DE60125555T2 - 5-aminolaevulinsäure-ester als mittel zur photosensibilisierung in der chemotherapie - Google Patents
5-aminolaevulinsäure-ester als mittel zur photosensibilisierung in der chemotherapie Download PDFInfo
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- DE60125555T2 DE60125555T2 DE60125555T DE60125555T DE60125555T2 DE 60125555 T2 DE60125555 T2 DE 60125555T2 DE 60125555 T DE60125555 T DE 60125555T DE 60125555 T DE60125555 T DE 60125555T DE 60125555 T2 DE60125555 T2 DE 60125555T2
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0061—5-aminolevulinic acid-based PDT: 5-ALA-PDT involving porphyrins or precursors of protoporphyrins generated in vivo from 5-ALA
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- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
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- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
Landscapes
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
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| GBGB0018528.0A GB0018528D0 (en) | 2000-07-27 | 2000-07-27 | Compounds |
| GB0018528 | 2000-07-27 | ||
| PCT/GB2001/003336 WO2002010120A1 (en) | 2000-07-27 | 2001-07-25 | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
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| DE60125555D1 DE60125555D1 (de) | 2007-02-08 |
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| US20090297602A1 (en) * | 1998-11-02 | 2009-12-03 | Devane John G | Modified Release Loxoprofen Compositions |
| AU770645B2 (en) * | 1998-11-02 | 2004-02-26 | Alkermes Pharma Ireland Limited | Multiparticulate modified release composition |
| WO2002100347A2 (en) | 2001-06-11 | 2002-12-19 | Xenoport, Inc. | Prodrugs of gaba analogs, compositions and uses thereof |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
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| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7232924B2 (en) | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
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| JP2006501936A (ja) * | 2002-10-04 | 2006-01-19 | エラン ファーマ インターナショナル，リミティド | 固体ナノ粒子活性薬剤のガンマ線照射 |
| DE10312659A1 (de) * | 2003-03-21 | 2004-10-07 | Universität Regensburg | 5-Aminolävulinsäurederivate und ihre Verwendung |
| JP2007501683A (ja) * | 2003-05-22 | 2007-02-01 | エラン ファーマ インターナショナル リミテッド | γ線照射によるナノ粒子活性物質分散体の滅菌法 |
| CA2437638A1 (en) | 2003-08-20 | 2005-02-20 | John Robert North | Photodynamic therapy |
| CA2457214A1 (en) | 2004-02-06 | 2005-08-06 | Qlt Inc. | Photodynamic therapy for the treatment of acne |
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| JP2005350418A (ja) * | 2004-06-11 | 2005-12-22 | Shibuya Kogyo Co Ltd | 標的細胞の死滅方法と標的細胞を死滅させるための薬剤及び該薬剤の製造装置 |
| EP1785132B1 (en) | 2004-09-02 | 2014-04-09 | Cosmo Oil Co., Ltd. | Constitutional function-improving agents |
| RU2440112C2 (ru) | 2004-11-04 | 2012-01-20 | Ксенопорт, Инк. | Пероральная дозированная форма габапентина замедленного высвобождения |
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| JP4934293B2 (ja) * | 2005-07-05 | 2012-05-16 | コスモ石油株式会社 | 植物活力剤組成物 |
| JP4934292B2 (ja) * | 2005-07-05 | 2012-05-16 | コスモ石油株式会社 | ５−アミノレブリン酸エステルリン酸類塩、その製造方法及びその用途 |
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| EP2043623A4 (en) * | 2006-07-12 | 2013-03-20 | Elan Pharma Int Ltd | NANOPARTICLE FORMULATIONS OF MODAFINIL |
