JP2016505058A5 - - Google Patents
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- Publication number
- JP2016505058A5 JP2016505058A5 JP2015554138A JP2015554138A JP2016505058A5 JP 2016505058 A5 JP2016505058 A5 JP 2016505058A5 JP 2015554138 A JP2015554138 A JP 2015554138A JP 2015554138 A JP2015554138 A JP 2015554138A JP 2016505058 A5 JP2016505058 A5 JP 2016505058A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- formula
- acceptable salt
- halo
- 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 description 19
- 239000000203 mixture Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- SRUMDQQNHCQNPK-UHFFFAOYSA-N 3-fluoro-4-(2-fluoropyridin-4-yl)oxybenzaldehyde Chemical compound C1=NC(F)=CC(OC=2C(=CC(C=O)=CC=2)F)=C1 SRUMDQQNHCQNPK-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BRLSDLHMGRDAPF-UHFFFAOYSA-N 2-fluoro-1h-pyridin-4-one Chemical compound FC1=CC(=O)C=CN1 BRLSDLHMGRDAPF-UHFFFAOYSA-N 0.000 description 1
- JPHKMYXKNKLNDF-UHFFFAOYSA-N 3,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1F JPHKMYXKNKLNDF-UHFFFAOYSA-N 0.000 description 1
- UXWXSKWBTIWJBS-UHFFFAOYSA-N 3-fluoro-4-[3-fluoro-5-(trifluoromethyl)phenoxy]benzaldehyde Chemical compound FC(F)(F)C1=CC(F)=CC(OC=2C(=CC(C=O)=CC=2)F)=C1 UXWXSKWBTIWJBS-UHFFFAOYSA-N 0.000 description 1
- YHLZLQSMYFVIPE-BFWBPSQCSA-N 7-chloro-3,3-dideuterio-1,2,2-trimethylimidazo[1,2-c]pyrimidin-5-one Chemical compound CN1C(C)(C)C([2H])([2H])N2C1=CC(Cl)=NC2=O YHLZLQSMYFVIPE-BFWBPSQCSA-N 0.000 description 1
- OYQQBKFKXHCTNG-UHFFFAOYSA-N [3-fluoro-4-(2-fluoropyridin-4-yl)oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=NC(F)=C1 OYQQBKFKXHCTNG-UHFFFAOYSA-N 0.000 description 1
- ASBHBYHIPVMRNJ-UHFFFAOYSA-N [3-fluoro-4-[3-fluoro-5-(trifluoromethyl)phenoxy]phenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC(F)=CC(C(F)(F)F)=C1 ASBHBYHIPVMRNJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013070976 | 2013-01-25 | ||
| CNPCT/CN2013/070976 | 2013-01-25 | ||
| CN2013001556 | 2013-12-12 | ||
| CNPCT/CN2013/001556 | 2013-12-21 | ||
| PCT/EP2014/051286 WO2014114694A1 (en) | 2013-01-25 | 2014-01-23 | 2,3-dihydroimidazol[1,2-c]pyrimidin-5(1h)-one based lipoprotein-associated phospholipase a2 (lp-pla2) inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016505058A JP2016505058A (ja) | 2016-02-18 |
| JP2016505058A5 true JP2016505058A5 (enExample) | 2017-02-23 |
| JP6306053B2 JP6306053B2 (ja) | 2018-04-04 |
Family
ID=50002724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015554138A Expired - Fee Related JP6306053B2 (ja) | 2013-01-25 | 2014-01-23 | ２，３−ジヒドロイミダゾール［１，２−ｃ］ピリミジン−５（１Ｈ）−オンに基づくリポタンパク質関連ホスホリパーゼＡ２（Ｌｐ−ＰＬＡ２）阻害剤 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9708330B2 (enExample) |
| EP (1) | EP2948452B1 (enExample) |
| JP (1) | JP6306053B2 (enExample) |
| KR (1) | KR20150108897A (enExample) |
| CN (1) | CN105008368B (enExample) |
| AU (1) | AU2014209949B2 (enExample) |
| BR (1) | BR112015017759B1 (enExample) |
| CA (1) | CA2899091A1 (enExample) |
| CL (1) | CL2015002060A1 (enExample) |
| CR (1) | CR20150390A (enExample) |
| EA (1) | EA025885B1 (enExample) |
| ES (1) | ES2642762T3 (enExample) |
| HK (1) | HK1216425A1 (enExample) |
| IL (1) | IL240046A0 (enExample) |
| MA (1) | MA38284B1 (enExample) |
| MX (1) | MX2015009633A (enExample) |
| PE (1) | PE20151251A1 (enExample) |
| PH (1) | PH12015501586A1 (enExample) |
| SG (1) | SG11201505520WA (enExample) |
| TW (1) | TW201443054A (enExample) |
| UY (1) | UY35276A (enExample) |
| WO (1) | WO2014114694A1 (enExample) |
| ZA (1) | ZA201505025B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014114694A1 (en) | 2013-01-25 | 2014-07-31 | Glaxosmithkline Intellectual Property Development Limited | 2,3-dihydroimidazol[1,2-c]pyrimidin-5(1h)-one based lipoprotein-associated phospholipase a2 (lp-pla2) inhibitors |
