ES2967410T3 - Compuestos de bencenosulfonamida y sus usos en forma de agentes terapéuticos - Google Patents
Compuestos de bencenosulfonamida y sus usos en forma de agentes terapéuticos Download PDFInfo
- Publication number
- ES2967410T3 ES2967410T3 ES17728326T ES17728326T ES2967410T3 ES 2967410 T3 ES2967410 T3 ES 2967410T3 ES 17728326 T ES17728326 T ES 17728326T ES 17728326 T ES17728326 T ES 17728326T ES 2967410 T3 ES2967410 T3 ES 2967410T3
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- Spain
- Prior art keywords
- amino
- compound
- benzenesulfonamide
- difluoro
- pharmaceutically acceptable
- 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.)
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
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- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
- C07D263/50—Benzene-sulfonamido oxazoles
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3023465C (en) | 2016-05-20 | 2024-09-24 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| AU2017371674B2 (en) | 2016-12-09 | 2021-07-22 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| CN112262142B (zh) * | 2018-06-13 | 2023-11-14 | 泽农医药公司 | 苯磺酰胺化合物及其作为治疗剂的用途 |
| US10752623B2 (en) | 2018-08-31 | 2020-08-25 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors |
| MA53489A (fr) * | 2018-08-31 | 2021-12-08 | Xenon Pharmaceuticals Inc | Composés de sulfonamide substitués par hétéroaryle et leur utilisation en tant qu'agents thérapeutiques |
| CN111285825B (zh) * | 2018-12-10 | 2023-02-17 | 中国科学院上海药物研究所 | 一类苯磺酰胺取代的衍生物,其制法及其用途 |
| CN112125838B (zh) * | 2020-08-31 | 2021-07-27 | 浙江工业大学 | 一种三氟甲基化苯胺类化合物及其应用 |
| WO2023028056A1 (en) | 2021-08-24 | 2023-03-02 | Genentech, Inc. | 3-amino piperidyl sodium channel inhibitors |
| CN113698357A (zh) * | 2021-09-29 | 2021-11-26 | 守恒(厦门)医疗科技有限公司 | 磺胺嘧啶类衍生物及其在抗肿瘤药物的应用 |
| CN113861130A (zh) * | 2021-09-29 | 2021-12-31 | 守恒(厦门)医疗科技有限公司 | 联苯磺胺噻二唑类衍生物及其在抗肿瘤药物的应用 |
| US20250034108A1 (en) * | 2023-07-07 | 2025-01-30 | Novartis Ag | Sodium channel blockers |
Family Cites Families (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US4326525A (en) | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US5877193A (en) | 1996-07-19 | 1999-03-02 | Hoffmann-La Roche Inc. | Use of N-(4-aryl-thiazol-2-yl)-sulfonamides |
| ATE227120T1 (de) | 1997-05-07 | 2002-11-15 | Galen Chemicals Ltd | Vorrichtungen zur intravaginalen verabreichung von testosteron und testosteron- vorläuferverbindungen |
| US6440966B1 (en) | 1999-01-13 | 2002-08-27 | Warner-Lambert Company | Benzenesulfonamide derivatives and their use as MEK inhibitors |
| HK1047895A1 (zh) | 1999-07-16 | 2003-03-14 | 沃尼尔‧朗伯公司 | 使用mek抑制剂治疗慢性疼痛的方法 |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| FR2836917B1 (fr) | 2002-03-11 | 2006-02-24 | Lipha | Derives nitroso de la diphenylamine, compositions pharmaceutiques les contenant en tant que medicaments utilisables dans le traitement des pathologies caracterisees par une situation de stress oxydatif |
| WO2004002481A1 (en) | 2002-06-27 | 2004-01-08 | Novo Nordisk A/S | Aryl carbonyl derivatives as therapeutic agents |
