JP2008531638A - 抗マラリアピリジノン誘導体 - Google Patents
抗マラリアピリジノン誘導体 Download PDFInfo
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- JP2008531638A JP2008531638A JP2007557451A JP2007557451A JP2008531638A JP 2008531638 A JP2008531638 A JP 2008531638A JP 2007557451 A JP2007557451 A JP 2007557451A JP 2007557451 A JP2007557451 A JP 2007557451A JP 2008531638 A JP2008531638 A JP 2008531638A
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- JP
- Japan
- Prior art keywords
- dimethyl
- bipyridin
- chloro
- phenyl
- trifluoromethyl
- 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.)
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- 239000003430 antimalarial agent Substances 0.000 title description 5
- 230000000078 anti-malarial effect Effects 0.000 title description 3
- 150000005299 pyridinones Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 201000004792 malaria Diseases 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 321
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- -1 methylenedioxyphenyl Chemical group 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229910052763 palladium Inorganic materials 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 241000223960 Plasmodium falciparum Species 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 7
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- WTQWKCRZZGEDMM-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[2-[3-(trifluoromethyl)phenyl]ethyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1CCC1=CC=CC(C(F)(F)F)=C1 WTQWKCRZZGEDMM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- IMOIIKLMCIJYJK-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[2-[3-(trifluoromethyl)phenyl]ethyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1CCC1=CC=CC(C(F)(F)F)=C1 IMOIIKLMCIJYJK-UHFFFAOYSA-N 0.000 claims description 3
- VNXGLTIRWVQRLY-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(OC(F)(F)F)=CC=2)N=C1 VNXGLTIRWVQRLY-UHFFFAOYSA-N 0.000 claims description 3
- YISCDAWSGMIIAZ-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[[4-(trifluoromethoxy)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 YISCDAWSGMIIAZ-UHFFFAOYSA-N 0.000 claims description 3
- KZCXOKMDRDIOHV-UHFFFAOYSA-N 3-bromo-5-[6-(4-butylphenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one;hydrochloride Chemical compound Cl.C1=CC(CCCC)=CC=C1C1=CC=C(C=2C(C(Br)=C(C)NC=2C)=O)C=N1 KZCXOKMDRDIOHV-UHFFFAOYSA-N 0.000 claims description 3
- PDJIDUOXIMNJSY-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-(5-nonylpyrimidin-2-yl)-1h-pyridin-4-one Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=C(C)NC(C)=C(Cl)C1=O PDJIDUOXIMNJSY-UHFFFAOYSA-N 0.000 claims description 3
- QVWFYMYHZRDRMO-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[2-[4-(trifluoromethyl)phenyl]pyrimidin-5-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CN=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1 QVWFYMYHZRDRMO-UHFFFAOYSA-N 0.000 claims description 3
- FBXRGLBXRLRIFC-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[5-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridin-2-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(N=C1)=CC=C1CCC1=CC=C(C(F)(F)F)C=C1 FBXRGLBXRLRIFC-UHFFFAOYSA-N 0.000 claims description 3
- VPSYQEKHLBDCIH-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[2-[4-(trifluoromethyl)phenyl]ethynyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C#CC=2C=CC(=CC=2)C(F)(F)F)N=C1 VPSYQEKHLBDCIH-UHFFFAOYSA-N 0.000 claims description 3
- MKWKRUUHKKPELZ-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=C(C=CC=2)C(F)(F)F)N=C1 MKWKRUUHKKPELZ-UHFFFAOYSA-N 0.000 claims description 3
- CSCVNCAJXMMUNB-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(OC(F)(F)F)=CC=2)N=C1 CSCVNCAJXMMUNB-UHFFFAOYSA-N 0.000 claims description 3
- YZERDFWTZACKFS-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]-1h-pyridin-4-one;hydrochloride Chemical compound Cl.O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(OC(F)(F)F)=CC=2)N=C1 YZERDFWTZACKFS-UHFFFAOYSA-N 0.000 claims description 3
- JMUBMEOGVZOWCI-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[[4-(trifluoromethoxy)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 JMUBMEOGVZOWCI-UHFFFAOYSA-N 0.000 claims description 3
- CPRMMJHUHCXNKL-UHFFFAOYSA-N 3-chloro-5-(6-heptylpyridin-3-yl)-2,6-dimethyl-1h-pyridin-4-one;hydrochloride Chemical compound Cl.C1=NC(CCCCCCC)=CC=C1C1=C(C)NC(C)=C(Cl)C1=O CPRMMJHUHCXNKL-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- ZUIVRLNCWYVLGK-UHFFFAOYSA-N 3-[6-(2-butoxyphenyl)pyridin-3-yl]-5-chloro-2,6-dimethyl-1h-pyridin-4-one Chemical compound CCCCOC1=CC=CC=C1C1=CC=C(C=2C(C(Cl)=C(C)NC=2C)=O)C=N1 ZUIVRLNCWYVLGK-UHFFFAOYSA-N 0.000 claims description 2
- KHEXLIPZWHUSCX-UHFFFAOYSA-N 3-[6-[2,4-bis(trifluoromethyl)phenyl]pyridin-3-yl]-5-bromo-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC(=CC=2)C(F)(F)F)C(F)(F)F)N=C1 KHEXLIPZWHUSCX-UHFFFAOYSA-N 0.000 claims description 2
- MVXDWSSBDVRPHJ-UHFFFAOYSA-N 3-[6-[3,5-bis(trifluoromethyl)phenyl]pyridin-3-yl]-5-bromo-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)N=C1 MVXDWSSBDVRPHJ-UHFFFAOYSA-N 0.000 claims description 2
- FYXYWZVYOLWBNV-UHFFFAOYSA-N 3-[6-[[3,5-bis(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-5-bromo-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FYXYWZVYOLWBNV-UHFFFAOYSA-N 0.000 claims description 2
- JHWFACBPRWEMPY-UHFFFAOYSA-N 3-[6-[[3,5-bis(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-5-chloro-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JHWFACBPRWEMPY-UHFFFAOYSA-N 0.000 claims description 2
- BYFRPARTTAVAPP-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[2-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1 BYFRPARTTAVAPP-UHFFFAOYSA-N 0.000 claims description 2
- PJTLURISAIGCBN-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C=C(C=CC=2)C(F)(F)F)N=C1 PJTLURISAIGCBN-UHFFFAOYSA-N 0.000 claims description 2
- YWSBVXIMBZMIHJ-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1 YWSBVXIMBZMIHJ-UHFFFAOYSA-N 0.000 claims description 2
- RAJMXUPETADXPT-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[[2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=CC=C1C(F)(F)F RAJMXUPETADXPT-UHFFFAOYSA-N 0.000 claims description 2
- SKSSJLUQENPPMH-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[[3-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 SKSSJLUQENPPMH-UHFFFAOYSA-N 0.000 claims description 2
- RLLBLWKMQTWMQL-UHFFFAOYSA-N 3-bromo-2,6-dimethyl-5-[6-[[4-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 RLLBLWKMQTWMQL-UHFFFAOYSA-N 0.000 claims description 2
- XQHMHFDOURAUIQ-UHFFFAOYSA-N 3-bromo-5-[6-(2-chlorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC=CC=2)Cl)N=C1 XQHMHFDOURAUIQ-UHFFFAOYSA-N 0.000 claims description 2
- IMXQLRJLFQEWPG-UHFFFAOYSA-N 3-bromo-5-[6-(2-fluorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC=CC=2)F)N=C1 IMXQLRJLFQEWPG-UHFFFAOYSA-N 0.000 claims description 2
- PMMMJQQHWNAXMT-UHFFFAOYSA-N 3-bromo-5-[6-(3-chlorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C=C(Cl)C=CC=2)N=C1 PMMMJQQHWNAXMT-UHFFFAOYSA-N 0.000 claims description 2
- ZFFWYKFHSDOWRG-UHFFFAOYSA-N 3-bromo-5-[6-(4-butylphenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound C1=CC(CCCC)=CC=C1C1=CC=C(C=2C(C(Br)=C(C)NC=2C)=O)C=N1 ZFFWYKFHSDOWRG-UHFFFAOYSA-N 0.000 claims description 2
- MVGXJMRCECBOKA-UHFFFAOYSA-N 3-bromo-5-[6-(4-chlorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(Cl)=CC=2)N=C1 MVGXJMRCECBOKA-UHFFFAOYSA-N 0.000 claims description 2
