AU2004289174B2 - Amino acid prodrugs - Google Patents
Amino acid prodrugs Download PDFInfo
- Publication number
- AU2004289174B2 AU2004289174B2 AU2004289174A AU2004289174A AU2004289174B2 AU 2004289174 B2 AU2004289174 B2 AU 2004289174B2 AU 2004289174 A AU2004289174 A AU 2004289174A AU 2004289174 A AU2004289174 A AU 2004289174A AU 2004289174 B2 AU2004289174 B2 AU 2004289174B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- amino acid
- group
- drug
- product
- 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.)
- Ceased
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- 229940002612 prodrug Drugs 0.000 title claims description 120
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07K—PEPTIDES
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
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- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
- C07K7/645—Cyclosporins; Related peptides
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- 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)
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- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
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- Hematology (AREA)
- Neurosurgery (AREA)
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- Gastroenterology & Hepatology (AREA)
- Biomedical Technology (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)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49133103P | 2003-07-29 | 2003-07-29 | |
| US60/491,331 | 2003-07-29 | ||
| PCT/US2004/024901 WO2005046575A2 (en) | 2003-07-29 | 2004-07-29 | Amino acid prodrugs |
Publications (3)
| Publication Number | Publication Date |
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| AU2004289174A2 AU2004289174A2 (en) | 2005-05-26 |
| AU2004289174A1 AU2004289174A1 (en) | 2005-05-26 |
| AU2004289174B2 true AU2004289174B2 (en) | 2011-05-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004289174A Ceased AU2004289174B2 (en) | 2003-07-29 | 2004-07-29 | Amino acid prodrugs |
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| Country | Link |
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| EP (1) | EP1660017A4 (https=) |
| JP (2) | JP2007510621A (https=) |
| KR (3) | KR20130081319A (https=) |
| CN (1) | CN101123878A (https=) |
| AU (1) | AU2004289174B2 (https=) |
| CA (1) | CA2534342C (https=) |
| IL (1) | IL173382A0 (https=) |
| NZ (3) | NZ601780A (https=) |
| SG (2) | SG178721A1 (https=) |
| WO (1) | WO2005046575A2 (https=) |
| ZA (1) | ZA200600660B (https=) |
Families Citing this family (117)
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| EP1603512A2 (en) | 2003-03-17 | 2005-12-14 | Albany Molecular Research, Inc. | Novel cyclosporins |
| CN101123878A (zh) * | 2003-07-29 | 2008-02-13 | 信号研发控股有限责任公司 | 氨基酸前药 |
| US7589233B2 (en) | 2003-07-29 | 2009-09-15 | Signature R&D Holdings, Llc | L-Threonine derivatives of high therapeutic index |
| US8173840B2 (en) | 2003-07-29 | 2012-05-08 | Signature R&D Holdings, Llc | Compounds with high therapeutic index |
| JP2007517056A (ja) | 2003-12-29 | 2007-06-28 | セプラコア インコーポレーテッド | ピロール及びピラゾールｄａａｏ阻害剤 |
| WO2005066214A1 (ja) * | 2004-01-07 | 2005-07-21 | Seikagaku Corporation | ヒアルロン酸誘導体及びそれを含む薬剤 |
| WO2006017351A1 (en) | 2004-07-12 | 2006-02-16 | Xenoport, Inc. | Prodrugs of propofol, compositions and uses thereof |
| US7378391B2 (en) | 2004-09-29 | 2008-05-27 | Amr Technology, Inc. | Cyclosporin alkyne analogues and their pharmaceutical uses |
| WO2006039164A2 (en) | 2004-09-29 | 2006-04-13 | Amr Technology, Inc. | Novel cyclosporin analogues and their pharmaceutical uses |
