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WO2011033366A3 - Procédé amelioré pour la préparation de duloxetine et de sel acceptable sur le plan pharmaceutique de celle-ci - Google Patents

Procédé amelioré pour la préparation de duloxetine et de sel acceptable sur le plan pharmaceutique de celle-ci 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
English (en)
Other versions
WO2011033366A2 (fr
WO2011033366A8 (fr
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/fr
Publication of WO2011033366A8 publication Critical patent/WO2011033366A8/fr
Publication of WO2011033366A3 publication Critical patent/WO2011033366A3/fr
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

La présente invention concerne un procédé amélioré pour racémiser un des énantiomères, ou un mélange enrichi de manière énantiomérique, d'un composé optiquement actif (S)-N, N-diméthyl-3-(2-thiényl)-3-hydroxypropanamine, un intermédiaire clé utilisé pour la préparation de (S)-N-méthyl-3-(1-naphthalènyloxy)-3-(2- thiényl) propanamine (duloxétine) ou un chlorhydrate de celle-ci. L'invention concerne également un procédé amélioré pour la préparation de (S)-N-méthyl-3- (1-naphthalènyloxy)-3-(2-thiényl) propanamine (duloxétine) ou un chlorhydrate de celle-ci présentant une faible teneur en R-isomères non désirés et une pureté chirale non inférieure à 99 %.
PCT/IB2010/002320 2009-09-16 2010-09-16 Procédé amelioré pour la préparation de duloxetine et de sel acceptable sur le plan pharmaceutique de celle-ci Ceased WO2011033366A2 (fr)

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 (fr) 2011-03-24
WO2011033366A8 WO2011033366A8 (fr) 2011-05-05
WO2011033366A3 true WO2011033366A3 (fr) 2011-09-01

Family

ID=43501584

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/002320 Ceased WO2011033366A2 (fr) 2009-09-16 2010-09-16 Procédé amelioré pour la préparation de duloxetine et de sel acceptable sur le plan pharmaceutique de celle-ci

Country Status (1)

Country Link
WO (1) WO2011033366A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104163811A (zh) * 2013-05-16 2014-11-26 重庆圣华曦药业股份有限公司 一种制备度洛西汀盐酸盐的新方法
CN104829587B (zh) * 2015-05-08 2017-07-21 上海万巷制药有限公司 盐酸度洛西汀的制备
CN107382958B (zh) * 2017-07-05 2021-11-09 浙江华海药业股份有限公司 一种度洛西汀中间体的结晶方法
CN114790146B (zh) * 2022-05-19 2024-03-29 河南省科学院高新技术研究中心 一种3-(甲基氨基)-1-芳香基丙酮的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006126213A1 (fr) * 2005-05-24 2006-11-30 Matrix Laboratories Ltd Ameliorations apportees a un procede de preparation de duloxetine
WO2007098250A2 (fr) * 2006-02-21 2007-08-30 Teva Pharmaceutical Industries Ltd. Procédé de préparation de (s)-(-)-n,n-diméthyl-3-(2-thiényl)-3-hydroxypropanamine, un composant de la duloxétine
WO2008093360A2 (fr) * 2007-01-31 2008-08-07 Usv Limited Procédé de préparation d'hydrochlorure de (s)-(+)-n-méthyl-3(1-naphthyloxy)-3(2-thienyl)propylamine

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 (fr) 2002-10-07 2004-04-15 Lonza Ag Procedes et produits intermediaires pour la preparation de derives de 3-amino-1-(2-thienyl)-1-propanol optiquement actifs
GB0229583D0 (en) 2002-12-19 2003-01-22 Cipla Ltd A process for preparing duloxetine and intermediates for use therein
CZ297560B6 (cs) 2004-10-26 2007-02-07 Zentiva, A. S. Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (duloxetinu)
ITMI20051970A1 (it) 2005-10-18 2007-04-19 Solmag S P A Processo per la preparazione di eteri misti derivanti dall'inaftolo e intermedi di forme cristalline definite di + e - duloxetina

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006126213A1 (fr) * 2005-05-24 2006-11-30 Matrix Laboratories Ltd Ameliorations apportees a un procede de preparation de duloxetine
WO2007098250A2 (fr) * 2006-02-21 2007-08-30 Teva Pharmaceutical Industries Ltd. Procédé de préparation de (s)-(-)-n,n-diméthyl-3-(2-thiényl)-3-hydroxypropanamine, un composant de la duloxétine
WO2008093360A2 (fr) * 2007-01-31 2008-08-07 Usv Limited Procédé de préparation d'hydrochlorure de (s)-(+)-n-méthyl-3(1-naphthyloxy)-3(2-thienyl)propylamine

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 (fr) 2011-03-24
WO2011033366A8 (fr) 2011-05-05

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