AU2007262670B2 - Method of treatment of glioma brain tumour - Google Patents
Method of treatment of glioma brain tumour Download PDFInfo
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- AU2007262670B2 AU2007262670B2 AU2007262670A AU2007262670A AU2007262670B2 AU 2007262670 B2 AU2007262670 B2 AU 2007262670B2 AU 2007262670 A AU2007262670 A AU 2007262670A AU 2007262670 A AU2007262670 A AU 2007262670A AU 2007262670 B2 AU2007262670 B2 AU 2007262670B2
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- alkynyl
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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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81577906P | 2006-06-22 | 2006-06-22 | |
| US60/815,779 | 2006-06-22 | ||
| PCT/AU2007/000876 WO2007147217A1 (en) | 2006-06-22 | 2007-06-22 | Method of treatment of glioma brain tumour |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2007262670A1 AU2007262670A1 (en) | 2007-12-27 |
| AU2007262670A2 AU2007262670A2 (en) | 2009-03-26 |
| AU2007262670B2 true AU2007262670B2 (en) | 2012-12-20 |
Family
ID=38833006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007262670A Ceased AU2007262670B2 (en) | 2006-06-22 | 2007-06-22 | Method of treatment of glioma brain tumour |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8163760B2 (OSRAM) |
| EP (1) | EP2044026B1 (OSRAM) |
| JP (1) | JP5415942B2 (OSRAM) |
| CN (1) | CN101589026B (OSRAM) |
| AU (1) | AU2007262670B2 (OSRAM) |
| CA (1) | CA2656825C (OSRAM) |
| DK (1) | DK2044026T3 (OSRAM) |
| ES (1) | ES2474865T3 (OSRAM) |
| WO (1) | WO2007147217A1 (OSRAM) |
Families Citing this family (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002950217A0 (en) | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| EP2012789B1 (en) * | 2006-04-14 | 2013-09-25 | Prana Biotechnology Limited | Method of treatment of age-related macular degeneration (AMD) |
| US8163779B2 (en) * | 2006-12-20 | 2012-04-24 | Takeda San Diego, Inc. | Glucokinase activators |
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| US9321730B2 (en) * | 2007-08-21 | 2016-04-26 | The Hong Kong Polytechnic University | Method of making and administering quinoline derivatives as anti-cancer agents |
| MY150596A (en) | 2008-02-01 | 2014-01-30 | Takeda Pharmaceutical | Hsp90 inhibitors |
| GB0806794D0 (en) * | 2008-04-15 | 2008-05-14 | Ludwig Inst Cancer Res | Therapeutic compounds |
| JP2011530596A (ja) * | 2008-08-11 | 2011-12-22 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | ｔＲＮＡ合成酵素の阻害のためのハロフジノン類似体およびそれらの使用 |
| JP5719779B2 (ja) * | 2008-12-24 | 2015-05-20 | プラナ バイオテクノロジー リミティッド | キナゾリノン化合物 |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| EP2565186A1 (en) * | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| FR2984317B1 (fr) * | 2011-12-20 | 2015-02-27 | Univ Rennes | Composes chelateurs de metal presentant au moins une chaine polyaminee. |
| US10155742B2 (en) | 2012-01-13 | 2018-12-18 | President And Fellows Of Harvard College | Halofuginol derivatives and their use in cosmetic and pharmaceutical compositions |
| UA125503C2 (uk) | 2012-06-13 | 2022-04-13 | Інсайт Холдинґс Корпорейшн | Заміщені трициклічні сполуки як інгібітори fgfr |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| CN104903300B (zh) * | 2012-12-27 | 2018-04-17 | 霍夫曼-拉罗奇有限公司 | Comt抑制剂 |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| MY181497A (en) | 2013-04-19 | 2020-12-23 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| EP3061749B1 (en) * | 2013-10-23 | 2019-02-27 | Chugai Seiyaku Kabushiki Kaisha | Quinazolinone and isoquinolinone derivative |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
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| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
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| PE20210919A1 (es) | 2018-05-04 | 2021-05-19 | Incyte Corp | Sales de un inhibidor de fgfr |
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| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
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| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
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| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
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| PE20221504A1 (es) | 2019-12-04 | 2022-09-30 | Incyte Corp | Derivados de un inhibidor de fgfr |
