US20090239846A1 - Novel Compounds - Google Patents
Novel Compounds Download PDFInfo
- Publication number
- US20090239846A1 US20090239846A1 US11/908,435 US90843506A US2009239846A1 US 20090239846 A1 US20090239846 A1 US 20090239846A1 US 90843506 A US90843506 A US 90843506A US 2009239846 A1 US2009239846 A1 US 2009239846A1
- Authority
- US
- United States
- Prior art keywords
- alkyl
- hydrogen
- optionally substituted
- aryl
- occurrence
- 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.)
- Abandoned
Links
- 0 CC.CC.[1*]C1=CC(C2=CC(C)=CC3=C2C=CC(=O)N3[3*])=CC=C1.[1*]C1=CC(C2=CC(C)=CC3=C2CCC(=O)N3[3*])=CC=C1 Chemical compound CC.CC.[1*]C1=CC(C2=CC(C)=CC3=C2C=CC(=O)N3[3*])=CC=C1.[1*]C1=CC(C2=CC(C)=CC3=C2CCC(=O)N3[3*])=CC=C1 0.000 description 42
- BYCYLIOZKNXKQC-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 BYCYLIOZKNXKQC-UHFFFAOYSA-N 0.000 description 2
- JEQUPSTWWNYTMN-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCCCl)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(NCCCNCC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCCCl)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(NCCCNCC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 JEQUPSTWWNYTMN-UHFFFAOYSA-N 0.000 description 2
- UPVTXPPWXLCYTL-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCCN)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCCN)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 UPVTXPPWXLCYTL-UHFFFAOYSA-N 0.000 description 2
- ZTICTTZHBJMMQD-UHFFFAOYSA-N CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 Chemical compound CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 ZTICTTZHBJMMQD-UHFFFAOYSA-N 0.000 description 2
- VASIOZCTSJTAFS-UHFFFAOYSA-N NC1=CC2=C(C=C1)C(C1=CC=C(C(=O)NCC3=CC=C(C4=NC(C5=CC(O)=C(Cl)C=C5)=C(C5=CC=NC=C5)N4)C=C3)C=C1C(=O)[O-])=C1C=CC(=[NH2+])C=C1C2 Chemical compound NC1=CC2=C(C=C1)C(C1=CC=C(C(=O)NCC3=CC=C(C4=NC(C5=CC(O)=C(Cl)C=C5)=C(C5=CC=NC=C5)N4)C=C3)C=C1C(=O)[O-])=C1C=CC(=[NH2+])C=C1C2 VASIOZCTSJTAFS-UHFFFAOYSA-N 0.000 description 2
- JFWPGFONOCSPMR-UHFFFAOYSA-N BC.C.C.C.C.C.C.C.C.C.C=C.CC1=CCC23CCCC2(C1)C3.CC1=CCCC1.CC1CC23CCCC2(C1)C3.CC1CCC1 Chemical compound BC.C.C.C.C.C.C.C.C.C.C=C.CC1=CCC23CCCC2(C1)C3.CC1=CCCC1.CC1CC23CCCC2(C1)C3.CC1CCC1 JFWPGFONOCSPMR-UHFFFAOYSA-N 0.000 description 1
- OQIQSCZAKRRZPC-UHFFFAOYSA-N C=CCN.C=CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound C=CCN.C=CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 OQIQSCZAKRRZPC-UHFFFAOYSA-N 0.000 description 1
- QFLZUWHETGEUEI-UHFFFAOYSA-N CC(=O)C1=CC=C(N)C=C1.CC(=O)C1=CC=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1 Chemical compound CC(=O)C1=CC=C(N)C=C1.CC(=O)C1=CC=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1 QFLZUWHETGEUEI-UHFFFAOYSA-N 0.000 description 1
- OTRQPBVGGJOUDC-UHFFFAOYSA-N CC(C)N(CCN)C(C)C.CC1=C(C2=NC(NCCN(C(C)C)C(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC(C)N(CCN)C(C)C.CC1=C(C2=NC(NCCN(C(C)C)C(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 OTRQPBVGGJOUDC-UHFFFAOYSA-N 0.000 description 1
- KDTUHRDJSZILSB-UHFFFAOYSA-N CC(C)NC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=CC=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 Chemical compound CC(C)NC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=CC=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 KDTUHRDJSZILSB-UHFFFAOYSA-N 0.000 description 1
- NEFMMFSEWAZAEF-UHFFFAOYSA-N CC(C)NC(=O)C1=CC=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 Chemical compound CC(C)NC(=O)C1=CC=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 NEFMMFSEWAZAEF-UHFFFAOYSA-N 0.000 description 1
- XYRWMWFCITWAJF-UHFFFAOYSA-N CC(N)CN(C)C.CC1=C(C2=NC(NC(C)CN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC(N)CN(C)C.CC1=C(C2=NC(NC(C)CN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 XYRWMWFCITWAJF-UHFFFAOYSA-N 0.000 description 1
- JBFSVMPPSQMIDI-UHFFFAOYSA-N CC([Ar])C(C)(C)C(C)(C)N(C)C.[Ar] Chemical compound CC([Ar])C(C)(C)C(C)(C)N(C)C.[Ar] JBFSVMPPSQMIDI-UHFFFAOYSA-N 0.000 description 1
- KFUITQRBAQZOIY-UHFFFAOYSA-M CC.CC.CC(C)(C)OC(=O)C1=CC(B(O)O)=CC=C1.CC(C)(C)OC(=O)C1=CC([Mg]Br)=CC=C1 Chemical compound CC.CC.CC(C)(C)OC(=O)C1=CC(B(O)O)=CC=C1.CC(C)(C)OC(=O)C1=CC([Mg]Br)=CC=C1 KFUITQRBAQZOIY-UHFFFAOYSA-M 0.000 description 1
- WRYWBJXHSNKYMA-UHFFFAOYSA-N CC1=C(/C2=N/C(N(C)CCN)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 Chemical compound CC1=C(/C2=N/C(N(C)CCN)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 WRYWBJXHSNKYMA-UHFFFAOYSA-N 0.000 description 1
- LUYAKDAYEWIYEP-UHFFFAOYSA-N CC1=C(/C2=N/C(N3CCC(N)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2CCC2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2CCC2)C=C1 Chemical compound CC1=C(/C2=N/C(N3CCC(N)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2CCC2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2CCC2)C=C1 LUYAKDAYEWIYEP-UHFFFAOYSA-N 0.000 description 1
- URGLPXCZOHDXRH-UHFFFAOYSA-N CC1=C(/C2=N/C(N3CCC(N)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 Chemical compound CC1=C(/C2=N/C(N3CCC(N)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 URGLPXCZOHDXRH-UHFFFAOYSA-N 0.000 description 1
- PWEIOCIWJAIQNL-UHFFFAOYSA-N CC1=C(/C2=N/C(N3CCC(N)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCCC2=CC=C(F)C=C2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCCC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(/C2=N/C(N3CCC(N)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCCC2=CC=C(F)C=C2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCCC2=CC=C(F)C=C2)C=C1 PWEIOCIWJAIQNL-UHFFFAOYSA-N 0.000 description 1
- BUSVGGYVDRZCQN-UHFFFAOYSA-N CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1 Chemical compound CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1 BUSVGGYVDRZCQN-UHFFFAOYSA-N 0.000 description 1
- GQDPJTXFMMBAAN-UHFFFAOYSA-N CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCCC2=CC=C(F)C=C2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1 Chemical compound CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCCC2=CC=C(F)C=C2)C=C1.CC1=C(/C2=N/C(N3CCC(NC(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1 GQDPJTXFMMBAAN-UHFFFAOYSA-N 0.000 description 1
- GSWLHCXBRACEJQ-UHFFFAOYSA-N CC1=C(/C2=N/C(NC3CC(C)(C)NC(C)(C)C3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 Chemical compound CC1=C(/C2=N/C(NC3CC(C)(C)NC(C)(C)C3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 GSWLHCXBRACEJQ-UHFFFAOYSA-N 0.000 description 1
- ODBJDGAUTRFGPO-UHFFFAOYSA-N CC1=C(/C2=N/C(NC3CCN(C(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(NC3CCNCC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 Chemical compound CC1=C(/C2=N/C(NC3CCN(C(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(NC3CCNCC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 ODBJDGAUTRFGPO-UHFFFAOYSA-N 0.000 description 1
- ILRNOZNXEXRUGO-UHFFFAOYSA-N CC1=C(/C2=N/C(NC3CCN(C(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 Chemical compound CC1=C(/C2=N/C(NC3CCN(C(=O)OC(C)(C)C)CC3)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1 ILRNOZNXEXRUGO-UHFFFAOYSA-N 0.000 description 1
- DLJCMXCVVFKFSJ-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=C(F)C=C(F)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=C(F)C=C(F)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=C(F)C=C(F)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=C(F)C=C(F)C=C1 DLJCMXCVVFKFSJ-UHFFFAOYSA-N 0.000 description 1
- VAKSLTLPSCWHNN-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=C(F)C=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=C(F)C=CC=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=C(F)C=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=C(F)C=CC=C1 VAKSLTLPSCWHNN-UHFFFAOYSA-N 0.000 description 1
- HBVPPYZLUIIUTO-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=C/C3=C(\C=C/2)OCCO3)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC2=C(C=C1)OCCO2 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=C/C3=C(\C=C/2)OCCO3)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC2=C(C=C1)OCCO2 HBVPPYZLUIIUTO-UHFFFAOYSA-N 0.000 description 1
- PMLXPEFUQLDIOD-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(C#N)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.N#CC1=CC=CC(N)=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(C#N)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.N#CC1=CC=CC(N)=C1 PMLXPEFUQLDIOD-UHFFFAOYSA-N 0.000 description 1
- OGOCAWBRZFHDRO-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(C3=CC=C(F)C=C3)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(C2=CC=C(F)C=C2)=CC=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(C3=CC=C(F)C=C3)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(C2=CC=C(F)C=C2)=CC=C1 OGOCAWBRZFHDRO-UHFFFAOYSA-N 0.000 description 1
- YYNQNMJPCGTNDV-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(Cl)=C(F)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(Cl)=C(F)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(Cl)=C(F)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(Cl)=C(F)C=C1 YYNQNMJPCGTNDV-UHFFFAOYSA-N 0.000 description 1
- UDZRAUGBARXBNG-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(Cl)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(Cl)=CC=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(Cl)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(Cl)=CC=C1 UDZRAUGBARXBNG-UHFFFAOYSA-N 0.000 description 1
- CBZNIGRWUIUGJY-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(F)=CC(F)=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(F)=CC(F)=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(F)=CC(F)=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(F)=CC(F)=C1 CBZNIGRWUIUGJY-UHFFFAOYSA-N 0.000 description 1
- HPHGBXKCNQPSDV-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(OC3=CC=CC=C3)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(OC2=CC=CC=C2)=CC=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(OC3=CC=CC=C3)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(OC2=CC=CC=C2)=CC=C1 HPHGBXKCNQPSDV-UHFFFAOYSA-N 0.000 description 1
- TUFKSOXKMWRLKM-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(S(N)(=O)=O)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(S(N)(=O)=O)=CC=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(S(N)(=O)=O)=CC=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC(S(N)(=O)=O)=CC=C1 TUFKSOXKMWRLKM-UHFFFAOYSA-N 0.000 description 1
- HUBRKXKDULVIFG-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC3=C(C=C2)C=NN3)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC2=C(C=C1)C=NN2 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC3=C(C=C2)C=NN3)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC2=C(C=C1)C=NN2 HUBRKXKDULVIFG-UHFFFAOYSA-N 0.000 description 1
- DUZRDYCTLLRDSQ-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC3=C(C=C2)OCO3)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC2=C(C=C1)OCO2 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC3=C(C=C2)OCO3)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC2=C(C=C1)OCO2 DUZRDYCTLLRDSQ-UHFFFAOYSA-N 0.000 description 1
- FINLJSSDEQVSNN-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C(F)(F)F)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(C(F)(F)F)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C(F)(F)F)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(C(F)(F)F)C=C1 FINLJSSDEQVSNN-UHFFFAOYSA-N 0.000 description 1
- VGACACPSTIXZSR-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C3=CC=CC=C3)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(C2=CC=CC=C2)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C3=CC=CC=C3)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(C2=CC=CC=C2)C=C1 VGACACPSTIXZSR-UHFFFAOYSA-N 0.000 description 1
- SAFUYDUJIOVBDO-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(Cl)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(Cl)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(Cl)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(Cl)C=C1 SAFUYDUJIOVBDO-UHFFFAOYSA-N 0.000 description 1
- QDGPACHUGXOYOC-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(N(C)C)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CN(C)C1=CC=C(N)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(N(C)C)C=C2)C=C1.CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CN(C)C1=CC=C(N)C=C1 QDGPACHUGXOYOC-UHFFFAOYSA-N 0.000 description 1
- SZYHKOZLEFLGGR-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=C(N)C=CC=C1.CC1=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=CC=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=C(N)C=CC=C1.CC1=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=CC=C1 SZYHKOZLEFLGGR-UHFFFAOYSA-N 0.000 description 1
- HLZUYSMEPDLCDF-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=CC=CC(N)=C1.CC1=CC=CC(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=CC=CC(N)=C1.CC1=CC=CC(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)=C1 HLZUYSMEPDLCDF-UHFFFAOYSA-N 0.000 description 1
- ISWYSDLLOFIWPD-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=NC2=C(C=CC(N)=C2)S1.CC1=NC2=C(C=CC(NC(=O)C3=CC(/C4=N/C(NCCN(C)C)=N\C5=C4CNC(=O)N5C4=C(F)C=CC=C4F)=C(C)C=C3)=C2)S1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=NC2=C(C=CC(N)=C2)S1.CC1=NC2=C(C=CC(NC(=O)C3=CC(/C4=N/C(NCCN(C)C)=N\C5=C4CNC(=O)N5C4=C(F)C=CC=C4F)=C(C)C=C3)=C2)S1 ISWYSDLLOFIWPD-UHFFFAOYSA-N 0.000 description 1
- VBQJADUPDLMDQC-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CCOC1=CC=C(N)C=C1.CCOC1=CC=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CCOC1=CC=C(N)C=C1.CCOC1=CC=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1 VBQJADUPDLMDQC-UHFFFAOYSA-N 0.000 description 1
- ASRBQFDFVORNIX-UHFFFAOYSA-N CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.COC1=CC=C(N)C=C1.COC1=CC=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1 Chemical compound CC1=C(/C2=N/C(NCCN(C)C)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.COC1=CC=C(N)C=C1.COC1=CC=C(NC(=O)C2=CC(/C3=N/C(NCCN(C)C)=N\C4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1 ASRBQFDFVORNIX-UHFFFAOYSA-N 0.000 description 1
- DNHIMKMUAFNTPK-UHFFFAOYSA-N CC1=C(/C2=N/C(S(C)(=O)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3=CC=CC=C3)=C2)=N\1 Chemical compound CC1=C(/C2=N/C(S(C)(=O)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3=CC=CC=C3)=C2)=N\1 DNHIMKMUAFNTPK-UHFFFAOYSA-N 0.000 description 1
- FEYYQBCAIAXXDW-UHFFFAOYSA-N CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CNCCNC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3CC3)=C2)=N\1 Chemical compound CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CNCCNC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3CC3)=C2)=N\1 FEYYQBCAIAXXDW-UHFFFAOYSA-N 0.000 description 1
- KDACFLJPLXBCBU-UHFFFAOYSA-N CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3CC3)=C2)=N\1 Chemical compound CC1=C(/C2=N/C(S(C)=O)=N\C3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2CC2)C=C1.CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3CC3)=C2)=N\1 KDACFLJPLXBCBU-UHFFFAOYSA-N 0.000 description 1
- BCCAKPUVFWEALW-UHFFFAOYSA-N CC1=C(B2OC(C)(C)C(C)(C)O2)C=C(N)C=C1.CC1=C(I)C=C(N)C=C1 Chemical compound CC1=C(B2OC(C)(C)C(C)(C)O2)C=C(N)C=C1.CC1=C(I)C=C(N)C=C1 BCCAKPUVFWEALW-UHFFFAOYSA-N 0.000 description 1
- QBAQTRGGOYAOQK-UHFFFAOYSA-N CC1=C(B2OC(C)(C)C(C)(C)O2)C=C(NC(=O)C2=CSC=C2)C=C1 Chemical compound CC1=C(B2OC(C)(C)C(C)(C)O2)C=C(NC(=O)C2=CSC=C2)C=C1 QBAQTRGGOYAOQK-UHFFFAOYSA-N 0.000 description 1
- HWVOMBCJCGXBBB-UHFFFAOYSA-N CC1=C(B2OC(C)(C)C(C)(C)O2)C=CC(C(=O)O)=C1.CC1=C(C)C=C(C(=O)O)C=C1 Chemical compound CC1=C(B2OC(C)(C)C(C)(C)O2)C=CC(C(=O)O)=C1.CC1=C(C)C=C(C(=O)O)C=C1 HWVOMBCJCGXBBB-UHFFFAOYSA-N 0.000 description 1
- YZZFVCSURLWDLW-UHFFFAOYSA-N CC1=C(C2=C3CNC(=O)N(C4=C(F)C=CC=C4F)C3=NC(N3CCC(NC(=O)OC(C)(C)C)CC3)=N2)C=C(C(=O)NC2CCC2)C=C1.CC1=C(C2=C3CNC(=O)N(C4=C(F)C=CC=C4F)C3=NC(N3CCC(NC(=O)OC(C)(C)C)CC3)=N2)C=C(C(=O)O)C=C1 Chemical compound CC1=C(C2=C3CNC(=O)N(C4=C(F)C=CC=C4F)C3=NC(N3CCC(NC(=O)OC(C)(C)C)CC3)=N2)C=C(C(=O)NC2CCC2)C=C1.CC1=C(C2=C3CNC(=O)N(C4=C(F)C=CC=C4F)C3=NC(N3CCC(NC(=O)OC(C)(C)C)CC3)=N2)C=C(C(=O)O)C=C1 YZZFVCSURLWDLW-UHFFFAOYSA-N 0.000 description 1
- UCDGVRWIFTUDLG-UHFFFAOYSA-N CC1=C(C2=C3CNC(=O)N(C4=C(F)C=CC=C4F)C3=NC(N3CCC(NC(=O)OC(C)(C)C)CC3)=N2)C=C(C(=O)O)C=C1.CSC1=NC(C2=C(C)C=CC(C(=O)O)=C2)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1 Chemical compound CC1=C(C2=C3CNC(=O)N(C4=C(F)C=CC=C4F)C3=NC(N3CCC(NC(=O)OC(C)(C)C)CC3)=N2)C=C(C(=O)O)C=C1.CSC1=NC(C2=C(C)C=CC(C(=O)O)=C2)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1 UCDGVRWIFTUDLG-UHFFFAOYSA-N 0.000 description 1
- QBFBAEKGEZJYNN-UHFFFAOYSA-N CC1=C(C2=NC(N(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1 Chemical compound CC1=C(C2=NC(N(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1 QBFBAEKGEZJYNN-UHFFFAOYSA-N 0.000 description 1
- PBCSSKLMBKMPCM-UHFFFAOYSA-N CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 Chemical compound CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 PBCSSKLMBKMPCM-UHFFFAOYSA-N 0.000 description 1
- GMLXOOVKGTVCOO-UHFFFAOYSA-N CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 GMLXOOVKGTVCOO-UHFFFAOYSA-N 0.000 description 1
- PCEYSBNNNQHDJD-UHFFFAOYSA-N CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 PCEYSBNNNQHDJD-UHFFFAOYSA-N 0.000 description 1
- DSTRRIVXQDDOAO-UHFFFAOYSA-N CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 DSTRRIVXQDDOAO-UHFFFAOYSA-N 0.000 description 1
- LRRLGZDKAQLDIE-UHFFFAOYSA-N CC1=C(C2=NC(N(C)CCCN(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N(C)CCCN(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 LRRLGZDKAQLDIE-UHFFFAOYSA-N 0.000 description 1
- TWDMVYHJXUJXMM-UHFFFAOYSA-N CC1=C(C2=NC(N(C)CCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N(C)CCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 TWDMVYHJXUJXMM-UHFFFAOYSA-N 0.000 description 1
- AWJIZLGGTDFZKA-UHFFFAOYSA-N CC1=C(C2=NC(N(C)CCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(N(C)CCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 AWJIZLGGTDFZKA-UHFFFAOYSA-N 0.000 description 1
- XZQWFCFELPUDSN-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N(C)C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N(C)C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 XZQWFCFELPUDSN-UHFFFAOYSA-N 0.000 description 1
- JGPUQJKSGZRXPM-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N(C)C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CNC1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC4=CC=C(F)C=C4)=C3)=N2)CC1 Chemical compound CC1=C(C2=NC(N3CCC(N(C)C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CNC1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC4=CC=C(F)C=C4)=C3)=N2)CC1 JGPUQJKSGZRXPM-UHFFFAOYSA-N 0.000 description 1
- MKAWVFCMDKNMFO-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N(C)C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N(C)C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 MKAWVFCMDKNMFO-UHFFFAOYSA-N 0.000 description 1
- HBUXWTUERRWSEX-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N(C)C)C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N(C)C)C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 HBUXWTUERRWSEX-UHFFFAOYSA-N 0.000 description 1
- XBIKFRQBAMQSPQ-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 XBIKFRQBAMQSPQ-UHFFFAOYSA-N 0.000 description 1
- ZTFFDQGCJFKQPX-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1 ZTFFDQGCJFKQPX-UHFFFAOYSA-N 0.000 description 1
- UVOBOPAHOFPNNB-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4C(=O)NC5=C4C=CC(Cl)=C5)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N4C(=O)NC5=C4C=CC(Cl)=C5)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 UVOBOPAHOFPNNB-UHFFFAOYSA-N 0.000 description 1
- PGIPHBKWVUDUJE-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4CCC(C)CC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N4CCC(C)CC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 PGIPHBKWVUDUJE-UHFFFAOYSA-N 0.000 description 1
- ILMOPCBNDNSQIY-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 ILMOPCBNDNSQIY-UHFFFAOYSA-N 0.000 description 1
- VYTOVDYKRLFUKM-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.O=C1NCC2=C(N=C(N3CCC(N4CCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F Chemical compound CC1=C(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.O=C1NCC2=C(N=C(N3CCC(N4CCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F VYTOVDYKRLFUKM-UHFFFAOYSA-N 0.000 description 1
- AFGWYCKPTHXADB-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 AFGWYCKPTHXADB-UHFFFAOYSA-N 0.000 description 1
- MFBHMZMZHTZCLF-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.O=C1NCC2=C(N=C(N3CCC(N4CCCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F Chemical compound CC1=C(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.O=C1NCC2=C(N=C(N3CCC(N4CCCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F MFBHMZMZHTZCLF-UHFFFAOYSA-N 0.000 description 1
- TYJQWMQAQHVURX-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4CCN(C)CC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N4CCN(C)CC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 TYJQWMQAQHVURX-UHFFFAOYSA-N 0.000 description 1
- NCOIXISSPVDSLY-UHFFFAOYSA-N CC1=C(C2=NC(N3CCC(N4CCOCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCC(N4CCOCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 NCOIXISSPVDSLY-UHFFFAOYSA-N 0.000 description 1
- SXPBKJIFGPIFMA-UHFFFAOYSA-N CC1=C(C2=NC(N3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 SXPBKJIFGPIFMA-UHFFFAOYSA-N 0.000 description 1
- PHQRPLUVSRNTGP-UHFFFAOYSA-N CC1=C(C2=NC(N3CCCCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCCCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 PHQRPLUVSRNTGP-UHFFFAOYSA-N 0.000 description 1
- ZFJRORXMTKCRHY-UHFFFAOYSA-N CC1=C(C2=NC(N3CCCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CN1CCCNCC1 Chemical compound CC1=C(C2=NC(N3CCCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CN1CCCNCC1 ZFJRORXMTKCRHY-UHFFFAOYSA-N 0.000 description 1
- XJSRXFGKARITBL-UHFFFAOYSA-N CC1=C(C2=NC(N3CCN(C(C4=CC=CC=C4)C4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCN(C(C4=CC=CC=C4)C4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 XJSRXFGKARITBL-UHFFFAOYSA-N 0.000 description 1
- ONFFBYCWJVRMLY-UHFFFAOYSA-N CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 ONFFBYCWJVRMLY-UHFFFAOYSA-N 0.000 description 1
- WCFCGJBIPUBLPY-UHFFFAOYSA-N CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 WCFCGJBIPUBLPY-UHFFFAOYSA-N 0.000 description 1
- RDMWUZODFWUQTO-UHFFFAOYSA-N CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 RDMWUZODFWUQTO-UHFFFAOYSA-N 0.000 description 1
- ZAOMQQLYLSLYKR-UHFFFAOYSA-N CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 ZAOMQQLYLSLYKR-UHFFFAOYSA-N 0.000 description 1
- OBWQKPLNUFVEDQ-UHFFFAOYSA-N CC1=C(C2=NC(N3CCN(C4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCN(C4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 OBWQKPLNUFVEDQ-UHFFFAOYSA-N 0.000 description 1
- WDELANADUOBEAL-UHFFFAOYSA-N CC1=C(C2=NC(N3CCOCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(N3CCOCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 WDELANADUOBEAL-UHFFFAOYSA-N 0.000 description 1
- NUHSJTADHZDBFY-UHFFFAOYSA-N CC1=C(C2=NC(NC(CN3CCCC3)C3=CC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NC(CN1CCCC1)C1=CC=CC=C1 Chemical compound CC1=C(C2=NC(NC(CN3CCCC3)C3=CC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NC(CN1CCCC1)C1=CC=CC=C1 NUHSJTADHZDBFY-UHFFFAOYSA-N 0.000 description 1
- PMNFFKOAWUCYNA-UHFFFAOYSA-N CC1=C(C2=NC(NC(CO)CO)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NC(CO)CO Chemical compound CC1=C(C2=NC(NC(CO)CO)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NC(CO)CO PMNFFKOAWUCYNA-UHFFFAOYSA-N 0.000 description 1
- JLFKFMUAWCNFEI-UHFFFAOYSA-N CC1=C(C2=NC(NC3CC(C)(C)NC(C)(C)C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NC3CC(C)(C)NC(C)(C)C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 JLFKFMUAWCNFEI-UHFFFAOYSA-N 0.000 description 1
- QSBLWVHMICTRMI-UHFFFAOYSA-N CC1=C(C2=NC(NC3CCN(C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(NC3CCNCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NC3CCN(C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(NC3CCNCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 QSBLWVHMICTRMI-UHFFFAOYSA-N 0.000 description 1
- KWZQEJFBEWGWRM-UHFFFAOYSA-N CC1=C(C2=NC(NC3CCN(C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NC3CCN(C(=O)OC(C)(C)C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 KWZQEJFBEWGWRM-UHFFFAOYSA-N 0.000 description 1
- IMHMWHUTKKAHHV-UHFFFAOYSA-N CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 Chemical compound CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 IMHMWHUTKKAHHV-UHFFFAOYSA-N 0.000 description 1
- PPHIAMPWRICBIV-UHFFFAOYSA-N CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 PPHIAMPWRICBIV-UHFFFAOYSA-N 0.000 description 1
- BERQENKCPGDFFD-UHFFFAOYSA-N CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 BERQENKCPGDFFD-UHFFFAOYSA-N 0.000 description 1
- CNGSHTLZMSTDSN-UHFFFAOYSA-N CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 CNGSHTLZMSTDSN-UHFFFAOYSA-N 0.000 description 1
- SMSCVQACFFPXTN-UHFFFAOYSA-N CC1=C(C2=NC(NC3CCN(CC4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NC1CCN(CC2=CC=CC=C2)CC1 Chemical compound CC1=C(C2=NC(NC3CCN(CC4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NC1CCN(CC2=CC=CC=C2)CC1 SMSCVQACFFPXTN-UHFFFAOYSA-N 0.000 description 1
- NHMOHYXEMLBJSG-UHFFFAOYSA-N CC1=C(C2=NC(NCC(C)(C)CN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCC(C)(C)CN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 NHMOHYXEMLBJSG-UHFFFAOYSA-N 0.000 description 1
