ES2765036T3 - Composiciones farmacéuticas que comprenden esteres de ácidos grasos - Google Patents
Composiciones farmacéuticas que comprenden esteres de ácidos grasos Download PDFInfo
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- ES2765036T3 ES2765036T3 ES13764158T ES13764158T ES2765036T3 ES 2765036 T3 ES2765036 T3 ES 2765036T3 ES 13764158 T ES13764158 T ES 13764158T ES 13764158 T ES13764158 T ES 13764158T ES 2765036 T3 ES2765036 T3 ES 2765036T3
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 113
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 86
- 239000000194 fatty acid Substances 0.000 title claims abstract description 86
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 86
- -1 fatty acid esters Chemical class 0.000 title claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims abstract description 87
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 82
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 80
- 229960004372 aripiprazole Drugs 0.000 claims abstract description 76
- 239000000203 mixture Substances 0.000 claims abstract description 69
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims abstract description 41
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims abstract description 40
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims abstract description 40
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 30
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
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- 125000005122 aminoalkylamino group Chemical group 0.000 claims abstract 7
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- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 6
- 206010026749 Mania Diseases 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
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- 239000008363 phosphate buffer Substances 0.000 claims description 3
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- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
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- 229950008882 polysorbate Drugs 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 239000000306 component Substances 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 235000002639 sodium chloride Nutrition 0.000 description 31
- 239000007924 injection Substances 0.000 description 25
- 238000002347 injection Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- 229940079593 drug Drugs 0.000 description 18
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- 238000006243 chemical reaction Methods 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000651 prodrug Substances 0.000 description 15
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- 210000001519 tissue Anatomy 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000007972 injectable composition Substances 0.000 description 12
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- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 9
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- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 5
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- MMKRHZKQPFCLLS-UHFFFAOYSA-N tetradecanoic acid ethyl ester Natural products CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 5
