JP2000505084A - アゾリルピペラジニルフェニルオキサゾリジノン抗微生物剤 - Google Patents
アゾリルピペラジニルフェニルオキサゾリジノン抗微生物剤Info
- Publication number
- JP2000505084A JP2000505084A JP9530192A JP53019297A JP2000505084A JP 2000505084 A JP2000505084 A JP 2000505084A JP 9530192 A JP9530192 A JP 9530192A JP 53019297 A JP53019297 A JP 53019297A JP 2000505084 A JP2000505084 A JP 2000505084A
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- methyl
- phenyl
- piperazinyl
- oxazolidinyl
- 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.)
- Withdrawn
Links
- 239000004599 antimicrobial Substances 0.000 title description 4
- UBNIPSDNVLNRMR-UHFFFAOYSA-N 3-phenyl-4-piperazin-1-yl-4-(1h-pyrrol-2-yl)-1,3-oxazolidin-2-one Chemical compound O=C1OCC(C=2NC=CC=2)(N2CCNCC2)N1C1=CC=CC=C1 UBNIPSDNVLNRMR-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 36
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 208000015181 infectious disease Diseases 0.000 claims abstract description 5
- 230000000813 microbial effect Effects 0.000 claims abstract description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 122
- 238000000034 method Methods 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- -1 phenyl - Chemical class 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 239000011737 fluorine Substances 0.000 claims description 31
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 30
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 17
- 150000003536 tetrazoles Chemical class 0.000 claims description 12
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 11
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 10
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- OGVWWGVZVJUPHF-UHFFFAOYSA-N 1,2,4-thiadiazol-3-one Chemical compound O=C1N=CSN1 OGVWWGVZVJUPHF-UHFFFAOYSA-N 0.000 claims description 5
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 5
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 5
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 5
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 4
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 4
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 4
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 4
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 claims description 4
- GJGROPRLXDXIAN-UHFFFAOYSA-N 1,3-thiazol-4-one Chemical compound O=C1CSC=N1 GJGROPRLXDXIAN-UHFFFAOYSA-N 0.000 claims description 4
- AXTPKYQMUDUCFW-UHFFFAOYSA-N 1,3-thiazole 1,1-dioxide Chemical compound O=S1(=O)C=CN=C1 AXTPKYQMUDUCFW-UHFFFAOYSA-N 0.000 claims description 4
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- NQBUERYLUPYOEL-UHFFFAOYSA-N isoindol-4-one Chemical compound O=C1C=CC=C2C=NC=C12 NQBUERYLUPYOEL-UHFFFAOYSA-N 0.000 claims description 4
- VIBLXFJNXHLPKR-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(6-nitro-1,3-benzothiazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SC3=CC(=CC=C3N=2)[N+]([O-])=O)CC1 VIBLXFJNXHLPKR-KRWDZBQOSA-N 0.000 claims description 4
- PJCFLHUCYONHAS-UHFFFAOYSA-N oxathiazolone Chemical compound O=C1OC=NS1 PJCFLHUCYONHAS-UHFFFAOYSA-N 0.000 claims description 4
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 4
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 claims description 3
- PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical compound O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 claims description 3
- QWSQNLKNOPXCKY-UHFFFAOYSA-N 3h-1,2,4-dithiazole 1-oxide Chemical compound O=S1SCN=C1 QWSQNLKNOPXCKY-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- JLXZMLLNPNOODV-UHFFFAOYSA-N imidazol-4-one Chemical compound O=C1C=NC=N1 JLXZMLLNPNOODV-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- QXMJAMBPNHRAPD-UHFFFAOYSA-N 1-oxido-3h-oxathiazol-1-ium Chemical compound [O-][O+]1SNC=C1 QXMJAMBPNHRAPD-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- OVZHELCFKSFINS-UHFFFAOYSA-N 3h-1,3,4-thiadiazol-2-one Chemical compound O=C1NN=CS1 OVZHELCFKSFINS-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- MQTAXEWLLDRGGF-IBGZPJMESA-N n-[[(5s)-3-[3-fluoro-4-[4-(3-oxo-2-phenyl-1,2,4-thiadiazol-5-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SN(C(=O)N=2)C=2C=CC=CC=2)CC1 MQTAXEWLLDRGGF-IBGZPJMESA-N 0.000 claims description 2
