BR0318690A - polimorfos estáveis de (e)-n,n-dietil-2-ciano-3-(3,4-dihidróxi-5-nitrofenil)acril amida - Google Patents
polimorfos estáveis de (e)-n,n-dietil-2-ciano-3-(3,4-dihidróxi-5-nitrofenil)acril amidaInfo
- 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
Links
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 title abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- -1 3,4-DIHYDROXY-5-NITROPHENYL Chemical class 0.000 abstract 1
- BBFJODMCHICIAA-UHFFFAOYSA-N 3,4-dihydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=CC([N+]([O-])=O)=C1O BBFJODMCHICIAA-UHFFFAOYSA-N 0.000 abstract 1
- RYSHIRFTLKZVIH-UHFFFAOYSA-N N,N-diethylcyanoacetamide Chemical compound CCN(CC)C(=O)CC#N RYSHIRFTLKZVIH-UHFFFAOYSA-N 0.000 abstract 1
- 238000002441 X-ray diffraction Methods 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 229960003337 entacapone Drugs 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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).
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 (pt) | 2006-12-26 |
Family
ID=34746624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0318690-3A BR0318690A (pt) | 2003-12-29 | 2003-12-29 | polimorfos estáveis de (e)-n,n-dietil-2-ciano-3-(3,4-dihidróxi-5-nitrofenil)acril amida |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1701937A4 (pt) |
| AU (1) | AU2003292465A1 (pt) |
| BR (1) | BR0318690A (pt) |
| CA (1) | CA2551791A1 (pt) |
| WO (1) | WO2005066117A1 (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE445591T1 (de) * | 2005-11-09 | 2009-10-15 | Usv Ltd | Verfahren zur herstellung von hochreinem (e)-n,n- diethyl-2-cyano-3-(3,4-dihydro-5- nitrophenyl)acrylamid (entacapon) |
| CN101460451A (zh) * | 2006-01-02 | 2009-06-17 | 阿克塔维什集团Ptc公司 | A型恩他卡朋的制备方法 |
| 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 (es) * | 2006-11-15 | 2009-08-07 | Quimica Sintetica, S.A. | Nueva forma cristalina de entacapona y procedimiento para su obtencion. |
| ES2319024B1 (es) | 2007-02-13 | 2009-12-11 | Quimica Sintetica, S.A. | Procedimiento para la obtencion de entacapona sustancialmente libre de isomero z, sus intermedios de sintesis y nueva forma cristalina. |
Family Cites Families (2)
| 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 |
-
2003
- 2003-12-29 BR BRPI0318690-3A patent/BR0318690A/pt not_active IP Right Cessation
- 2003-12-29 CA CA002551791A patent/CA2551791A1/en not_active Abandoned
- 2003-12-29 EP EP03768046A patent/EP1701937A4/en not_active Ceased
- 2003-12-29 WO PCT/IB2003/006200 patent/WO2005066117A1/en not_active Ceased
- 2003-12-29 AU AU2003292465A patent/AU2003292465A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2551791A1 (en) | 2005-07-21 |
| AU2003292465A1 (en) | 2005-08-12 |
| EP1701937A4 (en) | 2007-05-02 |
| WO2005066117A1 (en) | 2005-07-21 |
| EP1701937A1 (en) | 2006-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application fees: dismissal - article 86 of industrial property law |
Free format text: REFERENTE A 4A,5A E 6A ANUIDADES |
|
| B08K | Lapse as no evidence of payment of the annual fee has been furnished to inpi (acc. art. 87) |
Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 2073 DE 28/09/2010. |