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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| US201261612734P | 2012-03-19 | 2012-03-19 | |
| PCT/US2013/030916 WO2013142198A1 (en) | 2012-03-19 | 2013-03-13 | Pharmaaceutical compositions comprising fatty acid esters |
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| ES2765036T3 true ES2765036T3 (es) | 2020-06-05 |
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Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2445502T5 (pl) | 2009-06-25 | 2023-03-13 | Alkermes Pharma Ireland Limited | Związki heterocykliczne do leczenia zaburzeń neurologicznych i psychologicznych |
| PT2685979T (pt) | 2011-03-18 | 2016-12-02 | Alkermes Pharma Ireland Ltd | Composições farmacêuticas injetáveis compreendendo um antipsicótico solúvel em água, laurato de sorbitano e polissorbato 20 |
| AU2013235526B2 (en) | 2012-03-19 | 2017-11-30 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| JP6219918B2 (ja) | 2012-03-19 | 2017-10-25 | アルカームス ファーマ アイルランド リミテッド | グリセロールエステルを含む医薬組成物 |
| CA2867121C (en) | 2012-03-19 | 2021-05-25 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising fatty acid esters |
| US9193685B2 (en) | 2012-09-19 | 2015-11-24 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| WO2015143145A1 (en) * | 2014-03-20 | 2015-09-24 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| WO2016026822A1 (en) * | 2014-08-18 | 2016-02-25 | Alkermes Pharma Ireland Limited | Aripiprazole prodrug compositions |
| US10016415B2 (en) | 2014-08-18 | 2018-07-10 | Alkermes Pharma Ireland Limited | Aripiprazole prodrug compositions |
| DK3185867T3 (da) * | 2014-08-25 | 2021-03-15 | Alkermes Pharma Ireland Ltd | Krystalliseringsfremgangsmåde af aripiprazolderivater i forlængede frigivelsesformuleringer til behandling af skizofreni |
| EP3761983A1 (en) | 2018-03-05 | 2021-01-13 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| BR112020016576A2 (pt) * | 2018-05-11 | 2020-12-15 | Alar Pharmaceuticals Inc. | Formulações injetáveis de ação prolongada e formas cristalinas de derivados de buprenorfina |
| CN110669057A (zh) * | 2018-07-02 | 2020-01-10 | 成都阿奇生物医药科技有限公司 | 一种奥氮平衍生物及其制备方法和用途 |
Family Cites Families (130)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2418499A (en) | 1944-06-20 | 1947-04-08 | Du Pont | 2-alkoxymethylmercapto-thiazoles and thiazolines and a process for preparing the same |
| DE1273533B (de) | 1962-09-08 | 1968-07-25 | Hoechst Ag | Verfahren zur Herstellung von N-(ª‡-Alkoxy-alkyl)-carbonsaeureamiden |
| NL128370C (cg-RX-API-DMAC7.html) | 1964-08-28 | |||
| US3452034A (en) | 1967-03-09 | 1969-06-24 | American Cyanamid Co | Substituted 2-(1,3,4-thiadiazol-2-yl)-4(5)-nitroimidazoles |
| US3573308A (en) | 1969-04-03 | 1971-03-30 | Hoffmann La Roche | 3-lower alkoxy methyl-3,4-dihydro-4-hydroxy-4-aryl quinazolin-2(1h) ones and related compounds |
| US3957808A (en) | 1969-09-03 | 1976-05-18 | Rohm And Haas Company | 3-alkoxyisothiazoles |
| US4727151A (en) | 1974-06-24 | 1988-02-23 | Interx Research Corporation | Labile quaternary ammonium salts as prodrugs |
| US3998815A (en) | 1974-06-24 | 1976-12-21 | Interx Research Corporation | 1-hydrocarbonoyloxymethyl-3-carbamoyl or 3-carboethoxy-pyridinium salts |
| US4204065A (en) | 1975-09-22 | 1980-05-20 | Interx Research Corporation | Soft quaternary surface active agents and method of using same |
| US4260769A (en) | 1977-04-22 | 1981-04-07 | Interx Research Corporation | 5,5-Diphenylhydantoins |
