JP2016537346A5 - - Google Patents
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- JP2016537346A5 JP2016537346A5 JP2016529944A JP2016529944A JP2016537346A5 JP 2016537346 A5 JP2016537346 A5 JP 2016537346A5 JP 2016529944 A JP2016529944 A JP 2016529944A JP 2016529944 A JP2016529944 A JP 2016529944A JP 2016537346 A5 JP2016537346 A5 JP 2016537346A5
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- JP
- Japan
- Prior art keywords
- compound
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- methyl
- composition
- 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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- 150000001875 compounds Chemical class 0.000 claims description 135
- 238000000034 method Methods 0.000 claims description 81
- 150000003840 hydrochlorides Chemical class 0.000 claims description 55
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 46
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 24
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 24
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 20
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 16
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 16
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 16
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 16
- 238000001228 spectrum Methods 0.000 claims description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
- 239000013078 crystal Substances 0.000 claims description 14
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 14
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 14
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 12
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 12
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 12
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 12
- 229940011051 isopropyl acetate Drugs 0.000 claims description 12
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 12
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 12
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 229940090181 propyl acetate Drugs 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 12
- 229940126062 Compound A Drugs 0.000 claims description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 8
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 8
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 8
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003443 antiviral agent Substances 0.000 claims description 6
- 241000712461 unidentified influenza virus Species 0.000 claims description 6
- -1 methyl ethyl Chemical group 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 229940123424 Neuraminidase inhibitor Drugs 0.000 claims description 4
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
- NPUUWZQAVJYUTO-UHFFFAOYSA-N anisole;propan-2-one Chemical compound CC(C)=O.COC1=CC=CC=C1 NPUUWZQAVJYUTO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 206010022000 influenza Diseases 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002911 sialidase inhibitor Substances 0.000 claims description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 241000712431 Influenza A virus Species 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- ZCGNOVWYSGBHAU-UHFFFAOYSA-N favipiravir Chemical group NC(=O)C1=NC(F)=CNC1=O ZCGNOVWYSGBHAU-UHFFFAOYSA-N 0.000 claims description 2
- 229950008454 favipiravir Drugs 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical group CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims description 2
- 229960003752 oseltamivir Drugs 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 229960001028 zanamivir Drugs 0.000 claims description 2
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims description 2
- 230000010076 replication Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- JGPXDNKSIXAZEQ-UHFFFAOYSA-N OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c(nc3)c2cc3F)ncc1F)=O Chemical compound OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c(nc3)c2cc3F)ncc1F)=O JGPXDNKSIXAZEQ-UHFFFAOYSA-N 0.000 description 2
