JP2004149527A5 - - Google Patents
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- JP2004149527A5 JP2004149527A5 JP2003353868A JP2003353868A JP2004149527A5 JP 2004149527 A5 JP2004149527 A5 JP 2004149527A5 JP 2003353868 A JP2003353868 A JP 2003353868A JP 2003353868 A JP2003353868 A JP 2003353868A JP 2004149527 A5 JP2004149527 A5 JP 2004149527A5
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- JP
- Japan
- Prior art keywords
- group
- substituted
- halogen
- unsubstituted
- phenyl
- 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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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 346
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 313
- 125000005843 halogen group Chemical group 0.000 claims 174
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 147
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 75
- -1 Biphenylyl Chemical group 0.000 claims 60
- 125000001424 substituent group Chemical group 0.000 claims 38
- 125000003277 amino group Chemical class 0.000 claims 36
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 27
- 125000004043 oxo group Chemical group O=* 0.000 claims 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 23
- 125000002252 acyl group Chemical group 0.000 claims 21
- 125000004193 piperazinyl group Chemical group 0.000 claims 17
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000004076 pyridyl group Chemical group 0.000 claims 13
- 125000003386 piperidinyl group Chemical group 0.000 claims 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 9
- 125000005936 piperidyl group Chemical group 0.000 claims 9
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000002971 oxazolyl group Chemical group 0.000 claims 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 7
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 4
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 3
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical group C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical group C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical group C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000005606 carbostyryl group Chemical group 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- FIYNYEBSXNUVMP-QGZVFWFLSA-N (2r)-2-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1C1=CC=C(Cl)C=C1 FIYNYEBSXNUVMP-QGZVFWFLSA-N 0.000 claims 1
- AKNCGQAEIOXCDV-XMMPIXPASA-N (2r)-2-[[4-[4-(4-chlorophenoxy)piperidin-1-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(Cl)C=C1 AKNCGQAEIOXCDV-XMMPIXPASA-N 0.000 claims 1
- LYOIGYXSILNCGD-HSZRJFAPSA-N (2r)-2-[[4-[4-(4-chlorophenyl)piperazin-1-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1C1=CC=C(Cl)C=C1 LYOIGYXSILNCGD-HSZRJFAPSA-N 0.000 claims 1
- GFILILIJROUKQX-XMMPIXPASA-N (2r)-2-[[4-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=C(Cl)C=C1 GFILILIJROUKQX-XMMPIXPASA-N 0.000 claims 1
- YKTNEBRVZQRHBY-AMOIIXHWSA-N (2r)-2-methyl-6-nitro-2-[[4-[3-[4-(trifluoromethoxy)phenoxy]-8-azabicyclo[3.2.1]octan-8-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N1C(C2)CCC1CC2OC1=CC=C(OC(F)(F)F)C=C1 YKTNEBRVZQRHBY-AMOIIXHWSA-N 0.000 claims 1
- LWBIDBQNZCECSS-QGZVFWFLSA-N (2r)-2-methyl-6-nitro-2-[[4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1C1=CC=C(OC(F)(F)F)C=C1 LWBIDBQNZCECSS-QGZVFWFLSA-N 0.000 claims 1
