FI80673C - Foerfarande foer framstaellning av terapeutiskt aktivt (s)-alfa-etyl-oxo-1-pyrrolidinacetamid. - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktivt (s)-alfa-etyl-oxo-1-pyrrolidinacetamid. Download PDFInfo
- Publication number
- FI80673C FI80673C FI851875A FI851875A FI80673C FI 80673 C FI80673 C FI 80673C FI 851875 A FI851875 A FI 851875A FI 851875 A FI851875 A FI 851875A FI 80673 C FI80673 C FI 80673C
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- Finland
- Prior art keywords
- alpha
- radical
- ethyl
- oxo
- formula
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- HPHUVLMMVZITSG-LURJTMIESA-N levetiracetam Chemical compound CC[C@@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-LURJTMIESA-N 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- HNNJFUDLLWOVKZ-VKHMYHEASA-N (2s)-2-aminobutanamide Chemical compound CC[C@H](N)C(N)=O HNNJFUDLLWOVKZ-VKHMYHEASA-N 0.000 claims abstract description 9
- IODGAONBTQRGGG-LURJTMIESA-N Levetiracetam acid Chemical compound CC[C@@H](C(O)=O)N1CCCC1=O IODGAONBTQRGGG-LURJTMIESA-N 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 4
- -1 C1-C4 alkyl radical Chemical class 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 4
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- 239000000126 substance Substances 0.000 claims description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 4
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
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- QBJNYRYTZPBHFT-LURJTMIESA-N (2s)-2-(4-chlorobutanoylamino)butanamide Chemical compound CC[C@@H](C(N)=O)NC(=O)CCCCl QBJNYRYTZPBHFT-LURJTMIESA-N 0.000 description 2
- HDBMIDJFXOYCGK-DFWYDOINSA-N (2s)-2-aminobutanamide;hydrochloride Chemical compound Cl.CC[C@H](N)C(N)=O HDBMIDJFXOYCGK-DFWYDOINSA-N 0.000 description 2
- XYOXIERJKILWCG-UHFFFAOYSA-N 4-chlorobutanamide Chemical compound NC(=O)CCCCl XYOXIERJKILWCG-UHFFFAOYSA-N 0.000 description 2
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 2
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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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
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Detergent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Seasonings (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8412357 | 1984-05-15 | ||
| GB848412357A GB8412357D0 (en) | 1984-05-15 | 1984-05-15 | Pharmaceutical composition |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI851875A0 FI851875A0 (fi) | 1985-05-13 |
| FI851875L FI851875L (fi) | 1985-11-16 |
| FI80673B FI80673B (fi) | 1990-03-30 |
| FI80673C true FI80673C (fi) | 1990-07-10 |
Family
ID=10560974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI851875A FI80673C (fi) | 1984-05-15 | 1985-05-13 | Foerfarande foer framstaellning av terapeutiskt aktivt (s)-alfa-etyl-oxo-1-pyrrolidinacetamid. |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US4696943A (en:Method) |