| JPS54130587A (en) | 1978-03-30 | 1979-10-09 | Otsuka Pharmaceut Co Ltd | Carbostyryl derivative |
| JPS568318A (en) | 1979-06-28 | 1981-01-28 | Janssen Pharmaceutica Nv | Non oral long acting composition of haloperidol and bromperidol derivative |
| DE3149010A1 (de) | 1981-12-10 | 1983-07-07 | A. Nattermann & Cie GmbH, 5000 Köln | (+)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3- diazacyclopent-2-en, dessen herstellung und seine verwendung in pharamazeutischen praeparaten |
| US4428935A (en) | 1982-05-24 | 1984-01-31 | Pfizer Inc. | Penicillanic acid dioxide prodrug |
| IT1212743B (it) | 1983-05-17 | 1989-11-30 | Dompe Farmaceutici Spa | Sali quaternari di derivati di benzo[ 1,4 ]diazepinonici,pirido [1,4]benzodiazepinonici,prido [1,5]benzodiazepinonici e loro atti vita' farmacologica |
| JPS602331A (ja) | 1983-06-20 | 1985-01-08 | Yoshino Kogyosho Co Ltd | 飽和ポリエステル樹脂製壜の成形方法 |
| US4760057A (en) | 1983-06-23 | 1988-07-26 | Merck & Co., Inc. | (Acyloxyalkoxy)carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs |
| DK302883D0 (da) | 1983-06-30 | 1983-06-30 | Hans Bundgaard | Allopurinol prodrugs |
| DE3544134A1 (de) | 1984-12-15 | 1986-06-19 | Mitsubishi Chemical Industries Ltd., Tokio/Tokyo | Verfahren zur herstellung von n-((alpha)-alkoxyethyl) pyrrolidon |
| GB8513754D0 (en) | 1985-05-31 | 1985-07-03 | Jones T R | Anti-cancer quinazoline derivatives |
| DK588486A (da) | 1985-12-09 | 1987-06-10 | Otsuka Pharma Co Ltd | Anvendelse af en forbindelse til behandling af hypoxi |
| GB8607683D0 (en) | 1986-03-27 | 1986-04-30 | Ici Plc | Anti-tumor agents |
| US4925860A (en) | 1987-08-05 | 1990-05-15 | E. I. Du Pont De Nemours And Company | Stable pharmaceutical composition of 3-(hydroxymethyl)-5,5-diphenylhydantoin disodium phosphate ester |
| US5006528A (en) | 1988-10-31 | 1991-04-09 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
| US5350747A (en) | 1989-07-07 | 1994-09-27 | Pfizer Inc | Heteroaryl piperazine antipsychotic agents |
| WO1991000863A1 (en) | 1989-07-07 | 1991-01-24 | Pfizer Inc. | Heteroaryl piperazine antipsychotic agents |
| US5229382A (en) | 1990-04-25 | 1993-07-20 | Lilly Industries Limited | 2-methyl-thieno-benzodiazepine |
| JP2800953B2 (ja) * | 1990-07-06 | 1998-09-21 | 住友製薬株式会社 | 新規なイミド誘導体 |
| US5206386A (en) | 1991-03-20 | 1993-04-27 | Isp Investments Inc. | Controlled release N-substituted pyrrolidone esters and process for the use thereof |
| AU645681B2 (en) | 1991-05-02 | 1994-01-20 | John Wyeth & Brother Limited | Piperazine derivatives |
| TW226016B (cg-RX-API-DMAC7.html) | 1991-12-30 | 1994-07-01 | Sterling Winthrop Inc | |
| US5462934A (en) | 1992-03-09 | 1995-10-31 | Takeda Chemical Industries | Condensed heterocyclic ketone derivatives and their use |
| AU4534593A (en) | 1992-06-12 | 1994-01-04 | Affymax Technologies N.V. | Compositions and methods for enhanced drug delivery |
| EP0688325A1 (en) | 1993-03-08 | 1995-12-27 | Eisai Co., Ltd. | Phosphonic acid derivatives |
| TW376319B (en) | 1993-04-28 | 1999-12-11 | Janssen Pharmaceutica Nv | Pharmaceutical composition containing risperidone pamoate and having a long acting activity for treating psychoses induced by the release of dopamine |