| WO2016012917A1 (en) * | 2014-07-22 | 2016-01-28 | Glaxosmithkline Intellectual Property Development Limited | 1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2 |
| WO2016012916A1 (en) * | 2014-07-22 | 2016-01-28 | Glaxosmithkline Intellectual Property Development Limited | 1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidine derivatives useful in the treatment of diseases and disorders mediated by lp-pla2 |
| 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 |
| CN104892459A (zh) * | 2015-06-16 | 2015-09-09 | 苏州明锐医药科技有限公司 | 利奥西呱中间体及其制备方法 |
| 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 |
| CN114805389B (zh) * | 2019-11-09 | 2023-08-29 | 上海赛默罗生物科技有限公司 | 三环二氢咪唑并嘧啶酮衍生物、其制备方法、药物组合物和用途 |
| CN111533699B (zh) * | 2020-05-27 | 2023-12-01 | 龙曦宁（上海）医药科技有限公司 | 一种2-（三氟甲基）嘧啶-5-醇的合成方法 |
| CN113861220B (zh) * | 2020-06-30 | 2023-06-16 | 上海纽思克生物科技有限公司 | 三环嘧啶酮类化合物、其制备方法、其组合物和用途 |
| CN113912622B (zh) | 2020-07-10 | 2023-12-01 | 上海纽思克生物科技有限公司 | 三环嘧啶酮类化合物、其制备方法、其组合物和用途 |
| CN115304620A (zh) | 2021-05-07 | 2022-11-08 | 上海赛默罗生物科技有限公司 | 嘧啶酮衍生物、其制备方法、药物组合物和用途 |
| CN114057740B (zh) * | 2021-12-15 | 2024-04-02 | 上海赛默罗生物科技有限公司 | 螺环嘧啶酮衍生物、其制备方法、药物组合物和用途 |
| JP2025527291A (ja) * | 2022-08-04 | 2025-08-20 | ４ビー テクノロジーズ （ベイジン） カンパニー リミテッド | Ｌｐ－ＰＬＡ２阻害剤としてのジヒドロイミダゾピリミジノン化合物およびその使用 |
| CN118221687B (zh) | 2023-07-17 | 2024-12-31 | 上海枢境生物科技有限公司 | 双环[5,6]咪唑嘧啶酮类衍生物、其制备方法和应用 |
| CN116925023B (zh) * | 2023-07-18 | 2025-11-21 | 江苏桐孚高新材料有限公司 | 2-全氟烷基-4h-吡喃-4-酮衍生物的改进合成方法 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993018035A1 (en) | 1992-03-04 | 1993-09-16 | Abbott Laboratories | Angiotensin ii receptor antagonists |
| GB9421816D0 (en) | 1994-10-29 | 1994-12-14 | Smithkline Beecham Plc | Novel compounds |
| WO1996019451A1 (en) | 1994-12-22 | 1996-06-27 | Smithkline Beecham Plc | Substituted azetidin-2-ones for treatment of atherosclerosis |
| 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. |
| HUP9901153A3 (en) | 1995-07-01 | 1999-11-29 | Smithkline Beecham Plc | Azetidinone derivatives for the treatment of atherosclerosis, their production and pharmaceutical compositions containing them |
| WO1997012963A2 (en) | 1995-09-29 | 1997-04-10 | Smithkline Beecham Plc | A paf-acetylhydrolase and use in therapy |
| EP0869943A1 (en) | 1995-12-08 | 1998-10-14 | Smithkline Beecham Plc | Monocyclic beta-lactame derivatives for treatment of atherosclerosis |
| EP0865429A1 (en) | 1995-12-08 | 1998-09-23 | Smithkline Beecham Plc | Azetidinone compounds for the treatment of atherosclerosis |
| CZ341098A3 (cs) | 1996-04-26 | 1999-03-17 | Smithkline Beecham Plc | Azetidinonové deriváty pro ošetřování aterosklerózy |
| GB9608649D0 (en) | 1996-04-26 | 1996-07-03 | Smithkline Beecham Plc | 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 |
| GB9626616D0 (en) | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| WO1999024420A1 (en) | 1997-11-06 | 1999-05-20 | Smithkline Beecham Plc | Pyrimidinone compounds and pharmaceutical compositions containing them |
| DE69911980T2 (de) | 1998-08-21 | 2004-09-09 | Smithkline Beecham P.L.C., Brentford | Pyrimidinonderivate zur behandlung von atheroscleros |
| GB9910079D0 (en) | 1999-05-01 | 1999-06-30 | Smithkline Beecham Plc | Novel compounds |
| DE60042286D1 (de) | 1999-05-01 | 2009-07-09 | Smithkline Beecham Plc | Pyrimidinon Verbindungen |
| 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 |
| DE60139429D1 (de) | 2000-02-16 | 2009-09-10 | Smithkline Beecham Plc | Pyrimidin-5-Onderivate als LDL-PLA2 Inhibitoren |
| 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 |
| GB0119793D0 (en) | 2001-08-14 | 2001-10-03 | Smithkline Beecham Plc | Novel compounds |
| GB0119795D0 (en) | 2001-08-14 | 2001-10-03 | Smithkline Beecham Plc | Novel process |
| GB0127143D0 (en) * | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Novel compounds |
| GB0127141D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham Plc | Novel compounds |
| GB0127139D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Novel compounds |
| GB0127140D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Novel compounds |
| GB0208280D0 (en) | 2002-04-10 | 2002-05-22 | Glaxo Group Ltd | Novel compounds |
| GB0208279D0 (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 |
| DE102004061008A1 (de) | 2004-12-18 | 2006-06-22 | Bayer Healthcare Ag | 3-Arylalkyl- und 3-Heteroarylalkyl-substituierte 1,2,4-Triazin-5(2H)-one |
| DE102004061009A1 (de) | 2004-12-18 | 2006-06-22 | Bayer Healthcare Ag | Substituierte 1,2,4-Triazin-5(2H)-one |
| US20080090852A1 (en) | 2006-10-13 | 2008-04-17 | Colin Andrew Leach | Bicyclic Heteroaromatic Compounds |
| US7705005B2 (en) | 2006-10-13 | 2010-04-27 | Glaxo Group Limited | 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 |
| US8338437B2 (en) | 2007-02-28 | 2012-12-25 | Methylgene Inc. | Amines as small molecule inhibitors |
| US20080279846A1 (en) | 2007-05-11 | 2008-11-13 | Thomas Jefferson University | Methods of treatment and prevention of neurodegenerative diseases and disorders |
| US9029383B2 (en) | 2007-05-11 | 2015-05-12 | The Trustees Of The University Of Pennsylvania | Methods of treatment of skin ulcers |
| US8962633B2 (en) | 2007-05-11 | 2015-02-24 | Thomas Jefferson University | Methods of treatment and prevention of metabolic bone 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 |
| EP2619203A4 (en) * | 2010-09-20 | 2014-04-16 | Glaxo Group Ltd | TRICYCLIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND APPLICATIONS THEREOF |
| WO2012075917A1 (en) * | 2010-12-06 | 2012-06-14 | Glaxo Group Limited | Compounds |
| EP2651403B1 (en) | 2010-12-17 | 2020-12-02 | Glaxo Group Limited | Use of lp-pla2 inhibitors in the treatment and prevention of eye diseases |
| EP2739627A4 (en) * | 2011-07-27 | 2015-01-21 | Glaxo Group Ltd | 2,3-DIHYDROIMIDAZO- [1,2-C-] PYRIMIDIN-5 (1H) -ONE COMPOUNDS AS LP-PLA² INHIBITORS |
| WO2014114694A1 (en) | 2013-01-25 | 2014-07-31 | Glaxosmithkline Intellectual Property Development Limited | 2,3-dihydroimidazol[1,2-c]pyrimidin-5(1h)-one based lipoprotein-associated phospholipase a2 (lp-pla2) inhibitors |
-
2014
- 2014-01-23 WO PCT/EP2014/051286 patent/WO2014114694A1/en not_active Ceased
- 2014-01-23 PE PE2015001537A patent/PE20151251A1/es not_active Application Discontinuation
- 2014-01-23 CN CN201480013675.8A patent/CN105008368B/zh not_active Expired - Fee Related
- 2014-01-23 ES ES14701355.1T patent/ES2642762T3/es active Active
- 2014-01-23 EA EA201591379A patent/EA025885B1/ru not_active IP Right Cessation
- 2014-01-23 HK HK16104389.3A patent/HK1216425A1/zh unknown
- 2014-01-23 MA MA38284A patent/MA38284B1/fr unknown
- 2014-01-23 US US14/761,636 patent/US9708330B2/en not_active Expired - Fee Related
- 2014-01-23 TW TW103102388A patent/TW201443054A/zh unknown
- 2014-01-23 BR BR112015017759-0A patent/BR112015017759B1/pt not_active IP Right Cessation
- 2014-01-23 UY UY0001035276A patent/UY35276A/es not_active Application Discontinuation
- 2014-01-23 CA CA2899091A patent/CA2899091A1/en not_active Abandoned
- 2014-01-23 KR KR1020157022396A patent/KR20150108897A/ko not_active Ceased
- 2014-01-23 SG SG11201505520WA patent/SG11201505520WA/en unknown
- 2014-01-23 JP JP2015554138A patent/JP6306053B2/ja not_active Expired - Fee Related
- 2014-01-23 AU AU2014209949A patent/AU2014209949B2/en not_active Ceased
- 2014-01-23 EP EP14701355.1A patent/EP2948452B1/en active Active
- 2014-01-23 MX MX2015009633A patent/MX2015009633A/es unknown
-
2015
- 2015-07-13 ZA ZA2015/05025A patent/ZA201505025B/en unknown
- 2015-07-20 IL IL240046A patent/IL240046A0/en unknown
- 2015-07-20 PH PH12015501586A patent/PH12015501586A1/en unknown
- 2015-07-23 CL CL2015002060A patent/CL2015002060A1/es unknown
- 2015-07-24 CR CR20150390A patent/CR20150390A/es unknown
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