WO2013175361A1 - Procédé de préparation de chlorhydrate de vilazodone - Google Patents

Procédé de préparation de chlorhydrate de vilazodone Download PDF

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Publication number
WO2013175361A1
WO2013175361A1 PCT/IB2013/054021 IB2013054021W WO2013175361A1 WO 2013175361 A1 WO2013175361 A1 WO 2013175361A1 IB 2013054021 W IB2013054021 W IB 2013054021W WO 2013175361 A1 WO2013175361 A1 WO 2013175361A1
Authority
WO
WIPO (PCT)
Prior art keywords
process according
formula
compound
reaction mixture
hydrochloric acid
Prior art date
Application number
PCT/IB2013/054021
Other languages
English (en)
Inventor
Prasenjit Das
Nitin Maheshwari
Hashim Nizar Poovanathil Nagoor Meeran
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 WO2013175361A1 publication Critical patent/WO2013175361A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a process for the preparation of vilazodone hydrochloride without isolating vilazodone free base.
  • the present inventors have developed a simple and efficient process for the preparation of vilazodone hydrochloride without isolating vilazodone free base.
  • Vilazodone hydrochloride obtained by the present process can be directly isolated from the reaction mixture obtained after reacting 3-(4-chlorobutyl)- lH-indole-5-carbonitrile of Formula II, 5-(piperazin- 1 -yl)- 1 -benzofuran-2-carboxamide of Formula III, and hydrochloric acid.
  • An aspect of the present invention provides a process for the preparation of vilazodone hydrochloride of Formula I,
  • step b) treating the reaction mixture obtained in step a) with hydrochloric acid; and c) isolating vilazodone hydrochloride of Formula I from the reaction mixture thereof.
  • reaction of the compound of Formula II and the compound of Formula III may be carried out in the presence of a base and solvent.
  • the solvent used for the reaction of the compound of Formula II and the compound of Formula III may be selected from the group consisting of water, organic solvent, or a mixture thereof.
  • Suitable organic solvents may be selected from the group consisting of alcohol, ketone, nitrile, amide, aromatic, aliphatic hydrocarbon, or dimethyl sulfoxide.
  • Suitable alcoholic solvents may include methanol, 2-propanol, or 1 -propanol.
  • Suitable nitrile solvents may include acetonitrile.
  • Suitable amide solvents may include N- methylpyrrolidone, dimethylacetamide, and ⁇ , ⁇ -dimethylformamide.
  • Suitable ketone solvents may include acetone or methyl isobutyl ketone.
  • Suitable aromatic hydrocarbon solvents may include toluene.
  • Preferable solvents may include N-methylpyrrolidone or N,N-dimethylformamide.
  • the base used for the reaction of the compound of Formula II and the compound of Formula III may be selected from organic or inorganic bases.
  • Suitable organic bases may include tributylamine, triethylamine, diisopropylamine, diisopropylethylamine, 4- dimethylaminopyridine, pyrollidine, or N-methylmorpholine.
  • a preferable organic base is tributylamine.
  • Suitable inorganic bases may include hydroxides or carbonates and bicarbonates of alkali or alkaline metals. Suitable carbonates or bicarbonates of alkali or alkaline metals may include sodium carbonate, potassium carbonate, magnesium carbonate, sodium bicarbonate, or potassium bicarbonate.
  • a preferable inorganic base is potassium carbonate.
  • the treatment of the compound of Formula II and the compound of Formula III may be carried out in the presence of alkali metal halides, for example, sodium iodide.
  • the reaction of the compound of Formula II and the compound of Formula III may be carried out at a temperature of about 5°C to about 130°C, preferably at about 10°C to about 120°C.
  • the treatment of the compound of Formula II and the compound of Formula III may be carried out for about 1 hour to about 10 hours, preferably for about 2 hours to about 6 hours. This reaction mixture may be cooled to 30°C.
  • the reaction mixture obtained in step a) may be directly treated with hydrochloric acid without isolating vilazodone free base.
  • the hydrochloric acid may be diluted or concentrated.
  • the hydrochloric acid may be used in solution form or gaseous form.
  • the solution of hydrochloric acid may be aqueous or in an alcoholic solvent.
  • the alcoholic solvent used for the preparation of hydrochloric acid solution may preferably be 2- propanol.
  • the treatment of the reaction mixture obtained in step a) with hydrochloric acid may be carried out at a temperature of about 10°C to about 100°C, preferably at about 25°C to about 80°C.
  • the treatment of the reaction mixture obtained in step a) with hydrochloric acid may be carried out for about 2 hours to about 25 hours, preferably for about 3 hours to about 20 hours.
  • the vilazodone hydrochloride of Formula I may be isolated by filtration, concentration, precipitation, cooling, centrifugation, decantation, or a combination thereof.
  • the vilazodone hydrochloride prepared by the present invention may be characterized using X-ray powder diffraction pattern (XRPD).
  • the reaction mixture was decanted and 2-propanol (100 mL) was added to the reaction mixture.
  • the reaction mixture was heated at 80°C for 60 minutes.
  • the reaction mixture was cooled to 30°C and stirred for 16 hours, filtered, and washed with 2-propanol (10 mL).
  • the solid obtained was dried in an air oven at 50°C to 55°C for 8 hours to obtain the title compound.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un procédé de préparation de chlorhydrate de vilazodone sans isolement de la base libre de vilazodone.
PCT/IB2013/054021 2012-05-24 2013-05-16 Procédé de préparation de chlorhydrate de vilazodone WO2013175361A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1592/DEL/2012 2012-05-24
IN1592DE2012 2012-05-24

Publications (1)

Publication Number Publication Date
WO2013175361A1 true WO2013175361A1 (fr) 2013-11-28

Family

ID=48699897

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2013/054021 WO2013175361A1 (fr) 2012-05-24 2013-05-16 Procédé de préparation de chlorhydrate de vilazodone

Country Status (1)

Country Link
WO (1) WO2013175361A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20131598A1 (it) * 2013-09-27 2015-03-28 Dipharma Francis Srl Procedimento per la preparazione di un principio attivo farmaceutico in forma amorfa

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0648767A1 (fr) 1993-09-30 1995-04-19 MERCK PATENT GmbH Dérivés de piperidine et piperazine qui puissent agir sur le "CNS"
EP0738722A1 (fr) * 1995-04-20 1996-10-23 MERCK PATENT GmbH Dérivés d'acides 5-amino-benzofuran-2-carboxyliques
EP1397357A2 (fr) 2001-06-19 2004-03-17 MERCK PATENT GmbH Formes polymorphes de chlorhydrate de 1-'4-(5-cyanoindol-3-yl)butyl-4-(2-carbamoylbenzofuran-5-yl)piperazine
WO2006114202A1 (fr) * 2005-04-26 2006-11-02 Merck Patent Gmbh Procede de production de 5-(4-[4-(5-cyano-3-indolyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0648767A1 (fr) 1993-09-30 1995-04-19 MERCK PATENT GmbH Dérivés de piperidine et piperazine qui puissent agir sur le "CNS"
US5532241A (en) 1993-09-30 1996-07-02 Merck Patent Gesellschaft Mit Beschrankter Haftung Piperidines and piperazines
EP0738722A1 (fr) * 1995-04-20 1996-10-23 MERCK PATENT GmbH Dérivés d'acides 5-amino-benzofuran-2-carboxyliques
EP1397357A2 (fr) 2001-06-19 2004-03-17 MERCK PATENT GmbH Formes polymorphes de chlorhydrate de 1-'4-(5-cyanoindol-3-yl)butyl-4-(2-carbamoylbenzofuran-5-yl)piperazine
US7834020B2 (en) 2001-06-19 2010-11-16 Merck Patent Gesellschaft Polymorphic forms of 1-′4-(5-cyanoindol-3-yl)butyl-4-(2-carbamoylbenzofuran-5-yl) piperazine hydrochloride
WO2006114202A1 (fr) * 2005-04-26 2006-11-02 Merck Patent Gmbh Procede de production de 5-(4-[4-(5-cyano-3-indolyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HEINRICH T ET AL: "Synthesis and Structure-Activity Relationship in a Class of Indolebutylpiperazines as Dual 5-HT1A Receptor Agonists and Serotonin Reuptake Inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 47, no. 19, 1 January 2004 (2004-01-01), pages 4684 - 4692, XP002388367, ISSN: 0022-2623, DOI: 10.1021/JM040793Q *
SORBERA L A ET AL: "VILAZODONE HYDROCHLORIDE", DRUGS OF THE FUTURE, PROUS SCIENCE, ES, vol. 26, no. 3, 1 January 2001 (2001-01-01), pages 247 - 252, XP009035003, ISSN: 0377-8282, DOI: 10.1358/DOF.2001.026.03.611242 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20131598A1 (it) * 2013-09-27 2015-03-28 Dipharma Francis Srl Procedimento per la preparazione di un principio attivo farmaceutico in forma amorfa

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