JP2013538230A5 - - Google Patents
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- JP2013538230A5 JP2013538230A5 JP2013529139A JP2013529139A JP2013538230A5 JP 2013538230 A5 JP2013538230 A5 JP 2013538230A5 JP 2013529139 A JP2013529139 A JP 2013529139A JP 2013529139 A JP2013529139 A JP 2013529139A JP 2013538230 A5 JP2013538230 A5 JP 2013538230A5
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- JP
- Japan
- Prior art keywords
- alkyl
- independently
- formula
- alkenyl
- aryl
- 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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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 24
- 239000003112 inhibitor Substances 0.000 claims description 24
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 239000002777 nucleoside Substances 0.000 claims description 8
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- -1 -C ( = O) OR 11 Chemical compound 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- KJTLQQUUPVSXIM-ZCFIWIBFSA-M (R)-mevalonate Chemical compound OCC[C@](O)(C)CC([O-])=O KJTLQQUUPVSXIM-ZCFIWIBFSA-M 0.000 claims description 4
- 229940123073 Angiotensin antagonist Drugs 0.000 claims description 4
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 4
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 claims description 4
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 4
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 230000003510 anti-fibrotic effect Effects 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000134 cyclophilin inhibitor Substances 0.000 claims description 4
- 239000002308 endothelin receptor antagonist Substances 0.000 claims description 4
- 239000003623 enhancer Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000002773 nucleotide Substances 0.000 claims description 4
- 125000003729 nucleotide group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229960000329 ribavirin Drugs 0.000 claims description 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229940044616 toll-like receptor 7 agonist Drugs 0.000 claims description 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 206010054261 Flavivirus infection Diseases 0.000 claims description 2
- 241000711549 Hepacivirus C Species 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- 238000000034 method Methods 0.000 description 5
- JLTWKDTWEKYNOG-ZCKHLOCKSA-N CC(C)NP(OC[C@H]1O[C@H]2c3cnc4[n]3ncnc4N)(O[C@H]1[C@@]2(C)F)=O Chemical compound CC(C)NP(OC[C@H]1O[C@H]2c3cnc4[n]3ncnc4N)(O[C@H]1[C@@]2(C)F)=O JLTWKDTWEKYNOG-ZCKHLOCKSA-N 0.000 description 1
- FILMSNVIFXMGLK-ZCKHLOCKSA-N CC(C)OP(OC[C@H]1O[C@H]2c3cnc4[n]3ncnc4N)(O[C@H]1[C@@]2(C)F)=O Chemical compound CC(C)OP(OC[C@H]1O[C@H]2c3cnc4[n]3ncnc4N)(O[C@H]1[C@@]2(C)F)=O FILMSNVIFXMGLK-ZCKHLOCKSA-N 0.000 description 1
- QFJJGVDPVAQMDP-CZLJTSCOSA-N C[C@@H](C(OC1CCCC1)=O)NP(OC[C@H](C[C@@]1(C)F)O[C@H]1c1cnc2[n]1ncnc2N)([O]=C)=O Chemical compound C[C@@H](C(OC1CCCC1)=O)NP(OC[C@H](C[C@@]1(C)F)O[C@H]1c1cnc2[n]1ncnc2N)([O]=C)=O QFJJGVDPVAQMDP-CZLJTSCOSA-N 0.000 description 1
- YRGVZEKWHSBGBS-OSOWUJPXSA-N C[C@@H](C(OCC(C)(C)C)=O)NP(OC[C@H](C[C@@]1(C)F)O[C@H]1c1cnc2[n]1ncnc2N)([O]=C)=O Chemical compound C[C@@H](C(OCC(C)(C)C)=O)NP(OC[C@H](C[C@@]1(C)F)O[C@H]1c1cnc2[n]1ncnc2N)([O]=C)=O YRGVZEKWHSBGBS-OSOWUJPXSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/885,917 US7973013B2 (en) | 2009-09-21 | 2010-09-20 | 2'-fluoro substituted carba-nucleoside analogs for antiviral treatment |
| US12/885,917 | 2010-09-20 | ||
| US13/050,820 | 2011-03-17 | ||
| US13/050,820 US8455451B2 (en) | 2009-09-21 | 2011-03-17 | 2'-fluoro substituted carba-nucleoside analogs for antiviral treatment |
| PCT/US2011/029441 WO2012039791A1 (en) | 2010-09-20 | 2011-03-22 | 2' -fluoro substituted carba-nucleoside analogs for antiviral treatment |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016006833A Division JP2016074732A (ja) | 2010-09-20 | 2016-01-18 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013538230A JP2013538230A (ja) | 2013-10-10 |
| JP2013538230A5 true JP2013538230A5 (https=) | 2014-05-08 |
Family
ID=47748238
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013529139A Withdrawn JP2013538230A (ja) | 2010-09-20 | 2011-03-22 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
| JP2016006833A Withdrawn JP2016074732A (ja) | 2010-09-20 | 2016-01-18 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
| JP2017077366A Active JP6475280B2 (ja) | 2010-09-20 | 2017-04-10 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
| JP2018173758A Withdrawn JP2019014726A (ja) | 2010-09-20 | 2018-09-18 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016006833A Withdrawn JP2016074732A (ja) | 2010-09-20 | 2016-01-18 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
| JP2017077366A Active JP6475280B2 (ja) | 2010-09-20 | 2017-04-10 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
| JP2018173758A Withdrawn JP2019014726A (ja) | 2010-09-20 | 2018-09-18 | 抗ウイルス治療用の２’−フルオロ置換カルバヌクレオシド類似体 |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP2619206A1 (https=) |
| JP (4) | JP2013538230A (https=) |
| KR (1) | KR101879887B1 (https=) |
| CN (1) | CN103108876A (https=) |
| AP (1) | AP3699A (https=) |
| AU (1) | AU2011306066B2 (https=) |
| BR (1) | BR112013008017A2 (https=) |
| CA (1) | CA2807496C (https=) |
| CL (1) | CL2013000727A1 (https=) |
| CO (1) | CO6680669A2 (https=) |
| CR (1) | CR20130172A (https=) |
| EA (1) | EA026523B1 (https=) |
| EC (1) | ECSP13012560A (https=) |
| IL (1) | IL225221A0 (https=) |
| MA (1) | MA34593B1 (https=) |
| MX (1) | MX2013003179A (https=) |
| NZ (1) | NZ608070A (https=) |
| PE (3) | PE20171624A1 (https=) |
| PH (1) | PH12013500311B1 (https=) |
| SG (1) | SG188223A1 (https=) |
| WO (1) | WO2012039791A1 (https=) |
| ZA (1) | ZA201301042B (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| HUE025528T2 (en) | 2008-04-23 | 2016-05-30 | Gilead Sciences Inc | 1'-substituted carba-nucleoside analogs for antiviral treatment |
| MX2012003126A (es) | 2009-09-21 | 2012-06-19 | Gilead Sciences Inc | Procesos e intermedios para la preparacion de analogos de 1'-carbonucleosidos sustituidos. |
| AU2011282241B2 (en) | 2010-07-19 | 2015-07-30 | Gilead Sciences, Inc. | Methods for the preparation of diasteromerically pure phosphoramidate prodrugs |
| ES2524356T3 (es) | 2010-07-22 | 2014-12-05 | Gilead Sciences, Inc. | Métodos y compuestos para tratar infecciones provocadas por virus Paramyxoviridae |
| US20130273005A1 (en) | 2010-12-20 | 2013-10-17 | Gilead Sciences, Inc. | Methods for treating hcv |
| AR088441A1 (es) | 2011-09-12 | 2014-06-11 | Idenix Pharmaceuticals Inc | Compuestos de carboniloximetilfosforamidato sustituido y composiciones farmaceuticas para el tratamiento de infecciones virales |
| EP2709613B2 (en) | 2011-09-16 | 2020-08-12 | Gilead Pharmasset LLC | Methods for treating hcv |
| EP2950786B1 (en) | 2013-01-31 | 2019-11-27 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| UA119050C2 (uk) * | 2013-11-11 | 2019-04-25 | Ґілеад Саєнсиз, Інк. | ПІРОЛО[1.2-f][1.2.4]ТРИАЗИНИ, ЯКІ ВИКОРИСТОВУЮТЬСЯ ДЛЯ ЛІКУВАННЯ РЕСПІРАТОРНО-СИНЦИТІАЛЬНИХ ВІРУСНИХ ІНФЕКЦІЙ |
| TWI678369B (zh) | 2014-07-28 | 2019-12-01 | 美商基利科學股份有限公司 | 用於治療呼吸道合胞病毒感染之噻吩並［３,２-ｄ］嘧啶、呋喃並［３,２-ｄ］嘧啶及吡咯並［３,２-ｄ］嘧啶化合物類 |
| CN104230985B (zh) * | 2014-09-01 | 2017-01-18 | 北京天弘天达医药科技有限公司 | (s)‑2‑[(s)‑(4‑硝基‑苯氧基)‑苯氧基‑磷酰基氨基]丙酸异丙酯的制备方法 |
| TWI687432B (zh) | 2014-10-29 | 2020-03-11 | 美商基利科學股份有限公司 | 絲狀病毒科病毒感染之治療 |
| JP7381190B2 (ja) | 2014-12-26 | 2023-11-15 | エモリー・ユニバーシテイ | Ｎ４－ヒドロキシシチジン及び誘導体並びにそれに関連する抗ウイルス用途 |
| DK3785717T3 (da) | 2015-09-16 | 2022-03-21 | Gilead Sciences Inc | Fremgangsmåder til behandling af coronaviridae-infektioner |
| US10682368B2 (en) | 2017-03-14 | 2020-06-16 | Gilead Sciences, Inc. | Methods of treating feline coronavirus infections |
