JP2005500315A - 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 - Google Patents
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 Download PDFInfo
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- JP2005500315A JP2005500315A JP2003507092A JP2003507092A JP2005500315A JP 2005500315 A JP2005500315 A JP 2005500315A JP 2003507092 A JP2003507092 A JP 2003507092A JP 2003507092 A JP2003507092 A JP 2003507092A JP 2005500315 A JP2005500315 A JP 2005500315A
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- JP
- Japan
- Prior art keywords
- imidazo
- pyridin
- het
- cyclopentylamino
- pyrimidinyl
- 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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- 238000011282 treatment Methods 0.000 title claims abstract description 41
- 208000029433 Herpesviridae infectious disease Diseases 0.000 title claims abstract description 35
- 230000002265 prevention Effects 0.000 title claims abstract description 32
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 379
- 238000000034 method Methods 0.000 claims abstract description 96
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 120
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- 125000003342 alkenyl group Chemical group 0.000 claims description 75
- -1 azido Compound Chemical class 0.000 claims description 75
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 125000000623 heterocyclic group Chemical group 0.000 claims description 52
- 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 description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000004429 atom Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 241001465754 Metazoa Species 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- 150000001540 azides Chemical class 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 241000700605 Viruses Species 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 13
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 10
- 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 9
- LKQXJYDAALZCAF-UHFFFAOYSA-N imidazo[1,2-a]pyridin-8-amine Chemical compound NC1=CC=CN2C=CN=C12 LKQXJYDAALZCAF-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- 230000008569 process Effects 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 8
- 241000701027 Human herpesvirus 6 Species 0.000 claims description 8
- 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 8
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 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 7
- FLKGKNOQNITLBY-UHFFFAOYSA-N 4-[8-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]benzonitrile Chemical compound N1=C2C(Cl)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(C#N)C=C1 FLKGKNOQNITLBY-UHFFFAOYSA-N 0.000 claims description 7
- 201000006082 Chickenpox Diseases 0.000 claims description 7
- 241000701022 Cytomegalovirus Species 0.000 claims description 7
- 241000701041 Human betaherpesvirus 7 Species 0.000 claims description 7
- 206010046980 Varicella Diseases 0.000 claims description 7
- 229960004150 aciclovir Drugs 0.000 claims description 7
- 241001529453 unidentified herpesvirus Species 0.000 claims description 7
- 229940093257 valacyclovir Drugs 0.000 claims description 7
- USHPMQFDRAFIHZ-UHFFFAOYSA-N 3-[8-chloro-3-[2-(cyclopentylamino)pyrimidin-4-yl]imidazo[1,2-a]pyridin-2-yl]benzonitrile Chemical compound N1=C2C(Cl)=CC=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=CC(C#N)=C1 USHPMQFDRAFIHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003443 antiviral agent Substances 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
- 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 5
- KLWNBJWBJACQJR-UHFFFAOYSA-N 4-[6-bromo-2-(4-fluorophenyl)-8-methylimidazo[1,2-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound N1=C2C(C)=CC(Br)=CN2C(C=2N=C(NC3CCCC3)N=CC=2)=C1C1=CC=C(F)C=C1 KLWNBJWBJACQJR-UHFFFAOYSA-N 0.000 claims description 5
- FTCYXGSDEVJSSB-UHFFFAOYSA-N 4-[8-chloro-2-(3-nitrophenyl)imidazo[1,2-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound [O-][N+](=O)C1=CC=CC(C2=C(N3C=CC=C(Cl)C3=N2)C=2N=C(NC3CCCC3)N=CC=2)=C1 FTCYXGSDEVJSSB-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
