175591-23-8

Usage

Uses

Analgesic (μ-agonist).

Pharmacology

Tapentadol, a relatively new opioid, also has distinct mechanisms of analgesic action. It is a MOP receptor agonist more potent than tramadol. It also acts by selectively inhibiting reuptake of noradrenaline, and therefore there may be a rationale for using it in patients with pain with neuropathic features.

InChI:InChI=1/C14H23NO/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12/h6-9,11,14,16H,5,10H2,1-4H3

Upstream product

• 37951-49-8 1-(3-methoxyphenyl)propan-1-one 
• 1353891-30-1 C₈H₈O₃*C₁₉H₂₃NO₂ 
• 1353891-28-7 (S)-3-(benzyl-methylamino)-2-methyl-1-(3-methoxy-phenyl)-propan-1-one 
• 1353941-01-1 (2R,3R)-3-(3-methoxyphenyl)-2-methyl-pentyl-methyl-amine 
• 1353891-32-3 (2S,3R)-1-(benzyl(methyl)amino)-3-(3-methoxyphenyl)-2-methyl-3-pentanol 
• 13103-80-5 1-(3-hydroxyphenyl)propan-1-one 
• 1343471-61-3 rac-3-(dimethylamino)-1-(3-hydroxyphenyl)-2-methylpropan-1-one 
• 1369205-94-6 toluene-4-sulfonic acid 3-(3-dimethylamino-2-methylpropionyl)phenyl ester 
• 1369205-95-7 [2S]-toluene-4-sulfonic acid 3-(3-dimethylamino-2-methylpropionyl)phenyl ester 
• 1369205-97-9 dibenzoyl-L-tartaric acid [2S]-toluene-4-sulfonic acid 3-(3-dimethylamino-2-methylpropionyl)phenyl ester 
• 1369205-82-2 [2S,3RS]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-1-hydroxy-2-methylpropyl)phenyl ester 
• 1369206-01-8 [2S,3RS]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-1-hydroxy-2-methylpropyl)phenyl ester hydrochloride 
• 1369206-03-0 (1R)-toluene-4-sulfonic acid 3-[1-(2-dimethylamino-1-methylethyl)propenyl]phenyl ester 
• 1369205-85-5 [1R,2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenyl ester 

Downstream Products

• 175591-09-0 tapentadol hydrochloride 
• 1277097-35-4 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol salicylate 
• 1313429-31-0 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol D-dibenzoyl tartaric acid salt 
• 1314003-88-7 (R,R)-tapentadol-(PABA tert-butyl ester) carbamate 
• 1356394-24-5 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol nitrate 
• 1356394-25-6 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol nicotinate 
• 1356394-28-9 (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol malonate 
• 1356394-26-7 tapentadol bisulfate 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF TAPENTADOL AND ANALOGS THEREOF

The present invention relates to a process for the preparation of tapentadol and analogs or compounds or stereoisomers of formula (I), Formula I wherein, A is aryl, heteroaryl, and cycloalkyl; R is H, OH, OR1, halogen, C1-C12 alkyl, cycloalkyl, aryl or heteroaryl; R1 is C1-C12 alkyl, cycloalkyl, aryl or heteroaryl, wherein each of these groups may further be substituted with one or more substituent selected from H, OH, halogen, CN, NO2, C1-C4 alkyl or phenyl. Further, the multi-step process involves no column chromatography purification until the very last step. This makes this process highly commercially viable and industrially useful.

A kind of dual role of analgesic of the center of the new compound, preparation method and use thereof

The invention relates to a central-analgesic novel compound having double effects, or a pharmaceutical salt or a hydrate thereof, a preparation method of the novel compound and an application of the novel compound in drugs. The compound is represented as

TWO-STEP PROCESS FOR PREPARING 3-SUBSTITUTED PHENYLALKYLAMINES

Processes for preparing 3-substituted phenylalkylamines comprising reacting a phenyl boronic compound with an α-β unsaturated carbonyl-containing compound via an asymmetric 1,4-addition reaction, followed by reductive alkylation. The processes may be useful in the synthesis of tapentadol.

NEW SYNTHESIS OF TAPENTADOL-HCl INTERMEDIATES

The present invention relates to a process for the synthesis of tapentadol intermediates comprising the following route of synthesis: (I) → (II) → (III) → (IV) → (V).

PROCESS FOR PREPARING SUBSTITUTED PHENYLALKANES

The invention provides methods for preparing substituted phenylalkanes. In particular, the processes comprise reacting a phenyl boronic compound with an α-β unsaturated carbonyl-containing compound via an asymmetric 1,4-addition reaction. The processes may be useful in the synthesis of tapentadol.

PROCESS FOR THE PREPARATION OF 3-[(1R,2R)-3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL]-PHENOL

A process for the preparation of a compound of formula (I) and of a acid salt (T) wherein R1 is selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R2 and R3, are, independently of each other, selected from the group consisting of alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, R4, R5, R6 and R7, are independently of each other, selected from the group consisting of H, alkyl, aryl, cycloalkyl, heteroalkyl, heteroaryl and heterocycloalkyl, and wherein the acid salt is a 2,3-Ditoluoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid salt, 2,3-Dianisoyl tartaric acid salt, 2,3-Dibenzoyl tartaric acid mono(dimethylamide) salt or a mixture of two or more thereof, wherein the tartaric acid salt (T) of the compound of formula (I) contains at least 90 % by weight of the tartaric salt of the compound of formula (Ia) based on the total weight of the acid salt of the compound of formula (I).

Compounds and Methods for Preparing Substituted 3-(1-amino-2-methylpentane-3-yl)phenyl Compounds

Compounds and methods for preparing substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds from an isomerically pure starting material are described. In particular, methods of preparing a 3-(1-(dimethylamino)-2-methylpentane-3-yl)phenol as a substan

TAPENTADOL MALEATE AND CRYSTALLINE FORMS THEREOF

Disclosed herein is a novel and stable salt of tapentadol, tapentadol maleate, its polymorphic Forms as well as processes for its preparation, pharmaceutical compositions, and preparation thereof.

Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds

The present invention refers to the preparation of 1-aryl-1-alkyl-2-alkyl-3-dialkylamino-propane compounds, such as tapentadol, using a diastereoselective Eschenmoser-Claisen or Ireland-Claisen rearrangement.

METHOD FOR THE PREPARATION OF 1-ARYL-1-ALKYL-2-ALKYL-3-DIALKYLAMINOPROPANE COMPOUNDS

The present invention refers to the preparation of 1-aryl-1-alkyl-2-alkyl-3-dialkylamino-propane compounds, such as tapentadol, using a diastereoselective Eschenmoser-Claisen or Ireland-Claisen rearrangement.