| EP (1) | EP0162036B1 (en:Method) |
| JP (1) | JPH0629186B2 (en:Method) |
| KR (1) | KR920003819B1 (en:Method) |
| CN (1) | CN1015541B (en:Method) |
| AT (1) | ATE45567T1 (en:Method) |
| AU (1) | AU574465B2 (en:Method) |
| BG (2) | BG50156A3 (en:Method) |
| CA (1) | CA1235129A (en:Method) |
| CY (2) | CY1567A (en:Method) |
| DE (3) | DE10075021I1 (en:Method) |
| DK (1) | DK163501C (en:Method) |
| ES (2) | ES8704893B9 (en:Method) |
| FI (1) | FI80673C (en:Method) |
| GB (1) | GB8412357D0 (en:Method) |
| GE (1) | GEP20002001B (en:Method) |
| GR (1) | GR851155B (en:Method) |
| HK (1) | HK52391A (en:Method) |
| IE (1) | IE59950B1 (en:Method) |
| IL (1) | IL75179A (en:Method) |
| LT (1) | LT2584B (en:Method) |
| LU (2) | LU90615I2 (en:Method) |
| LV (1) | LV5233A3 (en:Method) |
| MY (2) | MY101726A (en:Method) |
| NL (1) | NL300028I2 (en:Method) |
| NO (2) | NO164534C (en:Method) |
| PL (2) | PL144346B1 (en:Method) |
| PT (1) | PT80460B (en:Method) |
| SA (1) | SA01210656A (en:Method) |
| SG (1) | SG80090G (en:Method) |
| SU (3) | SU1402260A3 (en:Method) |
| UA (1) | UA6158A1 (en:Method) |
| ZA (1) | ZA853635B (en:Method) |
Families Citing this family (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8827389D0 (en) * | 1988-11-23 | 1988-12-29 | Ucb Sa | Process for preparation of(s)alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| IT1231477B (it) * | 1989-07-12 | 1991-12-07 | Sigma Tau Ind Farmaceuti | (pirrolidin-2-one-1-il) acetammidi quali attivatori dei processi di apprendimento e della memoria e composizioni farmaceutiche comprendenti tali composti |
| GB9319732D0 (en) * | 1993-09-24 | 1993-11-10 | Ucb Sa | Use of (s)-alpha-ethyl-2-oxo-l-pyrrolidineacetamide for the treatment of anxiety |
| US6124473A (en) * | 1998-05-08 | 2000-09-26 | Ucb, S.A. | Process for preparing (s)- and (R)-α-ethyl-2-oxo-1-pyrrolidineacetamide |
| US6107492A (en) * | 1998-05-08 | 2000-08-22 | Ucb, S.A. | Process for the preparation of levetiracetam |
| EA002380B1 (ru) * | 1999-07-21 | 2002-04-25 | Российский Государственный Педагогический Университет Им. А.И.Герцена | Антиишемическое средство |
| EA002379B1 (ru) * | 1999-07-21 | 2002-04-25 | Российский Государственный Педагогический Университет Им. А.И.Герцена | Средство, обладающее антиишемической, гипотензивной и антигипоксической активностью |
| CA2392879C (en) * | 1999-12-01 | 2005-03-29 | Ucb, S.A. | A pyrrolidineacetamide derivative alone or in combination for treatment of cns disorders |
| GB0004297D0 (en) | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
| US6686477B2 (en) * | 2000-09-29 | 2004-02-03 | Eastman Chemical Company | Highly enantiomerically pure lactam-substituted propanoic acid derivatives and methods of making and using same |
| EP1339669B1 (en) | 2000-11-21 | 2008-06-04 | UCB Pharma, S.A. | N-alkylated gaba compounds, processes for their preparation and their use as medicaments |
| KR100823668B1 (ko) * | 2000-12-28 | 2008-04-21 | 해밀턴 파마슈티컬스 인코포레이티드 | 신경성 통증 치료 및 예방약 |