- AWDXPROPYRAKLT-GOSISDBHSA-N (2r)-2-methyl-6-nitro-2-[[4-[4-(trifluoromethyl)phenoxy]piperidin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCC1OC1=CC=C(C(F)(F)F)C=C1 AWDXPROPYRAKLT-GOSISDBHSA-N 0.000 claims 1
- QJIFSMDAAMROGJ-QGZVFWFLSA-N (2r)-2-methyl-6-nitro-2-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 QJIFSMDAAMROGJ-QGZVFWFLSA-N 0.000 claims 1
- DMAIXEPFPJEFMX-XMMPIXPASA-N (2r)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethyl)phenoxy]piperidin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(C(F)(F)F)C=C1 DMAIXEPFPJEFMX-XMMPIXPASA-N 0.000 claims 1
- ZMQUUTLDDPXMNF-HSZRJFAPSA-N (2r)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 ZMQUUTLDDPXMNF-HSZRJFAPSA-N 0.000 claims 1
- GZEWSZWWEUTZIP-XMMPIXPASA-N (2r)-2-methyl-6-nitro-2-[[4-[4-[[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=C(OC(F)(F)F)C=C1 GZEWSZWWEUTZIP-XMMPIXPASA-N 0.000 claims 1
- JMBCEUCFQUVBIJ-XMMPIXPASA-N (2r)-2-methyl-6-nitro-2-[[4-[4-[[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=C(C(F)(F)F)C=C1 JMBCEUCFQUVBIJ-XMMPIXPASA-N 0.000 claims 1
- VVIPVTJEVUGSRO-XMMPIXPASA-N (2r)-2-methyl-6-nitro-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]piperazin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VVIPVTJEVUGSRO-XMMPIXPASA-N 0.000 claims 1
- UCWWPISVZMWAJC-OAQYLSRUSA-N (2r)-6-nitro-2-[[4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenoxy]methyl]-2,3-dihydroimidazo[2,1-b][1,3]oxazole Chemical compound C([C@H]1CN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 UCWWPISVZMWAJC-OAQYLSRUSA-N 0.000 claims 1
- FIYNYEBSXNUVMP-KRWDZBQOSA-N (2s)-2-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1C1=CC=C(Cl)C=C1 FIYNYEBSXNUVMP-KRWDZBQOSA-N 0.000 claims 1
- IBYBLYXYIMYXLC-VWLOTQADSA-N (2s)-2-[[4-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1C(CC1)CCN1CC1=CC=C(Cl)C=C1 IBYBLYXYIMYXLC-VWLOTQADSA-N 0.000 claims 1
- AKNCGQAEIOXCDV-DEOSSOPVSA-N (2s)-2-[[4-[4-(4-chlorophenoxy)piperidin-1-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(Cl)C=C1 AKNCGQAEIOXCDV-DEOSSOPVSA-N 0.000 claims 1
- LYOIGYXSILNCGD-QHCPKHFHSA-N (2s)-2-[[4-[4-(4-chlorophenyl)piperazin-1-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1C1=CC=C(Cl)C=C1 LYOIGYXSILNCGD-QHCPKHFHSA-N 0.000 claims 1
- GFILILIJROUKQX-DEOSSOPVSA-N (2s)-2-[[4-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]phenoxy]methyl]-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=C(Cl)C=C1 GFILILIJROUKQX-DEOSSOPVSA-N 0.000 claims 1
- YKTNEBRVZQRHBY-NYJDFHIHSA-N (2s)-2-methyl-6-nitro-2-[[4-[3-[4-(trifluoromethoxy)phenoxy]-8-azabicyclo[3.2.1]octan-8-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N1C(C2)CCC1CC2OC1=CC=C(OC(F)(F)F)C=C1 YKTNEBRVZQRHBY-NYJDFHIHSA-N 0.000 claims 1
- LXWLEHKPRBDYGL-SFHVURJKSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 LXWLEHKPRBDYGL-SFHVURJKSA-N 0.000 claims 1
- LWBIDBQNZCECSS-KRWDZBQOSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-(trifluoromethoxy)phenyl]piperazin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1C1=CC=C(OC(F)(F)F)C=C1 LWBIDBQNZCECSS-KRWDZBQOSA-N 0.000 claims 1
- QJIFSMDAAMROGJ-KRWDZBQOSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 QJIFSMDAAMROGJ-KRWDZBQOSA-N 0.000 claims 1
- XDAOLTSRNUSPPH-DEOSSOPVSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 XDAOLTSRNUSPPH-DEOSSOPVSA-N 0.000 claims 1
- DMAIXEPFPJEFMX-DEOSSOPVSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethyl)phenoxy]piperidin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(C(F)(F)F)C=C1 DMAIXEPFPJEFMX-DEOSSOPVSA-N 0.000 claims 1
