ZA200303432B - SN-38 lipid complexes and methods of use. - Google Patents
SN-38 lipid complexes and methods of use. Download PDFInfo
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- ZA200303432B ZA200303432B ZA200303432A ZA200303432A ZA200303432B ZA 200303432 B ZA200303432 B ZA 200303432B ZA 200303432 A ZA200303432 A ZA 200303432A ZA 200303432 A ZA200303432 A ZA 200303432A ZA 200303432 B ZA200303432 B ZA 200303432B
- Authority
- ZA
- South Africa
- Prior art keywords
- composition
- lipid
- compound
- liposomes
- cardiolipin
- Prior art date
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- -1 SN-38 lipid Chemical class 0.000 title claims description 9
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- ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 claims description 30
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- 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
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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
- A61K9/127—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
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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
- A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6905—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion
- A61K47/6911—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a liposome
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
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- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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EP (1) | EP1355634B8 (fr) |
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CN (1) | CN1531424A (fr) |
AT (1) | ATE413164T1 (fr) |
AU (1) | AU2002246510B2 (fr) |
BG (1) | BG107862A (fr) |
BR (1) | BR0115260A (fr) |
CA (1) | CA2427467C (fr) |
CZ (1) | CZ20031515A3 (fr) |
DE (1) | DE60136490D1 (fr) |
EA (1) | EA006741B1 (fr) |
HU (1) | HUP0302352A3 (fr) |
IL (1) | IL155696A0 (fr) |
MX (1) | MXPA03004095A (fr) |
NO (1) | NO20032069L (fr) |
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SK (1) | SK7092003A3 (fr) |
WO (1) | WO2002058622A2 (fr) |
ZA (1) | ZA200303432B (fr) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7262173B2 (en) | 1997-03-21 | 2007-08-28 | Georgetown University | Chemosensitizing with liposomes containing oligonucleotides |
WO2003030864A1 (fr) * | 2001-05-29 | 2003-04-17 | Neopharm, Inc. | Formulation liposomale d'irinotecan |
WO2003018018A2 (fr) * | 2001-08-24 | 2003-03-06 | Neopharm, Inc. | Compositions de vinorelbine et methodes d'utilisation |
EP1448237A1 (fr) * | 2001-11-09 | 2004-08-25 | Neopharm, Inc. | Traitement selectif des tumeurs exprimant l'interleukine 13 |
US7138512B2 (en) * | 2002-04-10 | 2006-11-21 | Georgetown University | Gene SHINC-2 and diagnostic and therapeutic uses thereof |
EP1513853A2 (fr) * | 2002-05-24 | 2005-03-16 | Neopharm, Inc. | Compositions de cardiolipine, leurs procedes de preparation et d'utilisation |
EA200401565A1 (ru) * | 2002-05-24 | 2005-04-28 | Неофарм, Инк. | Способ получения кардиолипина или аналога кардиолипина (варианты), способ получения липосомы и композиция кардиолипина для лечения заболеваний (варианты) |
AU2003240934A1 (en) * | 2002-05-29 | 2003-12-19 | Neopharm, Inc. | Method for determining oligonucleotide concentration |
