USRE40245E1 - Gyrase inhibitors and uses thereof - Google Patents
Gyrase inhibitors and uses thereof Download PDFInfo
- Publication number
- USRE40245E1 USRE40245E1 US10/833,995 US83399504A USRE40245E US RE40245 E1 USRE40245 E1 US RE40245E1 US 83399504 A US83399504 A US 83399504A US RE40245 E USRE40245 E US RE40245E
- Authority
- US
- United States
- Prior art keywords
- con
- halogen
- cor
- ring
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 0 [1*]C1=C([2*])C([3*])=C2CC(N[5*])=NC2=[W]1 Chemical compound [1*]C1=C([2*])C([3*])=C2CC(N[5*])=NC2=[W]1 0.000 description 12
- OCOTWEZCDOSZKT-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CC(C)CC(C)C4)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CC(C)CC(C)C4)N=C3)=C2)N1 OCOTWEZCDOSZKT-UHFFFAOYSA-N 0.000 description 7
- VMFOCQGPXUINDE-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(OCC1=CC=CC=C1)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(OCC1=CC=CC=C1)=CC(C1=CC=CN=C1)=C2 VMFOCQGPXUINDE-UHFFFAOYSA-N 0.000 description 4
- FYHABMRDSHIXAM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)N4CCOCC4)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)N4CCOCC4)=C3)=CC=C2N1 FYHABMRDSHIXAM-UHFFFAOYSA-N 0.000 description 4
- SRNYLRGHRFWLHD-UHFFFAOYSA-N CCCCNC(=O)C1=CN(C2=C/C=C3/NC(NC(=O)NCC)=N/C3=C\2)C=N1 Chemical compound CCCCNC(=O)C1=CN(C2=C/C=C3/NC(NC(=O)NCC)=N/C3=C\2)C=N1 SRNYLRGHRFWLHD-UHFFFAOYSA-N 0.000 description 3
- GAURHMPYZJBUNA-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CNC(=O)OC(C)(C)C)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CNC(=O)OC(C)(C)C)C=C3)=C2)N1 GAURHMPYZJBUNA-UHFFFAOYSA-N 0.000 description 3
- TUKNDDDZSAUAIM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CNC(C)=O)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CNC(C)=O)C=C3)=C2)N1 TUKNDDDZSAUAIM-UHFFFAOYSA-N 0.000 description 3
- VLBSZAGWUWFDIK-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CNS(C)(=O)=O)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CNS(C)(=O)=O)C=C3)=C2)N1 VLBSZAGWUWFDIK-UHFFFAOYSA-N 0.000 description 3
- JBERTWJRRRBQFW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCC(O)C4)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCC(O)C4)C=C3)=C2)N1 JBERTWJRRRBQFW-UHFFFAOYSA-N 0.000 description 3
- BPOFTYYMARHJNS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCCC4COC)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCCC4COC)N=C3)=C2)N1 BPOFTYYMARHJNS-UHFFFAOYSA-N 0.000 description 3
- RXPLLIHZVWJHCB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCN(C(C)=O)CC4)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCN(C(C)=O)CC4)N=C3)=C2)N1 RXPLLIHZVWJHCB-UHFFFAOYSA-N 0.000 description 3
- IZXGRHIRFITZBT-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCCC4CCCN4C)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCCC4CCCN4C)N=C3)=C2)N1 IZXGRHIRFITZBT-UHFFFAOYSA-N 0.000 description 3
- SESAERSGFTYBSW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(C)=C(OCCOC)C(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(C)=C(OCCOC)C(C1=CC=CN=C1)=C2 SESAERSGFTYBSW-UHFFFAOYSA-N 0.000 description 3
- GEUXPDLFAFVLLQ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(C)=CC(C1=CN=C(NC(C)COC)N=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(C)=CC(C1=CN=C(NC(C)COC)N=C1)=C2 GEUXPDLFAFVLLQ-UHFFFAOYSA-N 0.000 description 3
- AAMJLGQSXNCSMJ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(O)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(O)=CC(C1=CC=CN=C1)=C2 AAMJLGQSXNCSMJ-UHFFFAOYSA-N 0.000 description 3
- GRNJVQSQKRYYAX-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(Br)=CC(C1=CN=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(Br)=CC(C1=CN=CC=C1)=C2 GRNJVQSQKRYYAX-UHFFFAOYSA-N 0.000 description 3
- VDOMKTNIGVSSKI-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(N3CCNCC3)N=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(N3CCNCC3)N=C1)=C2 VDOMKTNIGVSSKI-UHFFFAOYSA-N 0.000 description 3
- RBVHMFIHCOEOKQ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(NC3CC3)N=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(NC3CC3)N=C1)=C2 RBVHMFIHCOEOKQ-UHFFFAOYSA-N 0.000 description 3
- VPDYZBADPKLJGB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC(=O)C(O)=CN3C)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC(=O)C(O)=CN3C)=CC=C2N1 VPDYZBADPKLJGB-UHFFFAOYSA-N 0.000 description 3
- KTSXUVAYRIMMMK-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(OC)=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(OC)=C2N1 KTSXUVAYRIMMMK-UHFFFAOYSA-N 0.000 description 3
- NPQDLAMGUSTRMY-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 NPQDLAMGUSTRMY-UHFFFAOYSA-N 0.000 description 3
- YHAWSIIVCHWREE-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(N4CCN(C)CC4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(N4CCN(C)CC4)N=C3)=CC=C2N1 YHAWSIIVCHWREE-UHFFFAOYSA-N 0.000 description 3
- LEAWRHKHWKNFOG-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(N4CCOCC4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(N4CCOCC4)N=C3)=CC=C2N1 LEAWRHKHWKNFOG-UHFFFAOYSA-N 0.000 description 3
- ORKUWUMSXWRCQZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCCC4=NC=CC=C4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCCC4=NC=CC=C4)N=C3)=CC=C2N1 ORKUWUMSXWRCQZ-UHFFFAOYSA-N 0.000 description 3
- ZDNVTYWJSDPCNA-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCCN4CCCC4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCCN4CCCC4)N=C3)=CC=C2N1 ZDNVTYWJSDPCNA-UHFFFAOYSA-N 0.000 description 3
- NPCPQYQRLVNXNZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(OC(C)COC)N=C3)=C(OC)C=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(OC(C)COC)N=C3)=C(OC)C=C2N1 NPCPQYQRLVNXNZ-UHFFFAOYSA-N 0.000 description 3
- JBPPYSHNMUQHEH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=CC(C(=O)OCC)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=CC(C(=O)OCC)=C3)=CC=C2N1 JBPPYSHNMUQHEH-UHFFFAOYSA-N 0.000 description 3
- BZHOCXNKZAJZJC-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=C(F)C=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=C(F)C=C2N1 BZHOCXNKZAJZJC-UHFFFAOYSA-N 0.000 description 3
- GLPQAUAZYLTDND-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)N4CCOCC4)C=N3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)N4CCOCC4)C=N3)=CC=C2N1 GLPQAUAZYLTDND-UHFFFAOYSA-N 0.000 description 3
- XFDFXZNTPMRCOT-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)O)C=N3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)O)C=N3)=CC=C2N1 XFDFXZNTPMRCOT-UHFFFAOYSA-N 0.000 description 3
- POJJZVOCMITNKY-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)O)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)O)=C3)=CC=C2N1 POJJZVOCMITNKY-UHFFFAOYSA-N 0.000 description 3
- PCIUSZUXYBBKRH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)OC)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)OC)=C3)=CC=C2N1 PCIUSZUXYBBKRH-UHFFFAOYSA-N 0.000 description 3
- ITCPCAUYGAINMX-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C\C(C3=CN=C(N4CCOCC4)C=C3)=C/C=C\2N1 Chemical compound CCNC(=O)NC1=NC2=C\C(C3=CN=C(N4CCOCC4)C=C3)=C/C=C\2N1 ITCPCAUYGAINMX-UHFFFAOYSA-N 0.000 description 3
- WDURDFHCJNEZNR-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(N)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(N)N=C3)=CC=C2N1 WDURDFHCJNEZNR-UHFFFAOYSA-N 0.000 description 3
- XWVPWCCWKAZKGX-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(N4CCN(S(C)(=O)=O)CC4)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(N4CCN(S(C)(=O)=O)CC4)N=C3)=CC=C2N1 XWVPWCCWKAZKGX-UHFFFAOYSA-N 0.000 description 3
- VOUQYUQSJLKDTP-UHFFFAOYSA-N O=C(NC1=NC2=C(O1)C(Br)=CC(C1=CN=CC=C1)=C2)NC1CCCC1 Chemical compound O=C(NC1=NC2=C(O1)C(Br)=CC(C1=CN=CC=C1)=C2)NC1CCCC1 VOUQYUQSJLKDTP-UHFFFAOYSA-N 0.000 description 3
- JDQHFJKPCXGWEB-UHFFFAOYSA-N C=CCCCOC1=CC=C(C2=CC3=C(C=C2)NC(NC(=O)NCC)=N3)C=N1 Chemical compound C=CCCCOC1=CC=C(C2=CC3=C(C=C2)NC(NC(=O)NCC)=N3)C=N1 JDQHFJKPCXGWEB-UHFFFAOYSA-N 0.000 description 2
- NHRMSVAKKCKJNM-UHFFFAOYSA-N C=CCNC(=O)C1=CN(C2=C/C=C3/NC(NC(=O)NCC)=N/C3=C\2)C=N1 Chemical compound C=CCNC(=O)C1=CN(C2=C/C=C3/NC(NC(=O)NCC)=N/C3=C\2)C=N1 NHRMSVAKKCKJNM-UHFFFAOYSA-N 0.000 description 2
- MDNVUKFBEBIZTP-SFHVURJKSA-N CC(C)(C)OC[C@H](NC1=NC=C(C2=CC=C3NC(NC#N)=NC3=C2)C=N1)C(=O)OC(C)(C)C Chemical compound CC(C)(C)OC[C@H](NC1=NC=C(C2=CC=C3NC(NC#N)=NC3=C2)C=N1)C(=O)OC(C)(C)C MDNVUKFBEBIZTP-SFHVURJKSA-N 0.000 description 2
- LMMQZMJWODGHCJ-UHFFFAOYSA-N CC(C)CNC(=O)NC1=NC2=C(C=CC(C3=CN=C(F)C=C3)=C2)N1 Chemical compound CC(C)CNC(=O)NC1=NC2=C(C=CC(C3=CN=C(F)C=C3)=C2)N1 LMMQZMJWODGHCJ-UHFFFAOYSA-N 0.000 description 2
- NHWNVDRJVPKTEC-UHFFFAOYSA-N CC(C)NC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=CN=CC=C1)=C2 Chemical compound CC(C)NC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=CN=CC=C1)=C2 NHWNVDRJVPKTEC-UHFFFAOYSA-N 0.000 description 2
- NYUXHEHFOIBTSA-UHFFFAOYSA-N CC(C)NC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 Chemical compound CC(C)NC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 NYUXHEHFOIBTSA-UHFFFAOYSA-N 0.000 description 2
- YAMRHCJFBHBUGX-UHFFFAOYSA-N CCCN(CC1CC1)C1=NC=C(C2=CC3=C(C=C2)NC(NC(=O)NCC)=N3)C=N1 Chemical compound CCCN(CC1CC1)C1=NC=C(C2=CC3=C(C=C2)NC(NC(=O)NCC)=N3)C=N1 YAMRHCJFBHBUGX-UHFFFAOYSA-N 0.000 description 2
- RIHWVVSFHKULSY-UHFFFAOYSA-N CCCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 Chemical compound CCCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 RIHWVVSFHKULSY-UHFFFAOYSA-N 0.000 description 2
- BOWITHQQEGFEPA-UHFFFAOYSA-N CCNC(=N)NC1=NC2=C(O1)C(C)=CC(C1=CN=CN=C1)=C2 Chemical compound CCNC(=N)NC1=NC2=C(O1)C(C)=CC(C1=CN=CN=C1)=C2 BOWITHQQEGFEPA-UHFFFAOYSA-N 0.000 description 2
- PCWGVOYQPPLYQR-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=C(C)C(C3=CN=CC=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=C(C)C(C3=CN=CC=C3)=C2)N1 PCWGVOYQPPLYQR-UHFFFAOYSA-N 0.000 description 2
- PVYWXBISBIBYSL-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=C(F)C(C3=CN=C(N)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=C(F)C(C3=CN=C(N)N=C3)=C2)N1 PVYWXBISBIBYSL-UHFFFAOYSA-N 0.000 description 2
- LQIWZWBJYQKLJX-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=C(N3CCCC3)C(C3=CC=CN=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=C(N3CCCC3)C(C3=CC=CN=C3)=C2)N1 LQIWZWBJYQKLJX-UHFFFAOYSA-N 0.000 description 2
- PLOXFAGTUANPSB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=C(OC)C(C3=CN=C(N)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=C(OC)C(C3=CN=C(N)N=C3)=C2)N1 PLOXFAGTUANPSB-UHFFFAOYSA-N 0.000 description 2
- YYFQOKQDHSGDQW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=C(OC)C(C3=CN=C(NC(C)COC)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=C(OC)C(C3=CN=C(NC(C)COC)N=C3)=C2)N1 YYFQOKQDHSGDQW-UHFFFAOYSA-N 0.000 description 2
- ADASGIIHCQJGMX-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=C(OC)C(C3=CN=C(OC)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=C(OC)C(C3=CN=C(OC)N=C3)=C2)N1 ADASGIIHCQJGMX-UHFFFAOYSA-N 0.000 description 2
- DQAATYRTZOSBDE-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=C3CN(C)CC4=C(/C=N\C=C/4)C3=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=C3CN(C)CC4=C(/C=N\C=C/4)C3=C2)N1 DQAATYRTZOSBDE-UHFFFAOYSA-N 0.000 description 2
- ZEUKCEZCJGADOP-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=C(F)C(F)=CC=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=C(F)C(F)=CC=C3)=C2)N1 ZEUKCEZCJGADOP-UHFFFAOYSA-N 0.000 description 2
- XBTHGTVVAJFCFN-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=C(O)C(=O)C=CO3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=C(O)C(=O)C=CO3)=C2)N1 XBTHGTVVAJFCFN-UHFFFAOYSA-N 0.000 description 2
- YATWRTAEMOCGKB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC(F)=CC=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC(F)=CC=C3)=C2)N1 YATWRTAEMOCGKB-UHFFFAOYSA-N 0.000 description 2
- RRHWOEDVSVMOIT-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CN)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CN)C=C3)=C2)N1 RRHWOEDVSVMOIT-UHFFFAOYSA-N 0.000 description 2
- ORXCRDTZNSWKPS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CNC(C)=O)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CNC(C)=O)C=C3)=C2)N1 ORXCRDTZNSWKPS-UHFFFAOYSA-N 0.000 description 2
- KSTZBWPMLFVMTM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CNS(C)(=O)=O)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C(CNS(C)(=O)=O)C=C3)=C2)N1 KSTZBWPMLFVMTM-UHFFFAOYSA-N 0.000 description 2
- QBWCMHPKMXYRDD-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C4C=CNC4=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=C4C=CNC4=C3)=C2)N1 QBWCMHPKMXYRDD-UHFFFAOYSA-N 0.000 description 2
- STRSDIDXEZXBJE-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC(=O)N3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC(=O)N3)=C2)N1 STRSDIDXEZXBJE-UHFFFAOYSA-N 0.000 description 2
- LLFSDONXOVNKSH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC(C(=O)O)=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC(C(=O)O)=C3)=C2)N1 LLFSDONXOVNKSH-UHFFFAOYSA-N 0.000 description 2
- VUNKBVUHVGQCDO-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC4=C3N=CC=C4)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC4=C3N=CC=C4)=C2)N1 VUNKBVUHVGQCDO-UHFFFAOYSA-N 0.000 description 2
- QQUCSVLLUFNELZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 QQUCSVLLUFNELZ-UHFFFAOYSA-N 0.000 description 2
- RTOVSEAZGKSHEH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC=C3O)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CC=CC=C3O)=C2)N1 RTOVSEAZGKSHEH-UHFFFAOYSA-N 0.000 description 2
