ES2770575T3 - Formulación de liberación sostenida de un fármaco antiinflamatorio no esteroideo - Google Patents
Formulación de liberación sostenida de un fármaco antiinflamatorio no esteroideo Download PDFInfo
- Publication number
- ES2770575T3 ES2770575T3 ES11837126T ES11837126T ES2770575T3 ES 2770575 T3 ES2770575 T3 ES 2770575T3 ES 11837126 T ES11837126 T ES 11837126T ES 11837126 T ES11837126 T ES 11837126T ES 2770575 T3 ES2770575 T3 ES 2770575T3
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- Prior art keywords
- cyclodextrin
- multivesicular
- emulsion
- multivesicular liposomes
- injection
- Prior art date
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- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
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Applications Claiming Priority (2)
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Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012058483A1 (en) | 2010-10-28 | 2012-05-03 | Pacira Pharmaceuticals, Inc. | A sustained release formulation of a non-steroidal anti-inflammatory drug |
| JP5813011B2 (ja) * | 2010-12-27 | 2015-11-17 | テルモ株式会社 | リポソーム組成物およびその製造方法 |
| US20130337051A1 (en) * | 2011-03-01 | 2013-12-19 | To-Bbb Holding B.V. | Advanced active liposomal loading of poorly water-soluble substances |
| EP2846773A4 (en) | 2012-05-10 | 2015-12-30 | Painreform Ltd | DEPOT FORMULATIONS OF A LOCAL ANESTHETICS AND METHOD FOR THE MANUFACTURE THEREOF |
| HUE062466T2 (hu) | 2012-07-05 | 2023-11-28 | Taiwan Liposome Co Ltd | Eljárások arthritis kezelésére |
| CN106659683A (zh) * | 2014-01-14 | 2017-05-10 | 约翰斯·霍普金斯大学 | 包封修饰的环糊精复合物的脂质体组合物及其应用 |
| GB2541835B (en) * | 2015-01-21 | 2018-09-12 | Pacira Pharmaceuticals Inc | Multivesicular liposome formulations of tranexamic acid |
| GB201505527D0 (en) | 2015-03-31 | 2015-05-13 | Jmedtech Pte Ltd | Composition |
| EP3317448B1 (en) | 2015-06-30 | 2021-09-08 | Tela Bio, Inc. | Corner-lock stitch patterns |
| US10426587B2 (en) | 2015-07-21 | 2019-10-01 | Tela Bio, Inc. | Compliance control stitching in substrate materials |
| WO2017079563A1 (en) | 2015-11-06 | 2017-05-11 | The Johns Hopkins University | Methods of treating liver fibrosis by administering 3-bromopyruvate |
| EP3448308B1 (en) | 2016-04-26 | 2024-08-14 | Tela Bio, Inc. | Hernia repair grafts having anti-adhesion barriers |
| CN106491533B (zh) * | 2016-11-11 | 2019-08-20 | 江苏九旭药业有限公司 | 一种稳定的氟比洛芬酯组合物及制备方法 |
| CN109983013A (zh) * | 2016-11-18 | 2019-07-05 | 帕西拉制药有限公司 | 美洛昔康锌复合物微粒多囊脂质体制剂及其制备方法 |
| KR102069670B1 (ko) * | 2017-03-02 | 2020-01-23 | 단디바이오사이언스 주식회사 | 면역활성물질을 포함하는 다중도메인캡슐, 이의 제조방법, 및 이를 포함하는 면역조절 조성물 |
| WO2019071245A1 (en) | 2017-10-06 | 2019-04-11 | Foundry Therapeutics, Inc. | IMPLANTABLE DEPOSITS FOR REGULATED RELEASE OF ANALGESICS TO TREAT POSTHOPERATIVE PAIN ASSOCIATED WITH ORTHOPEDIC SURGERY, AND RELATED DEVICES, SYSTEMS, AND METHODS |
| EP3737433A1 (en) | 2018-01-08 | 2020-11-18 | Foundry Therapeutics, Inc. | Devices, systems, and methods for treating intraluminal cancer via controlled delivery of therapeutic agents |
| US11590262B2 (en) | 2018-03-09 | 2023-02-28 | Tela Bio, Inc. | Surgical repair graft |
