DE60313299T2 - Selbstemulgierende systeme zur abgabe von taxoiden - Google Patents
Selbstemulgierende systeme zur abgabe von taxoiden Download PDFInfo
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- DE60313299T2 DE60313299T2 DE60313299T DE60313299T DE60313299T2 DE 60313299 T2 DE60313299 T2 DE 60313299T2 DE 60313299 T DE60313299 T DE 60313299T DE 60313299 T DE60313299 T DE 60313299T DE 60313299 T2 DE60313299 T2 DE 60313299T2
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- paclitaxel
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cash Registers Or Receiving Machines (AREA)
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| US361090P | 2002-03-01 | ||
| EP02290513A EP1340497A1 (en) | 2002-03-01 | 2002-03-01 | Self emulsifying drug delivery systems for poorly soluble drugs |
| PCT/IB2003/001336 WO2003074027A2 (en) | 2002-03-01 | 2003-02-28 | Self emulsifying drug delivery systems for poorly soluble drugs |
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| EP1498120A1 (en) * | 2003-07-18 | 2005-01-19 | Aventis Pharma S.A. | Semi-solid formulations for the oral administration of taxoids |
| WO2005027906A1 (en) | 2003-09-18 | 2005-03-31 | Macusight, Inc. | Transscleral delivery |
| FR2861992B1 (fr) * | 2003-11-10 | 2007-07-20 | Sanofi Synthelabo | Composition pharmaceutique destinee a l'administration orale d'un derive de pyrazole-3-carboxamide. |
| US7989490B2 (en) * | 2004-06-02 | 2011-08-02 | Cordis Corporation | Injectable formulations of taxanes for cad treatment |
| US8557861B2 (en) | 2004-09-28 | 2013-10-15 | Mast Therapeutics, Inc. | Low oil emulsion compositions for delivering taxoids and other insoluble drugs |
| US8663639B2 (en) | 2005-02-09 | 2014-03-04 | Santen Pharmaceutical Co., Ltd. | Formulations for treating ocular diseases and conditions |
| GB2438544A (en) | 2005-02-09 | 2007-11-28 | Cooper Internat Corp | Liquid formulations for treatment of diseases or conditions |
| TWI376239B (en) * | 2006-02-01 | 2012-11-11 | Andrew Xian Chen | Vitamin e succinate stabilized pharmaceutical compositions, methods for the preparation and the use thereof |
| CA2635797C (en) | 2006-02-09 | 2015-03-31 | Macusight, Inc. | Stable formulations, and methods of their preparation and use |
| CN101443004B (zh) | 2006-03-23 | 2013-03-06 | 参天制药株式会社 | 用于与血管通透性有关的疾病或病症的制剂 |
| WO2008042841A2 (en) * | 2006-10-02 | 2008-04-10 | Dr. Reddy's Laboratories Limited | Docetaxel compositions |
| US8178564B2 (en) * | 2006-11-06 | 2012-05-15 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8168661B2 (en) | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8173686B2 (en) | 2006-11-06 | 2012-05-08 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8168662B1 (en) | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| CN101677987A (zh) * | 2007-06-22 | 2010-03-24 | 赛多斯有限责任公司 | 不含吐温80的多西他赛的增溶制剂 |
| US20100260832A1 (en) * | 2007-06-27 | 2010-10-14 | Poniard Pharmaceuticals, Inc. | Combination therapy for ovarian cancer |
| CN101809024A (zh) * | 2007-07-16 | 2010-08-18 | 铂雅制药公司 | 吡铂的口服制剂 |
| EP2200613B1 (en) | 2007-09-21 | 2018-09-05 | The Johns Hopkins University | Phenazine derivatives and uses thereof |
| EP2262369A4 (en) * | 2008-04-04 | 2013-05-29 | Robert Shorr | LIPID-OIL-WATER-NANOEMULSION-DELIVERY SYSTEM FOR ACTIVE SUBSTANCES WITH MICROTUBULI INTERACTION |
