CA2797757C - New process for the synthesis of tapentadol and intermediates thereof - Google Patents

New process for the synthesis of tapentadol and intermediates thereof Download PDF

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Publication number
CA2797757C
CA2797757C CA2797757A CA2797757A CA2797757C CA 2797757 C CA2797757 C CA 2797757C CA 2797757 A CA2797757 A CA 2797757A CA 2797757 A CA2797757 A CA 2797757A CA 2797757 C CA2797757 C CA 2797757C
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CA
Canada
Prior art keywords
process according
acid
compound
tapentadol
halide
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CA2797757A
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English (en)
French (fr)
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CA2797757A1 (en
Inventor
Giuseppe Motta
Domenico Vergani
Giorgio Bertolini
Nicola Landoni
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Curia Italy SRL
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Euticals SpA
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • 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
    • 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
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • 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
    • C07C213/08—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 not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • 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
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
    • C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
    • C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/20—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C219/22—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2797757A 2010-07-02 2011-06-20 New process for the synthesis of tapentadol and intermediates thereof Active CA2797757C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ITMI2010A001224A IT1401109B1 (it) 2010-07-02 2010-07-02 Nuovo processo per la preparazione di tapentadol e suoi intermedi.
ITMI2010A001224 2010-07-02
PCT/IB2011/052685 WO2012001571A1 (en) 2010-07-02 2011-06-20 New process for the synthesis of tapentadol and intermediates thereof

Publications (2)

Publication Number Publication Date
CA2797757A1 CA2797757A1 (en) 2012-01-05
CA2797757C true CA2797757C (en) 2018-09-25

Family

ID=43432160

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2797757A Active CA2797757C (en) 2010-07-02 2011-06-20 New process for the synthesis of tapentadol and intermediates thereof

Country Status (13)

Country Link
US (1) US8791287B2 (https=)
EP (1) EP2588429B1 (https=)
JP (1) JP5857044B2 (https=)
CN (1) CN102958868B (https=)
AU (1) AU2011273044B2 (https=)
BR (1) BR112012029882A2 (https=)
CA (1) CA2797757C (https=)
CL (1) CL2012003760A1 (https=)
ES (1) ES2572637T3 (https=)
IL (1) IL223066A (https=)
IT (1) IT1401109B1 (https=)
MX (1) MX340833B (https=)
WO (1) WO2012001571A1 (https=)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013111161A2 (en) * 2012-01-10 2013-08-01 Msn Laboratories Limited Process for the preparation of 3-aryl-2-methyl-propanamine derivatives and polymorphs thereof
EP2674414A1 (en) 2012-06-15 2013-12-18 Siegfried AG Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds
US9090539B2 (en) 2013-05-24 2015-07-28 Ampac Fine Chemicals Llc Compounds and methods for preparing substituted 3-(1-amino-2-methylpentane-3-yl)phenyl compounds
CZ307492B6 (cs) 2014-02-04 2018-10-17 Zentiva, K.S. Pevná forma maleátu tapentadolu a způsob její přípravy
EP4116288A1 (en) 2021-07-08 2023-01-11 KRKA, d.d., Novo mesto Racemization of (s) and/or (r)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1- one and its mixtures
CN113861155A (zh) * 2021-10-21 2021-12-31 华南师范大学 一种二氢异香豆素类衍生物及其制备方法与应用
CN119191999A (zh) * 2024-11-26 2024-12-27 苏州盛迪亚生物医药有限公司 一种制备他喷他多或其可药用盐的方法
CN119176758B (zh) * 2024-11-26 2025-05-09 苏州盛迪亚生物医药有限公司 一种固载催化制备他喷他多或其可药用盐的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US429833A (en) 1890-06-10 Means for creating artificial currents
US3888901A (en) 1972-07-20 1975-06-10 American Cyanamid Co Process of preparing 3-alkyl-3-(benzoyl)propionitriles
DE2901180A1 (de) * 1979-01-13 1980-07-24 Basf Ag Hexahydro-1,4-oxazepine, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE4426245A1 (de) 1994-07-23 1996-02-22 Gruenenthal Gmbh 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung
DE10326097A1 (de) 2003-06-06 2005-01-05 Grünenthal GmbH Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen
TWI496762B (zh) * 2006-07-24 2015-08-21 製備（１ｒ，２ｒ）-３-（３-二甲胺基-１-乙基-２-甲基-丙基）-酚之方法
TWI401237B (zh) * 2006-07-24 2013-07-11 ３-〔（１ｒ，２ｒ）-３-（二甲基氨基）-１-乙基-２-甲基丙基〕酚之製備
BRPI0714671B8 (pt) * 2006-07-24 2023-03-21 Janssen Pharmaceutica Nv Preparação de (2r,3r)-3-(3-metoxifenil)-n,n,2-trimetilpentanamina e compostos intermediários

Also Published As

Publication number Publication date
CN102958868B (zh) 2014-11-05
AU2011273044A1 (en) 2012-11-15
WO2012001571A1 (en) 2012-01-05
US8791287B2 (en) 2014-07-29
MX2012015161A (es) 2013-06-28
IL223066A (en) 2015-09-24
CA2797757A1 (en) 2012-01-05
US20130178644A1 (en) 2013-07-11
EP2588429A1 (en) 2013-05-08
IT1401109B1 (it) 2013-07-12
IL223066A0 (en) 2013-02-03
EP2588429B1 (en) 2016-02-24
JP2013529676A (ja) 2013-07-22
ITMI20101224A1 (it) 2012-01-03
CL2012003760A1 (es) 2013-12-13
JP5857044B2 (ja) 2016-02-10
ES2572637T3 (es) 2016-06-01
MX340833B (es) 2016-07-27
BR112012029882A2 (pt) 2018-05-15
AU2011273044B2 (en) 2015-02-12
CN102958868A (zh) 2013-03-06

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