JP2013500997A5 - - Google Patents
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- JP2013500997A5 JP2013500997A5 JP2012523088A JP2012523088A JP2013500997A5 JP 2013500997 A5 JP2013500997 A5 JP 2013500997A5 JP 2012523088 A JP2012523088 A JP 2012523088A JP 2012523088 A JP2012523088 A JP 2012523088A JP 2013500997 A5 JP2013500997 A5 JP 2013500997A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- nitro
- oxy
- oxazine
- imidazo
- 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.)
- Granted
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- 125000001424 substituent group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 208000015181 infectious disease Diseases 0.000 claims 4
- 230000000813 microbial effect Effects 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 241000222727 Leishmania donovani Species 0.000 claims 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 2
- 241000223109 Trypanosoma cruzi Species 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 230000002924 anti-infective effect Effects 0.000 claims 2
- 239000000872 buffer Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- YMBWFCMEEHOGSZ-SECBINFHSA-N (6r)-2-nitro-6-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])OC1=CC=C(OC(F)(F)F)C=C1 YMBWFCMEEHOGSZ-SECBINFHSA-N 0.000 claims 1
- YMBWFCMEEHOGSZ-VIFPVBQESA-N (6s)-2-nitro-6-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])OC1=CC=C(OC(F)(F)F)C=C1 YMBWFCMEEHOGSZ-VIFPVBQESA-N 0.000 claims 1
- NTTCBTHLOZNZJK-OAQYLSRUSA-N (7r)-7-methyl-2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C([C@]1(C)OC2=NC(=CN2CC1)[N+]([O-])=O)OCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NTTCBTHLOZNZJK-OAQYLSRUSA-N 0.000 claims 1
- NTTCBTHLOZNZJK-NRFANRHFSA-N (7s)-7-methyl-2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C([C@@]1(C)OC2=NC(=CN2CC1)[N+]([O-])=O)OCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NTTCBTHLOZNZJK-NRFANRHFSA-N 0.000 claims 1
- ZVCBWYISQGQTBZ-UHFFFAOYSA-N 2-[[2-(4-fluorophenyl)pyrimidin-5-yl]oxymethyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CN=C1C1=CC=C(F)C=C1 ZVCBWYISQGQTBZ-UHFFFAOYSA-N 0.000 claims 1
- QMDDMCVXYCYGRO-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(F)C=C1 QMDDMCVXYCYGRO-UHFFFAOYSA-N 0.000 claims 1
- CYOWZVHJZBXWDW-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)phenoxy]methyl]-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole Chemical compound O1C2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(F)C=C1 CYOWZVHJZBXWDW-UHFFFAOYSA-N 0.000 claims 1
- TYAJTYRDTVICDL-UHFFFAOYSA-N 2-[[4-(6-methoxypyridin-3-yl)phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1=NC(OC)=CC=C1C(C=C1)=CC=C1OCC1(C)OC2=NC([N+]([O-])=O)=CN2C1 TYAJTYRDTVICDL-UHFFFAOYSA-N 0.000 claims 1
- ZCQDJADLEOACNA-UHFFFAOYSA-N 2-[[5-(4-fluorophenyl)pyrazin-2-yl]oxymethyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CN=C1C1=CC=C(F)C=C1 ZCQDJADLEOACNA-UHFFFAOYSA-N 0.000 claims 1
