JP2007505102A5 - - Google Patents
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- Publication number
- JP2007505102A5 JP2007505102A5 JP2006526008A JP2006526008A JP2007505102A5 JP 2007505102 A5 JP2007505102 A5 JP 2007505102A5 JP 2006526008 A JP2006526008 A JP 2006526008A JP 2006526008 A JP2006526008 A JP 2006526008A JP 2007505102 A5 JP2007505102 A5 JP 2007505102A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- ylmethyl
- oxazolidine
- 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.)
- Granted
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- -1 Carbamoyloxy Chemical group 0.000 claims description 72
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 150000003857 carboxamides Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 claims description 8
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 150000003536 tetrazoles Chemical class 0.000 claims description 7
- 150000003852 triazoles Chemical class 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims description 2
- 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 2
- WMGVUVWYPFXMSP-HNNXBMFYSA-N N-[[(5S)-3-[3-fluoro-4-(4-sulfinyl-1,8-diazaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S(=O)=C1CCNC11CCN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)F WMGVUVWYPFXMSP-HNNXBMFYSA-N 0.000 claims description 2
- CBVPHTHVJSUOBJ-INIZCTEOSA-N N-[[(5S)-3-[3-fluoro-4-(4-sulfinyl-1-oxa-9-azaspiro[5.5]undecan-9-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S(=O)=C1CCOC2(C1)CCN(CC2)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)F CBVPHTHVJSUOBJ-INIZCTEOSA-N 0.000 claims description 2
- GWMXTLPXRIYYCY-AWEZNQCLSA-N O=C1O[C@@H](CNC(=O)C)CN1C(CC1(F)F)=CC=C1N1CCC(O)(CN=[N+]=[N-])CC1 Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(CC1(F)F)=CC=C1N1CCC(O)(CN=[N+]=[N-])CC1 GWMXTLPXRIYYCY-AWEZNQCLSA-N 0.000 claims description 2
- 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 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YXTYRPFLERNOHB-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-fluoro-4-methylpiperidin-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(C)(F)CC1 YXTYRPFLERNOHB-AWEZNQCLSA-N 0.000 claims description 2
- CZANNGHFKPLUFK-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(4-hydroxy-4-methylpiperidin-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(C)(O)CC1 CZANNGHFKPLUFK-AWEZNQCLSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- WMSRYSCEHMWXLU-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-fluoro-4-(iodomethyl)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)(CI)CC1 WMSRYSCEHMWXLU-AWEZNQCLSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- DTIBVFOYPBEUEF-HNNXBMFYSA-N n-[[(5s)-3-[4-(1,3-dioxa-8-azaspiro[4.5]decan-8-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=C1N1CCC2(OCOC2)CC1 DTIBVFOYPBEUEF-HNNXBMFYSA-N 0.000 claims description 2
- BMOJYTOGPHZWEU-AWEZNQCLSA-N n-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC(F)=C1N1CCC2(OCCO2)CC1 BMOJYTOGPHZWEU-AWEZNQCLSA-N 0.000 claims description 2
- GNHMYRZWZMSGCL-INIZCTEOSA-N n-[[(5s)-3-[4-(1,4-dioxa-9-azaspiro[5.5]undecan-9-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=C1N1CCC2(OCCOC2)CC1 GNHMYRZWZMSGCL-INIZCTEOSA-N 0.000 claims description 2
