EA030679B1 - Соединения и способы лечения гриппа - Google Patents
Соединения и способы лечения гриппа Download PDFInfo
- Publication number
- EA030679B1 EA030679B1 EA201270077A EA201270077A EA030679B1 EA 030679 B1 EA030679 B1 EA 030679B1 EA 201270077 A EA201270077 A EA 201270077A EA 201270077 A EA201270077 A EA 201270077A EA 030679 B1 EA030679 B1 EA 030679B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- virus
- influenza
- compound
- nitazoxanide
- pharmaceutically acceptable
- Prior art date
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Landscapes
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| US22089109P | 2009-06-26 | 2009-06-26 | |
| PCT/US2010/039638 WO2010151577A1 (en) | 2009-06-26 | 2010-06-23 | Compounds and methods for treating influenza |
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| EA201270077A1 EA201270077A1 (ru) | 2012-12-28 |
| EA030679B1 true EA030679B1 (ru) | 2018-09-28 |
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| EP (2) | EP2445349B1 (enExample) |
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| EA021587B1 (ru) | 2009-05-12 | 2015-07-30 | РОМАРК ЛЭБОРЕТЕРИЗ Эл. Си. | Соединения галогеналкилгетероарилбензамида |
| EA030679B1 (ru) * | 2009-06-26 | 2018-09-28 | РОМАРК ЛЭБОРЕТЕРИЗ Эл.Си. | Соединения и способы лечения гриппа |
| WO2012061190A1 (en) * | 2010-11-01 | 2012-05-10 | Romark Laboratories L.C. | Alkylsulfinyl-substituted thiazolide compounds |
| AU2016201747B2 (en) * | 2011-05-16 | 2017-06-01 | Romark Laboratories, L.C. | Use of thiazolide compounds for the prevention and treatment of viral diseases, cancer and diseases caused by intracellular infections |
| CN107096032A (zh) * | 2011-05-16 | 2017-08-29 | 罗马克实验室有限公司 | 在有需要的对象中刺激免疫应答的方法 |
| PT107894A (pt) | 2011-10-21 | 2014-10-31 | Abbvie Inc | Métodos para o tratamento de hcv compreendendo pelo menos dois agentes antivirais de actuação directa, ribavirina, mas não interferão. |
| US8466159B2 (en) | 2011-10-21 | 2013-06-18 | Abbvie Inc. | Methods for treating HCV |
| GB2515942A (en) | 2011-10-21 | 2015-01-07 | Abbvie Inc | Combination treatment (e.g. with ABT-072 or ABT-333) of DAAs for use in treating HCV |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| US10131643B2 (en) | 2013-07-04 | 2018-11-20 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China | Tizoxanide carbamate and pharmaceutical use thereof |
| CN104771398B (zh) * | 2014-01-09 | 2017-01-18 | 湖南大学 | N‑[5‑（2‑硝基乙基）噻唑‑2‑基]苯甲酰胺及其医药用途 |
| BR112017009651A2 (pt) | 2014-11-11 | 2017-12-19 | Romark Laboratories Lc | composto, composição farmacêutica, e, método para tratamento de uma infecção por protozoário intracelular, uma infecção viral ou um câncer. |
| EA201890618A1 (ru) | 2015-09-01 | 2018-10-31 | Ферст Вэйв Байо, Инк. | Способы и композиции для лечения состояний, ассоциированных с аномальными воспалительными ответами |
| PT3436074T (pt) | 2016-03-31 | 2020-08-21 | Romark Laboratories Lc | Compostos tiazolida para tratamento de infeções virais |
| SG11201808402RA (en) | 2016-04-11 | 2018-10-30 | Genfit | Methods of treatment for cholestatic and fibrotic diseases |
