JP2010502576A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010502576A5 JP2010502576A5 JP2009525630A JP2009525630A JP2010502576A5 JP 2010502576 A5 JP2010502576 A5 JP 2010502576A5 JP 2009525630 A JP2009525630 A JP 2009525630A JP 2009525630 A JP2009525630 A JP 2009525630A JP 2010502576 A5 JP2010502576 A5 JP 2010502576A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorophenyl
- alkyl
- purin
- dihydro
- methyl
- 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 23
- 125000001424 substituent group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 10
- -1 amino, hydroxy Chemical group 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 4
- 102000011040 TRPV Cation Channels Human genes 0.000 claims 4
- 108010062740 TRPV Cation Channels Proteins 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- LLBLFQITYLTANI-UHFFFAOYSA-N 1-(4-bromophenyl)-9-methyl-2-(2,3,4-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2OC1=CC=C(F)C(F)=C1F LLBLFQITYLTANI-UHFFFAOYSA-N 0.000 claims 1
- UFDHZKZCLGSHCD-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,3-difluorophenoxy)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=CC(F)=C1F UFDHZKZCLGSHCD-UHFFFAOYSA-N 0.000 claims 1
- GJXOUFXYDLIAPY-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-difluorophenoxy)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(F)C=C1F GJXOUFXYDLIAPY-UHFFFAOYSA-N 0.000 claims 1
- NVZKVRSPSHMFOP-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[2-fluoro-3-(trifluoromethyl)phenoxy]-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=CC(C(F)(F)F)=C1F NVZKVRSPSHMFOP-UHFFFAOYSA-N 0.000 claims 1
- BICXCCNCLGHDTK-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-methyl-2-(2,3,4-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(F)C(F)=C1F BICXCCNCLGHDTK-UHFFFAOYSA-N 0.000 claims 1
- GOCBGUTZCMCBQY-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-methyl-2-(2,3,5-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC(F)=CC(F)=C1F GOCBGUTZCMCBQY-UHFFFAOYSA-N 0.000 claims 1
- RDZATZYARLCMSW-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-methyl-2-(2,3,6-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=C(F)C=CC(F)=C1F RDZATZYARLCMSW-UHFFFAOYSA-N 0.000 claims 1
- YEOTUUZZHCYVRA-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-methyl-2-(2,4,5-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC(F)=C(F)C=C1F YEOTUUZZHCYVRA-UHFFFAOYSA-N 0.000 claims 1
- KZKMCTARWGFOMA-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-methyl-2-(2,4,6-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=C(F)C=C(F)C=C1F KZKMCTARWGFOMA-UHFFFAOYSA-N 0.000 claims 1
- RLANIOOGDDLPAC-UHFFFAOYSA-N 1-(4-chlorophenyl)-9-methyl-2-(3,4,5-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC(F)=C(F)C(F)=C1 RLANIOOGDDLPAC-UHFFFAOYSA-N 0.000 claims 1
- GGWKXPRZXGXJFP-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[2-fluoro-3-(trifluoromethyl)phenoxy]-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=CC(C(F)(F)F)=C1F GGWKXPRZXGXJFP-UHFFFAOYSA-N 0.000 claims 1
- VUUIPVONBOEDKY-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[3-fluoro-5-(trifluoromethyl)phenoxy]-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC(F)=CC(C(F)(F)F)=C1 VUUIPVONBOEDKY-UHFFFAOYSA-N 0.000 claims 1