WO2004035032A2 (fr) * | 2002-08-20 | 2004-04-29 | Neopharm, Inc. | Formulation de sn-38 a base de lipides pharmaceutiquement actifs |
WO2004017944A1 (fr) * | 2002-08-23 | 2004-03-04 | Neopharm, Inc. | Compositions de gemcitabine pour une administration de medicaments amelioree |
US20050277611A1 (en) * | 2002-10-16 | 2005-12-15 | Neopharm, Inc. | Cationic cardiolipin analoges and its use thereof |
BRPI0407096A (pt) * | 2003-02-03 | 2006-01-24 | Neopharm Inc | Taxano encapsulado em lipossomo estável, estéril e filtrável e outros fármacos antineoplásicos |
EA200501285A1 (ru) * | 2003-02-11 | 2006-02-24 | Неофарм, Инк. | Способ получения липосомальных препаратов |
WO2004087758A2 (fr) * | 2003-03-26 | 2004-10-14 | Neopharm, Inc. | Anticorps du recepteur alpha 2 il 13 et procedes d'utilisation |
WO2005000266A2 (fr) * | 2003-05-22 | 2005-01-06 | Neopharm, Inc. | Formulations liposomales combinees |
US20060078560A1 (en) * | 2003-06-23 | 2006-04-13 | Neopharm, Inc. | Method of inducing apoptosis and inhibiting cardiolipin synthesis |
EP1759699B1 (fr) * | 2004-06-18 | 2016-01-20 | Kabushiki Kaisha Yakult Honsha | Préparation de liposome contenant du camptothecin legérement soluble dans l'eau |
EA200700626A1 (ru) * | 2004-09-15 | 2007-10-26 | Васоджен Айеленд Лимитед | Лечение множественного склероза |
CA2699184A1 (fr) * | 2006-09-22 | 2008-03-27 | Labopharm Inc. | Compositions et procedes d'administration de medicament ciblee par rapport au ph |
US20100008998A1 (en) * | 2006-09-26 | 2010-01-14 | Samyang Corporation | Submicron nanoparticle of poorly water soluble camptothecin derivatives and process for preparation thereof |
WO2008127358A2 (fr) * | 2006-10-10 | 2008-10-23 | Jina Pharmaceuticals, Inc. | Systèmes aqueux pour la préparation de composés pharmaceutiques à base lipidique et leurs compositions, procédés et utilisations |
EP2088865B1 (fr) | 2006-11-06 | 2015-10-21 | Jina Pharmaceuticals Inc. | Procédés et compositions autour de guggulphospholipides |
US8067432B2 (en) * | 2008-03-31 | 2011-11-29 | University Of Kentucky Research Foundation | Liposomal, ring-opened camptothecins with prolonged, site-specific delivery of active drug to solid tumors |
WO2010045199A2 (fr) * | 2008-10-13 | 2010-04-22 | University Of South Florida | Méthode de modulation de l'activité de ship |
JP2012526049A (ja) * | 2009-05-04 | 2012-10-25 | インテザイン テクノロジーズ, インコーポレイテッド | 腫瘍治療のためのsn−38を含有するポリマーミセル |
US20110207764A1 (en) * | 2010-02-23 | 2011-08-25 | Valery Alakhov | Cyclopolysaccharide compositions |
US20110207760A1 (en) * | 2010-02-23 | 2011-08-25 | Valery Alakhov | Sn-38 compositions |
WO2011119995A2 (fr) | 2010-03-26 | 2011-09-29 | Cerulean Pharma Inc. | Formulations et procédés d'utilisation |
CN104856931B (zh) * | 2014-02-24 | 2019-06-18 | 石药集团中奇制药技术(石家庄)有限公司 | 一种两性霉素b纳米复合物及其制备方法 |
MX2016010998A (es) | 2014-02-27 | 2017-03-31 | Lycera Corp | Terapia celular adoptiva que usa un agonista de receptor huérfano gamma relacionado con receptor de ácido retinoico y métodos terapéuticos relacionados. |
EP3140291A4 (fr) | 2014-05-05 | 2018-01-10 | Lycera Corporation | Sulfonamide de tétrahydroquinoline et composés apparentés destinés à servir d'agonistes de rory et pour le traitement de maladies |
EP3292119A4 (fr) | 2015-05-05 | 2018-10-03 | Lycera Corporation | SULFONAMIDES DE DIHYDRO-2H-BENZO[B][1,4]OXAZINE ET COMPOSÉS APPARENTÉS DESTINÉS À ÊTRE UTILISÉS COMME AGONISTES DE RORy ET POUR LE TRAITEMENT DE MALADIES |