- JUPDYVXKZASNGH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CN)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CN)C=C3)=C2)N1 JUPDYVXKZASNGH-UHFFFAOYSA-N 0.000 description 2
- LBZSGTRCZNDFSS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CNC(=O)OC(C)(C)C)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CNC(=O)OC(C)(C)C)C=C3)=C2)N1 LBZSGTRCZNDFSS-UHFFFAOYSA-N 0.000 description 2
- LKDJQQUZKANZFJ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(F)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(F)C=C3)=C2)N1 LKDJQQUZKANZFJ-UHFFFAOYSA-N 0.000 description 2
- ZQQRLTGLJWKABL-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(F)C=C3)=C2)O1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(F)C=C3)=C2)O1 ZQQRLTGLJWKABL-UHFFFAOYSA-N 0.000 description 2
- OKAYSHFNKWTLJW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCC(O)C4)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCC(O)C4)N=C3)=C2)N1 OKAYSHFNKWTLJW-UHFFFAOYSA-N 0.000 description 2
- XOCXQUCZYVTLII-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCC(O)CC4)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCC(O)CC4)N=C3)=C2)N1 XOCXQUCZYVTLII-UHFFFAOYSA-N 0.000 description 2
- SJFOWZRBECPBCZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCCC4)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCCC4)C=C3)=C2)N1 SJFOWZRBECPBCZ-UHFFFAOYSA-N 0.000 description 2
- MWDBFEISKJGRBG-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCCCC4)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCCCC4)C=C3)=C2)N1 MWDBFEISKJGRBG-UHFFFAOYSA-N 0.000 description 2
- VDYVWQDPCBGAMS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCN(S(C)(=O)=O)CC4)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCN(S(C)(=O)=O)CC4)N=C3)=C2)N1 VDYVWQDPCBGAMS-UHFFFAOYSA-N 0.000 description 2
- RTHZKXKKPJGPKP-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCOCC4)C=C3)=C2)O1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(N4CCOCC4)C=C3)=C2)O1 RTHZKXKKPJGPKP-UHFFFAOYSA-N 0.000 description 2
- LWWGXULARDKLKG-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCC4=CC5=C(C=C4)OCO5)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCC4=CC5=C(C=C4)OCO5)N=C3)=C2)N1 LWWGXULARDKLKG-UHFFFAOYSA-N 0.000 description 2
- VWEWTGXMDDACFV-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCC4=CC=CC=C4)N=C3)=C2)O1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCC4=CC=CC=C4)N=C3)=C2)O1 VWEWTGXMDDACFV-UHFFFAOYSA-N 0.000 description 2
- OQLGPVZKDZIQRN-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCCCOC)N=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(NCCCOC)N=C3)=C2)N1 OQLGPVZKDZIQRN-UHFFFAOYSA-N 0.000 description 2
- QGOUHZCYDQKCIZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(OC)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(OC)C=C3)=C2)N1 QGOUHZCYDQKCIZ-UHFFFAOYSA-N 0.000 description 2
- XKPTWGLARXJVLZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(OCC)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(OCC)C=C3)=C2)N1 XKPTWGLARXJVLZ-UHFFFAOYSA-N 0.000 description 2
- FEDSVTRWFVFCKQ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=CC=C3)=C2)O1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=CC=C3)=C2)O1 FEDSVTRWFVFCKQ-UHFFFAOYSA-N 0.000 description 2
- VGWBDAHJKKIURQ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(N3C=NC(C(=O)NC(C)=O)=C3)=N2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(N3C=NC(C(=O)NC(C)=O)=C3)=N2)N1 VGWBDAHJKKIURQ-UHFFFAOYSA-N 0.000 description 2
- WPWTYYXYCGEALB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(F)C(C3=CC=CN=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=C(F)C(C3=CC=CN=C3)=CC=C2N1 WPWTYYXYCGEALB-UHFFFAOYSA-N 0.000 description 2
- MUWWAOOMSUFGMT-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(C#N)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(C#N)=CC(C1=CC=CN=C1)=C2 MUWWAOOMSUFGMT-UHFFFAOYSA-N 0.000 description 2
- FFELBJRPOVTGQF-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(C(=O)O)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(C(=O)O)=CC(C1=CC=CN=C1)=C2 FFELBJRPOVTGQF-UHFFFAOYSA-N 0.000 description 2
- VSFZCGIZXKQHJW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(C)=C(C)C(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(C)=C(C)C(C1=CC=CN=C1)=C2 VSFZCGIZXKQHJW-UHFFFAOYSA-N 0.000 description 2
- NVFLIFFUBIMVCH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(C)=C(OC)C(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(C)=C(OC)C(C1=CC=CN=C1)=C2 NVFLIFFUBIMVCH-UHFFFAOYSA-N 0.000 description 2
- CMFXYOVHRRAQJJ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(Cl)=CC(C1=CN=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(Cl)=CC(C1=CN=CC=C1)=C2 CMFXYOVHRRAQJJ-UHFFFAOYSA-N 0.000 description 2
- WDROVRRGGHZDMK-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(F)=C(OC)C(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(F)=C(OC)C(C1=CC=CN=C1)=C2 WDROVRRGGHZDMK-UHFFFAOYSA-N 0.000 description 2
- HHTSJHMSAZYDHT-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(F)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(F)=CC(C1=CC=CN=C1)=C2 HHTSJHMSAZYDHT-UHFFFAOYSA-N 0.000 description 2
- WXCHDWNCCJLOEF-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(N)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(N)=CC(C1=CC=CN=C1)=C2 WXCHDWNCCJLOEF-UHFFFAOYSA-N 0.000 description 2
- METDTFOTTXQFHX-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(OC)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(OC)=CC(C1=CC=CN=C1)=C2 METDTFOTTXQFHX-UHFFFAOYSA-N 0.000 description 2
- KSFYRBUEKLCZNR-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C1=C(CN(C)CC1)C(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C1=C(CN(C)CC1)C(C1=CC=CN=C1)=C2 KSFYRBUEKLCZNR-UHFFFAOYSA-N 0.000 description 2
- QBYVUXJLSNZGLS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C1=C(OC(F)(F)O1)C(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C1=C(OC(F)(F)O1)C(C1=CC=CN=C1)=C2 QBYVUXJLSNZGLS-UHFFFAOYSA-N 0.000 description 2
- ZVHPCALOGKOEEN-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O)C(C3=CC=CN=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=C(O)C(C3=CC=CN=C3)=CC=C2N1 ZVHPCALOGKOEEN-UHFFFAOYSA-N 0.000 description 2
- HFFYHOYWFPCFBM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(Br)=CC(C1=CN=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(Br)=CC(C1=CN=CN=C1)=C2 HFFYHOYWFPCFBM-UHFFFAOYSA-N 0.000 description 2
- GJIPAKMNLFTBST-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C#N)=C(C)C(C1=CN=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C#N)=C(C)C(C1=CN=CC=C1)=C2 GJIPAKMNLFTBST-UHFFFAOYSA-N 0.000 description 2
- GJRGREWPWKTJLJ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=C(NC(C)=O)C=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=C(NC(C)=O)C=CC=C1)=C2 GJRGREWPWKTJLJ-UHFFFAOYSA-N 0.000 description 2
- QEBAHXGAUODIKN-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=C(O)C=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=C(O)C=CC=C1)=C2 QEBAHXGAUODIKN-UHFFFAOYSA-N 0.000 description 2
- KSRHWHQEFZFUSJ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=CN=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C#N)=CC(C1=CN=CC=C1)=C2 KSRHWHQEFZFUSJ-UHFFFAOYSA-N 0.000 description 2
- ZAHBQNHPFGLLSO-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C(=O)O)=CC(C1=CC=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C(=O)O)=CC(C1=CC=CC=C1)=C2 ZAHBQNHPFGLLSO-UHFFFAOYSA-N 0.000 description 2
- SOWDJEMDUSLJPB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(N)N=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(N)N=C1)=C2 SOWDJEMDUSLJPB-UHFFFAOYSA-N 0.000 description 2
- UBYYPAIVQMAUPY-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(NCC)N=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(NCC)N=C1)=C2 UBYYPAIVQMAUPY-UHFFFAOYSA-N 0.000 description 2
- FVQXFHQZLBGBCB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(SC)N=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CN=C(SC)N=C1)=C2 FVQXFHQZLBGBCB-UHFFFAOYSA-N 0.000 description 2
- RAMIFTRVOMLOAI-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CNC(=O)C=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(C1=CNC(=O)C=C1)=C2 RAMIFTRVOMLOAI-UHFFFAOYSA-N 0.000 description 2
- KJOZBKXOIYPMLO-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(N1C=CC=N1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(N1C=CC=N1)=C2 KJOZBKXOIYPMLO-UHFFFAOYSA-N 0.000 description 2
- AYBVXJGMQXOCKL-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(N1C=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(N1C=CN=C1)=C2 AYBVXJGMQXOCKL-UHFFFAOYSA-N 0.000 description 2
- MLGCCBUIPKANNC-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(C)=CC(N1C=NC(C(=O)O)=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(C)=CC(N1C=NC(C(=O)O)=C1)=C2 MLGCCBUIPKANNC-UHFFFAOYSA-N 0.000 description 2
- ZDUNMSZRUNXEDB-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(O1)C(O)=CC(C1=CC=CC=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(O1)C(O)=CC(C1=CC=CC=C1)=C2 ZDUNMSZRUNXEDB-UHFFFAOYSA-N 0.000 description 2
- NJMAKUDXZFTBGF-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C(=O)NOC(C)(C)C)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C(=O)NOC(C)(C)C)=CC=C2N1 NJMAKUDXZFTBGF-UHFFFAOYSA-N 0.000 description 2
- PPDCUOUHOYFJER-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C(=O)O)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C(=O)O)=CC=C2N1 PPDCUOUHOYFJER-UHFFFAOYSA-N 0.000 description 2
- JYAOMKXVBCMPFW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=C(OC)N=C(OC)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=C(OC)N=C(OC)N=C3)=CC=C2N1 JYAOMKXVBCMPFW-UHFFFAOYSA-N 0.000 description 2
- YXZOMBKYXMIJBU-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC(=O)N(O)C(C)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC(=O)N(O)C(C)=C3)=CC=C2N1 YXZOMBKYXMIJBU-UHFFFAOYSA-N 0.000 description 2
- XZJWHOJXQMEWSK-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=C(O)C(=O)N3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=C(O)C(=O)N3)=CC=C2N1 XZJWHOJXQMEWSK-UHFFFAOYSA-N 0.000 description 2
- ZNKNBDPQIFLPNN-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=C(OCCOCC)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=C(OCCOCC)N=C3)=CC=C2N1 ZNKNBDPQIFLPNN-UHFFFAOYSA-N 0.000 description 2
- BPPXYIZDIBYQGD-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(Br)=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(Br)=C2N1 BPPXYIZDIBYQGD-UHFFFAOYSA-N 0.000 description 2
- QFOSJZYLOWGNQM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(C)=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(C)=C2N1 QFOSJZYLOWGNQM-UHFFFAOYSA-N 0.000 description 2
- IBJAJADLKDYQDR-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(F)=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(F)=C2N1 IBJAJADLKDYQDR-UHFFFAOYSA-N 0.000 description 2
- OTZGDJFOSDFRBQ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CN=C3)=C(N3CCCCC3)C=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CN=C3)=C(N3CCCCC3)C=C2N1 OTZGDJFOSDFRBQ-UHFFFAOYSA-N 0.000 description 2
- GSOUHRPQHRUKPH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(N)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(N)N=C3)=CC=C2N1 GSOUHRPQHRUKPH-UHFFFAOYSA-N 0.000 description 2
- DUTHOWJNOPGBKO-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(N4CCCC4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(N4CCCC4)N=C3)=CC=C2N1 DUTHOWJNOPGBKO-UHFFFAOYSA-N 0.000 description 2
- BDJNKMIRSYLHPI-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NC(C)COC)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NC(C)COC)N=C3)=CC=C2N1 BDJNKMIRSYLHPI-UHFFFAOYSA-N 0.000 description 2
- KKBYWPXXWFZXEI-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NC4CC4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NC4CC4)N=C3)=CC=C2N1 KKBYWPXXWFZXEI-UHFFFAOYSA-N 0.000 description 2
- VFBDTGLMAIXTRK-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NC4CCCC4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NC4CCCC4)N=C3)=CC=C2N1 VFBDTGLMAIXTRK-UHFFFAOYSA-N 0.000 description 2
- ZVBHYKIVPOHGLW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC(=O)O)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC(=O)O)N=C3)=CC=C2N1 ZVBHYKIVPOHGLW-UHFFFAOYSA-N 0.000 description 2
- LBMLOKYDIXXRAK-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC)N=C3)=CC=C2N1 LBMLOKYDIXXRAK-UHFFFAOYSA-N 0.000 description 2
- SEWNSQRNYCPLGS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=C(F)C(Cl)=C4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=C(F)C(Cl)=C4)N=C3)=CC=C2N1 SEWNSQRNYCPLGS-UHFFFAOYSA-N 0.000 description 2
- PUSYGDSSIJEZQD-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=C(OC)C=C4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=C(OC)C=C4)N=C3)=CC=C2N1 PUSYGDSSIJEZQD-UHFFFAOYSA-N 0.000 description 2
- HGYBPTUZMRDRBM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=CC(F)=C4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=CC(F)=C4)N=C3)=CC=C2N1 HGYBPTUZMRDRBM-UHFFFAOYSA-N 0.000 description 2
- SRZFYCSVCYSFRV-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=CC=N4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CC=CC=N4)N=C3)=CC=C2N1 SRZFYCSVCYSFRV-UHFFFAOYSA-N 0.000 description 2
- DKDOFURLSBAHOC-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CN=CC=C4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4=CN=CC=C4)N=C3)=CC=C2N1 DKDOFURLSBAHOC-UHFFFAOYSA-N 0.000 description 2
- HKENDDZUYDFQOQ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4CCCO4)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(NCC4CCCO4)N=C3)=CC=C2N1 HKENDDZUYDFQOQ-UHFFFAOYSA-N 0.000 description 2
