JP2017533232A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017533232A5 JP2017533232A5 JP2017523862A JP2017523862A JP2017533232A5 JP 2017533232 A5 JP2017533232 A5 JP 2017533232A5 JP 2017523862 A JP2017523862 A JP 2017523862A JP 2017523862 A JP2017523862 A JP 2017523862A JP 2017533232 A5 JP2017533232 A5 JP 2017533232A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- thiazolo
- purin
- cycloalkyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 108091007960 PI3Ks Proteins 0.000 claims 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- -1 chloro, methyl Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052757 nitrogen Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- NUYCHCBEWHGVIX-UHFFFAOYSA-N 2-amino-4-methyl-6-[1-(3-methyl-5-oxo-6-phenyl-[1,3]thiazolo[3,2-a]pyridin-7-yl)ethylamino]pyrimidine-5-carbonitrile Chemical compound NC1=NC(=C(C(=N1)C)C#N)NC(C)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)C NUYCHCBEWHGVIX-UHFFFAOYSA-N 0.000 claims 1
- ILQHNGJJMXUTON-UHFFFAOYSA-N 3-chloro-6-(3-fluorophenyl)-7-[1-(7H-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)Cl ILQHNGJJMXUTON-UHFFFAOYSA-N 0.000 claims 1
- WSCSMFORJDLXGY-UHFFFAOYSA-N 3-chloro-6-(3-fluorophenyl)-7-[1-(7H-purin-6-ylamino)propyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)Cl WSCSMFORJDLXGY-UHFFFAOYSA-N 0.000 claims 1
- DXCXHGPXMXIRNK-UHFFFAOYSA-N 3-chloro-6-phenyl-7-[1-(7H-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)Cl DXCXHGPXMXIRNK-UHFFFAOYSA-N 0.000 claims 1
- SXNVMJZYPPCDLY-UHFFFAOYSA-N 3-chloro-6-phenyl-7-[1-(7H-purin-6-ylamino)propyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)Cl SXNVMJZYPPCDLY-UHFFFAOYSA-N 0.000 claims 1
- MRGCQBOQCFGTNI-UHFFFAOYSA-N 3-chloro-7-[cyclopropyl-(7H-purin-6-ylamino)methyl]-6-(3-fluorophenyl)-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)Cl)C1CC1 MRGCQBOQCFGTNI-UHFFFAOYSA-N 0.000 claims 1
- VRDZBLOZCCLQDO-UHFFFAOYSA-N 3-chloro-7-[cyclopropyl-(7H-purin-6-ylamino)methyl]-6-phenyl-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)Cl)C1CC1 VRDZBLOZCCLQDO-UHFFFAOYSA-N 0.000 claims 1
- DZPOKLRWERUUTG-UHFFFAOYSA-N 3-ethyl-6-phenyl-7-[1-(7H-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)CC DZPOKLRWERUUTG-UHFFFAOYSA-N 0.000 claims 1
- GGFMIRIKNCYXKE-UHFFFAOYSA-N 3-methyl-6-phenyl-7-[1-(7H-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)C GGFMIRIKNCYXKE-UHFFFAOYSA-N 0.000 claims 1
- CVWBEDROSVSEEG-UHFFFAOYSA-N 3-methyl-6-phenyl-7-[1-(7H-purin-6-ylamino)propyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)C CVWBEDROSVSEEG-UHFFFAOYSA-N 0.000 claims 1
- GYKIIJNWTSFZAX-UHFFFAOYSA-N 3-phenyl-2-[1-(7H-purin-6-ylamino)ethyl]quinolizin-4-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2C=CC=CN2C(C=1C1=CC=CC=C1)=O GYKIIJNWTSFZAX-UHFFFAOYSA-N 0.000 claims 1
- URWYQWDYELVLEP-UHFFFAOYSA-N 3-phenyl-2-[1-(7H-purin-6-ylamino)propyl]quinolizin-4-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2C=CC=CN2C(C=1C1=CC=CC=C1)=O URWYQWDYELVLEP-UHFFFAOYSA-N 0.000 claims 1
- GRSFZFGMSHSRSB-UHFFFAOYSA-N 6-(2-fluorophenyl)-3-methyl-7-[1-(7H-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=C(C=CC=C1)F)=O)C(=CS2)C GRSFZFGMSHSRSB-UHFFFAOYSA-N 0.000 claims 1
