JP2016505053A5 - - Google Patents
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- JP2016505053A5 JP2016505053A5 JP2015554039A JP2015554039A JP2016505053A5 JP 2016505053 A5 JP2016505053 A5 JP 2016505053A5 JP 2015554039 A JP2015554039 A JP 2015554039A JP 2015554039 A JP2015554039 A JP 2015554039A JP 2016505053 A5 JP2016505053 A5 JP 2016505053A5
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- JP
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- Prior art keywords
- title compound
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- prepared
- Prior art date
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- Pending
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- 150000001875 compounds Chemical class 0.000 description 9
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZPQJAHPDJSZNTL-UHFFFAOYSA-N methyl 3-fluoro-4-propan-2-yloxybenzoate Chemical compound COC(=O)C1=CC=C(OC(C)C)C(F)=C1 ZPQJAHPDJSZNTL-UHFFFAOYSA-N 0.000 description 3
- DWUCOQMNRGTMCC-MRVPVSSYSA-N (2r)-8-chloro-2-methyl-1-propan-2-yl-3,4-dihydro-2h-pyrimido[1,2-c]pyrimidin-6-one Chemical compound C([C@@H](C)N1C(C)C)CN2C1=CC(Cl)=NC2=O DWUCOQMNRGTMCC-MRVPVSSYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- SUHJJLDEYCLBFT-SSDOTTSWSA-N methyl (3r)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound COC(=O)C[C@@H](C)NC(=O)OC(C)(C)C SUHJJLDEYCLBFT-SSDOTTSWSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AGMZSYQMSHMXLT-SCSAIBSYSA-N (3r)-3-aminobutan-1-ol Chemical compound C[C@@H](N)CCO AGMZSYQMSHMXLT-SCSAIBSYSA-N 0.000 description 1
- WKMHXZZXRCWDRR-UHFFFAOYSA-N 2-(4-fluorophenoxy)-5-formylbenzonitrile Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=O)C=C1C#N WKMHXZZXRCWDRR-UHFFFAOYSA-N 0.000 description 1
- MOFRJTLODZILCR-UHFFFAOYSA-N 2-fluoro-5-formylbenzonitrile Chemical compound FC1=CC=C(C=O)C=C1C#N MOFRJTLODZILCR-UHFFFAOYSA-N 0.000 description 1
- RVAVWRRHYAUVKU-UHFFFAOYSA-N 3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 RVAVWRRHYAUVKU-UHFFFAOYSA-N 0.000 description 1
- YKPGJPZMQMHOBQ-UHFFFAOYSA-N 3,5-difluoro-4-[2-(trifluoromethyl)pyrimidin-5-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1OC1=CN=C(C(F)(F)F)N=C1 YKPGJPZMQMHOBQ-UHFFFAOYSA-N 0.000 description 1
- XTLJKHBPNDOAGE-UHFFFAOYSA-N 3-fluoro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C(F)=C1 XTLJKHBPNDOAGE-UHFFFAOYSA-N 0.000 description 1
- IUSDEKNMCOUBEE-UHFFFAOYSA-N 3-fluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(F)=C1 IUSDEKNMCOUBEE-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- AMIAYJANCJPAQD-UHFFFAOYSA-N 5-formyl-2-[6-(trifluoromethyl)pyridin-3-yl]oxybenzonitrile Chemical compound C1=NC(C(F)(F)F)=CC=C1OC1=CC=C(C=O)C=C1C#N AMIAYJANCJPAQD-UHFFFAOYSA-N 0.000 description 1
- VFOBDHYPESAMAF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridin-3-ol Chemical compound OC1=CC=C(C(F)(F)F)N=C1 VFOBDHYPESAMAF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- MQFCPCQSLYHJEX-UHFFFAOYSA-N methyl 4-cyclopentyloxy-3-fluorobenzoate Chemical compound FC1=CC(C(=O)OC)=CC=C1OC1CCCC1 MQFCPCQSLYHJEX-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013070977 | 2013-01-25 | ||
| CNPCT/CN2013/070977 | 2013-01-25 | ||
| PCT/CN2014/071206 WO2014114249A1 (en) | 2013-01-25 | 2014-01-23 | Bicyclic pyrimidone compounds as inhibitors of lp-pla2 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016505053A JP2016505053A (ja) | 2016-02-18 |
| JP2016505053A5 true JP2016505053A5 (enExample) | 2016-07-14 |
Family