- JGPXDNKSIXAZEQ-AHYVENMTSA-N OC(C(C1CCC2CC1)[C@H]2Nc1nc(-c(c2c3)c[nH]c2ncc3F)ncc1F)=O Chemical compound OC(C(C1CCC2CC1)[C@H]2Nc1nc(-c(c2c3)c[nH]c2ncc3F)ncc1F)=O JGPXDNKSIXAZEQ-AHYVENMTSA-N 0.000 description 2
- 230000029812 viral genome replication Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361903572P | 2013-11-13 | 2013-11-13 | |
| US61/903,572 | 2013-11-13 | ||
| PCT/US2014/065114 WO2015073476A1 (en) | 2013-11-13 | 2014-11-12 | Inhibitors of influenza viruses replication |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019000201A Division JP2019048898A (ja) | 2013-11-13 | 2019-01-04 | インフルエンザウイルスの複製の阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016537346A JP2016537346A (ja) | 2016-12-01 |
| JP2016537346A5 true JP2016537346A5 (enExample) | 2017-12-21 |
| JP6615755B2 JP6615755B2 (ja) | 2019-12-04 |
Family
ID=51952043
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016529944A Expired - Fee Related JP6615755B2 (ja) | 2013-11-13 | 2014-11-12 | インフルエンザウイルスの複製の阻害剤 |
| JP2019000201A Pending JP2019048898A (ja) | 2013-11-13 | 2019-01-04 | インフルエンザウイルスの複製の阻害剤 |
| JP2020098516A Withdrawn JP2020128441A (ja) | 2013-11-13 | 2020-06-05 | インフルエンザウイルスの複製の阻害剤 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019000201A Pending JP2019048898A (ja) | 2013-11-13 | 2019-01-04 | インフルエンザウイルスの複製の阻害剤 |
| JP2020098516A Withdrawn JP2020128441A (ja) | 2013-11-13 | 2020-06-05 | インフルエンザウイルスの複製の阻害剤 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US9771361B2 (enExample) |
| EP (2) | EP3068776B1 (enExample) |
| JP (3) | JP6615755B2 (enExample) |
| KR (1) | KR102353413B1 (enExample) |
| CN (2) | CN105849100B (enExample) |
| AU (1) | AU2014348840B2 (enExample) |
| CA (1) | CA2930103A1 (enExample) |
| CL (1) | CL2016001110A1 (enExample) |
| CY (1) | CY1121919T1 (enExample) |
| DK (1) | DK3068776T3 (enExample) |
| ES (1) | ES2741444T3 (enExample) |
| HR (1) | HRP20191525T1 (enExample) |
| HU (1) | HUE044667T2 (enExample) |
| IL (1) | IL245585B (enExample) |
| LT (1) | LT3068776T (enExample) |
| ME (1) | ME03460B (enExample) |
| MX (1) | MX382171B (enExample) |
| NZ (1) | NZ719729A (enExample) |
| PL (1) | PL3068776T3 (enExample) |
| PT (1) | PT3068776T (enExample) |
| RS (1) | RS59144B1 (enExample) |
| RU (1) | RU2700415C1 (enExample) |
| SG (1) | SG10201804026WA (enExample) |
| SI (1) | SI3068776T1 (enExample) |
| SM (1) | SMT201900450T1 (enExample) |
| UA (1) | UA121376C2 (enExample) |
| WO (1) | WO2015073476A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GEAP202213376A (en) | 2009-06-17 | 2022-02-25 | Vertex Pharmaceuticals Incorporated Us | Inhibitors of influenza viruses replication |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| LT3068776T (lt) * | 2013-11-13 | 2019-08-12 | Vertex Pharmaceuticals Incorporated | Gripo virusų replikacijos inhibitoriai |
| HUE052178T2 (hu) | 2013-11-13 | 2021-04-28 | Vertex Pharma | Eljárások influenzavírus-replikáció inhibitorainak elõállítására |
| MA40547A (fr) | 2014-08-08 | 2017-06-14 | Janssen Sciences Ireland Uc | Indoles pouvant être utilisés dans l'infection par le virus influenza |
| WO2016183116A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| JP6857617B2 (ja) | 2015-05-13 | 2021-04-14 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤 |
| JP6952695B2 (ja) * | 2015-12-09 | 2021-10-20 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | インフルエンザウイルス複製の阻害剤、その適用方法および使用 |
| WO2018137670A1 (zh) * | 2017-01-24 | 2018-08-02 | 苏州科睿思制药有限公司 | 一种病毒蛋白抑制剂药物vx-787的晶型及其制备方法和用途 |
| JP2020516634A (ja) * | 2017-04-12 | 2020-06-11 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルス感染の処置方法および併用療法 |
| JP2021520363A (ja) | 2018-04-06 | 2021-08-19 | ヤンセン ファーマシューティカルズ，インコーポレーテッド | 結晶形態のピモジビル塩酸塩半水和物を調製するための等温反応性結晶化方法 |
| CN120078782A (zh) * | 2018-11-13 | 2025-06-03 | 共晶制药公司 | 流感治疗剂的配制物 |