- AFZFYXJGJDXKBA-WMCAAGNKSA-N n-[[(5s)-3-[4-(2-cyano-6-azaspiro[2.5]octan-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=C1N1CCC2(C(C2)C#N)CC1 AFZFYXJGJDXKBA-WMCAAGNKSA-N 0.000 claims description 2
- QDNRIYLNGXKDJS-PKHIMPSTSA-N n-[[(5s)-3-[4-(2-cyano-6-azaspiro[2.5]octan-6-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CCC3(C(C3)C#N)CC2)C=C1 QDNRIYLNGXKDJS-PKHIMPSTSA-N 0.000 claims description 2
- CPDYRAAJSBSFQY-ZDUSSCGKSA-N n-[[(5s)-3-[4-(4,4-difluoropiperidin-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)(F)CC1 CPDYRAAJSBSFQY-ZDUSSCGKSA-N 0.000 claims description 2
- ZKEHLMJXGHKXFP-DBCMNUGHSA-N n-[[(5s)-3-[4-(4-acetamido-4-fluoro-2-methylpiperidin-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CC1CC(F)(NC(C)=O)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F ZKEHLMJXGHKXFP-DBCMNUGHSA-N 0.000 claims description 2
- QBEFBNQWPKYHBW-AWEZNQCLSA-N n-[[(5s)-3-[4-(4-cyano-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)(C#N)CC1 QBEFBNQWPKYHBW-AWEZNQCLSA-N 0.000 claims description 2
- 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 2
- AFZFYXJGJDXKBA-HOCLYGCPSA-N n-[[(5s)-3-[4-[(2r)-2-cyano-6-azaspiro[2.5]octan-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=C1N1CCC2([C@@H](C2)C#N)CC1 AFZFYXJGJDXKBA-HOCLYGCPSA-N 0.000 claims description 2
- AFZFYXJGJDXKBA-ZBFHGGJFSA-N n-[[(5s)-3-[4-[(2s)-2-cyano-6-azaspiro[2.5]octan-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=C1N1CCC2([C@H](C2)C#N)CC1 AFZFYXJGJDXKBA-ZBFHGGJFSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- JJQROJUAPJUQGP-INIZCTEOSA-N n-[[(5s)-3-[4-[4-(azidomethyl)-4-hydroxypiperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CCC(O)(CN=[N+]=[N-])CC2)C=C1 JJQROJUAPJUQGP-INIZCTEOSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 6
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 6
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 4
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 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 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- LVZKLNPRCBWIBH-UHFFFAOYSA-N (2-amino-2-oxoethyl) methanesulfonate Chemical compound CS(=O)(=O)OCC(N)=O LVZKLNPRCBWIBH-UHFFFAOYSA-N 0.000 claims 1
- XQZCLEBNIGLRJG-INIZCTEOSA-N (5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-fluorophenyl]-5-(1,2-oxazol-3-ylmethyl)-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C(O[C@@H](CC3=NOC=C3)C2)=O)=CC=C1N(CC1)CCC21OCCO2 XQZCLEBNIGLRJG-INIZCTEOSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- OMAMURWOQKMKLO-ZDUSSCGKSA-N 1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-hydroxypiperidine-4-carboxamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC(O)(C(N)=O)CC1 OMAMURWOQKMKLO-ZDUSSCGKSA-N 0.000 claims 1
- HVIMQUQJSWTRAE-MRXNPFEDSA-N 1-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]triazole-4-carbonitrile Chemical compound FC1=CC(N2C(O[C@H](CN3N=NC(=C3)C#N)C2)=O)=CC=C1N(CC1)CCC21OCCO2 HVIMQUQJSWTRAE-MRXNPFEDSA-N 0.000 claims 1
- 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 1
- HDZHLBOUNDUJBH-BBYVJXSUSA-N 2-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-cyanopiperidin-2-yl]-2-cyanoacetic acid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1C(C(C#N)C(O)=O)CC(C#N)CC1 HDZHLBOUNDUJBH-BBYVJXSUSA-N 0.000 claims 1