- QPZHXZFVLOCORM-UHFFFAOYSA-N CC1=C(C2=NC(NCC(C3=CC=CC=C3)N3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCC(C1=CC=CC=C1)N1CCCC1 Chemical compound CC1=C(C2=NC(NCC(C3=CC=CC=C3)N3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCC(C1=CC=CC=C1)N1CCCC1 QPZHXZFVLOCORM-UHFFFAOYSA-N 0.000 description 1
- GAPPURBVLNJNQE-UHFFFAOYSA-N CC1=C(C2=NC(NCC3=NC=CN3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCC3=NC=CN3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 GAPPURBVLNJNQE-UHFFFAOYSA-N 0.000 description 1
- IFFGSAVQQGQIBF-UHFFFAOYSA-N CC1=C(C2=NC(NCC3=NC=CN3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCC3=NC=CN3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 IFFGSAVQQGQIBF-UHFFFAOYSA-N 0.000 description 1
- KWRZFOWCOYCIEE-UHFFFAOYSA-N CC1=C(C2=NC(NCCC3=NC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCC3=NC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 KWRZFOWCOYCIEE-UHFFFAOYSA-N 0.000 description 1
- YGXBWPPIUYICFF-UHFFFAOYSA-N CC1=C(C2=NC(NCCC3CCCN3C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CN1CCCC1CCN Chemical compound CC1=C(C2=NC(NCCC3CCCN3C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CN1CCCC1CCN YGXBWPPIUYICFF-UHFFFAOYSA-N 0.000 description 1
- PCWMXINGQLLJBN-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 PCWMXINGQLLJBN-UHFFFAOYSA-N 0.000 description 1
- SQFZLBDTQGJGNK-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 SQFZLBDTQGJGNK-UHFFFAOYSA-N 0.000 description 1
- GMNJGLYVZOQEOL-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 GMNJGLYVZOQEOL-UHFFFAOYSA-N 0.000 description 1
- UWLOWQOBDAMWBB-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN(C)C3=CC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CN(CCCN)C1=CC=CC=C1 Chemical compound CC1=C(C2=NC(NCCCN(C)C3=CC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CN(CCCN)C1=CC=CC=C1 UWLOWQOBDAMWBB-UHFFFAOYSA-N 0.000 description 1
- WRETZPMERUMTAI-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN3C=CN=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCCN1C=CN=C1 Chemical compound CC1=C(C2=NC(NCCCN3C=CN=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCCN1C=CN=C1 WRETZPMERUMTAI-UHFFFAOYSA-N 0.000 description 1
- RHKPVCCECWSCGR-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCCN1CCCC1 Chemical compound CC1=C(C2=NC(NCCCN3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCCN1CCCC1 RHKPVCCECWSCGR-UHFFFAOYSA-N 0.000 description 1
- OKMOZMIUHCGQLS-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN3CCCC3=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCCN3CCCC3=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 OKMOZMIUHCGQLS-UHFFFAOYSA-N 0.000 description 1
- PVFJVPWNXNNTSN-UHFFFAOYSA-N CC1=C(C2=NC(NCCCN3CCOCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCCN3CCOCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 PVFJVPWNXNNTSN-UHFFFAOYSA-N 0.000 description 1
- FDHCZSQJKIWUNG-UHFFFAOYSA-N CC1=C(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 FDHCZSQJKIWUNG-UHFFFAOYSA-N 0.000 description 1
- FONKHNKQYNVCGS-UHFFFAOYSA-N CC1=C(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 FONKHNKQYNVCGS-UHFFFAOYSA-N 0.000 description 1
- XLJHWHICXBOGDA-UHFFFAOYSA-N CC1=C(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 XLJHWHICXBOGDA-UHFFFAOYSA-N 0.000 description 1
- RVKMFVYTOIIIAA-UHFFFAOYSA-N CC1=C(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 RVKMFVYTOIIIAA-UHFFFAOYSA-N 0.000 description 1
- MNQIFWYKLSDWDR-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 MNQIFWYKLSDWDR-UHFFFAOYSA-N 0.000 description 1
- XJYZGKPXLAOGEQ-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CNCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CNCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 XJYZGKPXLAOGEQ-UHFFFAOYSA-N 0.000 description 1
- QPIGINQJKSDTCF-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 QPIGINQJKSDTCF-UHFFFAOYSA-N 0.000 description 1
- UHTFLEAXRNQTHX-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CNCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CNCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 UHTFLEAXRNQTHX-UHFFFAOYSA-N 0.000 description 1
- IBNCVNJUEBKQPU-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 IBNCVNJUEBKQPU-UHFFFAOYSA-N 0.000 description 1
- HAVMUDSEFJXQQX-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CNCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NCC3=CC=CC=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(NCCN(C)C(=O)OC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CNCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NCC3=CC=CC=C3)=C2)=N1 HAVMUDSEFJXQQX-UHFFFAOYSA-N 0.000 description 1
- SRCNFHMAKOKNLN-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 SRCNFHMAKOKNLN-UHFFFAOYSA-N 0.000 description 1
- IZEHUZURKKAPFR-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F IZEHUZURKKAPFR-UHFFFAOYSA-N 0.000 description 1
- KWMAHUPZUUOYGF-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 KWMAHUPZUUOYGF-UHFFFAOYSA-N 0.000 description 1
- OFZOMCJYVUTUBP-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F OFZOMCJYVUTUBP-UHFFFAOYSA-N 0.000 description 1
- ZFXGPZYKMGCCEG-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(C(N)=O)=CC=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC(=O)C1=CC=CC(N)=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC(C(N)=O)=CC=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC(=O)C1=CC=CC(N)=C1 ZFXGPZYKMGCCEG-UHFFFAOYSA-N 0.000 description 1
- YASZSXNYYBZKHV-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C#N)C=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.N#CC1=CC=C(N)N=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C#N)C=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.N#CC1=CC=C(N)N=C1 YASZSXNYYBZKHV-UHFFFAOYSA-N 0.000 description 1
- JNEYARGCOQZLDM-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C(=O)C3=CC=CC=C3)C=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(C(=O)C2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(C(=O)C3=CC=CC=C3)C=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(C(=O)C2=CC=CC=C2)C=C1 JNEYARGCOQZLDM-UHFFFAOYSA-N 0.000 description 1
- MRKNOYMCJFMOTG-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 MRKNOYMCJFMOTG-UHFFFAOYSA-N 0.000 description 1
- ZRGBOVFWHSPPGO-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F ZRGBOVFWHSPPGO-UHFFFAOYSA-N 0.000 description 1
- FFSDLAMXOYCUOO-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(S(=O)(=O)N3CCCCC3)C=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(S(=O)(=O)N2CCCCC2)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(S(=O)(=O)N3CCCCC3)C=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=C(S(=O)(=O)N2CCCCC2)C=C1 FFSDLAMXOYCUOO-UHFFFAOYSA-N 0.000 description 1
- LYRXAHNQFKTXMT-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=CC=C2)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=CC=C2)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F LYRXAHNQFKTXMT-UHFFFAOYSA-N 0.000 description 1
- QLJGXSAGZBQFRI-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=NC=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=NC=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=NC=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=CC=NC=C1 QLJGXSAGZBQFRI-UHFFFAOYSA-N 0.000 description 1
- CAVFLHLGKINOJX-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=NC=C3C=CC=CC3=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=NC=C2/C=C\C=C/C2=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=NC=C3C=CC=CC3=C2)C=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.NC1=NC=C2/C=C\C=C/C2=C1 CAVFLHLGKINOJX-UHFFFAOYSA-N 0.000 description 1
- PZMJIMVZPIVVKX-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 PZMJIMVZPIVVKX-UHFFFAOYSA-N 0.000 description 1
- YSJYXQLVWAKVST-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=CN=C(N)S1.CC1=CN=C(NC(=O)C2=CC(C3=NC(NCCN(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)S1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CC1=CN=C(N)S1.CC1=CN=C(NC(=O)C2=CC(C3=NC(NCCN(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)S1 YSJYXQLVWAKVST-UHFFFAOYSA-N 0.000 description 1
- JWJXNWVEMRZEHA-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CCCCOC(=O)C1=CC=C(N)C=C1.CCCCOC(=O)C1=CC=C(NC(=O)C2=CC(C3=C4CNC(=O)N(C5=C(F)C=CC=C5F)C4=NC(NCCN(C)C)=N3)=C(C)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CCCCOC(=O)C1=CC=C(N)C=C1.CCCCOC(=O)C1=CC=C(NC(=O)C2=CC(C3=C4CNC(=O)N(C5=C(F)C=CC=C5F)C4=NC(NCCN(C)C)=N3)=C(C)C=C2)C=C1 JWJXNWVEMRZEHA-UHFFFAOYSA-N 0.000 description 1
- NFACSESWCXIAFZ-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CSC1=CC(NC(=O)C2=CC(C3=C4CNC(=O)N(C5=C(F)C=CC=C5F)C4=NC(NCCN(C)C)=N3)=C(C)C=C2)=CC=C1.CSC1=NC(N)=CC=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CSC1=CC(NC(=O)C2=CC(C3=C4CNC(=O)N(C5=C(F)C=CC=C5F)C4=NC(NCCN(C)C)=N3)=C(C)C=C2)=CC=C1.CSC1=NC(N)=CC=C1 NFACSESWCXIAFZ-UHFFFAOYSA-N 0.000 description 1
- OUWUELRNPNARLJ-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)OC(C)(C)C)C=C1F Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)OC(C)(C)C)C=C1F OUWUELRNPNARLJ-UHFFFAOYSA-N 0.000 description 1
- LHHVMVXNGLRDIQ-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F.CNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C(F)=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1F.CNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C(F)=C1 LHHVMVXNGLRDIQ-UHFFFAOYSA-N 0.000 description 1
- YCWBTZLIGGIQHB-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)OC(C)(C)C)C=C1F.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)OC(C)(C)C)C=C1F.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 YCWBTZLIGGIQHB-UHFFFAOYSA-N 0.000 description 1
- QFCUELGEEJJOAS-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)N(C)C)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)N(C)C)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 QFCUELGEEJJOAS-UHFFFAOYSA-N 0.000 description 1
- BVRVBSKZHDXNOG-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)NC(C)C)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)NC(C)C)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 BVRVBSKZHDXNOG-UHFFFAOYSA-N 0.000 description 1
- FIHJLPLKHKOIOU-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)NC2=CC=C(F)C=C2)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)NC2=CC=C(F)C=C2)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 FIHJLPLKHKOIOU-UHFFFAOYSA-N 0.000 description 1
- YSCRKWZXUINSFH-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)NC2=CC=CC=C2)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)NC2=CC=CC=C2)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1 YSCRKWZXUINSFH-UHFFFAOYSA-N 0.000 description 1
- ZTBAFDDXPPZOEZ-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(N)=O)=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(N)=O)=C1 ZTBAFDDXPPZOEZ-UHFFFAOYSA-N 0.000 description 1
- LLUBVZNNVBLSGU-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CCCNC(=O)C1=CC(C)=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CCCNC(=O)C1=CC(C)=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1 LLUBVZNNVBLSGU-UHFFFAOYSA-N 0.000 description 1
- CSAUIGAJYUAALT-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 CSAUIGAJYUAALT-UHFFFAOYSA-N 0.000 description 1
- PKOMPPBEWANMFC-UHFFFAOYSA-N CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CNC(=O)C1=CC(C)=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1 Chemical compound CC1=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=CC(C(=O)O)=C1.CNC(=O)C1=CC(C)=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1 PKOMPPBEWANMFC-UHFFFAOYSA-N 0.000 description 1
- XTIYKZUSICQEAY-UHFFFAOYSA-N CC1=C(C2=NC(NCCN3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCN3CCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 XTIYKZUSICQEAY-UHFFFAOYSA-N 0.000 description 1
- LYBKFTIBISLHIP-UHFFFAOYSA-N CC1=C(C2=NC(NCCN3CCCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCN1CCCCC1 Chemical compound CC1=C(C2=NC(NCCN3CCCCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCN1CCCCC1 LYBKFTIBISLHIP-UHFFFAOYSA-N 0.000 description 1
- RJNLQAMWOSCDEO-UHFFFAOYSA-N CC1=C(C2=NC(NCCN3CCN(CC4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCN1CCN(CC2=CC=CC=C2)CC1 Chemical compound CC1=C(C2=NC(NCCN3CCN(CC4=CC=CC=C4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCN1CCN(CC2=CC=CC=C2)CC1 RJNLQAMWOSCDEO-UHFFFAOYSA-N 0.000 description 1
- PXCKWMLZOUCWEF-UHFFFAOYSA-N CC1=C(C2=NC(NCCN3CCOCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCN3CCOCC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 PXCKWMLZOUCWEF-UHFFFAOYSA-N 0.000 description 1
- UKGSEDWQPVXKKV-UHFFFAOYSA-N CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1 UKGSEDWQPVXKKV-UHFFFAOYSA-N 0.000 description 1
- FSBUBBFLCFUOCT-UHFFFAOYSA-N CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 Chemical compound CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1 FSBUBBFLCFUOCT-UHFFFAOYSA-N 0.000 description 1
- VYWPSPMCKOXFIS-UHFFFAOYSA-N CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1 VYWPSPMCKOXFIS-UHFFFAOYSA-N 0.000 description 1
- ICRRBQBWBQRRSB-UHFFFAOYSA-N CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound CC1=C(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1.CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NCC2=CC=CC=C2)C=C1 ICRRBQBWBQRRSB-UHFFFAOYSA-N 0.000 description 1
- SOHWKCZKBZAZAZ-UHFFFAOYSA-N CC1=C(C2=NC(NCCNC3=CC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCNC1=CC=CC=C1 Chemical compound CC1=C(C2=NC(NCCNC3=CC=CC=C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.NCCNC1=CC=CC=C1 SOHWKCZKBZAZAZ-UHFFFAOYSA-N 0.000 description 1
- YAXVUYQBECZHLC-VVNVZEFBSA-N CC1=C(C2=NC(N[C@H]3CCN(CC4=CC=CC=C4)C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.N[C@H]1CCN(CC2=CC=CC=C2)C1 Chemical compound CC1=C(C2=NC(N[C@H]3CCN(CC4=CC=CC=C4)C3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.N[C@H]1CCN(CC2=CC=CC=C2)C1 YAXVUYQBECZHLC-VVNVZEFBSA-N 0.000 description 1
- CBBSUALNKMIJOG-UHFFFAOYSA-N CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)N(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)N(C)C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)N(C)C)=C2)=N1 CBBSUALNKMIJOG-UHFFFAOYSA-N 0.000 description 1
- MISWBCJTSDEAMY-UHFFFAOYSA-N CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 MISWBCJTSDEAMY-UHFFFAOYSA-N 0.000 description 1
- KXFQDYMTKFGPJT-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCC(CC)N1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)C1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCC(CC)N1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)C1 KXFQDYMTKFGPJT-UHFFFAOYSA-N 0.000 description 1
- WFJPWPCFJDGPPU-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 WFJPWPCFJDGPPU-UHFFFAOYSA-N 0.000 description 1
- MMMOOQFZFVVAES-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCCCN1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)CC1.CCCCN1CCNCC1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCCCN1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)CC1.CCCCN1CCNCC1 MMMOOQFZFVVAES-UHFFFAOYSA-N 0.000 description 1
- HMTYLHRIFNPEOZ-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCCN1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)CC1.CCCN1CCNCC1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCCN1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)CC1.CCCN1CCNCC1 HMTYLHRIFNPEOZ-UHFFFAOYSA-N 0.000 description 1
- NNRLUEOOTAPWBR-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CC)CCCC(C)NC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CC)CCCC(C)NC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 NNRLUEOOTAPWBR-UHFFFAOYSA-N 0.000 description 1
- GCCHFNTUDAWZDP-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 GCCHFNTUDAWZDP-UHFFFAOYSA-N 0.000 description 1
- SOCZTHKOHMOPNQ-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CC)CCN(C)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1.CCN(CC)CCNC Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CC)CCN(C)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1.CCN(CC)CCNC SOCZTHKOHMOPNQ-UHFFFAOYSA-N 0.000 description 1
- WKEIUNIQDUTKML-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1)C1=CC(C)=CC=C1.CNC(CCN)C1=CC(C)=CC=C1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN(CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1)C1=CC(C)=CC=C1.CNC(CCN)C1=CC(C)=CC=C1 WKEIUNIQDUTKML-UHFFFAOYSA-N 0.000 description 1
- PKHCAWDLPDIDAP-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN1CCCC1CNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN1CCCC1CNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 PKHCAWDLPDIDAP-UHFFFAOYSA-N 0.000 description 1
- HYVKDEZQVCDNSF-JLOGUVRSSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN1CCC[C@H]1CN.CCN1CCC[C@H]1CNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN1CCC[C@H]1CN.CCN1CCC[C@H]1CNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 HYVKDEZQVCDNSF-JLOGUVRSSA-N 0.000 description 1
- KMYRIHSKLLJVBA-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)CC1.CCN1CCNCC1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CCN1CCN(C2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=C(C)C=CC(C(=O)NC(C)C)=C3)=N2)CC1.CCN1CCNCC1 KMYRIHSKLLJVBA-UHFFFAOYSA-N 0.000 description 1
- DWJFXALCWMEIDK-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.COCCN.COCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.COCCN.COCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 DWJFXALCWMEIDK-UHFFFAOYSA-N 0.000 description 1
- JGDGZFFKCGZTQO-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC(C)C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 JGDGZFFKCGZTQO-UHFFFAOYSA-N 0.000 description 1
- HVXUAXOQVVISTH-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 HVXUAXOQVVISTH-UHFFFAOYSA-N 0.000 description 1
- WRQWJMWWRYJFRT-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)NC2=CC=C(F)C=C2)C=C1.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1 WRQWJMWWRYJFRT-UHFFFAOYSA-N 0.000 description 1
- PGUZHGZEYGSLDI-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(C(=O)O)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC(C)C)=C2)=N1 PGUZHGZEYGSLDI-UHFFFAOYSA-N 0.000 description 1
- GGHJDYWRZQDQOD-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CCOC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CCOC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 GGHJDYWRZQDQOD-UHFFFAOYSA-N 0.000 description 1
- YXYWEJYTVGKTMU-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 YXYWEJYTVGKTMU-UHFFFAOYSA-N 0.000 description 1
- XOGSPLWKMNKUNQ-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.COC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.COC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 XOGSPLWKMNKUNQ-UHFFFAOYSA-N 0.000 description 1
- HHVZKMYQHVIPBR-UHFFFAOYSA-N CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 Chemical compound CC1=C(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C(NC(=O)C2=CSC=C2)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 HHVZKMYQHVIPBR-UHFFFAOYSA-N 0.000 description 1
- HPIKELXKZGYROQ-UHFFFAOYSA-N CC1=C(F)C=C(C(=O)NC2=CC(C3=NC(N(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F Chemical compound CC1=C(F)C=C(C(=O)NC2=CC(C3=NC(N(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F HPIKELXKZGYROQ-UHFFFAOYSA-N 0.000 description 1
- GSUVKSBLLTVWHA-UHFFFAOYSA-N CC1=C(I)C=C(NC(=O)C2=CSC=C2)C=C1 Chemical compound CC1=C(I)C=C(NC(=O)C2=CSC=C2)C=C1 GSUVKSBLLTVWHA-UHFFFAOYSA-N 0.000 description 1
- LBNMNIRTEFAKJE-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(B3OC(C)(C)C(C)(C)O3)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(I)=C(C)C=C2)C=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC(B3OC(C)(C)C(C)(C)O3)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(I)=C(C)C=C2)C=C1F LBNMNIRTEFAKJE-UHFFFAOYSA-N 0.000 description 1
- KVOSITWNACMDAB-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(C3=NC(C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(NC4CCC(C(=O)OC(C)(C)C)CC4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.NC1CCNCC1 Chemical compound CC1=CC=C(C(=O)NC2=CC(C3=NC(C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(NC4CCC(C(=O)OC(C)(C)C)CC4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.NC1CCNCC1 KVOSITWNACMDAB-UHFFFAOYSA-N 0.000 description 1
- MEPCTXAFLWPQPG-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(C3=NC(N4CCC(N)CC4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC(C3=NC(N4CCC(N)CC4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F MEPCTXAFLWPQPG-UHFFFAOYSA-N 0.000 description 1
- GRXVFATVPFDGCF-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(C3=NC(NC4CC(C)(C)NC(C)(C)C4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC(C3=NC(NC4CC(C)(C)NC(C)(C)C4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F GRXVFATVPFDGCF-UHFFFAOYSA-N 0.000 description 1
- NXJGOCQMMBALFW-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(C3=NC(NC4CCN(C(=O)OC(C)(C)C)CC4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC(C3=NC(NC4CCN(C(=O)OC(C)(C)C)CC4)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F NXJGOCQMMBALFW-UHFFFAOYSA-N 0.000 description 1
- SDHNIXJTTFVQLM-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(C3=NC(OC(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC(C3=NC(OC(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F SDHNIXJTTFVQLM-UHFFFAOYSA-N 0.000 description 1
- GLEQWMJLDCPZQT-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CCOC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CC=C(C)C(F)=C3)=C2)=N1 Chemical compound CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CCOC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CC=C(C)C(F)=C3)=C2)=N1 GLEQWMJLDCPZQT-UHFFFAOYSA-N 0.000 description 1
- MXGPZLIPISPPOY-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CC=C(C)C(F)=C3)=C2)=N1 Chemical compound CC1=CC=C(C(=O)NC2=CC(C3=NC(S(C)(=O)=O)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C(C)C=C2)C=C1F.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CC=C(C)C(F)=C3)=C2)=N1 MXGPZLIPISPPOY-UHFFFAOYSA-N 0.000 description 1
- IORSZSQFVWUFNB-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(F)=C(F)C=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC(F)=C(F)C=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F IORSZSQFVWUFNB-UHFFFAOYSA-N 0.000 description 1
- BNSUUXRPHFOIOS-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC(I)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)O)C=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC(I)=C(C)C=C2)C=C1F.CC1=CC=C(C(=O)O)C=C1F BNSUUXRPHFOIOS-UHFFFAOYSA-N 0.000 description 1
- DFCZXQXGPZNKPY-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CC=CC=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=CC=CC=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F DFCZXQXGPZNKPY-UHFFFAOYSA-N 0.000 description 1
- NPNBPXMJWHCCFG-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=CN=CC=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=CN=CC=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F NPNBPXMJWHCCFG-UHFFFAOYSA-N 0.000 description 1
- HCIHSVUJTDLTTL-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(N(C)CCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(N(C)CCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F HCIHSVUJTDLTTL-UHFFFAOYSA-N 0.000 description 1
- LZGSCXLHFHHXMC-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(N(C)CCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(N(C)CCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F LZGSCXLHFHHXMC-UHFFFAOYSA-N 0.000 description 1
- KJHMETTXXIEKON-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCC(C)(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCC(C)(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F KJHMETTXXIEKON-UHFFFAOYSA-N 0.000 description 1
- JBPRQYFUUYFVHM-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCC2=NC=CN2)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCC2=NC=CN2)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F JBPRQYFUUYFVHM-UHFFFAOYSA-N 0.000 description 1
- GONXMSKEVYJJEX-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F GONXMSKEVYJJEX-UHFFFAOYSA-N 0.000 description 1
- MRODYNANVBVSKC-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCCNC(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCCNC(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F MRODYNANVBVSKC-UHFFFAOYSA-N 0.000 description 1
- NZBDGPUAARXUNY-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F NZBDGPUAARXUNY-UHFFFAOYSA-N 0.000 description 1
- JSUQXWUAMDENGR-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCNC(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCNC(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F JSUQXWUAMDENGR-UHFFFAOYSA-N 0.000 description 1
- JNKVUGVDKFIUFY-PFEQFJNWSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NC[C@@H](C)O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NC[C@@H](C)O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F JNKVUGVDKFIUFY-PFEQFJNWSA-N 0.000 description 1
- JNKVUGVDKFIUFY-UQKRIMTDSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NC[C@H](C)O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NC[C@H](C)O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F JNKVUGVDKFIUFY-UQKRIMTDSA-N 0.000 description 1
- YPANGHUHGPJKBG-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 YPANGHUHGPJKBG-UHFFFAOYSA-N 0.000 description 1
- JJIRIUOJAWAVHP-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 JJIRIUOJAWAVHP-UHFFFAOYSA-N 0.000 description 1
- CBHGVRSHXMMHKU-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 CBHGVRSHXMMHKU-UHFFFAOYSA-N 0.000 description 1
- JUJGVFUDYMKLHZ-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.COC1=C(CCNC2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=CC(C(=O)NC4=NC=CS4)=CC=C3C)=N2)C=CC=C1 Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.COC1=C(CCNC2=NC3=C(CNC(=O)N3C3=C(F)C=CC=C3F)C(C3=CC(C(=O)NC4=NC=CS4)=CC=C3C)=N2)C=CC=C1 JUJGVFUDYMKLHZ-UHFFFAOYSA-N 0.000 description 1
