JP2005500315A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005500315A5 JP2005500315A5 JP2003507092A JP2003507092A JP2005500315A5 JP 2005500315 A5 JP2005500315 A5 JP 2005500315A5 JP 2003507092 A JP2003507092 A JP 2003507092A JP 2003507092 A JP2003507092 A JP 2003507092A JP 2005500315 A5 JP2005500315 A5 JP 2005500315A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- imidazo
- cyclopentylamino
- pyrimidinyl
- cyclopentyl
- 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.)
- Pending
Links
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 108020005497 Nuclear hormone receptors Proteins 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004429 atoms Chemical group 0.000 claims 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- GVJZSWGXJJEWND-UHFFFAOYSA-N 2-(3-aminophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 GVJZSWGXJJEWND-UHFFFAOYSA-N 0.000 claims 1
- ZMYVMTMGMQNEIO-UHFFFAOYSA-N 2-(3-azidophenyl)-N-butyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(NCCCC)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=CC(N=[N+]=[N-])=C1 ZMYVMTMGMQNEIO-UHFFFAOYSA-N 0.000 claims 1
- FVIINQSYAIPCRO-UHFFFAOYSA-N 2-phenylimidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(N)=CC=CN2C=C1C1=CC=CC=C1 FVIINQSYAIPCRO-UHFFFAOYSA-N 0.000 claims 1
- SXLDLEPYDDYCTE-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(NCCOC)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 SXLDLEPYDDYCTE-UHFFFAOYSA-N 0.000 claims 1
- XNTPUOGJBALJKE-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(N)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 XNTPUOGJBALJKE-UHFFFAOYSA-N 0.000 claims 1
- UQKWYOKJTAQZEW-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-ol Chemical compound N1=C2C(O)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 UQKWYOKJTAQZEW-UHFFFAOYSA-N 0.000 claims 1
- DYLAIORIRDNGHX-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-N-(2-methoxyethyl)-2-(4-methylphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(NCCOC)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(C)C=C1 DYLAIORIRDNGHX-UHFFFAOYSA-N 0.000 claims 1
- LSTRFFKQHUBMHU-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-N-cyclopropyl-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CC3)C2=N1 LSTRFFKQHUBMHU-UHFFFAOYSA-N 0.000 claims 1
- MANUOFORAPEBLY-UHFFFAOYSA-N 4-(8-chloro-2-naphthalen-2-ylimidazo[1,2-a]pyridin-3-yl)-N-cyclopropylpyrimidin-2-amine Chemical compound C=1C=C2C=CC=CC2=CC=1C=1N=C2C(Cl)=CC=CN2C=1C(N=1)=CC=NC=1NC1CC1 MANUOFORAPEBLY-UHFFFAOYSA-N 0.000 claims 1
- NMRKSOZKKZYDSI-UHFFFAOYSA-N 4-[2-(3-aminophenyl)-8-chloroimidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine Chemical compound NC1=CC=CC(C2=C(N3C=CC=C(Cl)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 NMRKSOZKKZYDSI-UHFFFAOYSA-N 0.000 claims 1
- OHSONDFUJCMTMO-UHFFFAOYSA-N 4-[3-[2-(cyclopentylamino)pyrimidin-4-yl]-8-morpholin-4-ylimidazo[1,2-a]pyridin-2-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(N3CCOCC3)C2=N1 OHSONDFUJCMTMO-UHFFFAOYSA-N 0.000 claims 1
- FTFUULGTMRAHAY-UHFFFAOYSA-N 4-[3-[2-(cyclopentylamino)pyrimidin-4-yl]-8-morpholin-4-ylimidazo[1,2-a]pyridin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(N3CCOCC3)C2=N1 FTFUULGTMRAHAY-UHFFFAOYSA-N 0.000 claims 1
- SMLNJXMGWIHMTO-UHFFFAOYSA-N 4-[8-chloro-2-(3-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine Chemical compound COC1=CC=CC(C2=C(N3C=CC=C(Cl)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 SMLNJXMGWIHMTO-UHFFFAOYSA-N 0.000 claims 1
- OZTUYGIDUAVWAA-UHFFFAOYSA-N 4-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyridin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C(NC3CCCC3)N=CC=2)N2C=CC=C(Cl)C2=N1 OZTUYGIDUAVWAA-UHFFFAOYSA-N 0.000 claims 1
- ULQMUCVMULQROI-UHFFFAOYSA-N 4-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(Cl)C2=N1 ULQMUCVMULQROI-UHFFFAOYSA-N 0.000 claims 1