- ZMQUUTLDDPXMNF-QHCPKHFHSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 ZMQUUTLDDPXMNF-QHCPKHFHSA-N 0.000 claims 1
- GZEWSZWWEUTZIP-DEOSSOPVSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-[[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=C(OC(F)(F)F)C=C1 GZEWSZWWEUTZIP-DEOSSOPVSA-N 0.000 claims 1
- JMBCEUCFQUVBIJ-DEOSSOPVSA-N (2s)-2-methyl-6-nitro-2-[[4-[4-[[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]phenoxy]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=C(C(F)(F)F)C=C1 JMBCEUCFQUVBIJ-DEOSSOPVSA-N 0.000 claims 1
- VVIPVTJEVUGSRO-DEOSSOPVSA-N (2s)-2-methyl-6-nitro-2-[[4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]piperazin-1-yl]methyl]-3h-imidazo[2,1-b][1,3]oxazole Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VVIPVTJEVUGSRO-DEOSSOPVSA-N 0.000 claims 1
- UCWWPISVZMWAJC-NRFANRHFSA-N (2s)-6-nitro-2-[[4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenoxy]methyl]-2,3-dihydroimidazo[2,1-b][1,3]oxazole Chemical compound C([C@@H]1CN2C=C(N=C2O1)[N+](=O)[O-])OC(C=C1)=CC=C1N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 UCWWPISVZMWAJC-NRFANRHFSA-N 0.000 claims 1
- KLYOKTHRMAYFJG-UHFFFAOYSA-N (3,4-dichlorophenyl)methyl 4-[4-[(2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl)methoxy]phenyl]piperazine-1-carboxylate Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1N(CC1)CCN1C(=O)OCC1=CC=C(Cl)C(Cl)=C1 KLYOKTHRMAYFJG-UHFFFAOYSA-N 0.000 claims 1
- KLYOKTHRMAYFJG-RUZDIDTESA-N (3,4-dichlorophenyl)methyl 4-[4-[[(2r)-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl]methoxy]phenyl]piperazine-1-carboxylate Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1C(=O)OCC1=CC=C(Cl)C(Cl)=C1 KLYOKTHRMAYFJG-RUZDIDTESA-N 0.000 claims 1
- KLYOKTHRMAYFJG-VWLOTQADSA-N (3,4-dichlorophenyl)methyl 4-[4-[[(2s)-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl]methoxy]phenyl]piperazine-1-carboxylate Chemical compound C([C@@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1N(CC1)CCN1C(=O)OCC1=CC=C(Cl)C(Cl)=C1 KLYOKTHRMAYFJG-VWLOTQADSA-N 0.000 claims 1
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- PBHHVJAUXOFMRE-UHFFFAOYSA-N n-[4-[(2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl)methyl]piperazin-1-yl]-1-[4-(trifluoromethyl)phenyl]methanimine Chemical compound C1N2C=C([N+]([O-])=O)N=C2OC1(C)CN(CC1)CCN1N=CC1=CC=C(C(F)(F)F)C=C1 PBHHVJAUXOFMRE-UHFFFAOYSA-N 0.000 claims 1
- TXRSPJFTVZSLCH-UHFFFAOYSA-N n-[4-[(2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl)methyl]piperazin-1-yl]-1-[5-(trifluoromethoxy)-1-benzofuran-2-yl]methanimine Chemical compound FC(F)(F)OC1=CC=C2OC(C=NN3CCN(CC3)CC3(C)OC4=NC(=CN4C3)[N+]([O-])=O)=CC2=C1 TXRSPJFTVZSLCH-UHFFFAOYSA-N 0.000 claims 1
- YBSBINDRCMOTTG-UHFFFAOYSA-N n-[4-[(2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl)methyl]piperazin-1-yl]-1-[5-(trifluoromethyl)-1-benzofuran-2-yl]methanimine Chemical compound FC(F)(F)C1=CC=C2OC(C=NN3CCN(CC3)CC3(C)OC4=NC(=CN4C3)[N+]([O-])=O)=CC2=C1 YBSBINDRCMOTTG-UHFFFAOYSA-N 0.000 claims 1
- PBHHVJAUXOFMRE-SFHVURJKSA-N n-[4-[[(2s)-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl]methyl]piperazin-1-yl]-1-[4-(trifluoromethyl)phenyl]methanimine Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)N(CC1)CCN1N=CC1=CC=C(C(F)(F)F)C=C1 PBHHVJAUXOFMRE-SFHVURJKSA-N 0.000 claims 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000005543 phthalimide group Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000001725 pyrenyl group Chemical group 0.000 claims 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 1
