HUP0400266A2 - Imidazo[1,2-a]piridin-származékok, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk herpeszvírus-fertőzések megelőzésére vagy kezelésére - Google Patents

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Publication number

HUP0400266A2

HUP0400266A2 HU0400266A HUP0400266A HUP0400266A2 HU P0400266 A2 HUP0400266 A2 HU P0400266A2 HU 0400266 A HU0400266 A HU 0400266A HU P0400266 A HUP0400266 A HU P0400266A HU P0400266 A2 HUP0400266 A2 HU P0400266A2

Authority

HU

Hungary

Prior art keywords

imidazo

pyridin

het

cyclopentylamino

pyrimidinyl

Prior art date

2001-06-21

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• 238000011282 treatment Methods 0.000 title claims description 32
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 24
• 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title description 2
• 206010019972 Herpes viral infections Diseases 0.000 title 1
• 238000011321 prophylaxis Methods 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 425
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 120
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 100
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 78
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 66
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
• 239000001257 hydrogen Substances 0.000 claims abstract description 61
• 125000003118 aryl group Chemical group 0.000 claims abstract description 60
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 46
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 42
• 150000002367 halogens Chemical group 0.000 claims abstract description 41
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 33
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 31
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 30
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 25
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 24
• 239000012453 solvate Substances 0.000 claims abstract description 23
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 18
• 238000000034 method Methods 0.000 claims description 149
• 125000004429 atom Chemical group 0.000 claims description 38
• 230000008569 process Effects 0.000 claims description 37
• 238000002360 preparation method Methods 0.000 claims description 35
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 30
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 29
• 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 241001465754 Metazoa Species 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
• 230000002265 prevention Effects 0.000 claims description 27
• 125000005843 halogen group Chemical group 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 241000282412 Homo Species 0.000 claims description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• LKQXJYDAALZCAF-UHFFFAOYSA-N imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C=CN=C12 LKQXJYDAALZCAF-UHFFFAOYSA-N 0.000 claims description 14
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 13
• 150000004820 halides Chemical class 0.000 claims description 13
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 9
• MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 9
• 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 description 8
• 229960004150 aciclovir Drugs 0.000 claims description 8
• 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 description 8
• 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 description 7
• HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 claims description 7
• 239000003443 antiviral agent Substances 0.000 claims description 7
• 229940093257 valacyclovir Drugs 0.000 claims description 7
• 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 description 6
• QDFWKBAGOVAQKX-UHFFFAOYSA-N 4-[6-bromo-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=C(Br)C=CC2=N1 QDFWKBAGOVAQKX-UHFFFAOYSA-N 0.000 claims description 6
• WJDLDBKLZHQTFK-UHFFFAOYSA-N 4-[8-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[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(NC3CCCC3)C2=N1 WJDLDBKLZHQTFK-UHFFFAOYSA-N 0.000 claims description 6
• 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 description 6
• VAWWTVSHFJTEMP-UHFFFAOYSA-N chembl230944 Chemical compound C1=CC(O)=CC=C1C1=C(C=2N=C(NC3CCCC3)N=CC=2)N2C=CC=C(NC3CCCC3)C2=N1 VAWWTVSHFJTEMP-UHFFFAOYSA-N 0.000 claims description 6
• 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 description 6
• 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 description 6
• 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 description 5
• 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 description 5
• 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 description 5
• 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 description 5
• 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 description 5
• HYXROYJLXWGOOT-UHFFFAOYSA-N 6-bromo-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=C(Br)C=C(NC3CCCC3)C2=N1 HYXROYJLXWGOOT-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• 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 description 5
• 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 description 5
• 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 description 5
• 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 description 4
• 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 description 4
• 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 description 4
• DNLJGGVFRLKDHN-UHFFFAOYSA-N 3-[8-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 DNLJGGVFRLKDHN-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• NJQHGIUYPDLKAA-UHFFFAOYSA-N 2-[3-[bis(cyclopropylmethyl)amino]phenyl]-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-8-amine Chemical compound C1CC1CN(C=1C=C(C=CC=1)C1=C(N2C=CC=C(NC3CCCC3)C2=N1)C=1N=C(NC2CCCC2)N=CC=1)CC1CC1 NJQHGIUYPDLKAA-UHFFFAOYSA-N 0.000 claims description 3
• XYSGNRYFSMZFMA-UHFFFAOYSA-N 3-[8-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 XYSGNRYFSMZFMA-UHFFFAOYSA-N 0.000 claims description 3
• OVSHPICGFUGIQF-UHFFFAOYSA-N 3-[8-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]phenol Chemical compound OC1=CC=CC(C2=C(N3C=CC=C(NC4CCCC4)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 OVSHPICGFUGIQF-UHFFFAOYSA-N 0.000 claims description 3
• MTTIDVFMRGXMBZ-UHFFFAOYSA-N 6-chloro-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=C(Cl)C=C(NC3CCCC3)C2=N1 MTTIDVFMRGXMBZ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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