| EP1379236A4 (en) * | 2001-02-23 | 2009-01-21 | Ucb Sa | TREATMENT OF TICS, TREMORS AND RELATED DISORDERS |
| JP4334344B2 (ja) | 2001-08-10 | 2009-09-30 | ユセベ ファルマ ソシエテ アノニム | オキソピロリジン化合物、当該化合物の調製、並びにレベチラセタム及び類似体の製造におけるその化合物の使用 |
| EP1435943B1 (en) * | 2001-10-08 | 2007-02-14 | Ucb, S.A. | Use of 2-oxo-1-pyrrolidine derivatives for the preparation of a drug for treating dyskinesia |
| RU2216322C1 (ru) * | 2002-02-28 | 2003-11-20 | Закрытое акционерное общество "АСГЛ-Фармацевтические Инновации" | Средство, обладающее антиишемической, гипотензивной, противоаритмической и ноотропной активностью |
| AU2003242538A1 (en) * | 2002-05-14 | 2003-11-11 | Ucb, S.A. | Use of 2-oxo-1-pyrrolidone derivatives for the preparation of a drug |
| CN1802352A (zh) * | 2003-02-03 | 2006-07-12 | 特瓦制药工业有限公司 | 制备左乙拉西坦的方法 |
| ES2214147B1 (es) | 2003-02-28 | 2005-10-01 | Farma-Lepori S.A. | Procedimiento de obtencion de un agente antiepileptico. |
| AU2003217438A1 (en) * | 2003-03-18 | 2004-10-11 | Hetero Drugs Limited | Novel crystalline forms of levetiracetam |
| WO2005023763A1 (en) * | 2003-09-05 | 2005-03-17 | Ranbaxy Laboratories Limited | Process for the preparation of pure levetiracetam |
| EP1667967B1 (en) * | 2003-09-24 | 2012-08-01 | UCB Pharma, S.A. | Process for preparing 2-oxo-1-pyrrolidine derivatives |
| KR20060110349A (ko) | 2003-12-02 | 2006-10-24 | 유씨비 소시에떼아노님 | 이미다졸 유도체, 이들의 제조 방법 및 이들의 용도 |
| US7531673B2 (en) | 2004-02-18 | 2009-05-12 | Dr. Reddy's Laboratories Limited | Preparation of amino acid amides |
| 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 |
| AU2005325930B2 (en) * | 2005-01-27 | 2012-01-19 | Alembic Limited | Extended release formulation of Levetiracetam |
| WO2006088864A1 (en) * | 2005-02-16 | 2006-08-24 | Elan Pharma International Limited | Controlled release compositions comprising levetiracetam |
| US20070298098A1 (en) * | 2005-02-16 | 2007-12-27 | Elan Pharma International Limited | Controlled Release Compositions Comprising Levetiracetam |
| WO2006090265A2 (en) * | 2005-02-28 | 2006-08-31 | Ranbaxy Laboratories Limited | Processes for the preparation of levetiracetam, its intermediate and the use of levetiracetam in pharmaceutical compositions |
| WO2006095362A1 (en) * | 2005-03-10 | 2006-09-14 | Rubamin Limited | Process for preparing levetiracetam |
| WO2006102750A1 (en) * | 2005-03-30 | 2006-10-05 | Genpharm Inc. | Combined-step process for pharmaceutical compositions |
| US20080194840A1 (en) * | 2005-04-01 | 2008-08-14 | Rubamin Laboratories Limited | Process for Preparing Levetiracetam and Racemization of (R)- and (S)-2-Amino Butynamide and the Corresponding Acid Derivatives |
| AU2006254336B9 (en) | 2005-06-01 | 2013-02-28 | Ucb Pharma, S.A. | 2 -oxo-I -pyrrolidine derivatives/ processes for preparing them and their therapeutic use on the central nervous system |
| BRPI0606121A2 (pt) * | 2005-07-26 | 2009-10-06 | Ucb Pharma Sa | composição farmacêutica, processo de manufaturar a mesma, e, uso de uma composição farmacêutica |
