TW200942243A - Antiviral therapeutic agents - Google Patents
Antiviral therapeutic agents Download PDFInfo
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- TW200942243A TW200942243A TW098107018A TW98107018A TW200942243A TW 200942243 A TW200942243 A TW 200942243A TW 098107018 A TW098107018 A TW 098107018A TW 98107018 A TW98107018 A TW 98107018A TW 200942243 A TW200942243 A TW 200942243A
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- 239000003814 drug Substances 0.000 title claims description 31
- 230000000840 anti-viral effect Effects 0.000 title description 7
- 229940124597 therapeutic agent Drugs 0.000 title description 6
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- 238000000034 method Methods 0.000 claims description 69
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- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 6
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- 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims description 5
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 4
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- 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
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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| EP2155758B1 (en) | 2007-05-10 | 2012-08-22 | Biocryst Pharmaceuticals, Inc. | Tetrahydrofuro[3,4-d]dioxolane compounds for use in the treatment of viral infections and cancer |
| US20090247750A1 (en) * | 2008-03-28 | 2009-10-01 | Biocryst Pharmaceuticals, Inc. | Process for preparing nucleoside analogs |
| CN102046626A (zh) | 2008-04-23 | 2011-05-04 | 吉里德科学公司 | 用于抗病毒治疗的carba-核苷类似物 |
| EP2313102A2 (en) | 2008-07-03 | 2011-04-27 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| DK2480559T3 (da) | 2009-09-21 | 2013-08-05 | Gilead Sciences Inc | Fremgangsmåder og mellemprodukter til fremstillingen af 1'-cyano-carbanukleosid-analoger |
| TW201201815A (en) | 2010-05-28 | 2012-01-16 | Gilead Sciences Inc | 1'-substituted-carba-nucleoside prodrugs for antiviral treatment |
| PH12013500033A1 (en) | 2010-07-19 | 2017-07-26 | Gilead Sciences Inc | Methods for the preparation of diasteromerically pure phosphoramidate prodrugs |
| MA34470B1 (fr) | 2010-07-22 | 2013-08-01 | Gilead Sciences Inc | Procédés et composés pour traiter des infections à virus paramyxoviridae |
| BR112013009029B1 (pt) | 2010-10-15 | 2021-06-29 | Biocryst Pharmaceuticals, Inc. | Métodos e composições para inibição de polimerase |
| WO2013033093A1 (en) * | 2011-08-29 | 2013-03-07 | Biocryst Pharmaceuticals, Inc. | Heterocyclic compounds as janus kinase inhibitors |
| AR090699A1 (es) | 2012-04-18 | 2014-12-03 | Biocryst Pharm Inc | Compuestos inhibidores de la actividad de la arn polimerasa viral |
| US8906929B2 (en) * | 2012-08-16 | 2014-12-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP2970297A1 (en) * | 2013-03-14 | 2016-01-20 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| CN104946646B (zh) * | 2014-03-25 | 2020-03-31 | 中国医学科学院基础医学研究所 | 用于预防和/或治疗埃博拉病毒性出血热的小核酸分子、dna分子、蛋白及应用 |
