AU2006297462A1 - 5- (phenylisoxazolylethoxy) -triazol- 3 -yl substituted pyridine compounds for the treatment of neurological, psychiatric or pain disorders - Google Patents
5- (phenylisoxazolylethoxy) -triazol- 3 -yl substituted pyridine compounds for the treatment of neurological, psychiatric or pain disorders Download PDFInfo
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- AU2006297462A1 AU2006297462A1 AU2006297462A AU2006297462A AU2006297462A1 AU 2006297462 A1 AU2006297462 A1 AU 2006297462A1 AU 2006297462 A AU2006297462 A AU 2006297462A AU 2006297462 A AU2006297462 A AU 2006297462A AU 2006297462 A1 AU2006297462 A1 AU 2006297462A1
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72152705P | 2005-09-29 | 2005-09-29 | |
| US60/721,527 | 2005-09-29 | ||
| PCT/US2006/036423 WO2007040982A1 (en) | 2005-09-29 | 2006-09-20 | 5- (phenylisoxazolylethoxy) -triazol- 3 -yl substituted pyridine compounds for the treatment of neurological, psychiatric or pain disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2006297462A1 true AU2006297462A1 (en) | 2007-04-12 |
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| AU2006297462A Abandoned AU2006297462A1 (en) | 2005-09-29 | 2006-09-20 | 5- (phenylisoxazolylethoxy) -triazol- 3 -yl substituted pyridine compounds for the treatment of neurological, psychiatric or pain disorders |
Country Status (18)
| Country | Link |
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| US (4) | US20080227824A1 (https=) |
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| AU (1) | AU2006297462A1 (https=) |
| BR (1) | BRPI0616228A2 (https=) |
| CA (1) | CA2623009A1 (https=) |
| EC (1) | ECSP088283A (https=) |
| IL (1) | IL189990A0 (https=) |
| NO (1) | NO20081434L (https=) |
| RU (1) | RU2008108219A (https=) |
| TW (1) | TW200800976A (https=) |
| UA (1) | UA92503C2 (https=) |
| UY (1) | UY29796A1 (https=) |
| WO (1) | WO2007040982A1 (https=) |
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| US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| UY29796A1 (es) * | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
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| BRPI0818448A2 (pt) * | 2007-10-19 | 2015-05-12 | Astrazeneca Ab | Composto, composição farmacêutica, uso de um composto, e, métodos para o tratamento ou prevenção de um distúrbio madiano pelo receptor mglur5. |
| TW200922585A (en) * | 2007-10-26 | 2009-06-01 | Astrazeneca Ab | Amino 1,2,4-triazole derivatives as modulators of mGluR5 |
| EP2324019A4 (en) * | 2008-08-12 | 2011-10-05 | Astrazeneca Ab | CRYSTALLINE FORM OF (5- {(IR) -1- [5- (3-CHLOROPHENYL) ISOXAZOL-3-YL] ETHOXY} -4-METHYL-4H-L, 2, 4-TRIAZOL-3-YL) -PYRIDINE |
| WO2010019100A1 (en) * | 2008-08-12 | 2010-02-18 | Astrazeneca Ab | A new crystalline form of 4- (5- { (ir) -1- [5- (3- chlorophenyl) isoxazol-3-yl] ethoxy } -4-methyl-4h-l, 2, 4- triazol-3-yl) pyridine |
| CA2751761A1 (en) | 2008-10-22 | 2010-04-29 | House Ear Institute | Treatment and/or prevention of inner ear conditions by modulation of a metabotropic glutamate receptor |
| BRPI0923215A2 (pt) * | 2008-12-12 | 2017-06-06 | Astrazeneca Ab | método para fabricar um composto. |
| CA2747507A1 (en) * | 2008-12-18 | 2010-06-24 | Astrazeneca Ab | New process for the preparation of 1- [5-(3-chloro-phenyl)-isooxazol-3-yl]-ethanone and (r)-1-[5-(3-chloro-phenyl)-isooxazol-3-yl]-ethanol |