- FRCDCFJCGUOZQH-ZDUSSCGKSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](CO)C(=O)O)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](CO)C(=O)O)N=C3)=CC=C2N1 FRCDCFJCGUOZQH-ZDUSSCGKSA-N 0.000 description 2
- QNEAHQBACWDQTD-IBGZPJMESA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](COC(C)(C)C)C(=O)OC(C)(C)C)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](COC(C)(C)C)C(=O)OC(C)(C)C)N=C3)=CC=C2N1 QNEAHQBACWDQTD-IBGZPJMESA-N 0.000 description 2
- CCRATUQRSGLHBY-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=C(SC)N=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=C(SC)N=C3)=CC=C2N1 CCRATUQRSGLHBY-UHFFFAOYSA-N 0.000 description 2
- GGEGMYKXLIDQBU-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=CC(C(=O)O)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=CC(C(=O)O)=C3)=CC=C2N1 GGEGMYKXLIDQBU-UHFFFAOYSA-N 0.000 description 2
- SIJUCHAWQHDVQI-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=C(OC)C=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=C(OC)C=C2N1 SIJUCHAWQHDVQI-UHFFFAOYSA-N 0.000 description 2
- PQKDDDBZWXJHFA-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC(C)=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC(C)=C2N1 PQKDDDBZWXJHFA-UHFFFAOYSA-N 0.000 description 2
- KWSSMBHDMXPYIA-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 KWSSMBHDMXPYIA-UHFFFAOYSA-N 0.000 description 2
- JEFPRNWTSVQGMU-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=NN=C(C)O3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=NN=C(C)O3)=CC=C2N1 JEFPRNWTSVQGMU-UHFFFAOYSA-N 0.000 description 2
- KYIZEBSIOGJCCT-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=NN=CO3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=NN=CO3)=CC=C2N1 KYIZEBSIOGJCCT-UHFFFAOYSA-N 0.000 description 2
- ZJDHWWFCGBLIPZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)NCC(C)C)C=N3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)NCC(C)C)C=N3)=CC=C2N1 ZJDHWWFCGBLIPZ-UHFFFAOYSA-N 0.000 description 2
- KWZOWZCZSSUYJO-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)NCC4=CC=CN=C4)C=N3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)NCC4=CC=CN=C4)C=N3)=CC=C2N1 KWZOWZCZSSUYJO-UHFFFAOYSA-N 0.000 description 2
- YFVSSGUNHBKTCM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)O)C4=C3C=CC=N4)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=C(C(=O)O)C4=C3C=CC=N4)=CC=C2N1 YFVSSGUNHBKTCM-UHFFFAOYSA-N 0.000 description 2
- OARQOMHIMSVMJS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=CC(=O)C(O)=C3C)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=CC(=O)C(O)=C3C)=CC=C2N1 OARQOMHIMSVMJS-UHFFFAOYSA-N 0.000 description 2
- XUYRTHUGJYYKNL-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=CC(=O)C(OCC4=CC=CC=C4)=C3C)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=CC(=O)C(OCC4=CC=CC=C4)=C3C)=CC=C2N1 XUYRTHUGJYYKNL-UHFFFAOYSA-N 0.000 description 2
- ULFIHHOZULSWER-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)NC4CC4)=C3)=C(F)C=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)NC4CC4)=C3)=C(F)C=C2N1 ULFIHHOZULSWER-UHFFFAOYSA-N 0.000 description 2
- WWNNEKKFXXIGLP-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)NC4CC4)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)NC4CC4)=C3)=CC=C2N1 WWNNEKKFXXIGLP-UHFFFAOYSA-N 0.000 description 2
- JZPKCNLDHCTKSL-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)NCC4=CC=CN=C4)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)NCC4=CC=CN=C4)=C3)=CC=C2N1 JZPKCNLDHCTKSL-UHFFFAOYSA-N 0.000 description 2
- QDTTXOINFBSLSZ-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)O)=C3)=C(OCCN(C)C)C=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(C(=O)O)=C3)=C(OCCN(C)C)C=C2N1 QDTTXOINFBSLSZ-UHFFFAOYSA-N 0.000 description 2
- KYTXJUAUURBPFV-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3C=NC(CP(=O)(OC)OC)=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3C=NC(CP(=O)(OC)OC)=C3)=CC=C2N1 KYTXJUAUURBPFV-UHFFFAOYSA-N 0.000 description 2
- MTHXOSFFMYCRDM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(N3CCOCC3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(N3CCOCC3)=CC=C2N1 MTHXOSFFMYCRDM-UHFFFAOYSA-N 0.000 description 2
- AMLIMNZDWHRNDG-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C\C(C3=C(C)C=C(C(=O)O)N3)=C/C=C\2N1 Chemical compound CCNC(=O)NC1=NC2=C\C(C3=C(C)C=C(C(=O)O)N3)=C/C=C\2N1 AMLIMNZDWHRNDG-UHFFFAOYSA-N 0.000 description 2
- PZRIKZXUXJHPSM-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C\C(C3=CC=CN=C3)=C(N3CCOCC3)/C=C\2N1 Chemical compound CCNC(=O)NC1=NC2=C\C(C3=CC=CN=C3)=C(N3CCOCC3)/C=C\2N1 PZRIKZXUXJHPSM-UHFFFAOYSA-N 0.000 description 2
- ZMWJLZRIKHSAMO-UHFFFAOYSA-N CCNC(=O)NC1=NC2=NC(N3C=C(C(=O)NC(C)=O)C=N3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=NC(N3C=C(C(=O)NC(C)=O)C=N3)=CC=C2N1 ZMWJLZRIKHSAMO-UHFFFAOYSA-N 0.000 description 2
- NKTPGZXOOSEDRH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=N\C(N3C=NC(C(=O)O)=C3)=C/C=C\2N1 Chemical compound CCNC(=O)NC1=NC2=N\C(N3C=NC(C(=O)O)=C3)=C/C=C\2N1 NKTPGZXOOSEDRH-UHFFFAOYSA-N 0.000 description 2
- GPJRKTREAVPGTL-UHFFFAOYSA-N CCNC(=O)NC1=NC2=N\C(N3C=NC(C(=O)OC)=C3)=C/C=C\2N1 Chemical compound CCNC(=O)NC1=NC2=N\C(N3C=NC(C(=O)OC)=C3)=C/C=C\2N1 GPJRKTREAVPGTL-UHFFFAOYSA-N 0.000 description 2
- BJRSYLMDSLUEQX-UHFFFAOYSA-N CCNC(=S)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound CCNC(=S)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 BJRSYLMDSLUEQX-UHFFFAOYSA-N 0.000 description 2
- ZQJZPFSLSLMADO-UHFFFAOYSA-N CCNC(=S)NC1=NC2=CC(C3=CN=C(NCC(=O)O)N=C3)=CC=C2N1 Chemical compound CCNC(=S)NC1=NC2=CC(C3=CN=C(NCC(=O)O)N=C3)=CC=C2N1 ZQJZPFSLSLMADO-UHFFFAOYSA-N 0.000 description 2
- SEGZVIXUBMSEQU-UHFFFAOYSA-N CCNC(=S)NC1=NC2=CC(C3=CN=C(NCC(=O)OC(C)(C)C)N=C3)=CC=C2N1 Chemical compound CCNC(=S)NC1=NC2=CC(C3=CN=C(NCC(=O)OC(C)(C)C)N=C3)=CC=C2N1 SEGZVIXUBMSEQU-UHFFFAOYSA-N 0.000 description 2
- UWQCJDUZNKTNLK-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC(C(=O)OC)=CC=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC(C(=O)OC)=CC=C3)=CC=C2N1 UWQCJDUZNKTNLK-UHFFFAOYSA-N 0.000 description 2
- BIJVHHZDUWYMHR-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=CN=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=CN=C3)=CC=C2N1 BIJVHHZDUWYMHR-UHFFFAOYSA-N 0.000 description 2
- VMIHZDPCBJQGHG-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=NC=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=NC=C3)=CC=C2N1 VMIHZDPCBJQGHG-UHFFFAOYSA-N 0.000 description 2
- YWJUZWSSWBEVEY-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(N4CCN(C(=O)OC(C)(C)C)CC4)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(N4CCN(C(=O)OC(C)(C)C)CC4)N=C3)=CC=C2N1 YWJUZWSSWBEVEY-UHFFFAOYSA-N 0.000 description 2
- RERMNTJRMIEVAO-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(N4CCNCC4)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(N4CCNCC4)N=C3)=CC=C2N1 RERMNTJRMIEVAO-UHFFFAOYSA-N 0.000 description 2
- QIXDMTHSINWOSM-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(NC(CO)C(=O)O)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(NC(CO)C(=O)O)N=C3)=CC=C2N1 QIXDMTHSINWOSM-UHFFFAOYSA-N 0.000 description 2
- KJBCXLRZBISANK-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(NCC(=O)O)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(NCC(=O)O)N=C3)=CC=C2N1 KJBCXLRZBISANK-UHFFFAOYSA-N 0.000 description 2
- QAHMEKYQACDLRR-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(NCCN)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(NCCN)N=C3)=CC=C2N1 QAHMEKYQACDLRR-UHFFFAOYSA-N 0.000 description 2
- WEODJIPVTMWDIR-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(NCCNC(=O)OC(C)(C)C)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(NCCNC(=O)OC(C)(C)C)N=C3)=CC=C2N1 WEODJIPVTMWDIR-UHFFFAOYSA-N 0.000 description 2
- ZKLBOBRDPYWWKV-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(OC)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(OC)N=C3)=CC=C2N1 ZKLBOBRDPYWWKV-UHFFFAOYSA-N 0.000 description 2
- QYEIMVCOUDLKND-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=CN=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=CN=C3)=CC=C2N1 QYEIMVCOUDLKND-UHFFFAOYSA-N 0.000 description 2
- BTPXITGSPPLOLU-UHFFFAOYSA-N CCOC(=O)NC1=NC=C(C2=CC=C3NC(NC(=O)OCC)=NC3=C2)C=N1 Chemical compound CCOC(=O)NC1=NC=C(C2=CC=C3NC(NC(=O)OCC)=NC3=C2)C=N1 BTPXITGSPPLOLU-UHFFFAOYSA-N 0.000 description 2
- OBHFFZAAAAGATH-UHFFFAOYSA-N COC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound COC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 OBHFFZAAAAGATH-UHFFFAOYSA-N 0.000 description 2
- QALHGZCAHRXVDV-UHFFFAOYSA-N COC(=O)NC1=NC2=CC(C3=CN=C(NCC(=O)OC(C)(C)C)N=C3)=CC=C2N1 Chemical compound COC(=O)NC1=NC2=CC(C3=CN=C(NCC(=O)OC(C)(C)C)N=C3)=CC=C2N1 QALHGZCAHRXVDV-UHFFFAOYSA-N 0.000 description 2
- WHGSTJDJNJJUIX-UHFFFAOYSA-N CSC1=NC=C(C2=CC=C3NC(NC(=O)NC(C)C)=NC3=C2)C=N1 Chemical compound CSC1=NC=C(C2=CC=C3NC(NC(=O)NC(C)C)=NC3=C2)C=N1 WHGSTJDJNJJUIX-UHFFFAOYSA-N 0.000 description 2
- UGCICQFRMNMBNM-UHFFFAOYSA-N CSC1=NC=C(C2=CC=C3NC(NC(=O)NC4CCCC4)=NC3=C2)C=N1 Chemical compound CSC1=NC=C(C2=CC=C3NC(NC(=O)NC4CCCC4)=NC3=C2)C=N1 UGCICQFRMNMBNM-UHFFFAOYSA-N 0.000 description 2
- DLBCZNBWXJPPER-UHFFFAOYSA-N NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 DLBCZNBWXJPPER-UHFFFAOYSA-N 0.000 description 2
- XLXIMPCKYYCMEQ-UHFFFAOYSA-N O=C(NC1=NC2=CC(C3=CC=CC=C3)=CC(Br)=C2N1)N1CCCCC1 Chemical compound O=C(NC1=NC2=CC(C3=CC=CC=C3)=CC(Br)=C2N1)N1CCCCC1 XLXIMPCKYYCMEQ-UHFFFAOYSA-N 0.000 description 2
- PHHZXIXRYFFCOM-UHFFFAOYSA-N O=C(NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1)NC1CC1 Chemical compound O=C(NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1)NC1CC1 PHHZXIXRYFFCOM-UHFFFAOYSA-N 0.000 description 2
- HOVNAVKZZKLPRN-UHFFFAOYSA-N O=C(NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1)NC1CCCC1 Chemical compound O=C(NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1)NC1CCCC1 HOVNAVKZZKLPRN-UHFFFAOYSA-N 0.000 description 2
- DPOQPYOEJDZFJY-UHFFFAOYSA-N C#CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound C#CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 DPOQPYOEJDZFJY-UHFFFAOYSA-N 0.000 description 1
- SAHMNFNLSZNQSP-UHFFFAOYSA-N C1=CN=CC(C2=CC=C3NC(NC4=NC=CN4)=NC3=C2)=C1 Chemical compound C1=CN=CC(C2=CC=C3NC(NC4=NC=CN4)=NC3=C2)=C1 SAHMNFNLSZNQSP-UHFFFAOYSA-N 0.000 description 1
- GYVHUWUQUDWKKN-UHFFFAOYSA-N CC(C)(C)OC(=O)NCCN.CC(C)(C)OC(=O)NCCNC1=NC=C(Br)C=N1.CC(C)(C)OC(=O)NCCNC1=NC=C(C2=CC=C(N)C(N)=C2)C=N1.CC(C)(C)OC(=O)NCCNC1=NC=C(C2=CC=C(N)C([N+](=O)[O-])=C2)C=N1.CC1(C)OB(C2=CC=C(N)C([N+](=O)[O-])=C2)OC1(C)C.CCOC(=O)NC1=NC2=CC(C3=CN=C(NCCNC(=O)OC(C)(C)C)N=C3)=CC=C2N1.CSC(=N)N.ClC1=NC=C(Br)C=N1.O=S(OO)OS(=O)OOO Chemical compound CC(C)(C)OC(=O)NCCN.CC(C)(C)OC(=O)NCCNC1=NC=C(Br)C=N1.CC(C)(C)OC(=O)NCCNC1=NC=C(C2=CC=C(N)C(N)=C2)C=N1.CC(C)(C)OC(=O)NCCNC1=NC=C(C2=CC=C(N)C([N+](=O)[O-])=C2)C=N1.CC1(C)OB(C2=CC=C(N)C([N+](=O)[O-])=C2)OC1(C)C.CCOC(=O)NC1=NC2=CC(C3=CN=C(NCCNC(=O)OC(C)(C)C)N=C3)=CC=C2N1.CSC(=N)N.ClC1=NC=C(Br)C=N1.O=S(OO)OS(=O)OOO GYVHUWUQUDWKKN-UHFFFAOYSA-N 0.000 description 1
- SOBBHYDDNWGZCN-UHFFFAOYSA-N CC(C)(C)OC(=O)NCCNC1=NC=C(Br)C=N1 Chemical compound CC(C)(C)OC(=O)NCCNC1=NC=C(Br)C=N1 SOBBHYDDNWGZCN-UHFFFAOYSA-N 0.000 description 1
- BDZIDQXFZNUCGC-UHFFFAOYSA-N CC1(C)OB(C2=CC=C(N)C([N+](=O)[O-])=C2)OC1(C)C.NC1=CC=C(Br)C=C1[N+](=O)[O-].NC1=CC=C([Ar])C=C1[N+](=O)[O-] Chemical compound CC1(C)OB(C2=CC=C(N)C([N+](=O)[O-])=C2)OC1(C)C.NC1=CC=C(Br)C=C1[N+](=O)[O-].NC1=CC=C([Ar])C=C1[N+](=O)[O-] BDZIDQXFZNUCGC-UHFFFAOYSA-N 0.000 description 1
- YOGBCRDTQUXBHM-UHFFFAOYSA-N CC1=CN=C(NC2=NC3=CC(C4=CC=CN=C4)=CC=C3N2)N1 Chemical compound CC1=CN=C(NC2=NC3=CC(C4=CC=CN=C4)=CC=C3N2)N1 YOGBCRDTQUXBHM-UHFFFAOYSA-N 0.000 description 1
- NORZTUIVOVPBMS-UHFFFAOYSA-N CCCC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound CCCC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 NORZTUIVOVPBMS-UHFFFAOYSA-N 0.000 description 1
- FWBHAZMVMVZMOW-UHFFFAOYSA-N CCCC1=C2NC(NC(=O)OCC)=NC2=CC(C2=CC=CC=C2)=C1 Chemical compound CCCC1=C2NC(NC(=O)OCC)=NC2=CC(C2=CC=CC=C2)=C1 FWBHAZMVMVZMOW-UHFFFAOYSA-N 0.000 description 1
- BXFVYQGUBCMOGE-UHFFFAOYSA-N CCCCNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 Chemical compound CCCCNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 BXFVYQGUBCMOGE-UHFFFAOYSA-N 0.000 description 1
- AKGNWBGUBZWSRE-UHFFFAOYSA-N CCCNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 Chemical compound CCCNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 AKGNWBGUBZWSRE-UHFFFAOYSA-N 0.000 description 1
- JATRMHHENNFOJX-UHFFFAOYSA-N CCN/C(=N\C)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound CCN/C(=N\C)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 JATRMHHENNFOJX-UHFFFAOYSA-N 0.000 description 1
- PGXJUEHOAKFCAN-UHFFFAOYSA-N CCNC(=N)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)N1 Chemical compound CCNC(=N)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)N1 PGXJUEHOAKFCAN-UHFFFAOYSA-N 0.000 description 1
- KKYDQXUDEWCAFG-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CN(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CN(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C=C3)=C2)N1 KKYDQXUDEWCAFG-UHFFFAOYSA-N 0.000 description 1
- ZFFRMUXLLQGRLW-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CN(C(=O)OC(C)(C)C)C(C)(C)C)C=C3)=C2)N1 Chemical compound CCNC(=O)NC1=NC2=C(C=CC(C3=CN=C(CN(C(=O)OC(C)(C)C)C(C)(C)C)C=C3)=C2)N1 ZFFRMUXLLQGRLW-UHFFFAOYSA-N 0.000 description 1