- XUVCWSPRHKGBNO-UHFFFAOYSA-N 1-(4-fluorophenyl)-9-methyl-2-(2,3,4-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(F)C(F)=C1F XUVCWSPRHKGBNO-UHFFFAOYSA-N 0.000 claims 1
- KQWWMJUVKWGELV-UHFFFAOYSA-N 1-(4-fluorophenyl)-9-methyl-2-(2,3,5-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC(F)=CC(F)=C1F KQWWMJUVKWGELV-UHFFFAOYSA-N 0.000 claims 1
- MSQALPUSJZKFKD-UHFFFAOYSA-N 1-(4-fluorophenyl)-9-methyl-2-(2,3,6-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=C(F)C=CC(F)=C1F MSQALPUSJZKFKD-UHFFFAOYSA-N 0.000 claims 1
- YNOXTIRZIPKHIO-UHFFFAOYSA-N 1-(4-fluorophenyl)-9-methyl-2-(2,4,5-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC(F)=C(F)C=C1F YNOXTIRZIPKHIO-UHFFFAOYSA-N 0.000 claims 1
- FRXPIJUPJPPPDR-UHFFFAOYSA-N 1-(4-fluorophenyl)-9-methyl-2-(2,4,6-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=C(F)C=C(F)C=C1F FRXPIJUPJPPPDR-UHFFFAOYSA-N 0.000 claims 1
- PWZBGSFKNLUUNT-UHFFFAOYSA-N 1-(4-fluorophenyl)-9-methyl-2-[3-(trifluoromethyl)phenoxy]purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=CC(C(F)(F)F)=C1 PWZBGSFKNLUUNT-UHFFFAOYSA-N 0.000 claims 1
- FJJUGCOHLVRVFB-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)-9-methyl-2-(3,4,5-trifluorophenoxy)purin-6-one Chemical compound CN1C=NC(C(N2C=3C=NC(Cl)=CC=3)=O)=C1N=C2OC1=CC(F)=C(F)C(F)=C1 FJJUGCOHLVRVFB-UHFFFAOYSA-N 0.000 claims 1
- XZCQLTBHLKVBAN-UHFFFAOYSA-N 2-(2,3-difluoro-4-methoxyphenoxy)-1-(4-fluorophenyl)-9-methylpurin-6-one Chemical compound FC1=C(F)C(OC)=CC=C1OC(N(C1=O)C=2C=CC(F)=CC=2)=NC2=C1N=CN2C XZCQLTBHLKVBAN-UHFFFAOYSA-N 0.000 claims 1
- WJMYENCITRBGSP-UHFFFAOYSA-N 2-(2,3-difluoro-4-methoxyphenoxy)-9-ethyl-1-(4-fluorophenyl)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(OC)C(F)=C1F WJMYENCITRBGSP-UHFFFAOYSA-N 0.000 claims 1
- XLSGYAGDGZHLHT-UHFFFAOYSA-N 2-(2,3-difluorophenoxy)-1-(4-fluorophenyl)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=CC(F)=C1F XLSGYAGDGZHLHT-UHFFFAOYSA-N 0.000 claims 1
- UHDWEXDYGOACOY-UHFFFAOYSA-N 2-(2,3-difluorophenoxy)-9-ethyl-1-(4-fluorophenyl)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=CC(F)=C1F UHDWEXDYGOACOY-UHFFFAOYSA-N 0.000 claims 1
- WZOFQUHLSGPGHX-UHFFFAOYSA-N 2-(2,3-dimethoxyphenoxy)-3-(4-fluorophenyl)-7-methylthieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC=CC(OC=2N(C(=O)C=3SC=C(C)C=3N=2)C=2C=CC(F)=CC=2)=C1OC WZOFQUHLSGPGHX-UHFFFAOYSA-N 0.000 claims 1
- WAQKDZPJBDTUCK-UHFFFAOYSA-N 2-(2,3-dimethylphenoxy)-1-(4-fluorophenyl)-9-methylpurin-6-one Chemical compound CC1=CC=CC(OC=2N(C(=O)C=3N=CN(C)C=3N=2)C=2C=CC(F)=CC=2)=C1C WAQKDZPJBDTUCK-UHFFFAOYSA-N 0.000 claims 1
- FZWKTYDFBPTNOQ-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-1-(4-fluorophenyl)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(F)C=C1F FZWKTYDFBPTNOQ-UHFFFAOYSA-N 0.000 claims 1
- FPBJTJQJJNNKEY-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-3-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=NC=CC=C2N=C1OC1=CC=C(F)C=C1F FPBJTJQJJNNKEY-UHFFFAOYSA-N 0.000 claims 1
- GFDNJODKLFEYSI-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-9-ethyl-1-(4-fluorophenyl)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(F)C=C1F GFDNJODKLFEYSI-UHFFFAOYSA-N 0.000 claims 1
- RFRJIHXTWHXQAC-UHFFFAOYSA-N 2-(2,6-dimethylphenoxy)-1-(4-fluorophenyl)-9-methylpurin-6-one Chemical compound CC1=CC=CC(C)=C1OC(N(C1=O)C=2C=CC(F)=CC=2)=NC2=C1N=CN2C RFRJIHXTWHXQAC-UHFFFAOYSA-N 0.000 claims 1