- 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 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
- 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 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 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 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
- 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 description 5
- 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 description 5
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-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
- 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 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
- 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 4
- 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 description 4
- 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 4
- 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 4
- 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 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
- 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 4
- 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 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
- 150000004820 halides Chemical class 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 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
- 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 4
- 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 4
- 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 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
- 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
- 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
- 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 3
- 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 description 3
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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 |
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| JP2005500315A true JP2005500315A (ja) | 2005-01-06 |
| JP2005500315A5 JP2005500315A5 (enExample) | 2005-09-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| 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 |
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| JP (1) | JP2005500315A (enExample) |
| KR (1) | KR20040018281A (enExample) |
| CN (1) | CN1518550A (enExample) |
| AT (1) | ATE337316T1 (enExample) |
| BR (1) | BR0210464A (enExample) |
| CA (1) | CA2451008A1 (enExample) |
| CO (1) | CO5540312A2 (enExample) |
| CZ (1) | CZ20033518A3 (enExample) |
| DE (1) | DE60214179T2 (enExample) |
| ES (1) | ES2271273T3 (enExample) |
| HU (1) | HUP0400266A2 (enExample) |
| IL (1) | IL158667A0 (enExample) |
| MX (1) | MXPA03011906A (enExample) |
| NO (1) | NO20035583D0 (enExample) |
| PL (1) | PL366827A1 (enExample) |
| WO (1) | WO2003000689A1 (enExample) |
| ZA (1) | ZA200308726B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008059714A1 (en) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Novel compounds with affinity for amyloid |
| 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 |
| WO2009057577A1 (ja) * | 2007-10-30 | 2009-05-07 | Nihon Medi-Physics Co., Ltd. | 新規アミロイド親和性化合物の使用及び製造方法 |
| JP2020505419A (ja) * | 2017-02-01 | 2020-02-20 | オーセントラ セラピュティクス ピーティーワイ エルティーディーＡｕｃｅｎｔｒａ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｐｔｙ Ｌｔｄ | 治療薬としてのＮ−シクロアルキル／ヘテロシクロアルキル−４−（イミダゾ［１，２−ａ］ピリジン）ピリミジン−２−アミン誘導体 |
Families Citing this family (29)
| 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 |
| PL366827A1 (en) * | 2001-06-21 | 2005-02-07 | Smithkline Beecham Corporation | Imidazo[1,2-a]pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| AU2003217712A1 (en) | 2002-03-07 | 2003-09-22 | Smithkline Beecham Corporation | Pyrazolopyrimidine and pyrazolotriazine derivatives and pharmaceutical compositions containing them |
| CA2577947A1 (en) * | 2004-08-31 | 2006-03-09 | Banyu Pharmaceutical Co., Ltd. | Novel substituted imidazole derivative |