- NPHMIBPREUSWQP-UHFFFAOYSA-N 4-[8-chloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]-N-methylpyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2N3C=CC=C(Cl)C3=NC=2C=2C=CC(F)=CC=2)=N1 NPHMIBPREUSWQP-UHFFFAOYSA-N 0.000 claims 1
- JFQXAAAFFBEQNR-UHFFFAOYSA-N 4-[8-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(Cl)C2=N1 JFQXAAAFFBEQNR-UHFFFAOYSA-N 0.000 claims 1
- OSVNQLYQUHVVAG-UHFFFAOYSA-N 4-[8-chloro-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]-N-cyclopentylpyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(Cl)C2=N1 OSVNQLYQUHVVAG-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- PXKQLJBZGIJPDM-UHFFFAOYSA-N 6-bromo-N-butyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(NCCCC)=CC(Br)=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 PXKQLJBZGIJPDM-UHFFFAOYSA-N 0.000 claims 1
- FQNLYAUKXFCGMX-UHFFFAOYSA-N 8-chloro-2-(4-fluorophenyl)-3-(2-fluoropyridin-4-yl)imidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C(F)N=CC=2)N2C=CC=C(Cl)C2=N1 FQNLYAUKXFCGMX-UHFFFAOYSA-N 0.000 claims 1
- 208000006213 Herpesviridae Infection Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- CGZIWVFBQWMCFD-UHFFFAOYSA-N N-butyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound N1=C2C(NCCCC)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 CGZIWVFBQWMCFD-UHFFFAOYSA-N 0.000 claims 1
- SFZHOFPOUNTDEI-UHFFFAOYSA-N N-cyclopentyl-2-(4-fluorophenyl)-3-[2-(methylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-8-amine Chemical compound CNC1=NC=CC(C=2N3C=CC=C(NC4CCCC4)C3=NC=2C=2C=CC(F)=CC=2)=N1 SFZHOFPOUNTDEI-UHFFFAOYSA-N 0.000 claims 1
- UTDSTSHTAYLEKX-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyridin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 UTDSTSHTAYLEKX-UHFFFAOYSA-N 0.000 claims 1
- ZTIGLNXZTZDSSR-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(3-methoxyphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound COC1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 ZTIGLNXZTZDSSR-UHFFFAOYSA-N 0.000 claims 1
- QLKWIAJMBCQYCG-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(3-prop-2-enoxyphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C=CCOC1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 QLKWIAJMBCQYCG-UHFFFAOYSA-N 0.000 claims 1
- XYMXRVADPIBKBK-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=C(C(F)(F)F)C=C(NC3CCCC3)C2=N1 XYMXRVADPIBKBK-UHFFFAOYSA-N 0.000 claims 1
- AXMSBOPRFGDYRI-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyridin-6-amine Chemical compound C=1N2C(C=3N=C(NC4CCCC4)N=CC=3)=C(C=3C=CC(F)=CC=3)N=C2C(C)=CC=1NC1CCCC1 AXMSBOPRFGDYRI-UHFFFAOYSA-N 0.000 claims 1
- GFFDBCUDTYKXCG-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-6-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=C(NC3CCCC3)C=CC2=N1 GFFDBCUDTYKXCG-UHFFFAOYSA-N 0.000 claims 1
- KDCXXXLSBHIBQK-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 KDCXXXLSBHIBQK-UHFFFAOYSA-N 0.000 claims 1
- VPUGYGYLBZBBCE-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 VPUGYGYLBZBBCE-UHFFFAOYSA-N 0.000 claims 1
- UTSMIQYHCSZTSP-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methylphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(C)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 UTSMIQYHCSZTSP-UHFFFAOYSA-N 0.000 claims 1
- YMMFCUPZHSLJIM-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-prop-2-enoxyphenyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C1=CC(OCC=C)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 YMMFCUPZHSLJIM-UHFFFAOYSA-N 0.000 claims 1
- ZVFBUFIJHUDYHP-UHFFFAOYSA-N N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(cyclopropylmethoxy)phenyl]imidazo[1,2-a]pyridin-8-amine Chemical compound C1CC1COC(C=C1)=CC=C1C(=C(N1C=CC=2)C=3N=C(NC4CCCC4)N=CC=3)N=C1C=2NC1CCCC1 ZVFBUFIJHUDYHP-UHFFFAOYSA-N 0.000 claims 1
- DISYKLPBBBZJFY-UHFFFAOYSA-N N-cyclopentyl-4-[2-(4-fluorophenyl)-6,8-dimorpholin-4-ylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=C(N3CCOCC3)C=C(N3CCOCC3)C2=N1 DISYKLPBBBZJFY-UHFFFAOYSA-N 0.000 claims 1