| WO2020212399A1 (en) | 2019-04-15 | 2020-10-22 | Janssen Pharmaceutica Nv | Method for preparing an alkyl trans-3-aminobicyclo[2.2.2]octane-2-carboxylic acid ester compound |
| CN112079785B (zh) * | 2019-06-13 | 2023-08-04 | 中国科学院上海药物研究所 | 一种新型抗流感病毒奥司他韦衍生物、其制备方法及用途 |
| WO2021038480A1 (en) * | 2019-08-27 | 2021-03-04 | Janssen Pharmaceuticals, Inc. | Combinations for treating influenza virus |
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| MX2014005565A (es) | 2011-11-07 | 2014-05-30 | Vertex Pharma | Metodos para tratar enfermedades inflamatorias y composiciones farmaceuticas utiles para los mismos. |
| EP2858984A1 (en) | 2012-06-08 | 2015-04-15 | Vertex Pharmaceuticals Inc. | Inhibitors of influenza viruses replication |
| WO2014201332A1 (en) | 2013-06-14 | 2014-12-18 | Vertex Pharmaceuticals Incorporated | Pharmaceutical combinations useful for treating rheumatoid arthritis |
| CA2921198A1 (en) | 2013-08-22 | 2015-02-26 | Vertex Pharmaceuticals Incorporated | Isotopically enriched azaindoles |
| US9296727B2 (en) | 2013-10-07 | 2016-03-29 | Vertex Pharmaceuticals Incorporated | Methods of regioselective synthesis of 2,4-disubstituted pyrimidines |
| LT3068776T (lt) * | 2013-11-13 | 2019-08-12 | Vertex Pharmaceuticals Incorporated | Gripo virusų replikacijos inhibitoriai |
| HUE052178T2 (hu) | 2013-11-13 | 2021-04-28 | Vertex Pharma | Eljárások influenzavírus-replikáció inhibitorainak elõállítására |
| AU2014348762A1 (en) | 2013-11-13 | 2016-05-26 | Vertex Pharmaceuticals Incorporated | Formulations of azaindole compounds |
| MA40773A (fr) | 2014-10-02 | 2017-08-08 | Vertex Pharma | Variants du virus influenza a |
| MA40772A (fr) | 2014-10-02 | 2017-08-08 | Vertex Pharma | Variants du virus de la grippe a |
-
2014
- 2014-11-12 LT LTEP14802787.3T patent/LT3068776T/lt unknown
- 2014-11-12 RS RS20191054A patent/RS59144B1/sr unknown
- 2014-11-12 DK DK14802787.3T patent/DK3068776T3/da active
- 2014-11-12 SG SG10201804026WA patent/SG10201804026WA/en unknown
- 2014-11-12 HR HRP20191525 patent/HRP20191525T1/hr unknown
- 2014-11-12 MX MX2016006199A patent/MX382171B/es unknown
- 2014-11-12 PT PT14802787T patent/PT3068776T/pt unknown
- 2014-11-12 CN CN201480071165.6A patent/CN105849100B/zh not_active Expired - Fee Related
- 2014-11-12 CA CA2930103A patent/CA2930103A1/en not_active Abandoned
- 2014-11-12 HU HUE14802787 patent/HUE044667T2/hu unknown
- 2014-11-12 AU AU2014348840A patent/AU2014348840B2/en not_active Ceased
- 2014-11-12 NZ NZ719729A patent/NZ719729A/en not_active IP Right Cessation
- 2014-11-12 JP JP2016529944A patent/JP6615755B2/ja not_active Expired - Fee Related
- 2014-11-12 EP EP14802787.3A patent/EP3068776B1/en active Active
- 2014-11-12 SM SM20190450T patent/SMT201900450T1/it unknown
- 2014-11-12 KR KR1020167015720A patent/KR102353413B1/ko not_active Expired - Fee Related
- 2014-11-12 CN CN201910583102.3A patent/CN110156779A/zh active Pending
- 2014-11-12 SI SI201431295T patent/SI3068776T1/sl unknown
- 2014-11-12 ES ES14802787T patent/ES2741444T3/es active Active
- 2014-11-12 WO PCT/US2014/065114 patent/WO2015073476A1/en not_active Ceased
- 2014-11-12 EP EP19165859.0A patent/EP3578554A1/en not_active Withdrawn
- 2014-11-12 PL PL14802787T patent/PL3068776T3/pl unknown
- 2014-11-12 RU RU2016122611A patent/RU2700415C1/ru active
- 2014-11-12 UA UAA201606307A patent/UA121376C2/uk unknown
- 2014-11-12 ME MEP-2019-226A patent/ME03460B/me unknown
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2016
- 2016-05-10 IL IL245585A patent/IL245585B/en unknown
- 2016-05-10 CL CL2016001110A patent/CL2016001110A1/es unknown
- 2016-05-10 US US15/150,459 patent/US9771361B2/en active Active
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2019
- 2019-01-04 JP JP2019000201A patent/JP2019048898A/ja active Pending
- 2019-08-22 CY CY20191100902T patent/CY1121919T1/el unknown
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2020
- 2020-06-05 JP JP2020098516A patent/JP2020128441A/ja not_active Withdrawn
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