- 125000005554 pyridyloxy group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000003536 tetrazoles Chemical group 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 C*(*=C(*)O1)C1=* Chemical compound C*(*=C(*)O1)C1=* 0.000 description 1
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US10851079B2 (en) | 2016-02-26 | 2020-12-01 | Otsuka Pharmaceutical Co., Ltd. | Piperidine derivative |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1330444B1 (en) | 2000-11-01 | 2011-03-23 | Millennium Pharmaceuticals, Inc. | Nitrogenous heterocyclic compounds and process for making them |
| AR041605A1 (es) * | 2002-10-15 | 2005-05-26 | Otsuka Pharma Co Ltd | Compuesto 1- sustituido-4-nitroimidazol y metodo para preparar el mismo |
| CA2539335A1 (en) * | 2003-10-31 | 2005-05-12 | Otsuka Pharmaceutical Co., Ltd. | 2,3-dihydro-6-nitroimidazo (2,1-b) oxazole compounds for the treatment of tuberculosis |
| 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 |
| TWI300409B (en) | 2004-02-18 | 2008-09-01 | Otsuka Pharma Co Ltd | Method for producing 4-nitroimidazole compound |
| PT1731518E (pt) | 2004-03-31 | 2014-09-18 | Nippon Soda Co | Composto amina cíclico e agente de controlo de pragas |
| 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 |
| EP1896453B1 (en) * | 2005-06-20 | 2009-12-02 | Schering Corporation | Carbon-linked substituted piperidines and derivatives thereof useful as histamine h3 antagonists |
| CA2610749C (en) * | 2005-07-28 | 2013-06-04 | Otsuka Pharmaceutical Co., Ltd. | Pharmaceutical composition comprising 2,3-dihydro-6-nitroimidazo [2,1-b]oxazole derivatives |
| TWI368509B (en) * | 2005-10-05 | 2012-07-21 | Otsuka Pharma Co Ltd | Antituberculous therapeutic drugs and kit containing the same |
| JP5105818B2 (ja) * | 2005-10-05 | 2012-12-26 | 大塚製薬株式会社 | 医薬組成物 |
| WO2007040280A1 (ja) * | 2005-10-06 | 2007-04-12 | Nippon Soda Co., Ltd. | 環状アミン化合物および有害生物防除剤 |
| TW200800268A (en) * | 2005-11-04 | 2008-01-01 | Otsuka Pharma Co Ltd | Medicinal composition showing improved drug absorbability |
| EP1968961A2 (en) | 2005-12-21 | 2008-09-17 | Decode Genetics EHF | Biaryl nitrogen heterocycle inhibitors of lta4h for treating inflammation |
| US20090018169A1 (en) * | 2006-02-13 | 2009-01-15 | Laboratoires Serono Sa | Sulfonamide Derivatives for the Treatment of Bacterial Infections |
| JP2007297305A (ja) * | 2006-04-28 | 2007-11-15 | Daiso Co Ltd | Ｎ−（２，３−エポキシ−２−メチルプロピル）フタルイミドの製造法 |
| EP2125750B1 (en) * | 2007-02-26 | 2014-05-21 | Vitae Pharmaceuticals, Inc. | Cyclic urea and carbamate inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| AR070301A1 (es) * | 2007-05-08 | 2010-03-31 | Otsuka Pharma Co Ltd | Compuesto epoxi y metodo para producir el mismo |
| US8329897B2 (en) * | 2007-07-26 | 2012-12-11 | Vitae Pharmaceuticals, Inc. | Synthesis of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 |
| TW200922581A (en) * | 2007-08-15 | 2009-06-01 | Glaxo Group Ltd | Compounds |
| WO2009050204A1 (en) * | 2007-10-16 | 2009-04-23 | Glaxo Group Limited | Quinoline derivatives used to treat inflammatory and allergic diseases |
| AR069207A1 (es) * | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| CA2708303A1 (en) | 2007-12-11 | 2009-06-18 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11.beta.-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) * | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| JP5490020B2 (ja) | 2008-01-24 | 2014-05-14 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状カルバゼート及びセミカルバジドインヒビター |
