CA2537559C - Substituted piperidino phenyloxazolidinones having antimicriobial activity with improved in vivo efficacy - Google Patents
Substituted piperidino phenyloxazolidinones having antimicriobial activity with improved in vivo efficacy Download PDFInfo
- Publication number
- CA2537559C CA2537559C CA2537559A CA2537559A CA2537559C CA 2537559 C CA2537559 C CA 2537559C CA 2537559 A CA2537559 A CA 2537559A CA 2537559 A CA2537559 A CA 2537559A CA 2537559 C CA2537559 C CA 2537559C
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- CA
- Canada
- Prior art keywords
- oxo
- ylmethyl
- oxazolidin
- fluorophenyl
- 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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- DNRCUMDULWDBQC-UHFFFAOYSA-N 3-phenyl-4-piperidin-1-yl-1,3-oxazolidin-2-one Chemical class O=C1OCC(N2CCCCC2)N1C1=CC=CC=C1 DNRCUMDULWDBQC-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000001727 in vivo Methods 0.000 title description 12
- 230000000694 effects Effects 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 347
- 239000000203 mixture Substances 0.000 claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 90
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 10
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 10
- -1 cyano, nitro, amino, mercapto Chemical class 0.000 claims description 128
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
- 239000002904 solvent Substances 0.000 claims description 76
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 48
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 33
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000005518 carboxamido group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 11
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- SVOLSLCLNUIRAX-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(azidomethyl)-4-fluoropiperidin-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=C1N1CCC(F)(CN=[N+]=[N-])CC1 SVOLSLCLNUIRAX-AWEZNQCLSA-N 0.000 claims description 6
- OIHXXNVTJVKSBV-HNNXBMFYSA-N n-[[(5s)-3-[4-[4-(cyanomethyl)-4-fluoropiperidin-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=C1N1CCC(F)(CC#N)CC1 OIHXXNVTJVKSBV-HNNXBMFYSA-N 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- CCBGOVZUUGKWPP-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-fluoro-4-(hydroxymethyl)piperidin-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=C1N1CCC(F)(CO)CC1 CCBGOVZUUGKWPP-AWEZNQCLSA-N 0.000 claims description 5
- RDJZPECEBXWQPW-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-fluoro-4-(methanesulfonamidomethyl)piperidin-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=C1N1CCC(F)(CNS(C)(=O)=O)CC1 RDJZPECEBXWQPW-HNNXBMFYSA-N 0.000 claims description 5
- WUSDDDGVFYBUDG-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-fluoro-4-(methoxymethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(COC)(F)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F WUSDDDGVFYBUDG-HNNXBMFYSA-N 0.000 claims description 5
- ISDJNKMBJSFUNC-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-4-(methoxymethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(COC)(O)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F ISDJNKMBJSFUNC-HNNXBMFYSA-N 0.000 claims description 5
- PBMWVGVUXXCUAY-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(azidomethyl)-4-hydroxypiperidin-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=C1N1CCC(O)(CN=[N+]=[N-])CC1 PBMWVGVUXXCUAY-AWEZNQCLSA-N 0.000 claims description 5
- GNCORSNDGQUUBG-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-hydroxy-4-(methoxymethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(COC)(O)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1 GNCORSNDGQUUBG-KRWDZBQOSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- XMYQWUYFRFPERD-UHFFFAOYSA-N 4-(1-oxa-6-azaspiro[2.5]octan-6-yl)-3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1OCC(N2CCC3(OC3)CC2)N1C1=CC=CC=C1 XMYQWUYFRFPERD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- SCUBACWOLDXCBN-HNNXBMFYSA-N [1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-fluoropiperidin-4-yl]methyl methanesulfonate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(F)(COS(C)(=O)=O)CC1 SCUBACWOLDXCBN-HNNXBMFYSA-N 0.000 claims description 4