- NAOHKASSFPTVBY-UHFFFAOYSA-N CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 Chemical compound CC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(S(C)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1 NAOHKASSFPTVBY-UHFFFAOYSA-N 0.000 description 1
- HZHMWGZWFKDCOI-UHFFFAOYSA-N CC1=CC=C(C(=O)NCC(C)(C)C)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NCC(C)(C)C)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F HZHMWGZWFKDCOI-UHFFFAOYSA-N 0.000 description 1
- QILBTYVHVDRCCX-PKLMIRHRSA-N CC1=CC=C(C(=O)NC[C@@H](C)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC[C@@H](C)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F QILBTYVHVDRCCX-PKLMIRHRSA-N 0.000 description 1
- QILBTYVHVDRCCX-NTISSMGPSA-N CC1=CC=C(C(=O)NC[C@H](C)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CC1=CC=C(C(=O)NC[C@H](C)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F QILBTYVHVDRCCX-NTISSMGPSA-N 0.000 description 1
- GAOKIEMTQUTSCA-UHFFFAOYSA-N CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 GAOKIEMTQUTSCA-UHFFFAOYSA-N 0.000 description 1
- MMNNJXMDFFGCQW-UHFFFAOYSA-N CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.COC(=O)C1=CC=C(C)C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C1 Chemical compound CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.COC(=O)C1=CC=C(C)C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C1 MMNNJXMDFFGCQW-UHFFFAOYSA-N 0.000 description 1
- IVNVNXPHFBZLIR-UHFFFAOYSA-N CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.COC1=NC=C(NC(=O)C2=CC=C(C)C(C3=NC(NCCN(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C2)C=C1 Chemical compound CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.COC1=NC=C(NC(=O)C2=CC=C(C)C(C3=NC(NCCN(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C2)C=C1 IVNVNXPHFBZLIR-UHFFFAOYSA-N 0.000 description 1
- RUTBKMNJUAFEIX-UHFFFAOYSA-N CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CSC1=CC=C(NC(=O)C2=CC=C(C)C(C3=NC(NCCN(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C2)C=C1 Chemical compound CC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CSC1=CC=C(NC(=O)C2=CC=C(C)C(C3=NC(NCCN(C)C)=NC4=C3CNC(=O)N4C3=C(F)C=CC=C3F)=C2)C=C1 RUTBKMNJUAFEIX-UHFFFAOYSA-N 0.000 description 1
- ZJHNMQLHGNGJBT-UHFFFAOYSA-N CCC1=CC=C(C(=O)NC2=CC(F)=C(F)C=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CCC1=CC=C(C(=O)NC2=CC(F)=C(F)C=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F ZJHNMQLHGNGJBT-UHFFFAOYSA-N 0.000 description 1
- CUYRTABYCMDAMO-UHFFFAOYSA-N CCC1=CC=C(C(=O)NC2=CC=C(F)C=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CCC1=CC=C(C(=O)NC2=CC=C(F)C=C2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F CUYRTABYCMDAMO-UHFFFAOYSA-N 0.000 description 1
- VRCQLZSYUYDDBY-UHFFFAOYSA-N CCC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CCC1=CC=C(C(=O)NC2=NC=CS2)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F VRCQLZSYUYDDBY-UHFFFAOYSA-N 0.000 description 1
- SLLFYWNGOFIEMQ-UHFFFAOYSA-N CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(N)=O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F Chemical compound CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CCC1=CC=C(C(N)=O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F SLLFYWNGOFIEMQ-UHFFFAOYSA-N 0.000 description 1
- NHVYDXGBANHSAW-UHFFFAOYSA-N CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CCC1=CC=C(C(=O)O)C=C1C1=NC(NCCN(C)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 NHVYDXGBANHSAW-UHFFFAOYSA-N 0.000 description 1
- PVMXDKLJAQBFSO-UHFFFAOYSA-N CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC)=C2)=N1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC)=C2)=N1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 PVMXDKLJAQBFSO-UHFFFAOYSA-N 0.000 description 1
- NTPIRFIMCKRXDE-UHFFFAOYSA-N CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NCCC)=C2)=N1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCCN(CCCC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NCCC)=C2)=N1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 NTPIRFIMCKRXDE-UHFFFAOYSA-N 0.000 description 1
- LCHDNGDQESTWSX-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 LCHDNGDQESTWSX-UHFFFAOYSA-N 0.000 description 1
- ANHABZLTEWLCPN-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 ANHABZLTEWLCPN-UHFFFAOYSA-N 0.000 description 1
- VDGJWBAVALMXPE-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 VDGJWBAVALMXPE-UHFFFAOYSA-N 0.000 description 1
- DBBPYWYROIOHIL-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 DBBPYWYROIOHIL-UHFFFAOYSA-N 0.000 description 1
- PCMOBJTUAMXBKN-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCC(=O)O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCC(=O)O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 PCMOBJTUAMXBKN-UHFFFAOYSA-N 0.000 description 1
- RKUBHILLPAWTMA-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCCCl)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCCCl)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 RKUBHILLPAWTMA-UHFFFAOYSA-N 0.000 description 1
- WVIVTGOCRMZMHG-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 WVIVTGOCRMZMHG-UHFFFAOYSA-N 0.000 description 1
- FZECESBUWNBYDW-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCCN(CC)CC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCCN(CC)CC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 FZECESBUWNBYDW-UHFFFAOYSA-N 0.000 description 1
- HEUQQSBRPBFLOT-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 HEUQQSBRPBFLOT-UHFFFAOYSA-N 0.000 description 1
- GXAASBIGNIMVCR-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 GXAASBIGNIMVCR-UHFFFAOYSA-N 0.000 description 1
- KWFRUUJPFNLECN-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 KWFRUUJPFNLECN-UHFFFAOYSA-N 0.000 description 1
- IQNOCWQGURCWFB-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=CC=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=CC=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 IQNOCWQGURCWFB-UHFFFAOYSA-N 0.000 description 1
- IEJDBPNDSBTSFZ-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 IEJDBPNDSBTSFZ-UHFFFAOYSA-N 0.000 description 1
- ROXFFOLHMBIEOC-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 ROXFFOLHMBIEOC-UHFFFAOYSA-N 0.000 description 1
- NFBSVJWURBKEOH-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCCNC(=O)C1=CC(C2=NC(S(C)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCCNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 NFBSVJWURBKEOH-UHFFFAOYSA-N 0.000 description 1
- UKZKOAQKGQWHHI-UHFFFAOYSA-N CCCNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 Chemical compound CCCNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 UKZKOAQKGQWHHI-UHFFFAOYSA-N 0.000 description 1
- GLYHKYKCCLOYTH-UHFFFAOYSA-N CCCNC(=O)C1=CC=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 Chemical compound CCCNC(=O)C1=CC=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 GLYHKYKCCLOYTH-UHFFFAOYSA-N 0.000 description 1
- NGMJALFZSHHNBA-UHFFFAOYSA-N CCN(CC)C(=O)C1=CC(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCN(CC)C(=O)C1=CC(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 NGMJALFZSHHNBA-UHFFFAOYSA-N 0.000 description 1
- AGJRYPSYFRTVMK-UHFFFAOYSA-N CCN(CC)C(=O)C1=CC(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCN(CC)C(=O)C1=CC(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 AGJRYPSYFRTVMK-UHFFFAOYSA-N 0.000 description 1
- RICVAPZVKWPLSI-UHFFFAOYSA-N CCN(CC)C(=O)C1=CC(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCN(CC)C(=O)C1=CC(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 RICVAPZVKWPLSI-UHFFFAOYSA-N 0.000 description 1
- SVCBZODRJBRWRG-UHFFFAOYSA-N CCN(CC)C(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCN(CC)C(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 SVCBZODRJBRWRG-UHFFFAOYSA-N 0.000 description 1
- DXUZDMVOMMFMNJ-UHFFFAOYSA-N CCN(CC)C(=O)C1=CC(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCN(CC)C(=O)C1=CC(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 DXUZDMVOMMFMNJ-UHFFFAOYSA-N 0.000 description 1
- CAGUBTXMWIXHBC-UHFFFAOYSA-N CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCN(CC)C(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CCN(CC)C(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 CAGUBTXMWIXHBC-UHFFFAOYSA-N 0.000 description 1
- GTLPUCPHVWTAEH-UHFFFAOYSA-N CCN(CC)C(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CCN(CC)C(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 GTLPUCPHVWTAEH-UHFFFAOYSA-N 0.000 description 1
- PCHLSILRQNNVBT-UHFFFAOYSA-N CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC)=C2)=N1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)NC)=C2)=N1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 PCHLSILRQNNVBT-UHFFFAOYSA-N 0.000 description 1
- AOLVGNMDLBFEOC-UHFFFAOYSA-N CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1.CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 AOLVGNMDLBFEOC-UHFFFAOYSA-N 0.000 description 1
- FJZONHRRVMKOBT-UHFFFAOYSA-N CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CCN(CC)CCCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 FJZONHRRVMKOBT-UHFFFAOYSA-N 0.000 description 1
- MREOEIUPJYSGBS-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)N(C)C)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)N(C)C)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 MREOEIUPJYSGBS-UHFFFAOYSA-N 0.000 description 1
- VLELVFAIQOQBBS-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)NC3=CC=C(F)C=C3)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)NC3=CC=C(F)C=C3)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 VLELVFAIQOQBBS-UHFFFAOYSA-N 0.000 description 1
- DCZJODMKVNBIFJ-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)NC3=CC=CC=C3)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)NC3=CC=CC=C3)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 DCZJODMKVNBIFJ-UHFFFAOYSA-N 0.000 description 1
- TZHUZGOMAPSLMG-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)NC3=NC=CS3)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)NC3=NC=CS3)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1 TZHUZGOMAPSLMG-UHFFFAOYSA-N 0.000 description 1
- AOVPQNQYNQNJHA-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(N)=O)C=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(N)=O)C=C2)=N1 AOVPQNQYNQNJHA-UHFFFAOYSA-N 0.000 description 1
- VHGLGYCIWVYHNA-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 VHGLGYCIWVYHNA-UHFFFAOYSA-N 0.000 description 1
- BMLAZNUXXDEEEW-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1.CNC(=O)C1=CC=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=C(C(=O)O)C=C2)=N1.CNC(=O)C1=CC=C(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)C=C1 BMLAZNUXXDEEEW-UHFFFAOYSA-N 0.000 description 1
- SWQMIOMPVYFLQC-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)N(C)C)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)N(C)C)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 SWQMIOMPVYFLQC-UHFFFAOYSA-N 0.000 description 1
- WUONCUGDKNPLQI-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)NC3=CC=C(F)C=C3)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 WUONCUGDKNPLQI-UHFFFAOYSA-N 0.000 description 1
- GUXQMVJOIJMDPQ-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)NC3=CC=CC=C3)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)NC3=CC=CC=C3)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 GUXQMVJOIJMDPQ-UHFFFAOYSA-N 0.000 description 1
- GLMFTQJAZRNJNR-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)NC3=NC=CS3)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)NC3=NC=CS3)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1 GLMFTQJAZRNJNR-UHFFFAOYSA-N 0.000 description 1
- XOWHREHKOATLDC-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(N)=O)=C2)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(N)=O)=C2)=N1 XOWHREHKOATLDC-UHFFFAOYSA-N 0.000 description 1
- ZHIUXSMLHRYXFH-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1.CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 ZHIUXSMLHRYXFH-UHFFFAOYSA-N 0.000 description 1
- RQNRESCKDOLONS-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1.CNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=CC=C1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC=CC(C(=O)O)=C2)=N1.CNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=CC=C1 RQNRESCKDOLONS-UHFFFAOYSA-N 0.000 description 1
- HOOAPHLAFGXASU-UHFFFAOYSA-N CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CN(C)CCNC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 HOOAPHLAFGXASU-UHFFFAOYSA-N 0.000 description 1
- JUDZNERRDHLLOV-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(N(C)CCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 JUDZNERRDHLLOV-UHFFFAOYSA-N 0.000 description 1
- RCULSUWHWDOKAN-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(N3CCC(N4CCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 RCULSUWHWDOKAN-UHFFFAOYSA-N 0.000 description 1
- ICGWZRZEGBHXBM-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(N3CCC(N4CCCCC4)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 ICGWZRZEGBHXBM-UHFFFAOYSA-N 0.000 description 1
- XVYKREBIIWVVNP-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(N3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 XVYKREBIIWVVNP-UHFFFAOYSA-N 0.000 description 1
- MUUZLBHMSZDMFR-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(NC3CCN(C)CC3)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 MUUZLBHMSZDMFR-UHFFFAOYSA-N 0.000 description 1
- OUDOFTLPDCLOCX-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(NCCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 OUDOFTLPDCLOCX-UHFFFAOYSA-N 0.000 description 1
- VRSIQUABTMSOOL-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(NCCCNC(C)(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 VRSIQUABTMSOOL-UHFFFAOYSA-N 0.000 description 1
- QOGWGGBCFGXWDA-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(NCCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 QOGWGGBCFGXWDA-UHFFFAOYSA-N 0.000 description 1
- RUVXFTPZOGRBJX-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(NCCN(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 RUVXFTPZOGRBJX-UHFFFAOYSA-N 0.000 description 1
- CGPICIHKQOABCX-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(NCCNC(C)C)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 CGPICIHKQOABCX-UHFFFAOYSA-N 0.000 description 1
- KMUGDBDSGPUGRF-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 Chemical compound CNC(=O)C1=CC(C2=NC(S(C)(=O)=O)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1 KMUGDBDSGPUGRF-UHFFFAOYSA-N 0.000 description 1
- KURDKKVJXNUXSC-UHFFFAOYSA-N CNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 Chemical compound CNC(=O)C1=CC(C2=NC(SC)=NC3=C2CNC(=O)N3C2=C(F)C=CC=C2F)=C(C)C=C1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 KURDKKVJXNUXSC-UHFFFAOYSA-N 0.000 description 1
- FTXXZXHOBRJJFP-UHFFFAOYSA-N CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 FTXXZXHOBRJJFP-UHFFFAOYSA-N 0.000 description 1
- VQIRYDWBWIVDCI-UHFFFAOYSA-N CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.O=C1NCC2=C(N=C(N3CCC(N4CCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F Chemical compound CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.O=C1NCC2=C(N=C(N3CCC(N4CCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F VQIRYDWBWIVDCI-UHFFFAOYSA-N 0.000 description 1
- KTDLMONXPBJIPJ-UHFFFAOYSA-N CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.O=C1NCC2=C(N=C(N3CCC(N4CCCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F Chemical compound CS(=O)C1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1.O=C1NCC2=C(N=C(N3CCC(N4CCCCC4)CC3)N=C2Cl)N1C1=C(F)C=CC=C1F KTDLMONXPBJIPJ-UHFFFAOYSA-N 0.000 description 1
- MQQZACHUEZQBSU-UHFFFAOYSA-N CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3=CC=CC=C3)=C2)=N\1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 Chemical compound CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3=CC=CC=C3)=C2)=N\1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)O)=C2)=N1 MQQZACHUEZQBSU-UHFFFAOYSA-N 0.000 description 1
- SMUNYGXKZADRSU-UHFFFAOYSA-N CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3CC3)=C2)=N\1.CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)O)=C2)=N\1 Chemical compound CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)NCC3CC3)=C2)=N\1.CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(C(=O)O)=C2)=N\1 SMUNYGXKZADRSU-UHFFFAOYSA-N 0.000 description 1
- LQRLZDJEOXHLTA-UHFFFAOYSA-N CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N\1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CSC1=N/C2=C(CNC(=O)N2C2=C(F)C=CC=C2F)/C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N\1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 LQRLZDJEOXHLTA-UHFFFAOYSA-N 0.000 description 1
- FKGBMQRFJGTAMT-UHFFFAOYSA-N CSC1=NC(C2=C(C)C=CC(C(=O)O)=C2)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1.CSC1=NC(Cl)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1 Chemical compound CSC1=NC(C2=C(C)C=CC(C(=O)O)=C2)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1.CSC1=NC(Cl)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1 FKGBMQRFJGTAMT-UHFFFAOYSA-N 0.000 description 1
- DLSMVAHIMQAWEU-UHFFFAOYSA-N CSC1=NC(Cl)=C(C#N)C(Cl)=N1.CSC1=NC(Cl)=C(C#N)C(NC2=C(F)C=CC=C2F)=N1.CSC1=NC(Cl)=C(C=NO)C(Cl)=N1.CSC1=NC(O)=CC(O)=N1.[H]C(=O)C1=C(Cl)N=C(SC)N=C1Cl Chemical compound CSC1=NC(Cl)=C(C#N)C(Cl)=N1.CSC1=NC(Cl)=C(C#N)C(NC2=C(F)C=CC=C2F)=N1.CSC1=NC(Cl)=C(C=NO)C(Cl)=N1.CSC1=NC(O)=CC(O)=N1.[H]C(=O)C1=C(Cl)N=C(SC)N=C1Cl DLSMVAHIMQAWEU-UHFFFAOYSA-N 0.000 description 1
- VUGWUDMNPGDFLC-UHFFFAOYSA-N CSC1=NC(Cl)=C(C#N)C(NC2=C(F)C=CC=C2F)=N1.CSC1=NC(Cl)=C(CN)C(NC2=C(F)C=CC=C2F)=N1 Chemical compound CSC1=NC(Cl)=C(C#N)C(NC2=C(F)C=CC=C2F)=N1.CSC1=NC(Cl)=C(CN)C(NC2=C(F)C=CC=C2F)=N1 VUGWUDMNPGDFLC-UHFFFAOYSA-N 0.000 description 1
- JSIJKIUIKKNPMX-UHFFFAOYSA-N CSC1=NC(Cl)=C(CN)C(NC2=C(F)C=CC=C2F)=N1.CSC1=NC(Cl)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1 Chemical compound CSC1=NC(Cl)=C(CN)C(NC2=C(F)C=CC=C2F)=N1.CSC1=NC(Cl)=C2CNC(=O)N(C3=C(F)C=CC=C3F)C2=N1 JSIJKIUIKKNPMX-UHFFFAOYSA-N 0.000 description 1
- JQELKLLITNKCAN-UHFFFAOYSA-N CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)N(C)C)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(C(=O)N(C)C)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 JQELKLLITNKCAN-UHFFFAOYSA-N 0.000 description 1
- AFRTUVRLFPAVMY-UHFFFAOYSA-N CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(N)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 Chemical compound CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(N)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CSC=C3)=C2)=N1 AFRTUVRLFPAVMY-UHFFFAOYSA-N 0.000 description 1
- IJEBIDFLDCBPGG-UHFFFAOYSA-N CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(N)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(N)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 IJEBIDFLDCBPGG-UHFFFAOYSA-N 0.000 description 1
- ZGTXEEUGHUTOII-UHFFFAOYSA-N CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CC(F)=C(C)C=C3)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 Chemical compound CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=C(C)C=CC(NC(=O)C3=CC(F)=C(C)C=C3)=C2)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(Cl)=N1 ZGTXEEUGHUTOII-UHFFFAOYSA-N 0.000 description 1
- ZNTGMMVVDQPBJS-UHFFFAOYSA-N CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)O)=CC=C2C)=N1 Chemical compound CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)NC3=NC=CS3)=CC=C2C)=N1.CSC1=NC2=C(CNC(=O)N2C2=C(F)C=CC=C2F)C(C2=CC(C(=O)O)=CC=C2C)=N1 ZNTGMMVVDQPBJS-UHFFFAOYSA-N 0.000 description 1
- NUWLVKPZSCEDQM-UHFFFAOYSA-N Cc(c(F)c1)ccc1/C(/O)=[O]/C Chemical compound Cc(c(F)c1)ccc1/C(/O)=[O]/C NUWLVKPZSCEDQM-UHFFFAOYSA-N 0.000 description 1
- LTOYXFJHJURXMO-UHFFFAOYSA-N Cc(c(F)c1)ccc1C(Nc1ccc(C)c(I)c1)=O Chemical compound Cc(c(F)c1)ccc1C(Nc1ccc(C)c(I)c1)=O LTOYXFJHJURXMO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- This invention relates to novel 1,5,7-trisubstituted-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-[1H]-one compounds and their use as pharmaceuticals, particularly as p38 kinase inhibitors, for the treatment of certain diseases and conditions.
- Intracellular signal transduction is the means by which cells respond to extracellular stimuli. Regardless of the nature of the cell surface receptor (e.g. protein tyrosine kinase or seven-transmembrane G-protein coupled), protein kinases and phosphatases along with phospholipases are the essential machinery by which the signal is further transmitted within the cell [Marshall, J. C. Cell, 80, 179-278 (1995)].
- the cell surface receptor e.g. protein tyrosine kinase or seven-transmembrane G-protein coupled
- protein kinases and phosphatases along with phospholipases are the essential machinery by which the signal is further transmitted within the cell [Marshall, J. C. Cell, 80, 179-278 (1995)].
- Protein kinases can be categorized into five classes with the two major classes being tyrosine kinases and serine/threonine kinases, depending upon whether the enzyme phosphorylates its substrate(s) on specific tyrosine(s) or serine/threonine(s) residues [Hunter, T., Methods in Enzymology ( Protein Kinase Classification ) p. 3, Hunter, T.; Sefton, B. M.; eds. vol. 200, Academic Press; San Diego, 1991].
- the mitogen-activated kinases are now understood to transduce signals from many extracellular stimuli such as environmental stress, infectious agents, cytokines and growth factors.
- the MAPKs modulate the activity of numerous cell functions such as translocation and activation of transcription factors that control transcription of effector molecules such as cytokines, COX-2, iNOS; the activity of downstream kinases that effect translation of mRNAs; and cell cycle pathways through transcription or modification of enzymes.
- One of these three major pathways is the p38 MAPK pathway, which refers in most cell types to the isoform p38a which is ubiquitously expressed.
- Extracellular stimuli such as those described above are generated in a number of chronic diseases which are now understood to have a common underlying pathophysiology termed inflammation.
- An environmental insult or local cell damage activates cellular response pathways, including but not limited to p38; local cells then generate cytokines and chemokines, in turn recruiting lymphocytes such as neutrophils and other granulocytes.
- lymphocytes such as neutrophils and other granulocytes.
- the consequences include recruitment of additional lymphocytes such as additional phagocytic cells or cytotoxic T cells, and ultimately the adaptive immune response is initiated through activation of T cells.
- Atherosclerosis is regarded as a chronic inflammatory disease, which develops in response to injury of the vessel wall and is characterized by the complex development of an occlusive and prothrombotic atheroma.
- the pathogenesis of this lesion generally involves endothelial dysfunction (reduced bioavailable NO), adhesion molecule expression, adhesion and infiltration of leukocytes, cytokine and growth factor generation, accumulation of foam cells, expansion of extracellular lipid and matrix, activation of matrix metalloproteases (MMPs) and proliferation of vascular smooth muscle cells.
- endothelial dysfunction reduced bioavailable NO
- adhesion molecule expression adhesion and infiltration of leukocytes
- cytokine and growth factor generation accumulation of foam cells
- expansion of extracellular lipid and matrix activation of matrix metalloproteases (MMPs) and proliferation of vascular smooth muscle cells.
- MMPs matrix metalloproteases
- CSBP CSBP
- p38 the isoforms p38 ⁇ and p38 ⁇ are the targets of the compounds described
- SK&F 86002 was the prototypic example.
- These compounds inhibited IL-1 and TNF synthesis in human monocytes at concentrations in the low uM range [Lee, et al., Int. J. Immunopharmac. 10(7), 835 (1988)] and exhibited activity in animal models which are refractory to cyclooxygenase inhibitors [Lee; et al., Annals N.Y. Acad. Sci., 696, 149 (1993)].
- the mechanism by which stress signals (including bacterial and viral infection, pro-inflammatory cytokines, oxidants, UV light and osmotic stress) activate p38 is through activation of kinases upstream from p38 which in turn phosphorylate p38 at threonine 180 and tyrosine 182 resulting in p38 activation.
- MAPKAP kinase-2 and MAPKAP kinase-3 have been identified as downstream substrates of CSBP/p38 which in turn phosphorylate heat shock protein Hsp27 and other substrates. Additional downstream substrates known to be phosphorylated by p38 include kinases (Mnk1/2, MSK1/2 and PRAK) and transcription factors (CHOP, MEF2, ATF2 and CREB).
- p38 kinase inhibitors are effective in a number of different cell types in decreasing the synthesis of a wide variety of pro-inflammatory proteins including, IL-6, IL-8, GM-CSF, RANTES and COX-2.
- Inhibitors of p38 kinase have also been shown to suppress the TNF-induced expression of VCAM-1 on endothelial cells, the TNF-induced phosphorylation and activation of cytosolic PLA2 and the IL-1-stimulated synthesis of collagenase and stromelysin.
- Interleukin-1 IL-1
- Tumor Necrosis Factor TNF
- IL-1 Tumor Necrosis Factor
- monocytes a variety of cells
- macrophages a variety of cells
- smooth muscle cells IL-1
- IL-1 has been demonstrated to mediate a variety of biological activities thought to be important in immunoregulation and other physiological conditions such as inflammation [See, e.g., Dinarello et al., Rev. Infect. Disease, 6, 51 (1984)].