| TWI767201B (zh) | 2014-10-29 | 2022-06-11 | 美商基利科學股份有限公司 | 絲狀病毒科病毒感染之治療 |
| CN107427530B (zh) | 2015-03-06 | 2020-09-08 | 阿堤亚制药公司 | 用于HCV治疗的β-D-2’-脱氧-2’α-氟-2’-β-C-取代的-2-改性的-N6-取代的嘌呤核苷酸 |
| MX394858B (es) | 2015-09-16 | 2025-03-24 | Gilead Sciences Inc | Compuestos de formula i para usarse en el tratamiento de infecciones por virus arenaviridae y coronaviridae |
| EP3222292A1 (en) | 2016-03-03 | 2017-09-27 | Heidelberg Pharma GmbH | Amanitin conjugates |
| AU2017229105B2 (en) | 2016-03-06 | 2021-08-12 | Biocryst Pharmaceuticals, Inc. | Methods and compositions for treatment of Zika virus infection |
| WO2018013937A1 (en) | 2016-07-14 | 2018-01-18 | Atea Pharmaceuticals, Inc. | Beta-d-2'-deoxy-2'-alpha-fluoro-2'-beta-c-substituted-4'-fluoro-n6-substituted-6-amino-2-substituted purine nucleotides for the treatment of hepatitis c virus infection |
| AU2017324939B2 (en) | 2016-09-07 | 2021-10-14 | Atea Pharmaceuticals, Inc. | 2'-substituted-N6-substituted purine nucleotides for RNA virus treatment |
| US10519186B2 (en) | 2017-02-01 | 2019-12-31 | Atea Pharmaceuticals, Inc. | Nucleotide hemi-sulfate salt for the treatment of hepatitis C virus |
| CA3056072C (en) | 2017-03-14 | 2022-08-23 | Gilead Sciences, Inc. | Methods of treating feline coronavirus infections |
| KR20190141747A (ko) | 2017-05-01 | 2019-12-24 | 길리애드 사이언시즈, 인코포레이티드 | (S)-2-에틸부틸 2-(((S)-(((2R,3S,4R,5R)-5-(4-아미노피롤로[2,1-f] [1,2,4]트리아진-7-일)-5-시아노-3,4-디히드록시테트라히드로푸란-2-일)메톡시)(페녹시) 포스포릴)아미노)프로파노에이트의 결정질 형태 |
| EP4512475A3 (en) | 2017-07-11 | 2025-05-14 | Gilead Sciences, Inc. | Compositions comprising an rna polymerase inhibitor and cyclodextrin for treating viral infections |
| KR20200140865A (ko) | 2018-04-10 | 2020-12-16 | 아테아 파마슈티컬즈, 인크. | 간경변증을 갖는 hcv 감염 환자의 치료 |
| CN111471056B (zh) * | 2019-01-23 | 2021-07-02 | 成都先导药物开发股份有限公司 | 一种大环类免疫调节剂 |
| AU2021214911A1 (en) | 2020-01-27 | 2022-07-21 | Gilead Sciences, Inc. | Methods for treating SARS CoV-2 infections |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| AU2021224588B2 (en) | 2020-02-18 | 2024-07-18 | Gilead Sciences, Inc. | Antiviral compounds |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| KR20220153619A (ko) | 2020-03-12 | 2022-11-18 | 길리애드 사이언시즈, 인코포레이티드 | 1'-시아노 뉴클레오사이드의 제조 방법 |
| WO2021207049A1 (en) | 2020-04-06 | 2021-10-14 | Gilead Sciences, Inc. | Inhalation formulations of 1'-cyano substituted carbanucleoside analogs |
| JP7664287B2 (ja) | 2020-05-29 | 2025-04-17 | ギリアード サイエンシーズ， インコーポレイテッド | レムデシビル治療方法 |
| AU2021296841B2 (en) | 2020-06-24 | 2025-01-23 | Gilead Sciences, Inc. | 1'-cyano nucleoside analogs and uses thereof |
| KR20250111239A (ko) | 2020-08-27 | 2025-07-22 | 길리애드 사이언시즈, 인코포레이티드 | 바이러스 감염 치료를 위한 화합물 및 방법 |
| KR20230170745A (ko) | 2021-04-16 | 2023-12-19 | 길리애드 사이언시즈, 인코포레이티드 | 아미드를 사용한 카르바뉴클레오시드를 제조하는 방법 |
| CN117500494A (zh) | 2021-06-17 | 2024-02-02 | 阿堤亚制药公司 | 有利的抗hcv联合疗法 |
| US12116380B2 (en) | 2021-08-18 | 2024-10-15 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| CA3244278A1 (en) | 2022-03-02 | 2023-09-07 | Gilead Sciences Inc | COMPOUNDS AND METHODS FOR THE TREATMENT OF VIRAL INFECTIONS |