- YIDJRIWMXNYOOR-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-1-(4-chlorophenyl)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(F)C=C1Cl YIDJRIWMXNYOOR-UHFFFAOYSA-N 0.000 claims 1
- ZSNJAAODDRZQFC-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-1-(4-fluorophenyl)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(F)C=C1Cl ZSNJAAODDRZQFC-UHFFFAOYSA-N 0.000 claims 1
- AHYQPSBHKGSOMR-UHFFFAOYSA-N 2-(2-ethylphenoxy)-3-(4-fluorophenyl)-7-methylthieno[3,2-d]pyrimidin-4-one Chemical compound CCC1=CC=CC=C1OC(N(C1=O)C=2C=CC(F)=CC=2)=NC2=C1SC=C2C AHYQPSBHKGSOMR-UHFFFAOYSA-N 0.000 claims 1
- WVRFPTNMPIUVFK-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenoxy)-1-(4-chlorophenyl)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(Cl)C=C1F WVRFPTNMPIUVFK-UHFFFAOYSA-N 0.000 claims 1
- HCHBCCNMLUGNOW-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenoxy)-1-(4-fluorophenyl)-9-methylpurin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(Cl)C=C1F HCHBCCNMLUGNOW-UHFFFAOYSA-N 0.000 claims 1
- KZSYEPGGCPVYAL-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenoxy)-3-(4-chlorophenyl)-7-methylthieno[3,2-d]pyrimidin-4-one Chemical compound CC1=CSC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(Cl)C=C1F KZSYEPGGCPVYAL-UHFFFAOYSA-N 0.000 claims 1
- FGYQTRYWHUDUDA-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenoxy)-3-(4-fluorophenyl)-7-methylthieno[3,2-d]pyrimidin-4-one Chemical compound CC1=CSC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(Cl)C=C1F FGYQTRYWHUDUDA-UHFFFAOYSA-N 0.000 claims 1
- ZHWDTJJJCIHRGN-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenoxy)-9-ethyl-1-(4-fluorophenyl)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(Cl)C=C1F ZHWDTJJJCIHRGN-UHFFFAOYSA-N 0.000 claims 1
- GBFFMBKVGDEOHP-UHFFFAOYSA-N 2-[2-chloro-3-(trifluoromethyl)phenoxy]-3-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=NC=CC=C2N=C1OC1=CC=CC(C(F)(F)F)=C1Cl GBFFMBKVGDEOHP-UHFFFAOYSA-N 0.000 claims 1
- SACYJCHHAPQMPK-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(2,4-difluorophenoxy)-7-methylthieno[3,2-d]pyrimidin-4-one Chemical compound CC1=CSC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(F)C=C1F SACYJCHHAPQMPK-UHFFFAOYSA-N 0.000 claims 1
- RFUCQTHPQJOHGC-UHFFFAOYSA-N 3-(4-chlorophenyl)-7-methyl-2-(2,3,4-trifluorophenoxy)thieno[3,2-d]pyrimidin-4-one Chemical compound CC1=CSC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(F)C(F)=C1F RFUCQTHPQJOHGC-UHFFFAOYSA-N 0.000 claims 1
- NJLGBHPLSGFDKK-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(2,3,4-trifluorophenoxy)pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=NC=CC=C2N=C1OC1=CC=C(F)C(F)=C1F NJLGBHPLSGFDKK-UHFFFAOYSA-N 0.000 claims 1
- JBIVVRAWCUSPHV-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-(2-methoxyphenoxy)-7-methylthieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1OC(N(C1=O)C=2C=CC(F)=CC=2)=NC2=C1SC=C2C JBIVVRAWCUSPHV-UHFFFAOYSA-N 0.000 claims 1
- YIVVXNSLCGHZIL-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=NC=CC=C2N=C1OC1=CC=CC(C(F)(F)F)=C1 YIVVXNSLCGHZIL-UHFFFAOYSA-N 0.000 claims 1
