ES2395408T3 - Composiciones de fármaco lipófilas - Google Patents
Composiciones de fármaco lipófilas Download PDFInfo
- Publication number
- ES2395408T3 ES2395408T3 ES02766045T ES02766045T ES2395408T3 ES 2395408 T3 ES2395408 T3 ES 2395408T3 ES 02766045 T ES02766045 T ES 02766045T ES 02766045 T ES02766045 T ES 02766045T ES 2395408 T3 ES2395408 T3 ES 2395408T3
- Authority
- ES
- Spain
- Prior art keywords
- lipid
- drug
- substituted
- nitrotiazole
- composition
- 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.)
- Expired - Lifetime
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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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US134329 | 1993-10-12 | ||
| US31409201P | 2001-08-23 | 2001-08-23 | |
| US314092P | 2001-08-23 | ||
| US10/134,329 US7125568B2 (en) | 2001-08-23 | 2002-04-29 | Lipophilic drug compositions |
| PCT/US2002/026571 WO2003018064A2 (en) | 2001-08-23 | 2002-08-21 | Lipophilic drug compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2395408T3 true ES2395408T3 (es) | 2013-02-12 |
Family
ID=26832219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02766045T Expired - Lifetime ES2395408T3 (es) | 2001-08-23 | 2002-08-21 | Composiciones de fármaco lipófilas |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7125568B2 (https=) |
| EP (1) | EP1420828B1 (https=) |
| CA (1) | CA2458394C (https=) |
| ES (1) | ES2395408T3 (https=) |
| TW (1) | TWI302459B (https=) |
| WO (1) | WO2003018064A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050170004A1 (en) * | 2003-10-31 | 2005-08-04 | Vered Rosenberger | Nanoparticles for drug delivery |
| CA2604640A1 (en) * | 2005-04-12 | 2006-10-19 | Romark Laboratories L.C. | Methods for treating diseases through interruption of protein maturation, compounds that inhibit the function of molecular chaperones such as protein disulfide isomerases or interfere with glycosylation, pharmaceutical compositions comprising them, and screening methods for identifying therapeutic agents |
| AP2907A (en) | 2006-01-09 | 2014-05-31 | Romark Lab Lc | Viral hepatitis treatment |
| US20100119529A1 (en) * | 2006-05-12 | 2010-05-13 | Furgeson Darin Y | Elastin-like polymer delivery vehicles |
| US20100104625A1 (en) * | 2007-02-16 | 2010-04-29 | Cornell University | Biodegradable compositions and materials |
| US8354116B2 (en) * | 2007-06-18 | 2013-01-15 | Biochemics, Inc. | Bifunctional synthetic molecules |
| US7790401B2 (en) * | 2007-08-06 | 2010-09-07 | Siemens Healthcare Diagnostics | Methods for detection of immunosuppressant drugs |
| TW200936180A (en) * | 2007-11-27 | 2009-09-01 | Intervet Int Bv | Carrier particle for a microorganism or subunit thereof, pharmaceutical composition comprising such particles, method for preparation of this composition and its use in the treatment of animals |
| GB0724550D0 (en) * | 2007-12-18 | 2008-01-30 | Univ Hull | Formulations |
| GB0812513D0 (en) * | 2008-07-09 | 2008-08-13 | Univ Hull | Delivery vehicle |
| US20110082156A1 (en) * | 2009-10-05 | 2011-04-07 | Milne Jill C | Fatty acid acipimox derivatives and their uses |
| CA2811931C (en) | 2010-10-20 | 2015-06-16 | Galderma S.A. | Method of treating herpes virus infection using macrocyclic lactone compound |
| US20160289175A1 (en) * | 2013-11-05 | 2016-10-06 | Ultragenyx Pharmaceutical Inc. | Creatine analogs and the use thereof |
| EP3475442B1 (en) | 2016-06-23 | 2024-10-23 | The Regents of The University of Michigan | 12(s)-hydroxyeicosatrienoic acid compounds and their use as therapeutic agents |
| KR102678696B1 (ko) | 2017-12-01 | 2024-06-27 | 울트라제닉스 파마수티컬 인코포레이티드 | 크레아틴 전구약물, 조성물과 이의 사용 방법 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1437800A (en) | 1973-08-08 | 1976-06-03 | Phavic Sprl | Derivatives of 2-benzamido-5-nitro-thiazoles |
