NO311520B1 - Fenyloksazolidinoner med en C-C-binding til 4-8-leddede heterosykliske ringer, og anvendelse av disse for fremstilling avet medikament - Google Patents

Info

Publication number

NO311520B1

NO311520B1 NO19980855A NO980855A NO311520B1 NO 311520 B1 NO311520 B1 NO 311520B1 NO 19980855 A NO19980855 A NO 19980855A NO 980855 A NO980855 A NO 980855A NO 311520 B1 NO311520 B1 NO 311520B1

Authority

NO

Norway

Prior art keywords

methyl

oxo

oxazolidinyl

acetamide

phenyl

Prior art date

1995-09-01

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• 238000002360 preparation method Methods 0.000 title claims description 18
• 239000003814 drug Substances 0.000 title claims description 4
• 229940079593 drug Drugs 0.000 title claims description 3
• NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 title description 7
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims abstract description 199
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 150
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 102
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
• 150000003839 salts Chemical class 0.000 claims abstract description 9
• OBPBAFOOPYFELR-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)piperidin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CCN(C(=O)CO)CC1 OBPBAFOOPYFELR-HNNXBMFYSA-N 0.000 claims abstract description 5
• YKXQLFMJMPRKHB-KRWDZBQOSA-N n-[[(5s)-3-[4-[1-(2-hydroxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCN(CC=2)C(=O)CO)C=C1 YKXQLFMJMPRKHB-KRWDZBQOSA-N 0.000 claims abstract 2
• 150000001875 compounds Chemical class 0.000 claims description 228
• -1 3-isoxazolyl Chemical group 0.000 claims description 85
• 125000002393 azetidinyl group Chemical group 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• XBVOZOMXOGNJEF-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(3-methylazetidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C2(C)CNC2)C(F)=C1 XBVOZOMXOGNJEF-LBPRGKRZSA-N 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• IPBLZNHWVNEOCJ-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CCNCC1 IPBLZNHWVNEOCJ-AWEZNQCLSA-N 0.000 claims description 13
• SLQCJVDYHZRLLO-INIZCTEOSA-N n-[[(5s)-2-oxo-3-(4-piperidin-4-ylphenyl)-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C2CCNCC2)C=C1 SLQCJVDYHZRLLO-INIZCTEOSA-N 0.000 claims description 10
• YZBAZTPJQWTDFU-INIZCTEOSA-N n-[[(5s)-2-oxo-3-[4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCNCC=2)C=C1 YZBAZTPJQWTDFU-INIZCTEOSA-N 0.000 claims description 9
• UWWGHMAGNGMEGC-AWEZNQCLSA-N n-[[(5s)-3-[4-(3,6-dihydro-2h-thiopyran-4-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=C1C1=CCSCC1 UWWGHMAGNGMEGC-AWEZNQCLSA-N 0.000 claims description 9
• KTSYLLXCSUQNLJ-INIZCTEOSA-N n-[[(5s)-3-[4-(3,6-dihydro-2h-thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCSCC=2)C=C1 KTSYLLXCSUQNLJ-INIZCTEOSA-N 0.000 claims description 9
• OIHSIBMHBVXVJL-AWEZNQCLSA-N n-[[(5s)-3-[4-(3,6-dihydro-2h-pyran-4-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=C1C1=CCOCC1 OIHSIBMHBVXVJL-AWEZNQCLSA-N 0.000 claims description 8
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 7
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• VPCDTULQKWILHG-INIZCTEOSA-N n-[[(5s)-3-[4-(3,6-dihydro-2h-pyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCOCC=2)C=C1 VPCDTULQKWILHG-INIZCTEOSA-N 0.000 claims description 7
• VBXQAUGPKMTPLP-LBPRGKRZSA-N 2,2-dichloro-n-[[(5s)-3-(3-fluoro-4-piperidin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C(Cl)Cl)C2)=O)=CC=C1C1CCNCC1 VBXQAUGPKMTPLP-LBPRGKRZSA-N 0.000 claims description 5
• XCQRTPVQQYMVHU-KRWDZBQOSA-N [2-[4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CCN(C(=O)COC(C)=O)CC1 XCQRTPVQQYMVHU-KRWDZBQOSA-N 0.000 claims description 5
• XAZQGJZPXHLNPQ-IBGZPJMESA-N [2-[4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCN(CC=2)C(=O)COC(C)=O)C=C1 XAZQGJZPXHLNPQ-IBGZPJMESA-N 0.000 claims description 5
• 208000015181 infectious disease Diseases 0.000 claims description 5
• KLPIBFYFTKIGPO-KRWDZBQOSA-N [2-[5-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CCCN(C(=O)COC(C)=O)C1 KLPIBFYFTKIGPO-KRWDZBQOSA-N 0.000 claims description 4
• WTMGDUREMVIHDR-IBGZPJMESA-N benzyl 3-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-3-methylazetidine-1-carboxylate Chemical group O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C2(C)CN(C2)C(=O)OCC=2C=CC=CC=2)C(F)=C1 WTMGDUREMVIHDR-IBGZPJMESA-N 0.000 claims description 4
