AU2004245223C1 - Method for the production of substituted 3-aryl-butyl amine compounds - Google Patents

Method for the production of substituted 3-aryl-butyl amine compounds Download PDF

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Publication number
AU2004245223C1
AU2004245223C1 AU2004245223A AU2004245223A AU2004245223C1 AU 2004245223 C1 AU2004245223 C1 AU 2004245223C1 AU 2004245223 A AU2004245223 A AU 2004245223A AU 2004245223 A AU2004245223 A AU 2004245223A AU 2004245223 C1 AU2004245223 C1 AU 2004245223C1
Authority
AU
Australia
Prior art keywords
methyl
phenyl
dimethylamine
methoxy
dimethylamino
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
AU2004245223A
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English (en)
Other versions
AU2004245223B2 (en
AU2004245223A1 (en
Inventor
Bernhard Akteries
Helmut Buschmann
Hans-Joachim Drexler
Stefan Gladow
Wolfgang Hell
Detlef Heller
Jorg Holenz
Markus Kegel
Hartmut Lobermann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gruenenthal GmbH
Original Assignee
Gruenenthal GmbH
Chemie Gruenenthal GmbH
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
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Application filed by Gruenenthal GmbH, Chemie Gruenenthal GmbH filed Critical Gruenenthal GmbH
Publication of AU2004245223A1 publication Critical patent/AU2004245223A1/en
Publication of AU2004245223B2 publication Critical patent/AU2004245223B2/en
Application granted granted Critical
Publication of AU2004245223C1 publication Critical patent/AU2004245223C1/en
Anticipated expiration legal-status Critical
Expired legal-status Critical Current

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    • 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
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
    • 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
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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
    • C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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 hydroxy groups
    • C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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 hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C07C215/62—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having 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 hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2004245223A 2003-06-06 2004-06-04 Method for the production of substituted 3-aryl-butyl amine compounds Expired AU2004245223C1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10326097.8 2003-06-06
DE10326097A DE10326097A1 (de) 2003-06-06 2003-06-06 Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen
PCT/EP2004/006027 WO2004108658A1 (de) 2003-06-06 2004-06-04 Verfahren zur herstellung substituierter 3-aryl-butyl-aminverbindungen

Publications (3)

Publication Number Publication Date
AU2004245223A1 AU2004245223A1 (en) 2004-12-16
AU2004245223B2 AU2004245223B2 (en) 2010-01-28
AU2004245223C1 true AU2004245223C1 (en) 2010-06-10

Family

ID=33494923

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2004245223A Expired AU2004245223C1 (en) 2003-06-06 2004-06-04 Method for the production of substituted 3-aryl-butyl amine compounds

Country Status (25)

Country Link
US (1) US7417170B2 (enExample)
EP (1) EP1633697B1 (enExample)
JP (1) JP4848268B2 (enExample)
KR (1) KR101146205B1 (enExample)
CN (1) CN1829681B (enExample)
AT (1) ATE425136T1 (enExample)
AU (1) AU2004245223C1 (enExample)
BR (1) BRPI0411268C8 (enExample)
CA (1) CA2528087C (enExample)
CY (1) CY1109088T1 (enExample)
DE (2) DE10326097A1 (enExample)
DK (1) DK1633697T3 (enExample)
EC (1) ECSP056218A (enExample)
ES (1) ES2323870T3 (enExample)
HR (1) HRP20090333T1 (enExample)
IL (1) IL172357A (enExample)
MX (1) MXPA05013193A (enExample)
NO (1) NO335587B1 (enExample)
NZ (1) NZ544231A (enExample)
PL (1) PL1633697T3 (enExample)
PT (1) PT1633697E (enExample)
RU (1) RU2380355C2 (enExample)
SI (1) SI1633697T1 (enExample)
WO (1) WO2004108658A1 (enExample)
ZA (1) ZA200600109B (enExample)