- 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 1
- WCFVCBKDXXPNPZ-INIZCTEOSA-N 3-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]triazole-4-carbonitrile Chemical compound FC1=CC(N2C(O[C@H](CN3C(=CN=N3)C#N)C2)=O)=CC=C1N(CC1)CCC21OCCO2 WCFVCBKDXXPNPZ-INIZCTEOSA-N 0.000 claims 1
- DNRCUMDULWDBQC-UHFFFAOYSA-N 3-phenyl-4-piperidin-1-yl-1,3-oxazolidin-2-one Chemical compound O=C1OCC(N2CCCCC2)N1C1=CC=CC=C1 DNRCUMDULWDBQC-UHFFFAOYSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- DJABNYZRYVMURQ-UHFFFAOYSA-N CS(=O)(=O)OCC(=S)N Chemical compound CS(=O)(=O)OCC(=S)N DJABNYZRYVMURQ-UHFFFAOYSA-N 0.000 claims 1
- ZKESMLMPQYIAGG-UHFFFAOYSA-N CS(=O)(=O)OCS(=O)(=O)N Chemical compound CS(=O)(=O)OCS(=O)(=O)N ZKESMLMPQYIAGG-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- GIRMXAXOYHZLES-HNNXBMFYSA-N N-[[(5S)-3-[3-fluoro-4-(4-sulfinyl-1-oxa-8-azaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S(=O)=C1CCOC11CCN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)F GIRMXAXOYHZLES-HNNXBMFYSA-N 0.000 claims 1
- LJWBFZJGZHWEHM-HNNXBMFYSA-N N-[[(5S)-3-[3-fluoro-4-(4-sulfonyl-1-oxa-8-azaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound S(=O)(=O)=C1CCOC11CCN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)F LJWBFZJGZHWEHM-HNNXBMFYSA-N 0.000 claims 1
- ZSEIMLJOZRBCNG-JBZHPUCOSA-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]methanesulfonamide Chemical compound FC1C2(OCCO2)CCN(C1)C1=C(C=C(C=C1)N1C(O[C@@H](C1)CNS(=O)(=O)C)=O)F ZSEIMLJOZRBCNG-JBZHPUCOSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- UBAJGAAKKLTNJA-MRXNPFEDSA-N ethyl 1-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OCC)=CN1C[C@H]1OC(=O)N(C=2C=C(F)C(N3CCC4(CC3)OCCO4)=CC=2)C1 UBAJGAAKKLTNJA-MRXNPFEDSA-N 0.000 claims 1
- ZZPGPLXUTAMFDW-ZENAZSQFSA-N ethyl 2-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-cyanopiperidin-4-yl]-2-cyanoacetate Chemical compound C1CC(C(C#N)C(=O)OCC)(C#N)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F ZZPGPLXUTAMFDW-ZENAZSQFSA-N 0.000 claims 1
- MCAWGSVXAPRIGP-ZENAZSQFSA-N ethyl 2-cyano-2-[4-cyano-1-[4-[(5s)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-yl]acetate Chemical compound C1CC(C(C#N)C(=O)OCC)(C#N)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=S)C2)=O)C=C1F MCAWGSVXAPRIGP-ZENAZSQFSA-N 0.000 claims 1
- ZDQVTJNNERYTNS-INIZCTEOSA-N ethyl 3-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]triazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=NN1C[C@H]1OC(=O)N(C=2C=C(F)C(N3CCC4(CC3)OCCO4)=CC=2)C1 ZDQVTJNNERYTNS-INIZCTEOSA-N 0.000 claims 1
- LGJUHMCBHHTRST-BUSXIPJBSA-N ethyl 6-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-1-oxa-6-azaspiro[2.5]octane-2-carboxylate Chemical compound CCOC(=O)C1OC11CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 LGJUHMCBHHTRST-BUSXIPJBSA-N 0.000 claims 1
- ZJKMVQNENXXVIV-BHWOMJMDSA-N ethyl 6-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-6-azaspiro[2.5]octane-2-carboxylate Chemical compound CCOC(=O)C1CC11CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 ZJKMVQNENXXVIV-BHWOMJMDSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims 1
- FWTSKUHXLFNAGE-NRFANRHFSA-N methyl 4-[[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-cyanopiperidin-4-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1(C#N)CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 FWTSKUHXLFNAGE-NRFANRHFSA-N 0.000 claims 1