- JPLNWTQRWZCVJP-UHFFFAOYSA-N N-cyclopentyl-4-[2-(4-fluorophenyl)-6-morpholin-4-ylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=C(N3CCOCC3)C=CC2=N1 JPLNWTQRWZCVJP-UHFFFAOYSA-N 0.000 claims 1
- QXFHXADPSUXSBL-UHFFFAOYSA-N N-cyclopentyl-4-[2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N1=C2C(C)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 QXFHXADPSUXSBL-UHFFFAOYSA-N 0.000 claims 1
- WENYNNGFKKTUSB-UHFFFAOYSA-N N-cyclopentyl-4-[2-(4-fluorophenyl)-8-phenylmethoxyimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(OCC=3C=CC=CC=3)C2=N1 WENYNNGFKKTUSB-UHFFFAOYSA-N 0.000 claims 1
- HXLGDAAWRUWBGI-UHFFFAOYSA-N N-cyclopentyl-4-[2-(4-fluorophenyl)-8-pyrrolidin-1-ylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(N3CCCC3)C2=N1 HXLGDAAWRUWBGI-UHFFFAOYSA-N 0.000 claims 1
- LFAOAOFMOZLDCM-UHFFFAOYSA-N N-cyclopentyl-4-[2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=CC2=N1 LFAOAOFMOZLDCM-UHFFFAOYSA-N 0.000 claims 1
- BHTDWFAZQHBMRT-UHFFFAOYSA-N N-cyclopentyl-4-[2-(4-methylphenyl)-8-morpholin-4-ylimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(N3CCOCC3)C2=N1 BHTDWFAZQHBMRT-UHFFFAOYSA-N 0.000 claims 1
- CEYKJBAJFUSKPH-UHFFFAOYSA-N N-cyclopentyl-4-[6,8-dibromo-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=C(Br)C=C(Br)C2=N1 CEYKJBAJFUSKPH-UHFFFAOYSA-N 0.000 claims 1
- QEUYKZFRAGXCJT-UHFFFAOYSA-N N-cyclopentyl-4-[6,8-dichloro-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=C(Cl)C=C(Cl)C2=N1 QEUYKZFRAGXCJT-UHFFFAOYSA-N 0.000 claims 1
- XGNAKZXUNNMJLJ-UHFFFAOYSA-N N-cyclopentyl-4-[8-morpholin-4-yl-2-(3-nitrophenyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound [O-][N+](=O)C1=CC=CC(C2=C(N3C=CC=C(C3=N2)N2CCOCC2)C=2N=C(NC3CCCC3)N=CC=2)=C1 XGNAKZXUNNMJLJ-UHFFFAOYSA-N 0.000 claims 1
- GIYMAQODFWMRCG-UHFFFAOYSA-N N-cyclopropyl-3-[2-(cyclopropylamino)pyrimidin-4-yl]-2-naphthalen-2-ylimidazo[1,2-a]pyridin-8-amine Chemical compound C1CC1NC1=NC=CC(C=2N3C=CC=C(NC4CC4)C3=NC=2C=2C=C3C=CC=CC3=CC=2)=N1 GIYMAQODFWMRCG-UHFFFAOYSA-N 0.000 claims 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 101700078369 nhr-9 Proteins 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
Claims (4)
- 次式(I)の化合物またはその医薬的に許容される塩、溶媒和物もしくは生理学的に機能する誘導体。
pは0、1、2、3または4であり、
R1はそれぞれ同じであるかまたは異なっており、ハロ、アルキル、アルケニル、アルキニル、シクロアルキル、シクロアルケニル、Ay、Het、-OR7、-OAy、-OR10Ay、-OHet、-OR10Het、-C(O)R9、-C(O)Ay、-C(O)Het、-CO2R9、-C(O)NR7R8、-C(O)NR7Ay、-C(O)NHR10Ay、-C(O)NHR10Het、-C(S)NR9R11、-C(NH)NR7R8、-C(NH)NR7Ay、-S(O)nR9、-S(O)nAy、-S(O)nHet、-S(O)2NR7R8、-S(O)2NR7Ay、-NR7R8、-NR7Ay、-NHHet、-NHR10Ay、-NHR10Het、-R10シクロアルキル、-R10Ay、-R10Het、-R10O-C(O)R9、-R10O-C(O)Ay、-R10O-C(O)Het、-R10O-S(O)nR9、-R10OR9、-R10C(O)R9、-R10CO2R9、-R10C(O)NR9R11、-R10C(O)NR7Ay、-R10C(O)NHR10Het、-R10C(S)NR9R11、-R10C(NH)NR9R11、-R10SO2R9、-R10SO2NR9R11、-R10SO2NHCOR9、-R10NR7R8、-R10NR7Ay、-R10NHC(NH)NR9R11、シアノ、ニトロおよびアジドからなる群から独立に選択されるか、または
2つの隣接するR1基がそれらが結合している原子と一緒になってC5-6シクロアルキルまたは1もしくは2個のヘテロ原子を持つ5もしくは6員ヘテロ環を形成しており、
R7およびR8はそれぞれ同じであるかまたは異なっており、H、アルキル、シクロアルキル、アルケニル、シクロアルケニル、-OR9、-C(O)R9、-CO2R9、-C(O)NR9R11、-C(S)NR9R11、-C(NH)NR9R11、-SO2R10、-SO2NR9R11、-R10シクロアルキル、-R10OR9、-R10C(O)R9、-R10CO2R9、-R10C(O)NR9R11、-R10C(S)NR9R11、-R10C(NH)NR9R11、-R10SO2R10、-R10SO2NR9R11、-R10SO2NHCOR9、-R10NR9R11、-R10NHCOR9、-R10NHSO2R9および-R10NHC(NH)NR9R11からなる群から独立に選択され、
R9およびR11はそれぞれ同じであるかまたは異なっており、H、アルキル、シクロアルキル、-R10シクロアルキル、-R10OH、-R10(OR10)w[式中、wは1〜10である]、および-R10NR10R10からなる群から独立に選択されるものであり;
R10はそれぞれ同じであるかまたは異なっており、アルキル、アルケニル、アルキニル、シクロアルキルおよびシクロアルケニルからなる群から独立に選択され、
Ayはアリールであり、
Hetは5または6員ヘテロ環式またはヘテロアリール基であり、
R2はハロ、アルケニル、シクロアルキル、シクロアルケニル、Ay、Het、-OR7、-OAy、-OHet、-OR10Het、-S(O)nR9、-S(O)nAy、-S(O)nNR7R8、-S(O)nHet、-NR7R8、-NHHet、-NHR10Ay、-NHR10Het、-R10NR7R8および-R10NR7Ayからなる群から選択され、
nは0、1または2であり、
YはNまたはCHであり、
R3およびR4は同じであるかまたは異なっており、H、ハロ、アルキル、アルケニル、シクロアルキル、Ay、Het、-OR7、-OAy、-C(O)R7、-C(O)Ay、-CO2R7、-CO2Ay、-SO2NHR9、-NR7R8、-NR7Ay、-NHHet、-NHR10Het、-R10シクロアルキル、-R10OR7、-R10OAy、-R10NR7R8および-R10NR7Ayからなる群から独立に選択され、
qは0、1、2、3、4または5であり、