| DE4439493A1 (de) | 1994-10-25 | 1996-05-02 | Schering Ag | Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| JP3571795B2 (ja) | 1995-04-18 | 2004-09-29 | 株式会社日本触媒 | Ｎ−（１−アルキルオキシアルキル）カルバメート類の気相分子内脱アルコール反応用触媒およびｎ−ビニルカルバメート類の製造方法 |
| US7833543B2 (en) | 1995-06-07 | 2010-11-16 | Durect Corporation | High viscosity liquid controlled delivery system and medical or surgical device |
| CA2250187A1 (en) * | 1996-03-25 | 1997-10-02 | Eli Lilly And Company | Composition comprising olanzapine and a drug useful in the treatment of pain for use in the treatment of pain |
| DE19619819A1 (de) | 1996-05-16 | 1997-11-20 | Boehringer Mannheim Gmbh | Neue Thiazolidindione, Verfahren zu ihrer Herstellung und diese enthaltenden Arzneimittel |
| JP2000516244A (ja) | 1996-08-22 | 2000-12-05 | リサーチ・トライアングル・ファーマシューティカルズ | 水不溶性物質の微粒子を含む組成物およびその製造方法 |
| ES2210769T3 (es) | 1997-06-13 | 2004-07-01 | Cydex Inc. | Compuesto con vida de almacenamiento prolongada que comprende ciclodextrina y medicamentos y promedicamentos que se descomponen en componentes insolubles en agua. |
| EA002825B1 (ru) | 1997-09-30 | 2002-10-31 | Эли Лилли Энд Компани | Препарат 2-метилтиенобензодиазепина |
| UA72189C2 (uk) | 1997-11-17 | 2005-02-15 | Янссен Фармацевтика Н.В. | Фармацевтична композиція, що містить водну суспензію субмікронних ефірів 9-гідроксирисперидон жирних кислот |
| US6180095B1 (en) | 1997-12-17 | 2001-01-30 | Enzon, Inc. | Polymeric prodrugs of amino- and hydroxyl-containing bioactive agents |
| ATE261730T1 (de) | 1997-12-31 | 2004-04-15 | Univ Kansas | Wasserlösliche medikamentenvorstufen tertiärer amine enthaltender medikamente und verfahren zu ihrer herstellung |
| SK2612001A3 (en) | 1998-08-26 | 2001-11-06 | Aventis Pharma Ltd | Aza-bicycles which modulate the inhibition of cell adhesion |
| FR2783519B1 (fr) | 1998-09-23 | 2003-01-24 | Sod Conseils Rech Applic | Nouveaux derives d'amidines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
| US7374779B2 (en) * | 1999-02-26 | 2008-05-20 | Lipocine, Inc. | Pharmaceutical formulations and systems for improved absorption and multistage release of active agents |
| US20060034937A1 (en) * | 1999-11-23 | 2006-02-16 | Mahesh Patel | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| CA2311734C (en) | 2000-04-12 | 2011-03-08 | Bristol-Myers Squibb Company | Flash-melt oral dosage formulation |
| MY128449A (en) | 2000-05-24 | 2007-02-28 | Sugen Inc | Prodrugs of 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives |
| JP2003535884A (ja) * | 2000-06-16 | 2003-12-02 | スカイファーマ・カナダ・インコーポレーテッド | プロポフォールの改善された注射可能な分散物 |
| US6656505B2 (en) | 2000-07-21 | 2003-12-02 | Alpharma Uspd Inc. | Method for forming an aqueous flocculated suspension |
| US20030049320A1 (en) | 2000-12-18 | 2003-03-13 | Wockhardt Limited | Novel in-situ forming controlled release microcarrier delivery system |
| US7053092B2 (en) | 2001-01-29 | 2006-05-30 | Otsuka Pharmaceutical Co., Ltd. | 5-HT1a receptor subtype agonist |
| DE60201665T2 (de) | 2001-02-14 | 2006-02-02 | Warner-Lambert Co. Llc | Benzothiadiazine als matrix metallproteinase inhibitoren |
| WO2002074247A2 (en) | 2001-03-19 | 2002-09-26 | Praecis Pharmaceuticals Incorporated | Pharmaceutical formulations for sustained release |
| US20060293217A1 (en) | 2001-03-19 | 2006-12-28 | Praecis Pharmaceuticals, Inc. | Pharmaceutical formulations for sustained release |
| EP1383445A4 (en) * | 2001-03-20 | 2005-04-13 | Cydex Inc | FORMULATIONS WITH PROPOFOL AND A SULFOALKYL ETHER CYCLODEXTRIN |
