KR100958045B1 - 3-(3-디메틸아미노-1-에틸-2-메틸-프로필)페놀을 함유하고활성 성분의 방출이 지연되는 약제 - Google Patents
3-(3-디메틸아미노-1-에틸-2-메틸-프로필)페놀을 함유하고활성 성분의 방출이 지연되는 약제 Download PDFInfo
- Publication number
- KR100958045B1 KR100958045B1 KR1020047006113A KR20047006113A KR100958045B1 KR 100958045 B1 KR100958045 B1 KR 100958045B1 KR 1020047006113 A KR1020047006113 A KR 1020047006113A KR 20047006113 A KR20047006113 A KR 20047006113A KR 100958045 B1 KR100958045 B1 KR 100958045B1
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- Prior art keywords
- ethyl
- methyl
- propyl
- dimethylamino
- phenol
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Classifications
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10152469.2 | 2001-10-24 | ||
| DE10152469A DE10152469A1 (de) | 2001-10-24 | 2001-10-24 | 3-(3-Dimethylamino-1-ethyl-2-methyl-propyl)phenol enthaltendes Arzneimittel mit verzögerter Wirkstofffreisetzung |
| DE10248309.4 | 2002-10-16 | ||
| DE2002148309 DE10248309A1 (de) | 2002-10-16 | 2002-10-16 | 3-(3- Dimethylamino-1-ethyl-2-methyl-propyl) phenol enthaltendes Arzeimittel mit verzögerter Wirkstofffreisetzung |
| PCT/EP2002/011809 WO2003035053A1 (de) | 2001-10-24 | 2002-10-22 | 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)phenol enthaltendes arzneimittel mit verzögerter wirkstofffreisetzung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20040047964A KR20040047964A (ko) | 2004-06-05 |
| KR100958045B1 true KR100958045B1 (ko) | 2010-05-17 |
Family
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Family Applications (1)
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Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| EP1562567B1 (de) | 2002-11-22 | 2017-06-14 | Grünenthal GmbH | Kombination ausgewählter analgetika mit cox ii-inhibitoren |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE102004020220A1 (de) * | 2004-04-22 | 2005-11-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| DE10361596A1 (de) * | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE102004032051A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| ES2289542T3 (es) * | 2003-08-06 | 2008-02-01 | Grunenthal Gmbh | Forma farmaceutica protegida contra un posible abuso. |
| DE102005005446A1 (de) * | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE602004007905T2 (de) | 2004-06-28 | 2008-05-08 | Grünenthal GmbH | Kristalline Formen von (-)-(1R,2R)-3-(3-Dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochlorid |
| JP5700904B2 (ja) * | 2004-07-01 | 2015-04-15 | グリューネンタール・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | （１ｒ，２ｒ）−３−（３−ジメチルアミノ−１−エチル−２−メチル−プロピル）フェノールを含有する乱用防止経口投与形態物 |
| DE102004032103A1 (de) * | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102005005449A1 (de) * | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| EP2012764B1 (en) * | 2006-04-28 | 2011-01-12 | Grünenthal GmbH | Pharmaceutical combination comprising 3-(3-dimethylamino-1-ethyl-2-methyl-propyl) -phenol and paracetamol |
| PT2012763E (pt) * | 2006-04-28 | 2011-04-29 | Gruenenthal Gmbh | Combinação farmacêutica que compreende 3-(3-dimetilamino-1-etil-2-metil-propil)fenol e um aine |
| CN101091725A (zh) * | 2006-06-23 | 2007-12-26 | 天津天士力制药股份有限公司 | 一种中药颗粒及其制备方法 |
| SA07280459B1 (ar) | 2006-08-25 | 2011-07-20 | بيورديو فارما إل. بي. | أشكال جرعة صيدلانية للتناول عن طريق الفم مقاومة للعبث تشتمل على مسكن شبه أفيوني |
| DE102007011485A1 (de) * | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
| EP1985292A1 (en) * | 2007-04-23 | 2008-10-29 | Grünenthal GmbH | Titration of tapentadol |
| DE102007019417A1 (de) | 2007-04-23 | 2008-11-13 | Grünenthal GmbH | Tapentadol zur Schmerzbehandlung bei Arthrose |