- VAMUHCUEEDHZDW-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-[3-fluoro-5-(trifluoromethyl)phenoxy]pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C2=NC=CC=C2N=C1OC1=CC(F)=CC(C(F)(F)F)=C1 VAMUHCUEEDHZDW-UHFFFAOYSA-N 0.000 claims 1
- XYZXKEWGWJOOSN-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-oxo-2-(2,3,4-trifluorophenoxy)thieno[3,2-d]pyrimidine-7-carbonitrile Chemical compound C1=CC(F)=CC=C1N1C(=O)C(SC=C2C#N)=C2N=C1OC1=CC=C(F)C(F)=C1F XYZXKEWGWJOOSN-UHFFFAOYSA-N 0.000 claims 1
- WMLCRYBHDOYZJL-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-methyl-2-(2,3,4-trifluorophenoxy)thieno[3,2-d]pyrimidin-4-one Chemical compound CC1=CSC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(F)C(F)=C1F WMLCRYBHDOYZJL-UHFFFAOYSA-N 0.000 claims 1
- RIOAPNVMXKCLEW-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-methyl-2-(2,3,6-trifluorophenoxy)thieno[3,2-d]pyrimidin-4-one Chemical compound CC1=CSC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=C(F)C=CC(F)=C1F RIOAPNVMXKCLEW-UHFFFAOYSA-N 0.000 claims 1
- QTMBRBSSNJTNGF-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-methyl-2-(2-methylphenoxy)thieno[3,2-d]pyrimidin-4-one Chemical compound CC1=CSC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=CC=C1C QTMBRBSSNJTNGF-UHFFFAOYSA-N 0.000 claims 1
- YGWQIEKABHIJRY-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-methyl-2-(2-propan-2-ylphenoxy)thieno[3,2-d]pyrimidin-4-one Chemical compound CC(C)C1=CC=CC=C1OC(N(C1=O)C=2C=CC(F)=CC=2)=NC2=C1SC=C2C YGWQIEKABHIJRY-UHFFFAOYSA-N 0.000 claims 1
- DLAFBAQFGNLNEJ-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)-9-methyl-6-oxopurin-2-yl]oxy-2,3-difluorobenzonitrile Chemical compound CN1C=NC(C(N2C=3C=CC(Cl)=CC=3)=O)=C1N=C2OC1=CC=C(C#N)C(F)=C1F DLAFBAQFGNLNEJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- IXXIYWUTSLQSCH-UHFFFAOYSA-N 5-(2,3-difluorophenoxy)-6-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC=CC(F)=C1F IXXIYWUTSLQSCH-UHFFFAOYSA-N 0.000 claims 1
- CFGLPOQFUNXGMV-UHFFFAOYSA-N 5-(4-chloro-2-fluorophenoxy)-6-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC=C(Cl)C=C1F CFGLPOQFUNXGMV-UHFFFAOYSA-N 0.000 claims 1
- KSPPZGPPNFWIHH-UHFFFAOYSA-N 5-[2-chloro-3-(trifluoromethyl)phenoxy]-6-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC=CC(C(F)(F)F)=C1Cl KSPPZGPPNFWIHH-UHFFFAOYSA-N 0.000 claims 1
- FQFYZSSPEVHPPD-UHFFFAOYSA-N 5-[9-methyl-6-oxo-2-(3,4,5-trifluorophenoxy)purin-1-yl]pyridine-2-carbonitrile Chemical compound CN1C=NC(C(N2C=3C=NC(=CC=3)C#N)=O)=C1N=C2OC1=CC(F)=C(F)C(F)=C1 FQFYZSSPEVHPPD-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- ORALMELEOIFCMK-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-(2,3,4-trifluorophenoxy)-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC=C(F)C(F)=C1F ORALMELEOIFCMK-UHFFFAOYSA-N 0.000 claims 1
- JFXLIBJAUXDMIE-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-(2,3,5-trifluorophenoxy)-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC(F)=CC(F)=C1F JFXLIBJAUXDMIE-UHFFFAOYSA-N 0.000 claims 1
- GCVMRYFQUYQJIF-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-(2,4,5-trifluorophenoxy)-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC(F)=C(F)C=C1F GCVMRYFQUYQJIF-UHFFFAOYSA-N 0.000 claims 1
- DOBYGDXSWDMMQZ-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-(3,4,5-trifluorophenoxy)-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC(F)=C(F)C(F)=C1 DOBYGDXSWDMMQZ-UHFFFAOYSA-N 0.000 claims 1