ID=51226939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015554039A Pending JP2016505053A (ja) | 2013-01-25 | 2014-01-23 | Ｌｐ‐ＰＬＡ２の阻害剤としての二環式ピリミドン化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20150344485A1 (enExample) |
| EP (1) | EP2948456A4 (enExample) |
| JP (1) | JP2016505053A (enExample) |
| KR (1) | KR20150108896A (enExample) |
| AU (1) | AU2014210260B2 (enExample) |
| BR (1) | BR112015017397A2 (enExample) |
| CA (1) | CA2899143A1 (enExample) |
| RU (1) | RU2015135824A (enExample) |
| WO (1) | WO2014114249A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3172211B1 (en) * | 2014-07-22 | 2019-07-03 | GlaxoSmithKline Intellectual Property Development Limited | Tricyclic imidazo-pyrimidinone derivatives for the treatment of diseases mediated by lp-pla2 |
| CN105777653A (zh) | 2014-12-26 | 2016-07-20 | 中国科学院上海药物研究所 | 用作Lp-PLA2抑制剂的嘧啶酮类化合物及其药物组合物 |
| CN106188063A (zh) * | 2015-05-08 | 2016-12-07 | 中国科学院上海药物研究所 | 用作Lp-PLA2抑制剂的双环类化合物、其制备方法及医药用途 |
| CN105001098B (zh) * | 2015-07-26 | 2016-09-14 | 嵊州市油脂化工有限公司 | 一种3(r)/(s)-氨基-1-丁醇的制备方法 |
| EP4495030A3 (en) | 2018-06-08 | 2025-04-02 | Attabotics Inc. | Improved storage and retrieval systems |
| CN110683960A (zh) * | 2019-08-22 | 2020-01-14 | 台州达辰药业有限公司 | 一种（r）-3-氨基丁醇的合成方法 |
| CN112574221B (zh) * | 2019-09-30 | 2022-03-04 | 上海纽思克生物科技有限公司 | 四环嘧啶酮类化合物、其制备方法、其组合物和用途 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9421816D0 (en) | 1994-10-29 | 1994-12-14 | Smithkline Beecham Plc | Novel compounds |
| JPH11500415A (ja) | 1994-12-22 | 1999-01-12 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | アテローム性動脈硬化症治療用置換アゼチジン−２−オン |
| CH690264A5 (fr) | 1995-06-30 | 2000-06-30 | Symphar Sa | Dérivés aminophosphonates substitués, leur procédé de préparation et leur utilisation pour la préparation de compositions pharmaceutiques. |
| CA2225627A1 (en) | 1995-07-01 | 1997-01-23 | Deirdre Mary Bernadette Hickey | Azetidinone derivatives for the treatment of atherosclerosis |
| JP2002515728A (ja) | 1995-09-29 | 2002-05-28 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | 新規用途 |
| EP0869943A1 (en) | 1995-12-08 | 1998-10-14 | Smithkline Beecham Plc | Monocyclic beta-lactame derivatives for treatment of atherosclerosis |
| JP2000505063A (ja) | 1995-12-08 | 2000-04-25 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | アテローム性動脈硬化症の治療のためのアゼチジノン化合物 |
| GB9608649D0 (en) | 1996-04-26 | 1996-07-03 | Smithkline Beecham Plc | Novel compounds |
| IL126696A0 (en) | 1996-04-26 | 1999-08-17 | Smithkline Beecham Plc | Azetidinone derivatives for the treatment of atherosclerosis |
| GB9626616D0 (en) | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| GB9626615D0 (en) | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| GB9626536D0 (en) | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| JP2001522844A (ja) | 1997-11-06 | 2001-11-20 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ピリミジノン化合物およびそれを含有する医薬組成物 |
| JP2002523402A (ja) | 1998-08-21 | 2002-07-30 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | アテローム性動脈硬化症の治療用ピリミジノン |
| GB9910079D0 (en) | 1999-05-01 | 1999-06-30 | Smithkline Beecham Plc | Novel compounds |
| CZ20013904A3 (cs) | 1999-05-01 | 2002-04-17 | Smithkline Beecham Plc | Pyrimidinonové sloučeniny |
| GB9910378D0 (en) | 1999-05-05 | 1999-06-30 | Smithkline Beecham Plc | Novel compounds |
| JP3757703B2 (ja) | 1999-09-22 | 2006-03-22 | 凸版印刷株式会社 | 再封可能な開口維持部材付パウチ |
| HU229479B1 (en) | 2000-02-16 | 2014-01-28 | Glaxo Group Ltd | Pyrimidine-4-one derivatives |
| GB0024807D0 (en) | 2000-10-10 | 2000-11-22 | Smithkline Beecham Plc | Novel compounds |