| EP1414798A2 (en) | 2001-04-03 | 2004-05-06 | Aryx Therapeutics | Ultrashort-acting opioids for transdermal application |
| MY129350A (en) | 2001-04-25 | 2007-03-30 | Bristol Myers Squibb Co | Aripiprazole oral solution |
| AR033485A1 (es) | 2001-09-25 | 2003-12-26 | Otsuka Pharma Co Ltd | Sustancia medicinal de aripiprazol de baja higroscopicidad y proceso para la preparacion de la misma |
| AU2003245773A1 (en) | 2002-02-15 | 2003-09-04 | Glaxo Group Limited | Vanilloid receptor modulators |
| ATE375349T1 (de) | 2002-08-02 | 2007-10-15 | Merck & Co Inc | Substituierte furo(2,3-b)pyridin derivate |
| GEP20063996B (en) | 2002-08-20 | 2006-12-11 | Bristol Myers Squibb Co | Aripiprazole complex formulation and use thereof |
| BR0314393A (pt) | 2002-09-17 | 2005-07-19 | Warner Lambert Co | Piperazinas heterocìclicas substituìdas para o tratamento de esquizofrenia |
| US7148211B2 (en) | 2002-09-18 | 2006-12-12 | Genzyme Corporation | Formulation for lipophilic agents |
| US20040186182A1 (en) | 2002-12-18 | 2004-09-23 | Algorx | Administration of capsaicinoids |
| EA011708B1 (ru) | 2002-12-18 | 2009-04-28 | Алгоркс Фармасьютикалз, Инк. | Применение транс- капсаицина |
| DE10303669A1 (de) | 2003-01-28 | 2004-07-29 | Hans-Knöll-Institut für Naturstoff-Forschung e.V. | Tetraalkylammoniumsalze vom Kohlensäureestertyp, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| CN1826331A (zh) | 2003-04-03 | 2006-08-30 | 塞马福尔药业公司 | Pi－3激酶抑制剂前药 |
| BRPI0410786A (pt) | 2003-05-23 | 2006-06-20 | Otsuka Pharma Co Ltd | composição, uso da mesma, e, método de tratamento de um distúrbio de humor em um paciente |
| MXPA06000942A (es) | 2003-07-24 | 2006-03-30 | Merial Ltd | Nuevas formulaciones de vacunas. |
| US6987111B2 (en) | 2003-08-06 | 2006-01-17 | Alkermes Controlled Therapeutics, Ii | Aripiprazole, olanzapine and haloperidol pamoate salts |
| US20050032811A1 (en) | 2003-08-06 | 2005-02-10 | Josiah Brown | Methods for administering aripiprazole |
| US7160888B2 (en) | 2003-08-22 | 2007-01-09 | Warner Lambert Company Llc | [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia |
| TW200510721A (en) * | 2003-08-29 | 2005-03-16 | Toshiba Kk | Color reagent, concentration measuring kit, concentration measuring method and sensor chip for use therein |
| EP1675573B2 (en) | 2003-10-23 | 2012-06-13 | Otsuka Pharmaceutical Co., Ltd. | Controlled release sterile injectable aripiprazole formulation and method |
| EP1701954A1 (en) | 2003-12-31 | 2006-09-20 | Warner-Lambert Company LLC | N-substituted piperidine and piperazine derivatives |
| CN1917882A (zh) | 2004-02-13 | 2007-02-21 | 辉瑞产品公司 | 非典型抗精神病药物与促肾上腺皮质激素释放因子拮抗剂的治疗剂组合 |
| US7169803B2 (en) | 2004-03-15 | 2007-01-30 | Bristol-Myers Squibb Company | N-substituted prodrugs of fluorooxindoles |
| US7119214B2 (en) | 2004-04-13 | 2006-10-10 | Cephalon France | Thio-substituted tricyclic and bicyclic aromatic methanesulfinyl derivatives |
| GB2413795A (en) | 2004-05-05 | 2005-11-09 | Cipla Ltd | Process for the preparation of rosiglitazone |
| WO2006037090A2 (en) | 2004-09-28 | 2006-04-06 | Purdue Research Foundation | Drug-phosphate conjugates as prodrugs |
| AU2005307797B2 (en) | 2004-11-16 | 2011-06-02 | Alkermes Pharma Ireland Limited | Injectable nanoparticulate olanzapine formulations |