| ES2376491T3 (es) | 2006-05-19 | 2012-03-14 | Nihon Medi-Physics Co., Ltd. | Compuesto que tiene afinidad por amiloide. |
| CA2670436A1 (en) | 2006-11-30 | 2008-06-05 | Nihon Medi-Physics Co., Ltd. | Novel compound having affinity for amyloid |
| KR101485445B1 (ko) | 2007-02-13 | 2015-01-22 | 니혼 메디피직스 가부시키가이샤 | 방사성 화상진단제의 제조 방법 |
| EP1964840A1 (en) | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]pyridines and their use as pharmaceuticals |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| WO2010009139A2 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Imidazolyl pyrimidine inhibitor compounds |
| EP2303841A1 (en) | 2008-07-14 | 2011-04-06 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
| WO2010009155A2 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Fused heterocyclyc inhibitor compounds |
| MX2011001090A (es) | 2008-07-28 | 2011-03-15 | Gilead Sciences Inc | Compuestos de inhibidor de desacetilasa de histona de cicloalquilideno y heterocicloalquilideno. |
| 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 |
| EP2440519A1 (en) | 2009-06-08 | 2012-04-18 | Gilead Sciences, Inc. | Alkanoylamino benzamide aniline hdac inihibitor compounds |
| WO2011041713A2 (en) * | 2009-10-02 | 2011-04-07 | Glaxosmithkline Llc | Piperazinyl antiviral agents |
| EP2493889B1 (en) | 2009-10-30 | 2017-09-06 | Janssen Pharmaceutica, N.V. | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| 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 |
| MX344600B (es) | 2011-06-27 | 2016-12-20 | Janssen Pharmaceutica Nv | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina. |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 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 |
| ES2625744T3 (es) * | 2013-06-04 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | Imidazo[1,2-a]piridinas sustituidas con 3-arilo y su uso |
| WO2015103137A1 (en) | 2013-12-30 | 2015-07-09 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| 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 |
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Family Cites Families (52)
| 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 |
| 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 |
| 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 |
| 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 |
| AU6355190A (en) | 1989-06-13 | 1991-01-17 | Smithkline Beecham Corporation | Inhibition of interleukin-1 and tumor necrosis factor production by monocytes and/or macrophages |
| AU5921890A (en) | 1989-06-13 | 1991-01-08 | Smithkline Beecham Corporation | Monokine activity interference |
| 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 |
| KR930700104A (ko) * | 1990-06-12 | 1993-03-13 | 원본미기재 | 5-리프옥시게나제 및 사이클로옥시게나제 경로 개재된 질병의 억제 |
| 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 |
| AU9137591A (en) | 1990-12-13 | 1992-07-08 | Smithkline Beecham Corporation | Novel csaids |
| WO1992010498A1 (en) | 1990-12-13 | 1992-06-25 | Smithkline Beecham Corporation | Novel csaids |
| EP0497258B1 (en) | 1991-01-29 | 2002-01-02 | Fujisawa Pharmaceutical Co., Ltd. | Use of adenosine antagonists in the prevention and treatment of pancreatitis and ulcer |
| 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 |
| KR19980703559A (ko) | 1995-04-04 | 1998-11-05 | 그레이엄브레레톤 | 이미다조［1,2-ａ］피리딘 유도체 |
| 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 |
| 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 |
| CA2224517A1 (en) | 1995-06-12 | 1996-12-27 | G.D. Searle & Co. | Compositions comprising a cyclooxygenase-2 inhibitor and a 5-lipoxygenase inhibitor |
| US6342510B1 (en) | 1995-06-12 | 2002-01-29 | G. D. Searle & Co. | Treatment of inflammation and inflammation-related disorders with a combination of a cyclooxygenase-2 inhibitors and a leukotriene B4 receptor antagonist |
| 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 |
| ATE281458T1 (de) | 1997-09-05 | 2004-11-15 | Glaxo Group Ltd | Pharmazeutische zusammensetzung, enthaltend 2,3- diaryl-pyrazolo(1,5-b)pyridazin derivate |
