WO2014072998A9 - An improved process for preparation of agomelatine - Google Patents
An improved process for preparation of agomelatine Download PDFInfo
- 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
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
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).
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 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 (4)
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 |
Family Cites Families (10)
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 |
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 |
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 |
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 |
WO2011128413A1 (en) * | 2010-04-15 | 2011-10-20 | 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 |
-
2013
- 2013-11-06 WO PCT/IN2013/000682 patent/WO2014072998A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
WO2014072998A1 (en) | 2014-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2014072998A9 (en) | An improved process for preparation of agomelatine | |
NZ599549A (en) | Methods of synthesis and purification of heteroaryl compounds | |
MX2011011245A (en) | Processes for the preparation of morphinane and morphinone compounds. | |
Shinde et al. | Industrial application of the Forster reaction: Novel one-pot synthesis of cinacalcet hydrochloride, a calcimimetic agent | |
EA201170181A1 (en) | POLYMORPHIC FORMS OF RAZAGILINA HYDROCHLORIDE | |
WO2012086808A1 (en) | Process for production of aromatic alcohol or heterocyclic aromatic alcohol | |
WO2013132290A3 (en) | Improved process for preparing 4-aminodiphenylamine | |
CN102977098B (en) | Aryl-substituted indolizine derivative and preparation method and applications thereof | |
JP2011001364A5 (en) | ||
WO2009135598A8 (en) | Process for preparing substituted biphenylanilides | |
ZA201003751B (en) | Process for the synthesis of propargylated aminoindan derivatives | |
Xu et al. | A chiral primary-tertiary-1, 2-diamine as an efficient catalyst in asymmetric aldehyde–ketone or ketone–ketone aldol reactions | |
JP2013531058A5 (en) | ||
IT1398304B1 (en) | PROCEDURE FOR THE PRODUCTION OF DIALCOSSIMAGNESIUM SUPPORT FOR CATALYST FOR OLEFINE POLYMERIZATION, CATALYST PRODUCTION PROCEDURE FOR THE POLYMERIZATION OF OLEFINE USING THE SAME AND THE POLYMERIZATION PROCESS OF OLEFINE USING THE SAME. | |
NZ604081A (en) | Agomelatine intermediates and preparation method thereof | |
NZ630290A (en) | Process for preparation of fingolimod and its salts | |
NZ612592A (en) | Process for the enzymatic synthesis of (7s)-1-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl) n-methyl methanamine, and application in the synthesis of ivabradine and salts thereof | |
WO2015022702A3 (en) | Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof | |
SA113350005B1 (en) | New process for the synthesis of (2E)-3-(3,4-dimethoxyphenyl)prop-2-enenitrile, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid | |
CN104193645A (en) | Preparation method of chiral dimethyl cyclopropyl carboxamide | |
GEP20156350B (en) | New process for synthesis of ivabradine and their additional salts with pharmaceutically acceptable acid | |
Pourhanafi et al. | NaBH4/Ga (OH) 3: An Efficient Reducing System for Reductive Amination of Aldehydes | |
WO2011048612A3 (en) | Process for preparation of propargylated aminoindans or pharmaceutically acceptable salts thereof | |
Likhar et al. | Polyaniline-supported metal catalysts for green synthesis | |
MD4443B1 (en) | Process for the synthesis of 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, and application in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13826768 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase in: |
Ref country code: DE |
|
122 | Ep: pct app. not ent. europ. phase |
Ref document number: 13826768 Country of ref document: EP Kind code of ref document: A1 |