| WO2006082588A2 (en) | 2005-02-07 | 2006-08-10 | Pharmalight Inc. | Method and device for ophthalmic administration of active pharmaceutical ingredients |
| WO2006090273A2 (en) | 2005-02-22 | 2006-08-31 | Warner-Lambert Company Llc | [1,8]naphthyridin-2-ones and related compounds with keto or hydroxyl linkers for the treatment of schizophrenia |
| WO2006102079A1 (en) * | 2005-03-17 | 2006-09-28 | Novartis Ag | N- [3- (1-amin0-5, 6, 7, 8-tetrahydro-2 , 4, 4b-triazafluoren-9-yl)-phenyl] benzamides as tyrosine/threonine kinase inhibitors, in particular b-raf kinase |
| ES2390353T3 (es) | 2005-06-13 | 2012-11-12 | Dainippon Sumitomo Pharma Co., Ltd. | Preparación de disolución |
| EP2279727A3 (en) | 2005-09-15 | 2011-10-05 | Elan Pharma International Limited | Nanoparticulate aripiprazole formulations |
| EP1777222A1 (en) | 2005-09-22 | 2007-04-25 | Galantos Pharma GmbH | Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment |
| WO2007059111A2 (en) | 2005-11-14 | 2007-05-24 | Entremed, Inc. | Anti-angiogenic activity of 2-methoxyestradiol in combination with anti-cancer agents |
| US20090068290A1 (en) | 2006-08-31 | 2009-03-12 | Michel Bourin | Bifeprunox doses for treating schizophrenia |
| WO2008034041A2 (en) | 2006-09-15 | 2008-03-20 | Astrazeneca Ab | Therapeutic combinations |
| US20090291134A1 (en) | 2006-11-21 | 2009-11-26 | Jina Pharmaceuticals, Inc. | Endoxifen methods and compositions in the treatment of psychiatric and neurodegenerative diseases |
| AU2007328007A1 (en) | 2006-12-05 | 2008-06-12 | Neurogesx, Inc. | Prodrugs and methods of making and using the same |
| AU2007334343A1 (en) | 2006-12-15 | 2008-06-26 | Ordway Research Institute, Inc. | Treatments of therapy-resistant diseases comprising drug combinations |
| EP1961412A1 (en) | 2006-12-27 | 2008-08-27 | LEK Pharmaceuticals D.D. | Self-microemulsifying drug delivery systems |
| US20080186971A1 (en) | 2007-02-02 | 2008-08-07 | Tarari, Inc. | Systems and methods for processing access control lists (acls) in network switches using regular expression matching logic |
| CN101677971A (zh) | 2007-03-19 | 2010-03-24 | 阿卡蒂亚药品公司 | 5-ht2a反向激动剂和拮抗剂与抗精神病药物的组合 |
| JP5097265B2 (ja) * | 2007-04-04 | 2012-12-12 | メルク・シャープ・エンド・ドーム・コーポレイション | 治療薬 |
| WO2009012096A2 (en) | 2007-07-18 | 2009-01-22 | Research Development Foundation | Improved therapeutic methods and compositions comprising chroman ring compounds |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| WO2009052467A1 (en) | 2007-10-19 | 2009-04-23 | Board Of Regents Of The University Of Texas System | Methods of identifying pi-3-kinase inhibitor resistance |
| WO2009060473A2 (en) | 2007-11-06 | 2009-05-14 | Panacea Biotec Limited | Injectable compositions, processes and uses thereof |
| FI2234617T4 (fi) | 2007-12-19 | 2024-12-23 | Janssen Pharmaceutica Nv | Pitkävaikutteisiin injektoitaviin paliperidoniestereihin liittyvä annosteluohjelma |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| US9161943B2 (en) | 2007-12-31 | 2015-10-20 | Industrial Technology Research Institute | Sustained release composition and manufacturing method thereof |
| WO2009126931A2 (en) | 2008-04-11 | 2009-10-15 | Xvasive, Inc. | Combination therapy for bipolar disorder |
| KR20110050549A (ko) | 2008-09-03 | 2011-05-13 | 버텍스 파마슈티칼스 인코포레이티드 | 공-결정 및 이를 포함하는 제약 제제 |
| WO2010083843A1 (en) | 2009-01-26 | 2010-07-29 | Egalet A/S | Controlled release formulations with continuous efficacy |