US10611740B2 (en) | 2015-06-11 | 2020-04-07 | Lycera Corporation | Aryl dihydro-2H-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
CN110302171A (zh) * | 2019-07-12 | 2019-10-08 | 山东大学 | 一种瘤内注射用sn-38-plga缓释微球及其制备方法和应用 |
US11286344B2 (en) | 2020-01-10 | 2022-03-29 | Tyndall Formulation Services, LLC | Polymer excipients for drug delivery applications |
WO2021142020A1 (fr) * | 2020-01-10 | 2021-07-15 | Tyndall Formulation Services, LLC | Formulations de sn-38 avec des polymères séquencés de poly(acide aminé) |
CA3231432A1 (fr) * | 2021-10-15 | 2023-04-20 | Tianyi Ke | Composition contenant un medicament antitumoral, son procede de preparation et son utilisation |
Family Cites Families (119)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CS180644B2 (en) | 1973-09-29 | 1978-01-31 | Takeda Chemical Industries Ltd | Process for preparing nonapeptides |
US3993754A (en) | 1974-10-09 | 1976-11-23 | The United States Of America As Represented By The United States Energy Research And Development Administration | Liposome-encapsulated actinomycin for cancer chemotherapy |
JPS5186117A (en) | 1975-01-27 | 1976-07-28 | Tanabe Seiyaku Co | Johoseibiryushiseizainoseiho |
US4115544A (en) | 1976-08-18 | 1978-09-19 | Alza Corporation | Ocular system made of bioerodible esters having linear ether |
GB1575343A (en) | 1977-05-10 | 1980-09-17 | Ici Ltd | Method for preparing liposome compositions containing biologically active compounds |
CH621479A5 (fr) | 1977-08-05 | 1981-02-13 | Battelle Memorial Institute | |
CH624011A5 (fr) | 1977-08-05 | 1981-07-15 | Battelle Memorial Institute | |
US4235871A (en) | 1978-02-24 | 1980-11-25 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
US4263428A (en) | 1978-03-24 | 1981-04-21 | The Regents Of The University Of California | Bis-anthracycline nucleic acid function inhibitors and improved method for administering the same |
CA1173360A (fr) | 1979-06-22 | 1984-08-28 | Jurg Schrank | Produits pharmaceutiques |
HU184141B (en) | 1979-12-27 | 1984-07-30 | Human Oltoanyagtermelo | Adjuvant particles compositions containing said particles and biologically active substances adsorbed thereon and a process for the preparation thereof |
US4348384A (en) | 1980-10-17 | 1982-09-07 | Dainippon Pharmaceutical Co., Ltd. | Pharmaceutical composition for oral administration containing coagulation factor VIII or IX |
US4419348A (en) | 1981-04-27 | 1983-12-06 | Georgetown University | Anthracycline glycoside compositions, their use and preparation |
US4473692A (en) | 1981-09-04 | 1984-09-25 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives and process for preparing same |
US4522803A (en) | 1983-02-04 | 1985-06-11 | The Liposome Company, Inc. | Stable plurilamellar vesicles, their preparation and use |
US4515736A (en) | 1983-05-12 | 1985-05-07 | The Regents Of The University Of California | Method for encapsulating materials into liposomes |
US4610868A (en) | 1984-03-20 | 1986-09-09 | The Liposome Company, Inc. | Lipid matrix carriers for use in drug delivery systems |
US4721612A (en) | 1984-04-12 | 1988-01-26 | The Liposome Company, Inc. | Steroidal liposomes |
AU587600B2 (en) * | 1985-01-11 | 1989-08-24 | Regents Of The University Of California, The | Method for preserving liposomes |
US4857319A (en) | 1985-01-11 | 1989-08-15 | The Regents Of The University Of California | Method for preserving liposomes |