| CA3099890A1 (en) | 2018-05-12 | 2019-11-21 | Foundry Therapeutics, Inc. | Implantable polymer depots for the controlled release of therapeutic agents |
| US12303619B2 (en) | 2018-08-28 | 2025-05-20 | Foundry Therapeutics, Inc. | Polymer implants |
| BR112021003256A2 (pt) * | 2018-09-14 | 2021-05-18 | Pharmosa Biopharm Inc. | composição farmacêutica, método para tratar uma doença respiratória e método para reduzir o efeito colateral de uma droga de ácido fraco |
| JP7229012B2 (ja) * | 2018-12-25 | 2023-02-27 | 小林製薬株式会社 | 内服用医薬組成物 |
| WO2020185688A1 (en) | 2019-03-08 | 2020-09-17 | Tela Bio, Inc. | Textured medical textiles |
| CN114732786A (zh) * | 2021-01-07 | 2022-07-12 | 广州曼翔医药有限公司 | 一种注射用氯诺昔康脂质体 |
| US11357727B1 (en) | 2021-01-22 | 2022-06-14 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US11278494B1 (en) | 2021-01-22 | 2022-03-22 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US12151024B2 (en) | 2021-01-22 | 2024-11-26 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US11033495B1 (en) | 2021-01-22 | 2021-06-15 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| CN113509440B (zh) * | 2021-03-26 | 2022-08-30 | 中国药科大学 | 一种高包封率酮咯酸多囊脂质体制备及提高其稳定性方法 |
| CN113616597A (zh) * | 2021-08-02 | 2021-11-09 | 上海交通大学 | 一种美洛昔康的注射剂及其制备方法和用途 |
| WO2023064464A1 (en) | 2021-10-14 | 2023-04-20 | Pacira Pharmaceuticals, Inc. | Bupivacaine multivesicular liposome formulations and uses thereof |
| CN116077435B (zh) * | 2023-04-07 | 2023-06-02 | 山东恒邦中科生物工程有限公司 | 一种兽用高浓度美洛昔康注射剂的制备方法 |
| US12251472B1 (en) | 2024-05-20 | 2025-03-18 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US12280149B1 (en) | 2024-05-20 | 2025-04-22 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US12156940B1 (en) | 2024-05-20 | 2024-12-03 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
Family Cites Families (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547119A (en) | 1967-12-08 | 1970-12-15 | Baxter Laboratories Inc | Catheter assembly |
| US4311137A (en) | 1980-04-30 | 1982-01-19 | Sherwood Medical Industries Inc. | Infusion device |
| US4612370A (en) | 1982-04-02 | 1986-09-16 | The Regents Of The University Of California | Lipid-saccharide reaction products |
| US4531937A (en) | 1983-01-24 | 1985-07-30 | Pacesetter Systems, Inc. | Introducer catheter apparatus and method of use |
| US4565696A (en) | 1983-08-03 | 1986-01-21 | The Regents Of The University Of California | Production of immunogens by antigen conjugation to liposomes |
| US4897355A (en) * | 1985-01-07 | 1990-01-30 | Syntex (U.S.A.) Inc. | N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor |
| US5230899A (en) | 1985-08-07 | 1993-07-27 | Smithkline Beecham Corporation | Methods and compositions for making liposomes |
| US4755173A (en) | 1986-02-25 | 1988-07-05 | Pacesetter Infusion, Ltd. | Soft cannula subcutaneous injection set |
| GB8607717D0 (en) | 1986-03-27 | 1986-04-30 | Unilever Plc | Hydratable powders |
| JPH01501622A (ja) * | 1986-06-12 | 1989-06-08 | ザ リポソーム カンパニー，インコーポレイテッド | リポソームにカプセル包囲された非ステロイド性抗炎症薬を用いる方法および組成物 |
| US6759057B1 (en) * | 1986-06-12 | 2004-07-06 | The Liposome Company, Inc. | Methods and compositions using liposome-encapsulated non-steroidal anti-inflammatory drugs |
