BG60030A3 - Method for the preparation of /d/-ethyl-2-oxo-1-pirrolidineacetamide - Google Patents
Method for the preparation of /d/-ethyl-2-oxo-1-pirrolidineacetamideInfo
- Publication number
- BG60030A3 BG60030A3 BG94053A BG9405391A BG60030A3 BG 60030 A3 BG60030 A3 BG 60030A3 BG 94053 A BG94053 A BG 94053A BG 9405391 A BG9405391 A BG 9405391A BG 60030 A3 BG60030 A3 BG 60030A3
- Authority
- BG
- Bulgaria
- Prior art keywords
- radical
- oxo
- ethyl
- preparation
- alpha
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- HNNJFUDLLWOVKZ-GSVOUGTGSA-N (2r)-2-aminobutanamide Chemical compound CC[C@@H](N)C(N)=O HNNJFUDLLWOVKZ-GSVOUGTGSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- HPHUVLMMVZITSG-ZCFIWIBFSA-N levetiracetam Chemical compound CC[C@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-ZCFIWIBFSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Abstract
(R)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide, its preparation and pharmaceutical compositions containing the same. It can be prepared either by reacting (R)-alpha-ethyl-2-oxo-1-pyrrolidineactic acid successively with an alkyl haloformate and with ammonia, or, by cyclizing an (R)-2-amino-butanamide of the formula X-CH2CH2-Y-NHCH (C2H5)CONH2 wherein Y is a -CH2-radical when X represents a ZOOC-radical and Y is a -CO-radical when X represents a HalCH2-radical, Z being a C1-C4 alkyl radical and Hal a halogen atom. This dextrorotatory enantiomer has been found to have significantly higher mnemic activity and lower toxicity than the corresponding racemate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848412358A GB8412358D0 (en) | 1984-05-15 | 1984-05-15 | Pharmaceutical composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG60030A3 true BG60030A3 (en) | 1993-07-15 |
Family
ID=10560975
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG70237A BG50272A3 (en) | 1984-05-15 | 1985-05-14 | Method for the preparation of (d)- alpha- ethyl- 2- oxo- 1- pyrolydinacetamide |
| BG94053A BG60030A3 (en) | 1984-05-15 | 1985-05-14 | Method for the preparation of /d/-ethyl-2-oxo-1-pirrolidineacetamide |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG70237A BG50272A3 (en) | 1984-05-15 | 1985-05-14 | Method for the preparation of (d)- alpha- ethyl- 2- oxo- 1- pyrolydinacetamide |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US4696942A (en) |
| EP (1) | EP0165919B1 (en) |
| JP (1) | JPS60255764A (en) |
| AT (1) | ATE45348T1 (en) |
| AU (1) | AU574175B2 (en) |
| BG (2) | BG50272A3 (en) |
| CA (1) | CA1237138A (en) |
| CY (1) | CY1568A (en) |
| DE (1) | DE3572168D1 (en) |
| DK (1) | DK163500C (en) |
| ES (2) | ES8703419A1 (en) |
| FI (1) | FI80674C (en) |
| GB (1) | GB8412358D0 (en) |
| GR (1) | GR851156B (en) |
| HK (1) | HK62692A (en) |
| IE (1) | IE58393B1 (en) |
| IL (1) | IL75180A (en) |
| NO (1) | NO164535C (en) |
| PL (2) | PL144345B1 (en) |
| PT (1) | PT80461B (en) |
| SG (1) | SG80190G (en) |
| SU (3) | SU1417799A3 (en) |
| ZA (1) | ZA853636B (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8412357D0 (en) * | 1984-05-15 | 1984-06-20 | Ucb Sa | Pharmaceutical composition |
| DE3420193A1 (en) * | 1984-05-30 | 1985-12-05 | Boehringer Ingelheim KG, 6507 Ingelheim | NEW SUBSTITUTED PYRROLIDINONES, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS |
| GB8827389D0 (en) * | 1988-11-23 | 1988-12-29 | Ucb Sa | Process for preparation of(s)alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| US6124473A (en) * | 1998-05-08 | 2000-09-26 | Ucb, S.A. | Process for preparing (s)- and (R)-α-ethyl-2-oxo-1-pyrrolidineacetamide |
| GB0004297D0 (en) | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
| DE60134337D1 (en) * | 2000-11-21 | 2008-07-17 | Ucb Pharma Sa | N-ALKYLATED GABA COMPOUNDS, METHODS THEREOF |
| US20040092575A1 (en) * | 2001-03-22 | 2004-05-13 | Jacques Peuvot | Use of certain substituted pyrrolidones such as piracetam in the treatment of viral and other diseases |
| IL160045A0 (en) * | 2001-08-10 | 2004-06-20 | Ucb Sa | Oxopyrrolidine compounds, preparation of said compounds and their use in the manufacturing of levetiracetam and analogues |
| EP1706376B1 (en) | 2003-12-02 | 2009-03-04 | UCB Pharma, S.A. | Imidazole derivatives, processes for preparing them and their uses |
| CA2488325C (en) * | 2004-11-22 | 2010-08-24 | Apotex Pharmachem Inc. | Improved process for the preparation of (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide and (r)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| JP2008542322A (en) | 2005-06-01 | 2008-11-27 | ユセベ ファルマ ソシエテ アノニム | 2-Oxo-1-pyrrolidine derivatives |