US5023087A (en) | 1986-02-10 | 1991-06-11 | Liposome Technology, Inc. | Efficient method for preparation of prolonged release liposome-based drug delivery system |
US5187167A (en) | 1986-03-27 | 1993-02-16 | Imperial Chemical Industries Plc | Pharmaceutical compositions comprising quinazolin-4-one derivatives |
US4812312A (en) | 1987-03-03 | 1989-03-14 | Board Of Regents Of The University Of Texas System | Liposome-incorporated nystatin |
US5616334A (en) | 1987-03-05 | 1997-04-01 | The Liposome Company, Inc. | Low toxicity drug-lipid systems |
US5276019A (en) | 1987-03-25 | 1994-01-04 | The United States Of America As Represented By The Department Of Health And Human Services | Inhibitors for replication of retroviruses and for the expression of oncogene products |
US5264423A (en) | 1987-03-25 | 1993-11-23 | The United States Of America As Represented By The Department Of Health And Human Services | Inhibitors for replication of retroviruses and for the expression of oncogene products |
US4981968A (en) | 1987-03-31 | 1991-01-01 | Research Triangle Institute | Synthesis of camptothecin and analogs thereof |
JP2780755B2 (ja) * | 1987-05-22 | 1998-07-30 | ザ リポソーム カンパニー,インコーポレイテッド | プロスタグランジン‐脂質製剤 |
GB8727737D0 (en) | 1987-11-26 | 1987-12-31 | Ici Plc | Antitumour agents |
MX9203504A (es) | 1988-04-20 | 1992-07-01 | Liposome Co Inc | Complejo agente: lipido activo de alta proporcion. |
US4952408A (en) | 1988-05-23 | 1990-08-28 | Georgetown University | Liposome-encapsulated vinca alkaloids and their use in combatting tumors |
US5077057A (en) | 1989-04-05 | 1991-12-31 | The Regents Of The University Of California | Preparation of liposome and lipid complex compositions |
US5003097A (en) | 1989-10-02 | 1991-03-26 | The United States Of America As Represented By The Department Of Health And Human Services | Method for the sulfurization of phosphorous groups in compounds |
US5620689A (en) * | 1989-10-20 | 1997-04-15 | Sequus Pharmaceuuticals, Inc. | Liposomes for treatment of B-cell and T-cell disorders |
US5552154A (en) | 1989-11-06 | 1996-09-03 | The Stehlin Foundation For Cancer Research | Method for treating cancer with water-insoluble s-camptothecin of the closed lactone ring form and derivatives thereof |
US5389377A (en) | 1989-12-22 | 1995-02-14 | Molecular Bioquest, Inc. | Solid care therapeutic compositions and methods for making same |
US5665710A (en) | 1990-04-30 | 1997-09-09 | Georgetown University | Method of making liposomal oligodeoxynucleotide compositions |
US5422344A (en) | 1990-05-08 | 1995-06-06 | The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Method of treating retroviral infections in mammals |
US5543389A (en) | 1990-11-01 | 1996-08-06 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education On Behalf Of The Oregon Health Sciences University, A Non Profit Organization | Covalent polar lipid-peptide conjugates for use in salves |
US5162532A (en) | 1990-12-20 | 1992-11-10 | North Carolina State University | Intermediates and method of making camptothecin and camptothecin analogs |
US5247089A (en) | 1990-12-20 | 1993-09-21 | North Carolina State University | Method of making intermediates useful for the manufacture of camptothecin and camptothecin analogs |
US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