| US3931213A (en) | 1974-12-18 | 1976-01-06 | Interx Research Corporation | 3-Chloro-2-oxazolidinones |
| DE2655369A1 (de) | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| US4315018A (en) | 1978-12-07 | 1982-02-09 | Rossignol Jean F | Specific parasiticidal use of 2-benzamido-5-nitro-thiazole derivatives |
| US5340587A (en) | 1985-05-22 | 1994-08-23 | Liposome Technology, Inc. | Liposome/bronchodilator method & System |
| DE3686025T2 (de) | 1985-05-22 | 1993-01-07 | Liposome Technology Inc | Verfahren und system zum einatmen von liposomen. |
| JPH0751496B2 (ja) | 1986-04-02 | 1995-06-05 | 武田薬品工業株式会社 | リポソ−ムの製造法 |
| MX9203808A (es) | 1987-03-05 | 1992-07-01 | Liposome Co Inc | Formulaciones de alto contenido de medicamento: lipido, de agentes liposomicos-antineoplasticos. |
| EP0316594B1 (en) | 1987-10-21 | 1993-09-29 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
| US5994392A (en) | 1988-02-26 | 1999-11-30 | Neuromedica, Inc. | Antipsychotic prodrugs comprising an antipsychotic agent coupled to an unsaturated fatty acid |
| WO1990003795A1 (en) | 1988-10-05 | 1990-04-19 | Vestar, Inc. | Method of making liposomes with improved stability during drying |
| US5043165A (en) | 1988-12-14 | 1991-08-27 | Liposome Technology, Inc. | Novel liposome composition for sustained release of steroidal drugs |
| EP0458167B1 (en) | 1990-05-21 | 1997-04-23 | Abbott Laboratories | Fatty acid-pulmonary surfactant conjugates |
| US6147204A (en) | 1990-06-11 | 2000-11-14 | Nexstar Pharmaceuticals, Inc. | Nucleic acid ligand complexes |
| US6011020A (en) | 1990-06-11 | 2000-01-04 | Nexstar Pharmaceuticals, Inc. | Nucleic acid ligand complexes |
| US6168778B1 (en) | 1990-06-11 | 2001-01-02 | Nexstar Pharmaceuticals, Inc. | Vascular endothelial growth factor (VEGF) Nucleic Acid Ligand Complexes |
| US6060080A (en) | 1990-07-16 | 2000-05-09 | Daiichi Pharmaceutical Co., Ltd. | Liposomal products |
| DE69211691T2 (de) | 1991-04-19 | 1997-01-16 | Nexstar Pharmaceuticals Inc., Boulder, Col. | Pharmazeutische formulierung und pharmazeutisches verfahren |
| ATE146783T1 (de) | 1991-11-01 | 1997-01-15 | Upjohn Co | Substituierte aryl- und heteroaryl- phenyloxazolidinone |
| SK283420B6 (sk) | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| PL174222B1 (pl) | 1993-01-27 | 1998-06-30 | Inst Farmaceutyczny | Środek farmaceutyczny działający na ośrodkowy układ nerwowy |
| US5512671A (en) | 1993-02-16 | 1996-04-30 | Wake Forest University | Ether lipid-nucleoside covalent conjugates |
| US5576016A (en) | 1993-05-18 | 1996-11-19 | Pharmos Corporation | Solid fat nanoemulsions as drug delivery vehicles |
| US5688792A (en) | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
| US5668286A (en) | 1994-03-15 | 1997-09-16 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions containing them |
| US5534499A (en) | 1994-05-19 | 1996-07-09 | The University Of British Columbia | Lipophilic drug derivatives for use in liposomes |
| US5599831A (en) | 1994-05-27 | 1997-02-04 | Poretz; Ronald D. | Method of preparation of pharmaceutical compositions |
| EP0781138B1 (en) | 1994-08-29 | 2008-05-21 | Wake Forest University | Lipid analogs for treating viral infections |
| US5968961A (en) | 1997-05-07 | 1999-10-19 | Romark Laboratories, L.C. | Pharmaceutical compositions of tizoxanide and nitazoxanide |
| US5859038A (en) | 1994-09-08 | 1999-01-12 | Romark Laboratories, L.C. | Method for treatment of helicobacter pylori infections |
| MX9604483A (es) | 1994-09-08 | 1998-02-28 | Jean-Francois Rossignol | Derivados de benzamida, composiciones que contienen dicho derivado y uso de las mismas. |
| US5965590A (en) | 1994-09-08 | 1999-10-12 | Romark Lab Lc | Method for treatment of opportunistic infections with pharmaceutical compositions of tizoxanide and nitazoxanide |
