JP2005524660A - Ｎ−アリール−２−オキサゾリジノン−５−カルボキサミドおよびその誘導体ならびに抗細菌剤としてのそれらの使用 - Google Patents

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Publication number

JP2005524660A

JP2005524660A JP2003571259A JP2003571259A JP2005524660A JP 2005524660 A JP2005524660 A JP 2005524660A JP 2003571259 A JP2003571259 A JP 2003571259A JP 2003571259 A JP2003571259 A JP 2003571259A JP 2005524660 A JP2005524660 A JP 2005524660A

Authority

JP

Japan

Prior art keywords

oxo

oxazolidinecarboxamide

alkyl

dihydro

methyl

Prior art date

2002-02-25

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.)

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• 239000003242 anti bacterial agent Substances 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 331
• 125000003118 aryl group Chemical group 0.000 claims abstract description 61
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
• -1 -OH Chemical group 0.000 claims description 249
• 125000000217 alkyl group Chemical group 0.000 claims description 212
• 238000000034 method Methods 0.000 claims description 147
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 135
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 131
• 229910052717 sulfur Inorganic materials 0.000 claims description 109
• 125000005843 halogen group Chemical group 0.000 claims description 89
• 125000003545 alkoxy group Chemical group 0.000 claims description 54
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
• 229910052757 nitrogen Inorganic materials 0.000 claims description 45
• 125000001424 substituent group Chemical group 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 28
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 125000002252 acyl group Chemical group 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 17
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 13
• 125000003107 substituted aryl group Chemical group 0.000 claims description 13
• 239000011734 sodium Substances 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 208000015181 infectious disease Diseases 0.000 claims description 11
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• JCSCLHOUNBXMEE-CYBMUJFWSA-N (5r)-3-[4-(3,6-dihydro-2h-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1C1=CCSCC1 JCSCLHOUNBXMEE-CYBMUJFWSA-N 0.000 claims description 10
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• FQPPEKCCNRMKBJ-GFCCVEGCSA-N (5r)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1N1CCSCC1 FQPPEKCCNRMKBJ-GFCCVEGCSA-N 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 9
• ZTAAKFXBCMVLOG-LLVKDONJSA-N (5r)-3-(3,5-difluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC(F)=C1N1CCSCC1 ZTAAKFXBCMVLOG-LLVKDONJSA-N 0.000 claims description 8
• GCXVBAMUDDGHGW-GFCCVEGCSA-N (5r)-3-(3,5-difluoro-4-thiomorpholin-4-ylphenyl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC(F)=C1N1CCSCC1 GCXVBAMUDDGHGW-GFCCVEGCSA-N 0.000 claims description 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 230000000813 microbial effect Effects 0.000 claims description 8
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 229910052744 lithium Inorganic materials 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 229910052708 sodium Inorganic materials 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