| WO2009102428A2 (en) * | 2008-02-11 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | 1,3-OXAZEPAN-2-ONE AND 1,3-DIAZEPAN-2-ONE INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE 1 |
| US8598160B2 (en) * | 2008-02-15 | 2013-12-03 | Vitae Pharmaceuticals, Inc. | Cycloalkyl lactame derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| JP5538356B2 (ja) * | 2008-03-18 | 2014-07-02 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤 |
| US7666864B2 (en) * | 2008-03-26 | 2010-02-23 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazole-substituted phenyl oxazolidinones |
| CA2723034A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| US8569292B2 (en) | 2008-05-01 | 2013-10-29 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| US8242111B2 (en) * | 2008-05-01 | 2012-08-14 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| PL2300461T3 (pl) | 2008-05-01 | 2013-09-30 | Vitae Pharmaceuticals Inc | Cykliczne inhibitory dehydrogenazy 11beta-hydroksysteroidów 1 |
| JP5379160B2 (ja) | 2008-07-25 | 2013-12-25 | 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 | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状インヒビター |
| TW201016691A (en) | 2008-07-25 | 2010-05-01 | Boehringer Ingelheim Int | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| BRPI0917394A2 (pt) * | 2008-08-18 | 2019-09-24 | Univ Yale | moduladores de mif |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| WO2010143007A1 (en) * | 2009-06-10 | 2010-12-16 | Dynamit Nobel Gmbh Explosivstoff-Und Systemtechnik | Method for the production of 2-halogeno-4-nitroimidazole |
| JP5525515B2 (ja) | 2008-08-21 | 2014-06-18 | デイナミート ノーベル ゲゼルシャフト ミット ベシュレンクテル ハフツング エクスプロジーフシュトッフ− ウント ジステームテヒニク | ２−ハロ−４−ニトロイミダゾール及びその中間体の製造方法 |
| EP2393807B1 (en) | 2009-02-04 | 2013-08-14 | Boehringer Ingelheim International GmbH | Cyclic inhibitors of 11 -hydroxysteroid dehydrogenase 1 |
| TW201039034A (en) * | 2009-04-27 | 2010-11-01 | Chunghwa Picture Tubes Ltd | Pixel structure and the method of forming the same |
| GEP20156309B (en) * | 2009-04-30 | 2015-07-10 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| MA33216B1 (fr) | 2009-04-30 | 2012-04-02 | Boehringer Ingelheim Int | Inhibiteurs cycliques de la 11béta-hydroxysteroïde déshydrogénase 1 |
| JP5656986B2 (ja) | 2009-06-11 | 2015-01-21 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １，３−オキサジナン−２−オン構造に基づく１１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状阻害剤 |
| JP5749263B2 (ja) | 2009-07-01 | 2015-07-15 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状インヒビター |
| CN102741259B (zh) * | 2009-07-31 | 2016-04-13 | 全球结核病药物研发联盟 | 硝基咪唑并噁嗪和硝基咪唑并噁唑的类似物及其用途 |
| US9198913B2 (en) | 2009-07-31 | 2015-12-01 | Global Alliance For Tb Drug Development | Nitroimidazooxazines and their uses in anti-tubercular therapy |
| WO2011014774A1 (en) * | 2009-07-31 | 2011-02-03 | Global Alliance For Tb Drug Development | Nitroimidazooxazines and their uses in anti-tubercular therapy |
| EP2495563A4 (en) | 2009-10-26 | 2013-04-10 | Fujifilm Ri Pharma Co Ltd | DIAGNOSTIC AGENT FOR INFECTIOUS DISEASES |
| TW201200523A (en) * | 2010-01-29 | 2012-01-01 | Otsuka Pharma Co Ltd | Synthetic intermediate of oxazole compound and method for producing the same |
| GB201012209D0 (en) * | 2010-05-31 | 2010-09-08 | Ge Healthcare Ltd | In vivo imaging agent |
