ES2657942T3 - Compuestos de metanotiona que tienen actividad antiviral - Google Patents
Compuestos de metanotiona que tienen actividad antiviral Download PDFInfo
- Publication number
- ES2657942T3 ES2657942T3 ES13722781.5T ES13722781T ES2657942T3 ES 2657942 T3 ES2657942 T3 ES 2657942T3 ES 13722781 T ES13722781 T ES 13722781T ES 2657942 T3 ES2657942 T3 ES 2657942T3
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- Prior art keywords
- formula
- alkyl
- ring
- compound
- pharmaceutically acceptable
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- 150000001875 compounds Chemical class 0.000 description 131
- 238000006243 chemical reaction Methods 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 229910052736 halogen Inorganic materials 0.000 description 30
- 150000002367 halogens Chemical class 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- -1 heterocyclic amides Chemical class 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002609 medium Substances 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 11
- 230000009385 viral infection Effects 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 241000700605 Viruses Species 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 10
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
- 241000712461 unidentified influenza virus Species 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 7
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 7
- 208000036142 Viral infection Diseases 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 206010022000 influenza Diseases 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000007832 Na2SO4 Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
- FNXYZOLJMOAKIU-UHFFFAOYSA-N [4-(2-chloro-4-nitrophenyl)piperazin-1-yl]-(5-methyl-3-phenyl-1,2-oxazol-4-yl)methanethione Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C(=S)N(CC1)CCN1C1=CC=C([N+]([O-])=O)C=C1Cl FNXYZOLJMOAKIU-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
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- 230000003612 virological effect Effects 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 241000712431 Influenza A virus Species 0.000 description 4
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- UZIXCCMXZQWTPB-UHFFFAOYSA-N trimethyl(2-phenylethynyl)silane Chemical class C[Si](C)(C)C#CC1=CC=CC=C1 UZIXCCMXZQWTPB-UHFFFAOYSA-N 0.000 description 4
- LKQDOONGSYFUQZ-UHFFFAOYSA-N (5-methyl-3-phenyl-1,2-oxazol-4-yl)-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methanethione Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C(=S)N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 LKQDOONGSYFUQZ-UHFFFAOYSA-N 0.000 description 3
- BWHNMVHDXATHDF-UHFFFAOYSA-N (5-methyl-3-phenyl-1,2-oxazol-4-yl)-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methanone Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C(=O)N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 BWHNMVHDXATHDF-UHFFFAOYSA-N 0.000 description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- DSSJOZCNGHJXAC-UHFFFAOYSA-N 3-(2-methoxyphenyl)-5-methyltriazole-4-carbothialdehyde Chemical compound COc1ccccc1-n1nnc(C)c1C=S DSSJOZCNGHJXAC-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 239000012124 Opti-MEM Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 102000004142 Trypsin Human genes 0.000 description 3
- 108090000631 Trypsin Proteins 0.000 description 3
- 241000711975 Vesicular stomatitis virus Species 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
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- 229940125782 compound 2 Drugs 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 208000037797 influenza A Diseases 0.000 description 3
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- 239000012071 phase Substances 0.000 description 3
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- 125000004076 pyridyl group Chemical group 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- HXEVQMXCHCDPSO-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carbonyl chloride Chemical compound ClC(=O)C1=C(C)ON=C1C1=CC=CC=C1 HXEVQMXCHCDPSO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
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- QJNGODOYMOPVAI-UHFFFAOYSA-N 5-(2,6-dimethoxyphenyl)-3-methyltriazole-4-carbothialdehyde Chemical compound COc1cccc(OC)c1-c1nnn(C)c1C=S QJNGODOYMOPVAI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261648700P | 2012-05-18 | 2012-05-18 | |
| US201261648700P | 2012-05-18 | ||
| US201261659516P | 2012-06-14 | 2012-06-14 | |
| US201261659516P | 2012-06-14 | ||
| US201261666286P | 2012-06-29 | 2012-06-29 | |
| US201261666286P | 2012-06-29 | ||
| US201361774991P | 2013-03-08 | 2013-03-08 | |
| US201361774991P | 2013-03-08 | ||
| PCT/EP2013/060266 WO2013171334A1 (en) | 2012-05-18 | 2013-05-17 | Methanethione compounds having antiviral activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2657942T3 true ES2657942T3 (es) | 2018-03-07 |
Family
ID=48444409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13722781.5T Active ES2657942T3 (es) | 2012-05-18 | 2013-05-17 | Compuestos de metanotiona que tienen actividad antiviral |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US9359310B2 (OSRAM) |
| EP (1) | EP2870141B1 (OSRAM) |
| JP (2) | JP6484168B2 (OSRAM) |
| KR (1) | KR102092207B1 (OSRAM) |
| CN (1) | CN104540810B (OSRAM) |
| AU (1) | AU2013261735B2 (OSRAM) |
| BR (1) | BR112014028632B1 (OSRAM) |
| CA (1) | CA2879816C (OSRAM) |
| CL (1) | CL2014003116A1 (OSRAM) |
| DK (1) | DK2870141T3 (OSRAM) |
| EA (1) | EA029044B1 (OSRAM) |
| ES (1) | ES2657942T3 (OSRAM) |
| IL (1) | IL235742A0 (OSRAM) |
| IN (1) | IN2014DN10658A (OSRAM) |
| MX (1) | MX356846B (OSRAM) |
| MY (1) | MY169094A (OSRAM) |
| NZ (1) | NZ702073A (OSRAM) |
| SG (1) | SG11201407703QA (OSRAM) |
| WO (1) | WO2013171334A1 (OSRAM) |
| ZA (1) | ZA201409220B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104540810B (zh) * | 2012-05-18 | 2017-01-18 | 维洛诺瓦流感公司 | 具有抗病毒活性的甲硫酮化合物 |
| CN107056762B (zh) * | 2016-12-22 | 2020-08-28 | 四川百利药业有限责任公司 | 一种用作抗流感病毒的双羰基类似物 |
| WO2021204923A1 (en) | 2020-04-09 | 2021-10-14 | Vironova Medical Ab | Antiviral agents |
| WO2021204924A1 (en) | 2020-04-09 | 2021-10-14 | Vironova Medical Ab | Compounds for use in the treatment of hypercytokinemia |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6642390B2 (en) | 2001-07-11 | 2003-11-04 | Lexicon Pharmaceuticals, Inc. | One step synthesis of 1,2,3-triazole carboxylic acids |
| JP2006516656A (ja) * | 2003-01-28 | 2006-07-06 | アヴェンティス ファーマ エス．エー． | Ｎ−アリールヘテロ芳香族物質、それを含む組成物およびその用途 |
| US8207205B2 (en) | 2008-04-21 | 2012-06-26 | Institute For Oneworld Health | Compounds, compositions and methods comprising oxadiazole derivatives |
| WO2011015037A1 (en) * | 2009-08-05 | 2011-02-10 | The University Of Hongkong | Antiviral compounds and methods of making and using there of cross reference to related applications |
| JP2013542201A (ja) | 2010-09-28 | 2013-11-21 | ブリストル−マイヤーズ スクイブ カンパニー | 広域スペクトルのインフルエンザ抗ウイルス剤としての置換されたヘテロアリール基を有する新規ピペラジン類似体 |
| EP2484655A1 (en) | 2011-02-04 | 2012-08-08 | Vironova AB | A thionation process and a thionating agent |
| CN104540810B (zh) * | 2012-05-18 | 2017-01-18 | 维洛诺瓦流感公司 | 具有抗病毒活性的甲硫酮化合物 |
| JP6762767B2 (ja) * | 2016-06-01 | 2020-09-30 | キヤノン株式会社 | 撮像素子、撮像装置、および撮像信号処理方法 |
-
2013
- 2013-05-17 CN CN201380038170.2A patent/CN104540810B/zh not_active Expired - Fee Related
- 2013-05-17 NZ NZ702073A patent/NZ702073A/en not_active IP Right Cessation
- 2013-05-17 EA EA201401277A patent/EA029044B1/ru not_active IP Right Cessation
- 2013-05-17 CA CA2879816A patent/CA2879816C/en active Active
- 2013-05-17 BR BR112014028632A patent/BR112014028632B1/pt not_active IP Right Cessation
- 2013-05-17 US US14/401,545 patent/US9359310B2/en not_active Expired - Fee Related
- 2013-05-17 SG SG11201407703QA patent/SG11201407703QA/en unknown
- 2013-05-17 KR KR1020147035090A patent/KR102092207B1/ko not_active Expired - Fee Related
- 2013-05-17 ES ES13722781.5T patent/ES2657942T3/es active Active
- 2013-05-17 EP EP13722781.5A patent/EP2870141B1/en active Active
- 2013-05-17 MX MX2014014007A patent/MX356846B/es active IP Right Grant
- 2013-05-17 JP JP2015512081A patent/JP6484168B2/ja not_active Expired - Fee Related
- 2013-05-17 IN IN10658DEN2014 patent/IN2014DN10658A/en unknown
- 2013-05-17 WO PCT/EP2013/060266 patent/WO2013171334A1/en not_active Ceased
- 2013-05-17 AU AU2013261735A patent/AU2013261735B2/en not_active Ceased
- 2013-05-17 DK DK13722781.5T patent/DK2870141T3/da active
- 2013-05-17 MY MYPI2014003200A patent/MY169094A/en unknown
-
2014
- 2014-11-17 IL IL235742A patent/IL235742A0/en active IP Right Grant
- 2014-11-17 CL CL2014003116A patent/CL2014003116A1/es unknown
- 2014-12-15 ZA ZA2014/09220A patent/ZA201409220B/en unknown
-
2017
- 2017-11-09 JP JP2017216649A patent/JP2018065817A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150012289A (ko) | 2015-02-03 |
| CA2879816C (en) | 2020-07-07 |
| JP6484168B2 (ja) | 2019-03-13 |
| AU2013261735A1 (en) | 2015-01-22 |
| NZ702073A (en) | 2017-07-28 |
| CN104540810B (zh) | 2017-01-18 |
| EP2870141A1 (en) | 2015-05-13 |
| BR112014028632A2 (pt) | 2017-06-27 |
| ZA201409220B (en) | 2016-08-31 |
| SG11201407703QA (en) | 2015-01-29 |
| HK1210165A1 (en) | 2016-04-15 |
| US9359310B2 (en) | 2016-06-07 |
| US20150133468A1 (en) | 2015-05-14 |
| WO2013171334A1 (en) | 2013-11-21 |
| IL235742A0 (en) | 2015-02-01 |
| JP2015517516A (ja) | 2015-06-22 |
| KR102092207B1 (ko) | 2020-03-23 |
| JP2018065817A (ja) | 2018-04-26 |
| CL2014003116A1 (es) | 2015-08-07 |
| DK2870141T3 (da) | 2018-01-29 |
| EA029044B1 (ru) | 2018-02-28 |
| MX356846B (es) | 2018-06-18 |
| AU2013261735B2 (en) | 2017-07-20 |
| CN104540810A (zh) | 2015-04-22 |
| MY169094A (en) | 2019-02-18 |
| CA2879816A1 (en) | 2013-11-21 |
| BR112014028632B1 (pt) | 2020-01-28 |
| EA201401277A1 (ru) | 2015-04-30 |
| EP2870141B1 (en) | 2017-11-22 |
| BR112014028632A8 (pt) | 2018-04-03 |
| IN2014DN10658A (OSRAM) | 2015-08-28 |
| MX2014014007A (es) | 2015-05-11 |
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