R5はそれぞれ同じであるかまたは異なっており、ハロ、アルキル、アルケニル、アルキニル、シクロアルキル、シクロアルケニル、Ay、Het、-OR7、-OAy、-OHet、-OR10Ay、-OR10Het、-C(O)R9、-C(O)Ay、-C(O)Het、-CO2R9、-C(O)NR7R8、-C(O)NR7Ay、-C(O)NHR10Het、-C(S)NR9R11、-C(NH)NR7R8、-C(NH)NR7Ay、-S(O)nR9、-S(O)2NR7R8、-S(O)2NR7Ay、-NR7R8、-NR7Ay、-NHHet、-NHR10Ay、-NHR10Het、-R10シクロアルキル、-R10Het、-R10OR9、-R10C(O)R9、-R10CO2R9、-R10C(O)NR9R11,-R10C(O)NR7Ay、-R10C(O)NHR10Het、-R10C(S)NR9R11、-R10C(NH)NR9R11、-R10SO2R9、-R10SO2NR9R11、-R10SO2NHCOR9、-R10NR7R8、-R10NR7Ay、-R10NHC(NH)NR9R11、シアノ、ニトロおよびアジドからなる群から独立に選択されるか、または
2つの隣接するR5基がそれらが結合している原子と一緒になってC5-6シクロアルキルまたはアリールを形成している。但し、YがCHである場合、R3は-NR7Ayではない。 - 3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
4-[8-クロロ-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-N-シクロペンチル-2-ピリミジンアミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
N-シクロペンチル-4-[2-(4-フルオロフェニル)-8-(1-ピロリジニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
N-ブチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)-N-(2-メトキシエチル)イミダゾ[1,2-a]ピリジン-8-アミン;
4-[8-クロロ-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-N-メチル-2-ピリミジンアミン;
N-シクロペンチル-2-(4-フルオロフェニル)-3-[2-(メチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-8-アミン;
4-[8-クロロ-2-(4-メトキシフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-N-シクロペンチル-2-ピリミジンアミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-メトキシフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
4-8-(シクロペンチルアミノ)-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-2-イルフェノール;
8-クロロ-2-(4-フルオロフェニル)-3-(2-フルオロ-4-ピリジニル)イミダゾ[1,2-a]ピリジン;
4-[8-クロロ-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-N-シクロペンチル-2-ピリジンアミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリジニル]-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
4-[8-クロロ-2-(3-メトキシフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-N-シクロペンチル-2-ピリミジンアミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(3-メトキシフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
3-8-(シクロペンチルアミノ)-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-2-イルフェノール;
2-[3-(アリルオキシ)フェニル]-N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-8-アミン;
4-[8-クロロ-2-(4-メチルフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-N-シクロペンチル-2-ピリミジンアミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-メチルフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-N-(2-メトキシエチル)-2-(4-メチルフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
N-シクロペンチル-4-[2-(4-メチルフェニル)-8-(4-モルホリニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
4-[8-クロロ-2-(2-ナフチル)イミダゾ[1,2-a]ピリジン-3-イル]-N-シクロプロピル-2-ピリミジンアミン;
N-シクロプロピル-3-[2-(シクロプロピルアミノ)-4-ピリミジニル]-2-(2-ナフチル)イミダゾ[1,2-a]ピリジン-8-アミン;
4-8-クロロ-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-2-イルベンゾニトリル;
4-8-(シクロペンチルアミノ)-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-2-イルベンゾニトリル;
4-[3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-8-(4-モルホリニル)イミダゾ[1,2-a]ピリジン-2-イル]ベンゾニトリル;
4-[3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-8-(4-モルホリニル)イミダゾ[1,2-a]ピリジン-2-イル]ベンザミド;
4-8-(シクロペンチルアミノ)-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-2-イルベンザミド;
N-4-[8-クロロ-2-(3-ニトロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジニル-N-シクロペンチルアミン;
N-シクロペンチル-4-[8-(4-モルホリニル)-2-(3-ニトロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
4-[2-(3-アミノフェニル)-8-クロロイミダゾ[1,2-a]ピリジン-3-イル]-N-シクロペンチル-2-ピリミジンアミン;
2-(3-アミノフェニル)-N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-8-アミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-3-[(シクロプロピルメチル)アミノ]フェニルイミダゾ[1,2-a]ピリジン-8-アミン;
2-3-[ビス(シクロプロピルメチル)アミノ]フェニル-N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-8-アミン;
3-8-クロロ-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-2-イルベンゾニトリル;
3-8-(シクロペンチルアミノ)-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-2-イルベンゾニトリル;
N-シクロペンチル-4-[6,8-ジクロロ-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
N-4-[6-クロロ-8-(シクロペンチルアミノ)-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジニル-N-シクロペンチルアミン;
N-シクロペンチル-4-[6,8-ジブロモ-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
N-4-[6-ブロモ-8-(シクロペンチルアミノ)-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジニル-N-シクロペンチルアミン;