- VPGSJPCBGQHKKH-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-nitro-1,3-benzoxazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2OC3=CC=C(C=C3N=2)[N+]([O-])=O)CC1 VPGSJPCBGQHKKH-KRWDZBQOSA-N 0.000 claims description 2
- KKSMBAFOLNYRHG-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-(1,3-benzoxazol-2-yl)piperazin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2OC3=CC=CC=C3N=2)CC1 KKSMBAFOLNYRHG-KRWDZBQOSA-N 0.000 claims description 2
- SSBINBKROWNWOR-HNNXBMFYSA-N n-[[(5s)-3-[4-[4-(6,7-difluoro-1,3-benzoxazol-2-yl)piperazin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2OC3=C(F)C(F)=CC=C3N=2)CC1 SSBINBKROWNWOR-HNNXBMFYSA-N 0.000 claims description 2
- CIVRAVQIWCBWJV-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-fluoro-1,3-benzoxazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2OC3=CC=C(F)C=C3N=2)CC1 CIVRAVQIWCBWJV-KRWDZBQOSA-N 0.000 claims 6
- MEHWMCBRDRPNSM-AWEZNQCLSA-N FC=1C=C(C=CC=1N1CCN(CC1)C1=CN=NN1)N1C(O[C@H](C1)CNC(C)=O)=O Chemical compound FC=1C=C(C=CC=1N1CCN(CC1)C1=CN=NN1)N1C(O[C@H](C1)CNC(C)=O)=O MEHWMCBRDRPNSM-AWEZNQCLSA-N 0.000 claims 2
- HHYUQROEEXLPQP-ZDUSSCGKSA-N N-[[(5S)-3-[4-[4-(4,5-dioxo-1,3-thiazol-2-yl)piperazin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SC(=O)C(=O)N=2)CC1 HHYUQROEEXLPQP-ZDUSSCGKSA-N 0.000 claims 2
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 2
- STAGCARWPQISMC-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1,2,4-oxadiazol-5-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2ON=CN=2)CC1 STAGCARWPQISMC-AWEZNQCLSA-N 0.000 claims 2
- QYAWDRJHPZFYRM-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1,3,4-oxadiazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2OC=NN=2)CC1 QYAWDRJHPZFYRM-AWEZNQCLSA-N 0.000 claims 2
- LXZKSYVKEUEFCM-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1h-imidazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2NC=CN=2)CC1 LXZKSYVKEUEFCM-HNNXBMFYSA-N 0.000 claims 2
- GZVRDFGOXZZTGH-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-oxo-1,2,4-triazol-3-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2N=NC(=O)N=2)CC1 GZVRDFGOXZZTGH-ZDUSSCGKSA-N 0.000 claims 2
- PDIZFGRQAJCXAJ-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-oxo-2h-1,2,4-oxadiazol-3-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2NOC(=O)N=2)CC1 PDIZFGRQAJCXAJ-ZDUSSCGKSA-N 0.000 claims 2
- FPBUUQCZDSJHMB-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-[4-(thiatriazol-5-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SN=NN=2)CC1 FPBUUQCZDSJHMB-ZDUSSCGKSA-N 0.000 claims 2
- NIFXEFLWHOFEQJ-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-(1h-benzimidazol-2-yl)piperazin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2NC3=CC=CC=C3N=2)CC1 NIFXEFLWHOFEQJ-KRWDZBQOSA-N 0.000 claims 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims 1
- 125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- LBEJCEINAPDREK-AWEZNQCLSA-N N-[[(5S)-3-[3-fluoro-4-[4-(1,2,4-thiadiazol-5-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SN=CN=2)CC1 LBEJCEINAPDREK-AWEZNQCLSA-N 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- NIJBZHNDZAJWCU-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1,2,4-oxadiazol-3-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C2=NOC=N2)CC1 NIJBZHNDZAJWCU-AWEZNQCLSA-N 0.000 claims 1
- KNXLOCRYMMBHJV-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1,3-oxazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2OC=CN=2)CC1 KNXLOCRYMMBHJV-HNNXBMFYSA-N 0.000 claims 1
- RAZBRAORPBIYSV-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-(3-methyl-1,2,4-thiadiazol-5-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SN=C(C)N=2)CC1 RAZBRAORPBIYSV-HNNXBMFYSA-N 0.000 claims 1