- the myriad of known biological activities of IL-1 include the activation of T helper cells, induction of fever, stimulation of prostaglandin or collagenase production, neutrophil chemotaxis, induction of acute phase proteins and the suppression of plasma iron levels.
- IL-1 IL-1-induced arthritis
- osteoarthritis IL-1-induced arthritis
- toxic shock syndrome other acute or chronic inflammatory disease states
- other acute or chronic inflammatory disease states such as the inflammatory reaction induced by endotoxin or inflammatory bowel disease; tuberculosis, atherosclerosis, muscle degeneration, cachexia, psoriatic arthritis, Reiter's syndrome, rheumatoid arthritis, gout, traumatic arthritis, rubella arthritis, and acute synovitis.
- Evidence also links IL-1 activity to diabetes and pancreatic ⁇ cells [review of the biological activities which have been attributed to IL-1 Dinarello, J. Clinical Immunology, 5 (5), 287-297 (1985)].
- TNF production has been implicated in mediating or exacerbating a number of diseases including rheumatoid arthritis, rheumatoid spondylitis, osteoarthritis, gouty arthritis and other arthritic conditions; sepsis, septic shock, endotoxic shock, gram negative sepsis, toxic shock syndrome, adult respiratory distress syndrome, cerebral malaria, chronic obstructive pulmonary disease, silicosis, pulmonary sarcoidosis, bone resorption diseases, reperfusion injury, graft vs.
- diseases including rheumatoid arthritis, rheumatoid spondylitis, osteoarthritis, gouty arthritis and other arthritic conditions; sepsis, septic shock, endotoxic shock, gram negative sepsis, toxic shock syndrome, adult respiratory distress syndrome, cerebral malaria, chronic obstructive pulmonary disease, silicosis, pulmonary sarcoidosis, bone resorption diseases,
- allograft rejections fever and myalgias due to infection, such as influenza, cachexia secondary to infection or malignancy, cachexia, secondary to acquired immune deficiency syndrome (AIDS), AIDS, ARC (AIDS related complex), keloid formation, scar tissue formation, Crohn's disease, ulcerative colitis, or pyresis.
- AIDS cachexia secondary to infection or malignancy
- cachexia secondary to acquired immune deficiency syndrome
- AIDS AIDS
- ARC AIDS related complex
- keloid formation scar tissue formation
- Crohn's disease Crohn's disease
- ulcerative colitis or pyresis.
- Inflammatory diseases are also marked by increases in IL-6 and C-reactive protein (CRP), both of which are sensitive to inhibition by p38 inhibitors.
- IL-6 stimulation of CRP production is directly inhibited by p38 inhibitors in human vascular endothelial cells, and CRP is produced by hepatocytes in response to IL-6.
- CRP is considered a major risk factor for cardiovascular disease [Circulation 2003.107: 363-369] and may be a significant independent risk factor for chronic obstructive pulmonary disease [Circulation 2003. 107:1514-1519].
- IL-6 is also upregulated in endometriosis [Bedaiwy et al., 2002, Human Reproduction 17:426-431; Witz, 2000, Fertility and Sterility 73: 212-214].
- Interleukin-8 (IL-8) and RANTES are chemotactic factors produced by several cell types including mononuclear cells, fibroblasts, endothelial cells, epithelial cells, neutrophils and T cells. Chemokine production is induced by pro-inflammatory stimuli such as IL-1, TNF, or lipopolysaccharide (LPS), or viral infection. IL-8 stimulates a number of functions in vitro. It has been shown to have chemoattractant properties for neutrophils, T-lymphocytes, and basophils. In addition it induces histamine release from basophils from both normal and atopic individuals as well as lysosomal enzyme release and respiratory burst from neutrophils.
- pro-inflammatory stimuli such as IL-1, TNF, or lipopolysaccharide (LPS), or viral infection.
- IL-8 stimulates a number of functions in vitro. It has been shown to have chemoattractant properties for neutrophils, T-ly
- IL-8 has also been shown to increase the surface expression of Mac-1 (CD11b/CD18) on neutrophils without de novo protein synthesis, which may contribute to increased adhesion of the neutrophils to vascular endothelial cells.
- Mac-1 CD11b/CD18
- Many diseases are characterized by massive neutrophil infiltration.
- Conditions such as chronic obstructive pulmonary disease associated with an increase in IL-8 production would benefit by compounds which are suppressive of IL-8 production.
- RANTES is produced by cells such as epithelial cells and airway smooth muscle in response to infection or cytokine stimulation. Its main chemoattraction is for T cell subtypes and blood-borne monocytes.
- IL-1, TNF and other cytokines affect a wide variety of cells and tissues and these cytokines as well as other leukocyte derived cytokines are important as critical inflammatory mediators of a wide variety of disease states and conditions. The inhibition of these cytokines is of benefit in controlling, reducing and alleviating many of these disease states.
- CSBP/p38 signal transduction via CSBP/p38 is required for the effector functions of several of these same pro-inflammatory proteins plus many others.
- growth factors such as VEGF, PDGF, NGF signal through surface receptors which in turn activate cellular signaling pathways including p38 MAPK [Ono, K. and Han, J., Cellular Signalling, 12 1-13 (2000); Kyriakis, J M and Avruch, J. Physiol Rev 81: 807-869 (2001)].
- TGF ⁇ a key molecule in the control of inflammatory response, also activates p38 as a consequence of engagement of the TGF ⁇ receptor.
- the involvement of CSBP/p38 in multiple stress-induced signal transduction pathways provides additional rationale for the potential utility of CSBP/p38 in the treatment of diseases resulting from the excessive and destructive activation of the immune system, or chronic inflammation. This expectation is supported by the potent and diverse activities described for CSBP/p38 kinase inhibitors [Badger, et al., J. Pharm. Exp. Thera. 279 (3): 1453-1461. (1996); Griswold, et al, Pharmacol. Comm. 7, 323-229 (1996); Jackson, et al., J. Pharmacol.
- TGF- ⁇ transforming growth factor beta
- p38 inhibitor SB-242235 inhibited the TGF- ⁇ -induced increases in fibronectin and thrombospondin (Laping et al., 2002, Molec. Pharmacol. 62:58-64). These results show that p38 MAPK is a key signaling intermediate for the effect of the pro-fibrotic cytokine TGF- ⁇ on components of the extracellular matrix and markers of fibrosis.
- P38 also plays a role in directing survival and apoptosis of cells in response to various stimuli. Both survival and apoptosis can be p38 regulated depending on the stimulus and the cell type [Morin and Huot, Cancer Research. 64:1893-1898 (2004)].
- TGF-beta can stimulate apoptosis in murine hepatocytes through activation of gadd45b, a protein involved in cell-cycle control, in a p38 mediated process [Yoo et al, J. Biol. Chem. 278:43001-43007, (2003)].
- UV-stress can activate p38 and trigger apoptosis of a damaged cell.
- P38 has also been shown to promote survival of lymphocytes in response to stress, including neutrophils and CD8+ T cells.
- the present invention is directed to such novel compounds which are inhibitors of p38 kinase.
- This invention relates to the novel compounds of Formula (I) and (Ia), (II) and (IIa), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A1), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof; and pharmaceutical compositions comprising a compound of Formula (I) and (Ia), (II) and (Ia), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A1), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof, in admixture with a pharmaceutically acceptable diluent or carrier.
- This invention relates to a method of treating a CSBP/RK/p38 kinase mediated disease in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of Formula (I) and (Ia), (II) and (IIa), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A1), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
- This invention also relates to a method of inhibiting cytokines and the treatment of a cytokine mediated disease, in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound of Formula (I) and (Ia), (II) and (IIa), (III) and (IIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A1), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
- This invention also relates to a method of inhibiting the production of IL-1 in a mammal in need thereof which comprises administering to said mammal an effective amount of a compound of Formula (I) and (Ia), (II) and (IIa), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A 1 ), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
- This invention also relates to a method of inhibiting the production of IL-6 in a mammal in need thereof which comprises administering to said mammal an effective amount of a compound of Formula (I) and (Ia), (II) and (Ia), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A 1 ), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
- This invention also relates to a method of inhibiting the production of IL-8 in a mammal in need thereof which comprises administering to said mammal an effective amount of a compound of Formula (I) and (Ia), (II) and (Ia), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A 1 ), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
- This invention also relates to a method of inhibiting the production of TNF in a mammal in need thereof which comprises administering to said mammal an effective amount of a compound of Formula (I) and (Ia), (II) and (IIa), (III) and (IIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (IX) and (IXa), (A), (A 1 ), (B), and (B1), and a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
- the present invention is directed to novel compounds of Formula (I) and (Ia), (II) and (IIa), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI) and (VIa-VIi), (A), (A 1 ), (B), (BI), (VI), (Via), (VIII) and (VIIIa), (IX) and (IXa), or a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
- the difference between compounds of Formula (I) and (Ia) lies in unsaturation of the ring system.
- R 1 , R 1′ , R 2 , R 3 , R x , X and R 3 , etc. terms are the same for both groups within the formulas themselves, for instance, in Formula (I) and (Ia), and except for the additional G5/G6/G7/G8 terms, applicable across all formulas herein.
- everything applicable to Formula (I) is also applicable to Formula (Ia) unless otherwise indicated, and for the remaining compounds of Formula (II) and (IIa), etc. unless specified otherwise.
- R 1 is C(Z)N(R 10′ )(CR 10 R 20 ) v R b , C(Z)O(CR 10 R 20 ) v R b , N(R 10′ )C(Z)(CR 10 R 20 ) v R b , N(R 10′ )C(Z)N(R 10′ )(CR 10 R 20 ) v R b , or N(R 10′ )OC(Z)(CR 10 R 20 ) v R b .
- R 1 is C(Z)N(R 10′ )(CR 10 R 20 ) v R b , or N(R 10′ )C(Z)(CR 10 R 20 ) v R b . In another embodiment of the invention R 1 is C(Z)N(R 10′ )(CR 10 R 20 ) v R b .
- R 1′ is independently selected at each occurrence from halogen, C 1-4 alkyl, halo-substituted-C 1-4 alkyl, cyano, nitro, (CR 10 R 20 ) v′ NR d R d′ , (CR 10 R 20 ) v′ C(O)R 12 , SR 5 , S(O)R 5 , S(O) 2 R 5 , or (CR 10 R 20 ) v′ OR 13 .
- R 1′ is independently selected at each occurrence from halogen, C 1-4 alkyl, or halo-substituted-C 1-4 alkyl. In another embodiment, R 1′ is independently selected at each occurrence from fluorine, chlorine, methyl, or CF 3 .
- g is 0 or an integer having a value of 1, 2, 3, or 4. In one embodiment of the invention, g is 0, 1 or 2.
- R 1′ when R 1′ is substituted on a phenyl ring in the ortho position, and a second R 1′ moiety is also substituted on the ring, then preferably the second substitution is not in the other ortho position.
- the phenyl ring is substituted in the 2-position and if a second substituent is present, in the 3-position with the R 1 moiety in the 5-position.
- the R 1′ moiety may be in the other ortho 2-position and the R 1 moiety in the 3-position, which will change the ring position numbering.
- R d and R d′ are each independently selected at each occurrence from hydrogen, C 1-4 alkyl, C 3-5 cycloalkyl, C 3-5 cycloalkylC 1-4 alkyl, or the R d and R d′ together with the nitrogen which they are attached form an optionally substituted heterocyclic ring of 5 to 6 members, which ring optionally contains an additional heteroatom selected from oxygen, sulfur or NR 9′ , and wherein the R d and R d′ moieties which are C 1-4 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-4 alkyl, and the R d and R d′ cyclized ring are optionally substituted, 1 to 4 times, independently at each occurrence by halogen; halosubstituted C 1-4 alkyl; hydroxy; hydroxy substituted C 1-4 alkyl; C 1-4 alkoxy; halosubstituted C 1-4 alkoxy; S(O)m
- R 9′ is independently selected at each occurrence from hydrogen, or C 1-4 alkyl.
- Z is independently selected at each occurrence from oxygen or sulfur.
- v is 0 or an integer having a value of 1 to 2.
- v′ is 0 or an integer having a value of 1 or 2.
- R 10 and R 20 are independently selected at each occurrence from hydrogen or C 1-4 alkyl.
- R 10′ is independently selected at each occurrence from hydrogen or C 1-4 alkyl.
- R 12 is independently selected at each occurrence from hydrogen, C 1-4 alkyl, halo-substituted C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkyl C 1-4 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenyl C 1-4 alkyl, aryl, arylC 1-4 alkyl, heteroaryl, heteroarylC 1-4 alkyl, heterocyclyl, or heterocyclylC 1-4 alkyl, and wherein these moieties, excluding hydrogen, may be optionally substituted.
- R 13 is independently selected at each occurrence from hydrogen, C 1-4 alkyl, halo-substituted C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenyl C 1-4 alkyl, aryl, arylC 1-4 alkyl, heteroaryl, heteroarylC 1-4 alkyl, heterocyclyl, or a heterocyclylC 1-4 alkyl moiety, and wherein each of these moieties, excluding hydrogen, may be optionally substituted and wherein these moieties, excluding hydrogen, may be optionally substituted 1 to 4 times by halogen; halosubstituted C 1-4 alkyl; C 1-4 alkyl; hydroxy; hydroxy substituted C 1-4 alkyl; C 1-4 alkoxy; halosubstit
- R 21 , and R 31 are each independently selected at each occurrence from hydrogen or C 1-4 alkyl, or R 21 , and R 31′ together with the nitrogen to which they are attached cyclize to form a 5 to 7 membered ring which optionally contains an additional heteroatom selected from oxygen, nitrogen, or sulfur.
- R b is hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-10 alkyl, aryl, arylC 1-10 alkyl, heteroaryl, heteroarylC 1-10 alkyl, heterocyclic, or a heterocyclylC 1-10 alkyl moiety, which moieties, excluding hydrogen, are all optionally substituted.
- R b moieties may be optionally substituted, one or more times, preferably 1 to 4 times independently at each occurrence by halogen, such as fluorine, chlorine, bromine or iodine; hydroxy; hydroxy substituted C 1-10 alkyl; C 1-10 alkoxy, such as methoxy or ethoxy; halosubstituted C 1-10 alkoxy; OR 8 , such as methoxy, ethoxy or phenoxy; SR 5 , S(O)R 5 , S(O) 2 R 5 , such as methyl thio, methylsulfinyl or methyl sulfonyl; C(O)R j ; C(O)OR j ; C(O)NR 4′′ R 14′′ ; cyano; nitro; NR 15 R 25 ; -Z′-(CR 10 R 20 )s-Z′; C 1-10 alkyl; C 3-7 cycloalkyl or a C 3-7
- the moiety -Z′-(CR 10 R 20 )s-Z′ forms a cyclic ring, such as a dioxolane ring.
- Z′ is independently selected at each occurrence from oxygen, or sulfur.
- s is independently selected at each occurrence from an integer having a value of 1, 2, or 3.
- R 5 is independently selected at each occurrence from hydrogen, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl or NR 4′ R 14′ , excluding the moieties SR 5 being SNR 4 R 14′ , S(O) 2 R 5 being SO 2 H and S(O)R 5 being SOH.
- R 4′ and R 14′ are each independently selected at each occurrence from hydrogen or C 1-4 alkyl, or R 4′ and R 14′ can cyclize together with the nitrogen to which they are attached to form an optionally substituted 5 to 7 membered ring which optionally contains an additional heteroatom selected from oxygen, sulfur or NR 9′ .
- R 4′ and R 14′ cyclize to form an optionally substituted ring, such rings include, but are not limited to pyrrolidine, piperidine, piperazine, morpholine, and thiomorpholine (including oxidizing the sulfur).
- R 4′′ and R 14′′ are each independently selected at each occurrence from hydrogen or C 1-10 alkyl, or R 4′′ and R 14′′ can cyclize together with the nitrogen to which they are attached to form an optionally substituted 5 to 7 membered ring which optionally contains an additional heteroatom selected from oxygen, sulfur or NR 9′ .
- R 4′′ and R 14′′ cyclize to form an optionally substituted ring, such rings include, but are not limited to pyrrolidine, piperidine, piperazine, morpholine, and thiomorpholine (including oxidizing the sulfur).
- R f is independently selected at each occurrence from hydrogen, C 1-10 alkyl, aryl, aryl C 1-10 alkyl, heteroaryl, heteroaryl C 1-10 alkyl, heterocyclic, or a heterocyclic C 1-10 alkyl moiety, and wherein these moieties, excluding hydrogen, may be optionally substituted.
- R j is independently selected at each occurrence from C 1-10 alkyl, aryl, aryl C 1-10 alkyl, heteroaryl, heteroaryl C 1-10 alkyl, heterocyclic, or a heterocyclic C 1-10 alkyl moiety, which moieties may all be optionally substituted.
- R b is an optionally substituted C 1-10 alkyl
- the moiety includes but is not limited to a methyl, ethyl, n-propyl, isopropyl, t-butyl, n-butyl, isobutyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, heptyl, 2-methylpropyl; a halosubstituted alkyl, such as 2,2,2-trifluoroethyl, trifluoromethyl, 2-fluoroethyl; a cyano substituted alkyl, such as cyanomethyl, cyanoethyl; an alkoxy, thio or hydroxy substituted alkyl, such as 2-methoxy-ethyl, 2-hydroxy propyl or serinol, or an ethylthioethyl.
- R b is an optionally substituted C 1-10 alkyl the moiety is a methyl, ethyl, n-propyl, isopropyl, t-butyl, n-butyl, or 2,2-dimethylpropyl or 2-hydroxy propyl group.
- the heteroaryl containing moiety includes but is not limited to, furyl, pyranyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, oxathiadiazolyl, triazolyl, tetrazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and uracil, indolyl, isoindolyl, indazolyl, indolizinyl, azaindolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzofuranyl, benzothiophenyl, quinolyl
- R b when R b is an optionally substituted heteroaryl it is a 1,3-thiazol-2-yl or 5-methyl-1,3-thiazol-2-yl, isoquinolinyl, thiophene, e.g. a 3-thiophene, indol-5-yl, pyridinyl, e.g. a pyridin3-yl, or pyridine-4-yl, indazolyl, benzothiazolyl, 2-methyl-1,3-benzothiazol-5-yl, 1H-imidazol-4-yl or 1H-imidazol-4-ylethyl.
- the heteroaryl ring is an optionally substituted thiazolyl, pyridyl, or thiophene ring.
- R b is an optionally substituted 1,3-thiazol-2-yl.
- the heterocyclic containing moiety includes but is not limited to tetrahydropyrrole, tetrahydropyran, tetrahydrofuran, tetrahydrothiophene (including oxidized versions of the sulfur moiety), azepine, diazepine, aziridinyl, pyrrolinyl, pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 3-oxo-1-pyrrolidinyl, 1,3-benzdioxol-5-yl, imidazolinyl, imidazolidinyl, indolinyl, pyrazolinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino (including oxidized versions of the sulfur moiety).
- the heterocyclic, or heterocyclic alkyl group is pyrazol-3-yl, 4-morpholino, unsubstituted and substituted 2-furanyl, or 2-furanylmethyl, 2-thienyl or 2-thienylmethyl, tetrahydro-2H-pyran-4-yl, or tetrahydro-2H-pyran-4-yl methyl, tetrahydro-2-furanyl, or tetrahydro-2-furanylmethyl.
- R b is an optionally substituted aryl or arylalkyl moiety
- the aryl containing moiety is unsubstituted or substituted independently at each occurrence one or more times by halogen, alkyl, cyano, OR 8 , SR 5 , S(O) 2 R 5 , C(O)R j , C(O)OR j , -Z′-(CR 10 R 20 )s-Z′, halosubstituted C 1-10 alkyl, or an optionally substituted aryl.
- R b is a phenyl, or napthylene, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-chloro-4-fluorophenyl, 2-methyl phenyl, 3-methylphenyl, 4-methylphenyl, 6-methyl phenyl, 2-methyl phenyl, 3-amino phenyl, 3,4-dimethyl phenyl, 4-methyl-3-fluorophenyl, 4-trifluorophenyl, 4-ethoxyphenyl, 4-methoxyphenyl, 3-cyanophenyl, 4-cyanophenyl, 4-thiomethylphenyl, 4-acetylphenyl, 4-dimethylaminophenyl, benzy
- R b is a phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-chloro-4-fluorophenyl, 4-methyl-3-fluorophenyl, 4-trifluorophenyl, 2-methylphenyl, 3-methylphenyl, 4-ethoxyphenyl, 4-methoxyphenyl, 3-cyanophenyl, 4-cyanophenyl, 4-thiomethylphenyl, 4-acetylphenyl, 4-dimethylaminophenyl, biphenyl, 4′-fluorobiphenyl, 4-sulfonamido-2-methylphenyl, 3-phenyloxyphenyl, benzyl, or phenethyl.
- R b is a 4-
- R b is an optionally substituted cycloalkyl or cycloalkyl alkyl moiety
- the moiety is a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, or a cyclopentylmethyl.
- R b is a cyclopropyl or cyclopropylmethyl group.
- R b is C 1-10 alkyl, heteroaryl, or aryl, all optionally substituted.
- R b is hydrogen, or an optionally substituted alkyl.
- R b is an alkyl, such as propyl or isopropyl; heteroaryl, such as a thiazolyl; an aryl, such phenyl, or 4-F phenyl; an arylalkyl, or a cycloalkylalkyl moiety, all optionally substituted.
- R b is alkyl, heteroaryl, or aryl, all optionally substituted.
- m is independently selected at each occurrence from 0 or an integer having a value of 1 or 2.
- n, n′, m, q′, s, t, or v′, etc. are independently chosen at each occurrence.
- R 8 is independently selected at each occurrence from hydrogen, C 1-4 alkyl, halo-substituted C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkyl C 1-4 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenyl C 1-4 alkyl, aryl, arylC 1-4 alkyl, heteroaryl, heteroarylC 1-4 alkyl, heterocyclyl, or a heterocyclylC 1-4 alkyl moiety, and wherein these moieties, excluding hydrogen, may be optionally substituted independently at each occurrence, 1 to 4 times, by halogen; halosubstituted C 1-4 alkyl; C 1-4 alkyl; C 3-5 cycloalkyl; C 3-5 cycloalkyl C 1-4 alkyl; halosubstituted C 1-4 alkyl
- R 15 and R 25 are each independently selected at each occurrence from hydrogen, C 1-4 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, aryl, or aryl-C 1-4 alkyl, heteroaryl or heteroaryl C 1-4 alkyl moiety, and wherein these moieties, excluding hydrogen may be optionally substituted; or R 15 and R 25 together with the nitrogen which they are attached form an optionally substituted heterocyclic ring of 4 to 7 members, which ring optionally contains an additional heteroatom selected from oxygen, sulfur or NR 9 ; and wherein these moieties are optionally substituted 1 to 4 times, independently at each occurrence by halogen; hydroxy; hydroxy substituted C 1-10 alkyl; C 1-10 alkoxy; halosubstituted C 1-10 alkoxy; SR 5 , S(O)R 5 , S(O) 2 R 5 ; C(O)R j ; C(O)OR
- R 4 and R 14 are each independently selected at each occurrence from hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, aryl, aryl-C 1-4 alkyl, heterocyclic, heterocyclic C 1-4 alkyl, heteroaryl or heteroaryl C 1-4 alkyl; or the R 4 and R 14 together with the nitrogen which they are attached form an unsubstituted or substituted heterocyclic ring of 4 to 7 members, which ring optionally contains an additional heteroatom selected from oxygen, sulfur or nitrogen.
- R 4 and R 14 moieties, excluding hydrogen, of C 1-10 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, aryl, aryl-C 1-4 alkyl, heteroaryl and heteroaryl C 1-4 alkyl moieties, heterocyclic, or heterocyclic C 1-4 alkyl moieties, and the R 4 and R 14 cyclized ring are optionally substituted, one or more times, preferably 1 to 4 times, independently at each occurrence, by halogen; hydroxy; hydroxy substituted C 1-10 alkyl; C 1-10 alkoxy; halosubstituted C 1-10 alkoxy; C 1-10 alkyl; halosubstituted C 1-10 alkyl; SR 5 ; S(O)R 5 ; S(O) 2 R 5 ; C(O)Rj; C(O)ORj; C(O)NR 4′ R 14′ ; (CR 10 R 20 ) n N
- such rings include, but are not limited to pyrrolidine, piperidine, piperazine, diazepine, morpholine, and thiomorpholine (including oxidizing the sulfur).
- R 6 is independently selected at each occurrence from hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, heterocyclyl, heterocyclyl C 1-10 alkyl, aryl, arylC 1-10 alkyl, heteroaryl or a heteroarylC 1-10 alkyl moiety, and wherein these moieties, excluding hydrogen may be optionally substituted independently at each occurrence, one or more times, suitably 1 to 2 times, by halogen; hydroxy; hydroxy substituted C 1-10 alkyl; C 1-10 alkoxy; halosubstituted C 1-10 alkoxy; S(O) m alkyl; C(O); NR 4′ R 14′ ; C 1-10 alkyl; C 3-7 cycloalkyl; C 3-7 cycloalkyl C 1-10 alkyl; halosubstituted C 1-10 alkyl; an unsubstituted or substituted aryl or aryl C 1-4 alkyl, an unsubsubstit
- R 9 is independently selected at each occurrence from hydrogen, C(Z)R 6 , optionally substituted C 1-10 alkyl, optionally substituted aryl or optionally substituted aryl-C 1-4 alkyl.
