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WO2014072998A9 - An improved process for preparation of agomelatine - Google Patents

An improved process for preparation of agomelatine Download PDF

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Publication number
WO2014072998A9
WO2014072998A9 PCT/IN2013/000682 IN2013000682W WO2014072998A9 WO 2014072998 A9 WO2014072998 A9 WO 2014072998A9 IN 2013000682 W IN2013000682 W IN 2013000682W WO 2014072998 A9 WO2014072998 A9 WO 2014072998A9
Authority
WO
WIPO (PCT)
Prior art keywords
formula
agomelatine
methoxy
organic solvent
compound
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/IN2013/000682
Other languages
French (fr)
Other versions
WO2014072998A1 (en
Inventor
Shri Prakash Dhar Dwivedi
Ashok Prasad
Niraj Shyamlal Shah
Mayur Ramnikbhai Patel
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.)
Zydus Lifesciences Ltd
Original Assignee
Cadila Healthcare 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 Cadila Healthcare Ltd filed Critical Cadila Healthcare Ltd
Publication of WO2014072998A1 publication Critical patent/WO2014072998A1/en
Publication of WO2014072998A9 publication Critical patent/WO2014072998A9/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07C213/02—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 involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention provides an improved process for preparing agomelatine of formula (I). The process comprises reacting 7-methoxy tetralone with cyanoacetic acid in an organic solvent to obtain (7-methoxy-3,4-dihydro- 1 -naphthalenyl)acetonitrile of Formula (B); treating compound of Formula (B) with a catalyst to obtain (7-methoxy- 1 - naphthyl)acetonitrile of Formula (C); reducing compound of formula (C) with hydrogen in presence of Raney nickel in ammoniacal methanol medium and subsequently converting to a salt using hydrochloric acid to obtain 2-(7-methoxy- 1 -naphthyI)ethanamine hydrochloride of formula (D); iv) reacting compound of formula (D) with acetic anhydride or acetic chloride in an organic solvent in presence of a base and a catalyst to obtain agomelatine of Formula (I); and optionally purifying agomelatine of Formula (I). The present invention also provides a process for preparing polymorphic Form-I of agomelatine of formula (I) comprising treating agomelatine of formula (I) in a suitable organic solvent; and isolating polymorphic Form-I of agomelatine of formula (I).
PCT/IN2013/000682 2012-11-07 2013-11-06 An improved process for preparation of agomelatine Ceased WO2014072998A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN3234MU2012 2012-11-07
IN3234/MUM/2012 2012-11-07

Publications (2)

Publication Number Publication Date
WO2014072998A1 WO2014072998A1 (en) 2014-05-15
WO2014072998A9 true WO2014072998A9 (en) 2015-01-15

Family

ID=50031400

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2013/000682 Ceased WO2014072998A1 (en) 2012-11-07 2013-11-06 An improved process for preparation of agomelatine

Country Status (1)

Country Link
WO (1) WO2014072998A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105601537B (en) * 2016-01-25 2018-11-06 江西同和药业股份有限公司 A kind of preparation method of 2- (7- methoxy-1-naphthyls) acetonitrile
CN106543034A (en) * 2016-10-31 2017-03-29 苏州弘森药业股份有限公司 A kind of method of 7 methoxynaphthalene acetonitriles of synthesis
CN107353229B (en) * 2017-08-08 2019-04-30 许昌恒生制药有限公司 A kind of preparation method of agomelatine intermediate body
CN113527139A (en) * 2020-04-17 2021-10-22 上海法默生物科技有限公司 Method for synthesizing 7-methoxy-1-naphthylacetonitrile and intermediate
CN117567321B (en) * 2023-10-17 2025-08-29 湖南省湘中制药有限公司 A kind of preparation method of 7-methoxynaphthaleneacetonitrile

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2658818B1 (en) 1990-02-27 1993-12-31 Adir Cie NOVEL DERIVATIVES WITH NAPHTHALENIC STRUCTURE, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
FR2866335B1 (en) 2004-02-13 2006-05-26 Servier Lab NEW PROCESS FOR THE SYNTHESIS OF AGOMELATIN
US7645905B2 (en) 2005-08-03 2010-01-12 Les Laboratoires Servier Crystalline form IV of agomelatine, a process for its preparation and pharmaceutical compositions containing it
US7358395B2 (en) 2005-08-03 2008-04-15 Les Laboratories Servier Crystalline form V of agomelatine, a process for its preparation and pharmaceutical compositions containing it
US7635721B2 (en) 2005-08-03 2009-12-22 Les Laboratoires Servier Crystalline form III of agomelatine, a process for its preparation and pharmaceutical compositions containing it
FR2923482B1 (en) 2007-11-09 2010-01-29 Servier Lab NOVEL VI CRYSTALLINE FORM OF AGOMELATIN, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
FR2934859B1 (en) 2008-08-05 2010-08-13 Servier Lab NEW PROCESS FOR THE SYNTHESIS OF AGOMELATIN
EP2319827A1 (en) * 2009-11-09 2011-05-11 Ratiopharm GmbH Process for the production of polymorph form I of agomelatine
EP2558440B1 (en) * 2010-04-15 2016-11-16 ratiopharm GmbH Process for the production of polymorph form i of agomelatine
WO2012127483A1 (en) * 2011-03-24 2012-09-27 Symed Labs Limited Processes for the preparation of intermediates of n-[2-(7-methoxy-1-naphthyl) ethyl] acetamide

Also Published As

Publication number Publication date
WO2014072998A1 (en) 2014-05-15

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