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| WO2022006456A1 (en) | 2020-07-02 | 2022-01-06 | Incyte Corporation | Tricyclic pyridone compounds as jak2 v617f inhibitors |
| RS66978B1 (sr) | 2020-07-02 | 2025-07-31 | Incyte Corp | Triciklična jedinjenja uree kao inhibitori jak2 v617f |
| US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
| US11919908B2 (en) | 2020-12-21 | 2024-03-05 | Incyte Corporation | Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors |
| WO2022182839A1 (en) | 2021-02-25 | 2022-09-01 | Incyte Corporation | Spirocyclic lactams as jak2 v617f inhibitors |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| CN113214249B (zh) * | 2021-04-23 | 2023-09-19 | 成都大学 | 吡啶并[1,2-a]嘧啶-4-硫酮化合物的合成方法 |
| TW202313611A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之三環雜環 |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| KR20240144096A (ko) | 2021-11-02 | 2024-10-02 | 플레어 테라퓨틱스 인크. | Pparg 역 효능제 및 그의 용도 |
| KR20240163688A (ko) | 2022-03-17 | 2024-11-19 | 인사이트 코포레이션 | Jak2 v617f 억제제로서의 삼환계 우레아 화합물 |
| CN116410132B (zh) * | 2023-02-23 | 2024-07-09 | 广东工业大学 | 一种8-羟基喹啉类化合物及其制备方法和在制备抗肿瘤药物上的应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6977255B2 (en) * | 2000-01-24 | 2005-12-20 | Kinacia Pty. Ltd. | Therapeutic morpholino-substituted compounds |
| AU2007240120A1 (en) * | 2006-04-14 | 2007-10-25 | Prana Biotechnology Ltd | Method of treatment of age-related macular degeneration (AMD) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003524620A (ja) | 1999-03-24 | 2003-08-19 | アノーメッド インコーポレイティド | ケモカインレセプター結合複素環化合物 |
| AU2002230056A1 (en) | 2001-01-29 | 2002-08-12 | Insight Strategy And Marketing Ltd | Indole derivatives and their uses as heparanase inhibitors |
| AU2002313633B2 (en) | 2001-06-08 | 2007-03-01 | Cytovia, Inc. | Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs |
| CA2475773A1 (en) * | 2002-02-20 | 2003-09-04 | Pharmacia & Upjohn Company | Azabicyclic compounds with alfa7 nicotinic acetylcholine receptor activity |
| CA2500727A1 (en) | 2002-10-03 | 2004-04-15 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| NZ539211A (en) * | 2002-10-04 | 2008-05-30 | Prana Biotechnology Ltd | Neurologically-active compounds |
| WO2005063213A1 (en) * | 2003-12-19 | 2005-07-14 | Biodelivery Sciences International, Inc. | Rigid liposomal cochleate and methods of use and manufacture |
| US20060100226A1 (en) | 2004-09-10 | 2006-05-11 | Sikorski James A | 2-Thiopyrimidinones as therapeutic agents |
| NZ568666A (en) * | 2005-11-30 | 2011-09-30 | Vertex Pharma | [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole derivative as inhibitors of c-Met |
| DE102005059479A1 (de) * | 2005-12-13 | 2007-06-14 | Merck Patent Gmbh | Hydroxychinolinderivate |
-
2007
- 2007-06-22 CA CA2656825A patent/CA2656825C/en not_active Expired - Fee Related
- 2007-06-22 WO PCT/AU2007/000876 patent/WO2007147217A1/en not_active Ceased
- 2007-06-22 JP JP2009515675A patent/JP5415942B2/ja not_active Expired - Fee Related
- 2007-06-22 DK DK07719115.3T patent/DK2044026T3/da active
- 2007-06-22 EP EP07719115.3A patent/EP2044026B1/en not_active Not-in-force
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- 2007-06-22 CN CN2007800311672A patent/CN101589026B/zh not_active Expired - Fee Related
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6977255B2 (en) * | 2000-01-24 | 2005-12-20 | Kinacia Pty. Ltd. | Therapeutic morpholino-substituted compounds |
| AU2007240120A1 (en) * | 2006-04-14 | 2007-10-25 | Prana Biotechnology Ltd | Method of treatment of age-related macular degeneration (AMD) |
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| US8163760B2 (en) | 2012-04-24 |
| WO2007147217A1 (en) | 2007-12-27 |
| CA2656825A1 (en) | 2007-12-27 |
| AU2007262670A2 (en) | 2009-03-26 |
| JP5415942B2 (ja) | 2014-02-12 |
| CA2656825C (en) | 2013-12-10 |
| JP2009541223A (ja) | 2009-11-26 |
| ES2474865T3 (es) | 2014-07-09 |
| EP2044026A1 (en) | 2009-04-08 |
| EP2044026B1 (en) | 2014-03-26 |
| EP2044026A4 (en) | 2009-08-05 |
| CN101589026B (zh) | 2013-10-16 |
| US20100069393A1 (en) | 2010-03-18 |
| AU2007262670A1 (en) | 2007-12-27 |
| CN101589026A (zh) | 2009-11-25 |
| DK2044026T3 (da) | 2014-06-30 |
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