CA2243706C - Antimicrobiens a base d'azolyl piperazinyl phenyl oxazolidone - Google Patents
Antimicrobiens a base d'azolyl piperazinyl phenyl oxazolidone Download PDFInfo
- Publication number
- CA2243706C CA2243706C CA002243706A CA2243706A CA2243706C CA 2243706 C CA2243706 C CA 2243706C CA 002243706 A CA002243706 A CA 002243706A CA 2243706 A CA2243706 A CA 2243706A CA 2243706 C CA2243706 C CA 2243706C
- Authority
- CA
- Canada
- Prior art keywords
- oxo
- methyl
- phenyl
- piperazinyl
- acetamide
- 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.)
- Expired - Fee Related
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- 239000004599 antimicrobial Substances 0.000 title description 3
- 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 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 208000015181 infectious disease Diseases 0.000 claims abstract description 11
- 230000000813 microbial effect Effects 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 69
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 32
- 239000011737 fluorine Substances 0.000 claims description 31
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
- 150000003536 tetrazoles Chemical class 0.000 claims description 13
- -1 phenyl- Chemical group 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-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
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-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
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-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
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 claims description 4
- OVZHELCFKSFINS-UHFFFAOYSA-N 3h-1,3,4-thiadiazol-2-one Chemical compound O=C1NN=CS1 OVZHELCFKSFINS-UHFFFAOYSA-N 0.000 claims description 4
- NQBUERYLUPYOEL-UHFFFAOYSA-N isoindol-4-one Chemical class O=C1C=CC=C2C=NC=C12 NQBUERYLUPYOEL-UHFFFAOYSA-N 0.000 claims description 4
- PJCFLHUCYONHAS-UHFFFAOYSA-N oxathiazolone Chemical compound O=C1OC=NS1 PJCFLHUCYONHAS-UHFFFAOYSA-N 0.000 claims description 4
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 3
- GJGROPRLXDXIAN-UHFFFAOYSA-N 1,3-thiazol-4-one Chemical compound O=C1CSC=N1 GJGROPRLXDXIAN-UHFFFAOYSA-N 0.000 claims description 3
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- JPVBKGBISODDNG-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(4-oxo-1,3-thiazol-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=2SCC(=O)N=2)CC1 JPVBKGBISODDNG-AWEZNQCLSA-N 0.000 claims description 3
- RGBXGGZPUGEWDE-KNVGNIICSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-oxo-2h-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(C2N=NC(=O)S2)CC1 RGBXGGZPUGEWDE-KNVGNIICSA-N 0.000 claims description 3
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 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
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 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
- AXTPKYQMUDUCFW-UHFFFAOYSA-N 1,3-thiazole 1,1-dioxide Chemical compound O=S1(=O)C=CN=C1 AXTPKYQMUDUCFW-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- JLXZMLLNPNOODV-UHFFFAOYSA-N imidazol-4-one Chemical compound O=C1C=NC=N1 JLXZMLLNPNOODV-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-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
- 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 description 2
- 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 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 2
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 claims description 2
- SNWVNYROVXZKMI-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-nitro-1,3-thiazol-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(=CN=2)[N+]([O-])=O)CC1 SNWVNYROVXZKMI-AWEZNQCLSA-N 0.000 claims 3
- TVLKRCWEBYHFJP-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-(1,3-benzothiazol-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=2SC3=CC=CC=C3N=2)CC1 TVLKRCWEBYHFJP-KRWDZBQOSA-N 0.000 claims 3
- 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
- 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 2
- ARWSBSRQLXKQQE-HNNXBMFYSA-N N-[[(5S)-3-[3-fluoro-4-[4-(5-oxo-4H-imidazol-3-yl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound FC=1C=C(C=CC=1N1CCN(CC1)N1C=NC(C1)=O)N1C(O[C@H](C1)CNC(C)=O)=O ARWSBSRQLXKQQE-HNNXBMFYSA-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
- JJBNRTWTFMOFQO-AWEZNQCLSA-N O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C2=NSN=C2)CC1 Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C2=NSN=C2)CC1 JJBNRTWTFMOFQO-AWEZNQCLSA-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
- 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 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
- NPXRPBDKHGEXEG-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-[4-(3-oxo-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=2SNC(=O)N=2)CC1 NPXRPBDKHGEXEG-ZDUSSCGKSA-N 0.000 claims 2
- LFCZVOWNPMQANP-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(4-oxo-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=2OCC(=O)N=2)CC1 LFCZVOWNPMQANP-AWEZNQCLSA-N 0.000 claims 2
- YAZIWXQXNQASOF-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-[4-(5-oxo-1,2,4-dithiazol-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=2SSC(=O)N=2)CC1 YAZIWXQXNQASOF-ZDUSSCGKSA-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
- DEPPVEMCTZHOHH-HNNXBMFYSA-N n-[[(5s)-3-[4-[4-(4,5-dihydro-1,3-oxazol-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=2OCCN=2)CC1 DEPPVEMCTZHOHH-HNNXBMFYSA-N 0.000 claims 2
- ZEMOQIBQVWJELW-HNNXBMFYSA-N n-[[(5s)-3-[4-[4-(4,5-dihydro-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=2SCCN=2)CC1 ZEMOQIBQVWJELW-HNNXBMFYSA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 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 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
- VIAQQEOFFHGANP-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1,3-thiazol-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=CN=2)CC1 VIAQQEOFFHGANP-HNNXBMFYSA-N 0.000 claims 1
- SXODNFVYBDGMAV-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(1h-1,2,4-triazol-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=2NN=CN=2)CC1 SXODNFVYBDGMAV-AWEZNQCLSA-N 0.000 claims 1
- 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 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
- CMHAOELTLODFBG-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(3h-oxathiazol-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=2OSNC=2)CC1 CMHAOELTLODFBG-AWEZNQCLSA-N 0.000 claims 1
- 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 1
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- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
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- 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
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- 230000029936 alkylation Effects 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
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- 239000011230 binding agent Substances 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
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- DUZSKFCAULBHGX-BHWOMJMDSA-N ethyl 5-[4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-2-fluoropiperazin-1-yl]-1,3,4-thiadiazole-2-carboxylate Chemical compound S1C(C(=O)OCC)=NN=C1N1C(F)CN(C=2C=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)CC1 DUZSKFCAULBHGX-BHWOMJMDSA-N 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
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- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 238000002955 isolation Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 150000002545 isoxazoles Chemical class 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
- 238000003541 multi-stage reaction Methods 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
- 125000004433 nitrogen atom Chemical group N* 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
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
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- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- PEEXCRJDFUVJRT-UHFFFAOYSA-M potassium;methoxymethanedithioate Chemical compound [K+].COC([S-])=S PEEXCRJDFUVJRT-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 201000006681 severe congenital neutropenia Diseases 0.000 description 1
- 208000027390 severe congenital neutropenia 3 Diseases 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 229910000029 sodium carbonate Inorganic materials 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
- 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
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 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
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 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
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne des composés utiles dans la préparation de substances pharmaceutiques pour le traitement d'infections microbiennes, représentés par la formule structurelle (I) ou leurs sels pharmaceutiquement acceptables où: R<1> représente -CHO, -COCH3, -COCHCl2, -COCHF2, -SO2CH3, ou -COCH2OH; X<1> et X<2> représentent de manière indépendante H, F ou Cl; et Q représente un hétérocycle avec un noyau à cinq chaînons (noyau azolyl) dont la forme générale est (a) où A, B, et C représentent de manière indépendante oxygène (O), azote (N), soufre (S) ou carbone (C). Dans tous les cas, l'atome d'azote de la pipérazine est attaché à l'atome de carbone de la liaison double carbone-azote.
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 (fr) | 1996-02-26 | 1997-02-18 | Antimicrobiens a base d'azolyl piperazinyl phenyl oxazolidone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2243706A1 CA2243706A1 (fr) | 1997-08-28 |
| CA2243706C true CA2243706C (fr) | 2005-10-04 |
Family
ID=35395933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002243706A Expired - Fee Related CA2243706C (fr) | 1996-02-26 | 1997-02-18 | Antimicrobiens a base d'azolyl piperazinyl phenyl oxazolidone |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2243706C (fr) |
-
1997
- 1997-02-18 CA CA002243706A patent/CA2243706C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2243706A1 (fr) | 1997-08-28 |
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