- LAFDJQJGBQAICQ-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-[2-fluoro-3-(trifluoromethyl)phenoxy]-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC=CC(C(F)(F)F)=C1F LAFDJQJGBQAICQ-UHFFFAOYSA-N 0.000 claims 1
- HBTCRNFJSJBEHL-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenoxy]-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC=CC(C(F)(F)F)=C1 HBTCRNFJSJBEHL-UHFFFAOYSA-N 0.000 claims 1
- VIGGOQWTDZWAOM-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-[3-fluoro-5-(trifluoromethyl)phenoxy]-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1N1C(=O)C(N=CS2)=C2N=C1OC1=CC(F)=CC(C(F)(F)F)=C1 VIGGOQWTDZWAOM-UHFFFAOYSA-N 0.000 claims 1
- GYKCVCZBZNMUGI-UHFFFAOYSA-N 9-ethyl-1-(4-fluorophenyl)-2-(2,3,4-trifluorophenoxy)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC=C(F)C(F)=C1F GYKCVCZBZNMUGI-UHFFFAOYSA-N 0.000 claims 1
- UPSOAYOVDVWBKT-UHFFFAOYSA-N 9-ethyl-1-(4-fluorophenyl)-2-(2,3,5-trifluorophenoxy)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC(F)=CC(F)=C1F UPSOAYOVDVWBKT-UHFFFAOYSA-N 0.000 claims 1
- CCHPTVIQGBXOHD-UHFFFAOYSA-N 9-ethyl-1-(4-fluorophenyl)-2-(2,4,5-trifluorophenoxy)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=CC(F)=C(F)C=C1F CCHPTVIQGBXOHD-UHFFFAOYSA-N 0.000 claims 1
- ASXJGOFAPOIRQH-UHFFFAOYSA-N 9-ethyl-1-(4-fluorophenyl)-2-(2,4,6-trifluorophenoxy)purin-6-one Chemical compound CCN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2OC1=C(F)C=C(F)C=C1F ASXJGOFAPOIRQH-UHFFFAOYSA-N 0.000 claims 1
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- 235000002566 Capsicum Nutrition 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 208000031361 Hiccup Diseases 0.000 claims 1
- 206010020853 Hypertonic bladder Diseases 0.000 claims 1
- 206010027304 Menopausal symptoms Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 1
- 239000006002 Pepper Substances 0.000 claims 1
- 235000016761 Piper aduncum Nutrition 0.000 claims 1
- 235000017804 Piper guineense Nutrition 0.000 claims 1
- 244000203593 Piper nigrum Species 0.000 claims 1
- 235000008184 Piper nigrum Nutrition 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000003915 air pollution Methods 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000007885 bronchoconstriction Effects 0.000 claims 1
- 229960002504 capsaicin Drugs 0.000 claims 1
- 235000017663 capsaicin Nutrition 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 239000012678 infectious agent Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 208000020629 overactive bladder Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 239000003491 tear gas Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82325806P | 2006-08-23 | 2006-08-23 | |
| US60/823,258 | 2006-08-23 | ||
| PCT/US2007/018654 WO2008024438A2 (en) | 2006-08-23 | 2007-08-22 | 2-phenoxy pyrimidinone analogues |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010502576A JP2010502576A (ja) | 2010-01-28 |
| JP2010502576A5 true JP2010502576A5 (enExample) | 2010-10-07 |
| JP5421108B2 JP5421108B2 (ja) | 2014-02-19 |
Family
ID=39107411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009525630A Expired - Fee Related JP5421108B2 (ja) | 2006-08-23 | 2007-08-22 | ２−フェノキシピリミジノン類縁体 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8003656B2 (enExample) |