| US8338621B2 (en) | 2005-12-21 | 2012-12-25 | Ucb S.A. | Process for the preparation of 2-oxo-1-pyrrolidine derivatives |
| PL1810676T3 (pl) * | 2006-01-24 | 2009-04-30 | Teva Pharmaceutical Industries Ltd | Formulacje lewetiracetamu i sposoby ich wytwarzania |
| US20080014271A1 (en) * | 2006-07-13 | 2008-01-17 | Ucb, S.A. | Novel pharmaceutical compositions comprising levetiracetam |
| EP2049476A1 (en) * | 2006-07-25 | 2009-04-22 | ZaCh System S.p.A. | Process for the preparation of levetiracetam |
| EP2051696A2 (en) * | 2006-08-18 | 2009-04-29 | Morton Grove Pharmaceuticals, Inc. | Stable liquid levetiracetam compositions and methods |
| CN101130504B (zh) * | 2006-08-25 | 2010-07-28 | 苏州雅本化学股份有限公司 | 经合成、拆分与消旋化制备手性药物左乙拉西坦中间体(s)-(+)-2-氨基丁酰胺盐酸盐的方法 |
| EP1932922A1 (de) * | 2006-12-13 | 2008-06-18 | Desitin Arzneimittel GmbH | Schnelltest zum Nachweis von DNA-Sequenzen |
| WO2008077035A2 (en) * | 2006-12-18 | 2008-06-26 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of levetiracetam |
| CN101333180B (zh) * | 2007-06-29 | 2011-05-18 | 浙江华海药业股份有限公司 | 一种制备左乙拉西坦中间体的方法 |
| US20090082422A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched levetiracetam |
| WO2009050735A1 (en) * | 2007-10-15 | 2009-04-23 | Lupin Limited | A novel polymorph of levetiracetam and a process for its preparation |
| US20090263481A1 (en) * | 2008-04-17 | 2009-10-22 | Atul Vishvanath Patil | Levetiracetam formulations |
| US20100003322A1 (en) * | 2008-07-03 | 2010-01-07 | Lai Felix S | Enteric coated hydrophobic matrix formulation |
| EP2147911A1 (en) | 2008-07-24 | 2010-01-27 | ZaCh System S.p.A. | Process for the preparation of levetiracetam |
| US20100190752A1 (en) | 2008-09-05 | 2010-07-29 | Gruenenthal Gmbh | Pharmaceutical Combination |
| ES2637497T3 (es) * | 2008-10-16 | 2017-10-13 | The Johns Hopkins University | Procedimientos y composiciones para la mejora de la función cognitiva |
| EP2179725A1 (en) | 2008-10-23 | 2010-04-28 | LEK Pharmaceuticals D.D. | Pharmaceutical composition comprising levetiracetam |
| WO2010054009A1 (en) * | 2008-11-07 | 2010-05-14 | Novabay Pharmaceuticals, Inc. | Antimicrobial oxazolidinone, hydantoin and imidazolidinone compositions |
| US20100172979A1 (en) * | 2008-12-24 | 2010-07-08 | Zhongshui Yu | Controlled-release formulations |
| US20100159009A1 (en) * | 2008-12-24 | 2010-06-24 | Zhongshui Yu | Controlled-release formulations |
| US8785661B2 (en) | 2009-05-13 | 2014-07-22 | Nektar Therapeutics | Oligome-containing pyrrolidine compounds |
| CN101885696A (zh) * | 2009-05-14 | 2010-11-17 | 上海华理生物医药有限公司 | 一种合成高纯度左乙拉西坦的方法 |
| EP2461808A2 (en) | 2009-08-07 | 2012-06-13 | UCB Pharma S.A. | Methods for enhancing the cognitive function |
| EP2298290A1 (en) | 2009-09-16 | 2011-03-23 | LEK Pharmaceuticals d.d. | Controlled release composition comprising levetiracetam |
| US7939676B2 (en) * | 2009-09-17 | 2011-05-10 | Zach System S.P.A. | Process for the preparation of levetiracetam |