| EP2379531A1 (en) * | 2008-12-18 | 2011-10-26 | AstraZeneca AB | Processes for the manufacture of 3-{4-methyl-5- [ (ir) -1- (2- (3-methylphenyl) -2h-tetrazol-5-yl) -ethoxy]-4h- [1,2, 4]triazol-3-yl} -pyridine, 4-methyl-3-methylthio-5- (3- pyridyl)-l,2,4-triazole, and (ir) -1- [2- (3-methylphenyl) -2h- tetrazol-5-yl]ethanol |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| CA2764339A1 (en) * | 2009-06-05 | 2010-12-09 | Oslo University Hospital Hf | Azole derivatives as wtn pathway inhibitors |
| ES2443578T3 (es) | 2009-12-29 | 2014-02-19 | Eli Lilly And Company | Compuestos de tetrahidrotriazolopiridina como potenciadores de receptores selectivos de mGlu5 útiles para el tratamiento de la esquizofrenia |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| JP2013518085A (ja) | 2010-02-01 | 2013-05-20 | ノバルティス アーゲー | ＣＲＦ−１受容体アンタゴニストとしてのピラゾロ［５，１ｂ］オキサゾール誘導体 |
| JP5748777B2 (ja) | 2010-02-02 | 2015-07-15 | ノバルティス アーゲー | Ｃｒｆ受容体アンタゴニストとしてのシクロヘキシルアミド誘導体 |
| US8080568B1 (en) * | 2010-06-29 | 2011-12-20 | Ewha University - Industry Collaboration Foundation | 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors |
| UA112418C2 (uk) * | 2010-09-07 | 2016-09-12 | Астеллас Фарма Інк. | Терапевтичний болезаспокійливий засіб |
| RU2013128448A (ru) | 2010-12-08 | 2015-01-20 | Осло Юниверсити Хоспитал Хф | Производные триазола в качестве ингибиторов сигнального пути wnt |
| AU2012232711B2 (en) | 2011-03-18 | 2016-04-28 | Novartis Ag | Combinations of alpha 7 nicotinic acetylcholine receptor activators and mGluR5 antagonists for use in dopamine induced dyskinesia in Parkinson's Disease |
| WO2016163754A1 (en) * | 2015-04-07 | 2016-10-13 | Medpacto Inc. | Pharmaceutical composition for preventing or treating cancer and method using thereof |
| KR20160120157A (ko) | 2015-04-07 | 2016-10-17 | 주식회사 메드팩토 | 암 예방 또는 치료용 약학적 조성물 및 이를 이용한 방법 |
| KR102027368B1 (ko) * | 2018-05-29 | 2019-10-01 | 서울대학교산학협력단 | 통증의 강도를 측정하는 방법 |
| AU2019384074B2 (en) | 2018-11-20 | 2025-04-10 | Sparrow Pharmaceuticals, Inc. | Methods for administering corticosteroids |
| CN113811297B (zh) * | 2019-05-15 | 2024-03-26 | 克拉斯·图林 | 用于预防和/或治疗动物中的疼痛的4-[5-[(rac)-1-[5-(3-氯苯基)-3-异噁唑基]乙氧基]-4-甲基-4H-1,2,4-三唑-3-基]吡啶 |
| KR20220097405A (ko) | 2019-11-05 | 2022-07-07 | 클라에스 툴린 | 포유동물에서의 혹사의 예방 및/또는 치료에 사용하기 위한 4-[5-[(rac)-1-[5-(3-클로로페닐)-3-이속사졸일]에톡시]-4-메틸-4H-1,2,4-트리아졸-3-일]피리딘 |
| EP4525983A4 (en) | 2022-05-16 | 2025-09-03 | Sparrow Pharmaceuticals Inc | METHODS AND COMPOSITIONS FOR TREATING GLUCOCORTICOID EXCESS |
| EP4583872A1 (en) | 2022-10-28 | 2025-07-16 | Orphelion Ab | Mglur5 receptor antagonists for use in prevention and/or treatment of bone marrow lesions (bml) and/or osteoporosis, cartilage loss, osteosclerosis, osteitis in a mammal |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100875222B1 (ko) | 1999-08-19 | 2008-12-19 | 아스트라제네카 아베 | 헤테로폴리사이클릭 화합물 및 간접 글루타메이트 수용체길항제로서의 그들의 용도 |
| MXPA03007513A (es) | 2001-02-21 | 2004-07-30 | Nps Pharma Inc | Compuestos heteropoliciclicos y su uso como antagonistas del receptor metabotropico de glutamato. |
| WO2004014881A2 (en) | 2002-08-09 | 2004-02-19 | Astra Zeneca Ab | '1,2,4'oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| US7074809B2 (en) | 2002-08-09 | 2006-07-11 | Astrazeneca Ab | Compounds |
| TW200424183A (en) | 2002-08-09 | 2004-11-16 | Nps Pharma Inc | New compounds |
| WO2005060971A1 (en) | 2003-12-18 | 2005-07-07 | Astrazeneca Ab | Treatment of reflux-related diseases |
| CA2548039A1 (en) | 2003-12-19 | 2005-07-21 | Astrazenca Ab | 5-fluoro-, chloro- and cyano-pyridin-2-yl-tetrazoles as ligands of the metabotropic glutamate receptor-5 |
| WO2005077345A1 (en) | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Compounds for the treatment of gastro-esophageal reflux disease |
| WO2005077368A2 (en) | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Treatment of gastro-esophageal reflux disease (gerd) |
| DE602005008558D1 (de) | 2004-02-18 | 2008-09-11 | Astrazeneca Ab | Kondensierte heterocyclische verbindungen und deren verwendung als antagonisten des metabotropen reznkungen |
| TW200531694A (en) | 2004-02-18 | 2005-10-01 | Astrazeneca Ab | Acetylinic piperazine compounds and their use as metabotropic glutamate receptor antagonists |
| US20070185100A1 (en) | 2004-02-18 | 2007-08-09 | Astrazeneca Ab | Poly-heterocyclic compounds and their use as metabotropic glutamate receptor antagonists |
| WO2005080356A1 (en) | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
| US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| RU2006127575A (ru) | 2004-02-18 | 2008-03-27 | Астразенека Аб (Se) | Соединение триазола и их применение в качестве антагонистов метаботропного рецептора глутамата |
| UY29796A1 (es) * | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
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- 2006-09-15 AR ARP060104038A patent/AR058807A1/es not_active Application Discontinuation
- 2006-09-19 TW TW095134584A patent/TW200800976A/zh unknown
- 2006-09-20 UA UAA200802884A patent/UA92503C2/ru unknown
- 2006-09-20 AU AU2006297462A patent/AU2006297462A1/en not_active Abandoned
- 2006-09-20 CN CNA2006800343984A patent/CN101273037A/zh active Pending
- 2006-09-20 CA CA002623009A patent/CA2623009A1/en not_active Abandoned
- 2006-09-20 RU RU2008108219/04A patent/RU2008108219A/ru not_active Application Discontinuation
- 2006-09-20 KR KR1020087006537A patent/KR20080050421A/ko not_active Withdrawn
- 2006-09-20 EP EP06803836A patent/EP1934209A1/en not_active Withdrawn
- 2006-09-20 US US12/067,270 patent/US20080227824A1/en not_active Abandoned
- 2006-09-20 JP JP2008533434A patent/JP2009510064A/ja active Pending
- 2006-09-20 WO PCT/US2006/036423 patent/WO2007040982A1/en not_active Ceased
- 2006-09-20 US US11/523,717 patent/US7476684B2/en not_active Expired - Fee Related
- 2006-09-20 BR BRPI0616228-2A patent/BRPI0616228A2/pt not_active IP Right Cessation
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2007
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- 2007-07-27 US US11/829,867 patent/US20070270469A1/en not_active Abandoned
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2008
- 2008-03-06 IL IL189990A patent/IL189990A0/en unknown
- 2008-03-07 ZA ZA200802163A patent/ZA200802163B/xx unknown
- 2008-03-14 EC EC2008008283A patent/ECSP088283A/es unknown
- 2008-03-19 NO NO20081434A patent/NO20081434L/no not_active Application Discontinuation
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2009
- 2009-09-14 JP JP2009211258A patent/JP2010013476A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20070270469A1 (en) | 2007-11-22 |
| BRPI0616228A2 (pt) | 2011-06-14 |
| ECSP088283A (es) | 2008-04-28 |
| US7476684B2 (en) | 2009-01-13 |
| UY29796A1 (es) | 2007-04-30 |
| US20070129408A1 (en) | 2007-06-07 |
| JP2010013476A (ja) | 2010-01-21 |
| RU2008108219A (ru) | 2009-11-10 |
| AR058807A1 (es) | 2008-02-27 |
| CA2623009A1 (en) | 2007-04-12 |
| ZA200802163B (en) | 2009-09-30 |
| CN101273037A (zh) | 2008-09-24 |
| NO20081434L (no) | 2008-05-19 |
| UA92503C2 (ru) | 2010-11-10 |
| WO2007040982A1 (en) | 2007-04-12 |
| EP1934209A1 (en) | 2008-06-25 |
| US20070270468A1 (en) | 2007-11-22 |
| US20080227824A1 (en) | 2008-09-18 |
| IL189990A0 (en) | 2008-08-07 |
| KR20080050421A (ko) | 2008-06-05 |
| TW200800976A (en) | 2008-01-01 |
| JP2009510064A (ja) | 2009-03-12 |
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