| WO1987007506A1 (en) | 1986-06-12 | 1987-12-17 | The Liposome Company, Inc. | Methods and compositions using liposome-encapsulated non-steroidal anti-inflammatory drugs |
| US5204112A (en) | 1986-06-16 | 1993-04-20 | The Liposome Company, Inc. | Induction of asymmetry in vesicles |
| US4877619A (en) | 1986-08-25 | 1989-10-31 | Vestar, Inc. | Liposomal vesicles for intraperitoneal administration of therapeutic agents |
| GB8704171D0 (en) * | 1987-02-23 | 1987-04-01 | Clayton Found Res | Multivesicular liposomes |
| US5723147A (en) | 1987-02-23 | 1998-03-03 | Depotech Corporation | Multivesicular liposomes having a biologically active substance encapsulated therein in the presence of a hydrochloride |
| US5576017A (en) | 1988-05-30 | 1996-11-19 | Depotech Corporation | Heterovesicular liposomes |
| AU664359B2 (en) * | 1990-12-03 | 1995-11-16 | Nexstar Pharmaceuticals, Inc. | Prevention of synovial adhesions |
| US5230800A (en) | 1992-02-20 | 1993-07-27 | Minnesota Mining And Manufacturing Company | Scrim inserted electrostatic fibrous filter web |
| US5545143A (en) | 1993-01-21 | 1996-08-13 | T. S. I. Medical | Device for subcutaneous medication delivery |
| US5759573A (en) | 1993-04-22 | 1998-06-02 | Depotech Corporation | Cyclodextrin liposomes encapsulating pharmacologic compounds and methods for their use |
| US5766627A (en) | 1993-11-16 | 1998-06-16 | Depotech | Multivescular liposomes with controlled release of encapsulated biologically active substances |
| RO116341B1 (ro) * | 1993-11-16 | 2001-01-30 | Depotech Corp La Jolia | Lipozom multivezicular si procedeu de obtinere a acestuia |
| US5993850A (en) | 1994-09-13 | 1999-11-30 | Skyepharma Inc. | Preparation of multivesicular liposomes for controlled release of encapsulated biologically active substances |
| US6193963B1 (en) | 1996-10-17 | 2001-02-27 | The Regents Of The University Of California | Method of treating tumor-bearing patients with human plasma hyaluronidase |
| US5891467A (en) | 1997-01-31 | 1999-04-06 | Depotech Corporation | Method for utilizing neutral lipids to modify in vivo release from multivesicular liposomes |
| FR2763958A1 (fr) | 1997-05-29 | 1998-12-04 | Transgene Sa | Produit de combinaison associant un acide nucleique a une substance desorganisant la matrice extracellulaire pour la therapie genique |
| US6306432B1 (en) * | 1997-09-08 | 2001-10-23 | Chiron Corporation | High and low load formulations of IGF-I in multivesicular liposomes |
| US6106858A (en) | 1997-09-08 | 2000-08-22 | Skyepharma, Inc. | Modulation of drug loading in multivescular liposomes |
| PT1014946E (pt) | 1997-09-18 | 2010-07-06 | Pacira Pharmaceuticals Inc | COMPOSIÃES ANESTéSICAS LIPOSSOMAIS DE LIBERTAÃO SUSTENTADA |
| EP1028629A4 (en) | 1997-11-05 | 2003-06-04 | Biozone Lab Inc | IMPROVED FOOD PREPARATION FOR INFANTS CONTAINING NUTRIENTS AND ACTIVE SUBSTANCES ENCLOSED IN LIPOSOMES |
| JP4575592B2 (ja) * | 1997-11-14 | 2010-11-04 | パシラ ファーマシューティカルズ インコーポレーテッド | 多小胞リポソームの製造 |
| JP4740455B2 (ja) | 1998-08-12 | 2011-08-03 | イーサム リサーチ ディベロップメント カンパニー オブ ザ ヘブリュー ユニバーシティー オブ エルサレム | 硫酸アンモニウム勾配を使用して調製されるリポソーム性ブピバカイン組成物 |
