WO2012146978A3 - A novel process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof - Google Patents

A novel process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof Download PDF

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Publication number
WO2012146978A3
WO2012146978A3 PCT/IB2012/000919 IB2012000919W WO2012146978A3 WO 2012146978 A3 WO2012146978 A3 WO 2012146978A3 IB 2012000919 W IB2012000919 W IB 2012000919W WO 2012146978 A3 WO2012146978 A3 WO 2012146978A3
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutically acceptable
tapentadol
acceptable salt
preparation
novel process
Prior art date
Application number
PCT/IB2012/000919
Other languages
French (fr)
Other versions
WO2012146978A2 (en
Inventor
Sandipan Prabhurao Bondge
Mayur Devjibhai Khunt
Nitin Sharadchandra Pradhan
Original Assignee
Actavis Group Ptc Ehf
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Actavis Group Ptc Ehf filed Critical Actavis Group Ptc Ehf
Publication of WO2012146978A2 publication Critical patent/WO2012146978A2/en
Publication of WO2012146978A3 publication Critical patent/WO2012146978A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

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.
PCT/IB2012/000919 2011-04-28 2012-04-25 A novel process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof WO2012146978A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1467/CHE/2011 2011-04-28
IN1467CH2011 2011-04-28

Publications (2)

Publication Number Publication Date
WO2012146978A2 WO2012146978A2 (en) 2012-11-01
WO2012146978A3 true WO2012146978A3 (en) 2013-01-03

Family

ID=46172808

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2012/000919 WO2012146978A2 (en) 2011-04-28 2012-04-25 A novel process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof

Country Status (1)

Country Link
WO (1) WO2012146978A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3083551B1 (en) 2013-12-16 2018-02-14 Farma GRS, d.o.o. Crystalline form of tapentadol intermediate
CN103787898B (en) * 2014-01-17 2016-05-25 暨明医药科技（苏州）有限公司 A kind of synthetic method of tapentadol hydrochloride
CN104803861B (en) * 2014-01-27 2017-05-24 上海博邦医药科技有限公司 Method for synthesizing tapentadol hydrochloride
ES2940904T3 (en) * 2014-07-10 2023-05-12 SpecGx LLC Procedure for preparing substituted phenylalkanes
CN105801500B (en) * 2014-12-31 2018-08-24 四川科伦药物研究院有限公司 The method for splitting Chinese mugwort Saperconazole intermediate compound raceme

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248737B1 (en) * 1994-07-23 2001-06-19 Gruenenthal Gmbh 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
WO2005000788A1 (en) * 2003-06-23 2005-01-06 Grünenthal GmbH Method for dehydrating substituted 4-dimethylamino-2-aryl-butan-2-ol compounds and method for producing substituted dimethyl-(3-aryl-butyl)-amine compounds by means of heterogeneous catalysis
WO2011080736A1 (en) * 2009-12-29 2011-07-07 Mapi Pharma Hk Limited Intermediate compounds and processes for the preparation of tapentadol and related compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10326097A1 (en) 2003-06-06 2005-01-05 Grünenthal GmbH Process for the preparation of dimethyl (3-aryl-butyl) -amine compounds
DE102005033732B4 (en) 2005-05-27 2014-02-13 Grünenthal GmbH Separation of stereoisomeric N, N-dialkylamino-2-alkyl-3-hydroxy-3-phenyl-alkanes
TWI401237B (en) 2006-07-24 2013-07-11 Preparation of 3-[(1r, 2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol monohydrochloride
AU2007278224C1 (en) 2006-07-24 2012-06-21 Grünenthal GmbH Preparation of (2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentanamine
TWI448447B (en) 2006-07-24 2014-08-11 Gruenenthal Chemie Process for the preparation of (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248737B1 (en) * 1994-07-23 2001-06-19 Gruenenthal Gmbh 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
WO2005000788A1 (en) * 2003-06-23 2005-01-06 Grünenthal GmbH Method for dehydrating substituted 4-dimethylamino-2-aryl-butan-2-ol compounds and method for producing substituted dimethyl-(3-aryl-butyl)-amine compounds by means of heterogeneous catalysis
WO2011080736A1 (en) * 2009-12-29 2011-07-07 Mapi Pharma Hk Limited Intermediate compounds and processes for the preparation of tapentadol and related compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
VAJDA M: "Preparation of 1-Aryl-Isobenzpyrylium salts", ACTA CHIMICA ACADEMIAE SCIENTIARUM HUNGARICA, BUDAPEST, HU, vol. 40, 1 January 1964 (1964-01-01), pages 295 - 307, XP009164384, ISSN: 0001-5407 *

Also Published As

Publication number Publication date
WO2012146978A2 (en) 2012-11-01

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