EA030604B1 - Соединения, применимые в качестве ингибиторов s100 - Google Patents
Соединения, применимые в качестве ингибиторов s100 Download PDFInfo
- Publication number
- EA030604B1 EA030604B1 EA201692405A EA201692405A EA030604B1 EA 030604 B1 EA030604 B1 EA 030604B1 EA 201692405 A EA201692405 A EA 201692405A EA 201692405 A EA201692405 A EA 201692405A EA 030604 B1 EA030604 B1 EA 030604B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- oxo
- trifluoromethyl
- dodeca
- triazatricyclo
- tetraen
- Prior art date
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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Landscapes
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (2)
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|---|---|---|---|
| EP14169757 | 2014-05-23 | ||
| PCT/EP2015/061468 WO2015177367A1 (en) | 2014-05-23 | 2015-05-22 | Novel compounds useful as s100-inhibitors |
Publications (2)
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|---|---|
| EA201692405A1 EA201692405A1 (ru) | 2017-06-30 |
| EA030604B1 true EA030604B1 (ru) | 2018-08-31 |
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| EA201692405A EA030604B1 (ru) | 2014-05-23 | 2015-05-22 | Соединения, применимые в качестве ингибиторов s100 |
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| EP (1) | EP2991990B1 (enExample) |
| JP (1) | JP6580074B2 (enExample) |
| KR (1) | KR20170005868A (enExample) |
| CN (1) | CN106414448B (enExample) |
| AU (1) | AU2015261775B2 (enExample) |
| BR (1) | BR112016024749A2 (enExample) |
| CA (1) | CA2948436A1 (enExample) |
| EA (1) | EA030604B1 (enExample) |
| ES (1) | ES2620751T3 (enExample) |
| MX (1) | MX2016014483A (enExample) |
| WO (1) | WO2015177367A1 (enExample) |
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| WO2019208290A1 (ja) | 2018-04-27 | 2019-10-31 | 国立大学法人 岡山大学 | 抗s100a8/a9抗体とその用途 |
| US11197908B2 (en) | 2018-07-17 | 2021-12-14 | The Board Of Trustees Of The University Of Arkansas | Peptoids and methods for attenuating inflammatory response |
| EP4052725A4 (en) | 2019-10-30 | 2024-07-17 | National University Corporation Okayama University | PROPHYLACTIC AND/OR THERAPEUTIC AGENT FOR INFLAMMATORY LUNG DISEASE |
| WO2023209141A1 (en) | 2022-04-29 | 2023-11-02 | Westfälische Wilhelms-Universität Münster | Benzo[d]imidazo[1,2-a]imidazoles and their use in diagnosis |
| WO2025132458A1 (en) | 2023-12-18 | 2025-06-26 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as alk5 inhibitors |
Citations (2)
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|---|---|---|---|---|
| WO2002069965A1 (en) * | 2001-03-05 | 2002-09-12 | Transtech Pharma, Inc. | Benzimidazole derivatives as therapeutic agents |
| US20090186879A1 (en) * | 2008-01-22 | 2009-07-23 | Takeda Pharmaceutical Company Limited | Tricyclic compounds and use thereof |
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| US6248755B1 (en) | 1999-04-06 | 2001-06-19 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| AR029489A1 (es) | 2000-03-10 | 2003-07-02 | Euro Celtique Sa | Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento |
| DE60125373T2 (de) | 2000-07-26 | 2007-10-18 | Smithkline Beecham P.L.C., Brentford | Aminopiperidin chinoline und ihre azaisosteren analoga mit antibakterieller wirkung |
| GB0117506D0 (en) | 2001-07-18 | 2001-09-12 | Bayer Ag | Imidazopyridinones |
| SE0104331D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Novel compounds |
| CN101597262A (zh) * | 2002-03-05 | 2009-12-09 | 特兰斯泰克制药公司 | 抑制配体与高级糖化终产物受体相互作用的单和双环吡咯衍生物 |
| US20060111416A1 (en) | 2004-11-24 | 2006-05-25 | Lane Charlotte A L | Octahydropyrrolo[3,4-C]pyrrole derivatives |
| CA2663856A1 (en) | 2006-09-28 | 2008-04-10 | Exelixis, Inc. | Jak-2 modulators and methods of use |
| AU2008231384B2 (en) | 2007-03-23 | 2011-09-15 | Amgen Inc. | Heterocyclic compounds and their use |
