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
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- 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 |
|---|---|---|---|
| CNPCT/CN2013/070976 | 2013-01-25 | ||
| CN2013070976 | 2013-01-25 | ||
| CN2013001556 | 2013-12-12 | ||
| CNPCT/CN2013/001556 | 2013-12-12 | ||
| 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 (cg-RX-API-DMAC7.html) | 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)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014209949B2 (en) | 2013-01-25 | 2016-09-08 | 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 |
| CN106536525B (zh) * | 2014-07-22 | 2019-05-03 | 葛兰素史密斯克莱知识产权发展有限公司 | 化合物 |
| 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 |
| 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 |
| IL292668A (en) * | 2019-11-09 | 2022-07-01 | Shanghai Simr Biotechnology Co Ltd | A tricyclic derivative of dihydroimidazopyrimidone, its preparation method, pharmaceutical preparation and its use |
| 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 |
| KR20250055539A (ko) * | 2022-08-04 | 2025-04-24 | 4비 테크놀로지스 (베이징) 컴퍼니 리미티드 | Lp-pla2 억제제로서의 디하이드로이미다조-피리미디논 화합물 및 이의 용도 |
| 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 (48)
| 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 |
| BR9510420A (pt) | 1994-12-22 | 2004-04-20 | Smithkline Beecham Plc | Azetidin-2-onas substituìdas para o tratamento de aterosclerose |
| 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 |
| 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 |
| IL126696A0 (en) | 1996-04-26 | 1999-08-17 | Smithkline Beecham Plc | Azetidinone derivatives for the treatment of atherosclerosis |
| GB9608649D0 (en) | 1996-04-26 | 1996-07-03 | Smithkline Beecham Plc | 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 |
| GB9626615D0 (en) | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| DE69816471T2 (de) | 1997-11-06 | 2004-05-27 | Smithkline Beecham P.L.C., Brentford | Pyrimidinon verbindungen und diese enthaltende pharmazeutische zusammenstellungen |
| EP1105377B1 (en) | 1998-08-21 | 2003-10-08 | SmithKline Beecham plc | Pyrimidinone derivatives for the treatment of atherosclerosis |
| GB9910079D0 (en) | 1999-05-01 | 1999-06-30 | Smithkline Beecham Plc | Novel compounds |
| WO2000066567A1 (en) | 1999-05-01 | 2000-11-09 | Smithkline Beecham Plc | Pyrimidinone compounds |
| 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 |
| PT1263740E (pt) | 2000-02-16 | 2006-11-30 | Smithkline Beecham Plc | Derivado de pirimidin-4- ona como inibidor de ldl-pla2 |
| GB0024808D0 (en) | 2000-10-10 | 2000-11-22 | Smithkline Beecham Plc | Novel compounds |
| GB0024807D0 (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 |
| GB0127139D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | 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 |
| 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 |
| CA2530816A1 (en) | 2003-07-02 | 2005-01-13 | Bayer Healthcare Ag | Amide-substituted 1,2,4-triazin-5(2h)-ones for the treatment of chronic inflammatory diseases |
| 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 |
| US20080090851A1 (en) | 2006-10-13 | 2008-04-17 | Colin Andrew Leach | Bicyclic Heteroaromatic Compounds |
| JP2010506852A (ja) | 2006-10-13 | 2010-03-04 | グラクソ グループ リミテッド | 二環式ヘテロ芳香族化合物 |
| 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 |
| WO2008104077A1 (en) | 2007-02-28 | 2008-09-04 | Methylgene Inc. | Small molecule inhibitors of protein arginine methyltransferases (prmts) |
| US8962633B2 (en) | 2007-05-11 | 2015-02-24 | Thomas Jefferson University | Methods of treatment and prevention of metabolic bone diseases and disorders |
| US9029383B2 (en) | 2007-05-11 | 2015-05-12 | 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 |
| EP2619203A4 (en) * | 2010-09-20 | 2014-04-16 | Glaxo Group Ltd | TRICYCLIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND APPLICATIONS THEREOF |
| EP2649050A4 (en) * | 2010-12-06 | 2014-04-23 | Glaxo Group Ltd | LINKS |
| JP2013545792A (ja) | 2010-12-17 | 2013-12-26 | グラクソ グループ リミテッド | 眼疾患の処置および防止方法 |
| JP2014521611A (ja) * | 2011-07-27 | 2014-08-28 | グラクソ グループ リミテッド | Ｌｐ−ＰＬＡ２阻害剤としての２，３−ジヒドロイミダゾ［１，２−ｃ］ピリミジン−５（１Ｈ）−オン化合物の使用 |
| CN103827116B (zh) * | 2011-07-27 | 2016-08-31 | 葛兰素集团有限公司 | 用作LP-PLA2抑制剂的2,3-二氢咪唑并[1,2-c]嘧啶-5(1H)-酮化合物 |
| AU2014209949B2 (en) | 2013-01-25 | 2016-09-08 | Glaxosmithkline Intellectual Property Development Limited | 2,3-dihydroimidazol(1,2-c)pyrimidin-5(1h)-one based lipoprotein-associated phospholipase a2 (Lp-PLA2) inhibitors |
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2014
- 2014-01-23 AU AU2014209949A patent/AU2014209949B2/en not_active Ceased
- 2014-01-23 ES ES14701355.1T patent/ES2642762T3/es active Active
- 2014-01-23 MA MA38284A patent/MA38284B1/fr unknown
- 2014-01-23 MX MX2015009633A patent/MX2015009633A/es unknown
- 2014-01-23 TW TW103102388A patent/TW201443054A/zh unknown
- 2014-01-23 CN CN201480013675.8A patent/CN105008368B/zh not_active Expired - Fee Related
- 2014-01-23 EA EA201591379A patent/EA025885B1/ru not_active IP Right Cessation
- 2014-01-23 EP EP14701355.1A patent/EP2948452B1/en active Active
- 2014-01-23 JP JP2015554138A patent/JP6306053B2/ja not_active Expired - Fee Related
- 2014-01-23 KR KR1020157022396A patent/KR20150108897A/ko not_active Ceased
- 2014-01-23 BR BR112015017759-0A patent/BR112015017759B1/pt not_active IP Right Cessation
- 2014-01-23 CA CA2899091A patent/CA2899091A1/en not_active Abandoned
- 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 UY UY0001035276A patent/UY35276A/es not_active Application Discontinuation
- 2014-01-23 US US14/761,636 patent/US9708330B2/en not_active Expired - Fee Related
- 2014-01-23 SG SG11201505520WA patent/SG11201505520WA/en unknown
- 2014-01-23 HK HK16104389.3A patent/HK1216425A1/zh unknown
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2015
- 2015-07-13 ZA ZA2015/05025A patent/ZA201505025B/en unknown
- 2015-07-20 PH PH12015501586A patent/PH12015501586A1/en unknown
- 2015-07-20 IL IL240046A patent/IL240046A0/en unknown
- 2015-07-23 CL CL2015002060A patent/CL2015002060A1/es unknown
- 2015-07-24 CR CR20150390A patent/CR20150390A/es unknown