- FXIZKAUTUCTOOE-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-methyl-1,3,4-thiadiazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SC(C)=NN=2)CC1 FXIZKAUTUCTOOE-HNNXBMFYSA-N 0.000 claims 1
- FNKCRWBEYPKWFC-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S1C(SC)=NN=C1N1CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 FNKCRWBEYPKWFC-AWEZNQCLSA-N 0.000 claims 1
- AHACLWCQWMLMMW-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-propyl-1,3,4-thiadiazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S1C(CCC)=NN=C1N1CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 AHACLWCQWMLMMW-INIZCTEOSA-N 0.000 claims 1
- GAAKDSAJGDVNPY-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-[4-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2SC(=NN=2)C(F)(F)F)CC1 GAAKDSAJGDVNPY-ZDUSSCGKSA-N 0.000 claims 1
- PEKDKOZHGKKISE-VYRBHSGPSA-N n-[[(5s)-3-[4-[4-(5-cyano-1,3,4-thiadiazol-2-yl)-3-fluoropiperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CC(F)N(CC2)C=2SC(=NN=2)C#N)C=C1 PEKDKOZHGKKISE-VYRBHSGPSA-N 0.000 claims 1
- BWPQOYRUVBXFRP-HNNXBMFYSA-N n-[[(5s)-3-[4-[4-(5-ethyl-1,3,4-thiadiazol-2-yl)piperazin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S1C(CC)=NN=C1N1CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 BWPQOYRUVBXFRP-HNNXBMFYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003943 azolyl group Chemical group 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 239000000203 mixture Substances 0.000 description 61
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- 239000000314 lubricant Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
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- 229940017219 methyl propionate Drugs 0.000 description 1
- VYHVQEYOFIYNJP-UHFFFAOYSA-N methyl thiocyanate Chemical compound CSC#N VYHVQEYOFIYNJP-UHFFFAOYSA-N 0.000 description 1
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- GBOCTLJIKBPFJY-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[4-(6-fluoro-1,3-benzoxazol-2-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C=2OC3=CC(F)=CC=C3N=2)CC1 GBOCTLJIKBPFJY-KRWDZBQOSA-N 0.000 description 1
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- PEEXCRJDFUVJRT-UHFFFAOYSA-M potassium;methoxymethanedithioate Chemical compound [K+].COC([S-])=S PEEXCRJDFUVJRT-UHFFFAOYSA-M 0.000 description 1
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- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
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- 125000005580 triphenylene group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1231696P | 1996-02-26 | 1996-02-26 | |
| US60/012,316 | 1996-02-26 | ||
| PCT/US1997/001970 WO1997030981A1 (en) | 1996-02-26 | 1997-02-18 | Azolyl piperazinyl phenyl oxazolidinone antimicrobials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000505084A true JP2000505084A (ja) | 2000-04-25 |
| JP2000505084A5 JP2000505084A5 (enExample) | 2004-11-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9530192A Withdrawn JP2000505084A (ja) | 1996-02-26 | 1997-02-18 | アゾリルピペラジニルフェニルオキサゾリジノン抗微生物剤 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5736545A (enExample) |
| EP (1) | EP0883611B1 (enExample) |
| JP (1) | JP2000505084A (enExample) |
| KR (1) | KR19990087238A (enExample) |
| CN (1) | CN1082952C (enExample) |
| AT (1) | ATE221521T1 (enExample) |
| AU (1) | AU703831B2 (enExample) |
| DE (1) | DE69714418T2 (enExample) |
| DK (1) | DK0883611T3 (enExample) |
| ES (1) | ES2180945T3 (enExample) |
| ID (1) | ID18467A (enExample) |
| MY (1) | MY116093A (enExample) |
| NZ (1) | NZ331011A (enExample) |
| PE (1) | PE55898A1 (enExample) |
| PT (1) | PT883611E (enExample) |
| TW (1) | TW442460B (enExample) |
| WO (1) | WO1997030981A1 (enExample) |
| ZA (1) | ZA971287B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007521281A (ja) * | 2003-07-02 | 2007-08-02 | メルク アンド カンパニー インコーポレーテッド | シクロプロピル基置換されたオキサゾリジノン抗生物質およびこれらの誘導体 |