- BGUPBFLSCKYCLE-UHFFFAOYSA-N 3-bromo-5-[6-(4-fluorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(F)=CC=2)N=C1 BGUPBFLSCKYCLE-UHFFFAOYSA-N 0.000 claims description 2
- FCTOCXXWEQGGHU-UHFFFAOYSA-N 3-bromo-5-[6-[(3,5-difluorophenyl)methoxy]pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC(F)=CC(F)=C1 FCTOCXXWEQGGHU-UHFFFAOYSA-N 0.000 claims description 2
- KOHNAVCUPVLLIB-UHFFFAOYSA-N 3-bromo-5-[6-[(4-fluorophenyl)methoxy]pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Br)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=C(F)C=C1 KOHNAVCUPVLLIB-UHFFFAOYSA-N 0.000 claims description 2
- RAIMOPHTHDYIOY-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[2-(trifluoromethoxy)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC=CC=2)OC(F)(F)F)N=C1 RAIMOPHTHDYIOY-UHFFFAOYSA-N 0.000 claims description 2
- MTMFRZBGTKKKMK-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[2-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC=CC=2)C(F)(F)F)N=C1 MTMFRZBGTKKKMK-UHFFFAOYSA-N 0.000 claims description 2
- XZBGAEGFPVSFBW-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[2-[4-(trifluoromethyl)phenyl]ethyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1CCC1=CC=C(C(F)(F)F)C=C1 XZBGAEGFPVSFBW-UHFFFAOYSA-N 0.000 claims description 2
- KHIRIWRUHUYBAS-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=C(OC(F)(F)F)C=CC=2)N=C1 KHIRIWRUHUYBAS-UHFFFAOYSA-N 0.000 claims description 2
- SRODXJSLBYYOGG-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(OCC(F)(F)F)=CC=2)N=C1 SRODXJSLBYYOGG-UHFFFAOYSA-N 0.000 claims description 2
- MVQZTNYZZXAACM-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1 MVQZTNYZZXAACM-UHFFFAOYSA-N 0.000 claims description 2
- BLGHRRWOMWOELW-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[[2-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=CC=C1C(F)(F)F BLGHRRWOMWOELW-UHFFFAOYSA-N 0.000 claims description 2
- OACMRIHGWJGRCG-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[[3-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 OACMRIHGWJGRCG-UHFFFAOYSA-N 0.000 claims description 2
- UINWROKSLGMRBI-UHFFFAOYSA-N 3-chloro-2,6-dimethyl-5-[6-[[4-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 UINWROKSLGMRBI-UHFFFAOYSA-N 0.000 claims description 2
- JVFMVRAXJAWBJW-UHFFFAOYSA-N 3-chloro-5-(6-heptylpyridin-3-yl)-2,6-dimethyl-1h-pyridin-4-one Chemical compound C1=NC(CCCCCCC)=CC=C1C1=C(C)NC(C)=C(Cl)C1=O JVFMVRAXJAWBJW-UHFFFAOYSA-N 0.000 claims description 2
- ZSNDRSHGZITMIP-UHFFFAOYSA-N 3-chloro-5-[6-(2-chlorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC=CC=2)Cl)N=C1 ZSNDRSHGZITMIP-UHFFFAOYSA-N 0.000 claims description 2
- BSEVEQUYICLZPZ-UHFFFAOYSA-N 3-chloro-5-[6-(2-fluorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C(=CC=CC=2)F)N=C1 BSEVEQUYICLZPZ-UHFFFAOYSA-N 0.000 claims description 2
- PSLYUHHUBIFJAO-UHFFFAOYSA-N 3-chloro-5-[6-(3-chlorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=C(Cl)C=CC=2)N=C1 PSLYUHHUBIFJAO-UHFFFAOYSA-N 0.000 claims description 2
- PHTJVNUZJAULPR-UHFFFAOYSA-N 3-chloro-5-[6-(4-chlorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(Cl)=CC=2)N=C1 PHTJVNUZJAULPR-UHFFFAOYSA-N 0.000 claims description 2
- OMLXLKLQYGIMDT-UHFFFAOYSA-N 3-chloro-5-[6-(4-fluorophenyl)pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C1=CC=C(C=2C=CC(F)=CC=2)N=C1 OMLXLKLQYGIMDT-UHFFFAOYSA-N 0.000 claims description 2
- ARAPYZAHCWUISR-UHFFFAOYSA-N 3-chloro-5-[6-[(3,5-difluorophenyl)methoxy]pyridin-3-yl]-2,6-dimethyl-1h-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(C)=C1C(C=N1)=CC=C1OCC1=CC(F)=CC(F)=C1 ARAPYZAHCWUISR-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011976 maleic acid Substances 0.000 description 1
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- 230000003211 malignant effect Effects 0.000 description 1