| US8541465B2 (en) | 2009-10-19 | 2013-09-24 | Scidose, Llc | Docetaxel formulations with lipoic acid and/or dihydrolipoic acid |
| US8476310B2 (en) | 2009-10-19 | 2013-07-02 | Scidose Llc | Docetaxel formulations with lipoic acid |
| US8912228B2 (en) | 2009-10-19 | 2014-12-16 | Scidose Llc | Docetaxel formulations with lipoic acid |
| US7772274B1 (en) | 2009-10-19 | 2010-08-10 | Scidose, Llc | Docetaxel formulations with lipoic acid |
| US20110092579A1 (en) * | 2009-10-19 | 2011-04-21 | Scidose Llc | Solubilized formulation of docetaxel |
| RU2603833C2 (ru) | 2010-11-08 | 2016-11-27 | Кадила Фармасьютикалз Лимитед | Фармацевтическая композиция таксоидов |
| EP2857043B1 (en) | 2012-05-31 | 2019-01-23 | Terumo Kabushiki Kaisha | pH-SENSITIVE CARRIER AND METHOD FOR PRODUCTION THEREOF, pH-SENSITIVE MEDICINE AND pH-SENSITIVE PHARMACEUTICAL COMPOSITION EACH CONTAINING SAID CARRIER, AND CULTURE METHOD USING SAID pH-SENSITIVE MEDICINE OR SAID pH-SENSITIVE PHARMACEUTICAL COMPOSITION |
| EP3424493A1 (en) * | 2017-07-07 | 2019-01-09 | SolMic Research GmbH | Stable cannabinoid compositions |
| CN109589305B (zh) * | 2018-12-03 | 2021-03-19 | 昆明积大制药股份有限公司 | 多西他赛-环孢素a共包载自乳化制剂及其制备方法 |
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| US5567424A (en) * | 1994-06-10 | 1996-10-22 | Reliv International, Inc. | Fiber, antioxidant, herbal and enzyme supplemented beverage composition for human consumption |
| US5536516A (en) * | 1994-08-24 | 1996-07-16 | Renaissance Herbs, Inc. | Hydroxycitric acid concentrate and food products prepared therefrom |
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| IT1276253B1 (it) * | 1995-12-15 | 1997-10-27 | Sigma Tau Ind Farmaceuti | Composizione farmaceutica contenente l-carnitina o alcanoil l-carnitine per la prevenzione ed il trattamento di stati morbosi |
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| US6071904A (en) * | 1996-12-11 | 2000-06-06 | Alcon Laboratories, Inc. | Process for manufacturing ophthalmic suspensions |
| US6458373B1 (en) * | 1997-01-07 | 2002-10-01 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| GB9715759D0 (en) * | 1997-07-26 | 1997-10-01 | Danbiosyst Uk | New emulsion formulations |
| PT999826E (pt) * | 1997-07-29 | 2004-09-30 | Upjohn Co | Formulacao auto-emulsionante para compostos lipofilos |
| US6160172A (en) * | 1997-08-27 | 2000-12-12 | Vittal Mallya Scientific Research Foundation | Soluble double metal salt of group IA and IIA of (-) hydroxycitric acid, process of preparing the same and its use in beverages and other food products without effecting their flavor and properties |
| IL131217A0 (en) * | 1998-03-10 | 2001-01-28 | Napro Biotherapeutics Inc | Novel methods and compositions for delivery of taxanes |
| AU5802499A (en) * | 1998-09-01 | 2000-03-21 | Amway Corporation | Diet composition and method of weight management |
| US6294192B1 (en) * | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
| US6207714B1 (en) * | 1999-09-14 | 2001-03-27 | Dallas L. Clouatre | Methods and pharmaceutical preparations for improving glucose metabolism with (−)-hydroxycitric acid |
| US6447807B1 (en) * | 1999-09-14 | 2002-09-10 | Dallas L. Clouatre | Potassium (-)-hydroxycitric acid methods for pharmaceutical preparations for stable and controlled delivery |