- UBRRCZFKYPGMPW-HNNXBMFYSA-N [1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-hydroxypiperidin-4-yl]methyl methanesulfonate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(O)(COS(C)(=O)=O)CC1 UBRRCZFKYPGMPW-HNNXBMFYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- CPYPHPPGEPTGJN-MBIQTGHCSA-N n-[[(5s)-3-[3-fluoro-4-(6-fluoro-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC(F)C2(OCCO2)CC1 CPYPHPPGEPTGJN-MBIQTGHCSA-N 0.000 claims description 4
- INGIHHKDHJBOGW-WONDXTMASA-N n-[[(5s)-3-[3-fluoro-4-(6-fluoro-3-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O1C(C)COC11C(F)CN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 INGIHHKDHJBOGW-WONDXTMASA-N 0.000 claims description 4
- VGXZENRUZSOHKX-BHWOMJMDSA-N n-[[(5s)-3-[4-(6-fluoro-1,4-dioxa-8-azaspiro[4.5]decan-8-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)C3(OCCO3)CC2)C=C1 VGXZENRUZSOHKX-BHWOMJMDSA-N 0.000 claims description 4
- AYJPEQIJIFCQHD-CYBMUJFWSA-N n-[[(5s)-3-[4-[4-(azidomethyl)-4-hydroxypiperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]methanesulfonamide Chemical compound O=C1O[C@H](CNS(=O)(=O)C)CN1C(C=C1F)=CC=C1N1CCC(O)(CN=[N+]=[N-])CC1 AYJPEQIJIFCQHD-CYBMUJFWSA-N 0.000 claims description 4
- HWDSXTVTRJZRGO-HNNXBMFYSA-N n-[[(5s)-3-[4-[4-(cyanomethyl)-4-hydroxypiperidin-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=C1N1CCC(O)(CC#N)CC1 HWDSXTVTRJZRGO-HNNXBMFYSA-N 0.000 claims description 4
- MAKYHLSPEQZPAV-INIZCTEOSA-N n-[[(5s)-3-[4-[4-(ethoxymethyl)-4-fluoropiperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(COCC)(F)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F MAKYHLSPEQZPAV-INIZCTEOSA-N 0.000 claims description 4
- IVNRKOMAMHSLHF-INIZCTEOSA-N n-[[(5s)-3-[4-[4-(ethoxymethyl)-4-hydroxypiperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(COCC)(O)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F IVNRKOMAMHSLHF-INIZCTEOSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- QOYNACXTCDEQET-CYBMUJFWSA-N 2-[(5R)-3-[3-fluoro-4-[4-hydroxy-4-(hydroxymethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]ethanesulfonic acid Chemical compound C1CC(CO)(O)CCN1C1=CC=C(N2C(O[C@H](CCS(O)(=O)=O)C2)=O)C=C1F QOYNACXTCDEQET-CYBMUJFWSA-N 0.000 claims description 3
- KZUKJZRMQPOCNS-AWEZNQCLSA-N 2-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-hydroxypiperidin-4-yl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(O)(CC(N)=O)CC1 KZUKJZRMQPOCNS-AWEZNQCLSA-N 0.000 claims description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 3
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 3
- QAOAXOKFSCLYRA-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-fluoro-4-(fluoromethyl)piperidin-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=C1N1CCC(F)(CF)CC1 QAOAXOKFSCLYRA-AWEZNQCLSA-N 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 229940050390 benzoate Drugs 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 229940114081 cinnamate Drugs 0.000 claims description 2
- 229940001468 citrate Drugs 0.000 claims description 2
- 229940050410 gluconate Drugs 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- SIBYWFQFHQRKNA-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-(4-hydroxy-4-prop-2-ynylpiperidin-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=C1N1CCC(O)(CC#C)CC1 SIBYWFQFHQRKNA-INIZCTEOSA-N 0.000 claims description 2
- CFJLKYBPHISSEL-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-4-(nitromethyl)piperidin-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=C1N1CCC(O)(C[N+]([O-])=O)CC1 CFJLKYBPHISSEL-AWEZNQCLSA-N 0.000 claims description 2
- QGFIHXRRJMELNU-SFHVURJKSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-4-(piperazin-1-ylmethyl)piperidin-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=C1N1CCC(O)(CN2CCNCC2)CC1 QGFIHXRRJMELNU-SFHVURJKSA-N 0.000 claims description 2
- BCRMNRRHTPNBQS-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-[(cyclopropylamino)methyl]-4-hydroxypiperidin-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=C1N1CCC(O)(CNC2CC2)CC1 BCRMNRRHTPNBQS-KRWDZBQOSA-N 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