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| US20090036952A1 (en) | 2007-07-30 | 2009-02-05 | National Yang-Ming University | Induction driven light module and use thereof |
| GB0718957D0 (en) * | 2007-09-28 | 2007-11-07 | Ge Healthcare Ltd | Optical imaging agents |
| KR100883560B1 (ko) * | 2007-08-23 | 2009-02-17 | (주) 위디어 | 신규한 5-아미노레불린 산 유도체 및 이의 제조방법 |
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| CA2735426A1 (en) * | 2008-09-01 | 2010-03-04 | Swedish Pharma Ab | New 5-aminolevulinic acid prodrugs for use in photodynamic therapy and photodynamic diagnosis |
| GB0823472D0 (en) | 2008-12-23 | 2009-01-28 | Photocure Asa | Product |
| GB0900461D0 (en) | 2009-01-12 | 2009-02-11 | Photocure Asa | Photodynamic therapy device |
| BRPI1011650A2 (pt) * | 2009-06-11 | 2016-03-22 | Photocure Asa | composições sólidas compreendendo ácido 5-aminolevulínico |
| MX2011013127A (es) | 2009-06-11 | 2012-02-21 | Photocure Asa | Composiciones semi-solidas y productos farmaceuticos. |
| EP2542208A1 (en) | 2010-03-01 | 2013-01-09 | Photocure ASA | Cosmetic compositions |
| EP2394642A1 (en) | 2010-06-10 | 2011-12-14 | Universite De Geneve | 5-ALA ester formulations and use thereof |
| EP2585111A1 (en) | 2010-06-23 | 2013-05-01 | Photocure ASA | Hyperosmotic preparations comprising 5 -amino levulinic acid or derivative as photosensitizing agent |
| JP5991970B2 (ja) | 2010-07-09 | 2016-09-14 | フォトキュア エイエスエイ | 光力学的治療または光力学的診断で使用する乾燥組成物および当該乾燥組成物を含む装置 |
| CN104152530B (zh) | 2010-12-24 | 2017-09-19 | 爱科来株式会社 | 癌细胞的检测方法 |
| EP2663285A2 (en) | 2011-01-13 | 2013-11-20 | Qlt Inc. | Pharmaceutical compositions for topical delivery of photosensitizers and uses thereof |
| EP2766049A1 (en) | 2011-10-14 | 2014-08-20 | Photocure ASA | Photodynamic diagnosis of abnormalities of the epithelial lining of the oesophagus with the means of a 5-ala ester |
| US20140316534A1 (en) | 2011-10-14 | 2014-10-23 | Photocure Asa | Stent |
| RU2615870C2 (ru) | 2011-12-19 | 2017-04-11 | ФотоКьюэр АСА | Устройство облучения |
| WO2013092936A2 (en) | 2011-12-20 | 2013-06-27 | Galderma Research & Development | Use of 5-aminolevulinic acid and esters, in combination with a vitamin d derivative or analog in photochemotherapy, and their uses in treating acne |
| US20150209428A1 (en) | 2012-07-11 | 2015-07-30 | Dermira, Inc. | Pharmaceutical compositions for topical delivery of photosensitizers and uses thereof |
| KR102180174B1 (ko) | 2012-08-03 | 2020-11-19 | 포토큐어 에이에스에이 | 화합물 |
| GB201215675D0 (en) * | 2012-09-03 | 2012-10-17 | Univ Exeter | Compound |
| GB201221123D0 (en) | 2012-11-23 | 2013-01-09 | Photocure As | Device for photodynamic treatment |
| GB201306369D0 (en) | 2013-04-09 | 2013-05-22 | Photocure As | Irradiation device |
| BR112016014073A2 (pt) | 2013-12-20 | 2017-08-08 | Galderma Res & Dev | Tratamento fotodinâmico de pulso de pele fotodanificada |
| ES2896882T3 (es) | 2014-02-03 | 2022-02-28 | Quadriga Biosciences Inc | Beta-aminoácidos beta sustituidos y análogos como agentes quimioterapéuticos |
| EP3095464A1 (en) | 2015-05-19 | 2016-11-23 | Universite De Geneve | 5-ala derivatives and use thereof |
| WO2017024009A1 (en) | 2015-08-03 | 2017-02-09 | Quadriga Biosciences, Inc. | Beta-substituted beta-amino acids and analogs as chemotherapeutic agents and uses thereof |
