WO2015022702A3 - Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof - Google Patents

Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof Download PDF

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Publication number
WO2015022702A3
WO2015022702A3 PCT/IN2014/000522 IN2014000522W WO2015022702A3 WO 2015022702 A3 WO2015022702 A3 WO 2015022702A3 IN 2014000522 W IN2014000522 W IN 2014000522W WO 2015022702 A3 WO2015022702 A3 WO 2015022702A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
ivabradine
salts
formula
relates
Prior art date
Application number
PCT/IN2014/000522
Other languages
French (fr)
Other versions
WO2015022702A2 (en
Inventor
Rajesh Vinodrai Naik
Gurdeep Singh Sarin
Pranav Gupta
Dilpreet Singh
Original Assignee
Ind-Swift 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 Ind-Swift Laboratories Limited filed Critical Ind-Swift Laboratories Limited
Priority claimed from IN3349DE2013 external-priority patent/IN2013DE03349A/en
Publication of WO2015022702A2 publication Critical patent/WO2015022702A2/en
Publication of WO2015022702A3 publication Critical patent/WO2015022702A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/84—Purification
    • 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
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/06—One of the condensed rings being a six-membered aromatic ring the other ring being four-membered

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

Abstract

The present invention relates to an improved process for preparation of 4,5-dimethoxybenzene derivatives, which are important key intermediates in the preparation of ivabradine and salts thereof. Mainly present invention relates to an efficient and industrially advantageous process for purification of 4,5-dimethoxy benzocyclbbutane derivatives, which are important key intermediates in the preparation of ivabradine and salts thereof. Particularly, the present invention relates to a process for purification of 4,5-dimethoxy- 1-cyano-benzocyclobutane of formula I, and a process for purification of (S)-N-[(4,5-dimethoxybenzocyclobut-1-yl)-methyl]-N- (methyl)amine camphosulphonic acid salt of formula II. The present invention also relates to an efficient and industrially advantageous process for preparation of 3-(2-bromo-4,5-dimethoxybenzene)propionitrile of formula III, with high purity and high yield, wherein compound of formula III is an important precursor of 4,5-dimethoxy- 1-cyano-benzocyclobutane of formula I, a key intermediate used in the preparation of ivabradine and salts thereof.
PCT/IN2014/000522 2013-08-10 2014-08-11 Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof WO2015022702A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN2383/DEL/2013 2013-08-10
IN2383DE2013 2013-08-10
IN3349/DEL/2013 2013-11-14
IN3349DE2013 IN2013DE03349A (en) 2013-11-14 2014-08-11

Publications (2)

Publication Number Publication Date
WO2015022702A2 WO2015022702A2 (en) 2015-02-19
WO2015022702A3 true WO2015022702A3 (en) 2015-04-09

Family

ID=52468758

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2014/000522 WO2015022702A2 (en) 2013-08-10 2014-08-11 Process for preparation of 4,5-dimethoxybenzene derivatives and use in the synthesis of ivabradine and salts thereof

Country Status (1)

Country Link
WO (1) WO2015022702A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3101010A1 (en) 2015-06-03 2016-12-07 Urquima S.A. New method for the preparation of highly pure ivabradine base and salts thereof
CN108530359A (en) * 2017-03-01 2018-09-14 浙江京新药业股份有限公司 A kind of preparation method of Ivabradine impurity
CN112724001B (en) * 2019-10-28 2022-12-13 鲁南制药集团股份有限公司 Ivabradine chiral intermediate compound

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050261376A1 (en) * 2004-05-19 2005-11-24 Jean-Michel Lerestif Process for the synthesis of (is)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and to the application thereof in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
WO2008146308A2 (en) * 2007-05-30 2008-12-04 Ind-Swift Laboratories Limited Process for the preparation of ivabradine hydrochloride and polymorph thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050261376A1 (en) * 2004-05-19 2005-11-24 Jean-Michel Lerestif Process for the synthesis of (is)-4,5-dimethoxy-1-(methylaminomethyl)-benzocyclobutane and addition salts thereof, and to the application thereof in the synthesis of ivabradine and addition salts thereof with a pharmaceutically acceptable acid
WO2008146308A2 (en) * 2007-05-30 2008-12-04 Ind-Swift Laboratories Limited Process for the preparation of ivabradine hydrochloride and polymorph thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SCHIESS P. ET AL.: "Formation of substituted benzocyclobutenes through flash vacuum pyrolysis.", TETRAHEDRON LETTERS, vol. 23, no. ISSUE, 1982, pages 3669 - 3672, XP028085805, DOI: doi:10.1016/S0040-4039(00)88653-0 *

Also Published As

Publication number Publication date
WO2015022702A2 (en) 2015-02-19

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