6-ブロモ-N-ブチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
N-シクロペンチル-4-[2-(4-フルオロフェニル)-6,8-ジ(4-モルホリニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
N-4-[6-ブロモ-2-(4-フルオロフェニル)-8-メチルイミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジニル-N-シクロペンチルアミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)-8-メチルイミダゾ[1,2-a]ピリジン-6-アミン;
N-シクロペンチル-4-[2-(4-フルオロフェニル)-8-メチルイミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
N-4-[6-ブロモ-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジニル-N-シクロペンチルアミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-6-アミン;
N-シクロペンチル-4-[2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
N-シクロペンチル-4-[2-(4-フルオロフェニル)-6-(4-モルホリニル)イミダゾ[1,2-a]ピリジン-3-イル]-2-ピリミジンアミン;
3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-N-シクロプロピル-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-8-アミン;
2-[4-(アリルオキシ)フェニル]-N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]イミダゾ[1,2-a]ピリジン-8-アミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-[4-(シクロプロピルメトキシ)フェニル]イミダゾ[1,2-a]ピリジン-8-アミン;
N-シクロペンチル-3-[2-(シクロペンチルアミノ)-4-ピリミジニル]-2-(4-フルオロフェニル)-6-(トリフルオロメチル)イミダゾ[1,2-a]ピリジン-8-アミン;
3-8-(シクロペンチルアミノ)-3-[2-(シクロペンチルアミノ)ピリミジン-4-イル]イミダゾ[1,2-a]ピリジン-2-イル安息香酸;
2-(3-アジドフェニル)-N-ブチル-3-[2-(シクロペンチルアミノ)ピリミジン-4-イル]イミダゾ[1,2-a]ピリジン-8-アミン;
4-[8-(ベンジルオキシ)-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-3-イル]-N-シクロペンチルピリミジン-2-アミン;および
3-[2-(シクロペンチルアミノ)ピリミジン-4-イル]-2-(4-フルオロフェニル)イミダゾ[1,2-a]ピリジン-8-オール
からなる群から選択される化合物またはその医薬的に許容される塩、溶媒和物もしくは生理学的に機能する誘導体。 - 請求項1または2に記載の化合物を含む医薬組成物。
- 動物のヘルペスウイルス感染の予防または治療で使用される、請求項1または2に記載の化合物を含む医薬組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30000901P | 2001-06-21 | 2001-06-21 | |
PCT/US2002/018520 WO2003000689A1 (en) | 2001-06-21 | 2002-06-10 | Imidazo`1,2-a!pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005500315A JP2005500315A (ja) | 2005-01-06 |
JP2005500315A5 true JP2005500315A5 (ja) | 2005-09-02 |
Family
ID=23157269
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003507092A Pending JP2005500315A (ja) | 2001-06-21 | 2002-06-10 | ヘルペスウイルス感染の予防および治療用イミダゾ[1,2−a]ピリジン誘導体 |
Country Status (19)
Country | Link |
---|---|
US (3) | US7186714B2 (ja) |
EP (1) | EP1401836B1 (ja) |
JP (1) | JP2005500315A (ja) |
KR (1) | KR20040018281A (ja) |
CN (1) | CN1518550A (ja) |
AT (1) | ATE337316T1 (ja) |
BR (1) | BR0210464A (ja) |
CA (1) | CA2451008A1 (ja) |
CO (1) | CO5540312A2 (ja) |
CZ (1) | CZ20033518A3 (ja) |
DE (1) | DE60214179T2 (ja) |
ES (1) | ES2271273T3 (ja) |
HU (1) | HUP0400266A2 (ja) |
IL (1) | IL158667A0 (ja) |
MX (1) | MXPA03011906A (ja) |
NO (1) | NO20035583D0 (ja) |
PL (1) | PL366827A1 (ja) |
WO (1) | WO2003000689A1 (ja) |
ZA (1) | ZA200308726B (ja) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6977574B1 (en) * | 1997-02-14 | 2005-12-20 | Denso Corporation | Stick-type ignition coil having improved structure against crack or dielectric discharge |
CA2451008A1 (en) * | 2001-06-21 | 2003-01-03 | Smithkline Beecham Corporation | Imidazo[1,2-a!pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
DE60301339T2 (de) | 2002-03-07 | 2006-03-09 | Smithkline Beecham Corp. | Pyrazolopyrimidin- und pyrazolotriazinderivate und diese enthaltende pharmazeutische zubereitungen |
CN101048406B (zh) * | 2004-08-31 | 2010-12-22 | 万有制药株式会社 | 新型取代的咪唑衍生物 |
NZ573363A (en) | 2006-05-19 | 2012-01-12 | Nihon Mediphysics Co Ltd | Compound having affinity for amyloid based on an imidazopyridine-phenyl skeleton |
WO2008059714A1 (fr) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Composés inédits présentant une affinité pour la substance amyloïde |
KR20090083414A (ko) | 2006-11-30 | 2009-08-03 | 니혼 메디피직스 가부시키가이샤 | 신규 아밀로이드 친화성 화합물 |
EP2119458B9 (en) | 2007-02-13 | 2013-08-21 | Nihon Medi-Physics Co., Ltd. | Method for production of radiation diagnostic imaging agent |
EP1964840A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]pyridines and their use as pharmaceuticals |
