JP2011525171A - 抗ウイルス性治療用薬剤 - Google Patents
抗ウイルス性治療用薬剤 Download PDFInfo
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- JP2011525171A JP2011525171A JP2010549889A JP2010549889A JP2011525171A JP 2011525171 A JP2011525171 A JP 2011525171A JP 2010549889 A JP2010549889 A JP 2010549889A JP 2010549889 A JP2010549889 A JP 2010549889A JP 2011525171 A JP2011525171 A JP 2011525171A
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- Prior art keywords
- alkyl
- substituted
- compound
- aryl
- prodrug
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- 239000003814 drug Substances 0.000 title claims description 22
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- 229940124597 therapeutic agent Drugs 0.000 title description 6
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- 239000000651 prodrug Substances 0.000 claims abstract description 90
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- 238000000034 method Methods 0.000 claims abstract description 51
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- 108010014303 DNA-directed DNA polymerase Proteins 0.000 claims abstract description 10
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- 125000003118 aryl group Chemical group 0.000 claims description 63
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 44
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- 238000011282 treatment Methods 0.000 claims description 36
- 125000002252 acyl group Chemical group 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 28
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- 125000001424 substituent group Chemical group 0.000 claims description 27
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
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- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
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- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
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- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 229910052721 tungsten Inorganic materials 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
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- AAJXJLYUWKMQNO-UHFFFAOYSA-N 4-chloro-2-(1,2-oxazol-5-yl)phenol Chemical compound OC1=CC=C(Cl)C=C1C1=CC=NO1 AAJXJLYUWKMQNO-UHFFFAOYSA-N 0.000 claims description 4
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- OSBKZZCHLHZCDB-PBXRRBTRSA-N (2r,3r,4r)-2,3,4,5-tetrahydroxy-2-methylpentanal Chemical compound O=C[C@@](O)(C)[C@H](O)[C@H](O)CO OSBKZZCHLHZCDB-PBXRRBTRSA-N 0.000 claims description 2
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- SQXRWAVEVYDDBF-LMVFSUKVSA-N (2r,3r,4r)-2-fluoro-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](F)C=S SQXRWAVEVYDDBF-LMVFSUKVSA-N 0.000 claims description 2
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- DITIGNGDSVRJFX-UHFFFAOYSA-N 3-(hydroxymethyl)-4-methylidenecyclopentane-1,2-diol Chemical compound OCC1C(O)C(O)CC1=C DITIGNGDSVRJFX-UHFFFAOYSA-N 0.000 claims description 2
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- WQSIEHZPHQVPFS-UHFFFAOYSA-N 3-fluoro-4-(hydroxymethyl)pyrrolidin-2-ol Chemical compound OCC1CNC(O)C1F WQSIEHZPHQVPFS-UHFFFAOYSA-N 0.000 claims description 2
- BSQXZHMREYHKOM-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidin-3-ol Chemical compound OCC1CNCC1O BSQXZHMREYHKOM-UHFFFAOYSA-N 0.000 claims description 2
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- 229940121740 Inosine monophosphate dehydrogenase inhibitor Drugs 0.000 claims description 2
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/99—Enzyme inactivation by chemical treatment
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- 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
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D491/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
- C12N9/1241—Nucleotidyltransferases (2.7.7)
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/10—Internal combustion engine [ICE] based vehicles
- Y02T10/30—Use of alternative fuels, e.g. biofuels
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Molecular Biology (AREA)
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- Oncology (AREA)
- Biotechnology (AREA)
- Communicable Diseases (AREA)
- Microbiology (AREA)