| WO2019208812A1 (ja) * | 2018-04-27 | 2019-10-31 | 国立大学法人大阪大学 | ベンゾイソオキサゾール化合物 |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| GB9702213D0 (en) | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| AU729745B2 (en) * | 1997-07-11 | 2001-02-08 | Pharmacia & Upjohn Company | Thiadiazolyl and oxadiazolyl phenyl oxazolidinone antibacterial agents |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| US6562844B2 (en) | 1998-01-23 | 2003-05-13 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| US7002020B1 (en) | 1998-01-23 | 2006-02-21 | Pharmacia & Upjohn Company | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| WO1999037630A1 (en) * | 1998-01-23 | 1999-07-29 | Versicor, Inc. | Oxazolidinone combinatorial libraries, compositions and methods of preparation |
| NZ508174A (en) | 1998-06-05 | 2003-10-31 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| DE59905341D1 (de) * | 1998-08-04 | 2003-06-05 | Ciba Sc Holding Ag | Verwendung von Oxathiazolonen als Mikrobizide |
| JP2002535680A (ja) | 1999-01-27 | 2002-10-22 | ファルマシア・アンド・アップジョン・カンパニー | 延長因子ｐ活性モジュレーターのアッセイ方法 |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
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| WO1995014684A1 (en) * | 1993-11-22 | 1995-06-01 | The Upjohn Company | Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones |
-
1997
- 1997-01-31 MY MYPI97000373A patent/MY116093A/en unknown
- 1997-02-14 ZA ZA971287A patent/ZA971287B/xx unknown
- 1997-02-18 WO PCT/US1997/001970 patent/WO1997030981A1/en not_active Ceased
- 1997-02-18 KR KR1019980706639A patent/KR19990087238A/ko not_active Abandoned
- 1997-02-18 PE PE1997000112A patent/PE55898A1/es not_active Application Discontinuation
- 1997-02-18 NZ NZ331011A patent/NZ331011A/xx unknown
- 1997-02-18 AU AU19547/97A patent/AU703831B2/en not_active Ceased
- 1997-02-18 EP EP97907574A patent/EP0883611B1/en not_active Expired - Lifetime
- 1997-02-18 DE DE69714418T patent/DE69714418T2/de not_active Expired - Fee Related
- 1997-02-18 AT AT97907574T patent/ATE221521T1/de not_active IP Right Cessation
- 1997-02-18 ES ES97907574T patent/ES2180945T3/es not_active Expired - Lifetime
- 1997-02-18 JP JP9530192A patent/JP2000505084A/ja not_active Withdrawn
- 1997-02-18 PT PT97907574T patent/PT883611E/pt unknown
- 1997-02-18 CN CN97191516A patent/CN1082952C/zh not_active Expired - Fee Related
- 1997-02-18 DK DK97907574T patent/DK0883611T3/da active
- 1997-02-20 US US08/803,469 patent/US5736545A/en not_active Expired - Fee Related
- 1997-02-21 TW TW086102075A patent/TW442460B/zh not_active IP Right Cessation
- 1997-02-24 ID IDP970548A patent/ID18467A/id unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007521281A (ja) * | 2003-07-02 | 2007-08-02 | メルク アンド カンパニー インコーポレーテッド | シクロプロピル基置換されたオキサゾリジノン抗生物質およびこれらの誘導体 |
| WO2019208812A1 (ja) * | 2018-04-27 | 2019-10-31 | 国立大学法人大阪大学 | ベンゾイソオキサゾール化合物 |
| JPWO2019208812A1 (ja) * | 2018-04-27 | 2021-05-13 | 国立大学法人大阪大学 | ベンゾイソオキサゾール化合物 |
| JP7175481B2 (ja) | 2018-04-27 | 2022-11-21 | 国立大学法人大阪大学 | ベンゾイソオキサゾール化合物 |
| US11548882B2 (en) | 2018-04-27 | 2023-01-10 | Osaka University | Benzisoxazole compound |
| US11976062B2 (en) | 2018-04-27 | 2024-05-07 | Osaka University | Benzisoxazole compound |
Also Published As
| Publication number | Publication date |
|---|---|
| MY116093A (en) | 2003-11-28 |
| DE69714418D1 (de) | 2002-09-05 |
| ATE221521T1 (de) | 2002-08-15 |
| US5736545A (en) | 1998-04-07 |
| AU1954797A (en) | 1997-09-10 |
| ZA971287B (en) | 1998-08-14 |
| ES2180945T3 (es) | 2003-02-16 |
| CN1206410A (zh) | 1999-01-27 |
| PE55898A1 (es) | 1998-09-16 |
| CN1082952C (zh) | 2002-04-17 |
| DK0883611T3 (da) | 2002-12-02 |
| AU703831B2 (en) | 1999-04-01 |
| EP0883611B1 (en) | 2002-07-31 |
| NZ331011A (en) | 2000-04-28 |
| EP0883611A1 (en) | 1998-12-16 |
| PT883611E (pt) | 2002-12-31 |
| TW442460B (en) | 2001-06-23 |
| KR19990087238A (ko) | 1999-12-15 |
| WO1997030981A1 (en) | 1997-08-28 |
| DE69714418T2 (de) | 2003-01-16 |
| HK1017033A1 (en) | 1999-11-12 |
| ID18467A (id) | 1998-04-09 |
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