| EP1986009A1 (en) * | 2007-04-26 | 2008-10-29 | Active Biotech AB | Screening method |
| BRPI0812521A2 (pt) | 2007-06-13 | 2015-06-23 | Glaxosmithkline Llc | Composto, composição farmacêutica, método para o tratamento de doença em um mamífero, processo para a preparação de um composto, e, uso de um composto |
| TW201004941A (en) | 2008-07-16 | 2010-02-01 | Wyeth Corp | Alpha7 nicotinic acetylcholine receptor inhibitors |
| MX2011009213A (es) | 2009-03-02 | 2011-12-14 | Sirtris Pharmaceuticals Inc | Quinolinas 8-sustituidas y analogos relacionados como moduladores de sirtuina. |
| BR112014010391A2 (pt) | 2011-11-03 | 2017-04-18 | Hoffmann La Roche | composto, composição farmacêutica, processo de produção de uma composição farmacêutica, método de tratamento, kit e uso de uma composição farmacêutica |
| GB201321728D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
-
2015
- 2015-05-22 KR KR1020167035803A patent/KR20170005868A/ko not_active Withdrawn
- 2015-05-22 MX MX2016014483A patent/MX2016014483A/es unknown
- 2015-05-22 ES ES15724640.6T patent/ES2620751T3/es active Active
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- 2015-05-22 JP JP2016568812A patent/JP6580074B2/ja not_active Expired - Fee Related
- 2015-05-22 AU AU2015261775A patent/AU2015261775B2/en not_active Ceased
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- 2015-05-22 CN CN201580026356.5A patent/CN106414448B/zh not_active Expired - Fee Related
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002069965A1 (en) * | 2001-03-05 | 2002-09-12 | Transtech Pharma, Inc. | Benzimidazole derivatives as therapeutic agents |
| US20090186879A1 (en) * | 2008-01-22 | 2009-07-23 | Takeda Pharmaceutical Company Limited | Tricyclic compounds and use thereof |
Non-Patent Citations (3)
| Title |
|---|
| DESCOURS DENIS; FESTAL DIDIER: "Reactions of N-(.omega.-Chloroalkanoyl)-carbonimidic Dichlorides: A New Synthesis of 2-Oxo-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoles, 2-Oxo-2, 3-dihydro-1H-imidazo[1,2-a]benzimidazoles, and 2-Oxo-2,3,5,10-tetrahydro-1H-imidazo[1,2-b][2,4]benzodiazepines", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 1983, no. 12, 1 December 1983 (1983-12-01), STUTTGART, DE., pages 1033 - 1036, XP002727411, ISSN: 0039-7881, DOI: 10.1055/s-1983-30617 * |
| IVANO MESSINA , IGOR POPA , VÍTĚZSLAV MAIER , AND MIROSLAV SOURAL: "Solid-Phase Synthesis of 5-Noranagrelide Derivatives", ACS COMBINATORIAL SCIENCE, AMERICAN CHEMICAL SOCIETY, US, vol. 16, no. 1, 1 January 2014 (2014-01-01), US, pages 33 - 38, XP002727412, ISSN: 2156-8952, DOI: 10.1021/co40013151 * |
| TROXLER FRANZ., WEBER HANS PETER: "Synthese von Pyrimido[1,2-a]benzimidazolen durch Umsetzung von 2-Aminobenzimidazol mit Acetylendicarbonsäure-dimethylester und ihre Überführung in Imidazol[1,2-a]benzimidazole.", HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA., CH, vol. 57, no. 8, 1 August 1974 (1974-08-01), CH, pages 2356 - 2364, XP002727410, ISSN: 0018-019X, DOI: 10.1002/hlca.19740570807 * |
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| MX2016014483A (es) | 2017-01-23 |
| ES2620751T3 (es) | 2017-06-29 |
| BR112016024749A2 (pt) | 2017-08-15 |
| AU2015261775A1 (en) | 2016-12-08 |
| HK1221463A1 (en) | 2017-06-02 |
| EA201692405A1 (ru) | 2017-06-30 |
| AU2015261775B2 (en) | 2019-07-11 |
| WO2015177367A1 (en) | 2015-11-26 |
| EP2991990B1 (en) | 2017-02-01 |
| US9771372B2 (en) | 2017-09-26 |
| JP2017516772A (ja) | 2017-06-22 |
| JP6580074B2 (ja) | 2019-09-25 |
| CA2948436A1 (en) | 2015-11-26 |
| CN106414448A (zh) | 2017-02-15 |
| US20170204098A1 (en) | 2017-07-20 |
| KR20170005868A (ko) | 2017-01-16 |
| CN106414448B (zh) | 2019-04-19 |
| EP2991990A1 (en) | 2016-03-09 |
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