| US11192914B2 (en) | 2016-04-28 | 2021-12-07 | Emory University | Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
| US11173149B2 (en) | 2017-04-18 | 2021-11-16 | Romark Laboratories L.C. | Inhibition of protein disulfide-isomerase A3 |
| CN107286149B (zh) * | 2017-05-10 | 2021-02-12 | 南华大学 | N-(5-胡椒基噻唑-2-基)哌啶基酰胺及其应用 |
| CN107141267B (zh) * | 2017-06-22 | 2019-04-09 | 湖南大学 | N-(5-酰基噻唑-2-基)酰胺及其制备方法与应用 |
| CN107235927B (zh) * | 2017-06-22 | 2019-04-16 | 湖南大学 | N-(5-酰基噻唑-2-基)哌嗪基酰胺及其医药用途 |
| KR102077833B1 (ko) * | 2018-12-10 | 2020-02-14 | 류형준 | 기능성 식품조성물 |
| US20220193021A1 (en) * | 2019-05-03 | 2022-06-23 | President And Fellows Of Harvard College | Combination therapy for treating influenza virus infection |
| WO2021046446A1 (en) * | 2019-09-06 | 2021-03-11 | Yourchoice Therapeutics, Inc. | Compositions and methods of use for enhancing fertility |
| CN112480104B (zh) * | 2019-09-11 | 2024-06-18 | 绍兴君科臻元医药科技有限公司 | 硝唑尼特衍生物及其医药用途 |
| EP4101449A4 (en) * | 2020-01-21 | 2024-02-21 | Academy of Military Medical Sciences | Application of nitazoxanide and active form thereof, tizoxanide, in treatment of sars-cov-2 infection |
| US20230241037A1 (en) * | 2020-03-09 | 2023-08-03 | 1Globe Health Institute, Nanjing | Cross-linked medication for treatment of coronaviral infection and method of treatment |
| US10980756B1 (en) | 2020-03-16 | 2021-04-20 | First Wave Bio, Inc. | Methods of treatment |
| RU2726070C1 (ru) * | 2020-03-23 | 2020-07-08 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский Государственный медицинский университет" Министерства здравоохранения Российской Федерации | Способ патогенетической коррекции метаболических нарушений при инфекционном мононуклеозе, вызванном вирусом Эпштейна-Барр |
| EP4126853A1 (en) * | 2020-03-30 | 2023-02-08 | The Scripps Research Institute | Small molecule inhibitors of influenza hemagglutinin |
| EP4182304A1 (en) | 2020-07-20 | 2023-05-24 | Romark Laboratories, L.C. | Crystalline salts of tizoxanide and 2-hydroxy-n-(5-chloro-1,3-thiazol-2-yl)benzamide (rm-4848) with ethanolamine, morpholine, propanolamine, piperazine and n-methylpiperazine |
| JP2023538136A (ja) | 2020-08-24 | 2023-09-06 | ロマーク ラボラトリーズ，リミティド カンパニー | コロナウイルスに対するチアゾリドの利用 |
| US20240002332A1 (en) * | 2020-11-18 | 2024-01-04 | Wenwei HUANG | Small Molecule Inhibitors of SARS-CoV-2 Infections |
| WO2022206084A1 (zh) * | 2021-03-29 | 2022-10-06 | 北京大学 | 噻唑类化合物在制备治疗和预防癌症药物中的用途 |
| WO2022214855A1 (es) * | 2021-04-10 | 2022-10-13 | Siegfried Rhein, S.A. De C.V. | Uso de nitazoxanida para la preparación de medicamento para prevenir o tratar infección causada por coronavirus sars-cov-2 |
| WO2022218239A1 (zh) * | 2021-04-12 | 2022-10-20 | 杜心赟 | 新型噻唑类化合物及其制备方法和用途 |
| CN113277994A (zh) * | 2021-05-18 | 2021-08-20 | 杜心赟 | 噻唑类化合物及其制备方法和用途 |
| WO2023198095A1 (zh) * | 2022-04-12 | 2023-10-19 | 成都贝诺科成生物科技有限公司 | 一种硝基噻唑衍生物在制备抑制幽门螺杆菌的抑菌剂中的用途 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6136835A (en) * | 1999-05-17 | 2000-10-24 | The Procter & Gamble Company | Methods of treatment for viral infections |
| US20040242518A1 (en) * | 2002-09-28 | 2004-12-02 | Massachusetts Institute Of Technology | Influenza therapeutic |
| US6849254B1 (en) * | 1999-04-19 | 2005-02-01 | Schering Corporation | HCV combination therapy |