| EP2582698B1 (en) | 2010-06-16 | 2016-09-14 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| JP5813106B2 (ja) | 2010-06-25 | 2015-11-17 | 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 | 代謝障害の処置のための１１−β−ＨＳＤ１のインヒビターとしてのアザスピロヘキサノン |
| WO2012059416A1 (en) | 2010-11-02 | 2012-05-10 | Boehringer Ingelheim International Gmbh | Pharmaceutical combinations for the treatment of metabolic disorders |
| JP5916739B2 (ja) | 2011-04-15 | 2016-05-11 | 大塚製薬株式会社 | ６，７−ジヒドロイミダゾ［２，１−ｂ］［１，３］オキサジン化合物 |
| 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 |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| FR3000064A1 (fr) * | 2012-12-21 | 2014-06-27 | Univ Lille Ii Droit & Sante | Composes de type spiroisoxazoline ayant une activite potentialisatrice de l'activite d'un antibiotique-composition et produit pharmaceutiques comprenant de tels composes |
| ES2707362T3 (es) | 2013-10-04 | 2019-04-03 | Council Scient Ind Res | 6-nitro-2,3-dihidroimidazo [2,1-b] oxazoles y un procedimiento de preparación de los mismos |
| CN103524492A (zh) * | 2013-10-23 | 2014-01-22 | 中国药科大学 | 侧链含硝基咪唑基团取代的喹诺酮类化合物、其制备及用途 |
| 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 |
| CN107108650B (zh) * | 2014-10-21 | 2019-10-18 | 印度科学工业研究所 | 抗分枝杆菌剂取代的1,2,3-三唑-1-基-甲基-2,3-二氢-2-甲基-6-硝基咪唑并[2,1-b]噁唑及其制备方法 |
| CN105732659B (zh) * | 2014-12-12 | 2019-07-16 | 上海阳帆医药科技有限公司 | 硝基咪唑类化合物及其制备方法和在制药中的用途 |
| 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 |
| EP3275862B1 (en) | 2015-03-27 | 2020-08-12 | Otsuka Pharmaceutical Co., Ltd. | Method for producing 1-(4-hydroxyphenyl)-4-(4-trifluoromethoxyphenoxy)piperidine or salt thereof |
| CN106317072B (zh) * | 2015-06-17 | 2020-03-17 | 盟科医药技术(上海)有限公司 | 用于分枝杆菌感染治疗的杂环化合物及其应用 |
| CN105859628B (zh) * | 2016-04-19 | 2018-08-07 | 清远职业技术学院 | 一种抗菌化合物对n咪唑苯甲醛缩邻甲苯胺希夫碱及其制备方法和应用 |
| EP3489242A4 (en) * | 2016-07-22 | 2020-06-24 | Medshine Discovery Inc. | NITROIMIDAZOLE CRYSTAL AND SALT, AND THEIR MANUFACTURING METHOD |
| SI3668879T1 (sl) * | 2017-08-16 | 2022-04-29 | Glaxosmithkline Intellectual Property Development Limited | Nove spojine |
| AU2019287313B2 (en) | 2018-06-11 | 2024-08-01 | Otsuka Pharmaceutical Co., Ltd. | Delamanid-containing composition |
| CN109705022A (zh) * | 2018-12-28 | 2019-05-03 | 上海彩迩文生化科技有限公司 | 一种芳香胺中间体的制备方法 |
| CN112300192B (zh) * | 2019-08-02 | 2023-08-11 | 南京长澳医药科技有限公司 | 硝基咪唑类化合物及其制备方法和用途 |
| CN110483549B (zh) * | 2019-08-30 | 2021-03-05 | 沈阳药科大学 | 一种硝基咪唑吡喃类抗结核药物的制备方法 |
| CN110615800A (zh) * | 2019-10-16 | 2019-12-27 | 李丽丽 | 硝基咪唑类化合物及其制备方法和用途 |
| CN112156088B (zh) * | 2020-10-30 | 2021-08-31 | 健民药业集团股份有限公司 | 一种化合物在制备结核分枝杆菌抑制剂中的用途 |
| CN113603706A (zh) * | 2021-08-04 | 2021-11-05 | 深圳市泰力生物医药有限公司 | 德拉马尼的晶型、含有该晶型的活性药物和药物组合物 |
| WO2024024938A1 (ja) | 2022-07-29 | 2024-02-01 | 大塚製薬株式会社 | デラマニド含有固体分散体 |
| CN115368252B (zh) * | 2022-09-19 | 2024-01-12 | 西北农林科技大学 | 一种4-胺基酚类衍生物及应用 |
| CN116640106B (zh) * | 2023-05-11 | 2024-03-08 | 郑州大学 | 一种苯基哌嗪类化合物及其制备方法、应用 |
| CN119059990B (zh) * | 2024-11-01 | 2025-02-07 | 安徽昊帆生物有限公司 | 1-氨基甲酸叔丁酯哌嗪的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5668127A (en) | 1995-06-26 | 1997-09-16 | Pathogenesis Corporation | Nitroimidazole antibacterial compounds and methods of use thereof |
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2005
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10851079B2 (en) | 2016-02-26 | 2020-12-01 | Otsuka Pharmaceutical Co., Ltd. | Piperidine derivative |
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