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DE10328316A1 (de) 2003-06-23 2005-01-20 Grünenthal GmbH Verfahren zur Herstellung von Dimethyl-(3-aryl-buthyl)-aminverbindungen als pharmazeutische Wirkstoffe
DE102005052588A1 (de) 2005-11-02 2007-05-10 Grünenthal GmbH Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse
MX2009000911A (es) * 2006-07-24 2009-02-04 Janssen Pharmaceutica Nv Preparacion de (2r,3r)-3-(3-metoxifenil)-n,n,2-trimetilpentanamina .
TWI496762B (zh) * 2006-07-24 2015-08-21 歌林達股份有限公司 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
CN101939287B (zh) * 2007-12-07 2014-10-22 格吕伦塔尔有限公司 (1r,2r)-3-(3-二甲基氨基-1-乙基-2-甲基-丙基)-苯酚的结晶变体
US20100227921A1 (en) * 2009-03-03 2010-09-09 Shire Llc Amino acid and peptide carbamate prodrugs of tapentadol and uses thereof
CN102002065B (zh) * 2009-09-02 2014-09-10 上海特化医药科技有限公司 他喷他多的制备方法及其中间体
US8288592B2 (en) 2009-09-22 2012-10-16 Actavis Group Ptc Ehf Solid state forms of tapentadol salts
IT1397189B1 (it) * 2009-12-01 2013-01-04 Archimica Srl Nuovo processo per la preparazione di tapentadol e suoi intermedi.
WO2011080736A1 (en) 2009-12-29 2011-07-07 Mapi Pharma Hk Limited Intermediate compounds and processes for the preparation of tapentadol and related compounds
WO2011092719A2 (en) * 2010-02-01 2011-08-04 Ind-Swift Laboratories Limited Process for the preparation of l-phenyl-3-dimethylaminopropane derivatives
US20130096346A1 (en) 2010-03-05 2013-04-18 Actavis Group Ptc Ehf Resolution methods for isolating desired enantiomers of tapentadol intermediates and use thereof for the preparation of tapentadol
WO2011128784A2 (en) 2010-04-05 2011-10-20 Actavis Group Ptc Ehf Novel process for preparing highly pure tapentadol or a pharmaceutically acceptable salt thereof
ITMI20100924A1 (it) * 2010-05-21 2011-11-22 Fidia Farmaceutici Nuovo metodo di sintesi delle due forme enantiomeriche del tapentadol
CN103168025B (zh) * 2010-06-15 2015-02-25 格吕伦塔尔有限公司 用于制备取代的3-(1-氨基-2-甲基戊烷-3-基)苯基化合物的方法
IT1401109B1 (it) 2010-07-02 2013-07-12 Archimica Srl Nuovo processo per la preparazione di tapentadol e suoi intermedi.
ES2860676T3 (es) * 2010-07-23 2021-10-05 Gruenenthal Gmbh Sales o cocristales de 3- (3-dimetilamino-1-etil-2-metil-propil) -fenol
EP2606030B1 (en) 2010-08-16 2016-05-18 Indoco Remedies Limited Process for the preparation of tapentadol
US8552219B2 (en) 2010-09-20 2013-10-08 Ind-Swift Laboratories Limited Process for preparing L-phenyl-3-dimethylaminopropane derivative
CN102477016B (zh) * 2010-11-26 2014-12-17 中国医学科学院药物研究所 他喷他多的中间体的合成与应用
HUP1300623A2 (en) * 2010-12-30 2014-03-28 Zentiva Ks O-substituted (2r,3r)-3-(3-hidroxiphenil)-2-metyil-4-pentenoic acids and a method of obtaining the same
CZ2010998A3 (cs) * 2010-12-30 2012-02-08 Zentiva, K.S. Zpusob výroby (2R,3R)-N,N-dimethyl-3-(3-hydroxyfenyl)-2-methylpentylaminu (tapentadolu)
CZ2010997A3 (cs) * 2010-12-30 2012-02-08 Zentiva, K.S. Zpusob výroby (2R,3R)-N,N-dimethyl-3-(3-hydroxyfenyl)-2-methylpentylaminu (tapentadolu)
WO2012146978A2 (en) 2011-04-28 2012-11-01 Actavis Group Ptc Ehf A novel process for the preparation of tapentadol or a pharmaceutically acceptable salt thereof
EP2530072A1 (en) 2011-06-03 2012-12-05 Lacer, S.A. New compounds, synthesis and use thereof in the treatment of pain
WO2013016840A1 (zh) 2011-07-29 2013-02-07 安徽省新星药物开发有限责任公司 用于合成他喷他多或其类似物的新中间体
WO2013105109A1 (en) 2011-11-09 2013-07-18 Indoco Remedies Limited Process for the preparation of tapentadol
US20130150622A1 (en) 2011-12-12 2013-06-13 Boehringer Ingelheim International Gmbh Stereoselective synthesis of tapentadol and its salts
WO2013120466A1 (en) 2012-02-17 2013-08-22 Zentiva, K.S. A new solid form of tapentadol and a method of its preparation
EP2674414A1 (en) 2012-06-15 2013-12-18 Siegfried AG Method for the preparation of 1-aryl-1-alkyl-3-dialkylaminopropane compounds
CN103159633B (zh) * 2012-07-06 2015-08-12 江苏恩华药业股份有限公司 他喷他多的制备方法及用于制备他喷他多的化合物
IN2013MU03670A (enExample) 2013-11-21 2015-07-31 Unimark Remedies Ltd
SI3083551T1 (en) 2013-12-16 2018-04-30 Farma Grs, D.O.O. CRYSTAL FORM INTERMEDIATE TAPENTADOL
CZ307492B6 (cs) 2014-02-04 2018-10-17 Zentiva, K.S. Pevná forma maleátu tapentadolu a způsob její přípravy
CA2991421C (en) 2015-07-10 2019-04-30 Mallinckrodt Llc A two-step process for preparing 3-substituted phenylalkylamines
EP4269384A1 (en) 2022-04-26 2023-11-01 KRKA, d.d., Novo mesto Method for crystallizing tapentadol intermediate, tapentadol intermediate of high purity, method of making tapentadol and tapentadol of high purity