| US12357577B1 (en) | 2024-02-02 | 2025-07-15 | Gilead Sciences, Inc. | Pharmaceutical formulations and uses thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100488947C (zh) | 1999-01-13 | 2009-05-20 | 杰南技术公司 | 丝氨酸蛋白酶抑制剂 |
| JP2002279640A (ja) | 2001-03-21 | 2002-09-27 | Ricoh Co Ltd | ウォブル検出回路とその装置 |
| JP5069463B2 (ja) | 2003-04-25 | 2012-11-07 | ギリアード サイエンシーズ， インコーポレイテッド | 抗ウイルス性ホスホネート類似物 |
| KR20060123707A (ko) | 2003-08-27 | 2006-12-04 | 바이오타, 인코포레이티드 | 치료제로서의 신규 트리시클릭 뉴클레오시드 또는뉴클레오티드 |
| US20050182252A1 (en) | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| EP1814561A4 (en) | 2004-10-29 | 2012-12-19 | Biocryst Pharm Inc | THEROPUTICAL FUROPYRIMIDINES AND THIENOPYRIMIDINES |
| WO2006093987A1 (en) | 2005-02-28 | 2006-09-08 | Genelabs Technologies, Inc. | Tricyclic-nucleoside compounds for treating viral infections |
| US7842672B2 (en) * | 2006-07-07 | 2010-11-30 | Gilead Sciences, Inc. | Phosphonate inhibitors of HCV |
| EP2114980B1 (en) * | 2007-01-12 | 2012-06-27 | BioCryst Pharmaceuticals, Inc. | Antiviral nucleoside analogs |
| EP2155758B1 (en) | 2007-05-10 | 2012-08-22 | Biocryst Pharmaceuticals, Inc. | Tetrahydrofuro[3,4-d]dioxolane compounds for use in the treatment of viral infections and cancer |
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2009
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- 2009-03-05 AU AU2009221770A patent/AU2009221770A1/en not_active Abandoned
- 2009-03-05 JP JP2010549889A patent/JP2011525171A/ja not_active Withdrawn
- 2009-03-05 PE PE2009000334A patent/PE20091727A1/es not_active Application Discontinuation
- 2009-03-05 BR BRPI0910388A patent/BRPI0910388A2/pt not_active IP Right Cessation
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- 2009-03-05 WO PCT/US2009/036213 patent/WO2009111653A2/en not_active Ceased
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- 2009-03-05 MX MX2010009646A patent/MX2010009646A/es not_active Application Discontinuation
- 2009-03-05 KR KR1020107022136A patent/KR20100137494A/ko not_active Withdrawn
- 2009-03-05 NZ NZ588179A patent/NZ588179A/xx not_active IP Right Cessation
- 2009-03-05 AR ARP090100788A patent/AR071745A1/es not_active Application Discontinuation
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2010
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| MX2010009646A (es) | 2010-09-28 |
| US20090227524A1 (en) | 2009-09-10 |
| EP2265275A2 (en) | 2010-12-29 |
| IL207826A0 (en) | 2010-12-30 |
| WO2009111653A3 (en) | 2011-09-22 |
| KR20100137494A (ko) | 2010-12-30 |
| AU2009221770A1 (en) | 2009-09-11 |
| CA2717173A1 (en) | 2009-09-11 |
| PE20091727A1 (es) | 2009-12-04 |
| US20120142617A1 (en) | 2012-06-07 |
| AR071745A1 (es) | 2010-07-14 |
| BRPI0910388A2 (pt) | 2019-06-11 |
| US7994139B2 (en) | 2011-08-09 |
| EA201070988A1 (ru) | 2011-12-30 |
| WO2009111653A2 (en) | 2009-09-11 |
| NZ588179A (en) | 2012-09-28 |
| JP2011525171A (ja) | 2011-09-15 |
| CN102834513A (zh) | 2012-12-19 |
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