| WO2006041631A2 (en) | 2004-10-06 | 2006-04-20 | Amr Technology, Inc. | Novel cyclosporin alkynes and their utility as pharmaceutical agents |
| BRPI0610368A8 (pt) * | 2005-05-05 | 2015-09-08 | Glaxosmithkline Ip Dev Ltd | Modulação de enzima e de receptor |
| JP5713535B2 (ja) * | 2005-11-11 | 2015-05-07 | チャンドラン, ブイ., ラビChandran, V., Ravi | 血小板凝集低下用薬学的組成物、血小板凝集低下用栄養組成物、および血小板凝集低下用食品又は飲料あるいは水性液体 |
| US20070203111A1 (en) | 2006-01-06 | 2007-08-30 | Sepracor Inc. | Cycloalkylamines as monoamine reuptake inhibitors |
| NZ569608A (en) | 2006-01-06 | 2011-09-30 | Sepracor Inc | Tetralone-based monoamine reuptake inhibitors |
| US7696165B2 (en) | 2006-03-28 | 2010-04-13 | Albany Molecular Research, Inc. | Use of cyclosporin alkyne analogues for preventing or treating viral-induced disorders |
| US7696166B2 (en) | 2006-03-28 | 2010-04-13 | Albany Molecular Research, Inc. | Use of cyclosporin alkyne/alkene analogues for preventing or treating viral-induced disorders |
| CN101421228B (zh) | 2006-03-31 | 2014-05-21 | 塞普拉柯公司 | 手性酰胺和胺的制备 |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| JP2009542701A (ja) * | 2006-07-06 | 2009-12-03 | サイトビア インコーポレイティッド | カスパーゼの活性化因子およびアポトーシスの誘導因子としてのならびに抗血管剤としての置換された４−アリール−クロメンおよびその使用法 |
| CN1907954B (zh) * | 2006-08-16 | 2011-11-23 | 重庆医科大学医药研究所 | 麻醉药2,6-二异丙基苯酚的水溶性衍生物及其制备方法 |
| US8962825B2 (en) | 2006-10-30 | 2015-02-24 | Glaxosmithkline Intellectual Property Development Limited | Hydroxamates as inhibitors of histone deacetylase |
| US7902252B2 (en) | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| CA2688493C (en) | 2007-05-31 | 2016-04-19 | Sepracor Inc. | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors |
| WO2008157537A2 (en) * | 2007-06-19 | 2008-12-24 | Ironwood Pharmaceuticals, Inc | Compositions and methods of use for treating or preventing lipid related disorders |
| US8778953B2 (en) | 2008-02-29 | 2014-07-15 | Chroma Therapeutics Ltd. | Inhibitors of P38 map kinase |
| TWI503101B (zh) * | 2008-12-15 | 2015-10-11 | 波提亞斯數位康健公司 | 與身體有關的接收器及其方法 |
| KR20110082601A (ko) * | 2008-12-19 | 2011-07-19 | 피너클 파마수티칼스, 인코포레이티드 | 페나조피리딘 화합물 |
| CN102596896A (zh) * | 2009-06-24 | 2012-07-18 | 夏尔有限责任公司 | 美西律氨基酸和肽前药以及它们的用途 |
| KR20120099462A (ko) | 2009-11-12 | 2012-09-10 | 더 리젠츠 오브 더 유니버시티 오브 미시건 | 스피로-옥신돌 ｍｄｍ2 길항제 |
| KR101798128B1 (ko) | 2010-02-01 | 2017-11-16 | 프로테우스 디지털 헬스, 인코포레이티드 | 데이터 수집 시스템 |
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| MX2010011006A (es) * | 2010-10-06 | 2012-04-18 | Senosiain S A De C V Lab | Nueva sal de un derivado de pirimidina. |
| AU2011326395B2 (en) | 2010-11-12 | 2016-01-07 | Ascenta Licensing Corporation | Spiro-oxindole MDM2 antagonists |
| US20120196933A1 (en) * | 2010-12-23 | 2012-08-02 | Richard Franklin | Mexiletine prodrugs |
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| FR2976944A1 (fr) | 2011-06-21 | 2012-12-28 | Centre Nat Rech Scient | Prodrogues peptidiques |
| WO2015112603A1 (en) | 2014-01-21 | 2015-07-30 | Proteus Digital Health, Inc. | Masticable ingestible product and communication system therefor |
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| AU2013202982C1 (en) * | 2012-01-06 | 2017-01-05 | Novartis Ag | Heterocyclic compounds and methods for their use |
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| WO2013168012A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
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| CN102924398B (zh) * | 2012-11-22 | 2015-11-18 | 安徽贝克生物制药有限公司 | 用于除去依非韦伦对应异构体的方法 |
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| WO2014151929A1 (en) | 2013-03-15 | 2014-09-25 | Proteus Digital Health, Inc. | Personal authentication apparatus system and method |
| CN103263405B (zh) * | 2013-05-08 | 2015-04-22 | 南京医科大学 | 用于治疗糖尿病的药物组合物及其应用 |
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| WO2015042411A1 (en) | 2013-09-20 | 2015-03-26 | Proteus Digital Health, Inc. | Methods, devices and systems for receiving and decoding a signal in the presence of noise using slices and warping |
| US10084880B2 (en) | 2013-11-04 | 2018-09-25 | Proteus Digital Health, Inc. | Social media networking based on physiologic information |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650803A (en) * | 1985-12-06 | 1987-03-17 | University Of Kansas | Prodrugs of rapamycin |
| US5972379A (en) * | 1995-02-14 | 1999-10-26 | Sequus Pharmaceuticals, Inc. | Liposome composition and method for administering a quinolone |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5411947A (en) * | 1989-06-28 | 1995-05-02 | Vestar, Inc. | Method of converting a drug to an orally available form by covalently bonding a lipid to the drug |
| WO1992021341A1 (en) * | 1991-05-31 | 1992-12-10 | Pfizer Inc. | Use of rapamycin prodrugs as immunosuppressant agents |
| JPH1143467A (ja) * | 1997-05-14 | 1999-02-16 | Ikeda Mohandou:Kk | 脂肪酸グリセライド誘導体及びグリセライド誘導体、並びにそれらの製造方法 |
| IT1294205B1 (it) * | 1997-07-23 | 1999-03-24 | Farmigea Spa | Procedimento per la solubilizzazione in acqua e in veicoli acquosi di sostanze farmacologicamente attive |
| WO2002016395A1 (en) * | 2000-08-18 | 2002-02-28 | The Board Of Trustees Of The University Of Illinois | Prodrugs of betulinic acid derivatives for the treatment of cancer and hiv |
| US20020160988A1 (en) * | 2001-02-20 | 2002-10-31 | Israel Institute For Biological Research | Compounds co-inducing cholinergic up-regulation and inflammation down-regulation and uses thereof |
| US7045543B2 (en) * | 2001-11-05 | 2006-05-16 | Enzrel Inc. | Covalent conjugates of biologically-active compounds with amino acids and amino acid derivatives for targeting to physiologically-protected sites |
| ATE396731T1 (de) * | 2003-03-25 | 2008-06-15 | Vertex Pharma | Thiazole zur verwendung als inhibitoren von protein-kinasen |
| CN101123878A (zh) * | 2003-07-29 | 2008-02-13 | 信号研发控股有限责任公司 | 氨基酸前药 |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650803A (en) * | 1985-12-06 | 1987-03-17 | University Of Kansas | Prodrugs of rapamycin |
| US5972379A (en) * | 1995-02-14 | 1999-10-26 | Sequus Pharmaceuticals, Inc. | Liposome composition and method for administering a quinolone |
Non-Patent Citations (1)
| Title |
|---|
| Yang C. et al, Journal of Pharmaceutical Sciences (2001) Vol 90 No 5 pages 617 - 624 and PubMed abstract PMID: 11288106 * |
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| WO2005046575A2 (en) | 2005-05-26 |
| KR20060073584A (ko) | 2006-06-28 |
| IL173382A0 (en) | 2006-06-11 |
| KR20120116991A (ko) | 2012-10-23 |
| CA2534342C (en) | 2016-05-10 |
| EP1660017A2 (en) | 2006-05-31 |
| WO2005046575A3 (en) | 2007-10-04 |
| SG178721A1 (en) | 2012-03-29 |
| SG145693A1 (en) | 2008-09-29 |
| JP2007510621A (ja) | 2007-04-26 |
| AU2004289174A2 (en) | 2005-05-26 |
| NZ545570A (en) | 2012-07-27 |
| AU2004289174A1 (en) | 2005-05-26 |
| CA2534342A1 (en) | 2005-05-26 |
| ZA200600660B (en) | 2007-04-25 |
| EP1660017A4 (en) | 2011-03-09 |
| NZ601780A (en) | 2012-10-26 |
| CN101123878A (zh) | 2008-02-13 |
| NZ601772A (en) | 2012-10-26 |
| KR20130081319A (ko) | 2013-07-16 |
| JP2013035863A (ja) | 2013-02-21 |
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