| WO2004092123A2 (en) * | 2003-04-10 | 2004-10-28 | Microbia, Inc. | Inhibitors of fungal invasion |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| US7538135B2 (en) | 2003-07-08 | 2009-05-26 | Novartis Ag | Benzenesulfonylamino compounds and pharmaceutical compositions containing these compounds |
| KR20060073930A (ko) | 2003-08-08 | 2006-06-29 | 버텍스 파마슈티칼스 인코포레이티드 | 통증 치료시 나트륨 또는 칼슘 채널 차단제로서 유용한헤테로아릴아미노설포닐페닐 유도체 |
| JP2008524244A (ja) * | 2004-12-17 | 2008-07-10 | タケダ サン ディエゴ インコーポレイテッド | 水酸化ステロイド脱水素酵素阻害剤 |
| GB0510139D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| CN101277940A (zh) | 2005-10-06 | 2008-10-01 | 塞诺菲-安万特股份有限公司 | 4-氧基-n-[1,3,4]-噻二唑-2-基-苯磺酰胺、它们的制备方法及它们作为药物的用途 |
| CA2633653A1 (en) | 2005-12-21 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Heterocyclic derivatives as modulators of ion channels |
| US7754744B2 (en) | 2006-08-15 | 2010-07-13 | Hoffmann-La Roche Inc. | Substituted piperidinamines as somatostatin receptor subtype 5 (SSTR5) antagonists |
| ZA200902384B (en) | 2006-10-19 | 2010-07-28 | Signal Pharm Llc | Heteroaryl compounds, compositions thereof, and use thereof as protein kinase inhibitors |
| EP2173743A2 (en) * | 2007-07-13 | 2010-04-14 | Icagen, Inc. | Sodium channel inhibitors |
| WO2009012241A1 (en) * | 2007-07-13 | 2009-01-22 | Icagen, Inc. | Sodium channel inhibitors |
| WO2009013171A2 (en) | 2007-07-24 | 2009-01-29 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| EP2289868B1 (en) | 2008-06-25 | 2014-08-13 | Daiichi Sankyo Company, Limited | Carboxylic acid compound |
| KR20110025855A (ko) | 2008-07-01 | 2011-03-11 | 버텍스 파마슈티칼스 인코포레이티드 | 이온 채널의 조절제로서의 헤테로사이클릭 유도체 |
| WO2010029300A1 (en) | 2008-09-12 | 2010-03-18 | Biolipox Ab | Bis aromatic compounds for use in the treatment of inflammation |
| GEP20135992B (en) * | 2009-01-12 | 2013-12-25 | Icagen Inc | Sulfonamide derivatives |
| EP2590951B1 (en) | 2010-07-09 | 2015-01-07 | Pfizer Limited | Benzenesulfonamides useful as sodium channel inhibitors |
| KR101541086B1 (ko) | 2010-08-20 | 2015-08-03 | 허치슨 메디파르마 리미티드 | 피롤로피리미딘 화합물 및 그 용도 |
| JP2014521749A (ja) | 2011-08-17 | 2014-08-28 | アムジエン・インコーポレーテツド | ヘテロアリールナトリウムチャネル阻害剤 |
| KR20140095067A (ko) | 2011-10-28 | 2014-07-31 | 머크 샤프 앤드 돔 코포레이션 | 전압-게이팅 나트륨 채널에서의 선택적 활성을 갖는 벤족사졸리논 화합물 |
| RU2014121983A (ru) * | 2011-10-31 | 2015-12-10 | Ксенон Фармасьютикалз Инк. | Биарильные простоэфирные сульфонамиды и их применение в качестве терапевтических средств |
| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| US8889741B2 (en) * | 2012-02-09 | 2014-11-18 | Daiichi Sankyo Company, Limited | Cycloalkane derivatives |
| US9346798B2 (en) | 2012-02-13 | 2016-05-24 | Amgen Inc. | Dihydrobenzoxazine and tetrahydroquinoxaline sodium channel inhibitors |
| US8952169B2 (en) | 2012-05-22 | 2015-02-10 | Xenon Pharmaceuticals Inc. | N-substituted benzamides and methods of use thereof |
| CA2887845C (en) * | 2012-10-15 | 2020-12-15 | Daewoong Pharmaceutical Co., Ltd. | Sodium channel blockers, preparation method thereof and use thereof |
