BR0318690A - (e) -n, n-diethyl-2-cyano-3- (3,4-dihydroxy-5-nitrophenyl) acrylamide stable polymorphs - Google Patents

(e) -n, n-diethyl-2-cyano-3- (3,4-dihydroxy-5-nitrophenyl) acrylamide stable polymorphs

Info

Publication number
BR0318690A
BR0318690A BRPI0318690-3A BR0318690A BR0318690A BR 0318690 A BR0318690 A BR 0318690A BR 0318690 A BR0318690 A BR 0318690A BR 0318690 A BR0318690 A BR 0318690A
Authority
BR
Brazil
Prior art keywords
dihydroxy
nitrophenyl
diethyl
entacapone
acrylamide
Prior art date
Application number
BRPI0318690-3A
Other languages
Portuguese (pt)
Inventor
Siddiqui Mohammed Jaw Mukarram
Rashid Abdul Rehman Khan
Ram Prasad Yadav
Zakir Gafoor Shaikh
Original Assignee
Wockhardt 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 Wockhardt Ltd filed Critical Wockhardt Ltd
Publication of BR0318690A publication Critical patent/BR0318690A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

"POLIMORFOS ESTáVEIS DE (E)-N,N-DIETIL-2CIANO-3-(3,4-DIHIDRóXI-5-NITROFENIL)ACRIL AMIDA". A presente invenção refere-se a formas polimórficas cristalinas estáveis C e D de (E)-N,N,-dietil-2-ciano-3-(3,4-dihidróxi-5nitrofenil)acrilamida (Entacapona) e seus processos de preparação. A Forma C de (E)-Entacapona é obtida por condensação de 3,4-dihidróxi-5nitrobenzaldeído e N,N-dietilcianoacetamida na presença de uma base seguida por adição de ácido acético após terminar a reação, e etapa de cristalização. A Forma D de (E)-Entacapona é preparada a partir de Forma C de Entacapona, Forma A de (E)-Entacapona cristalograficamente pura ou Forma A de (E)-Entacapona cristalograficamente essencialmente pura. As formas polimórficas C e D de (E)-Entacapona são caracterizadas por valores específicos de pico de difração de Raios-X em pó e lnfravermelho (IR)."STABLE POLYMORPHS OF (E) -N, N-DIETHYL-2CIAN-3- (3,4-DIHYDROXY-5-NITROPHENYL) ACRIL AMIDE". The present invention relates to stable crystalline polymorphic forms C and D of (E) -N, N, diethyl-2-cyano-3- (3,4-dihydroxy-5-nitrophenyl) acrylamide (Entacapone) and its preparation processes . (C) -Entacapone Form C is obtained by condensation of 3,4-dihydroxy-5-nitrobenzaldehyde and N, N-diethylcyanoacetamide in the presence of a base followed by addition of acetic acid after completion of the reaction, and crystallization step. Form D of (E) -Entacapone is prepared from Entanapone Form C, Crystallographically Pure (E) -Etacapone Form A or Crystallographically pure (E) -Etacapone Form A. Polymorphic forms C and D of (E) -Entacapone are characterized by specific powder and infrared (IR) X-ray diffraction peak values.

BRPI0318690-3A 2003-12-29 2003-12-29 (e) -n, n-diethyl-2-cyano-3- (3,4-dihydroxy-5-nitrophenyl) acrylamide stable polymorphs BR0318690A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2003/006200 WO2005066117A1 (en) 2003-12-29 2003-12-29 Stable polymorphs of (e)-n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide

Publications (1)

Publication Number Publication Date
BR0318690A true BR0318690A (en) 2006-12-26

Family

ID=34746624

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0318690-3A BR0318690A (en) 2003-12-29 2003-12-29 (e) -n, n-diethyl-2-cyano-3- (3,4-dihydroxy-5-nitrophenyl) acrylamide stable polymorphs

Country Status (5)

Country Link
EP (1) EP1701937A4 (en)
AU (1) AU2003292465A1 (en)
BR (1) BR0318690A (en)
CA (1) CA2551791A1 (en)
WO (1) WO2005066117A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080319226A1 (en) * 2005-11-09 2008-12-25 Usv Limited Process For the Preparation of Highly Pure (E) N,N-Diethyl-2-Cyano-3-(3,4-Dihydroxy-5-Nitro Phenyl) Acrylamide (Entacapone)
EP1976824A1 (en) * 2006-01-02 2008-10-08 Actavis Group PTC EHF A process for the preparation of entacapone form-a
CA2641396C (en) * 2006-02-06 2014-07-22 Orion Corporation Process for manufacturing entacapone
GB0610207D0 (en) * 2006-05-23 2006-07-05 Pliva Istrazivanje I Razvoj D New forms of active pharmaceutical ingredient
WO2008023380A1 (en) * 2006-08-24 2008-02-28 Srinivasa Reddy Battula Improved and simplified procedure for the preparation of (e) n,n-diethyl-2-cyano-3(3,4-dihydroxy-5-nitrophenyl)acrylamide
ES2306587B1 (en) * 2006-11-15 2009-08-07 Quimica Sintetica, S.A. NEW CRYSTAL FORM OF ENTACAPONA AND PROCEDURE FOR OBTAINING.
ES2319024B1 (en) 2007-02-13 2009-12-11 Quimica Sintetica, S.A. PROCEDURE FOR OBTAINING ENTACAPONA SUBSTANTIALLY FREE OF ISOMERO Z, ITS SYNTHESIS INTERMEDIATES AND NEW CRYSTAL FORM.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
YU213587A (en) * 1986-11-28 1989-06-30 Orion Yhtymae Oy Process for obtaining new pharmacologic active cateholic derivatives
GB2238047B (en) * 1989-11-03 1993-02-10 Orion Yhtymae Oy Stable polymorphic form of (e)-n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide and the process for its preparation

Also Published As

Publication number Publication date
EP1701937A4 (en) 2007-05-02
EP1701937A1 (en) 2006-09-20
WO2005066117A1 (en) 2005-07-21
AU2003292465A1 (en) 2005-08-12
CA2551791A1 (en) 2005-07-21

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