DE10075021I1 - (S)-Alpha-ethyl-2-oxo-1-pyrrolidin-Acetamid - Google Patents
(S)-Alpha-ethyl-2-oxo-1-pyrrolidin-AcetamidInfo
- Publication number
- DE10075021I1 DE10075021I1 DE2000175021 DE10075021C DE10075021I1 DE 10075021 I1 DE10075021 I1 DE 10075021I1 DE 2000175021 DE2000175021 DE 2000175021 DE 10075021 C DE10075021 C DE 10075021C DE 10075021 I1 DE10075021 I1 DE 10075021I1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- oxo
- alpha
- ethyl
- pyrrolidine acetamide
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
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
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB848412357A GB8412357D0 (en) | 1984-05-15 | 1984-05-15 | Pharmaceutical composition |
Publications (1)
Publication Number | Publication Date |
---|---|
DE10075021I1 true DE10075021I1 (de) | 2000-10-19 |
Family
ID=10560974
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2001199005 Active DE10199005I2 (de) | 1984-05-15 | 1985-05-14 | (S)-Alpha-ethyl-2-oxo-1-pyrrolidin-Acetamid |
DE2000175021 Pending DE10075021I1 (de) | 1984-05-15 | 1985-05-14 | (S)-Alpha-ethyl-2-oxo-1-pyrrolidin-Acetamid |
DE8585870069T Expired DE3572348D1 (de) | 1984-05-15 | 1985-05-14 | (s)-alpha-ethyl-2-oxo-1-pyrrolidinacetamide |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2001199005 Active DE10199005I2 (de) | 1984-05-15 | 1985-05-14 | (S)-Alpha-ethyl-2-oxo-1-pyrrolidin-Acetamid |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE8585870069T Expired DE3572348D1 (de) | 1984-05-15 | 1985-05-14 | (s)-alpha-ethyl-2-oxo-1-pyrrolidinacetamide |
Country Status (33)
Country | Link |
---|---|
US (3) | US4696943A (de) |
EP (1) | EP0162036B1 (de) |
JP (1) | JPH0629186B2 (de) |
KR (1) | KR920003819B1 (de) |
CN (1) | CN1015541B (de) |
AT (1) | ATE45567T1 (de) |
AU (1) | AU574465B2 (de) |
BG (2) | BG50156A3 (de) |
CA (1) | CA1235129A (de) |
CY (2) | CY1567A (de) |
DE (3) | DE10199005I2 (de) |
DK (1) | DK163501C (de) |
ES (2) | ES8608485A1 (de) |
FI (1) | FI80673C (de) |
GB (1) | GB8412357D0 (de) |
GE (1) | GEP20002001B (de) |
GR (1) | GR851155B (de) |
HK (1) | HK52391A (de) |
IE (1) | IE59950B1 (de) |
IL (1) | IL75179A (de) |
LT (1) | LT2584B (de) |
LU (2) | LU90615I2 (de) |
LV (1) | LV5233A3 (de) |
MY (2) | MY101726A (de) |
NL (1) | NL300028I2 (de) |
NO (2) | NO164534C (de) |
PL (2) | PL147386B1 (de) |
PT (1) | PT80460B (de) |
SA (1) | SA01210656A (de) |
SG (1) | SG80090G (de) |
SU (3) | SU1402260A3 (de) |
UA (1) | UA6158A1 (de) |
ZA (1) | ZA853635B (de) |
Families Citing this family (95)
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 |
EA002379B1 (ru) * | 1999-07-21 | 2002-04-25 | Российский Государственный Педагогический Университет Им. А.И.Герцена | Средство, обладающее антиишемической, гипотензивной и антигипоксической активностью |
EA002380B1 (ru) * | 1999-07-21 | 2002-04-25 | Российский Государственный Педагогический Университет Им. А.И.Герцена | Антиишемическое средство |
EP1600169A3 (de) * | 1999-12-01 | 2009-09-23 | Ucb, S.A. | Pyrrolidinacetamid-Derivat, allein oder kombiniert, zur Behandlung von ZNS-Störungen |
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 |
WO2002042256A2 (en) * | 2000-11-21 | 2002-05-30 | Ucb, S.A. | N-alkylated gaba compounds, processes for their preparation and their use as medicaments |
WO2002053153A1 (fr) * | 2000-12-28 | 2002-07-11 | Daiichi Pharmaceutical Co., Ltd. | Medicaments permettant de traiter et de prevenir une douleur neurologique |
JP2004523557A (ja) * | 2001-02-23 | 2004-08-05 | ジョンズ・ホプキンス・ユニバーシティ | チック、振せん、および関連疾患の治療 |
