ATE445591T1 - Verfahren zur herstellung von hochreinem (e)-n,n- diethyl-2-cyano-3-(3,4-dihydro-5- nitrophenyl)acrylamid (entacapon) - Google Patents
Verfahren zur herstellung von hochreinem (e)-n,n- diethyl-2-cyano-3-(3,4-dihydro-5- nitrophenyl)acrylamid (entacapon)Info
- Publication number
- ATE445591T1 ATE445591T1 AT05826478T AT05826478T ATE445591T1 AT E445591 T1 ATE445591 T1 AT E445591T1 AT 05826478 T AT05826478 T AT 05826478T AT 05826478 T AT05826478 T AT 05826478T AT E445591 T1 ATE445591 T1 AT E445591T1
- Authority
- AT
- Austria
- Prior art keywords
- diethyl
- cyano
- nitrophenyl
- acrylamide
- organic
- 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 3
- 229960003337 entacapone Drugs 0.000 title abstract 2
- SGHLQSOQZHDBIS-UHFFFAOYSA-N C(C)N(C(C(=CC1=CCCC(=C1)[N+](=O)[O-])C#N)=O)CC Chemical compound C(C)N(C(C(=CC1=CCCC(=C1)[N+](=O)[O-])C#N)=O)CC SGHLQSOQZHDBIS-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000012043 crude product Substances 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- JRURYQJSLYLRLN-UHFFFAOYSA-N 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide Chemical compound CCN(CC)C(=O)C(C#N)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-UHFFFAOYSA-N 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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- 239000002253 acid Substances 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
Classifications
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2005/000363 WO2007054950A1 (en) | 2005-11-09 | 2005-11-09 | A process for the preparation of highly pure (e) n,n-diethyl-2-cyano-3-(3,4-dihydroxy- 5-nitro phenyl) acrylamide (entacapone) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE445591T1 true ATE445591T1 (de) | 2009-10-15 |
Family
ID=36910913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT05826478T ATE445591T1 (de) | 2005-11-09 | 2005-11-09 | Verfahren zur herstellung von hochreinem (e)-n,n- diethyl-2-cyano-3-(3,4-dihydro-5- nitrophenyl)acrylamid (entacapon) |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080319226A1 (de) |
| EP (1) | EP1945607B1 (de) |
| AT (1) | ATE445591T1 (de) |
| DE (1) | DE602005017204D1 (de) |
| WO (1) | WO2007054950A1 (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009084031A2 (en) * | 2007-12-03 | 2009-07-09 | Neuland Laboratories Ltd | An improved process for preparation of (2e)-2-cyano-3-(3,4- dihydroxy-5-nitrophenyl)n,n-diethyl-2-propenamide polymorphic form a |
| EP2251323B1 (de) * | 2009-05-14 | 2014-04-23 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Verfahren zur Reinigung von Entacapon |
| CN104402764A (zh) * | 2014-11-26 | 2015-03-11 | 千辉药业（安徽）有限责任公司 | 一种恩他卡朋的制备方法 |
| CN105061259A (zh) * | 2015-08-25 | 2015-11-18 | 重庆植恩药业有限公司 | 一种恩他卡朋a型晶的制备方法 |
Family Cites Families (6)
| 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 |
| EP1701936A4 (de) * | 2003-12-24 | 2007-01-24 | Wockhardt Ltd | Effizientes verfahren zur herstellung der polymorphen form a von (e)-entacapon |
| CA2551791A1 (en) * | 2003-12-29 | 2005-07-21 | Wockhardt Limited | Stable polymorphs of (e)-n,n-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide |
| CA2552099C (en) * | 2003-12-29 | 2011-10-04 | Suven Life Sciences Ltd | Improved process for the preparation of entacapone |
| EP1713768A2 (de) * | 2003-12-31 | 2006-10-25 | Cilag AG | Neue kristalline formen von entacapone und deren herstellung |
-
2005
- 2005-11-09 US US12/092,657 patent/US20080319226A1/en not_active Abandoned
- 2005-11-09 EP EP05826478A patent/EP1945607B1/de not_active Expired - Lifetime
- 2005-11-09 AT AT05826478T patent/ATE445591T1/de not_active IP Right Cessation
- 2005-11-09 DE DE602005017204T patent/DE602005017204D1/de not_active Expired - Lifetime
- 2005-11-09 WO PCT/IN2005/000363 patent/WO2007054950A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20080319226A1 (en) | 2008-12-25 |
| WO2007054950A1 (en) | 2007-05-18 |
| EP1945607A1 (de) | 2008-07-23 |
| EP1945607B1 (de) | 2009-10-14 |
| DE602005017204D1 (de) | 2009-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |