WO2013054273A2 - Procédé pour la préparation d'agomélatine - Google Patents

Procédé pour la préparation d'agomélatine Download PDF

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Publication number
WO2013054273A2
WO2013054273A2 PCT/IB2012/055485 IB2012055485W WO2013054273A2 WO 2013054273 A2 WO2013054273 A2 WO 2013054273A2 IB 2012055485 W IB2012055485 W IB 2012055485W WO 2013054273 A2 WO2013054273 A2 WO 2013054273A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
methoxynaphthalen
agomelatine
ethanamine
Prior art date
Application number
PCT/IB2012/055485
Other languages
English (en)
Other versions
WO2013054273A3 (fr
WO2013054273A9 (fr
Inventor
Anu Mittal
Mahavir Singh Khanna
Rajesh Kumar Thaper
Mohan Prasad
Sudershan Kumar Arora
Original Assignee
Ranbaxy Laboratories Limited
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 Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Publication of WO2013054273A2 publication Critical patent/WO2013054273A2/fr
Publication of WO2013054273A9 publication Critical patent/WO2013054273A9/fr
Publication of WO2013054273A3 publication Critical patent/WO2013054273A3/fr

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Classifications

    • 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
    • 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
    • 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
    • C07C213/08—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 not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C247/08—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated
    • C07C247/10—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated and containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the present invention provides a process for the preparation of agomelatine and its intermediate compounds.
  • the invention also provides intermediate compounds of agomelatine, represented by Formula IV, Formula V and Formula VIII.
  • Agomelatine is chemically known as N-[2-(7-methoxynaphthalen-l- yl)ethyl]acetamide. It is indicated for the treatment of major depressive episodes in adults and is represented by Formula I.
  • Agomelatine and its preparation are disclosed in U.S. Patent No. 5,225,442.
  • the preparation comprises converting (7-methoxy- l-naphthyl)acetic acid to (7-methoxy- 1 - naphthyl)ethanamine via preparation of (7-methoxy- l-naphthyl)acetamide or (7-methoxy- 1 -naphthyl)acetonitrile intermediate compounds.
  • 2010/0137628 and 2010/0036161 describe a process for the preparation of agomelatine comprising reduction of (7-methoxy- 1 -naphthyl)acetonitrile into (7-methoxy- 1 - naphthyl)ethylamine followed by an acetylation step.
  • U.S. Publication No. 201 1/0130571 describes a process for the preparation of agomelatine comprising reacting 7-methoxy- 1 -naphthyl ethanol with benzenesulfonyl chloride to obtain 7-methoxy- l-naphthylethyl benzene sulfonate and condensing it with potassium phthalimide, followed by sequential hydrolysis and acetylation steps.
  • the present invention provides an alternate process for the preparation of agomelatine and its intermediate compounds.
  • the present invention provides a process for the preparation of agomelatine using 2-(7-methoxynaphthalen- 1 -yl)ethyl 4-nitrobenzene sulfonate (Formula IV), l-[2-(7- methoxynaphthalen-l-yl)ethyl]-2 ⁇ 5 -triaz- l-en-2-yne (Formula V) and the carbon dioxide adduct of 2-(7-methoxynaphthalen- 1 -yl)ethanamine (Formula VIII) as intermediate compounds.
  • the present invention is also directed towards compounds of Formula IV, Formula V and Formula VIII. Brief Description of the Drawing
  • Figure 1 depicts the X-ray powder diffraction pattern of the crystalline adduct of Formula VIII recorded on a PANalytical X'pert Pro instrument. The measurements were done using CuK a radiation at 45kV.
  • organic solvent is meant to comprise polar solvent (for example, dichloromethane, methanol, tetrahydrofuran, dimethylformamide, ethyl acetate, etc.) and/or non-polar solvents (for example, cyclohexane, diethyl ether, toluene, etc.).
  • polar solvent for example, dichloromethane, methanol, tetrahydrofuran, dimethylformamide, ethyl acetate, etc.
  • non-polar solvents for example, cyclohexane, diethyl ether, toluene, etc.
  • organic solvents are dichloromethane, ethyl acetate, butyl acetate, dichloroethane, tetrahydrofuran, acetonitrile, acetone, cyclohexane, toluene, chloroform, 1 ,4-dioxane, dimethylsulfoxide, dimethylformamide, methanol, ethanol, propanol and/or butanol.
  • base is meant to comprise organic bases (for example, pyridine, triethylamine, etc.) and/or inorganic bases (for example, sodium hydride, ammonium hydroxide, sodium carbonate, etc.).
  • organic bases for example, pyridine, triethylamine, etc.
  • inorganic bases for example, sodium hydride, ammonium hydroxide, sodium carbonate, etc.
  • bases are sodium hydroxide, potassium hydroxide, magnesium hydroxide, dipotassium hydrogen orthophosphate, magnesium carbonate, sodium carbonate, potassium carbonate, pyridine, trimethylamine, triethylamine, diisopropylethylamine and/or N-methyl morpholine.
  • a first aspect of the present invention provides a process for the preparation of agomelatine wherein the process comprises converting a carbon dioxide adduct of 2-(7- methoxynaphthalen- 1 -yl)ethanamine (Formula VIII) into agomelatine.
  • the carbon dioxide adduct (Formula VIII) is acetylated to obtain agomelatine.
  • the adduct compound of Formula VIII can be acetylated using acetyl chloride or acetic anhydride.
  • the compound of Formula VIII is acetylated using acetic anhydride in the presence of methanol to obtain agomelatine.
  • a second aspect of the present invention provides a process for the preparation of agomelatine comprising a step of converting l-[2-(7-methoxynaphthalen- l-yl)ethyl] ⁇ 5 - triaz-l-en-2-yne (Formula V)