- YJADYDWJKUFPDP-UHFFFAOYSA-N CCNC(=O)NC1=NC2=C(N1)C(C(F)(F)F)=CC(C1=CC=CN=C1)=C2 Chemical compound CCNC(=O)NC1=NC2=C(N1)C(C(F)(F)F)=CC(C1=CC=CN=C1)=C2 YJADYDWJKUFPDP-UHFFFAOYSA-N 0.000 description 1
- OMDXFHNPJDQRHG-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=C(N4CCC(N)C4)N=C3)=CC=C2N1.CCNC(=O)NC1=NC2=CC(N3CCC(N)C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=C(N4CCC(N)C4)N=C3)=CC=C2N1.CCNC(=O)NC1=NC2=CC(N3CCC(N)C3)=CC=C2N1 OMDXFHNPJDQRHG-UHFFFAOYSA-N 0.000 description 1
- SBULRINCRBSEOC-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1.NC1=CC=C(C2=CC=CC=C2)C=C1N.NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1.NC1=CC=C(C2=CC=CC=C2)C=C1N.NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 SBULRINCRBSEOC-UHFFFAOYSA-N 0.000 description 1
- VXYWUENQBVLBQF-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1.NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1 Chemical compound CCNC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1.NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1 VXYWUENQBVLBQF-UHFFFAOYSA-N 0.000 description 1
- QVYNZPBVCBIFQH-UHFFFAOYSA-N CCNC(=O)NC1=NC2=CC=C(N3C=NC(C(=O)O)=C3)C=C2N1.CCNC(=O)NC1=NC2=CC=C(N3C=NC(C(=O)OC)=C3)C=C2N1.COC(=O)C1=CN(C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C2)C=N1.COC(=O)C1=CNC=N1.O=[N+]([O-])C1=CC=C(F)C=C1[N+](=O)[O-] Chemical compound CCNC(=O)NC1=NC2=CC=C(N3C=NC(C(=O)O)=C3)C=C2N1.CCNC(=O)NC1=NC2=CC=C(N3C=NC(C(=O)OC)=C3)C=C2N1.COC(=O)C1=CN(C2=CC([N+](=O)[O-])=C([N+](=O)[O-])C=C2)C=N1.COC(=O)C1=CNC=N1.O=[N+]([O-])C1=CC=C(F)C=C1[N+](=O)[O-] QVYNZPBVCBIFQH-UHFFFAOYSA-N 0.000 description 1
- YSXWFWLDHVWUHS-UHFFFAOYSA-N CCNC(=O)NC1=NC2=N\C(N3C=NC(C(=O)NC4CC4)=C3)=C/C=C\2N1 Chemical compound CCNC(=O)NC1=NC2=N\C(N3C=NC(C(=O)NC4CC4)=C3)=C/C=C\2N1 YSXWFWLDHVWUHS-UHFFFAOYSA-N 0.000 description 1
- VSLIYZBHTMRNEM-UHFFFAOYSA-N CCNC(=S)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 Chemical compound CCNC(=S)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 VSLIYZBHTMRNEM-UHFFFAOYSA-N 0.000 description 1
- ZUFAADPNLHYMLP-UHFFFAOYSA-N CCNC(=S)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 Chemical compound CCNC(=S)NC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 ZUFAADPNLHYMLP-UHFFFAOYSA-N 0.000 description 1
- ARJIMGGYUKSKOP-UHFFFAOYSA-N CCNC(Nc1nc2cc(N(CC3)CC3N)ccc2[nH]1)=O Chemical compound CCNC(Nc1nc2cc(N(CC3)CC3N)ccc2[nH]1)=O ARJIMGGYUKSKOP-UHFFFAOYSA-N 0.000 description 1
- SGDPKTJTMBAFKX-UHFFFAOYSA-N CCOC(=O)NC1=CN=CC(C2=CC3=C(C=C2)NC(NC(=O)OCC)=N3)=C1 Chemical compound CCOC(=O)NC1=CN=CC(C2=CC3=C(C=C2)NC(NC(=O)OCC)=N3)=C1 SGDPKTJTMBAFKX-UHFFFAOYSA-N 0.000 description 1
- WVNQCJMMRZANJL-UHFFFAOYSA-N CCOC(=O)NC1=NC2=C(C=CC(C3=CC=C(OC)C(OC)=C3)=C2)N1 Chemical compound CCOC(=O)NC1=NC2=C(C=CC(C3=CC=C(OC)C(OC)=C3)=C2)N1 WVNQCJMMRZANJL-UHFFFAOYSA-N 0.000 description 1
- NFNCTLZMJKAEFO-UHFFFAOYSA-N CCOC(=O)NC1=NC2=C(C=CC(C3=CC=C(OC)C=C3OC)=C2)N1 Chemical compound CCOC(=O)NC1=NC2=C(C=CC(C3=CC=C(OC)C=C3OC)=C2)N1 NFNCTLZMJKAEFO-UHFFFAOYSA-N 0.000 description 1
- DAJZAHQJPXPBNZ-UHFFFAOYSA-N CCOC(=O)NC1=NC2=C(C=CC(C3=CC=CC(C(=O)O)=C3)=C2)N1 Chemical compound CCOC(=O)NC1=NC2=C(C=CC(C3=CC=CC(C(=O)O)=C3)=C2)N1 DAJZAHQJPXPBNZ-UHFFFAOYSA-N 0.000 description 1
- TXASPSXHDQVNMN-UHFFFAOYSA-N CCOC(=O)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 Chemical compound CCOC(=O)NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 TXASPSXHDQVNMN-UHFFFAOYSA-N 0.000 description 1
- LHCZFUNACMJCSA-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=C(C(F)(F)F)C=CC=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=C(C(F)(F)F)C=CC=C3)=CC=C2N1 LHCZFUNACMJCSA-UHFFFAOYSA-N 0.000 description 1
- CPHYUPGUDVJUSY-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=C(F)C=C(F)C(F)=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=C(F)C=C(F)C(F)=C3)=CC=C2N1 CPHYUPGUDVJUSY-UHFFFAOYSA-N 0.000 description 1
- HHBIFVLHEDDOCT-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=C(OC)N=C(OC)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=C(OC)N=C(OC)N=C3)=CC=C2N1 HHBIFVLHEDDOCT-UHFFFAOYSA-N 0.000 description 1
- FZPPDWWHMHYUES-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC4=C(C=C3)NC(NC(=O)OCC)=N4)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC4=C(C=C3)NC(NC(=O)OCC)=N4)=CC=C2N1 FZPPDWWHMHYUES-UHFFFAOYSA-N 0.000 description 1
- GWRHOOURVPVGQK-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=C(N(C)C)C=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=C(N(C)C)C=C3)=CC=C2N1 GWRHOOURVPVGQK-UHFFFAOYSA-N 0.000 description 1
- QAXAVOXQGPETRF-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=C(OC)C=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=C(OC)C=C3)=CC=C2N1 QAXAVOXQGPETRF-UHFFFAOYSA-N 0.000 description 1
- VRJVEIJPIDYQOX-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=C(OC)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=C(OC)N=C3)=CC=C2N1 VRJVEIJPIDYQOX-UHFFFAOYSA-N 0.000 description 1
- PJBOYFFCYAVJPJ-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=CC(OCC)=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=CC(OCC)=C3)=CC=C2N1 PJBOYFFCYAVJPJ-UHFFFAOYSA-N 0.000 description 1
- SFALBXTVFMPLEK-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(Br)=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC(Br)=C2N1 SFALBXTVFMPLEK-UHFFFAOYSA-N 0.000 description 1
- UPWFWVPKWFCFJU-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 UPWFWVPKWFCFJU-UHFFFAOYSA-N 0.000 description 1
- WINROLQDPRYIEI-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1C Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1C WINROLQDPRYIEI-UHFFFAOYSA-N 0.000 description 1
- HOCSQYWBUOOECP-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1.NC1=CC(C2=CC=CC=C2)=CC=C1O.NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1.NC1=CC(C2=CC=CC=C2)=CC=C1O.NC1=NC2=CC(C3=CC=CC=C3)=CC=C2O1 HOCSQYWBUOOECP-UHFFFAOYSA-N 0.000 description 1
- HTCGLMVLWKJZPB-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CC=CN=C3)=CC(Br)=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CC=CN=C3)=CC(Br)=C2N1 HTCGLMVLWKJZPB-UHFFFAOYSA-N 0.000 description 1
- WJMPQIYCBCEEAS-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(NC(COC(C)(C)C)C(=O)OC(C)(C)C)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(NC(COC(C)(C)C)C(=O)OC(C)(C)C)N=C3)=CC=C2N1 WJMPQIYCBCEEAS-UHFFFAOYSA-N 0.000 description 1
- QIXDMTHSINWOSM-ZDUSSCGKSA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](CO)C(=O)O)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](CO)C(=O)O)N=C3)=CC=C2N1 QIXDMTHSINWOSM-ZDUSSCGKSA-N 0.000 description 1
- WJMPQIYCBCEEAS-IBGZPJMESA-N CCOC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](COC(C)(C)C)C(=O)OC(C)(C)C)N=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=C(N[C@@H](COC(C)(C)C)C(=O)OC(C)(C)C)N=C3)=CC=C2N1 WJMPQIYCBCEEAS-IBGZPJMESA-N 0.000 description 1
- LHUMQUSOKHYMSN-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=CC(N)=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=CC(N)=C3)=CC=C2N1 LHUMQUSOKHYMSN-UHFFFAOYSA-N 0.000 description 1
- MQSCWPIQCBPQOX-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=CN=CC(NC(C)=O)=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=CN=CC(NC(C)=O)=C3)=CC=C2N1 MQSCWPIQCBPQOX-UHFFFAOYSA-N 0.000 description 1
- IOGAPHHZOIHSKC-UHFFFAOYSA-N CCOC(=O)NC1=NC2=CC(C3=NC=CC=C3)=CC=C2N1 Chemical compound CCOC(=O)NC1=NC2=CC(C3=NC=CC=C3)=CC=C2N1 IOGAPHHZOIHSKC-UHFFFAOYSA-N 0.000 description 1
- CCVLQDFFYBODCC-UHFFFAOYSA-N CCOC(Nc1nc2cc(C(C=C3)=CNC3=O)ccc2[nH]1)=O Chemical compound CCOC(Nc1nc2cc(C(C=C3)=CNC3=O)ccc2[nH]1)=O CCVLQDFFYBODCC-UHFFFAOYSA-N 0.000 description 1
- IUKWIMJNJQZCPY-UHFFFAOYSA-N CN(C)CCN1C2=CC=C(C3=CN=CC=C3)C=C2N=C1N Chemical compound CN(C)CCN1C2=CC=C(C3=CN=CC=C3)C=C2N=C1N IUKWIMJNJQZCPY-UHFFFAOYSA-N 0.000 description 1
- CAEYLOMGSQZTMK-UHFFFAOYSA-N CN1CCCC1C(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound CN1CCCC1C(=O)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 CAEYLOMGSQZTMK-UHFFFAOYSA-N 0.000 description 1
- ZMEPEIZBNDRWBT-UHFFFAOYSA-N CNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1CCN(C)C Chemical compound CNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1CCN(C)C ZMEPEIZBNDRWBT-UHFFFAOYSA-N 0.000 description 1
- VCOPKUIGBSHJCF-UHFFFAOYSA-N COC(=O)C1=CN(C2=CC=C([N+](=O)[O-])C([N+](=O)[O-])=C2)C=N1 Chemical compound COC(=O)C1=CN(C2=CC=C([N+](=O)[O-])C([N+](=O)[O-])=C2)C=N1 VCOPKUIGBSHJCF-UHFFFAOYSA-N 0.000 description 1
- HYNAYALXRHBYMB-UHFFFAOYSA-N COC(=O)CCNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 Chemical compound COC(=O)CCNC1=NC2=CC(C3=CN=CC=C3)=CC=C2N1 HYNAYALXRHBYMB-UHFFFAOYSA-N 0.000 description 1
- CFSJTORSJCNFRA-UHFFFAOYSA-N N=C(N)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 Chemical compound N=C(N)NC1=NC2=CC(C3=CC=CC=C3)=CC=C2N1 CFSJTORSJCNFRA-UHFFFAOYSA-N 0.000 description 1
- DXVYFNFQIYZBIU-UHFFFAOYSA-N NC1=CC=C(C2=CC=CN=C2)C=C1N Chemical compound NC1=CC=C(C2=CC=CN=C2)C=C1N DXVYFNFQIYZBIU-UHFFFAOYSA-N 0.000 description 1
- HUWQSHAKHTVWEM-UHFFFAOYSA-N NC1=CC=C(C2=CC=CN=C2)C=C1[N+](=O)[O-] Chemical compound NC1=CC=C(C2=CC=CN=C2)C=C1[N+](=O)[O-] HUWQSHAKHTVWEM-UHFFFAOYSA-N 0.000 description 1
- OEPIONHEDWZNDO-UHFFFAOYSA-N NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 Chemical compound NC1=NC2=C(C=CC(C3=CC=CC=C3)=C2)O1 OEPIONHEDWZNDO-UHFFFAOYSA-N 0.000 description 1
- MMVIYDASTGTOEB-UHFFFAOYSA-N O=C1CCC(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)=N1 Chemical compound O=C1CCC(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)=N1 MMVIYDASTGTOEB-UHFFFAOYSA-N 0.000 description 1
- UKRCKFLLNIXHSZ-UHFFFAOYSA-N O=C1CNC(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)=N1 Chemical compound O=C1CNC(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)=N1 UKRCKFLLNIXHSZ-UHFFFAOYSA-N 0.000 description 1
- WJDIGJGTZQSUNQ-UHFFFAOYSA-N O=C1N=C(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)C2CC12 Chemical compound O=C1N=C(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)C2CC12 WJDIGJGTZQSUNQ-UHFFFAOYSA-N 0.000 description 1
- FTXMCLAFDJSBQH-UHFFFAOYSA-N O=C1N=NC(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)=N1 Chemical compound O=C1N=NC(NC2=NC3=C(C=CC(C4=CC=CN=C4)=C3)N2)=N1 FTXMCLAFDJSBQH-UHFFFAOYSA-N 0.000 description 1
- KJCRRJRYXVYHJR-UHFFFAOYSA-N [H]N(C(=O)OCC)C1=NC2=CC(C3=CC=CS3)=CC=C2N1[H] Chemical compound [H]N(C(=O)OCC)C1=NC2=CC(C3=CC=CS3)=CC=C2N1[H] KJCRRJRYXVYHJR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
or a pharmaceutically acceptable derivative or prodrug thereof. The compounds are useful as inhibitors of bacterial gyrase activity. The present invention also relates to methods for treating bacterial infections in mammala. The present invention also relates to methods for decreasing bacterial quantity in a biological sample.
Description
or a pharmaceutically acceptable derivative or prodrug thereof, wherein:
-
- Z is O or N—R4;
- W is nitrogen or CRa;
- Ra is selected from hydrogen, halogen, —CF3, R7, —OR7, or —N(R7)2;
- R1 is an aryl or heteroaryl ring, wherein said ring is optionally substituted by up to four R9; wherein an R9 substituent in the ortho-position of R1 taken together with R2 may form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring having 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R2 and R3 are each independently selected from R6, halogen, CN, SR6, OR6, N(R6)2, NRCO2R6, NRCON (R6)2, CON(R6)2, NRCOR6, NRN(R6)2, COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or NRSO2R6; or R2 and R3 are taken together to form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R4 is selected from R6, CON(R6), COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or (CH2)yR2;
- y is 1-6;
- R5 is selected from R7, Ar, COAr, CON(R7)Ar, (CH2)yCO2R, (CH2)yN(R7)2, C(═NR10)—N(R7)2, C(═NR10)—NRCOR, C(═S)—N(R7)2, CON(R7)2, COR, SO2R, or SO2N(R7)2;
- Ar is a five membered heteroaryl, heterocyclyl, or carbocyclyl ring, wherein said ring is optionally substituted by up to three substituents selected from oxo, halogen, CN, NO2, R8, OR8, NHR8, NHCOR8, NHCONHR8, COR8, CONHR8, SO2R8, NHSO2NHR8 or SO2NHR8;
- each R6 is independently selected from R7 or an optionally substituted group selected from alkoxy, hydroxylalkyl, heterocyclyl, heterocyclcylalkyl, aryl, aralkyl, aralkoxy, aryloxyalkyl, heteroaryl, heteroaralkyl, heteroaralkoxy, or heteroarayloxyalkyl;
- each R7 is independently selected from hydrogen or an optionally substituted aliphatic group having one to six carbons, or two R7 on the same nitrogen taken together with the nitrogen optionally form a four to six member, saturated or unsaturated heterocyclic ring having one to three heteroatoms;
- R8 is a C1-C4 aliphatic group, wherein two R8 on adjacent positions of Ar, or an aryl or heteroaryl ring, may be taken together with their intervening atoms to form a three to six membered fused ring;
- each R9 is independently selected from oxo, halogen, CN, NO2, Tn(haloalkyl), R6, SR6, OR6, OR8, N(R6)2, CON (R6)2, CON(R)COR6, COR6, CO2R6, CO2N(R6)2, COCOR6, SO2R6, SO2N(R6)2, N(R)TnCO2R6, N(R) TnCON(R6)2, N(R)TnN(R6)2, N(R)TnNRCO2R6, N(R) TnNRCON(R6)2, N(R)TnCOR6, N(R)TnNRCOR6, N(R)TnSO2N(R6)2, N(R)TnSO2R6, TnPO(OR7)2, TnOPO(OR7)2, TnSP(OR7)2, TnPO(OR7)2, or TnNPO (OR7)2;
- each Q is an independently selected C1-C3 branched or straight alkyl;
- T is selected from —Q— or —Qm—CH(Qm—R2)—;
- each m and n are independently selected from zero or one;
- and R10 is selected from R7 or Ar.
or a pharmaceutically acceptable derivative or prodrug thereof, wherein R1, R2, R3, R4, and R5 are as described above.