- MAZIZQWSTKHBIC-UHFFFAOYSA-N 6-(2-fluorophenyl)-3-methyl-7-[1-(7H-purin-6-ylamino)propyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=C(C=CC=C1)F)=O)C(=CS2)C MAZIZQWSTKHBIC-UHFFFAOYSA-N 0.000 claims 1
- YBKOKELSGNIMPO-UHFFFAOYSA-N 6-(3-fluorophenyl)-3-methyl-7-[1-(7H-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)C YBKOKELSGNIMPO-UHFFFAOYSA-N 0.000 claims 1
- IXBLLRJVLUOGLC-UHFFFAOYSA-N 6-(3-fluorophenyl)-3-methyl-7-[1-(7H-purin-6-ylamino)propyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)C IXBLLRJVLUOGLC-UHFFFAOYSA-N 0.000 claims 1
- BIXFXZXTIOBBRF-UHFFFAOYSA-N 6-(3-fluorophenyl)-7-[1-(7H-purin-6-ylamino)ethyl]-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)C(F)(F)F BIXFXZXTIOBBRF-UHFFFAOYSA-N 0.000 claims 1
- HSWBSRVSIHUXDT-UHFFFAOYSA-N 6-(3-fluorophenyl)-7-[1-(7H-purin-6-ylamino)propyl]-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)C(F)(F)F HSWBSRVSIHUXDT-UHFFFAOYSA-N 0.000 claims 1
- OUCBQVQFOMQIQR-UHFFFAOYSA-N 6-(4-fluorophenyl)-3-methyl-7-[1-(7H-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC=C(C=C1)F)=O)C(=CS2)C OUCBQVQFOMQIQR-UHFFFAOYSA-N 0.000 claims 1
- KQEAXKUEXMUGMH-UHFFFAOYSA-N 6-(4-fluorophenyl)-3-methyl-7-[1-(7H-purin-6-ylamino)propyl]-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=CC=C(C=C1)F)=O)C(=CS2)C KQEAXKUEXMUGMH-UHFFFAOYSA-N 0.000 claims 1
- JNGBXTJNOAVHRJ-UHFFFAOYSA-N 6-phenyl-7-[1-(7H-purin-6-ylamino)ethyl]-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)C(F)(F)F JNGBXTJNOAVHRJ-UHFFFAOYSA-N 0.000 claims 1
- IYKZJAXKDBMYCL-UHFFFAOYSA-N 6-phenyl-7-[1-(7H-purin-6-ylamino)propyl]-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(CC)C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)C(F)(F)F IYKZJAXKDBMYCL-UHFFFAOYSA-N 0.000 claims 1
- CPURWLMHDQOTSB-UHFFFAOYSA-N 7-[cyclopropyl-(7H-purin-6-ylamino)methyl]-3-methyl-6-phenyl-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)C)C1CC1 CPURWLMHDQOTSB-UHFFFAOYSA-N 0.000 claims 1
- QRWABWUGCFYPMA-UHFFFAOYSA-N 7-[cyclopropyl-(7H-purin-6-ylamino)methyl]-6-(3-fluorophenyl)-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)C(F)(F)F)C1CC1 QRWABWUGCFYPMA-UHFFFAOYSA-N 0.000 claims 1
- DCIRWAOWQSDYKJ-UHFFFAOYSA-N 7-[cyclopropyl-(7H-purin-6-ylamino)methyl]-6-(3-fluorophenyl)-3-methyl-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C=1C=C2N(C(C=1C1=CC(=CC=C1)F)=O)C(=CS2)C)C1CC1 DCIRWAOWQSDYKJ-UHFFFAOYSA-N 0.000 claims 1
- KTZZKZTVRGWBDO-UHFFFAOYSA-N 7-[cyclopropyl-(7H-purin-6-ylamino)methyl]-6-phenyl-3-(trifluoromethyl)-[1,3]thiazolo[3,2-a]pyridin-5-one Chemical compound N1=CN=C2NC=NC2=C1NC(C=1C=C2N(C(C=1C1=CC=CC=C1)=O)C(=CS2)C(F)(F)F)C1CC1 KTZZKZTVRGWBDO-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462073993P | 2014-11-01 | 2014-11-01 | |
| US62/073,993 | 2014-11-01 | ||
| PCT/CN2015/093551 WO2016066142A1 (en) | 2014-11-01 | 2015-11-01 | Certain protein kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017533232A JP2017533232A (ja) | 2017-11-09 |
| JP2017533232A5 true JP2017533232A5 (enExample) | 2018-12-06 |
| JP6831324B2 JP6831324B2 (ja) | 2021-02-17 |
Family