WO2009054496A1 (ja) * | 2007-10-24 | 2009-04-30 | Nihon Medi-Physics Co., Ltd. | 新規アミロイド親和性化合物 |
CA2704137A1 (en) * | 2007-10-30 | 2009-05-07 | Nihon Medi-Physics Co., Ltd. | Use of novel compound having affinity for amyloid, and process for production of the same |
UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
NZ590283A (en) | 2008-07-14 | 2012-11-30 | Gilead Sciences Inc | Imidazolylpyrimidine compounds as hdac and / or cdk inhibitors |
WO2010009155A2 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Fused heterocyclyc inhibitor compounds |
EP2303841A1 (en) | 2008-07-14 | 2011-04-06 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
EP2326622A1 (en) | 2008-07-28 | 2011-06-01 | Gilead Sciences, Inc. | Cycloalkylidene and heterocycloalkylidene histone deacetylase inhibitor compounds |
US20100204265A1 (en) * | 2009-02-09 | 2010-08-12 | Genelabs Technologies, Inc. | Certain Nitrogen Containing Bicyclic Chemical Entities for Treating Viral Infections |
AU2010259042A1 (en) | 2009-06-08 | 2011-12-15 | Gilead Sciences, Inc. | Cycloalkylcarbamate benzamide aniline HDAC inhibitor compounds |
US8258316B2 (en) | 2009-06-08 | 2012-09-04 | Gilead Sciences, Inc. | Alkanoylamino benzamide aniline HDAC inhibitor compounds |
WO2011041713A2 (en) * | 2009-10-02 | 2011-04-07 | Glaxosmithkline Llc | Piperazinyl antiviral agents |
ES2651296T3 (es) | 2009-10-30 | 2018-01-25 | Janssen Pharmaceutica, N.V. | Derivados de imidazo[1,2-b]piridacina y su uso como inhibidores de PDE10 |
AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
WO2013000924A1 (en) | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
EP2863909B1 (en) | 2012-06-26 | 2020-11-04 | Janssen Pharmaceutica N.V. | Combinations comprising 4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline compounds as pde 2 inhibitors and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
CN104411314B (zh) | 2012-07-09 | 2017-10-20 | 詹森药业有限公司 | 磷酸二酯酶10的抑制剂 |
WO2014195333A1 (de) * | 2013-06-04 | 2014-12-11 | Bayer Pharma Aktiengesellschaft | 3-aryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
MX2016008624A (es) | 2013-12-30 | 2017-01-06 | Genentech Inc | Inhibidores de serina/treonina cinasa. |
CA2939793A1 (en) | 2014-02-19 | 2015-08-27 | Bayer Pharma Aktiengesellschaft | 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines |
US11071745B2 (en) * | 2014-07-07 | 2021-07-27 | Elian Llc | Viral prophylaxis treatment methods and pre-exposure prophylaxis kits |
CN107001361A (zh) | 2014-12-02 | 2017-08-01 | 拜耳医药股份有限公司 | 杂芳基取代的咪唑并[1,2‑a]吡啶及其用途 |
US11111245B2 (en) | 2017-02-01 | 2021-09-07 | Aucentra Therapeutics Pty Ltd | Derivatives of N-cycloalkyl/heterocycloalkyl-4-(imidazo[1,2-a]pyridine)pyrimidin-2-amine as therapeutic agents |
CN110483506B (zh) * | 2019-08-02 | 2022-04-19 | 桂林理工大学 | 以DMF为甲酰化试剂构建2-(2-噻吩基)咪唑[1,2-a]吡啶-3-醛的新方法 |
CN110483504B (zh) * | 2019-08-02 | 2022-04-26 | 桂林理工大学 | 以DMF为甲酰化试剂构建2-(2-萘基)咪唑[1,2-a]吡啶-3-醛的新方法 |
Family Cites Families (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0151962A3 (en) | 1984-01-25 | 1985-10-02 | Beecham Group Plc | Pyrazolopyridine derivatives |
GB8404584D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
GB8404586D0 (en) | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
US5145858A (en) | 1985-12-12 | 1992-09-08 | Smithkline Beecham Corp. | Pyrrolo [1,2-a] imidazole and imidazo [1,2a] pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
US4719218A (en) | 1985-12-12 | 1988-01-12 | Smithkline Beckman Corporation | Pyrrolo[1,2-a]imidazole and pyrrolo[1,2-a]pyridine derivatives and their use as 5-lipoxygenase pathway inhibitor |
US5002941A (en) | 1985-12-12 | 1991-03-26 | Smithkline Beecham Corporation | Pyrrolo(1,2-a)imidazole and imidazo(1,2-a)pyridine derivatives and their use as 5-lipoxygenase pathway inhibitors |
US4794114A (en) | 1986-08-19 | 1988-12-27 | Smithkline Beckman Corporation | Inhibition of interleukin-1 production by monocytes and/or macrophages |