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- 239000003762 serotonin receptor affecting agent Substances 0.000 description 1
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- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- 229940075931 sodium dithionate Drugs 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
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- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- 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
-
- 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
- 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
- C07D413/10—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 carbon chain containing aromatic rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN924MU2003 | 2003-09-08 | ||
| IN924/MUM/2003 | 2003-09-08 | ||
| PCT/IN2004/000276 WO2005054234A2 (en) | 2003-09-08 | 2004-09-08 | Substituted piperidino phenyloxazolidinones having antimicriobial activity with improved in vivo efficacy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2537559A1 CA2537559A1 (en) | 2005-06-16 |
| CA2537559C true CA2537559C (en) | 2012-11-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2537559A Expired - Fee Related CA2537559C (en) | 2003-09-08 | 2004-09-08 | Substituted piperidino phenyloxazolidinones having antimicriobial activity with improved in vivo efficacy |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7687627B2 (enExample) |
| EP (1) | EP1664038A2 (enExample) |
| JP (1) | JP4917432B2 (enExample) |
| AU (1) | AU2004295208A1 (enExample) |
| BR (1) | BRPI0413413A (enExample) |
| CA (1) | CA2537559C (enExample) |
| EA (1) | EA200600374A1 (enExample) |
| WO (1) | WO2005054234A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
| WO2007004049A1 (en) * | 2005-07-06 | 2007-01-11 | Pharmacia & Upjohn Company Llc | Oxazolidinones containing azetidine as antibacterial agents |
| JP5313126B2 (ja) * | 2006-05-09 | 2013-10-09 | ウォックハート リミテッド | 置換ピペリジノフェニルオキサゾリジノン |
| CN101616588B (zh) * | 2006-09-25 | 2013-09-25 | 沃克哈特研究中心 | 取代的哌啶子基苯基噁唑烷酮 |
| WO2009037542A2 (en) * | 2007-09-20 | 2009-03-26 | Glenmark Pharmaceuticals, S.A. | Spirocyclic compounds as stearoyl coa desaturase inhibitors |
| EP2072513A1 (en) * | 2007-12-17 | 2009-06-24 | Ferrer Internacional, S.A. | A cyano piperidinyl-phenil-oxazolidinone and use thereof |
| EP2254892B1 (en) | 2008-03-26 | 2014-04-23 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazoles covalently linked to substituted phenyl oxazolidinones |
| EP2141161A1 (en) * | 2008-07-01 | 2010-01-06 | Ferrer Internacional, S.A. | 3-cyanopyrrolidinyl-phenyl-oxazolidinones as antibacterial agents |
| EP2410854B1 (en) * | 2009-03-27 | 2016-06-29 | Council of Scientific & Industrial Research | Substituted 1, 4-dioxa-8-azaspiro ý4,5¨decanes useful as fungicides and a process for the preparation thereof |
| CA2816515A1 (en) * | 2010-11-03 | 2012-05-10 | Wockhardt Limited | Process for the preparation of phosphoric acid mono-(1-{4-[(s)-5-(acetylaminomethyl)-2-oxo-oxazolidin-3-yl]-2,6-difluorophenyl}-4-methoxymethylpiperidin-4-yl) ester |
| US9359344B2 (en) | 2011-09-29 | 2016-06-07 | Xuanzhu Pharma Co., Ltd. | Biaryl heterocycle substituted oxazolidinone antibacterial agents |
| WO2015066413A1 (en) * | 2013-11-01 | 2015-05-07 | Novartis Ag | Oxazolidinone hydroxamic acid compounds for the treatment of bacterial infections |
| WO2016079757A2 (en) * | 2014-11-19 | 2016-05-26 | Symed Labs Limited | Novel processes for preparing 5-hydroxymethyl-oxazolidin-2-one derivatives |
| WO2019081210A1 (en) * | 2017-10-27 | 2019-05-02 | Huntsman International Llc | CATALYSTS FOR MANUFACTURING OXAZOLIDINONE MATERIALS |
| CN112543756A (zh) * | 2018-07-25 | 2021-03-23 | 卡迪拉保健有限公司 | 用于治疗哺乳动物感染的经取代噁唑烷酮类 |
| WO2020234636A1 (en) | 2019-05-17 | 2020-11-26 | Cadila Healthcare Limited | Novel compounds for the treatment of mammalian infections |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3344145A (en) * | 1963-10-21 | 1967-09-26 | Geschickter Fund Med Res | N-substituted phenoxyalkyl or phenylthioalkyl-mono azaspiroalkanes |
| 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. |
| US5489689A (en) * | 1993-09-30 | 1996-02-06 | Mallinckrodt Chemical, Inc. | Preparation of piperidine derivatives |
| US5668286A (en) * | 1994-03-15 | 1997-09-16 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions containing them |
| JPH0873455A (ja) * | 1994-03-15 | 1996-03-19 | Upjohn Co:The | オキサゾリジノン誘導体及びこれを有効成分とする医薬組成物 |
| SI0788498T1 (en) * | 1994-10-26 | 2001-12-31 | Upjohn Co | Phenyloxazolidinone antimicrobials |
| ES2214546T3 (es) * | 1995-09-15 | 2004-09-16 | PHARMACIA & UPJOHN COMPANY | N-oxidos de aminoariloxazolidinona. |
| GB9702213D0 (en) * | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| RU2208613C2 (ru) * | 1997-05-30 | 2003-07-20 | Фармация Энд Апджон Компани | Оксазолидиноновые антибактериальные агенты, содержащие тиокарбонильную функциональную группу |
| CA2333332A1 (en) * | 1998-06-05 | 1999-12-16 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| GB9821938D0 (en) * | 1998-10-09 | 1998-12-02 | Zeneca Ltd | Chemical compounds |
| JP2000204084A (ja) * | 1998-11-11 | 2000-07-25 | Hokuriku Seiyaku Co Ltd | チオカルバミド酸誘導体 |
| JP3270834B2 (ja) * | 1999-01-27 | 2002-04-02 | ファイザー・プロダクツ・インク | 抗がん剤として有用なヘテロ芳香族二環式誘導体 |
| CA2374383A1 (en) * | 1999-07-28 | 2001-02-08 | Pharmacia & Upjohn Company | Oxazolidinones and their use as antiinfectives |
| US6608081B2 (en) * | 1999-08-12 | 2003-08-19 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
| GB2356389B (en) * | 1999-09-02 | 2003-07-16 | Bruce Stanley Gunton | Loading bay dock control |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| WO2002046156A2 (en) * | 2000-12-06 | 2002-06-13 | Sepracor, Inc. | 4,4-disubstituted piperidines for use as dopamine, serotonin and norepinephrine ligands |
| JP2005503435A (ja) * | 2001-04-17 | 2005-02-03 | メルク アンド カンパニー インコーポレーテッド | ビシクロ[3.1.0]ヘキサン含有オキサゾリジノン抗生物質及びその誘導体 |
| DE10129725A1 (de) * | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
| CA2492194A1 (en) * | 2002-07-11 | 2004-01-22 | Wockhardt Limited | Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoproteins sites |
| US7405228B2 (en) * | 2002-07-11 | 2008-07-29 | Wockhardt Limited | Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoprotein sites |
| AU2003274676A1 (en) * | 2002-07-11 | 2004-02-02 | Yati Chugh | Antimicrobial oxazolidinones, process of their preparation, and pharmaceutical compositions containing them |
| KR100490643B1 (ko) * | 2002-10-29 | 2005-05-19 | 한국과학기술연구원 | 새로운 메틸리덴 피페리딘일 옥사졸리딘온 유도체 및이들의 제조방법 |
| US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
| JP5313126B2 (ja) * | 2006-05-09 | 2013-10-09 | ウォックハート リミテッド | 置換ピペリジノフェニルオキサゾリジノン |
-
2004
- 2004-09-07 US US10/935,708 patent/US7687627B2/en not_active Expired - Fee Related
- 2004-09-08 WO PCT/IN2004/000276 patent/WO2005054234A2/en not_active Ceased
- 2004-09-08 AU AU2004295208A patent/AU2004295208A1/en not_active Abandoned
- 2004-09-08 JP JP2006526008A patent/JP4917432B2/ja not_active Expired - Fee Related
- 2004-09-08 CA CA2537559A patent/CA2537559C/en not_active Expired - Fee Related
- 2004-09-08 BR BRPI0413413-3A patent/BRPI0413413A/pt not_active IP Right Cessation
- 2004-09-08 EA EA200600374A patent/EA200600374A1/ru unknown
- 2004-09-08 EP EP04817639A patent/EP1664038A2/en not_active Withdrawn
-
2010
- 2010-02-12 US US12/705,258 patent/US8729269B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005054234A3 (en) | 2005-09-29 |
| CA2537559A1 (en) | 2005-06-16 |
| US20050143421A1 (en) | 2005-06-30 |
| US7687627B2 (en) | 2010-03-30 |
| AU2004295208A1 (en) | 2005-06-16 |
| JP2007505102A (ja) | 2007-03-08 |
| WO2005054234A2 (en) | 2005-06-16 |
| US8729269B2 (en) | 2014-05-20 |
| EA200600374A1 (ru) | 2006-08-25 |
| EP1664038A2 (en) | 2006-06-07 |
| BRPI0413413A (pt) | 2007-01-09 |
| JP4917432B2 (ja) | 2012-04-18 |
| WO2005054234A8 (en) | 2006-11-23 |
| US20100144735A1 (en) | 2010-06-10 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20220308 |
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| MKLA | Lapsed |
Effective date: 20200908 |