- CSLSSIUGFJHMLO-UHFFFAOYSA-N 2-[[5-(4-fluorophenyl)pyridin-2-yl]oxymethyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(F)C=C1 CSLSSIUGFJHMLO-UHFFFAOYSA-N 0.000 claims 1
- TYEIBEKUCJZHMX-UHFFFAOYSA-N 2-[[5-(4-fluorophenyl)pyrimidin-2-yl]oxymethyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=NC=C1C1=CC=C(F)C=C1 TYEIBEKUCJZHMX-UHFFFAOYSA-N 0.000 claims 1
- AWBRPWXFUXJVEG-UHFFFAOYSA-N 2-[[6-(4-fluorophenyl)pyridin-3-yl]oxymethyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(F)C=C1 AWBRPWXFUXJVEG-UHFFFAOYSA-N 0.000 claims 1
- WGAMHROVWXKGKW-UHFFFAOYSA-N 2-methyl-6-nitro-2-[[2-[4-(trifluoromethoxy)phenyl]pyrimidin-5-yl]oxymethyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CN=C1C1=CC=C(OC(F)(F)F)C=C1 WGAMHROVWXKGKW-UHFFFAOYSA-N 0.000 claims 1
- SKMAQZSSDQYMHA-UHFFFAOYSA-N 2-methyl-6-nitro-2-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 SKMAQZSSDQYMHA-UHFFFAOYSA-N 0.000 claims 1
- YLVQZTKLHNULPT-UHFFFAOYSA-N 2-methyl-6-nitro-2-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 YLVQZTKLHNULPT-UHFFFAOYSA-N 0.000 claims 1
- AFKAYDDCLGFYBU-UHFFFAOYSA-N 2-methyl-6-nitro-2-[[5-[4-(trifluoromethoxy)phenyl]pyrazin-2-yl]oxymethyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CN=C1C1=CC=C(OC(F)(F)F)C=C1 AFKAYDDCLGFYBU-UHFFFAOYSA-N 0.000 claims 1
- VGWKSCHHKMKBGM-UHFFFAOYSA-N 2-methyl-6-nitro-2-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]oxymethyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 VGWKSCHHKMKBGM-UHFFFAOYSA-N 0.000 claims 1
- WECLZTDASODIEH-UHFFFAOYSA-N 2-methyl-6-nitro-2-[[5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]oxymethyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=NC=C1C1=CC=C(OC(F)(F)F)C=C1 WECLZTDASODIEH-UHFFFAOYSA-N 0.000 claims 1
- FRXJIYQUHHMQRA-UHFFFAOYSA-N 2-methyl-6-nitro-2-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxymethyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 FRXJIYQUHHMQRA-UHFFFAOYSA-N 0.000 claims 1
- DKBRVRXAPWANPM-UHFFFAOYSA-N 2-nitro-6-[(4-phenylmethoxyphenyl)methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC(C=C1)=CC=C1OCC1=CC=CC=C1 DKBRVRXAPWANPM-UHFFFAOYSA-N 0.000 claims 1
- ZHRASUMKCIRTES-UHFFFAOYSA-N 2-nitro-6-[[3-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC1=CC=CC(OC(F)(F)F)=C1 ZHRASUMKCIRTES-UHFFFAOYSA-N 0.000 claims 1
- XDFSBIUYBLENFF-UHFFFAOYSA-N 2-nitro-6-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC(C=1)=CC=CC=1C1=CC=C(OC(F)(F)F)C=C1 XDFSBIUYBLENFF-UHFFFAOYSA-N 0.000 claims 1
- YMBWFCMEEHOGSZ-UHFFFAOYSA-N 2-nitro-6-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC1=CC=C(OC(F)(F)F)C=C1 YMBWFCMEEHOGSZ-UHFFFAOYSA-N 0.000 claims 1
- UIPIZMADAJJXSA-UHFFFAOYSA-N 2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC1=CC=C(OC(F)(F)F)C=C1 UIPIZMADAJJXSA-UHFFFAOYSA-N 0.000 claims 1
- DLBVAKLECIGBHD-UHFFFAOYSA-N 2-nitro-6-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DLBVAKLECIGBHD-UHFFFAOYSA-N 0.000 claims 1
