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- Withdrawn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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 51
- 239000007787 solid Substances 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 229910052740 iodine Inorganic materials 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- 239000012141 concentrate Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 244000309464 bull Species 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 4
- HFULRRXNTBESRB-UHFFFAOYSA-N 5-bromo-2h-tetrazole Chemical compound BrC=1N=NNN=1 HFULRRXNTBESRB-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 3
- DQBCRVIBTFHJLM-UHFFFAOYSA-N 2-bromo-1,3,4-thiadiazole Chemical compound BrC1=NN=CS1 DQBCRVIBTFHJLM-UHFFFAOYSA-N 0.000 description 3
- VAXCPOSTDXAXMH-UHFFFAOYSA-N 4-chlorooxathiazolidine Chemical compound ClC1COSN1 VAXCPOSTDXAXMH-UHFFFAOYSA-N 0.000 description 3
- HHIZISRHAQPAMY-UHFFFAOYSA-N 5-bromo-1h-1,2,4-triazole Chemical compound BrC1=NC=NN1 HHIZISRHAQPAMY-UHFFFAOYSA-N 0.000 description 3
- QGOUKZPSCTVYLX-UHFFFAOYSA-N 5-chloro-1h-1,2,4-triazole Chemical compound ClC1=NC=NN1 QGOUKZPSCTVYLX-UHFFFAOYSA-N 0.000 description 3
- VPGCAABOWGUEFY-UHFFFAOYSA-N 5-chlorothiatriazole Chemical compound ClC1=NN=NS1 VPGCAABOWGUEFY-UHFFFAOYSA-N 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 2
- LGTVLLPQCMJOGT-UHFFFAOYSA-N 2-bromo-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound FC(F)(F)C1=NN=C(Br)S1 LGTVLLPQCMJOGT-UHFFFAOYSA-N 0.000 description 2
- NSMKWTGDPQHTDH-UHFFFAOYSA-N 2-bromo-5-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=C(Br)S1 NSMKWTGDPQHTDH-UHFFFAOYSA-N 0.000 description 2
- SSXYKBHZZRYLLY-UHFFFAOYSA-N 2-chloro-1,3-oxazole Chemical compound ClC1=NC=CO1 SSXYKBHZZRYLLY-UHFFFAOYSA-N 0.000 description 2
- SDEKPTRCZDOESK-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-1,3,4-oxadiazole Chemical compound CC1=NN=C(S(C)(=O)=O)O1 SDEKPTRCZDOESK-UHFFFAOYSA-N 0.000 description 2
- GGRBHXPTYNPANC-UHFFFAOYSA-N 2-nitroindazole Chemical compound C1=CC=CC2=NN([N+](=O)[O-])C=C21 GGRBHXPTYNPANC-UHFFFAOYSA-N 0.000 description 2
- BCPVKLRBQLRWDQ-UHFFFAOYSA-N 3-chloro-1,2-benzothiazole Chemical compound C1=CC=C2C(Cl)=NSC2=C1 BCPVKLRBQLRWDQ-UHFFFAOYSA-N 0.000 description 2
- GLYQQFBHCFPEEU-UHFFFAOYSA-N 5-bromo-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(Br)S1 GLYQQFBHCFPEEU-UHFFFAOYSA-N 0.000 description 2
- IBGNUSRLIIGHBS-UHFFFAOYSA-N 5-chloro-1,3,4-thiadiazole-2-carboxamide Chemical compound NC(=O)C1=NN=C(Cl)S1 IBGNUSRLIIGHBS-UHFFFAOYSA-N 0.000 description 2
- DHELIGKVOGTMGF-UHFFFAOYSA-N 5-chloro-1-phenyltetrazole Chemical compound ClC1=NN=NN1C1=CC=CC=C1 DHELIGKVOGTMGF-UHFFFAOYSA-N 0.000 description 2
- PCLAZAJARAIGGD-UHFFFAOYSA-N 5-methylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CSC1=NN=C(N)S1 PCLAZAJARAIGGD-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- 238000007269 dehydrobromination reaction Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical class 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 150000002473 indoazoles Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- GMQOZFVOGGIFIX-UHFFFAOYSA-N oxathiazolidine Chemical compound C1COSN1 GMQOZFVOGGIFIX-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical compound O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- ZUWFBQUHBOUPFK-UHFFFAOYSA-N 1-chloro-2-isothiocyanatoethane Chemical compound ClCCN=C=S ZUWFBQUHBOUPFK-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- KEGOHDCHURMFKX-UHFFFAOYSA-N 2,3-difluoro-6-nitrophenol Chemical compound OC1=C(F)C(F)=CC=C1[N+]([O-])=O KEGOHDCHURMFKX-UHFFFAOYSA-N 0.000 description 1
