JP2014510695A5 - - Google Patents
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- Publication number
- JP2014510695A5 JP2014510695A5 JP2013532004A JP2013532004A JP2014510695A5 JP 2014510695 A5 JP2014510695 A5 JP 2014510695A5 JP 2013532004 A JP2013532004 A JP 2013532004A JP 2013532004 A JP2013532004 A JP 2013532004A JP 2014510695 A5 JP2014510695 A5 JP 2014510695A5
- Authority
- JP
- Japan
- Prior art keywords
- nitro
- imidazo
- dihydro
- oxazine
- phenoxymethyl
- 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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- -1 tetrahydroisoquinolinediyl Chemical group 0.000 claims description 128
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- HRCMXYXVAWHBTH-UHFFFAOYSA-N 2,3-dihydro-1,3-benzoxazole Chemical compound C1=CC=C2OCNC2=C1 HRCMXYXVAWHBTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- RHOPXRDSDRPILC-LJQANCHMSA-N (7r)-2-nitro-7-[[2-[[4-(trifluoromethoxy)phenyl]methoxy]quinolin-6-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1C=C2)=CC=C1N=C2OCC1=CC=C(OC(F)(F)F)C=C1 RHOPXRDSDRPILC-LJQANCHMSA-N 0.000 claims 1
- KJKCCIMKGISYLV-MUUNZHRXSA-N (7r)-2-nitro-7-[[2-[[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]-3,4-dihydro-1h-isoquinolin-6-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1CC2)=CC=C1CN2CC(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 KJKCCIMKGISYLV-MUUNZHRXSA-N 0.000 claims 1
- HTIXZKRAPJDIIC-SSEXGKCCSA-N (7r)-2-nitro-7-[[4-[1-[[4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]methyl]piperidin-4-yl]oxyphenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1OC(CC1)CCN1CC(C=C1)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 HTIXZKRAPJDIIC-SSEXGKCCSA-N 0.000 claims 1
- XWQQWTLFQJHFMA-MUUNZHRXSA-N (7r)-2-nitro-7-[[4-[4-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]piperidin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1C(CC1)CCN1CC1=CC=C(C(F)(F)F)C=C1 XWQQWTLFQJHFMA-MUUNZHRXSA-N 0.000 claims 1
- UOCVPJPYMKKUCZ-SSEXGKCCSA-N (7r)-2-nitro-7-[[4-[4-[2-[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]propan-2-yl]piperazin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1CN(C=2C=CC(OC[C@@H]3OC4=NC(=CN4CC3)[N+]([O-])=O)=CC=2)CCN1C(C)(C)C(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 UOCVPJPYMKKUCZ-SSEXGKCCSA-N 0.000 claims 1
- LTXXIPIWANUIPO-RUZDIDTESA-N (7r)-2-nitro-7-[[4-[4-[3-[3-(trifluoromethyl)phenoxy]propyl]piperidin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1CCCOC1=CC=CC(C(F)(F)F)=C1 LTXXIPIWANUIPO-RUZDIDTESA-N 0.000 claims 1
- FNYZFRPNTZOXNY-RUZDIDTESA-N (7r)-2-nitro-7-[[4-[4-[3-[4-(trifluoromethyl)phenyl]propyl]piperidin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1CCCC1=CC=C(C(F)(F)F)C=C1 FNYZFRPNTZOXNY-RUZDIDTESA-N 0.000 claims 1
- SUFXRGDFGVTLBB-OAQYLSRUSA-N (7r)-2-nitro-7-[[4-[4-[4-(trifluoromethylsulfanyl)phenoxy]piperidin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(SC(F)(F)F)C=C1 SUFXRGDFGVTLBB-OAQYLSRUSA-N 0.000 claims 1
- BCGNVZKCAYDDIR-MUUNZHRXSA-N (7r)-2-nitro-7-[[4-[4-[4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]piperazin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCN1C(C=C1)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 BCGNVZKCAYDDIR-MUUNZHRXSA-N 0.000 claims 1
- QPGHIZAPZQVXFZ-HSZRJFAPSA-N (7r)-2-nitro-7-[[4-[4-[[4-(trifluoromethoxy)phenyl]methyl]piperidin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1CC1=CC=C(OC(F)(F)F)C=C1 QPGHIZAPZQVXFZ-HSZRJFAPSA-N 0.000 claims 1
- WAUIWMWBDVMUSM-OBFZPWGMSA-N (7r)-2-nitro-7-[[4-[4-[[4-(trifluoromethyl)cyclohexyl]methyl]piperazin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCN1CC1CCC(C(F)(F)F)CC1 WAUIWMWBDVMUSM-OBFZPWGMSA-N 0.000 claims 1
- DPRJLOBFJWBPTQ-GDLZYMKVSA-N (7r)-2-nitro-7-[[4-[4-[[4-[4-(trifluoromethoxy)phenoxy]phenyl]methyl]piperidin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1CC(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 DPRJLOBFJWBPTQ-GDLZYMKVSA-N 0.000 claims 1
- FDBVQXYMWRGACY-GDLZYMKVSA-N (7r)-2-nitro-7-[[4-[4-[[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]piperazin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCN1CC(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 FDBVQXYMWRGACY-GDLZYMKVSA-N 0.000 claims 1
- KWPFAJJLPVFSAP-WVXBCFDCSA-N (7r)-7-[[4-[(3r)-3-methyl-4-[[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]piperazin-1-yl]phenoxy]methyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1C)N(C=2C=CC(OC[C@@H]3OC4=NC(=CN4CC3)[N+]([O-])=O)=CC=2)CCN1CC(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 KWPFAJJLPVFSAP-WVXBCFDCSA-N 0.000 claims 1
- UBSXNNFCLZZKIX-JOCHJYFZSA-N (7r)-7-[[4-[4-methoxy-4-[4-(trifluoromethyl)phenyl]piperidin-1-yl]phenoxy]methyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1CN(C=2C=CC(OC[C@@H]3OC4=NC(=CN4CC3)[N+]([O-])=O)=CC=2)CCC1(OC)C1=CC=C(C(F)(F)F)C=C1 UBSXNNFCLZZKIX-JOCHJYFZSA-N 0.000 claims 1
- FNYJTYRLLXMNFQ-LJAQVGFWSA-N (7s)-2-nitro-7-[[4-[4-[[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]methyl]phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@@H]1CCN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1C(C=C1)=CC=C1CN(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 FNYJTYRLLXMNFQ-LJAQVGFWSA-N 0.000 claims 1
- WNCCYOQDKJZVBP-OAQYLSRUSA-N 1-[4-[4-[[(7r)-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazin-7-yl]methoxy]phenyl]phenyl]-4-(trifluoromethyl)piperidin-4-ol Chemical compound C1CC(O)(C(F)(F)F)CCN1C1=CC=C(C=2C=CC(OC[C@@H]3OC4=NC(=CN4CC3)[N+]([O-])=O)=CC=2)C=C1 WNCCYOQDKJZVBP-OAQYLSRUSA-N 0.000 claims 1
- GWTGPIFIJCPKNL-UHFFFAOYSA-N 2-nitro-7-[[1-[3-[4-(trifluoromethoxy)phenoxy]propyl]-3,4-dihydro-2h-quinolin-6-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1CCC2)=CC=C1N2CCCOC1=CC=C(OC(F)(F)F)C=C1 GWTGPIFIJCPKNL-UHFFFAOYSA-N 0.000 claims 1
- SBFDEKAGNIJSMQ-UHFFFAOYSA-N 2-nitro-7-[[4-[1-[[4-(trifluoromethoxy)phenyl]methyl]piperidin-4-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C(CC1)CCN1CC1=CC=C(OC(F)(F)F)C=C1 SBFDEKAGNIJSMQ-UHFFFAOYSA-N 0.000 claims 1
- CALBGXXQKYNRLO-UHFFFAOYSA-N 2-nitro-7-[[4-[2-[4-(trifluoromethoxy)phenyl]-1,3-thiazol-4-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C(N=1)=CSC=1C1=CC=C(OC(F)(F)F)C=C1 CALBGXXQKYNRLO-UHFFFAOYSA-N 0.000 claims 1
- AXSGSFPUZALTPB-UHFFFAOYSA-N 2-nitro-7-[[4-[2-[[4-(trifluoromethoxy)phenoxy]methyl]-1,3-oxazol-4-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C(N=1)=COC=1COC1=CC=C(OC(F)(F)F)C=C1 AXSGSFPUZALTPB-UHFFFAOYSA-N 0.000 claims 1
- SXCVNTHRLFSBOY-UHFFFAOYSA-N 2-nitro-7-[[4-[4-[3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]propyl]piperazin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1N(CC1)CCN1CCCC(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 SXCVNTHRLFSBOY-UHFFFAOYSA-N 0.000 claims 1
- ABFDBSSJEQJATF-UHFFFAOYSA-N 2-nitro-7-[[4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 ABFDBSSJEQJATF-UHFFFAOYSA-N 0.000 claims 1
- NEDDDYNVZBXBMF-UHFFFAOYSA-N 2-nitro-7-[[4-[4-[[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=C(OC(F)(F)F)C=C1 NEDDDYNVZBXBMF-UHFFFAOYSA-N 0.000 claims 1
- XICRSBZYTPYINV-UHFFFAOYSA-N 2-nitro-7-[[6-[4-[2-[4-(trifluoromethoxy)phenoxy]ethyl]piperidin-1-yl]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=C1N(CC1)CCC1CCOC1=CC=C(OC(F)(F)F)C=C1 XICRSBZYTPYINV-UHFFFAOYSA-N 0.000 claims 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- GGMZNCHFQWBFFQ-UHFFFAOYSA-N 7-[[3-fluoro-4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenoxy]methyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1F)=CC=C1N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 GGMZNCHFQWBFFQ-UHFFFAOYSA-N 0.000 claims 1
