CA2938703C - Substituted thiazole or oxazole p2x7 receptor antagonists - Google Patents

Substituted thiazole or oxazole p2x7 receptor antagonists Download PDF

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CA2938703C
CA2938703C CA2938703A CA2938703A CA2938703C CA 2938703 C CA2938703 C CA 2938703C CA 2938703 A CA2938703 A CA 2938703A CA 2938703 A CA2938703 A CA 2938703A CA 2938703 C CA2938703 C CA 2938703C
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compound
formula
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CA2938703A1 (en
Inventor
Paolo Pevarello
Stefan Lohmer
Chiara Liberati
Pierfausto Seneci
Cristina PESENTI
Adolfo Prandi
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Breye Therapeutics ApS
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AXXAM SpA
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    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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EP2905282A1 (en) * 2014-02-05 2015-08-12 AXXAM S.p.A. Substituted thiazole or oxazole as P2X7 receptor antagonists
EP3290417A1 (en) 2016-08-31 2018-03-07 AXXAM S.p.A. 2-chloro-n-[2-(1,3-thiazol-5-yl)ethyl]-5-(5-fluoropyrimidin-2-yl)-benzamides and their use as p2x7 receptor antagonists
EP3290416A1 (en) 2016-08-31 2018-03-07 AXXAM S.p.A. Substituted n-[2-(4-phenoxypiperidin-1-yl)-2-(1,3-thiazol-5-yl)ethyl]benzamide and n-[2-(4-benzyloxypiperidin-1-yl)-2-(1,3-thiazol-5-yl)ethyl]benzamide derivatives and their use as p2x7 receptor antagonist
CN106562947A (zh) * 2016-11-03 2017-04-19 南昌大学 亮蓝g在制备人类免疫缺陷病毒糖蛋白120诱导神经病理痛药物中的应用
CN111377867B (zh) * 2018-12-28 2022-09-06 南京药石科技股份有限公司 一种合成2-(1-烷基-1h-吡唑-4-基)吗啉的中间体及其制备方法和应用
KR20210135521A (ko) 2019-03-06 2021-11-15 다이이찌 산쿄 가부시키가이샤 피롤로피라졸 유도체
EP3962493A2 (en) 2019-05-03 2022-03-09 Flagship Pioneering Innovations V, Inc. Methods of modulating immune activity/level of irf or sting or of treating cancer, comprising the administration of a sting modulator and/or purinergic receptor modulator or postcellular signaling factor
EP4015039A1 (en) * 2020-12-18 2022-06-22 AXXAM S.p.A. Heterocyclic derivatives as p2x7 receptor antagonists
CN113968806A (zh) * 2021-10-12 2022-01-25 北京科技大学 一种非对称硫代酰胺类萃取剂及其合成方法
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WO2025261412A1 (zh) * 2024-06-18 2025-12-26 武汉人福创新药物研发中心有限公司 氨基酯类化合物及其作为p2x7拮抗剂的用途
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CN121248499A (zh) * 2025-09-22 2026-01-02 广州国家实验室 四氢异喹啉类木瓜蛋白酶样蛋白酶抑制剂及其用途

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US9718812B2 (en) 2017-08-01
WO2015118019A9 (en) 2016-04-21
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CA2938703A1 (en) 2015-08-13
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US20170008883A1 (en) 2017-01-12
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