US4925849A (en) | 1987-06-15 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | Pharmaceutically useful pyrazolopyridines |
US5155114A (en) | 1989-01-23 | 1992-10-13 | Fujisawa Pharmaceutical Company, Ltd. | Method of treatment using pyrazolopyridine compound |
GB8901423D0 (en) | 1989-01-23 | 1989-03-15 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
CA2058952A1 (en) | 1989-06-13 | 1990-12-14 | Nabil Hanna | Monokine activity interference |
CA2060309A1 (en) * | 1989-06-13 | 1990-12-14 | Alison M. Badger | Inhibition of interleukin-1 and tumor necrosis factor production by monocytes and/or macrophages |
AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
EP0533837A4 (en) | 1990-06-12 | 1994-11-17 | Smithkline Beecham Corp | Inhibition of 5-lipoxygenase and cyclooxygenase pathway mediated diseases |
GB9015764D0 (en) | 1990-07-18 | 1990-09-05 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
GB9026926D0 (en) | 1990-12-12 | 1991-01-30 | Smith Kline French Lab | Novel process |
AU9169991A (en) | 1990-12-13 | 1992-07-08 | Smithkline Beecham Corporation | Novel csaids |
EP0565582A4 (en) | 1990-12-13 | 1995-01-11 | Smithkline Beecham Corp | NOVEL CYTOKINE SUPPRESSIVE ANTI-INFLAMMATORY DRUGS. |
ATE211384T1 (de) | 1991-01-29 | 2002-01-15 | Fujisawa Pharmaceutical Co | Verwendung von adenosinantagonisten zur vorbeugung und behandlung von pankreatitis und ulcera |
GB9107513D0 (en) | 1991-04-10 | 1991-05-29 | Fujisawa Pharmaceutical Co | Pyrazolopyridine compound and processes for preparation thereof |
US5300478A (en) | 1993-01-28 | 1994-04-05 | Zeneca Limited | Substituted fused pyrazolo compounds |
US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
US5521213A (en) | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
CN1088062C (zh) | 1994-11-23 | 2002-07-24 | 纽罗根公司 | 某些4-氨基甲基-2-取代的咪唑衍生物2-氨基甲基-4-取代的咪唑衍生物新的一族多巴胺受体亚型特异性配体 |
US5552422A (en) | 1995-01-11 | 1996-09-03 | Merck Frosst Canada, Inc. | Aryl substituted 5,5 fused aromatic nitrogen compounds as anti-inflammatory agents |
HUP9801602A3 (en) | 1995-04-04 | 1999-01-28 | Glaxo Group Ltd | Imidazo[1,2-a]pyridine derivatives, process for their production, pharmaceutical compositions and use thereof |
WO1996034866A1 (en) | 1995-05-01 | 1996-11-07 | Fujisawa Pharmaceutical Co., Ltd. | Imidazo 1,2-a pyridine and imidazo 1,2-a pyridezine derivatives and their use as bone resorption inhibitors |
EP0833664A1 (en) | 1995-06-12 | 1998-04-08 | G.D. SEARLE & CO. | Combination of a cyclooxygenase-2 inhibitor and a leukotriene b 4? receptor antagonist for the treatment of inflammations |
US5700816A (en) | 1995-06-12 | 1997-12-23 | Isakson; Peter C. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitor and a leukotriene A4 hydrolase inhibitor |
DE69635048T2 (de) | 1995-06-12 | 2006-02-16 | G.D. Searle & Co. | Mittel, enthaltend einen cyclooxygenase-2 inhibitor und einen 5-lipoxygenase inhibitor |
FR2757166B1 (fr) | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
FR2757059B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Nouvelle application therapeutique des derives du pyrrole |
AU7966198A (en) | 1997-06-13 | 1998-12-30 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
PL194557B1 (pl) | 1997-09-05 | 2007-06-29 | Glaxo Group Ltd | Pochodna 2,3-diarylopirazolo[1,5-b]pirydazyny, jej wytwarzanie, kompozycja farmaceutyczna zawierająca pochodną i jej zastosowanie |
JP2002514640A (ja) | 1998-05-14 | 2002-05-21 | ジー・ディー・サール・アンド・カンパニー | p38キナーゼ阻害剤としての1,5−ジアリール置換ピラゾール類 |
US6245789B1 (en) | 1998-05-19 | 2001-06-12 | The Procter & Gamble Company | HIV and viral treatment |
FR2779724B1 (fr) | 1998-06-10 | 2001-04-20 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
CN1263755C (zh) | 1998-11-03 | 2006-07-12 | 葛兰素集团有限公司 | 作为选择性cox-2抑制剂的吡唑并吡啶衍生物 |
DE69915519T2 (de) | 1999-02-27 | 2005-02-03 | Glaxo Group Ltd., Greenford | Pyrazolopyridine |
JP4032566B2 (ja) | 1999-06-21 | 2008-01-16 | 東レ株式会社 | 発光素子 |