| CA2331878A1 (en) | 1998-05-14 | 1999-11-18 | G.D. Searle & Co. | 1,5-diaryl substituted pyrazoles as p38 kinase inhibitors |
| 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 |
| US7223772B1 (en) | 1998-11-03 | 2007-05-29 | Smithkline Beecham Corporation | Pyrazolopyridine derivatives as selective cox-2 inhibitors |
| EP1157025B1 (en) | 1999-02-27 | 2004-03-10 | Glaxo Group Limited | Pyrazolopyridines |
| 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 |
| ATE301653T1 (de) | 2000-12-15 | 2005-08-15 | Glaxo Group Ltd | Pyrazolopyridine |
| AU2002239348A1 (en) | 2000-12-15 | 2002-06-24 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| PL366827A1 (en) * | 2001-06-21 | 2005-02-07 | Smithkline Beecham Corporation | Imidazo[1,2-a]pyridine derivatives for the prophylaxis and treatment of herpes viral infections |
| WO2003000682A1 (en) | 2001-06-25 | 2003-01-03 | Merck & Co., Inc. | (pyrimidyl)(phenyl)substituted fused heteroaryl p38 inhibiting and pkg kinase inhibiting compounds |
| ATE326466T1 (de) * | 2001-10-05 | 2006-06-15 | Smithkline Beecham Corp | Imidazopyridinderivate zur verwendung bei der behandlung von herpes-vireninfektion |
| US6711762B2 (en) | 2002-01-30 | 2004-03-30 | Ktk Services, Inc. | Method of using a truck cab bridge bed |
-
2002
- 2002-06-10 PL PL02366827A patent/PL366827A1/xx not_active Application Discontinuation
- 2002-06-10 CA CA002451008A patent/CA2451008A1/en not_active Abandoned
- 2002-06-10 CN CNA028124499A patent/CN1518550A/zh active Pending
- 2002-06-10 EP EP02739833A patent/EP1401836B1/en not_active Expired - Lifetime
- 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 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 US US10/479,526 patent/US7186714B2/en not_active Expired - Fee Related
- 2002-06-10 DE DE60214179T patent/DE60214179T2/de not_active Expired - Fee Related
- 2002-06-10 WO PCT/US2002/018520 patent/WO2003000689A1/en not_active Ceased
- 2002-06-10 IL IL15866702A patent/IL158667A0/xx unknown
- 2002-06-10 JP JP2003507092A patent/JP2005500315A/ja active Pending
- 2002-06-10 KR KR10-2003-7016716A patent/KR20040018281A/ko not_active Withdrawn
- 2002-06-10 MX MXPA03011906A patent/MXPA03011906A/es unknown
- 2002-06-10 CZ CZ20033518A patent/CZ20033518A3/cs 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
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008059714A1 (en) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Novel compounds with affinity for amyloid |
| JPWO2008059714A1 (ja) * | 2006-11-17 | 2010-03-04 | 日本メジフィジックス株式会社 | 新規アミロイド親和性化合物 |
| 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 |
| JPWO2009054496A1 (ja) * | 2007-10-24 | 2011-03-10 | 日本メジフィジックス株式会社 | 新規アミロイド親和性化合物 |
| WO2009057577A1 (ja) * | 2007-10-30 | 2009-05-07 | Nihon Medi-Physics Co., Ltd. | 新規アミロイド親和性化合物の使用及び製造方法 |
| JP2020505419A (ja) * | 2017-02-01 | 2020-02-20 | オーセントラ セラピュティクス ピーティーワイ エルティーディーＡｕｃｅｎｔｒａ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｐｔｙ Ｌｔｄ | 治療薬としてのＮ−シクロアルキル／ヘテロシクロアルキル−４−（イミダゾ［１，２−ａ］ピリジン）ピリミジン−２−アミン誘導体 |
| JP7113528B2 (ja) | 2017-02-01 | 2022-08-05 | オーセントラ セラピュティクス ピーティーワイ エルティーディー | 治療薬としてのＮ－シクロアルキル／ヘテロシクロアルキル－４－（イミダゾ［１，２－ａ］ピリジン）ピリミジン－２－アミン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE337316T1 (de) | 2006-09-15 |
| MXPA03011906A (es) | 2004-03-26 |
| NO20035583D0 (no) | 2003-12-15 |
| CA2451008A1 (en) | 2003-01-03 |
| CZ20033518A3 (en) | 2004-05-12 |
| ZA200308726B (en) | 2005-02-10 |
| CO5540312A2 (es) | 2005-07-29 |
| HUP0400266A2 (hu) | 2004-08-30 |
| US20050228004A1 (en) | 2005-10-13 |
| BR0210464A (pt) | 2004-07-20 |
| DE60214179T2 (de) | 2007-01-04 |
| US7186714B2 (en) | 2007-03-06 |
| US20060167252A1 (en) | 2006-07-27 |
| US20070135451A1 (en) | 2007-06-14 |
| EP1401836B1 (en) | 2006-08-23 |
| CN1518550A (zh) | 2004-08-04 |
| KR20040018281A (ko) | 2004-03-02 |
| WO2003000689A1 (en) | 2003-01-03 |
| IL158667A0 (en) | 2004-05-12 |
| DE60214179D1 (de) | 2006-10-05 |
| ES2271273T3 (es) | 2007-04-16 |
| PL366827A1 (en) | 2005-02-07 |
| EP1401836A1 (en) | 2004-03-31 |
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