CA2770140A1 - Antiviral compounds and methods of making and using thereof cross reference to related applications - Google Patents
Antiviral compounds and methods of making and using thereof cross reference to related applications Download PDFInfo
- Publication number
- CA2770140A1 CA2770140A1 CA2770140A CA2770140A CA2770140A1 CA 2770140 A1 CA2770140 A1 CA 2770140A1 CA 2770140 A CA2770140 A CA 2770140A CA 2770140 A CA2770140 A CA 2770140A CA 2770140 A1 CA2770140 A1 CA 2770140A1
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- Prior art keywords
- compound
- branched
- linear
- nitro
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- 238000000034 method Methods 0.000 title claims abstract description 45
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 17
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- -1 heterocyclic amides Chemical class 0.000 claims abstract description 54
- 206010022000 influenza Diseases 0.000 claims abstract description 26
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
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- 125000003118 aryl group Chemical group 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
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- BUFQZEHPOKLSTP-UHFFFAOYSA-M sodium;oxido hydrogen sulfate Chemical compound [Na+].OS(=O)(=O)O[O-] BUFQZEHPOKLSTP-UHFFFAOYSA-M 0.000 description 1
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 239000003760 tallow Substances 0.000 description 1
- 229940061367 tamiflu Drugs 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- 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
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
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- 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 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
- A61K31/42—Oxazoles
-
- 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
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Molecular Biology (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23143109P | 2009-08-05 | 2009-08-05 | |
| US61/231,431 | 2009-08-05 | ||
| PCT/CN2010/001187 WO2011015037A1 (en) | 2009-08-05 | 2010-08-05 | Antiviral compounds and methods of making and using there of cross reference to related applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2770140A1 true CA2770140A1 (en) | 2011-02-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2770140A Abandoned CA2770140A1 (en) | 2009-08-05 | 2010-08-05 | Antiviral compounds and methods of making and using thereof cross reference to related applications |
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| Country | Link |
|---|---|
| EP (1) | EP2462138B1 (enExample) |
| JP (1) | JP2013501008A (enExample) |
| KR (1) | KR20120092567A (enExample) |
| CN (1) | CN102596946B (enExample) |
| AU (1) | AU2010281265A1 (enExample) |
| BR (1) | BR112012002331A2 (enExample) |
| CA (1) | CA2770140A1 (enExample) |
| IL (1) | IL217745A0 (enExample) |
| IN (1) | IN2012DN01254A (enExample) |
| MX (1) | MX2012001504A (enExample) |
| RU (1) | RU2012104214A (enExample) |
| SG (1) | SG178106A1 (enExample) |
| WO (1) | WO2011015037A1 (enExample) |
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| GB0918249D0 (en) | 2009-10-19 | 2009-12-02 | Respivert Ltd | Compounds |
| WO2011147198A1 (en) * | 2010-05-28 | 2011-12-01 | Versitech Limited | Compounds and methods for treatment of proliferative diseases |
| RS53844B1 (sr) * | 2010-09-08 | 2015-08-31 | Bristol-Myers Squibb Company | Novi analozi piperazina kao antivirusna sredstva širokog spektra protiv influenca virusa |
| BR112013007651A2 (pt) * | 2010-09-28 | 2019-09-24 | Bristol-Myers Squibb Company | análogos de piperazina com grupos heteroarila substituídos como antivirais de influenza de amplo espectro |
| UY33337A (es) | 2010-10-18 | 2011-10-31 | Respivert Ltd | DERIVADOS SUSTITUIDOS DE 1H-PIRAZOL[ 3,4-d]PIRIMIDINA COMO INHIBIDORES DE LAS FOSFOINOSITIDA 3-QUINASAS |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| GB201104267D0 (en) | 2011-03-14 | 2011-04-27 | Cancer Rec Tech Ltd | Pyrrolopyridineamino derivatives |
| US20140011700A1 (en) * | 2011-03-25 | 2014-01-09 | Bristol-Myers Squibb Company | Three-dimensional structure of h1n1 nucleoprotein in complex with antiviral compounds |
| KR101369584B1 (ko) * | 2011-04-19 | 2014-03-06 | 일양약품주식회사 | 페닐-이속사졸 유도체 및 그의 제조방법 |
| CN102432555A (zh) * | 2011-09-09 | 2012-05-02 | 中国科学院广州生物医药与健康研究院 | 1,2,3-三氮唑-4（5）羧酰胺类化合物及其应用 |
| NZ627963A (en) | 2012-03-13 | 2015-08-28 | Respivert Ltd | Dry powder pharmaceutical formulations for inhalation of a compound that inhibits pi3 kinase |
| JP6484168B2 (ja) | 2012-05-18 | 2019-03-13 | ヴィロノヴァ・インフルエンザ・アクチェボラーグ | 抗ウイルス活性を有するメタンチオン化合物 |
| US9676734B2 (en) | 2012-05-18 | 2017-06-13 | Vironova Influenza Ab | Compounds and methods |
| CA2876689C (en) | 2012-06-13 | 2022-04-26 | Incyte Corporation | Substituted tricyclic compounds as fgfr inhibitors |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
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| JPH05117150A (ja) * | 1991-10-25 | 1993-05-14 | Sanwa Kagaku Kenkyusho Co Ltd | 抗ウイルス剤 |
| KR200293242Y1 (ko) * | 2002-04-18 | 2002-11-01 | 전이범 | 산소 절단기호스 |
| DE10236564A1 (de) * | 2002-08-08 | 2004-05-19 | Ursapharm Arzneimittel Gmbh & Co. Kg | Verwendung von papaverinartigem Vasodilatator und pharmazeutische Zusammensetzung |
| NZ560712A (en) * | 2005-02-17 | 2010-12-24 | Synta Pharmaceuticals Corp | (3,4,5-trisubstituted-phenyl)isoxazole combretastin derivatives for the treatment of disorders |
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
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- 2010-08-05 EP EP10805941.1A patent/EP2462138B1/en active Active
- 2010-08-05 AU AU2010281265A patent/AU2010281265A1/en not_active Abandoned
- 2010-08-05 BR BR112012002331A patent/BR112012002331A2/pt not_active IP Right Cessation
- 2010-08-05 KR KR1020127005837A patent/KR20120092567A/ko not_active Withdrawn
- 2010-08-05 SG SG2012005450A patent/SG178106A1/en unknown
- 2010-08-05 JP JP2012523184A patent/JP2013501008A/ja active Pending
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- 2010-08-05 IN IN1254DEN2012 patent/IN2012DN01254A/en unknown
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| AU2010281265A2 (en) | 2012-04-05 |
| SG178106A1 (en) | 2012-03-29 |
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| EP2462138B1 (en) | 2014-09-24 |
| AU2010281265A1 (en) | 2012-03-22 |
| RU2012104214A (ru) | 2013-09-10 |
| BR112012002331A2 (pt) | 2019-09-24 |
| IN2012DN01254A (enExample) | 2015-05-15 |
| CN102596946B (zh) | 2015-06-17 |
| KR20120092567A (ko) | 2012-08-21 |
| EP2462138A1 (en) | 2012-06-13 |
| IL217745A0 (en) | 2012-03-29 |
| EP2462138A4 (en) | 2013-01-23 |
| JP2013501008A (ja) | 2013-01-10 |
| CN102596946A (zh) | 2012-07-18 |
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