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 | 2010-09-20 | ||
| US12/885,917 US7973013B2 (en) | 2009-09-21 | 2010-09-20 | 2'-fluoro substituted carba-nucleoside analogs for antiviral treatment |
| 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 (enExample) | 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 (enExample) |
| JP (4) | JP2013538230A (enExample) |
| KR (1) | KR101879887B1 (enExample) |
| CN (1) | CN103108876A (enExample) |
| AP (1) | AP3699A (enExample) |
| AU (1) | AU2011306066B2 (enExample) |
| BR (1) | BR112013008017A2 (enExample) |
| CA (1) | CA2807496C (enExample) |
| CL (1) | CL2013000727A1 (enExample) |
| CO (1) | CO6680669A2 (enExample) |
| CR (1) | CR20130172A (enExample) |
| EA (1) | EA026523B1 (enExample) |
| EC (1) | ECSP13012560A (enExample) |
| IL (1) | IL225221A0 (enExample) |
| MA (1) | MA34593B1 (enExample) |
| MX (1) | MX2013003179A (enExample) |
| NZ (1) | NZ608070A (enExample) |
| PE (3) | PE20131165A1 (enExample) |
| PH (1) | PH12013500311B1 (enExample) |
| SG (1) | SG188223A1 (enExample) |
| WO (1) | WO2012039791A1 (enExample) |
| ZA (1) | ZA201301042B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| HRP20130048T1 (hr) | 2008-04-23 | 2013-02-28 | Gilead Sciences, Inc. | Karba-nukleozidni analozi za antivirusnu terapiju |
| WO2011035250A1 (en) | 2009-09-21 | 2011-03-24 | Gilead Sciences, Inc. | Processes and intermediates for the preparation of 1'-substituted carba-nucleoside analogs |
| EA025311B1 (ru) | 2010-07-19 | 2016-12-30 | Гайлид Сайэнсиз, Инк. | Способы получения диастереомерно чистых фосфорамидатных пролекарств |
| ES2524356T3 (es) | 2010-07-22 | 2014-12-05 | Gilead Sciences, Inc. | Métodos y compuestos para tratar infecciones provocadas por virus Paramyxoviridae |
| AU2011349844B2 (en) | 2010-12-20 | 2017-06-01 | Gilead Sciences, Inc. | Combinations 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 |
| SI2709613T2 (sl) | 2011-09-16 | 2020-12-31 | Gilead Pharmasset LLC c/o Gilead Sciences, Inc. | Postopki za zdravljenje HCV |
| NZ729172A (en) | 2013-01-31 | 2018-06-29 | 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 |
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| TWI740546B (zh) | 2014-10-29 | 2021-09-21 | 美商基利科學股份有限公司 | 製備核糖苷的方法 |
| IL296496B2 (en) | 2014-12-26 | 2024-10-01 | Univ Emory | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| HRP20220355T1 (hr) | 2015-09-16 | 2022-05-13 | Gilead Sciences, Inc. | Postupci za liječenje infekcija coronaviridae |
| CN116036112A (zh) | 2017-03-14 | 2023-05-02 | 吉利德科学公司 | 治疗猫冠状病毒感染的方法 |
| WO2018204198A1 (en) | 2017-05-01 | 2018-11-08 | 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 |
| EP4512475A3 (en) | 2017-07-11 | 2025-05-14 | Gilead Sciences, Inc. | Compositions comprising an rna polymerase inhibitor and cyclodextrin for treating viral infections |
| KR102626210B1 (ko) | 2017-12-07 | 2024-01-18 | 에모리 유니버시티 | N4-하이드록시사이티딘 및 유도체 및 이와 관련된 항-바이러스 용도 |
| AU2021214911A1 (en) | 2020-01-27 | 2022-07-21 | Gilead Sciences, Inc. | Methods for treating SARS CoV-2 infections |
| CN118994170A (zh) | 2020-03-12 | 2024-11-22 | 吉利德科学公司 | 制备1'-氰基核苷的方法 |
| EP4132651B1 (en) | 2020-04-06 | 2026-03-18 | Gilead Sciences, Inc. | Inhalation formulations of 1'-cyano substituted carbanucleoside analogs |
| ES3041698T3 (en) | 2020-05-29 | 2025-11-13 | Gilead Sciences Inc | Remdesivir for the treatment of viral infections |
| CA3187821A1 (en) | 2020-06-24 | 2021-12-30 | Gilead Sciences, Inc. | 1'-cyano nucleoside analogs and uses thereof |
| WO2022047065A2 (en) | 2020-08-27 | 2022-03-03 | Gilead Sciences, Inc. | Compounds and methods for treatment of viral infections |
| TW202525810A (zh) | 2022-03-02 | 2025-07-01 | 美商基利科學股份有限公司 | 用於治療病毒感染的化合物及方法 |
| EP4504341A1 (en) | 2022-04-08 | 2025-02-12 | Shy Therapeutics LLC | Compounds that interact with ras superfamily proteins for treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| CA3256146A1 (en) * | 2022-04-25 | 2025-07-03 | Miracure Biotechnology Limited | NUCLEOSIDE MEDICINE FOR THE TREATMENT OR PREVENTION OF CORONAVIRUS INFECTION, AND ITS USE |
| US12357577B1 (en) | 2024-02-02 | 2025-07-15 | Gilead Sciences, Inc. | Pharmaceutical formulations and uses thereof |
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| EP2313102A2 (en) * | 2008-07-03 | 2011-04-27 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| CA2751277C (en) * | 2009-02-10 | 2018-10-30 | Gilead Sciences, Inc. | Carba-nucleoside analogs for antiviral treatment |
| AU2010295373B2 (en) * | 2009-09-21 | 2016-09-29 | Gilead Sciences, Inc. | 2' -fluoro substituted carba-nucleoside analogs for antiviral treatment |
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2011
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- 2011-03-22 CN CN2011800449231A patent/CN103108876A/zh active Pending
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