US5603872A (en) * | 1991-02-14 | 1997-02-18 | Baxter International Inc. | Method of binding recognizing substances to liposomes |
US5747469A (en) | 1991-03-06 | 1998-05-05 | Board Of Regents, The University Of Texas System | Methods and compositions comprising DNA damaging agents and p53 |
PT706373E (pt) | 1992-03-23 | 2000-11-30 | Univ Georgetown | Taxol encapsulado num liposoma e um metodo |
US5391745A (en) | 1992-07-23 | 1995-02-21 | Sloan-Kettering Institute For Cancer Research | Methods of preparation of camptothecin analogs |
WO1994005259A1 (fr) | 1992-09-02 | 1994-03-17 | Georgetown University | Procede d'encapsulation de glucosides d'anthracycline dans des liposomes |
US5552156A (en) * | 1992-10-23 | 1996-09-03 | Ohio State University | Liposomal and micellular stabilization of camptothecin drugs |
US5916596A (en) | 1993-02-22 | 1999-06-29 | Vivorx Pharmaceuticals, Inc. | Protein stabilized pharmacologically active agents, methods for the preparation thereof and methods for the use thereof |
US5352789A (en) | 1993-02-25 | 1994-10-04 | The Stehlin Foundation For Cancer Research | Methods for purifying camptothecin compounds |
US5527913A (en) | 1993-02-25 | 1996-06-18 | The Stehlin Foundation For Cancer Research | Methods for purifying camptothecin compounds |
US5776486A (en) | 1993-05-28 | 1998-07-07 | Aphios Corporation | Methods and apparatus for making liposomes containing hydrophobic drugs |
US5405963A (en) | 1993-06-10 | 1995-04-11 | Smithkline Beecham Corporation | Process for asymmetric total synthesis of camptothecin analogues |
US5475108A (en) | 1993-08-31 | 1995-12-12 | North Carolina State University | Camptothecin intermediates and method of making camptothecin and comptothecin analogs |
WO1995008986A1 (fr) * | 1993-09-27 | 1995-04-06 | Smithkline Beecham Corporation | Compositions de camptothecine |
TW406020B (en) | 1993-09-29 | 2000-09-21 | Bristol Myers Squibb Co | Stabilized pharmaceutical composition and its method for preparation and stabilizing solvent |
JP2828391B2 (ja) * | 1993-10-29 | 1998-11-25 | 東燃株式会社 | オリゴ糖を表面に有するリポソーム |
US5447936A (en) | 1993-12-22 | 1995-09-05 | Bionumerik Pharmaceuticals, Inc. | Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin and methods for uses thereof |
US5786344A (en) | 1994-07-05 | 1998-07-28 | Arch Development Corporation | Camptothecin drug combinations and methods with reduced side effects |
US5626862A (en) | 1994-08-02 | 1997-05-06 | Massachusetts Institute Of Technology | Controlled local delivery of chemotherapeutic agents for treating solid tumors |
DE69535665T2 (de) | 1994-08-19 | 2009-04-02 | La Region Wallonne | Konjugate enthaltend ein antitumorales mittel und deren verwendung |
US5776743A (en) | 1994-09-06 | 1998-07-07 | La Jolla Cancer Research Foundation | Method of sensitizing tumor cells with adenovirus E1A |
US5496830A (en) | 1994-09-14 | 1996-03-05 | Johns Hopkins University | Inhibition of hemoflagellates by camptothecin compounds |
US6214388B1 (en) | 1994-11-09 | 2001-04-10 | The Regents Of The University Of California | Immunoliposomes that optimize internalization into target cells |
US5919816A (en) | 1994-11-14 | 1999-07-06 | Bionumerik Pharmaceuticals, Inc. | Formulations and methods of reducing toxicity of antineoplastic agents |
US5736156A (en) | 1995-03-22 | 1998-04-07 | The Ohio State University | Liposomal anf micellular stabilization of camptothecin drugs |
