ES2614086T3 - Análogos de poliéter de desferritiocina - Google Patents
Análogos de poliéter de desferritiocina Download PDFInfo
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- ES2614086T3 ES2614086T3 ES06739627.5T ES06739627T ES2614086T3 ES 2614086 T3 ES2614086 T3 ES 2614086T3 ES 06739627 T ES06739627 T ES 06739627T ES 2614086 T3 ES2614086 T3 ES 2614086T3
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- dadft
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- iron
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/04—Chelating agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Toxicology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66804505P | 2005-04-04 | 2005-04-04 | |
| US668045P | 2005-04-04 | ||
| PCT/US2006/010945 WO2006107626A1 (en) | 2005-04-04 | 2006-03-22 | Desferrithiocin polyether analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2614086T3 true ES2614086T3 (es) | 2017-05-29 |
Family
ID=36676582
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06739627.5T Active ES2614086T3 (es) | 2005-04-04 | 2006-03-22 | Análogos de poliéter de desferritiocina |
| ES16196408T Active ES2732625T3 (es) | 2005-04-04 | 2006-03-22 | Análogos de poliéter de desferritiocina |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16196408T Active ES2732625T3 (es) | 2005-04-04 | 2006-03-22 | Análogos de poliéter de desferritiocina |
Country Status (14)
| Country | Link |
|---|---|
| US (6) | US8278458B2 (enExample) |
| EP (2) | EP3190106B1 (enExample) |
| JP (3) | JP5202299B2 (enExample) |
| CN (1) | CN101189216B (enExample) |
| AU (1) | AU2006232929B9 (enExample) |
| BR (1) | BRPI0610644B8 (enExample) |
| CA (1) | CA2603385C (enExample) |
| CY (1) | CY1119002T1 (enExample) |
| DK (2) | DK3190106T3 (enExample) |
| ES (2) | ES2614086T3 (enExample) |
| MX (1) | MX2007012226A (enExample) |
| PL (2) | PL1866296T3 (enExample) |
| TR (1) | TR201910900T4 (enExample) |
| WO (1) | WO2006107626A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6083966A (en) | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| AU2003270473A1 (en) | 2003-09-09 | 2005-04-27 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| BRPI0610644B8 (pt) | 2005-04-04 | 2021-05-25 | Univ Florida | composto e composição farmacêutica que compreende tal composto e um veículo ou diluente farmaceuticamente aceitável. |
| JP2010512398A (ja) * | 2006-12-12 | 2010-04-22 | ユニバーシティ オブ フロリダ | デスフェリチオシン類縁体アクチニド除染剤 |
| US8324397B2 (en) * | 2007-03-15 | 2012-12-04 | University Of Florida Research Foundation, Inc. | Desferrithiocin polyether analogues |
| MY163516A (en) * | 2008-07-14 | 2017-09-15 | Ferrokin Biosciences Inc | Novel salts and polymorphs of desazadesferrithiocin polyether analogues as metal chelation agents |
| BR112012001761A2 (pt) * | 2009-07-27 | 2017-05-09 | Ferrokin Bioscience Inc | composto de formula i, composto farmacêutica e método de tratamento de uma condição mediada por metal em um indivduo |
| JP5925679B2 (ja) * | 2009-08-25 | 2016-05-25 | ユニバーシティ オブ フロリダ リサーチ ファウンデーション，インコーポレイティド | デスフェリチオシンポリエーテル類似体およびその使用 |
| US20130053387A1 (en) * | 2010-05-04 | 2013-02-28 | FerroKin BioScience, Inc. | Desazadesferrothiocin and desazadesferrothiocin polyether analogues as metal chelation agents |
| AU2012347595A1 (en) | 2011-12-09 | 2014-06-26 | Ferrokin Biosciences, Inc. | Oral formulations for treating metal overload |
| KR102111176B1 (ko) * | 2011-12-16 | 2020-05-15 | 유니버시티 오브 플로리다 리서치 파운데이션, 인코포레이티드 | 4'-데스페리티오신 유사체의 용도 |