ATE410412T1 (de) | 2001-08-10 | 2008-10-15 | Ucb Pharma Sa | Oxopyrrolidin verbindungen, verfahren zur herstellung dieser verbindungen und deren verwendung zur herstellung von levetiracetam und analogen |
MXPA04002714A (es) * | 2001-10-08 | 2004-07-05 | Ucb Sa | Uso de derivados de 2-oxo-1-pirrolidina para el tratamiento de trastornos del movimiento y de la discinesia. |
WO2003094913A1 (en) * | 2002-05-14 | 2003-11-20 | Ucb, S.A. | Use of 2-oxo-1-pyrrolidone derivatives for the preparation of a drug |
US7132552B2 (en) * | 2003-02-03 | 2006-11-07 | Teva Pharmaceutical Industries, Ltd. | Process for producing levetiracetam |
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 (de) | 2003-09-24 | 2012-08-01 | UCB Pharma, S.A. | Verfahren zur herstellung von 2-oxo-1-pyrrolidinderivaten |
EP1706376B1 (de) | 2003-12-02 | 2009-03-04 | UCB Pharma, S.A. | Imidazolderivate, verfahren zu deren herstellung und deren anwendungen |
CA2497062A1 (en) | 2004-02-18 | 2005-08-18 | 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 |
US20070298098A1 (en) * | 2005-02-16 | 2007-12-27 | Elan Pharma International Limited | Controlled Release Compositions Comprising Levetiracetam |
WO2006088864A1 (en) * | 2005-02-16 | 2006-08-24 | 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 |
JP2008534522A (ja) * | 2005-03-30 | 2008-08-28 | ジェンファーム インク | 医薬組成物のための複合ステップ製造方法 |
WO2006103696A2 (en) * | 2005-04-01 | 2006-10-05 | Rubamin Laboratories Limited | Process for preparing levetiracetam and racemization of (r)- and (s)-2-amino butynamide and the corresponding acid derivatives |
US8183241B2 (en) | 2005-06-01 | 2012-05-22 | Ucb Pharma, S.A. | 2-oxo-1-pyrrolidine derivatives |
MX2007004294A (es) * | 2005-07-26 | 2008-03-11 | Ucb Pharma Sa | Composiciones farmaceuticas que comprenden levetiracetam y proceso para su preparacion. |
US8338621B2 (en) | 2005-12-21 | 2012-12-25 | Ucb S.A. | Process for the preparation of 2-oxo-1-pyrrolidine derivatives |
PT1810676E (pt) * | 2006-01-24 | 2009-01-02 | Teva Pharma | Formulações de levetiracetam e métodos para a sua preparação |
US20080014264A1 (en) * | 2006-07-13 | 2008-01-17 | Ucb, S.A. | Novel pharmaceutical compositions comprising levetiracetam |
US20100076204A1 (en) * | 2006-07-25 | 2010-03-25 | Zach System S.P.A. | Process for the preparation of levetiracetam |
EP2051696A2 (de) * | 2006-08-18 | 2009-04-29 | Morton Grove Pharmaceuticals, Inc. | Stabile flüssige levetiracetam-zusammensetzungen und verfahren |
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 (de) | 2008-07-24 | 2010-01-27 | ZaCh System S.p.A. | Verfahren zur Herstellung von Levetiracetam |
US20100190752A1 (en) * | 2008-09-05 | 2010-07-29 | Gruenenthal Gmbh | Pharmaceutical Combination |
DK3260118T3 (da) * | 2008-10-16 | 2021-04-19 | Univ Johns Hopkins | Fremgangsmåder og sammensætninger til forbedring af kognitiv funktion |
EP2179725A1 (de) | 2008-10-23 | 2010-04-28 | LEK Pharmaceuticals D.D. | Pharmazeutische Zusammensetzung mit Levetiracetan |
US8722715B2 (en) * | 2008-11-07 | 2014-05-13 | NovaBay Pharmaceuticals | 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 (de) | 2009-08-07 | 2012-06-13 | UCB Pharma S.A. | Verfahren zur verbesserung der kognitiven funktion |
EP2298290A1 (de) | 2009-09-16 | 2011-03-23 | LEK Pharmaceuticals d.d. | Zusammensetzung mit Levetiracetam zur gesteuerten Abgabe |
US7939676B2 (en) * | 2009-09-17 | 2011-05-10 | Zach System S.P.A. | Process for the preparation of levetiracetam |
US8822508B2 (en) | 2009-10-23 | 2014-09-02 | Ucb Pharma, S.A. | 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives |
CA2789014C (en) | 2010-02-09 | 2019-01-15 | Michela Gallagher | Methods and compositions for improving cognitive function |
WO2011106696A2 (en) | 2010-02-26 | 2011-09-01 | The Regents Of The University Of California | Compositions and methods for the production of l-homoalanine |
EP2563340A2 (de) | 2010-04-26 | 2013-03-06 | Mahmut Bilgic | Wasserlösliche pharmazeutische zusammensetzung |
US9333175B2 (en) | 2010-06-16 | 2016-05-10 | Mylan Inc. | Controlled release levetiracetam formulations and methods for producing the same |
EP2492354A1 (de) | 2011-02-23 | 2012-08-29 | Institut National De La Recherche Agronomique (INRA) | Verfahren zur Identifizierung von Verbindungen zur Behandlung lichtempfindlicher Reflexepilepsie |
PL2699581T3 (pl) | 2011-04-18 | 2016-05-31 | Ucb Biopharma Sprl | Pochodne 2-okso-1-imidazolidynyloimidazotiadiazolu |
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 |
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US9339489B2 (en) | 2013-03-15 | 2016-05-17 | Aprecia Pharmaceuticals Company | Rapid disperse dosage form containing levetiracetam |
WO2014144663A1 (en) | 2013-03-15 | 2014-09-18 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
CA2904767C (en) | 2013-03-15 | 2022-06-21 | Agenebio, Inc. | Methods and compositions for improving cognitive function |
WO2014144512A1 (en) | 2013-03-15 | 2014-09-18 | Aprecia Pharmaceuticals Company | Rapid disperse dosage form containing levetiracetam |
ES2860298T3 (es) | 2014-01-21 | 2021-10-04 | Janssen Pharmaceutica Nv | Combinaciones que comprenden moduladores alostéricos positivos del receptor glutamatérgico metabotrópico de subtipo 2 y su uso |
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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 |
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 |
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 |
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US10973783B2 (en) | 2015-12-30 | 2021-04-13 | Adamas Pharmaceuticals, Inc. | Methods and compositions for the treatment of seizure-related disorders |
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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 |
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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 |
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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 |
EP4297749A1 (de) | 2021-02-26 | 2024-01-03 | Syndesi Therapeutics SA | Verbindung zur behandlung von kognitiven störungen |
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 |
-
1984
- 1984-05-15 GB GB848412357A patent/GB8412357D0/en active Pending
-
1985
- 1985-05-04 BG BG89449/89A patent/BG50156A3/xx unknown
- 1985-05-13 IL IL75179A patent/IL75179A/xx not_active IP Right Cessation
- 1985-05-13 GR GR851155A patent/GR851155B/el unknown
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1986
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1987
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1989
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1990
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1991
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1993
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1999
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2000
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2001
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2004
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