US5834012A (en) * | 1995-05-03 | 1998-11-10 | Roman Perez-Soler | Lipid complexed topoisomerase I inhibitors |
US5726181A (en) | 1995-06-05 | 1998-03-10 | Bionumerik Pharmaceuticals, Inc. | Formulations and compositions of poorly water soluble camptothecin derivatives |
US5972955A (en) | 1995-06-06 | 1999-10-26 | Dr. Reddy's Research Foundation | Water soluble C-ring analogues of 20(S)-camptothecin |
SG50747A1 (en) | 1995-08-02 | 1998-07-20 | Tanabe Seiyaku Co | Comptothecin derivatives |
AU7732996A (en) | 1995-11-22 | 1997-06-11 | Research Triangle Institute | Camptothecin compounds with combined topoisomerase i inhibition and dna alkylation properties |
GB9601779D0 (en) | 1996-01-30 | 1996-04-03 | Pharmacia Spa | 9, 10 Disubstituted camptothecin derivatives |
US6096336A (en) * | 1996-01-30 | 2000-08-01 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
US6056973A (en) * | 1996-10-11 | 2000-05-02 | Sequus Pharmaceuticals, Inc. | Therapeutic liposome composition and method of preparation |
US5759767A (en) | 1996-10-11 | 1998-06-02 | Joseph R. Lakowicz | Two-photon and multi-photon measurement of analytes in animal and human tissues and fluids |
US5837282A (en) | 1996-10-30 | 1998-11-17 | University Of British Columbia | Ionophore-mediated liposome loading |
US5948750A (en) | 1996-10-30 | 1999-09-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
TW464652B (en) | 1996-10-30 | 2001-11-21 | Tanabe Seiyaku Co | S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof |
US6495579B1 (en) * | 1996-12-02 | 2002-12-17 | Angiotech Pharmaceuticals, Inc. | Method for treating multiple sclerosis |
US5827533A (en) | 1997-02-06 | 1998-10-27 | Duke University | Liposomes containing active agents aggregated with lipid surfactants |
US7262173B2 (en) * | 1997-03-21 | 2007-08-28 | Georgetown University | Chemosensitizing with liposomes containing oligonucleotides |
US20030229040A1 (en) * | 1997-03-21 | 2003-12-11 | Georgetown University | Cationic liposomal delivery system and therapeutic use thereof |
US6126965A (en) | 1997-03-21 | 2000-10-03 | Georgetown University School Of Medicine | Liposomes containing oligonucleotides |
US6559129B1 (en) * | 1997-03-21 | 2003-05-06 | Georgetown University | Cationic liposomal delivery system and therapeutic use thereof |
NZ503293A (en) * | 1997-09-16 | 2002-09-27 | Nexstar Pharmaceuticals Inc | Liposomal camptothecin formulations also comprising at least one phospholipid |
US6090407A (en) | 1997-09-23 | 2000-07-18 | Research Development Foundation | Small particle liposome aerosols for delivery of anti-cancer drugs |
US6183958B1 (en) | 1998-05-06 | 2001-02-06 | Variagenics, Inc. | Probes for variance detection |
WO1999066072A2 (fr) | 1998-06-16 | 1999-12-23 | Nova Molecular, Inc. | Procedes relatifs au traitement d'une maladie neurologique par determination du genotype de butyrylcholinesterase (bche) |
US6461637B1 (en) * | 2000-09-01 | 2002-10-08 | Neopharm, Inc. | Method of administering liposomal encapsulated taxane |
US6146659A (en) | 1998-07-01 | 2000-11-14 | Neopharm, Inc. | Method of administering liposomal encapsulated taxane |
US6664062B1 (en) * | 1998-07-20 | 2003-12-16 | Nuvelo, Inc. | Thymidylate synthase gene sequence variances having utility in determining the treatment of disease |
ATE238039T1 (de) * | 1998-09-16 | 2003-05-15 | Alza Corp | In liposomen eingeschlossene topoisomerase inhibitoren |