| AU2014228308A1 (en) | 2013-03-15 | 2015-08-27 | Ferrokin Biosciences, Inc. | Polymorph forms of desazadesferrithiocin analogs |
| JP6838966B2 (ja) * | 2013-11-22 | 2021-03-03 | ユニバーシティー オブ フロリダ リサーチ ファンデーション， インク． | デスフェリチオシン類似体およびその使用 |
| JP2017526815A (ja) * | 2014-07-18 | 2017-09-14 | アプライド マテリアルズ インコーポレイテッドＡｐｐｌｉｅｄ Ｍａｔｅｒｉａｌｓ，Ｉｎｃｏｒｐｏｒａｔｅｄ | レーザ及びプラズマを用いた付加製造 |
| JP2018515475A (ja) * | 2015-04-27 | 2018-06-14 | ユニバーシティー オブ フロリダ リサーチ ファンデーション， インク． | 代謝的にプログラムされた金属キレーターおよびその使用 |
| US10982136B2 (en) | 2016-02-26 | 2021-04-20 | The Regents Of The University Of California | Ligand-sensitized lanthanide nanocrystals as ultraviolet downconverters |
| US20180036228A1 (en) | 2016-08-05 | 2018-02-08 | Steven Keith BURKE | Dosing regimens for treating metal-mediated conditions |
| EP3503930B1 (en) | 2016-08-29 | 2024-12-11 | Fred Hutchinson Cancer Center | Chelating platform for delivery of radionuclides |
| CA3035966A1 (en) | 2016-09-06 | 2018-03-15 | The Regents Of The University Of California | Formulations of hydroxypyridonate actinide/lanthanide decorporation agents |
| CA3038670A1 (en) | 2016-09-29 | 2018-04-05 | The Regents Of The University Of California | Chelating molecules |
| EP3520117B1 (en) | 2016-09-29 | 2023-11-08 | The Regents of The University of California | Separation of metal ions by liquid-liquid extraction |
Family Cites Families (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274207A (en) * | 1966-09-20 | Processes for preparing thiazole carboxylic acids | ||
| US3809754A (en) * | 1968-12-31 | 1974-05-07 | Medial De Toledo & Cie | Method of treating diseases of the mucous membrane using compounds of a thiazolidine carboxylic acid and pharmaceutical preparations thereof |
| US3882110A (en) * | 1969-06-11 | 1975-05-06 | Roussel Uclaf | Novel 2-alkyl-5-thiazole-carboxylic acid derivatives |
| FR2062210A5 (enExample) | 1969-09-17 | 1971-06-25 | Godo Shusei Kk | |
| FR2062120A5 (enExample) | 1969-10-10 | 1971-06-25 | Messier Fa | |
| FR2141526B1 (enExample) | 1971-06-14 | 1975-05-30 | Roussel Uclaf | |
| DE2245560A1 (de) | 1972-09-16 | 1974-03-21 | Basf Ag | Verfahren zur herstellung von 4alkoxycarbonyl-2-thiazolinen |
| US4430344A (en) * | 1978-04-08 | 1984-02-07 | Santen Pharmaceutical Co., Ltd. | Antihypertensive 4-thiazolidinecarboxylic acids |
| CS205217B1 (cs) | 1979-04-05 | 1981-05-29 | Zdenek Vitamvas | Dozimetr ionizujícího záření |
| US4270537A (en) | 1979-11-19 | 1981-06-02 | Romaine Richard A | Automatic hypodermic syringe |
| DE3002989A1 (de) * | 1980-01-29 | 1981-07-30 | Hoechst Ag, 6000 Frankfurt | Hydroxyphenyl-thiazol, -thiazolin und -thiazolidin-carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des kollagenstoffwechsels |
| JPS5758682A (en) | 1980-07-28 | 1982-04-08 | Ciba Geigy Ag | Thiazoline derivatives, manufacture and medicinal composition containing same |
| EP0045281B1 (de) * | 1980-07-28 | 1985-05-08 | Ciba-Geigy Ag | Thiazolinderivate und Verfahren zu ihrer Herstellung |
| JPS5772975A (en) * | 1980-10-24 | 1982-05-07 | Kureha Chem Ind Co Ltd | 2-substituted phenylthiazole derviative, and medicine for peptic ulcer containing said derivative as active component |
| US4367233A (en) * | 1981-10-02 | 1983-01-04 | American Home Products Corporation | Inhibitors of mammalian collagenase |
| JPS62501769A (ja) * | 1984-12-18 | 1987-07-16 | デイビツト ラビン | 細胞毒性アルデヒドとベニシラミンとの反応性成物を含有する抗腫瘍組成物及びその使用方法 |