BR0011997A (pt) | 1999-06-28 | 2002-03-05 | Janssen Pharmaceutica Nv | Inibidores da replicação do vìrus sincicial respiratório |
GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
CA2311483A1 (en) | 2000-06-12 | 2001-12-12 | Gregory N Beatch | IMIDAZO [1,2-A] PYRIDINIC ETHERS AND USES THEREOF |
PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
AUPQ969800A0 (en) | 2000-08-28 | 2000-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
AU2002239348A1 (en) | 2000-12-15 | 2002-06-24 | Glaxo Group Limited | Pyrazolopyridine derivatives |
DE60112609T2 (de) | 2000-12-15 | 2006-01-19 | Glaxo Group Ltd., Greenford | Pyrazolopyridine |
GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
CA2451008A1 (en) * | 2001-06-21 | 2003-01-03 | Smithkline Beecham Corporation | Imidazo[1,2-a!pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
US7196095B2 (en) * | 2001-06-25 | 2007-03-27 | Merck & Co., Inc. | (Pyrimidinyl) (phenyl) substituted fused heteroaryl p38 inhibiting and PKG kinase inhibiting compounds |
ES2262893T3 (es) * | 2001-10-05 | 2006-12-01 | Smithkline Beecham Corporation | Derivados de imidazo-piridina para su uso en el tratamiento de infeccion virica por herpes. |
-
2002
- 2002-06-10 CA CA002451008A patent/CA2451008A1/en not_active Abandoned
- 2002-06-10 WO PCT/US2002/018520 patent/WO2003000689A1/en active IP Right Grant
- 2002-06-10 PL PL02366827A patent/PL366827A1/xx not_active Application Discontinuation
- 2002-06-10 CN CNA028124499A patent/CN1518550A/zh active Pending
- 2002-06-10 DE DE60214179T patent/DE60214179T2/de not_active Expired - Fee Related
- 2002-06-10 IL IL15866702A patent/IL158667A0/xx unknown
- 2002-06-10 BR BR0210464-4A patent/BR0210464A/pt not_active Application Discontinuation
- 2002-06-10 ES ES02739833T patent/ES2271273T3/es not_active Expired - Lifetime
- 2002-06-10 KR KR10-2003-7016716A patent/KR20040018281A/ko not_active Application Discontinuation
- 2002-06-10 JP JP2003507092A patent/JP2005500315A/ja active Pending
- 2002-06-10 CZ CZ20033518A patent/CZ20033518A3/cs unknown
- 2002-06-10 US US10/479,526 patent/US7186714B2/en not_active Expired - Fee Related
- 2002-06-10 EP EP02739833A patent/EP1401836B1/en not_active Expired - Lifetime
- 2002-06-10 AT AT02739833T patent/ATE337316T1/de not_active IP Right Cessation
- 2002-06-10 HU HU0400266A patent/HUP0400266A2/hu unknown
- 2002-06-10 MX MXPA03011906A patent/MXPA03011906A/es unknown
-
2003
- 2003-11-10 ZA ZA200308726A patent/ZA200308726B/en unknown
- 2003-12-15 NO NO20035583A patent/NO20035583D0/no not_active Application Discontinuation
- 2003-12-16 CO CO03109957A patent/CO5540312A2/es not_active Application Discontinuation
-
2006
- 2006-03-29 US US11/391,867 patent/US20060167252A1/en not_active Abandoned
-
2007
- 2007-01-25 US US11/627,078 patent/US20070135451A1/en not_active Abandoned
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2005500315A5 (ja) | ||
JP2004527560A5 (ja) | ||
JP2004525149A5 (ja) | ||
JP2004518651A5 (ja) | ||
JP2020504136A5 (ja) | ||
JP2022184886A5 (ja) | ||
KR101110530B1 (ko) | 증식성 질환의 치료에 유용한 키나제 억제제 | |
RU2424242C2 (ru) | Азолопиримидины в качестве ингибиторов активности каннабиноидного рецептора 1 | |
HRP20150837T1 (hr) | Heteroaril supstituirani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze | |
RU97100192A (ru) | Антагонисты кортикотропин-рилизинг фактора | |
US20050209250A1 (en) | Therapeutic combinations of atypical antipsychotics with corticotropin releasing factor antagonists | |
JP2017535561A5 (ja) | ||
JP2007522200A5 (ja) | ||
RU2017106742A (ru) | Комбинированная терапия для лечения парамиксовируса | |
JP2008506644A5 (ja) | ||
JP2016520116A5 (ja) | ||
KR20160023684A (ko) | 신규한 바이사이클릭 브로모도메인 억제제 | |
JP2015504061A5 (ja) | ||
JP2010513447A5 (ja) | ||
RU2014115476A (ru) | Производные пиразоло[4, 3-с]птридина в качестве ингибиторов киназ | |
JP2013522354A5 (ja) | ||
JP2016504290A5 (ja) | ||
JP2018529731A5 (ja) | ||
JP2014531449A5 (ja) | ||
JP2004515550A5 (ja) |