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- 239000002207 metabolite Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 102000039446 nucleic acids Human genes 0.000 description 1
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- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 description 1
- 229960005179 primaquine Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 229960005385 proguanil Drugs 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 201000002612 sleeping sickness Diseases 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000007886 soft shell capsule Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960004673 sulfadoxine Drugs 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05381011 | 2005-03-04 | ||
| PCT/EP2006/002160 WO2006094799A2 (en) | 2005-03-04 | 2006-03-02 | Pyridinone derivatives against malaria |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008531638A true JP2008531638A (ja) | 2008-08-14 |
| JP2008531638A5 JP2008531638A5 (https=) | 2009-04-16 |
Family
ID=36593784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007557451A Pending JP2008531638A (ja) | 2005-03-04 | 2006-03-02 | 抗マラリアピリジノン誘導体 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US7579353B2 (https=) |
| EP (1) | EP1858876A2 (https=) |
| JP (1) | JP2008531638A (https=) |
| WO (1) | WO2006094799A2 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011504914A (ja) * | 2007-11-30 | 2011-02-17 | グラクソ グループ リミテッド | 抗マラリア化合物の結晶形態 |
| US8598354B2 (en) | 2008-12-05 | 2013-12-03 | University Of South Florida | Compounds having antiparasitic or anti-infectious activity |
| WO2010081904A1 (en) | 2009-01-19 | 2010-07-22 | Glaxo Group Limited | 4 ( 1h) -pyridinone derivatives and their use as antimalaria agents |
| EP2246329A1 (en) | 2009-01-19 | 2010-11-03 | Glaxo Group Limited | 4(1H)-pyridinone derivatives and their use as antimalaria agents |
| WO2010142741A1 (en) * | 2009-06-12 | 2010-12-16 | Glaxo Group Limited | Phenylpyridylpyridones for use as antimalarial agents |
| WO2011072064A1 (en) | 2009-12-08 | 2011-06-16 | Array Biopharma Inc. | S piro [chroman - 4, 4 ' - imidazol] ones as beta - secretase inhibitors |
| CN103209975B (zh) | 2010-09-16 | 2016-01-13 | 日东电工株式会社 | 用于有机发光装置的取代的联吡啶 |
| US8585926B2 (en) | 2011-03-03 | 2013-11-19 | Nitto Denko Corporation | Substituted bipyridines for use in light-emitting devices |
| US9328094B2 (en) | 2011-09-19 | 2016-05-03 | Nitto Denko Corporation | Substituted biaryl compounds for light-emitting devices |
| CN105237483B (zh) * | 2015-11-10 | 2018-04-20 | 东华大学 | 一种对称型嘧啶基碘鎓盐及其制备方法 |
| US11766435B2 (en) | 2016-02-18 | 2023-09-26 | Merck Sharp & Dohme Llc | N3-substituted iminopyrimidinones as antimalarial agents |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05140107A (ja) * | 1991-02-11 | 1993-06-08 | Imperial Chem Ind Plc <Ici> | ピリジン化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9005518D0 (en) * | 1990-03-12 | 1990-05-09 | Wellcome Found | Heterocyclic compounds |
-
2006
- 2006-03-02 JP JP2007557451A patent/JP2008531638A/ja active Pending
- 2006-03-02 US US11/817,508 patent/US7579353B2/en not_active Expired - Fee Related
- 2006-03-02 WO PCT/EP2006/002160 patent/WO2006094799A2/en not_active Ceased
- 2006-03-02 EP EP06707486A patent/EP1858876A2/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05140107A (ja) * | 1991-02-11 | 1993-06-08 | Imperial Chem Ind Plc <Ici> | ピリジン化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1858876A2 (en) | 2007-11-28 |
| US7579353B2 (en) | 2009-08-25 |
| WO2006094799A3 (en) | 2007-03-29 |
| WO2006094799A2 (en) | 2006-09-14 |
| US20080287461A1 (en) | 2008-11-20 |
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