-
- (a) R1 is an optionally substituted aryl or heteroaryl ring;
- (b) R2 and R3 are each independently selected from halogen, CN, CO2R6, OR6, or R6;
- (c) R5 is CO2R, COAr, COR, CON(R7)2, Ar, (CH2)yCO2R, or (CH2)yN(R7)2; and
- (d) R9 is halogen, CN, oxo, R6, SR6, OR6, N(R6)2, CON(R6)2, CO2R6, CON(R)COR6, N(R)TnCO2R6, N(R)TnNRCO2R6, N(R)TnN(R6)2, NO2, Tn(haloalkyl), CO2N(R6)2, COR6, SO2R6, or SO2N(R6)2.
-
- (a) R1 is an optionally substituted ring selected from phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, thienyl, pyrimidyl, imidazol-1-yl, imidazol-2-yl, pyrazol-1-yl, amino-pyrimidinyl, quinolinyl, aminobenzimidazole, or indolyl;
- (b) R2 is hydrogen, alkoxy, aminoalkyl, or halogen;
- (c) R3 is hydrogen, alkoxy, aralkoxy, or halogen;
- (d) R4 is hydrogen or (CH2)yR2;
- (e) R5 is CON(R7)2, Ar, (CH2)yCO2R, or (CH2)yN(R7)2; and
- (f) R9 is halogen, CN, oxo, R6, SR6, OR6, N(R6)2, CON(R6)2, CO2R6, CON(R)COR6, or N(R)TnCO2R6.
TABLE 1 | |
No. Ia- | Structure |
1 |
|
2 |
|
3 |
|
4 |
|
5 |
|
6 |
|
7 |
|
8 |
|
9 |
|
10 |
|
11 |
|
12 |
|
13 |
|
14 |
|
15 |
|
16 |
|
17 |
|
18 |
|
19 |
|
20 |
|
21 |
|
22 |
|
23 |
|
24 |
|
25 |
|
26 |
|
27 |
|
28 |
|
29 |
|
30 |
|
31 |
|
32 |
|
33 |
|
34 |
|
35 |
|
36 |
|
37 |
|
38 |
|
39 |
|
40 |
|
41 |
|
42 |
|
43 |
|
44 |
|
45 |
|
46 |
|
47 |
|
48 |
|
49 |
|
50 |
|
51 |
|
52 |
|
53 |
|
54 |
|
55 |
|
56 |
|
57 |
|
58 |
|
59 |
|
60 |
|
61 |
|
62 |
|
63 |
|
64 |
|
65 |
|
66 |
|
67 |
|
68 |
|
69 |
|
70 |
|
71 |
|
72 |
|
73 |
|
74 |
|
75 |
|
76 |
|
77 |
|
78 |
|
79 |
|
80 |
|
81 |
|
82 |
|
83 |
|
84 |
|
85 |
|
86 |
|
87 |
|
88 |
|
89 |
|
90 |
|
91 |
|
92 |
|
93 |
|
94 |
|
95 |
|
96 |
|
97 |
|
98 |
|
99 |
|
100 |
|
101 |
|
102 |
|
103 |
|
104 |
|
105 |
|
106 |
|
107 |
|
108 |
|
109 |
|
110 |
|
111 |
|
112 |
|
113 |
|
114 |
|
115 |
|
116 |
|
117 |
|
118 |
|
119 |
|
120 |
|
121 |
|
122 |
|
123 |
|
124 |
|
125 |
|
126 |
|
127 |
|
128 |
|
129 |
|
130 |
|
131 |
|
132 |
|
133 |
|
134 |
|
135 |
|
136 |
|
137 |
|
138 |
|
139 |
|
140 |
|
141 |
|
142 |
|
143 |
|
144 |
|
145 |
|
146 |
|
147 |
|
148 |
|
149 |
|
150 |
|
151 |
|
152 |
|
153 |
|
154 |
|
155 |
|
156 |
|
157 |
|
158 |
|
159 |
|
160 |
|
161 |
|
162 |
|
163 |
|
164 |
|
165 |
|
166 |
|
167 |
|
168 |
|
169 |
|
170 |
|
171 |
|
172 |
|
173 |
|
174 |
|
175 |
|
176 |
|
177 |
|
178 |
|
179 |
|
180 |
|
181 |
|
182 |
|
183 |
|
184 |
|
185 |
|
186 |
|
187 |
|
188 |
|
189 |
|
190 |
|
191 |
|
192 |
|
193 |
|
194 |
|
195 |
|
196 |
|
197 |
|
198 |
|
199 |
|
200 |
|
TABLE 2 | |
No. Ib- | Structure |
1 |
|
2 |
|
3 |
|
4 |
|
5 |
|
6 |
|
7 |
|
8 |
|
9 |
|
10 |
|
11 |
|
12 |
|
13 |
|
14 |
|
15 |
|
16 |
|
17 |
|
18 |
|
19 |
|
20 |
|
21 |
|
22 |
|
23 |
|
24 |
|
25 |
|
26 |
|
27 |
|
28 |
|
or a pharmaceutically acceptable derivative or prodrug thereof, wherein:
-
- W is nitrogen or CRa;
- Ra is selected from hydrogen, halogen, —CF3, R7, —OR7, or —N(R7)2;
- R1 is an aryl or heteroaryl ring, wherein said ring is optionally substituted by up to four R9; wherein an R9 substituent in the ortho-position of R1 taken together with R2 may form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring having 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R2 and R3 are each independently selected from R6, halogen, CN, SR6, OR6, N(R6)2, NRCO2R6, NRCON (R6)2, CON(R6)2, NRCOR6, NRN(R6)2, COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or NRSO2R6; or R2 and R3 are taken together to form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R4 is selected from R6, CON(R6), COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or (CH2)yR2;
- y is 1-6;
- Ar is a five membered heteroaryl, heterocyclyl, or carbocyclyl ring, wherein said ring is optionally substituted by up to three substituents selected from oxo, halogen, CN, NO2, R8, OR8, NHR8, NHCOR8, NHCONHR8, COR8, CONHR8, SO2R8, NHSO2NHR8 or SO2NHR8;
- each R6 is independently selected from R7 or an optionally substituted group selected from alkoxy, hydroxyalkyl, heterocyclyl, heterocyclcylalkyl, aryl, aralkyl, aralkoxy, aryloxyalkyl, heteroaryl, heteroaralkyl, heteroaralkoxy, or heteroarayloxyalkyl;
- each R7 is independently selected from hydrogen or an optionally substituted aliphatic group having one to six carbons, or two R7 on the same nitrogen taken together with the nitrogen optionally form a four to six member, saturated or unsaturated heterocyclic ring having one to three heteroatoms;
- R8 is a C1-C4 aliphatic group, wherein two R8 on adjacent positions of Ar, or an aryl or heteroaryl ring, may be taken together with their intervening atoms to form a three to six membered fused ring;
- each R9 is independently selected from oxo, halogen, CN, NO2, Tn(haloalkyl), R6, SR6, OR6, OR8, N(R6)2, CON (R6)2, CON(R)COR6, COR6, CO2R6, CO2N(R6)2, COCOR6, SO2R6, SO2N(R6)2, N(R)TnCO2R6, N(R) TnCON(R6)2, N(R)TnN(R6)2, N(R)TnNRCO2R6, N(R) TnNRCON(R6)2, N(R)TnCOR6, N(R)TnNRCOR6, N(R)TnSO2N(R6)2, N(R)TnSO2R6, TnPO(OR7)2, TnOPO(OR7)2, TnSP(OR7)2, TnPO(OR7)2, or TnNPO (OR7)2;
- each Q is an independently selected C1-C3 branched or straight alkyl;
- T is selected from —Q— or —Qm—CH(Qm—R2)—; and
- each m and n are independently selected from zero or one.
-
- (a) R1 is an optionally substituted aryl or heteroaryl ring;
- (b) R2 and R3 are each independently selected from halogen, CN, CO2R6, OR6, or R6;
- (c) R9 is halogen, CN, oxo, R6, SR6, OR6, N(R6)2, CON(R6)2, CO2R6, CON(R)COR6, N(R)TnCO2R6, N(R)TnNRCO2R6, N(R)TnN(R6)2, NO2, Tn(haloalkyl), CO2N(R6)2, COR6, SO2R6, or SO2N(R6)2.
-
- (a) R1 is an optionally substituted ring selected from phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, thienyl, pyrimidyl, imidazol-1-yl, imidazol-2-yl, pyrazol-1-yl, amino-pyrimidinyl, quinolinyl, aminobenzimidazole, or indolyl;
- (b) R2 is hydrogen, alkoxy, aminoalkyl, or halogen;
- (c) R3 is hydrogen, alkoxy, aralkoxy, or halogen;
- (d) R4 is hydrogen or (CH2)yR2; and
- (e) R9 is halogen, CN, oxo, R6, SR6, OR6, N(R6)2, CON(R6)2, CO2R6, CON(R)COR6, or N(R)TnCO2R6.
or a pharmaceutically acceptable derivative or prodrug thereof, wherein:
-
- W is nitrogen or CRa;
- Ra is selected from hydrogen, halogen, —CF3, R7, —OR7, or —N(R7)2;
- Ring A is optionally substituted with up to three R9; wherein when an R9 substituent is in the ortho-position of Ring A, said R9 substituent may be taken together with R2 to form an optionally substituted 5-7 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R2 and R3 are each independently selected from R6, halogen, CN, SR6, OR6, N(R6)2, NRCO2R6, NRCON (R6)2, CON(R6)2, NRCOR6, NRN(R6)2, COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or NRSO2R6; or R2 and R3 are taken together to form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R4 is selected from R6, CON(R6), COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or (CH2)yR2;
- y is 1-6;
- R5 is selected from R7, Ar, COAr, CON(R7)Ar, (CH2)yCO2R, (CH2)yN(R7)2, C(═NR10)—N(R7)2, C(═NR10)—NRCOR, C(═S)—N(R7)2, CON(R7)2, COR, SO2R, or SO2N(R7)2;
- Ar is a five membered heteroaryl, heterocyclyl, or carbocyclyl ring, wherein said ring is optionally substituted by up to three substituents selected from oxo, halogen, CN, NO2, R8, OR8, NHR8, NHCOR8, NHCONHR8, COR8, CONHR8, SO2R8, NHSO2NHR8 or SO2NHR8;
- each R6 is independently selected from R7 or an optionally substituted group selected from alkoxy, hydroxylalkyl, heterocyclyl, heterocyclcylalkyl, aryl, aralkyl, aralkoxy, aryloxyalkyl, heteroaryl, heteroaralkyl, heteroaralkoxy, or heteroarayloxyalkyl;
- each R7 is independently selected from hydrogen or an optionally substituted aliphatic group having one to six carbons, or two R7 on the same nitrogen taken together with the nitrogen optionally form a four to six member, saturated or unsaturated heterocyclic ring having one to three heteroatoms;
- R8 is a C1-C4 aliphatic group, wherein two R8 on adjacent positions of Ar, or an aryl or heteroaryl ring, may be taken together with their intervening atoms to form a three to six membered fused ring;
- each R9 is independently selected from oxo, halogen, CN, NO2, Tn(haloalkyl), R6, SR6, OR6, OR8, N(R6)2, CON (R6)2, CON(R)COR6, COR6, CO2R6, CO2N(R6)2, COCOR6, SO2R6, SO2N(R6)2, N(R)TnCO2R6, N(R) TnCON(R6)2, N(R)TnN(R6)2, N(R)TnNRCO2R6, N(R) TnNRCON(R6)2, N(R)TnCOR6, N(R)TnNRCOR6, N(R)TnSO2N(R6)2, N(R)TnSO2R6, TnPO(OR7)2, TnOPO(OR7)2, TnSP(OR7)2, TnPO(OR7)2, or TnNPO (OR7)2;
- each Q is an independently selected C1-C3 branched or straight alkyl;
- T is selected from —Q— or —Qm—CH(Qm—R2)—;
- each m and n are independently selected from zero or one;
- and R10 is selected from R7 or Ar.
-
- (a) R2 and R3 are each independently selected from halogen, CN, CO2R6, OR6, or R6;
- (b) R5 is CO2R, COAr, COR, CON(R7)2, Ar, (CH2)yCO2R, or (CH2)yN(R7)2; and
- (c) R9 is halogen, CN, oxo, R6, SR6, OR6, N(R6)2, CON(R6)2, CO2R6, CON(R)COR6, N(R)TnCO2R6, N(R)TnNRCO2R6, N(R)TnN(R6)2, NO2, Tn(haloalkyl), CO2N(R6)2, COR6, SO2R6, or SO2N(R6)2.
-
- (a) R2 is hydrogen, alkoxy, aminoalkyl, or halogen;
- (b) R3 is hydrogen, alkoxy, aralkoxy, or halogen;
- (c) R4 is hydrogen or (CH2)yR2;
- (d) R5 is CON(R7)2, Ar, (CH2)yCO2R, or (CH2)yN(R7)2; and
- (e) R9 is halogen, CN, oxo, R6, SR6, OR6, N(R6)2, CON(R6)2, CO2R6, CON(R)COR6, or N(R)TnCO2R6.
Reagents and conditions: (a) Ar-boronic acid, PdCl2(dppf), K3PO4, DMF, 95° C., 18 hours; (b) 40 psi H2, 10% Pd/C, EtOAc; (c) ROCOCl, NaOH, H2O, 0° C.; (d) p-TsOH, ROH, reflux, 1 hour.
Reagents and conditions: (a) bis(pinacolato)diboron, KOAc, PdCl2(dppf), DMSO, 80° C.; (b) ArBr, K3PO4, PdCl2(dppf), DMSO, 95° C;
Reagents and conditions: (a) BrCN, THF, MeOH, water, room temperature; (b) EtNCO, THF, reflux.
Reagents and conditions: (a) EtOH, 80° C., 4 hours; (b) PdCl2(dppf), K3PO4, 95° C., 48 hours; (c) Pd/C, H2, 50 psi, 6 hours; (d) 2-methyl-2-thiopseudourea (14), EtOCOCl, 80° C., 18 hours.
Reagents and conditions: (a) BrCN, THF, MeOH, water, room temperature; (b) EtOCOCl, pyridine.
Reagents and conditions: (a) (b) EtNCO, THF, reflux.