ID=55856639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017523862A Expired - Fee Related JP6831324B2 (ja) | 2014-11-01 | 2015-11-01 | 特定のタンパク質キナーゼ阻害剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10328060B2 (enExample) |
| EP (1) | EP3224248B1 (enExample) |
| JP (1) | JP6831324B2 (enExample) |
| CN (1) | CN107207441B (enExample) |
| AU (1) | AU2015341186B2 (enExample) |
| BR (1) | BR112017008867A2 (enExample) |
| CA (1) | CA2966252C (enExample) |
| ES (1) | ES2879809T3 (enExample) |
| WO (1) | WO2016066142A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201610770PA (en) * | 2014-07-04 | 2017-01-27 | Lupin Ltd | Quinolizinone derivatives as pi3k inhibitors |
| WO2017103825A1 (en) | 2015-12-18 | 2017-06-22 | Lupin Limited | Quinolizinone derivatives as pi3k inhibitors |
| CA3178569A1 (en) * | 2020-05-16 | 2021-11-25 | Zuwen ZHOU | Compounds as protein kinase inhibitors |
| WO2022228387A1 (en) * | 2021-04-26 | 2022-11-03 | Fochon Biosciences, Ltd. | Compounds as parp inhibitors |
| WO2023078401A1 (en) * | 2021-11-05 | 2023-05-11 | Fochon Biosciences, Ltd. | Compounds as protein kinase inhibitors |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS545996A (en) * | 1977-06-15 | 1979-01-17 | Yamanouchi Pharmaceut Co Ltd | Heterocyclic compounds and process for their preparation |
| US6630488B1 (en) * | 1998-09-21 | 2003-10-07 | Biochem Pharma, Inc. | Quinolizinones as integrin inhibitors |
| US6667300B2 (en) | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| EP1761540B1 (en) | 2004-05-13 | 2016-09-28 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
| JP5313909B2 (ja) | 2006-11-13 | 2013-10-09 | アイコス コーポレイション | 炎症性疾患および癌の処置のためのチエノピリミジノン |
| WO2008153947A2 (en) | 2007-06-07 | 2008-12-18 | Amgen Inc. | Heterocyclic compounds as raf kinase modulators |
| EP2845856A1 (en) * | 2009-06-29 | 2015-03-11 | Incyte Corporation | Pyrimidinones as PI3K inhibitors |
| US8916593B2 (en) | 2010-05-04 | 2014-12-23 | Pfizer Inc. | Alkoxy-substituted 2-aminopyridines as ALK inhibitors |
| EP2518070A1 (en) * | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone derivatives as PI3K inhibitors |
| ES2697174T3 (es) * | 2012-02-10 | 2019-01-22 | Ptc Therapeutics Inc | Compuestos para tratar atrofia muscular espinal |
| WO2013149362A1 (en) | 2012-04-06 | 2013-10-10 | Glaxosmithkline Llc | 1-(dihydronaphthalenyl)pyridones as melanin-concentrating hormone receptor 1 antagonists |
| SG11201610770PA (en) * | 2014-07-04 | 2017-01-27 | Lupin Ltd | Quinolizinone derivatives as pi3k inhibitors |
-
2015
- 2015-11-01 ES ES15855878T patent/ES2879809T3/es active Active
- 2015-11-01 JP JP2017523862A patent/JP6831324B2/ja not_active Expired - Fee Related
- 2015-11-01 WO PCT/CN2015/093551 patent/WO2016066142A1/en not_active Ceased
- 2015-11-01 CA CA2966252A patent/CA2966252C/en active Active
- 2015-11-01 CN CN201580071637.2A patent/CN107207441B/zh not_active Expired - Fee Related
- 2015-11-01 BR BR112017008867A patent/BR112017008867A2/pt not_active Application Discontinuation
- 2015-11-01 US US15/523,315 patent/US10328060B2/en active Active
- 2015-11-01 AU AU2015341186A patent/AU2015341186B2/en not_active Ceased
- 2015-11-01 EP EP15855878.3A patent/EP3224248B1/en active Active