| GB0024808D0 (en) | 2000-10-10 | 2000-11-22 | Smithkline Beecham Plc | Novel compounds |
| GB0119795D0 (en) | 2001-08-14 | 2001-10-03 | Smithkline Beecham Plc | Novel process |
| GB0119793D0 (en) | 2001-08-14 | 2001-10-03 | Smithkline Beecham Plc | Novel compounds |
| GB0127141D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham Plc | Novel compounds |
| GB0127140D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Novel compounds |
| GB0127143D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Novel compounds |
| GB0127139D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Novel compounds |
| GB0208279D0 (en) | 2002-04-10 | 2002-05-22 | Glaxo Group Ltd | Novel compounds |
| GB0208280D0 (en) * | 2002-04-10 | 2002-05-22 | Glaxo Group Ltd | Novel compounds |
| EP1644353A1 (de) | 2003-07-02 | 2006-04-12 | Bayer HealthCare AG | Amid-substituierte 1, 2, 4-triazin-5 (2h) - one zur behandlung von chronisch inflammatorischen krankheiten |
| DE102004061009A1 (de) | 2004-12-18 | 2006-06-22 | Bayer Healthcare Ag | Substituierte 1,2,4-Triazin-5(2H)-one |
| DE102004061008A1 (de) | 2004-12-18 | 2006-06-22 | Bayer Healthcare Ag | 3-Arylalkyl- und 3-Heteroarylalkyl-substituierte 1,2,4-Triazin-5(2H)-one |
| US7705005B2 (en) | 2006-10-13 | 2010-04-27 | Glaxo Group Limited | Bicyclic heteroaromatic compounds |
| US20080090852A1 (en) | 2006-10-13 | 2008-04-17 | Colin Andrew Leach | Bicyclic Heteroaromatic Compounds |
| WO2008048867A2 (en) | 2006-10-13 | 2008-04-24 | Glaxo Group Limited | Bicyclic heteroaromatic compounds |
| US20080090851A1 (en) | 2006-10-13 | 2008-04-17 | Colin Andrew Leach | Bicyclic Heteroaromatic Compounds |
| US8962633B2 (en) | 2007-05-11 | 2015-02-24 | Thomas Jefferson University | Methods of treatment and prevention of metabolic bone diseases and disorders |
| WO2008141176A1 (en) | 2007-05-11 | 2008-11-20 | The Trustees Of The University Of Pennsylvania | Methods of treatment of skin ulcers |
| US20080279846A1 (en) | 2007-05-11 | 2008-11-13 | Thomas Jefferson University | Methods of treatment and prevention of neurodegenerative diseases and disorders |
| JP2011088847A (ja) * | 2009-10-21 | 2011-05-06 | Takeda Chem Ind Ltd | 三環性化合物およびその用途 |
| WO2012037782A1 (en) * | 2010-09-20 | 2012-03-29 | Glaxo Group Limited | Tricyclic compounds, preparation methods, and their uses |
| US8859573B2 (en) * | 2010-12-06 | 2014-10-14 | Glaxo Group Limited | Pyrimidinone and pyridinone compounds for use in the treatment of diseases or conditions mediated by Lp-PLA2 |
| EP2651403B1 (en) | 2010-12-17 | 2020-12-02 | Glaxo Group Limited | Use of lp-pla2 inhibitors in the treatment and prevention of eye diseases |
| EP2736908A1 (en) * | 2011-07-27 | 2014-06-04 | Glaxo Group Limited | Bicyclic pyrimidone compounds |
-
2014
- 2014-01-23 AU AU2014210260A patent/AU2014210260B2/en not_active Ceased
- 2014-01-23 BR BR112015017397A patent/BR112015017397A2/pt not_active IP Right Cessation
- 2014-01-23 WO PCT/CN2014/071206 patent/WO2014114249A1/en not_active Ceased
- 2014-01-23 CA CA2899143A patent/CA2899143A1/en not_active Abandoned
- 2014-01-23 KR KR1020157022394A patent/KR20150108896A/ko not_active Withdrawn
- 2014-01-23 RU RU2015135824A patent/RU2015135824A/ru not_active Application Discontinuation
- 2014-01-23 EP EP14743086.2A patent/EP2948456A4/en not_active Withdrawn
- 2014-01-23 US US14/761,631 patent/US20150344485A1/en not_active Abandoned
- 2014-01-23 JP JP2015554039A patent/JP2016505053A/ja active Pending
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