| GB201522309D0 (en) * | 2015-12-17 | 2016-02-03 | Photocure Asa | Use |
| GB201522398D0 (en) | 2015-12-18 | 2016-02-03 | Photocure As | Device for photodynamic therapy |
| CN106187793A (zh) | 2016-01-26 | 2016-12-07 | 赵鸣 | 5‑氨基酮戊酸及其衍生物的盐化合物和应用 |
| ES2859777T3 (es) | 2017-02-06 | 2021-10-04 | 3Skin As | Composición de filtro solar |
| DK3641882T3 (da) * | 2017-06-21 | 2023-12-18 | Photocure Asa | Fremgangsmåde til fremstilling af en flydende farmaceutisk sammensætning og indretning til anvendelse i en sådan fremgangsmåde |
| EP3868372A1 (en) | 2020-02-19 | 2021-08-25 | JLP Health GmbH | A pharmaceutical combination of an artemisinin compound and a heme synthesis modulator for treating cancer |
| CN111635464B (zh) * | 2020-05-12 | 2022-03-25 | 上海易全化学有限公司 | 一种5-氨基酮戊酸葡聚糖酯的制备方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2411382C3 (de) | 1974-03-09 | 1979-09-06 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-Tetrahydrofurfuryl-6,7-benzomorphane, Verfahren zur Herstellung und deren Verwendung |
| US4087532A (en) * | 1974-03-09 | 1978-05-02 | Boehringer Ingelheim Gmbh | Analgesically useful 2-tetrahydrofurfuryl-5-lower alkyl-2-oxy-6,7-benzomorphans and salts thereof |
| GB2058077B (en) | 1979-06-08 | 1983-03-09 | Szelke M | Enkephalin analogues |
| CA1236029A (en) * | 1984-05-14 | 1988-05-03 | Edmund Sandborn | Pharmaceutical solutions comprising dimethyl sulfoxide |
| SE460947B (sv) | 1986-08-26 | 1989-12-11 | Lejus Medical Ab | En multiple-unit-dos komposition av l-dopa |
| JPS6452778A (en) * | 1987-05-30 | 1989-02-28 | Tokuyama Soda Kk | Fulgide compound and production thereof |
| JPH0745502B2 (ja) | 1987-11-10 | 1995-05-17 | 株式会社トクヤマ | 新規化合物及びそれを含む組成物 |
| US5422093A (en) * | 1989-07-28 | 1995-06-06 | Queen's University | Photochemotherapeutic method using 5-aminolevulinic acid and precursors thereof |
| US5234940A (en) | 1989-07-28 | 1993-08-10 | Queen's University | Photochemotherapeutic method using 5-aminolevulinic acid and precursors thereof |
| US5955490A (en) * | 1989-07-28 | 1999-09-21 | Queen's University At Kingston | Photochemotherapeutic method using 5-aminolevulinic acid and other precursors of endogenous porphyrins |
| US5079262A (en) * | 1989-07-28 | 1992-01-07 | Queen's University At Kingston | Method of detection and treatment of malignant and non-malignant lesions utilizing 5-aminolevulinic acid |
| JP2767318B2 (ja) | 1990-04-11 | 1998-06-18 | 株式会社コスモ総合研究所 | ５―アミノレブリン酸アルキルエステル又はその塩及びその製造方法並びにこれを有効成分とする除草剤 |
| US5219878A (en) * | 1990-10-05 | 1993-06-15 | Queen's University | Tetrapyrrole hydroxyalkylamide photochemotherapeutic agents |
| EP0553116A1 (en) | 1990-10-05 | 1993-08-04 | Queen's University At Kingston | Porphyrin derivatives |
| JP2747644B2 (ja) * | 1993-08-19 | 1998-05-06 | 株式会社コスモ総合研究所 | 植物成長調節剤 |
| GB9318841D0 (en) | 1993-09-10 | 1993-10-27 | Res Foundation Of The Norwegia | Composition |
| JP2896963B2 (ja) * | 1994-11-28 | 1999-05-31 | 株式会社コスモ総合研究所 | 植物の耐塩性向上剤 |
| US6492420B2 (en) * | 1995-03-10 | 2002-12-10 | Photocure As | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| US7530461B2 (en) | 1995-03-10 | 2009-05-12 | Photocure Asa | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| GB9504948D0 (en) * | 1995-03-10 | 1995-04-26 | Norwegian Radium Hospital Rese | Compounds |
| US6992107B1 (en) * | 1995-03-10 | 2006-01-31 | Photocure Asa | Esters of 5-aminolevulinic acid and their use as photosensitizing compounds in photochemotherapy |
| CA2215069C (en) * | 1995-03-10 | 2006-09-12 | Photocure As | Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy |
| GB9700396D0 (en) * | 1997-01-10 | 1997-02-26 | Photocure As | Photochemotherapeutic compositions |
| FR2777782B1 (fr) | 1998-04-22 | 2001-05-18 | Alexandre Marti | Solution pour la preparation d'une substance pharmaceutique pour le diagnostic et/ou le traitement de lesions tissulaires |
| GB0018527D0 (en) * | 2000-07-27 | 2000-09-13 | Photocure Asa | Composition |
| GB0118251D0 (en) | 2001-07-26 | 2001-09-19 | Photocure Asa | Method |
| GB0128052D0 (en) | 2001-11-22 | 2002-01-16 | Drug Discovery Lab As | Compounds |
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2000
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2001
- 2001-07-25 NZ NZ523927A patent/NZ523927A/en not_active IP Right Cessation
- 2001-07-25 AU AU2002227495A patent/AU2002227495B2/en not_active Ceased
- 2001-07-25 RU RU2003105460/04A patent/RU2246483C2/ru not_active IP Right Cessation
- 2001-07-25 DE DE60125555T patent/DE60125555T2/de not_active Expired - Lifetime
- 2001-07-25 HU HU0301427A patent/HUP0301427A2/hu unknown
- 2001-07-25 AU AU2749502A patent/AU2749502A/xx active Pending
- 2001-07-25 JP JP2002516252A patent/JP5010088B2/ja not_active Expired - Fee Related
- 2001-07-25 KR KR10-2003-7001213A patent/KR20030028554A/ko not_active Withdrawn
- 2001-07-25 CA CA2416307A patent/CA2416307C/en not_active Expired - Fee Related
- 2001-07-25 DK DK01984415T patent/DK1313695T3/da active
- 2001-07-25 PT PT01984415T patent/PT1313695E/pt unknown
- 2001-07-25 ES ES01984415T patent/ES2276844T3/es not_active Expired - Lifetime
- 2001-07-25 WO PCT/GB2001/003336 patent/WO2002010120A1/en not_active Ceased
- 2001-07-25 AT AT01984415T patent/ATE349417T1/de active
- 2001-07-25 CZ CZ2003260A patent/CZ2003260A3/cs unknown
- 2001-07-25 EP EP01984415A patent/EP1313695B1/en not_active Expired - Lifetime
- 2001-07-25 CN CNB018146953A patent/CN1318388C/zh not_active Expired - Fee Related
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2003
- 2003-01-24 NO NO20030398A patent/NO20030398L/no not_active Application Discontinuation
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| CA2416307C (en) | 2013-01-22 |
| RU2246483C2 (ru) | 2005-02-20 |
| KR20030028554A (ko) | 2003-04-08 |
| EP1313695B1 (en) | 2006-12-27 |
| JP5010088B2 (ja) | 2012-08-29 |
| GB0018528D0 (en) | 2000-09-13 |
| NZ523927A (en) | 2004-07-30 |
| HUP0301427A2 (hu) | 2003-09-29 |
| DK1313695T3 (da) | 2007-04-30 |
| US7563819B1 (en) | 2009-07-21 |
| ES2276844T3 (es) | 2007-07-01 |
| AU2749502A (en) | 2002-02-13 |
| CN1460099A (zh) | 2003-12-03 |
| CN1318388C (zh) | 2007-05-30 |
| US20040106679A1 (en) | 2004-06-03 |
| CZ2003260A3 (cs) | 2003-06-18 |
| WO2002010120A1 (en) | 2002-02-07 |
| DE60125555D1 (de) | 2007-02-08 |
| JP2004505105A (ja) | 2004-02-19 |
| NO20030398D0 (no) | 2003-01-24 |
| ATE349417T1 (de) | 2007-01-15 |
| US7217736B2 (en) | 2007-05-15 |
| CA2416307A1 (en) | 2002-02-07 |
| NO20030398L (no) | 2003-03-12 |
| AU2002227495B2 (en) | 2006-01-05 |
| PT1313695E (pt) | 2007-01-31 |
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