| KR101607112B1 (ko) * | 2007-11-23 | 2016-03-29 | 그뤼넨탈 게엠베하 | 타펜타돌 조성물 |
| PT2240431T (pt) * | 2007-12-07 | 2017-05-03 | Gruenenthal Gmbh | Modificações cristalinas de (1r,2r)-3-(3-dimetilamino-1- etil-2-metil-propil)fenol |
| US8383152B2 (en) | 2008-01-25 | 2013-02-26 | Gruenenthal Gmbh | Pharmaceutical dosage form |
| TWI524904B (zh) | 2008-05-09 | 2016-03-11 | 歌林達股份有限公司 | 製備醫藥用固體劑型，尤指錠劑之方法，及製備固體劑型，尤指錠劑之前驅物之方法 |
| US20100190752A1 (en) | 2008-09-05 | 2010-07-29 | Gruenenthal Gmbh | Pharmaceutical Combination |
| ES2758831T3 (es) | 2008-10-30 | 2020-05-06 | Gruenenthal Gmbh | Nuevas y potentes formas de dosificación de tapentadol |
| NZ596668A (en) | 2009-07-22 | 2013-09-27 | Gruenenthal Chemie | Oxidation-stabilized tamper-resistant dosage form |
| JP5667183B2 (ja) | 2009-07-22 | 2015-02-12 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 加熱溶融押出成型した制御放出性投与剤型 |
| EP2531176B1 (en) * | 2010-02-03 | 2016-09-07 | Grünenthal GmbH | Preparation of a powdery pharmaceutical composition by means of an extruder |
| JP5905872B2 (ja) * | 2010-04-07 | 2016-04-20 | ルピン・リミテッド | タペンタドールの制御放出医薬組成物 |
| US20130116333A1 (en) * | 2010-05-05 | 2013-05-09 | Ratiopharm Gmbh | Solid tapentadol in non-crystalline form |
| US8846765B2 (en) | 2010-06-15 | 2014-09-30 | Gruenenthal Gmbh | Pharmaceutical combination |
| PT2588093T (pt) | 2010-06-30 | 2016-09-21 | Gruenenthal Gmbh | Tapentadol para utilização no tratamento de síndrome do intestino irritável |
| MX341072B (es) | 2010-07-23 | 2016-08-05 | Grünenthal Gmbh * | Sales o co-cristales de 3-(3-dimetilamino-1-etil-2-metil-propil)-f enol. |
| MX2013002293A (es) | 2010-09-02 | 2013-05-09 | Gruenenthal Gmbh | Forma de dosificacion resistente a alteracion que comprende un polimero anionico. |
| ES2486791T3 (es) | 2010-09-02 | 2014-08-19 | Grünenthal GmbH | Forma de dosificación resistente a la manipulación que comprende una sal inorgánica |
| DK2680833T3 (en) | 2011-03-04 | 2016-05-23 | Gruenenthal Gmbh | PARENTERAL SUBMISSION OF TAPENTADOL |
| CN103501773A (zh) | 2011-03-04 | 2014-01-08 | 格吕伦塔尔有限公司 | 用于口服给予的他喷他多含水药物制剂 |
| LT2694049T (lt) | 2011-04-05 | 2018-12-27 | GrĆ¼nenthal GmbH | Tapentadolis, skirtas skausmo perėjimo į lėtinį prevencijai |
| JP6040219B2 (ja) | 2011-04-05 | 2016-12-07 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 三叉神経因性痛に伴う疼痛の治療用タペンタドール |
| SI2701693T1 (sl) | 2011-04-29 | 2017-11-30 | Gruenenthal Gmbh | Tapentadol za preprečevanje in zdravljenje depresije in anksioznosti |
| NO2680834T3 (enExample) | 2011-05-03 | 2018-03-17 | ||
| WO2013017233A1 (en) | 2011-07-29 | 2013-02-07 | Grünenthal GmbH | Intrathecal or epidural administration of 3-[(1s,2s)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol |
| EA201400172A1 (ru) | 2011-07-29 | 2014-06-30 | Грюненталь Гмбх | Устойчивая к разрушению таблетка, которая обеспечивает немедленное высвобождение лекарственного средства |
| PE20141650A1 (es) | 2011-07-29 | 2014-11-22 | Gruenenthal Chemie | Tableta a prueba de alteracion que proporciona liberacion inmediata del farmaco |
| EP2606879A1 (en) | 2011-12-21 | 2013-06-26 | Hexal AG | Multiple unit pellet tablet formulation comprising an opioid |
| WO2013127831A1 (en) | 2012-02-28 | 2013-09-06 | Grünenthal GmbH | Tamper-resistant dosage form comprising pharmacologically active compound and anionic polymer |
| ES2692944T3 (es) | 2012-04-18 | 2018-12-05 | Grünenthal GmbH | Forma de dosificación farmacéutica resistente a la manipulación y resistente a la descarga rápida de la dosis |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| BR112015026549A2 (pt) | 2013-05-29 | 2017-07-25 | Gruenenthal Gmbh | forma de dosagem à prova de violação contendo uma ou mais partículas |
