AU2010273184B2 - Anti -influenza agents - Google Patents
Anti -influenza agents Download PDFInfo
- Publication number
- AU2010273184B2 AU2010273184B2 AU2010273184A AU2010273184A AU2010273184B2 AU 2010273184 B2 AU2010273184 B2 AU 2010273184B2 AU 2010273184 A AU2010273184 A AU 2010273184A AU 2010273184 A AU2010273184 A AU 2010273184A AU 2010273184 B2 AU2010273184 B2 AU 2010273184B2
- Authority
- AU
- Australia
- Prior art keywords
- optionally substituted
- alkenyl
- dideoxy
- acetamido
- alkyl
- 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.)
- Ceased
Links
- 206010022000 influenza Diseases 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 229910052739 hydrogen Inorganic materials 0.000 claims description 280
- -1 R 3 Chemical class 0.000 claims description 153
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 47
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 45
- 125000002252 acyl group Chemical group 0.000 claims description 42
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 239000003153 chemical reaction reagent Substances 0.000 claims description 21
- 150000003852 triazoles Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 238000003379 elimination reaction Methods 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- LBIDPYADBXDPCT-RWOPYEJCSA-N (4r,5s,6s,7r,8r)-2,3,4,5,6,7,8,9-octahydroxynon-2-enoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=C(O)C(O)=O LBIDPYADBXDPCT-RWOPYEJCSA-N 0.000 claims description 14
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- 150000002367 halogens Chemical class 0.000 claims description 10
- 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 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
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- 239000000651 prodrug Substances 0.000 claims description 9
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- 125000006239 protecting group Chemical group 0.000 claims description 9
- 150000001540 azides Chemical class 0.000 claims description 8
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- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 5
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- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
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- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
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- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 5
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 102000005348 Neuraminidase Human genes 0.000 abstract description 41
- 108010006232 Neuraminidase Proteins 0.000 abstract description 41
- 241000712431 Influenza A virus Species 0.000 abstract description 30
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
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- 230000002829 reductive effect Effects 0.000 description 20
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 19
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
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- 150000007942 carboxylates Chemical class 0.000 description 14
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- 239000000706 filtrate Substances 0.000 description 14
- 230000005764 inhibitory process Effects 0.000 description 14
- 241000712461 unidentified influenza virus Species 0.000 description 14
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- 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 13
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- 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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- YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- NQPHMXWPDCSHTE-UHFFFAOYSA-N trifluoromethanesulfonyl azide Chemical compound FC(F)(F)S(=O)(=O)N=[N+]=[N-] NQPHMXWPDCSHTE-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000007501 viral attachment Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2010273184A AU2010273184B2 (en) | 2009-07-16 | 2010-07-16 | Anti -influenza agents |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2009903329A AU2009903329A0 (en) | 2009-07-16 | Anti-influenza agents | |
| AU2009903329 | 2009-07-16 | ||
| AU2010273184A AU2010273184B2 (en) | 2009-07-16 | 2010-07-16 | Anti -influenza agents |
| PCT/AU2010/000905 WO2011006208A1 (en) | 2009-07-16 | 2010-07-16 | Anti -influenza agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2010273184A1 AU2010273184A1 (en) | 2012-03-01 |
| AU2010273184B2 true AU2010273184B2 (en) | 2015-07-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010273184A Ceased AU2010273184B2 (en) | 2009-07-16 | 2010-07-16 | Anti -influenza agents |
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) |
Families Citing this family (7)
| 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 |
| WO2014055988A1 (en) | 2012-10-05 | 2014-04-10 | Velico Medical, Inc. | Platelet additive solution having a beta-galactosidase inhibitor |
| JP6453050B2 (ja) * | 2013-11-15 | 2019-01-16 | 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 |
| JP6786095B2 (ja) * | 2016-07-27 | 2020-11-18 | 国立研究開発法人理化学研究所 | シアル酸類縁体 |
| WO2018213933A1 (en) | 2017-05-25 | 2018-11-29 | The Governors Of The University Of Alberta | Methods of preventing or treating atherosclerosis with inhibitors of specific isoenzymes of human neuraminidase |
| CN114423754A (zh) * | 2019-07-30 | 2022-04-29 | 格里菲斯大学 | 抗病毒剂和其用途 |
| US12116382B2 (en) | 2022-11-28 | 2024-10-15 | Hongene Biotech Corporation | Functionalized N-acetylgalactosamine analogs |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991016320A1 (en) * | 1990-04-24 | 1991-10-31 | Biota Scientific Management Pty Ltd | Derivatives and analogues of 2-deoxy-2,3-didehydro-n-acetyl neuraminic acid and their use as antiviral agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11279168A (ja) * | 1996-07-22 | 1999-10-12 | Sankyo Co Ltd | ノイラミン酸誘導体 |
| US5948816A (en) * | 1996-09-10 | 1999-09-07 | Daikin Industries, Ltd. | 4-substituted-2,7-dideoxy-7-fluoro-2,3-didehydro-sialic acid compounds |
| AUPR001000A0 (en) * | 2000-09-08 | 2000-10-05 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| US7045535B2 (en) * | 2001-03-08 | 2006-05-16 | Biocryst Pharmaceuticals, Inc. | Compounds useful for inhibiting paramyxovirus neuraminidase |
-
2010
- 2010-07-16 US US13/384,198 patent/US20120202877A1/en not_active Abandoned
- 2010-07-16 RU RU2012105073/04A patent/RU2012105073A/ru not_active Application Discontinuation
- 2010-07-16 CN CN201080040870.1A patent/CN102612514B/zh not_active Expired - Fee Related
- 2010-07-16 AU AU2010273184A patent/AU2010273184B2/en not_active Ceased
- 2010-07-16 SG SG2012002341A patent/SG177633A1/en unknown
- 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 EP EP20100799291 patent/EP2454248A4/en not_active Withdrawn
- 2010-07-16 JP JP2012519850A patent/JP2012532894A/ja active Pending
- 2010-07-16 CA CA2768081A patent/CA2768081A1/en not_active Abandoned
-
2012
- 2012-01-12 IL IL217523A patent/IL217523A0/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991016320A1 (en) * | 1990-04-24 | 1991-10-31 | Biota Scientific Management Pty Ltd | Derivatives and analogues of 2-deoxy-2,3-didehydro-n-acetyl neuraminic acid and their use as antiviral agents |
Non-Patent Citations (2)
| Title |
|---|
| GARCiA-SOSA, A. T. et al. J. Chem. Inf. Model. (2008) Vol. 48, pages 2074-2080. * |
| RUSSELL, R. J. et al. The structure of H5N1 avian influenza neuraminidase suggests new opportunities for drug design. Nature .(2006) Vol. 443, pages 45-49. * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2010273184A1 (en) | 2012-03-01 |
| IL217523A0 (en) | 2012-02-29 |
| SG177633A1 (en) | 2012-02-28 |
| CA2768081A1 (en) | 2011-01-20 |
| US20120202877A1 (en) | 2012-08-09 |
| WO2011006208A1 (en) | 2011-01-20 |
| RU2012105073A (ru) | 2013-08-27 |
| CN102612514A (zh) | 2012-07-25 |
| CN102612514B (zh) | 2016-01-13 |
| MX2012000576A (es) | 2012-07-20 |
| EP2454248A1 (en) | 2012-05-23 |
| JP2012532894A (ja) | 2012-12-20 |
| EP2454248A4 (en) | 2013-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |