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
- ppm
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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 (OSRAM) | 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 (OSRAM) |
| EP (2) | EP3068776B1 (OSRAM) |
| JP (3) | JP6615755B2 (OSRAM) |
| KR (1) | KR102353413B1 (OSRAM) |
| CN (2) | CN105849100B (OSRAM) |
| AU (1) | AU2014348840B2 (OSRAM) |
| CA (1) | CA2930103A1 (OSRAM) |
| CL (1) | CL2016001110A1 (OSRAM) |
| CY (1) | CY1121919T1 (OSRAM) |
| DK (1) | DK3068776T3 (OSRAM) |
| ES (1) | ES2741444T3 (OSRAM) |
| HR (1) | HRP20191525T1 (OSRAM) |
| HU (1) | HUE044667T2 (OSRAM) |
| IL (1) | IL245585B (OSRAM) |
| LT (1) | LT3068776T (OSRAM) |
| ME (1) | ME03460B (OSRAM) |
| MX (1) | MX382171B (OSRAM) |
| NZ (1) | NZ719729A (OSRAM) |
| PL (1) | PL3068776T3 (OSRAM) |
| PT (1) | PT3068776T (OSRAM) |
| RS (1) | RS59144B1 (OSRAM) |
| RU (1) | RU2700415C1 (OSRAM) |
| SG (1) | SG10201804026WA (OSRAM) |
| SI (1) | SI3068776T1 (OSRAM) |
| SM (1) | SMT201900450T1 (OSRAM) |
| UA (1) | UA121376C2 (OSRAM) |
| WO (1) | WO2015073476A1 (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010262905B2 (en) | 2009-06-17 | 2015-04-16 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| ES2741444T3 (es) * | 2013-11-13 | 2020-02-11 | Vertex Pharma | Inhibidores de la replicación de virus de la gripe |
| EP3068782B1 (en) | 2013-11-13 | 2018-05-23 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| UA124609C2 (uk) | 2014-08-08 | 2021-10-20 | Янссен Саєнсиз Айрленд Юсі | Індоли для застосування при інфекції, спричиненій вірусом грипу |
| WO2016183116A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| EP3362451B1 (en) * | 2015-12-09 | 2023-04-12 | Sunshine Lake Pharma Co., Ltd. | Inhibitors of influenza virus replication, application methods and uses thereof |
| 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 |
| EP3609502A1 (en) * | 2017-04-12 | 2020-02-19 | Vertex Pharmaceuticals Incorporated | Combination therapies for treating influenza virus infection |
| CA3094588A1 (en) | 2018-04-06 | 2019-10-10 | Janssen Pharmaceuticals, Inc. | Isothermal reactive crystallisation process for the preparation of a crystalline form of pimodivir hydrochloride hemihydrate |
| JP7706362B2 (ja) * | 2018-11-13 | 2025-07-11 | コクリスタル ファーマ，インコーポレイテッド | インフルエンザ治療薬の製剤 |
| 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 |
| US11462418B2 (en) | 2020-01-17 | 2022-10-04 | Taiwan Semiconductor Manufacturing Co., Ltd. | Integrated circuit package and method |
| JP2023511956A (ja) * | 2020-01-24 | 2023-03-23 | レゲネロン ファーマシューティカルス，インコーポレーテッド | タンパク質－抗ウイルス化合物コンジュゲート |
| CN112578034B (zh) * | 2020-11-04 | 2022-02-11 | 广东众生睿创生物科技有限公司 | 一种手性胺小分子及其盐的质量控制方法 |
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| US4349552A (en) | 1978-10-30 | 1982-09-14 | Fujisawa Pharmaceutical Company, Ltd. | 5-Fluorouracil derivatives, and their pharmaceutical compositions |
| NZ221717A (en) | 1986-09-10 | 1990-08-28 | Sandoz Ltd | Azaindole and indolizine derivatives and pharmaceutical compositions |
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| KR20160045070A (ko) | 2013-08-22 | 2016-04-26 | 버텍스 파마슈티칼스 인코포레이티드 | 동위원소 풍부 아자인돌 |
| US9296727B2 (en) | 2013-10-07 | 2016-03-29 | Vertex Pharmaceuticals Incorporated | Methods of regioselective synthesis of 2,4-disubstituted pyrimidines |
| CA2930105A1 (en) | 2013-11-13 | 2015-05-21 | Vertex Pharmaceuticals Incorporated | Formulations of azaindole compounds |
| ES2741444T3 (es) * | 2013-11-13 | 2020-02-11 | Vertex Pharma | Inhibidores de la replicación de virus de la gripe |
| EP3068782B1 (en) | 2013-11-13 | 2018-05-23 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| MA40772A (fr) | 2014-10-02 | 2017-08-08 | Vertex Pharma | Variants du virus de la grippe a |
| MA40773A (fr) | 2014-10-02 | 2017-08-08 | Vertex Pharma | Variants du virus influenza a |
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2014
- 2014-11-12 ES ES14802787T patent/ES2741444T3/es active Active
- 2014-11-12 LT LTEP14802787.3T patent/LT3068776T/lt unknown
- 2014-11-12 ME MEP-2019-226A patent/ME03460B/me unknown
- 2014-11-12 KR KR1020167015720A patent/KR102353413B1/ko not_active Expired - Fee Related
- 2014-11-12 PT PT14802787T patent/PT3068776T/pt unknown
- 2014-11-12 EP EP14802787.3A patent/EP3068776B1/en active Active
- 2014-11-12 MX MX2016006199A patent/MX382171B/es unknown
- 2014-11-12 SM SM20190450T patent/SMT201900450T1/it unknown
- 2014-11-12 SG SG10201804026WA patent/SG10201804026WA/en unknown
- 2014-11-12 RU RU2016122611A patent/RU2700415C1/ru active
- 2014-11-12 HR HRP20191525 patent/HRP20191525T1/hr unknown
- 2014-11-12 HU HUE14802787 patent/HUE044667T2/hu unknown
- 2014-11-12 NZ NZ719729A patent/NZ719729A/en not_active IP Right Cessation
- 2014-11-12 AU AU2014348840A patent/AU2014348840B2/en not_active Ceased
- 2014-11-12 CA CA2930103A patent/CA2930103A1/en not_active Abandoned
- 2014-11-12 CN CN201480071165.6A patent/CN105849100B/zh not_active Expired - Fee Related
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- 2014-11-12 SI SI201431295T patent/SI3068776T1/sl unknown
- 2014-11-12 WO PCT/US2014/065114 patent/WO2015073476A1/en not_active Ceased
- 2014-11-12 DK DK14802787.3T patent/DK3068776T3/da active
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- 2014-11-12 UA UAA201606307A patent/UA121376C2/uk unknown
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- 2014-11-12 EP EP19165859.0A patent/EP3578554A1/en not_active Withdrawn
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2016
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2019
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