| US9737490B2 (en) | 2013-05-29 | 2017-08-22 | Grünenthal GmbH | Tamper resistant dosage form with bimodal release profile |
| EP2808319A1 (en) | 2013-05-31 | 2014-12-03 | Arevipharma GmbH | 3-[3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol resin complex |
| AU2014289187B2 (en) | 2013-07-12 | 2019-07-11 | Grunenthal Gmbh | Tamper-resistant dosage form containing ethylene-vinyl acetate polymer |
| EP2845625A1 (en) | 2013-09-04 | 2015-03-11 | Grünenthal GmbH | Tapentadol for use in the treatment of fibromyalgia and chronic fatigue syndrome |
| WO2015071248A1 (en) | 2013-11-15 | 2015-05-21 | Synthon B.V. | Abuse-proofed extended release pharmaceutical composition comprising tapentadol |
| AU2014356581C1 (en) | 2013-11-26 | 2020-05-28 | Grunenthal Gmbh | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
| EP2942054A1 (en) * | 2014-05-09 | 2015-11-11 | G.L. Pharma GmbH | Slow-release pharmaceutical formulation |
| MX2016014738A (es) | 2014-05-12 | 2017-03-06 | Gruenenthal Gmbh | Formulacion en capsula de liberacion inmediata resistente a alteraciones que comprende tapentadol. |
| CN106456550A (zh) | 2014-05-26 | 2017-02-22 | 格吕伦塔尔有限公司 | 避免乙醇剂量倾泻的多颗粒 |
| ES2710299T3 (es) | 2015-03-27 | 2019-04-24 | Gruenenthal Gmbh | Formulación estable para la administración parenteral de tapentadol |
| BR112017021475A2 (pt) | 2015-04-24 | 2018-07-10 | Gruenenthal Gmbh | forma de dosagem resistente à adulteração (tamper) com liberação imediata e resistência contra extração de solvente |
| CA2998259A1 (en) | 2015-09-10 | 2017-03-16 | Grunenthal Gmbh | Protecting oral overdose with abuse deterrent immediate release formulations |
| EP3231420A1 (en) | 2016-02-29 | 2017-10-18 | G.L. Pharma GmbH | Abuse-deterrent pharmaceutical compositions |
| ES3027562T3 (en) | 2016-09-23 | 2025-06-16 | Gruenenthal Gmbh | Stable formulation for parenteral administration of tapentadol |
| WO2018153947A1 (en) | 2017-02-23 | 2018-08-30 | Grünenthal GmbH | Tapentadol as local anesthetic |
| US20180369151A1 (en) * | 2017-05-29 | 2018-12-27 | Grünenthal GmbH | Multiparticulate oral dosage form providing prolonged release of tapentadol |
| EP3875080A1 (en) | 2020-03-02 | 2021-09-08 | Grünenthal GmbH | Dosage form providing prolonged release of tapentadol phosphoric acid salt |
| AU2020100441B4 (en) * | 2020-03-02 | 2020-06-18 | Grünenthal GmbH | Dosage form providing prolonged release of tapentadol phosphoric acid salt |
| BR112022017700A2 (pt) | 2020-03-02 | 2023-01-17 | Gruenenthal Gmbh | Forma de dosagem fornecendo liberação prolongada de sal de ácido fosfórico de tapentadol |
| AU2020100442B4 (en) * | 2020-03-02 | 2020-06-18 | Grünenthal GmbH | Dosage form providing prolonged release of tapentadol phosphoric acid salt |
| HUE064779T2 (hu) * | 2020-03-02 | 2024-04-28 | Gruenenthal Gmbh | A tapentadol foszforsav sójának elnyújtott hatóanyag-leadást biztosító adagolási formája |
| ES3010208T3 (en) * | 2020-03-16 | 2025-04-01 | Gruenenthal Gmbh | Scored tablet comprising tapentadol |
| DE202020104285U1 (de) | 2020-07-24 | 2020-12-18 | Grünenthal GmbH | Ethylcellulose-beschichtete Partikel enthaltend ein Salz aus Tapentadol und Phosphorsäure |
| HUE059465T2 (hu) | 2020-11-10 | 2022-11-28 | Gruenenthal Gmbh | A tapentadol L-(+)- borkõsav-só késleltetett felszabadulású adagolási formája |
| DE202020005470U1 (de) | 2020-11-10 | 2022-01-25 | Grünenthal GmbH | Darreichungsformen mit verlängerter Freisetzung eines Salzes von Tapentadol mit L-(+)-Weinsäure |