| EP (1) | EP2061794B1 (enExample) |
| JP (1) | JP5421108B2 (enExample) |
| KR (1) | KR20090043583A (enExample) |
| CN (2) | CN101506210A (enExample) |
| AU (1) | AU2007288203B2 (enExample) |
| BR (1) | BRPI0716582A2 (enExample) |
| CA (1) | CA2660957C (enExample) |
| CO (1) | CO6150167A2 (enExample) |
| CR (1) | CR10675A (enExample) |
| EA (1) | EA200900330A1 (enExample) |
| ES (1) | ES2399928T3 (enExample) |
| GT (1) | GT200900040A (enExample) |
| IL (1) | IL197043A0 (enExample) |
| MA (1) | MA30720B1 (enExample) |
| MX (1) | MX2009002066A (enExample) |
| NI (1) | NI200900023A (enExample) |
| NO (1) | NO20091182L (enExample) |
| SV (1) | SV2009003173A (enExample) |
| TW (1) | TW200825089A (enExample) |
| WO (1) | WO2008024438A2 (enExample) |
| ZA (1) | ZA200901163B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0509573D0 (en) * | 2005-05-11 | 2005-06-15 | Merck Sharp & Dohme | Therapeutic compounds |
| ZA200901163B (en) | 2006-08-23 | 2010-08-25 | Neurogen Corp | 2-Phenoxy pyrimidinone analogues |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| ES2784454T3 (es) | 2013-09-09 | 2020-09-25 | Peloton Therapeutics Inc | Aril éteres y usos de los mismos |
| JP6667093B2 (ja) * | 2014-08-11 | 2020-03-18 | ハイドラ・バイオサイエンシーズ・リミテッド・ライアビリティ・カンパニーＨｙｄｒａ Ｂｉｏｓｃｉｅｎｃｅｓ， ＬＬＣ | ピリド［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）−ジオン誘導体 |
| WO2016145045A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Compositions for use in treating glioblastoma |
| EP3267792A4 (en) | 2015-03-11 | 2018-09-26 | Peloton Therapeutics, Inc. | Compositions for use in treating pulmonary arterial hypertension |
| US10807948B2 (en) | 2015-03-11 | 2020-10-20 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
| EP3268362B1 (en) | 2015-03-11 | 2021-10-20 | Peloton Therapeutics, Inc. | Substituted pyridines and uses thereof |
| US10335388B2 (en) | 2015-04-17 | 2019-07-02 | Peloton Therapeutics, Inc. | Combination therapy of a HIF-2-alpha inhibitor and an immunotherapeutic agent and uses thereof |
| WO2020146449A1 (en) * | 2019-01-08 | 2020-07-16 | Texas Tech University System | Small molecule analogs of the protein e4orf1 in the treatment and prevention of metabolic disorders |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0364598A4 (en) * | 1988-03-02 | 1992-01-15 | Yoshitomi Pharmaceutical Industries, Ltd. | 3,4-dihydrothieno 2,3-d¨pyrimidine compounds and pharmaceutical application thereof |
| US5202328A (en) * | 1991-03-06 | 1993-04-13 | Merck & Co., Inc. | Substituted fused pyrimidinones |
| ES2184960T3 (es) * | 1996-05-15 | 2003-04-16 | Pfizer | Nuevas pirimidin-4-onas-(5,6)-heteroaril condensadas 2,3 disustituidas. |
| ATE224643T1 (de) | 1997-05-08 | 2002-10-15 | Aventis Cropscience Uk Ltd | Verwendung von thienopyrimidinen als fungizide |
| US6627755B1 (en) * | 1997-06-09 | 2003-09-30 | Pfizer Inc | Quinazolin-4-one AMPA antagonists |
| US6323208B1 (en) * | 1997-09-05 | 2001-11-27 | Pfizer Inc | Atropisomers of 2,3-disubstituted-(5.6)-heteroaryl fused-pyrimidin-4-ones |
| IL125950A0 (en) * | 1997-09-05 | 1999-04-11 | Pfizer Prod Inc | Methods of administering ampa receptor antagonists to treat dyskinesias associated with dopamine agonist therapy |
