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WO2009084031A3 - An improved process for preparation of (2e)-2-cyano-3-(3,4- dihydroxy-5-nitrophenyl)n,n-diethyl-2-propenamide polymorphic form a - Google Patents

An improved process for preparation of (2e)-2-cyano-3-(3,4- dihydroxy-5-nitrophenyl)n,n-diethyl-2-propenamide polymorphic form a Download PDF

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Publication number
WO2009084031A3
WO2009084031A3 PCT/IN2008/000806 IN2008000806W WO2009084031A3 WO 2009084031 A3 WO2009084031 A3 WO 2009084031A3 IN 2008000806 W IN2008000806 W IN 2008000806W WO 2009084031 A3 WO2009084031 A3 WO 2009084031A3
Authority
WO
WIPO (PCT)
Prior art keywords
cyano
diethyl
propenamide
nitrophenyl
dihydroxy
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/IN2008/000806
Other languages
French (fr)
Other versions
WO2009084031A2 (en
Inventor
Arul Ramakrishnan
Guruswamy Bathani
Srilatha Taduri
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.)
Neuland Laboratories Ltd
Original Assignee
Neuland Laboratories 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 Neuland Laboratories Ltd filed Critical Neuland Laboratories Ltd
Publication of WO2009084031A2 publication Critical patent/WO2009084031A2/en
Anticipated expiration legal-status Critical
Publication of WO2009084031A3 publication Critical patent/WO2009084031A3/en
Ceased legal-status Critical Current

Links

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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids

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

Abstract

The present invention relates to an improved, cost effective, eco-friendly and easy t handle process to manufacture substantially pure form of (2E)-2-Cyano-3-(3,4-dihydroxy-5 nitrophenyl)-N,N-diethyl-2-propenamide or (E)- N,N-diethyl-2-cyano-3-(3,4-dihyroxy-5 nitroρhenyl)-acrylamide polymorphic form A commonly known as (E)-Entacapone represente by Formula I, using ammonium acetate as a base.
PCT/IN2008/000806 2007-12-03 2008-12-02 An improved process for preparation of (2e)-2-cyano-3-(3,4- dihydroxy-5-nitrophenyl)n,n-diethyl-2-propenamide polymorphic form a Ceased WO2009084031A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2864CH2007 2007-12-03
IN2864/CHE/2007 2007-12-03

Publications (2)

Publication Number Publication Date
WO2009084031A2 WO2009084031A2 (en) 2009-07-09
WO2009084031A3 true WO2009084031A3 (en) 2010-11-25

Family

ID=40824846

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000806 Ceased WO2009084031A2 (en) 2007-12-03 2008-12-02 An improved process for preparation of (2e)-2-cyano-3-(3,4- dihydroxy-5-nitrophenyl)n,n-diethyl-2-propenamide polymorphic form a

Country Status (1)

Country Link
WO (1) WO2009084031A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105061259A (en) * 2015-08-25 2015-11-18 重庆植恩药业有限公司 Preparing method for entacapone A-type crystals
CN105237437B (en) * 2015-12-03 2017-05-17 重庆植恩药业有限公司 Entacapone impurity compound and preparation method thereof
IL307739A (en) * 2021-04-15 2023-12-01 Univ Brown Nitrophenyl-acrylamides and uses thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4963590A (en) * 1986-11-28 1990-10-16 Orion-Yhtyma Oy Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same
US5135950A (en) * 1989-11-03 1992-08-04 Orion-Yhtyma Oy Stable polymorphic form of (e)-n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide and the process for its preparation
WO2005070881A1 (en) * 2003-12-24 2005-08-04 Wockhardt Limited An efficient process for the manufacture of (e)-entacapone polymorphic form a
WO2007054950A1 (en) * 2005-11-09 2007-05-18 Usv Limited A process for the preparation of highly pure (e) n,n-diethyl-2-cyano-3-(3,4-dihydroxy- 5-nitro phenyl) acrylamide (entacapone)
WO2007094007A1 (en) * 2006-02-13 2007-08-23 Suven Life Sciences Ltd., An improved process for the preparation of entacapone
WO2007144169A2 (en) * 2006-06-16 2007-12-21 Schwarz Pharma Ag Entacapone-derivatives

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4963590A (en) * 1986-11-28 1990-10-16 Orion-Yhtyma Oy Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same
US5135950A (en) * 1989-11-03 1992-08-04 Orion-Yhtyma Oy Stable polymorphic form of (e)-n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide and the process for its preparation
WO2005070881A1 (en) * 2003-12-24 2005-08-04 Wockhardt Limited An efficient process for the manufacture of (e)-entacapone polymorphic form a
WO2007054950A1 (en) * 2005-11-09 2007-05-18 Usv Limited A process for the preparation of highly pure (e) n,n-diethyl-2-cyano-3-(3,4-dihydroxy- 5-nitro phenyl) acrylamide (entacapone)
WO2007094007A1 (en) * 2006-02-13 2007-08-23 Suven Life Sciences Ltd., An improved process for the preparation of entacapone
WO2007144169A2 (en) * 2006-06-16 2007-12-21 Schwarz Pharma Ag Entacapone-derivatives

Also Published As

Publication number Publication date
WO2009084031A2 (en) 2009-07-09

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