- XJRSSTCKTZZGHE-UHFFFAOYSA-N 2-bromo-5-methylsulfanyl-1,3,4-thiadiazole Chemical compound CSC1=NN=C(Br)S1 XJRSSTCKTZZGHE-UHFFFAOYSA-N 0.000 description 1
- ANIJFZVZXZQFDH-UHFFFAOYSA-N 2-bromo-5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=C(Br)S1 ANIJFZVZXZQFDH-UHFFFAOYSA-N 0.000 description 1
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 1
- POPCHMUHLLLJMV-UHFFFAOYSA-N 2-chloro-3h-1,2,4-thiadiazole Chemical compound ClN1CN=CS1 POPCHMUHLLLJMV-UHFFFAOYSA-N 0.000 description 1
- QFKHKBJLBBASAZ-UHFFFAOYSA-N 2-chloro-5-fluoro-1,3-benzoxazole Chemical compound FC1=CC=C2OC(Cl)=NC2=C1 QFKHKBJLBBASAZ-UHFFFAOYSA-N 0.000 description 1
- CFIFJVIHMFCZDA-UHFFFAOYSA-N 2-chloro-6,7-difluoro-1,3-benzoxazole Chemical compound FC1=CC=C2N=C(Cl)OC2=C1F CFIFJVIHMFCZDA-UHFFFAOYSA-N 0.000 description 1
- KUCSJGBXJBQHNI-UHFFFAOYSA-N 2-chloro-6-nitro-1,3-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2N=C(Cl)SC2=C1 KUCSJGBXJBQHNI-UHFFFAOYSA-N 0.000 description 1
- USZLFNXVGKQFGW-UHFFFAOYSA-N 2-chloro-7-fluoro-1,3-benzoxazole Chemical compound FC1=CC=CC2=C1OC(Cl)=N2 USZLFNXVGKQFGW-UHFFFAOYSA-N 0.000 description 1
- HIGRXCJEFUYRNW-UHFFFAOYSA-N 2-fluoro-6-nitrophenol Chemical compound OC1=C(F)C=CC=C1[N+]([O-])=O HIGRXCJEFUYRNW-UHFFFAOYSA-N 0.000 description 1
- OYGMAHAEORYXIG-UHFFFAOYSA-N 2-methylsulfanyl-1,3,4-thiadiazole Chemical compound CSC1=NN=CS1 OYGMAHAEORYXIG-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- LKAYAMCKQCBSOU-UHFFFAOYSA-N 3-chloro-1,2,4-thiadiazole Chemical compound ClC=1N=CSN=1 LKAYAMCKQCBSOU-UHFFFAOYSA-N 0.000 description 1
- HSANMQQDOIDQOM-UHFFFAOYSA-N 3-methoxy-1,2,5-thiadiazole Chemical compound COC=1C=NSN=1 HSANMQQDOIDQOM-UHFFFAOYSA-N 0.000 description 1
- ZHRLVDHMIJDWSS-UHFFFAOYSA-N 4-fluoro-2-nitrophenol Chemical compound OC1=CC=C(F)C=C1[N+]([O-])=O ZHRLVDHMIJDWSS-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- DYJTVBYTWZEIDV-UHFFFAOYSA-N 5-(trichloromethyl)-1,2,4-oxadiazole Chemical compound ClC(Cl)(Cl)C1=NC=NO1 DYJTVBYTWZEIDV-UHFFFAOYSA-N 0.000 description 1
- STSPRWNSMJRTNZ-MLCCFXAWSA-N 5-[4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-2-fluoropiperazin-1-yl]-1,3,4-thiadiazole-2-carboxamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CC(F)N(CC2)C=2SC(=NN=2)C(N)=O)C=C1 STSPRWNSMJRTNZ-MLCCFXAWSA-N 0.000 description 1
- GDGIVSREGUOIJZ-UHFFFAOYSA-N 5-amino-3h-1,3,4-thiadiazole-2-thione Chemical compound NC1=NN=C(S)S1 GDGIVSREGUOIJZ-UHFFFAOYSA-N 0.000 description 1
- JFYIYTCVPQGLSL-UHFFFAOYSA-N 5-bromo-2,3-dihydro-1h-pyrazole Chemical compound BrC1=CCNN1 JFYIYTCVPQGLSL-UHFFFAOYSA-N 0.000 description 1
- CNSGTVFPDJGHOG-UHFFFAOYSA-N 5-chloro-1,3,4-thiadiazole-2-carbonitrile Chemical compound ClC1=NN=C(C#N)S1 CNSGTVFPDJGHOG-UHFFFAOYSA-N 0.000 description 1
- NIMUOHHAYCKTTI-UHFFFAOYSA-N 5-chloro-2-phenyl-1,2,4-thiadiazol-3-one Chemical compound S1C(Cl)=NC(=O)N1C1=CC=CC=C1 NIMUOHHAYCKTTI-UHFFFAOYSA-N 0.000 description 1
- ILTLLMVRPBXCSX-UHFFFAOYSA-N 5-chloro-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(Cl)=N1 ILTLLMVRPBXCSX-UHFFFAOYSA-N 0.000 description 1