| WO2022101247A1 (de) | 2020-11-10 | 2022-05-19 | Grünenthal GmbH | Darreichungsformen mit verlängerter freisetzung eines salzes von tapentadol mit l-(+)-weinsäure |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4389393A (en) * | 1982-03-26 | 1983-06-21 | Forest Laboratories, Inc. | Sustained release therapeutic compositions based on high molecular weight hydroxypropylmethylcellulose |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870790A (en) * | 1970-01-22 | 1975-03-11 | Forest Laboratories | Solid pharmaceutical formulations containing hydroxypropyl methyl cellulose |
| DE2117239A1 (de) | 1971-04-08 | 1972-11-16 | König, Wilhelm, 4712 Werne | Verfahren zum Erstellen von Wänden aus Schalungssteinen |
| US4126672A (en) * | 1976-02-04 | 1978-11-21 | Hoffmann-La Roche Inc. | Sustained release pharmaceutical capsules |
| US4443428A (en) * | 1982-06-21 | 1984-04-17 | Euroceltique, S.A. | Extended action controlled release compositions |
| US5641632A (en) | 1983-01-10 | 1997-06-24 | Gen-Probe Incorporated | Method for preparing rRNA for hybridization with a probe |
| US4783337A (en) * | 1983-05-11 | 1988-11-08 | Alza Corporation | Osmotic system comprising plurality of members for dispensing drug |
| US4765989A (en) * | 1983-05-11 | 1988-08-23 | Alza Corporation | Osmotic device for administering certain drugs |
| US4612008A (en) * | 1983-05-11 | 1986-09-16 | Alza Corporation | Osmotic device with dual thermodynamic activity |
| GB8519310D0 (en) | 1985-07-31 | 1985-09-04 | Zyma Sa | Granular active substances |
| GB8626098D0 (en) * | 1986-10-31 | 1986-12-03 | Euro Celtique Sa | Controlled release hydromorphone composition |
| US5126145A (en) * | 1989-04-13 | 1992-06-30 | Upsher Smith Laboratories Inc | Controlled release tablet containing water soluble medicament |
| US5266331A (en) * | 1991-11-27 | 1993-11-30 | Euroceltique, S.A. | Controlled release oxycodone compositions |
| US5478577A (en) * | 1993-11-23 | 1995-12-26 | Euroceltique, S.A. | Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level |
| US5286493A (en) * | 1992-01-27 | 1994-02-15 | Euroceltique, S.A. | Stabilized controlled release formulations having acrylic polymer coating |
| AU682827B2 (en) * | 1992-09-18 | 1997-10-23 | Astellas Pharma Inc. | Sustained-release hydrogel preparation |
| IL119660A (en) * | 1993-05-10 | 2002-09-12 | Euro Celtique Sa | Controlled release formulation comprising tramadol |
| IL110014A (en) * | 1993-07-01 | 1999-11-30 | Euro Celtique Sa | Solid controlled-release oral dosage forms of opioid analgesics |
| DE4329794C2 (de) | 1993-09-03 | 1997-09-18 | Gruenenthal Gmbh | Tramadolsalz enthaltende Arzneimittel mit verzögerter Wirkstofffreisetzung |
| WO1995014480A1 (en) | 1993-11-17 | 1995-06-01 | Traditional Chinese Medicine Research Laboratory Inc. | Composition for curing lesioned tissue, process for producing the same, and use thereof |
| US5891471A (en) * | 1993-11-23 | 1999-04-06 | Euro-Celtique, S.A. | Pharmaceutical multiparticulates |
| US5843480A (en) * | 1994-03-14 | 1998-12-01 | Euro-Celtique, S.A. | Controlled release diamorphine formulation |
| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| US5478572A (en) * | 1994-09-06 | 1995-12-26 | Bristol-Myers Squibb Co. | Gepirone dosage form |
| CN1125572A (zh) * | 1994-12-28 | 1996-07-03 | 顺德市广容制药厂 | 一种罗通定痛释片的制作方法 |
| IL116674A (en) * | 1995-01-09 | 2003-05-29 | Mendell Co Inc Edward | Microcrystalline cellulose-based excipient having improved compressibility, pharmaceutical compositions containing the same and methods for the preparation of said excipient and of solid dosage form thereof |