• IBXSKLWVJHRUJN-CYBMUJFWSA-N (5r)-3-[3-fluoro-4-(thian-4-yl)phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1C1CCSCC1 IBXSKLWVJHRUJN-CYBMUJFWSA-N 0.000 claims description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• 230000037396 body weight Effects 0.000 claims description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 239000011591 potassium Substances 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
• WITWMANCORVTOM-SNVBAGLBSA-N (5r)-2-oxo-3-(2-oxo-3-propan-2-yl-1,3-benzothiazol-6-yl)-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2SC(=O)N(C(C)C)C2=CC=C1N1C[C@H](C(N)=O)OC1=O WITWMANCORVTOM-SNVBAGLBSA-N 0.000 claims description 4
• BKSSCIZNJVZMEX-LLVKDONJSA-N (5r)-2-oxo-3-(2-oxo-3-propan-2-yl-1,3-benzoxazol-6-yl)-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2OC(=O)N(C(C)C)C2=CC=C1N1C[C@H](C(N)=O)OC1=O BKSSCIZNJVZMEX-LLVKDONJSA-N 0.000 claims description 4
• UWKBPPOUKCZHEF-GFCCVEGCSA-N (5r)-2-oxo-3-(4-thiomorpholin-4-ylphenyl)-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C1=CC=C(N2CCSCC2)C=C1 UWKBPPOUKCZHEF-GFCCVEGCSA-N 0.000 claims description 4
• UYNQRPSGYOWXKS-CYBMUJFWSA-N (5r)-2-oxo-3-[4-(thian-4-yl)phenyl]-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C1=CC=C(C2CCSCC2)C=C1 UYNQRPSGYOWXKS-CYBMUJFWSA-N 0.000 claims description 4
• MDCWSPZMNORBOW-LLVKDONJSA-N (5r)-3-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C=C2N(C)C(=O)CCC2=CC=1N1C[C@H](C(N)=O)OC1=O MDCWSPZMNORBOW-LLVKDONJSA-N 0.000 claims description 4
• CWTYBIOALFDHGB-SNVBAGLBSA-N (5r)-3-(3-ethyl-2-oxo-1,3-benzoxazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2OC(=O)N(CC)C2=CC=C1N1C[C@H](C(N)=O)OC1=O CWTYBIOALFDHGB-SNVBAGLBSA-N 0.000 claims description 4
• WXYYFVRFZOIINO-GFCCVEGCSA-N (5r)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1N1CCOCC1 WXYYFVRFZOIINO-GFCCVEGCSA-N 0.000 claims description 4
• KDNJZJMUFCQUDR-GFCCVEGCSA-N (5r)-3-(3-fluoro-4-morpholin-4-ylphenyl)-n-hydroxy-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NO)CN1C(C=C1F)=CC=C1N1CCOCC1 KDNJZJMUFCQUDR-GFCCVEGCSA-N 0.000 claims description 4
• NRYRVJNSXGWOMJ-SECBINFHSA-N (5r)-3-(3-methyl-2-oxo-1,3-benzoxazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2OC(=O)N(C)C2=CC=C1N1C[C@H](C(N)=O)OC1=O NRYRVJNSXGWOMJ-SECBINFHSA-N 0.000 claims description 4
• DVNYMQCCQJDHQG-SECBINFHSA-N (5r)-3-(4-methyl-3-oxo-1,4-benzothiazin-7-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C=C2N(C)C(=O)CSC2=CC=1N1C[C@H](C(N)=O)OC1=O DVNYMQCCQJDHQG-SECBINFHSA-N 0.000 claims description 4
• ZXECHFBZDGVJIM-SNVBAGLBSA-N (5r)-3-(4-methyl-3-oxo-1,4-benzoxazin-7-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C=C2N(C)C(=O)COC2=CC=1N1C[C@H](C(N)=O)OC1=O ZXECHFBZDGVJIM-SNVBAGLBSA-N 0.000 claims description 4
• FQJBZAVZDYNYMC-PRHODGIISA-N (5r)-3-[(2r)-1-(2-hydroxyacetyl)-2-methyl-2,3-dihydroindol-5-yl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C([C@H](N(C1=CC=2)C(=O)CO)C)C1=CC=2N1C[C@H](C(N)=O)OC1=O FQJBZAVZDYNYMC-PRHODGIISA-N 0.000 claims description 4
• UFAPAAHPPROOHH-PRHODGIISA-N (5r)-3-[(2r)-1-formyl-2-methyl-2,3-dihydroindol-5-yl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C([C@H](N(C1=CC=2)C=O)C)C1=CC=2N1C[C@H](C(N)=O)OC1=O UFAPAAHPPROOHH-PRHODGIISA-N 0.000 claims description 4
• KQUOQZMXYWNMKZ-GFCCVEGCSA-N (5r)-3-[3,5-difluoro-4-(thian-4-yl)phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC(F)=C1C1CCSCC1 KQUOQZMXYWNMKZ-GFCCVEGCSA-N 0.000 claims description 4