| CA3059777C (en) | 2017-05-01 | 2023-02-21 | Gilead Sciences, Inc. | Crystalline forms of (s)-2-ethylbutyl 2-(((s)-(((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f] [1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy) phosphoryl)amino)propanoate |
| WO2019014247A1 (en) | 2017-07-11 | 2019-01-17 | Gilead Sciences, Inc. | COMPOSITIONS COMPRISING POLYMERASE RNA INHIBITOR AND CYCLODEXTRIN FOR THE TREATMENT OF VIRAL INFECTIONS |
| PT3706762T (pt) | 2017-12-07 | 2024-12-05 | Univ Emory | N4-hidroxicitidina e derivados e utilizações antivirais relacionadas com os mesmos |
| 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 |
| KR20220153619A (ko) | 2020-03-12 | 2022-11-18 | 길리애드 사이언시즈, 인코포레이티드 | 1'-시아노 뉴클레오사이드의 제조 방법 |
| CA3172483A1 (en) | 2020-04-06 | 2021-10-14 | Scott Ellis | Inhalation formulations of 1'-cyano substituted carbanucleoside analogs |
| TW202203941A (zh) | 2020-05-29 | 2022-02-01 | 美商基利科學股份有限公司 | 瑞德西韋之治療方法 |
| PE20230618A1 (es) | 2020-06-24 | 2023-04-14 | Gilead Sciences Inc | Analogos de nucleosido de 1'-ciano y usos de los mismos |
| IL300453A (en) * | 2020-08-27 | 2023-04-01 | Gilead Sciences Inc | COMPOSITIONS AND METHODS FOR THE TREATMENT OF VIRAL INFECTIONS |
| KR20240154647A (ko) | 2022-03-02 | 2024-10-25 | 길리애드 사이언시즈, 인코포레이티드 | 바이러스성 감염 치료를 위한 화합물 및 방법 |
| IL315733A (en) | 2022-04-08 | 2024-11-01 | SHY Therapeutics LLC | Compounds that Interact with RAS Superfamily Proteins for the Treatment of Cancer, Inflammatory, Basoplastic, and Fibrotic Diseases |
| WO2023207942A1 (zh) * | 2022-04-25 | 2023-11-02 | 北京沐华生物科技有限责任公司 | 用于治疗或预防冠状病毒感染的核苷类药物及其用途 |
| US12357577B1 (en) | 2024-02-02 | 2025-07-15 | Gilead Sciences, Inc. | Pharmaceutical formulations and uses thereof |
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| HRP20120914T1 (hr) | 2007-05-10 | 2012-12-31 | Biocryst Pharmaceuticals, Inc. | Spojevi tetrahidrofuro[3,4-d]dioksolana, namijenjeni upotrebi u lijeäśenju virusnih infekcija i raka |
| HUE025528T2 (en) * | 2008-04-23 | 2016-05-30 | Gilead Sciences Inc | 1'-substituted carba-nucleoside analogs for antiviral treatment |
| WO2010036407A2 (en) * | 2008-05-15 | 2010-04-01 | Biocryst Pharmaceuticals, Inc. | Antiviral nucleoside analogs |
| WO2010002877A2 (en) * | 2008-07-03 | 2010-01-07 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| MX2011008409A (es) * | 2009-02-10 | 2011-10-21 | Gilead Sciences Inc | Análogos de carba-nucléosido para tratamiento antiviral. |
| CN102596958A (zh) * | 2009-09-21 | 2012-07-18 | 吉里德科学公司 | 用于抗病毒治疗的2’-氟代carba-核苷类似物 |
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2011
- 2011-03-22 BR BR112013008017A patent/BR112013008017A2/pt not_active Application Discontinuation
- 2011-03-22 EA EA201390141A patent/EA026523B1/ru unknown
- 2011-03-22 PE PE2017001530A patent/PE20171624A1/es unknown
- 2011-03-22 MX MX2013003179A patent/MX2013003179A/es not_active Application Discontinuation
- 2011-03-22 AU AU2011306066A patent/AU2011306066B2/en active Active
- 2011-03-22 EP EP11715792.5A patent/EP2619206A1/en not_active Withdrawn
- 2011-03-22 AP AP2013006767A patent/AP3699A/en active
- 2011-03-22 NZ NZ608070A patent/NZ608070A/en unknown
- 2011-03-22 JP JP2013529139A patent/JP2013538230A/ja not_active Withdrawn
- 2011-03-22 PH PH1/2013/500311A patent/PH12013500311B1/en unknown
- 2011-03-22 KR KR1020137010012A patent/KR101879887B1/ko active Active
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- 2011-03-22 CN CN2011800449231A patent/CN103108876A/zh active Pending
- 2011-03-22 WO PCT/US2011/029441 patent/WO2012039791A1/en not_active Ceased
- 2011-03-22 PE PE2013000530A patent/PE20131165A1/es active IP Right Grant
- 2011-03-22 SG SG2013011325A patent/SG188223A1/en unknown
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2013
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2016
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2017
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