- FYNAXAJOXWPULF-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-[4-[2-[4-(trifluoromethoxy)phenyl]ethyl]piperidin-1-yl]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=C1N(CC1)CCC1CCC1=CC=C(OC(F)(F)F)C=C1 FYNAXAJOXWPULF-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 201000008827 tuberculosis Diseases 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 description 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161476003P | 2011-04-15 | 2011-04-15 | |
| US61/476,003 | 2011-04-15 | ||
| PCT/JP2012/060645 WO2012141338A1 (en) | 2011-04-15 | 2012-04-13 | 6,7 - dihydroimidazo [2, 1 - b] [1, 3] oxazine bactericides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014510695A JP2014510695A (ja) | 2014-05-01 |
| JP2014510695A5 true JP2014510695A5 (https=) | 2015-05-28 |
| JP5916739B2 JP5916739B2 (ja) | 2016-05-11 |
Family
ID=46168570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013532004A Expired - Fee Related JP5916739B2 (ja) | 2011-04-15 | 2012-04-13 | ６，７−ジヒドロイミダゾ［２，１−ｂ］［１，３］オキサジン化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9051333B2 (https=) |
| EP (1) | EP2697232B1 (https=) |
| JP (1) | JP5916739B2 (https=) |
| CN (1) | CN103596960B (https=) |
| WO (1) | WO2012141338A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN105753817A (zh) * | 2015-01-01 | 2016-07-13 | 成都贝斯凯瑞生物科技有限公司 | 一类取代氮杂环衍生物及其应用 |
| WO2016119706A1 (zh) * | 2015-01-29 | 2016-08-04 | 南京明德新药研发股份有限公司 | 抗肺结核病的硝基咪唑衍生物 |
| EP3421454B9 (en) * | 2016-02-26 | 2023-08-09 | Otsuka Pharmaceutical Co., Ltd. | Piperidine derivative |
| RU2657168C2 (ru) * | 2016-04-29 | 2018-06-08 | Общество с ограниченной ответственностью "Общество Сферического Кино" | Программно-аппаратный комплекс для автоматической калибровки многопроекторных систем с возможностью воспроизводить контент в высоком разрешении с использованием средств шифрования и цифровой дистрибьюции, способ шифрования контента для использования в способе воспроизведения контента |
| WO2019128963A1 (zh) * | 2017-12-26 | 2019-07-04 | 南京明德新药研发股份有限公司 | 抗肺结核病的硝基咪唑衍生物 |
| EP3908578A4 (en) * | 2019-01-08 | 2023-03-08 | B.G. Negev Technologies and Applications Ltd., at Ben-Gurion University | ANTIMICROBIAL COMPOUNDS AND COMPOSITIONS THEREOF |
| WO2020179859A1 (ja) | 2019-03-06 | 2020-09-10 | 第一三共株式会社 | ピロロピラゾール誘導体 |
| CN110452188A (zh) * | 2019-09-12 | 2019-11-15 | 蚌埠学院 | 一种伏硫西汀的制备方法 |
Family Cites Families (8)
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|---|---|---|---|---|
| JPH07330B2 (ja) | 1991-07-06 | 1995-01-11 | 日精樹脂工業株式会社 | 駆動装置 |
| US5668127A (en) | 1995-06-26 | 1997-09-16 | Pathogenesis Corporation | Nitroimidazole antibacterial compounds and methods of use thereof |
| AR041198A1 (es) | 2002-10-11 | 2005-05-04 | Otsuka Pharma Co Ltd | Compuesto 2,3-dihidro-6-nitroimidazo[2,1-b] oxaxol, y composiciones farmaceuticas que lo contienen |
| JP4761756B2 (ja) * | 2003-10-31 | 2011-08-31 | 大塚製薬株式会社 | ２，３−ジヒドロイミダゾ［２，１−ｂ］オキサゾ−ル化合物 |
| PT1678185E (pt) | 2003-10-31 | 2009-01-13 | Otsuka Pharma Co Ltd | Compostos 2,3-di-hidro-6-nitroimidazo[2,1-b]oxazole para o tratamento da tuberculose |
| JP5613656B2 (ja) * | 2008-03-26 | 2014-10-29 | グローバル、アライアンス、フォア、ティービー、ドラッグ、ディベロップメント | 置換されたフェニルオキサゾリジノンと共有結合した二環式ニトロイミダゾール |
| BR112012002214B1 (pt) * | 2009-07-31 | 2022-01-25 | Global Alliance For Tb Drug Development | Análogos de nitroimidazooxazina e nitroimidazooxazol, seus usos e composição farmacêutica |
| CA2769359C (en) * | 2009-07-31 | 2017-03-07 | Global Alliance For Tb Drug Development | Nitroimidazooxazines and their uses in anti-tubercular therapy |
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2012
- 2012-04-13 US US14/111,262 patent/US9051333B2/en not_active Expired - Fee Related
- 2012-04-13 JP JP2013532004A patent/JP5916739B2/ja not_active Expired - Fee Related
- 2012-04-13 EP EP12723752.7A patent/EP2697232B1/en not_active Not-in-force
- 2012-04-13 CN CN201280029213.6A patent/CN103596960B/zh not_active Expired - Fee Related
- 2012-04-13 WO PCT/JP2012/060645 patent/WO2012141338A1/en not_active Ceased
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