 1313429-25-2 2-cyano-3-(3-methoxy-phenyl)-2-methyl-pentanoic acid 
• 1616-70-2 2-methyl-3-(3-methoxyphenyl)valeric acid 
• 1313429-26-3 diethyl 1-(3-methoxyphenyl)propylmethylmalonate 

Downstream Products

• 175591-09-0 tapentadol hydrochloride 
• 175591-23-8 tapentadol 
• 175591-22-7 (βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine 
• 1313429-37-6 (R),(R)-3-(3-methoxy-phenyl)-2-methyl-pentanoyl chloride 
• 1313374-09-2 (αR,βR)-β-ethyl-3-methoxy-N,N,α-trimethyl benzenepropanamide 
• 1313374-08-1 (R,R)-3-(3-methoxy-phenyl)-2-methyl-pentanoic acid methyl ester 
• 1322723-50-1 (βR,γR)-γ-ethyl-3-methoxy-β-methylbenzenepropanol 
• 1322723-68-1 (R),(R)-toluene-4-sulfonic acid 3-(3-methoxy-phenyl)-2-methyl-pentyl ester 
• 1313429-38-7 (S),(S)-3-(3-methoxy-phenyl)-2-methyl-pentanoic acid dimethylamide 

Relevant academic research and scientific papers

Substituted n-pentanamide compounds, preparation method and the use thereof

The present invention relates to a (2R, 3R)-3-(3-substituted phenyl)-2-methyl n-pentanamide compounds as shown in the formula I and the preparation method thereof, wherein, the substituents are as defined in the specification, the present invention further relates to a use of the above compounds for the preparation of tapentadol II or its pharmaceutically acceptable salt, and the intermediates involved in the preparation process.

SUBSTITUTED N-PENTANAMIDE COMPOUNDS, PREPARATION METHODS AND USES THEREOF

The present invention relates to a (2R, 3R)-3-(3-substituted phenyl)-2-methyl n-pentanamide compounds as shown in the formula I and the preparation method thereof, wherein, the substituents are as defined in the specification, the present invention further relates to a use of the above compounds for the preparation of tapentadol II or its pharmaceutically acceptable salt, and the intermediates involved in the preparation process.

O-SUBSTITUTED (2R,3R)-3-(3-HYDROXYPHENYL)-2-METHYL-4-PENTENOIC ACIDS AND A METHOD OF OBTAINING THE SAME

The compounds of general formula II are new and represent important intermediates in the synthesis of tapentadol. In the synthesis of tapentadol of formula I and its pharmaceutically acceptable salts, O-protected (2R,3R)-acids of general formula II, in step A, are reacted in an inert organic solvent with an activating agent, optionally in presence of a catalyst or a base; in step B, the obtained compounds of general formula V, wherein R has the above mentioned meaning and X stands for chlorine or alkoxycarbonyloxyl group O-CO-OR1 or pivaloyloxyl O-CO-t-Bu group, wherein R1 is methyl or ethyl, are reacted with dimethylamine or its salts optionally in presence of a base; in step C, the obtained N, N-dimethylamides of general formula VI, wherein R has the above mentioned meaning, are reduced by means of hydride agents in a suitable solvent; in step D, the produced alkeneamines of general formula VII, wherein R has the above mentioned meaning, are hydrogenated on a metal catalysts in a suitable solvent; and, finally, in step E, the produced alkaneamines of general formula VIII, wherein R has the above mentioned meaning, are O-dealkylated by means of dealkylating agents, and, if required, the obtained tapentadol is converted by the action of a pharmaceutically acceptable acid to respective salts, e.g. hydrochloride.

A NOVEL PROCESS FOR THE PREPARATION OF TAPENTADOL OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Disclosed herein is a novel, commercially viable and industrially advantageous process for the preparation of 3-[(1R,2R))-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol (Tapentadol), or a pharmaceutically acceptable salt thereof, in high yield and purity. Also described are novel intermediates useful for preparing tapentadol or a pharmaceutically acceptable salt thereof.

PROCESS FOR THE PREPARATION OF 1-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVES

A process for the preparation of 1-phenyl-3-dimethylaminopropane derivatives of formula (I) and its pharmaceutically acceptable salts thereof from cyano intermediate of formula (II), wherein R1 can be selected from -OR2, halo, -CH2OR2, -SR2, -SOR2, SO2R2, -SO3H, -NO2, -NR2R2', -CONR2R2', carboxylic esters, sulfonate esters or phosphate esters, R2 and R2' can be same or different, and can be selected from hydrogen, alkyl, aryl, aralkyl, heteroaryl, -COR2", -P03(R2")2 wherein R2" can be selected from alkyl, aryl, aralkyl, heteroaryl and the like.

PROCESS FOR THE PREPARATION OF L-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVES

The present invention provides a process for the preparation of 1-phenyl-3-dimethylaminopropane derivatives of formula I, and its pharmaceutically acceptable salts thereof from intermediate of formula II, wherein R1 can be selected from -OR2, halo, -CH2OR2, -SR2, SOR2, SO2R2, -SO3H, -NO2, -NR2R2', - CONR2R2 ', carboxylic esters, sulfonate esters or phosphate esters and the like; R ' can be selected from hydrogen, alkyl, aryl, aralkyl, alkaryl, heteroaryl, and the like; or OR ' can be selected from -NR2R2 '; or R2 and R2 ' can be same or different and can be selected from hydrogen, alkyl, aryl, aralkyl, heteroaryl,-OR3, - COR3, -PO3(R3R4) wherein R3 and R4 can be same or different and can be selected from alkyl, aryl, aralkyl, heteroaryl and the like.