JP2012532894A - 抗インフルエンザ薬 - Google Patents
抗インフルエンザ薬 Download PDFInfo
- Publication number
- JP2012532894A JP2012532894A JP2012519850A JP2012519850A JP2012532894A JP 2012532894 A JP2012532894 A JP 2012532894A JP 2012519850 A JP2012519850 A JP 2012519850A JP 2012519850 A JP2012519850 A JP 2012519850A JP 2012532894 A JP2012532894 A JP 2012532894A
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- acetamido
- dideoxy
- anhydro
- glycero
- 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.)
- Pending
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- 239000003814 drug Substances 0.000 title claims abstract description 15
- 206010022000 influenza Diseases 0.000 title claims abstract description 15
- 229940079593 drug Drugs 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 196
- 102000005348 Neuraminidase Human genes 0.000 claims abstract description 43
- 108010006232 Neuraminidase Proteins 0.000 claims abstract description 43
- 241000712431 Influenza A virus Species 0.000 claims abstract description 29
- -1 R 3 Chemical class 0.000 claims description 129
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000002252 acyl group Chemical group 0.000 claims description 33
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000003852 triazoles Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000003379 elimination reaction Methods 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 10
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- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
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- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- QHIROPCGBMZKSC-XSMZZKNVSA-N methyl (2r,3r,4s)-3-acetamido-4-acetyloxy-5-(3-acetyloxypropyl)-2-[(1s,2r)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2h-pyran-6-carboxylate Chemical compound COC(=O)C1=C(CCCOC(C)=O)[C@H](OC(C)=O)[C@@H](NC(C)=O)[C@H]([C@H](OC(C)=O)[C@@H](COC(C)=O)OC(C)=O)O1 QHIROPCGBMZKSC-XSMZZKNVSA-N 0.000 claims description 7
- 229940124639 Selective inhibitor Drugs 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- CCPSTGRFUHTVNN-ZSEVYCOTSA-N (2r,3r,4s)-3-acetamido-4-hydroxy-5-[(e)-3-(4-methylphenyl)prop-2-enyl]-2-[(1r,2r)-1,2,3-trihydroxypropyl]-3,4-dihydro-2h-pyran-6-carboxylic acid Chemical compound O1[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(=O)C)[C@@H](O)C(C\C=C\C=2C=CC(C)=CC=2)=C1C(O)=O CCPSTGRFUHTVNN-ZSEVYCOTSA-N 0.000 claims description 3
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 3
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- 238000006138 lithiation reaction Methods 0.000 claims description 3
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- 125000003441 thioacyl group Chemical group 0.000 claims description 3
- 238000005852 acetolysis reaction Methods 0.000 claims description 2
- 239000012039 electrophile Substances 0.000 claims description 2
- 238000003795 desorption Methods 0.000 claims 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
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- 125000001033 ether group Chemical group 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
- 235000019439 ethyl acetate Nutrition 0.000 description 68
- 239000000243 solution Substances 0.000 description 65
- 239000011734 sodium Substances 0.000 description 59
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 45
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- 239000000203 mixture Substances 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 239000012043 crude product Substances 0.000 description 32
- 150000002500 ions Chemical class 0.000 description 32
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- 239000000377 silicon dioxide Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- 239000006260 foam Substances 0.000 description 19
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 18
- JINJZWSZQKHCIP-UFGQHTETSA-N 2-deoxy-2,3-dehydro-N-acetylneuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO JINJZWSZQKHCIP-UFGQHTETSA-N 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- JINJZWSZQKHCIP-UHFFFAOYSA-N Neu5Ac2en Natural products CC(=O)NC1C(O)C=C(C(O)=O)OC1C(O)C(O)CO JINJZWSZQKHCIP-UHFFFAOYSA-N 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Chemical group 0.000 description 16
- 241000712461 unidentified influenza virus Species 0.000 description 16
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
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- 241000700605 Viruses Species 0.000 description 11
- 150000007942 carboxylates Chemical class 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
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- 239000007858 starting material Substances 0.000 description 11
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- 238000004440 column chromatography Methods 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- FCDPQMAOJARMTG-UHFFFAOYSA-M benzylidene-[1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]-dichlororuthenium;tricyclohexylphosphanium Chemical compound C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.CC1=CC(C)=CC(C)=C1N(CCN1C=2C(=CC(C)=CC=2C)C)C1=[Ru](Cl)(Cl)=CC1=CC=CC=C1 FCDPQMAOJARMTG-UHFFFAOYSA-M 0.000 description 9
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- 239000003112 inhibitor Substances 0.000 description 9
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- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 8
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 8
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- NENPYTRHICXVCS-YNEHKIRRSA-N oseltamivir acid Chemical compound CCC(CC)O[C@@H]1C=C(C(O)=O)C[C@H](N)[C@H]1NC(C)=O NENPYTRHICXVCS-YNEHKIRRSA-N 0.000 description 7
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- 229930003231 vitamin Natural products 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2009903329A AU2009903329A0 (en) | 2009-07-16 | Anti-influenza agents | |
| AU2009903329 | 2009-07-16 | ||
| PCT/AU2010/000905 WO2011006208A1 (en) | 2009-07-16 | 2010-07-16 | Anti -influenza agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012532894A true JP2012532894A (ja) | 2012-12-20 |
| JP2012532894A5 JP2012532894A5 (enExample) | 2013-09-05 |
Family
ID=43448806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012519850A Pending JP2012532894A (ja) | 2009-07-16 | 2010-07-16 | 抗インフルエンザ薬 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20120202877A1 (enExample) |
| EP (1) | EP2454248A4 (enExample) |
| JP (1) | JP2012532894A (enExample) |
| CN (1) | CN102612514B (enExample) |
| AU (1) | AU2010273184B2 (enExample) |
| CA (1) | CA2768081A1 (enExample) |
| IL (1) | IL217523A0 (enExample) |
| MX (1) | MX2012000576A (enExample) |
| RU (1) | RU2012105073A (enExample) |
| SG (1) | SG177633A1 (enExample) |
| WO (1) | WO2011006208A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015117233A (ja) * | 2013-11-15 | 2015-06-25 | 国立大学法人富山大学 | 2−デオキシ−2,3−ジデヒドロシアル酸誘導体およびその製造法 |
| JP2018016579A (ja) * | 2016-07-27 | 2018-02-01 | 国立研究開発法人理化学研究所 | シアル酸類縁体 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9788539B2 (en) | 2011-05-17 | 2017-10-17 | Velico Medical, Inc. | Platelet protection solution having beta-galactosidase and sialidase inhibitors |
| EP2903430A1 (en) | 2012-10-05 | 2015-08-12 | Velico Medical, Inc. | Platelet additive solution having a beta-galactosidase inhibitor |
| US11773129B2 (en) | 2017-05-25 | 2023-10-03 | The Governors Of The University Of Alberta | Methods of preventing or treating atherosclerosis with inhibitors of specific isoenzymes of human neuraminidase |
| JP2022543006A (ja) * | 2019-07-30 | 2022-10-07 | グリフィス・ユニバーシティ | 抗ウイルス剤およびその使用 |
| US12116382B2 (en) | 2022-11-28 | 2024-10-15 | Hongene Biotech Corporation | Functionalized N-acetylgalactosamine analogs |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05507068A (ja) * | 1990-04-24 | 1993-10-14 | バイオタ、サイアンティフィック、マネージメント、プロプライエタリ、リミテッド | 2―デオキシ―2,3―ジデヒドロ―n―アセチルノイラミン酸の誘導体及び類似体と抗ウイルス剤としてのそれらの用途 |
| WO1998011083A1 (en) * | 1996-09-10 | 1998-03-19 | Daikin Industries, Ltd. | 4-substituted-2,7-dideoxy-7-fluoro-2,3-didehydrosialic acids |
| JPH11279168A (ja) * | 1996-07-22 | 1999-10-12 | Sankyo Co Ltd | ノイラミン酸誘導体 |
| WO2002076971A1 (en) * | 2001-03-08 | 2002-10-03 | Biocryst Pharmaceuticals, Inc. | Compounds useful for inhibiting paramyxovirus neuraminidase |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPR001000A0 (en) * | 2000-09-08 | 2000-10-05 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
-
2010
- 2010-07-16 JP JP2012519850A patent/JP2012532894A/ja active Pending
- 2010-07-16 US US13/384,198 patent/US20120202877A1/en not_active Abandoned
- 2010-07-16 EP EP20100799291 patent/EP2454248A4/en not_active Withdrawn
- 2010-07-16 SG SG2012002341A patent/SG177633A1/en unknown
- 2010-07-16 CA CA2768081A patent/CA2768081A1/en not_active Abandoned
- 2010-07-16 MX MX2012000576A patent/MX2012000576A/es not_active Application Discontinuation
- 2010-07-16 WO PCT/AU2010/000905 patent/WO2011006208A1/en not_active Ceased
- 2010-07-16 RU RU2012105073/04A patent/RU2012105073A/ru not_active Application Discontinuation
- 2010-07-16 AU AU2010273184A patent/AU2010273184B2/en not_active Ceased
- 2010-07-16 CN CN201080040870.1A patent/CN102612514B/zh not_active Expired - Fee Related
-
2012
- 2012-01-12 IL IL217523A patent/IL217523A0/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05507068A (ja) * | 1990-04-24 | 1993-10-14 | バイオタ、サイアンティフィック、マネージメント、プロプライエタリ、リミテッド | 2―デオキシ―2,3―ジデヒドロ―n―アセチルノイラミン酸の誘導体及び類似体と抗ウイルス剤としてのそれらの用途 |
| JPH11279168A (ja) * | 1996-07-22 | 1999-10-12 | Sankyo Co Ltd | ノイラミン酸誘導体 |
| WO1998011083A1 (en) * | 1996-09-10 | 1998-03-19 | Daikin Industries, Ltd. | 4-substituted-2,7-dideoxy-7-fluoro-2,3-didehydrosialic acids |
| WO2002076971A1 (en) * | 2001-03-08 | 2002-10-03 | Biocryst Pharmaceuticals, Inc. | Compounds useful for inhibiting paramyxovirus neuraminidase |
Non-Patent Citations (4)
| Title |
|---|
| JPN6014033226; J.Org.Chem. 69, 2004, p.665-679 * |
| JPN6014033228; J.Chem.Inf.Model. 48, 2008, p.2074-2080 * |
| JPN6014033231; Nature 443, 2006, 45-49 * |
| JPN6014033234; Virology 58, 1974, p.457-463 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015117233A (ja) * | 2013-11-15 | 2015-06-25 | 国立大学法人富山大学 | 2−デオキシ−2,3−ジデヒドロシアル酸誘導体およびその製造法 |
| JP2018016579A (ja) * | 2016-07-27 | 2018-02-01 | 国立研究開発法人理化学研究所 | シアル酸類縁体 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2454248A1 (en) | 2012-05-23 |
| MX2012000576A (es) | 2012-07-20 |
| AU2010273184A1 (en) | 2012-03-01 |
| SG177633A1 (en) | 2012-02-28 |
| CA2768081A1 (en) | 2011-01-20 |
| WO2011006208A1 (en) | 2011-01-20 |
| US20120202877A1 (en) | 2012-08-09 |
| RU2012105073A (ru) | 2013-08-27 |
| AU2010273184B2 (en) | 2015-07-09 |
| CN102612514A (zh) | 2012-07-25 |
| IL217523A0 (en) | 2012-02-29 |
| EP2454248A4 (en) | 2013-04-03 |
| CN102612514B (zh) | 2016-01-13 |
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