- ARJCLTGRRMCFFC-NRFANRHFSA-N methyl 4-[[4-cyano-1-[4-[(5s)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperidin-4-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1(C#N)CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=S)C2)=O)F)CC1 ARJCLTGRRMCFFC-NRFANRHFSA-N 0.000 claims 1
- DISVDXBWTFCPPN-HNNXBMFYSA-N methyl n-[[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-4-cyanopiperidin-4-yl]amino]carbamate Chemical compound C1CC(NNC(=O)OC)(C#N)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F DISVDXBWTFCPPN-HNNXBMFYSA-N 0.000 claims 1
- UEWXIGOCNHZKJN-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxa-3-thia-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=C1N1CCC2(OCSC2)CC1 UEWXIGOCNHZKJN-HNNXBMFYSA-N 0.000 claims 1
- MPSWZEHHXKCAMU-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxa-4,8-diazaspiro[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=C1N1CCC2(OCCN2)CC1 MPSWZEHHXKCAMU-HNNXBMFYSA-N 0.000 claims 1
- DVDNQRXNUDWHFV-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxa-4-thia-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=C1N1CCC2(SCCO2)CC1 DVDNQRXNUDWHFV-HNNXBMFYSA-N 0.000 claims 1
- CCJSAMRFAKCJSV-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxa-4-thia-9-azaspiro[5.5]undecan-9-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC2(OCCSC2)CC1 CCJSAMRFAKCJSV-INIZCTEOSA-N 0.000 claims 1
- UBNOGFKMNUEPIW-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxa-6-azaspiro[2.5]octan-6-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC2(OC2)CC1 UBNOGFKMNUEPIW-AWEZNQCLSA-N 0.000 claims 1
- IBRRDCWRBXVUCT-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxa-7-azaspiro[3.5]nonan-7-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC2(OCC2)CC1 IBRRDCWRBXVUCT-HNNXBMFYSA-N 0.000 claims 1
- ULAWMLGJDCVJOY-HNNXBMFYSA-N n-[[(5s)-3-[3-fluoro-4-(1-thia-4,8-diazaspiro[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=C1N1CCC2(SCCN2)CC1 ULAWMLGJDCVJOY-HNNXBMFYSA-N 0.000 claims 1
- RJZMURRKYXVRKJ-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(1-thia-6-azaspiro[2.5]octan-6-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC2(SC2)CC1 RJZMURRKYXVRKJ-AWEZNQCLSA-N 0.000 claims 1
- XWTCCHFWZTZDJN-WMCAAGNKSA-N n-[[(5s)-3-[3-fluoro-4-(2-methyl-1,3-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O1C(C)OCC11CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 XWTCCHFWZTZDJN-WMCAAGNKSA-N 0.000 claims 1
- KMIJARBXDSVKMN-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(2-oxo-1-oxa-3,8-diazaspiro[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=C1N1CCC2(OC(=O)NC2)CC1 KMIJARBXDSVKMN-AWEZNQCLSA-N 0.000 claims 1
- MSPZKNOJKITYKP-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(2-sulfinyl-6-azaspiro[2.5]octan-6-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCC2(C(C2)=S=O)CC1 MSPZKNOJKITYKP-AWEZNQCLSA-N 0.000 claims 1
- MZVBGKHOLSBVER-VYIIXAMBSA-N n-[[(5s)-3-[3-fluoro-4-(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)COC11CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 MZVBGKHOLSBVER-VYIIXAMBSA-N 0.000 claims 1
