RU2014120421A - Производные гетероарилгидроксамовой кислоты и их применение при лечении, облегчении течения или профилактике вирусных заболеваний - Google Patents
Производные гетероарилгидроксамовой кислоты и их применение при лечении, облегчении течения или профилактике вирусных заболеваний Download PDFInfo
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- RU2014120421A RU2014120421A RU2014120421/04A RU2014120421A RU2014120421A RU 2014120421 A RU2014120421 A RU 2014120421A RU 2014120421/04 A RU2014120421/04 A RU 2014120421/04A RU 2014120421 A RU2014120421 A RU 2014120421A RU 2014120421 A RU2014120421 A RU 2014120421A
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- Prior art keywords
- alkyl
- optionally substituted
- compound
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- hal
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- 201000010099 disease Diseases 0.000 title claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims 13
- 230000003612 virological effect Effects 0.000 title claims 13
- 230000002265 prevention Effects 0.000 title claims 4
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 41
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 125000001424 substituent group Chemical group 0.000 claims abstract 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 21
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract 15
- 125000005842 heteroatom Chemical group 0.000 claims abstract 15
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 15
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 5
- 229940002612 prodrug Drugs 0.000 claims abstract 5
- 239000000651 prodrug Substances 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 239000012453 solvate Substances 0.000 claims abstract 5
- UPIOIHHILZMAPM-UHFFFAOYSA-N N-(3-chlorophenyl)-N-hydroxy-2-quinolin-2-ylacetamide Chemical compound ClC=1C=C(C=CC1)N(O)C(=O)CC1=NC2=CC=CC=C2C=C1 UPIOIHHILZMAPM-UHFFFAOYSA-N 0.000 claims abstract 2
- GEOMGEWWDPCHKY-UHFFFAOYSA-N N-(3-chlorophenyl)-N-hydroxypyridine-2-carboxamide Chemical compound ClC=1C=C(C=CC1)N(O)C(C1=NC=CC=C1)=O GEOMGEWWDPCHKY-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 238000003556 assay Methods 0.000 claims 8
- 241000712892 Arenaviridae Species 0.000 claims 4
- 241000711573 Coronaviridae Species 0.000 claims 4
- 102100031780 Endonuclease Human genes 0.000 claims 4
- 108010042407 Endonucleases Proteins 0.000 claims 4
- 241000711950 Filoviridae Species 0.000 claims 4
- 241000710781 Flaviviridae Species 0.000 claims 4
- 241000700586 Herpesviridae Species 0.000 claims 4
- 241000712464 Orthomyxoviridae Species 0.000 claims 4
- 241000711504 Paramyxoviridae Species 0.000 claims 4
- 241000150350 Peribunyaviridae Species 0.000 claims 4
- 241000709664 Picornaviridae Species 0.000 claims 4
- 241000712907 Retroviridae Species 0.000 claims 4
- 241000711931 Rhabdoviridae Species 0.000 claims 4
- 241000710924 Togaviridae Species 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 238000002866 fluorescence resonance energy transfer Methods 0.000 claims 4
- 206010022000 influenza Diseases 0.000 claims 4
- 239000003446 ligand Substances 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- 101800004538 Bradykinin Proteins 0.000 claims 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims 1
- 102100035792 Kininogen-1 Human genes 0.000 claims 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims 1
- 229940123424 Neuraminidase inhibitor Drugs 0.000 claims 1
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 1
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims 1
- 229930003827 cannabinoid Natural products 0.000 claims 1
- 239000003557 cannabinoid Substances 0.000 claims 1
- 229940125400 channel inhibitor Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000002911 sialidase inhibitor Substances 0.000 claims 1
- 241000712461 unidentified influenza virus Species 0.000 claims 1
- FBTFYVPGZQXGLX-UHFFFAOYSA-N ON(C(c1nc(cccc2)c2cc1)=O)c(cc1)ccc1Cl Chemical compound ON(C(c1nc(cccc2)c2cc1)=O)c(cc1)ccc1Cl FBTFYVPGZQXGLX-UHFFFAOYSA-N 0.000 description 1
- IJIVLPMKWAFWNQ-UHFFFAOYSA-N ON(C(c1nc(cccc2)c2cc1)=O)c1ccccc1 Chemical compound ON(C(c1nc(cccc2)c2cc1)=O)c1ccccc1 IJIVLPMKWAFWNQ-UHFFFAOYSA-N 0.000 description 1
- KMMCFEXAAGIVLT-UHFFFAOYSA-N ONC(c1nccc(-c2cccnc2)c1)=O Chemical compound ONC(c1nccc(-c2cccnc2)c1)=O KMMCFEXAAGIVLT-UHFFFAOYSA-N 0.000 description 1
- AWJLBFXUZYCIIH-UHFFFAOYSA-N ONC(c1ncccc1)=O Chemical compound ONC(c1ncccc1)=O AWJLBFXUZYCIIH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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- 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
- C07D491/10—Spiro-condensed systems
- C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161550045P | 2011-10-21 | 2011-10-21 | |
| US61/550,045 | 2011-10-21 | ||
| PCT/EP2012/070757 WO2013057251A2 (en) | 2011-10-21 | 2012-10-19 | Heteroaryl hydroxamic acid derivatives and their use in the treatment, amelioration or prevention of a viral disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014120421A true RU2014120421A (ru) | 2015-11-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| RU2014120421/04A RU2014120421A (ru) | 2011-10-21 | 2012-10-19 | Производные гетероарилгидроксамовой кислоты и их применение при лечении, облегчении течения или профилактике вирусных заболеваний |
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| US (2) | US20130102600A1 (OSRAM) |
| EP (1) | EP2776396A2 (OSRAM) |
| JP (1) | JP6047168B2 (OSRAM) |
| KR (1) | KR20140100476A (OSRAM) |
| CN (1) | CN103958475B (OSRAM) |
| BR (1) | BR112014001369A2 (OSRAM) |
| CA (1) | CA2852750A1 (OSRAM) |
| HK (2) | HK1199640A1 (OSRAM) |
| MX (1) | MX2014003803A (OSRAM) |
| RU (1) | RU2014120421A (OSRAM) |
| WO (1) | WO2013057251A2 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2727772C1 (ru) * | 2016-09-05 | 2020-07-23 | Гуандун Рэйновент Байотек Ко., Лтд. | Производные пиримидина против вируса гриппа |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014177514A1 (en) | 2013-04-30 | 2014-11-06 | Bayer Cropscience Ag | Nematicidal n-substituted phenethylcarboxamides |
| CN107074880A (zh) | 2014-07-07 | 2017-08-18 | 萨维拉制药有限公司 | 二氢吡啶并吡嗪‑1,8‑二酮和它们在治疗、改善或预防病毒疾病中的用途 |
| WO2016033150A1 (en) * | 2014-08-28 | 2016-03-03 | X-Chem, Inc. | Soluble epoxide hydrolase inhibitors and uses thereof |
| MX394421B (es) | 2015-04-28 | 2025-03-24 | Shionogi & Co | Derivados de piridona policiclica sustituida y profarmaco de los mismos |
| WO2016175224A1 (ja) | 2015-04-28 | 2016-11-03 | 塩野義製薬株式会社 | 置換された多環性ピリドン誘導体およびそのプロドラッグ |
| US20170081331A1 (en) | 2015-09-18 | 2017-03-23 | F. Hoffmann-La Roche Ag | Pyrazolopyrazines and their use in the treatment, amelioration or prevention of a viral disease |
| EP3391888B1 (en) | 2015-12-15 | 2023-09-27 | Shionogi & Co., Ltd. | Medicine for treating influenza characterized by comprising combination of cap-dependent endonuclease inhibitor with anti-influenza drug |
| JP6957535B2 (ja) | 2016-06-29 | 2021-11-02 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ピリダジノンベースの広域スペクトル抗インフルエンザ阻害剤 |
| KR20190018469A (ko) | 2016-08-10 | 2019-02-22 | 시오노기세야쿠 가부시키가이샤 | 치환된 다환성 피리돈 유도체 및 그의 프로드러그를 함유하는 의약 조성물 |
| WO2022146755A1 (en) * | 2020-12-29 | 2022-07-07 | Merck Sharp & Dohme Corp. | Amido-substituted pyridyl compounds and methods of use thereof for the treatment of herpesviruses |
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| US5475109A (en) | 1994-10-17 | 1995-12-12 | Merck & Co., Inc. | Dioxobutanoic acid derivatives as inhibitors of influenza endonuclease |
| US6680385B2 (en) * | 2002-01-25 | 2004-01-20 | The Hong Kong Polytechnic University | Catalytic preparation of aryl methyl ketones using a molecular oxygen-containing gas as the oxidant |
| US7550463B2 (en) | 2004-09-15 | 2009-06-23 | Shionogi & Co., Ltd. | Carbamoylpyridone derivatives having inhibitory activity against HIV integrase |
| WO2010100475A1 (en) * | 2009-03-02 | 2010-09-10 | Astrazeneca Ab | Hydroxamic acid derivatives as gram-negative antibacterial agents |
| TWI518084B (zh) | 2009-03-26 | 2016-01-21 | 鹽野義製藥股份有限公司 | 哌喃酮與吡啶酮衍生物之製造方法 |
| US8835461B2 (en) | 2009-03-26 | 2014-09-16 | Shionogi & Co., Ltd. | Substituted 3-hydroxy-4-pyridone derivative |
| WO2011000566A2 (en) * | 2009-06-30 | 2011-01-06 | Savira Pharmaceuticals Gmbh | Compounds and pharmaceutical compositions for the treatment of negative-sense ssrna virus infections |
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2012
- 2012-10-18 US US13/655,394 patent/US20130102600A1/en not_active Abandoned
- 2012-10-19 BR BR112014001369A patent/BR112014001369A2/pt not_active IP Right Cessation
- 2012-10-19 EP EP12786860.2A patent/EP2776396A2/en not_active Withdrawn
- 2012-10-19 CA CA2852750A patent/CA2852750A1/en not_active Abandoned
- 2012-10-19 JP JP2014536252A patent/JP6047168B2/ja not_active Expired - Fee Related
- 2012-10-19 KR KR1020147013723A patent/KR20140100476A/ko not_active Withdrawn
- 2012-10-19 MX MX2014003803A patent/MX2014003803A/es unknown
- 2012-10-19 RU RU2014120421/04A patent/RU2014120421A/ru not_active Application Discontinuation
- 2012-10-19 CN CN201280051750.0A patent/CN103958475B/zh not_active Expired - Fee Related
- 2012-10-19 WO PCT/EP2012/070757 patent/WO2013057251A2/en not_active Ceased
- 2012-10-19 HK HK14113138.0A patent/HK1199640A1/xx unknown
- 2012-10-19 HK HK14110437.4A patent/HK1197059A1/xx unknown
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2016
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2727772C1 (ru) * | 2016-09-05 | 2020-07-23 | Гуандун Рэйновент Байотек Ко., Лтд. | Производные пиримидина против вируса гриппа |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1197059A1 (en) | 2015-01-02 |
| US20130102600A1 (en) | 2013-04-25 |
| BR112014001369A2 (pt) | 2017-01-10 |
| JP6047168B2 (ja) | 2016-12-21 |
| WO2013057251A2 (en) | 2013-04-25 |
| CA2852750A1 (en) | 2013-04-25 |
| EP2776396A2 (en) | 2014-09-17 |
| KR20140100476A (ko) | 2014-08-14 |
| MX2014003803A (es) | 2015-03-23 |
| JP2014530837A (ja) | 2014-11-20 |
| CN103958475B (zh) | 2015-11-25 |
| HK1199640A1 (en) | 2015-07-10 |
| WO2013057251A3 (en) | 2013-06-06 |
| CN103958475A (zh) | 2014-07-30 |
| US20160297763A1 (en) | 2016-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20171002 |