HRP20040717A2 - N-aryl-2-oxazolidinone-5-carboxamides and their derivatives and their use as antibacterials - Google Patents

Info

Publication number

HRP20040717A2

HRP20040717A2 HR20040717A HRP20040717A HRP20040717A2 HR P20040717 A2 HRP20040717 A2 HR P20040717A2 HR 20040717 A HR20040717 A HR 20040717A HR P20040717 A HRP20040717 A HR P20040717A HR P20040717 A2 HRP20040717 A2 HR P20040717A2

Authority

HR

Croatia

Prior art keywords

oxo

oxazolidinecarboxamide

alkyl

dihydro

methyl

Prior art date

2002-02-25

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• 230000000844 anti-bacterial effect Effects 0.000 title description 6
• 229940088710 antibiotic agent Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 349
• -1 -OH Chemical group 0.000 claims description 186
• 238000000034 method Methods 0.000 claims description 168
• 125000000623 heterocyclic group Chemical group 0.000 claims description 97
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 229910052736 halogen Inorganic materials 0.000 claims description 91
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 88
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 80
• 150000002367 halogens Chemical class 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 42
• 238000011282 treatment Methods 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
• 229910052717 sulfur Inorganic materials 0.000 claims description 36
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 30
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 30
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 30
• 125000005843 halogen group Chemical group 0.000 claims description 26
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 23
• 125000002252 acyl group Chemical group 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 15
• 239000000825 pharmaceutical preparation Substances 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
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 125000003107 substituted aryl group Chemical group 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 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 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000005842 heteroatom Chemical group 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
• 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 8
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 8
• 125000002393 azetidinyl group Chemical group 0.000 claims description 8
• 230000000813 microbial effect Effects 0.000 claims description 8
• 239000003937 drug carrier Substances 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
• 239000011734 sodium Substances 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 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 6
• 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 6
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
• 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 5
• 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 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
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 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
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 229910052744 lithium Inorganic materials 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 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
• 229910052708 sodium Inorganic materials 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
• 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
• 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 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
• 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 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
• 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
• 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 4
• 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 4
• RYZIGHGVLLKQPY-CYBMUJFWSA-N (5r)-3-[3-fluoro-4-(oxan-4-yl)phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1C1CCOCC1 RYZIGHGVLLKQPY-CYBMUJFWSA-N 0.000 claims description 4
• 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 4
• 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 4
• WNDLFHFRKPCLBD-LLVKDONJSA-N (5r)-3-[4-(1,1-dioxo-2,3-dihydro-1,4-thiazin-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)=C1N1C=CS(=O)(=O)CC1 WNDLFHFRKPCLBD-LLVKDONJSA-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
• BABHQPQBNKBUBH-OAHLLOKOSA-N (5r)-3-[4-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound O=C1O[C@@H](C(=O)N)CN1C(C=C1F)=CC=C1N1CC2=NC=CC=C2C1 BABHQPQBNKBUBH-OAHLLOKOSA-N 0.000 claims description 4
• MZSMUCCCNLQYJL-SECBINFHSA-N (5r)-n-methyl-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)NC)CN1C1=CC=C(N(C)C(=O)S2)C2=C1 MZSMUCCCNLQYJL-SECBINFHSA-N 0.000 claims description 4
• 125000006555 (C3-C5) cycloalkyl 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
• 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
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
• ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims description 4
• 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
• PFJNWSSPBAXUQD-SNVBAGLBSA-N (5r)-3-(3-ethyl-2-oxo-1,3-benzothiazol-6-yl)-n-methyl-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound C1=C2SC(=O)N(CC)C2=CC=C1N1C[C@H](C(=O)NC)OC1=O PFJNWSSPBAXUQD-SNVBAGLBSA-N 0.000 claims description 3
• 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 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
• JPERMSZUEANIQN-LLVKDONJSA-N (5r)-3-[3,5-difluoro-4-(1-formyl-3-methylazetidin-3-yl)phenyl]-2-oxo-1,3-oxazolidine-5-carboxamide Chemical compound FC=1C=C(N2C(O[C@H](C2)C(N)=O)=O)C=C(F)C=1C1(C)CN(C=O)C1 JPERMSZUEANIQN-LLVKDONJSA-N 0.000 claims description 3
• 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 3
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