| US4596556A (en) | 1985-03-25 | 1986-06-24 | Bioject, Inc. | Hypodermic injection apparatus |
| HU200177B (en) * | 1985-06-18 | 1990-04-28 | Biogal Gyogyszergyar | Process for producing thiazolidinecarboxylic acids and pharmaceutical compositions comprising such compounds |
| US4736060A (en) * | 1985-08-06 | 1988-04-05 | Nippon Rikagakuyakuhin Co., Ltd. | Method for optical resolution of DL-cysteine and (R,S)-1-(1-naphthyl) ethylamine |
| EP0214101A3 (de) | 1985-09-03 | 1989-05-31 | Ciba-Geigy Ag | Verwendung von Eisen(III)-Chelatoren vom Typ Desferrioxamin B und Desferriferrithiocin zur Behandlung von Malaria |
| EP0214933A3 (de) | 1985-09-03 | 1989-05-24 | Ciba-Geigy Ag | Kombinationspräparate zur Behandlung von Malaria |
| JPS62142168A (ja) * | 1985-10-16 | 1987-06-25 | Mitsubishi Chem Ind Ltd | チアゾ−ル誘導体及びそれを有効成分とするロイコトリエンきつ抗剤 |
| DE3621540A1 (de) | 1986-06-27 | 1988-01-07 | Basf Ag | Chinolinderivate, verfahren zu ihrer herstellung, diese enthaltende mikrobizide und ihre verwendung zur bekaempfung von bakterien und pilzen |
| US4886499A (en) | 1986-12-18 | 1989-12-12 | Hoffmann-La Roche Inc. | Portable injection appliance |
| GB8704027D0 (en) | 1987-02-20 | 1987-03-25 | Owen Mumford Ltd | Syringe needle combination |
| US4790824A (en) | 1987-06-19 | 1988-12-13 | Bioject, Inc. | Non-invasive hypodermic injection device |
| US4940460A (en) | 1987-06-19 | 1990-07-10 | Bioject, Inc. | Patient-fillable and non-invasive hypodermic injection device assembly |
| US4941880A (en) | 1987-06-19 | 1990-07-17 | Bioject, Inc. | Pre-filled ampule and non-invasive hypodermic injection device assembly |
| DE3735757A1 (de) * | 1987-10-22 | 1989-05-03 | Degussa | Optisch aktive salze aus einem substituierten thiazolidin-4-carboxylat und 3-chlor-2-hydroxypropyltrimethylammonium, deren herstellung und verwendung |
| ES2047149T3 (es) | 1988-01-20 | 1994-02-16 | Ciba Geigy Ag | Procedimiento para la obtencion de compuestos complejos. |
| US5339163A (en) | 1988-03-16 | 1994-08-16 | Canon Kabushiki Kaisha | Automatic exposure control device using plural image plane detection areas |
| FR2638359A1 (fr) | 1988-11-03 | 1990-05-04 | Tino Dalto | Guide de seringue avec reglage de la profondeur de penetration de l'aiguille dans la peau |
| GB8826035D0 (en) * | 1988-11-07 | 1988-12-14 | Ici Plc | Herbicidal compositions |
| US5182402A (en) * | 1988-11-07 | 1993-01-26 | Imperial Chemical Industries Plc | Herbicidal compositions |
| US5106992A (en) * | 1989-07-28 | 1992-04-21 | E. R. Squibb & Sons, Inc. | 3,5-dihydroxypentanoic acid derivatives useful as antihypercholesterolemic agents and method for preparing same |
| US5312335A (en) | 1989-11-09 | 1994-05-17 | Bioject Inc. | Needleless hypodermic injection device |
| US5064413A (en) | 1989-11-09 | 1991-11-12 | Bioject, Inc. | Needleless hypodermic injection device |
| US5190521A (en) | 1990-08-22 | 1993-03-02 | Tecnol Medical Products, Inc. | Apparatus and method for raising a skin wheal and anesthetizing skin |
| NL9001955A (nl) * | 1990-09-05 | 1992-04-01 | Cedona Pharm Bv | Nieuwe thiazolidinederivaten. |
| US5393777A (en) * | 1990-11-15 | 1995-02-28 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon Health Sciences University | Deferration using anguibactin siderophore |
| KR100221041B1 (ko) * | 1990-11-30 | 1999-09-15 | 야스이 쇼사꾸 | 2-아릴티아졸 유도체 및 그의 약제학적 조성물 |
| TW311136B (enExample) * | 1990-11-30 | 1997-07-21 | Otsuka Pharma Co Ltd | |
