- PROCESS FOR THE PREPARATION OF TAPENTADOL AND ANALOGS THEREOF
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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.
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- A kind of dual role of analgesic of the center of the new compound, preparation method and use thereof
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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
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- TWO-STEP PROCESS FOR PREPARING 3-SUBSTITUTED PHENYLALKYLAMINES
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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.
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- NEW SYNTHESIS OF TAPENTADOL-HCl INTERMEDIATES
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The present invention relates to a process for the synthesis of tapentadol intermediates comprising the following route of synthesis: (I) → (II) → (III) → (IV) → (V).
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- PROCESS FOR THE PREPARATION OF 3-[(1R,2R)-3-(DIMETHYLAMINO)-1-ETHYL-2-METHYLPROPYL]-PHENOL
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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).
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- PROCESS FOR PREPARING SUBSTITUTED PHENYLALKANES
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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.
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- Compounds and Methods for Preparing Substituted 3-(1-amino-2-methylpentane-3-yl)phenyl Compounds
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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
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- TAPENTADOL MALEATE AND CRYSTALLINE FORMS THEREOF
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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.
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- Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds
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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.
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- METHOD FOR THE PREPARATION OF 1-ARYL-1-ALKYL-2-ALKYL-3-DIALKYLAMINOPROPANE COMPOUNDS
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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.
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- STEREOSELECTIVE SYNTHESIS OF TAPENTADOL AND ITS SALTS
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A process for the synthesis of a salt of tapentadol.
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- PROCESS FOR THE PREPARATION OF TAPENTADOL
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Disclosed herein is an improved process for the preparation of 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol of Formula-I and its pharmaceutically acceptable salt which comprises the reaction of (S)-1-(dimethylamino)-2-methylpentan-3-one of formula VIII with 3-bromo anisole of formula II under Grignard conditions to get the compound (2S, 3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol of formula V followed by activation of the —OH group of the formula V to convert into sulfonate esters of formula IX, which are on reductive deoxygenation to yield (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentan-1-amine of formula VII and demethylation of formula VII to obtain the compound 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol of Formula-1.
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Paragraph 0060; 0061; 0062
(2013/06/05)
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- PROCESS FOR THE SYNTHESIS OF TAPENTADOL AND INTERMEDIATES THEREOF
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The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high
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Paragraph 0097; 0098
(2013/07/19)
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- PROCESS FOR PREPARING L-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVE
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Provided is a process for the preparing 1-phenyl-3-dimethylaminopropane derivatives of formula I, (The formula should be inserted here) and its pharmaceutically acceptable salts thereof via novel intermediates.
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- NEW PROCESS FOR THE SYNTHESIS OF TAPENTADOL AND INTERMEDIATES THEREOF
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The object of the present invention is a new process for the synthesis of tapentadol, both as free base and in hydrochloride form, which comprises the step of alkylation of the ketone (VII) to yield the compound (VIII), as reported in Diagram 1, with high
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Page/Page column 9; 17
(2012/01/14)
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- TAPENTADOL HYDROBROMIDE AND CRYSTALLINE FORMS THEREOF
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The present invention provides a salt of Tapentadol, Tapentadol liydrobromide, and crystalline forms of Tapentadol hydrobromide.
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Page/Page column 6
(2012/05/04)
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- METHOD OF PRODUCING (2R,3R)-NA-DIMETHYL-3-(3-HYDROXYPHENYI)-2-METHYLPENTYLAMINE (TAPENTADOL)
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The present solution relates to a method comprising, as a key step, production of optically pure or optically enriched tapentadol of formula I, in which optically pure or optically enriched (2R,3R)-amines of general formula V, wherein R stands for a phenylmethyl group, substituted or non-substituted in the benzene ring, e.g. benzyl or 4-methoxybenzyl, benzhydryl or trityl group, are hydrogenated on a metal catalyst and, if desired, the obtained tapentadol is converted by the action of pharmaceutically acceptable acids to respective salts, such as to hydrochloride.
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- PROCESS FOR PREPARING L-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVE
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Provided is a process for the preparing l-phenyl-3-dimethylaminopropane derivatives of formula I, (The formula should be inserted here) and its pharmaceutically acceptable salts thereof via novel intermediates.
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- PROCESS FOR THE PREPARATION OF TAPENTADOL
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Disclosed herein is an improved process for the preparation of 3-[(2R,3R)-1- (dimethylamino)-2-methylpentan-3-yl] phenol of Formula - I and its pharmaceutically acceptable salt which comprises the reaction of (S)-1-(dimethylamino)-2-methylpentan- 3-one of formula VIII with 3 - bromo anisole of formula II under Grignard conditions to get the compound (2S, 3R)-1- (dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3- ol of formula V followed by activation of the -OH group of the formula V to convert into sulfonate esters of formula IX, which are on reductive deoxygenation to yield (2R,3R)-3- (3-methoxyphenyl)-N,N,2-trimethylpentan-1 -amine of formula VII and demethylation of formula VII to obtain the compound 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3- yl]phenol of Formula - 1.
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- Process for Preparing Substituted 3-(1-amino-2-methylpentane-3-yl)phenyl Compounds
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A process for the preparation of substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds.
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Page/Page column 17
(2012/01/03)
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- PRODRUGS OF OPIOIDS AND USES THEREOF
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The present invention concerns prodrugs of opioid analgesics and pharmaceutical compositions containing such prodrugs. Methods for providing more consistent pain relief by increasing the bioavailability of the opioid analgesic with the aforementioned prodrugs are provided. The invention also provides for decreasing the adverse GI side effects of opioid analgesics.
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- PROCESS FOR THE PREPARATION OF 1-PHENYL-3-DIMETHYLAMINOPROPANE DERIVATIVES
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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.
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- PROCESS FOR THE PREPARATION OF (1R,2R)-3-(3-DIMETHYLAMINO-1-ETHYL-2-METHYL-PROPYL)-PHENOL
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The present invention relates to a process for the preparation of (1 R,2R)-3- dimethylamino-1-ethyl-2-methyl-propyl)-phenol.
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Page/Page column 23
(2008/06/13)
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This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.