• DXDRDTGEPCSZKE-LLVKDONJSA-N (5r)-3-[4-(2,5-dihydropyrrol-1-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC(F)=C1N1CC=CC1 DXDRDTGEPCSZKE-LLVKDONJSA-N 0.000 claims description 4
• NIWCGQZRUBFWOX-CYBMUJFWSA-N (5r)-3-[4-(3,6-dihydro-2h-pyran-4-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1C1=CCOCC1 NIWCGQZRUBFWOX-CYBMUJFWSA-N 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• PPHTXSXTXAEQGB-LLVKDONJSA-N methyl 3-[4-[(5r)-5-carbamoyl-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl]-3-methylazetidine-1-carboxylate Chemical compound C1N(C(=O)OC)CC1(C)C1=C(F)C=C(N2C(O[C@H](C2)C(N)=O)=O)C=C1F PPHTXSXTXAEQGB-LLVKDONJSA-N 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
• DJUZFAHLCSKESR-LLVKDONJSA-N (5r)-3-(3,5-difluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC(F)=C1N1CCOCC1 DJUZFAHLCSKESR-LLVKDONJSA-N 0.000 claims description 3
• CJPBTUBBXNYPCV-GFCCVEGCSA-N (5r)-3-(3,5-difluoro-4-morpholin-4-ylphenyl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC(F)=C1N1CCOCC1 CJPBTUBBXNYPCV-GFCCVEGCSA-N 0.000 claims description 3
• NMUWCDITKDTXCY-SECBINFHSA-N (5r)-3-(3-ethyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2SC(=O)N(CC)C2=CC=C1N1C[C@H](C(N)=O)OC1=O NMUWCDITKDTXCY-SECBINFHSA-N 0.000 claims description 3
• DRTVZEUJGKZSRI-LLVKDONJSA-N (5r)-3-(3-ethyl-2-oxo-1,3-benzoxazol-6-yl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2OC(=O)N(CC)C2=CC=C1N1C[C@H](C(=O)NC)OC1=O DRTVZEUJGKZSRI-LLVKDONJSA-N 0.000 claims description 3
• RQABAESQBKRWLX-OAHLLOKOSA-N (5r)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-n-prop-2-enyl-1,3-oxazolidine-5-carboxamide Chemical compound FC1=CC(N2C(O[C@H](C2)C(=O)NCC=C)=O)=CC=C1N1CCOCC1 RQABAESQBKRWLX-OAHLLOKOSA-N 0.000 claims description 3
• QQIXWRAJTSBLER-OAHLLOKOSA-N (5r)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-n-propyl-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NCCC)CN1C(C=C1F)=CC=C1N1CCOCC1 QQIXWRAJTSBLER-OAHLLOKOSA-N 0.000 claims description 3
• QRTUBJBBRLVBHE-CYBMUJFWSA-N (5r)-3-(3-fluoro-4-morpholin-4-ylphenyl)-n-methoxy-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NOC)CN1C(C=C1F)=CC=C1N1CCOCC1 QRTUBJBBRLVBHE-CYBMUJFWSA-N 0.000 claims description 3
• URCRLDDNCLOAMA-CYBMUJFWSA-N (5r)-3-(3-fluoro-4-morpholin-4-ylphenyl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC=C1N1CCOCC1 URCRLDDNCLOAMA-CYBMUJFWSA-N 0.000 claims description 3
• IPLJXFWUBZYCKS-CYBMUJFWSA-N (5r)-3-(3-fluoro-4-pyridin-3-ylphenyl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C1=CC=C(C=2C=NC=CC=2)C(F)=C1 IPLJXFWUBZYCKS-CYBMUJFWSA-N 0.000 claims description 3
• UROLCMGOKNJOLW-CYBMUJFWSA-N (5r)-3-(3-fluoro-4-pyridin-4-ylphenyl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C1=CC=C(C=2C=CN=CC=2)C(F)=C1 UROLCMGOKNJOLW-CYBMUJFWSA-N 0.000 claims description 3
• WAGKFNIYFRFVPU-MRVPVSSYSA-N (5r)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2SC(=O)N(C)C2=CC=C1N1C[C@H](C(N)=O)OC1=O WAGKFNIYFRFVPU-MRVPVSSYSA-N 0.000 claims description 3
• RHYNLXCUCXAWGM-CYBMUJFWSA-N (5r)-3-[3-fluoro-4-(4-oxo-2,3-dihydropyridin-1-yl)phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1N1C=CC(=O)CC1 RHYNLXCUCXAWGM-CYBMUJFWSA-N 0.000 claims description 3
• CJRFJXGGLQYNMI-SECBINFHSA-N (5r)-3-[3-fluoro-4-(5-oxo-4h-1,3,4-thiadiazin-2-yl)phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1C1=NNC(=O)CS1 CJRFJXGGLQYNMI-SECBINFHSA-N 0.000 claims description 3