  • the conversion of the compound of Formula V into the compound of Formula VIII can be performed with or without isolating the 2-(7- methoxynaphthalen- 1 -yl)ethanamine intermediate compound of Formula VII.
  • the conversion of the compound of Formula V into the compound of Formula VIII can be performed without isolating the 2-(7- methoxynaphthalen- 1 -yl)ethanamine intermediate compound of Formula VII.
  • the compound of Formula V is converted to the compound of Formula VIII by reducing the compound of Formula V, followed then treating the reduced product with carbon dioxide.
  • the reduced product is 2-(7- methoxynaphthalen- 1 -yl)ethanamine of Formula VII.
  • the compound of Formula V is reduced and then treated with carbon dioxide to obtain an adduct compound of Formula VIII which is acetylated to get agomelatine.
  • the reduction of the compound of Formula V can be performed using hydrogen gas in the presence of a reduction catalyst.
  • the reduction catalyst can be platinum, palladium, rhodium and/or Raney nickel.
  • the reduction can be carried out at a temperature range of about 10°C to about 70°C.
  • the hydrogen pressure can be in the range of about 1.0 kg/cm 2 to about 3.0 kg/cm 2 .
  • the compound of Formula VII (reduction product), if isolated or in concentrated form (wet), can be dissolved in non-polar solvent and then treated with carbon dioxide to obtain the adduct compound of Formula VIII.
  • the obtained adduct can be converted into agomelatine by following the process described hereinabove in the first aspect of the present invention.
  • a third aspect of the present invention provides a process for the preparation of agomelatine comprising a step of converting 2-(7-methoxynaphthalen- 1 -yl)ethyl 4- nitrobenzene sulfonate of Formula IV
  • the compound of Formula IV is converted to the compound of Formula V by treatment of the compound of Formula IV with an azide salt.
  • the azide salt can be selected from the group comprised of sodium azide, silver azide and phenyl azide.
  • the compound of Formula IV is treated with sodium azide to obtain the compound of Formula V, which is reduced, then treated with carbon dioxide to provide an adduct compound of Formula VIII. This adduct is then acetylated to obtain agomelatine.
  • the compound of Formula V can be converted into the carbon dioxide adduct of Formula VIII by following the process described hereinabove in the second aspect of the present invention.
  • the obtained adduct (Formula VIII) can be converted into agomelatine by following the process described hereinabove in the first aspect of the present invention.
  • a fourth aspect of the present invention provides a process for the preparation of agomelatine comprising the steps of: (a) reacting (7-methoxy- 1 -naphthyl)ethanol of Formula III
  • step (b) converting the compound of Formula IV obtained in step (a) into
  • the compound of Formula III is reacted with 4-nitrobenzene sulfonyl chloride in the presence of a base and an organic solvent.
  • the base used is triethylamine.
  • the organic solvent is dichloromethane.
  • the conversion of the compound of Formula IV into agomelatine can be performed via preparation of l-[2-(7-methoxynaphthalen-l-yl)ethyl]- 2 ⁇ 5 - ⁇ 3 ⁇ - 1 -en-2-yne (Formula V), 2-(7-methoxynaphthalen- 1 -yl)ethanamine (Formula VII), and/or a carbon dioxide adduct of 2-(7-methoxynaphthalen- 1 -yl)ethanamine (Formula VIII) intermediate compounds.
  • the compound of Formula IV can be converted into the compound of Formula V by following the process described hereinabove in the third aspect of the present invention.
  • the compound of Formula V can be converted into the carbon dioxide adduct of Formula VIII by following the process described hereinabove in the second aspect of the present invention.
  • the obtained adduct (Formula VIII) can be converted into agomelatine by following the process described hereinabove in the first aspect of the present invention.
  • a fifth aspect of the present invention provides 2-(7-methoxynaphthalen- 1 -yl)ethyl 4-nitrobenzene sulfonate compound of Formula IV.
  • the compound of Formula IV can be used as an intermediate for the preparation of agomelatine.
  • the compound of Formula IV can be used to prepare agomelatine described hereinabove in the third aspect of the present invention.
  • a sixth aspect of the present invention provides l-[2-(7-methoxynaphthalen-l- yl)ethyl]-2 ⁇ 5 -triaz-l-en-2-yne compound of Formula V.
  • the compound of Formula V can be used as an intermediate for the preparation of agomelatine.
  • the compound of Formula V can be used to prepare agomelatine as described hereinabove in the second aspect of the present invention.
  • a seventh aspect of the present invention provides a carbon dioxide adduct of 2-(7- methoxynaphthalen-l-yl)ethanamine represented by Formula VIII.
  • the compound of Formula VIII can be used as an intermediate for the preparation of agomelatine.
  • the compound of Formula V can be used to prepare agomelatine as described hereinabove in the first aspect of the present invention.
  • compound of Formula VIII can be crystalline.
  • the crystalline adduct of Formula VIII can be any suitable adduct of Formula VIII.
  • the crystalline adduct of Formula VIII can be any suitable adduct of Formula VIII.
  • the starting material (7-methoxy- l-naphthyl)ethanol, as used herein, in this invention can be prepared by treating 7-methoxy- 1 -naphthyl acetic acid represented by Formula II with lithium aluminum hydride in the presence of tetrahydrofuran.
  • the 7-methoxy- l-naphthyl acetic acid of Formula II can be prepared by any method known in the art, for example, by following the process described in U.S. Patent No. 5,225,442.
  • XRPD X-ray powder diffractograms