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• IBMYQCVTKCXCPL-PYMCNQPYSA-N methyl 3-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC)CCC1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F IBMYQCVTKCXCPL-PYMCNQPYSA-N 0.000 claims description 4
• MXBWLINJNLVUIP-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-(1-formylazetidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CN(C=O)C1 MXBWLINJNLVUIP-ZDUSSCGKSA-N 0.000 claims description 4
• COBRKPQWZMUJNL-PYMCNQPYSA-N n-[[(5s)-3-[3-fluoro-4-(1-formylpyrrolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CN(C=O)CC1 COBRKPQWZMUJNL-PYMCNQPYSA-N 0.000 claims description 4
• WZENWQPVABAUCQ-LNHXHEARSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxo-2,5-dihydrothiophen-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CCS(=O)C1 WZENWQPVABAUCQ-LNHXHEARSA-N 0.000 claims description 4
• LXTWELYWOPQBRG-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)-2,3,6,7-tetrahydroazepin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCN(CCC=2)C(=O)CO)C(F)=C1 LXTWELYWOPQBRG-INIZCTEOSA-N 0.000 claims description 4
• SHAZGXQGMWOJSM-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)-3,6-dihydro-2h-pyridin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CCN(C(=O)CO)CC1 SHAZGXQGMWOJSM-HNNXBMFYSA-N 0.000 claims description 4
• DRVJEHFMULYREF-PYMCNQPYSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)pyrrolidin-3-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CN(C(=O)CO)CC1 DRVJEHFMULYREF-PYMCNQPYSA-N 0.000 claims description 4
• SFMMFSBVGVEELX-QFIPXVFZSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-phenylmethoxyacetyl)piperidin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CCN(C(=O)COCC=2C=CC=CC=2)CC1 SFMMFSBVGVEELX-QFIPXVFZSA-N 0.000 claims description 4
• LFXYZYGGRMSPSZ-ZDUSSCGKSA-N n-[[(5s)-3-[4-(1,1-dioxo-2,5-dihydrothiophen-3-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=C1C1=CCS(=O)(=O)C1 LFXYZYGGRMSPSZ-ZDUSSCGKSA-N 0.000 claims description 4
• AXOQIBACZPIAQQ-LBPRGKRZSA-N n-[[(5s)-3-[4-(azetidin-3-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=C1C1CNC1 AXOQIBACZPIAQQ-LBPRGKRZSA-N 0.000 claims description 4
• DREXBRVYJRQWKZ-INIZCTEOSA-N n-[[(5s)-3-[4-(oxan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C2CCOCC2)C=C1 DREXBRVYJRQWKZ-INIZCTEOSA-N 0.000 claims description 4
• GKMGMCDJOCWRSP-HNNXBMFYSA-N tert-butyl 4-[4-[(5s)-5-[[(2,2-dichloroacetyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(N2C(O[C@@H](CNC(=O)C(Cl)Cl)C2)=O)C=C1F GKMGMCDJOCWRSP-HNNXBMFYSA-N 0.000 claims description 4
• LQNWAVYIMPPQBW-SFHVURJKSA-N [2-[4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-2,3,6,7-tetrahydroazepin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCN(CCC=2)C(=O)COC(C)=O)C(F)=C1 LQNWAVYIMPPQBW-SFHVURJKSA-N 0.000 claims description 3
• WACJEDUSHOIJJD-HNNXBMFYSA-N [2-[4-[4-[(5s)-5-[[(2,2-dichloroacetyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-1-yl]-2-oxoethyl] acetate Chemical compound C1CN(C(=O)COC(=O)C)CCC1C1=CC=C(N2C(O[C@@H](CNC(=O)C(Cl)Cl)C2)=O)C=C1F WACJEDUSHOIJJD-HNNXBMFYSA-N 0.000 claims description 3
• RCKTXUPDAOKZAG-SFHVURJKSA-N [2-[5-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-2,3,4,7-tetrahydroazepin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCCN(CC=2)C(=O)COC(C)=O)C(F)=C1 RCKTXUPDAOKZAG-SFHVURJKSA-N 0.000 claims description 3
• ISUDGADPLVDWGP-KRWDZBQOSA-N [2-[5-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-3,4-dihydro-2h-pyridin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CN(C(=O)COC(C)=O)CCC1 ISUDGADPLVDWGP-KRWDZBQOSA-N 0.000 claims description 3
• RETXWTHHXYQJSS-IBGZPJMESA-N benzyl 3-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]azetidine-1-carboxylate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CN(C(=O)OCC=2C=CC=CC=2)C1 RETXWTHHXYQJSS-IBGZPJMESA-N 0.000 claims description 3
• 230000037396 body weight Effects 0.000 claims description 3
• 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
• 230000000813 microbial effect Effects 0.000 claims description 3
• HJYVQNUHPDNYGS-DEOSSOPVSA-N n-[[(5s)-2-oxo-3-[4-[1-(2-phenylmethoxyacetyl)piperidin-4-yl]phenyl]-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C2CCN(CC2)C(=O)COCC=2C=CC=CC=2)C=C1 HJYVQNUHPDNYGS-DEOSSOPVSA-N 0.000 claims description 3
• UPFYCCZKWQCASW-NRFANRHFSA-N n-[[(5s)-3-[3,5-difluoro-4-[1-(2-phenylmethoxyacetyl)piperidin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC(F)=C1C1CCN(C(=O)COCC=2C=CC=CC=2)CC1 UPFYCCZKWQCASW-NRFANRHFSA-N 0.000 claims description 3
• OFOQZVWPLKQXCV-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(1-formylpiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CCN(C=O)CC1 OFOQZVWPLKQXCV-HNNXBMFYSA-N 0.000 claims description 3
• XULRLMYVBPAUAP-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)-2,3,4,7-tetrahydroazepin-5-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCCN(CC=2)C(=O)CO)C(F)=C1 XULRLMYVBPAUAP-INIZCTEOSA-N 0.000 claims description 3
• MEGBYMRVHYMTID-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[1-(4-oxo-1,3-thiazol-2-yl)-3,6-dihydro-2h-pyridin-5-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CCCN(C=2SCC(=O)N=2)C1 MEGBYMRVHYMTID-HNNXBMFYSA-N 0.000 claims description 3
• HNUWAVGQRDSRHM-ZDUSSCGKSA-N n-[[(5s)-3-[4-(3,4-dihydro-2h-pyran-6-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=C1C1=CCCCO1 HNUWAVGQRDSRHM-ZDUSSCGKSA-N 0.000 claims description 3
• 238000007911 parenteral administration Methods 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 claims description 2
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 2
• 125000004522 1,3,4-thiadiazol-5-yl group Chemical group S1C=NN=C1* 0.000 claims description 2
• KLHSNNLBTPYOFO-ZDUSSCGKSA-N 2-[3-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]azetidin-1-yl]acetic acid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CN(CC(O)=O)C1 KLHSNNLBTPYOFO-ZDUSSCGKSA-N 0.000 claims description 2
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
• WWWRFJPWQDMLRH-KRWDZBQOSA-N [2-[4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-1-yl]-2-oxoethyl] acetate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CCN(C(=O)COC(C)=O)CC1 WWWRFJPWQDMLRH-KRWDZBQOSA-N 0.000 claims description 2
• OLVVIMKCTVHIIU-QHCPKHFHSA-N benzyl 4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C=2CCN(CC=2)C(=O)OCC=2C=CC=CC=2)C=C1 OLVVIMKCTVHIIU-QHCPKHFHSA-N 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
• KLKFXXGUMMCODH-HNNXBMFYSA-N methyl 4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F KLKFXXGUMMCODH-HNNXBMFYSA-N 0.000 claims description 2
• ZLZDQOSYWUSDAX-KRWDZBQOSA-N methyl 4-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC)CCC(C=2C=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)=C1 ZLZDQOSYWUSDAX-KRWDZBQOSA-N 0.000 claims description 2
• MGFYEKBRXCRYRJ-AWEZNQCLSA-N n-[[(5s)-3-[3,5-difluoro-4-[1-(2-hydroxyacetyl)piperidin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC(F)=C1C1CCN(C(=O)CO)CC1 MGFYEKBRXCRYRJ-AWEZNQCLSA-N 0.000 claims description 2
• KHVFIFULUZQFAC-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(1-formyl-3,6-dihydro-2h-pyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1=CCN(C=O)CC1 KHVFIFULUZQFAC-HNNXBMFYSA-N 0.000 claims description 2
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• XKGNXICPKFZNGF-WMCAAGNKSA-N n-[[(5s)-3-[3-fluoro-4-[1-(2-hydroxyacetyl)azepan-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CCN(C(=O)CO)CCC1 XKGNXICPKFZNGF-WMCAAGNKSA-N 0.000 claims description 2
• XBYJRDMCOMNVIP-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-[1-(4-oxo-1,3-thiazol-2-yl)piperidin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CCN(C=2SCC(=O)N=2)CC1 XBYJRDMCOMNVIP-HNNXBMFYSA-N 0.000 claims description 2
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• MVJGFQOWZHVTMW-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CCN(C=2SC(C)=NN=2)CC1 MVJGFQOWZHVTMW-INIZCTEOSA-N 0.000 claims description 2
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• VSUPIMNZUDJHLW-YUZLPWPTSA-N n-[[(5s)-3-[4-(2,3-dihydrothiophen-3-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=C1C1C=CSC1 VSUPIMNZUDJHLW-YUZLPWPTSA-N 0.000 claims description 2
• SXFXQOMRJBXZBL-KRWDZBQOSA-N n-[[(5s)-3-[4-[1-(2-hydroxyacetyl)piperidin-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C2CCN(CC2)C(=O)CO)C=C1 SXFXQOMRJBXZBL-KRWDZBQOSA-N 0.000 claims description 2
• UZNPZAJJFSZIHI-INIZCTEOSA-N n-[[(5s)-3-[4-[1-(cyanomethyl)piperidin-4-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=C1C1CCN(CC#N)CC1 UZNPZAJJFSZIHI-INIZCTEOSA-N 0.000 claims description 2
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