| US5856348A (en) | 1994-09-08 | 1999-01-05 | Romark Laboratories, L.C. | Method for treatment of trematodes with pharmaceutical compositions of tizoxanide and nitazoxanide |
| US5952499A (en) | 1995-01-16 | 1999-09-14 | Commonwealth Scientific And Industrial Research Organisation | Therapeutic compound-fatty acid conjugates |
| US5907030A (en) | 1995-01-25 | 1999-05-25 | University Of Southern California | Method and compositions for lipidization of hydrophilic molecules |
| EP0825852B1 (en) | 1995-04-18 | 2004-07-07 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Liposome drug-loading method and composition |
| RU2175324C2 (ru) | 1995-09-01 | 2001-10-27 | Фармация Энд Апджон Компани | Фенилоксазолидиноны, имеющие с-с-связь с 4-8-членными гетероциклическими кольцами |
| ES2192221T3 (es) | 1995-10-30 | 2003-10-01 | Oleoyl Estrone Developments S | Monoesteres de oleato de estrogenos para el tratamiento de la obesidad o el sobrepeso. |
| ZA969622B (en) | 1995-12-13 | 1998-05-15 | Upjohn Co | Oxazolidinone antibacterial agents having a six-membered heteroaromatic ring. |
| IL117773A (en) | 1996-04-02 | 2000-10-31 | Pharmos Ltd | Solid lipid compositions of coenzyme Q10 for enhanced oral bioavailability |
| US5997899A (en) | 1996-10-01 | 1999-12-07 | Skyepharma Inc. | Method for producing liposomes with increased percent of compound encapsulated |
| US6071532A (en) | 1996-10-15 | 2000-06-06 | Emory University | Synthesis of glycophospholipid and peptide-phospholipid conjugates and uses thereof |
| US5874111A (en) | 1997-01-07 | 1999-02-23 | Maitra; Amarnath | Process for the preparation of highly monodispersed polymeric hydrophilic nanoparticles |
| US6120751A (en) | 1997-03-21 | 2000-09-19 | Imarx Pharmaceutical Corp. | Charged lipids and uses for the same |
| US6153119A (en) | 1997-05-09 | 2000-11-28 | Sung; Michael | Method and product for reducing tar and nicotine in cigarettes |
| CA2289702C (en) | 1997-05-14 | 2008-02-19 | Inex Pharmaceuticals Corp. | High efficiency encapsulation of charged therapeutic agents in lipid vesicles |
| US6080725A (en) | 1997-05-20 | 2000-06-27 | Galenica Pharmaceuticals, Inc. | Immunostimulating and vaccine compositions employing saponin analog adjuvants and uses thereof |
| US5935591A (en) | 1998-01-15 | 1999-08-10 | Romark Laboratories, L.C. | Method for treatment of equine protozoal myeloencephalitis with thiazolides |
| CN1305374A (zh) | 1998-07-14 | 2001-07-25 | 法玛西雅厄普约翰美国公司 | 治疗眼部感染的噁唑烷酮 |
| US6180136B1 (en) | 1998-11-10 | 2001-01-30 | Idexx Laboratories, Inc. | Phospholipid-coated microcrystals for the sustained release of pharmacologically active compounds and methods of their manufacture and use |
| GB9907715D0 (en) | 1999-04-01 | 1999-05-26 | Scherer Corp R P | Pharmaceutical compositions |
| GB9930026D0 (en) | 1999-12-21 | 2000-02-09 | Univ Sheffield | Novel compounds of unsaturated fatty acids |
| US6288238B1 (en) | 2000-09-19 | 2001-09-11 | Board Of Trustees Operating Michigan State University | Process for the preparation of 5-hydroxymethyl 2-oxazolidinone and novel intermediate |
| ATE556706T1 (de) | 2001-03-23 | 2012-05-15 | Luitpold Pharm Inc | Fettalkohol-arzneimittel-konjugate |
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- 2002-08-19 TW TW091118723A patent/TWI302459B/zh active
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- 2002-08-21 CA CA2458394A patent/CA2458394C/en not_active Expired - Fee Related
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| US20030108596A1 (en) | 2003-06-12 |
| EP1420828B1 (en) | 2012-09-26 |
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| WO2003018064A2 (en) | 2003-03-06 |
| CA2458394C (en) | 2013-04-23 |
| US20060147525A1 (en) | 2006-07-06 |
| EP1420828A2 (en) | 2004-05-26 |
| WO2003018064A3 (en) | 2003-09-25 |
| US7125568B2 (en) | 2006-10-24 |
| CA2458394A1 (en) | 2003-03-06 |
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