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EP0693475B1 (de) * 1994-07-23 1998-02-11 Grünenthal GmbH 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung
WO2001049651A2 (de) * 2000-01-05 2001-07-12 Grünenthal GmbH Aminomethyl-phenyl-cyclohexanonderivate
EP0799819B1 (de) * 1996-03-13 2002-09-11 Grünenthal GmbH 1-Dimethylaminomethyl-2-phenyl-cycloalk-2-enverbindungen mit analgetischer Wirkung

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Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
EP0693475B1 (de) * 1994-07-23 1998-02-11 Grünenthal GmbH 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung
EP0799819B1 (de) * 1996-03-13 2002-09-11 Grünenthal GmbH 1-Dimethylaminomethyl-2-phenyl-cycloalk-2-enverbindungen mit analgetischer Wirkung
WO2001049651A2 (de) * 2000-01-05 2001-07-12 Grünenthal GmbH Aminomethyl-phenyl-cyclohexanonderivate

Also Published As

Publication number Publication date
BRPI0411268B8 (pt) 2021-01-19
MXPA05013193A (es) 2006-03-09
CA2528087C (en) 2012-05-01
EP1633697A1 (de) 2006-03-15
KR20060036923A (ko) 2006-05-02
IL172357A0 (en) 2009-02-11
BRPI0411268B1 (pt) 2020-11-03
US20060194988A1 (en) 2006-08-31
EP1633697B1 (de) 2009-03-11
ATE425136T1 (de) 2009-03-15
WO2004108658A1 (de) 2004-12-16
PT1633697E (pt) 2009-06-04
AU2004245223B2 (en) 2010-01-28
HRP20090333T1 (hr) 2009-07-31
NZ544231A (en) 2009-06-26
BRPI0411268C1 (pt) 2021-05-25
JP4848268B2 (ja) 2011-12-28
RU2380355C2 (ru) 2010-01-27
PL1633697T3 (pl) 2009-08-31
CN1829681B (zh) 2013-02-06
AU2004245223A1 (en) 2004-12-16
KR101146205B1 (ko) 2012-05-25
ECSP056218A (es) 2006-04-19
HK1088597A1 (zh) 2006-11-10
DK1633697T3 (da) 2009-06-02
BRPI0411268A (pt) 2006-08-01
NO335587B1 (no) 2015-01-05
DE10326097A1 (de) 2005-01-05
CN1829681A (zh) 2006-09-06
CY1109088T1 (el) 2014-07-02
RU2005141518A (ru) 2007-07-20
US7417170B2 (en) 2008-08-26
CA2528087A1 (en) 2004-12-16
JP2006527178A (ja) 2006-11-30
IL172357A (en) 2014-09-30
ZA200600109B (en) 2007-01-31
DE502004009142D1 (de) 2009-04-23
NO20060044L (no) 2006-01-04
BRPI0411268C8 (pt) 2021-11-16
SI1633697T1 (sl) 2009-08-31
ES2323870T3 (es) 2009-07-27

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