- These alkyl, aryl and arylalkyl moieties may be optionally substituted 1 or 2 times, independently at each occurrence by halogen; hydroxy; hydroxy substituted C 1-10 alkyl; C 1-10 alkoxy; halosubstituted C 1-10 alkoxy; S(O) m alkyl; —C(O); NR 4′ R 14′ ; C 1-10 alkyl, C 3-7 cycloalkyl; C 3-7 cycloalkyl C 1-10 alkyl; halosubstituted C 1-10 alkyl; an aryl or aryl C 1-4 alkyl, and wherein these aryl containing moieties may also be substituted one or two times independently by halogen, hydroxy, hydroxy substituted
- R 3 is a C 1-10 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkyl C 1-10 alkyl, aryl, arylC 1-10 alkyl, heteroaryl, heteroarylC 1-10 alkyl, heterocyclic, or heterocyclylC 1-10 alkyl moiety, which moieties may be optionally substituted one or more times, suitably 1 to 4 times, independently at each occurrence by hydrogen, halogen, nitro, C 1-10 alkyl, halo-substituted C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-10 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenylC 1-10 alkyl, (CR 10 R 20 ) n OR 6 , (CR 10 R 20 ) n SH, (CR 10 R 20 ) n S(O
- the R 3 moieties are optionally substituted 1 to 4 times, independently at each occurrence by halogen, nitro, C 1-4 alkyl, halo-substituted C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkylC 1-4 alkyl, C 5-6 cycloalkenyl, C 5-6 cycloalkenylC 1-4 alkyl, (CR 10 R 20 ) n OR 6 , (CR 10 R 20 ) n SH, (CR 10 R 20 ) n S(O) m R 7 , (CR 10 R 20 ) n NHS(O) 2 R 7 , (CR 10 R 20 ) n S(O) 2 NR 16 R 26 , (CR 10 R 20 ) n NR 16 R 26 , (CR 10 R 20 ) n CN, (CR 10 R 20 ) n C(Z)R 6 , (CR 10 R
- the R 3 moieties are optionally substituted independently, one or more times, suitably 1 to 4 times, independently at each occurrence by the R 3 optional substitutent is independently selected from halogen, C 1-10 alkyl, (CR 10 R 20 ) n OR 6 , (CR 10 R 20 ) n NR 16 R 26 , or halo-substituted C 1-10 alkyl.
- the optional substitutents are independently selected at each occurrence from halogen, C 1-10 alkyl, hydroxy, C 1-10 alkoxy, cyano, nitro, amino, or halosubstituted C 1-10 alkyl.
- the R 3 substituents are selected independently from halogen, such as fluorine, chlorine, bromine or iodine, or C 1-10 alkyl, such as methyl.
- R 3 moieties are an optionally substituted C 1-10 alkyl, optionally substituted C 3-7 cycloalkyl, optionally substituted C 3-7 cycloalkylalkyl, or optionally substituted aryl.
- the R 3 moiety is an optionally substituted C 1-10 alkyl, or an optionally substituted aryl.
- R 3 is an optionally substituted phenyl.
- R 3 is a phenyl ring substituted one or more times by independently at each occurrence by fluorine, chlorine, hydroxy, methoxy, amino, methyl, or trifluoromethyl.
- R 3 is a 2,6-difluorophenyl.
- R 3 is an aryl moiety, it is an optionally substituted phenyl ring.
- the phenyl is optionally substituted one or more times, independently at each occurrence, suitably 1 to 4 times by halogen, C 1-4 alkyl, or halo-substituted-C 1-4 alkyl.
- the phenyl ring may be substituted in the 2,4, or 6-position, or di-substituted in the 2,4-position or 2,6-position, such as 2-fluoro, 4-fluoro, 2,4-difluoro, 2,6-difluoro, or 2-methyl-4-fluoro; or tri-substituted in the 2,4,6-position, such as 2,4,6-trifluoro.
- R 7 is independently selected at each occurrence from C 1-6 alkyl, aryl, arylC 1-6 alkyl, heterocyclic, heterocyclylC 1-6 alkyl, heteroaryl, or heteroarylC 1-6 alkyl; and wherein each of these moieties may be optionally substituted one or two times independently at each occurrence, by halogen; hydroxy; hydroxy substituted C 1-10 alkyl; C 1-10 alkoxy; halosubstituted C 1-10 alkoxy; S(O) m alkyl; C(O); NR 4′ R 14′ ; C 1-10 alkyl; C 3-7 cycloalkyl; C 3-7 cycloalkylC 1-10 alkyl; halosubstituted C 1-10 alkyl; an aryl or aryl C 1-4 alkyl moiety, and wherein these aryl containing moieties may also be substituted independently at each occurrence, one to two times by halogen, hydroxy,
- R 16 and R 26 are each independently selected at each occurrence from hydrogen, or C 1-4 alkyl; or the R 16 and R 26 together with the nitrogen which they are attached form an unsubstituted or substituted heterocyclic ring of 4 to 7 members, which ring optionally contains an additional heteroatom selected from oxygen, sulfur or NR 9′ .
- n is 0, or an integer having a value of 1 to 10.
- X is R 2 , OR 2′ , S(O) m R 2′ , (CH 2 ) n N(R 11 )S(O) m R 2′ , (CH 2 ) n N(R 11 )C(O)R 2′ , (CH 2 ) n NR 4 R 14 , (CH 2 ) n N(R 2′ )(R 2′′ ), or N(R 10′ )R h NH—C( ⁇ N—CN)NRqRq′.
- X is N(R 10′ )R h NH—C( ⁇ N—CN)NRqRq′.
- X 1 is N(R 11 ), O, S(O) m , or CR 10 R 20 .
- X 1 is N(R 11 ), or O.
- R h is selected from an optionally substituted C 1-10 alkyl, —CH 2 —C(O)—CH 2 —, —CH 2 —CH 2 —O—CH 2 —CH 2 —, —CH 2 —C(O)N(R 10′ )CH 2 —CH 2 —, —CH 2 —N(R 10′ )C(O)CH 2 —, —CH 2 —CH(OR 10′ )—CH 2 , —CH 2 —C(O)O—CH 2 —CH 2 —, or —CH 2 —CH 2 —O—C(O)CH 2 —.
- R q and R q′ are independently selected at each occurrence from hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-10 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenyl-C 1-10 alkyl, aryl, arylC 1-10 alkyl, heteroaryl, heteroarylC 1-10 alkyl, heterocyclic, or a heterocyclylC 1-10 alkyl moiety, and wherein all of the moieties, excluding hydrogen, are optionally substituted, or R q and R q′ together with the nitrogen to which they are attached form an optionally substituted heterocyclic ring of 5 to 7 members, which ring may contain an additional heteroatom selected from oxygen, nitrogen or sulphur.
- R 11 is independently selected at each occurrence from hydrogen, or C 1-4 alkyl.
- R 2 is independently selected from hydrogen, optionally substituted C 1-10 alkyl, optionally substituted C 3-7 cycloalkyl, optionally substituted C 3-7 cycloalkylalkyl, optionally substituted aryl, optionally substituted arylC 1-10 alkyl, optionally substituted heteroaryl, optionally substituted heteroarylC 1-10 alkyl, optionally substituted heterocyclic, optionally substituted heterocyclylC 1-10 alkyl moiety; or R 2 is the moiety (CR 10 R 20 ) q′ X 1 (CR 10 R 20 ) q C(A 1 )(A 2 )(A 3 ), or (CR 10 R 20 ) q C(A 1 )(A 2 )(A 3 ).
- q′ is 0, or an integer having a value of 1 to 6.
- the R 2 moieties may be optionally substituted one or more times, preferably 1 to 4 times, independently at each occurrence by C 1-10 alkyl, halo-substituted C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-10 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenyl C 1-10 alkyl, halogen, —C(O), cyano, nitro, aryl, aryl C 1-10 alkyl, heterocyclic, heterocyclic C 1-10 alkyl, heteroaryl, heteroaryl C 1-10 alkyl, (CR 10 R 20 ) n OR 6 , (CR 10 R 20 ) n SH, (CR 10 R 20 ) n S(O) m R 7 , (CR 10 R 20 ) n N(R 10′ )S(O) 2 R 7
- R e and R e′ are each independently selected at each occurrence from hydrogen, C 1-4 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, aryl, aryl-C 1-4 alkyl, heterocyclic, heterocyclic C 1-4 alkyl, heteroaryl or a heteroaryl C 1-4 alkyl moiety, which moieties may be optionally substituted; or R e and R e′ together with the nitrogen which they are attached form an optionally substituted heterocyclic ring of 4 to 7 members, which ring optionally contains an additional heteroatom selected from oxygen, sulfur or nitrogen; and wherein each of these moieties, including the cyclized ring and excluding hydrogen, may be substituted 1 to 4 times, independently at each occurrence by halogen; hydroxy; hydroxy substituted C 1-10 alkyl; C 1-10 alkoxy; halosubstituted C 1-10 alkoxy; C 1-10 alkyl; halosubsti
- R f′ is independently selected at each occurrence from hydrogen, C 1-10 alkyl, aryl, aryl C 1-10 alkyl, heteroaryl, heteroaryl C 1-10 alkyl, heterocyclic, heterocyclic C 1-10 alkyl or NR 4′ R 14′ , and wherein these moieties, excluding hydrogen, and NR 4′ R 14 , may be optionally substituted.
- the heterocyclic containing moiety is suitably selected from tetrahydropyrrole, tetrahydropyran, tetrahydrofuran, tetrahydrothiophene (including oxidized versions of the sulfur moiety), aziridinyl, pyrrolinyl, pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 3-oxo-1-pyrrolidinyl, 1,3-benzdioxol-5-yl, imidazolinyl, imidazolidinyl, indolinyl, pyrazolinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino (including oxidized versions of the sulfur moiety).
- R 2 is an optionally substituted piperidinyl or piperazinyl ring.
- R 2 when R 2 is an optionally substituted heterocyclic or heterocyclic alkyl ring the ring is substituted one or mores times independently by an optionally substituted heterocyclic, heterocyclic alkyl, aryl, arylalkyl, alkyl, (CR 10 R 20 ) n NR e R e′ , or (CR 10 R 20 ) n N(R 10′ )C(Z)OR 7 .
- the second heterocyclic ring is suitably selected from an optionally substituted tetrahydropyrrole, tetrahydropyran, tetrahydrofuran, tetrahydrothiophene (including oxidized versions of the sulfur moiety), aziridinyl, pyrrolinyl, pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 3-oxo-1-pyrrolidinyl, 1,3-benzdioxol-5-yl, imidazolinyl, imidazolidinyl, indolinyl, pyrazolinyl, pyrazolidinyl, piperidinyl, piperazinyl, diazepine, morpholino or thiomorpholino (including oxidized versions of the sulfur moiety).
- the second heterocyclic ring is selected from morpholino, piperidine, or pyrrolidinyl.
- R 2 is a 4-amino-1-piperidinyl, 1,1-dimethylethyl)oxy]-carbonyl ⁇ amino)-1-piperidinyl, 4-methyl-1-piperazinyl, 4-ethyl-1-piperazinyl, 4-propyl-1-piperazinyl, 4-butyl-1-piperazinyl, 4-(methylamino)-1-piperidinyl, 1,1-dimethylethyl-4-piperidinyl ⁇ methylcarbamate, 4-phenyl-1-piperazinyl, 1,4′-bipiperidin-1′-yl, 4-(1-pyrrolidinyl)-1-piperidinyl, 4-methyl-1,4′-bipiperidin-1′-yl, 4-(4-morpholinyl)-1-piperidinyl, 4-(diphenylmethyl)-1-piperazinyl, or 4-methylhexahydro-1H-1,4-diazepin-1-yl, 4-
- R 2′ is independently selected at each occurrence from hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylalkyl, aryl, arylC 1-10 alkyl, heteroaryl, heteroarylC 1-10 alkyl, heterocyclic, or a heterocyclylC 1-10 alkyl moiety, and wherein each of these moieties, excluding hydrogen, may be optionally substituted 1 to 4 times, independently, at each occurrence, by C 1-10 alkyl, halo-substituted C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-10 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenylC 1-10 alkyl, halogen, —C(O), cyano, nitro, aryl, aryl C 1-10 alkyl, heteroary
- R 2′ when X is (CH 2 ) n N(R 2′ )(R 2′′ ), one of R 2′ , or R 2′′ is hydrogen, or methyl.
- R 2′ when R 2′ is an optionally substituted heterocyclic or heterocyclylC 1-10 alkyl the heterocyclic containing moiety is substituted one or more time independently by C 1-10 alkyl, aryl, heterocyclic, (CR 10 R 20 ) n NR e R e′ , (CR 10 R 20 ) n N(R 10′ )C(Z)OR 7 , or (CR 10 R 20 ) n C(Z)OR 6 .
- R 2′ is an optionally substituted C 1-10 alkyl, cycloalkyl, heterocyclic, heterocyclyl C 1-10 alkyl, heteroarylalkyl.
- R 2′ is an optionally substituted cycloalkyl it is a cyclohexyl ring.
- the cyclohexyl ring is optionally substituted one or more times by (CR 10 R 20 ) n NR e R e′ .
- R 2′ is an optionally substituted heterocyclic, or a heterocyclylC 1-10 alkyl
- the ring is selected from tetrahydropyrrole, tetrahydropyran, tetrahydrofuran, tetrahydrothiophene (including oxidized versions of the sulfur moiety), aziridinyl, pyrrolinyl, pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 3-oxo-1-pyrrolidinyl, 1,3-benzdioxol-5-yl, imidazolinyl, imidazolidinyl, indolinyl, pyrazolinyl, pyrazolidinyl, piperidinyl, piperazinyl, diazepine, hexahydro-1-H-azepine, morpholino or thiomorpholino (including oxidized versions of the sulfur moiety).
- the ring is a piperidine, piperazine, pyrrolidinyl, 2-oxo-1-pyrrolidinyl, morpholino, hexahydro-1-H-azepine ring.
- the rings are substituted one or more times, suitably 1 to 4 times, independently by C 1-10 alkyl, aryl, arylalkyl, (CR 10 R 20 ) n NR e R e′ , or (CR 10 R 20 ) n N(R 10′ )C(Z)OR 7 .
- (CH 2 ) n N(R 2′ )(R 2′′ ) is 1-(phenylmethyl)-4-piperidinamine, 2-[4-(phenylmethyl)-1-piperazinyl]ethylamine, 2-(1-piperidinyl)ethylamine, 2-(1-methyl-2-pyrrolidinyl)ethylamine, 1-[(phenylmethyl)-3-pyrrolidinyl]amine, 3-[(1-pyrrolidinyl)propyl]amine, 3-[(hexahydro-1H-azepin-1-yl)propyl]amine, (1-methyl-4-piperidinyl)amine, 3-[(4-morpholinyl)propyl]amine, 3-[(2-oxo-1-pyrrolidinyl)propyl]-amine, 2-[(4-morpholinyl)ethyl]amine, 2-[(1-pyrrolidinyl)ethyl]-amine, or [(1-
- R 2′ is an optionally substituted C 1-10 alkyl
- the alkyl is substituted one or more times independently by (CR 10 R 20 ) n NR e R e′ or (CR 10 R 20 ) n NR e R e′ C 1-4 alkylNR e R e′ .
- R e and R e′ are independently an optionally substituted C 1-4 alkyl, such as methyl, ethyl, isopropyl, n-butyl, or t-butyl.
- (CH 2 ) n N(R 2′ )(R 2′′ ) is 3-(dimethylamino)propyl(methyl)amine, 3-(diethylamino)propylamine, propylamine, (2,2-dimethylpropyl)amine, (2-hydroxypropyl)amino, 2-(dimethylamino)ethylamine, 2-(dimethylamino)ethyl(methyl)amine, 3-(dimethylamino)propylamine, 2-(dimethylamino)ethyl(methyl)amine, 3-(diethylamino)propylamine, 2-(methylamino)ethylamine, [(1-methylethyl)amino]ethylamine, 3-(diethylamino)propylamine, 3-(dibutylamino)propylamine, 3-[(1-methylethyl)amino]propylamine, 3-(1,1-dimethyleth
- R 2′′ is selected from hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkylalkyl, aryl, arylC 1-10 alkyl, heteroaryl, heteroarylC 1-10 alkyl, heterocyclic, or a heterocyclylC 1-10 alkyl moiety, and wherein these moieties, excluding hydrogen, may be optionally substituted 1 to 4 times, independently at each occurrence, by C 1-10 alkyl, halo-substituted C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-10 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenyl C 1-10 alkyl, halogen, —C(O), cyano, nitro, aryl, aryl C 1-10 alkyl, heteroaryl, heteroarylC 1-10 alkyl
- t is an integer having a value of 2 to 6.
- q is 0 or an integer having a value of 1 to 10.
- a 1 is an optionally substituted C 1-10 alkyl, heterocyclic, heterocyclic C 1-10 alkyl, heteroaryl, heteroaryl C 1-10 alkyl, aryl, or aryl C 1-10 alkyl.
- a 2 is an optionally substituted C 1-10 alkyl, heterocyclic, heterocyclic C 1-10 alkyl, heteroaryl, heteroaryl C 1-10 alkyl, aryl, or aryl C 1-10 alkyl.
- a 3 is hydrogen or is an optionally substituted C 1-10 alkyl.
- the A 1 , A 2 , and A 3 C 1-10 alkyl moieties may optionally substituted one or more times independently at each occurrence, preferably from 1 to 4 times, with halogen, such as chlorine, fluorine, bromine, or iodine; halo-substituted C 1-10 alkyl, such as CF 3 , or CHF 2 CF 3 ; C 2-10 alkenyl, C 2-10 alkynyl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-10 alkyl, C 5-7 cycloalkenyl, C 5-7 cycloalkenylC 1-10 alkyl, (CR 10 R 20 ) n OR 6 , (CR 10 R 20 ) n SH, (CR 10 R 20 ) n S(O) m R 7 , (CR 10 R 20 ) n N(R 10′ )S(O) 2 R 7 , (CR 10 R 20 ) n NR 4 R 14 ,
- X is R 2
- R 2 is (CR 10 R 20 ) q′ X 1 (CR 10 R 20 ) q C(A 1 )(A 2 )(A 3 ), or (CR 10 R 20 ) q′ C(A 1 )(A 2 )(A 3 ).
- q′ is 0.
- R 2 is the moiety (CR 10 R 20 ) q′ X 1 (CR 10 R 20 ) q C(A 1 )(A 2 )(A 3 ), q′ is 0, X 1 is nitrogen, q is 0 or 1, A 1 is an optionally substituted heterocyclic or heterocyclic alkyl, and A 2 is an optionally substituted aryl. More specifically, R 2 is 2-phenyl-2-(1-pyrrolidinyl)ethyl]amino, or 1-phenyl-2-(1-pyrrolidinyl)ethyl]amino.
- one or more of the A 1 , A 2 and A 3 moieties are substituted with (CR 10 R 20 ) n OR 6 .
- the R 6 substituent in (CR 10 R 20 ) n OR 6 is hydrogen.
- X is R 2 and R 2 is (CR 10 R 20 ) q′ C(A 1 )(A 2 )(A 3 ), such as CH(CH 2 OH) 2 , or C(CH 3 )(CH 2 OH) 2 ; or wherein R 2 is (CR 10 R 20 ) q′ X 1 (CR 10 R 20 ) q C(A 1 )(A 2 )(A 3 ) and q′ is 0, and the moiety is X 1 (CR 10 R 20 ) q CH(CH 2 OH) 2 , or X 1 (CR 10 R 20 ) q C(CH 3 )(CH 2 OH) 2 ; in another embodiment X 1 is oxygen or nitrogen.
- X is R 2 , OR 2′ , (CH 2 ) n NR 4 R 14 , or (CH 2 ) n N(R 2′ )(R 2′′ ).
- X is S(O) m R 2′ , (CH 2 ) n NR 4 R 14 , or (CH 2 ) n N(R 2′ )(R 2′′ ).
- X is (CH 2 ) n NR 4 R 14 , or (CH 2 ) n N(R 2′ )(R 2′′ ).
- X is (CH 2 ) n NR 4 R 14 .
- X is (CH 2 ) n N(R 2′ )(R 2′′ ).
- X is R 2 , OR 2′ , (CH 2 ) n NR 4 R 14 , or (CH 2 ) n N(R 2′ )(R 2′′ ).
- NR 4 R 14 when X is (CH 2 ) n NR 4 R 14 , and R 4 and R 14 are C 1-10 alkyl, aryl, aryl-C 1-4 alkyl, heterocyclic, heterocyclic C 1-4 alkyl, heteroaryl or heteroaryl C 1-4 alkyl, the C 1-4 alkyl is suitably substituted one or more times, independently at each occurrence with NR 4′ R 14′ ; halogen, hydroxy, alkoxy, C(O)NR 4′ R 14′ ; or NR 4′ C(O)C 1-10 alkyl.
- the C 1-4 alkyl is substituted with NR 4′ R 14′ .
- R 4 and R 14 may be hydrogen when R 4 and R 14 are not cyclized. In another embodiment neither R 4 nor R 14 is hydrogen.
- one of R 4 and R 14 are hydrogen, and the other is an optionally substituted heteroaryl C 1-4 alkyl.
- the optionally substituted heteroaryl alkyl is an imidazolyl alkyl, such as a 1H-imidazol-2-yl-methyl group.
- the heteroaryl ring is selected from an optionally substituted thienyl, pyrrolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, pyrazolyl, triazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, benzoxazolyl, benzimidazolyl, and benzothiazolyl.
- the heteroaryl C 1-4 alkyl is selected from an optionally substituted pyrrolyl, oxazolyl, thiazolyl, isoxazolyl, imidazolyl, benzoxazolyl, benzimidazolyl, and benzothiazolyl.
- the heterocyclic ring is selected from an optionally substituted tetrahydropyrrole, tetrahydropyran, tetrahydrofuran, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, indolinyl, pyrazolinyl, pyrazolidinyl, piperidinyl, piperazinyl, and morpholino.
- the heterocyclic C 1-4 alkyl moiety is selected an optionally substituted from pyrrolinyl, pyrrolidinyl, piperidinyl, piperazinyl, and morpholino.
- X is (CH 2 ) n NR 4 R 14 and R 4 and R 14 together with the nitrogen cyclize to form an optionally substituted ring, such as described above, such rings include, but are not limited to pyrrolidine, piperidine, piperazine, diazepine, and morpholine.
- the R 4 and R 14 substituents cyclize to form a heterocyclic 5 or 6 membered ring, which ring is optionally substituted as defined herein.
- the optional substitutents are suitably selected from an optionally substituted alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, optionally substituted heterocyclic, (CR 10 R 20 ) n N(R 10′ )C(Z)OR 7 , NR 4′ R 14′ , or a C 1-10 alkyl substituted one or more times by an optionally substituted aryl.
- Such substitutents more specifically include phenyl, pyrrolidinyl, morpholino, piperazinyl, 4-methyl-1-piperazinyl, piperidinyl, 2-oxo-2,3-dihydro-1H-benzimidazol-1-yl, 5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl, diphenylmethyl, methyl, ethyl, propyl, butyl, amino, methylamino, and dimethylamino.
- the X substituent is a 1,4′-bipiperin-1-yl ring which may be optionally substituted such as in 4-methyl-1,4′-bipiperin-1-yl; 4-piperidinylamino, 4-amino-1-piperidinyl, 2,2,6,6-tetramethyl-4-piperidinyl)amino, 4-methyl-1-piperazinyl, (4-morpholinyl)-1-piperidinyl, (4-methyl-1-piperazinyl)-1-piperidinyl, 4-ethyl-1-piperazinyl, (2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl, 5-chloro-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl, 4-(1-pyrrolidinyl)-1-piperidinyl, 4-(diphenylmethyl)-1-piperidin
- the X substituent is an optionally substituted 1,4′-bipiperin-1′yl ring, a 4-amino-1-piperidinyl, or a 2,2,6,6-tetramethyl-4-piperidinyl)amino.
- R 2′ is an optionally substituted C 1-10 alkyl moiety
- the alkyl is substituted by (CR 10 R 20 ) n NR e R e′
- R e and R e′ are hydrogen, or an optionally substituted C 1-10 alkyl.
- the X moiety is 3-(diethylamino)propylamino, 3-(dimethylamino)propyl(methyl)amino, 3-(dimethylamino)propyl(methyl)amino, 2-(dimethylamino)ethylamino, 1-(methylethyl)amino-propylamino, (1,1-dimethylethyl)aminopropylamino, (1-methylethyl)aminoethylamino, 2-(methylamino)ethylamino, 2-aminoethyl(methyl)amino, or a 2-(dimethylamino)ethyl(methyl)amino.
- heteroaryl moiety is suitably an optionally substituted imidazole.
- At least one of R 4 and R 14 may be hydrogen when R 4 and R 14 are not cyclized.
- R 3 is a 2,6-difluoro phenyl
- R 1′ is independently selected at each occurrence from hydrogen, fluorine, or methyl
- g is 1 or 2
- R 1 is selected from C(Z)N(R 10′ )(CR 10 R 20 ) v R b , or C(Z)O(CR 10 R 20 ) v R b , or N(R 10′ )C(Z)(CR 10 R 20 ) v R b
- R 1 is selected from C(Z)N(R 10′ )(CR 10 R 20 ) v R b
- the R b moiety is selected from thiazolyl, C 1-10 alkyl or an optionally substituted aryl.
- the R b moiety is propyl or 4-fluorophenyl.
- X is suitably selected from (1H-imidazol-2-ylmethyl)amino or 4-methyl-1,4′-bipiperidin-1′-yl, 2,2,6,6-tetramethyl-4-piperidinyl)amino, 4-amino-1-piperidinyl, 3-(diethylamino)propylamino, 3-(dimethylamino)propyl(methyl)amino, 3-(dimethylamino)propyl(methyl)amino, 2-(dimethylamino)ethylamino, 1-methylethyl)amino-propylamino, (1,1-dimethylethyl)aminopropylamino, (1-methylethyl)aminoethylamino, 2-(methylamino)ethylamino, 2-aminoethyl(methyl)amino, or 2-(dimethylamino)ethyl(methyl)amino.
- R 3 is a 2,6-difluoro phenyl
- R 1′ is independently selected at each occurrence from hydrogen, fluorine, or methyl
- g is 1 or 2
- R 1 is selected from C(Z)N(R 10′ )(CR 10 R 20 ) v R b
- R b moiety is C 1-10 alkyl or an optionally substituted aryl, preferably propyl or 4-fluorophenyl
- X is (CH 2 ) n N(R 2′ )(R 2′′ ), and n is 0.