| US20050112751A1 (en) * | 2002-11-22 | 2005-05-26 | Fang Fang | Novel class of therapeutic protein based molecules |
| US20060194853A1 (en) * | 2004-10-08 | 2006-08-31 | Rossignol Jean F | Alkyl benzamides |
| US20070004661A1 (en) * | 2004-10-26 | 2007-01-04 | Stein David A | Antisense antiviral compound and method for treating influenza viral infection |
| US20090036467A1 (en) * | 2007-08-03 | 2009-02-05 | Romark Laboratories L.C. | Alkylsulfonyl-substituted thiazolide compounds |
| US20100009970A1 (en) * | 2008-03-19 | 2010-01-14 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
Family Cites Families (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1177206A (en) | 1967-11-28 | 1970-01-07 | Pfizer & Co C | Lung Antiviral Factor |
| GB1437800A (en) | 1973-08-08 | 1976-06-03 | Phavic Sprl | Derivatives of 2-benzamido-5-nitro-thiazoles |
| US4343945A (en) | 1979-01-23 | 1982-08-10 | Olin Corporation | 5-Benzamido-3-trichloromethyl-1,2,4-thiadiazoles and their use as herbicides, fungicides and insecticides |
| US4337081A (en) | 1979-01-23 | 1982-06-29 | Olin Corporation | 5-Amido-3-trihalomethyl-1,2,4-thiadiazoles and their use as herbicides |
| SU910628A1 (ru) | 1980-04-22 | 1982-03-07 | Гродненский государственный медицинский институт | Способ получени 2-ациламинотиазолов |
| JPS56158703A (en) | 1980-05-10 | 1981-12-07 | Sankyo Co Ltd | Fungicide |
| US4416683A (en) | 1980-09-16 | 1983-11-22 | Eli Lilly And Company | Benzamides, compositions and agricultural method |
| JPS649978A (en) | 1987-07-02 | 1989-01-13 | Shionogi & Co | Perfluoroalkylisoxazole derivative |
| US4874864A (en) | 1988-05-24 | 1989-10-17 | Pfizer Inc. | Benzamide protease inhibitors |
| US5169846A (en) | 1989-10-12 | 1992-12-08 | Crooks Michael J | Non-aqueous micellar solutions of anthelmintic benzimidazoles, closantel, or phenothiazine, and insect growth regulators |
| ES2222455T3 (es) | 1994-01-28 | 2005-02-01 | University Of Kentucky Research Foundation | Cofarmacos como un metodo de liberacion controlada de farmacos. |
| US5578621A (en) | 1994-09-08 | 1996-11-26 | Romark Lab Lc | Benzamide derivatives |
| DK0755386T3 (da) * | 1994-04-13 | 2002-08-26 | Romark Lab Lc | Benzamid-derivater, sammensætninger indeholdende nævnte derivat og anvendelse deraf |
| MX9604483A (es) | 1994-09-08 | 1998-02-28 | Jean-Francois Rossignol | Derivados de benzamida, composiciones que contienen dicho derivado y uso de las mismas. |
| US5968961A (en) * | 1997-05-07 | 1999-10-19 | Romark Laboratories, L.C. | Pharmaceutical compositions of tizoxanide and nitazoxanide |
| AU740022B2 (en) | 1997-05-07 | 2001-10-25 | Romark Laboratories, L.C. | Pharmaceutical compositions of tizoxanide and nitazoxanide |
| GB9725298D0 (en) | 1997-11-28 | 1998-01-28 | Zeneca Ltd | Insecticidal thiazole derivatives |
| WO2000002851A1 (en) | 1998-07-08 | 2000-01-20 | Aventis Pharma Deutschland Gmbh | Sulfur substituted sulfonylaminocarboxylic acid n-arylamides, their preparation, their use and pharmaceutical preparations comprising them |
| GB9823871D0 (en) | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
