EA200801635A1 - Способ получения (s)-n-метил-3-(1-нафтилокси)-3(2-тиенил)пропиламина гидрохлорида (дулоксетина) - Google Patents

Способ получения (s)-n-метил-3-(1-нафтилокси)-3(2-тиенил)пропиламина гидрохлорида (дулоксетина)

Info

Publication number
EA200801635A1
EA200801635A1 EA200801635A EA200801635A EA200801635A1 EA 200801635 A1 EA200801635 A1 EA 200801635A1 EA 200801635 A EA200801635 A EA 200801635A EA 200801635 A EA200801635 A EA 200801635A EA 200801635 A1 EA200801635 A1 EA 200801635A1
Authority
EA
Eurasian Patent Office
Prior art keywords
naphthyloxy
propylamine
thienyl
base
dimethyl
Prior art date
Application number
EA200801635A
Other languages
English (en)
Other versions
EA014559B1 (ru
Inventor
Лудек Ридван
Камал Ярраг
Йосеф Цинибулк
Моника Затопкова
Лукас Плацек
Original Assignee
ЗЕНТИВА, а.с.
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 ЗЕНТИВА, а.с. filed Critical ЗЕНТИВА, а.с.
Publication of EA200801635A1 publication Critical patent/EA200801635A1/ru
Publication of EA014559B1 publication Critical patent/EA014559B1/ru

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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Способ получения (S)-N-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина формулы (I) и его фармацевтически приемлемых солей, включающий: а) взаимодействие (RS)-N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина формулы (III) с оптически активной D-винной кислотой или кислой солью, являющейся производным D-винной кислоты, с образованием смеси диастереоизомерных солей N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина и D-винной кислоты (2:1), б) выделение соли (S)-N,N-диметил-3-(нафтилокси)-3-(2-тиенил)пропиламин/D-тартрат (2:1) из смеси диастереоизомерных солей в органическом растворителе, воде или их смеси и выделение (S)-N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина формулы (S)-(III) действием неорганического или органического основания, в) деметилирование (S)-N,N-диметил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина действием алкилированного производного хлороформа формулы CICOOR (R = C
EA200801635A 2006-01-04 2006-12-22 Способ получения (s)-n-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина гидрохлорида (дулоксетина) EA014559B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZ20060007A CZ299270B6 (cs) 2006-01-04 2006-01-04 Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu
PCT/CZ2006/000096 WO2007076733A2 (en) 2006-01-04 2006-12-22 A METHOD FOR THE PREPARATION OF (S)-N-METΗYL-3-(l-NAPHTHYLOXY)-3-(2-THIENYL)PROPYLAMINE HYDROCHLORIDE (DULOXETINE)

Publications (2)

Publication Number Publication Date
EA200801635A1 true EA200801635A1 (ru) 2008-10-30
EA014559B1 EA014559B1 (ru) 2010-12-30

Family

ID=38042666

Family Applications (1)

Application Number Title Priority Date Filing Date
EA200801635A EA014559B1 (ru) 2006-01-04 2006-12-22 Способ получения (s)-n-метил-3-(1-нафтилокси)-3-(2-тиенил)пропиламина гидрохлорида (дулоксетина)

Country Status (9)

Country Link
US (2) US8071791B2 (ru)
EP (2) EP2172464B1 (ru)
AT (1) ATE523503T1 (ru)
CZ (1) CZ299270B6 (ru)
EA (1) EA014559B1 (ru)
PL (1) PL1968965T3 (ru)
PT (1) PT1968965E (ru)
UA (1) UA94931C2 (ru)
WO (1) WO2007076733A2 (ru)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE602006021628D1 (de) * 2005-12-12 2011-06-09 Medichem Sa Verbesserte synthese und zubereitungen von duloxetinsalzen
EP2107057A1 (en) 2008-04-04 2009-10-07 Ranbaxy Laboratories Limited Process for the preparation of pure duloxetine hydrochloride
WO2016137667A1 (en) * 2015-02-24 2016-09-01 Coiled Tubing Specialties, Llc Steerable hydraulic jetting nozzle, and guidance system for downhole boring device
EP3356562A4 (en) * 2015-10-02 2019-06-12 Phylagen, Inc. PRODUCT AUTHENTICATION AND TRACKING
CN114163415B (zh) * 2021-12-01 2023-03-03 珠海润都制药股份有限公司 一种盐酸度洛西汀中间体的制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR880007433A (ko) 1986-12-22 1988-08-27 메리 앤 터커 3-아릴옥시-3-치환된 프로판아민
US5362886A (en) * 1993-10-12 1994-11-08 Eli Lilly And Company Asymmetric synthesis
DE10212301A1 (de) 2002-03-20 2003-10-02 Bayer Ag Verfahren zur Herstellung von Aryl-aminopropanolen
CN103058986A (zh) 2002-07-09 2013-04-24 隆萨股份公司 N-单取代β-氨基醇的制备方法
GB0229583D0 (en) * 2002-12-19 2003-01-22 Cipla Ltd A process for preparing duloxetine and intermediates for use therein
GB0410470D0 (en) 2004-05-11 2004-06-16 Cipla Ltd Pharmaceutical compound and polymorphs thereof
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)
CZ297555B6 (cs) * 2004-10-26 2007-02-07 Zentiva, A. S. Zpusob výroby hydrochloridu (S)-N-methyl-3-(1-naftyloxy)-3-(2-thienyl)propylaminu (duloxetinu)
WO2006099459A1 (en) * 2005-03-14 2006-09-21 Teva Pharmaceutical Industries Ltd. Process for the preparation of optically active (s)-(+)-n,n-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine
WO2006126213A1 (en) 2005-05-24 2006-11-30 Matrix Laboratories Ltd An improved process for the preparation of duloxetine

Also Published As

Publication number Publication date
CZ299270B6 (cs) 2008-06-04
EP2172464A3 (en) 2010-05-12
EP2172464A2 (en) 2010-04-07
US8207356B2 (en) 2012-06-26
WO2007076733A2 (en) 2007-07-12
UA94931C2 (ru) 2011-06-25
US8071791B2 (en) 2011-12-06
PT1968965E (pt) 2011-11-10
US20120029212A1 (en) 2012-02-02
CZ20067A3 (cs) 2007-07-11
EP1968965A2 (en) 2008-09-17
EP2172464B1 (en) 2015-08-26
WO2007076733A3 (en) 2007-08-23
EA014559B1 (ru) 2010-12-30
ATE523503T1 (de) 2011-09-15
EP1968965B1 (en) 2011-09-07
PL1968965T3 (pl) 2011-12-30
US20080293952A1 (en) 2008-11-27

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Legal Events

Date Code Title Description
MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AM AZ BY KZ KG MD TJ TM

MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): RU