- Biomedical Technology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
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| US3405308P | 2008-03-05 | 2008-03-05 | |
| US61/034,053 | 2008-03-05 | ||
| US7937008P | 2008-07-09 | 2008-07-09 | |
| US61/079,370 | 2008-07-09 | ||
| PCT/US2009/036213 WO2009111653A2 (en) | 2008-03-05 | 2009-03-05 | Antiviral therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
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| JP2011525171A true JP2011525171A (ja) | 2011-09-15 |
| JP2011525171A5 JP2011525171A5 (enExample) | 2013-03-14 |
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| JP2010549889A Withdrawn JP2011525171A (ja) | 2008-03-05 | 2009-03-05 | 抗ウイルス性治療用薬剤 |
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| EP (1) | EP2265275A2 (enExample) |
| JP (1) | JP2011525171A (enExample) |
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| AU (1) | AU2009221770A1 (enExample) |
| BR (1) | BRPI0910388A2 (enExample) |
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| EA (1) | EA201070988A1 (enExample) |
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| MX (1) | MX2010009646A (enExample) |
| NZ (1) | NZ588179A (enExample) |
| PE (1) | PE20091727A1 (enExample) |
| TW (1) | TW200942243A (enExample) |
| WO (1) | WO2009111653A2 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SG177974A1 (en) * | 2007-01-12 | 2012-02-28 | Biocryst Pharm Inc | Antiviral nucleoside analogs |
| CA2685520A1 (en) * | 2007-05-10 | 2008-11-20 | 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 |
| AR071395A1 (es) | 2008-04-23 | 2010-06-16 | Gilead Sciences Inc | Analogos carba-nucleosidos 1'-sustituidos para tratamiento antiviral |
| EP2313102A2 (en) | 2008-07-03 | 2011-04-27 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| HRP20130862T1 (hr) | 2009-09-21 | 2013-10-25 | Gilead Sciences, Inc. | Procesi i intermedijeri za pripravu analoga 1'-cijanokarbanukleozida |
| TW201201815A (en) | 2010-05-28 | 2012-01-16 | Gilead Sciences Inc | 1'-substituted-carba-nucleoside prodrugs for antiviral treatment |
| NZ606141A (en) | 2010-07-19 | 2015-03-27 | Gilead Sciences Inc | Methods for the preparation of diasteromerically pure phosphoramidate prodrugs |
| UA111163C2 (uk) | 2010-07-22 | 2016-04-11 | Гайлід Сайєнсіз, Інк. | Способи й сполуки для лікування вірусних інфекцій paramyxoviridae |
| EP2627334B1 (en) | 2010-10-15 | 2015-04-29 | Biocryst Pharmaceuticals, Inc. | Compositions for use in the treatment of viral infections |
| 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 |
| MY190867A (en) | 2015-03-06 | 2022-05-13 | Atea Pharmaceuticals Inc | ? -d-2'-deoxy-2'-?-fluoro-2'- ? -c-substituted-2-modified-n6-substituted purine nucleotides for hcv treatment |
| MA52371A (fr) | 2015-09-16 | 2021-09-22 | Gilead Sciences Inc | Méthodes de traitement d'infections dues aux coronaviridae |
| EP3222292A1 (en) | 2016-03-03 | 2017-09-27 | Heidelberg Pharma GmbH | Amanitin conjugates |
| JP7046015B2 (ja) | 2016-03-06 | 2022-04-01 | バイオクライスト ファーマシューティカルズ， インコーポレイテッド | ジカウイルス感染の治療のための方法及び組成物 |
| US10711029B2 (en) | 2016-07-14 | 2020-07-14 | 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 |
| PL3512863T3 (pl) | 2016-09-07 | 2022-04-04 | Atea Pharmaceuticals, Inc. | 2'-Podstawione-N6-podstawione nukleotydy purynowe do leczenia zakażeń wirusem RNA |
| IL295609B2 (en) | 2017-02-01 | 2023-11-01 | Atea Pharmaceuticals Inc | Nucleotide hemisulfate 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 |
| JP2020518578A (ja) | 2017-05-01 | 2020-06-25 | ギリアード サイエンシーズ， インコーポレイテッド | （Ｓ）−２−エチルブチル２−（（（Ｓ）−（（（２Ｒ，３Ｓ，４Ｒ，５Ｒ）−５−（４−アミノピロロ［２，１−ｆ］［１，２，４］トリアジン−７−イル）−５−シアノ−３，４−ジヒドロキシテトラヒドロフラン−２−イル）メトキシ）（フェノキシ）ホスホリル）アミノ）プロパノエートの結晶形態 |
| ES3000461T3 (en) | 2017-07-11 | 2025-02-28 | Gilead Sciences Inc | Compositions comprising an rna polymerase inhibitor and cyclodextrin for treating viral infections |
| CN112351799A (zh) | 2018-04-10 | 2021-02-09 | 阿堤亚制药公司 | 具有硬化的hcv感染患者的治疗 |
| WO2020151682A1 (zh) * | 2019-01-23 | 2020-07-30 | 成都先导药物开发股份有限公司 | 一种大环类免疫调节剂 |
| JP2023512656A (ja) | 2020-01-27 | 2023-03-28 | ギリアード サイエンシーズ， インコーポレイテッド | ＳＡＲＳ ＣｏＶ－２感染を治療するための方法 |
| AR121356A1 (es) | 2020-02-18 | 2022-05-11 | Gilead Sciences Inc | Compuestos antivirales |
| 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 |
| TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| TWI890963B (zh) | 2020-03-12 | 2025-07-21 | 美商基利科學股份有限公司 | 1'-氰基核苷之製備方法 |
| AU2021251689B2 (en) | 2020-04-06 | 2024-06-13 | Gilead Sciences, Inc. | Inhalation formulations of 1'-cyano substituted carbanucleoside analogs |
| TW202532084A (zh) | 2020-05-29 | 2025-08-16 | 美商基利科學股份有限公司 | 瑞德西韋之治療方法 |
| IL299202A (en) | 2020-06-24 | 2023-02-01 | Gilead Sciences Inc | 1'-cyano nucleoside analogs and uses thereof |
| PE20231983A1 (es) | 2020-08-27 | 2023-12-12 | Gilead Sciences Inc | Compuestos y metodos para el tratamiento de infecciones virales |
| ES3028915T3 (en) | 2021-04-16 | 2025-06-20 | Gilead Sciences Inc | Methods of preparing carbanucleosides using amides |
| BR112023026356A2 (pt) | 2021-06-17 | 2024-03-05 | Atea Pharmaceuticals Inc | Método para tratar vírus da hepatite c ou uma condição resultante de uma infecção por hepatite c, combinação, uso da combinação, composição farmacêutica, e, kit para o tratamento de vírus da hepatite c |
| EP4387977A1 (en) | 2021-08-18 | 2024-06-26 | 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ512736A (en) | 1999-01-13 | 2003-11-28 | Genentech Inc | Serine protease inhibitors |
| JP2002279640A (ja) | 2001-03-21 | 2002-09-27 | Ricoh Co Ltd | ウォブル検出回路とその装置 |
| AU2004233898B2 (en) | 2003-04-25 | 2010-12-23 | Gilead Sciences, Inc. | Antiviral phosphonate analogs |
| CA2537114C (en) * | 2003-08-27 | 2012-10-02 | Biota, Inc. | Tricyclic nucleosides or nucleotides as therapeutic agents |
| US20050182252A1 (en) | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| KR20070100237A (ko) | 2004-10-29 | 2007-10-10 | 바이오크리스트 파마수티컬즈, 인코퍼레이티드 | 치료용 푸로피리미딘 및 티에노피리미딘 |
| US7524825B2 (en) | 2005-02-28 | 2009-04-28 | Smithkline Beecham Corporation | Tricyclic-nucleoside compounds for treating viral infections |
| WO2008005542A2 (en) * | 2006-07-07 | 2008-01-10 | Gilead Sciences, Inc., | Antiviral phosphinate compounds |
| SG177974A1 (en) | 2007-01-12 | 2012-02-28 | Biocryst Pharm Inc | Antiviral nucleoside analogs |
| CA2685520A1 (en) | 2007-05-10 | 2008-11-20 | Biocryst Pharmaceuticals, Inc. | Tetrahydrofuro [3 4-d] dioxolane compounds for use in the treatment of viral infections and cancer |
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2009
- 2009-03-04 TW TW098107018A patent/TW200942243A/zh unknown
- 2009-03-05 AR ARP090100788A patent/AR071745A1/es not_active Application Discontinuation
- 2009-03-05 EP EP09716971A patent/EP2265275A2/en not_active Withdrawn
- 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 WO PCT/US2009/036213 patent/WO2009111653A2/en not_active Ceased
- 2009-03-05 PE PE2009000334A patent/PE20091727A1/es not_active Application Discontinuation
- 2009-03-05 JP JP2010549889A patent/JP2011525171A/ja not_active Withdrawn
- 2009-03-05 EA EA201070988A patent/EA201070988A1/ru unknown
- 2009-03-05 AU AU2009221770A patent/AU2009221770A1/en not_active Abandoned
- 2009-03-05 BR BRPI0910388A patent/BRPI0910388A2/pt not_active IP Right Cessation
- 2009-03-05 MX MX2010009646A patent/MX2010009646A/es not_active Application Discontinuation
- 2009-03-05 CN CN2009801168793A patent/CN102834513A/zh active Pending
- 2009-03-05 US US12/398,866 patent/US7994139B2/en not_active Expired - Fee Related
- 2009-03-05 CA CA2717173A patent/CA2717173A1/en not_active Abandoned
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2010
- 2010-08-26 IL IL207826A patent/IL207826A0/en unknown
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2011
- 2011-07-12 US US13/181,078 patent/US20120142617A1/en not_active Abandoned
Also Published As
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| NZ588179A (en) | 2012-09-28 |
| TW200942243A (en) | 2009-10-16 |
| MX2010009646A (es) | 2010-09-28 |
| AR071745A1 (es) | 2010-07-14 |
| PE20091727A1 (es) | 2009-12-04 |
| US7994139B2 (en) | 2011-08-09 |
| EA201070988A1 (ru) | 2011-12-30 |
| WO2009111653A2 (en) | 2009-09-11 |
| CN102834513A (zh) | 2012-12-19 |
| CA2717173A1 (en) | 2009-09-11 |
| BRPI0910388A2 (pt) | 2019-06-11 |
| KR20100137494A (ko) | 2010-12-30 |
| EP2265275A2 (en) | 2010-12-29 |
| WO2009111653A3 (en) | 2011-09-22 |
| IL207826A0 (en) | 2010-12-30 |
| AU2009221770A1 (en) | 2009-09-11 |
| US20120142617A1 (en) | 2012-06-07 |
| US20090227524A1 (en) | 2009-09-10 |
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