- PICDIDORINAMBJ-UHFFFAOYSA-N 2-nitro-6-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 PICDIDORINAMBJ-UHFFFAOYSA-N 0.000 claims 1
- GYRYSVKOTZBBPG-UHFFFAOYSA-N 2-nitro-6-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 GYRYSVKOTZBBPG-UHFFFAOYSA-N 0.000 claims 1
- DIZRPICDSULNDS-UHFFFAOYSA-N 2-nitro-6-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DIZRPICDSULNDS-UHFFFAOYSA-N 0.000 claims 1
- KKUKKUOZYLQOMW-UHFFFAOYSA-N 2-nitro-6-[[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(N=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 KKUKKUOZYLQOMW-UHFFFAOYSA-N 0.000 claims 1
- QQLOFOVQUMKHPJ-UHFFFAOYSA-N 2-nitro-6-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 QQLOFOVQUMKHPJ-UHFFFAOYSA-N 0.000 claims 1
- XIKLEESAKIVDNK-UHFFFAOYSA-N 2-nitro-6-[[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 XIKLEESAKIVDNK-UHFFFAOYSA-N 0.000 claims 1
- YFAXAFFUGBLZOP-UHFFFAOYSA-N 2-nitro-7-[(4-phenylmethoxyphenoxy)methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 YFAXAFFUGBLZOP-UHFFFAOYSA-N 0.000 claims 1
- AFYYMFBWQPYVNA-UHFFFAOYSA-N 2-nitro-7-[(4-phenylmethoxyphenyl)methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC(C=C1)=CC=C1OCC1=CC=CC=C1 AFYYMFBWQPYVNA-UHFFFAOYSA-N 0.000 claims 1
- KEPDMMNFWQRFEA-UHFFFAOYSA-N 2-nitro-7-[[3-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC1=CC=CC(OC(F)(F)F)=C1 KEPDMMNFWQRFEA-UHFFFAOYSA-N 0.000 claims 1
- FJQBCEDWCKWTBL-UHFFFAOYSA-N 2-nitro-7-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC1=CC=C(OC(F)(F)F)C=C1 FJQBCEDWCKWTBL-UHFFFAOYSA-N 0.000 claims 1
- AKYSJCGKQJLIEI-UHFFFAOYSA-N 2-nitro-7-[[4-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC1=CC=C(OC(F)(F)F)C=C1 AKYSJCGKQJLIEI-UHFFFAOYSA-N 0.000 claims 1
- YRZTVAYXNMPEHK-UHFFFAOYSA-N 2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 YRZTVAYXNMPEHK-UHFFFAOYSA-N 0.000 claims 1
- YXWALFWDXOZXLM-UHFFFAOYSA-N 2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 YXWALFWDXOZXLM-UHFFFAOYSA-N 0.000 claims 1
- YHIHNLZSXHLZRO-UHFFFAOYSA-N 2-nitro-7-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 YHIHNLZSXHLZRO-UHFFFAOYSA-N 0.000 claims 1
- FLPCAIYJNUVZIV-UHFFFAOYSA-N 2-nitro-7-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 FLPCAIYJNUVZIV-UHFFFAOYSA-N 0.000 claims 1
- HCEUKUYCMKEOMQ-UHFFFAOYSA-N 2-nitro-7-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 HCEUKUYCMKEOMQ-UHFFFAOYSA-N 0.000 claims 1
- JOWOAMMSABIQDN-UHFFFAOYSA-N 4-[4-[(2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl)methoxy]phenyl]benzonitrile Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(C#N)C=C1 JOWOAMMSABIQDN-UHFFFAOYSA-N 0.000 claims 1
- VCENEFJSXTYRJF-UHFFFAOYSA-N 6-[[4-(4-fluorophenyl)phenoxy]methyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(F)C=C1 VCENEFJSXTYRJF-UHFFFAOYSA-N 0.000 claims 1
- YCDRNIZCGKVAJS-UHFFFAOYSA-N 6-[[5-(4-fluorophenyl)pyridin-2-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(N=C1)=CC=C1C1=CC=C(F)C=C1 YCDRNIZCGKVAJS-UHFFFAOYSA-N 0.000 claims 1
- NBORUIOPRKKLHI-UHFFFAOYSA-N 6-[[6-(4-fluorophenyl)pyridin-3-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=N1)=CC=C1C1=CC=C(F)C=C1 NBORUIOPRKKLHI-UHFFFAOYSA-N 0.000 claims 1
- PRVWQOCOTCCZQI-UHFFFAOYSA-N 6-nitro-2-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-2,3-dihydroimidazo[2,1-b][1,3]oxazole Chemical compound O1C2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 PRVWQOCOTCCZQI-UHFFFAOYSA-N 0.000 claims 1
- LEYAILDYSKNETJ-UHFFFAOYSA-N 6-nitro-2-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-2,3-dihydroimidazo[2,1-b][1,3]oxazole Chemical compound O1C2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 LEYAILDYSKNETJ-UHFFFAOYSA-N 0.000 claims 1
- AMDZXSOAYLNZSB-UHFFFAOYSA-N 6-nitro-2-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]oxymethyl]-2,3-dihydroimidazo[2,1-b][1,3]oxazole Chemical compound O1C2=NC([N+](=O)[O-])=CN2CC1COC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 AMDZXSOAYLNZSB-UHFFFAOYSA-N 0.000 claims 1
- QACAURHEZMYCGU-UHFFFAOYSA-N 7-[[4-(4-fluorophenyl)phenoxy]methyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C1=CC=C(F)C=C1 QACAURHEZMYCGU-UHFFFAOYSA-N 0.000 claims 1
- IQJFYFAKNUOHAE-UHFFFAOYSA-N 7-[[4-(4-fluorophenyl)phenoxy]methyl]-7-methyl-2-nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(F)C=C1 IQJFYFAKNUOHAE-UHFFFAOYSA-N 0.000 claims 1
- MCPRPFWJSZDYBF-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)pyridin-2-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(N=C1)=CC=C1C1=CC=C(F)C=C1 MCPRPFWJSZDYBF-UHFFFAOYSA-N 0.000 claims 1
- AGWAOZJROKGNRO-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)pyridin-2-yl]oxymethyl]-7-methyl-2-nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(F)C=C1 AGWAOZJROKGNRO-UHFFFAOYSA-N 0.000 claims 1
- USIKCXQLXHGVDD-UHFFFAOYSA-N 7-[[6-(4-fluorophenyl)pyridin-3-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=N1)=CC=C1C1=CC=C(F)C=C1 USIKCXQLXHGVDD-UHFFFAOYSA-N 0.000 claims 1
- GQEZVYKTQWMCCO-UHFFFAOYSA-N 7-[[6-(4-fluorophenyl)pyridin-3-yl]oxymethyl]-7-methyl-2-nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(F)C=C1 GQEZVYKTQWMCCO-UHFFFAOYSA-N 0.000 claims 1
- YVHHDRCXDTWXRG-UHFFFAOYSA-N 7-methyl-2-nitro-7-[(4-phenylmethoxyphenoxy)methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1OCC1=CC=CC=C1 YVHHDRCXDTWXRG-UHFFFAOYSA-N 0.000 claims 1
- VWGRTYXITWEZSS-UHFFFAOYSA-N 7-methyl-2-nitro-7-[(4-phenylmethoxyphenyl)methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC(C=C1)=CC=C1OCC1=CC=CC=C1 VWGRTYXITWEZSS-UHFFFAOYSA-N 0.000 claims 1
- SPAYDMYBDJTUPR-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[3-(trifluoromethoxy)phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC1=CC=CC(OC(F)(F)F)=C1 SPAYDMYBDJTUPR-UHFFFAOYSA-N 0.000 claims 1
- ALHDHSLKVWVIHN-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC(C=1)=CC=CC=1C1=CC=C(OC(F)(F)F)C=C1 ALHDHSLKVWVIHN-UHFFFAOYSA-N 0.000 claims 1
- PAYUNELULSPXRL-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-(trifluoromethoxy)phenoxy]methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC1=CC=C(OC(F)(F)F)C=C1 PAYUNELULSPXRL-UHFFFAOYSA-N 0.000 claims 1
- UOHVERHTRSLFEH-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-(trifluoromethoxy)phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC1=CC=C(OC(F)(F)F)C=C1 UOHVERHTRSLFEH-UHFFFAOYSA-N 0.000 claims 1
- NUSXIGWKAHRZFJ-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NUSXIGWKAHRZFJ-UHFFFAOYSA-N 0.000 claims 1
- NTTCBTHLOZNZJK-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NTTCBTHLOZNZJK-UHFFFAOYSA-N 0.000 claims 1
- JHWOUTVKJWPBQN-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 JHWOUTVKJWPBQN-UHFFFAOYSA-N 0.000 claims 1
- DTEROJRFJGXHNX-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DTEROJRFJGXHNX-UHFFFAOYSA-N 0.000 claims 1
- VYTTWAYUURNVAL-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VYTTWAYUURNVAL-UHFFFAOYSA-N 0.000 claims 1
- OMUSZRWPEMVKON-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 OMUSZRWPEMVKON-UHFFFAOYSA-N 0.000 claims 1
- DSVKLHUIYADEGR-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 DSVKLHUIYADEGR-UHFFFAOYSA-N 0.000 claims 1
- 239000005414 inactive ingredient Substances 0.000 claims 1
- -1 inert ingredients Substances 0.000 claims 1
- 229940060367 inert ingredients Drugs 0.000 claims 1
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| GB201012209D0 (en) * | 2010-05-31 | 2010-09-08 | Ge Healthcare Ltd | In vivo imaging agent |
| US9051333B2 (en) | 2011-04-15 | 2015-06-09 | Otsuka Pharmaceutical Co., Ltd. | 6,7-dihydroimidazo [2,1-b] [1,3]oxazine bactericides |
| JP2015006994A (ja) * | 2011-10-28 | 2015-01-15 | 大正製薬株式会社 | ジヒドロイミダゾオキサゾール誘導体 |
| KR101918469B1 (ko) * | 2012-06-04 | 2018-11-15 | 한국화학연구원 | 바이사이클릭 니트로이미다졸 유도체 또는 이들의 광학이성질체, 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약제학적 조성물 |
| US10301294B2 (en) * | 2013-03-13 | 2019-05-28 | The Broad Institute Inc. | Compounds for the treatment of tuberculosis |
| CN104059082B (zh) * | 2013-03-21 | 2016-08-03 | 苏州迈泰生物技术有限公司 | 硝基咪唑杂环类化合物及其在制备治疗结核病药物中的应用 |
| KR101564425B1 (ko) | 2013-11-26 | 2015-10-30 | 한국화학연구원 | 신규한 바이사이클릭 니트로이미다졸 카바메이트 화합물, 이를 제조하는 방법 및 이를 유효성분으로 함유하는 결핵 질환의 예방 또는 치료용 약제학적 조성물 |
| TWI687409B (zh) | 2014-08-28 | 2020-03-11 | 日商大塚製藥股份有限公司 | 稠合雜環化合物 |
| KR101682356B1 (ko) | 2014-11-04 | 2016-12-06 | 한국화학연구원 | 이미다조 옥사진 유도체, 이의 약학적으로 허용 가능한 염 또는 이의 광학이성질체 및 이를 유효성분으로 함유하는 약제학적 조성물 |
| JP6542900B2 (ja) | 2015-01-29 | 2019-07-10 | メッドシャイン ディスカバリー インコーポレイテッド | 抗肺結核症のニトロイミダゾール誘導体 |
| GB201519054D0 (en) * | 2015-10-28 | 2015-12-09 | Univ Dundee | Composition |
| US10851079B2 (en) | 2016-02-26 | 2020-12-01 | Otsuka Pharmaceutical Co., Ltd. | Piperidine derivative |
| CN108727406B (zh) | 2017-03-28 | 2021-12-07 | 北京协和制药二厂 | 含氮杂环取代的苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 |
| JP7530384B2 (ja) * | 2019-05-01 | 2024-08-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | （ｒ）－（２－メチルオキシラン－２－イル）メチル ４－ブロモベンゼンスルホネート |
| WO2023114170A1 (en) | 2021-12-14 | 2023-06-22 | Boehringer Ingelheim International Gmbh | Aldosterone synthase inhibitors for treating chronic kidney disease |
| CN114249747A (zh) * | 2021-12-27 | 2022-03-29 | 苏州虞美景盛新药开发有限公司 | 一种用于治疗广泛耐药性结核病的硝基咪唑吡喃类药物的新合成工艺 |
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| CH568715A5 (enExample) | 1972-03-16 | 1975-11-14 | Ciba Geigy Ag | |
| IL41744A0 (en) | 1972-03-16 | 1973-05-31 | Ciba Geigy Ag | New aryl ether derivatives,their production and their use as pesticides |
| FR2575158B1 (fr) | 1984-12-20 | 1987-10-02 | Pf Medicament | Arylalcoyloxymethyl-2 morpholines, leur preparation et leur application en tant que medicaments utiles dans le traitement des troubles du systeme nerveux central |
| SU1271861A1 (ru) * | 1985-05-07 | 1986-11-23 | Иркутский институт органической химии СО АН СССР | Способ получени 2,2-диметил-3-цианометилиденбензимидазо @ 2,1- @ -1,3-оксазолидина |
| US6087358A (en) | 1995-06-26 | 2000-07-11 | Pathogenesis Corporation | Nitro-[2,1-b]imidazopyran compounds and antibacterial uses thereof |
| US5668127A (en) | 1995-06-26 | 1997-09-16 | Pathogenesis Corporation | Nitroimidazole antibacterial compounds and methods of use thereof |
| TWI347946B (en) * | 2002-10-11 | 2011-09-01 | Otsuka Pharma Co Ltd | 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound |
| RU2365593C2 (ru) | 2003-10-31 | 2009-08-27 | Оцука Фармасьютикал Ко., Лтд. | ПРОИЗВОДНЫЕ 2,3-ДИГИДРО-6-НИТРОИМИДАЗО [2,1-b] ОКСАЗОЛА ДЛЯ ЛЕЧЕНИЯ ТУБЕРКУЛЕЗА |
| JP4787529B2 (ja) | 2004-04-09 | 2011-10-05 | 大塚製薬株式会社 | 医薬組成物 |
| JP4789966B2 (ja) | 2004-04-09 | 2011-10-12 | 大塚製薬株式会社 | 医薬組成物 |
| US7115736B2 (en) | 2004-09-17 | 2006-10-03 | Daiso Co., Ltd. | Process for preparing imidazopyran derivatives |
| CN101268084A (zh) * | 2005-07-28 | 2008-09-17 | 沃泰克斯药物股份有限公司 | 天冬氨酸特异性半胱氨酸蛋白酶抑制剂前体药物 |
| JP2009521464A (ja) | 2005-12-23 | 2009-06-04 | ノバルティス アクチエンゲゼルシャフト | ニトロイミダゾール化合物 |
| US20070213341A1 (en) | 2006-03-13 | 2007-09-13 | Li Chen | Spiroindolinone derivatives |
| US7678791B2 (en) | 2006-07-12 | 2010-03-16 | Cumbre Ip Ventures, L.P. | Nitroheteroaryl-containing rifamycin derivatives |
| SG179453A1 (en) | 2007-03-09 | 2012-04-27 | Sanofi Aventis | Substituted dihydro and tetrahydro oxazolopyrimidinones, preparation and use thereof |
| CA2712613C (en) | 2008-03-26 | 2017-02-28 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazoles covalently linked to substituted phenyl oxazolidinones |
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- 2010-07-30 BR BR112012002214-8A patent/BR112012002214B1/pt not_active IP Right Cessation
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2012
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