| US5527288A (en) | 1990-12-13 | 1996-06-18 | Elan Medical Technologies Limited | Intradermal drug delivery device and method for intradermal delivery of drugs |
| FR2677021B1 (fr) * | 1991-05-31 | 1993-10-01 | Upsa Laboratoires | Nouveaux derives de thiazole antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| GB9118204D0 (en) | 1991-08-23 | 1991-10-09 | Weston Terence E | Needle-less injector |
| SE9102652D0 (sv) | 1991-09-13 | 1991-09-13 | Kabi Pharmacia Ab | Injection needle arrangement |
| US5328483A (en) | 1992-02-27 | 1994-07-12 | Jacoby Richard M | Intradermal injection device with medication and needle guard |
| US5383851A (en) | 1992-07-24 | 1995-01-24 | Bioject Inc. | Needleless hypodermic injection device |
| US5569189A (en) | 1992-09-28 | 1996-10-29 | Equidyne Systems, Inc. | hypodermic jet injector |
| US5334144A (en) | 1992-10-30 | 1994-08-02 | Becton, Dickinson And Company | Single use disposable needleless injector |
| US5840739A (en) * | 1992-11-16 | 1998-11-24 | University Of Florida Research Foundation, Inc. | Thiazoline acid derivatives |
| AU5602594A (en) | 1992-11-16 | 1994-06-08 | University Of Florida Research Foundation, Inc. | 2-(pyrid-2'-yl)-2-thiazoline-4(s)-carboxylic acid derivatives |
| DE4301356A1 (de) * | 1993-01-20 | 1994-07-21 | Basf Ag | Verfahren zur Herstellung von 2-Alkyl-4-fluormethyl-thiazolcarbonsäure-alkylestern |
| WO1995024176A1 (en) | 1994-03-07 | 1995-09-14 | Bioject, Inc. | Ampule filling device |
| US5466220A (en) | 1994-03-08 | 1995-11-14 | Bioject, Inc. | Drug vial mixing and transfer device |
| US5599302A (en) | 1995-01-09 | 1997-02-04 | Medi-Ject Corporation | Medical injection system and method, gas spring thereof and launching device using gas spring |
| US5730723A (en) | 1995-10-10 | 1998-03-24 | Visionary Medical Products Corporation, Inc. | Gas pressured needle-less injection device and method |
| US5893397A (en) | 1996-01-12 | 1999-04-13 | Bioject Inc. | Medication vial/syringe liquid-transfer apparatus |
| GB9607549D0 (en) | 1996-04-11 | 1996-06-12 | Weston Medical Ltd | Spring-powered dispensing device |
| FR2749583B1 (fr) * | 1996-06-07 | 1998-08-21 | Lipha | Nouveaux derives de thiazolidine -2,4- dione substitues, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| US20020049316A1 (en) * | 1997-04-29 | 2002-04-25 | Halbert Stacie Marie | Protease inhibitors |
| US5993412A (en) | 1997-05-19 | 1999-11-30 | Bioject, Inc. | Injection apparatus |
| US6373912B1 (en) * | 1997-06-16 | 2002-04-16 | Legerity, Inc. | Phase-locked loop arrangement with fast lock mode |
| IT1298087B1 (it) | 1998-01-08 | 1999-12-20 | Fiderm S R L | Dispositivo per il controllo della profondita' di penetrazione di un ago, in particolare applicabile ad una siringa per iniezioni |
| ES2235461T3 (es) * | 1998-02-04 | 2005-07-01 | University Of Florida Research Foundation, Inc. | Acido n,n'-bis (2-hidroxibencil)etilendiamina-n,n'-diacetico y sales de sodio de este para terapia quelante de hierro. |
| MA26618A1 (fr) | 1998-04-09 | 2004-12-20 | Smithkline Beecham Corp | Composes et compositions pharmaceutiques pour le traitement du paludisme |
| US6147070A (en) * | 1998-06-05 | 2000-11-14 | Facchini; Francesco | Methods and compositions for controlling iron stores to treat and cure disease states |
| US6083966A (en) | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| US6159983A (en) * | 1998-09-18 | 2000-12-12 | University Of Florida | Method and composition for treatment of inflammatory bowel disease |
