CA2809624A1 - Novel piperazine analogs as broad-spectrum influenza antivirals - Google Patents
Novel piperazine analogs as broad-spectrum influenza antivirals Download PDFInfo
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- CA2809624A1 CA2809624A1 CA2809624A CA2809624A CA2809624A1 CA 2809624 A1 CA2809624 A1 CA 2809624A1 CA 2809624 A CA2809624 A CA 2809624A CA 2809624 A CA2809624 A CA 2809624A CA 2809624 A1 CA2809624 A1 CA 2809624A1
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- -1 -CH2F Chemical group 0.000 claims abstract description 81
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 241000712461 unidentified influenza virus Species 0.000 claims abstract description 11
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 7
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- 238000000034 method Methods 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
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- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000003368 amide group Chemical group 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 16
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
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- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 12
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
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- PJKUSRSBYCRKCJ-UHFFFAOYSA-N tert-butyl 5-(bromomethyl)-3-(2-methoxyphenyl)-1,2-oxazole-4-carboxylate Chemical compound COC1=CC=CC=C1C1=NOC(CBr)=C1C(=O)OC(C)(C)C PJKUSRSBYCRKCJ-UHFFFAOYSA-N 0.000 description 1
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- QPLKXDQLRIQYIA-UHFFFAOYSA-N tert-butyl n-(5-bromo-2-chlorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Br)=CC=C1Cl QPLKXDQLRIQYIA-UHFFFAOYSA-N 0.000 description 1
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- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38072810P | 2010-09-08 | 2010-09-08 | |
| US61/380,728 | 2010-09-08 | ||
| PCT/US2011/050504 WO2012033736A1 (en) | 2010-09-08 | 2011-09-06 | Novel piperazine analogs as broad-spectrum influenza antivirals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2809624A1 true CA2809624A1 (en) | 2012-03-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2809624A Abandoned CA2809624A1 (en) | 2010-09-08 | 2011-09-06 | Novel piperazine analogs as broad-spectrum influenza antivirals |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8362004B2 (enExample) |
| EP (1) | EP2614052B1 (enExample) |
| JP (1) | JP5902172B2 (enExample) |
| CN (1) | CN103201268B (enExample) |
| BR (1) | BR112013005552A2 (enExample) |
| CA (1) | CA2809624A1 (enExample) |
| DK (1) | DK2614052T3 (enExample) |
| EA (1) | EA023258B1 (enExample) |
| ES (1) | ES2533068T3 (enExample) |
| HR (1) | HRP20150228T1 (enExample) |
| MX (1) | MX2013002557A (enExample) |
| PL (1) | PL2614052T3 (enExample) |
| PT (1) | PT2614052E (enExample) |
| RS (1) | RS53844B1 (enExample) |
| SI (1) | SI2614052T1 (enExample) |
| SM (1) | SMT201500068B (enExample) |
| WO (1) | WO2012033736A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101369584B1 (ko) * | 2011-04-19 | 2014-03-06 | 일양약품주식회사 | 페닐-이속사졸 유도체 및 그의 제조방법 |
| JP6293770B2 (ja) * | 2012-11-05 | 2018-03-14 | ナント ホールディングス アイピー，エルエルシー | ヘッジホッグシグナル伝達経路阻害剤としての環状スルホンアミド含有誘導体 |
| KR102089122B1 (ko) | 2016-08-25 | 2020-03-13 | 주식회사 엘지화학 | 디아민 화합물 및 이를 이용하여 제조된 플렉시블 소자용 기판 |
| CA3052353A1 (en) * | 2017-02-02 | 2018-08-09 | Janssen Vaccines & Prevention B.V. | Piperazine derivatives for influenza virus inhibition |
| WO2018141854A1 (en) | 2017-02-02 | 2018-08-09 | Janssen Vaccines & Prevention B.V. | Piperazine derivatives for influenza virus inhibition |
| WO2021204924A1 (en) * | 2020-04-09 | 2021-10-14 | Vironova Medical Ab | Compounds for use in the treatment of hypercytokinemia |
| WO2021204923A1 (en) * | 2020-04-09 | 2021-10-14 | Vironova Medical Ab | Antiviral agents |
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| GB9914371D0 (en) * | 1999-06-18 | 1999-08-18 | Smithkline Beecham Plc | Novel compounds |
| US7196080B2 (en) * | 2001-06-15 | 2007-03-27 | Astellas Pharma Inc. | Phenylpyridinecarbonylpiperazinederivative |
| AU2003246972A1 (en) | 2002-08-06 | 2004-02-23 | Astrazeneca Ab | Condensed pyridines and pyrimidines with tie2 (tek) activity |
| WO2004078732A1 (fr) * | 2003-01-28 | 2004-09-16 | Aventis Pharma S.A. | Produits n-aryl-heteroaromatiques, compositions les contenant et utilisation |
| US6949865B2 (en) * | 2003-01-31 | 2005-09-27 | Betabatt, Inc. | Apparatus and method for generating electrical current from the nuclear decay process of a radioactive material |
| GB0428235D0 (en) | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Novel compounds |
| EP1834954A1 (en) * | 2006-03-15 | 2007-09-19 | 4Sc Ag | Thiazoles as NF-kB Inhibitors (proteasome inhibitors) |
| RU2012104214A (ru) * | 2009-08-05 | 2013-09-10 | Верситек Лимитед | Противовирусные соединения и способы их получения и применения |
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2011
- 2011-09-06 JP JP2013528244A patent/JP5902172B2/ja not_active Expired - Fee Related
- 2011-09-06 PT PT11758034T patent/PT2614052E/pt unknown
- 2011-09-06 CA CA2809624A patent/CA2809624A1/en not_active Abandoned
- 2011-09-06 BR BR112013005552A patent/BR112013005552A2/pt not_active Application Discontinuation
- 2011-09-06 WO PCT/US2011/050504 patent/WO2012033736A1/en not_active Ceased
- 2011-09-06 MX MX2013002557A patent/MX2013002557A/es active IP Right Grant
- 2011-09-06 DK DK11758034.0T patent/DK2614052T3/en active
- 2011-09-06 PL PL11758034T patent/PL2614052T3/pl unknown
- 2011-09-06 HR HRP20150228AT patent/HRP20150228T1/hr unknown
- 2011-09-06 EP EP11758034.0A patent/EP2614052B1/en active Active
- 2011-09-06 US US13/225,851 patent/US8362004B2/en active Active
- 2011-09-06 RS RS20150127A patent/RS53844B1/sr unknown
- 2011-09-06 ES ES11758034.0T patent/ES2533068T3/es active Active
- 2011-09-06 EA EA201390362A patent/EA023258B1/ru not_active IP Right Cessation
- 2011-09-06 CN CN201180053649.4A patent/CN103201268B/zh not_active Expired - Fee Related
- 2011-09-06 SI SI201130411T patent/SI2614052T1/sl unknown
-
2015
- 2015-03-18 SM SM201500068T patent/SMT201500068B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN103201268B (zh) | 2015-08-12 |
| HRP20150228T1 (hr) | 2015-04-10 |
| EA023258B1 (ru) | 2016-05-31 |
| ES2533068T3 (es) | 2015-04-07 |
| SMT201500068B (it) | 2015-05-05 |
| PT2614052E (pt) | 2015-03-31 |
| MX2013002557A (es) | 2013-05-28 |
| PL2614052T3 (pl) | 2015-06-30 |
| BR112013005552A2 (pt) | 2016-05-03 |
| US8362004B2 (en) | 2013-01-29 |
| CN103201268A (zh) | 2013-07-10 |
| EP2614052B1 (en) | 2014-12-31 |
| EP2614052A1 (en) | 2013-07-17 |
| JP5902172B2 (ja) | 2016-04-13 |
| SI2614052T1 (sl) | 2015-04-30 |
| WO2012033736A1 (en) | 2012-03-15 |
| JP2013537193A (ja) | 2013-09-30 |
| US20120238539A1 (en) | 2012-09-20 |
| DK2614052T3 (en) | 2015-04-07 |
| RS53844B1 (sr) | 2015-08-31 |
| EA201390362A1 (ru) | 2013-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160831 |
|
| FZDE | Discontinued |
Effective date: 20181219 |