• KFWKTPVZIZYTGO-CQSZACIVSA-N (5r)-3-[3-fluoro-4-(thian-4-yl)phenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC=C1C1CCSCC1 KFWKTPVZIZYTGO-CQSZACIVSA-N 0.000 claims description 3
• GNUMQVDIQCVLSO-CYBMUJFWSA-N (5r)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1N1CCN(C(=O)CO)CC1 GNUMQVDIQCVLSO-CYBMUJFWSA-N 0.000 claims description 3
• QDBQEWHDGZHOEJ-SNVBAGLBSA-N (5r)-n-(2-fluoroethyl)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2SC(=O)N(C)C2=CC=C1N1C[C@H](C(=O)NCCF)OC1=O QDBQEWHDGZHOEJ-SNVBAGLBSA-N 0.000 claims description 3
• GXAPJUAYPFLWTE-GFCCVEGCSA-N (5r)-n-(2-fluoroethyl)-3-(4-methyl-3-oxo-1,4-benzoxazin-7-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C=C2N(C)C(=O)COC2=CC=1N1C[C@H](C(=O)NCCF)OC1=O GXAPJUAYPFLWTE-GFCCVEGCSA-N 0.000 claims description 3
• JJWRKIMHGCEUMX-SNVBAGLBSA-N (5r)-n-(2-hydroxyethyl)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2SC(=O)N(C)C2=CC=C1N1C[C@H](C(=O)NCCO)OC1=O JJWRKIMHGCEUMX-SNVBAGLBSA-N 0.000 claims description 3
• USCNSXWQKOQGOB-SNVBAGLBSA-N (5r)-n-ethyl-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NCC)CN1C1=CC=C(N(C)C(=O)S2)C2=C1 USCNSXWQKOQGOB-SNVBAGLBSA-N 0.000 claims description 3
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• YXJLHTGVTPQZOX-SNVBAGLBSA-N (5r)-n-methyl-3-(3-methyl-2-oxo-1,3-benzoxazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC=C(N(C)C(=O)O2)C2=C1 YXJLHTGVTPQZOX-SNVBAGLBSA-N 0.000 claims description 3
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• IWURKKQULNDEEN-GFCCVEGCSA-N methyl 3-[2,6-difluoro-4-[(5r)-5-(methylcarbamoyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-3-methylazetidine-1-carboxylate Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC(F)=C(C2(C)CN(C2)C(=O)OC)C(F)=C1 IWURKKQULNDEEN-GFCCVEGCSA-N 0.000 claims description 3
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• GRDXHMKGPWSGPF-SSDOTTSWSA-N (5r)-3-(4-fluoro-3-methyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2SC(=O)N(C)C2=C(F)C=C1N1C[C@H](C(N)=O)OC1=O GRDXHMKGPWSGPF-SSDOTTSWSA-N 0.000 claims description 2
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• NUZHYTLBLZEQNG-MRVPVSSYSA-N (5r)-3-(4-fluoro-3-methyl-2-oxo-1,3-benzoxazol-6-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2OC(=O)N(C)C2=C(F)C=C1N1C[C@H](C(N)=O)OC1=O NUZHYTLBLZEQNG-MRVPVSSYSA-N 0.000 claims description 2
• HNPLAXYMRQAUST-SECBINFHSA-N (5r)-3-(4-fluoro-3-methyl-2-oxo-1,3-benzoxazol-6-yl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC(F)=C(N(C)C(=O)O2)C2=C1 HNPLAXYMRQAUST-SECBINFHSA-N 0.000 claims description 2
• CPFQRZBIICTUNK-SECBINFHSA-N (5r)-3-(4-methyl-3-sulfanylidene-1,4-benzothiazin-7-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C=C2N(C)C(=S)CSC2=CC=1N1C[C@H](C(N)=O)OC1=O CPFQRZBIICTUNK-SECBINFHSA-N 0.000 claims description 2
• XZYXQESZFQAFRM-MRVPVSSYSA-N (5r)-3-(5-fluoro-4-methyl-3-oxo-1,4-benzothiazin-7-yl)-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C=1C(F)=C2N(C)C(=O)CSC2=CC=1N1C[C@H](C(N)=O)OC1=O XZYXQESZFQAFRM-MRVPVSSYSA-N 0.000 claims description 2
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• HVYJVJGGLXRKPA-LLVKDONJSA-N (5r)-3-(8-fluoro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC(F)=C(N(C)C(=O)CC2)C2=C1 HVYJVJGGLXRKPA-LLVKDONJSA-N 0.000 claims description 2
• CYKKTHSKKBEKGO-CYBMUJFWSA-N (5r)-3-[2-(2-hydroxyacetyl)-1,3,4,5-tetrahydro-2-benzazepin-7-yl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C1=CC=C(CN(CCC2)C(=O)CO)C2=C1 CYKKTHSKKBEKGO-CYBMUJFWSA-N 0.000 claims description 2
