JP2016523908A5 - - Google Patents
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- Publication number
- JP2016523908A5 JP2016523908A5 JP2016523870A JP2016523870A JP2016523908A5 JP 2016523908 A5 JP2016523908 A5 JP 2016523908A5 JP 2016523870 A JP2016523870 A JP 2016523870A JP 2016523870 A JP2016523870 A JP 2016523870A JP 2016523908 A5 JP2016523908 A5 JP 2016523908A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- dioxo
- carbazole
- methylphenyl
- fluoro
- 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
- 150000003839 salts Chemical class 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- -1 3- (6-Fluoro-1-methyl-2,4-dioxo-1,2-dihydroquinazoline-3 (4H) -Yl) -2-methylphenyl Chemical group 0.000 claims 4
- BPINSDADQGFXNS-UHFFFAOYSA-N 4-[2-chloro-3-(1-methyl-2,4-dioxoquinazolin-3-yl)phenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(Cl)C(N2C(=O)C3=CC=CC=C3N(C2=O)C)=CC=C1 BPINSDADQGFXNS-UHFFFAOYSA-N 0.000 claims 2
- IWVCATOVLJOXMB-UHFFFAOYSA-N 4-[3-(4-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=CC3=C(F)C2=O)=O)=CC=C1 IWVCATOVLJOXMB-UHFFFAOYSA-N 0.000 claims 2
- RXHAROKPHMWUME-UHFFFAOYSA-N 4-[3-(5-chloro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=C(Cl)C3=CC2=O)=O)=CC=C1 RXHAROKPHMWUME-UHFFFAOYSA-N 0.000 claims 2
- RNLHORWOBQSYJE-UHFFFAOYSA-N 4-[3-(5-chloro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(methoxymethyl)-9h-carbazole-1-carboxamide Chemical compound O=C1C=C2C(Cl)=CC=CN2C(=O)N1C1=C(C)C(C=2C=CC(=C3NC=4C(C=23)=CC=C(C=4)COC)C(N)=O)=CC=C1 RNLHORWOBQSYJE-UHFFFAOYSA-N 0.000 claims 2
- BEKXRKQECXXKGJ-UHFFFAOYSA-N 4-[3-(5-chloro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(pyrrolidin-1-ylmethyl)-9h-carbazole-1-carboxamide Chemical compound C1=CC=C(N2C(N3C=CC=C(Cl)C3=CC2=O)=O)C(C)=C1C(C=1C2=CC=3)=CC=C(C(N)=O)C=1NC2=CC=3CN1CCCC1 BEKXRKQECXXKGJ-UHFFFAOYSA-N 0.000 claims 2
- AXNKUCHUGAZVMO-UHFFFAOYSA-N 4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=C(F)C3=CC2=O)=O)=CC=C1 AXNKUCHUGAZVMO-UHFFFAOYSA-N 0.000 claims 2
- JPJRIRSPLLYPRY-UHFFFAOYSA-N 4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(hydroxymethyl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(CO)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=C(F)C3=CC2=O)=O)=CC=C1 JPJRIRSPLLYPRY-UHFFFAOYSA-N 0.000 claims 2
- VIRRHNLXPOCKII-UHFFFAOYSA-N 4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(methoxymethyl)-9h-carbazole-1-carboxamide Chemical compound O=C1C=C2C(F)=CC=CN2C(=O)N1C1=C(C)C(C=2C=CC(=C3NC=4C(C=23)=CC=C(C=4)COC)C(N)=O)=CC=C1 VIRRHNLXPOCKII-UHFFFAOYSA-N 0.000 claims 2
- OPCHAIUSSHIEQR-UHFFFAOYSA-N 4-[3-[3-(4-fluorophenyl)-2,6-dioxopyrimidin-1-yl]-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound CC1=C(C=2C=3C4=CC=C(C=C4NC=3C(C(N)=O)=CC=2)C(C)(C)O)C=CC=C1N(C1=O)C(=O)C=CN1C1=CC=C(F)C=C1 OPCHAIUSSHIEQR-UHFFFAOYSA-N 0.000 claims 2