| US9388179B2 (en) | 2012-10-26 | 2016-07-12 | Merck Sharp & Dohme Corp. | N-substituted indazole sulfonamide compounds with selective activity in voltage-gated sodium channels |
| KR20150074122A (ko) | 2012-10-26 | 2015-07-01 | 머크 샤프 앤드 돔 코포레이션 | 전압-게이팅 나트륨 채널에서 선택적 활성을 갖는 벤족사졸리논 화합물 |
| TW201443025A (zh) * | 2013-04-19 | 2014-11-16 | Pfizer Ltd | 化學化合物 |
| TW201512171A (zh) * | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| US9776995B2 (en) | 2013-06-12 | 2017-10-03 | Amgen Inc. | Bicyclic sulfonamide compounds as sodium channel inhibitors |
| GB201310542D0 (en) | 2013-06-13 | 2013-07-31 | Antabio Sas | Compounds |
| CN105705501B (zh) | 2013-09-09 | 2019-04-19 | 百时美施贵宝公司 | RORγ调节剂 |
| CN105611923B (zh) | 2013-09-10 | 2019-08-23 | 卓莫赛尔公司 | 用于治疗疼痛和糖尿病的钠通道调节剂 |
| CA2931732A1 (en) | 2013-11-27 | 2015-06-04 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| WO2015077905A1 (en) | 2013-11-29 | 2015-06-04 | Merck Sharp & Dohme Corp. | Bicycloamine-substituted-n-benzenesulfonamide compounds with selective activity in voltage-gated sodium channels |
| WO2015099841A1 (en) * | 2013-12-23 | 2015-07-02 | Purdue Pharma L.P. | Indazoles and use thereof |
| CN106795149B (zh) * | 2015-05-05 | 2019-09-24 | 上海海雁医药科技有限公司 | 双环取代的苯磺酰胺衍生物、其制法与医药上的用途 |
| MA44085A (fr) | 2015-12-18 | 2021-04-21 | Merck Sharp & Dohme | Composés d'arylsulfonamide à liaisons diamino-alkylamino ayant une activité sélective vis-à-vis des canaux sodiques voltage-dépendants |
| EP3484464B1 (en) * | 2016-03-22 | 2020-10-28 | Merck Sharp & Dohme Corp. | N1-phenylpropane-1,2-diamine compounds with selective activity in voltage-gated sodium channels |
| CA3023465C (en) | 2016-05-20 | 2024-09-24 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| EP3532462B1 (en) * | 2016-10-27 | 2021-10-13 | Bristol-Myers Squibb Company | Acyl sulfonamide nav1.7 inhibitors |
| EP3541373B1 (en) * | 2016-11-17 | 2023-11-01 | Merck Sharp & Dohme LLC | Diamino-alkylamino-linked arylsulfonamide compounds with selective activity in voltage-gated sodium channels |
| AU2017371674B2 (en) | 2016-12-09 | 2021-07-22 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| CN112262142B (zh) | 2018-06-13 | 2023-11-14 | 泽农医药公司 | 苯磺酰胺化合物及其作为治疗剂的用途 |
| MA53489A (fr) | 2018-08-31 | 2021-12-08 | Xenon Pharmaceuticals Inc | Composés de sulfonamide substitués par hétéroaryle et leur utilisation en tant qu'agents thérapeutiques |
| US10752623B2 (en) | 2018-08-31 | 2020-08-25 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors |
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| RU2760303C2 (ru) | 2021-11-23 |
| CO2019005552A2 (es) | 2019-05-31 |
| KR20190086772A (ko) | 2019-07-23 |
| PH12019501074A1 (en) | 2019-08-19 |
| TN2019000175A1 (en) | 2020-10-05 |
| US11174268B2 (en) | 2021-11-16 |
| EP3551626A1 (en) | 2019-10-16 |
| US20180162868A1 (en) | 2018-06-14 |
| MA48583A (fr) | 2021-04-21 |
| EP3551626B1 (en) | 2023-10-25 |
| CN110325531B (zh) | 2022-05-27 |
| CA3042004A1 (en) | 2018-06-14 |
| WO2018106284A1 (en) | 2018-06-14 |
| AU2017371674B2 (en) | 2021-07-22 |
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