JP2005500315A5 - - Google Patents
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- 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
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- 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.)
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- 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。
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|---|---|---|---|
| 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 |
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| US11071745B2 (en) * | 2014-07-07 | 2021-07-27 | Elian Llc | Viral prophylaxis treatment methods and pre-exposure prophylaxis kits |
| WO2016087343A1 (de) | 2014-12-02 | 2016-06-09 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
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2002
- 2002-06-10 IL IL15866702A patent/IL158667A0/xx unknown
- 2002-06-10 CN CNA028124499A patent/CN1518550A/zh active Pending
- 2002-06-10 JP JP2003507092A patent/JP2005500315A/ja active Pending
- 2002-06-10 KR KR10-2003-7016716A patent/KR20040018281A/ko not_active Application Discontinuation
- 2002-06-10 WO PCT/US2002/018520 patent/WO2003000689A1/en active IP Right Grant
- 2002-06-10 MX MXPA03011906A patent/MXPA03011906A/es unknown
- 2002-06-10 BR BR0210464-4A patent/BR0210464A/pt not_active Application Discontinuation
- 2002-06-10 HU HU0400266A patent/HUP0400266A2/hu unknown
- 2002-06-10 EP EP02739833A patent/EP1401836B1/en not_active Expired - Lifetime
- 2002-06-10 ES ES02739833T patent/ES2271273T3/es not_active Expired - Lifetime
- 2002-06-10 AT AT02739833T patent/ATE337316T1/de not_active IP Right Cessation
- 2002-06-10 CA CA002451008A patent/CA2451008A1/en not_active Abandoned
- 2002-06-10 CZ CZ20033518A patent/CZ20033518A3/cs unknown
- 2002-06-10 DE DE60214179T patent/DE60214179T2/de not_active Expired - Fee Related
- 2002-06-10 US US10/479,526 patent/US7186714B2/en not_active Expired - Fee Related
- 2002-06-10 PL PL02366827A patent/PL366827A1/xx not_active Application Discontinuation
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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
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2007
- 2007-01-25 US US11/627,078 patent/US20070135451A1/en not_active Abandoned
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