- HPPFVYVYCRLUIG-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(6-methoxy-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(=O)C=C3N(C2=O)C=CC(=C3)OC)=CC=C1 HPPFVYVYCRLUIG-UHFFFAOYSA-N 0.000 claims 2
- HMFXPCSTCHRNIX-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(7-methoxy-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(=O)C=C3C=CC(=CN3C2=O)OC)=CC=C1 HMFXPCSTCHRNIX-UHFFFAOYSA-N 0.000 claims 2
- RAGWYGVSFHQCQZ-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(8-methoxy-1-methyl-2,4-dioxoquinazolin-3-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(=O)N(C)C3=C(C2=O)C=CC=C3OC)=CC=C1 RAGWYGVSFHQCQZ-UHFFFAOYSA-N 0.000 claims 2
- YPILWBQSRHPXDB-UHFFFAOYSA-N 7-(acetamidomethyl)-4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound O=C1C=C2C(F)=CC=CN2C(=O)N1C1=C(C)C(C=2C=CC(=C3NC=4C(C=23)=CC=C(C=4)CNC(=O)C)C(N)=O)=CC=C1 YPILWBQSRHPXDB-UHFFFAOYSA-N 0.000 claims 2
- IPQVQJPUHHTPSI-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound O=C1C=C2C(F)=CC=CN2C(=O)N1C1=C(C)C(C=2C=CC(=C3NC=4C(C=23)=CC=C(C=4)N(C)C)C(N)=O)=CC=C1 IPQVQJPUHHTPSI-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- YMWYOJJLYOKDOF-UHFFFAOYSA-N 4-[3-(8-fluoro-2,4-dioxo-1h-quinazolin-3-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(C3=CC=CC(F)=C3NC2=O)=O)=CC=C1 YMWYOJJLYOKDOF-UHFFFAOYSA-N 0.000 claims 1
- LTRXOULEFZSBFQ-UHFFFAOYSA-N 5-fluoropyrido[1,2-c]pyrimidine-1,3-dione Chemical compound FC1=CC=CN2C(NC(C=C21)=O)=O LTRXOULEFZSBFQ-UHFFFAOYSA-N 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 0 CN(C(c(cccc1)c1N1*)=O)C1=O Chemical compound CN(C(c(cccc1)c1N1*)=O)C1=O 0.000 description 3
- NMSIVYJYWHQYNP-UHFFFAOYSA-N CN(C(C=C1SC=CN11)=O)C1=O Chemical compound CN(C(C=C1SC=CN11)=O)C1=O NMSIVYJYWHQYNP-UHFFFAOYSA-N 0.000 description 1
- OKJBDIUGZAWYAE-UHFFFAOYSA-N CN(C(C=CN1c(cc2)ccc2F)=O)C1=O Chemical compound CN(C(C=CN1c(cc2)ccc2F)=O)C1=O OKJBDIUGZAWYAE-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361839130P | 2013-06-25 | 2013-06-25 | |
| US61/839,130 | 2013-06-25 | ||
| PCT/US2014/043980 WO2014210087A1 (en) | 2013-06-25 | 2014-06-25 | Carbazole carboxamide compounds useful as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016523908A JP2016523908A (ja) | 2016-08-12 |
| JP2016523908A5 true JP2016523908A5 (enExample) | 2017-07-06 |
| JP6353530B2 JP6353530B2 (ja) | 2018-07-04 |
Family
ID=51210832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016523870A Expired - Fee Related JP6353530B2 (ja) | 2013-06-25 | 2014-06-25 | キナーゼ阻害剤として有用なカルバゾールカルボキサミド化合物 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9714234B2 (enExample) |
| EP (1) | EP3013815B1 (enExample) |
| JP (1) | JP6353530B2 (enExample) |
| KR (1) | KR102345381B1 (enExample) |
| CN (1) | CN105473573B (enExample) |
| AU (1) | AU2014302550A1 (enExample) |
| BR (1) | BR112015031432A2 (enExample) |
| CA (1) | CA2916504A1 (enExample) |
| EA (1) | EA025863B1 (enExample) |
| IL (1) | IL243295A0 (enExample) |
| MX (1) | MX2015016771A (enExample) |
| SG (1) | SG11201510028PA (enExample) |
| WO (1) | WO2014210087A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT3209651T (lt) * | 2014-10-24 | 2020-01-10 | Bristol-Myers Squibb Company | Karbazolo dariniai |
| LT3461821T (lt) | 2014-10-24 | 2020-08-10 | Bristol-Myers Squibb Company | Indolo karboksamido junginiai, naudotini kaip kinazės inhibitoriai |
| AU2015335783B2 (en) | 2014-10-24 | 2019-10-03 | Bristol-Myers Squibb Company | Tricyclic atropisomer compounds |
| CN105802100A (zh) * | 2016-04-22 | 2016-07-27 | 宁波硫华聚合物有限公司 | 橡胶促进剂粘合剂六甲氧基甲基蜜胺预分散母胶粒及其制备方法 |
| CN105670057A (zh) * | 2016-04-25 | 2016-06-15 | 无锡智谷锐拓技术服务有限公司 | 一种耐油橡胶的制备方法 |
| CN105694150A (zh) * | 2016-04-25 | 2016-06-22 | 无锡智谷锐拓技术服务有限公司 | 一种耐油橡胶 |
| CN106084903A (zh) * | 2016-06-02 | 2016-11-09 | 扬州兰都塑料科技有限公司 | 一种电缆外部涂覆的水性防火涂料的制备方法 |
| CN105907150A (zh) * | 2016-06-02 | 2016-08-31 | 扬州兰都塑料科技有限公司 | 一种电缆涂料用阻燃剂 |
| CN106045972B (zh) * | 2016-06-03 | 2018-11-16 | 中山大学 | 咔唑-利凡斯的明二联体及其药物组合物和应用 |
| WO2021158498A1 (en) | 2020-02-03 | 2021-08-12 | Bristol-Myers Squibb Company | Tricyclic heteroaryl compounds useful as irak4 inhibitors |
| WO2022140246A1 (en) | 2020-12-21 | 2022-06-30 | Hangzhou Jijing Pharmaceutical Technology Limited | Methods and compounds for targeted autophagy |
| CN115232061B (zh) * | 2021-09-18 | 2024-01-30 | 山西紫罗蓝新材料科技有限公司 | 一种3-硝基-9-乙基咔唑粗产物的提取工艺 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200750A (en) | 1977-01-07 | 1980-04-29 | Westwood Pharmaceuticals Inc. | 4-Substituted imidazo [1,2-a]quinoxalines |
| CA2140722A1 (en) | 1994-01-24 | 1995-07-25 | Joseph A. Jakubowski | Beta-carboline thromboxane synthase inhibitors |
| US7405295B2 (en) | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| US7393848B2 (en) | 2003-06-30 | 2008-07-01 | Cgi Pharmaceuticals, Inc. | Certain heterocyclic substituted imidazo[1,2-A]pyrazin-8-ylamines and methods of inhibition of Bruton's tyrosine kinase by such compounds |
| WO2005047290A2 (en) | 2003-11-11 | 2005-05-26 | Cellular Genomics Inc. | Imidazo[1,2-a] pyrazin-8-ylamines as kinase inhibitors |
| WO2006044687A2 (en) | 2004-10-15 | 2006-04-27 | Takeda San Diego, Inc. | Kinase inhibitors |
| SG159549A1 (en) | 2004-11-10 | 2010-03-30 | Cgi Pharmaceuticals Inc | Imidazo[1,2-a] pyrazin-8-ylamines useful as modulators of kinase activity |
| PL1831227T3 (pl) | 2004-12-17 | 2013-10-31 | Glenmark Pharmaceuticals Sa | Nowe związki heterocykliczne użyteczne w leczeniu stanów zapalnych i dolegliwości alergicznych |
| AU2006223409B2 (en) | 2005-03-10 | 2011-07-21 | Gilead Connecticut, Inc. | Certain substituted amides, method of making, and method of use thereof |
| US20070078136A1 (en) | 2005-09-22 | 2007-04-05 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| ES2390135T3 (es) | 2005-11-22 | 2012-11-06 | Merck Sharp & Dohme Corp. | Compuestos tricíclicos útiles como inhibidores de quinasas |
| JP2010502751A (ja) | 2006-09-11 | 2010-01-28 | シージーアイ ファーマシューティカルズ，インコーポレイティド | キナーゼ阻害物質、およびキナーゼ阻害物質の使用および同定方法 |
| CA2663178C (en) | 2006-09-11 | 2016-01-12 | Matrix Laboratories Ltd. | Dibenzofuran derivatives as inhibitors of pde-4 and pde-10 |
| US20090062251A1 (en) | 2007-08-17 | 2009-03-05 | Astrazeneca Ab | Novel Compounds 002 |
| US8431569B2 (en) | 2007-12-13 | 2013-04-30 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| US20110046378A1 (en) | 2008-02-14 | 2011-02-24 | Siemens Medical Solutions Usa, Inc. | Novel Imaging Agents for Detecting Neurological Dysfunction |
| GB0809360D0 (en) | 2008-05-22 | 2008-07-02 | Isis Innovation | Calcium modulation |
| CA2725512C (en) * | 2008-07-18 | 2016-06-28 | F. Hoffmann-La Roche Ag | Novel phenylimidazopyrazines |
| EP2151441A1 (en) | 2008-08-06 | 2010-02-10 | Julius-Maximilians-Universität Würzburg | Beta-carbolin-derivates as substrates for an enzyme |
| PE20110819A1 (es) * | 2008-12-19 | 2011-11-02 | Bristol Myers Squibb Co | Compuestos de carbazol carboxamida utiles como inhibidores de cinasa |
| CN101475571B (zh) | 2009-01-21 | 2011-06-22 | 中国药科大学 | β-咔啉类细胞周期蛋白依赖性激酶2抑制剂及其用途 |
| US8242260B2 (en) | 2009-08-28 | 2012-08-14 | Novartis Ag | Compounds and compositions as protein kinase inhibitors |
| US8685969B2 (en) | 2010-06-16 | 2014-04-01 | Bristol-Myers Squibb Company | Carboline carboxamide compounds useful as kinase inhibitors |
| EP2455378A1 (en) | 2010-11-03 | 2012-05-23 | Philip Morris Products S.A. | Carbazole and carboline derivatives, and preparation and therapeutic applications thereof |
| AU2011330850B2 (en) | 2010-11-15 | 2016-01-28 | Viiv Healthcare Uk Limited | Inhibitors of HIV replication |
| WO2012156334A1 (en) | 2011-05-17 | 2012-11-22 | F. Hoffmann-La Roche Ag | Inhibitors of bruton's tyrosine kinase |
| AR096721A1 (es) | 2013-06-25 | 2016-01-27 | Bristol Myers Squibb Co | Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos |
-
2014
- 2014-06-25 AU AU2014302550A patent/AU2014302550A1/en not_active Abandoned
- 2014-06-25 CA CA2916504A patent/CA2916504A1/en not_active Abandoned
- 2014-06-25 WO PCT/US2014/043980 patent/WO2014210087A1/en not_active Ceased
- 2014-06-25 EA EA201690012A patent/EA025863B1/ru not_active IP Right Cessation
- 2014-06-25 BR BR112015031432A patent/BR112015031432A2/pt not_active Application Discontinuation
- 2014-06-25 JP JP2016523870A patent/JP6353530B2/ja not_active Expired - Fee Related
- 2014-06-25 SG SG11201510028PA patent/SG11201510028PA/en unknown
- 2014-06-25 US US14/392,355 patent/US9714234B2/en active Active
- 2014-06-25 CN CN201480046669.2A patent/CN105473573B/zh not_active Expired - Fee Related
- 2014-06-25 EP EP14740096.4A patent/EP3013815B1/en not_active Not-in-force
- 2014-06-25 KR KR1020167001634A patent/KR102345381B1/ko not_active Expired - Fee Related
- 2014-06-25 MX MX2015016771A patent/MX2015016771A/es unknown
-
2015
- 2015-12-22 IL IL243295A patent/IL243295A0/en unknown
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