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WO2013175499A3 - Process for the preparation of 5-(4-[4-(5-cyano-1 h-indol-3-yl)butyl]piperazin-1 -yl)benzofuran-2-carboxamide and intermediates thereof, polymorphic forms thereof - Google Patents

Process for the preparation of 5-(4-[4-(5-cyano-1 h-indol-3-yl)butyl]piperazin-1 -yl)benzofuran-2-carboxamide and intermediates thereof, polymorphic forms thereof Download PDF

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Publication number
WO2013175499A3
WO2013175499A3 PCT/IN2013/000262 IN2013000262W WO2013175499A3 WO 2013175499 A3 WO2013175499 A3 WO 2013175499A3 IN 2013000262 W IN2013000262 W IN 2013000262W WO 2013175499 A3 WO2013175499 A3 WO 2013175499A3
Authority
WO
WIPO (PCT)
Prior art keywords
benzofuran
carboxamide
piperazin
indol
cyano
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/IN2013/000262
Other languages
French (fr)
Other versions
WO2013175499A2 (en
Inventor
Shriprakash Dhar DWIVEDI
Ramesh Chandra SINGH
Rajendra Gokalbhai CHAVDA
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 WO2013175499A2 publication Critical patent/WO2013175499A2/en
Anticipated expiration legal-status Critical
Publication of WO2013175499A3 publication Critical patent/WO2013175499A3/en
Ceased legal-status Critical Current

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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

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

Abstract

The present invention relates to a process for the preparation of 5-(4-[4-(5- cyano- 1 H-indol-3 -yl)butyl] piperazin- 1 -yl)benzofuran-2-carboxamide of Formula (1) or its pharmaceutically acceptable salt, solvates or hydrates thereof. In particular, the present invention provides a novel intermediate compound, 5-(4-substitutedpiperazin- 1-yl)benzofuran-2-carboxamide of Formula (X). The present invention further provides solid state form of 5-(4-[4-(5-cyano-1H-indol-3- yl) butyl]piperazin-1-yl)benzofuran-2-carboxamide of Formula (1) and process for its preparation.
PCT/IN2013/000262 2012-04-20 2013-04-22 Polymorphic form of 5-(4-[4-(5-cyano-1h-indol-3- yl)butyl]piperazin-1-yl) benzofuran-2-carboxamide Ceased WO2013175499A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1260MU2012 2012-04-20
IN1260/MUM/2012 2012-04-20

Publications (2)

Publication Number Publication Date
WO2013175499A2 WO2013175499A2 (en) 2013-11-28
WO2013175499A3 true WO2013175499A3 (en) 2014-10-23

Family

ID=49036619

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2013/000262 Ceased WO2013175499A2 (en) 2012-04-20 2013-04-22 Polymorphic form of 5-(4-[4-(5-cyano-1h-indol-3- yl)butyl]piperazin-1-yl) benzofuran-2-carboxamide

Country Status (1)

Country Link
WO (1) WO2013175499A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013185209A1 (en) 2012-06-13 2013-12-19 Apotex Technologies Inc. Forms of vilazodone and processes for the preparation thereof
CA2884676A1 (en) 2012-09-12 2014-03-20 Apotex Pharmachem Inc. Processes for the preparation of 3-alkyl indoles
WO2014061004A2 (en) * 2012-10-19 2014-04-24 Ranbaxy Laboratories Limited Process for the preparation of vilazodone or pharmaceutically acceptable salt thereof
US20140179713A1 (en) * 2012-11-05 2014-06-26 Cadila Healthcare Limited Polymorphic form of 5-(4-[4-(5-cyano-1h-indol-3-yl) butyl] piperazin-1-yl) benzofuran-2-carboxamide and process for preparing thereof
CN104926804B (en) * 2015-06-04 2019-01-25 天津渤海职业技术学院 One kind has compound, the preparation method and use of antitumor action
CN105541811A (en) * 2016-01-08 2016-05-04 万特制药(海南)有限公司 Refining method for antidepressant drug vilazodone

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0738722A1 (en) * 1995-04-20 1996-10-23 MERCK PATENT GmbH 5-Amino-benzofuran-2-carboxylic acid derivatives
CN102267985A (en) * 2011-06-15 2011-12-07 上海医药工业研究院 Preparation method for vilazodone and hydrochloride thereof
WO2013114338A1 (en) * 2012-02-01 2013-08-08 Ranbaxy Laboratories Limited Process for the preparation of vilazodone or its pharmaceutically acceptable salts

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0738722A1 (en) * 1995-04-20 1996-10-23 MERCK PATENT GmbH 5-Amino-benzofuran-2-carboxylic acid derivatives
CN102267985A (en) * 2011-06-15 2011-12-07 上海医药工业研究院 Preparation method for vilazodone and hydrochloride thereof
WO2013114338A1 (en) * 2012-02-01 2013-08-08 Ranbaxy Laboratories Limited Process for the preparation of vilazodone or its pharmaceutically acceptable salts

Non-Patent Citations (1)

* 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, vol. 47, no. 19, 1 January 2004 (2004-01-01), pages 4684 - 4692, XP002388367, ISSN: 0022-2623, DOI: 10.1021/JM040793Q *

Also Published As

Publication number Publication date
WO2013175499A2 (en) 2013-11-28

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