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WO2011033366A3 - Process for the preparation of duloxetine hydrochloride and its precursors - Google Patents

Process for the preparation of duloxetine hydrochloride and its precursors Download PDF

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Publication number
WO2011033366A3
WO2011033366A3 PCT/IB2010/002320 IB2010002320W WO2011033366A3 WO 2011033366 A3 WO2011033366 A3 WO 2011033366A3 IB 2010002320 W IB2010002320 W IB 2010002320W WO 2011033366 A3 WO2011033366 A3 WO 2011033366A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
thienyl
duloxetine
precursors
naphthalenyloxy
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.)
Ceased
Application number
PCT/IB2010/002320
Other languages
French (fr)
Other versions
WO2011033366A2 (en
WO2011033366A8 (en
Inventor
Sujay Biswas
Archana Trivedi
Manita Kharbanda
Shailendra Dubey
Sandeep Singla
Mansukhlal Bodheka Yogiraj
Dharam Vir
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.)
Jubilant Pharmova Ltd
Original Assignee
Jubilant Life Sciences Ltd
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 Jubilant Life Sciences Ltd filed Critical Jubilant Life Sciences Ltd
Publication of WO2011033366A2 publication Critical patent/WO2011033366A2/en
Publication of WO2011033366A8 publication Critical patent/WO2011033366A8/en
Publication of WO2011033366A3 publication Critical patent/WO2011033366A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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

Landscapes

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

Abstract

The present invention relates to an improved process for racemizing one of the enantiomers, or an enantiomerically enriched mixture, of an optically active compound (S)-N, N-dimethyl-3-(2-thienyl)-3-hydroxypropanamine, a key intermediate used for the preparation of (S)-N-methyl-3-(1-naphthalenyloxy)-3-(2- thienyl) propanamine (duloxetine) or its hydrochloride salt. Moreover, the present invention also relates to an improved process for the preparation of (S)-N-methyl-3- (1-naphthalenyloxy)-3-(2-thienyl) propanamine (duloxetine) or its hydrochloride salt having low content of undesired R-isomer and chiral purity not less than 99%.
PCT/IB2010/002320 2009-09-16 2010-09-16 Process for the preparation of duloxetine hydrochloride and its precursors Ceased WO2011033366A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1923/DEL/2009 2009-09-16
IN1922DE2009 2009-09-16
IN1922/DEL/2009 2009-09-16
IN1923DE2009 2009-09-16

Publications (3)

Publication Number Publication Date
WO2011033366A2 WO2011033366A2 (en) 2011-03-24
WO2011033366A8 WO2011033366A8 (en) 2011-05-05
WO2011033366A3 true WO2011033366A3 (en) 2011-09-01

Family

ID=43501584

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/002320 Ceased WO2011033366A2 (en) 2009-09-16 2010-09-16 Process for the preparation of duloxetine hydrochloride and its precursors

Country Status (1)

Country Link
WO (1) WO2011033366A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104163811A (en) * 2013-05-16 2014-11-26 重庆圣华曦药业股份有限公司 New method for preparation of duloxetine hydrochloride
CN104829587B (en) * 2015-05-08 2017-07-21 上海万巷制药有限公司 The preparation of duloxetine hydrochloride
CN107382958B (en) * 2017-07-05 2021-11-09 浙江华海药业股份有限公司 Crystallization method of duloxetine intermediate
CN114790146B (en) * 2022-05-19 2024-03-29 河南省科学院高新技术研究中心 Preparation method of 3- (methylamino) -1-aryl acetone

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006126213A1 (en) * 2005-05-24 2006-11-30 Matrix Laboratories Ltd An improved process for the preparation of duloxetine
WO2007098250A2 (en) * 2006-02-21 2007-08-30 Teva Pharmaceutical Industries Ltd. Process for the preparation of (s)-(-)-n,n-dimethyl-3-(2-thienyl)-3-hydroxypropanamine, a duloxetine intermediate
WO2008093360A2 (en) * 2007-01-31 2008-08-07 Usv Limited A process for preparation of (s)-(+)-n-methyl-3(1-naphthyloxy)-3(2-thienyl)propylamine hydrochloride

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4956388A (en) 1986-12-22 1990-09-11 Eli Lilly And Company 3-aryloxy-3-substituted propanamines
US5362886A (en) 1993-10-12 1994-11-08 Eli Lilly And Company Asymmetric synthesis
AU2003253036A1 (en) 2002-07-09 2004-01-23 Lonza Ag Process for the preparation of optically active 3-n-methylamino-1-(2-thienyl)-1-propanol
WO2004031168A2 (en) 2002-10-07 2004-04-15 Lonza Ag Processes and intermediates for the preparation of optically active 3-amino-1-(2-thienyl)-1-propanol derivatives
GB0229583D0 (en) 2002-12-19 2003-01-22 Cipla Ltd A process for preparing duloxetine and intermediates for use therein
CZ297560B6 (en) 2004-10-26 2007-02-07 Zentiva, A. S. Process for preparing (S)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (duloxetine)
ITMI20051970A1 (en) 2005-10-18 2007-04-19 Solmag S P A PROCESS FOR THE PREPARATION OF MIXED HETERENTS DERIVING FROM INHTHOLE AND INTERMEDIATES OF CRYSTALLINE FORMS DEFINED BY + E - DULOXETINE

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006126213A1 (en) * 2005-05-24 2006-11-30 Matrix Laboratories Ltd An improved process for the preparation of duloxetine
WO2007098250A2 (en) * 2006-02-21 2007-08-30 Teva Pharmaceutical Industries Ltd. Process for the preparation of (s)-(-)-n,n-dimethyl-3-(2-thienyl)-3-hydroxypropanamine, a duloxetine intermediate
WO2008093360A2 (en) * 2007-01-31 2008-08-07 Usv Limited A process for preparation of (s)-(+)-n-methyl-3(1-naphthyloxy)-3(2-thienyl)propylamine hydrochloride

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
COLINS A N ET AL: "Resolution versus stereoselective synthesis in drug development: some case histories, dulexetine", CHIRALITY IN INDUSTRY. THE COMMERCIAL MANUFACTURE ANDAPPLICATIONS OF OPTICALLY ACTIVE COMPOUNTS, XX, XX, 1 January 1997 (1997-01-01), pages 99 - 117, XP009086064 *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 2006, XIAO, HEQING ET AL: "Study of racemization reaction of (R)-(+)-N,N-dimethyl-3-hydroxy-3-(2-thienyl) propanamine", XP002620119, retrieved from STN Database accession no. 2006:1318626 *
FUJIMA YOSHITO ET AL: "Synthesis of (S)-3-(N-Methylamino)-1-(2-thienyl)propan-1-ol: Revisiting Eli Lilly's Resolution-Racemization-Recycle Synthesis of Duloxetine for Its Robust Processes", ORGANIC PROCESS RESEARCH AND DEVELOPMENT, CAMBRIDGE, GB, vol. 10, no. 5, 1 January 2006 (2006-01-01), pages 905 - 913, XP002447767 *
JINGXI HUAGONG , 23(7), 717-720 CODEN: JIHUFJ; ISSN: 1003-5214, 2006 *

Also Published As

Publication number Publication date
WO2011033366A2 (en) 2011-03-24
WO2011033366A8 (en) 2011-05-05

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