| US20020114829A1 (en) | 1998-12-18 | 2002-08-22 | Hayat Onyuksel | Materials and methods for making improved liposome compositions |
| US20020009466A1 (en) | 1999-08-31 | 2002-01-24 | David J. Brayden | Oral vaccine compositions |
| US20020035107A1 (en) | 2000-06-20 | 2002-03-21 | Stefan Henke | Highly concentrated stable meloxicam solutions |
| ATE444735T1 (de) | 2001-03-21 | 2009-10-15 | Madash Llc | Thermisch reversible wasser-in-öl-in-wasser- emulsionen |
| US20020169102A1 (en) | 2001-04-03 | 2002-11-14 | Frey William H. | Intranasal delivery of agents for regulating development of implanted cells in the CNS |
| US6709663B2 (en) * | 2001-08-31 | 2004-03-23 | Healthpoint, Ltd. | Multivesicular emulsion drug delivery systems |
| US8043602B2 (en) | 2002-02-07 | 2011-10-25 | Endocyte, Inc. | Folate targeted enhanced tumor and folate receptor positive tissue optical imaging technology |
| US20030235610A1 (en) | 2002-06-21 | 2003-12-25 | Piedmont Pharmaceuticals, Llc | Liposomes containing biologically active compounds |
| US7485670B2 (en) | 2002-08-02 | 2009-02-03 | Cambridge Polymer Group, Inc. | Systems and methods for controlling and forming polymer gels |
| US7473432B2 (en) * | 2002-10-11 | 2009-01-06 | Idea Ag | NSAID formulations, based on highly adaptable aggregates, for improved transport through barriers and topical drug delivery |
| US20040224010A1 (en) * | 2002-11-15 | 2004-11-11 | Optime Therapeutics, Inc. | Ophthalmic liposome compositions and uses thereof |
| US20060104968A1 (en) | 2003-03-05 | 2006-05-18 | Halozyme, Inc. | Soluble glycosaminoglycanases and methods of preparing and using soluble glycosaminogly ycanases |
| CN102943067B (zh) | 2003-03-05 | 2016-06-22 | 海洋酶公司 | 可溶性透明质酸酶糖蛋白(sHASEGP)、制备它们的方法、它们的用途和包含它们的药物组合物 |
| US20070009583A1 (en) | 2003-10-10 | 2007-01-11 | Qvist Michael H | Dressing |
| US20050268425A1 (en) | 2004-04-20 | 2005-12-08 | Clemons William E Sr | Surface cleaner |
| US8129359B2 (en) | 2004-06-04 | 2012-03-06 | Ethicon, Inc. | Composition and method for treating post-surgical pain |
| ES2490595T3 (es) | 2005-02-17 | 2014-09-04 | Abbott Laboratories | Administración transmucosal de composiciones de fármacos para tratar y prevenir trastornos en animales |
| EP2248578B1 (en) | 2005-03-04 | 2012-06-06 | President and Fellows of Harvard College | Method for forming multiple emulsions |
| US20070009434A1 (en) | 2005-07-05 | 2007-01-11 | Low Philip S | Imaging and therapeutic method using monocytes |
| WO2007049278A2 (en) | 2005-10-26 | 2007-05-03 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | A method for preparing liposomes and uses thereof |
| US8097646B2 (en) | 2005-11-07 | 2012-01-17 | Alpharx, Inc. | Ophthalmic preparation containing menthyl ester of indomethacin |
| AU2007230716B2 (en) | 2006-03-28 | 2012-05-03 | Javelin Pharmaceuticals, Inc. | Formulations of low dose diclofenac and beta-cyclodextrin |
| WO2007134819A1 (en) | 2006-05-18 | 2007-11-29 | Medigene Ag | Cationic liposomal preparations for the treatment of rheumatoid arthritis |
| WO2008030818A2 (en) | 2006-09-05 | 2008-03-13 | Mebiopharm Co., Ltd. | Novel liposome compositions |