- JABNABHFABNMBI-OOJLDXBWSA-N n-[[(5s)-3-[3-fluoro-4-(4-hydroxy-3,3,4-trimethylpiperidin-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=C1N1CC(C)(C)C(C)(O)CC1 JABNABHFABNMBI-OOJLDXBWSA-N 0.000 claims 1
- IVVKMIGCDDNYEI-MBIQTGHCSA-N n-[[(5s)-3-[3-fluoro-4-(4-hydroxy-3,3-dimethylpiperidin-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=C1N1CC(C)(C)C(O)CC1 IVVKMIGCDDNYEI-MBIQTGHCSA-N 0.000 claims 1
- 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 1
- GKEFWWBJBCMNTH-VYIIXAMBSA-N n-[[(5s)-3-[3-fluoro-4-(6-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CC1CN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CCC11OCCO1 GKEFWWBJBCMNTH-VYIIXAMBSA-N 0.000 claims 1
- HXIASHGETYAPBG-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-(7-oxa-11-thia-3-azaspiro[5.6]dodecan-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=C1N1CCC2(OCCCSC2)CC1 HXIASHGETYAPBG-KRWDZBQOSA-N 0.000 claims 1
- 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 1
- UNAHCZYDWQOVLL-QNNTWYEPSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-3-methyl-4-(trifluoromethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1CC(C(F)(F)F)(O)C(C)CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F UNAHCZYDWQOVLL-QNNTWYEPSA-N 0.000 claims 1
- HPTBTZUVWPLYQX-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-4-(1h-imidazol-2-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)(CC=2NC=CN=2)CC1 HPTBTZUVWPLYQX-INIZCTEOSA-N 0.000 claims 1
- ILFFFUZEFYIPCV-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-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(O)(CO)CC1 ILFFFUZEFYIPCV-AWEZNQCLSA-N 0.000 claims 1
- SSOBZMMMALQFQN-SFHVURJKSA-N n-[[(5s)-3-[3-fluoro-4-[4-hydroxy-4-(morpholin-4-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)(CN2CCOCC2)CC1 SSOBZMMMALQFQN-SFHVURJKSA-N 0.000 claims 1
- 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 1
- DOEIWVZQBGXZFC-KRWDZBQOSA-N n-[[(5s)-3-[4-(1,3-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(N2CCC3(OCOC3)CC2)C=C1 DOEIWVZQBGXZFC-KRWDZBQOSA-N 0.000 claims 1
- PDOOFKGRIFZKMV-HNNXBMFYSA-N n-[[(5s)-3-[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCC2(OCCO2)CC1 PDOOFKGRIFZKMV-HNNXBMFYSA-N 0.000 claims 1
- IAJBGMCGLRRLGH-KRWDZBQOSA-N n-[[(5s)-3-[4-(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(N2CCC3(CC2)OCCO3)C=C1 IAJBGMCGLRRLGH-KRWDZBQOSA-N 0.000 claims 1
- PPMQSIBFPRHVSB-INIZCTEOSA-N n-[[(5s)-3-[4-(2,2-dicyano-6-azaspiro[2.5]octan-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=C1N1CCC2(C(C2)(C#N)C#N)CC1 PPMQSIBFPRHVSB-INIZCTEOSA-N 0.000 claims 1
- BPKLPRAJWIUYDP-SFHVURJKSA-N n-[[(5s)-3-[4-(2,2-dicyano-6-azaspiro[2.5]octan-6-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CCC3(C(C3)(C#N)C#N)CC2)C=C1 BPKLPRAJWIUYDP-SFHVURJKSA-N 0.000 claims 1
- YXCYYDCTEOAEPD-INIZCTEOSA-N n-[[(5s)-3-[4-(2,4-dioxa-9-azaspiro[5.5]undecan-9-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=C1N1CCC2(COCOC2)CC1 YXCYYDCTEOAEPD-INIZCTEOSA-N 0.000 claims 1
- CLGINZDWYFRWNB-AWEZNQCLSA-N n-[[(5s)-3-[4-(4-amino-4-cyanopiperidin-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(N)(C#N)CC1 CLGINZDWYFRWNB-AWEZNQCLSA-N 0.000 claims 1
- JWPJRRZWECZUHS-FQEVSTJZSA-N n-[[(5s)-3-[4-(4-anilino-4-cyanopiperidin-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(C#N)(NC=2C=CC=CC=2)CC1 JWPJRRZWECZUHS-FQEVSTJZSA-N 0.000 claims 1
- GRHUNYJFVQUWQY-OOJLDXBWSA-N n-[[(5s)-3-[4-(4-cyano-4-hydroxy-3,3-dimethylpiperidin-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=C1N1CC(C)(C)C(O)(C#N)CC1 GRHUNYJFVQUWQY-OOJLDXBWSA-N 0.000 claims 1
- STDPKEISUXUMII-INIZCTEOSA-N n-[[(5s)-3-[4-(4-hydroxypiperidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CCC(O)CC2)C=C1 STDPKEISUXUMII-INIZCTEOSA-N 0.000 claims 1
- QEAGARZZZGZDSX-IBYPIGCZSA-N n-[[(5s)-3-[4-(6-methyl-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CC1CN(C=2C=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)CCC11OCCO1 QEAGARZZZGZDSX-IBYPIGCZSA-N 0.000 claims 1
- KYUWYMAHPWDVJE-KRWDZBQOSA-N n-[[(5s)-3-[4-(7,11-dithia-3-azaspiro[5.6]dodecan-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=C1N1CCC2(SCCCSC2)CC1 KYUWYMAHPWDVJE-KRWDZBQOSA-N 0.000 claims 1
- CKVGWUDDKGHEFL-KRWDZBQOSA-N n-[[(5s)-3-[4-(7,12-dioxa-3-azaspiro[5.6]dodecan-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=C1N1CCC2(OCCCCO2)CC1 CKVGWUDDKGHEFL-KRWDZBQOSA-N 0.000 claims 1
- SMWVVYYYRYKCBC-INIZCTEOSA-N n-[[(5s)-3-[4-[4-(2-acetylhydrazinyl)-4-cyanopiperidin-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(C#N)(NNC(C)=O)CC1 SMWVVYYYRYKCBC-INIZCTEOSA-N 0.000 claims 1
- GUMYXCURYAMRCA-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(2-carbamothioylhydrazinyl)-4-cyanopiperidin-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(C#N)(NNC(N)=S)CC1 GUMYXCURYAMRCA-AWEZNQCLSA-N 0.000 claims 1
- YWLXIIGFRNJOMU-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(2-carbamothioylhydrazinyl)-4-cyanopiperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCC(C#N)(NNC(N)=S)CC1 YWLXIIGFRNJOMU-AWEZNQCLSA-N 0.000 claims 1
- DAMCWZNZFOENFG-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(2-carbamoylhydrazinyl)-4-cyanopiperidin-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(C#N)(NNC(N)=O)CC1 DAMCWZNZFOENFG-AWEZNQCLSA-N 0.000 claims 1
- ABIUBMNYZPHNGW-FQEVSTJZSA-N n-[[(5s)-3-[4-[4-(3-aminoanilino)-4-cyanopiperidin-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(C#N)(NC=2C=C(N)C=CC=2)CC1 ABIUBMNYZPHNGW-FQEVSTJZSA-N 0.000 claims 1
- OCFOBKRTDLAYQB-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(aminomethyl)-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)CC1 OCFOBKRTDLAYQB-AWEZNQCLSA-N 0.000 claims 1
- FPVLEYZSBXYHOK-IBGZPJMESA-N n-[[(5s)-3-[4-[4-(benzenesulfonamido)-4-cyanopiperidin-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(C#N)(NS(=O)(=O)C=2C=CC=CC=2)CC1 FPVLEYZSBXYHOK-IBGZPJMESA-N 0.000 claims 1
- JODANYNPBOUXAT-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(chloromethyl)-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)(CCl)CC1 JODANYNPBOUXAT-AWEZNQCLSA-N 0.000 claims 1
- UJAQVZBKSPPSEI-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-(cyanomethyl)-4-hydroxypiperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2CCC(O)(CC#N)CC2)C=C1 UJAQVZBKSPPSEI-KRWDZBQOSA-N 0.000 claims 1
- JUHDJCAAYHUNDD-FOCKTWCOSA-N n-[[(5s)-3-[4-[4-(dimethylamino)-4-fluoro-2-methylpiperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CC1CC(F)(N(C)C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F JUHDJCAAYHUNDD-FOCKTWCOSA-N 0.000 claims 1
- VHPTYQPNWJKCRZ-FOCKTWCOSA-N n-[[(5s)-3-[4-[4-(dimethylamino)-4-hydroxy-2-methylpiperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CC1CC(O)(N(C)C)CCN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F VHPTYQPNWJKCRZ-FOCKTWCOSA-N 0.000 claims 1
- 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 1
- 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 1
- LHHBVMBDUWTEGB-IBGZPJMESA-N n-[[(5s)-3-[4-[4-[2-(1-benzothiophene-3-carbonyl)hydrazinyl]-4-cyanopiperidin-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(C#N)(NNC(=O)C=2C3=CC=CC=C3SC=2)CC1 LHHBVMBDUWTEGB-IBGZPJMESA-N 0.000 claims 1
- JQGHKUCWKJCVPO-ZENAZSQFSA-N n-[[(5s)-3-[4-[4-[cyano(cyclopropyl)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)(C(C#N)C2CC2)CC1 JQGHKUCWKJCVPO-ZENAZSQFSA-N 0.000 claims 1
- HPHRZEKAXCPXCJ-LBVATQBMSA-N n-[[(5s)-3-[4-[4-cyano-2-[2-(4-methoxybenzoyl)hydrazinyl]piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)NNC1N(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CCC(C#N)C1 HPHRZEKAXCPXCJ-LBVATQBMSA-N 0.000 claims 1
- BQJBTWOXVXFGST-WLBKGHODSA-N n-[[(5s)-3-[4-[4-cyano-2-[2-(4-methylphenyl)sulfonylhydrazinyl]piperidin-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=C1N1C(NNS(=O)(=O)C=2C=CC(C)=CC=2)CC(C#N)CC1 BQJBTWOXVXFGST-WLBKGHODSA-N 0.000 claims 1
- ITQWJFZEOLLVIH-WFFHQLTOSA-N n-[[(5s)-3-[4-[4-cyano-3,3-dimethyl-4-(2,3,4-trifluoroanilino)piperidin-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=C1N1CC(C)(C)C(NC=2C(=C(F)C(F)=CC=2)F)(C#N)CC1 ITQWJFZEOLLVIH-WFFHQLTOSA-N 0.000 claims 1
- HCWWQUBFRZXZEF-GVNKFJBHSA-N n-[[(5s)-3-[4-[4-cyano-3,3-dimethyl-4-(4-nitroanilino)piperidin-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=C1N1CC(C)(C)C(NC=2C=CC(=CC=2)[N+]([O-])=O)(C#N)CC1 HCWWQUBFRZXZEF-GVNKFJBHSA-N 0.000 claims 1
- FAUTVFHRIIVGHZ-JINQPTGOSA-N n-[[(5s)-3-[4-[4-cyano-3,3-dimethyl-4-(pyridin-3-ylamino)piperidin-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=C1N1CC(C)(C)C(NC=2C=NC=CC=2)(C#N)CC1 FAUTVFHRIIVGHZ-JINQPTGOSA-N 0.000 claims 1
- QGSXPLDEMWKTBI-MHVXWQKQSA-N n-[[(5s)-3-[4-[4-cyano-3-methyl-4-(4-nitroanilino)piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CC1CN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CCC1(C#N)NC1=CC=C([N+]([O-])=O)C=C1 QGSXPLDEMWKTBI-MHVXWQKQSA-N 0.000 claims 1
- HZFQJBQKFBFZKT-INIZCTEOSA-N n-[[(5s)-3-[4-[4-cyano-4-(2,3,4-trifluoroanilino)piperidin-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(C#N)(NC=2C(=C(F)C(F)=CC=2)F)CC1 HZFQJBQKFBFZKT-INIZCTEOSA-N 0.000 claims 1
- FLNGGWJZFGKZHX-SFHVURJKSA-N n-[[(5s)-3-[4-[4-cyano-4-(2,4-difluoroanilino)piperidin-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(C#N)(NC=2C(=CC(F)=CC=2)F)CC1 FLNGGWJZFGKZHX-SFHVURJKSA-N 0.000 claims 1
- JBPDEMZEXDIDJW-FQEVSTJZSA-N n-[[(5s)-3-[4-[4-cyano-4-(2-cyanoanilino)piperidin-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(C#N)(NC=2C(=CC=CC=2)C#N)CC1 JBPDEMZEXDIDJW-FQEVSTJZSA-N 0.000 claims 1
- MKVLTGYULXYDIZ-SVQMELKDSA-N n-[[(5s)-3-[4-[4-cyano-4-(2-methoxyanilino)-3,3-dimethylpiperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound COC1=CC=CC=C1NC1(C#N)C(C)(C)CN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 MKVLTGYULXYDIZ-SVQMELKDSA-N 0.000 claims 1
- FLOCJIOKTSXLPA-IBGZPJMESA-N n-[[(5s)-3-[4-[4-cyano-4-(2-methoxyanilino)piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound COC1=CC=CC=C1NC1(C#N)CCN(C=2C(=CC(=CC=2)N2C(O[C@@H](CNC(C)=O)C2)=O)F)CC1 FLOCJIOKTSXLPA-IBGZPJMESA-N 0.000 claims 1