US6610492B1 (en) * | 1998-10-01 | 2003-08-26 | Variagenics, Inc. | Base-modified nucleotides and cleavage of polynucleotides incorporating them |
US6500650B1 (en) * | 1998-10-01 | 2002-12-31 | Variagenics, Inc. | Method for identifying polymorphisms |
US6458945B1 (en) * | 1998-10-01 | 2002-10-01 | Variagenics, Inc. | Method for analyzing polynucleotides |
US6777188B2 (en) * | 1998-10-01 | 2004-08-17 | Variagenics, Inc. | Genotyping by mass spectrometric analysis of allelic fragments |
WO2000020634A1 (fr) * | 1998-10-01 | 2000-04-13 | Nova Molecular, Inc. | Procedes pour traiter ou identifier un sujet susceptible de souffrir d'une maladie neurologique par une detection de la presence d'un allele du gene gpiiia variant et/ou du polypeptide gpiib variant |
US6395481B1 (en) * | 1999-02-16 | 2002-05-28 | Arch Development Corp. | Methods for detection of promoter polymorphism in a UGT gene promoter |
EP1216309A2 (fr) * | 1999-03-01 | 2002-06-26 | Variagenics, Inc. | Methodes permettant de cibler des molecules d'arn |
US6291676B1 (en) * | 1999-03-03 | 2001-09-18 | University Of Kentucky Research Foundation | Water-soluble derivatives of camptothecin/homocamptothecin |
US6573049B1 (en) * | 1999-07-26 | 2003-06-03 | Nuvelo, Inc. | Genotyping of the paraoxonase 1 gene for prognosing, diagnosing, and treating a disease |
US6475736B1 (en) * | 2000-05-23 | 2002-11-05 | Variagenics, Inc. | Methods for genetic analysis of DNA using biased amplification of polymorphic sites |
EA200300473A1 (ru) * | 2000-10-16 | 2003-08-28 | Неофарм, Инк. | Терапевтическая композиция на основе митоксантрона (варианты) и липидный препарат, способ его получения и способ лечения заболевания млекопитающего с его использованием |
WO2002059337A1 (fr) * | 2001-01-26 | 2002-08-01 | Georgetown University School Of Medicine | Gène anti-apoptotique scc-s2 et ses utilisations diagnostiques et thérapeutiques |
AU2002303261A1 (en) * | 2001-04-06 | 2002-10-21 | Georgetown University | Gene brcc2 and diagnostic and therapeutic uses thereof |
AU2002305151A1 (en) * | 2001-04-06 | 2002-10-21 | Georgetown University | Gene scc-112 and diagnostic and therapeutic uses thereof |
WO2002081642A2 (fr) * | 2001-04-06 | 2002-10-17 | Georgetown University | Gene brcc-3 et ses utilisations diagnostiques et therapeutiques |
WO2003030864A1 (fr) * | 2001-05-29 | 2003-04-17 | Neopharm, Inc. | Formulation liposomale d'irinotecan |
EP1448237A1 (fr) * | 2001-11-09 | 2004-08-25 | Neopharm, Inc. | Traitement selectif des tumeurs exprimant l'interleukine 13 |
US7138512B2 (en) * | 2002-04-10 | 2006-11-21 | Georgetown University | Gene SHINC-2 and diagnostic and therapeutic uses thereof |
US7244565B2 (en) * | 2002-04-10 | 2007-07-17 | Georgetown University | Gene shinc-3 and diagnostic and therapeutic uses thereof |
WO2003099213A2 (fr) * | 2002-05-20 | 2003-12-04 | Neopharm, Inc. | Methode de reduction du nombre de plaquettes |
US20030228317A1 (en) * | 2002-05-22 | 2003-12-11 | Prafulla Gokhale | Gene BRCC-1 and diagnostic and therapeutic uses thereof |
EP1513853A2 (fr) * | 2002-05-24 | 2005-03-16 | Neopharm, Inc. | Compositions de cardiolipine, leurs procedes de preparation et d'utilisation |
EA200401565A1 (ru) * | 2002-05-24 | 2005-04-28 | Неофарм, Инк. | Способ получения кардиолипина или аналога кардиолипина (варианты), способ получения липосомы и композиция кардиолипина для лечения заболеваний (варианты) |