Reagents and conditions: (a) NaH, THF, 0° C.; (b) H2 (45 psi), Pd-C, MeOH; (c) BrCN, MeCN, MeOH, room temperature; (d) i EtNCO, DMSO, 80° C., ii NH3, MeOH, 80° C.
or a pharmaceutically acceptable derivative or prodrug thereof, wherein:
-
- W is nitrogen or CRa;
- Ra is selected from hydrogen, halogen, —CF3, R7, —OR7, or —N(R7)2;
- R1 is an aryl or heteroaryl ring, wherein said ring is optionally substituted by up to four R9; wherein an R9 substituent in the ortho-position of R1 taken together with R2 may form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring having 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R2 and R3 are each independently selected from R6, halogen, CN, SR6, OR6, N(R6)2, NRCO2R6, NRCON (R6)2, CON(R6)2, NRCOR6, NRN(R6)2, COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2 or NRSO2R6; or R2 and R3 are taken together to form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R4 is selected from R6, CON(R6), COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or (CH2)yR2;
- y is 1-6;
- Ar is a five membered heteroaryl, heterocyclyl, or carbocyclyl ring, wherein said ring is optionally substituted by up to three substituents selected from oxo, halogen, CN, NO2, R8, OR8, NHR8, NHCOR8, NHCONHR8, COR8, CONHR8, SO2R8, NHSO2NHR8 or SO2NHR8;
- each R6 is independently selected from R7 or an optionally substituted group selected from alkoxy, hydroxyalkyl, heterocyclyl, heterocyclcylalkyl, aryl, aralkyl, aralkoxy, aryloxyalkyl, heteroaryl, heteroaralkyl, heteroaralkoxy, or heteroarayloxyalkyl;
- each R7 is independently selected from hydrogen or an optionally substituted aliphatic group having one to six carbons, or two R7 on the same nitrogen taken together with the nitrogen optionally form a four to six member, saturated or unsaturated heterocyclic ring having one to three heteroatoms;
- R8 is a C1-C4 aliphatic group, wherein two R8 on adjacent positions of Ar, or an aryl or heteroaryl ring, may be taken together with their intervening atoms to form a three to six membered fused ring;
- each R9 is independently selected from oxo, halogen, CN, NO2, Tn(haloalkyl), R6, SR6, OR6, OR8, N(R6)2, CON (R6)2, CON(R)COR6, COR6, CO2R6, CO2N(R6)2, COCOR6, SO2R6, SO2N(R6)2, N(R)TnCO2R6, N(R) TnCON(R6)2, N(R)TnN(R6)2, N(R)TnNRCO2R6, N(R) TnNRCON(R6)2, N(R)TnCOR6, N(R)TnNRCOR6, N(R)TnSO2N(R6)2, N(R)TnSO2R6, TnPO(OR7)2, TnOPO(OR7)2, TnSP(OR7)2, TnPO(OR7)2, or TnNPO (OR7)2;
- each Q is an independently selected C1-C3 branched or straight alkyl;
- T is selected from —Q— or —Qm—CH(Qm—R2)—; and
- each m and n are independently selected from zero or one.
or a pharmaceutically acceptable derivative or prodrug thereof, wherein:
-
- W is nitrogen or CRa;
- Ra is selected from hydrogen, halogen, —CF3, R7, —OR7, or —N(R7)2;
- Ring A is optionally substituted with up to three R9; wherein when an R9 substituent is in the ortho-position of Ring A, said R9 substituent may be taken together with R2 to form an optionally substituted 5-7 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R2 and R3 are each independently selected from R6, halogen, CN, SR6, OR6, N(R6)2, NRCO2R6, NRCON (R6)2, CON(R6)2, NRCOR6, NRN(R6)2, COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or NRSO2R6; or R2 and R3 are taken together to form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R4 is selected from R6, CON(R6), COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or (CH2)yR2;
- y is 1-6;
- R5 is selected from R7, Ar, COAr, CON(R7)Ar, (CH2)yCO2R, (CH2)yN(R7)2, C(═NR10)—N(R7)2, C(═NR10)—NRCOR, C(═S)—N(R7)2, CON(R7)2, COR, SO2R, or SO2N(R7)2;
- Ar is a five membered heteroaryl, heterocyclyl, or carbocyclyl ring, wherein said ring is optionally substituted by up to three substituents selected from oxo, halogen, CN, NO2, R8, OR8, NHR8, NHCOR8, NHCONHR8, COR8, CONHR8, SO2R8, NHSO2NHR8 or SO2NHR8;
- each R6 is independently selected from R7 or an optionally substituted group selected from alkoxy, hydroxyalkyl, heterocyclyl, heterocyclcylalkyl, aryl, aralkyl, aralkoxy, aryloxyalkyl, heteroaryl, heteroaralkyl, heteroaralkoxy, or heteroarayloxyalkyl;
- each R7 is independently selected from hydrogen or an optionally substituted aliphatic group having one to six carbons, or two R7 on the same nitrogen taken together with the nitrogen optionally form a four to six member, saturated or unsaturated heterocyclic ring having one to three heteroatoms;
- R8 is a C1-C4 aliphatic group, wherein two R8 on adjacent positions of Ar, or an aryl or heteroaryl ring, may be taken together with their intervening atoms to form a three to six membered fused ring;
- each R9 is independently selected from oxo, halogen, CN, NO2, Tn(haloalkyl), R6, SR6, OR6, OR8, N(R6)2, CON (R6)2, CON(R)COR6, COR6, CO2R6, CO2N(R6)2, COCOR6, SO2R6, SO2N(R6)2, N(R)TnCO2R6, N(R) TnCON(R6)2, N(R)TnN(R6)2, N(R)TnNRCO2R6, N(R) TnNRCON(R6)2, N(R)TnCOR6, N(R)TnNRCOR6, N(R)TnSO2N(R6)2, N(R)TnSO2R6, TnPO(OR7)2, TnOPO(OR7)2, TnSP(OR7)2, TnPO(OR7)2, or TnNPO (OR7)2;
- each Q is an independently selected C1-C3 branched or straight alkyl;
- T is selected from —Q— or —Qm—CH(Qm—R2)—;
- each m and n are independently selected from zero or one;
- and R10 is selected from R7 or Ar.
or a pharmaceutically acceptable derivative or prodrug thereof, wherein:
-
- Z is O or N—R4;
- W is nitrogen or CRa;
- Ra is selected from hydrogen, halogen, —CF3, R7, —OR7, or —N(R7)2;
- R1 is an aryl or heteroaryl ring, wherein said ring is optionally substituted by up to four R9; wherein an R9 substituent in the ortho-position of R1 taken together with R2 may form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring having 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R2 and R3 are each independently selected from R6, halogen, CN, SR6, OR6, N(R6)2, NRCO2R6, NRCON (R6)2, CON(R6)2, NRCOR6, NRN(R6)2, COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or NRSO2R6; or R2 and R3 are taken together to form a fused, unsaturated or partially unsaturated, optionally substituted 5-8 membered ring containing 0-2 ring heteroatoms selected from nitrogen, oxygen, or sulfur;
- R4 is selected from R6, CON(R6), COR6, CO2R6, COCOR6, SO2R6, SO2N(R6)2, or (CH2)yR2;
- y is 1-6;
- R5 is selected from R7, Ar, COAr, CON(R7)Ar, (CH2)yCO2R, (CH2)yN(R7)2, C(═NR10)—N(R7)2, C(═NR10)—NRCOR, C(═S)—N(R7)2, CON(R7)2, COR, SO2R, or SO2N(R7)2;
- Ar is a five membered heteroaryl, heterocyclyl, or carbocyclyl ring, wherein said ring is optionally substituted by up to three substituents selected from oxo, halogen, CN, NO2, R8, OR8, NHR8, NHCOR8, NHCONHR8, COR8, CONHR8, SO2R8, NHSO2NHR8 or SO2NHR8;
- each R6 is independently selected from R7 or an optionally substituted group selected from alkoxy, hydroxylalkyl, heterocyclyl, heterocyclcylalkyl, aryl, aralkyl, aralkoxy, aryloxyalkyl, heteroaryl, heteroaralkyl, heteroaralkoxy, or heteroarayloxyalkyl;
- each R7 is independently selected from hydrogen or an optionally substituted aliphatic group having one to six carbons, or two R7 on the same nitrogen taken together with the nitrogen optionally form a four to six member, saturated or unsaturated heterocyclic ring having one to three heteroatoms;
- R8 is a C1-C4 aliphatic group, wherein two R8 on adjacent positions of Ar, or an aryl or heteroaryl ring, may be taken together with their intervening atoms to form a three to six membered fused ring;
- each R9 is independently selected from oxo, halogen, CN, NO2, Tn(haloalkyl), R6, SR6, OR6, OR8, N(R6)2, CON (R6)2, CON(R)COR6, COR6, CO2R6, CO2N(R6)2, COCOR6, SO2R6, SO2N(R6)2, N(R)TnCO2R6, N(R) TnCON(R6)2, N(R)TnN(R6)2, N(R)TnNRCO2R6, N(R) TnNRCON(R6)2, N(R)TnCOR6, N(R)TnNRCOR6, N(R)TnSO2N(R6)2, N(R)TnSO2R6, TnPO(OR7)2, TnOP(OR7)2, TnSP(OR7)2, TnPO(OR7)2, or TnNPO (OR7)2;
- each Q is an independently selected C1-C3 branched or straight alkyl;
- T is selected from —Q— or —Qm—CH(Qm—R2)—;
- each m and n are independently selected from zero or one;
- and R10 is selected from R7 or Ar.
TABLE 3 |
Characterization Data for Selected Compounds |
No. Ia- | M + 1 | 1H NMR |
1 | 282 | Y |
2 | 288 | Y |
3 | 283 | Y |
4 | 283 | Y |
6 | 210 | Y |
7 | 268 | Y |
8 | 292 | — |
9 | 350 | Y |
10 | 296 | Y |
11 | 283 | Y |
12 | 325 | Y |
13 | 324 | Y |
14 | 336 | Y |
15 | 326 | Y |
16 | 344 | Y |
17 | 361 | Y |
18 | 313 | Y |
19 | 360 | Y |
20 | 399 | Y |
21 | 284 | Y |
22 | 314 | Y |
23 | 312 | Y |
24 | 215 | Y |
26 | 342 | Y |
33 | 249 | Y |
34 | 298 | Y |
35 | 356 | Y |
36 | 283 | Y |
37 | 428 | Y |
38 | 294 | Y |
39 | 272 | Y |
40 | 498 | Y |
41 | 452 | Y |
42 | 312 | Y |
43 | 295.1 | Y |
44 | 338 | — |
45 | 386 | Y |
46 | 320 | Y |
47 | 382 | — |
48 | 389 | — |
49 | 418 | — |
50 | 311 | Y |
51 | 299 | Y |
52 | 343 | Y |
53 | 368 | Y |
54 | 298 | Y |
55 | 395 | Y |
56 | 406 | — |
57 | 366 | Y |
58 | 296 | Y |
59 | 354 | Y |
60 | 326 | Y |
61 | 440 | Y |
62 | 300 | Y |
63 | 403 | — |
64 | 381 | — |
65 | 352 | — |
66 | 326 | — |
67 | 409 | Y |
69 | 468 | Y |
70 | 368 | Y |
71 | 299 | Y |
72 | 299 | Y |
73 | 267 | — |
74 | 253 | — |
75 | 297 | — |
76 | 413 | Y |
77 | 371 | — |
78 | 282 | Y |
79 | 296 | Y |
80 | 357 | Y |
81 | 340 | Y |
82 | 280 | Y |
84 | 281 | Y |
85 | 321 | — |
86 | 442 | Y |
87 | 370 | Y |
88 | 342 | — |
89 | 359 | Y |
90 | 298 | Y |
91 | 446 | Y |
92 | 329 | — |
93 | 499 | Y |
94 | 387 | Y |
97 | 294 | Y |
98 | 389 | — |
100 | 370 | — |
101 | 280 | — |
102 | 370 | — |
103 | 312 | Y |
106 | 409 | — |
108 | 300 | Y |
109 | 394 | — |
110 | 467 | Y |
111 | 367 | Y |
112 | 343 | Y |
113 | 409 | — |
115 | 298 | Y |
116 | 343 | — |
117 | 369 | — |
116 | 282 | Y |
119 | 296 | Y |
120 | 296 | Y |
121 | 322 | Y |
122 | 340 | Y |
124 | 445 | — |
125 | 382 | — |
126 | 328 | Y |
127 | 394 | — |
128 | 432 | — |
129 | 368 | — |
130 | 396 | Y |
131 | 316 | Y |
132 | 312 | Y |
133 | 296 | Y |
134 | 316 | Y |
135 | 410 | Y |
136 | 300 | Y |
137 | 310 | Y |
138 | 388 | — |
139 | 352 | Y |
140 | 401 | Y |
141 | 384 | Y |
142 | 310 | Y |
143 | 511 | Y |
144 | 311 | Y |
145 | 353 | — |
146 | 400 | Y |
147 | 326 | Y |
148 | 411 | Y |
149 | 370 | Y |
150 | — | — |
151 | — | — |
152 | 317 | Y |
153 | 362 | Y |
154 | 389 | Y |
155 | 299 | — |
156 | — | — |
157 | — | — |
158 | — | — |
159 | 328 | — |
160 | — | — |
161 | — | — |
162 | — | — |
163 | 326 | Y |
164 | 367 | Y |
165 | 297 | Y |
166 | 367 | Y |
167 | 350 | — |
168 | 298 | Y |
169 | — | Y |
170 | — | — |
171 | — | — |
172 | — | — |
173 | — | — |
174 | — | — |
175 | 365 | Y |
176 | — | Y |
177 | — | — |
178 | — | Y |
179 | 367 | Y |
180 | — | Y |
181 | 315 | Y |
182 | 366 | Y |
183 | 330 | Y |
184 | — | — |
185 | — | — |
186 | — | — |
187 | — | — |
188 | — | — |
TABLE 4 |
Gyrase Inhibitory Activity of Selected Compounds |
No. Ia- | Activity | ||
1 | B | ||
2 | B | ||
3 | B | ||
4 | C | ||
6 | A | ||
7 | A | ||
8 | A | ||
9 | A | ||
10 | A | ||
11 | C | ||
12 | B | ||
13 | A | ||
14 | B | ||
15 | B | ||
16 | C | ||
17 | C | ||
18 | C | ||
19 | C | ||
20 | A | ||
21 | C | ||
22 | C | ||
23 | C | ||
24 | C | ||
26 | B | ||
33 | A | ||
34 | C | ||
35 | C | ||
36 | A | ||
37 | C | ||
38 | B | ||
39 | C | ||
40 | C | ||
41 | A | ||
42 | C | ||
43 | C | ||
44 | C | ||
45 | C | ||
46 | A | ||
47 | C | ||
48 | C | ||
49 | C | ||
50 | B | ||
52 | C | ||
53 | C | ||
54 | C | ||
55 | C | ||
56 | C | ||
57 | C | ||
58 | C | ||
59 | C | ||
60 | C | ||
61 | C | ||
62 | C | ||
63 | C | ||
64 | C | ||
65 | C | ||
66 | C | ||
67 | C | ||
69 | B | ||
70 | C | ||
71 | A | ||
72 | C | ||
73 | A | ||
74 | A | ||
75 | A | ||
76 | C | ||
77 | C | ||
78 | A | ||
79 | A | ||
80 | C | ||
81 | B | ||
82 | A | ||
84 | C | ||
85 | A | ||
86 | C | ||
87 | C | ||
88 | C | ||
89 | C | ||
90 | C | ||
91 | A | ||
92 | C | ||
93 | C | ||
94 | C | ||
97 | A | ||
98 | C | ||
100 | C | ||
101 | A | ||
102 | C | ||
103 | C | ||
106 | C | ||
108 | C | ||
109 | C | ||
110 | C | ||
111 | C | ||
112 | C | ||
113 | C | ||
115 | A | ||
116 | B | ||
117 | A | ||
118 | C | ||
119 | C | ||
120 | B | ||
121 | A | ||
122 | C | ||
124 | B | ||
125 | C | ||
126 | C | ||
127 | C | ||
128 | C | ||
129 | C | ||
130 | C | ||
131 | C | ||
132 | C | ||
133 | C | ||
134 | C | ||
135 | C | ||
136 | C | ||
137 | C | ||
138 | C | ||
139 | C | ||
140 | C | ||
141 | C | ||
142 | C | ||
143 | C | ||
144 | C | ||
145 | C | ||
146 | C | ||
147 | B | ||
148 | C | ||
149 | C | ||
150 | B | ||
151 | C | ||
152 | C | ||
153 | B | ||
154 | C | ||
155 | A | ||
156 | C | ||
157 | C | ||
158 | C | ||
159 | A | ||
160 | C | ||
161 | A | ||
162 | C | ||
163 | C | ||
164 | C | ||
165 | C | ||
166 | C | ||
167 | C | ||
168 | C | ||
169 | C | ||
170 | C | ||
171 | C | ||
172 | C | ||
173 | C | ||
174 | C | ||
175 | C | ||
176 | A | ||
177 | C | ||
178 | C | ||
179 | C | ||
180 | C | ||
181 | B | ||
182 | C | ||
183 | B | ||
184 | B | ||
185 | C | ||
186 | C | ||
187 | C | ||
188 | C | ||
— | — | ||
TABLE 5 |
MIC Values of Selected Compounds |
No. Ia- | Activity | ||
42 | B | ||
58 | A | ||
90 | A | ||
92 | A | ||
98 | B | ||
112 | A | ||
116 | C | ||
117 | C | ||
118 | A | ||
119 | C | ||
120 | C | ||
121 | C | ||
122 | C | ||
133 | A | ||
137 | C | ||
138 | C | ||
139 | C | ||
140 | A | ||
141 | A | ||
142 | A | ||
144 | B | ||
145 | B | ||
146 | A | ||
147 | C | ||
148 | B | ||
149 | C | ||
150 | C | ||
151 | C | ||
152 | B | ||
153 | C | ||
154 | C | ||
156 | B | ||
157 | C | ||
158 | C | ||
159 | C | ||
160 | C | ||
161 | C | ||
162 | C | ||
163 | A | ||
164 | C | ||
165 | B | ||
166 | C | ||
167 | C | ||
168 | A | ||
169 | B | ||
170 | C | ||
171 | B | ||