| BR112012009310B8 (pt) | 2009-10-23 | 2021-05-25 | Ucb Biopharma Sprl | composto derivados de 2-oxo-1-pirrolidinil imidazotiadiazol, uso dos mesmos e composição farmacêutica compreendendo os mesmos |
| CN102905532A (zh) | 2010-02-09 | 2013-01-30 | 约翰斯.霍普金斯大学 | 用于改善认知功能的方法和组合物 |
| EP2539444A4 (en) | 2010-02-26 | 2013-09-18 | Univ California | COMPOSITIONS AND METHODS FOR THE PRODUCTION OF L-HOMOALANINE |
| EP2563340A2 (en) | 2010-04-26 | 2013-03-06 | Mahmut Bilgic | Water soluble pharmaceutical composition |
| US9333175B2 (en) | 2010-06-16 | 2016-05-10 | Mylan Inc. | Controlled release levetiracetam formulations and methods for producing the same |
| EP2492354A1 (en) | 2011-02-23 | 2012-08-29 | Institut National De La Recherche Agronomique (INRA) | Method for identifying compounds useful in the treatment of photosensitive reflex epilepsy |
| SI2699581T1 (sl) | 2011-04-18 | 2016-02-29 | Ucb Biopharma Sprl | Derivati 2-okso-1-imidazolidinil imidazotiadiazola |
| EP2524910A1 (en) | 2011-05-17 | 2012-11-21 | DSM IP Assets B.V. | Process for the resolution of aminobutyramide |
| CN102382027B (zh) * | 2011-09-20 | 2013-11-13 | 浙江江北药业有限公司 | 一种左乙拉西坦的制备方法 |
| CN102617436B (zh) * | 2012-03-20 | 2014-02-12 | 浙江洪波化工有限公司 | 2-(2-氧代吡咯烷基）丁酰胺的制备方法 |
| CN102633675A (zh) * | 2012-04-10 | 2012-08-15 | 南京大学 | 一种dl-2-氨基丁酰胺制备方法 |
| CN102675181B (zh) * | 2012-06-07 | 2013-11-20 | 北京师宏药物研制中心 | 一种左乙拉西坦的制备方法 |
| CN102702063B (zh) * | 2012-06-15 | 2013-09-04 | 孙威 | 一种左乙拉西坦制备方法 |
| WO2014012563A1 (en) | 2012-07-20 | 2014-01-23 | Ucb Pharma, S.A. | Compounds for enhancing the cognitive function |
| JP6440625B2 (ja) | 2012-11-14 | 2018-12-19 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 精神分裂病を処置するための方法および組成物 |
| CN103012190B (zh) * | 2012-12-05 | 2015-03-18 | 江苏拜克新材料有限公司 | 一种s-2-氨基丁酰胺盐酸盐的合成方法 |
| US9339489B2 (en) | 2013-03-15 | 2016-05-17 | Aprecia Pharmaceuticals Company | Rapid disperse dosage form containing levetiracetam |
| WO2014144512A1 (en) | 2013-03-15 | 2014-09-18 | Aprecia Pharmaceuticals Company | Rapid disperse dosage form containing levetiracetam |
| DK2968220T3 (da) | 2013-03-15 | 2021-06-14 | Agenebio Inc | Fremgangsmåder og sammensætninger til forbedring af kognitiv funktion |
| WO2014144663A1 (en) | 2013-03-15 | 2014-09-18 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| LT3096790T (lt) | 2014-01-21 | 2019-10-10 | Janssen Pharmaceutica, N.V. | Deriniai, apimantys 2 potipio metabotropinio glutamaterginio receptoriaus teigiamus alosterinius moduliatorius arba ortosterinius agonistus, ir jų panaudojimas |
| UA127921C2 (uk) | 2014-01-21 | 2024-02-14 | Янссен Фармацевтика Нв | Комбінації, які містять позитивні алостеричні модулятори або ортостеричні агоністи метаботропного глутаматергічного рецептора 2 підтипу, та їх застосування |
| CN103922988A (zh) * | 2014-04-29 | 2014-07-16 | 苏州天马精细化学品股份有限公司 | 一种左乙拉西坦粗品的纯化方法 |
| CN103910649A (zh) * | 2014-04-29 | 2014-07-09 | 苏州天马精细化学品股份有限公司 | 一种左乙拉西坦中间体（s）-n-[1-(氨基羰基)丙基]-4-氯代丁酰胺的合成方法 |
| CN104860863B (zh) * | 2015-04-10 | 2017-06-20 | 惠州信立泰药业有限公司 | 左乙拉西坦和含其的药物组合物 |
| BR112017025031B1 (pt) | 2015-05-22 | 2023-03-21 | Agenebio, Inc | Composições farmacêuticas de liberação prolongada de levetiracetam |
| AU2016381366A1 (en) | 2015-12-30 | 2018-06-28 | Adamas Pharmaceuticals, Inc. | Methods and compositions for the treatment of seizure-related disorders |
| CN106432032B (zh) * | 2016-09-14 | 2019-07-12 | 苏州天马药业有限公司 | 一种左乙拉西坦的制备方法 |
| CN106591179B (zh) * | 2016-12-05 | 2018-07-03 | 长兴制药股份有限公司 | 甲基包囊菌及其在选择性拆分制备(S)-α-乙基-2-氧-1-吡咯烷乙酸盐上的应用 |
| MA49114A (fr) | 2016-12-16 | 2020-03-25 | Idorsia Pharmaceuticals Ltd | Combinaison pharmaceutique comprenant un bloqueur de canal calcique de type t |
| CN108503610B (zh) | 2017-02-24 | 2019-09-13 | 北京艾百诺医药股份有限公司 | 一种光学纯的(r)-4-正丙基-二氢呋喃-2(3h)-酮的制备方法 |
| CN107337628B (zh) | 2017-08-10 | 2022-02-08 | 浙江华海药业股份有限公司 | 一种制备左乙拉西坦的方法 |
| TWI826531B (zh) | 2018-09-21 | 2023-12-21 | 南韓商愛思開生物製藥股份有限公司 | 具有㗁二唑之化合物及包含該化合物之醫藥組合物 |
| CN110003074A (zh) | 2019-04-23 | 2019-07-12 | 浙江华海药业股份有限公司 | 一种左乙拉西坦中间体的制备方法 |
| TW202114655A (zh) | 2019-08-14 | 2021-04-16 | 瑞士商辛鐵堤卡公司 | 左乙拉西坦(levetiracetam)之鞘內投藥 |
| US11384050B1 (en) | 2021-02-03 | 2022-07-12 | Vitaworks Ip, Llc | Method for preparing levetiracetam and intermediates thereof |
| CN117177746A (zh) | 2021-02-26 | 2023-12-05 | 辛德斯治疗股份公司 | 用于治疗认知病症的化合物 |
| CN113979911A (zh) * | 2021-11-12 | 2022-01-28 | 汤斌 | 一种从大鲵肽中提取乙拉西坦的方法 |
| US20240368080A1 (en) * | 2023-05-05 | 2024-11-07 | Suzhou Brighthope Pharmatech Co., Ltd | Process for the production of levetiracetam and intermediate thereof |
| US20240368081A1 (en) * | 2023-05-05 | 2024-11-07 | Suzhou Brighthope Pharmatech Co., Ltd | Process for the production of levetiracetam and intermediate thereof |
| US20240368082A1 (en) * | 2023-05-05 | 2024-11-07 | Suzhou Brighthope Pharmatech Co., Ltd | Process for the production of levetiracetam and intermediate thereof |
| US20240409511A1 (en) * | 2023-06-12 | 2024-12-12 | Suzhou Brighthope Pharmatech Co., Ltd | Process for the production of levetiracetam and intermediates thereof |
| WO2025132331A1 (en) | 2023-12-21 | 2025-06-26 | UCB Biopharma SRL | Compounds for treatment of a hyperkinetic movement disorder |
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 (fr) * | 1978-03-02 | 1979-09-28 | Philagro Sa | Nouveaux derives de pyrrolidinone-2 et compositions herbicides les contenant |
| GB8412358D0 (en) * | 1984-05-15 | 1984-06-20 | Ucb Sa | Pharmaceutical composition |
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1984
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1985
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1986
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1989
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1990
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L175 Extension date: 20100512 |
|
| FG | Patent granted |
Owner name: UCB S.A. |
|
| MA | Patent expired |