WO2004031168A3 - Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives - Google Patents

Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives Download PDF

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Publication number
WO2004031168A3
WO2004031168A3 PCT/EP2003/011073 EP0311073W WO2004031168A3 WO 2004031168 A3 WO2004031168 A3 WO 2004031168A3 EP 0311073 W EP0311073 W EP 0311073W WO 2004031168 A3 WO2004031168 A3 WO 2004031168A3
Authority
WO
WIPO (PCT)
Prior art keywords
thienyl
amino
optically active
intermediates
processes
Prior art date
Application number
PCT/EP2003/011073
Other languages
French (fr)
Other versions
WO2004031168A2 (en
Inventor
Rudolf Fuchs
Dominique Michel
Walter Brieden
Original Assignee
Lonza Ag
Rudolf Fuchs
Dominique Michel
Walter Brieden
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 Lonza Ag, Rudolf Fuchs, Dominique Michel, Walter Brieden filed Critical Lonza Ag
Priority to AU2003276066A priority Critical patent/AU2003276066A1/en
Publication of WO2004031168A2 publication Critical patent/WO2004031168A2/en
Publication of WO2004031168A3 publication Critical patent/WO2004031168A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Enantiomerically enriched 3-amino-1-(2-thienyl)-1-propanols of the formulae ((S)-I) or ((R)-I) wherein R1 and R2 independently denote H, C1-6-alkyl, C5-7-cycloalkyl, aralkyl or aryl, were prepared by reducing a 3-amino-1-(2-thienyl)-1-propanone of the formula (II) wherein R1 and R2 are defined as above, using a hydrogen donor in the presence of a metal catalyst, an optically active nitrogen-containing ligand and optionally a base.
PCT/EP2003/011073 2002-10-07 2003-10-07 Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives WO2004031168A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003276066A AU2003276066A1 (en) 2002-10-07 2003-10-07 Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP02022540 2002-10-07
EP02022540.5 2002-10-07

Publications (2)

Publication Number Publication Date
WO2004031168A2 WO2004031168A2 (en) 2004-04-15
WO2004031168A3 true WO2004031168A3 (en) 2004-08-26

Family

ID=32049979

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/011073 WO2004031168A2 (en) 2002-10-07 2003-10-07 Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives

Country Status (2)

Country Link
AU (1) AU2003276066A1 (en)
WO (1) WO2004031168A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005000867A1 (en) * 2005-01-05 2006-07-13 Basf Ag Process for the purification of (1S) -3-methylamino-1- (2-thienyl) -1-propanol
EP1838692A2 (en) 2005-09-22 2007-10-03 Teva Pharmaceutical Industries Ltd Dnt-maleate and methods of preparation thereof
EP1888554A2 (en) 2006-02-21 2008-02-20 Teva Pharmaceutical Industries Ltd Process for the preparation of (s)-(-)-n,n-dimethyl-3-(2-thienyl)-3-hydroxypropanamine, a duloxetine intermediate
CA2656128A1 (en) 2006-07-03 2008-01-10 Ranbaxy Laboratories Limited Process for the preparation of enantiomerically pure salts of n-methyl-3(1-naphthaleneoxy)-3-(2-thienyl)propanamine
WO2008077645A1 (en) 2006-12-22 2008-07-03 Synthon B.V. Process for making duloxetine and related compounds
HU227730B1 (en) * 2006-12-22 2012-01-30 Richter Gedeon Nyrt Process for the preparation of duloxetine and for their the intermediates
SI22839A (en) * 2008-07-07 2010-01-29 Krka, Tovarna Zdravil, D.D. Synthesis of duloxetine and its pharmaceutically acceptable salts by using the procedure of asymmetric transfer hydrogenation
WO2010025287A2 (en) 2008-08-27 2010-03-04 Codexis, Inc. Ketoreductase polypeptides for the production of 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine
US8426178B2 (en) 2008-08-27 2013-04-23 Codexis, Inc. Ketoreductase polypeptides for the production of a 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine
WO2011033366A2 (en) 2009-09-16 2011-03-24 Jubilant Life Sciences Limited Process for the preparation of duloxetine hydrochloride and its precursors
SI2558455T1 (en) 2010-04-13 2017-12-29 Krka, D.D., Novo Mesto Synthesis of duloxetine and/or pharmaceutically acceptable salts thereof
EP2426116B1 (en) 2010-08-30 2013-06-26 Saltigo GmbH Method for producing (S)-3-N-Methylamino-1-(2-thienyl)-1-propanol
CN105061393B (en) * 2015-08-07 2017-06-27 浙江华义医药有限公司 (S) synthetic method of () 3 methylamino 1 (2 thienyl) 1 propyl alcohol
CN111793056A (en) * 2020-07-27 2020-10-20 广州康瑞泰药业有限公司 Preparation method of duloxetine intermediate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3682925A (en) * 1969-01-30 1972-08-08 Hoffmann La Roche ({31 )-di-o-isopropylidene-2-keto-l-gulonates
EP0650965A1 (en) * 1993-10-12 1995-05-03 Eli Lilly And Company Asymmetric synthesis of (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine an intermediate in the preparation of duloxetine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3682925A (en) * 1969-01-30 1972-08-08 Hoffmann La Roche ({31 )-di-o-isopropylidene-2-keto-l-gulonates
EP0650965A1 (en) * 1993-10-12 1995-05-03 Eli Lilly And Company Asymmetric synthesis of (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine an intermediate in the preparation of duloxetine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PALMER M ET AL: "(1R,2S)-(+)-cis-1-Amino-2-indanol: an effective ligand for asymmetric catalysis of transfer hydrogenations of ketones", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 62, no. 15, 25 July 1997 (1997-07-25), pages 5226 - 5228, XP002150567, ISSN: 0022-3263 *
TAKESHI OHKUMA ET AL: "General Asymmetric Hydrogenation of Hetero-aromatic Ketones", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 2, no. 12, 2000, pages 1749 - 1751, XP002255184, ISSN: 1523-7060 *

Also Published As

Publication number Publication date
WO2004031168A2 (en) 2004-04-15
AU2003276066A1 (en) 2004-04-23

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