| EP3260118B1 (en) | 2008-10-16 | 2021-03-24 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| CN102574869A (en) | 2009-10-23 | 2012-07-11 | Ucb医药有限公司 | 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives |
| EA037187B1 (en) | 2010-02-09 | 2021-02-17 | Дзе Джонс Хопкинс Юниверсити | Method and composition for treating a cognitive disorder |
| DK2699581T3 (en) | 2011-04-18 | 2016-01-11 | Ucb Biopharma Sprl | 2-oxo-1-IMIDAZOLIDINYLIMIDAZOTHIADIAZOLDERIVATIVER |
| CN102633675A (en) * | 2012-04-10 | 2012-08-15 | 南京大学 | Method for preparing DL-2-amino butyrylamide |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| EP2968237A4 (en) | 2013-03-15 | 2016-08-31 | Univ Johns Hopkins | Methods and compositions for improving cognitive function |
| US11160785B2 (en) | 2013-03-15 | 2021-11-02 | Agenebio Inc. | Methods and compositions for improving cognitive function |
| UA127921C2 (en) | 2014-01-21 | 2024-02-14 | Янссен Фармацевтика Нв | Combinations containing positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| DK3096790T3 (en) | 2014-01-21 | 2019-10-07 | Janssen Pharmaceutica Nv | COMBINATIONS INCLUDING POSITIVE ALLOSTERIC MODULATORS OR ORTHOSTERIC AGONISTS OF METABOTROP GLUTAMATERG SUBTYPE 2 RECEPTOR AND APPLICATION OF THESE |
| AU2016268096B2 (en) | 2015-05-22 | 2021-04-01 | Agenebio, Inc. | Extended release pharmaceutical compositions of levetiracetam |
| JP2022510363A (en) | 2018-12-04 | 2022-01-26 | メティス ファーマシューティカルズ アクチェンゲゼルシャフト | A synergistic composition comprising (R) -2- (2-oxopyrrolidine-1-yl) butaneamide and (S) -2- (2-oxopyrrolidine-1-yl) butaneamide in a non-racemic ratio. |
| US11384050B1 (en) | 2021-02-03 | 2022-07-12 | Vitaworks Ip, Llc | Method for preparing levetiracetam and intermediates thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1309692A (en) * | 1970-02-13 | 1973-03-14 | Ucb Sa | N-substituted lactams |
| GB1583871A (en) * | 1976-10-19 | 1981-02-04 | Ucb Sa | Anti-aggregants |
| FR2418790A1 (en) * | 1978-03-02 | 1979-09-28 | Philagro Sa | NEW DERIVATIVES OF PYRROLIDINONE-2 AND HERBICIDE COMPOSITIONS CONTAINING THEM |
| AU579863B2 (en) * | 1984-05-16 | 1988-12-15 | Williams, David Andrew | A parking control apparatus |
-
1984
- 1984-05-15 GB GB848412358A patent/GB8412358D0/en active Pending
-
1985
- 1985-05-13 GR GR851156A patent/GR851156B/el unknown
- 1985-05-13 FI FI851876A patent/FI80674C/en not_active IP Right Cessation
- 1985-05-13 IL IL75180A patent/IL75180A/en unknown
- 1985-05-14 SU SU3892951A patent/SU1417799A3/en active
- 1985-05-14 EP EP85870068A patent/EP0165919B1/en not_active Expired
- 1985-05-14 BG BG70237A patent/BG50272A3/en unknown
- 1985-05-14 DE DE8585870068T patent/DE3572168D1/en not_active Expired
- 1985-05-14 PL PL1985253373A patent/PL144345B1/en unknown
- 1985-05-14 PT PT80461A patent/PT80461B/en not_active IP Right Cessation
- 1985-05-14 IE IE119285A patent/IE58393B1/en not_active IP Right Cessation
- 1985-05-14 DK DK212885A patent/DK163500C/en not_active IP Right Cessation
- 1985-05-14 AU AU42529/85A patent/AU574175B2/en not_active Ceased
- 1985-05-14 ZA ZA853636A patent/ZA853636B/en unknown
- 1985-05-14 JP JP60102530A patent/JPS60255764A/en active Pending
- 1985-05-14 BG BG94053A patent/BG60030A3/en unknown
- 1985-05-14 AT AT85870068T patent/ATE45348T1/en not_active IP Right Cessation
- 1985-05-14 NO NO851934A patent/NO164535C/en not_active IP Right Cessation
- 1985-05-14 CA CA000481511A patent/CA1237138A/en not_active Expired
- 1985-05-14 PL PL1985257386A patent/PL147387B1/en unknown
- 1985-05-14 US US06/733,791 patent/US4696942A/en not_active Expired - Lifetime
- 1985-05-14 ES ES543125A patent/ES8703419A1/en not_active Expired
- 1985-10-25 SU SU853968801A patent/SU1320207A1/en active
-
1986
- 1986-01-29 ES ES551366A patent/ES8706114A1/en not_active Expired
- 1986-08-13 SU SU4027936A patent/SU1428194A3/en active
-
1987
- 1987-03-12 US US07/025,278 patent/US4837224A/en not_active Expired - Lifetime
-
1990
- 1990-10-02 SG SG801/90A patent/SG80190G/en unknown
-
1991
- 1991-12-20 CY CY1568A patent/CY1568A/en unknown
-
1992
- 1992-08-20 HK HK626/92A patent/HK62692A/en not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BG60030A3 (en) | Method for the preparation of /d/-ethyl-2-oxo-1-pirrolidineacetamide | |
| MY101725A (en) | (r)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide. |