173 | B | ||
174 | C | ||
175 | C | ||
177 | C | ||
178 | A | ||
179 | C | ||
180 | B | ||
181 | C | ||
182 | C | ||
183 | C | ||
184 | C | ||
185 | C | ||
186 | A | ||
187 | B | ||
188 | A | ||
196 | B | ||
197 | B | ||
198 | B | ||
— | — | ||
Claims (26)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/833,995 USRE40245E1 (en) | 2000-12-15 | 2004-04-28 | Gyrase inhibitors and uses thereof |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25609400P | 2000-12-15 | 2000-12-15 | |
US27529201P | 2001-03-13 | 2001-03-13 | |
US10/015,332 US6632809B2 (en) | 2000-12-15 | 2001-12-12 | Gyrase inhibitors and uses thereof |
US10/833,995 USRE40245E1 (en) | 2000-12-15 | 2004-04-28 | Gyrase inhibitors and uses thereof |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/015,332 Reissue US6632809B2 (en) | 2000-12-15 | 2001-12-12 | Gyrase inhibitors and uses thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE40245E1 true USRE40245E1 (en) | 2008-04-15 |
Family
ID=26945154
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/015,332 Ceased US6632809B2 (en) | 2000-12-15 | 2001-12-12 | Gyrase inhibitors and uses thereof |
US10/444,588 Expired - Fee Related US7414046B2 (en) | 2000-12-15 | 2003-05-23 | Gyrase inhibitors and uses thereof |
US10/833,995 Expired - Fee Related USRE40245E1 (en) | 2000-12-15 | 2004-04-28 | Gyrase inhibitors and uses thereof |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/015,332 Ceased US6632809B2 (en) | 2000-12-15 | 2001-12-12 | Gyrase inhibitors and uses thereof |
US10/444,588 Expired - Fee Related US7414046B2 (en) | 2000-12-15 | 2003-05-23 | Gyrase inhibitors and uses thereof |
Country Status (28)
Country | Link |
---|---|
US (3) | US6632809B2 (en) |
EP (2) | EP1341769B1 (en) |
JP (2) | JP4516272B2 (en) |
KR (1) | KR100944645B1 (en) |
CN (1) | CN1266138C (en) |
AP (1) | AP2003002824A0 (en) |
AR (1) | AR054963A1 (en) |
AT (2) | ATE443052T1 (en) |
AU (1) | AU2006201397B2 (en) |
BR (1) | BR0116216A (en) |
CA (1) | CA2433197C (en) |
CO (1) | CO7250441A2 (en) |
CY (1) | CY1107854T1 (en) |
DE (2) | DE60139964D1 (en) |
DK (1) | DK1341769T3 (en) |
ES (2) | ES2294046T3 (en) |
HK (1) | HK1061851A1 (en) |
HU (1) | HUP0303494A3 (en) |
IL (2) | IL156031A0 (en) |
MX (1) | MXPA03005298A (en) |
MY (1) | MY138797A (en) |
NO (1) | NO327312B1 (en) |
NZ (1) | NZ526241A (en) |
PL (1) | PL362691A1 (en) |
PT (1) | PT1341769E (en) |
RU (1) | RU2262932C2 (en) |
SI (1) | SI1341769T1 (en) |
WO (1) | WO2002060879A2 (en) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090176771A1 (en) * | 2003-01-31 | 2009-07-09 | Paul Charifson | Gyrase inhibitors and uses thereof |
US20090325935A1 (en) * | 2003-01-31 | 2009-12-31 | Paul Charifson | Gyrase inhibitors and uses thereof |
US20090325955A1 (en) * | 2003-01-31 | 2009-12-31 | Paul Charifson | Gyrase inhibitors and uses thereof |
US20100063284A1 (en) * | 2007-12-07 | 2010-03-11 | Vertex Pharmaceuticals Incorporated | SOLID FORMS OF 1-ethyl-3-(5-(5-FLUOROPYRIDIN-3-YL)-7-(PYRIMIDIN-2-YL)-1H-BENZO[D]IMIDAZOL-2-YL)UREA |
US20100105701A1 (en) * | 2002-06-13 | 2010-04-29 | Charifson Paul S | Gyrase inhibitors and uses thereof |
WO2012097274A1 (en) | 2011-01-14 | 2012-07-19 | Vertex Pharmaceuticals Incorporation | Process of making gyrase and topoisomerase iv inhibitors |
WO2012097269A1 (en) | 2011-01-14 | 2012-07-19 | Vertex Pharmaceuticals Incorporated | Pyrimidine gyrase and topoisomerase iv inhibitors |
WO2012177707A1 (en) | 2011-06-20 | 2012-12-27 | Vertex Pharmaceuticals Incorporated | Phosphate esters of gyrase and topoisomerase inhibitors |
US8394803B2 (en) | 2005-11-07 | 2013-03-12 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US8404852B2 (en) | 2003-01-31 | 2013-03-26 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US8476281B2 (en) | 2011-01-14 | 2013-07-02 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (R)-1-ethyl-3-[6-fluoro-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl)-1H-benzimidazol-2-yl]urea |
US8481552B2 (en) | 2011-01-14 | 2013-07-09 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (R)-1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-YL]-7-(tetrahydrofuran-2-yl)-1H-benzimidazol-2-YL]urea |
WO2014015105A1 (en) | 2012-07-18 | 2014-01-23 | Vertex Pharmaceuticals Incorporated | Solid forms of (r)-2-(5-(2-(3-ethylureido)-6-fluoro-7-(tetrahydrofuran-2-yl)-1h-benzo[d]imidazol-5-yl)pyrimidin-2-yl)propan-2-yl dihydrogen phosphate and salts thereof |
US9085560B2 (en) | 2009-08-17 | 2015-07-21 | Intellikine, Inc. | Heterocyclic compounds and uses thereof |
US9096590B2 (en) | 2010-05-24 | 2015-08-04 | Intellikine Llc | Substituted benzoxazoles as PI3 kinase inhibitors |
US9127000B2 (en) | 2011-02-23 | 2015-09-08 | Intellikine, LLC. | Heterocyclic compounds and uses thereof |
US9295673B2 (en) | 2011-02-23 | 2016-03-29 | Intellikine Llc | Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof |
US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
Families Citing this family (62)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4487774B2 (en) * | 2002-09-30 | 2010-06-23 | 萬有製薬株式会社 | 2-aminobenzimidazole derivatives |
US8193352B2 (en) | 2003-01-31 | 2012-06-05 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US7618974B2 (en) | 2003-01-31 | 2009-11-17 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
FR2852957B1 (en) * | 2003-03-31 | 2005-06-10 | Sod Conseils Rech Applic | NOVEL IMIDAZO-PYRIDINE DERIVATIVES AND THEIR USE AS A MEDICINAL PRODUCT |
US6984652B2 (en) * | 2003-09-05 | 2006-01-10 | Warner-Lambert Company Llc | Gyrase inhibitors |
US20060029948A1 (en) * | 2003-09-19 | 2006-02-09 | Gary Lim | Sealing cover and dye compatibility selection |
US7417726B2 (en) | 2003-09-19 | 2008-08-26 | Applied Biosystems Inc. | Normalization of data using controls |
US20060024690A1 (en) * | 2003-09-19 | 2006-02-02 | Kao H P | Normalization of data using controls |
US20050221357A1 (en) * | 2003-09-19 | 2005-10-06 | Mark Shannon | Normalization of gene expression data |
US20050255485A1 (en) * | 2004-05-14 | 2005-11-17 | Livak Kenneth J | Detection of gene duplications |
WO2005121132A1 (en) * | 2004-06-11 | 2005-12-22 | Shionogi & Co., Ltd. | Fused heterocyclic compound having anti-hcv effect |
MX2007004179A (en) * | 2004-10-07 | 2007-06-07 | Warner Lambert Co | Triazolopyridine derivatives as antibacterial agents. |
WO2007037782A2 (en) * | 2005-02-08 | 2007-04-05 | The University Of North Carolina At Chapel Hill | Method for treating prostate conditions |
TW200804345A (en) * | 2005-08-30 | 2008-01-16 | Novartis Ag | Substituted benzimidazoles and methods of preparation |
EP2028936A4 (en) * | 2006-02-13 | 2014-02-26 | Univ Boston | Compositions and methods for antibiotic potentiation and drug discovers |
PE20070978A1 (en) * | 2006-02-14 | 2007-11-15 | Novartis Ag | HETEROCICLIC COMPOUNDS AS INHIBITORS OF PHOSPHATIDYLINOSITOL 3-KINASES (PI3Ks) |
GB0612428D0 (en) * | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
AU2012200669B2 (en) * | 2006-06-22 | 2012-11-01 | Biota Europe Ltd | Antibacterial compositions |
US8481544B2 (en) | 2006-06-22 | 2013-07-09 | Biota Europe Limited | Antibacterial compositions |
WO2008016123A1 (en) | 2006-08-03 | 2008-02-07 | Takeda Pharmaceutical Company Limited | GSK-3β INHIBITOR |
WO2008019292A2 (en) * | 2006-08-04 | 2008-02-14 | Trustees Of Boston University | Compositions and methods for potentiating antibiotic activity |
JP2010511682A (en) * | 2006-12-04 | 2010-04-15 | アストラゼネカ アクチボラグ | Antibacterial polycyclic urea compounds |
WO2009001915A1 (en) * | 2007-06-28 | 2008-12-31 | Takeda Pharmaceutical Company Limited | Substituted imidazole compound and use thereof |
WO2009027732A1 (en) * | 2007-08-24 | 2009-03-05 | Astrazeneca Ab | 5-6-bicyclic heteroaromatic compounds with antibacterial activity |
GB0724342D0 (en) * | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
UY31864A (en) | 2008-06-04 | 2010-01-29 | Astrazeneca Ab | DERIVATIVES OF UREA HETERICÍCLICA AND METHODS OF USE OF THE SAME-332 |
MX2010013249A (en) * | 2008-06-04 | 2010-12-21 | Astrazeneca Ab | Thiazolo [5, 4-b] pyridine and oxazolo [5, 4-b] pyridine derivatives as antibacterial agents. |
CL2009001345A1 (en) * | 2008-06-04 | 2010-06-11 | Astrazeneca Ab | Substituted 1-pyridin-2-yl-urea and 1-pyrimidin-2-yl-urea derivative compounds, dna gyrase and topoisomerase inhibitors iv; pharmaceutical composition; and its use in the treatment of bacterial infections such as intrahospital acquired pneumonia, skin infections, bronchitis, sinusitis, among other diseases. |
GB0821913D0 (en) | 2008-12-02 | 2009-01-07 | Price & Co | Antibacterial compounds |
US8071605B2 (en) | 2008-12-12 | 2011-12-06 | Astrazeneca Ab | Piperidine compounds for use in the treatment of bacterial infections |
TW201026694A (en) | 2008-12-12 | 2010-07-16 | Astrazeneca Ab | Compound 468 |
TW201102065A (en) * | 2009-05-29 | 2011-01-16 | Astrazeneca Ab | Heterocyclic urea derivatives and methods of use thereof |
MX2011012961A (en) | 2009-06-05 | 2012-01-30 | Cephalon Inc | PREPARATION AND USES OF 1,2,4-TRIAZOLO [1,5a] PYRIDINE DERIVATIVES. |
AR077971A1 (en) | 2009-08-26 | 2011-10-05 | Astrazeneca Ab | UREA HETEROCICLICAL DERIVATIVES AND METHODS OF USE OF THE SAME |
WO2011032050A2 (en) * | 2009-09-11 | 2011-03-17 | Trius Therapeutics, Inc. | Gyrase inhibitors |
BR112012024705A2 (en) | 2010-03-31 | 2016-06-07 | Actelion Pharmaceuticals Ltd | antibacterial isoquinolin-3-ylurea derivatives |
WO2011151617A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
EP3011960B1 (en) | 2010-06-01 | 2020-04-15 | Summit Therapeutics plc | Compounds for the treatment of clostridium difficile-associated disease |
WO2011151618A2 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile-associated disease |
WO2011151619A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
WO2011151620A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
EP2625178A4 (en) | 2010-10-08 | 2014-04-30 | Biota Europe Ltd | Bacteria topoisomerase ii inhibiting 2-ethylcarbamoylamino-1, 3-benzothiazol-5-yls |
AR088729A1 (en) | 2011-03-29 | 2014-07-02 | Actelion Pharmaceuticals Ltd | DERIVATIVES OF 3-UREIDOISOQUINOLIN-8-ILO AND A PHARMACEUTICAL COMPOSITION |
WO2013016720A2 (en) * | 2011-07-28 | 2013-01-31 | Gerinda Therapeutics, Inc. | Novel substituted biarylheterocycle derivatives as protein kinase inhibitors for the treatment of cancer and other diseases |
KR101546743B1 (en) | 2012-01-16 | 2015-08-24 | 한국과학기술원 | Indole derivatives, Abl kinase inhibiting composition and pharmaceutical compositions for prevention and treatment of abnormal cell growth diseases comprising the same |
US9079935B2 (en) | 2012-08-13 | 2015-07-14 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Reducing risk of contracting Clostridium-difficile associated disease |
JP2015526520A (en) | 2012-08-31 | 2015-09-10 | プリンシピア バイオファーマ インコーポレイテッド | Benzimidazole derivatives as ITK inhibitors |
US9988373B2 (en) | 2013-12-26 | 2018-06-05 | Shionogi & Co., Ltd. | Nitrogen-containing six-membered cyclic derivatives and pharmaceutical composition comprising the same |
BR112016018048A2 (en) | 2014-02-03 | 2017-08-08 | Spero Gyrase Inc | METHOD FOR THE TREATMENT OR PREVENTION OF A BACTERIAL INFECTION, USE OF A BACTERIAL TOPOISOMERASE TYPE II INHIBTOR IN COMBINATION WITH A POLYMYXIN OR POLYMIXIN DERIVATIVE IN THE TREATMENT OR PREVENTION OF A BACTERIAL INFECTION, USE OF A BACTERIAL TYPE II INHIBTOR IN COMBINATION WITH A POLYMIXIN OR POLYMYXIN DERIVATIVE IN THE PREPARATION OF A DRUG FOR THE TREATMENT OR PREVENTION OF A BACTERIAL INFECTION, METHOD FOR ENHANCEMENT OF THE ANTIBACTERIAL ACTIVITY OF A BACTERIAL TOPOISOMERASE TYPE II INHIBITOR, METHOD FOR ENHANCEMENT OF THE BACTERICIDAL EFFECTIVENESS OF A BACTERIAL TOPOISOMERASE TYPE II INHIBITOR , COMPOSITION, ANTIBACTERIAL AGENT, PROCESS, AND, COMPOUND |
CN104876878B (en) * | 2014-02-27 | 2018-04-27 | 中国科学院广州生物医药与健康研究院 | - 2 alkyl substituted urea benzimidazoles compound of 5- aryl phenols and its application |
US20180000793A1 (en) | 2015-02-06 | 2018-01-04 | Ernesto Abel-Santos | Inhibiting Germination of Clostridium Perfringens Spores to Reduce Necrotic Enteritis |
CN107641118B (en) * | 2016-07-22 | 2020-11-06 | 爱科诺生物医药股份有限公司 | Compound with cell necrosis inhibition activity, composition and application thereof |
US11180459B2 (en) * | 2017-03-10 | 2021-11-23 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
EP3604281A4 (en) | 2017-03-24 | 2020-08-19 | Taisho Pharmaceutical Co., Ltd. | 2(1h)-quinolinone derivative |
US11666555B2 (en) | 2017-05-17 | 2023-06-06 | Drexel University | RelA inhibitors for biofilm disruption |
AU2018310749A1 (en) * | 2017-08-01 | 2020-02-20 | Opal Biosciences Limited | Treatment of Staphylococcal and Enterococcal infections using substituted nitrostyrene compounds |
RU2643372C1 (en) * | 2017-08-07 | 2018-02-01 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | METHOD FOR PREPARATION OF ETHYL 3-(3-HYDROXY-1,4-DIOXO-1,4-DIHYDRONAPHTHALEN-2-YL)-2,5,10-TRIOXO-10b-PHENYL-1,2,3,5,10,10b -HEXAGYDRO-3aH-NAPHTO [2',3':4,5]FURO[3,2-b]PYRROL-3a-CARBOXYLATES |
US20210323957A1 (en) | 2018-09-03 | 2021-10-21 | Univerza V Ljubljani | New class of dna gyrase and/or topoisomerase iv inhibitors with activity against gram-positive and gram-negative bacteria |
BR112022000484A2 (en) | 2019-07-17 | 2022-03-08 | Summit Oxford Ltd | Ridinylazole preparation process and crystalline forms thereof |
CN110622973B (en) * | 2019-11-06 | 2020-11-10 | 海南大学 | Application of 1-aryl-4-pyridone compounds |
WO2022129327A1 (en) | 2020-12-17 | 2022-06-23 | Univerza V Ljubljani | New n-phenylpyrrolamide inhibitors of dna gyrase and topoisomerase iv with antibacterial activity |
GB202100471D0 (en) | 2021-01-14 | 2021-03-03 | Summit Oxford Ltd | Preparation of antibacterial compounds |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4174400A (en) | 1978-09-13 | 1979-11-13 | Merck & Co., Inc. | Anthelmintic benzimidazoles |
US4512998A (en) | 1980-10-20 | 1985-04-23 | Schering Corporation | Anthelmintic benzimidazole carbamates |
US5529998A (en) | 1994-08-03 | 1996-06-25 | Bayer Aktiengesellschaft | Benzoxazolyl- and benzothiazolyloxazolidinones |
EP0738726A1 (en) | 1995-04-21 | 1996-10-23 | Bayer Ag | Heterobenzocyclopentane oxazolidinones having antibacterial activity |
WO1999035155A1 (en) | 1998-01-08 | 1999-07-15 | Hoechst Marion Roussel | Novel aromatic amides, preparation method and application as medicines |
WO2000049015A1 (en) | 1999-02-17 | 2000-08-24 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds and their pharmaceutical use |
EP1055668A1 (en) | 1999-05-28 | 2000-11-29 | Pfizer Inc. | New 4-arylpiperidine derivatives for the treatment of pruritus |
WO2000071522A1 (en) | 1999-05-19 | 2000-11-30 | Smithkline Beecham Plc | Benzimidazole derivatives and their use as methionyl t-rna synthetase inhibitors |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4338315A (en) * | 1979-11-14 | 1982-07-06 | Eli Lilly And Company | Antiviral method employing thiazinyl benzimidazole derivatives |
US4401817A (en) * | 1981-04-20 | 1983-08-30 | Eli Lilly And Company | Carbonyl-substituted 1-sulfonylbenzimidazoles |
GB8803429D0 (en) * | 1988-02-15 | 1988-03-16 | Fujisawa Pharmaceutical Co | Imidazole compounds processes for preparation thereof & pharmaceutical composition comprising same |
FR2643903A1 (en) * | 1989-03-03 | 1990-09-07 | Union Pharma Scient Appl | NOVEL BENZIMIDAZOLE DERIVATIVES, PROCESSES FOR PREPARING SAME, SYNTHESIS INTERMEDIATES, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, IN PARTICULAR FOR THE TREATMENT OF CARDIOVASCULAR DISEASES, AND DUODENIAL ULCERS |
US5296486A (en) * | 1991-09-24 | 1994-03-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | Leukotriene biosynthesis inhibitors |
DE4317657C1 (en) * | 1993-05-27 | 1994-07-14 | Voith Gmbh J M | Coating device for coating running webs |
CA2172245C (en) | 1993-09-22 | 2003-04-08 | Jonathan Cohen | Method of treating gram-negative bacterial infection by administration of bactericidal/permeability-increasing (bpi) protein |
EP0754050B1 (en) | 1994-01-14 | 2002-06-26 | XOMA Technology Ltd. | Anti gram positive bacterial methods and materials |
-
2001
- 2001-12-12 DE DE60139964T patent/DE60139964D1/en not_active Expired - Lifetime
- 2001-12-12 DE DE60131015T patent/DE60131015T2/en not_active Expired - Lifetime
- 2001-12-12 BR BR0116216-0A patent/BR0116216A/en not_active IP Right Cessation
- 2001-12-12 MX MXPA03005298A patent/MXPA03005298A/en active IP Right Grant
- 2001-12-12 EP EP01994269A patent/EP1341769B1/en not_active Expired - Lifetime
- 2001-12-12 CN CNB01820547XA patent/CN1266138C/en not_active Expired - Fee Related
- 2001-12-12 ES ES01994269T patent/ES2294046T3/en not_active Expired - Lifetime
- 2001-12-12 DK DK01994269T patent/DK1341769T3/en active
- 2001-12-12 PT PT01994269T patent/PT1341769E/en unknown
- 2001-12-12 EP EP05008137A patent/EP1557410B1/en not_active Expired - Lifetime
- 2001-12-12 JP JP2002561029A patent/JP4516272B2/en not_active Expired - Fee Related
- 2001-12-12 KR KR1020037007970A patent/KR100944645B1/en not_active IP Right Cessation
- 2001-12-12 PL PL01362691A patent/PL362691A1/en not_active Application Discontinuation
- 2001-12-12 CA CA002433197A patent/CA2433197C/en not_active Expired - Fee Related
- 2001-12-12 WO PCT/US2001/048855 patent/WO2002060879A2/en active IP Right Grant
- 2001-12-12 AT AT05008137T patent/ATE443052T1/en active
- 2001-12-12 AT AT01994269T patent/ATE375983T1/en not_active IP Right Cessation
- 2001-12-12 MY MYPI20015634A patent/MY138797A/en unknown
- 2001-12-12 HU HU0303494A patent/HUP0303494A3/en unknown
- 2001-12-12 US US10/015,332 patent/US6632809B2/en not_active Ceased
- 2001-12-12 IL IL15603101A patent/IL156031A0/en unknown
- 2001-12-12 RU RU2003121398/15A patent/RU2262932C2/en not_active IP Right Cessation
- 2001-12-12 NZ NZ526241A patent/NZ526241A/en not_active IP Right Cessation
- 2001-12-12 SI SI200130794T patent/SI1341769T1/en unknown
- 2001-12-12 ES ES05008137T patent/ES2331250T3/en not_active Expired - Lifetime
- 2001-12-12 AP APAP/P/2003/002824A patent/AP2003002824A0/en unknown
- 2001-12-14 AR ARP010105831A patent/AR054963A1/en unknown
-
2003
- 2003-05-21 IL IL156031A patent/IL156031A/en not_active IP Right Cessation
- 2003-05-23 US US10/444,588 patent/US7414046B2/en not_active Expired - Fee Related
- 2003-06-12 NO NO20032668A patent/NO327312B1/en not_active IP Right Cessation
- 2003-06-13 CO CO03050487A patent/CO7250441A2/en unknown
-
2004
- 2004-04-28 US US10/833,995 patent/USRE40245E1/en not_active Expired - Fee Related
- 2004-07-06 HK HK04104843A patent/HK1061851A1/en not_active IP Right Cessation
-
2006
- 2006-04-04 AU AU2006201397A patent/AU2006201397B2/en not_active Ceased
-
2008
- 2008-01-11 CY CY20081100042T patent/CY1107854T1/en unknown
-
2009
- 2009-02-19 JP JP2009037223A patent/JP5196660B2/en not_active Expired - Fee Related
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4174400A (en) | 1978-09-13 | 1979-11-13 | Merck & Co., Inc. | Anthelmintic benzimidazoles |
US4512998A (en) | 1980-10-20 | 1985-04-23 | Schering Corporation | Anthelmintic benzimidazole carbamates |
US5529998A (en) | 1994-08-03 | 1996-06-25 | Bayer Aktiengesellschaft | Benzoxazolyl- and benzothiazolyloxazolidinones |
EP0738726A1 (en) | 1995-04-21 | 1996-10-23 | Bayer Ag | Heterobenzocyclopentane oxazolidinones having antibacterial activity |
WO1999035155A1 (en) | 1998-01-08 | 1999-07-15 | Hoechst Marion Roussel | Novel aromatic amides, preparation method and application as medicines |
WO2000049015A1 (en) | 1999-02-17 | 2000-08-24 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds and their pharmaceutical use |
WO2000071522A1 (en) | 1999-05-19 | 2000-11-30 | Smithkline Beecham Plc | Benzimidazole derivatives and their use as methionyl t-rna synthetase inhibitors |
EP1055668A1 (en) | 1999-05-28 | 2000-11-29 | Pfizer Inc. | New 4-arylpiperidine derivatives for the treatment of pruritus |
Non-Patent Citations (7)
Title |
---|
Beers, M. H., and Berkow, R., "The Merck Manual of Diagnosis and Therapy", 7<SUP>th </SUP>Edition, Chapter 156-Bacteremia and Septic Shock, Merck Research Laboratories, Whitehouse Station, NJ pp. 1143-1147 (1999). |
Kus, C., "Synthesis and antimicrobial activities of 5-fluoro-1, 2, 6-trisubstituted benzimidazole carboxamide and acetamide derivatives," Arch. Pharm. Pharm. Med. Chem. 334(11):361-365 (2001). |
Nicolaus B. J. R., "Symbiotic Approach to Drug Design," Decision Making in Drug Research, pp. 173-186 (1983). |
Pea et al., PubMed Abstract (Clin Pharmacokinet. 44(10):1009-34) 2005. * |
Singh, S.K., et al., "Studies in antiparastic agents: Part 13-Synthtesis of 4-aryl-2-substitutedamino-thiazoles as potential anthelmintics," Indian J. Chem., 28B(9):786-789 (1989). |
Snyder et al., PubMed Abstract (J Med Liban. 48(4):208-14), Jul.-Aug. 2000. * |
U.S. Appl. No. 10/015,332, filed Dec. 12, 2001, Anne-Laure Grillot et al. |
Cited By (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100105701A1 (en) * | 2002-06-13 | 2010-04-29 | Charifson Paul S | Gyrase inhibitors and uses thereof |
US8426426B2 (en) | 2002-06-13 | 2013-04-23 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US20110104207A1 (en) * | 2002-06-13 | 2011-05-05 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US7727992B2 (en) | 2002-06-13 | 2010-06-01 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US8067606B2 (en) | 2003-01-31 | 2011-11-29 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US8404852B2 (en) | 2003-01-31 | 2013-03-26 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US20090325955A1 (en) * | 2003-01-31 | 2009-12-31 | Paul Charifson | Gyrase inhibitors and uses thereof |
US8034832B2 (en) | 2003-01-31 | 2011-10-11 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US20090176771A1 (en) * | 2003-01-31 | 2009-07-09 | Paul Charifson | Gyrase inhibitors and uses thereof |
US8188095B2 (en) * | 2003-01-31 | 2012-05-29 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US20090325935A1 (en) * | 2003-01-31 | 2009-12-31 | Paul Charifson | Gyrase inhibitors and uses thereof |
US8394803B2 (en) | 2005-11-07 | 2013-03-12 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
US20100063284A1 (en) * | 2007-12-07 | 2010-03-11 | Vertex Pharmaceuticals Incorporated | SOLID FORMS OF 1-ethyl-3-(5-(5-FLUOROPYRIDIN-3-YL)-7-(PYRIMIDIN-2-YL)-1H-BENZO[D]IMIDAZOL-2-YL)UREA |
US8217172B2 (en) | 2007-12-07 | 2012-07-10 | Vertex Pharmaceuticals Incorporated | Solid forms of 1-ethyl-3-(5-(5-fluoropyridin-3-yl)-7-(pyrimidin-2-yl)-1H-benzo[d]imidazol-2-yl)urea |
US9085560B2 (en) | 2009-08-17 | 2015-07-21 | Intellikine, Inc. | Heterocyclic compounds and uses thereof |
US11547697B2 (en) | 2009-08-17 | 2023-01-10 | Millennium Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
US9359352B2 (en) | 2010-05-24 | 2016-06-07 | Intellikine Llc | Substituted benzimidazoles as PI3 kinase inhibitors |
US9096590B2 (en) | 2010-05-24 | 2015-08-04 | Intellikine Llc | Substituted benzoxazoles as PI3 kinase inhibitors |
WO2012097269A1 (en) | 2011-01-14 | 2012-07-19 | Vertex Pharmaceuticals Incorporated | Pyrimidine gyrase and topoisomerase iv inhibitors |
US8471014B2 (en) | 2011-01-14 | 2013-06-25 | Vertex Pharmaceuticals Incorporated | Process of making gyrase and topoisomerase IV inhibitors |
US8481552B2 (en) | 2011-01-14 | 2013-07-09 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (R)-1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-YL]-7-(tetrahydrofuran-2-yl)-1H-benzimidazol-2-YL]urea |
WO2012097274A1 (en) | 2011-01-14 | 2012-07-19 | Vertex Pharmaceuticals Incorporation | Process of making gyrase and topoisomerase iv inhibitors |
US8912326B2 (en) | 2011-01-14 | 2014-12-16 | Vertex Pharmaceuticals Incorporated | Process of making gyrase and topoisomerase inhibitors |
US8969359B2 (en) | 2011-01-14 | 2015-03-03 | Vertex Pharmaceuticals Incorporated | Gyrase and topoisomerase IV inhibitors |
US8481551B2 (en) | 2011-01-14 | 2013-07-09 | Vertex Pharmaceuticals Incorporated | Gyrase and topoisomerase IV inhibitors |
US9040542B2 (en) | 2011-01-14 | 2015-05-26 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (R)-1-ethyl-3-[6-fluoro-5-[2-(1-hydroxy-1-methyl-ethyl)pryimidin-5-yl]-7-(tetrahydrofuran-2-yl)-1H-benzimidazol-2-yl]urea |
US8476281B2 (en) | 2011-01-14 | 2013-07-02 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (R)-1-ethyl-3-[6-fluoro-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl)-1H-benzimidazol-2-yl]urea |
US9127000B2 (en) | 2011-02-23 | 2015-09-08 | Intellikine, LLC. | Heterocyclic compounds and uses thereof |
US9295673B2 (en) | 2011-02-23 | 2016-03-29 | Intellikine Llc | Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof |
US9125922B2 (en) | 2011-06-20 | 2015-09-08 | Vertex Pharmaceuticals Incorporated | Phosphate esters of gyrase and topoisomerase inhibitors |
WO2012177707A1 (en) | 2011-06-20 | 2012-12-27 | Vertex Pharmaceuticals Incorporated | Phosphate esters of gyrase and topoisomerase inhibitors |
US9018216B2 (en) | 2012-07-18 | 2015-04-28 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-2-(5-(2-(3-ethylureido)-6-fluoro-7-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazol-5-yl)pyrimidin-2-yl)propan-2-yl dihydrogen phosphate and salts thereof |
US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
US9937192B2 (en) | 2012-07-18 | 2018-04-10 | Spero Trinem, Inc. | Combination therapy to treat mycobacterium diseases |
WO2014015105A1 (en) | 2012-07-18 | 2014-01-23 | Vertex Pharmaceuticals Incorporated | Solid forms of (r)-2-(5-(2-(3-ethylureido)-6-fluoro-7-(tetrahydrofuran-2-yl)-1h-benzo[d]imidazol-5-yl)pyrimidin-2-yl)propan-2-yl dihydrogen phosphate and salts thereof |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
USRE40245E1 (en) | Gyrase inhibitors and uses thereof | |
US7727992B2 (en) | Gyrase inhibitors and uses thereof | |
EP1592686B1 (en) | Gyrase inhibitors and uses thereof | |
JP2006528677A5 (en) | ||
KR20070048762A (en) | Gyrase inhibitors and uses thereof | |
AU2002246684A1 (en) | Bacterial gyrase inhibitors and uses thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: VERTEX PHARMACEUTICALS INCORPORATED, MASSACHUSETTS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:GRILLOT, ANNE-LAURE;CHARIFSON, PAUL S.;STAMOS, DEAN;AND OTHERS;REEL/FRAME:014873/0519;SIGNING DATES FROM 20040629 TO 20040713 |
|
FPAY | Fee payment |
Year of fee payment: 8 |
|
AS | Assignment |
Owner name: MACQUARIE US TRADING LLC, NEW YORK Free format text: SECURITY INTEREST;ASSIGNORS:VERTEX PHARMACEUTICALS INCORPORATED;VERTEX PHARMACEUTICALS (SAN DIEGO) LLC;REEL/FRAME:033292/0311 Effective date: 20140709 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
AS | Assignment |
Owner name: VERTEX PHARMACEUTICALS INCORPORATED, MASSACHUSETTS Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:MACQUARIE US TRADING LLC;REEL/FRAME:040357/0001 Effective date: 20161013 Owner name: VERTEX PHARMACEUTICALS (SAN DIEGO) LLC, CALIFORNIA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:MACQUARIE US TRADING LLC;REEL/FRAME:040357/0001 Effective date: 20161013 |