| DE19525137C2 (de) | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE19609847A1 (de) | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| US6096339A (en) | 1997-04-04 | 2000-08-01 | Alza Corporation | Dosage form, process of making and using same |
| IL123505A (en) * | 1996-07-08 | 2004-12-15 | Penwest Pharmaceuticals Compan | Sustained release matrix for high-dose insoluble drugs |
| DE19630035A1 (de) | 1996-07-25 | 1998-01-29 | Asta Medica Ag | Tramadol Multiple Unit Formulierungen |
| EP0998271B3 (en) * | 1997-06-06 | 2014-10-29 | Depomed, Inc. | Gastric-retentive oral drug dosage forms for controlled release of highly soluble drugs |
| US6245357B1 (en) * | 1998-03-06 | 2001-06-12 | Alza Corporation | Extended release dosage form |
| US6106862A (en) * | 1998-08-13 | 2000-08-22 | Andrx Corporation | Once daily analgesic tablet |
| DE19901683B4 (de) | 1999-01-18 | 2005-07-21 | Grünenthal GmbH | Analgetikum mit kontrollierter Wirkstofffreisetzung |
| WO2001032148A1 (en) * | 1999-10-29 | 2001-05-10 | Euro-Celtique, S.A. | Controlled release hydrocodone formulations |
| DE10109763A1 (de) | 2001-02-28 | 2002-09-05 | Gruenenthal Gmbh | Pharmazeutische Salze |
| DE10248309A1 (de) | 2002-10-16 | 2004-04-29 | Grünenthal GmbH | 3-(3- Dimethylamino-1-ethyl-2-methyl-propyl) phenol enthaltendes Arzeimittel mit verzögerter Wirkstofffreisetzung |
-
2002
- 2002-10-18 PE PE2002001030A patent/PE20030527A1/es active IP Right Grant
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- 2002-10-22 WO PCT/EP2002/011809 patent/WO2003035053A1/de not_active Ceased
- 2002-10-22 HU HU0402104A patent/HU230161B1/hu unknown
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- 2002-10-22 WO PCT/EP2002/011806 patent/WO2003035054A1/de not_active Ceased
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- 2002-10-22 DE DE50204198T patent/DE50204198D1/de not_active Expired - Lifetime
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- 2002-10-23 AR ARP020104010A patent/AR036943A1/es not_active Application Discontinuation
- 2002-10-24 MY MYPI20023979A patent/MY127797A/en unknown
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- 2004-04-22 IL IL161587A patent/IL161587A/en active IP Right Grant
- 2004-04-22 CO CO04037005A patent/CO5570662A2/es not_active Application Discontinuation
- 2004-04-26 US US10/831,368 patent/US20050058706A1/en not_active Abandoned
- 2004-05-11 NO NO20041924A patent/NO331896B1/no not_active IP Right Cessation
- 2004-05-12 EC EC2004005102A patent/ECSP045102A/es unknown
- 2004-05-20 ZA ZA2004/03928A patent/ZA200403928B/en unknown
-
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- 2010-08-05 JP JP2010176084A patent/JP2010280697A/ja active Pending
-
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- 2011-09-23 US US13/242,800 patent/US20120034304A1/en not_active Abandoned
-
2012
- 2012-05-08 NO NO2012007C patent/NO2012007I2/no unknown
- 2012-08-13 CY CY2012022C patent/CY2012022I1/el unknown
-
2013
- 2013-04-23 US US13/868,635 patent/US20130237608A1/en not_active Abandoned
-
2016
- 2016-02-08 US US15/018,529 patent/US20160151309A1/en not_active Abandoned
- 2016-12-13 US US15/377,628 patent/US20170087103A1/en not_active Abandoned
-
2018
- 2018-04-02 US US15/943,175 patent/US20180221308A1/en not_active Abandoned
-
2019
- 2019-10-14 US US16/600,974 patent/US11007156B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4389393A (en) * | 1982-03-26 | 1983-06-21 | Forest Laboratories, Inc. | Sustained release therapeutic compositions based on high molecular weight hydroxypropylmethylcellulose |
| US4389393B1 (enExample) * | 1982-03-26 | 1985-10-22 |
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