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

Abstract

La présente invention concerne un procédé pour la préparation d'agomélatine et de ses composés intermédiaires. L'invention concerne également des composés intermédiaires d'agomélatine représentés par la formule IV, la formule V et la formule VIII.
PCT/IB2012/055485 2011-10-11 2012-10-10 Procédé pour la préparation d'agomélatine WO2013054273A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2921DE2011 2011-10-11
IN2921/DEL/2011 2011-10-11

Publications (3)

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WO2013054273A2 true WO2013054273A2 (fr) 2013-04-18
WO2013054273A9 WO2013054273A9 (fr) 2013-07-11
WO2013054273A3 WO2013054273A3 (fr) 2013-09-06

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110141935A (zh) * 2019-05-13 2019-08-20 华侨大学 一种用于二氧化碳捕集的功能化离子液体相变体系及应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5225442A (en) 1990-02-27 1993-07-06 Adir Et Compagnie Compounds having a naphthalene structure
US7470806B2 (en) 2004-02-13 2008-12-30 Les Laboratories Servier Process for the synthesis of (7-methoxy-1-naphthyl) acetonitrile and its application in the synthesis of agomelatine
US7476751B2 (en) 2004-02-13 2009-01-13 Les Laboratoires Servier Process for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and its application in the synthesis of agomelatine
US7479569B2 (en) 2004-02-13 2009-01-20 Les Laboratoires Servier Process for the synthesis of (7-methoxy-3,4-dihydro-1-naphthalenyl) acetonitrile and its application in the synthesis of agomelatine
US20100036161A1 (en) 2008-08-05 2010-02-11 Les Laboratoires Servier Process for the synthesis of agomelatine
US20100137628A1 (en) 2007-08-03 2010-06-03 Les Laboratoires Servier Process for the synthesis of (methoxy-1-naphthyl) acetonitrile and application in the synthesis of agomelatine
US20110130571A1 (en) 2008-07-29 2011-06-02 Guisen Zhang Process for the manufacture of agomelatine and its intermediate

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5225442A (en) 1990-02-27 1993-07-06 Adir Et Compagnie Compounds having a naphthalene structure
US7470806B2 (en) 2004-02-13 2008-12-30 Les Laboratories Servier Process for the synthesis of (7-methoxy-1-naphthyl) acetonitrile and its application in the synthesis of agomelatine
US7476751B2 (en) 2004-02-13 2009-01-13 Les Laboratoires Servier Process for the synthesis of (7-methoxy-1-naphthyl)acetonitrile and its application in the synthesis of agomelatine
US7479569B2 (en) 2004-02-13 2009-01-20 Les Laboratoires Servier Process for the synthesis of (7-methoxy-3,4-dihydro-1-naphthalenyl) acetonitrile and its application in the synthesis of agomelatine
US20100137628A1 (en) 2007-08-03 2010-06-03 Les Laboratoires Servier Process for the synthesis of (methoxy-1-naphthyl) acetonitrile and application in the synthesis of agomelatine
US20110130571A1 (en) 2008-07-29 2011-06-02 Guisen Zhang Process for the manufacture of agomelatine and its intermediate
US20100036161A1 (en) 2008-08-05 2010-02-11 Les Laboratoires Servier Process for the synthesis of agomelatine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110141935A (zh) * 2019-05-13 2019-08-20 华侨大学 一种用于二氧化碳捕集的功能化离子液体相变体系及应用
CN110141935B (zh) * 2019-05-13 2021-06-01 华侨大学 一种用于二氧化碳捕集的功能化离子液体相变体系及应用

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WO2013054273A3 (fr) 2013-09-06
WO2013054273A9 (fr) 2013-07-11

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