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• FGPXVQBWCSAZLP-GFCCVEGCSA-N (5r)-3-[3,5-difluoro-4-(1-formyl-3-methylazetidin-3-yl)phenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC(F)=C(C2(C)CN(C2)C=O)C(F)=C1 FGPXVQBWCSAZLP-GFCCVEGCSA-N 0.000 claims description 2
• ULWADQJJGRUNFC-GFCCVEGCSA-N (5r)-3-[3,5-difluoro-4-(4-oxo-2,3-dihydropyridin-1-yl)phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC(F)=C1N1C=CC(=O)CC1 ULWADQJJGRUNFC-GFCCVEGCSA-N 0.000 claims description 2
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• YMEXXOOHJUPCFN-CYBMUJFWSA-N (5r)-3-[3,5-difluoro-4-(4-oxo-2,3-dihydropyridin-1-yl)phenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC(F)=C1N1C=CC(=O)CC1 YMEXXOOHJUPCFN-CYBMUJFWSA-N 0.000 claims description 2
• SCDRIVUYGBNXMD-ZIAGYGMSSA-N (5r)-3-[3,5-difluoro-4-[1-[(2s)-2-hydroxy-3-(oxo-$l^{5}-phosphanylidyne)propanoyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC(F)=C1C1=CCN(C(=O)[C@H](O)C#P=O)CC1 SCDRIVUYGBNXMD-ZIAGYGMSSA-N 0.000 claims description 2
• FDJDVQBIFQGZQD-HUUCEWRRSA-N (5r)-3-[3,5-difluoro-4-[1-[(2s)-2-hydroxy-3-(oxo-$l^{5}-phosphanylidyne)propanoyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC(F)=C1C1=CCN(C(=O)[C@H](O)C#P=O)CC1 FDJDVQBIFQGZQD-HUUCEWRRSA-N 0.000 claims description 2
• PHIUQBRDVQHLSF-CYBMUJFWSA-N (5r)-3-[3-(2-hydroxyacetyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C1=CC=C(CCN(CC2)C(=O)CO)C2=C1 PHIUQBRDVQHLSF-CYBMUJFWSA-N 0.000 claims description 2
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• BFCYCWXUPMUIKV-CYBMUJFWSA-N (5r)-3-[3-fluoro-4-(1-formyl-3-methylazetidin-3-yl)phenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C1=CC=C(C2(C)CN(C2)C=O)C(F)=C1 BFCYCWXUPMUIKV-CYBMUJFWSA-N 0.000 claims description 2
• OJYPEHVDDYZBLI-CQSZACIVSA-N (5r)-3-[3-fluoro-4-(4-oxo-2,3-dihydropyridin-1-yl)phenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC=C1N1C=CC(=O)CC1 OJYPEHVDDYZBLI-CQSZACIVSA-N 0.000 claims description 2
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• XBZWCAGFNPJAMO-HUUCEWRRSA-N (5r)-3-[3-fluoro-4-[1-[(2s)-2-hydroxy-3-(oxo-$l^{5}-phosphanylidyne)propanoyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1C1=CCN(C(=O)[C@H](O)C#P=O)CC1 XBZWCAGFNPJAMO-HUUCEWRRSA-N 0.000 claims description 2
• WGOPRXGMVLHDRW-HZPDHXFCSA-N (5r)-3-[3-fluoro-4-[1-[(2s)-2-hydroxy-3-(oxo-$l^{5}-phosphanylidyne)propanoyl]-3,6-dihydro-2h-pyridin-4-yl]phenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC=C1C1=CCN(C(=O)[C@H](O)C#P=O)CC1 WGOPRXGMVLHDRW-HZPDHXFCSA-N 0.000 claims description 2
• QTZDPVIMVDPSEF-GFCCVEGCSA-N (5r)-3-[4-(3,6-dihydro-2h-thiopyran-4-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC(F)=C1C1=CCSCC1 QTZDPVIMVDPSEF-GFCCVEGCSA-N 0.000 claims description 2
• JQMIXARXMAGQCC-CYBMUJFWSA-N (5r)-3-[4-(3,6-dihydro-2h-thiopyran-4-yl)-3,5-difluorophenyl]-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NC)CN1C(C=C1F)=CC(F)=C1C1=CCSCC1 JQMIXARXMAGQCC-CYBMUJFWSA-N 0.000 claims description 2
• ABEMHOHHWQOSBC-OAHLLOKOSA-N (5r)-n-(2-fluoroethyl)-2-oxo-3-[4-(4-oxo-2,3-dihydropyridin-1-yl)phenyl]-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)NCCF)CN1C1=CC=C(N2C=CC(=O)CC2)C=C1 ABEMHOHHWQOSBC-OAHLLOKOSA-N 0.000 claims description 2
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