- QQURWFRNETXFTN-UHFFFAOYSA-N 5-fluoro-2-nitrophenol Chemical compound OC1=CC(F)=CC=C1[N+]([O-])=O QQURWFRNETXFTN-UHFFFAOYSA-N 0.000 description 1
- UVHVJSJZCPFGET-UHFFFAOYSA-N 5-fluoro-3h-1,3-benzoxazole-2-thione Chemical compound FC1=CC=C2OC(S)=NC2=C1 UVHVJSJZCPFGET-UHFFFAOYSA-N 0.000 description 1
- UBAMSEMTGGHLSX-UHFFFAOYSA-N 6,7-difluoro-3h-1,3-benzoxazole-2-thione Chemical compound FC1=CC=C2N=C(S)OC2=C1F UBAMSEMTGGHLSX-UHFFFAOYSA-N 0.000 description 1
- RPTXVOBIDXKEFW-UHFFFAOYSA-N 6-fluoro-3h-1,3-benzoxazole-2-thione Chemical compound FC1=CC=C2N=C(S)OC2=C1 RPTXVOBIDXKEFW-UHFFFAOYSA-N 0.000 description 1
- KQULXBZFTSJHJQ-UHFFFAOYSA-N 7-fluoro-3h-1,3-benzoxazole-2-thione Chemical compound FC1=CC=CC2=C1OC(S)=N2 KQULXBZFTSJHJQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000606125 Bacteroides Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- CLCTZVRHDOAUGJ-UHFFFAOYSA-N N-[4-(3-chloro-4-cyanophenoxy)cyclohexyl]-6-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl]piperazin-1-yl]methyl]piperidin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC2=C(C=C1N1CCN(CC3CCN(CC3)C3=CC=C(N=N3)C(=O)NC3CCC(CC3)OC3=CC(Cl)=C(C=C3)C#N)CC1)C(=O)N(C1CCC(=O)NC1=O)C2=O CLCTZVRHDOAUGJ-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 101001051524 Parabuthus granulatus Toxin PgKL2 Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000194022 Streptococcus sp. Species 0.000 description 1
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical class CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 241000748245 Villanova Species 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YQWCUJDSRXQJRN-UHFFFAOYSA-N ethyl 5-chloro-1,3,4-thiadiazole-2-carboxylate Chemical compound CCOC(=O)C1=NN=C(Cl)S1 YQWCUJDSRXQJRN-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 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
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- VYHVQEYOFIYNJP-UHFFFAOYSA-N methyl thiocyanate Chemical compound CSC#N VYHVQEYOFIYNJP-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- GKAQFCVKMRYUFT-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(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)CC1 GKAQFCVKMRYUFT-AWEZNQCLSA-N 0.000 description 1
- SRDHQJGXDQINOW-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-methyl-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(C)=NN=2)CC1 SRDHQJGXDQINOW-HNNXBMFYSA-N 0.000 description 1
- 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- PEEXCRJDFUVJRT-UHFFFAOYSA-M potassium;methoxymethanedithioate Chemical compound [K+].COC([S-])=S PEEXCRJDFUVJRT-UHFFFAOYSA-M 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 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
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 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
- 230000000699 topical effect Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 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
- 210000001835 viscera Anatomy 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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 (index.php) | 2004-11-25 |
Family
ID=21754387
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 (index.php) |
| EP (1) | EP0883611B1 (index.php) |
| JP (1) | JP2000505084A (index.php) |