| KR20010100194A (ko) * | 2000-03-13 | 2001-11-14 | 박호군 | 여러 가지 물질의 가용화용 조성물과 제형 및 그들의제조방법 |
| US6399089B1 (en) * | 2000-05-15 | 2002-06-04 | A. Glenn Braswell | Compositions and methods for regulating metabolism and balancing body weight |
| US6383482B1 (en) * | 2000-08-24 | 2002-05-07 | Vitacost.Com, Inc. | Weight loss composition containing green tea, hydroxycitric acid, 5-hydroxytryptophan, glucomannan, picolinate and lactobacillus |
| US6579866B2 (en) * | 2000-12-28 | 2003-06-17 | Mccleary Larry | Composition and method for modulating nutrient partitioning |
| US20040157929A1 (en) * | 2002-04-01 | 2004-08-12 | Ohia Sunny E. | Method for increasing serotonin levels in a person by administration of a composition incorporating(-)hydroxycitric acid, and related compositions thereof |
| US6476071B1 (en) * | 2001-05-07 | 2002-11-05 | Dallas L. Clouatre | Correcting polymorphic metabolic dysfunction with (−)-hydroxycitric acid |
| US6482858B1 (en) * | 2001-06-20 | 2002-11-19 | Dallas L Clouatre | (−)-hydroxycitric acid for wound healing and immunomodulation |
| US6441041B1 (en) * | 2001-06-20 | 2002-08-27 | Dallas L. Clouatre | (-)-hydroxycitric acid for the prevention of osteoporosis |
| US6638542B2 (en) * | 2001-09-20 | 2003-10-28 | Nutricia N.V. | Reducing appetite in mammals by administering procyanidin and hydroxycitric acid |
| US7119110B2 (en) * | 2001-10-05 | 2006-10-10 | Interhealth Nutraceuticals Incorporated | Method and composition for preventing or reducing the symptoms of insulin resistance syndrome |
| US20030119913A1 (en) * | 2001-12-20 | 2003-06-26 | Ohia Sunny E. | Method for increasing serotonin levels in a person by administration of a composition incorporating (-)-hydroxycitric acid, and related compositions thereof |
| US7507421B2 (en) * | 2002-04-30 | 2009-03-24 | Unibar Corporation | Hydroxycitric acid salt composition and method of making |
| US20040186181A1 (en) * | 2003-03-21 | 2004-09-23 | Interhealth Nutraceuticals, Incorporated | Method and composition for decreasing ghrelin levels |
-
2003
- 2003-02-28 IL IL16380803A patent/IL163808A0/xx unknown
- 2003-02-28 ES ES03710117T patent/ES2283756T3/es not_active Expired - Lifetime
- 2003-02-28 JP JP2003572547A patent/JP2005523295A/ja active Pending
- 2003-02-28 AU AU2003214538A patent/AU2003214538A1/en not_active Abandoned
- 2003-02-28 US US10/507,857 patent/US20050232952A1/en not_active Abandoned
- 2003-02-28 DE DE60313299T patent/DE60313299T2/de not_active Expired - Fee Related
- 2003-02-28 CA CA002478424A patent/CA2478424A1/en not_active Abandoned
- 2003-02-28 EP EP03710117A patent/EP1480636B1/en not_active Expired - Lifetime
- 2003-02-28 WO PCT/IB2003/001336 patent/WO2003074027A2/en not_active Ceased
- 2003-02-28 AT AT03710117T patent/ATE359779T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US20050232952A1 (en) | 2005-10-20 |
| WO2003074027A8 (en) | 2004-10-07 |
| CA2478424A1 (en) | 2003-09-12 |
| EP1480636A2 (en) | 2004-12-01 |
| DE60313299D1 (de) | 2007-05-31 |
| JP2005523295A (ja) | 2005-08-04 |
| ES2283756T3 (es) | 2007-11-01 |
| WO2003074027A2 (en) | 2003-09-12 |
| AU2003214538A1 (en) | 2003-09-16 |
| WO2003074027A3 (en) | 2003-12-18 |
| EP1480636B1 (en) | 2007-04-18 |
| IL163808A0 (en) | 2005-12-18 |
| ATE359779T1 (de) | 2007-05-15 |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |