JP2013537193A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013537193A5 JP2013537193A5 JP2013528244A JP2013528244A JP2013537193A5 JP 2013537193 A5 JP2013537193 A5 JP 2013537193A5 JP 2013528244 A JP2013528244 A JP 2013528244A JP 2013528244 A JP2013528244 A JP 2013528244A JP 2013537193 A5 JP2013537193 A5 JP 2013537193A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- alkyl
- group
- compound
- hydroxyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 8
- -1 cyano, hydroxyl Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 241000712461 unidentified influenza virus Species 0.000 claims 1
- 0 C[n]1nnc(-c(cccc2)c2OC)c1C(NCCNc(cc(c([N+]([O-])=O)c1)NC(c2ccc(*3CCC3)cc2)=O)c1Cl)=O Chemical compound C[n]1nnc(-c(cccc2)c2OC)c1C(NCCNc(cc(c([N+]([O-])=O)c1)NC(c2ccc(*3CCC3)cc2)=O)c1Cl)=O 0.000 description 72
- VGEREXVLSOWWIE-UHFFFAOYSA-N CC(Nc(cc1)ccc1C(Nc1cc(N(CC2)CCN2C(c2c(C)[o]nc2-c(cccc2)c2OC)=O)c(C)cc1[N+]([O-])=O)=O)=O Chemical compound CC(Nc(cc1)ccc1C(Nc1cc(N(CC2)CCN2C(c2c(C)[o]nc2-c(cccc2)c2OC)=O)c(C)cc1[N+]([O-])=O)=O)=O VGEREXVLSOWWIE-UHFFFAOYSA-N 0.000 description 1
- UNNVLFRKYZSWPV-UHFFFAOYSA-N Cc(cc(c(NC(c(cc1)ccc1N(C)C)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O Chemical compound Cc(cc(c(NC(c(cc1)ccc1N(C)C)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O UNNVLFRKYZSWPV-UHFFFAOYSA-N 0.000 description 1
- MTJFIUNLHHSSIY-UHFFFAOYSA-N Cc(cc(c(NC(c(cc1)ccc1N(CCC1)C1=O)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O Chemical compound Cc(cc(c(NC(c(cc1)ccc1N(CCC1)C1=O)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O MTJFIUNLHHSSIY-UHFFFAOYSA-N 0.000 description 1
- XJBHNNZZXKRONZ-UHFFFAOYSA-N Cc(cc(c(NC(c(cc1)ccc1N(CCC1)S1(=O)=O)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O Chemical compound Cc(cc(c(NC(c(cc1)ccc1N(CCC1)S1(=O)=O)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O XJBHNNZZXKRONZ-UHFFFAOYSA-N 0.000 description 1
- KVGJTIMAOSGCHG-UHFFFAOYSA-N Cc(cc(c(NC(c(cc1)ccc1N(CCO1)C1=O)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O Chemical compound Cc(cc(c(NC(c(cc1)ccc1N(CCO1)C1=O)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O KVGJTIMAOSGCHG-UHFFFAOYSA-N 0.000 description 1
- MJJABHHFAIFYQT-UHFFFAOYSA-N Cc(cc(c(NC(c(cc1)ccc1OC)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O Chemical compound Cc(cc(c(NC(c(cc1)ccc1OC)=O)c1)[N+]([O-])=O)c1N(CC1)CCN1C(c1c(-c(cccc2)c2OC)nn[n]1C)=O MJJABHHFAIFYQT-UHFFFAOYSA-N 0.000 description 1
- OILDCXJRWPGBFE-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc(c([N+]([O-])=O)c2)NC(c(cc3)ccc3N(C)C)=O)c2C#N)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc(c([N+]([O-])=O)c2)NC(c(cc3)ccc3N(C)C)=O)c2C#N)=O)c(-c(cccc2)c2OC)n[o]1 OILDCXJRWPGBFE-UHFFFAOYSA-N 0.000 description 1
- MQZMJVZJYAWKGF-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc(c([NH+]([O-])[O-])c2)NC(c(cc3)ccc3N(C)C)O)c2Cl)=O)c(-c(cccc2)c2O)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc(c([NH+]([O-])[O-])c2)NC(c(cc3)ccc3N(C)C)O)c2Cl)=O)c(-c(cccc2)c2O)n[o]1 MQZMJVZJYAWKGF-UHFFFAOYSA-N 0.000 description 1
- LHTCGVCBLXPNCG-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3-[n]3nnnc3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3-[n]3nnnc3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 LHTCGVCBLXPNCG-UHFFFAOYSA-N 0.000 description 1