| US7229822B1 (en) | 2000-02-29 | 2007-06-12 | Univ Columbia | Melanoma differentation associated gene-5 and vectors and cells containing same |
| HUP0303538A2 (hu) | 2000-12-21 | 2005-02-28 | Bristol-Myers Squibb Co. | Tirozin kinázok Tec családjának tiazolil-vegyület inhibitorai és ezeket tartalmazó gyógyszerkészítmények |
| ATE315555T1 (de) | 2001-05-11 | 2006-02-15 | Pfizer Prod Inc | Thiazolderivate und ihre verwendung als cdk- inhibitoren |
| WO2002092584A1 (en) | 2001-05-14 | 2002-11-21 | Nihon Nohyaku Co., Ltd. | Thiadiazole derivatives, pesticides for agricultural and horticultural use and usage thereof |
| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| JP2003335680A (ja) | 2002-05-21 | 2003-11-25 | Otsuka Pharmaceut Factory Inc | Ａｃａｔ−１阻害剤 |
| CN101103977A (zh) | 2002-06-05 | 2008-01-16 | 株式会社医药分子设计研究所 | 糖尿病治疗药 |
| AU2003279004B2 (en) | 2002-09-28 | 2009-10-08 | Massachusetts Institute Of Technology | Influenza therapeutic |
| US6737382B1 (en) | 2002-10-23 | 2004-05-18 | Nippon Soda Co. Ltd. | Insecticidal aminothiazole derivatives |
| MXPA05009059A (es) | 2003-02-26 | 2005-10-19 | Banyu Pharma Co Ltd | Derivados de heteroarilcarbamoilbenceno. |
| BRPI0408815A (pt) | 2003-03-28 | 2006-04-04 | Pharmacia & Upjohn Co Llc | moduladores alostéricos positivos do receptor nicotìnico da acetilcolina |
| JPWO2005007151A1 (ja) | 2003-07-16 | 2006-08-31 | 株式会社医薬分子設計研究所 | 皮膚色素沈着の治療剤 |
| US20050090506A1 (en) | 2003-10-24 | 2005-04-28 | Nippon Soda Co., Ltd. | Insecticidal perfluoroalkylthiazole derivatives |
| US7683097B2 (en) | 2004-05-27 | 2010-03-23 | Propharmacon Inc. | Topoisomerase inhibitors |
| UA90864C2 (en) | 2004-09-09 | 2010-06-10 | Ромарк Лебораториз, Л.К. | Halogenated benzamide derivatives |
| EP2047850A3 (en) * | 2005-04-12 | 2009-07-29 | Romark Laboratories, L.C. | Methods for treating diseases through inhibition of the function of molecular chaperones such as protein disulfide isomerases , pharmaceutical compositions comprising them, and screening methods for identifying therapeutic agents |
| KR20080019213A (ko) | 2005-05-09 | 2008-03-03 | 아칠리온 파르마세우티칼스 인코포레이티드 | 티아졸 화합물 및 그 사용방법 |
| EP2029138A1 (en) | 2005-06-03 | 2009-03-04 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| TW200711649A (en) * | 2005-06-17 | 2007-04-01 | Combinatorx Inc | Combination therapy for the treatment of immunoinflammatory disorders |
| MX2008000141A (es) | 2005-06-27 | 2008-04-07 | Exelixis Inc | Moduladores de lxr basados en imidazol. |
| WO2007008541A2 (en) | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| MX2008001605A (es) | 2005-08-02 | 2008-04-14 | Irm Llc | Compuestos y composiciones de tiazol-2-il amino 5-substituido como inhibidores de cinasa proteica. |
| RU2441869C2 (ru) | 2005-12-21 | 2012-02-10 | Эбботт Лэборетриз | Противовирусные соединения |
| CA2636527C (en) | 2006-01-09 | 2016-05-17 | Romark Laboratories, L.C. | Viral hepatitis treatment |
| JP2009535318A (ja) | 2006-04-28 | 2009-10-01 | トランステック ファーマ，インコーポレイティド | ベンズアミドグルコキナーゼ活性化剤 |
| CN101454302A (zh) | 2006-05-31 | 2009-06-10 | 艾博特公司 | 用作大麻素受体配位体的噻唑化合物及其用途 |
| BRPI0712795A2 (pt) | 2006-07-07 | 2012-09-04 | Boehringer Ingelheim Int | derivados de heteroarila substituìdos com fenila e uso dos mesmos como agentes antitumorais |
| WO2008033466A2 (en) | 2006-09-14 | 2008-03-20 | Combinatorx (Singapore) Pre. Ltd. | Compositions and methods for treatment of viral diseases |
| WO2008070707A1 (en) | 2006-12-05 | 2008-06-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO2009001214A2 (en) | 2007-06-28 | 2008-12-31 | Pfizer Products Inc. | Thieno[2,3-d]pyrimidin-4(3h)-one, isoxazolo[5,4-d]pyrimidin-4(5h)-one and isothiazolo[5,4-d]pyrimidin-4(5h)-one derivatives as calcium receptor antagonists |
| WO2009065096A1 (en) | 2007-11-16 | 2009-05-22 | University Of Medicine And Dentistry Of New Jersey | Mechanism-based small-molecule parasite inhibitors |
| US20100081713A1 (en) * | 2008-03-19 | 2010-04-01 | CombinatoRx, (Singapore) Pte. Ltd. | Compositions and methods for treating viral infections |
| EA201001847A1 (ru) | 2008-06-11 | 2011-08-30 | Айрм Ллк | Соединения и композиции, применяемые для лечения малярии |
| TW201014860A (en) | 2008-09-08 | 2010-04-16 | Boehringer Ingelheim Int | New chemical compounds |
| UY32138A (es) | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| EP2346853A2 (en) | 2008-11-19 | 2011-07-27 | Schering Corporation | Inhibitors of diacylglycerol acyltransferase |
| EP2408770B1 (en) * | 2009-03-20 | 2014-11-05 | University Of Virginia Patent Foundation | Broad spectrum benzothiophene-nitrothiazolide and other antimicrobials |
| EA021587B1 (ru) | 2009-05-12 | 2015-07-30 | РОМАРК ЛЭБОРЕТЕРИЗ Эл. Си. | Соединения галогеналкилгетероарилбензамида |
| EA030679B1 (ru) * | 2009-06-26 | 2018-09-28 | РОМАРК ЛЭБОРЕТЕРИЗ Эл.Си. | Соединения и способы лечения гриппа |
-
2010
- 2010-06-23 EA EA201270077A patent/EA030679B1/ru unknown
- 2010-06-23 PT PT107925992T patent/PT2445349T/pt unknown
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-
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Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6849254B1 (en) * | 1999-04-19 | 2005-02-01 | Schering Corporation | HCV combination therapy |
| US6136835A (en) * | 1999-05-17 | 2000-10-24 | The Procter & Gamble Company | Methods of treatment for viral infections |
| US20040242518A1 (en) * | 2002-09-28 | 2004-12-02 | Massachusetts Institute Of Technology | Influenza therapeutic |
| US20050112751A1 (en) * | 2002-11-22 | 2005-05-26 | Fang Fang | Novel class of therapeutic protein based molecules |
| US20060194853A1 (en) * | 2004-10-08 | 2006-08-31 | Rossignol Jean F | Alkyl benzamides |
| US20070004661A1 (en) * | 2004-10-26 | 2007-01-04 | Stein David A | Antisense antiviral compound and method for treating influenza viral infection |
| US20090036467A1 (en) * | 2007-08-03 | 2009-02-05 | Romark Laboratories L.C. | Alkylsulfonyl-substituted thiazolide compounds |
| US20100009970A1 (en) * | 2008-03-19 | 2010-01-14 | Combinatorx (Singapore) Pte. Ltd. | Compositions and methods for treatment of viral diseases |
Non-Patent Citations (1)
| Title |
|---|
| Kabanov. Polymer Genomics: An Insight into Pharmacology and Toxicology of Nanomedicines. Adv Drug Deliv Rev., 2006, Vol 58(15): pp 1597-1621; entire document esp. pg4 * |
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