| AU2002214546A1 (en) | 2000-09-29 | 2002-04-08 | Cor Therapeutics, Inc. | Bicyclic pyrimidin-4-one based inhibitors of factor xa |
| MXPA03004926A (es) * | 2001-02-14 | 2005-02-14 | Warner Lambert Co | Inhibidores de metaloproteinasas de matriz basados en pirimidinonas fusionadas. |
| KR20030083755A (ko) | 2001-03-26 | 2003-10-30 | 노파르티스 아게 | 동통 치료를 위한 바닐로이드 수용체 길항제로서의 용도를위한 융합 피리딘 유도체 |
| US20070125454A1 (en) * | 2001-09-28 | 2007-06-07 | Konrad Eipper | High-strength duplex/triplex steel for lightweight construction and use thereof |
| WO2003055848A2 (en) | 2001-12-26 | 2003-07-10 | Bayer Healthcare Ag | Urea derivatives as vr1- antagonists |
| ATE533743T1 (de) | 2002-05-17 | 2011-12-15 | Janssen Pharmaceutica Nv | Harnstoffderivate von aminotetralin als modulatoren des vanilloid-rezeptors vr1 |
| TW200401770A (en) | 2002-06-18 | 2004-02-01 | Sankyo Co | Fused-ring pyrimidin-4(3H)-one derivatives, processes for the preparation and uses thereof |
| WO2004028440A2 (en) | 2002-09-24 | 2004-04-08 | Bayer Healthcare Ag | Vr1 antagonists for the treatment of urological disorders |
| GB0223730D0 (en) | 2002-10-11 | 2002-11-20 | Novartis Ag | Organic compounds |
| AU2003301662A1 (en) | 2002-10-21 | 2004-05-13 | Bristol-Myers Squibb Company | Quinazolinones and derivatives thereof as factor xa inhibitors |
| WO2004087053A2 (en) * | 2003-03-25 | 2004-10-14 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| AU2004290626A1 (en) | 2003-11-14 | 2005-06-02 | Merck Sharp & Dohme Limited | Bicyclic pyrimidin-4-(3H)-ones and analogues and derivatives thereof which modulate the function of the vanilloid-1 receptor (VR1) |
| GB0326633D0 (en) | 2003-11-14 | 2003-12-17 | Merck Sharp & Dohme | Therapeutic agents |
| US7544803B2 (en) * | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| GB0412769D0 (en) | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
| AR051596A1 (es) * | 2004-10-26 | 2007-01-24 | Irm Llc | Compuestos heterociclicos condensados nitrogenados como inhibidores de la actividad del receptor canabinoide 1; composiciones farmaceuticas que los contienen y su empleo en la preparacion de medicamentos para el tratamiento de trastornos alimentarios |
| GB0509573D0 (en) * | 2005-05-11 | 2005-06-15 | Merck Sharp & Dohme | Therapeutic compounds |
| AU2006244027A1 (en) * | 2005-05-11 | 2006-11-16 | Merck Sharp & Dohme Limited | 2,3-substituted fused bicyclic pyrimidin-4(3H)-ones modulating the function of the vanilloid-1 receptor (VR1) |
| CN1318429C (zh) * | 2005-07-25 | 2007-05-30 | 华中师范大学 | 具有杀菌活性的取代噻吩并[3',2':5,6]吡啶并[4,3－d]嘧啶－4(3H)－酮及制备 |
| WO2007056124A2 (en) | 2005-11-04 | 2007-05-18 | Hydra Biosciences, Inc. | Compounds for modulating trpv3 function |
| WO2008024433A2 (en) * | 2006-08-23 | 2008-02-28 | Neurogen Corporation | Haloalkyl-substituted pyrimidinone derivatives |
| ZA200901163B (en) | 2006-08-23 | 2010-08-25 | Neurogen Corp | 2-Phenoxy pyrimidinone analogues |
| CA2668579A1 (en) * | 2006-11-06 | 2008-06-05 | Neurogen Corporation | Cis-cyclohexyl substituted pyrimidinone derivatives |
| WO2008156607A1 (en) | 2007-06-12 | 2008-12-24 | Neurogen Corporation | Substituted pyrimidinones |
| WO2009100403A1 (en) | 2008-02-07 | 2009-08-13 | Neurogen Corporation | Substituted aryl pyrimidinones |