| US20080075807A1 (en) | 2006-09-22 | 2008-03-27 | Baldwin Cheryl J | Methods Of Fortifying Foods With Vitamin D And Food Products Thereof |
| DE602006018467D1 (de) * | 2006-09-28 | 2011-01-05 | Losan Pharma Gmbh | Schnell lösliche Formulierung von nichtsteroidalen Antiphlogistika |
| EP2527345B1 (en) | 2006-10-16 | 2015-12-16 | Thesan Pharmaceuticals, Inc. | Therapeutic pyrazolyl thienopyridines |
| US8268347B1 (en) | 2006-10-24 | 2012-09-18 | Aradigm Corporation | Dual action, inhaled formulations providing both an immediate and sustained release profile |
| US8071127B2 (en) | 2006-10-24 | 2011-12-06 | Aradigm Corporation | Dual action, inhaled formulations providing both an immediate and sustained release profile |
| WO2008073317A2 (en) | 2006-12-08 | 2008-06-19 | Musc Foundation For Research Development | Cytarabine for treatment of glioma |
| EP1932516A1 (en) * | 2006-12-11 | 2008-06-18 | Universiteit Utrecht Holding B.V. | Anti-inflammatory compounds containing compositions for treatment of cancer |
| US20090311237A1 (en) | 2008-04-14 | 2009-12-17 | Frost Gregory I | Combination therapy using a soluble hyaluronidase and a bisphosphonate |
| US8062663B2 (en) | 2008-05-23 | 2011-11-22 | National Health Research Instittues | Methods and compostions for enhancing transdermal drug delivery |
| US8431692B2 (en) | 2008-06-06 | 2013-04-30 | Quark Pharmaceuticals, Inc. | Compositions and methods for treatment of ear disorders |
| US20110111044A1 (en) * | 2008-07-31 | 2011-05-12 | Enzon Pharmaceuticals, Inc. | Nanoparticle compositions for nucleic acids delivery system |
| US8361935B2 (en) * | 2008-08-29 | 2013-01-29 | Schlumberger Technology Corporation | Metal free crosslinking of galactomannan |
| CN102405286A (zh) * | 2008-09-22 | 2012-04-04 | 阿克赛医药公司 | 减小大小的自递送RNAi化合物 |
| CN101744764A (zh) * | 2008-12-09 | 2010-06-23 | 上海医药工业研究院 | 一种空白和含盐酸拓扑替康的多囊脂质体及其制备方法 |
| US20120027842A1 (en) | 2008-12-23 | 2012-02-02 | Amira Pharmaceuticals, Inc. | Topical formulations of flap inhibitors for administration to an eye |
| US9968583B2 (en) | 2009-03-30 | 2018-05-15 | Eisai R & D Management Co., Ltd. | Method of manufacture of liposome composition |
| US20110250264A1 (en) | 2010-04-09 | 2011-10-13 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| WO2012058483A1 (en) | 2010-10-28 | 2012-05-03 | Pacira Pharmaceuticals, Inc. | A sustained release formulation of a non-steroidal anti-inflammatory drug |
| HUE062466T2 (hu) * | 2012-07-05 | 2023-11-28 | Taiwan Liposome Co Ltd | Eljárások arthritis kezelésére |
| CA2843943A1 (en) | 2014-02-20 | 2014-05-28 | Pankaj Modi | Oral formulations of chemotherapeutic agents |
| US10137325B2 (en) * | 2014-03-24 | 2018-11-27 | Shantha Sarangapani | System and method for deactivation and disposal of a pharmaceutical dosage form |
| JP6584146B2 (ja) | 2015-05-27 | 2019-10-02 | キヤノン株式会社 | プリント装置 |
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| US20130189350A1 (en) | 2013-07-25 |
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| US10675245B2 (en) | 2020-06-09 |
| CN103260702A (zh) | 2013-08-21 |
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