- FCZZGWLIXWQLBW-HNNXBMFYSA-N n-[[(5s)-3-[4-[4-cyano-4-(2-methylsulfonylhydrazinyl)piperidin-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(C#N)(NNS(C)(=O)=O)CC1 FCZZGWLIXWQLBW-HNNXBMFYSA-N 0.000 claims 1
- VOBJJHOFRXMKJJ-SFHVURJKSA-N n-[[(5s)-3-[4-[4-cyano-4-(2-sulfanylanilino)piperidin-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(C#N)(NC=2C(=CC=CC=2)S)CC1 VOBJJHOFRXMKJJ-SFHVURJKSA-N 0.000 claims 1
- CRKHMIMZTXFBHY-FQEVSTJZSA-N n-[[(5s)-3-[4-[4-cyano-4-(3-nitroanilino)piperidin-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(C#N)(NC=2C=C(C=CC=2)[N+]([O-])=O)CC1 CRKHMIMZTXFBHY-FQEVSTJZSA-N 0.000 claims 1
- FZXRMKHCTVJQAY-NRFANRHFSA-N n-[[(5s)-3-[4-[4-cyano-4-(4-cyanoanilino)piperidin-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(C#N)(NC=2C=CC(=CC=2)C#N)CC1 FZXRMKHCTVJQAY-NRFANRHFSA-N 0.000 claims 1
- JRLFFPNEISPUNJ-FQEVSTJZSA-N n-[[(5s)-3-[4-[4-cyano-4-(4-nitroanilino)piperidin-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(C#N)(NC=2C=CC(=CC=2)[N+]([O-])=O)CC1 JRLFFPNEISPUNJ-FQEVSTJZSA-N 0.000 claims 1
- AQRWGQSSNBCUHL-INIZCTEOSA-N n-[[(5s)-3-[4-[4-cyano-4-(cyanomethyl)piperidin-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(CC#N)(C#N)CC1 AQRWGQSSNBCUHL-INIZCTEOSA-N 0.000 claims 1
- JERIDYFZMSBHNX-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-cyano-4-(dicyanomethyl)piperidin-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(C(C#N)C#N)(C#N)CC1 JERIDYFZMSBHNX-KRWDZBQOSA-N 0.000 claims 1
- YBUDICAIYINIGQ-IBGZPJMESA-N n-[[(5s)-3-[4-[4-cyano-4-(pyridin-3-ylamino)piperidin-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(C#N)(NC=2C=NC=CC=2)CC1 YBUDICAIYINIGQ-IBGZPJMESA-N 0.000 claims 1
- BWEPEMDRYPJJHF-IBGZPJMESA-N n-[[(5s)-3-[4-[4-cyano-4-(pyridin-3-ylamino)piperidin-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanethioamide Chemical compound O=C1O[C@@H](CNC(=S)C)CN1C(C=C1F)=CC=C1N1CCC(C#N)(NC=2C=NC=CC=2)CC1 BWEPEMDRYPJJHF-IBGZPJMESA-N 0.000 claims 1
- DTUKLSRWBAIZLW-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-cyano-4-[2-(furan-2-carbonyl)hydrazinyl]piperidin-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(C#N)(NNC(=O)C=2OC=CC=2)CC1 DTUKLSRWBAIZLW-KRWDZBQOSA-N 0.000 claims 1
- SWNZGYMOWHYOFL-IBGZPJMESA-N n-[[(5s)-3-[4-[4-cyano-4-[2-(pyridine-3-carbonyl)hydrazinyl]piperidin-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(C#N)(NNC(=O)C=2C=NC=CC=2)CC1 SWNZGYMOWHYOFL-IBGZPJMESA-N 0.000 claims 1
- FNGYLTJTZRLSIU-KRWDZBQOSA-N n-[[(5s)-3-[4-[4-cyano-4-[2-(thiophene-2-carbonyl)hydrazinyl]piperidin-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(C#N)(NNC(=O)C=2SC=CC=2)CC1 FNGYLTJTZRLSIU-KRWDZBQOSA-N 0.000 claims 1
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| 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 |
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| GB9821938D0 (en) * | 1998-10-09 | 1998-12-02 | Zeneca Ltd | Chemical compounds |
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| 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 |
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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
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