AU2003240934A1 (en) * | 2002-05-29 | 2003-12-19 | Neopharm, Inc. | Method for determining oligonucleotide concentration |
WO2004035032A2 (fr) * | 2002-08-20 | 2004-04-29 | Neopharm, Inc. | Formulation de sn-38 a base de lipides pharmaceutiquement actifs |
WO2004017944A1 (fr) * | 2002-08-23 | 2004-03-04 | Neopharm, Inc. | Compositions de gemcitabine pour une administration de medicaments amelioree |
US20050277611A1 (en) * | 2002-10-16 | 2005-12-15 | Neopharm, Inc. | Cationic cardiolipin analoges and its use thereof |
-
2001
- 2001-11-09 EA EA200300550A patent/EA006741B1/ru not_active IP Right Cessation
- 2001-11-09 CZ CZ20031515A patent/CZ20031515A3/cs unknown
- 2001-11-09 AU AU2002246510A patent/AU2002246510B2/en not_active Ceased
- 2001-11-09 WO PCT/US2001/043325 patent/WO2002058622A2/fr active IP Right Grant
- 2001-11-09 NZ NZ525552A patent/NZ525552A/en unknown
- 2001-11-09 HU HU0302352A patent/HUP0302352A3/hu unknown
- 2001-11-09 CA CA002427467A patent/CA2427467C/fr not_active Expired - Fee Related
- 2001-11-09 KR KR1020037006195A patent/KR100869824B1/ko not_active IP Right Cessation
- 2001-11-09 DE DE60136490T patent/DE60136490D1/de not_active Expired - Lifetime
- 2001-11-09 EP EP01994079A patent/EP1355634B8/fr not_active Expired - Lifetime
- 2001-11-09 MX MXPA03004095A patent/MXPA03004095A/es active IP Right Grant
- 2001-11-09 JP JP2002558957A patent/JP4524071B2/ja not_active Expired - Fee Related
- 2001-11-09 AT AT01994079T patent/ATE413164T1/de not_active IP Right Cessation
- 2001-11-09 CN CNA018186351A patent/CN1531424A/zh active Pending
- 2001-11-09 IL IL15569601A patent/IL155696A0/xx unknown
- 2001-11-09 SK SK709-2003A patent/SK7092003A3/sk unknown
- 2001-11-09 BR BR0115260-2A patent/BR0115260A/pt not_active IP Right Cessation
- 2001-11-09 PL PL01363618A patent/PL363618A1/xx not_active Application Discontinuation
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2003
- 2003-04-28 US US10/424,258 patent/US7390502B2/en not_active Expired - Fee Related
- 2003-05-05 ZA ZA200303432A patent/ZA200303432B/en unknown
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Also Published As
Publication number | Publication date |
---|---|
HUP0302352A3 (en) | 2007-03-28 |
KR100869824B1 (ko) | 2008-11-21 |
EP1355634A2 (fr) | 2003-10-29 |
BR0115260A (pt) | 2005-08-16 |
CN1531424A (zh) | 2004-09-22 |
EA200300550A1 (ru) | 2004-06-24 |
EP1355634B1 (fr) | 2008-11-05 |
CA2427467A1 (fr) | 2002-08-01 |
EA006741B1 (ru) | 2006-04-28 |
KR20030072352A (ko) | 2003-09-13 |
IL155696A0 (en) | 2003-11-23 |
US20030215492A1 (en) | 2003-11-20 |
DE60136490D1 (de) | 2008-12-18 |
JP2004529086A (ja) | 2004-09-24 |
CA2427467C (fr) | 2010-01-12 |
EP1355634A4 (fr) | 2005-07-06 |
MXPA03004095A (es) | 2004-09-10 |
US7390502B2 (en) | 2008-06-24 |
NO20032069D0 (no) | 2003-05-08 |
EP1355634B8 (fr) | 2009-03-04 |
ATE413164T1 (de) | 2008-11-15 |
CZ20031515A3 (cs) | 2003-09-17 |
AU2002246510B2 (en) | 2007-09-20 |
NO20032069L (no) | 2003-07-02 |
SK7092003A3 (en) | 2004-06-08 |
WO2002058622A2 (fr) | 2002-08-01 |
HUP0302352A2 (hu) | 2003-11-28 |
AU2002246510A2 (en) | 2002-08-06 |
BG107862A (bg) | 2004-06-30 |
WO2002058622A3 (fr) | 2003-08-28 |
JP4524071B2 (ja) | 2010-08-11 |
PL363618A1 (en) | 2004-11-29 |
NZ525552A (en) | 2005-04-29 |
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