| KR (1) | KR19990087238A (index.php) |
| CN (1) | CN1082952C (index.php) |
| AT (1) | ATE221521T1 (index.php) |
| AU (1) | AU703831B2 (index.php) |
| DE (1) | DE69714418T2 (index.php) |
| DK (1) | DK0883611T3 (index.php) |
| ES (1) | ES2180945T3 (index.php) |
| ID (1) | ID18467A (index.php) |
| MY (1) | MY116093A (index.php) |
| NZ (1) | NZ331011A (index.php) |
| PE (1) | PE55898A1 (index.php) |
| PT (1) | PT883611E (index.php) |
| TW (1) | TW442460B (index.php) |
| WO (1) | WO1997030981A1 (index.php) |
| ZA (1) | ZA971287B (index.php) |
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 |
| CA2294293A1 (en) * | 1997-07-11 | 1999-01-21 | 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 |
| JP2002501059A (ja) | 1998-01-23 | 2002-01-15 | ファルマシア・アンド・アップジョン・カンパニー | オキサゾリジノンの組合せライブラリー、組成物および調製方法 |
| US7002020B1 (en) | 1998-01-23 | 2006-02-21 | Pharmacia & Upjohn Company | 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 |
| EP1102536B1 (de) * | 1998-08-04 | 2003-05-02 | 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 |
| PE20010851A1 (es) * | 1999-12-14 | 2001-08-17 | Upjohn Co | Esteres del acido benzoico de oxazolidinonas que tienen un substituyente hidroxiacetilpiperazina |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| SK1402003A3 (en) * | 2000-07-17 | 2003-08-05 | Ranbaxy Lab Ltd | Oxazolidinone derivatives as antimicrobials |
| CA2443410A1 (en) * | 2001-04-17 | 2003-04-03 | Yasumichi Fukuda | Bicyclo[3,1,0]hexane containing oxazolidinone antibiotic and derivatives thereof |
| EP1409464A4 (en) * | 2001-07-16 | 2005-11-02 | Ranbaxy Lab Ltd | OXAZOLIDINONE DERIVATIVES AS POTENTIAL ANTIMICROBIALS |
| RU2004136573A (ru) * | 2002-05-15 | 2005-08-10 | Рэнбакси Лабораториз Лимитед (In) | Производные фенилоксазолидинона |
| BR0215921A (pt) * | 2002-07-29 | 2005-09-13 | Ranbaxy Lab Ltd | Derivados de oxazolidinona utilizáveis como antimicrobianos e processo de sua preparação |
| MXPA05001558A (es) | 2002-08-12 | 2005-09-08 | Pharmacia & Upjohn Co Llc | N-aril-2-oxazolidinonas y sus derivados. |
| WO2004026848A1 (en) * | 2002-09-20 | 2004-04-01 | Lupin Limited | Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents |
| AR042086A1 (es) | 2002-11-21 | 2005-06-08 | Upjohn Co | N-aril-2- oxazolidinon -5- carboxamidas y sus derivados, usados como agentes antibacterianos |
| CA2529293A1 (en) * | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Cyclopropyl group substituted oxazolidinone antibiotics and derivatives thereof |
| WO2005005399A1 (en) * | 2003-07-02 | 2005-01-20 | Merck & Co., Inc. | Oxazolidinone antibiotics and derivatives thereof |
| EP1646630A1 (en) * | 2003-07-02 | 2006-04-19 | Merck & Co., Inc. | Oxazolidinone antibiotics and derivatives thereof |
| WO2005051933A1 (en) * | 2003-11-28 | 2005-06-09 | Ranbaxy Laboratories Limited | An improved process for the synthesis of 4-(4-benzyloxy-carbonylamino-2-fluorophenyl)-piperazine-1-carboxylic acid tert-butyl ester, a key intermediate for oxazolidinone antimicrobials and compounds prepared thereby |
| WO2005082899A1 (en) * | 2004-01-28 | 2005-09-09 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| US8686011B2 (en) | 2004-05-24 | 2014-04-01 | Amgen Inc. | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
| US7253196B2 (en) * | 2004-05-24 | 2007-08-07 | Amgen, Inc. | Inhibitors of 11-β-hydroxy steroid dehydrogenase type 1 |