| WO2010129843A1 (en) | 2009-05-08 | 2010-11-11 | Cytopathfinder, Inc. | Dihydronaphthyridinyl and related compounds for use in treating ophthalmological disorders |
| PL2445502T5 (pl) | 2009-06-25 | 2023-03-13 | Alkermes Pharma Ireland Limited | Związki heterocykliczne do leczenia zaburzeń neurologicznych i psychologicznych |
| ES2885698T3 (es) | 2009-06-25 | 2021-12-15 | Alkermes Pharma Ireland Ltd | Profármacos de compuestos nh-ácidos |
| KR20120116401A (ko) | 2009-10-30 | 2012-10-22 | 얀센 파마슈티카 엔.브이. | 장기-작용성의 주사가능한 팔리페리돈 에스테르와 관련된 투약 요법 |
| WO2011084848A2 (en) | 2010-01-07 | 2011-07-14 | Alkermes, Inc. | Prodrugs of heteraromatic compounds |
| US20110166194A1 (en) | 2010-01-07 | 2011-07-07 | Alkermes, Inc. | Asenapine Prodrugs |
| US9670200B2 (en) | 2010-01-07 | 2017-06-06 | Alkermes Pharma Ireland Limited | Quaternary ammonium salt prodrugs |
| US20110166156A1 (en) | 2010-01-07 | 2011-07-07 | Alkermes, Inc. | Prodrugs for the Treatment of Schizophrenia and Bipolar Disease |
| US20110166128A1 (en) | 2010-01-07 | 2011-07-07 | Alkermes, Inc. | Diaryldiazepine Prodrugs for the Treatment of Neurological and Psychological Disorders |
| KR101792891B1 (ko) | 2010-02-16 | 2017-11-20 | 하마마츠 포토닉스 가부시키가이샤 | 가스 농도 산출 장치 및 가스 농도 계측 모듈 |
| ES2834973T3 (es) | 2010-05-04 | 2021-06-21 | Alkermes Pharma Ireland Ltd | Procedimiento de síntesis de compuestos de lactama oxidada |
| US8592427B2 (en) | 2010-06-24 | 2013-11-26 | Alkermes Pharma Ireland Limited | Prodrugs of NH-acidic compounds: ester, carbonate, carbamate and phosphonate derivatives |
| PT2685979T (pt) | 2011-03-18 | 2016-12-02 | Alkermes Pharma Ireland Ltd | Composições farmacêuticas injetáveis compreendendo um antipsicótico solúvel em água, laurato de sorbitano e polissorbato 20 |
| AU2013235526B2 (en) | 2012-03-19 | 2017-11-30 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| JP6219918B2 (ja) | 2012-03-19 | 2017-10-25 | アルカームス ファーマ アイルランド リミテッド | グリセロールエステルを含む医薬組成物 |
| CA2867121C (en) | 2012-03-19 | 2021-05-25 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising fatty acid esters |
| US9193685B2 (en) | 2012-09-19 | 2015-11-24 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| WO2015143145A1 (en) | 2014-03-20 | 2015-09-24 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
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2013
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- 2013-03-13 WO PCT/US2013/030916 patent/WO2013142198A1/en not_active Ceased
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- 2013-03-13 NZ NZ630643A patent/NZ630643A/en not_active IP Right Cessation
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| AU2013235519A1 (en) | 2014-09-25 |
| EP2827868B1 (en) | 2019-11-13 |
| AU2013235519B9 (en) | 2017-10-05 |
| NZ630643A (en) | 2017-08-25 |
| WO2013142198A1 (en) | 2013-09-26 |
| JP6471089B2 (ja) | 2019-02-13 |
| CA2867121C (en) | 2021-05-25 |
| AU2013235519B2 (en) | 2017-09-07 |
| US10004807B2 (en) | 2018-06-26 |
| HK1206596A1 (en) | 2016-01-15 |
| EP2827868A1 (en) | 2015-01-28 |
| JP2015510929A (ja) | 2015-04-13 |
| CA2867121A1 (en) | 2013-09-26 |
| JP2018009031A (ja) | 2018-01-18 |
| EP2827868A4 (en) | 2015-11-11 |
| AU2013235519C1 (en) | 2018-04-26 |
| US20130267503A1 (en) | 2013-10-10 |
| EP2827868B8 (en) | 2019-12-18 |
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