- DWWWGTCAGXYYPH-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(C)C)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(C)C)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 DWWWGTCAGXYYPH-UHFFFAOYSA-N 0.000 description 1
- PVBVVOSVHKXARW-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(C)C)=O)c(C)cc2[NH+]([O-])[O-])=O)c(-c(cccc2)c2O)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(C)C)=O)c(C)cc2[NH+]([O-])[O-])=O)c(-c(cccc2)c2O)n[o]1 PVBVVOSVHKXARW-UHFFFAOYSA-N 0.000 description 1
- QBJHUQKEQWWJQJ-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(C)S(C)(=O)=O)=O)c(C)cc2N([O-])OC)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(C)S(C)(=O)=O)=O)c(C)cc2N([O-])OC)=O)c(-c(cccc2)c2OC)n[o]1 QBJHUQKEQWWJQJ-UHFFFAOYSA-N 0.000 description 1
- QVNRIHHIGMJZLA-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(CCC3)C3=O)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N(CCC3)C3=O)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 QVNRIHHIGMJZLA-UHFFFAOYSA-N 0.000 description 1
- RAVVJIWLFORYIH-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N3CCCC3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3)ccc3N3CCCC3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 RAVVJIWLFORYIH-UHFFFAOYSA-N 0.000 description 1
- SONFFHAFWUKHSZ-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3F)ccc3N3CCC3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c(cc3F)ccc3N3CCC3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 SONFFHAFWUKHSZ-UHFFFAOYSA-N 0.000 description 1
- RZLKJOKSYFKFPD-UHFFFAOYSA-N Cc1c(C(N(CC2)CCN2c(cc2NC(c3ccc(CN(C)C)cc3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(N(CC2)CCN2c(cc2NC(c3ccc(CN(C)C)cc3)=O)c(C)cc2[N+]([O-])=O)=O)c(-c(cccc2)c2OC)n[o]1 RZLKJOKSYFKFPD-UHFFFAOYSA-N 0.000 description 1
- ZTZZZLHBBZEQHC-UHFFFAOYSA-N Cc1c(C(NCCNc(c(Cl)c2)cc(NC(c(cc3)ccc3N(C)C)=O)c2[N+]2([O-])[O-]C2)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(NCCNc(c(Cl)c2)cc(NC(c(cc3)ccc3N(C)C)=O)c2[N+]2([O-])[O-]C2)=O)c(-c(cccc2)c2OC)n[o]1 ZTZZZLHBBZEQHC-UHFFFAOYSA-N 0.000 description 1
- MGXPDHSTFZGLFB-UHFFFAOYSA-N Cc1c(C(NCCNc(cc(c([N+]([O-])=O)c2)NC(c(cc3)ccc3-[n]3ncnc3)=O)c2Cl)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(NCCNc(cc(c([N+]([O-])=O)c2)NC(c(cc3)ccc3-[n]3ncnc3)=O)c2Cl)=O)c(-c(cccc2)c2OC)n[o]1 MGXPDHSTFZGLFB-UHFFFAOYSA-N 0.000 description 1
- BNTAQYLHXSIKMV-UHFFFAOYSA-N Cc1c(C(NCCNc(cc(c([NH+]([O-])O)c2)NC(c(cc3)ccc3N(C)C)=O)c2C#N)=O)c(-c(cccc2)c2OC)n[o]1 Chemical compound Cc1c(C(NCCNc(cc(c([NH+]([O-])O)c2)NC(c(cc3)ccc3N(C)C)=O)c2C#N)=O)c(-c(cccc2)c2OC)n[o]1 BNTAQYLHXSIKMV-UHFFFAOYSA-N 0.000 description 1
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2013537193A JP2013537193A (ja) | 2013-09-30 |
| JP2013537193A5 true JP2013537193A5 (enExample) | 2014-10-23 |
| JP5902172B2 JP5902172B2 (ja) | 2016-04-13 |
Family
ID=44653573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013528244A Expired - Fee Related JP5902172B2 (ja) | 2010-09-08 | 2011-09-06 | 広範囲のインフルエンザ抗ウイルス薬としての新規ピペラジン類似体 |
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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
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