| WO2006035283A1 (en) * | 2004-09-27 | 2006-04-06 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| WO2006043121A1 (en) * | 2004-10-20 | 2006-04-27 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| WO2006051408A1 (en) * | 2004-11-11 | 2006-05-18 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| EP1912980A2 (en) * | 2005-06-20 | 2008-04-23 | Wockhardt Limited | Oxazolidinones bearing antimicrobial activity composition and methods of preparation |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| CN100406455C (zh) * | 2006-02-20 | 2008-07-30 | 中国科学院上海药物研究所 | 含三氮唑基的噁唑烷酮类化合物及其制备方法和用途 |
| JO2642B1 (en) * | 2006-12-08 | 2012-06-17 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| JO2849B1 (en) * | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| CA2682671C (en) * | 2007-04-23 | 2015-11-17 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
| KR20100016620A (ko) * | 2007-04-23 | 2010-02-12 | 얀센 파마슈티카 엔.브이. | 속해리성 도파민 2 수용체 길항제로서의 4-알콕시피리다진 유도체 |
| JP2010525013A (ja) * | 2007-04-23 | 2010-07-22 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 高速解離性ドパミン２受容体アンタゴニストとしてのピリジン誘導体 |
| AU2009228293B2 (en) * | 2008-03-26 | 2012-11-08 | Tennor Therapeutics (Suzhou) Limited | Bicyclic nitroimidazoles covalently linked to substituted phenyl oxazolidinones |
| EP2310374B1 (en) * | 2008-07-03 | 2012-10-31 | Janssen Pharmaceutica N.V. | Substituted 6- (1-piperazinyl) -pyridazines as 5-ht6 receptor antagonists |
| US8895562B2 (en) * | 2008-07-31 | 2014-11-25 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
| WO2011152442A1 (ja) * | 2010-06-03 | 2011-12-08 | 塩野義製薬株式会社 | 2－クロロ－6－フルオロベンゾオキサゾールの製造方法 |
| CN102079730B (zh) * | 2010-09-06 | 2013-10-16 | 贵州大学 | 一类含2,5-取代杂环基砜类衍生物及其合成方法和应用 |
| CN103450173B (zh) * | 2013-09-07 | 2015-06-03 | 吉首大学 | 吡咯酮-苯基-噁唑烷酮型化合物及其制法和用途 |
| CN103709119B (zh) * | 2013-12-04 | 2015-05-20 | 上海应用技术学院 | 一种制备5-氨基噻唑-4-甲酰胺的方法 |
| CN104202835A (zh) * | 2014-09-03 | 2014-12-10 | 苏州微站通信科技有限公司 | Ue进入静默期时让基站及时释放时频资源的方法 |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4921869A (en) * | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4801600A (en) * | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4977173A (en) * | 1987-10-21 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl ethenylbenzene derivatives useful as antibacterial agents |
| US5254577A (en) * | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| US4948801A (en) * | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| 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 JP JP9530192A patent/JP2000505084A/ja not_active Withdrawn
- 1997-02-18 EP EP97907574A patent/EP0883611B1/en not_active Expired - Lifetime
- 1997-02-18 AU AU19547/97A patent/AU703831B2/en not_active Ceased
- 1997-02-18 DE DE69714418T patent/DE69714418T2/de not_active Expired - Fee Related
- 1997-02-18 ES ES97907574T patent/ES2180945T3/es not_active Expired - Lifetime
- 1997-02-18 AT AT97907574T patent/ATE221521T1/de not_active IP Right Cessation
- 1997-02-18 CN CN97191516A patent/CN1082952C/zh not_active Expired - Fee Related
- 1997-02-18 WO PCT/US1997/001970 patent/WO1997030981A1/en not_active Ceased
- 1997-02-18 PT PT97907574T patent/PT883611E/pt unknown
- 1997-02-18 KR KR1019980706639A patent/KR19990087238A/ko not_active Abandoned
- 1997-02-18 DK DK97907574T patent/DK0883611T3/da active
- 1997-02-18 PE PE1997000112A patent/PE55898A1/es not_active Application Discontinuation
- 1997-02-18 NZ NZ331011A patent/NZ331011A/xx unknown
- 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 |
|---|---|
| ID18467A (id) | 1998-04-09 |
| ES2180945T3 (es) | 2003-02-16 |
| ZA971287B (en) | 1998-08-14 |
| DE69714418T2 (de) | 2003-01-16 |
| AU703831B2 (en) | 1999-04-01 |
| NZ331011A (en) | 2000-04-28 |
| PT883611E (pt) | 2002-12-31 |
| DK0883611T3 (da) | 2002-12-02 |
| MY116093A (en) | 2003-11-28 |
| PE55898A1 (es) | 1998-09-16 |
| DE69714418D1 (de) | 2002-09-05 |
| EP0883611A1 (en) | 1998-12-16 |
| US5736545A (en) | 1998-04-07 |
| EP0883611B1 (en) | 2002-07-31 |
| AU1954797A (en) | 1997-09-10 |
| ATE221521T1 (de) | 2002-08-15 |
| HK1017033A1 (en) | 1999-11-12 |
| WO1997030981A1 (en) | 1997-08-28 |
| TW442460B (en) | 2001-06-23 |
| CN1082952C (zh) | 2002-04-17 |
| CN1206410A (zh) | 1999-01-27 |
| KR19990087238A (ko) | 1999-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0883611B1 (en) | Azolyl piperazinyl phenyl oxazolidinone antimicrobials | |
| RU2414469C2 (ru) | Новые производные оксазолидинона | |
| US5977373A (en) | Thiadiazolyl and oxadiazolyl phenyl oxazolidinone antibacterial agents | |
| PL185872B1 (pl) | Nowe podstawione fenylooksazolidynonyNowe podstawione fenylooksazolidynony | |
| WO2006038100A1 (en) | Oxazolidinone derivatives as antimicrobials | |
| CA2377527A1 (en) | Heteroaromatic ring compounds | |
| AU1805801A (en) | Benzoic acid esters of oxazolidinones having a hydroxyacetylpiperazine substituent | |
| WO2003048136A1 (en) | Cyclopropyl hexane containing oxazolidinone antibiotics and derivatives thereof | |
| EP2560969A1 (en) | 4 - (5 - isoxazolyl or 5 - pyrrazolyl -1,2,4- oxadiazol - 3 - yl) -mandelic acid amides as sphingosin- 1 - phosphate 1 rreceptor agonists | |
| CA2243706C (en) | Azolyl piperazinyl phenyl oxazolidinone antimicrobials | |
| CA2399275A1 (en) | Novel benzosultam oxazolidinone antibacterial agents | |
| AU2001247540A1 (en) | Novel benzosultam oxazolidinone antibacterial agents | |
| WO2006056875A1 (en) | Thiazepine oxazolidinones as antibacterial agents | |
| WO2007088478A1 (en) | Indazole oxazolidinones as antibacterial agents | |
| HK1017033B (en) | Azolyl piperazinyl phenyl oxazolidinone antimicrobials | |
| CA2637811A1 (en) | Benzisoxazole oxazolidinones as antibacterial agents | |
| JP2008544979A (ja) | 抗菌剤としてのホモモルホリンオキサゾリジノン | |
| CA2575702A1 (en) | Oxindole oxazolidinones as antibacterial agents | |
| JPS6212784A (ja) | 抗生物質の使用方法および製剤 | |
| AU2002362028B2 (en) | Cyclopropyl hexane containing oxazolidinone antibiotics and derivatives thereof | |
| MXPA04007468A (es) | Derivados de tiadiazinona antimicrobianos y su aplicacion para el tratamiento de infecciones bacterianas. | |
| WO2006056877A2 (en) | Diazepine oxazolidinones as antibacterial agents | |
| MXPA00000374A (en) | Thiadiazolyl and oxadiazolyl phenyl oxazolidinone antibacterial agents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040203 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040203 |
|
| A72 | Notification of change in name of applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A721 Effective date: 20060215 |
|
| A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20060215 |