- X is (CH 2 ) n N(R 2′ )(R 2′′ ), R 2′′ is hydrogen, n is 0, and R 2′ is an alkyl substituted by (CR 10 R 20 ) n NR e R e′ .
- R e and R e′ are independently selected from an optionally substituted C 1-4 alkyl, such as methyl, ethyl, isopropyl, n-butyl, or t-butyl, preferably ethyl.
- Another embodiment of the invention is the genus of compounds of formula (Ic), a subgenus of compounds of Formula (I) and (Ia) wherein R 1 is C(Z)N(R 10′ )(CR 10 R 20 ) v R b , and R b is an optionally substituted heteroaryl, an optionally substituted heteroaryl C 1-10 alkyl, an optionally substituted heterocyclic or an optionally substituted heterocyclic C 1-10 alkyl.
- R 1 is C(Z)N(R 10′ )(CR 10 R 20 ) v R b
- R b is an optionally substituted heteroaryl, an optionally substituted heteroaryl C 1-10 alkyl, an optionally substituted heterocyclic or an optionally substituted heterocyclic C 1-10 alkyl.
- the remaining groups are the same as enumerated above for Formula (I) and (Ia).
- R 1 is C(Z)N(R 10′ )(CR 10 R 20 ) v R b
- R b is an optionally substituted heteroaryl, or an optionally substituted heteroaryl C 1-10 alkyl.
- heteroaryl, heteroarylalkyl, heterocyclic and heterocyclicalkyl moieties are as defined above for Formula (I) and (Ia).
- a preferred heteroaryl ring is an optionally substituted thiazolyl ring, pyridyl, or thiophene ring.
- R 1′ is independently selected hydrogen, halogen, C 1-4 alkyl, or halo-substituted-C 1-4 alkyl. In another embodiment, R 1′ is independently selected from hydrogen, fluorine, chlorine, methyl, or CF 3 . In one embodiment when R 1′ is substituted on the phenyl ring in the ortho position, and a second R 1′ moiety is also substituted on the ring, then preferably the second substitution is not in the other ortho position.
- g is 1 or 2.
- R 3 is an aryl moiety
- it is a phenyl ring
- the phenyl ring is optionally substituted, independently at each occurrence, one or more times, suitably 1 to 4 times by halogen, C 1-4 alkyl, or halo-substituted-C 1-4 alkyl.
- the phenyl ring may suitably be substituted in the 2,4, or 6-position, or di-substituted in the 2,4-position, such as 2-fluoro, 4-fluoro, 2,4-difluoro, 2,6-difluoro, 6-difluoro, or 2-methyl-4-fluoro; or tri-substituted in the 2,4,6-position, such as 2,4,6-trifluoro.
- R 3 is a 2,6-difluoro phenyl.
- R 3 is a 2,6-difluoro phenyl, R 1′ is independently selected at each occurrence from hydrogen, fluorine, or methyl; g is 1 or 2.
- the X term may also be the B-Non-Ar-cyc moiety as disclosed in U.S. Pat. No. 6,809,199 whose disclosure is incorporated by reference herein.
- Non-Ar-Cyc is suitably selected from;
- d is an integer having a value of 1, 2, 3, or 4;
- d′ is 0, or an integer having a value of 1, 2, or 3;
- d′′ is 0, or an integer having a value of 1, 2, or 3;
- e is 0, or is an integer having a value of 1, 2, 3, or 4;
- e′ is 0, or an integer having a value of 1, 2, or 3;
- e′′ is 0, or an integer having a value of 1, 2, or 3;
- f is 0, or is an integer having a value of 1, 2, or 3;
- d+e is 2,3,4,5, or 6;
- R 7′ , R 77 and R 77′′ are each independently selected from hydrogen, C 1-6 alkyl-group, C 2-6 alkenyl-group, C 4-6 cycloalkyl-C 0-6 alkyl-group, N(C 0-4 alkyl)(C 0-4 alkyl)-C 1-4 alkyl-N(C 0-4 alkyl)-group, —N(C 0-4 alkyl)(C 0-4 alkyl) group, C 1-3 alkyl-CO—C 0-4 alkyl-group, C 0-6 alkyl-O—C(O)—C 0-4 alkyl-group, C 0-6 alkyl-C(O)—O—C 0-4 alkyl-group, N(C 0-4 alkyl)(C 0-4 alkyl)-(C 0-4 alkyl)C(O)(C 0-4 alkyl)-group, phenyl-C 0-4 alkyl-group,
- B is —C 1-6 alkyl-, —C 0-3 alkyl-O—C 0-3 alkyl-, —C 0-3 alkyl-NH—C 0-3 alkyl-, —C 0-3 alkyl-NH—C 3-7 cycloalkyl-, —C 0-3 alkyl-N(C 0-3 alkyl)-C(O)—C 0-3 alkyl-, —C 0-3 alkyl-NH—SO 2 —C 0-3 alkyl-, —C 0-3 alkyl-, —C 0-3 alkyl-S—C 0-3 alkyl-, —C 0-3 alkyl-SO 2 —C 0-3 alkyl-, —C 0-3 alkyl-PH—C 0-3 alkyl-, C 0-3 alkyl —C(O)—C 0-3 alkyl, or a direct bond.
- E 1 is CH, N, or CR 66 ; or B and E 1 together form a double bond, i.e., —CH ⁇ C.
- E 2 is CH 2 , CHR 77 , C(OH)R 77 NH, NR 77 , O, S, —S(O)—, or —S(O) 2 —.
- R 66 is independently selected from at each occurrence from halogen, C 0-4 alkyl, —C(O)—O(C 0-4 alkyl), or —C(O)—N(C 0-4 alkyl)-(C 0-4 alkyl).
- Non-Ar-Cyc is:
- the X term may also be the X moiety as disclosed in WO 2004/073628, published September 2004, Boehm et al., whose disclosure is incorporated by reference herein.
- Another aspect of the invention are compounds of Formula (IV) and (IVa):
- Another aspect of the invention are compounds Formula (V) and (Va):
- Another aspect of the invention are compounds formula (VI) and (VIa):
- Another aspect of the invention are compounds of Formula (VIb) and (VIc):
- Another aspect of the invention are compounds of the formula (VIh) and (VIi):
- Another aspect of the invention are compounds of Formula (A) and (A1):
- the present invention is directed to novel compounds of Formula (A) and Formula (A1), or a pharmaceutically acceptable derivative thereof.
- the difference between compounds of Formula (A) and Formula (A1), and that of Formula (I) and (Ia) lies in the linker Y.
- the respective R 1 , R 2 , and R 3 , etc. terms are the same for both groups.
- everything applicable to Formula (I) is also applicable to Formula (A) unless otherwise indicated.
- Another aspect of the invention are compounds of Formulas (B) and (B1):
- linker Y may be present in a similar manner in the same position for all of the remaining formulas, Formula's (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI) and (VIa-VIi), herein.
- the respective R 1 , R 2 , and R 3 , etc. terms will be the same for all the groups.
- Another aspect of the invention are compounds of Formula (VIII) and (VIIIa):
- the X term may also be the B-Non-Ar-cyc moiety as disclosed above.
- the X term may also be the X moiety as disclosed in WO 2004/073628, published September 2004, Boehm et al., whose disclosure is incorporated by reference herein.
- the template containing the G 1 and G 2 moieties will have a numbering system that allows for different (R 1 and R 1′ ) substituents on the phenyl or pyridyl or pyrimidine ring at the C 4 position; the X term at the C 2 position, and at the R 3 substituent in the N 8 position.
- R 1 , R 2 , R x , X and R 3 , etc. terms are the same for both groups within the formulas themselves, for instance, in Formula (VIII) and (VIIIa). For purposes herein, everything applicable to Formula (VIII) is also applicable to Formula (VIIIa) unless otherwise indicated.
- the present invention covers all combinations of particular and preferred groups described hereinabove. It is also to be understood that the present invention encompasses compounds of formula (I) in which a particular group or parameter, for example R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , p, n, or q, etc. may occur more than once. In such compounds it will be appreciated that each group or parameter is independently selected from the values listed. When any variable occurs more than one time in a Formula (as described herein), its definition on each occurrence is independent of its definition at every other occurrence.
- Particular compounds according to the invention include those mentioned in the examples and their pharmaceutically derivatives.
- salts and solvates of compounds of the invention which are suitable for use in medicine are those wherein the counterion or associated solvent is pharmaceutically acceptable.
- salts and solvates having non-pharmaceutically acceptable counterions or associated solvents are within the scope of the present invention, for example, for use as intermediates in the preparation of other compounds of the invention and their pharmaceutically acceptable salts and solvates.
- pharmaceutically acceptable derivative means any pharmaceutically acceptable salt, solvate or prodrug e.g. ester, of a compound of the invention, which upon administration to the recipient is capable of providing (directly or indirectly) a compound of the invention, or an active metabolite or residue thereof.
- pharmaceutically acceptable derivatives are salts, solvates, esters, carbamates and phosphate esters.
- pharmaceutically acceptable derivatives are salts, solvates and esters.
- pharmaceutically acceptable derivatives are salts and esters, in particular salts.
- the compounds of the present invention may be in the form of and/or may be administered as a pharmaceutically acceptable salt.
- suitable salts see Berge et al., J. Pharm. Sci., 1977, 66, 1-19.
- a pharmaceutical acceptable salt may be readily prepared by using a desired acid or base as appropriate.
- the salt may precipitate from solution and be collected by filtration or may be recovered by evaporation of the solvent.
- Salts of the compounds of the present invention may, for example, comprise acid addition salts resulting from reaction of an acid with a nitrogen atom present in a compound of formula (I). Salts encompassed within the term “pharmaceutically acceptable salts” refer to non-toxic salts of the compounds of this invention.
- Suitable addition salts are formed from acids which form non-toxic salts and examples are acetate, benzenesulfonate, benzoate, bicarbonate, bisulfate, bitartrate, borate, bromide, calcium edetate, camsylate, carbonate, chloride, clavulanate, citrate, dihydrochloride, edetate, edisylate, estolate, esylate, ethanesulphonate, formate, fumarate, gluceptate, gluconate, glutamate, glycollylarsanilate, hexylresorcinate, hydrabamine, hydrobromide, hydrochloride, hydrogen phosphate, hydroiodide, hydroxynaphthoate, iodide, isethionate, lactate, lactobionate, laurate, malate, maleate, mandelate, mesylate, methylbromide, methylnitrate, methylsulf
- Pharmaceutically acceptable base salts include ammonium salts such as a trimethylammonium salt, alkali metal salts such as those of sodium and potassium, alkaline earth metal salts such as those of calcium and magnesium and salts with organic bases, including salts of primary, secondary and tertiary amines, such as isopropylamine, diethylamine, ethanolamine, trimethylamine, dicyclohexyl amine and N-methyl-D-glucamine.
- ammonium salts such as a trimethylammonium salt
- alkali metal salts such as those of sodium and potassium
- alkaline earth metal salts such as those of calcium and magnesium
- salts with organic bases including salts of primary, secondary and tertiary amines, such as isopropylamine, diethylamine, ethanolamine, trimethylamine, dicyclohexyl amine and N-methyl-D-glucamine.
- solvates refers to a complex of variable stoichiometry formed by a solute (in this invention, a compound of Formula (I), or a salt thereof) and a solvent.
- solvents for the purpose of the invention may not interfere with the biological activity of the solute.
- suitable solvents include water, methanol, ethanol and acetic acid.
- the solvent used is a pharmaceutically acceptable solvent.
- suitable pharmaceutically acceptable solvents include water, ethanol and acetic acid.
- the solvent used is water.
- a complex with water is known as a “hydrate”. Solvates of the compound of the invention are within the scope of the invention.
- prodrug means a compound which is converted within the body, e.g. by hydrolysis in the blood, into its active form that has medical effects.
- Pharmaceutically acceptable prodrugs are described in T. Higuchi and V. Stella, Prodrugs as Novel Delivery Systems, Vol. 14 of the A.C.S. Symposium Series; Edward B. Roche, ed., Bioreversible Carriers in Drug Design, American Pharmaceutical Association and Pergamon Press, 1987; and in D. Fleisher, S. Ramon and H. Barbra “Improved oral drug delivery: solubility limitations overcome by the use of prodrugs”, Advanced Drug Delivery Reviews (1996) 19(2) 115-130, each of which are incorporated herein by reference.
- Prodrugs are any covalently bonded carriers that release a compound of formula (I) in vivo when such prodrug is administered to a patient.
- Prodrugs are generally prepared by modifying functional groups in a way such that the modification is cleaved, either by routine manipulation or in vivo, yielding the parent compound.
- Prodrugs include, for example, compounds of this invention wherein hydroxy or amine groups are bonded to any group that, when administered to a patient, cleaves to form the hydroxy or amine groups.
- representative examples of prodrugs include (but are not limited to) acetate, formate and benzoate derivatives of alcohol and amine functional groups of the compounds of formula (I).
- esters may be employed, such as methyl esters, ethyl esters, and the like. Esters may be active in their own right and/or be hydrolysable under in vivo conditions in the human body. Suitable pharmaceutically acceptable in vivo hydrolysable ester groups include those which break down readily in the human body to leave the parent acid or its salt.
- halogen such as fluorine, chlorine, bromine or iodine
- hydroxy such as fluorine, chlorine, bromine or iodine
- C 1-10 alkoxy such as methoxy or ethoxy
- halosubstituted C 1-10 alkoxy S(O) m alkyl, such as methyl thio, methylsulfinyl or methyl sulfonyl; a ketone (—C(O)), or an aldehyde (—C(O)R 6′ ), such as C(O)C 1-10 alkyl or C(O)aryl
- R 6′ is hydrogen, C 1-10 alkyl, C 3-7 cycloalkyl, heterocyclyl, heterocyclyl C 1-10 alkyl, aryl, arylC 1-10 alkyl, heteroaryl or heteroarylC 1-10 alkyl (and wherein the R 6′ moieties,
- halosubstituted C 1-10 alkyl such CF 2 CF 2 H, or CF 3 ; an optionally substituted aryl, such as phenyl, or an optionally substituted arylalkyl, such as benzyl or phenethyl, wherein these aryl containing moieties may also be substituted one to two times by halogen; hydroxy; hydroxy substituted alkyl; C 1-4 alkoxy; S(O) m C 1-4 alkyl; amino, mono & di-substituted C 1-4 alkyl amino; C 1-4 alkyl, or CF 3 .
- Suitable pharmaceutically acceptable salts are well known to those skilled in the art and include salts formed with both organic and inorganic acids or bases.
- Pharmaceutically acceptable acid addition salts include those formed from hydrochloric, hydrobromic, sulphuric, citric, tartaric, phosphoric, lactic, pyruvic, acetic, trifluoroacetic, triphenylacetic, sulphamic, sulphanilic, succinic, oxalic, fumaric, maleic, malic, glutamic, aspartic, oxaloacetic, alkyl sulphonic acid derivatives, such as methanesulphonic, or ethanesulphonic, arylsulphonic acid derivatives, such as p-toluenesulphonic, m-toluenesulphonic, benzenesulphonic, camphor sulphonic, 4-chlorobenzenesulphonic, 4-bromobenzenesulphonic, 4-phenylbenzenes
- Pharmaceutically acceptable base salts include ammonium salts, alkali metal salts such as those of sodium and potassium, alkaline earth metal salts such as those of calcium and magnesium and salts with organic bases such as dicyclohexyl amine and N-methyl-D-glucamine.
- pharmaceutically acceptable salts of compounds of Formula (I) may also be formed with a pharmaceutically acceptable cation, for instance, if a substituent group comprises a carboxy moiety.
- Suitable pharmaceutically acceptable cations are well known to those skilled in the art and include alkaline, alkaline earth, ammonium and quaternary ammonium cations.
- halo or “halogens” is used herein to mean the halogens, chloro, fluoro, bromo and iodo.
- C 1-10 alkyl or “alkyl” or “alkyl 1-10 ” is used herein to mean both straight and branched hydrocarbon chain containing the specified number of carbon atoms, e.g. C 1-10 alkyl means a straight of branched alkyl chain of at least 1, and at most 10, carbon atoms, unless the chain length is otherwise limited.
- alkyl as used herein include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, isobutyl, isopropyl, sec-butyl, tert-butyl or t-butyl and hexyl and the like.
- alkenyl refers to straight or branched hydrocarbon chains containing the specified number of carbon atoms and containing at least one double bond.
- C 2-6 alkenyl means a straight or branched alkenyl containing at least 2, and at most 6, carbon atoms and containing at least one double bond.
- alkenyl as used herein include, but are not limited to ethenyl, 2-propenyl, 3-butenyl, 2-butenyl, 2-pentenyl, 3-pentenyl, 3-methyl-2-butenyl, 3-methylbut-2-enyl, 3-hexenyl, 1,1-dimethylbut-2-enyl and the like.
- alkoxy refers to straight or branched chain alkoxy groups containing the specified number of carbon atoms.
- C 1-6 alkoxy means a straight or branched alkoxy containing at least 1, and at most 6, carbon atoms.
- alkoxy as used herein include, but are not limited to, methoxy, ethoxy, propoxy, prop-2-oxy, butoxy, but-2-oxy, 2-methylprop-1-oxy, 2-methylprop-2-oxy, pentoxy and hexyloxy.
- cycloalkyl refers to cyclic radicals, such as a non-aromatic hydrocarbon ring containing a specified number of carbon atoms.
- C 3-7 cycloalkyl means a non-aromatic ring containing at least three, and at most seven, ring carbon atoms.
- Representative examples of “cycloalkyl” as used herein include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl and the like.
- cycloalkenyl is used herein to mean cyclic radicals, such as a non-aromatic hydrocarbon ring containing a specified number of carbon atoms preferably of 5 to 7 carbons, which have at least one bond including but not limited to cyclopentenyl, cyclohexenyl, and the like.
- alkenyl is used herein at all occurrences to mean straight or branched chain radical of 2-10 carbon atoms, unless the chain length is limited thereto, including, but not limited to ethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl and the like.
- aryl is used herein to mean phenyl, naphthyl, and indene.
- heteroaryl ring refers to a monocyclic five- to seven-membered unsaturated hydrocarbon ring containing at least one heteroatom selected from oxygen, nitrogen and sulfur.
- heteroaryl rings include, but are not limited to, furyl, pyranyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, oxathiadiazolyl, triazolyl, tetrazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and uracil.
- heteroaryl ring refers to fused aromatic rings comprising at least one heteroatom selected from oxygen, nitrogen and sulfur.
- Each of the fused rings may contain five or six ring atoms.
- fused aromatic rings include, but are not limited to, indolyl, isoindolyl, indazolyl, indolizinyl, azaindolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzofuranyl, benzothiophenyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, cinnolinyl, purinyl, and phthalazinyl.
- heterocyclic rings “heterocyclic moieties”, and “heterocyclyl” is used herein to mean a monocyclic three- to seven-membered saturated or non-aromatic, unsaturated hydrocarbon ring containing at least one heteroatom selected from nitrogen, oxygen, sulphur or oxidized sulphur moieties, such as S(O) m , and m is 0 or an integer having a value of 1 or 2.
- heterocyclic rings “heterocyclic moieties”, and “heterocyclyl” shall also refer to fused rings, saturated or partially unsaturated, and wherein one of the rings may be aromatic, or heteroaromatic.
- Each of the fused rings may have from four to seven ring atoms.
- heterocyclyl groups include, but are not limited to, the saturated or partially saturated versions of the heteroaryl moieties as defined above, such as tetrahydropyrrole, tetrahydropyran, tetrahydrofuran, tetrahydrothiophene (including oxidized versions of the sulfur moiety), azepine, diazepine, aziridinyl, pyrrolinyl, pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 3-oxo-1-pyrrolidinyl, 1,3-benzdioxol-5-yl, imidazolinyl, imidazolidinyl, indolinyl, pyrazolinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino (including oxidized versions of the sulfur moiety).
- arylalkyl or “heteroarylalkyl” or “heterocyclicalkyl” is used herein to mean a C 1-4 alkyl (as defined above) attached to an aryl, heteroaryl or heterocyclic moiety (as also defined above) unless otherwise indicated.
- sulfinyl is used herein to mean the oxide S(O) of the corresponding sulfide, the term “thio” refers to the sulfide, and the term “sulfonyl” refers to the fully oxidized S(O) 2 moiety.
- aroyl is used herein to mean C(O)Ar, wherein Ar is as phenyl, naphthyl, or aryl alkyl derivative such as defined above, such group include but are not limited to benzyl and phenethyl.
- alkanoyl is used herein to mean C(O)C 1-10 alkyl wherein the alkyl is as defined above.
- the term “optionally” means that the subsequently described event(s) may or may not occur, and includes both event(s) which occur and events that do not occur.
- substituted refers to substitution with the named substituent or substituents, multiple degrees of substitution being allowed unless otherwise stated.
- the present invention covers all combinations of particular and preferred groups described hereinabove. It is also to be understood that the present invention encompasses compounds of formula (I) in which a particular group or parameter, for example R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , n, m, or t, etc. may occur more than once. In such compounds it will be appreciated that each group or parameter is independently selected from the values listed. When any variable occurs more than one time in a Formula (as described herein), its definition on each occurrence is independent of its definition at every other occurrence.
- the compounds of the Formulas herein may have one or more asymmetric carbon atom and may occur as racemates, racemic mixtures and as individual enantiomers or diastereomers. All such isomeric forms are included within the present invention, including mixtures thereof.
- Cis (E) and trans (Z) isomerism may also occur.
- the present invention includes the individual stereoisomers of the compound of the invention and where appropriate, the individual tautomeric forms thereof, together with mixtures thereof.
- Separation of diastereoisomers or cis and trans isomers may be achieved by conventional techniques, e.g. by fractional crystallisation, chromatography or H.P.L.C.
- a stereoisomeric mixture of the agent may also be prepared from a corresponding optically pure intermediate or by resolution, such as H.P.L.C. of the corresponding racemate using a suitable chiral support or by fractional crystallisation of the diastereoisomeric salts formed by reaction of the corresponding racemate with a suitable optically active acid or base, as appropriate.
- Exemplified compounds of the compounds of this invention include the racemates, or optically active forms of the compounds of the working examples herein, and pharmaceutically acceptable salts thereof.
- the compounds of this invention may be made by a variety of methods, including standard chemistry. Any previously defined variable will continue to have the previously defined meaning unless otherwise indicated. Illustrative general synthetic methods are set out below and then specific compounds of the invention are prepared in the working Examples.
- the compounds of Formula (I) and (Ia), (II) and (IIa), (III) and (IIIa), (IV) and (IVa), (V) and (Va), (VI), (VIa-VIi), (VIII) and (VIIIa), (A), (A1), (B) and (B1) may be obtained by applying the synthetic procedures described herein.
- the synthesis provided for is applicable to producing compounds of the Formulas herein having a variety of different R 1 , R 2 , X, and R 3 groups which are reacted, employing optional substituents which are suitably protected, to achieve compatibility with the reactions outlined herein. Subsequent deprotection, in those cases, then affords compounds of the nature generally disclosed. While a particular formula with particular substituent groups is shown herein, the synthesis is applicable to all formulas and all substituent groups herein.
- R 4 N ⁇ C ⁇ O; NR 10 —C(O)R 6 from NHR 10 by treatment with Cl—C(O)R 6 in pyridine; C( ⁇ NR 10 )NR 4 R 14 from C(NR 4 R 14 )S with H 3 NR 10 + OAc ⁇ by heating in alcohol; C(NR 4 R 14 )SR 6 from C(S)NR 4 R 14 with R 6 —I in an inert solvent, e.g.
- Precursors of the groups R 1 , R 2 and R 3 can be other R 1 , R 2 and R 3 , etc. groups that may be interconverted by applying standard techniques for functional group interconversion.
- a moiety is a halo substituted C 1-10 alkyl
- a suitable azide salt e.g., sodium EDTA
- X′ is halo (e.g., chloro) to yield the corresponding C 1-10 alkylNHS(O) 2 R 7 compound.
- the moiety is a halo-substituted C 1-10 -alkyl it can be reacted with an amine R 4 R 14 NH to yield the corresponding C 1-10 -alkylNR 4 R 14 compound, or can be reacted with an alkali metal salt of R 7 SH to yield the corresponding C 1-10 alkylSR 7 compound.
- hydroxyl protecting groups include ether forming groups such as benzyl, and aryl groups such as tert-butoxycarbonyl (Boc), silyl ethers, such as t-butyldimethyl or t-butyldiphenyl, and alkyl ethers, such as methyl connected by an alkyl chain of variable link, (CR 10 R 20 ) n .
- Amino protecting groups may include benzyl, aryl such as acetyl and trialkylsilyl groups.
- Carboxylic acid groups are typically protected by conversion to an ester that can easily be hydrolyzed, for example, trichloethyl, tert-butyl, benzyl and the like.
- LG described as Leaving group 1 (LG1) & LG2) in 1 (or 2), or elsewhere, can be independently selected from —Cl, —Br, —I, or —OTf and these groups can be installed through the transformation of another functional group (e.g. —OH) by following the methods well known in the art (e.g., treatment of the —OH compound with POCl 3 ).
- Method A is for conversion of 1 to 2.
- the methods include, but are not limited to condensation with NH 2 OH followed by treatment with thionyl chloride (SOCl 2 ) [e.g., Santilli et al., J. Heterocycl. Chem . (1971), 445-53] or oxidation of —CHO group to —COOH followed by formation of a primary amide (—CONH 2 ) and treatment with POCl 3 .
- SOCl 2 thionyl chloride
- Suitable Method A can also be utilized to furnish the conversion of 4 to 3—Scheme I.
- Method B is for selective displacement of suitable aldehyde 1 or nitrile 2 with an amine (R 3 —NH 2 ).
- This type of displacement may be achieved using triethylamine and the desired amine R 3 NH 2 in chloroform at room temperature for 10 minutes.
- the reaction was very effective for a range of alkyl amines (78-95% yield).