| WO2009121036A2 (en) | 2008-03-27 | 2009-10-01 | Neurogen Corporation | Substituted aryl pyrimidinone derivatives |
-
2007
- 2007-08-22 ZA ZA200901163A patent/ZA200901163B/xx unknown
- 2007-08-22 US US11/895,286 patent/US8003656B2/en active Active
- 2007-08-22 CA CA2660957A patent/CA2660957C/en not_active Expired - Fee Related
- 2007-08-22 BR BRPI0716582-0A2A patent/BRPI0716582A2/pt not_active IP Right Cessation
- 2007-08-22 TW TW096131019A patent/TW200825089A/zh unknown
- 2007-08-22 ES ES07811503T patent/ES2399928T3/es active Active
- 2007-08-22 JP JP2009525630A patent/JP5421108B2/ja not_active Expired - Fee Related
- 2007-08-22 MX MX2009002066A patent/MX2009002066A/es unknown
- 2007-08-22 CN CNA2007800309530A patent/CN101506210A/zh active Pending
- 2007-08-22 AU AU2007288203A patent/AU2007288203B2/en not_active Ceased
- 2007-08-22 EP EP07811503A patent/EP2061794B1/en active Active
- 2007-08-22 CN CN201410468406.2A patent/CN104292229A/zh active Pending
- 2007-08-22 KR KR1020097005810A patent/KR20090043583A/ko not_active Withdrawn
- 2007-08-22 EA EA200900330A patent/EA200900330A1/ru unknown
- 2007-08-22 WO PCT/US2007/018654 patent/WO2008024438A2/en not_active Ceased
-
2009
- 2009-02-15 IL IL197043A patent/IL197043A0/en unknown
- 2009-02-20 NI NI200900023A patent/NI200900023A/es unknown
- 2009-02-20 SV SV2009003173A patent/SV2009003173A/es not_active Application Discontinuation
- 2009-02-23 GT GT200900040A patent/GT200900040A/es unknown
- 2009-03-18 CO CO09028167A patent/CO6150167A2/es unknown
- 2009-03-20 CR CR10675A patent/CR10675A/es not_active Application Discontinuation
- 2009-03-20 NO NO20091182A patent/NO20091182L/no not_active Application Discontinuation
- 2009-03-23 MA MA31732A patent/MA30720B1/fr unknown
-
2011
- 2011-08-22 US US13/215,195 patent/US8759361B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010502576A5 (enExample) | ||
| JP2007534687A5 (enExample) | ||
| JP6884102B2 (ja) | がんの治療のための化合物 | |
| JP5997335B2 (ja) | Ｎ含有複素環式化合物 | |
| JP2019052178A (ja) | ブロモドメイン阻害剤としての新規の置換された二環式化合物 | |
| CA2651363A1 (en) | Triazolopyrazine derivatives useful as anti-cancer agents | |
| RU2009136299A (ru) | Новые производные 3-({1,2,4}триазоло{4,3-а}пиридин-7-ил)бензамида | |
| JP2010509224A5 (enExample) | ||
| RU2012148246A (ru) | 5, 7- замещенные-имидазо[1, 2-с]пиримидины как ингибиторы jak-киназ | |
| JP2014528450A5 (enExample) | ||
| JP2017526711A5 (enExample) | ||
| JP2008523041A5 (enExample) | ||
| JP2007510689A5 (enExample) | ||
| RU2012134306A (ru) | Азотосодержащие производные гетероарилов | |
| JP2013523884A5 (enExample) | ||
| JP2017523223A5 (enExample) | ||
| NZ604004A (en) | Pyridone and aza-pyridone compounds and methods of use | |
| MX2013010140A (es) | Amino-quinolinas como inhibidores de cinasa. | |
| JP2016512511A5 (enExample) | ||
| US20130096149A1 (en) | Heteroaryl compounds and compositions as protein kinase inhibitors | |
| JP2018515525A5 (enExample) | ||
| CA2737999A1 (en) | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma | |
| RU2011125314A (ru) | Новое производное пиразол-3-карбоксамида, обладающее антагонистической активностью в отношении рецептора 5-нт2в | |
| SI3038622T1 (en) | Heterocyclic compounds and methods of use | |
| JP2009504792A5 (enExample) |