| NZ526880A (en) | 1998-09-21 | 2005-05-27 | Univ Florida | Antimalarial agents |
| US6251927B1 (en) * | 1999-04-20 | 2001-06-26 | Medinox, Inc. | Methods for treatment of sickle cell anemia |
| DE19948434A1 (de) | 1999-10-08 | 2001-06-07 | Gruenenthal Gmbh | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| US7160855B2 (en) | 2002-03-14 | 2007-01-09 | Children's Hospital & Research Center At Oakland | Enhancement of iron chelation therapy |
| WO2004017959A2 (en) | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| US20040044220A1 (en) | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| CA2538159A1 (en) * | 2003-09-09 | 2005-03-17 | University Of Florida Research Foundation, Inc. | Polyamine-metal chelator conjugates |
| AU2003270473A1 (en) * | 2003-09-09 | 2005-04-27 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| JP2008520669A (ja) | 2004-11-19 | 2008-06-19 | シバ バイオメディカル，エルエルシー | エリスロポエチン抵抗性を治療する方法 |
| BRPI0610644B8 (pt) | 2005-04-04 | 2021-05-25 | Univ Florida | composto e composição farmacêutica que compreende tal composto e um veículo ou diluente farmaceuticamente aceitável. |
| US20080194518A1 (en) | 2005-12-23 | 2008-08-14 | MOOKERJEE Pradip | Antimicrobial Compositions |
| CN101129381B (zh) | 2006-08-25 | 2012-02-01 | 天津和美生物技术有限公司 | 含β-内酰胺类抗生素和离子螯合剂的抗生素复方 |
| JP2010512398A (ja) | 2006-12-12 | 2010-04-22 | ユニバーシティ オブ フロリダ | デスフェリチオシン類縁体アクチニド除染剤 |
| US8324397B2 (en) | 2007-03-15 | 2012-12-04 | University Of Florida Research Foundation, Inc. | Desferrithiocin polyether analogues |
| FR2922210A1 (fr) | 2007-10-11 | 2009-04-17 | Univ Louis Pasteur Etablisseme | Nouveaux composes, preparation et utilisations |
| MY163516A (en) | 2008-07-14 | 2017-09-15 | Ferrokin Biosciences Inc | Novel salts and polymorphs of desazadesferrithiocin polyether analogues as metal chelation agents |
| PL385765A1 (pl) | 2008-07-28 | 2010-02-01 | Maciej Żurek | Sposób sterowania łopatą napędową względem kierunku wiatru, zwłaszcza w silniku wiatrowym i wodnym o osi prostopadłej do kierunku wiatru oraz silnik wiatrowy o osi prostopadłej do kierunku wiatru z łopatą napędową sterowaną względem kierunku wiatru |
| BR112012001761A2 (pt) | 2009-07-27 | 2017-05-09 | Ferrokin Bioscience Inc | composto de formula i, composto farmacêutica e método de tratamento de uma condição mediada por metal em um indivduo |
| JP5925679B2 (ja) | 2009-08-25 | 2016-05-25 | ユニバーシティ オブ フロリダ リサーチ ファウンデーション，インコーポレイティド | デスフェリチオシンポリエーテル類似体およびその使用 |
| US20130053387A1 (en) | 2010-05-04 | 2013-02-28 | FerroKin BioScience, Inc. | Desazadesferrothiocin and desazadesferrothiocin polyether analogues as metal chelation agents |
| WO2012027794A2 (en) | 2010-09-01 | 2012-03-08 | The Mental Health Research Institute Of Victoria | Method of treatment and agents useful for same |
| WO2013090766A1 (en) | 2011-12-16 | 2013-06-20 | University Of Florida Research Foundation, Inc. | Uses of 3'-desferrithiocin analogs |
| KR102111176B1 (ko) | 2011-12-16 | 2020-05-15 | 유니버시티 오브 플로리다 리서치 파운데이션, 인코포레이티드 | 4'-데스페리티오신 유사체의 용도 |
| WO2014134701A1 (en) | 2013-03-07 | 2014-09-12 | Kane Biotech Inc. | Antimicrobial-antibiofilm compositions and methods of use thereof |
| JP6838966B2 (ja) | 2013-11-22 | 2021-03-03 | ユニバーシティー オブ フロリダ リサーチ ファンデーション， インク． | デスフェリチオシン類似体およびその使用 |
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2006
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- 2006-03-22 CN CN2006800198675A patent/CN101189216B/zh active Active
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