- elevated temperatures (reflux), longer reaction time (24 hours) and presence of NaH (or Na) may be necessary for reaction completion.
- Use of the base could be omitted when 3 or more equivalent of the desired amine were used.
- Suitable bases include but are not limited to pyridine, diisopropyl ethylamine or pyrrolidine, which may also be used in an appropriate organic solvent, including but not limited to THF, diethyl ether, DCM, DMF, DMSO, toluene or dioxane.
- Method C is for the reduction of nitrile 3 to amine 5.
- 5 may be considered a primary amine (NH 2 ), a secondary amine (because of —NH(R3)) or an amine (as it contains basic nitrogen).
- This method includes, but is not limited to BH 3 in appropriate organic solvent, such as THF, DCM, toluene, DMSO, diethyl ether or dioxane.
- Other suitable reduction reagents include but are not limited to NaBH 4 , LAH or DIBAL.
- Method C may require elevated temperatures (e.g., heating, refluxing or irradiating with microwave).
- Another example of the method is hydrogenation (H 2 ) in the presence of transition metals (e.g., Pd/C, Raney-Ni, PdCl 2 ).
- Method D is for the cyclization of 5 to 6.
- This method requires the presence of a cyclization reagent (e.g., CDI, COCl 2 , tri-phosgene, or phenyl chloroformate methyl chloroformate).
- a cyclization reagent e.g., CDI, COCl 2 , tri-phosgene, or phenyl chloroformate methyl chloroformate.
- Presence of a suitable base may help the reaction to go to completion and examples of the base include, but not limited to triethyl amine, diisopropylethylamine or pyrrolidine.
- Reaction solvent can be DCM, THF, toluene, DMSO, or DMF.
- Method E is for the installation of group -X [e.g., 6 to 7, 10 to (I), 11 to (I) or 9 to 12]. This may or may not require first conversion of sulfide (—SMe) to sulfoxide (—SOMe) or sulfone (—SO 2 Me). This conversion can be achieved using meta-chloroperoxybenzoic acid (mCPBA) in high yield and purity. Suitable oxidation methods for use herein include use of one or two equivalents of meta-chloroperoxybenzoic acid (mCPBA) or Oxone® to afford either the sulfoxides or sulfones.
- mCPBA meta-chloroperoxybenzoic acid
- Oxone® Oxone®
- Oxidation of the sulfides to sulfoxides or sulfones can also be effected by OsO 4 and catalytic tertiary amine N-oxide, hydrogen peroxide, hydrogen peroxide/NaWO4, and other peracids, oxygen, ozone, organic peroxides, potassium and zinc permanganate, potassium persulfate, and sodium hypochlorite.
- the subsequent displacement of sulfone group —SO 2 Me (likewise, all displacement reactions mentioned below may be achieved using the sulfide —SMe or sulfoxide —SOMe) requires a suitable nucleophile (e.g., amine, alcohol) containing the unit —X.
- the sulfone may be displaced by primary and secondary alkylamines without additional base catalysis, preferably in a polar aprotic solvent, such as but not limited to, N-methylpyrrolidin-2-one (NMP), and at varying temperatures depending upon the nucleophilicity of the amine.
- NMP N-methylpyrrolidin-2-one
- displacement of the sulfone with ethanolamine, in NMP occurred in 30 min. at 65° C., while a more hindered amine such as tris(hydroxymethyl)-aminomethane may require elevated temperatures and extended reaction times (80° C. over a 24 hour reaction time).
- the sulfone can also be displaced by a primary or secondary amine with an additional non-nucleophilic base (e.g. DIPEA) in aprotic solvents like DCM, CH 3 CN, NMP, and at varying temperatures depending upon the nucleophilicity of the amine.
- DIPEA additional non-nucle
- the sulfone may also be displaced with a substituted arylamine, or heteroarylamine at elevated temperatures, sometimes requiring formation of the aryl or heteroarylamine anion with sodium hydride, or other suitable base, in DMSO.
- the sulfone may be readily displaced with aluminum salts of aryl or heteroaryl amines as previously described in the patent literature (see for example WO 99/32121, whose disclosure is incorporated by reference herein).
- sulfone may be displaced with aryl or heteroaryl or alkyl thiols or alkyl or aryl or heteroaryl alcohols.
- Analogs containing sulfones as the X substituents may be displaced with sodium alkoxide in the alcohol, or alternatively reactive alkoxide or phenoxide nucleophiles that may be generated from the alcohol or phenol with a suitable base such as sodium, NaH or sodium bistrimethylsilyl amide in a polar aprotic solvent such as DMSO, or run as a neat reaction.
- the sulfone may be displaced with carbon nucleophiles.
- Suitable carbon nucleophiles include, but not limited to aryl Grignard reagents, alkyl Grignard reagents or related organometallics such as organo lithium, zinc, tin, copper or boron. These reactions may, in some cases, require transition metal catalysis such as with Pd or Ni catalysts.
- Method F is for coupling with appropriate aryl groups to convert 7 to compounds of Formula (I) (or 6 to 10).
- This transformation may be achieved using, but not limited to boronic acids (e.g., F1A) under Suzuki cross-coupling conditions, employing a palladium catalyst, such as tetrakis(triphenylphosphine) palladium(0).
- the coupling conditions include the use of appropriate solvents. These solvents include, but are not limited to dioxane, THF, DMF, DMSO, NMP, acetone, water, or a combination or a mixture thereof.
- the solvent is THF/H 2 O, or dioxane/H 2 O.
- the coupling conditions also include the presence of catalytic amount of catalysts and these catalysts include, but not limited to tetrakis(triphenyl-phosphine)-palladium (0), PdCl2, Pd(OAc) 2 , (CH3CN) 2 PdCl2, Pd(dppf) 2 , or [1,1′-bis(diphenylphosphino)-ferrocene]-dichloropalladium(II).
- catalysts include, but not limited to tetrakis(triphenyl-phosphine)-palladium (0), PdCl2, Pd(OAc) 2 , (CH3CN) 2 PdCl2, Pd(dppf) 2 , or [1,1′-bis(diphenylphosphino)-ferrocene]-dichloropalladium(II).
- the coupling reaction may or may not require the presence of a base.
- Suitable bases include, but are not limited to NaHCO 3 , KHCO 3 , Na 2 CO 3 , K 2 CO 3 , KOAc or combination or mixture thereof.
- the base is K 2 CO 3 and KOAc.
- the coupling reaction may or may not require heating.
- the heating can be carried out with a regular oil bath or microwave irradiations and the temperature can be varied from room temperature to >100° C., i.e. reflux temperature of the solvent.
- the coupling reaction may or may not require a sealed reaction vessel and the internal pressure can be varied from one atmosphere to 100 atmospheres.
- the cross-coupling may be performed using aryl or heteroaryl organozinc [e.g., aryl/heteroaryl-ZnBr, aryl/heteroaryl —ZnCl, aryl/heteroaryl-Zn-aryl/heteroaryl], organocopper [e.g., (aryl/heteroaryl) 2 -CuLi], organotin [e.g., aryl/heteroaryl-Sn(CH 3 ) 3 , aryl/heteroaryl —Sn(CH 2 CH 2 CH 2 CH 3 ) 3 ], (e.g., F1C), or other organometallic reagents (e.g., FIB) known in the art [see for example Solberg, J.; Undheim, K.
- organozinc e.g., aryl/heteroaryl-ZnBr, aryl/heteroaryl —ZnCl
- Such solvents include, but are not limited to dioxane, THF, methylene chloride, chloroform, benzene, hexane, ethyl ether, tert-butyl methyl ether or a combination or a mixture thereof.
- the coupling reaction may, or may not, require the presence of catalytic amount of a catalyst.
- catalysts include, but are not limited to tetrakis(triphenylphosphine)palladium (0), PdCl 2 , Pd(OAc) 2 , (CH 3 CN) 2 PdCl 2 , Pd(dppf) 2 .
- the reaction temperature can be varied from ⁇ 78° C. to >100° C., i.e. reflux temperature of the solvent.
- this reaction process step may be performed under suitable microwave irradiation conditions, if needed.
- This reaction may, or may not, require a sealed reaction vessel and the internal pressure can be varied from one atmosphere to 100 atmospheres.
- Method G is for coupling of 7 (or 6 or 16) with an aryl group whose structure has a suitable precursor (e.g., acidic group —CO 2 H) to the final substituent R 1 in Formula (I).
- This transformation may be achieved using, but not limited to boronic acids (e.g., G1A) or protected acids (e.g., G1C) under Suzuki coupling conditions, (THF/H 2 O, and K 2 CO 3 ) employing a palladium catalyst, such as tetrakis(triphenylphosphine) palladium(0).
- a palladium catalyst such as tetrakis(triphenylphosphine) palladium(0).
- these Suzuki coupling reactions may be run under microwave conditions.
- the boronic acid (D1A or D1E) or ester can be synthesized either by the palladium catalyzed coupling of an aryl halide and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi1,3,2-dioxaborolane or the transmetalation of an aryl halide with a Grignard reagent, e.g., isopropylmagnesium bromide followed by a trialkylborate (e.g., triethylborate) in a suitable solvent like THF.
- a Grignard reagent e.g., isopropylmagnesium bromide followed by a trialkylborate (e.g., triethylborate) in a suitable solvent like THF.
- the cross-coupling may be performed using aryl or heteroaryl organozinc, organocopper, organotin (e.g., G1B), or other organometallic reagents (e.g., G1D) known in the art [see for example Solberg, J.; Undheim, K. Acta Chemica Scandinavia 1989, 62-68]. Suitable de-protection is followed if a protected precursor (e.g., G3, G4) is used.
- a protected precursor e.g., G3, G4
- Method H is for the transformation of the suitable precursor (e.g., acidic group —COOH in 8, 9, or 12) to the final substituent R 1 .
- This type of transformations can be achieved by utilizing well-established strategies in the art.
- the transformation may be done in one step (such as coupling with amines HN(R 10′ )R b under standard coupling conditions e.g. EDC/HOBT/ET 3 N in CH 3 CN; coupling with alcohol, HOR b under standard coupling conditions, e.g.
- DCC DCC, DMAP in DCM to form esters or reduction to alcohol
- step e.g., Curtuis rearrangement to form isocyanates followed by urea formation with amines or acid chloride formation followed by addition of an amine, HN(R 10′ )R b or an alcohol, HOR b plus a non-nucleophilic base, e.g. DIPEA in an aprotic solvent like DCM.
- This conversion may require a deprotection step to install the precursor at first (e.g., hydrolysis of —CO 2 Me with LiOH/THF/water to prepare —COOH).
- Method I is for urea formation to convert 4 to 13. This can be achieved by following strategies well-established in the art. Strategies include, but are not limited to reaction with ClSO 2 NCO (or Me 3 SiNCO) followed by treatment with H 2 O, reaction with COCl 2 (CDI, or triphosgene) followed by treatment with NH 3 (or NH 4 OH), reaction with ClCO 2 Me (or ClCO 2 Et) followed by treatment with NH 3 (or NH 4 OH) or reaction with NH 2 CO 2 (t-Bu).
- Strategies include, but are not limited to reaction with ClSO 2 NCO (or Me 3 SiNCO) followed by treatment with H 2 O, reaction with COCl 2 (CDI, or triphosgene) followed by treatment with NH 3 (or NH 4 OH), reaction with ClCO 2 Me (or ClCO 2 Et) followed by treatment with NH 3 (or NH 4 OH) or reaction with NH 2 CO 2 (t-Bu).
- Method J is for imine formation to convert 13 to 14. This can be achieved by following various strategies known in the art. Strategies include, but are not limited to treatment with an acid including TFA, HOAc, HCl, H 2 SO 4 or a Lewis acid (e.g., AlCl3). This conversion may require elevated temperatures (e.g., heat, solvent reflux, microwave irradiation) in appropriate organic solvents (e.g., THF, CH 2 Cl 2 , toluene, DMSO, CH 3 CN or dioxane).
- an acid including TFA, HOAc, HCl, H 2 SO 4 or a Lewis acid (e.g., AlCl3).
- This conversion may require elevated temperatures (e.g., heat, solvent reflux, microwave irradiation) in appropriate organic solvents (e.g., THF, CH 2 Cl 2 , toluene, DMSO, CH 3 CN or dioxane).
- Method K is an alternative strategy to prepare compounds in Scheme 2.
- This method is for the de-saturation (lose of 2H in the formula) of compounds in Scheme 1 resulting in the corresponding compounds in Scheme 2.
- This conversion includes, but not limited to Formula (Ia)-Scheme 2 from Formula (I)-Scheme 1,14-Scheme 2 from 6-Scheme 1.
- This type of transformations can be achieved by following methods well-known in the art (e.g., treatment with NBS and AIBN in CCl 4 under elevated temperatures, treatment with MnO 2 in chlorobenzene under elevated temperatures).
- Method L is for reduction of compounds in Scheme 2.
- This method provides an alternative strategy to synthesize compounds in Scheme 1 [e.g., Formula (Ia)-Scheme 2 to Formula (I)-Scheme 1, 14-Scheme 2 to 6-Scheme 1].
- This type of conversion can be achieved by using suitable imine reduction methods published in the art (e.g., treatment with Et 3 SiH, NaBH 4 , H 2 —Pd/C).
- Method F & G should be utilized. Examples of these reagents include, but not limited to those shown in Scheme 3. Suitable reagents in Method F & G for the preparation of compounds with Formula (VIb-VIi) require the presence of G5-8 in appropriate position.
- Preparation of compounds with Formula (A), (A1), (B) or (B1) can be achieved from appropriate intermediates in Scheme 1 (or Scheme 2) using proper synthetic methods known to the scientists with appropriate training in the literature.
- An example of these types of preparations is demonstrated, but not limited to, in Scheme 4.
- the preparation can be achieved by reacting compound 7 (for A or B) or 16 (for A1 or B1) with another reagent with appropriate structures as shown in Scheme 4 employing Method M.
- Method M is for the substitution of -LG 2 with appropriate compound containing the structural unit of —Y—H. This can be achieved by heating the reaction mixtures in appropriate solvents.
- the heating method can be selected from either a regular oil bath or microwave irradiations.
- Solvents can be CH 2 Cl 2 , DMSO, DMF, toluene, benzene, CH 3 CN or NMP.
- the reaction may or may not require the presence of bases.
- An example of the base can be selected from, but not limited to triethyl amine, diisopropyl ethyl amine, NaH, n-BuLi, tert-BuLi, tert-BuOK, Li 2 CO 3 , Cs 2 CO 3 and pyridine.
- This transformation may also require the presence of catalytic amount of catalysts containing transition metals (e.g., Pd, Cu, Ni, or W).
- catalysts include, but not limited to Pd/C, Pd(PPh 3 ) 4 and PdCl 2 .
- Compounds that have Y ⁇ S(O) m or S(O) m C(R y )(R z ) may also be prepared by the oxidation of their corresponding compounds with Y ⁇ S or SC(R y )(R z ). Suitable oxidation methods for use herein include, but not limited to mCPBA, Oxone, OsO 4 , H 2 O 2 , potassium and zinc permanganate.
- One aspect of the invention are the novel compounds of Formula (C) and (C1):
- R 9 is methyl. In another embodiment, m is 0 or 1.
- Another aspect of the invention are compounds of Formula (G):
- R 3 is substituted as defined herein for compounds of Formula (I).
- R 3 is substituted as defined herein for compounds of Formula (I).
- Compounds of Formula (H) may be made by reacting the compound disclosed as structure 4 in Scheme I found in WO 02/059083 with a suitably substituted isocyanate, such as ClS(O) 2 NCO, or TMS —NCO in a aprotic organic solvent, such as toluene, methylene chloride, chloroform, benzene, THF, hexane, optionally with a non-nucleophilic base, such as triethylamine, diisopropyl ethylamine, pyridine, followed by reaction with ammonia; or by reacting structure 4 with phosgene in an aprotic organic solvent, such as toluene, methylene chloride, chloroform, benzene, THF, hexane, optionally with a non-nucleophilic base, such as triethylamine, diisopropyl ethylamine, pyridine, followed by reaction with ammonia or by
- DMAP 4-(Dimethylamino)pyridine
- SPE Solid phase extraction
- DCM Dichloromethane
- m-CPBA 3-Chlorobenzene- carboperoxoic acid
- DMF N,N-Dimethylformamide
- MDAP Mass directed auto preparation
- dppf 1,1′-Bis(diphenylphosphino)-
- NIS N-Iodosuccinimide ferrocene
- DMSO Dimethylsulfoxide
- HATU O-(7-Azabenzotriazol-1- yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate
- DIPEA N,N- HBTU: O-Benzotriazol-1-yl- Diisopropylethylamine N,N,N′,N′-tetramethyluronium hexafluorophosphate
- DSC differential scanning HOBT: 1-Hydoxybenzo
- Liquid Chromatograph System Shimadzu LC system with SCL-10A Controller and dual UV detector
- Autosampler Leap CTC with a Valco six port injector
- Column Aquasil/Aquasil (C18 40 ⁇ 1 mm)
- Gradient linear Channel A: UV 214 nm Channel B: ELS Time Dura. Flow Step (min) (min) ( ⁇ L/min) Sol.
- Heating of reaction mixtures with microwave irradiations was carried out on a Smith Creator (purchased from Personal Chemistry, Forboro/MA, now owned by Biotage), a Emrys Optimizer (purchased from Personal Chemistry) or an Explorer (provided by CEM Discover, Matthews/NC) microwave.
- the sulfoxide/sulfone of the template is dissolved in THF/CHCl 3 (1:1) and the amine (5 eq) and diisopropylethylamine (3 eq) are added and allowed to stir for 1 h. The mixture is concentrated in vacuo.
- the acid is dissolved in DMF and HATU (1 eq) is added.
- DIEA is added (2 eq) followed by the amine (1.1 eq) and allowed to stir for 18 h.
- the reaction mixture is concentrated and redissolved in CHCl 3 .
- 3-Thiophenecarboxylic acid (2.0 g, 15.6 mmol) was dissolved in methylene chloride (100 mL) and 2 drops of DMF were added. The mixture was cooled to 0° C. and oxalyl chloride (1.5 mL, 17.1 mmol) was added slowly and allowed to warm to room temperature. Gas evolution was observed during warming.
- 3-Methyl-4-iodoaniline (5.45 g, 23.5 mmol), 4 drops of pyridine and K 2 CO 3 (2.58 g, 18.7 mmol) are dissolved in CH 2 Cl 2 (10 mL) and cooled to about 0° C.
- the acid chloride mixture is slowly added to the cooled aniline mixture and allowed to warm to room temperature and stirred for about 18 h.
- the resulting mixture is filtered, washed with ethyl acetate and the filtrate is concentrated to a brown oil.
- the crude material was purified via flash chromatography (10-30% ethyl acetate in hexanes) to afford the title compound (1.56 g, 29%) as an off-white solid.
- Example 23d N- ⁇ 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methylphenyl ⁇ -3-fluoro-4-methylbenzamide (0.070 g, 0.120 mmol) was added in iso-propanol (2 mL). The reaction was stirred under argon for 1 hour and then warmed to 80° C. for 3 hours.
- Example 27a The product of Example 27a (0.07 g, 0.1 mmol) was suspended in CH 2 Cl 2 (3 mL) and treated with TFA (2 mL) on ice under argon. The reaction mixture was stirred at 0° C. for 90 min before most of the solvent and TFA were removed in vacuo. The crude residue was basified with NaOH (1M) and extracted with EtOAc. The organics were washed with water, brine (twice), dried over Na 2 SO 4 , filtered and evaporated. The crude residue was purified by flash chromatography on silica gel, eluting with 6:0.5:0.025 CH 2 Cl 2 :EtOH:NH 4 OH and then by prep HPLC to afford the title compound as a white solid. mp 218-223.5° C.; LC-MS m/z 602 (M+H) + , 1.84 min (ret. time).
- Methyl t-butyl ether (MTBE) (21.2 mL) was added to partially crystalline 3-[2- ⁇ [3-(diethylamino)propyl]amino ⁇ -8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide free base (0.847 g).
- the resulting slurry was temperature-cycled with stirring from 10-40° C. overnight.
- the product was filtered, washed with MTBE, and dried overnight in a vacuum oven at 50° C. with a slow nitrogen bleed.
- Acetonitrile 140 mL was added to partially crystalline 3-[2- ⁇ [3-(diethylamino)propyl]amino ⁇ -8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide free base (0.867 g).
- the resulting mixture was temperature-cycled with stirring from 10-40° C. overnight at room temperature.
- the product was filtered, washed with acetonitrile, and dried overnight in a vacuum oven at 50° C. with a slow nitrogen bleed.
- Acetone (451 uL) was added to the partially crystalline 3-[2- ⁇ [3-(diethylamino)propyl]amino ⁇ -8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide free-base (25.2 mg).
- Hydrochloric acid was added (1.1 equivalents; IM in 1,4-dioxane), and the resulting mixture was temperature-cycled from 0-40° C. for a minimum of 48 hours. The product was filtered and dried in vacuo at room temperature.
- Acetone with 5% water (12.2 mL) was added to the crystalline 3-[2- ⁇ [3-(diethylamino)propyl]amino ⁇ -8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide free-base (0.608 g) and solid fumaric acid (1.0 equivalents; 124.8 mg).
- the resulting mixture was heated to 50° C. for one hour.
- the mixture was cooled to room temperature and stirred for 30 minutes.
- the product was filtered, washed with acetone with 5% water, and dried overnight in a vacuum oven at 50° C.
- Acetone (845 uL) was added to the crystalline 3-[2- ⁇ [3-(diethylamino)propyl]-amino ⁇ -8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide-free-base (46.9 mg), and the resulting mixture was heated to 50° C. Phosphoric acid was added (1.0 equivalents; IM in methanol). Additional methanol (5 uL) was added to the resulting oily mixture to increase solubility slightly. The mixture was cooled to room temperature and stirred overnight.
- the product was filtered and dried for at least one hour in a vacuum oven at 50° C. with a slow nitrogen bleed.
- the yield was 67.1% (36.9 mg) of partially crystalline 3-[2- ⁇ [3-(diethylamino)propyl]amino ⁇ -8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide phosphate salt.
- Acetonitrile (450 uL) was added to the crystalline 3-[2- ⁇ [3-(diethylamino)propyl]-amino ⁇ -8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide fee-base (25.0 mg), and the resulting mixture was heated to 50° C. Ethanedisulfonic acid was added (1.1 equivalents; 1M in methanol). The mixture was cooled to room temperature and stirred several hours. The product was filtered and dried for at least one hour in a vacuum oven at 50° C. with a slow nitrogen bleed.
- Example 86a To a solution of the title compound from Example 86a (250 mg, 0.70 mmol) in DCM (10 mL) were added 4-(1-pyrrolidinyl)piperidine (323 mg, 2.1 mmol) and N,N-diisopropylethylamine (0.3 mL, 1.7 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7]+NH 4 OH[3]) provided the title compound as a white solid (253 mg, 81%). LC-MS m/z 449 (M+H) + .
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Communicable Diseases (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/908,435 US20090239846A1 (en) | 2005-03-25 | 2006-03-24 | Novel Compounds |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US66534705P | 2005-03-25 | 2005-03-25 | |
PCT/US2006/010792 WO2006104889A2 (en) | 2005-03-25 | 2006-03-24 | Novel compounds |
US11/908,435 US20090239846A1 (en) | 2005-03-25 | 2006-03-24 | Novel Compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
US20090239846A1 true US20090239846A1 (en) | 2009-09-24 |
Family
ID=37053936
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/389,112 Expired - Fee Related US7674789B2 (en) | 2005-03-25 | 2006-03-24 | Compounds |
US11/908,435 Abandoned US20090239846A1 (en) | 2005-03-25 | 2006-03-24 | Novel Compounds |
US12/618,927 Abandoned US20100093765A1 (en) | 2005-03-25 | 2009-11-16 | Novel compounds |
US12/618,933 Abandoned US20100093766A1 (en) | 2005-03-25 | 2009-11-16 | Novel compounds |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/389,112 Expired - Fee Related US7674789B2 (en) | 2005-03-25 | 2006-03-24 | Compounds |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/618,927 Abandoned US20100093765A1 (en) | 2005-03-25 | 2009-11-16 | Novel compounds |
US12/618,933 Abandoned US20100093766A1 (en) | 2005-03-25 | 2009-11-16 | Novel compounds |
Country Status (23)
Country | Link |
---|---|
US (4) | US7674789B2 (ja) |
EP (1) | EP1866311A4 (ja) |
JP (1) | JP2008535820A (ja) |
KR (1) | KR20080005223A (ja) |
CN (1) | CN101184758B (ja) |
AP (1) | AP2281A (ja) |
AR (1) | AR053450A1 (ja) |
AU (1) | AU2006229967B2 (ja) |
BR (1) | BRPI0609579A2 (ja) |
CA (1) | CA2602546A1 (ja) |
EA (1) | EA200702074A1 (ja) |
IL (1) | IL185915A0 (ja) |
MA (1) | MA29340B1 (ja) |
MX (1) | MX2007011883A (ja) |
NO (1) | NO20075273L (ja) |
NZ (1) | NZ561438A (ja) |
PE (2) | PE20061193A1 (ja) |
SG (1) | SG166100A1 (ja) |
TW (1) | TW200724142A (ja) |
UA (1) | UA95230C2 (ja) |
UY (1) | UY29439A1 (ja) |
WO (1) | WO2006104889A2 (ja) |
ZA (1) | ZA200707798B (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070238743A1 (en) * | 2000-03-02 | 2007-10-11 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
US20090048444A1 (en) * | 2005-03-25 | 2009-02-19 | Glaxo Group Limited | Process for Preparing Pyrido[2,3-d]pyrimidin-7-one and 3,4-Dihydropyrimido[4,5-d]pyrimidin-2(1H)-one Derivatives |
US20100093766A1 (en) * | 2005-03-25 | 2010-04-15 | Callahan James F | Novel compounds |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL155367A0 (en) | 2000-10-23 | 2003-12-23 | Smithkline Beecham Corp | NOVEL 2,4,8-TRISUBSTITUTED-8h-PYRIDO[2,3,-d]PYRIMIDIN-7-ONE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME, PROCESSES FOR THE PREPARATION THEREOF, AND USE THEREOF IN THE PREPARATION OF MEDICAMENTS FOR TREATING CSBP/p38 KINASE MEDIATED DISEASES |
NZ533865A (en) | 2002-02-12 | 2006-02-24 | Smithkline Beecham Corp | Nicotinamide derivates useful as p38 inhibitors |
BR0309053A (pt) * | 2002-04-19 | 2005-02-22 | Smithkline Beecham Corp | Compostos |
JP2008535822A (ja) * | 2005-03-25 | 2008-09-04 | グラクソ グループ リミテッド | 新規化合物 |
PE20100737A1 (es) | 2005-03-25 | 2010-11-27 | Glaxo Group Ltd | Nuevos compuestos |
JP2009542818A (ja) * | 2006-06-16 | 2009-12-03 | グラクソ グループ リミテッド | 新規化合物 |
JP2009542816A (ja) * | 2006-06-16 | 2009-12-03 | グラクソ グループ リミテッド | 新規化合物 |
WO2007147104A2 (en) * | 2006-06-16 | 2007-12-21 | Glaxo Group Limited | Novel compounds |
CN101605760B (zh) * | 2007-02-09 | 2012-06-20 | 陶氏益农公司 | 将某些取代的硫亚胺氧化为杀虫性磺基肟的方法 |
EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
WO2009152356A2 (en) * | 2008-06-11 | 2009-12-17 | Irm Llc | Compounds and compositions useful for the treatment of malaria |
CN103827118B (zh) * | 2011-07-27 | 2016-03-09 | 葛兰素集团有限公司 | 双环嘧啶酮化合物 |
CA3128468A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd |
US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
CN111961034A (zh) * | 2019-05-20 | 2020-11-20 | 浙江同源康医药股份有限公司 | 用作ret激酶抑制剂的化合物及其应用 |
CN113750095B (zh) * | 2021-03-10 | 2023-07-04 | 中国医学科学院医药生物技术研究所 | 含有环丙基骨架的化合物在制备治疗和/或预防冠状病毒感染药物中的应用 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5945422A (en) * | 1997-02-05 | 1999-08-31 | Warner-Lambert Company | N-oxides of amino containing pyrido 2,3-D! pyrimidines |
US6248225B1 (en) * | 1998-05-26 | 2001-06-19 | Ppg Industries Ohio, Inc. | Process for forming a two-coat electrodeposited composite coating the composite coating and chip resistant electrodeposited coating composition |
US20030100756A1 (en) * | 2000-03-02 | 2003-05-29 | Adams Jerry L | 1,5- disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
US20040116697A1 (en) * | 2000-10-23 | 2004-06-17 | Adams Jerry L. | Novel compounds |
US20060217401A1 (en) * | 2005-03-25 | 2006-09-28 | Boehm Jeffrey C | Novel compounds |
US20060235030A1 (en) * | 2005-03-25 | 2006-10-19 | Callahan James F | Novel compounds |
US20060235029A1 (en) * | 2005-03-25 | 2006-10-19 | Callahan James F | Novel compounds |
US20060258687A1 (en) * | 2005-03-25 | 2006-11-16 | Boehm Jeffrey C | Process for preparing pyrido[2,3-d]pyrimidin-7-one and 3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one derivatives |
Family Cites Families (102)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA966134A (en) * | 1972-05-05 | 1975-04-15 | Haydn W.R. Williams | 1,8-naphthyridine compounds |
JPS5618982A (en) * | 1979-06-14 | 1981-02-23 | Wellcome Found | Pyrimidine derivatives and medicinal drug containing them |
CY1308A (en) | 1979-12-06 | 1985-12-06 | Glaxo Group Ltd | Device for dispensing medicaments |
US4353656A (en) | 1980-10-14 | 1982-10-12 | Xerox Corporation | Moving coil, multiple energy print hammer system including a closed loop servo |
CY1492A (en) | 1981-07-08 | 1990-02-16 | Draco Ab | Powder inhalator |
GB2123831B (en) | 1981-07-20 | 1986-01-15 | Ciba Geigy Ag | Trisubstituted oxazo compounds |
US4778054A (en) | 1982-10-08 | 1988-10-18 | Glaxo Group Limited | Pack for administering medicaments to patients |
LU85034A1 (fr) | 1982-10-08 | 1985-06-19 | Glaxo Group Ltd | Dispositifs en vue d'administrer des medicaments a des patients |
GB2169265B (en) | 1982-10-08 | 1987-08-12 | Glaxo Group Ltd | Pack for medicament |
JPS60226882A (ja) * | 1984-04-24 | 1985-11-12 | Nippon Zoki Pharmaceut Co Ltd | 新規ピリミドピリミジン誘導体 |
US4560691A (en) * | 1984-07-13 | 1985-12-24 | Sterling Drug Inc. | 5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use and preparation |
BE905189A (fr) | 1985-07-30 | 1987-01-29 | Glaxo Group Ltd | Dispositif pour administrer des medicaments a des patients. |
EP0278686A1 (en) | 1987-02-07 | 1988-08-17 | The Wellcome Foundation Limited | Pyridopyrimidines methods for their preparation and pharmaceutical formulations thereof |
JPH01261306A (ja) | 1988-04-13 | 1989-10-18 | Nippon Kayaku Co Ltd | 2−アルキルチオ−4−アミノピリミジン誘導体を有効成分とする開花促進剤 |
GB9004781D0 (en) | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
IE913473A1 (en) * | 1990-10-15 | 1992-04-22 | Fujisawa Pharmaceutical Co | Quinazoline derivatives and their preparation |
WO1992012154A1 (en) | 1990-12-31 | 1992-07-23 | Fujisawa Pharmaceutical Co., Ltd. | Imidazotriazine derivatives |
US5409930A (en) * | 1991-05-10 | 1995-04-25 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
IL102764A0 (en) | 1991-08-16 | 1993-01-31 | Merck & Co Inc | Quinazoline derivatives,and pharmaceutical compositions containing them |
DE4131029A1 (de) * | 1991-09-18 | 1993-07-29 | Basf Ag | Substituierte pyrido (2,3-d) pyrimidine als antidots |
GB9127376D0 (en) | 1991-12-24 | 1992-02-19 | Wellcome Found | Amidino derivatives |
GB9303993D0 (en) | 1993-02-26 | 1993-04-14 | Fujisawa Pharmaceutical Co | New heterocyclic derivatives |
US5466692A (en) * | 1993-03-24 | 1995-11-14 | American Home Products Corporation | Substituted pyridopyrimidines and antihypertensives |
US5426110A (en) * | 1993-10-06 | 1995-06-20 | Eli Lilly And Company | Pyrimidinyl-glutamic acid derivatives |
GB9325217D0 (en) | 1993-12-09 | 1994-02-09 | Zeneca Ltd | Pyrimidine derivatives |
IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
US5547954A (en) * | 1994-05-26 | 1996-08-20 | Fmc Corporation | 2,4-Diamino-5,6-disubstituted-and 5,6,7-trisubstituted-5-deazapteridines as insecticides |
TW574214B (en) | 1994-06-08 | 2004-02-01 | Pfizer | Corticotropin releasing factor antagonists |
JP2989010B2 (ja) | 1994-06-15 | 1999-12-13 | ザ、ウェルカム、ファンデーション、リミテッド | 酵素阻害剤 |
EP0779292A4 (en) * | 1994-08-29 | 1997-09-24 | Yamanouchi Pharma Co Ltd | NEW NAPHTHYRIDE DERIVATIVES AND MEDICAL COMPOSITIONS CONTAINING THEM |
IL115256A0 (en) * | 1994-11-14 | 1995-12-31 | Warner Lambert Co | 6-Aryl pyrido (2,3-d) pyrimidines and naphthyridines and their use |
CA2213442A1 (en) | 1995-03-10 | 1996-09-19 | The Minnesota Mining & Manufacturing Company | Aerosol valves |
US5620981A (en) * | 1995-05-03 | 1997-04-15 | Warner-Lambert Company | Pyrido [2,3-D]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation |
US5760220A (en) * | 1995-06-07 | 1998-06-02 | American Home Products Corporation | Process for preparation of biphenyl derivatives |
US5767097A (en) * | 1996-01-23 | 1998-06-16 | Icn Pharmaceuticals, Inc. | Specific modulation of Th1/Th2 cytokine expression by ribavirin in activated T-lymphocytes |
DE69718306D1 (de) | 1996-04-12 | 2003-02-13 | Sumitomo Pharma | Piperidinylpyrimidine derivate |
ZA973884B (en) * | 1996-05-23 | 1998-11-06 | Du Pont Merck Pharma | Tetrahydropteridines and pyridylpiperazines for treatment of neurological disorders |
US6875769B2 (en) * | 1996-05-23 | 2005-04-05 | Pfizer Inc. | Substituted6,6-hetero-bicyclicderivatives |
IL128188A0 (en) | 1996-08-06 | 1999-11-30 | Pfizer | ,7-bicyclic derivatives substituted pyrido-or pyrimido-containing 6,6-or 6 |
TW477787B (en) | 1996-08-27 | 2002-03-01 | Pfizer | Pyrido six-membered nitrogen-containing cyclic ring derivatives having corticotropin releasing factor antagonist activity and pharmaceutical composition containing same |
US6509320B1 (en) * | 1996-10-16 | 2003-01-21 | Icn Pharmaceuticals, Inc. | Purine L-nucleosides, analogs and uses thereof |
US6147080A (en) | 1996-12-18 | 2000-11-14 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
GB9700226D0 (en) | 1997-01-08 | 1997-02-26 | Glaxo Group Ltd | Inhalation device |
MY117948A (en) | 1997-01-13 | 2004-08-30 | Glaxo Group Ltd | Nitride oxide synthase inhibitors. |
US6498163B1 (en) * | 1997-02-05 | 2002-12-24 | Warner-Lambert Company | Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation |
WO1998033798A2 (en) | 1997-02-05 | 1998-08-06 | Warner Lambert Company | Pyrido[2,3-d]pyrimidines and 4-amino-pyrimidines as inhibitors of cell proliferation |
DE19723722A1 (de) | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
AR017219A1 (es) | 1997-12-19 | 2001-08-22 | Smithkline Beecham Corp | Derivados de imidazol 1,4,5 sustituidos, composiciones que los comprenden, procedimiento para la preparacion de dichos derivados, uso de los derivados parala manufactura de un medicamento |
US6506766B1 (en) | 1998-02-13 | 2003-01-14 | Abbott Laboratories | Glucocortiocoid-selective antinflammatory agents |
NZ506417A (en) * | 1998-02-17 | 2003-05-30 | Tularik Inc | Anti-viral pyrimidine derivatives |
JP2000038350A (ja) | 1998-05-18 | 2000-02-08 | Yoshitomi Pharmaceut Ind Ltd | 糖尿病治療薬 |
ID27589A (id) | 1998-05-26 | 2001-04-12 | Warner Lambert Comapny | Pirimidina bisiklik dan dihidropirimidina bisiklik 3,4 sebagai penghambat proliferasi selular |
GB9811599D0 (en) | 1998-05-30 | 1998-07-29 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
EP1086085A1 (en) * | 1998-06-12 | 2001-03-28 | Vertex Pharmaceuticals Incorporated | INHIBITORS OF p38 |
US6184226B1 (en) * | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
EP1117653B1 (en) * | 1998-10-01 | 2003-02-05 | AstraZeneca AB | Quinoline and quinazoline derivatives and their use as inhibitors of cytokine mediated diseases |
WO2000023444A1 (en) | 1998-10-21 | 2000-04-27 | Abbott Laboratories | 5,7-disubstituted-4-aminopyrido[2,3-d]pyrimidine compounds |
US6358959B1 (en) | 1999-01-26 | 2002-03-19 | Merck & Co., Inc. | Polyazanaphthalenone derivatives useful as alpha 1a adrenoceptor antagonists |
AU4501800A (en) | 1999-05-04 | 2000-11-17 | American Home Products Corporation | Tetracyclic progesterone receptor modulator compounds and methods |
CO5180649A1 (es) | 1999-09-01 | 2002-07-30 | Abbott Lab | Antagonistas de los receptores de los glucocorticoides para el tratamiento de la diabetes para el tratamiento de la diabetes |
ES2299434T3 (es) | 1999-09-17 | 2008-06-01 | ABBOTT GMBH & CO. KG | Inhibidores de kinasa utilizados como agentes terapeuticos. |
WO2001042243A2 (en) | 1999-12-08 | 2001-06-14 | Advanced Medicine, Inc. | Protein kinase inhibitors |
US6632666B2 (en) | 2000-01-14 | 2003-10-14 | Biolife Solutions, Inc. | Normothermic, hypothermic and cryopreservation maintenance and storage of cells, tissues and organs in gel-based media |
KR20020065939A (ko) | 2000-01-25 | 2002-08-14 | 워너-램버트 캄파니 | 피리도[2,3-d]피리미딘-2,7-디아민 카이나제 억제제 |
US20040224958A1 (en) * | 2000-01-27 | 2004-11-11 | Booth Richard John | Pyridopyrimidinone derivatives for treatment of neurodegenerative disease |
SK12472002A3 (sk) | 2000-03-06 | 2003-04-01 | Warner-Lambert Company | 5-Alkylpyrido[2,3-d]pyrimidínové inhibítory tyrosínových kináz |
AU2001283004A1 (en) * | 2000-07-24 | 2002-02-05 | Vivcom, Inc. | System and method for indexing, searching, identifying, and editing portions of electronic multimedia files |
KR20030031198A (ko) | 2000-09-29 | 2003-04-18 | 글락소 그룹 리미티드 | 염증 질환 치료용 모르폴린-아세트아미드 유도체 |
WO2002060869A2 (en) | 2000-10-19 | 2002-08-08 | Smithkline Beecham Corporation | Use of p38 inhibitors for the treatment of inflammation-enhanced cough |
JP2004521892A (ja) | 2000-12-20 | 2004-07-22 | メルク エンド カムパニー インコーポレーテッド | (ハロ−ベンゾカルボニル)複素環縮合フェニル系p38キナーゼ阻害剤 |
GB0031179D0 (en) | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
US6484903B2 (en) | 2001-01-09 | 2002-11-26 | Riverwood International Corporation | Carton with an improved dispensing feature in combination with a unique handle |
PE20030008A1 (es) * | 2001-06-19 | 2003-01-22 | Bristol Myers Squibb Co | Inhibidores duales de pde 7 y pde 4 |
WO2003010143A1 (en) | 2001-07-26 | 2003-02-06 | Samsung Electronics Co., Ltd. | Dialkylhydroxybenzoic acid derivatives containing metal chelating groups and their therapeutic uses |
JP4178783B2 (ja) | 2001-10-19 | 2008-11-12 | 三菱化学株式会社 | 光学記録媒体 |
US7019002B2 (en) * | 2001-12-11 | 2006-03-28 | Pharmacia & Upjohn, S.P.A. | Pyridopyrimidinones derivatives as telomerase inhibitors |
DE60309829T2 (de) | 2002-01-14 | 2007-09-13 | Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield | Glucocorticoidmimetika, verfahren zu ihrer herstellung, diese enthaltende pharmazeutische formulierungen und ihre verwendungen |
SI1470124T1 (sl) * | 2002-01-22 | 2006-04-30 | Warner Lambert Co | 2-(piridin-2-ilamino)-pirido(2,3-d)pirimidin-7-oni |
WO2003061651A1 (en) | 2002-01-22 | 2003-07-31 | The Regents Of The University Of California | Non-steroidal ligands for the glucocorticoid receptor, compositions and uses thereof |
ES2298508T3 (es) | 2002-03-26 | 2008-05-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Mimeticos de glucocorticoides, metodos para prepararlos, composiciones farmaceuticas y sus usos. |
AU2003230700A1 (en) | 2002-03-26 | 2003-10-13 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
DE10215316C1 (de) | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
JP4570878B2 (ja) | 2002-04-11 | 2010-10-27 | メルク・シャープ・エンド・ドーム・コーポレイション | 選択的糖質コルチコイド受容体モジュレーターとしての1H−ベンゾ[f]インダゾール−5−イル誘導体 |
AU2003232071A1 (en) * | 2002-05-06 | 2003-11-17 | Genelabs Technologies, Inc. | Nucleoside derivatives for treating hepatitis c virus infection |
US7186864B2 (en) | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
BR0312575A (pt) | 2002-07-08 | 2005-05-03 | Pfizer Prod Inc | Moduladores do receptor de glicocorticóides |
AU2003251970A1 (en) | 2002-07-18 | 2004-02-09 | Bristol-Myers Squibb Company | Modulators of the glucocorticoid receptor and method |
ATE456100T1 (de) | 2002-07-18 | 2010-02-15 | Bristol Myers Squibb Co | Zusammensetzungen und verfahren im zusammenhang mit der nuklearen hormon-rezeptor-stelle ii |
ATE403648T1 (de) | 2002-08-21 | 2008-08-15 | Boehringer Ingelheim Pharma | Substituierte dihydrochinoline als glucocorticoid-mmimetika,verfahren zu deren herstellung, pharmazeutische zubereitungen und deren verwendung |
AU2003270783C1 (en) | 2002-09-20 | 2010-05-20 | Merck Sharp & Dohme Corp. | Octahydro-2-H-naphtho[1,2-F] indole-4-carboxamide derivatives as selective glucocorticoid receptor modulators |
WO2004043367A2 (en) * | 2002-11-06 | 2004-05-27 | Bristol-Myers Squibb Company | Fused heterocyclic compounds and use thereof |
JP2004203751A (ja) | 2002-12-24 | 2004-07-22 | Pfizer Inc | 置換6,6−ヘテロ二環式誘導体 |
DE602004021558D1 (de) * | 2003-01-17 | 2009-07-30 | Warner Lambert Co | 2-aminopyridin-substituierteheterocyclen als inhibitoren der zellulären proliferation |
EP1596860A4 (en) | 2003-02-14 | 2009-05-27 | Smithkline Beecham Corp | NEW CONNECTIONS |
US7138412B2 (en) * | 2003-03-11 | 2006-11-21 | Bristol-Myers Squibb Company | Tetrahydroquinoline derivatives useful as serine protease inhibitors |
WO2004106308A1 (en) * | 2003-05-27 | 2004-12-09 | Pfizer Products Inc. | Quinazolines and pyrido [3,4-d] pyrimidines as receptor tyrosine kinase inhibitors |
TWI220897B (en) * | 2003-07-22 | 2004-09-11 | Benq Corp | Recording media feeding system and method |
CA2554566A1 (en) | 2003-08-05 | 2005-02-17 | Vertex Pharmaceuticals Incorporated | Condensed pyramidine compounds as inhibitors of voltage-gated ion channels |
US7098222B2 (en) * | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
US7712653B2 (en) * | 2004-09-29 | 2010-05-11 | Graphic Packaging International, Inc. | Carton with dispenser having access features |
JP5111113B2 (ja) * | 2004-12-13 | 2012-12-26 | サネシス ファーマシューティカルズ, インコーポレイテッド | Rafキナーゼ阻害剤として有用なピリドピリミジノン、ジヒドロピリミドピリミジノンおよびプテリジノン |
-
2006
- 2006-03-23 TW TW095109982A patent/TW200724142A/zh unknown
- 2006-03-23 PE PE2006000331A patent/PE20061193A1/es not_active Application Discontinuation
- 2006-03-23 UY UY29439A patent/UY29439A1/es unknown
- 2006-03-23 AR ARP060101148A patent/AR053450A1/es not_active Application Discontinuation
- 2006-03-23 PE PE2010000198A patent/PE20100741A1/es not_active Application Discontinuation
- 2006-03-24 KR KR1020077024433A patent/KR20080005223A/ko not_active Application Discontinuation
- 2006-03-24 EA EA200702074A patent/EA200702074A1/ru unknown
- 2006-03-24 NZ NZ561438A patent/NZ561438A/en not_active IP Right Cessation
- 2006-03-24 MX MX2007011883A patent/MX2007011883A/es active IP Right Grant
- 2006-03-24 BR BRPI0609579-8A patent/BRPI0609579A2/pt not_active IP Right Cessation
- 2006-03-24 AU AU2006229967A patent/AU2006229967B2/en not_active Ceased
- 2006-03-24 AP AP2007004171A patent/AP2281A/xx active
- 2006-03-24 WO PCT/US2006/010792 patent/WO2006104889A2/en active Application Filing
- 2006-03-24 CN CN2006800183985A patent/CN101184758B/zh not_active Expired - Fee Related
- 2006-03-24 CA CA002602546A patent/CA2602546A1/en not_active Abandoned
- 2006-03-24 SG SG201006926-8A patent/SG166100A1/en unknown
- 2006-03-24 US US11/389,112 patent/US7674789B2/en not_active Expired - Fee Related
- 2006-03-24 EP EP06748656A patent/EP1866311A4/en not_active Withdrawn
- 2006-03-24 UA UAA200710644A patent/UA95230C2/ru unknown
- 2006-03-24 JP JP2008503226A patent/JP2008535820A/ja active Pending
- 2006-03-24 US US11/908,435 patent/US20090239846A1/en not_active Abandoned
-
2007
- 2007-09-11 IL IL185915A patent/IL185915A0/en unknown
- 2007-09-12 ZA ZA200707798A patent/ZA200707798B/xx unknown
- 2007-09-24 MA MA30236A patent/MA29340B1/fr unknown
- 2007-10-15 NO NO20075273A patent/NO20075273L/no not_active Application Discontinuation
-
2009
- 2009-11-16 US US12/618,927 patent/US20100093765A1/en not_active Abandoned
- 2009-11-16 US US12/618,933 patent/US20100093766A1/en not_active Abandoned
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5945422A (en) * | 1997-02-05 | 1999-08-31 | Warner-Lambert Company | N-oxides of amino containing pyrido 2,3-D! pyrimidines |
US6248225B1 (en) * | 1998-05-26 | 2001-06-19 | Ppg Industries Ohio, Inc. | Process for forming a two-coat electrodeposited composite coating the composite coating and chip resistant electrodeposited coating composition |
US20030100756A1 (en) * | 2000-03-02 | 2003-05-29 | Adams Jerry L | 1,5- disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
US7235551B2 (en) * | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
US20040116697A1 (en) * | 2000-10-23 | 2004-06-17 | Adams Jerry L. | Novel compounds |
US20060217401A1 (en) * | 2005-03-25 | 2006-09-28 | Boehm Jeffrey C | Novel compounds |
US20060235030A1 (en) * | 2005-03-25 | 2006-10-19 | Callahan James F | Novel compounds |
US20060235029A1 (en) * | 2005-03-25 | 2006-10-19 | Callahan James F | Novel compounds |
US20060258687A1 (en) * | 2005-03-25 | 2006-11-16 | Boehm Jeffrey C | Process for preparing pyrido[2,3-d]pyrimidin-7-one and 3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one derivatives |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070238743A1 (en) * | 2000-03-02 | 2007-10-11 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
US20090048444A1 (en) * | 2005-03-25 | 2009-02-19 | Glaxo Group Limited | Process for Preparing Pyrido[2,3-d]pyrimidin-7-one and 3,4-Dihydropyrimido[4,5-d]pyrimidin-2(1H)-one Derivatives |
US20100093766A1 (en) * | 2005-03-25 | 2010-04-15 | Callahan James F | Novel compounds |
Also Published As
Publication number | Publication date |
---|---|
MX2007011883A (es) | 2007-11-13 |
US20060235030A1 (en) | 2006-10-19 |
MA29340B1 (fr) | 2008-03-03 |
WO2006104889A3 (en) | 2007-04-12 |
CA2602546A1 (en) | 2006-10-05 |
US20100093765A1 (en) | 2010-04-15 |
KR20080005223A (ko) | 2008-01-10 |
AU2006229967A1 (en) | 2006-10-05 |
EP1866311A4 (en) | 2010-03-31 |
US7674789B2 (en) | 2010-03-09 |
AR053450A1 (es) | 2007-05-09 |
TW200724142A (en) | 2007-07-01 |
WO2006104889A2 (en) | 2006-10-05 |
PE20100741A1 (es) | 2010-11-25 |
PE20061193A1 (es) | 2006-12-02 |
UA95230C2 (ru) | 2011-07-25 |
ZA200707798B (en) | 2009-08-26 |
NZ561438A (en) | 2011-02-25 |
EA200702074A1 (ru) | 2008-02-28 |
JP2008535820A (ja) | 2008-09-04 |
AP2281A (en) | 2011-10-31 |
IL185915A0 (en) | 2008-01-06 |
UY29439A1 (es) | 2006-10-02 |
BRPI0609579A2 (pt) | 2010-04-20 |
CN101184758A (zh) | 2008-05-21 |
EP1866311A2 (en) | 2007-12-19 |
SG166100A1 (en) | 2010-11-29 |
US20100093766A1 (en) | 2010-04-15 |
NO20075273L (no) | 2007-12-12 |
AP2007004171A0 (en) | 2007-10-31 |
CN101184758B (zh) | 2012-05-02 |
AU2006229967B2 (en) | 2012-02-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7674789B2 (en) | Compounds | |
US8354416B2 (en) | 7,8-dihydropyrido[2,3-d]pyrimidin-4-yl substituted compounds as inhibitors of p38 kinase | |
US7423042B2 (en) | Compounds | |
US20090318424A1 (en) | Novel compounds | |
US20100144755A1 (en) | Novel Compounds | |
US20100069409A1 (en) | "novel compounds" |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: GLAXO GROUP LIMITED, UNITED KINGDOM Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CALLAHAN, JAMES;WAN, ZEHONG;YAN, HONGXING;REEL/FRAME:019816/0314;SIGNING DATES FROM 20060420 TO 20060421 |
|
AS | Assignment |
Owner name: GLAXO GROUP LIMITED, UNITED KINGDOM Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CALLAHAN, JAMES FRANCIS;WAN, ZEHONG;YAN, HONGXING;AND OTHERS;REEL/FRAME:021057/0043;SIGNING DATES FROM 20080220 TO 20080221 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |