US20120053164A1 - Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd - Google Patents
Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd Download PDFInfo
- Publication number
- US20120053164A1 US20120053164A1 US13/140,591 US200913140591A US2012053164A1 US 20120053164 A1 US20120053164 A1 US 20120053164A1 US 200913140591 A US200913140591 A US 200913140591A US 2012053164 A1 US2012053164 A1 US 2012053164A1
- Authority
- US
- United States
- Prior art keywords
- amino
- alkyl
- phenyl
- quinazoline
- alkylene
- 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 [1*]*C1=NC([3*])=NC(C(=O)N2CCC([4*])([5*])C2)=C1[2*].[6*]C Chemical compound [1*]*C1=NC([3*])=NC(C(=O)N2CCC([4*])([5*])C2)=C1[2*].[6*]C 0.000 description 42
- OHVYRLNUMZHWIK-NTSWFWBYSA-N CO[C@@H]1COCC[C@@H]1N Chemical compound CO[C@@H]1COCC[C@@H]1N OHVYRLNUMZHWIK-NTSWFWBYSA-N 0.000 description 3
- SYQZVIXVLGSTNE-UHFFFAOYSA-N C=CCCC(O)C1=CC(C(F)(F)F)=CC=C1 Chemical compound C=CCCC(O)C1=CC(C(F)(F)F)=CC=C1 SYQZVIXVLGSTNE-UHFFFAOYSA-N 0.000 description 2
- VMQHTFXKOBPMJZ-UHFFFAOYSA-N CC(C)(C)OC(=O)NC1CCN(C2CCN(C(=O)OCC3=CC=CC=C3)CC2)CC1 Chemical compound CC(C)(C)OC(=O)NC1CCN(C2CCN(C(=O)OCC3=CC=CC=C3)CC2)CC1 VMQHTFXKOBPMJZ-UHFFFAOYSA-N 0.000 description 2
- JXSUTXZULNCOET-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC1=CC=C(C(C)(C)C)C=C1 JXSUTXZULNCOET-UHFFFAOYSA-N 0.000 description 2
- UAEMBGZGSUNOPQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 UAEMBGZGSUNOPQ-UHFFFAOYSA-N 0.000 description 2
- AXZJMLOXLMOCDI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CN=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CN=C(C(C)(C)C)C=C1 AXZJMLOXLMOCDI-UHFFFAOYSA-N 0.000 description 2
- VKSFJLLFIDMLEA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCC(/C2=N/C3=C(C=CC=C3)N2)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCC(/C2=N/C3=C(C=CC=C3)N2)CC1 VKSFJLLFIDMLEA-UHFFFAOYSA-N 0.000 description 2
- KWCLXIPOGGEYFL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1COC(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1COC(C2=CC=CC=C2)C1 KWCLXIPOGGEYFL-UHFFFAOYSA-N 0.000 description 2
- JDFTZOHQLAOCSN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OC1=CC=C(C(C)(C)C)C=C1 JDFTZOHQLAOCSN-UHFFFAOYSA-N 0.000 description 2
- JOZMYTWXCXZZES-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)C=CN=C1NCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)C=CN=C1NCC1=CC=C(Cl)C(Cl)=C1 JOZMYTWXCXZZES-UHFFFAOYSA-N 0.000 description 2
- PQEJHMRPZAORGH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 PQEJHMRPZAORGH-UHFFFAOYSA-N 0.000 description 2
- ZSFPLYIZHAGOAP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC=C(C(F)(F)F)C=C1F Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC=C(C(F)(F)F)C=C1F ZSFPLYIZHAGOAP-UHFFFAOYSA-N 0.000 description 2
- SWYLJSSDKTVMMF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1Cl Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1Cl SWYLJSSDKTVMMF-UHFFFAOYSA-N 0.000 description 2
- OLIVKVPLVRNJEK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCN(C(=O)OC(C)(C)C)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCN(C(=O)OC(C)(C)C)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 OLIVKVPLVRNJEK-UHFFFAOYSA-N 0.000 description 2
- ALRHYFBLLROTOZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 ALRHYFBLLROTOZ-UHFFFAOYSA-N 0.000 description 2
- MYZGNUFRYYMHGH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCC1CCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCC1CCN(C2=CC=CC=C2)C1 MYZGNUFRYYMHGH-UHFFFAOYSA-N 0.000 description 2
- SWOPCFMGXYTTLO-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(NC3CCOC4=C3N=CC=C4)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(NC3CCOC4=C3N=CC=C4)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 SWOPCFMGXYTTLO-UHFFFAOYSA-N 0.000 description 2
- KKZWTJFREIWFFG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(NC3CCOCC3N3N=CN=N3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(NC3CCOCC3N3N=CN=N3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 KKZWTJFREIWFFG-UHFFFAOYSA-N 0.000 description 2
- JWFSUMZOGDEHIB-UHFFFAOYSA-N CC1=C(C(=O)N2CCCN(C3CCOCC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCN(C3CCOCC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 JWFSUMZOGDEHIB-UHFFFAOYSA-N 0.000 description 2
- LTVSVWGRFVNUDX-UHFFFAOYSA-N CC1=C(C(=O)O)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 LTVSVWGRFVNUDX-UHFFFAOYSA-N 0.000 description 2
- CCOBAYWMTYQMNL-UHFFFAOYSA-N CC1=C(Cl)N=CN=C1C(=O)Cl Chemical compound CC1=C(Cl)N=CN=C1C(=O)Cl CCOBAYWMTYQMNL-UHFFFAOYSA-N 0.000 description 2
- OLWGXGDMZCRZPZ-WDEREUQCSA-N CC1=CC=C([C@@H]2CCC[C@H](CN)C2)O1 Chemical compound CC1=CC=C([C@@H]2CCC[C@H](CN)C2)O1 OLWGXGDMZCRZPZ-WDEREUQCSA-N 0.000 description 2
- UZGCUFICZYGVBM-MNOVXSKESA-N CC1=CC=C([C@H]2CCC[C@@H](C#N)C2)O1 Chemical compound CC1=CC=C([C@H]2CCC[C@@H](C#N)C2)O1 UZGCUFICZYGVBM-MNOVXSKESA-N 0.000 description 2
- OLWGXGDMZCRZPZ-MNOVXSKESA-N CC1=CC=C([C@H]2CCC[C@@H](CN)C2)O1 Chemical compound CC1=CC=C([C@H]2CCC[C@@H](CN)C2)O1 OLWGXGDMZCRZPZ-MNOVXSKESA-N 0.000 description 2
- OIAPLKBUEZWJCS-VXGBXAGGSA-N CC1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1 Chemical compound CC1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1 OIAPLKBUEZWJCS-VXGBXAGGSA-N 0.000 description 2
- WFPIOKZQVSDPRP-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(NCC2CC3=C(C=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(NCC2CC3=C(C=CC=C3)C2)=N1 WFPIOKZQVSDPRP-UHFFFAOYSA-N 0.000 description 2
- UDSXOEFIGKLKRQ-UHFFFAOYSA-N CC1CC(N(C)C2CCNCC2)CC(C)O1.Cl.Cl Chemical compound CC1CC(N(C)C2CCNCC2)CC(C)O1.Cl.Cl UDSXOEFIGKLKRQ-UHFFFAOYSA-N 0.000 description 2
- XSFRZTQHDWZNNL-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=NC=N1 XSFRZTQHDWZNNL-UHFFFAOYSA-N 0.000 description 2
- BRSBOGYXMMJMMY-CVEARBPZSA-N CCOC(=O)C1=C(C)C(NC[C@@H]2CCC[C@H](C3=CC=C(C)O3)C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(NC[C@@H]2CCC[C@H](C3=CC=C(C)O3)C2)=NC=N1 BRSBOGYXMMJMMY-CVEARBPZSA-N 0.000 description 2
- FHVRKQWDDAKADH-UHFFFAOYSA-N CCOC(=O)C1=NC(OC)=NC(O)=C1C Chemical compound CCOC(=O)C1=NC(OC)=NC(O)=C1C FHVRKQWDDAKADH-UHFFFAOYSA-N 0.000 description 2
- IDOQOZWAYXADDG-UHFFFAOYSA-N CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC(C)=N3)CC2)CC1 Chemical compound CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC(C)=N3)CC2)CC1 IDOQOZWAYXADDG-UHFFFAOYSA-N 0.000 description 2
- GZPFQVHFCYUJNX-UHFFFAOYSA-N COC1=C(Cl)C=C(CCNC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1 Chemical compound COC1=C(Cl)C=C(CCNC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1 GZPFQVHFCYUJNX-UHFFFAOYSA-N 0.000 description 2
- JXSMSHZTHWYUSY-UHFFFAOYSA-N COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(Cl)=N1 Chemical compound COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(Cl)=N1 JXSMSHZTHWYUSY-UHFFFAOYSA-N 0.000 description 2
- IIBABFFZSWNYKV-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCN(C5=CC=CC=C5)CC4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCN(C5=CC=CC=C5)CC4)=NC=N3)CC2)CC1 IIBABFFZSWNYKV-UHFFFAOYSA-N 0.000 description 2
- QNGHCFVWYKWWMU-RKDXNWHRSA-N CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1N Chemical compound CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1N QNGHCFVWYKWWMU-RKDXNWHRSA-N 0.000 description 2
- FFGCHCCFBCJKHK-RNFRBKRXSA-N CO[C@@H]1CNCC[C@H]1NS(C)(=O)=O.Cl Chemical compound CO[C@@H]1CNCC[C@H]1NS(C)(=O)=O.Cl FFGCHCCFBCJKHK-RNFRBKRXSA-N 0.000 description 2
- OHVYRLNUMZHWIK-PHDIDXHHSA-N CO[C@@H]1COCC[C@H]1N Chemical compound CO[C@@H]1COCC[C@H]1N OHVYRLNUMZHWIK-PHDIDXHHSA-N 0.000 description 2
- OHVYRLNUMZHWIK-RITPCOANSA-N CO[C@H]1COCC[C@H]1N Chemical compound CO[C@H]1COCC[C@H]1N OHVYRLNUMZHWIK-RITPCOANSA-N 0.000 description 2
- VQDUNMKHCMGXAW-UHFFFAOYSA-N N#CC1CCCC(C2=CC=C(Cl)C=C2)C1 Chemical compound N#CC1CCCC(C2=CC=C(Cl)C=C2)C1 VQDUNMKHCMGXAW-UHFFFAOYSA-N 0.000 description 2
- DMIOQYUUBYOBMS-UHFFFAOYSA-N N#CC1CCCC(C2=CC=CC=C2)C1 Chemical compound N#CC1CCCC(C2=CC=CC=C2)C1 DMIOQYUUBYOBMS-UHFFFAOYSA-N 0.000 description 2
- XQBYUQBIWSRBRO-UHFFFAOYSA-N NCC1CCCC(C2=CC=C(Cl)C=C2)C1 Chemical compound NCC1CCCC(C2=CC=C(Cl)C=C2)C1 XQBYUQBIWSRBRO-UHFFFAOYSA-N 0.000 description 2
- SLFCZCBUOSEXNF-UHFFFAOYSA-N NCC1CCCC(C2=CC=CC=C2)C1 Chemical compound NCC1CCCC(C2=CC=CC=C2)C1 SLFCZCBUOSEXNF-UHFFFAOYSA-N 0.000 description 2
- IDLNNHCBDQYOAP-JHJMLUEUSA-N O=C(O)C1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound O=C(O)C1CCC[C@@H](C2=CC=CC=C2)C1 IDLNNHCBDQYOAP-JHJMLUEUSA-N 0.000 description 2
- MJEUYRDDZQPRMA-XNMGPUDCSA-N C#CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound C#CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 MJEUYRDDZQPRMA-XNMGPUDCSA-N 0.000 description 1
- KAQDXTYLYOMGNX-NVXWUHKLSA-N C#CC1=C(C(=O)O)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound C#CC1=C(C(=O)O)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 KAQDXTYLYOMGNX-NVXWUHKLSA-N 0.000 description 1
- NSMDRNVLWZIJME-IEBWSBKVSA-N C#CC1=C(C(=O)OCC)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound C#CC1=C(C(=O)OCC)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 NSMDRNVLWZIJME-IEBWSBKVSA-N 0.000 description 1
- FRNBATJVERWKJS-UHFFFAOYSA-N C.C.C.C.CC1=C(C)C=CC=C1.CC1=CC=C(C)C=C1.CC1=CC=CC(C)=C1.CC1CCCCC1.CN1CCCCC1 Chemical compound C.C.C.C.CC1=C(C)C=CC=C1.CC1=CC=C(C)C=C1.CC1=CC=CC(C)=C1.CC1CCCCC1.CN1CCCCC1 FRNBATJVERWKJS-UHFFFAOYSA-N 0.000 description 1
- AGRCFJWZWVGJKO-PEWIYULNSA-N C.C/C=C\CC.C/C=C\OC.C/N=C\NC.C/N=C\OC.C=C/C=C\C=C.C=C/C=C\N=C.C=C/C=N\C=C.C=C/C=N\N=C.C=C/N=C\N=C.C=C/N=N\C=C.C=CNC=C.C=COC=C.C=N/C=C\N=C.CC/N=N\C.CCCCC.CCCCCC.CCCCCC.CCCCNC.CCCCOC.CCCNCC.CCCOC.CCCOCC.CCNCC.CCOCC.COCCOC.COCOC Chemical compound C.C/C=C\CC.C/C=C\OC.C/N=C\NC.C/N=C\OC.C=C/C=C\C=C.C=C/C=C\N=C.C=C/C=N\C=C.C=C/C=N\N=C.C=C/N=C\N=C.C=C/N=N\C=C.C=CNC=C.C=COC=C.C=N/C=C\N=C.CC/N=N\C.CCCCC.CCCCCC.CCCCCC.CCCCNC.CCCCOC.CCCNCC.CCCOC.CCCOCC.CCNCC.CCOCC.COCCOC.COCOC AGRCFJWZWVGJKO-PEWIYULNSA-N 0.000 description 1
- FCCRUBFGHXCLFG-WQIVSCFSSA-N C/C=C\CC.C/C=C\OC.C=C/C=C\C=C.CCCC1=C(C)C=CC=C1.CCCCC.CCCCC.CCCCCC.CCCCOC.CCCNC(C)=O.CCCNCC.CCCOCC.CCNC(=O)OC.CCNCC Chemical compound C/C=C\CC.C/C=C\OC.C=C/C=C\C=C.CCCC1=C(C)C=CC=C1.CCCCC.CCCCC.CCCCCC.CCCCOC.CCCNC(C)=O.CCCNCC.CCCOCC.CCNC(=O)OC.CCNCC FCCRUBFGHXCLFG-WQIVSCFSSA-N 0.000 description 1
- DOAAVVISDAWENW-UHFFFAOYSA-N C1=CC=C2NC=NC2=C1.C1=CC=NC=C1.C1=CN=CC1.C1=CN=CC=N1.C1=CN=CN=C1.C1=CN=CN=C1.C1=CNC=C1.C1=CNC=C1.C1=CNC=N1.C1=CNN=C1.C1=COC=C1.C1=COC=C1.C1=COC=N1.C1=COC=N1.C1=CSC=C1 Chemical compound C1=CC=C2NC=NC2=C1.C1=CC=NC=C1.C1=CN=CC1.C1=CN=CC=N1.C1=CN=CN=C1.C1=CN=CN=C1.C1=CNC=C1.C1=CNC=C1.C1=CNC=N1.C1=CNN=C1.C1=COC=C1.C1=COC=C1.C1=COC=N1.C1=COC=N1.C1=CSC=C1 DOAAVVISDAWENW-UHFFFAOYSA-N 0.000 description 1
- PQUJNWIURCTKKA-UHFFFAOYSA-N C1CCC2(CC1)OCCO2.C=C1NCC2(CCNCC2)O1.CCN1CC2(CCNC2)C1.CN1CC2(CCNC2)C1.CN1CCC2(CCNC2)C1 Chemical compound C1CCC2(CC1)OCCO2.C=C1NCC2(CCNCC2)O1.CCN1CC2(CCNC2)C1.CN1CC2(CCNC2)C1.CN1CCC2(CCNC2)C1 PQUJNWIURCTKKA-UHFFFAOYSA-N 0.000 description 1
- HDIHFPYGEQUSCH-UHFFFAOYSA-N C1CCCNCC1.C1CCNC1.C1CCNC1.C1CCNCC1.C1CCNCC1.C1CCNCC1.C1CCNCC1.C1CCOC1.C1CCOCC1.C1CCSC1.C1CCSCC1.C1CNCCOC1.C1COCO1 Chemical compound C1CCCNCC1.C1CCNC1.C1CCNC1.C1CCNCC1.C1CCNCC1.C1CCNCC1.C1CCNCC1.C1CCOC1.C1CCOCC1.C1CCSC1.C1CCSCC1.C1CNCCOC1.C1COCO1 HDIHFPYGEQUSCH-UHFFFAOYSA-N 0.000 description 1
- DBXYISGDKJJYPG-UHFFFAOYSA-N C1CCNCC1.C1CCNCC1.C=C1CCCNCC1.C=C1CNCCN1.C=S1(=O)CCCC1.C=S1(=O)CCCN1.O=C1CCCC1.O=C1CCCN1.O=C1CCCN1 Chemical compound C1CCNCC1.C1CCNCC1.C=C1CCCNCC1.C=C1CNCCN1.C=S1(=O)CCCC1.C=S1(=O)CCCN1.O=C1CCCC1.O=C1CCCN1.O=C1CCCN1 DBXYISGDKJJYPG-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N C=CC Chemical compound C=CC QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- COKHDRBCAKWFSP-XNMGPUDCSA-N C=CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound C=CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 COKHDRBCAKWFSP-XNMGPUDCSA-N 0.000 description 1
- YCGPSTGOVJHAQD-NVXWUHKLSA-N C=CC1=C(C(=O)O)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound C=CC1=C(C(=O)O)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 YCGPSTGOVJHAQD-NVXWUHKLSA-N 0.000 description 1
- HIVRJPLZBSCBHE-IEBWSBKVSA-N C=CC1=C(C(=O)OCC)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound C=CC1=C(C(=O)OCC)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 HIVRJPLZBSCBHE-IEBWSBKVSA-N 0.000 description 1
- BPUYDIXEVSRQJT-UHFFFAOYSA-N C=CCCC(O)C1=CC(C)=C(F)C=C1 Chemical compound C=CCCC(O)C1=CC(C)=C(F)C=C1 BPUYDIXEVSRQJT-UHFFFAOYSA-N 0.000 description 1
- KVMOFQZNJJPJHV-UHFFFAOYSA-N C=CCCC(O)C1=CC(C)=CC=C1 Chemical compound C=CCCC(O)C1=CC(C)=CC=C1 KVMOFQZNJJPJHV-UHFFFAOYSA-N 0.000 description 1
- GLCCFCAQJXNUDQ-UHFFFAOYSA-N C=CCCC(O)C1=CC(F)=C(C)C=C1 Chemical compound C=CCCC(O)C1=CC(F)=C(C)C=C1 GLCCFCAQJXNUDQ-UHFFFAOYSA-N 0.000 description 1
- RKXXZDNLTJRYDK-UHFFFAOYSA-N C=CCCC(O)C1=CC=C(C(F)(F)F)C=C1 Chemical compound C=CCCC(O)C1=CC=C(C(F)(F)F)C=C1 RKXXZDNLTJRYDK-UHFFFAOYSA-N 0.000 description 1
- YEPHMNQDHBUULF-UHFFFAOYSA-N C=CCCC(O)C1=CC=C(C)C=C1 Chemical compound C=CCCC(O)C1=CC=C(C)C=C1 YEPHMNQDHBUULF-UHFFFAOYSA-N 0.000 description 1
- YXPRUZITRUXZEF-UHFFFAOYSA-N C=CCCC(O)C1=CC=C(Cl)C=C1 Chemical compound C=CCCC(O)C1=CC=C(Cl)C=C1 YXPRUZITRUXZEF-UHFFFAOYSA-N 0.000 description 1
- JMVLUMQNHZSEEM-UHFFFAOYSA-N CC(=O)N(C)C1CCN(C2CCN(C(=O)C3=NC=NC(CCC4=CC=C(Cl)C(Cl)=C4)=C3C)CC2)CC1 Chemical compound CC(=O)N(C)C1CCN(C2CCN(C(=O)C3=NC=NC(CCC4=CC=C(Cl)C(Cl)=C4)=C3C)CC2)CC1 JMVLUMQNHZSEEM-UHFFFAOYSA-N 0.000 description 1
- STSHTNDLMCZVJR-SANMLTNESA-N CC(=O)N1CCC[C@@H](CC2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C1 Chemical compound CC(=O)N1CCC[C@@H](CC2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C1 STSHTNDLMCZVJR-SANMLTNESA-N 0.000 description 1
- COGAIDHYEDMFKT-UHFFFAOYSA-N CC(=O)N1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 Chemical compound CC(=O)N1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 COGAIDHYEDMFKT-UHFFFAOYSA-N 0.000 description 1
- OBADKZZMZJDIRQ-UHFFFAOYSA-N CC(=O)NC1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 Chemical compound CC(=O)NC1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 OBADKZZMZJDIRQ-UHFFFAOYSA-N 0.000 description 1
- UVSBNGQOMBMUSW-OUKQBFOZSA-N CC(C)(C)C1=CC=C(/C=C/B2OC3=C(C=CC=C3)O2)C=C1 Chemical compound CC(C)(C)C1=CC=C(/C=C/B2OC3=C(C=CC=C3)O2)C=C1 UVSBNGQOMBMUSW-OUKQBFOZSA-N 0.000 description 1
- NQFHNNONBAWVTJ-UHFFFAOYSA-N CC(C)(C)C1=CC=C(CCC2=NC=NC(C(=O)O)=C2C#N)C=C1 Chemical compound CC(C)(C)C1=CC=C(CCC2=NC=NC(C(=O)O)=C2C#N)C=C1 NQFHNNONBAWVTJ-UHFFFAOYSA-N 0.000 description 1
- JOCANRFPNCTFQT-UHFFFAOYSA-N CC(C)(C)C1CCC(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3N(C)S(C)(=O)=O)=O)ncn2)CC1 Chemical compound CC(C)(C)C1CCC(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3N(C)S(C)(=O)=O)=O)ncn2)CC1 JOCANRFPNCTFQT-UHFFFAOYSA-N 0.000 description 1
- CBWQVRKPXDFQMF-UHFFFAOYSA-N CC(C)(C)OC(=O)CCC1CCCN(C2=CC=C(C#N)C(Cl)=C2)C1 Chemical compound CC(C)(C)OC(=O)CCC1CCCN(C2=CC=C(C#N)C(Cl)=C2)C1 CBWQVRKPXDFQMF-UHFFFAOYSA-N 0.000 description 1
- GUWNHTRTGOLPFQ-UHFFFAOYSA-N CC(C)(C)OC(=O)CCC1CCCN(C2=CC=C(C(F)(F)F)C=C2)C1 Chemical compound CC(C)(C)OC(=O)CCC1CCCN(C2=CC=C(C(F)(F)F)C=C2)C1 GUWNHTRTGOLPFQ-UHFFFAOYSA-N 0.000 description 1
- WMLAOHYRZRQAJC-UHFFFAOYSA-N CC(C)(C)OC(=O)CCC1CCCN(C2=CC=CC=C2)C1 Chemical compound CC(C)(C)OC(=O)CCC1CCCN(C2=CC=CC=C2)C1 WMLAOHYRZRQAJC-UHFFFAOYSA-N 0.000 description 1
- YIAOQZWPQLMICQ-CQSZACIVSA-N CC(C)(C)OC(=O)CC[C@@H]1CCN(C2=CC=CC=C2)C1 Chemical compound CC(C)(C)OC(=O)CC[C@@H]1CCN(C2=CC=CC=C2)C1 YIAOQZWPQLMICQ-CQSZACIVSA-N 0.000 description 1
- YIAOQZWPQLMICQ-AWEZNQCLSA-N CC(C)(C)OC(=O)CC[C@H]1CCN(C2=CC=CC=C2)C1 Chemical compound CC(C)(C)OC(=O)CC[C@H]1CCN(C2=CC=CC=C2)C1 YIAOQZWPQLMICQ-AWEZNQCLSA-N 0.000 description 1
- NTGSLCDHAKRUKC-LLVKDONJSA-N CC(C)(C)OC(=O)N1CCC(N2CC[C@@H](C(N)=O)C2)CC1 Chemical compound CC(C)(C)OC(=O)N1CCC(N2CC[C@@H](C(N)=O)C2)CC1 NTGSLCDHAKRUKC-LLVKDONJSA-N 0.000 description 1
- DVPRPFJQZYGOCJ-GFCCVEGCSA-N CC(C)(C)OC(=O)N1CCC(N2CC[C@@H](NS(C)(=O)=O)C2)CC1 Chemical compound CC(C)(C)OC(=O)N1CCC(N2CC[C@@H](NS(C)(=O)=O)C2)CC1 DVPRPFJQZYGOCJ-GFCCVEGCSA-N 0.000 description 1
- NTGSLCDHAKRUKC-NSHDSACASA-N CC(C)(C)OC(=O)N1CCC(N2CC[C@H](C(N)=O)C2)CC1 Chemical compound CC(C)(C)OC(=O)N1CCC(N2CC[C@H](C(N)=O)C2)CC1 NTGSLCDHAKRUKC-NSHDSACASA-N 0.000 description 1
- DVPRPFJQZYGOCJ-LBPRGKRZSA-N CC(C)(C)OC(=O)N1CCC(N2CC[C@H](NS(C)(=O)=O)C2)CC1 Chemical compound CC(C)(C)OC(=O)N1CCC(N2CC[C@H](NS(C)(=O)=O)C2)CC1 DVPRPFJQZYGOCJ-LBPRGKRZSA-N 0.000 description 1
- PJAGEPKEHKYZCO-UHFFFAOYSA-N CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3(C)C(NC)=O)=O)ncn2)cc1 Chemical compound CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3(C)C(NC)=O)=O)ncn2)cc1 PJAGEPKEHKYZCO-UHFFFAOYSA-N 0.000 description 1
- NNBARXLLKIRCLV-UHFFFAOYSA-N CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3N(C)S(C)(=O)=O)=O)ncn2)cc1 Chemical compound CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3N(C)S(C)(=O)=O)=O)ncn2)cc1 NNBARXLLKIRCLV-UHFFFAOYSA-N 0.000 description 1
- PFFYXFJGRKWNSX-UHFFFAOYSA-N CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3Oc(cc3F)ccc3F)=O)ncn2)cc1 Chemical compound CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3Oc(cc3F)ccc3F)=O)ncn2)cc1 PFFYXFJGRKWNSX-UHFFFAOYSA-N 0.000 description 1
- YDVOMIDDDGPHQQ-UHFFFAOYSA-N CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3S(NC)(=O)=O)=O)ncn2)cc1 Chemical compound CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3S(NC)(=O)=O)=O)ncn2)cc1 YDVOMIDDDGPHQQ-UHFFFAOYSA-N 0.000 description 1
- ULKBUEZCOYYZGD-RUZDIDTESA-N CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N[C@H](CCC3)CN3C(C)=O)=O)ncn2)cc1 Chemical compound CC(C)(C)c1ccc(CNc2c(C)c(C(N(CC3)CCC3N[C@H](CCC3)CN3C(C)=O)=O)ncn2)cc1 ULKBUEZCOYYZGD-RUZDIDTESA-N 0.000 description 1
- UEVGLUYBPFOZSO-UHFFFAOYSA-N CC(C)(C)c1ccc(CNc2c(C)c(C(N(CCC3)CCN3C(OC(C)(C)C)=O)=O)ncn2)cc1 Chemical compound CC(C)(C)c1ccc(CNc2c(C)c(C(N(CCC3)CCN3C(OC(C)(C)C)=O)=O)ncn2)cc1 UEVGLUYBPFOZSO-UHFFFAOYSA-N 0.000 description 1
- VTJUPIDUDPKSNW-UHFFFAOYSA-N CC(C)(C)c1ccc(CNc2ncnc(C(N(CC3)CC3N3CCCCC3)=O)c2C)cc1 Chemical compound CC(C)(C)c1ccc(CNc2ncnc(C(N(CC3)CC3N3CCCCC3)=O)c2C)cc1 VTJUPIDUDPKSNW-UHFFFAOYSA-N 0.000 description 1
- KDPUTUVRMUPRPP-UHFFFAOYSA-N CC(C)C(N(CC1)CCN1C(CC1)CCN1C(c1ncnc(NCCc(cc2)cc(Cl)c2Cl)c1C)=O)=O Chemical compound CC(C)C(N(CC1)CCN1C(CC1)CCN1C(c1ncnc(NCCc(cc2)cc(Cl)c2Cl)c1C)=O)=O KDPUTUVRMUPRPP-UHFFFAOYSA-N 0.000 description 1
- VLYRCYYFYAJGML-UHFFFAOYSA-N CC(C)C1CCCC(C#N)C1 Chemical compound CC(C)C1CCCC(C#N)C1 VLYRCYYFYAJGML-UHFFFAOYSA-N 0.000 description 1
- HSGWONSVPJQURE-UHFFFAOYSA-N CC(C)C1CCCC(CN)C1 Chemical compound CC(C)C1CCCC(CN)C1 HSGWONSVPJQURE-UHFFFAOYSA-N 0.000 description 1
- BBVWGFOBGMSWHY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 BBVWGFOBGMSWHY-UHFFFAOYSA-N 0.000 description 1
- VAVHRXWXBYRCNS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 VAVHRXWXBYRCNS-UHFFFAOYSA-N 0.000 description 1
- CZGUDALYNCTVKQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 Chemical compound CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 CZGUDALYNCTVKQ-UHFFFAOYSA-N 0.000 description 1
- KICOSSVSQXEYEJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 KICOSSVSQXEYEJ-UHFFFAOYSA-N 0.000 description 1
- HWEXUYJAZNUVMR-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(C(N)=O)(N3CCCCC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(C(N)=O)(N3CCCCC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 HWEXUYJAZNUVMR-UHFFFAOYSA-N 0.000 description 1
- ORFHCPNHHJCKHH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N(C)C3CC(C)OC(C)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N(C)C3CC(C)OC(C)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 ORFHCPNHHJCKHH-UHFFFAOYSA-N 0.000 description 1
- DXGUQWBAXHEDPS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N(C)C3CCC(F)(F)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N(C)C3CCC(F)(F)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 DXGUQWBAXHEDPS-UHFFFAOYSA-N 0.000 description 1
- XKJJQHJCTIIHTP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N(C)C3CCCOC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N(C)C3CCCOC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 XKJJQHJCTIIHTP-UHFFFAOYSA-N 0.000 description 1
- JDWRDUJQVCVVAQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N(C)C3CCOCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N(C)C3CCOCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 JDWRDUJQVCVVAQ-UHFFFAOYSA-N 0.000 description 1
- PEYOOYJQYHYYQF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N(C)CC#N)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N(C)CC#N)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 PEYOOYJQYHYYQF-UHFFFAOYSA-N 0.000 description 1
- ISRLEPKXYQSTDQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N(C)CC3(C)COC3)CC2)N=CN=C1NCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N(C)CC3(C)COC3)CC2)N=CN=C1NCC1=CC(Cl)=C(Cl)C=C1 ISRLEPKXYQSTDQ-UHFFFAOYSA-N 0.000 description 1
- SWDUUWGQQGDQCE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1.Cl Chemical compound CC1=C(C(=O)N2CCC(N)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1.Cl SWDUUWGQQGDQCE-UHFFFAOYSA-N 0.000 description 1
- YJJDLGFFXLGTPN-AZUAARDMSA-N CC1=C(C(=O)N2CCC(N)CC2)N=CN=C1NC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1.Cl Chemical compound CC1=C(C(=O)N2CCC(N)CC2)N=CN=C1NC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1.Cl YJJDLGFFXLGTPN-AZUAARDMSA-N 0.000 description 1
- PTKZARPBIWCJOO-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3C4CCC3CC(O)C4)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3C4CCC3CC(O)C4)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 PTKZARPBIWCJOO-UHFFFAOYSA-N 0.000 description 1
- QARXPXGXTCUSIV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CC(C)OC(C)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC(C)OC(C)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 QARXPXGXTCUSIV-UHFFFAOYSA-N 0.000 description 1
- IDMUMDJNGOGFTL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CC(N(C)S(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC(N(C)S(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 IDMUMDJNGOGFTL-UHFFFAOYSA-N 0.000 description 1
- YWWOMLSILMOFEJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CC(NS(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC(NS(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 YWWOMLSILMOFEJ-UHFFFAOYSA-N 0.000 description 1
- QYBQQYQSSIBMEL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CC4=C(C=CC=C4)C3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC4=C(C=CC=C4)C3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 QYBQQYQSSIBMEL-UHFFFAOYSA-N 0.000 description 1
- ZNTFMUVMFXQELA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C#N)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C#N)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 ZNTFMUVMFXQELA-UHFFFAOYSA-N 0.000 description 1
- WJYYGSRFLHMZKP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C(C)(C)C)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C(C)(C)C)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 WJYYGSRFLHMZKP-UHFFFAOYSA-N 0.000 description 1
- ZBYKPQXEULPSBL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C(F)(F)F)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C(F)(F)F)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 ZBYKPQXEULPSBL-UHFFFAOYSA-N 0.000 description 1
- WLQPPWYADOFURP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C(N)=O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C(N)=O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 WLQPPWYADOFURP-UHFFFAOYSA-N 0.000 description 1
- QRLVQIPPYGZRQJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C4=CC=C(C#N)C=C4)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C4=CC=C(C#N)C=C4)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 QRLVQIPPYGZRQJ-UHFFFAOYSA-N 0.000 description 1
- XBHIEPARLWFOOR-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C4=CC=CC=C4)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C4=CC=CC=C4)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 XBHIEPARLWFOOR-UHFFFAOYSA-N 0.000 description 1
- REAUJZKCBQAHHG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C4=CC=CC=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C4=CC=CC=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 REAUJZKCBQAHHG-UHFFFAOYSA-N 0.000 description 1
- OCLRHHGHPULTKY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(C4=CC=NC=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(C4=CC=NC=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 OCLRHHGHPULTKY-UHFFFAOYSA-N 0.000 description 1
- LYRGPKPQPJPQRV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(CC4=CC=C(F)C(F)=C4)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(CC4=CC=C(F)C(F)=C4)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 LYRGPKPQPJPQRV-UHFFFAOYSA-N 0.000 description 1
- HTQFKPUYSJXKDE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(CC4=CC=CN=C4)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(CC4=CC=CN=C4)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 HTQFKPUYSJXKDE-UHFFFAOYSA-N 0.000 description 1
- LRRAWWWMGAJLJJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(CNS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(CNS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 LRRAWWWMGAJLJJ-UHFFFAOYSA-N 0.000 description 1
- SIBKFBDDUUNZFA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(COC4=CC=CC=C4)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(COC4=CC=CC=C4)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 SIBKFBDDUUNZFA-UHFFFAOYSA-N 0.000 description 1
- SKMLNHXZUMAUCY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(CS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(CS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 SKMLNHXZUMAUCY-UHFFFAOYSA-N 0.000 description 1
- KKMHPYMBIVPUOL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(CS(C)(=O)=O)CC3)CC2)N=CN=C1CCCC1=CC=C(OC(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(CS(C)(=O)=O)CC3)CC2)N=CN=C1CCCC1=CC=C(OC(F)(F)F)C=C1 KKMHPYMBIVPUOL-UHFFFAOYSA-N 0.000 description 1
- PRRXIHYUWAFAJZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(CS(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(CS(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 PRRXIHYUWAFAJZ-UHFFFAOYSA-N 0.000 description 1
- YIRXAWRSIVZTBH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(F)(F)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(F)(F)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 YIRXAWRSIVZTBH-UHFFFAOYSA-N 0.000 description 1
- GYEWQFBCSMIGSR-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(F)(F)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(F)(F)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 GYEWQFBCSMIGSR-UHFFFAOYSA-N 0.000 description 1
- JWPVUNLNDJEHPQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(F)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(F)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 JWPVUNLNDJEHPQ-UHFFFAOYSA-N 0.000 description 1
- ZUWMVXUJZBTXCP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)C)CC3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)C)CC3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 ZUWMVXUJZBTXCP-UHFFFAOYSA-N 0.000 description 1
- ZYEHHWFSFODINN-FMIVXFBMSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1/C=C/C1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1/C=C/C1=CC=C(C(C)(C)C)C=C1 ZYEHHWFSFODINN-FMIVXFBMSA-N 0.000 description 1
- YBCTZHJJJAGCCQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1C1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1C1=CC=C(C(C)(C)C)C=C1 YBCTZHJJJAGCCQ-UHFFFAOYSA-N 0.000 description 1
- SZHRYFWPYPIOKV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC2=CC=CC=C2N=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC2=CC=CC=C2N=C1 SZHRYFWPYPIOKV-UHFFFAOYSA-N 0.000 description 1
- LHURIERBAMHUFA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(F)(F)F)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(F)(F)F)C(Cl)=C1 LHURIERBAMHUFA-UHFFFAOYSA-N 0.000 description 1
- DDRKXYCSNOOAKJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 DDRKXYCSNOOAKJ-UHFFFAOYSA-N 0.000 description 1
- CZWCLBYONOJIAL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(F)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(F)=C1 CZWCLBYONOJIAL-UHFFFAOYSA-N 0.000 description 1
- YIPBDNNAFQLBPI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C=C1 YIPBDNNAFQLBPI-UHFFFAOYSA-N 0.000 description 1
- LBFVZPUVZLPCPJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=COC(C2=CC=CC=C2)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=COC(C2=CC=CC=C2)=C1 LBFVZPUVZLPCPJ-UHFFFAOYSA-N 0.000 description 1
- XWACHZHVGWAALO-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC(Cl)=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC(Cl)=C2)O1 XWACHZHVGWAALO-UHFFFAOYSA-N 0.000 description 1
- LFGPUGBLNUFJLU-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)C1 LFGPUGBLNUFJLU-UHFFFAOYSA-N 0.000 description 1
- ONTDQDRYVPAHRP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)O1 ONTDQDRYVPAHRP-UHFFFAOYSA-N 0.000 description 1
- ZHGRREAKLMLKCE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C1C=CC=C2 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C1C=CC=C2 ZHGRREAKLMLKCE-UHFFFAOYSA-N 0.000 description 1
- HUTAYGQZBNDNOS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C(C)(C)C)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C(C)(C)C)CC1 HUTAYGQZBNDNOS-UHFFFAOYSA-N 0.000 description 1
- FGTHLYMIVOWVHS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C(C)C)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C(C)C)CC1 FGTHLYMIVOWVHS-UHFFFAOYSA-N 0.000 description 1
- OTWPKMKFUOSMRP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C)C1 OTWPKMKFUOSMRP-UHFFFAOYSA-N 0.000 description 1
- YXIGBFXIWZJNFI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C)CC1 YXIGBFXIWZJNFI-UHFFFAOYSA-N 0.000 description 1
- MEVOUBKXRYYVKY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(C(F)(F)F)C=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(C(F)(F)F)C=C2)O1 MEVOUBKXRYYVKY-UHFFFAOYSA-N 0.000 description 1
- NLNLIVBHEFUNFC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(Cl)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(Cl)C=C2)C1 NLNLIVBHEFUNFC-UHFFFAOYSA-N 0.000 description 1
- CVCGYXLLQXOOMB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(Cl)C=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(Cl)C=C2)O1 CVCGYXLLQXOOMB-UHFFFAOYSA-N 0.000 description 1
- UMFAZEDFQCMRPF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(F)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=C(F)C=C2)C1 UMFAZEDFQCMRPF-UHFFFAOYSA-N 0.000 description 1
- OSVTZHNUZKATIE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC(C(F)(F)F)=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC(C(F)(F)F)=C2)O1 OSVTZHNUZKATIE-UHFFFAOYSA-N 0.000 description 1
- UMJXFHACJQEFBB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC=C2)C1 UMJXFHACJQEFBB-UHFFFAOYSA-N 0.000 description 1
- GWRYIYSWWXKJCW-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C(C=CC=C2)C1 GWRYIYSWWXKJCW-UHFFFAOYSA-N 0.000 description 1
- KACFVEIZHODKNM-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C(C=CC=C2)N1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C(C=CC=C2)N1 KACFVEIZHODKNM-UHFFFAOYSA-N 0.000 description 1
- NCGCETYGKLDIJF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C(C=CC=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C(C=CC=C2)O1 NCGCETYGKLDIJF-UHFFFAOYSA-N 0.000 description 1
- YANVMUABYPHMRR-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C1C=CC=C2 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCC2=C1C=CC=C2 YANVMUABYPHMRR-UHFFFAOYSA-N 0.000 description 1
- JTEJJUWUAPLQTP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C(C)C)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C(C)C)C1 JTEJJUWUAPLQTP-UHFFFAOYSA-N 0.000 description 1
- GRNZASTZIOADDP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C)(C)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C)(C)C1 GRNZASTZIOADDP-UHFFFAOYSA-N 0.000 description 1
- LAHYIAXIDNEPNQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C)C1 LAHYIAXIDNEPNQ-UHFFFAOYSA-N 0.000 description 1
- AICJWAKAABZTTB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC(F)=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC(F)=C2)C1 AICJWAKAABZTTB-UHFFFAOYSA-N 0.000 description 1
- QGBMSIHFGOEAJV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=N2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=N2)C1 QGBMSIHFGOEAJV-UHFFFAOYSA-N 0.000 description 1
- BIQYGBKZYXMTEJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCN(C2=CC(Cl)=C(C#N)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCN(C2=CC(Cl)=C(C#N)C=C2)C1 BIQYGBKZYXMTEJ-UHFFFAOYSA-N 0.000 description 1
- WYJIPWKAAILEDV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCOC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCOC1 WYJIPWKAAILEDV-UHFFFAOYSA-N 0.000 description 1
- HKKMGKVVRZTYOC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)C1 HKKMGKVVRZTYOC-UHFFFAOYSA-N 0.000 description 1
- CYWWLIMGOAHTGA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)CC1 CYWWLIMGOAHTGA-UHFFFAOYSA-N 0.000 description 1
- URJPWBKSLJQLKS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCOCC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCOCC1 URJPWBKSLJQLKS-UHFFFAOYSA-N 0.000 description 1
- MEVOUBKXRYYVKY-SVNIRARHSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC[C@H](C2=CC=C(C(F)(F)F)C=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC[C@H](C2=CC=C(C(F)(F)F)C=C2)O1 MEVOUBKXRYYVKY-SVNIRARHSA-N 0.000 description 1
- CVCGYXLLQXOOMB-SVNIRARHSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC[C@H](C2=CC=C(Cl)C=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC[C@H](C2=CC=C(Cl)C=C2)O1 CVCGYXLLQXOOMB-SVNIRARHSA-N 0.000 description 1
- OSVTZHNUZKATIE-SVNIRARHSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC[C@H](C2=CC=CC(C(F)(F)F)=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC[C@H](C2=CC=CC(C(F)(F)F)=C2)O1 OSVTZHNUZKATIE-SVNIRARHSA-N 0.000 description 1
- ALXXSIRMVPXROZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1COC2=C(C=C(Cl)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1COC2=C(C=C(Cl)C=C2)C1 ALXXSIRMVPXROZ-UHFFFAOYSA-N 0.000 description 1
- JEKRXERCCHWVOD-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 JEKRXERCCHWVOD-UHFFFAOYSA-N 0.000 description 1
- JEEILMOLDXUDLE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCCC1=CC=C(C(C)(C)C)C=C1 JEEILMOLDXUDLE-UHFFFAOYSA-N 0.000 description 1
- DQSRTALFVYTDIT-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCCC1=CN(C)C2=C1C=CC=C2 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCCC1=CN(C)C2=C1C=CC=C2 DQSRTALFVYTDIT-UHFFFAOYSA-N 0.000 description 1
- QUZTZMFADDDZPQ-AHKZPQOWSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 QUZTZMFADDDZPQ-AHKZPQOWSA-N 0.000 description 1
- QUZTZMFADDDZPQ-BDYUSTAISA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 QUZTZMFADDDZPQ-BDYUSTAISA-N 0.000 description 1
- MEVOUBKXRYYVKY-IAPPQJPRSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1CC[C@@H](C2=CC=C(C(F)(F)F)C=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1CC[C@@H](C2=CC=C(C(F)(F)F)C=C2)O1 MEVOUBKXRYYVKY-IAPPQJPRSA-N 0.000 description 1
- REBWULOJQIGZPU-BVAGGSTKSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1C[C@H]1C1=CC=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@@H]1C[C@H]1C1=CC=CC=C1 REBWULOJQIGZPU-BVAGGSTKSA-N 0.000 description 1
- QUZTZMFADDDZPQ-XNMGPUDCSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 QUZTZMFADDDZPQ-XNMGPUDCSA-N 0.000 description 1
- QUZTZMFADDDZPQ-VPUSJEBWSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1CCC[C@H](C2=CC=CC=C2)C1 QUZTZMFADDDZPQ-VPUSJEBWSA-N 0.000 description 1
- VTQVMBWJBSZKCP-QUPDYRNUSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@@H](C2=CC=C(Cl)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@@H](C2=CC=C(Cl)C=C2)C1 VTQVMBWJBSZKCP-QUPDYRNUSA-N 0.000 description 1
- RCOYOXYPOSYCIH-GUOBSTCESA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@@H](C2=CC=CC=C2)C1 RCOYOXYPOSYCIH-GUOBSTCESA-N 0.000 description 1
- VTQVMBWJBSZKCP-HCGLCNNCSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@H](C2=CC=C(Cl)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@H](C2=CC=C(Cl)C=C2)C1 VTQVMBWJBSZKCP-HCGLCNNCSA-N 0.000 description 1
- RCOYOXYPOSYCIH-ALOJWSFFSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CC[C@H]1C[C@H](C2=CC=CC=C2)C1 RCOYOXYPOSYCIH-ALOJWSFFSA-N 0.000 description 1
- IONFMEHZQYILPZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1Cl Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1Cl IONFMEHZQYILPZ-UHFFFAOYSA-N 0.000 description 1
- YEEMXASWPLCMHT-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1(C2=CC=CC=C2)CCCCC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1(C2=CC=CC=C2)CCCCC1 YEEMXASWPLCMHT-UHFFFAOYSA-N 0.000 description 1
- OMAHJEPEWHRATB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC(Cl)=C(F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC(Cl)=C(F)C=C1 OMAHJEPEWHRATB-UHFFFAOYSA-N 0.000 description 1
- FAUKILUZYQBJNE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC(Cl)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC(Cl)=CC=C1 FAUKILUZYQBJNE-UHFFFAOYSA-N 0.000 description 1
- JTGATRZYPKQHQG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC=C(C(C)C)C=C1 JTGATRZYPKQHQG-UHFFFAOYSA-N 0.000 description 1
- WISAASDXECNZHG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC=C(C2=CC=CC=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1=CC=C(C2=CC=CC=C2)O1 WISAASDXECNZHG-UHFFFAOYSA-N 0.000 description 1
- VYXJGWLCCZAETD-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CC(C2=CC=CC=C2)CO1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CC(C2=CC=CC=C2)CO1 VYXJGWLCCZAETD-UHFFFAOYSA-N 0.000 description 1
- DARQZDRWDRCSOP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(Cl)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(Cl)C=C2)C1 DARQZDRWDRCSOP-UHFFFAOYSA-N 0.000 description 1
- CYRCQGYVUTZSNZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(F)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(F)C=C2)C1 CYRCQGYVUTZSNZ-UHFFFAOYSA-N 0.000 description 1
- VXQYOMCOFSTAIE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC2=C1C=CC=C2 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC2=C1C=CC=C2 VXQYOMCOFSTAIE-UHFFFAOYSA-N 0.000 description 1
- KIMKSRCAGSPGBN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCCC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCCC1 KIMKSRCAGSPGBN-UHFFFAOYSA-N 0.000 description 1
- DRAJXUDCLDGJCB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCCCC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCCCC1 DRAJXUDCLDGJCB-UHFFFAOYSA-N 0.000 description 1
- YMDYYWQTSVOOLG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCN(C2=CC=C(C(F)(F)F)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCN(C2=CC=C(C(F)(F)F)C=C2)C1 YMDYYWQTSVOOLG-UHFFFAOYSA-N 0.000 description 1
- BXENDSDWGRFHCT-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCN(C2=CC=CC=C2)C1 BXENDSDWGRFHCT-UHFFFAOYSA-N 0.000 description 1
- RBDKDFDFKFEVEK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CN(C2=CC=CC=C2)CCO1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CN(C2=CC=CC=C2)CCO1 RBDKDFDFKFEVEK-UHFFFAOYSA-N 0.000 description 1
- XNAZWKCIBKMOPH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 XNAZWKCIBKMOPH-UHFFFAOYSA-N 0.000 description 1
- QNFKHEGDSJXJIK-QHCPKHFHSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NC[C@@H]1CCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NC[C@@H]1CCN(C2=CC=CC=C2)C1 QNFKHEGDSJXJIK-QHCPKHFHSA-N 0.000 description 1
- QNFKHEGDSJXJIK-HSZRJFAPSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NC[C@H]1CCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1NC[C@H]1CCN(C2=CC=CC=C2)C1 QNFKHEGDSJXJIK-HSZRJFAPSA-N 0.000 description 1
- LGUQSGSNJXOZGQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OC1=CC=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OC1=CC=C(Cl)C=C1 LGUQSGSNJXOZGQ-UHFFFAOYSA-N 0.000 description 1
- ASHOQPXCARCOMW-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OCC1=CC=C(C#N)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OCC1=CC=C(C#N)C=C1 ASHOQPXCARCOMW-UHFFFAOYSA-N 0.000 description 1
- BYDVJEYMQJWBDL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 BYDVJEYMQJWBDL-UHFFFAOYSA-N 0.000 description 1
- DXQUOBJFFDNYOO-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OCC1CCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1OCC1CCN(C2=CC=CC=C2)C1 DXQUOBJFFDNYOO-UHFFFAOYSA-N 0.000 description 1
- TYZGHGHSTCHGNI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N4CCCC4=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N4CCCC4=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 TYZGHGHSTCHGNI-UHFFFAOYSA-N 0.000 description 1
- LKBGLSQBLZNARX-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(N4CCCS4(=O)=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(N4CCCS4(=O)=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 LKBGLSQBLZNARX-UHFFFAOYSA-N 0.000 description 1
- OYNVLDDKXGZHPG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NC(=O)C(C)C)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NC(=O)C(C)C)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 OYNVLDDKXGZHPG-UHFFFAOYSA-N 0.000 description 1
- VCLYKUVTURWUST-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NC(N)=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NC(N)=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 VCLYKUVTURWUST-UHFFFAOYSA-N 0.000 description 1
- UCLQWGRWMSCJMC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(=O)(=O)C(C)C)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(=O)(=O)C(C)C)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 UCLQWGRWMSCJMC-UHFFFAOYSA-N 0.000 description 1
- DCQABJZVZUULRQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(=O)(=O)C(C)C)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(=O)(=O)C(C)C)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 DCQABJZVZUULRQ-UHFFFAOYSA-N 0.000 description 1
- AIOSABDYHIAVCI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 AIOSABDYHIAVCI-UHFFFAOYSA-N 0.000 description 1
- RTFPZYTYFWWRGB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(F)(F)F)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(F)(F)F)C(Cl)=C1 RTFPZYTYFWWRGB-UHFFFAOYSA-N 0.000 description 1
- JRRYPZYEAOWTQN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(F)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(F)=C1 JRRYPZYEAOWTQN-UHFFFAOYSA-N 0.000 description 1
- ZHOJIXPOOPQECA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)C1 ZHOJIXPOOPQECA-UHFFFAOYSA-N 0.000 description 1
- ZURKYAYRXXFDKS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=C2)C1 ZURKYAYRXXFDKS-UHFFFAOYSA-N 0.000 description 1
- XGQSQWOXSQIHAA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)C1 XGQSQWOXSQIHAA-UHFFFAOYSA-N 0.000 description 1
- DMBATVRJMXSAHC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1Cl Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1Cl DMBATVRJMXSAHC-UHFFFAOYSA-N 0.000 description 1
- RVSANYXYEYFDNC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(Cl)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(Cl)C=C2)C1 RVSANYXYEYFDNC-UHFFFAOYSA-N 0.000 description 1
- HZJDYXSFRFJMKM-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(F)C=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1NCC1CCCC(C2=CC=C(F)C=C2)C1 HZJDYXSFRFJMKM-UHFFFAOYSA-N 0.000 description 1
- UKHWSXLFJIEUPF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 UKHWSXLFJIEUPF-UHFFFAOYSA-N 0.000 description 1
- UCTNOGHGIICZFR-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)C3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)C3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 UCTNOGHGIICZFR-UHFFFAOYSA-N 0.000 description 1
- DDPVXSRFFZODDF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)C3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)C3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 DDPVXSRFFZODDF-UHFFFAOYSA-N 0.000 description 1
- BZGKBEMAFJJYJX-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 BZGKBEMAFJJYJX-UHFFFAOYSA-N 0.000 description 1
- JEVQZTAGLNMIBU-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)C=CC=C1NCC1=CC=CC(C2=CC=CC=C2)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)C=CC=C1NCC1=CC=CC(C2=CC=CC=C2)=C1 JEVQZTAGLNMIBU-UHFFFAOYSA-N 0.000 description 1
- FWIPUPJOIQYZCB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)C=CN=C1NCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)C=CN=C1NCC1=CC=C(Cl)C(Cl)=C1 FWIPUPJOIQYZCB-UHFFFAOYSA-N 0.000 description 1
- HMQBREDXESNTBE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC1CCC(C2=CC=CC=C2)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC1CCC(C2=CC=CC=C2)CC1 HMQBREDXESNTBE-UHFFFAOYSA-N 0.000 description 1
- LMFVSFCVDQWVCT-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC1CCCCC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC1CCCCC1 LMFVSFCVDQWVCT-UHFFFAOYSA-N 0.000 description 1
- CWWJHXHGLBTIGY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC1COC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC1COC2=C(C=CC=C2)C1 CWWJHXHGLBTIGY-UHFFFAOYSA-N 0.000 description 1
- GNUUYXOLRQEGFC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=C(Cl)C=C1 GNUUYXOLRQEGFC-UHFFFAOYSA-N 0.000 description 1
- YJSPQPHFBDSBAE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=CC(F)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=CC(F)=C1 YJSPQPHFBDSBAE-UHFFFAOYSA-N 0.000 description 1
- POCHNJOCQJZHNN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=CC=C1 POCHNJOCQJZHNN-UHFFFAOYSA-N 0.000 description 1
- RJNAYZJTTQINJI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(C(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(C(F)(F)F)C=C1 RJNAYZJTTQINJI-UHFFFAOYSA-N 0.000 description 1
- VLFQGJMQEGMNSG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(F)C=C1 VLFQGJMQEGMNSG-UHFFFAOYSA-N 0.000 description 1
- QAMSVTLJCPOTCQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(F)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC(F)=C(Cl)C=C1 QAMSVTLJCPOTCQ-UHFFFAOYSA-N 0.000 description 1
- LFAOFLNHNIHEHP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 LFAOFLNHNIHEHP-UHFFFAOYSA-N 0.000 description 1
- WGGSISWFFNDIRI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 WGGSISWFFNDIRI-UHFFFAOYSA-N 0.000 description 1
- AVBXCAACPWZCHX-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C=C1 AVBXCAACPWZCHX-UHFFFAOYSA-N 0.000 description 1
- NJRCDDKIYXAOEG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(OC(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=C(OC(F)(F)F)C=C1 NJRCDDKIYXAOEG-UHFFFAOYSA-N 0.000 description 1
- WEYMUBNNLOYONM-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=CC(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1=CC=CC(Cl)=C1 WEYMUBNNLOYONM-UHFFFAOYSA-N 0.000 description 1
- BYYZMHYZFPQTKJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)O1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)O1 BYYZMHYZFPQTKJ-UHFFFAOYSA-N 0.000 description 1
- DVEWDRLWBJRQTG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CC2=C1C=CC=C2 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CC2=C1C=CC=C2 DVEWDRLWBJRQTG-UHFFFAOYSA-N 0.000 description 1
- DVRCKGZHCOZNTD-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC=C2)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC=C2)CC1 DVRCKGZHCOZNTD-UHFFFAOYSA-N 0.000 description 1
- YDIPQAKPTNOKHM-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=C2)C1 YDIPQAKPTNOKHM-UHFFFAOYSA-N 0.000 description 1
- LZHASYYTJSASAG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCCCC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCCCC1 LZHASYYTJSASAG-UHFFFAOYSA-N 0.000 description 1
- FFFZTVLZAKFQQX-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)CC1 FFFZTVLZAKFQQX-UHFFFAOYSA-N 0.000 description 1
- HGFFVVPVVIKIED-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 HGFFVVPVVIKIED-UHFFFAOYSA-N 0.000 description 1
- JPJBGSPXVDECMM-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 JPJBGSPXVDECMM-UHFFFAOYSA-N 0.000 description 1
- UEJWUPXEPYLOST-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=CC=C1 UEJWUPXEPYLOST-UHFFFAOYSA-N 0.000 description 1
- QMCWIDWWHIYBOS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(C(C)(C)C)C=C1 QMCWIDWWHIYBOS-UHFFFAOYSA-N 0.000 description 1
- PRAOGJAVUHYNJE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(C(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(C(C)C)C=C1 PRAOGJAVUHYNJE-UHFFFAOYSA-N 0.000 description 1
- BITHVDZEDSUTJD-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(Cl)C=C1 BITHVDZEDSUTJD-UHFFFAOYSA-N 0.000 description 1
- VLHFEYISKFKOOQ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(F)C(F)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=C(F)C(F)=C1 VLHFEYISKFKOOQ-UHFFFAOYSA-N 0.000 description 1
- ANROFFBBWUEUQY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCC1=CC=CC=C1 ANROFFBBWUEUQY-UHFFFAOYSA-N 0.000 description 1
- WAVPNTLQHRVSIL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCCC1=CC=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCCC1=CC=CC=C1 WAVPNTLQHRVSIL-UHFFFAOYSA-N 0.000 description 1
- JUQFOOSNFDXVBK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCCCC1=CC=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCCCC1=CC=CC=C1 JUQFOOSNFDXVBK-UHFFFAOYSA-N 0.000 description 1
- NJHAZIJXXFNPIN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCOC1=CC=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCOC1=CC=CC=C1 NJHAZIJXXFNPIN-UHFFFAOYSA-N 0.000 description 1
- RWLIBYDICPOBHC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCOCC1=CC=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CCCOCC1=CC=CC=C1 RWLIBYDICPOBHC-UHFFFAOYSA-N 0.000 description 1
- YDIPQAKPTNOKHM-UKILVPOCSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 YDIPQAKPTNOKHM-UKILVPOCSA-N 0.000 description 1
- YDIPQAKPTNOKHM-ZCYQVOJMSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1CC[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 YDIPQAKPTNOKHM-ZCYQVOJMSA-N 0.000 description 1
- GFUNRPGQLWNZLZ-HXUWFJFHSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1C[C@@H]1CCC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1C[C@@H]1CCC2=C(C=CC=C2)C1 GFUNRPGQLWNZLZ-HXUWFJFHSA-N 0.000 description 1
- AADYHSJNJHCIMN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1Cl Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1Cl AADYHSJNJHCIMN-UHFFFAOYSA-N 0.000 description 1
- CPZQLKODDOXUGA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC(F)=C(C(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC(F)=C(C(F)(F)F)C=C1 CPZQLKODDOXUGA-UHFFFAOYSA-N 0.000 description 1
- BHYLNVBHWKCYCD-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC(OC(F)(F)F)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC(OC(F)(F)F)=CC=C1 BHYLNVBHWKCYCD-UHFFFAOYSA-N 0.000 description 1
- JXPPLQWOIRRDBH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC2=C(C=C1)OC=C2 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC2=C(C=C1)OC=C2 JXPPLQWOIRRDBH-UHFFFAOYSA-N 0.000 description 1
- DBLFRPKJWLNVKA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC=C(C(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC=C(C(F)(F)F)C=C1 DBLFRPKJWLNVKA-UHFFFAOYSA-N 0.000 description 1
- GGJCISQKFJSPLO-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1CC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1CC2=C(C=CC=C2)C1 GGJCISQKFJSPLO-UHFFFAOYSA-N 0.000 description 1
- CPMFBCFQKSQYJP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1CCC(C(F)(F)F)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1CCC(C(F)(F)F)CC1 CPMFBCFQKSQYJP-UHFFFAOYSA-N 0.000 description 1
- XMYPRVZKIFOPTJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1CCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1CCN(C2=CC=CC=C2)C1 XMYPRVZKIFOPTJ-UHFFFAOYSA-N 0.000 description 1
- XJNMRUWASYFPOZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC(C(F)(F)F)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC(C(F)(F)F)=CC=C1 XJNMRUWASYFPOZ-UHFFFAOYSA-N 0.000 description 1
- SECUIMGTWLXIAY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC=C(C(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC=C(C(F)(F)F)C=C1 SECUIMGTWLXIAY-UHFFFAOYSA-N 0.000 description 1
- MFTQUGVVOBNRSI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC=C(OC(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC=C(OC(F)(F)F)C=C1 MFTQUGVVOBNRSI-UHFFFAOYSA-N 0.000 description 1
- CZOZHXZMRYMZRK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 CZOZHXZMRYMZRK-UHFFFAOYSA-N 0.000 description 1
- LZMUDRWLKSHORC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(OC4=CC=C(F)C(F)=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(OC4=CC=C(F)C(F)=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 LZMUDRWLKSHORC-UHFFFAOYSA-N 0.000 description 1
- BJZCRWRNWHKOMF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(OC4=NC=CC=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(OC4=NC=CC=C4)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 BJZCRWRNWHKOMF-UHFFFAOYSA-N 0.000 description 1
- QHCLNHARVQUUCY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(S(=O)(=O)N(C)C)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(S(=O)(=O)N(C)C)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 QHCLNHARVQUUCY-UHFFFAOYSA-N 0.000 description 1
- RFWRHMOSXZAEEN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC(S(N)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC(S(N)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 RFWRHMOSXZAEEN-UHFFFAOYSA-N 0.000 description 1
- RORXBXBHGGTILS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC4(CC3)CCN(S(C)(=O)=O)C4)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC4(CC3)CCN(S(C)(=O)=O)C4)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 RORXBXBHGGTILS-UHFFFAOYSA-N 0.000 description 1
- YFPPACIZRGVQSX-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC4(CC3)CNC(=O)O4)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC4(CC3)CNC(=O)O4)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 YFPPACIZRGVQSX-UHFFFAOYSA-N 0.000 description 1
- OQENCRPZYJFHLB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC4(CCNC4=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC4(CCNC4=O)CC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 OQENCRPZYJFHLB-UHFFFAOYSA-N 0.000 description 1
- PRYOKTDDYZTTFK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCC4=C(C=C(C(F)(F)F)C=N4)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC4=C(C=C(C(F)(F)F)C=N4)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 PRYOKTDDYZTTFK-UHFFFAOYSA-N 0.000 description 1
- PEZBSWKNIITKPB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCC(F)C3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCC(F)C3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 PEZBSWKNIITKPB-UHFFFAOYSA-N 0.000 description 1
- LGZNLAQLUKQTQB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCC(O)C3)CC2)N=CN=C1Cl Chemical compound CC1=C(C(=O)N2CCC(N3CCCC(O)C3)CC2)N=CN=C1Cl LGZNLAQLUKQTQB-UHFFFAOYSA-N 0.000 description 1
- YDQFOUYKISNOKF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCC(O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCC(O)CC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 YDQFOUYKISNOKF-UHFFFAOYSA-N 0.000 description 1
- SXTWAMFPXMPQEE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCC(O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCC(O)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 SXTWAMFPXMPQEE-UHFFFAOYSA-N 0.000 description 1
- FLFKBIMQFPJRMT-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCC3)C2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCC3)C2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 FLFKBIMQFPJRMT-UHFFFAOYSA-N 0.000 description 1
- YQMWNOPJWOUPPP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 YQMWNOPJWOUPPP-UHFFFAOYSA-N 0.000 description 1
- VFMPBUCLFRZSIH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)C2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)C2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 VFMPBUCLFRZSIH-UHFFFAOYSA-N 0.000 description 1
- PPRVECBPSSMJLC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(C(F)(F)F)=C(Cl)C=C1 PPRVECBPSSMJLC-UHFFFAOYSA-N 0.000 description 1
- JCAMYCUEQMVWOM-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(C(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(C(F)(F)F)C=C1 JCAMYCUEQMVWOM-UHFFFAOYSA-N 0.000 description 1
- RNVWHAFRKKBVBN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(F)C=C1 RNVWHAFRKKBVBN-UHFFFAOYSA-N 0.000 description 1
- UOYLGBDNRDJZNR-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(F)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC(F)=C(Cl)C=C1 UOYLGBDNRDJZNR-UHFFFAOYSA-N 0.000 description 1
- VRUWYILOGGJBAZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC=C(Cl)C=C1 VRUWYILOGGJBAZ-UHFFFAOYSA-N 0.000 description 1
- JVMNIMDPCBMWOV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC=CC(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1=CC=CC(Cl)=C1 JVMNIMDPCBMWOV-UHFFFAOYSA-N 0.000 description 1
- WFIWJVSPBWXILC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC=C2)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1CCC(C2=CC=CC=C2)CC1 WFIWJVSPBWXILC-UHFFFAOYSA-N 0.000 description 1
- CGKQZCNQUNLIAJ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1CCCC(C2=CC=CC=C2)C1 CGKQZCNQUNLIAJ-UHFFFAOYSA-N 0.000 description 1
- JGZHPLJGTBENIN-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)CC1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCC1CCN(C2=CC=CC=C2)CC1 JGZHPLJGTBENIN-UHFFFAOYSA-N 0.000 description 1
- CUAGHJGJGNKAME-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 CUAGHJGJGNKAME-UHFFFAOYSA-N 0.000 description 1
- DJBUISKYYGEYMA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC(Cl)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC(Cl)=CC=C1 DJBUISKYYGEYMA-UHFFFAOYSA-N 0.000 description 1
- ZZDZCNZYWFMCDB-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC=C(C(C)(C)C)C=C1 ZZDZCNZYWFMCDB-UHFFFAOYSA-N 0.000 description 1
- LWPUYWHQKXNVLK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC=C(Cl)C=C1 LWPUYWHQKXNVLK-UHFFFAOYSA-N 0.000 description 1
- OOWVNAYLGIPQLK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC=C(F)C(F)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCC3)CC2)N=CN=C1CCCC1=CC=C(F)C(F)=C1 OOWVNAYLGIPQLK-UHFFFAOYSA-N 0.000 description 1
- KGODPLNZNINDQP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCCCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCCCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 KGODPLNZNINDQP-UHFFFAOYSA-N 0.000 description 1
- WECSERQWUPRYMY-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCOCC3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCOCC3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 WECSERQWUPRYMY-UHFFFAOYSA-N 0.000 description 1
- HAHHERKBQLKPFH-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCCOCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCCOCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 HAHHERKBQLKPFH-UHFFFAOYSA-N 0.000 description 1
- LXGDZPBCCSISPK-HXUWFJFHSA-N CC1=C(C(=O)N2CCC(N3CCC[C@@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 LXGDZPBCCSISPK-HXUWFJFHSA-N 0.000 description 1
- YKERFHQZKMUFOH-HXUWFJFHSA-N CC1=C(C(=O)N2CCC(N3CCC[C@@H](O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@@H](O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 YKERFHQZKMUFOH-HXUWFJFHSA-N 0.000 description 1
- HBSDZWUNAVINSX-AREMUKBSSA-N CC1=C(C(=O)N2CCC(N3CCC[C@@H]3CC(=O)N(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@@H]3CC(=O)N(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 HBSDZWUNAVINSX-AREMUKBSSA-N 0.000 description 1
- KTYNGASWKGGJTI-NRFANRHFSA-N CC1=C(C(=O)N2CCC(N3CCC[C@H](C(=O)N(C)C)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@H](C(=O)N(C)C)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 KTYNGASWKGGJTI-NRFANRHFSA-N 0.000 description 1
- MDTIRLYSQNQTQC-IBGZPJMESA-N CC1=C(C(=O)N2CCC(N3CCC[C@H](C(=O)O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@H](C(=O)O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 MDTIRLYSQNQTQC-IBGZPJMESA-N 0.000 description 1
- VJNAFDWWJQVBBF-IBGZPJMESA-N CC1=C(C(=O)N2CCC(N3CCC[C@H](C(N)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@H](C(N)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 VJNAFDWWJQVBBF-IBGZPJMESA-N 0.000 description 1
- LXGDZPBCCSISPK-FQEVSTJZSA-N CC1=C(C(=O)N2CCC(N3CCC[C@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 LXGDZPBCCSISPK-FQEVSTJZSA-N 0.000 description 1
- YKERFHQZKMUFOH-FQEVSTJZSA-N CC1=C(C(=O)N2CCC(N3CCC[C@H](O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@H](O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 YKERFHQZKMUFOH-FQEVSTJZSA-N 0.000 description 1
- HBSDZWUNAVINSX-SANMLTNESA-N CC1=C(C(=O)N2CCC(N3CCC[C@H]3CC(=O)N(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCC[C@H]3CC(=O)N(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 HBSDZWUNAVINSX-SANMLTNESA-N 0.000 description 1
- IIWFUJXMJDYMGM-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCN(C(=O)C(C)C)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCN(C(=O)C(C)C)CC3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 IIWFUJXMJDYMGM-UHFFFAOYSA-N 0.000 description 1
- RJMSKHGMTKHDCT-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCN(S(C)(=O)=O)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCN(S(C)(=O)=O)CC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 RJMSKHGMTKHDCT-UHFFFAOYSA-N 0.000 description 1
- FANRNRODFIWQLS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCNCC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCNCC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 FANRNRODFIWQLS-UHFFFAOYSA-N 0.000 description 1
- BGOGVYOJWXBAAV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOC(C)C3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOC(C)C3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 BGOGVYOJWXBAAV-UHFFFAOYSA-N 0.000 description 1
- DFADORAXDPPVTP-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOC(C)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOC(C)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 DFADORAXDPPVTP-UHFFFAOYSA-N 0.000 description 1
- SZBWYCPGWAAYTK-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOC(C)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOC(C)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 SZBWYCPGWAAYTK-UHFFFAOYSA-N 0.000 description 1
- OYMHSWRZMAQEAG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOC(C4=CC=CC=C4)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOC(C4=CC=CC=C4)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 OYMHSWRZMAQEAG-UHFFFAOYSA-N 0.000 description 1
- MPVQTISZSGNVAN-JXMROGBWSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1/C=C/C1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1/C=C/C1=CC=C(C(C)(C)C)C=C1 MPVQTISZSGNVAN-JXMROGBWSA-N 0.000 description 1
- AHYNWSXRTHLBLG-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CC1=CC=C(C(C)(C)C)C=C1 AHYNWSXRTHLBLG-UHFFFAOYSA-N 0.000 description 1
- GBMOQUWZGXHCLL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(C(F)(F)F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(Cl)=C(C(F)(F)F)C=C1 GBMOQUWZGXHCLL-UHFFFAOYSA-N 0.000 description 1
- HAHLYXMPKFSLJC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(F)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(F)=C(Cl)C=C1 HAHLYXMPKFSLJC-UHFFFAOYSA-N 0.000 description 1
- OXGSLRUNWYFXOF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(F)=C(F)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(F)=C(F)C=C1 OXGSLRUNWYFXOF-UHFFFAOYSA-N 0.000 description 1
- ARUZVCLGXSTENF-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 ARUZVCLGXSTENF-UHFFFAOYSA-N 0.000 description 1
- AHOTZKAQPSXBEV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 AHOTZKAQPSXBEV-UHFFFAOYSA-N 0.000 description 1
- KAPGUSZQJLEQNZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1CC2=C(C=CC=C2)C1 KAPGUSZQJLEQNZ-UHFFFAOYSA-N 0.000 description 1
- KPQUDEHAXMHOLE-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1CCCN(C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1CCCN(C2=CC=CC=C2)C1 KPQUDEHAXMHOLE-UHFFFAOYSA-N 0.000 description 1
- XDDNLUXHBPDPOS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1COC2=C(C=CC=C2)C1 XDDNLUXHBPDPOS-UHFFFAOYSA-N 0.000 description 1
- CCEWTMVMDFTLGA-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1Cl Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1Cl CCEWTMVMDFTLGA-UHFFFAOYSA-N 0.000 description 1
- PKLBFLDRFYGOFV-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 PKLBFLDRFYGOFV-UHFFFAOYSA-N 0.000 description 1
- IMSDSAPAPJFUNL-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1OCC1=CC=C(C(C)(C)C)C=C1 IMSDSAPAPJFUNL-UHFFFAOYSA-N 0.000 description 1
- PVOYYWDNAPABSZ-OAQYLSRUSA-N CC1=C(C(=O)N2CCC(N3CC[C@@H](C(N)=O)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@@H](C(N)=O)C3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 PVOYYWDNAPABSZ-OAQYLSRUSA-N 0.000 description 1
- YEGCVMYEPCBHFT-GOSISDBHSA-N CC1=C(C(=O)N2CCC(N3CC[C@@H](C(N)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@@H](C(N)=O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 YEGCVMYEPCBHFT-GOSISDBHSA-N 0.000 description 1
- HYMAFJJZKLJULA-GOSISDBHSA-N CC1=C(C(=O)N2CCC(N3CC[C@@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 HYMAFJJZKLJULA-GOSISDBHSA-N 0.000 description 1
- GXJJENVNIULXJK-GOSISDBHSA-N CC1=C(C(=O)N2CCC(N3CC[C@@H](O)C3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@@H](O)C3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 GXJJENVNIULXJK-GOSISDBHSA-N 0.000 description 1
- GZOIMFOWVYYRKL-PKTZIBPZSA-N CC1=C(C(=O)N2CCC(N3CC[C@@H](O)[C@@H](O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@@H](O)[C@@H](O)C3)CC2)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 GZOIMFOWVYYRKL-PKTZIBPZSA-N 0.000 description 1
- ORKHTPPAUPDVFJ-KRWDZBQOSA-N CC1=C(C(=O)N2CCC(N3CC[C@H](C(N)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@H](C(N)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 ORKHTPPAUPDVFJ-KRWDZBQOSA-N 0.000 description 1
- LRWPJLDPWBIBJI-FQEVSTJZSA-N CC1=C(C(=O)N2CCC(N3CC[C@H](N(C)S(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@H](N(C)S(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 LRWPJLDPWBIBJI-FQEVSTJZSA-N 0.000 description 1
- HYMAFJJZKLJULA-SFHVURJKSA-N CC1=C(C(=O)N2CCC(N3CC[C@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@H](NS(C)(=O)=O)C3)CC2)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 HYMAFJJZKLJULA-SFHVURJKSA-N 0.000 description 1
- GXJJENVNIULXJK-SFHVURJKSA-N CC1=C(C(=O)N2CCC(N3CC[C@H](O)C3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N3CC[C@H](O)C3)CC2)N=CN=C1NCCC1=CC(Cl)=C(Cl)C=C1 GXJJENVNIULXJK-SFHVURJKSA-N 0.000 description 1
- PUWHXSLTJWWIAZ-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(NC(=O)OC(C)(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(NC(=O)OC(C)(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 PUWHXSLTJWWIAZ-UHFFFAOYSA-N 0.000 description 1
- YZIQOLKQLWESTK-ISKFKSNPSA-N CC1=C(C(=O)N2CCC(NC(=O)OC(C)(C)C)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)N2CCC(NC(=O)OC(C)(C)C)CC2)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 YZIQOLKQLWESTK-ISKFKSNPSA-N 0.000 description 1
- AMMIAQKPSLBAFI-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(NC3CCOC4=C3C=CC=C4)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(NC3CCOC4=C3C=CC=C4)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 AMMIAQKPSLBAFI-UHFFFAOYSA-N 0.000 description 1
- DVYLQKXIBJLKEC-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(NC3CCOCC3F)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(NC3CCOCC3F)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 DVYLQKXIBJLKEC-UHFFFAOYSA-N 0.000 description 1
- ZKJZLMYDJAAEMS-UHFFFAOYSA-N CC1=C(C(=O)N2CCC(NCC3CCCCO3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(NCC3CCCCO3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 ZKJZLMYDJAAEMS-UHFFFAOYSA-N 0.000 description 1
- OMJWAEOZGUKYKQ-XMMPIXPASA-N CC1=C(C(=O)N2CCC(N[C@@H]3CCCN(S(C)(=O)=O)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCC(N[C@@H]3CCCN(S(C)(=O)=O)C3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 OMJWAEOZGUKYKQ-XMMPIXPASA-N 0.000 description 1
- OAJZJAGAMPGZPY-UHFFFAOYSA-N CC1=C(C(=O)N2CCCC(=O)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCC(=O)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 OAJZJAGAMPGZPY-UHFFFAOYSA-N 0.000 description 1
- KRGMHPKBJNACBW-UHFFFAOYSA-N CC1=C(C(=O)N2CCCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 KRGMHPKBJNACBW-UHFFFAOYSA-N 0.000 description 1
- ZAJOZVDTJRULPR-UHFFFAOYSA-N CC1=C(C(=O)N2CCCC(N3CCCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCC(N3CCCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 ZAJOZVDTJRULPR-UHFFFAOYSA-N 0.000 description 1
- QKQSLOMWXYBLMG-UHFFFAOYSA-N CC1=C(C(=O)N2CCCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 QKQSLOMWXYBLMG-UHFFFAOYSA-N 0.000 description 1
- WVTQRCFZHIWXMR-UHFFFAOYSA-N CC1=C(C(=O)N2CCCN(C(=O)OC(C)(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCN(C(=O)OC(C)(C)C)CC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 WVTQRCFZHIWXMR-UHFFFAOYSA-N 0.000 description 1
- PDQVULYRTCQPEM-UHFFFAOYSA-N CC1=C(C(=O)N2CCCN(C(C)C)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCN(C(C)C)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 PDQVULYRTCQPEM-UHFFFAOYSA-N 0.000 description 1
- UBSSAYFUFWGUND-UHFFFAOYSA-N CC1=C(C(=O)N2CCCN(C3CCCC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCN(C3CCCC3)CC2)N=CN=C1NCC1=CC=C(C(C)(C)C)C=C1 UBSSAYFUFWGUND-UHFFFAOYSA-N 0.000 description 1
- RSJCBFZDOCMIPX-UHFFFAOYSA-N CC1=C(C(=O)N2CCCNCC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)N2CCCNCC2)N=CN=C1CCC1=CC=C(C(C)(C)C)C=C1 RSJCBFZDOCMIPX-UHFFFAOYSA-N 0.000 description 1
- QPYNFVAIEDMQLW-UHFFFAOYSA-N CC1=C(C(=O)O)C=CC=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 Chemical compound CC1=C(C(=O)O)C=CC=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 QPYNFVAIEDMQLW-UHFFFAOYSA-N 0.000 description 1
- MGPIPDQERGMBAI-UHFFFAOYSA-N CC1=C(C(=O)O)C=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)O)C=CN=C1CCC1=CC(Cl)=C(Cl)C=C1 MGPIPDQERGMBAI-UHFFFAOYSA-N 0.000 description 1
- UEWONDOEJLULJD-JXMROGBWSA-N CC1=C(C(=O)O)N=CN=C1/C=C/C1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)O)N=CN=C1/C=C/C1=CC=C(C(C)(C)C)C=C1 UEWONDOEJLULJD-JXMROGBWSA-N 0.000 description 1
- HYWUFIXEOUOEAS-UHFFFAOYSA-N CC1=C(C(=O)O)N=CN=C1CC1=CC=C(C(C)(C)C)C=C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CC1=CC=C(C(C)(C)C)C=C1 HYWUFIXEOUOEAS-UHFFFAOYSA-N 0.000 description 1
- RXJHALIHLCCXEG-UHFFFAOYSA-N CC1=C(C(=O)O)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CCC1=CC=C(Cl)C(Cl)=C1 RXJHALIHLCCXEG-UHFFFAOYSA-N 0.000 description 1
- OJJSLHORHGVOPW-UHFFFAOYSA-N CC1=C(C(=O)O)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 OJJSLHORHGVOPW-UHFFFAOYSA-N 0.000 description 1
- VGYGSGLVDWQDNQ-UHFFFAOYSA-N CC1=C(C(=O)O)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 VGYGSGLVDWQDNQ-UHFFFAOYSA-N 0.000 description 1
- JZDUFGVBMFAVRF-NVXWUHKLSA-N CC1=C(C(=O)O)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 JZDUFGVBMFAVRF-NVXWUHKLSA-N 0.000 description 1
- GOBUAWXGIJZFPZ-OTVXOJSOSA-N CC1=C(C(=O)O)N=CN=C1CC[C@H]1C[C@@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CC[C@H]1C[C@@H](C2=CC=CC=C2)C1 GOBUAWXGIJZFPZ-OTVXOJSOSA-N 0.000 description 1
- GOBUAWXGIJZFPZ-CTYIDZIISA-N CC1=C(C(=O)O)N=CN=C1CC[C@H]1C[C@H](C2=CC=CC=C2)C1 Chemical compound CC1=C(C(=O)O)N=CN=C1CC[C@H]1C[C@H](C2=CC=CC=C2)C1 GOBUAWXGIJZFPZ-CTYIDZIISA-N 0.000 description 1
- HBVGHPKSQHXUMX-UHFFFAOYSA-N CC1=C(C)C=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1 Chemical compound CC1=C(C)C=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1 HBVGHPKSQHXUMX-UHFFFAOYSA-N 0.000 description 1
- MVCXAZPIGXNVPF-UHFFFAOYSA-N CC1=C(CCC2=CC(C3=CC=CC=C3)=CC=C2)N=CN=C1C(=O)N1CCC(N2CCC(O)CC2)CC1 Chemical compound CC1=C(CCC2=CC(C3=CC=CC=C3)=CC=C2)N=CN=C1C(=O)N1CCC(N2CCC(O)CC2)CC1 MVCXAZPIGXNVPF-UHFFFAOYSA-N 0.000 description 1
- XMZIDIVRQZVUKQ-UHFFFAOYSA-N CC1=C(CCC2=CC(C3=CC=CC=C3)=CC=C2)N=CN=C1C(=O)N1CCC(N2CCCC(O)C2)CC1 Chemical compound CC1=C(CCC2=CC(C3=CC=CC=C3)=CC=C2)N=CN=C1C(=O)N1CCC(N2CCCC(O)C2)CC1 XMZIDIVRQZVUKQ-UHFFFAOYSA-N 0.000 description 1
- HHJXUBUHRZHUCQ-UHFFFAOYSA-N CC1=C(CCC2=CC=C(C3=CC=CC=C3)C=C2)N=CN=C1C(=O)N1CCC(N2CCC(O)CC2)CC1 Chemical compound CC1=C(CCC2=CC=C(C3=CC=CC=C3)C=C2)N=CN=C1C(=O)N1CCC(N2CCC(O)CC2)CC1 HHJXUBUHRZHUCQ-UHFFFAOYSA-N 0.000 description 1
- RSFLXSISQMSKCP-UHFFFAOYSA-N CC1=C(F)C=C(CCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1 Chemical compound CC1=C(F)C=C(CCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1 RSFLXSISQMSKCP-UHFFFAOYSA-N 0.000 description 1
- SPWXUXBEHJRIBP-UHFFFAOYSA-N CC1=C(F)C=C(CCC2=NC=NC(C(=O)N3CCC(N4CCOCC4)CC3)=C2C)C=C1 Chemical compound CC1=C(F)C=C(CCC2=NC=NC(C(=O)N3CCC(N4CCOCC4)CC3)=C2C)C=C1 SPWXUXBEHJRIBP-UHFFFAOYSA-N 0.000 description 1
- QIKTXWJEMVXSGN-UHFFFAOYSA-N CC1=C(F)C=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1 Chemical compound CC1=C(F)C=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1 QIKTXWJEMVXSGN-UHFFFAOYSA-N 0.000 description 1
- WUTVQGUZBHFNBK-UHFFFAOYSA-N CC1=C(F)C=CC(CCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)=C1 Chemical compound CC1=C(F)C=CC(CCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)=C1 WUTVQGUZBHFNBK-UHFFFAOYSA-N 0.000 description 1
- OJDUOIGKCNQCFR-UHFFFAOYSA-N CC1=C(F)C=CC(CCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)=C1 Chemical compound CC1=C(F)C=CC(CCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)=C1 OJDUOIGKCNQCFR-UHFFFAOYSA-N 0.000 description 1
- WPFNOPCYQVQIIM-UHFFFAOYSA-N CC1=C(F)C=CC(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)=C1 Chemical compound CC1=C(F)C=CC(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)=C1 WPFNOPCYQVQIIM-UHFFFAOYSA-N 0.000 description 1
- UCGQDPAMFRDQOC-UHFFFAOYSA-N CC1=C(O)N=CN=C1C(=O)O Chemical compound CC1=C(O)N=CN=C1C(=O)O UCGQDPAMFRDQOC-UHFFFAOYSA-N 0.000 description 1
- WEKLVDWETBLZJV-UHFFFAOYSA-N CC1=CC(C2CCC(CBr)O2)=CC=C1 Chemical compound CC1=CC(C2CCC(CBr)O2)=CC=C1 WEKLVDWETBLZJV-UHFFFAOYSA-N 0.000 description 1
- FVQBVIQYJBIDET-UHFFFAOYSA-N CC1=CC(C2CCC(CBr)O2)=CC=C1F Chemical compound CC1=CC(C2CCC(CBr)O2)=CC=C1F FVQBVIQYJBIDET-UHFFFAOYSA-N 0.000 description 1
- JPVWQDATNMNICK-UHFFFAOYSA-N CC1=CC(C2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 Chemical compound CC1=CC(C2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 JPVWQDATNMNICK-UHFFFAOYSA-N 0.000 description 1
- FTFYDAIWCBUZNM-UHFFFAOYSA-N CC1=CC(C2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 Chemical compound CC1=CC(C2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 FTFYDAIWCBUZNM-UHFFFAOYSA-N 0.000 description 1
- KIQFBOSKMHEMNQ-UHFFFAOYSA-N CC1=CC(C2CCC(CN)O2)=CC=C1 Chemical compound CC1=CC(C2CCC(CN)O2)=CC=C1 KIQFBOSKMHEMNQ-UHFFFAOYSA-N 0.000 description 1
- WKULCSOQNRMSAB-UHFFFAOYSA-N CC1=CC(C2CCC(CN)O2)=CC=C1F Chemical compound CC1=CC(C2CCC(CN)O2)=CC=C1F WKULCSOQNRMSAB-UHFFFAOYSA-N 0.000 description 1
- OUHIGEAUWYAKHG-UHFFFAOYSA-N CC1=CC(COC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)=CC=C1Cl Chemical compound CC1=CC(COC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)=CC=C1Cl OUHIGEAUWYAKHG-UHFFFAOYSA-N 0.000 description 1
- WEKLVDWETBLZJV-NEPJUHHUSA-N CC1=CC([C@@H]2CC[C@H](CBr)O2)=CC=C1 Chemical compound CC1=CC([C@@H]2CC[C@H](CBr)O2)=CC=C1 WEKLVDWETBLZJV-NEPJUHHUSA-N 0.000 description 1
- FVQBVIQYJBIDET-PWSUYJOCSA-N CC1=CC([C@@H]2CC[C@H](CBr)O2)=CC=C1F Chemical compound CC1=CC([C@@H]2CC[C@H](CBr)O2)=CC=C1F FVQBVIQYJBIDET-PWSUYJOCSA-N 0.000 description 1
- KIQFBOSKMHEMNQ-NEPJUHHUSA-N CC1=CC([C@@H]2CC[C@H](CN)O2)=CC=C1 Chemical compound CC1=CC([C@@H]2CC[C@H](CN)O2)=CC=C1 KIQFBOSKMHEMNQ-NEPJUHHUSA-N 0.000 description 1
- WKULCSOQNRMSAB-PWSUYJOCSA-N CC1=CC([C@@H]2CC[C@H](CN)O2)=CC=C1F Chemical compound CC1=CC([C@@H]2CC[C@H](CN)O2)=CC=C1F WKULCSOQNRMSAB-PWSUYJOCSA-N 0.000 description 1
- JPVWQDATNMNICK-FUJFQHJFSA-N CC1=CC([C@H]2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 Chemical compound CC1=CC([C@H]2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 JPVWQDATNMNICK-FUJFQHJFSA-N 0.000 description 1
- FTFYDAIWCBUZNM-ZBAATNBSSA-N CC1=CC([C@H]2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 Chemical compound CC1=CC([C@H]2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1 FTFYDAIWCBUZNM-ZBAATNBSSA-N 0.000 description 1
- WEKLVDWETBLZJV-VXGBXAGGSA-N CC1=CC([C@H]2CC[C@H](CBr)O2)=CC=C1 Chemical compound CC1=CC([C@H]2CC[C@H](CBr)O2)=CC=C1 WEKLVDWETBLZJV-VXGBXAGGSA-N 0.000 description 1
- FVQBVIQYJBIDET-ZYHUDNBSSA-N CC1=CC([C@H]2CC[C@H](CBr)O2)=CC=C1F Chemical compound CC1=CC([C@H]2CC[C@H](CBr)O2)=CC=C1F FVQBVIQYJBIDET-ZYHUDNBSSA-N 0.000 description 1
- BFMGJJYETYOJBU-BHBYDHKZSA-N CC1=CC([C@H]2CC[C@H](CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1F Chemical compound CC1=CC([C@H]2CC[C@H](CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)=CC=C1F BFMGJJYETYOJBU-BHBYDHKZSA-N 0.000 description 1
- KIQFBOSKMHEMNQ-VXGBXAGGSA-N CC1=CC([C@H]2CC[C@H](CN)O2)=CC=C1 Chemical compound CC1=CC([C@H]2CC[C@H](CN)O2)=CC=C1 KIQFBOSKMHEMNQ-VXGBXAGGSA-N 0.000 description 1
- WKULCSOQNRMSAB-ZYHUDNBSSA-N CC1=CC([C@H]2CC[C@H](CN)O2)=CC=C1F Chemical compound CC1=CC([C@H]2CC[C@H](CN)O2)=CC=C1F WKULCSOQNRMSAB-ZYHUDNBSSA-N 0.000 description 1
- OIAPLKBUEZWJCS-UHFFFAOYSA-N CC1=CC=C(C2CCC(CBr)O2)C=C1 Chemical compound CC1=CC=C(C2CCC(CBr)O2)C=C1 OIAPLKBUEZWJCS-UHFFFAOYSA-N 0.000 description 1
- BCHCKGVMOJJBCW-UHFFFAOYSA-N CC1=CC=C(C2CCC(CBr)O2)C=C1F Chemical compound CC1=CC=C(C2CCC(CBr)O2)C=C1F BCHCKGVMOJJBCW-UHFFFAOYSA-N 0.000 description 1
- YWSMLHWRODQUKJ-UHFFFAOYSA-N CC1=CC=C(C2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 Chemical compound CC1=CC=C(C2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 YWSMLHWRODQUKJ-UHFFFAOYSA-N 0.000 description 1
- XYURMLSBDKTPIL-UHFFFAOYSA-N CC1=CC=C(C2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1F Chemical compound CC1=CC=C(C2CCC(CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1F XYURMLSBDKTPIL-UHFFFAOYSA-N 0.000 description 1
- ONKLASJYJMOOPV-UHFFFAOYSA-N CC1=CC=C(C2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 Chemical compound CC1=CC=C(C2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 ONKLASJYJMOOPV-UHFFFAOYSA-N 0.000 description 1
- APBZQAPCMWYHMJ-UHFFFAOYSA-N CC1=CC=C(C2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1F Chemical compound CC1=CC=C(C2CCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1F APBZQAPCMWYHMJ-UHFFFAOYSA-N 0.000 description 1
- COYRDOUCWSMXCF-UHFFFAOYSA-N CC1=CC=C(C2CCC(CN)O2)C=C1 Chemical compound CC1=CC=C(C2CCC(CN)O2)C=C1 COYRDOUCWSMXCF-UHFFFAOYSA-N 0.000 description 1
- RIYMOCBNKGQNQK-UHFFFAOYSA-N CC1=CC=C(C2CCC(CN)O2)C=C1F Chemical compound CC1=CC=C(C2CCC(CN)O2)C=C1F RIYMOCBNKGQNQK-UHFFFAOYSA-N 0.000 description 1
- QKLVYXRCCBQGBZ-UHFFFAOYSA-N CC1=CC=C(C2CCCC(C#N)C2)C=C1 Chemical compound CC1=CC=C(C2CCCC(C#N)C2)C=C1 QKLVYXRCCBQGBZ-UHFFFAOYSA-N 0.000 description 1
- UZGCUFICZYGVBM-UHFFFAOYSA-N CC1=CC=C(C2CCCC(C#N)C2)O1 Chemical compound CC1=CC=C(C2CCCC(C#N)C2)O1 UZGCUFICZYGVBM-UHFFFAOYSA-N 0.000 description 1
- QPJDQRONNPEMRS-UHFFFAOYSA-N CC1=CC=C(C2CCCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)C=C1 Chemical compound CC1=CC=C(C2CCCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)C=C1 QPJDQRONNPEMRS-UHFFFAOYSA-N 0.000 description 1
- ZHANHTIXYXSZJX-UHFFFAOYSA-N CC1=CC=C(C2CCCC(CN)C2)C=C1 Chemical compound CC1=CC=C(C2CCCC(CN)C2)C=C1 ZHANHTIXYXSZJX-UHFFFAOYSA-N 0.000 description 1
- OKUPDKRLFXQNTB-UHFFFAOYSA-N CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1Cl Chemical compound CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1Cl OKUPDKRLFXQNTB-UHFFFAOYSA-N 0.000 description 1
- AWOBXWMJSMQDEI-UHFFFAOYSA-N CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1Cl Chemical compound CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1Cl AWOBXWMJSMQDEI-UHFFFAOYSA-N 0.000 description 1
- QEIIFCLMWOFTJS-UHFFFAOYSA-N CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1F Chemical compound CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1F QEIIFCLMWOFTJS-UHFFFAOYSA-N 0.000 description 1
- KEZYTMYTGXWHBS-UHFFFAOYSA-N CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCOCC4)CC3)=C2C)C=C1Cl Chemical compound CC1=CC=C(CCC2=NC=NC(C(=O)N3CCC(N4CCOCC4)CC3)=C2C)C=C1Cl KEZYTMYTGXWHBS-UHFFFAOYSA-N 0.000 description 1
- BPXTZAPVZDUMBA-UHFFFAOYSA-N CC1=CC=C(CCCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1C Chemical compound CC1=CC=C(CCCC2=NC=NC(C(=O)N3CCC(N4CCC(O)CC4)CC3)=C2C)C=C1C BPXTZAPVZDUMBA-UHFFFAOYSA-N 0.000 description 1
- MQYQKLXZAUOGCP-UHFFFAOYSA-N CC1=CC=C(CCCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1C Chemical compound CC1=CC=C(CCCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1C MQYQKLXZAUOGCP-UHFFFAOYSA-N 0.000 description 1
- DGTRJEYJEQNJOB-UHFFFAOYSA-N CC1=CC=C(CNC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1F Chemical compound CC1=CC=C(CNC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1F DGTRJEYJEQNJOB-UHFFFAOYSA-N 0.000 description 1
- ZDMQDOSPILHFIV-UHFFFAOYSA-N CC1=CC=C(COC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1F Chemical compound CC1=CC=C(COC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1F ZDMQDOSPILHFIV-UHFFFAOYSA-N 0.000 description 1
- UZGCUFICZYGVBM-WDEREUQCSA-N CC1=CC=C([C@@H]2CCC[C@H](C#N)C2)O1 Chemical compound CC1=CC=C([C@@H]2CCC[C@H](C#N)C2)O1 UZGCUFICZYGVBM-WDEREUQCSA-N 0.000 description 1
- CIVRRRJBGHUPLK-HUUCEWRRSA-N CC1=CC=C([C@@H]2CCC[C@H](CCC3=NC=NC(C(=O)O)=C3C)C2)O1 Chemical compound CC1=CC=C([C@@H]2CCC[C@H](CCC3=NC=NC(C(=O)O)=C3C)C2)O1 CIVRRRJBGHUPLK-HUUCEWRRSA-N 0.000 description 1
- OIAPLKBUEZWJCS-NEPJUHHUSA-N CC1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1 Chemical compound CC1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1 OIAPLKBUEZWJCS-NEPJUHHUSA-N 0.000 description 1
- BCHCKGVMOJJBCW-PWSUYJOCSA-N CC1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1F Chemical compound CC1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1F BCHCKGVMOJJBCW-PWSUYJOCSA-N 0.000 description 1
- COYRDOUCWSMXCF-NEPJUHHUSA-N CC1=CC=C([C@@H]2CC[C@H](CN)O2)C=C1 Chemical compound CC1=CC=C([C@@H]2CC[C@H](CN)O2)C=C1 COYRDOUCWSMXCF-NEPJUHHUSA-N 0.000 description 1
- RIYMOCBNKGQNQK-PWSUYJOCSA-N CC1=CC=C([C@@H]2CC[C@H](CN)O2)C=C1F Chemical compound CC1=CC=C([C@@H]2CC[C@H](CN)O2)C=C1F RIYMOCBNKGQNQK-PWSUYJOCSA-N 0.000 description 1
- OLOZHBMWDRXVHT-UIOOFZCWSA-N CC1=CC=C([C@H]2CCC[C@@H](CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)O1 Chemical compound CC1=CC=C([C@H]2CCC[C@@H](CCC3=NC(C)=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)O1 OLOZHBMWDRXVHT-UIOOFZCWSA-N 0.000 description 1
- FRTMDBHNSQVLRF-DQEYMECFSA-N CC1=CC=C([C@H]2CCC[C@@H](CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)O1 Chemical compound CC1=CC=C([C@H]2CCC[C@@H](CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)O1 FRTMDBHNSQVLRF-DQEYMECFSA-N 0.000 description 1
- WAMPCYUWVWNYAK-KGLIPLIRSA-N CC1=CC=C([C@H]2CCC[C@@H](CNC3=NC=NC(C(=O)O)=C3C)C2)O1 Chemical compound CC1=CC=C([C@H]2CCC[C@@H](CNC3=NC=NC(C(=O)O)=C3C)C2)O1 WAMPCYUWVWNYAK-KGLIPLIRSA-N 0.000 description 1
- ONKLASJYJMOOPV-XRKRLSELSA-N CC1=CC=C([C@H]2CC[C@@H](CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 Chemical compound CC1=CC=C([C@H]2CC[C@@H](CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 ONKLASJYJMOOPV-XRKRLSELSA-N 0.000 description 1
- BCHCKGVMOJJBCW-ZYHUDNBSSA-N CC1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1F Chemical compound CC1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1F BCHCKGVMOJJBCW-ZYHUDNBSSA-N 0.000 description 1
- ONKLASJYJMOOPV-LMSSTIIKSA-N CC1=CC=C([C@H]2CC[C@H](CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 Chemical compound CC1=CC=C([C@H]2CC[C@H](CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)O2)C=C1 ONKLASJYJMOOPV-LMSSTIIKSA-N 0.000 description 1
- COYRDOUCWSMXCF-VXGBXAGGSA-N CC1=CC=C([C@H]2CC[C@H](CN)O2)C=C1 Chemical compound CC1=CC=C([C@H]2CC[C@H](CN)O2)C=C1 COYRDOUCWSMXCF-VXGBXAGGSA-N 0.000 description 1
- RIYMOCBNKGQNQK-ZYHUDNBSSA-N CC1=CC=C([C@H]2CC[C@H](CN)O2)C=C1F Chemical compound CC1=CC=C([C@H]2CC[C@H](CN)O2)C=C1F RIYMOCBNKGQNQK-ZYHUDNBSSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N CC1=CC=CC=C1 Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- JZUXUYSQVXBHOS-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(=O)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(=O)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 JZUXUYSQVXBHOS-UHFFFAOYSA-N 0.000 description 1
- AOBVTXIBVNERPG-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC(Cl)=C(Cl)C=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC(Cl)=C(Cl)C=C2)=N1 AOBVTXIBVNERPG-UHFFFAOYSA-N 0.000 description 1
- GXGPGUYIHAFCLM-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 GXGPGUYIHAFCLM-UHFFFAOYSA-N 0.000 description 1
- RCXVLTZGRSRQMT-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(C(F)(F)F)C(Cl)=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(C(F)(F)F)C(Cl)=C2)=N1 RCXVLTZGRSRQMT-UHFFFAOYSA-N 0.000 description 1
- IUNLDKPNEUBENH-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(Cl)C(F)=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(Cl)C(F)=C2)=N1 IUNLDKPNEUBENH-UHFFFAOYSA-N 0.000 description 1
- GZBZADQDNMFFOC-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCC(C3=CC=C(C(F)(F)F)C=C3)O2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCC(C3=CC=C(C(F)(F)F)C=C3)O2)=N1 GZBZADQDNMFFOC-UHFFFAOYSA-N 0.000 description 1
- CTZHTSIRQMDLJH-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCC(C3=CC=CC(C(F)(F)F)=C3)O2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCC(C3=CC=CC(C(F)(F)F)=C3)O2)=N1 CTZHTSIRQMDLJH-UHFFFAOYSA-N 0.000 description 1
- IJUSGBAKWMBZJA-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCCN(C3=CC=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCCN(C3=CC=CC=C3)C2)=N1 IJUSGBAKWMBZJA-UHFFFAOYSA-N 0.000 description 1
- WESLJWQJOJSBTF-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCN(C3=CC=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCN(C3=CC=CC=C3)C2)=N1 WESLJWQJOJSBTF-UHFFFAOYSA-N 0.000 description 1
- GZBZADQDNMFFOC-ZBAATNBSSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CC[C@H](C3=CC=C(C(F)(F)F)C=C3)O2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CC[C@H](C3=CC=C(C(F)(F)F)C=C3)O2)=N1 GZBZADQDNMFFOC-ZBAATNBSSA-N 0.000 description 1
- XMIYVZRXFYPSRX-ZBAATNBSSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CC[C@H](C3=CC=C(Cl)C=C3)O2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CC[C@H](C3=CC=C(Cl)C=C3)O2)=N1 XMIYVZRXFYPSRX-ZBAATNBSSA-N 0.000 description 1
- CTZHTSIRQMDLJH-ZBAATNBSSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CC[C@H](C3=CC=CC(C(F)(F)F)=C3)O2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CC[C@H](C3=CC=CC(C(F)(F)F)=C3)O2)=N1 CTZHTSIRQMDLJH-ZBAATNBSSA-N 0.000 description 1
- AERJDEJCEVLIGH-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2COC3=C(C=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2COC3=C(C=CC=C3)C2)=N1 AERJDEJCEVLIGH-UHFFFAOYSA-N 0.000 description 1
- NTZBLDJGFIFJOB-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(Cl)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(Cl)=N1 NTZBLDJGFIFJOB-UHFFFAOYSA-N 0.000 description 1
- MKZQBEDWSPJXLK-DEOSSOPVSA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(NC[C@@H]2CCN(C3=CC=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(NC[C@@H]2CCN(C3=CC=CC=C3)C2)=N1 MKZQBEDWSPJXLK-DEOSSOPVSA-N 0.000 description 1
- MKZQBEDWSPJXLK-XMMPIXPASA-N CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(NC[C@H]2CCN(C3=CC=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(NC[C@H]2CCN(C3=CC=CC=C3)C2)=N1 MKZQBEDWSPJXLK-XMMPIXPASA-N 0.000 description 1
- GNFDIBWDZBGUGW-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(CC2CCCC(C3=CC=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(CC2CCCC(C3=CC=CC=C3)C2)=N1 GNFDIBWDZBGUGW-UHFFFAOYSA-N 0.000 description 1
- MMRXHLGAGCKCOA-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC(Cl)=C(Cl)C=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC(Cl)=C(Cl)C=C2)=N1 MMRXHLGAGCKCOA-UHFFFAOYSA-N 0.000 description 1
- ZYXVDCVDZUCRRO-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(CCC2COC3=C(C=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(CCC2COC3=C(C=CC=C3)C2)=N1 ZYXVDCVDZUCRRO-UHFFFAOYSA-N 0.000 description 1
- ZOADBELKFSNFTA-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(Cl)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(NS(C)(=O)=O)CC3)CC2)=C(C)C(Cl)=N1 ZOADBELKFSNFTA-UHFFFAOYSA-N 0.000 description 1
- NCQUQQMWGVFFAC-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(O)CC3)CC2)=C(C)C(CCCC2=CC=C(Cl)C(Cl)=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(O)CC3)CC2)=C(C)C(CCCC2=CC=C(Cl)C(Cl)=C2)=N1 NCQUQQMWGVFFAC-UHFFFAOYSA-N 0.000 description 1
- XOIRMBFKGUHVAF-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(O)CC3)CC2)=C(C)C(Cl)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(O)CC3)CC2)=C(C)C(Cl)=N1 XOIRMBFKGUHVAF-UHFFFAOYSA-N 0.000 description 1
- OXJRFYRTWCAYAE-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(O)CC3)CC2)=C(C)C(NCC2=CC=C(Cl)C(Cl)=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(O)CC3)CC2)=C(C)C(NCC2=CC=C(Cl)C(Cl)=C2)=N1 OXJRFYRTWCAYAE-UHFFFAOYSA-N 0.000 description 1
- XXDILFQNHQFWLB-UHFFFAOYSA-N CC1=NC(C(=O)N2CCC(N3CCC(S(=O)(=O)N(C)C)CC3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CCC(S(=O)(=O)N(C)C)CC3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 XXDILFQNHQFWLB-UHFFFAOYSA-N 0.000 description 1
- PIRAPAJXOJZYGI-JOCHJYFZSA-N CC1=NC(C(=O)N2CCC(N3CC[C@@H](C(N)=O)C3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 Chemical compound CC1=NC(C(=O)N2CCC(N3CC[C@@H](C(N)=O)C3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 PIRAPAJXOJZYGI-JOCHJYFZSA-N 0.000 description 1
- QROSEVOQKJIJGE-UHFFFAOYSA-N CC1=NC(C(=O)O)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 Chemical compound CC1=NC(C(=O)O)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 QROSEVOQKJIJGE-UHFFFAOYSA-N 0.000 description 1
- UZFNLEDGWKRORZ-FZNQNYSPSA-N CC1=NC(C(=O)O)=C(C)C(CC[C@H]2C[C@@H](C3=CC=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)O)=C(C)C(CC[C@H]2C[C@@H](C3=CC=CC=C3)C2)=N1 UZFNLEDGWKRORZ-FZNQNYSPSA-N 0.000 description 1
- UZFNLEDGWKRORZ-KOMQPUFPSA-N CC1=NC(C(=O)O)=C(C)C(CC[C@H]2C[C@H](C3=CC=CC=C3)C2)=N1 Chemical compound CC1=NC(C(=O)O)=C(C)C(CC[C@H]2C[C@H](C3=CC=CC=C3)C2)=N1 UZFNLEDGWKRORZ-KOMQPUFPSA-N 0.000 description 1
- LAJRILJDIFUFAF-UHFFFAOYSA-N CC1=NC(Cl)=C(C)C(C(=O)Cl)=N1 Chemical compound CC1=NC(Cl)=C(C)C(C(=O)Cl)=N1 LAJRILJDIFUFAF-UHFFFAOYSA-N 0.000 description 1
- GZBCMTZHTVTOCF-UHFFFAOYSA-N CC1=NC(O)=C(C)C(C(=O)O)=N1 Chemical compound CC1=NC(O)=C(C)C(C(=O)O)=N1 GZBCMTZHTVTOCF-UHFFFAOYSA-N 0.000 description 1
- WXKLZSHXUGYZOV-UHFFFAOYSA-N CC1=NN=C(C)N1C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CC1=NN=C(C)N1C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 WXKLZSHXUGYZOV-UHFFFAOYSA-N 0.000 description 1
- YFUWWCPCYNYQBU-UHFFFAOYSA-N CC1=NOC(C2CCN(C3CCN(C(=O)C4=C(C)C(CCC5=CC=C(C(C)(C)C)C=C5)=NC=N4)CC3)CC2)=N1 Chemical compound CC1=NOC(C2CCN(C3CCN(C(=O)C4=C(C)C(CCC5=CC=C(C(C)(C)C)C=C5)=NC=N4)CC3)CC2)=N1 YFUWWCPCYNYQBU-UHFFFAOYSA-N 0.000 description 1
- HWJJVWXJGMHYKR-UHFFFAOYSA-N CC1CC(N(C)C2CCN(C(=O)OC(C)(C)C)CC2)CC(C)O1 Chemical compound CC1CC(N(C)C2CCN(C(=O)OC(C)(C)C)CC2)CC(C)O1 HWJJVWXJGMHYKR-UHFFFAOYSA-N 0.000 description 1
- ZWOXMCJSWFNOIA-UHFFFAOYSA-N CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC1 Chemical compound CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC1 ZWOXMCJSWFNOIA-UHFFFAOYSA-N 0.000 description 1
- OFXWWIVXCUSYPT-UHFFFAOYSA-N CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)CC1 Chemical compound CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)CC1 OFXWWIVXCUSYPT-UHFFFAOYSA-N 0.000 description 1
- HZELCLFDCWLCER-UHFFFAOYSA-N CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 Chemical compound CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 HZELCLFDCWLCER-UHFFFAOYSA-N 0.000 description 1
- SBZVWQHSBRTORS-UHFFFAOYSA-N CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(OCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CCC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(OCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 SBZVWQHSBRTORS-UHFFFAOYSA-N 0.000 description 1
- QUCPPJDTQZDUJA-UHFFFAOYSA-N CCC(=O)C1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)C1 Chemical compound CCC(=O)C1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)C1 QUCPPJDTQZDUJA-UHFFFAOYSA-N 0.000 description 1
- YXBKUXGFRRUUPZ-UHFFFAOYSA-N CCC(C)NC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CCC(C)NC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 YXBKUXGFRRUUPZ-UHFFFAOYSA-N 0.000 description 1
- SPHMXZOLOQCKAV-UHFFFAOYSA-N CCC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 Chemical compound CCC1=C(C(=O)N2CCC(=O)CC2)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 SPHMXZOLOQCKAV-UHFFFAOYSA-N 0.000 description 1
- GUHFUXQVLPGEFV-UHFFFAOYSA-N CCC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC=CC(C2=CC=CC=C2)=C1 Chemical compound CCC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCC1=CC=CC(C2=CC=CC=C2)=C1 GUHFUXQVLPGEFV-UHFFFAOYSA-N 0.000 description 1
- CRNRLTJRLXCSQW-UHFFFAOYSA-N CCC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CCC1=C(C(=O)N2CCC(N3CCC(O)CC3)CC2)N=CN=C1NCCC1=CC=C(Cl)C(Cl)=C1 CRNRLTJRLXCSQW-UHFFFAOYSA-N 0.000 description 1
- UYRZEBGYNWDAPH-UHFFFAOYSA-N CCC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 Chemical compound CCC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1CCC1=CC(C2=CC=CC=C2)=CC=C1 UYRZEBGYNWDAPH-UHFFFAOYSA-N 0.000 description 1
- WQOUXUMOZBWNNJ-UHFFFAOYSA-N CCC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCCC1=CC=C(Cl)C(Cl)=C1 Chemical compound CCC1=C(C(=O)N2CCC(N3CCOCC3)CC2)N=CN=C1NCCC1=CC=C(Cl)C(Cl)=C1 WQOUXUMOZBWNNJ-UHFFFAOYSA-N 0.000 description 1
- QTZQWJAEFCFEHK-UHFFFAOYSA-N CCC1=C(C(=O)O)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 Chemical compound CCC1=C(C(=O)O)N=CN=C1CCC1=CC=CC(C2=CC=CC=C2)=C1 QTZQWJAEFCFEHK-UHFFFAOYSA-N 0.000 description 1
- XHMDSAOSBXCCNS-UHFFFAOYSA-N CCC1=C(C(=O)O)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 Chemical compound CCC1=C(C(=O)O)N=CN=C1CCCC1=CC(Cl)=C(Cl)C=C1 XHMDSAOSBXCCNS-UHFFFAOYSA-N 0.000 description 1
- DHVXDEXTIZTMLG-UHFFFAOYSA-N CCC1=CC=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1 Chemical compound CCC1=CC=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1 DHVXDEXTIZTMLG-UHFFFAOYSA-N 0.000 description 1
- VGSBATPQQGGPEI-UHFFFAOYSA-N CCC1CCC(CCC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)CC1 Chemical compound CCC1CCC(CCC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)CC1 VGSBATPQQGGPEI-UHFFFAOYSA-N 0.000 description 1
- ZYISIMNZDISIOB-UHFFFAOYSA-N CCN(C1CCN(C(=O)OC(C)(C)C)CC1)S(C)(=O)=O Chemical compound CCN(C1CCN(C(=O)OC(C)(C)C)CC1)S(C)(=O)=O ZYISIMNZDISIOB-UHFFFAOYSA-N 0.000 description 1
- BUBBSQVWFQEWDP-UHFFFAOYSA-N CCN(C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O Chemical compound CCN(C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O BUBBSQVWFQEWDP-UHFFFAOYSA-N 0.000 description 1
- DQOHPCROUJRPMI-UHFFFAOYSA-N CCN(C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O Chemical compound CCN(C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O DQOHPCROUJRPMI-UHFFFAOYSA-N 0.000 description 1
- YGJDYCWESWZEDM-UHFFFAOYSA-N CCN(C1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O Chemical compound CCN(C1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O YGJDYCWESWZEDM-UHFFFAOYSA-N 0.000 description 1
- PHVFJUKZFYXZST-UHFFFAOYSA-N CCN(C1CCNCC1)S(C)(=O)=O.Cl Chemical compound CCN(C1CCNCC1)S(C)(=O)=O.Cl PHVFJUKZFYXZST-UHFFFAOYSA-N 0.000 description 1
- QZMLNNIQRSCEFB-UHFFFAOYSA-N CCNc1c(C)c(C(N(CC2)CCC2NC(OC(C)(C)C)=O)=O)ncn1 Chemical compound CCNc1c(C)c(C(N(CC2)CCC2NC(OC(C)(C)C)=O)=O)ncn1 QZMLNNIQRSCEFB-UHFFFAOYSA-N 0.000 description 1
- IYKMVYGPYOTGKS-JKSUJKDBSA-N CCNc1c(C)c(C(N(CC2)CCC2N[C@@H](CCOC2)[C@@H]2OC)=O)ncn1 Chemical compound CCNc1c(C)c(C(N(CC2)CCC2N[C@@H](CCOC2)[C@@H]2OC)=O)ncn1 IYKMVYGPYOTGKS-JKSUJKDBSA-N 0.000 description 1
- CXGDVIIRFIFULO-UHFFFAOYSA-N CCOC(=O)C1=C(Br)C(CCC2=CC=C(C(C)(C)C)C=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(Br)C(CCC2=CC=C(C(C)(C)C)C=C2)=NC=N1 CXGDVIIRFIFULO-UHFFFAOYSA-N 0.000 description 1
- MPPSMZAYTBYABY-UHFFFAOYSA-N CCOC(=O)C1=C(Br)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(Br)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 MPPSMZAYTBYABY-UHFFFAOYSA-N 0.000 description 1
- UKJBRVQGHGWJIY-NVXWUHKLSA-N CCOC(=O)C1=C(Br)C(CC[C@H]2CCC[C@@H](C3=CC=CC=C3)C2)=NC=N1 Chemical compound CCOC(=O)C1=C(Br)C(CC[C@H]2CCC[C@@H](C3=CC=CC=C3)C2)=NC=N1 UKJBRVQGHGWJIY-NVXWUHKLSA-N 0.000 description 1
- KDKBCWLXRMZVAV-FMIVXFBMSA-N CCOC(=O)C1=C(C)C(/C=C/C2=CC=C(C(C)(C)C)C=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(/C=C/C2=CC=C(C(C)(C)C)C=C2)=NC=N1 KDKBCWLXRMZVAV-FMIVXFBMSA-N 0.000 description 1
- PUHATBIWEREYTF-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CC2=CC=C(C(C)(C)C)C=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CC2=CC=C(C(C)(C)C)C=C2)=NC=N1 PUHATBIWEREYTF-UHFFFAOYSA-N 0.000 description 1
- SSWFSWGJBXMYIR-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CCC2=CC(Cl)=C(Cl)C=C2)=NC=C1 Chemical compound CCOC(=O)C1=C(C)C(CCC2=CC(Cl)=C(Cl)C=C2)=NC=C1 SSWFSWGJBXMYIR-UHFFFAOYSA-N 0.000 description 1
- KQWAKOAWKKBTNS-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=NC(C)=N1 Chemical compound CCOC(=O)C1=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=NC(C)=N1 KQWAKOAWKKBTNS-UHFFFAOYSA-N 0.000 description 1
- BBJAAUHIONZZHV-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CCC2=CC=C(Cl)C(Cl)=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CCC2=CC=C(Cl)C(Cl)=C2)=NC=N1 BBJAAUHIONZZHV-UHFFFAOYSA-N 0.000 description 1
- ARZAWUHZWPHATH-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=CC=C1 Chemical compound CCOC(=O)C1=C(C)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=CC=C1 ARZAWUHZWPHATH-UHFFFAOYSA-N 0.000 description 1
- UKECAIFHIVYUQN-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 UKECAIFHIVYUQN-UHFFFAOYSA-N 0.000 description 1
- MECACDWDVPLIFR-UHFFFAOYSA-N CCOC(=O)C1=C(C)C(CCCC2=CC(Cl)=C(Cl)C=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CCCC2=CC(Cl)=C(Cl)C=C2)=NC=N1 MECACDWDVPLIFR-UHFFFAOYSA-N 0.000 description 1
- HFGUWGCRKHZWKE-IAGOWNOFSA-N CCOC(=O)C1=C(C)C(CC[C@H]2CCC[C@@H](C3=CC=C(C)O3)C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CC[C@H]2CCC[C@@H](C3=CC=C(C)O3)C2)=NC=N1 HFGUWGCRKHZWKE-IAGOWNOFSA-N 0.000 description 1
- JRCJCHKUBWSJCB-IEBWSBKVSA-N CCOC(=O)C1=C(C)C(CC[C@H]2CCC[C@@H](C3=CC=CC=C3)C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CC[C@H]2CCC[C@@H](C3=CC=CC=C3)C2)=NC=N1 JRCJCHKUBWSJCB-IEBWSBKVSA-N 0.000 description 1
- ZFVWWYLFUZSABG-MAEOIBBWSA-N CCOC(=O)C1=C(C)C(CC[C@H]2C[C@@H](C3=CC=CC=C3)C2)=NC(C)=N1 Chemical compound CCOC(=O)C1=C(C)C(CC[C@H]2C[C@@H](C3=CC=CC=C3)C2)=NC(C)=N1 ZFVWWYLFUZSABG-MAEOIBBWSA-N 0.000 description 1
- WIWLXXXXEZBSCM-WOVMCDHWSA-N CCOC(=O)C1=C(C)C(CC[C@H]2C[C@@H](C3=CC=CC=C3)C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CC[C@H]2C[C@@H](C3=CC=CC=C3)C2)=NC=N1 WIWLXXXXEZBSCM-WOVMCDHWSA-N 0.000 description 1
- ZFVWWYLFUZSABG-SAABIXHNSA-N CCOC(=O)C1=C(C)C(CC[C@H]2C[C@H](C3=CC=CC=C3)C2)=NC(C)=N1 Chemical compound CCOC(=O)C1=C(C)C(CC[C@H]2C[C@H](C3=CC=CC=C3)C2)=NC(C)=N1 ZFVWWYLFUZSABG-SAABIXHNSA-N 0.000 description 1
- WIWLXXXXEZBSCM-JCNLHEQBSA-N CCOC(=O)C1=C(C)C(CC[C@H]2C[C@H](C3=CC=CC=C3)C2)=NC=N1 Chemical compound CCOC(=O)C1=C(C)C(CC[C@H]2C[C@H](C3=CC=CC=C3)C2)=NC=N1 WIWLXXXXEZBSCM-JCNLHEQBSA-N 0.000 description 1
- KJIAODWXWIMKQZ-UHFFFAOYSA-N CCOC(=O)C1=C(CC)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(CC)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 KJIAODWXWIMKQZ-UHFFFAOYSA-N 0.000 description 1
- VUSNHZIRXOCOCQ-UHFFFAOYSA-N CCOC(=O)C1=C(CC)C(CCCC2=CC(Cl)=C(Cl)C=C2)=NC=N1 Chemical compound CCOC(=O)C1=C(CC)C(CCCC2=CC(Cl)=C(Cl)C=C2)=NC=N1 VUSNHZIRXOCOCQ-UHFFFAOYSA-N 0.000 description 1
- PFJNNQORFKVGNM-UHFFFAOYSA-N CCOC(=O)C1=NC(C)=NC(Cl)=C1C Chemical compound CCOC(=O)C1=NC(C)=NC(Cl)=C1C PFJNNQORFKVGNM-UHFFFAOYSA-N 0.000 description 1
- SUXXMMJXOBCYRK-UHFFFAOYSA-N CCOC(=O)C1=NC=NC(Cl)=C1Br Chemical compound CCOC(=O)C1=NC=NC(Cl)=C1Br SUXXMMJXOBCYRK-UHFFFAOYSA-N 0.000 description 1
- CRWGVNPMHWCPJG-UHFFFAOYSA-N CCOC(=O)C1=NC=NC(Cl)=C1C Chemical compound CCOC(=O)C1=NC=NC(Cl)=C1C CRWGVNPMHWCPJG-UHFFFAOYSA-N 0.000 description 1
- DLGNJCDPGOWJCV-UHFFFAOYSA-N CCOC(=O)C1=NC=NC(Cl)=C1CC Chemical compound CCOC(=O)C1=NC=NC(Cl)=C1CC DLGNJCDPGOWJCV-UHFFFAOYSA-N 0.000 description 1
- YJAWAYQXMXPZFY-UHFFFAOYSA-N CCOC(=O)C1=NC=NC(O)=C1CC Chemical compound CCOC(=O)C1=NC=NC(O)=C1CC YJAWAYQXMXPZFY-UHFFFAOYSA-N 0.000 description 1
- WKDAAJNKWPGTBU-UHFFFAOYSA-N CCOC(=O)N1CCC(N2CCC(N(C)S(C)(=O)=O)CC2)C(OC)C1 Chemical compound CCOC(=O)N1CCC(N2CCC(N(C)S(C)(=O)=O)CC2)C(OC)C1 WKDAAJNKWPGTBU-UHFFFAOYSA-N 0.000 description 1
- XCANIDFCGHYXOL-UHFFFAOYSA-N CCOC(=O)N1CCC(NC2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C(OC)C1 Chemical compound CCOC(=O)N1CCC(NC2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C(OC)C1 XCANIDFCGHYXOL-UHFFFAOYSA-N 0.000 description 1
- QFMSXDUXEHZAPU-UHUGOGIASA-N CCOC(c(ncnc1NCC(CCC2)C[C@@H]2c2ccccc2)c1C#C)=O Chemical compound CCOC(c(ncnc1NCC(CCC2)C[C@@H]2c2ccccc2)c1C#C)=O QFMSXDUXEHZAPU-UHUGOGIASA-N 0.000 description 1
- AJKXDNGNIVSLAB-FUHWJXTLSA-N CCOC(c1c(C)c(NC[C@@H](CCC2)C[C@@H]2c2ccccc2)ncn1)=O Chemical compound CCOC(c1c(C)c(NC[C@@H](CCC2)C[C@@H]2c2ccccc2)ncn1)=O AJKXDNGNIVSLAB-FUHWJXTLSA-N 0.000 description 1
- GTJGXPSTHVTMMK-UHFFFAOYSA-N CCOC(c1ncnc(NCC(C2)CC2c2ccccc2)c1C)=O Chemical compound CCOC(c1ncnc(NCC(C2)CC2c2ccccc2)c1C)=O GTJGXPSTHVTMMK-UHFFFAOYSA-N 0.000 description 1
- HRKQSPQSTQLOMX-UHFFFAOYSA-N CCOC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CCOC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 HRKQSPQSTQLOMX-UHFFFAOYSA-N 0.000 description 1
- WUSUOAGDUFTOLD-UHFFFAOYSA-N CCS(=O)(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC1 WUSUOAGDUFTOLD-UHFFFAOYSA-N 0.000 description 1
- FVXWVGLBWTUVOG-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 FVXWVGLBWTUVOG-UHFFFAOYSA-N 0.000 description 1
- DOBVWYJXBCDTAX-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 DOBVWYJXBCDTAX-UHFFFAOYSA-N 0.000 description 1
- LALRGLWJXFHLSU-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 LALRGLWJXFHLSU-UHFFFAOYSA-N 0.000 description 1
- SAFJSIJPFRGSNU-SQHAQQRYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CC[C@@H]4C[C@H]4C4=CC=CC=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CC[C@@H]4C[C@H]4C4=CC=CC=C4)=NC=N3)CC2)CC1 SAFJSIJPFRGSNU-SQHAQQRYSA-N 0.000 description 1
- DOJKXADZPXLBBI-VWLOTQADSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CC[C@H]4CCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(CC[C@H]4CCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 DOJKXADZPXLBBI-VWLOTQADSA-N 0.000 description 1
- AUSVKNPJDPZITA-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)CC1 AUSVKNPJDPZITA-UHFFFAOYSA-N 0.000 description 1
- LOWVLLKXUNGYJX-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC(Cl)=C(C(F)(F)F)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC(Cl)=C(C(F)(F)F)C=C4)=NC=N3)CC2)CC1 LOWVLLKXUNGYJX-UHFFFAOYSA-N 0.000 description 1
- LWKSNIPHFKWULG-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC(F)=C(Cl)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC(F)=C(Cl)C=C4)=NC=N3)CC2)CC1 LWKSNIPHFKWULG-UHFFFAOYSA-N 0.000 description 1
- LYUDMLYJODEFKK-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC=C(C(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC=C(C(C)C)C=C4)=NC=N3)CC2)CC1 LYUDMLYJODEFKK-UHFFFAOYSA-N 0.000 description 1
- TWSNSDDVDDPHJF-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC=C(C)C(Cl)=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4=CC=C(C)C(Cl)=C4)=NC=N3)CC2)CC1 TWSNSDDVDDPHJF-UHFFFAOYSA-N 0.000 description 1
- CSWHYRUJEXXSSO-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 CSWHYRUJEXXSSO-UHFFFAOYSA-N 0.000 description 1
- OAHZSWLZIKUWKH-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCN(C5=CC=CC=C5)CC4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)C3=C(C)C(NCC4CCN(C5=CC=CC=C5)CC4)=NC=N3)CC2)CC1 OAHZSWLZIKUWKH-UHFFFAOYSA-N 0.000 description 1
- FYONUGJLBCSAPI-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 FYONUGJLBCSAPI-UHFFFAOYSA-N 0.000 description 1
- RMJNEIYIUHXVDG-UHFFFAOYSA-N CCS(=O)(=O)N(C)C1CCN(C2CCNCC2)CC1.Cl.Cl Chemical compound CCS(=O)(=O)N(C)C1CCN(C2CCNCC2)CC1.Cl.Cl RMJNEIYIUHXVDG-UHFFFAOYSA-N 0.000 description 1
- IUJHWBLCFYIRDE-UHFFFAOYSA-N CCS(=O)(=O)NC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)NC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC1 IUJHWBLCFYIRDE-UHFFFAOYSA-N 0.000 description 1
- ACEVLPHKMIFGBP-UHFFFAOYSA-N CCS(=O)(=O)NC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CCS(=O)(=O)NC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 ACEVLPHKMIFGBP-UHFFFAOYSA-N 0.000 description 1
- ZKCTUOXPXAKXQO-UHFFFAOYSA-N CCS(=O)(=O)NC1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 Chemical compound CCS(=O)(=O)NC1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 ZKCTUOXPXAKXQO-UHFFFAOYSA-N 0.000 description 1
- CPVYMGVWAACXLM-UHFFFAOYSA-N CCS(=O)(=O)NC1CCN(C2CCNCC2)CC1.Cl.Cl Chemical compound CCS(=O)(=O)NC1CCN(C2CCNCC2)CC1.Cl.Cl CPVYMGVWAACXLM-UHFFFAOYSA-N 0.000 description 1
- GCCNZNZPYQPBAO-UHFFFAOYSA-N CCS(NC(CC1)CCN1C(CC1)CCN1C(c1ncnc(NCc2ccc(C(C)(C)C)cc2)c1C)=O)(=O)=O Chemical compound CCS(NC(CC1)CCN1C(CC1)CCN1C(c1ncnc(NCc2ccc(C(C)(C)C)cc2)c1C)=O)(=O)=O GCCNZNZPYQPBAO-UHFFFAOYSA-N 0.000 description 1
- RWCOCSKNBIRHAT-UHFFFAOYSA-N CCc1c(C(N(CC2)CCC2=O)=O)ncnc1NCc1cccc(-c2ccccc2)c1 Chemical compound CCc1c(C(N(CC2)CCC2=O)=O)ncnc1NCc1cccc(-c2ccccc2)c1 RWCOCSKNBIRHAT-UHFFFAOYSA-N 0.000 description 1
- GAQGFHFXQVQEHZ-UHFFFAOYSA-N CN(C1CCN(C(=O)OC(C)(C)C)CC1)C1CCC(F)(F)CC1 Chemical compound CN(C1CCN(C(=O)OC(C)(C)C)CC1)C1CCC(F)(F)CC1 GAQGFHFXQVQEHZ-UHFFFAOYSA-N 0.000 description 1
- UAIUXCJJMPMLCJ-UHFFFAOYSA-N CN(C1CCN(C2CCN(C(=O)C3=C(C#N)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O Chemical compound CN(C1CCN(C2CCN(C(=O)C3=C(C#N)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1)S(C)(=O)=O UAIUXCJJMPMLCJ-UHFFFAOYSA-N 0.000 description 1
- UDGZZOMOCXWXHD-UHFFFAOYSA-N CN(C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1)S(C)(=O)=O Chemical compound CN(C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1)S(C)(=O)=O UDGZZOMOCXWXHD-UHFFFAOYSA-N 0.000 description 1
- NRBBFGVONYTRLZ-UHFFFAOYSA-N CN(C1CCN(C2CCNCC2)CC1)S(C)(=O)=O.Cl.Cl Chemical compound CN(C1CCN(C2CCNCC2)CC1)S(C)(=O)=O.Cl.Cl NRBBFGVONYTRLZ-UHFFFAOYSA-N 0.000 description 1
- ZWBMOWRNBORDOR-UHFFFAOYSA-N CN(C1CCNCC1)C1CCC(F)(F)CC1.Cl.Cl Chemical compound CN(C1CCNCC1)C1CCC(F)(F)CC1.Cl.Cl ZWBMOWRNBORDOR-UHFFFAOYSA-N 0.000 description 1
- QQWAERSFSGQLKL-UHFFFAOYSA-N CN(C1CCNCC1)C1CCOCC1.Cl.Cl Chemical compound CN(C1CCNCC1)C1CCOCC1.Cl.Cl QQWAERSFSGQLKL-UHFFFAOYSA-N 0.000 description 1
- JYVJIRQBIKCZGN-UHFFFAOYSA-N CN(C1CCOCC1)C1CCN(C(=O)OC(C)(C)C)CC1 Chemical compound CN(C1CCOCC1)C1CCN(C(=O)OC(C)(C)C)CC1 JYVJIRQBIKCZGN-UHFFFAOYSA-N 0.000 description 1
- CSHRHPUAGMQSEA-UHFFFAOYSA-N CNC(=O)C1(C)CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CNC(=O)C1(C)CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 CSHRHPUAGMQSEA-UHFFFAOYSA-N 0.000 description 1
- JWRQQDSKIZPEJJ-UHFFFAOYSA-N CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 JWRQQDSKIZPEJJ-UHFFFAOYSA-N 0.000 description 1
- HWOSDWIFEOVPIT-UHFFFAOYSA-N CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(Cl)C=C5)C4)=NC=N3)CC2)CC1 Chemical compound CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(Cl)C=C5)C4)=NC=N3)CC2)CC1 HWOSDWIFEOVPIT-UHFFFAOYSA-N 0.000 description 1
- AUPSNQUYWXPGPW-UHFFFAOYSA-N CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(F)C=C5)C4)=NC=N3)CC2)CC1 Chemical compound CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(F)C=C5)C4)=NC=N3)CC2)CC1 AUPSNQUYWXPGPW-UHFFFAOYSA-N 0.000 description 1
- VPHQXWUEAKPQNG-UHFFFAOYSA-N CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 Chemical compound CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 VPHQXWUEAKPQNG-UHFFFAOYSA-N 0.000 description 1
- VPHQXWUEAKPQNG-SHQCIBLASA-N CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CC[C@H]4CCC[C@@H](C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 Chemical compound CNC(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CC[C@H]4CCC[C@@H](C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 VPHQXWUEAKPQNG-SHQCIBLASA-N 0.000 description 1
- AUCAOSBLEPTXMZ-UHFFFAOYSA-N CNC(=O)C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 Chemical compound CNC(=O)C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 AUCAOSBLEPTXMZ-UHFFFAOYSA-N 0.000 description 1
- SHFVWIWDUNKONN-UHFFFAOYSA-N CNC(=O)C1CCN(C2CCNCC2)CC1.Cl.Cl Chemical compound CNC(=O)C1CCN(C2CCNCC2)CC1.Cl.Cl SHFVWIWDUNKONN-UHFFFAOYSA-N 0.000 description 1
- RYCKDNKXNCVJKM-VWLOTQADSA-N CNC(=O)C[C@@H]1CCCN1C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound CNC(=O)C[C@@H]1CCCN1C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 RYCKDNKXNCVJKM-VWLOTQADSA-N 0.000 description 1
- RYCKDNKXNCVJKM-RUZDIDTESA-N CNC(=O)C[C@H]1CCCN1C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound CNC(=O)C[C@H]1CCCN1C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 RYCKDNKXNCVJKM-RUZDIDTESA-N 0.000 description 1
- JOVLQLPSCZTMSR-GOSISDBHSA-N CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(F)(F)F)C(Cl)=C4)=NC=N3)CC2)C1 Chemical compound CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(F)(F)F)C(Cl)=C4)=NC=N3)CC2)C1 JOVLQLPSCZTMSR-GOSISDBHSA-N 0.000 description 1
- XHDQHGFVMDZLGF-GOSISDBHSA-N CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)C1 Chemical compound CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)C1 XHDQHGFVMDZLGF-GOSISDBHSA-N 0.000 description 1
- ONMQKUQHUIFOFX-GOSISDBHSA-N CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(F)=C4)=NC=N3)CC2)C1 Chemical compound CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(F)=C4)=NC=N3)CC2)C1 ONMQKUQHUIFOFX-GOSISDBHSA-N 0.000 description 1
- QXZFICHPWCOKMS-GFCCVEGCSA-N CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)C1 Chemical compound CNC(=O)[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)C1 QXZFICHPWCOKMS-GFCCVEGCSA-N 0.000 description 1
- FRNMVLYXFCRTFS-GFCCVEGCSA-N CNC(=O)[C@@H]1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)C1 Chemical compound CNC(=O)[C@@H]1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)C1 FRNMVLYXFCRTFS-GFCCVEGCSA-N 0.000 description 1
- ADVWTGFITIARAM-SECBINFHSA-N CNC(=O)[C@@H]1CCN(C2CCNCC2)C1.Cl.Cl Chemical compound CNC(=O)[C@@H]1CCN(C2CCNCC2)C1.Cl.Cl ADVWTGFITIARAM-SECBINFHSA-N 0.000 description 1
- VUANAZOYRLIYPQ-FQEVSTJZSA-N CNC(=O)[C@H]1CCCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)C1 Chemical compound CNC(=O)[C@H]1CCCN(C2CCN(C(=O)C3=C(C)C(CCCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)C1 VUANAZOYRLIYPQ-FQEVSTJZSA-N 0.000 description 1
- XHDQHGFVMDZLGF-SFHVURJKSA-N CNC(=O)[C@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)C1 Chemical compound CNC(=O)[C@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)C1 XHDQHGFVMDZLGF-SFHVURJKSA-N 0.000 description 1
- FRNMVLYXFCRTFS-LBPRGKRZSA-N CNC(=O)[C@H]1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)C1 Chemical compound CNC(=O)[C@H]1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)C1 FRNMVLYXFCRTFS-LBPRGKRZSA-N 0.000 description 1
- ADVWTGFITIARAM-VIFPVBQESA-N CNC(=O)[C@H]1CCN(C2CCNCC2)C1.Cl.Cl Chemical compound CNC(=O)[C@H]1CCN(C2CCNCC2)C1.Cl.Cl ADVWTGFITIARAM-VIFPVBQESA-N 0.000 description 1
- CGCRUUYENIJCDB-UHFFFAOYSA-N CNS(=O)(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC(C)=N3)CC2)CC1 Chemical compound CNS(=O)(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC(C)=N3)CC2)CC1 CGCRUUYENIJCDB-UHFFFAOYSA-N 0.000 description 1
- SVEMIGIGZXBOFO-UHFFFAOYSA-N CNS(=O)(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound CNS(=O)(=O)C1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 SVEMIGIGZXBOFO-UHFFFAOYSA-N 0.000 description 1
- ZGEWLZUWNAFBJR-UHFFFAOYSA-N CNS(=O)(=O)C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 Chemical compound CNS(=O)(=O)C1CCN(C2CCN(C(=O)OC(C)(C)C)CC2)CC1 ZGEWLZUWNAFBJR-UHFFFAOYSA-N 0.000 description 1
- SIUWKCHFXBJGBP-UHFFFAOYSA-N CNS(=O)(=O)C1CCN(C2CCNCC2)CC1.Cl.Cl Chemical compound CNS(=O)(=O)C1CCN(C2CCNCC2)CC1.Cl.Cl SIUWKCHFXBJGBP-UHFFFAOYSA-N 0.000 description 1
- GRAUAIMXHCNYPE-UHFFFAOYSA-N COC(COCC1)C1NC1CCNCC1 Chemical compound COC(COCC1)C1NC1CCNCC1 GRAUAIMXHCNYPE-UHFFFAOYSA-N 0.000 description 1
- SEVBEUZYGBYQIJ-UHFFFAOYSA-N COC1(OC)CCC(F)(F)CC1O Chemical compound COC1(OC)CCC(F)(F)CC1O SEVBEUZYGBYQIJ-UHFFFAOYSA-N 0.000 description 1
- FPSZYZQWFXXYRZ-UHFFFAOYSA-N COC1=CC=C(C2CCCC(C#N)C2)C=C1 Chemical compound COC1=CC=C(C2CCCC(C#N)C2)C=C1 FPSZYZQWFXXYRZ-UHFFFAOYSA-N 0.000 description 1
- JGIVZQIZZYLCRY-UHFFFAOYSA-N COC1=CC=C(C2CCCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)C=C1 Chemical compound COC1=CC=C(C2CCCC(CCC3=NC=NC(C(=O)N4CCC(N5CCC(N(C)S(C)(=O)=O)CC5)CC4)=C3C)C2)C=C1 JGIVZQIZZYLCRY-UHFFFAOYSA-N 0.000 description 1
- UUTJWGJVKMHYEJ-UHFFFAOYSA-N COC1=CC=C(C2CCCC(CN)C2)C=C1 Chemical compound COC1=CC=C(C2CCCC(CN)C2)C=C1 UUTJWGJVKMHYEJ-UHFFFAOYSA-N 0.000 description 1
- YJEGCTFFNAFSAS-UHFFFAOYSA-N COC1=CC=C(CCCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1Cl Chemical compound COC1=CC=C(CCCC2=NC=NC(C(=O)N3CCC(N4CCCCC4)CC3)=C2C)C=C1Cl YJEGCTFFNAFSAS-UHFFFAOYSA-N 0.000 description 1
- VSDDLGUVRMHRPX-UHFFFAOYSA-N COC1=CC=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1 Chemical compound COC1=CC=C(CNC2=NC=NC(C(=O)N3CCC(N4CCC(N(C)S(C)(=O)=O)CC4)CC3)=C2C)C=C1 VSDDLGUVRMHRPX-UHFFFAOYSA-N 0.000 description 1
- QAFGEJXBBXLWAD-UHFFFAOYSA-N COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 Chemical compound COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2=CC=C(C(C)(C)C)C=C2)=N1 QAFGEJXBBXLWAD-UHFFFAOYSA-N 0.000 description 1
- GWDKPEABPZVQES-UHFFFAOYSA-N COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCCC(C3=CC=CC=C3)C2)=N1 Chemical compound COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(CCC2CCCC(C3=CC=CC=C3)C2)=N1 GWDKPEABPZVQES-UHFFFAOYSA-N 0.000 description 1
- VQHMVMKUNSYJRR-UHFFFAOYSA-N COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(OCC2=CC=C(C(C)(C)C)C=C2)=N1 Chemical compound COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(OCC2=CC=C(C(C)(C)C)C=C2)=N1 VQHMVMKUNSYJRR-UHFFFAOYSA-N 0.000 description 1
- RSTOJJUKQLKEAN-UHFFFAOYSA-N COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(OCC2CCCC(C3=CC=CC=C3)C2)=N1 Chemical compound COC1=NC(C(=O)N2CCC(N3CCC(N(C)S(C)(=O)=O)CC3)CC2)=C(C)C(OCC2CCCC(C3=CC=CC=C3)C2)=N1 RSTOJJUKQLKEAN-UHFFFAOYSA-N 0.000 description 1
- BMPKNYPFSUGDPV-UHFFFAOYSA-N COC1=NC(Cl)=C(C)C(C(=O)Cl)=N1 Chemical compound COC1=NC(Cl)=C(C)C(C(=O)Cl)=N1 BMPKNYPFSUGDPV-UHFFFAOYSA-N 0.000 description 1
- MZZPEMJUOUZOIP-UHFFFAOYSA-N COC1=NC(O)=C(C)C(C(=O)O)=N1 Chemical compound COC1=NC(O)=C(C)C(C(=O)O)=N1 MZZPEMJUOUZOIP-UHFFFAOYSA-N 0.000 description 1
- QVSTZWZQKNVRHW-UHFFFAOYSA-N COC1CC(F)(F)CCC1=O Chemical compound COC1CC(F)(F)CCC1=O QVSTZWZQKNVRHW-UHFFFAOYSA-N 0.000 description 1
- NHYJCTFAQYJIAR-UHFFFAOYSA-N COC1CC(F)(F)CCC1NC1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound COC1CC(F)(F)CCC1NC1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 NHYJCTFAQYJIAR-UHFFFAOYSA-N 0.000 description 1
- XXMCBNSEXYEUIL-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(F)=C(Cl)C=C4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(F)=C(Cl)C=C4)=NC=N3)CC2)CC1 XXMCBNSEXYEUIL-UHFFFAOYSA-N 0.000 description 1
- JBUWRHPVMSVXFO-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)CC1 JBUWRHPVMSVXFO-UHFFFAOYSA-N 0.000 description 1
- YEXVVPTWXKTZDS-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)C)C=C4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)C)C=C4)=NC=N3)CC2)CC1 YEXVVPTWXKTZDS-UHFFFAOYSA-N 0.000 description 1
- RFTYYIKBROAEHO-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C)C(Cl)=C4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C)C(Cl)=C4)=NC=N3)CC2)CC1 RFTYYIKBROAEHO-UHFFFAOYSA-N 0.000 description 1
- VTVCQBHGOOVSDA-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(Cl)C=C5)C4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(Cl)C=C5)C4)=NC=N3)CC2)CC1 VTVCQBHGOOVSDA-UHFFFAOYSA-N 0.000 description 1
- SMEAZMOBAKMWNY-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(F)C=C5)C4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCC(C5=CC=C(F)C=C5)C4)=NC=N3)CC2)CC1 SMEAZMOBAKMWNY-UHFFFAOYSA-N 0.000 description 1
- QQRRJHMOQWUFPH-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(CCC4CCCN(C5=CC=CC=C5)C4)=NC=N3)CC2)CC1 QQRRJHMOQWUFPH-UHFFFAOYSA-N 0.000 description 1
- RPEYNLQHXZJSHH-UHFFFAOYSA-N COC1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)CC1 Chemical compound COC1CCN(C2CCN(C(=O)C3=C(C)C(Cl)=NC=N3)CC2)CC1 RPEYNLQHXZJSHH-UHFFFAOYSA-N 0.000 description 1
- NSGZWBDEBFCXKP-UHFFFAOYSA-N COC1CN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CCC1N1CCC(N(C)S(C)(=O)=O)CC1 Chemical compound COC1CN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CCC1N1CCC(N(C)S(C)(=O)=O)CC1 NSGZWBDEBFCXKP-UHFFFAOYSA-N 0.000 description 1
- MQZAJJBGHQBFFC-UHFFFAOYSA-N COC1CNCCC1N1CCC(N(C)S(C)(=O)=O)CC1 Chemical compound COC1CNCCC1N1CCC(N(C)S(C)(=O)=O)CC1 MQZAJJBGHQBFFC-UHFFFAOYSA-N 0.000 description 1
- GYOAUMVMZFXBHJ-UHFFFAOYSA-N COC1COCCC1CC1CCN(C(=O)C2=C(C)C(NCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound COC1COCCC1CC1CCN(C(=O)C2=C(C)C(NCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 GYOAUMVMZFXBHJ-UHFFFAOYSA-N 0.000 description 1
- JMEJXLFKLYEQEW-UHFFFAOYSA-N COC1COCCC1CC1CCN(C(=O)OC(C)(C)C)CC1 Chemical compound COC1COCCC1CC1CCN(C(=O)OC(C)(C)C)CC1 JMEJXLFKLYEQEW-UHFFFAOYSA-N 0.000 description 1
- XBFRKUZZSJGCEM-UHFFFAOYSA-N COC1COCCC1CC1CCNCC1.Cl.Cl Chemical compound COC1COCCC1CC1CCNCC1.Cl.Cl XBFRKUZZSJGCEM-UHFFFAOYSA-N 0.000 description 1
- AFXRONKCCGCZMW-UHFFFAOYSA-N COC1COCCC1N(C)C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound COC1COCCC1N(C)C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 AFXRONKCCGCZMW-UHFFFAOYSA-N 0.000 description 1
- XTFUZUVOFWYYEO-ZJFQCHHHSA-N COC1COCCC1N(C)C1CCN(C(=O)C2=C(C)C(CCC3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound COC1COCCC1N(C)C1CCN(C(=O)C2=C(C)C(CCC3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 XTFUZUVOFWYYEO-ZJFQCHHHSA-N 0.000 description 1
- XTFUZUVOFWYYEO-ULUKWQSDSA-N COC1COCCC1N(C)C1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound COC1COCCC1N(C)C1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 XTFUZUVOFWYYEO-ULUKWQSDSA-N 0.000 description 1
- JKCZSTWPLKUWBV-UHFFFAOYSA-N COC1COCCC1N(C)C1CCN(C(=O)OC(C)(C)C)CC1 Chemical compound COC1COCCC1N(C)C1CCN(C(=O)OC(C)(C)C)CC1 JKCZSTWPLKUWBV-UHFFFAOYSA-N 0.000 description 1
- RIOUPQKWBBAGHH-UHFFFAOYSA-N COC1COCCC1N(C)C1CCNCC1.Cl.Cl Chemical compound COC1COCCC1N(C)C1CCNCC1.Cl.Cl RIOUPQKWBBAGHH-UHFFFAOYSA-N 0.000 description 1
- MYCBGPCAGQFHGW-UHFFFAOYSA-N COC1COCCC1NC1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound COC1COCCC1NC1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 MYCBGPCAGQFHGW-UHFFFAOYSA-N 0.000 description 1
- IGNQUJPJHBQASF-UHFFFAOYSA-N COC1COCCC1NC1CCN(C(=O)C2=C(C)C(CCC3CC4=C(C=CC=C4)C3)=NC=N2)CC1 Chemical compound COC1COCCC1NC1CCN(C(=O)C2=C(C)C(CCC3CC4=C(C=CC=C4)C3)=NC=N2)CC1 IGNQUJPJHBQASF-UHFFFAOYSA-N 0.000 description 1
- KLHXGNOPMSZTNN-KPJQKESBSA-N COC1COCCC1NC1CCN(C(=O)C2=C(C)C(CCC3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound COC1COCCC1NC1CCN(C(=O)C2=C(C)C(CCC3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 KLHXGNOPMSZTNN-KPJQKESBSA-N 0.000 description 1
- HVBKVTIHLMKCBT-UHFFFAOYSA-N COC1COCCC1NC1CCN(C(=O)C2=C(C)C(Cl)=NC=N2)CC1 Chemical compound COC1COCCC1NC1CCN(C(=O)C2=C(C)C(Cl)=NC=N2)CC1 HVBKVTIHLMKCBT-UHFFFAOYSA-N 0.000 description 1
- LFMZKTSAOOQAHM-UHFFFAOYSA-N COC1COCCC1NC1CCN(C(=O)C2=C(C)C(NC3CC4=C(C=CC=C4)C3)=NC=N2)CC1 Chemical compound COC1COCCC1NC1CCN(C(=O)C2=C(C)C(NC3CC4=C(C=CC=C4)C3)=NC=N2)CC1 LFMZKTSAOOQAHM-UHFFFAOYSA-N 0.000 description 1
- UMCMLXBSAFDLCP-UHFFFAOYSA-N COC1COCCC1NC1CCN(C(=O)C2=C(C)C(NCC3CCCCC3)=NC=N2)CC1 Chemical compound COC1COCCC1NC1CCN(C(=O)C2=C(C)C(NCC3CCCCC3)=NC=N2)CC1 UMCMLXBSAFDLCP-UHFFFAOYSA-N 0.000 description 1
- BLLXSQHXISRQJP-UHFFFAOYSA-N COCCN(C)C1CCN(C(=O)C2=C(C)C(NCC3=CC(Cl)=C(Cl)C=C3)=NC=N2)CC1 Chemical compound COCCN(C)C1CCN(C(=O)C2=C(C)C(NCC3=CC(Cl)=C(Cl)C=C3)=NC=N2)CC1 BLLXSQHXISRQJP-UHFFFAOYSA-N 0.000 description 1
- ANPXXYGTFCOHAA-UHFFFAOYSA-N COCCN1N=CC2CCN(C3CCN(C(=O)C4=C(C)C(CCC5=CC=C(C(C)(C)C)C=C5)=NC=N4)CC3)CC21 Chemical compound COCCN1N=CC2CCN(C3CCN(C(=O)C4=C(C)C(CCC5=CC=C(C(C)(C)C)C=C5)=NC=N4)CC3)CC21 ANPXXYGTFCOHAA-UHFFFAOYSA-N 0.000 description 1
- KPHLAFOGEWRIRI-XMMPIXPASA-N CO[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C1 Chemical compound CO[C@@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C1 KPHLAFOGEWRIRI-XMMPIXPASA-N 0.000 description 1
- CQAIZYFWDYKFQI-GHMZBOCLSA-N CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1N(C)S(C)(=O)=O Chemical compound CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1N(C)S(C)(=O)=O CQAIZYFWDYKFQI-GHMZBOCLSA-N 0.000 description 1
- QJUBDGJWFFUOBE-NXEZZACHSA-N CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1NS(C)(=O)=O Chemical compound CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1NS(C)(=O)=O QJUBDGJWFFUOBE-NXEZZACHSA-N 0.000 description 1
- COSMAAFCGGXAIG-NBGIEHNGSA-N CO[C@@H]1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC[C@H]1CS(C)(=O)=O Chemical compound CO[C@@H]1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC[C@H]1CS(C)(=O)=O COSMAAFCGGXAIG-NBGIEHNGSA-N 0.000 description 1
- REGYSSGYROZKEJ-JWQCQUIFSA-N CO[C@@H]1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC[C@H]1N(C)S(C)(=O)=O Chemical compound CO[C@@H]1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(Cl)C(Cl)=C4)=NC=N3)CC2)CC[C@H]1N(C)S(C)(=O)=O REGYSSGYROZKEJ-JWQCQUIFSA-N 0.000 description 1
- APCJNIJAUFBQHQ-GOEBONIOSA-N CO[C@@H]1CN(C2CCN(C(=O)OC(C)(C)C)CC2)CC[C@H]1CS(C)(=O)=O Chemical compound CO[C@@H]1CN(C2CCN(C(=O)OC(C)(C)C)CC2)CC[C@H]1CS(C)(=O)=O APCJNIJAUFBQHQ-GOEBONIOSA-N 0.000 description 1
- QAQAPFAXBXKGAG-WCQYABFASA-N CO[C@@H]1CN(C2CCNCC2)CC[C@H]1CS(C)(=O)=O.Cl.Cl Chemical compound CO[C@@H]1CN(C2CCNCC2)CC[C@H]1CS(C)(=O)=O.Cl.Cl QAQAPFAXBXKGAG-WCQYABFASA-N 0.000 description 1
- MBDYXFJFDISVRD-HTQZYQBOSA-N CO[C@@H]1CNCC[C@H]1N(C)S(C)(=O)=O.Cl Chemical compound CO[C@@H]1CNCC[C@H]1N(C)S(C)(=O)=O.Cl MBDYXFJFDISVRD-HTQZYQBOSA-N 0.000 description 1
- AFXRONKCCGCZMW-RRPNLBNLSA-N CO[C@@H]1COCC[C@@H]1N(C)C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1N(C)C1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 AFXRONKCCGCZMW-RRPNLBNLSA-N 0.000 description 1
- MYCBGPCAGQFHGW-IZZNHLLZSA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 MYCBGPCAGQFHGW-IZZNHLLZSA-N 0.000 description 1
- PKDMTEVFERIIGI-BKTBCGHXSA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@@H]3CCC[C@H](C4=CC=C(C)O4)C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@@H]3CCC[C@H](C4=CC=C(C)O4)C3)=NC=N2)CC1 PKDMTEVFERIIGI-BKTBCGHXSA-N 0.000 description 1
- PKDMTEVFERIIGI-PKFNMVSESA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=C(C)O4)C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=C(C)O4)C3)=NC=N2)CC1 PKDMTEVFERIIGI-PKFNMVSESA-N 0.000 description 1
- KLHXGNOPMSZTNN-ADTKTOCISA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 KLHXGNOPMSZTNN-ADTKTOCISA-N 0.000 description 1
- JZOXYHAIBAFMTD-ZNSCEPEASA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@@H](C4=CC=CC=C4)C3)=NC(C)=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@@H](C4=CC=CC=C4)C3)=NC(C)=N2)CC1 JZOXYHAIBAFMTD-ZNSCEPEASA-N 0.000 description 1
- PHISPBBPVHZUNV-UZGGCZOTSA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 PHISPBBPVHZUNV-UZGGCZOTSA-N 0.000 description 1
- JZOXYHAIBAFMTD-JPQYBODWSA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@H](C4=CC=CC=C4)C3)=NC(C)=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@H](C4=CC=CC=C4)C3)=NC(C)=N2)CC1 JZOXYHAIBAFMTD-JPQYBODWSA-N 0.000 description 1
- PHISPBBPVHZUNV-HKTMPKTRSA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@H](C4=CC=CC=C4)C3)=NC=N2)CC1 PHISPBBPVHZUNV-HKTMPKTRSA-N 0.000 description 1
- LMCRIUZUEVRGDL-UONOGXRCSA-N CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)OC(C)(C)C)CC1 Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCN(C(=O)OC(C)(C)C)CC1 LMCRIUZUEVRGDL-UONOGXRCSA-N 0.000 description 1
- GRAUAIMXHCNYPE-WDEREUQCSA-N CO[C@@H]1COCC[C@@H]1NC1CCNCC1.Cl.Cl Chemical compound CO[C@@H]1COCC[C@@H]1NC1CCNCC1.Cl.Cl GRAUAIMXHCNYPE-WDEREUQCSA-N 0.000 description 1
- QXFNWFZQHYGEOC-QWHCGFSZSA-N CO[C@@H]1COCC[C@@H]1NCC1=CC=CC=C1 Chemical compound CO[C@@H]1COCC[C@@H]1NCC1=CC=CC=C1 QXFNWFZQHYGEOC-QWHCGFSZSA-N 0.000 description 1
- NCAVNBUJRNVPQK-FPMFFAJLSA-N CO[C@@H]1COCC[C@@H]1N[C@@H](C)C1=CC=CC=C1 Chemical compound CO[C@@H]1COCC[C@@H]1N[C@@H](C)C1=CC=CC=C1 NCAVNBUJRNVPQK-FPMFFAJLSA-N 0.000 description 1
- GYOAUMVMZFXBHJ-UKILVPOCSA-N CO[C@@H]1COCC[C@H]1CC1CCN(C(=O)C2=C(C)C(NCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 Chemical compound CO[C@@H]1COCC[C@H]1CC1CCN(C(=O)C2=C(C)C(NCC3=CC=C(C(C)(C)C)C=C3)=NC=N2)CC1 GYOAUMVMZFXBHJ-UKILVPOCSA-N 0.000 description 1
- VNGTVYIGXVMRIB-PHDIDXHHSA-N CO[C@@H]1COCC[C@H]1N=[N+]=[N-] Chemical compound CO[C@@H]1COCC[C@H]1N=[N+]=[N-] VNGTVYIGXVMRIB-PHDIDXHHSA-N 0.000 description 1
- GRJKHGCKUMAJDQ-VXGBXAGGSA-N CO[C@H](CN(CC1)C2CCNCC2)[C@@H]1NS(C)(=O)=O Chemical compound CO[C@H](CN(CC1)C2CCNCC2)[C@@H]1NS(C)(=O)=O GRJKHGCKUMAJDQ-VXGBXAGGSA-N 0.000 description 1
- KPHLAFOGEWRIRI-DEOSSOPVSA-N CO[C@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C1 Chemical compound CO[C@H]1CCN(C2CCN(C(=O)C3=C(C)C(CCC4=CC=C(C(C)(C)C)C=C4)=NC=N3)CC2)C1 KPHLAFOGEWRIRI-DEOSSOPVSA-N 0.000 description 1
- QJUBDGJWFFUOBE-ZJUUUORDSA-N CO[C@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1NS(C)(=O)=O Chemical compound CO[C@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1NS(C)(=O)=O QJUBDGJWFFUOBE-ZJUUUORDSA-N 0.000 description 1
- COSMAAFCGGXAIG-CPJSRVTESA-N CO[C@H]1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC[C@H]1CS(C)(=O)=O Chemical compound CO[C@H]1CN(C2CCN(C(=O)C3=C(C)C(CCC4=CC(Cl)=C(Cl)C=C4)=NC=N3)CC2)CC[C@H]1CS(C)(=O)=O COSMAAFCGGXAIG-CPJSRVTESA-N 0.000 description 1
- FFGCHCCFBCJKHK-RQJHMYQMSA-N CO[C@H]1CNCC[C@H]1NS(C)(=O)=O.O=C(O)C(F)(F)F Chemical compound CO[C@H]1CNCC[C@H]1NS(C)(=O)=O.O=C(O)C(F)(F)F FFGCHCCFBCJKHK-RQJHMYQMSA-N 0.000 description 1
- KLHXGNOPMSZTNN-BCAGLNGWSA-N CO[C@H]1COCC[C@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound CO[C@H]1COCC[C@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3CCC[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 KLHXGNOPMSZTNN-BCAGLNGWSA-N 0.000 description 1
- PHISPBBPVHZUNV-JWRZUHOQSA-N CO[C@H]1COCC[C@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 Chemical compound CO[C@H]1COCC[C@H]1NC1CCN(C(=O)C2=C(C)C(CC[C@H]3C[C@@H](C4=CC=CC=C4)C3)=NC=N2)CC1 PHISPBBPVHZUNV-JWRZUHOQSA-N 0.000 description 1
- LMCRIUZUEVRGDL-KGLIPLIRSA-N CO[C@H]1COCC[C@H]1NC1CCN(C(=O)OC(C)(C)C)CC1 Chemical compound CO[C@H]1COCC[C@H]1NC1CCN(C(=O)OC(C)(C)C)CC1 LMCRIUZUEVRGDL-KGLIPLIRSA-N 0.000 description 1
- GRAUAIMXHCNYPE-MNOVXSKESA-N CO[C@H]1COCC[C@H]1NC1CCNCC1.Cl.Cl Chemical compound CO[C@H]1COCC[C@H]1NC1CCNCC1.Cl.Cl GRAUAIMXHCNYPE-MNOVXSKESA-N 0.000 description 1
- NCAVNBUJRNVPQK-BNOWGMLFSA-N CO[C@H]1COCC[C@H]1N[C@H](C)C1=CC=CC=C1 Chemical compound CO[C@H]1COCC[C@H]1N[C@H](C)C1=CC=CC=C1 NCAVNBUJRNVPQK-BNOWGMLFSA-N 0.000 description 1
- WEVBYQPPTQNUDS-UHFFFAOYSA-N CS(=O)(=O)NC1CCN(C2CCN(C(=O)OCC3=CC=CC=C3)CC2)CC1 Chemical compound CS(=O)(=O)NC1CCN(C2CCN(C(=O)OCC3=CC=CC=C3)CC2)CC1 WEVBYQPPTQNUDS-UHFFFAOYSA-N 0.000 description 1
- UUFJIGOFIXLCLT-UHFFFAOYSA-N CS(=O)(=O)NC1CCN(C2CCNCC2)CC1 Chemical compound CS(=O)(=O)NC1CCN(C2CCNCC2)CC1 UUFJIGOFIXLCLT-UHFFFAOYSA-N 0.000 description 1
- ROUDBBDNGYJGNN-SECBINFHSA-N CS(=O)(=O)N[C@@H]1CCN(C2CCNCC2)C1.Cl.Cl Chemical compound CS(=O)(=O)N[C@@H]1CCN(C2CCNCC2)C1.Cl.Cl ROUDBBDNGYJGNN-SECBINFHSA-N 0.000 description 1
- ROUDBBDNGYJGNN-VIFPVBQESA-N CS(=O)(=O)N[C@H]1CCN(C2CCNCC2)C1.Cl.Cl Chemical compound CS(=O)(=O)N[C@H]1CCN(C2CCNCC2)C1.Cl.Cl ROUDBBDNGYJGNN-VIFPVBQESA-N 0.000 description 1
- RINOYHWVBUKAQE-UHFFFAOYSA-N Cc(cccc1)c1I Chemical compound Cc(cccc1)c1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 1
- DBYSALSGLCCTEI-IBGZPJMESA-N Cc1c(C(N(CC2)CCC2N(CC2)C[C@H]2N(C)S(C)(=O)=O)=O)ncnc1NCc(cc1Cl)ccc1Cl Chemical compound Cc1c(C(N(CC2)CCC2N(CC2)C[C@H]2N(C)S(C)(=O)=O)=O)ncnc1NCc(cc1Cl)ccc1Cl DBYSALSGLCCTEI-IBGZPJMESA-N 0.000 description 1
- NBQIUIDFKMQDNE-UHFFFAOYSA-N Cc1c(NCC(C2)COc3c2cccc3)ncnc1C(N(CC1)CCC1N(CC1)CCC1O)=O Chemical compound Cc1c(NCC(C2)COc3c2cccc3)ncnc1C(N(CC1)CCC1N(CC1)CCC1O)=O NBQIUIDFKMQDNE-UHFFFAOYSA-N 0.000 description 1
- VCBZWLYEGVCXME-UHFFFAOYSA-N Cc1c(NCC(CC2)CCN2c2ccccc2)ncnc1C(N(CC1)CCC1N(CC1)CCC1O)=O Chemical compound Cc1c(NCC(CC2)CCN2c2ccccc2)ncnc1C(N(CC1)CCC1N(CC1)CCC1O)=O VCBZWLYEGVCXME-UHFFFAOYSA-N 0.000 description 1
- JXMDQPUEBIQNJQ-UHFFFAOYSA-N Cc1c(NCC(CC2)CN2c2ccccc2)ncnc1C(N(CC1)CCC1N(CC1)CCC1C(NC)=O)=O Chemical compound Cc1c(NCC(CC2)CN2c2ccccc2)ncnc1C(N(CC1)CCC1N(CC1)CCC1C(NC)=O)=O JXMDQPUEBIQNJQ-UHFFFAOYSA-N 0.000 description 1
- ZUMPHNNFQLSNEU-UHFFFAOYSA-N Cc1c(NCCCCc2ccccc2)ncnc1C(N(CC1)CCC1N(CC1)CCC1O)=O Chemical compound Cc1c(NCCCCc2ccccc2)ncnc1C(N(CC1)CCC1N(CC1)CCC1O)=O ZUMPHNNFQLSNEU-UHFFFAOYSA-N 0.000 description 1
- SERVRTMWVLWOQP-UHFFFAOYSA-N Cc1c(NCCc(cc2)cc(Cl)c2Cl)ncnc1C(N(CC1)CCC1(C(N)=O)N1CCCCC1)=O Chemical compound Cc1c(NCCc(cc2)cc(Cl)c2Cl)ncnc1C(N(CC1)CCC1(C(N)=O)N1CCCCC1)=O SERVRTMWVLWOQP-UHFFFAOYSA-N 0.000 description 1
- SKXRZNWUSUPTJB-UHFFFAOYSA-N Cc1c(NCCc(cc2)cc(F)c2F)ncnc1C(N(CC1)CCC1N1CCCCC1)=O Chemical compound Cc1c(NCCc(cc2)cc(F)c2F)ncnc1C(N(CC1)CCC1N1CCCCC1)=O SKXRZNWUSUPTJB-UHFFFAOYSA-N 0.000 description 1
- MVURUHKOFNAGDQ-UHFFFAOYSA-N Cc1c(NCCc(cc2)ccc2OC(F)(F)F)ncnc1C(N(CC1)CCC1N(CC1)CCC1NS(C)(=O)=O)=O Chemical compound Cc1c(NCCc(cc2)ccc2OC(F)(F)F)ncnc1C(N(CC1)CCC1N(CC1)CCC1NS(C)(=O)=O)=O MVURUHKOFNAGDQ-UHFFFAOYSA-N 0.000 description 1
- NPCGQLFYIPIOAA-AFARHQOCSA-N Cc1c(NC[C@H](C2)C[C@@H]2c(cc2)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)CCC1N(C)S(C)(=O)=O)=O Chemical compound Cc1c(NC[C@H](C2)C[C@@H]2c(cc2)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)CCC1N(C)S(C)(=O)=O)=O NPCGQLFYIPIOAA-AFARHQOCSA-N 0.000 description 1
- ZHLAYFZZDRBFFZ-CTYIDZIISA-N Cc1c(NC[C@H](C2)C[C@@H]2c2ccccc2)nc(C)nc1C(O)=O Chemical compound Cc1c(NC[C@H](C2)C[C@@H]2c2ccccc2)nc(C)nc1C(O)=O ZHLAYFZZDRBFFZ-CTYIDZIISA-N 0.000 description 1
- JKZGCUQIIIFICC-UHFFFAOYSA-N Cc1c(NCc(cc2)cc(Cl)c2Cl)ncnc1C(N(CC1)CCC1N(CC1)CCC1NC(N)=O)=O Chemical compound Cc1c(NCc(cc2)cc(Cl)c2Cl)ncnc1C(N(CC1)CCC1N(CC1)CCC1NC(N)=O)=O JKZGCUQIIIFICC-UHFFFAOYSA-N 0.000 description 1
- MCUJYXFLDBITRW-FGZHOGPDSA-N Cc1c(NCc(cc2)cc(Cl)c2Cl)ncnc1C(N(CC1)CCC1N(CC[C@H]1NS(C)(=O)=O)C[C@H]1OC)=O Chemical compound Cc1c(NCc(cc2)cc(Cl)c2Cl)ncnc1C(N(CC1)CCC1N(CC[C@H]1NS(C)(=O)=O)C[C@H]1OC)=O MCUJYXFLDBITRW-FGZHOGPDSA-N 0.000 description 1
- CAKKCTRPAORRIZ-UHFFFAOYSA-N Cc1c(NCc(cc2Cl)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)CC1O)=O Chemical compound Cc1c(NCc(cc2Cl)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)CC1O)=O CAKKCTRPAORRIZ-UHFFFAOYSA-N 0.000 description 1
- YNFYIBBHVFUTFR-QGZVFWFLSA-N Cc1c(NCc(cc2Cl)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)C[C@@H]1NS(C)(=O)=O)=O Chemical compound Cc1c(NCc(cc2Cl)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)C[C@@H]1NS(C)(=O)=O)=O YNFYIBBHVFUTFR-QGZVFWFLSA-N 0.000 description 1
- YNFYIBBHVFUTFR-KRWDZBQOSA-N Cc1c(NCc(cc2Cl)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)C[C@H]1NS(C)(=O)=O)=O Chemical compound Cc1c(NCc(cc2Cl)ccc2Cl)ncnc1C(N(CC1)CCC1N(CC1)C[C@H]1NS(C)(=O)=O)=O YNFYIBBHVFUTFR-KRWDZBQOSA-N 0.000 description 1
- VMZVFUZKCCXBTP-UHFFFAOYSA-N Cc1c(NCc2cc(Cl)c(C(F)(F)F)cc2)ncnc1C(N(CC1)CCC1N1CCCCC1)=O Chemical compound Cc1c(NCc2cc(Cl)c(C(F)(F)F)cc2)ncnc1C(N(CC1)CCC1N1CCCCC1)=O VMZVFUZKCCXBTP-UHFFFAOYSA-N 0.000 description 1
- VTMKJVIJUXKZGI-UHFFFAOYSA-N Cc1cc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3O)=O)ncn2)ccc1F Chemical compound Cc1cc(CNc2c(C)c(C(N(CC3)CCC3N(CC3)CCC3O)=O)ncn2)ccc1F VTMKJVIJUXKZGI-UHFFFAOYSA-N 0.000 description 1
- MXCADAMOZGRLGV-RPWUZVMVSA-N Cc1ccc([C@@H]2C[C@H](CNc3c(C)c(C(N(CC4)CCC4N(CC4)CCC4N(C)S(C)(=O)=O)=O)ncn3)CCC2)[o]1 Chemical compound Cc1ccc([C@@H]2C[C@H](CNc3c(C)c(C(N(CC4)CCC4N(CC4)CCC4N(C)S(C)(=O)=O)=O)ncn3)CCC2)[o]1 MXCADAMOZGRLGV-RPWUZVMVSA-N 0.000 description 1
- IYAIFZSFNYUKRL-MRVPVSSYSA-N Cl.Cl.NC(=O)[C@@H]1CCN(C2CCNCC2)C1 Chemical compound Cl.Cl.NC(=O)[C@@H]1CCN(C2CCNCC2)C1 IYAIFZSFNYUKRL-MRVPVSSYSA-N 0.000 description 1
- IYAIFZSFNYUKRL-QMMMGPOBSA-N Cl.Cl.NC(=O)[C@H]1CCN(C2CCNCC2)C1 Chemical compound Cl.Cl.NC(=O)[C@H]1CCN(C2CCNCC2)C1 IYAIFZSFNYUKRL-QMMMGPOBSA-N 0.000 description 1
- VCACKTOTVISIQR-UHFFFAOYSA-N Cl.Cl.NC1CCN(C2CCN(C(=O)OCC3=CC=CC=C3)CC2)CC1 Chemical compound Cl.Cl.NC1CCN(C2CCN(C(=O)OCC3=CC=CC=C3)CC2)CC1 VCACKTOTVISIQR-UHFFFAOYSA-N 0.000 description 1
- IWWFIYSOOCLNTB-UHFFFAOYSA-N Cl.N#CC1=CC=C(N2CCCC(CN)C2)C=C1Cl Chemical compound Cl.N#CC1=CC=C(N2CCCC(CN)C2)C=C1Cl IWWFIYSOOCLNTB-UHFFFAOYSA-N 0.000 description 1
- ADDANAKZRANRIS-UHFFFAOYSA-N Cl.NCC1CCCN(C2=CC=C(C(F)(F)F)C=C2)C1 Chemical compound Cl.NCC1CCCN(C2=CC=C(C(F)(F)F)C=C2)C1 ADDANAKZRANRIS-UHFFFAOYSA-N 0.000 description 1
- YOYVLKMGXMXKMP-JTQLQIEISA-N Cl.NC[C@@H]1CCN(C2=CC=CC=C2)C1 Chemical compound Cl.NC[C@@H]1CCN(C2=CC=CC=C2)C1 YOYVLKMGXMXKMP-JTQLQIEISA-N 0.000 description 1
- YOYVLKMGXMXKMP-SNVBAGLBSA-N Cl.NC[C@H]1CCN(C2=CC=CC=C2)C1 Chemical compound Cl.NC[C@H]1CCN(C2=CC=CC=C2)C1 YOYVLKMGXMXKMP-SNVBAGLBSA-N 0.000 description 1
- GGQYUEPTMWXPAQ-UHFFFAOYSA-N ClC1=CC=C(C2CCC(CBr)O2)C=C1 Chemical compound ClC1=CC=C(C2CCC(CBr)O2)C=C1 GGQYUEPTMWXPAQ-UHFFFAOYSA-N 0.000 description 1
- GGQYUEPTMWXPAQ-MNOVXSKESA-N ClC1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1 Chemical compound ClC1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1 GGQYUEPTMWXPAQ-MNOVXSKESA-N 0.000 description 1
- GGQYUEPTMWXPAQ-GHMZBOCLSA-N ClC1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1 Chemical compound ClC1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1 GGQYUEPTMWXPAQ-GHMZBOCLSA-N 0.000 description 1
- SNFCOEMOEHLVSO-UHFFFAOYSA-N FC(F)(F)C1=CC(C2CCC(CBr)O2)=CC=C1 Chemical compound FC(F)(F)C1=CC(C2CCC(CBr)O2)=CC=C1 SNFCOEMOEHLVSO-UHFFFAOYSA-N 0.000 description 1
- SNFCOEMOEHLVSO-MNOVXSKESA-N FC(F)(F)C1=CC([C@@H]2CC[C@H](CBr)O2)=CC=C1 Chemical compound FC(F)(F)C1=CC([C@@H]2CC[C@H](CBr)O2)=CC=C1 SNFCOEMOEHLVSO-MNOVXSKESA-N 0.000 description 1
- SNFCOEMOEHLVSO-GHMZBOCLSA-N FC(F)(F)C1=CC([C@H]2CC[C@H](CBr)O2)=CC=C1 Chemical compound FC(F)(F)C1=CC([C@H]2CC[C@H](CBr)O2)=CC=C1 SNFCOEMOEHLVSO-GHMZBOCLSA-N 0.000 description 1
- DNLMKOUZCHWJQD-UHFFFAOYSA-N FC(F)(F)C1=CC=C(C2CCC(CBr)O2)C=C1 Chemical compound FC(F)(F)C1=CC=C(C2CCC(CBr)O2)C=C1 DNLMKOUZCHWJQD-UHFFFAOYSA-N 0.000 description 1
- DNLMKOUZCHWJQD-MNOVXSKESA-N FC(F)(F)C1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1 Chemical compound FC(F)(F)C1=CC=C([C@@H]2CC[C@H](CBr)O2)C=C1 DNLMKOUZCHWJQD-MNOVXSKESA-N 0.000 description 1
- DNLMKOUZCHWJQD-GHMZBOCLSA-N FC(F)(F)C1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1 Chemical compound FC(F)(F)C1=CC=C([C@H]2CC[C@H](CBr)O2)C=C1 DNLMKOUZCHWJQD-GHMZBOCLSA-N 0.000 description 1
- FGQSHUZAYIVLMB-UHFFFAOYSA-N IC1CCNCC1 Chemical compound IC1CCNCC1 FGQSHUZAYIVLMB-UHFFFAOYSA-N 0.000 description 1
- GAUKKFMRLMOULV-UHFFFAOYSA-N IN1CCCCC1 Chemical compound IN1CCCCC1 GAUKKFMRLMOULV-UHFFFAOYSA-N 0.000 description 1
- FGOCYNPJLSHHOW-UHFFFAOYSA-N N#CC1CCC(C2=CC=C(Cl)C=C2)C1 Chemical compound N#CC1CCC(C2=CC=C(Cl)C=C2)C1 FGOCYNPJLSHHOW-UHFFFAOYSA-N 0.000 description 1
- YNMVEIHNAXYQLW-UHFFFAOYSA-N N#CC1CCC(C2=CC=C(F)C=C2)C1 Chemical compound N#CC1CCC(C2=CC=C(F)C=C2)C1 YNMVEIHNAXYQLW-UHFFFAOYSA-N 0.000 description 1
- TWVOWEDLLBJYSQ-UHFFFAOYSA-N N#CC1CCC(C2=CC=CC=C2)C1 Chemical compound N#CC1CCC(C2=CC=CC=C2)C1 TWVOWEDLLBJYSQ-UHFFFAOYSA-N 0.000 description 1
- DWDWBUOHYKQORO-UHFFFAOYSA-N N#CC1CCCC(C2=CC=C(F)C=C2)C1 Chemical compound N#CC1CCCC(C2=CC=C(F)C=C2)C1 DWDWBUOHYKQORO-UHFFFAOYSA-N 0.000 description 1
- XGNAHPXUDUJLPS-UHFFFAOYSA-N N#CC1CCCC(C2=CC=CC(F)=C2)C1 Chemical compound N#CC1CCCC(C2=CC=CC(F)=C2)C1 XGNAHPXUDUJLPS-UHFFFAOYSA-N 0.000 description 1
- DMIOQYUUBYOBMS-GLGOKHISSA-N N#CC1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound N#CC1CCC[C@@H](C2=CC=CC=C2)C1 DMIOQYUUBYOBMS-GLGOKHISSA-N 0.000 description 1
- DMIOQYUUBYOBMS-YUZLPWPTSA-N N#CC1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound N#CC1CCC[C@H](C2=CC=CC=C2)C1 DMIOQYUUBYOBMS-YUZLPWPTSA-N 0.000 description 1
- TUJZEZGYYYPPSU-UHFFFAOYSA-N NC(=O)C1=COC(C2=CC=CC=C2)=C1 Chemical compound NC(=O)C1=COC(C2=CC=CC=C2)=C1 TUJZEZGYYYPPSU-UHFFFAOYSA-N 0.000 description 1
- QYFGDODQJCMIFM-VXGBXAGGSA-N NC(=O)[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound NC(=O)[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 QYFGDODQJCMIFM-VXGBXAGGSA-N 0.000 description 1
- QYFGDODQJCMIFM-NWDGAFQWSA-N NC(=O)[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound NC(=O)[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 QYFGDODQJCMIFM-NWDGAFQWSA-N 0.000 description 1
- QYFGDODQJCMIFM-NEPJUHHUSA-N NC(=O)[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound NC(=O)[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 QYFGDODQJCMIFM-NEPJUHHUSA-N 0.000 description 1
- QYFGDODQJCMIFM-RYUDHWBXSA-N NC(=O)[C@H]1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound NC(=O)[C@H]1CCC[C@H](C2=CC=CC=C2)C1 QYFGDODQJCMIFM-RYUDHWBXSA-N 0.000 description 1
- JEMSQMDCOCYCHW-DTORHVGOSA-N NC(=O)[C@H]1C[C@@H](C2=CC=C(Cl)C=C2)C1 Chemical compound NC(=O)[C@H]1C[C@@H](C2=CC=C(Cl)C=C2)C1 JEMSQMDCOCYCHW-DTORHVGOSA-N 0.000 description 1
- JEMSQMDCOCYCHW-KYZUINATSA-N NC(=O)[C@H]1C[C@H](C2=CC=C(Cl)C=C2)C1 Chemical compound NC(=O)[C@H]1C[C@H](C2=CC=C(Cl)C=C2)C1 JEMSQMDCOCYCHW-KYZUINATSA-N 0.000 description 1
- WBEVIMZYSNHMAN-UHFFFAOYSA-N NC1CCOC2=C1N=CC=C2 Chemical compound NC1CCOC2=C1N=CC=C2 WBEVIMZYSNHMAN-UHFFFAOYSA-N 0.000 description 1
- NWXWBNOVNWJPME-UHFFFAOYSA-N NCC1=COC(C2=CC=CC=C2)=C1 Chemical compound NCC1=COC(C2=CC=CC=C2)=C1 NWXWBNOVNWJPME-UHFFFAOYSA-N 0.000 description 1
- AUEHVTZPXZGHPK-UHFFFAOYSA-N NCC1CC(C2=CC=CC=C2)CO1 Chemical compound NCC1CC(C2=CC=CC=C2)CO1 AUEHVTZPXZGHPK-UHFFFAOYSA-N 0.000 description 1
- BVFACYWCLSRPFJ-UHFFFAOYSA-N NCC1CCC(C2=CC=C(C(F)(F)F)C=C2)O1 Chemical compound NCC1CCC(C2=CC=C(C(F)(F)F)C=C2)O1 BVFACYWCLSRPFJ-UHFFFAOYSA-N 0.000 description 1
- MAVPDTWSXVZZGQ-UHFFFAOYSA-N NCC1CCC(C2=CC=C(Cl)C=C2)C1 Chemical compound NCC1CCC(C2=CC=C(Cl)C=C2)C1 MAVPDTWSXVZZGQ-UHFFFAOYSA-N 0.000 description 1
- KHKLNHSDQIKVSU-UHFFFAOYSA-N NCC1CCC(C2=CC=C(Cl)C=C2)O1 Chemical compound NCC1CCC(C2=CC=C(Cl)C=C2)O1 KHKLNHSDQIKVSU-UHFFFAOYSA-N 0.000 description 1
- NOJGBVMGWPLFOB-UHFFFAOYSA-N NCC1CCC(C2=CC=C(F)C=C2)C1 Chemical compound NCC1CCC(C2=CC=C(F)C=C2)C1 NOJGBVMGWPLFOB-UHFFFAOYSA-N 0.000 description 1
- SJWDZYDEPUPPJQ-UHFFFAOYSA-N NCC1CCC(C2=CC=CC(C(F)(F)F)=C2)O1 Chemical compound NCC1CCC(C2=CC=CC(C(F)(F)F)=C2)O1 SJWDZYDEPUPPJQ-UHFFFAOYSA-N 0.000 description 1
- ARQITJXMBWHLFZ-UHFFFAOYSA-N NCC1CCC(C2=CC=CC=C2)C1 Chemical compound NCC1CCC(C2=CC=CC=C2)C1 ARQITJXMBWHLFZ-UHFFFAOYSA-N 0.000 description 1
- XVOZIEBVEQEFOM-UHFFFAOYSA-N NCC1CCCC(C2=CC=C(F)C=C2)C1 Chemical compound NCC1CCCC(C2=CC=C(F)C=C2)C1 XVOZIEBVEQEFOM-UHFFFAOYSA-N 0.000 description 1
- LOOJSCVYLUAMBC-UHFFFAOYSA-N NCC1CCCC(C2=CC=CC(F)=C2)C1 Chemical compound NCC1CCCC(C2=CC=CC(F)=C2)C1 LOOJSCVYLUAMBC-UHFFFAOYSA-N 0.000 description 1
- PUHARHOETXRMES-UHFFFAOYSA-N NCC1CCCN(C2=CC=CC=C2)C1 Chemical compound NCC1CCCN(C2=CC=CC=C2)C1 PUHARHOETXRMES-UHFFFAOYSA-N 0.000 description 1
- SLFCZCBUOSEXNF-DGCLKSJQSA-N NC[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound NC[C@@H]1CCC[C@@H](C2=CC=CC=C2)C1 SLFCZCBUOSEXNF-DGCLKSJQSA-N 0.000 description 1
- SLFCZCBUOSEXNF-YPMHNXCESA-N NC[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound NC[C@@H]1CCC[C@H](C2=CC=CC=C2)C1 SLFCZCBUOSEXNF-YPMHNXCESA-N 0.000 description 1
- SLFCZCBUOSEXNF-WCQYABFASA-N NC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 Chemical compound NC[C@H]1CCC[C@@H](C2=CC=CC=C2)C1 SLFCZCBUOSEXNF-WCQYABFASA-N 0.000 description 1
- SLFCZCBUOSEXNF-AAEUAGOBSA-N NC[C@H]1CCC[C@H](C2=CC=CC=C2)C1 Chemical compound NC[C@H]1CCC[C@H](C2=CC=CC=C2)C1 SLFCZCBUOSEXNF-AAEUAGOBSA-N 0.000 description 1
- BVFACYWCLSRPFJ-MNOVXSKESA-N NC[C@H]1CC[C@@H](C2=CC=C(C(F)(F)F)C=C2)O1 Chemical compound NC[C@H]1CC[C@@H](C2=CC=C(C(F)(F)F)C=C2)O1 BVFACYWCLSRPFJ-MNOVXSKESA-N 0.000 description 1
- KHKLNHSDQIKVSU-MNOVXSKESA-N NC[C@H]1CC[C@@H](C2=CC=C(Cl)C=C2)O1 Chemical compound NC[C@H]1CC[C@@H](C2=CC=C(Cl)C=C2)O1 KHKLNHSDQIKVSU-MNOVXSKESA-N 0.000 description 1
- SJWDZYDEPUPPJQ-MNOVXSKESA-N NC[C@H]1CC[C@@H](C2=CC=CC(C(F)(F)F)=C2)O1 Chemical compound NC[C@H]1CC[C@@H](C2=CC=CC(C(F)(F)F)=C2)O1 SJWDZYDEPUPPJQ-MNOVXSKESA-N 0.000 description 1
- BVFACYWCLSRPFJ-GHMZBOCLSA-N NC[C@H]1CC[C@H](C2=CC=C(C(F)(F)F)C=C2)O1 Chemical compound NC[C@H]1CC[C@H](C2=CC=C(C(F)(F)F)C=C2)O1 BVFACYWCLSRPFJ-GHMZBOCLSA-N 0.000 description 1
- KHKLNHSDQIKVSU-GHMZBOCLSA-N NC[C@H]1CC[C@H](C2=CC=C(Cl)C=C2)O1 Chemical compound NC[C@H]1CC[C@H](C2=CC=C(Cl)C=C2)O1 KHKLNHSDQIKVSU-GHMZBOCLSA-N 0.000 description 1
- SJWDZYDEPUPPJQ-GHMZBOCLSA-N NC[C@H]1CC[C@H](C2=CC=CC(C(F)(F)F)=C2)O1 Chemical compound NC[C@H]1CC[C@H](C2=CC=CC(C(F)(F)F)=C2)O1 SJWDZYDEPUPPJQ-GHMZBOCLSA-N 0.000 description 1
- MONLEWIXEYRPQD-WAAGHKOSSA-N NC[C@H]1C[C@@H](C2=CC=C(Cl)C=C2)C1 Chemical compound NC[C@H]1C[C@@H](C2=CC=C(Cl)C=C2)C1 MONLEWIXEYRPQD-WAAGHKOSSA-N 0.000 description 1
- OAYZCUQCMUYZBG-JGZJWPJOSA-N NC[C@H]1C[C@@H](C2=CC=CC=C2)C1 Chemical compound NC[C@H]1C[C@@H](C2=CC=CC=C2)C1 OAYZCUQCMUYZBG-JGZJWPJOSA-N 0.000 description 1
- MONLEWIXEYRPQD-CZMCAQCFSA-N NC[C@H]1C[C@H](C2=CC=C(Cl)C=C2)C1 Chemical compound NC[C@H]1C[C@H](C2=CC=C(Cl)C=C2)C1 MONLEWIXEYRPQD-CZMCAQCFSA-N 0.000 description 1
- OAYZCUQCMUYZBG-HOMQSWHASA-N NC[C@H]1C[C@H](C2=CC=CC=C2)C1 Chemical compound NC[C@H]1C[C@H](C2=CC=CC=C2)C1 OAYZCUQCMUYZBG-HOMQSWHASA-N 0.000 description 1
- XIKJFLZKRAPBCL-UHFFFAOYSA-N O=C(C1=C(Br)C(CCC2=CC(C3=CC=CC=C3)=CC=C2)=NC=N1)N1CCC(N2CCC(O)CC2)CC1 Chemical compound O=C(C1=C(Br)C(CCC2=CC(C3=CC=CC=C3)=CC=C2)=NC=N1)N1CCC(N2CCC(O)CC2)CC1 XIKJFLZKRAPBCL-UHFFFAOYSA-N 0.000 description 1
- SVGAVCXTRVMSAA-UHFFFAOYSA-N O=C(C1=C(Br)C(CCC2=CC(C3=CC=CC=C3)=CC=C2)=NC=N1)N1CCC(N2CCOCC2)CC1 Chemical compound O=C(C1=C(Br)C(CCC2=CC(C3=CC=CC=C3)=CC=C2)=NC=N1)N1CCC(N2CCOCC2)CC1 SVGAVCXTRVMSAA-UHFFFAOYSA-N 0.000 description 1
- NVPXORZVPIAQFB-UHFFFAOYSA-N O=C(C1=CC(NCC2=CC=C(C3=CC=CC=C3)C=C2)=NC=N1)N1CCC(N2CCCC(O)C2)CC1 Chemical compound O=C(C1=CC(NCC2=CC=C(C3=CC=CC=C3)C=C2)=NC=N1)N1CCC(N2CCCC(O)C2)CC1 NVPXORZVPIAQFB-UHFFFAOYSA-N 0.000 description 1
- XDLBDIPROCBMIS-UHFFFAOYSA-N O=C(O)C1=C(Br)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 Chemical compound O=C(O)C1=C(Br)C(CCC2=CC=CC(C3=CC=CC=C3)=C2)=NC=N1 XDLBDIPROCBMIS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
-
- 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
- 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- 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
-
- 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
- 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
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases where activation of CCR2 plays a causative role, especially pulmonary diseases like asthma and COPD, neurologic disease, especially of pain diseases, immune related diseases, especially diabetes mellitus including diabetes nephropathy, and cardiovascular diseases, especially atherosclerotic disease.
- CCR2 CCR2 chemokine receptor 2
- CC chemokine receptor 2 CC chemokine receptor 2
- the present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases where activation of CCR2 plays a causative role, especially pulmonary diseases like asthma and COPD, neurologic disease, especially of pain diseases, immune related diseases, especially diabetes mellitus including diabetes nephropathy, and cardiovascular diseases, especially atherosclerotic disease.
- the chemokines are a family of small, proinflammatory cytokines, with potent chemotactic activities. Chemokines are chemotactic cytokines that are released by a wide variety of cells to attract various cells, such as monocytes, macrophages, T cells, eosinophils, basophils and neutrophils to sites of inflammation.
- Chemokine receptors such as CCR2 or CCR5 have been implicated as being important mediators of inflammatory and immunoregulatory disorders and diseases as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis. Accordingly, agents which modulate chemokine receptors such as the CCR2 and CCR5 receptor would be useful in such disorders and diseases.
- monocytes are characterized by, e.g., a high expression of membrane-resident CCR2, whereas the CCR2 expression in macrophages is lower.
- CCR2 is a critical regulator of monocytes trafficking, which can be described as the movement of the monocytes towards an inflammation along a gradient of monocyte chemoattractant proteins (MCP-1, MCP-2, MCP-3, MCP-4).
- R 1 is -L 1 -R 7 , wherein L 1 is a linker selected from a bond or a group selected from —C 1 -C 2 -alkylene, and —C 1 -C 2 -alkenylene which optionally comprises one or more groups selected from —O—, —C(O)—, and —NH— in the chain and which is optionally substituted by a group selected from among —OH, —NH 2 , —C 1 -C 3 -alkyl, O—C 1 -C 6 -alkyl, and —CN, wherein R 7 is a ring selected from among —C 3 -C 8 -cycloalkyl, —C 3 -C 8 -heterocyclyl, —C 5 -C 10 -aryl, and —C 5 -C 10 -heteroaryl, wherein the ring R 7 is optionally substituted with one or more groups selected from among —CF 3 , —
- Z is C or N
- Preferred compounds of formula (I) according to the invention are compounds with R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ R 16 , R 17 , R 18 , A, L 2 , Z, Q, and n as herein before or below defined, wherein R 1 is -L 1 -R 7 ,
- L 1 being a linker selected from a bond or a group selected from among —C 1 -C 2 -alkylene, and —C 1 -C 2 -alkenylene optionally comprising one or more groups selected from among —O—, —C(O)—, and, —NH— in the chain and optionally being substituted by a group selected from among —OH, —NH 2 , —C 1 -C 3 -alkyl, O—C 1 -C 6 -alkyl, and —CN, wherein R 7 is a ring selected from among —C 3 -C 8 -cycloalkyl, —C 5 -C 10 -aryl, —C 3 -C 8 -heterocyclyl comprising 1 or 2 hetero atoms selected from among N, and O, and —C 5 -C 10 -heteroaryl comprising 1 or 2 hetero atoms selected from among N, and O, wherein the ring R 7 is optionally
- Preferred compounds of formula (I) according to the invention are compounds with R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ R 16 , R 17 , R 18 , A, L 2 , Z, Q, and n as herein before or below defined, wherein R 1 is -L 1 -R 7 ,
- L 1 is a linker selected from among a bond, methylene, ethylene, methenylene, and ethenylene, wherein L 1 , if different from a bond, is optionally substituted with one or more groups selected from among methyl, and ethyl
- R 7 is a ring selected from among cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, pyrrolidinyl, piperidinyl, azepanyl, tetrahydrofuranyl, tetrahydropyranyl, oxepanyl, phenyl, pyridyl, and furanyl
- the ring R 7 is optionally substituted with one or more groups selected from among —F, —Cl, -methyl, -ethyl, -propyl, -1-propyl, -cyclopropyl, -t-buty
- Preferred compounds of formula (I) according to the invention are compounds with R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ R 16 , R 17 , R 18 , A, L 2 , Z, Q, and n as herein before or below defined, wherein R 1 is -L 1 -R 7 ,
- L 1 is a linker selected from among a bond, methylene, ethylene, methenylene, and ethenylene and wherein L 1 is optionally substituted with one or more of methyl or ethyl and wherein L 1 optionally comprises one or more —O— atoms.
- Preferred compounds of formula (I) according to the invention are compounds with R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ R 16 , R 17 , R 18 , A, L 2 , Z, Q and n as herein before or below defined, wherein R 1 is selected from among
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 2 is selected from among —H, -methyl, -ethyl, -propyl, -1-propyl, -cyclopropyl, -butyl, -1-butyl, -t-butyl, —F, —Cl, —Br, —I, —CN, —CH ⁇ CH 2 , —C ⁇ CH, and —OCH 3 , more preferred from among H, -methyl, -
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13 ′′, R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 2 is selected from among —H, -Methyl, -Ethyl, —Br, and —OCH 3 .
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 3 is selected from among —H, and -methyl.
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 6 , R 7 , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 4 and R 5 are independently selected from among an electron pair, —H, -1-propyl, -amino, -pyrrolidinyl, -piperidinyl, -morpholinyl, -azepanyl, -oxazepanyl, -piperazinyl, -azetidinyl, -tetrahydropyranyl, -cyclopentyl, -cyclohexyl, and —C(O)—N(R 8
- R 4 and R 5 are optionally independently substituted with one or more groups selected from among -fluoro, -methyl, -ethyl, propyl, -1-propyl, -butyl, -1-butyl, -t-butyl, -hydroxy, —CF 3 , —OCF 3 , —CN, —O—CH 3 , —O—C 2 H 5 , —O—C 3 H 7 , —CH 2 —CN, —CH 2 —O—CH 3 , —(CH 2 ) 2 —O—CH 3 , —C(O)—CH 3 , —C(O)—C 2 H 5 , —C(O)—C 3 H 7 , —COOH, —C(O)—NH 2 , —C(O)—NH—CH 3 , —C(O)—N(CH 3 ) 2 , —NH—C(O)—CH 3 , —N(CH 3
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 4 and R 5 are independently selected from among an electron pair, —H, -amino, -piperidinyl, -tetrahydropyranyl, and -pyrrolidinyl, wherein R 4 and R 5 are optionally independently substituted with one or more groups selected from among -fluoro, —CF 3 , -hydroxy, —O—CH 3 , —OCF 3 , —CN, —NH—SO 2 —CH 3 , —
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , A, L 1 , Z, Q, and n as herein before or below defined, wherein R 4 and R 5 are independently a group of the structure -L 2 -R 18 , wherein L 2 is selected from among —NH—, —N(CH 3 )— and —N(C 2 H 5 )—, wherein R 18 is selected from among -tetrahydropyranyl, -cyclopropyl, -cyclobutyl, -cyclopentyl, -cyclohexyl, -cycloheptyl, -cyclooctyl, -
- R 18 is optionally substituted by one or more groups selected from among —F, —CF 3 , —OCF 3 , —CN, —OH, —O—CH 3 , —CH 3 , —NH—C(O)—CH 3 , —N(CH 3 )—C(O)—CH 3 , —C(O)—CH 3 , —S(O) 2 —CH 3 , —NH—S(O) 2 —CH 3 , —N(CH 3 )—S(O) 2 —CH 3 , and —C(O)—O—C 2 H 5 .
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 4 , R 5 and R 18 are optionally further bi-valently substituted by one or more groups selected from among
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 4 is selected from among
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 5 is selected from among an electron pair, —H, and —C(O)—NH 2 .
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein R 6 is selected from among —H, —CH 3 , —C 2 H 5 , —O—CH 3 , —O—C 2 H 5 , —F, —CF 3 , and —OCF 3 , and more preferred wherein R 6 is selected from among H, and —O—CH 3 , and most preferred wherein R 6 is —H.
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , L 1 , L 2 , Z, Q, and n as herein before or below defined, wherein A is selected from among a single bond, ⁇ CH—, —CH 2 , —O—, and —NH—, and more preferred wherein A is selected from among —O— and —NH—, and most preferred wherein A is —NH—.
- Preferred compounds of formula (I) according to the invention are compounds with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , R 11 , R 11′ , R 12 , R 13 , R 13′ , R 14 , R 15 , R 15′ , R 16 , R 17 , R 18 , A, L 1 , L 2 , Q, and n as herein before or below defined, wherein Z is selected from among C, and N, and more preferred wherein Z is C.
- substituents are independent of one another. If for example there might be a plurality of C 1 -C 6 -alkyl groups as substituents in one group, in the case of three substituents C 1 -C 6 -alkyl, one may represent methyl, one n-propyl and one tert-butyl.
- substituents may also be represented in the form of a structural formula.
- An asterisk (*) in the structural formula of the substituent is to be understood as being the linking point to the rest of the molecule.
- the atom of the substituent which follows the linking point is referred to as the atom in position number 1.
- the groups N-piperidinyl (Piperidin-A), 4-piperidinyl (Piperidin-B), 2-tolyl (Tolyl-C), 3-tolyl (Tolyl-D), and 4-tolyl (Tolyl-E) are shown as follows:
- each hydrogen atom may be removed from the substituent and the valency thus freed may act as a binding site to the rest of a molecule.
- (Tolyl-F) may represent 2-tolyl, 3-tolyl, 4-tolyl, and benzyl
- branched or unbranched, saturated or unsaturated C 1 -C 6 -carbon chain it is meant a chain of carbon atoms, which is constituted by six carbon atoms arranged in a row and which can optionally further comprise branches or one or more hetero atoms selected from N, O or S. Said carbon chain can be saturated or unsaturated by comprising double or triple bonds.
- C 1 -C 6 -alkyl (including those which are part of other groups) are meant branched and unbranched alkyl groups with 1 to 6 carbon atoms and by the term “C 1 -C 4 -alkyl” are meant branched and unbranched alkyl groups with 1 to 4 carbon atoms. Alkyl groups with 1 to 4 carbon atoms are preferred.
- alkyl groups with 1-6 carbon atoms examples include: methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl or hexyl.
- the abbreviations Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, t-Bu, etc. may also be used for the above-mentioned groups.
- the definitions propyl, butyl, pentyl and hexyl include all the possible isomeric forms of the groups in question.
- propyl includes n-propyl and iso-propyl
- butyl includes iso-butyl, sec-butyl and tert-butyl etc.
- C 1 -C 8 -alkylene (including those which are part of other groups) are meant branched and unbranched alkylene groups with 1 to 8 carbon atoms.
- C 2 -C 8 -alkylene are meant branched and unbranched alkylene groups with 2 to 8 carbon atoms.
- C 2 -C 6 -alkylene are meant branched and unbranched alkylene groups with 2 to 6 carbon atoms.
- C 1 -C 4 -alkylene are meant branched and unbranched alkylene groups with 1 to 4 carbon atoms.
- C 1 -C 2 -alkylene are meant branched and unbranched alkylene groups with 1 to 2 carbon atoms.
- C 0 -C 4 -alkylene are meant branched and unbranched alkylene groups with 0 to 4 carbon atoms, thus also a single bond is encompassed.
- C 1 -C 3 -alkylene are meant branched and unbranched alkylene groups with 1 to 3 carbon atoms.
- C 1 -C 8 -alkylene examples include: methylene, ethylene, propylene, 1-methylethylene, butylene, 1-methylpropylene, 1,1-dimethylethylene, 1,2-dimethylethylene, pentylene, 1,1-dimethylpropylene, 2,2-dimethylpropylene, 1,2-dimethylpropylene, 1,3-dimethylpropylene, hexylene, heptylene or octylene.
- the definitions propylene, butylene, pentylene, hexylene, heptylene and octylene include all the possible isomeric forms of the groups in question with the same number of carbons.
- propyl also includes 1-methylethylene and butylene includes 1-methylpropylene, 1,1-dimethylethylene, 1,2-dimethylethylene.
- carbon chain is to be substituted by a group which together with one or two carbon atoms of the alkylene chain forms a carbocyclic ring with 3, 5 or 6 carbon atoms, this includes the following examples of the rings:
- C 2 -C 6 -alkenyl (including those which are part of other groups) are meant branched and unbranched alkenyl groups with 2 to 6 carbon atoms and by the term “C 2 -C 4 -alkenyl” are meant branched and unbranched alkenyl groups with 2 to 4 carbon atoms, provided that they have at least one double bond. Alkenyl groups with 2 to 4 carbon atoms are preferred. Examples for C 2 -C 6 -alkenyls include: ethenyl or vinyl, propenyl, butenyl, pentenyl, or hexenyl.
- propenyl, butenyl, pentenyl and hexenyl include all the possible isomeric forms of the groups in question.
- propenyl includes 1-propenyl and 2-propenyl
- butenyl includes 1-, 2- and 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl etc.
- metal is meant a group with 1 carbon atom, provided that it is linked by a single bond as well as on the other side by a double bond:
- C 2 -C 8 -alkenylene (including those which are part of other groups) are meant branched and unbranched alkenylene groups with 2 to 8 carbon atoms and by the term “C 2 -C 6 -alkenylene” are meant branched and unbranched alkylene groups with 2 to 6 carbon atoms.
- C 1 -C 2 -alkenylene are meant alkenylene groups with 1 to 2 carbon atoms, provided that they have at least one double bond, whereas by the term “C 1 -alkenylene” is meant “methenylene”.
- C 2 -C 8 -alkenylenes include: ethenylene, propenylene, 1-methylethenylene, butenylene, 1-methylpropenylene, 1,1-dimethylethenylene, 1,2-dimethylethenylene, pentenylene, 1,1-dimethylpropenylene, 2,2-dimethylpropenylene, 1,2-dimethylpropenylene, 1,3-dimethylpropenylene, hexenylene, heptenylene or octenylene.
- propenylene, butenylene, pentenylene and hexenylene include all the possible isomeric forms of the groups in question with the same number of carbons.
- propenyl also includes 1-methylethenylene and butenylene includes 1-methylpropenylene, 1,1-dimethylethenylene, 1,2-dimethylethenylene.
- C 2 -C 6 -alkynyl (including those which are part of other groups) are meant branched and unbranched alkynyl groups with 2 to 6 carbon atoms and by the term “C 2 -C 4 -alkynyl” are meant branched and unbranched alkynyl groups with 2 to 4 carbon atoms, provided that they have at least one triple bond.
- Examples for C 2 -C 6 -alkynyls include: ethynyl, propynyl, butynyl, pentynyl or hexynyl.
- propynyl, butynyl, pentynyl and hexynyl include all the possible isomeric forms of the groups in question.
- propynyl includes 1-propynyl and 2-propynyl
- butynyl includes 1-, 2-, and 3-butynyl, 1-methyl-1-propynyl, 1-methyl-2-propynyl etc.
- C 2 -C 8 -alkynylene (including those which are part of other groups) are meant branched and unbranched alkynylene groups with 2 to 8 carbon atoms and by the term “C 2 -C 6 -alkynylene” are meant branched and unbranched alkylene groups with 2 to 6 carbon atoms.
- C 2 -C 8 -alkynylenes include: ethynylene, propynylene, 1-methylethynylene, butynylene, 1-methylpropynylene, 1,1-dimethylethynylene, 1,2-dimethylethynylene, pentynylene, 1,1-dimethylpropynylene, 2,2-dimethylpropynylene, 1,2-dimethylpropynylene, 1,3-dimethylpropynylene, hexynylene, heptynylene or octynylene.
- propynylene, butynylene, pentynylene and hexynylene include all the possible isomeric forms of the groups in question with the same number of carbons.
- propynyl also includes 1-methylethynylene and butynylene includes 1-methylpropynylene, 1,1-dimethylethynylene, 1,2-dimethylethynylene.
- ring carbocycles, which can be saturated, unsaturated or aromatic and which optionally can comprise one or more hetero atoms selected from N, O or S.
- —C 3 -C 8 -heterocyclyl are meant three-, four-, five-, six-, or seven-membered, saturated or unsaturated heterocyclic rings which may contain one, two, or three heteroatoms, selected from among oxygen, sulfur, and nitrogen, while the ring may be linked to the molecule through a carbon atom or through a nitrogen atom, if there is one.
- —C 5 -C 8 -heterocyclyl are meant five-, six-, or seven-membered, saturated or unsaturated heterocyclic rings which may contain one, two, or three heteroatoms, selected from among oxygen, sulfur, and nitrogen, while the ring may be linked to the molecule through a carbon atom or through a nitrogen atom, if there is one. Examples include:
- heterocyclic ring may be provided with a keto group.
- heterocycle may be provided with a keto group. Examples include:
- C 3 -C 8 -cycloalkyl (including those which are part of other groups) are meant cyclic alkyl groups with 3 to 8 carbon atoms.
- C 3 -C 6 -cycloalkyl are meant cyclic alkyl groups with 3 to 6 carbon atoms.
- Examples of C 3 -C 8 -cycloalkyls include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
- the cyclic alkyl groups may be substituted by one or more groups selected from among methyl, ethyl, isopropyl, tert-butyl, hydroxy, fluorine, chlorine, bromine, and iodine.
- aryl including those which are part of other groups
- C 5 -C 10 -aryl aromatic ring systems with 5 to 10 carbon atoms.
- Preferred are “C 6 -C 10 -aryl” groups whereas aromatic rings are meant with 6 to 10 carbon atoms. Examples include: phenyl or naphthyl.
- C 5 -C 6 -aryl whereas aromatic rings are meant with 5 to 6 carbon atoms Unless otherwise stated, the aromatic ring systems may be substituted by one or more groups selected from among methyl, ethyl, iso-propyl, tert-butyl, hydroxy, fluorine, chlorine, bromine and iodine.
- C 5 -C 10 -heteroaryl (including those which are part of other groups) are meant five- or six-membered heterocyclic aromatic groups or 5-10-membered, bicyclic heteroaryl rings which may contain one, two, or three heteroatoms selected from among oxygen, sulfur, and nitrogen, and contain so many conjugated double bonds that an aromatic system is formed.
- C 5 -C 6 -heteroaryl groups whereas aromatic rings are meant five- or six-membered heterocyclic aromatic groups. Unless otherwise stated, these heteroaryls may be substituted by one or more groups selected from among methyl, ethyl, isopropyl, tert-butyl, hydroxy, fluorine, chlorine, bromine, and iodine.
- X—C 1 -C 4 -alkyl- with X being a functional group such as —CO—, —NH—, —C(OH)— and the like
- the functional group X can be located at either of the ends of the —C 1 -C 4 -alkyl chain.
- spiro-C 3 -C 8 -cycloalkyl are meant 3-8 membered, spirocyclic rings while the ring is linked to the molecule through a carbon atom.
- spiro-C 3 -C 8 -heterocyclyl are meant 3-8 membered, spirocyclic rings which may contain one, two, or three heteroatoms selected from among oxygen, sulfur, and nitrogen, while the ring may be linked to the molecule through a carbon atom or through a nitrogen atom, if there is one.
- a spirocyclic ring may be provided with an oxo, methyl, or ethyl group. Examples include:
- Halogen within the scope of the present invention denotes fluorine, chlorine, bromine or iodine. Unless stated to the contrary, fluorine, chlorine and bromine are regarded as preferred halogens.
- Linker within the scope of the present invention denominates a bivalent group or a bond.
- Compounds of general formula (I) may have acid groups, chiefly carboxyl groups, and/or basic groups such as e.g. amino functions. Compounds of general formula (I) may therefore occur as internal salts, as salts with pharmaceutically useable inorganic acids such as hydrochloric acid, sulphuric acid, phosphoric acid, sulphonic acid or organic acids (such as for example maleic acid, fumaric acid, citric acid, tartaric acid or acetic acid) or as salts with pharmaceutically useable bases such as alkali or alklaline earth metal hydroxides or carbonates, zinc or ammonium hydroxides or organic amines such as e.g. diethylamine, triethylamine, triethanolamine inter alia.
- pharmaceutically useable inorganic acids such as hydrochloric acid, sulphuric acid, phosphoric acid, sulphonic acid or organic acids (such as for example maleic acid, fumaric acid, citric acid, tartaric acid or acetic acid
- the compounds of formula (I) may be converted into the salts thereof, particularly for pharmaceutical use, into the physiologically and pharmacologically acceptable salts thereof.
- These salts may on the one hand be in the form of the physiologically and pharmacologically acceptable acid addition salts of the compounds of formula (I) with inorganic or organic acids.
- R is hydrogen
- the compound of formula (I) may also be converted by reaction with inorganic bases into physiologically and pharmacologically acceptable salts with alkali or alkaline earth metal cations as counter ion.
- the acid addition salts may be prepared for example using hydrochloric acid, hydrobromic acid, sulphuric acid, phosphoric acid, methanesulphonic acid, acetic acid, fumaric acid, succinic acid, lactic acid, citric acid, tartaric acid or maleic acid. It is also possible to use mixtures of the above-mentioned acids.
- the alkali and alkaline earth metal salts of the compound of formula (I) are preferably prepared using the alkali and alkaline earth metal hydroxides and hydrides thereof, of which the hydroxides and hydrides of the alkaline earth metals, particularly of sodium and potassium, are preferred and sodium and potassium hydroxide are particularly preferred.
- the compounds of general formula (I) may be converted into the salts thereof, particularly, for pharmaceutical use, into the pharmacologically acceptable acid addition salts with an inorganic or organic acid.
- Suitable acids include for example succinic acid, hydrobromic acid, acetic acid, fumaric acid, maleic acid, methanesulphonic acid, lactic acid, phosphoric acid, hydrochloric acid, sulphuric acid, tartaric acid or citric acid. It is also possible to use mixtures of the above-mentioned acids.
- the invention relates to the compounds in question, optionally in the form of the individual optical isomers, mixtures of the individual enantiomers or racemates, in the form of the tautomers as well as in the form of the free bases or the corresponding acid addition salts with pharmacologically acceptable acids—such as for example acid addition salts with hydrohalic acids—for example hydrochloric or hydrobromic acid or organic acids—such as for example oxalic, fumaric, diglycolic or methanesulphonic acid.
- pharmacologically acceptable acids such as for example acid addition salts with hydrohalic acids—for example hydrochloric or hydrobromic acid or organic acids—such as for example oxalic, fumaric, diglycolic or methanesulphonic acid.
- the compounds according to the invention may optionally occur as racemates, but they may also be obtained as pure enantiomers/diastereomers.
- the invention relates to the compounds in question, optionally in the form of the individual optical isomers, mixtures of the individual enantiomers or racemates, in the form of the tautomers as well as in the form of the free bases or the corresponding acid addition salts with pharmacologically acceptable acids—such as for example acid addition salts with hydrohalic acids—for example hydrochloric or hydrobromic acid or organic acids—such as for example oxalic, fumaric, diglycolic or methanesulphonic acid.
- pharmacologically acceptable acids such as for example acid addition salts with hydrohalic acids—for example hydrochloric or hydrobromic acid or organic acids—such as for example oxalic, fumaric, diglycolic or methanesulphonic acid.
- THP-1 cells human acute monocytic leukaemia cells
- THP-1 cells were cultured under standardized conditions at 37° C. and 5% CO2 in a humidified incubator.
- THP-1 cells were cultivated in RPMI 1640 medium (Gibco 21875) containing 1% MEM-NEAA (Gibso 11140) 2 mM L-glutamine, 1.5 g/L sodium bicarbonate, 4.5 g/L glucose, 10 mM HEPES and 1.0 mM sodium pyruvate, 90%; 10% fetal calf serum (FCS Gibco 10500-064).
- Membranes were prepared from THP-1 cells. THP-1 cells were centrifuged at 300 ⁇ g at 4° C. for 10 min.
- the cell pellet was resuspendet in Phosphate Buffer Saline (PBS , including 10 ⁇ M Pefabloc and a protease inhibitor mix ‘complete’, Boehringer Mannheim (1 tablet/50 ml)), to a concentration of 80 cells/ml.
- PBS Phosphate Buffer Saline
- the membrane preparation was performed by disrupting the cells by nitrogen decomposition (at 50 bar, for 1 h) in a “Nitrogen Bombe” (Parr Instrument). Cell debris was removed by centrifugation (800 ⁇ g at 4° C., 1 min). The supernatant was centrifuged at 80000 ⁇ g , 4° C. for 30 min to sediment the cell membranes .
- Usually 50 mg of protein (Bradford assay) were yielded from 1 ⁇ 10E9 cells.
- the membranes were resuspendet in 25 mM HEPES, 25 mM MgCl2, 1 mM CaCl2, 10% Glycerine for storage in aliquots at ⁇ 80° C. in 25 mM HEPES, 25 mM MgCl2, 1 mM CaCl2, 10% Glycerine and stored at ⁇ 80° C.
- THP-1 membrane were adjusted with 25 mM HEPES, pH 7.2; 5 mM MgCl 2 ; 0.5 mM CaCl 2 ; 0.2% BSA assay buffer to a concentration of 2.5 ⁇ g/15 ⁇ l.
- Amersham Biosciences PVT-WGA Beads (RPNQ0001) were adjusted with assay buffer to a concentration of 0.24 mg/30 ⁇ l.
- For preparation of the membrane-bead-suspension membranes and beads were incubated for 30 min at RT under rotation (60 rpm) with a ratio of 1:2.
- the present invention provides a method for modulating or treating at least one MCP-1 related disease, in a cell, tissue, organ, animal, or patient, as known in the art or as described herein, using at least one CCR2 antagonist of the present invention.
- the present invention also provides a method for modulating or treating at least one MCP-1 related disease, in a cell, tissue, organ, animal, or patient including, but not limited to, at least one of malignant disease, metabolic disease, an immune or inflammatory related disease, a cardiovascular disease, an infectious disease, or a neurologic disease.
- Such conditions are selected from, but not limited to, diseases or conditions mediated by cell adhesion and/or angiogenesis.
- diseases or conditions include an immune disorder or disease, a cardiovascular disorder or disease, an infectious, malignant, and/or neurologic disorder or disease, or other known or specified MCP-1 related conditions.
- the CCR2 antagonists are useful for the treatment of diseases that involve inflammation such as COPD, angiogenesis such as disease of the eye and neoplastic disease, tissue remodeling such as restenosis, and proliferation of certain cells types particularly epithelial and squamous cell carcinomas.
- diseases that involve inflammation such as COPD, angiogenesis such as disease of the eye and neoplastic disease, tissue remodeling such as restenosis, and proliferation of certain cells types particularly epithelial and squamous cell carcinomas.
- Particular indications include use in the treatment of atherosclerosis, restenosis, cancer metastasis, rheumatoid arthritis, diabetic retinopathy and macular degeneration.
- the antagonists may also be useful in the treatment of various fibrotic diseases such as idiopathic pulmonary fibrosis, diabetic nephropathy, hepatitis, and cirrhosis.
- the present invention provides a method for modulating or treating at least one CCR2 related disease, in a cell, tissue, organ, animal, or patient, as known in the art or as described herein, using at least one CCR2 antagonist of the present invention. Particular indications are discussed below:
- the present invention also provides a method for modulating or treating at least one malignant disease in a cell, tissue, organ, animal or patient, including, but not limited to, at least one of: pneumonia; lung abscess; occupational lung diseases caused be agents in the form or dusts, gases, or mists; asthma, bronchiolitis fibrosa obliterans, respiratory failure, hypersensitivity diseases of the lungs iricludeing hypersensitivity pneumonitis (extrinsic allergic alveolitis), allergic bronchopulmonary aspergillosis, and drug reactions; adult respiratory distress syndrome (ARDS), Goodpasture's Syndrome, chronic obstructive airway disorders (COPD), idiopathic interstitial lung diseases such as idiopathic pulmonary fibrosis and sarcoidosis, desquamative interstitial pneumonia, acute interstitial pneumonia, respiratory bronchiolitis-associated interstitial lung disease, idiopathic bronchiolitis obliterans with organizing pneumonia, lymphocytic interstitial pneu
- the present invention also provides a method for modulating or treating at least one malignant disease in a cell, tissue, organ, animal or patient, including, but not limited to, at least one of: leukemia, acute leukemia, acute lymphoblastic leukemia (ALL), B-cell, T-cell or FAB ALL, acute myeloid leukemia (AML), chromic myelocytic leukemia (CML), chronic lymphocytic leukemia (CLL), hairy cell leukemia, myelodyplastic syndrome (MDS), a lymphoma, Hodgkin's disease, a malignant lymphoma, non-hodgkin's lymphoma, Burkitt's lymphoma, multiple myeloma, Kaposi's sarcoma, colorectal carcinoma, pancreatic carcinoma, renal cell carcinoma, breast cancer, nasopharyngeal carcinoma, malignant histiocytosis, paraneoplastic syndrome/hypercalcemia of malignancy, solid
- the present invention also provides a method for modulating or treating at least one immune related disease, in a cell, tissue, organ, animal, or patient including, but not limited to, at least one of rheumatoid arthritis, juvenile rheumatoid arthritis, systemic onset juvenile rheumatoid arthritis, psoriatic arthritis, ankylosing spondilitis, gastric ulcer, seronegative arthropathies, osteoarthritis, inflammatory bowel disease, ulcerative colitis, systemic lupus erythematosis, antiphospholipid syndrome, iridocyclitisluveitisloptic neuritis, idiopathic pulmonary fibrosis, systemic vasculitis/ admireer's granulomatosis, sarcoidosis, orchitislvasectomy reversal procedures, allergiclatopic diseases, asthma, allergic rhinitis, eczema, allergic contact dermatitis, allergic conjunctivitis, hypersensitivity pneumonit
- the present invention also provides a method for modulating or treating at least one cardiovascular disease in a cell, tissue, organ, animal, or patient, including, but not limited to, at least one of cardiac 25 stun syndrome, myocardial infarction, congestive heart failure, stroke, ischemic stroke, hemorrhage, arteriosclerosis, atherosclerosis, restenosis, diabetic ateriosclerotic disease, hypertension, arterial hypertension, renovascular hypertension, syncope, shock, syphilis of the cardiovascular system, heart failure, cor pulmonale, primary pulmonary hypertension, cardiac arrhythmias, atrial ectopic beats, atrial flutter, atrial fibrillation (sustained or paroxysmal), post perfusion syndrome, cardiopulmonary bypass inflammation response, chaotic or multifocal atrial tachycardia, regular narrow QRS tachycardia, specific arrythmias, ventricular fibrillation, His bundle arrythmias, atrioventricular block, bundle
- the present invention also provides a method for modulating or treating at least one neurologic disease in a cell, tissue, organ, animal or patient, including, but not limited to, at least one of: Neuropathic pain such as low back pain, hip pain, leg pain, non-herpetic neuralgia, post herpetic neuralgia, diabetic neuropathy, nerve injury-induced pain, acquired immune deficiency syndrome (AIDS) related neuropathic pain, head trauma, toxin and chemotherapy caused nerve injuries, phantom limb pain, multiple sclerosis, root avulsions, painful traumatic mononeuropathy, painful polyneuropathy, thalamic pain syndrome, post-stroke pain, central nervous system injury, post surgical pain, carpal tunnel syndrome, trigeminal neuralgia, post mastectomy syndrome, postthoracotomy syndrome, stump pain, repetitive motion pain, neuropathic pain associated hyperalgesia and allodynia, alcoholism and other drug-induced pain; neurodegenerative diseases, multiple sclerosis, migraine headache, AIDS dementia complex,
- the present invention also provides a method for modulating or treating fibrotic conditions of various etiologies such as liver fibrosis (including but not limited to alcohol-induced cirrhosis, viral-induced cirrhosis, autoirnrnune-induced hepatitis); lung fibrosis (including but not limited to scleroderma, idiopathic pulmonary fibrosis); kidney fibrosis (including but not limited to scleroderma, diabetic nephritis, glomerular pehpritis, lupus nephritis); dermal fibrosis (including but not limited to scleroderma, hypertrophic and keloid scarring, burns); myelofibrosis; Neurofibromatosis; fibroma; intestinal fibrosis; and fibrotic adhesions resulting from surgical procedures.
- liver fibrosis including but not limited to alcohol-induced cirrhosis, viral-induced cirrhosis, autoi
- the present invention also provides a method for modulating or treating at least one wound, trauma or tissue injury or chronic condition resulting from or related thereto, in a cell, tissue, organ, animal or patient, including, but not limited to, at least one of: bodily injury or a trauma associated with surgery including thoracic, abdominal, cranial, or oral surgery; or wherein the wound is selected from the group consisting of aseptic wounds, contused wounds, incised wounds, lacerated wounds, non-penetrating wounds, open wounds, penetrating wounds, perforating wounds, puncture wounds, septic wounds, infarctions and subcutaneous wounds; or wherein the wound is selected from the group consisting of ischemic ulcers, pressure sores, fistulae, severe bites, thermal burns and donor site wounds; or wherein the wound is anaphthous wound, a traumatic wound or a herpes associated wound.
- Donor site wounds are wounds which e.g. occur in connection with removal of hard tissue from one part of the body to another part of the body e.g. in connection with transplantation.
- the wounds resulting from such operations are very painful and an improved healing is therefore most valuable.
- Wound fibrosis is also amenable to CCR2 antagonist therapy as the first cells to invade the wound area are neutrophils followed by monocytes which are activated by macrophages.
- Macrophages are believed to be essential for efficient wound healing in that they also are responsible for phagocytosis of pathogenic organisms and a clearing up of tissue debris. Furthermore, they release numerous factors involved in subsequent events of the healing process.
- the macrophages attract fibroblasts which start the production of collagen.
- the CCR2 antagonist of the invention can be used in methods for modulating, treating or preventing such sequelae of wound healing.
- the present invention also provides a method for modulating or treating at least one infectious disease in a cell, tissue, organ, animal or patient, including, but not limited to, at least one of: acute or chronic bacterial infection, acute and chronic parasitic or infectious processes, including bacterial, viral and fungal infections, HIV infection, HIV neuropathy, meningitis, hepatitis (A, B or C, or the like), septic arthritis, peritonitis, pneumonia, epiglottitis, e.
- acute or chronic bacterial infection including acute and chronic parasitic or infectious processes, including bacterial, viral and fungal infections, HIV infection, HIV neuropathy, meningitis, hepatitis (A, B or C, or the like), septic arthritis, peritonitis, pneumonia, epiglottitis, e.
- coli 0157:h7 hemolytic uremic syndrome/thrombolytic thrombocytopenic purpura, malaria, dengue hemorrhagic fever, leishmaniasis, leprosy, toxic shock syndrome, streptococcal myositis, gas gangrene, mycobacterium tuberculosis, mycobacterium avium intracellulare, pneumocystis carinii pneumonia, pelvic inflammatory disease, orchitislepidydimitis, legionella , lyme disease, influenza a, epstein-barr virus, vital-associated hemaphagocytic syndrome, vital encephalitisiaseptic meningitis, and the like.
- Any method of the present invention can comprise administering an effective amount of a composition or pharmaceutical composition comprising at least one CCR2 antagonist to a cell, tissue, organ, animal or patient in need of such modulation, treatment or therapy.
- these compounds are also useful for veterinary treatment of companion animals, exotic animals and farm animals, including mammals, rodents, and the like.
- the compounds of formula I may be used on their own or in conjunction with other active substances of formula I according to the invention. If desired the compounds of formula I may also be used in combination with other pharmacologically active substances. It is preferable to use for this purpose active substances selected for example from among betamimetics, anticholinergics, corticosteroids, other PDE4-inhibitors, LTD4-antagonists, EGFR-inhibitors, MRP4-inhibitors, dopamine agonists, H1-antihistamines, PAF-antagonists and PI3-kinase inhibitors or double or triple combinations thereof, such as for example combinations of compounds of formula I with one or two compounds selected from among betamimetics, anticholinergics, corticosteroids, other PDE4-inhibitors, LTD4-antagonists, EGFR-inhibitors, MRP4-inhibitors, dopamine agonists, H1-antihistamines, PAF-antagonists and PI3-kinase inhibitors
- the invention also encompasses combinations of three active substances, each selected from one of the above-mentioned categories of compounds.
- the betamimetics used are preferably compounds selected from among albuterol, bambuterol, bitolterol, broxaterol, carbuterol, clenbuterol, fenoterol, formoterol, arformoterol, zinterol, hexoprenaline, ibuterol, isoetharine, isoprenaline, levosalbutamol, mabuterol, meluadrine, metaproterenol, orciprenaline, pirbuterol, procaterol, reproterol, rimiterol, ritodrine, salmeterol, salmefamol, soterenol, sulphonterol, tiaramide, terbutaline, tolubuterol, CHF-1035, HOKU-81, KUL-1248, 3-(4- ⁇ 6-[2-hydroxy-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-hexyl
- the beta mimetics are selected from among bambuterol, bitolterol, carbuterol, clenbuterol, fenoterol, formoterol, hexoprenaline, ibuterol, pirbuterol, procaterol, reproterol, salmeterol, sulphonterol, terbutaline, tolubuterol, 3-(4- ⁇ 6-[2-hydroxy-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-hexyloxy ⁇ -butyl)-benzenesulphonamide, 5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one , 4-hydroxy-7-[2- ⁇ [2- ⁇ [3-(2-phenylethoxy)propyl]sulphonyl ⁇ ethyl]-amino ⁇ ethyl]-2(3H)-benzothiazol
- betamimetics are selected from among fenoterol, formoterol, salmeterol, 3-(4- ⁇ 6-[2-hydroxy-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-hexyloxy ⁇ -butyl)-benzenesulphonamide, 5-[2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one, 1-[3-(4-methoxybenzyl-amino)-4-hydroxyphenyl]-2-[4-(1-benzimidazolyl)-2-methyl-2-butylamino]ethanol, 1-[2H-5-hydroxy-3-oxo-4H-1,4-benzoxazin-8-yl]-2-[3-(4-N,N-dimethylaminophenyl)-2-methyl-2-propylamino]ethanol, 1-[2H-5-hydroxy-3-oxo-4H-1
- betamimetics those which are particularly preferred according to the invention are formoterol, salmeterol, 3-(4- ⁇ 6-[2-hydroxy-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-hexyloxy ⁇ -butyl)-benzenesulphonamide, 6-hydroxy-8- ⁇ 1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl ⁇ -4H-benzo[1,4]oxazin-3-one, 6-hydroxy-8- ⁇ 1-hydroxy-2-[2-(ethyl 4-phenoxy-acetate)-1,1-dimethyl-ethylamino]-ethyl ⁇ -4H-benzo[1,4]oxazin-3-one, 6-hydroxy-8- ⁇ 1-hydroxy-2-[2-(4-phenoxy-acetic acid)-1,1-dimethyl-ethylamino]-ethyl ⁇ -4H-benzo[1,4]
- the acid addition salts of the betamimetics are preferably selected from among hydrochloride, hydrobromide, hydriodide, hydrosulphate, hydrophosphate, hydromethanesulphonate, hydronitrate, hydromaleate, hydroacetate, hydrobenzoate, hydrocitrate, hydrofumarate, hydrotartrate, hydroxalate, hydrosuccinate, hydrobenzoate and hydro-p-toluenesulphonat, preferably hydrochloride, hydrobromide, hydrosulphate, hydrophosphate, hydrofumarate and hydromethanesulphonate.
- the salts of hydrochloric acid, methanesulphonic acid, benzoic acid and acetic acid are particularly preferred according to the invention.
- the anticholinergics used are preferably compounds selected from among the tiotropium salts, oxitropium salts, flutropium salts, ipratropium salts, glycopyrronium salts, trospium salts, tropenol 2,2-diphenylpropionate methobromide, scopine 2,2-diphenylpropionate methobromide, scopine 2-fluoro-2,2-diphenylacetate methobromide, tropenol 2-fluoro-2,2-diphenylacetate methobromide, tropenol 3,3′,4,4′-tetrafluorobenzilate methobromide, scopine 3,3′,4,4′-tetrafluorobenzilate methobromide, tropenol 4,4′-difluorobenzilate methobromide, scopine 4,4′-difluorobenzilate methobromide, tropenol 3,3′-difluorobenzilate
- the cations tiotropium, oxitropium, flutropium, ipratropium, glycopyrronium and trospium are the pharmacologically active ingredients.
- the above-mentioned salts may preferably contain chloride, bromide, iodide, sulphate, phosphate, methanesulphonate, nitrate, maleate, acetate, citrate, fumarate, tartrate, oxalate, succinate, benzoate or p-toluenesulphonate, while chloride, bromide, iodide, sulphate, methanesulphonate or p-toluenesulphonate are preferred as counter-ions.
- the chlorides, bromides, iodides and methanesulphonate are particularly preferred.
- tiotropium bromide Of particular importance is tiotropium bromide.
- the pharmaceutical combinations according to the invention preferably contain it in the form of the crystalline tiotropium bromide monohydrate, which is known from WO 02/30928. If the tiotropium bromide is used in anhydrous form in the pharmaceutical combinations according to the invention, it is preferable to use anhydrous crystalline tiotropium bromide, which is known from WO 03/000265.
- Corticosteroids used here are preferably compounds selected from among prednisolone, prednisone, butixocortpropionate, flunisolide, beclomethasone, triamcinolone, budesonide, fluticasone, mometasone, ciclesonide, rofleponide, dexamethasone, betamethasone, deflazacort, RPR-106541, NS-126, (S)-fluoromethyl 6,9-difluoro-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carbothionate and (S)-(2-oxo-tetrahydro-furan-3S -yl) 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-propionyloxy-androsta-1,4-diene-17-carbothionate, optionally in the form of the racemates, enantio
- the steroid selected from among flunisolide, beclomethasone, triamcinolone, budesonide, fluticasone, mometasone, ciclesonide, rofleponide, dexamethasone, NS-126, (S)-fluoromethyl 6,9-difluoro-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carbothionate and (S)-(2-oxo-tetrahydro-furan-3S-yl) 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-propionyloxy-androsta-1,4-diene-17-carbothionate, optionally in the form of the racemates, enantiomers or diastereomers thereof and optionally in the form of the salts and derivatives, solvates and/or hydrates thereof.
- the steroid selected from among budesonide, fluticasone, mometasone, ciclesonide and (S)-fluoromethyl 6,9-difluoro-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carbothionate, optionally in the form of the racemates, enantiomers or diastereomers thereof and optionally in the form of the salts and derivatives, solvates and/or hydrates thereof.
- any reference to steroids includes a reference to any salts or derivatives, hydrates or solvates thereof which may exist.
- Examples of possible salts and derivatives of the steroids may be: alkali metal salts, such as for example sodium or potassium salts, sulphobenzoates, phosphates, isonicotinates, acetates, propionates, dihydrogen phosphates, palmitates, pivalates or furoates thereof.
- PDE4 inhibitors which may be used are preferably compounds selected from among enprofyllin, theophyllin, roflumilast, ariflo (cilomilast), tofimilast, pumafentrin, lirimilast, arofyllin, atizoram, D-4396 (Sch-351591), AWD-12-281 (GW-842470), NCS-613, CDP-840, D-4418, PD-168787, T-440, T-2585, V-11294A, CI-1018, CDC-801, CDC-3052, D-22888, YM-58997, Z-15370, N-(3,5-dichloro-1-oxo-pyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide, ( ⁇ )p-[(4aR*,10bS*)-9-ethoxy-1,2,3,4,4a,10b-hexahydro-8-methoxy-2
- the PDE4-inhibitor is selected from among enprofyllin, roflumilast, ariflo (cilomilast), arofyllin, atizoram, AWD-12-281 (GW-842470), T-440, T-2585, PD-168787, V-11294A, Cl-1018, CDC-801, D-22888, YM-58997, Z-15370, N-(3,5-dichloro-1-oxo-pyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide, cis[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylic acid], 2-carbomethoxy-4-cyano-4-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)cyclohexan-1-one, cis[4-cyano-4-(3-cyclo
- acid addition salts with pharmacologically acceptable acids which the above-mentioned PDE4-inhibitors might be in a position to form are meant, for example, salts selected from among the hydrochloride, hydrobromide, hydroiodide, hydrosulphate, hydrophosphate, hydromethanesulphonate, hydronitrate, hydromaleate, hydroacetate, hydrobenzoate, hydrocitrate, hydrofumarate, hydrotartrate, hydrooxalate, hydrosuccinate, hydrobenzoate and hydro-p-toluenesulphonate, preferably hydrochloride, hydrobromide, hydrosulphate, hydrophosphate, hydrofumarate and hydromethanesulphonate.
- LTD4-antagonists which may be used are preferably compounds selected from among montelukast, pranlukast, zafirlukast, MCC-847 (ZD-3523), MN-001, MEN-91507 (LM-1507), VUF-5078, VUF-K-8707, L-733321, 1-(((R)-(3-(2-(6,7-difluoro-2-quinolinyl)ethenyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)thio)methylcyclopropane-acetic acid, 1-(((1(R)-3(3-(2-(2.3-dichlorothieno[3,2-b]pyridin-5-yl)-(E)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane-acetic acid and [2-[[2-(4-
- the LTD4-antagonist is selected from among montelukast, pranlukast, zafirlukast, MCC-847 (ZD-3523), MN-001, MEN-91507 (LM-1507), VUF-5078, VUF-K-8707 and L-733321, optionally in the form of the racemates, enantiomers or diastereomers, optionally in the form of the pharmacologically acceptable acid addition salts and optionally in the form of the salts and derivatives, solvates and/or hydrates thereof.
- the LTD4-antagonist is selected from among montelukast, pranlukast, zafirlukast, MCC-847 (ZD-3523), MN-001 and MEN-91507 (LM-1507), optionally in the form of the racemates, enantiomers or diastereomers, optionally in the form of the pharmacologically acceptable acid addition salts and optionally in the form of the salts and derivatives, solvates and/or hydrates thereof.
- acid addition salts with pharmacologically acceptable acids which the LTD4-antagonists may be capable of forming are meant, for example, salts selected from among the hydrochloride, hydrobromide, hydroiodide, hydrosulphate, hydrophosphate, hydromethanesulphonate, hydronitrate, hydromaleate, hydroacetate, hydrobenzoate, hydrocitrate, hydrofumarate, hydrotartrate, hydrooxalate, hydrosuccinate, hydrobenzoate and hydro-p-toluenesulphonate, preferably hydrochloride, hydrobromide, hydrosulphate, hydrophosphate, hydrofumarate and hydromethanesulphonate.
- salts or derivatives which the LTD4-antagonists may be capable of forming are meant, for example: alkali metal salts, such as, for example, sodium or potassium salts, alkaline earth metal salts, sulphobenzoates, phosphates, isonicotinates, acetates, propionates, dihydrogen phosphates, palmitates, pivalates or furoates.
- alkali metal salts such as, for example, sodium or potassium salts, alkaline earth metal salts, sulphobenzoates, phosphates, isonicotinates, acetates, propionates, dihydrogen phosphates, palmitates, pivalates or furoates.
- the EGFR-inhibitors used are preferably compounds selected from among 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(morpholin-4-yl)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(N,N-diethylamino)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(N,N-dimethylamino)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(R)-(1-phenyl-ethyl)amino]-6
- Preferred EGFR inhibitors are selected from among 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(morpholin-4-yl)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(N,N-diethylamino)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(N,N-dimethylamino)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(R)-(1-phenyl-ethyl)amino]-6- ⁇ [4-
- EGFR-inhibitors which are selected from among 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(morpholin-4-yl)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(R)-(1-phenyl-ethyl)amino]-6- ⁇ [4-(morpholin-4-yl)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopentyloxy-quinazoline, 4-[(3-chloro-4-fluoro-phenyl)amino]-6- ⁇ [4-((R)-6-methyl-2-oxo-morpholin-4-yl)-1-oxo-2-buten-1-yl]amino ⁇ -7-[(S)-(tetrahydrofuran-3-yl)oxy]-quin
- Particularly preferred EGFR-inhibitors according to the invention are the compounds selected from among 4-[(3-chloro-4-fluorophenyl)amino]-6- ⁇ [4-(morpholin-4-yl)-1-oxo-2-buten-1-yl]amino ⁇ -7-cyclopropylmethoxy-quinazoline, 4-[(3-chloro-4-fluoro-phenyl)amino]-6- ⁇ [4-((R)-6-methyl-2-oxo-morpholin-4-yl)-1-oxo-2-buten-1-yl]amino ⁇ -7-[(S)-(tetrahydrofuran-3-yl)oxy]-quinazoline, 4-[(3-chloro-4-fluoro-phenyl)amino]-6-[2-((S)-6-methyl-2-oxo-morpholin-4-yl)-ethoxy]-7-methoxy-quinazoline, 4-[(3-chloro-4
- acid addition salts with pharmacologically acceptable acids which the EGFR-inhibitors may be capable of forming are meant, for example, salts selected from among the hydrochloride, hydrobromide, hydroiodide, hydrosulphate, hydrophosphate, hydromethanesulphonate, hydronitrate, hydromaleate, hydroacetate, hydrobenzoate, hydrocitrate, hydrofumarate, hydrotartrate, hydrooxalate, hydrosuccinate, hydrobenzoate and hydro-p-toluenesulphonate, preferably hydrochloride, hydrobromide, hydrosulphate, hydrophosphate, hydrofumarate and hydromethanesulphonate.
- dopamine agonists which may be used preferably include compounds selected from among bromocriptine, cabergoline, alpha-dihydroergocryptine, lisuride, pergolide, pramipexol, roxindol, ropinirol, talipexol, terguride and viozan.
- Any reference to the above-mentioned dopamine agonists within the scope of the present invention includes a reference to any pharmacologically acceptable acid addition salts and optionally hydrates thereof which may exist.
- physiologically acceptable acid addition salts which may be formed by the above-mentioned dopamine agonists are meant, for example, pharmaceutically acceptable salts which are selected from the salts of hydrochloric acid, hydrobromic acid, sulphuric acid, phosphoric acid, methanesulphonic acid, acetic acid, fumaric acid, succinic acid, lactic acid, citric acid, tartaric acid and maleic acid.
- H1-antihistamines preferably include compounds selected from among epinastine, cetirizine, azelastine, fexofenadine, levocabastine, loratadine, mizolastine, ketotifen, emedastine, dimetinden, clemastine, bamipin, cexchlorpheniramine, pheniramine, doxylamine, chlorophenoxamine, dimenhydrinate, diphenhydramine, promethazine, ebastine, desloratidine and meclozine.
- Any reference to the above-mentioned H1-antihistamines within the scope of the present invention includes a reference to any pharmacologically acceptable acid addition salts which may exist.
- PAF-antagonists preferably include compounds selected from among 4-(2-chlorophenyl)-9-methyl-2-[3(4-morpholinyl)-3-propanon-1-yl]-6H-thieno-[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepines, 6-(2-chlorophenyl)-8,9-dihydro-1-methyl-8-[(4-morpholinyl)carbonyl]-4H,7H-cyclo-penta-[4,5]thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepines.
- MRP4-inhibitors used are preferably compounds selected from among N-acetyl-dinitrophenyl-cysteine, cGMP, cholate, diclofenac, dehydroepiandrosterone 3-glucuronide, dehydroepiandrosterone 3-sulphate, dilazep, dinitrophenyl-s-glutathione, estradiol 17- ⁇ -glucuronide, estradiol 3,17-disulphate, estradiol 3-glucuronide, estradiol 3-sulphate, estrone 3-sulphate, flurbiprofen, folate, N5-formyl-tetrahydrofolate, glycocholate, clycolithocholic acid sulphate, ibuprofen, indomethacin, indoprofen, ketoprofen, lithocholic acid sulphate, methotrexate, MK571 ((E)-3-[[[3-[2-(7-ch
- the invention relates to the use of MRP4-inhibitors for preparing a pharmaceutical composition for the treatment of respiratory complaints, containing the PDE4B-inhibitors and MRP4-inhibitors, the MRP4-inhibitors preferably being selected from among N-acetyl-dinitrophenyl-cysteine, dehydroepiandrosterone 3-sulphate, dilazep, dinitrophenyl-S-glutathione, estradiol 3,17-disulphate, flurbiprofen, glycocholate, glycolithocholic acid sulphate, ibuprofen, indomethacin, indoprofen, lithocholic acid sulphate, MK571, PSC833, sildenafil, taurochenodeoxycholate, taurocholate, taurolithocholate, taurolithocholic acid sulphate, trequinsin and zaprinast, dipyridamole, optionally in the form of
- the invention relates more preferably to the use of MRP4-inhibitors for preparing a pharmaceutical composition for treating respiratory complaints, containing the PDE4B-inhibitors and MRP4-inhibitors according to the invention, the MRP4-inhibitors preferably being selected from among dehydroepiandrosterone 3-sulphate, estradiol 3,17-disulphate, flurbiprofen, indomethacin, indoprofen, MK571, taurocholate, optionally in the form of the racemates, enantiomers, diastereomers and the pharmacologically acceptable acid addition salts and hydrates thereof.
- the separation of enantiomers from the racemates can be carried out using methods known from the art (e.g. chromatography on chiral phases, etc.).
- acid addition salts with pharmacologically acceptable acids are meant, for example, salts selected from among the hydrochlorides, hydrobromides, hydroiodides, hydrosulphates, hydrophosphates, hydromethanesulphonates, hydronitrates, hydromaleates, hydroacetates, hydrobenzoates, hydrocitrates, hydrofumarates, hydrotartrates, hydrooxalates, hydrosuccinates, hydrobenzoates and hydro-p-toluenesulphonates, preferably the hydrochlorides, hydrobromides, hydrosulphates, hydrophosphates, hydrofumarates and hydromethanesulphonates.
- the invention further relates to pharmaceutical preparations which contain a triple combination of the PDE4B-inhibitors, MRP4-inhibitors and another active substance according to the invention, such as, for example, an anticholinergic, a steroid, an LTD4-antagonist or a betamimetic, and the preparation thereof and the use thereof for treating respiratory complaints.
- a triple combination of the PDE4B-inhibitors, MRP4-inhibitors and another active substance according to the invention such as, for example, an anticholinergic, a steroid, an LTD4-antagonist or a betamimetic, and the preparation thereof and the use thereof for treating respiratory complaints.
- the iNOS-inhibitors used are preferably compounds selected from among: S-(2-aminoethyl)isothiourea, aminoguanidine, 2-aminomethylpyridine, AMT, L-canavanine, 2-iminopiperidine, S-isopropylisothiourea, S-methylisothiourea, S-ethylisothiourea, S-methyltiocitrulline, S-ethylthiocitrulline, L-NA (N ⁇ -nitro-L-arginine), L-NAME (N ⁇ -nitro-L-arginine methylester), L-NMMA (N G -monomethyl-L-arginine), L-NIO (N ⁇ -iminoethyl-L-ornithine), L-NIL (N ⁇ -iminoethyl-lysine), (S)-6-acetimidoylamino-2-amino-
- AR-C102222 J. Med. Chem. 2003, 46, 913-916
- (1S,5S,6R)-7-chloro-5-methyl-2-aza-bicyclo[4.1.0]hept-2-en-3-ylamine ONO-1714
- (4R,5R)-5-ethyl-4-methyl-thiazolidin-2-ylideneamine Bioorg. Med. Chem. 2004, 12, 4101
- (4R,5R)-5-ethyl-4-methyl-selenazolidin-2-ylideneamine Bioorg. Med. Chem. Lett. 2005, 15, 1361
- 4-aminotetrahydrobiopterine Curr.
- iNOS-inhibitors which may be used within the scope of the present invention are antisense oligonucleotides, particularly antisense oligonucleotides that bind iNOS-coding nucleic acids.
- WO 01/52902 describes antisense oligonucleotides, particularly antisense-oligonucleotides, which bind iNOS-coding nucleic acids, for modulating the expression of iNOS.
- Those iNOS-antisense-oligonucleotides as described particularly in WO 01/52902 may therefore also be combined with the PDE4-inhibitors of the present invention on the basis of their similar activity to the iNOS inhibitors.
- Compounds which may be used as SYK-inhibitors are preferably compounds selected from among: R343 or R788.
- Suitable forms for administration are for example tablets, capsules, solutions, syrups, emulsions or inhalable powders or aerosols.
- the content of the pharmaceutically effective compound(s) in each case should be in the range from 0.1 to 90 wt. %, preferably 0.5 to 50 wt. % of the total composition, i.e. in amounts which are sufficient to achieve the dosage range specified hereinafter.
- the preparations may be administered orally in the form of a tablet, as a powder, as a powder in a capsule (e.g. a hard gelatine capsule), as a solution or suspension.
- a tablet e.g. a powder
- a capsule e.g. a hard gelatine capsule
- the active substance combination may be given as a powder, as an aqueous or aqueous-ethanolic solution or using a propellant gas formulation.
- pharmaceutical formulations are characterised in that they contain one or more compounds of formula I according to the preferred embodiments above.
- Suitable tablets may be obtained, for example, by mixing the active substance(s) with known excipients, for example inert diluents such as calcium carbonate, calcium phosphate or lactose, disintegrants such as corn starch or alginic acid, binders such as starch or gelatine, lubricants such as magnesium stearate or talc and/or agents for delaying release, such as carboxymethyl cellulose, cellulose acetate phthalate, or polyvinyl acetate.
- excipients for example inert diluents such as calcium carbonate, calcium phosphate or lactose, disintegrants such as corn starch or alginic acid, binders such as starch or gelatine, lubricants such as magnesium stearate or talc and/or agents for delaying release, such as carboxymethyl cellulose, cellulose acetate phthalate, or polyvinyl acetate.
- the tablets may also comprise several layers.
- Coated tablets may be prepared accordingly by coating cores produced analogously to the tablets with substances normally used for tablet coatings, for example collidone or shellac, gum arabic, talc, titanium dioxide or sugar.
- the core may also consist of a number of layers.
- the tablet coating may consist of a number of layers to achieve delayed release, possibly using the excipients mentioned above for the tablets.
- Syrups containing the active substances or combinations thereof according to the invention may additionally contain a sweetener such as saccharine, cyclamate, glycerol or sugar and a flavour enhancer, e.g. a flavouring such as vanillin or orange extract. They may also contain suspension adjuvants or thickeners such as sodium carboxymethyl cellulose, wetting agents such as, for example, condensation products of fatty alcohols with ethylene oxide, or preservatives such as p-hydroxybenzoates.
- a sweetener such as saccharine, cyclamate, glycerol or sugar
- a flavour enhancer e.g. a flavouring such as vanillin or orange extract.
- suspension adjuvants or thickeners such as sodium carboxymethyl cellulose, wetting agents such as, for example, condensation products of fatty alcohols with ethylene oxide, or preservatives such as p-hydroxybenzoates.
- Capsules containing one or more active substances or combinations of active substances may for example be prepared by mixing the active substances with inert carriers such as lactose or sorbitol and packing them into gelatine capsules.
- Suitable suppositories may be made for example by mixing with carriers provided for this purpose, such as neutral fats or polyethyleneglycol or the derivatives thereof.
- Excipients which may be used include, for example, water, pharmaceutically acceptable organic solvents such as paraffins (e.g. petroleum fractions), vegetable oils (e.g. groundnut or sesame oil), mono- or polyfunctional alcohols (e.g. ethanol or glycerol), carriers such as e.g. natural mineral powders (e.g. kaolins, clays, talc, chalk), synthetic mineral powders (e.g. highly dispersed silicic acid and silicates), sugars (e.g. cane sugar, lactose and glucose), emulsifiers (e.g.
- pharmaceutically acceptable organic solvents such as paraffins (e.g. petroleum fractions), vegetable oils (e.g. groundnut or sesame oil), mono- or polyfunctional alcohols (e.g. ethanol or glycerol), carriers such as e.g. natural mineral powders (e.g. kaolins, clays, talc, chalk), synthetic mineral powders (e.g. highly disper
- lignin e.g. lignin, spent sulphite liquors, methylcellulose, starch and polyvinylpyrrolidone
- lubricants e.g. magnesium stearate, talc, stearic acid and sodium lauryl sulphate.
- the tablets may, of course, contain, apart from the abovementioned carriers, additives such as sodium citrate, calcium carbonate and dicalcium phosphate together with various additives such as starch, preferably potato starch, gelatine and the like.
- additives such as sodium citrate, calcium carbonate and dicalcium phosphate together with various additives such as starch, preferably potato starch, gelatine and the like.
- lubricants such as magnesium stearate, sodium lauryl sulphate and talc may be used at the same time for the tabletting process.
- the active substances may be combined with various flavour enhancers or colourings in addition to the excipients mentioned above.
- the compounds of formula I are administered by inhalation, particularly preferably if they are administered once or twice a day.
- the compounds of formula I have to be made available in forms suitable for inhalation.
- Inhalable preparations include inhalable powders, propellant-containing metered-dose aerosols or propellant-free inhalable solutions, which are optionally present in admixture with conventional physiologically acceptable excipients.
- propellant-free inhalable solutions also includes concentrates or sterile ready-to-use inhalable solutions.
- the preparations which may be used according to the invention are described in more detail in the next part of the specification.
- physiologically acceptable excipients may be used to prepare the inhalable powders according to the invention: monosaccharides (e.g. glucose or arabinose), disaccharides (e.g. lactose, saccharose, maltose), oligo- and polysaccharides (e.g. dextran), polyalcohols (e.g. sorbitol, mannitol, xylitol), salts (e.g. sodium chloride, calcium carbonate) or mixtures of these excipients with one another.
- monosaccharides e.g. glucose or arabinose
- disaccharides e.g. lactose, saccharose, maltose
- oligo- and polysaccharides e.g. dextran
- polyalcohols e.g. sorbitol, mannitol, xylitol
- salts e.g. sodium chloride, calcium carbonate
- lactose is the particularly preferred excipient, while lactose monohydrate is most particularly preferred.
- the propellant-containing inhalable aerosols which may be used according to the invention may contain 1 dissolved in the propellant gas or in dispersed form.
- the propellant gases which may be used to prepare the inhalation aerosols according to the invention are known from the prior art. Suitable propellant gases are selected from among hydrocarbons such as n-propane, n-butane or isobutane and halohydrocarbons such as preferably fluorinated derivatives of methane, ethane, propane, butane, cyclopropane or cyclobutane.
- the propellant gases mentioned above may be used on their own or in mixtures thereof.
- propellant gases are fluorinated alkane derivatives selected from TG134a (1,1,1,2-tetrafluoroethane), TG227 (1,1,1,2,3,3,3-heptafluoropropane) and mixtures thereof.
- the propellant-driven inhalation aerosols used within the scope of the use according to the invention may also contain other ingredients such as co-solvents, stabilisers, surfactants, antioxidants, lubricants and pH adjusters. All these ingredients are known in the art.
- the compounds of formula I according to the invention are preferably used to prepare propellant-free inhalable solutions and inhalable suspensions.
- Solvents used for this purpose include aqueous or alcoholic, preferably ethanolic solutions.
- the solvent may be water on its own or a mixture of water and ethanol.
- the solutions or suspensions are adjusted to a pH of 2 to 7, preferably 2 to 5, using suitable acids.
- the pH may be adjusted using acids selected from inorganic or organic acids. Examples of particularly suitable inorganic acids include hydrochloric acid, hydrobromic acid, nitric acid, sulphuric acid and/or phosphoric acid.
- organic acids examples include ascorbic acid, citric acid, malic acid, tartaric acid, maleic acid, succinic acid, fumaric acid, acetic acid, formic acid and/or propionic acid etc.
- Preferred inorganic acids are hydrochloric and sulphuric acids. It is also possible to use the acids which have already formed an acid addition salt with one of the active substances.
- ascorbic acid, fumaric acid and citric acid are preferred.
- mixtures of the above acids may also be used, particularly in the case of acids which have other properties in addition to their acidifying qualities, e.g. as flavourings, antioxidants or complexing agents, such as citric acid or ascorbic acid, for example.
- co-solvents and/or other excipients may be added to the propellant-free inhalable solutions used for the purpose according to the invention.
- Preferred co-solvents are those which contain hydroxyl groups or other polar groups, e.g. alcohols—particularly isopropyl alcohol, glycols—particularly propyleneglycol, polyethyleneglycol, polypropyleneglycol, glycolether, glycerol, polyoxyethylene alcohols and polyoxyethylene fatty acid esters.
- excipients and additives in this context denote any pharmacologically acceptable substance which is not an active substance but which can be formulated with the active substance or substances in the pharmacologically suitable solvent in order to improve the qualitative properties of the active substance formulation.
- these substances Preferably, these substances have no pharmacological effect or, in connection with the desired therapy, no appreciable or at least no undesirable pharmacological effect.
- the excipients and additives include, for example, surfactants such as soya lecithin, oleic acid, sorbitan esters, such as polysorbates, polyvinylpyrrolidone, other stabilisers, complexing agents, antioxidants and/or preservatives which guarantee or prolong the shelf life of the finished pharmaceutical formulation, flavourings, vitamins and/or other additives known in the art.
- the additives also include pharmacologically acceptable salts such as sodium chloride as isotonic agents.
- the preferred excipients include antioxidants such as ascorbic acid, for example, provided that it has not already been used to adjust the pH, vitamin A, vitamin E, tocopherols and similar vitamins or provitamins occurring in the human body.
- Preservatives may be used to protect the formulation from contamination with pathogens. Suitable preservatives are those which are known in the art, particularly cetyl pyridinium chloride, benzalkonium chloride or benzoic acid or benzoates such as sodium benzoate in the concentration known from the prior art.
- ready-to-use packs of a medicament for the treatment of respiratory complaints are provided, containing an enclosed description including for example the words respiratory disease, COPD or asthma, a pteridine and one or more combination partners selected from those described above.
- 5-Bromo-6-hydroxy-pyrimidine-4-carboxylic acid ethyl ester (63 g, 0.26 mol) was suspended in 140 ml of phosphoroxychloride. Phosphorpentachloride (54 g, 0.26 mmol) was added and the reaction mixture was refluxed 72 h. The reaction mixture was concentrated in vacuum and the crude product was suspended and stirred in warmed-up hexane (50° C.); a precipitate was formed and filtered off. The filtrate was concentrated under vacuum to obtain 64 g (243 mmol) of the desired product which was used in the next steps without further purification.
- the reaction mixture was concentrated under vacuum, dissolved with dichloromethane, washed with a 1M aqueous solution of sodium hydroxide, washed with brine, dried over sodium sulfate and concentrated under vacuum.
- Intermediate 6f was synthesized in analogy to intermediate 6a, starting from trans 3-(4-chlorophenyl)-cyclobutan carboxylic acid (prepared as described in literature for the preparation of trans 3-phenyl-cyclobutan-carboxylic acid: Wiberg, K. B.; Dailey, W. P.; Walker, F. H.; Waddell, S. T.; Crocker, L. S.; Newton, M. Journal of the American Chemical Society; 1985, 107, 7247-7257).
- trans 3-(4-chlorophenyl)-cyclobutan carboxylic acid prepared as described in literature for the preparation of trans 3-phenyl-cyclobutan-carboxylic acid: Wiberg, K. B.; Dailey, W. P.; Walker, F. H.; Waddell, S. T.; Crocker, L. S.; Newton, M. Journal of the American Chemical Society; 1985, 107, 7247-7257).
- Intermediate 6g was synthesized in analogy to Intermediate 6a, starting from cis 3-(4-chlorophenyl)-cyclobutan carboxylic acid (prepared as described in literature for the preparation of cis 3-phenyl-cyclobutan-carboxylic acid: Wiberg, K. B.; Dailey, W. P.; Walker, F. H.; Waddell, S. T.; Crocker, L. S.; Newton, M. Journal of the American Chemical Society; 1985, 107, 7247-7257).
- Tris(dibenzylideneacetone)dipalladium (1.71 g, 1.87 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (2.32 g, 3.72 mmol) were stirred in 30 ml of toluene for 10 min under argon athmosphere.
- STRUCTURE mediate STRUCTURE (S)-1- Pyrrolidin-3- ylmethyl- carbamic acid tert- butyl ester bromo- benzene 8b 9b (R)-1- Pyrrolidin-3- ylmethyl- carbamic acid tert- butyl ester bromo- benzene 8c 9c Piperidine-3- yl-methyl- carbamic acid tert- butyl ester 1-bromo- 4-trifluoro methyl- benzene 8d 9d
- Piperidine-3-yl-methyl-carbamic acid tert-butyl ester (100 mg, 0.47 mmol), 2-chloro-4-fluoro-benzonitrile (72.5 mg, 0.47 mmol) and N,N-diisopropylethylamine (0.160 ml, 1.23 mmol) were dissolved in 10 ml of DMF and the reaction mixture was stirred at 125° C. overnight. The reaction mixture was concentrated under vacuum and the crude product was purified by flash chromatography (Isolute silica gel cartride: 5 g; eluent: ethyl acetate). 125 mg (0.36 mmol) of the desired compound were obtained.
- reaction mixture was concentrated under vacuum; the residue was dissolved in ethyl acetate and washed with an aqueous saturated sodium bicarbonate solution and then with water.
- N-methyl-N-piperidin-4-yl-methanesulfonamide hydrochloride (11 g, 47.91 mmol) was suspended in 200 ml of 1,2-dichloroethane, N,N-diisopropylethylamine (17.12 ml, 96.17 mmol) and 1-(tert-butoxycarbonyl)-piperidin-4-one (9.58 g, 48.08 mmol) were added and the reaction mixture was stirred at room temperature for 30 min.
- Sodium triacetoxyborohydride (12.23 g, 57.50 mmol) was added and the reaction mixture was stirred at room temperature for 72 h. The reaction mixture was diluted with dichloromethane and washed with an aqueous saturated sodium bicarbonate solution.
- the organic phase was dried over sodium sulfate and concentrated under vacuum.
- N-methyl-N-piperidin-4-yl-methanesulfonamide hydrochloride (1.13 g, 4.95 mmol) was suspended in 10 ml of 1,2-dichloroethane, N,N-diisopropylethylamine (2.6 ml, 14.9 mmol) and N-carbethoxy-3-methoxy-piperidin-4-one (1 g, 4.95 mmol) were added and the reaction mixture was stirred at room temperature for 30 min.
- Sodium triacetoxyborohydride (3.16 g, 14.85 mol) was added and the reaction mixture was stirred at room temperature for 72 h.
- the reaction mixture was diluted with dichloromethane and washed with an aqueous saturated sodium bicarbonate solution.
- the reaction mixture was concentrated under vacuum and the crude product was loaded on a SCX cartridge (25 g) and eluted with a 2M solution of ammonia in methanol. 1.2 g (3.97 mmol) of the desired compound were obtained.
- Piperidin-4-yl-carbamic acid tert-butyl ester (6 g, 30 mmol) and 1-(benzyloxycarbonyl)-4-oxopiperidine (9.6 g, 48 mmol) were dissolved in 50 ml of dichloromethane and the reaction mixture was stirred at room temperature for 30 min; sodium triacetoxyborohydride (12.23 g, 57.5 mmol) was added and the reaction mixture was stirred at room temperature overnight.
- the reaction mixture was diluted with dichloromethane and washed with an aqueous saturated sodium bicarbonate solution.
- the organic phase was dried over sodium sulfate and concentrated under vacuum.
- the crude product was treated with acetone/isopropyl ether and the precipitate obtained was filtered off 8.4 g (20 mmol) of the desired product were obtained.
- the organic phase was washed with a saturated aqueous solution of sodium bicarbonate, with a 1M aqueous solution of sodium hydroxide, with brine, then dried over sodium sulfate, filtered and concentrated under vacuum.
- the solvent was concentrated under vacuum and the crude product was loaded on a SCX cartridge (10 g) and eluted with a 2M solution of ammonia in methanol.
- the solvent was concentrated under vacuum and the crude product obtained was purified by flash chromatography (Biotage column 25M+; eluent: ethyl acetate). 250 mg (0.73 mmol) of the desired compound were obtained.
- 4,4-Difluorocyclohexanone 500 mg, 3.73 mmol
- potassium hydroxide 502 mg, 8.95 mmol
- the reaction mixture was cooled to 0° C. and a solution of iodine (1.04 g, 4.10 mmol) in 20 ml of methanol was added dropwise within 1 h.
- the reaction mixture was stirred at room temperature for 18 h, and then concentrated under vacuum.
- the crude product was stirred in 10 ml of dichlorometane and the precipitate was filtered off. The filtrate was concentrated under vacuum and 480 mg of the desired product (2.45 mmol) were obtained as an oil.
- 3-(trifluoromethyl)benzaldheyde (6.46 ml, 48.24 mmol) was dissolved in 80 ml of dry tetrahydrofurane, the reaction mixture was cooled to ⁇ 78° C. and a 0.5M solution of 3-butenylmagnesiumbromide in tetrahydrofurane (106.13 ml, 53.06 mmol) was added dropwise over 30 minutes. The reaction mixture was stirred at ⁇ 78° C. for 30 minutes. Then, the reaction mixture was allowed to reach room temperature and stirred 18 h. Then, 100 ml of a saturated aqueous solution of ammonium chloride and 200 ml of ethyl acetate were added. the organic layer was separated, dried over sodium sulfate and concentrated under vacuum. 7.75 g (33.69 mmol) of the desired product were obtained.
- the phtalimido intermediate (1.2 g, 3.2 mmol) was dissolved in 15 ml of methanol. Hydrazine hydrate (1.24 ml, 25.60 mmol) was added and the reaction mixture was stirred at room temperature for 48 h. The reaction mixture was concentrated under vacuum.
- the crude product was dissolved in 10 ml of dichlorometane, the organic layer was washed with water, separated, dried on sodium sulfate and concentrate under vacuum. 474 mg (1.93 mmol) of the desired product were obtained.
- Example 104 The following examples were synthesized in analogy to the preparation of Example 104.
- Example 228b (22 mg, 0.032 mmol), formaldehyde (0.003 ml, 0.096 mmol), N,N-diisopropyl-ethylamine (0.008 ml, 0.048 mmol) and trifluoroacetic acid (0.005 ml) in 1.5 ml of methanol were stirred at room temperature for 5 min.
- Sodium cyanoborohydride (10 mg, 0.160 mmol) was added and the reaction mixture was stirred at room temperature overnight. The organic phase was concentrated under vacuum.
- Example 290 The following example was synthesized in analogy to the preparation of Example 290.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08172336.3 | 2008-12-19 | ||
EP08172336 | 2008-12-19 | ||
EP09160416 | 2009-05-15 | ||
EP09160416.5 | 2009-05-15 | ||
PCT/EP2009/067378 WO2010070032A1 (en) | 2008-12-19 | 2009-12-17 | Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/067378 A-371-Of-International WO2010070032A1 (en) | 2008-12-19 | 2009-12-17 | Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/949,696 Continuation US8835440B2 (en) | 2008-12-19 | 2013-07-24 | Cyclic pyrimidin-4-carboxamides as CCR2 receptor antagonists for treatment of inflammation, asthma and COPD |
Publications (1)
Publication Number | Publication Date |
---|---|
US20120053164A1 true US20120053164A1 (en) | 2012-03-01 |
Family
ID=42049604
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/140,591 Abandoned US20120053164A1 (en) | 2008-12-19 | 2009-12-17 | Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd |
US13/949,696 Active US8835440B2 (en) | 2008-12-19 | 2013-07-24 | Cyclic pyrimidin-4-carboxamides as CCR2 receptor antagonists for treatment of inflammation, asthma and COPD |
US14/445,137 Active US9067951B2 (en) | 2008-12-19 | 2014-07-29 | Process and intermediates for the production of CCR2 antagonists |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/949,696 Active US8835440B2 (en) | 2008-12-19 | 2013-07-24 | Cyclic pyrimidin-4-carboxamides as CCR2 receptor antagonists for treatment of inflammation, asthma and COPD |
US14/445,137 Active US9067951B2 (en) | 2008-12-19 | 2014-07-29 | Process and intermediates for the production of CCR2 antagonists |
Country Status (28)
Country | Link |
---|---|
US (3) | US20120053164A1 (zh) |
EP (2) | EP2816040B1 (zh) |
JP (2) | JP2012512834A (zh) |
KR (1) | KR101754698B1 (zh) |
CN (2) | CN102256963B (zh) |
AR (1) | AR074814A1 (zh) |
AU (1) | AU2009327127C1 (zh) |
BR (1) | BRPI0923051B1 (zh) |
CA (1) | CA2747677C (zh) |
CL (1) | CL2011001322A1 (zh) |
CO (1) | CO6382124A2 (zh) |
DK (1) | DK2379525T3 (zh) |
EA (1) | EA020548B1 (zh) |
EC (1) | ECSP11011163A (zh) |
ES (1) | ES2551557T3 (zh) |
HK (1) | HK1159099A1 (zh) |
HU (1) | HUE025547T2 (zh) |
IL (1) | IL212605A (zh) |
MA (1) | MA33085B1 (zh) |
MX (1) | MX2011005150A (zh) |
NZ (1) | NZ592723A (zh) |
PE (1) | PE20120061A1 (zh) |
PL (1) | PL2379525T3 (zh) |
SG (1) | SG172289A1 (zh) |
TN (1) | TN2011000310A1 (zh) |
TW (1) | TWI478913B (zh) |
WO (1) | WO2010070032A1 (zh) |
ZA (1) | ZA201103158B (zh) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100204209A1 (en) * | 2007-05-31 | 2010-08-12 | Boehringer Ingelheim International Gmbh | CCR2 Receptor Antagonists and Uses Thereof |
US20110053912A1 (en) * | 2009-03-30 | 2011-03-03 | Astellas Pharma Inc. | Pyrimidine compound |
US8765949B2 (en) | 2009-12-17 | 2014-07-01 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists and uses thereof |
US8835440B2 (en) | 2008-12-19 | 2014-09-16 | Boehringer Ingelheim International Gmbh | Cyclic pyrimidin-4-carboxamides as CCR2 receptor antagonists for treatment of inflammation, asthma and COPD |
US8841313B2 (en) | 2010-05-17 | 2014-09-23 | Boehringer Ingelheim International Gmbh | CCR2 antagonists and uses thereof |
US8877745B2 (en) | 2010-05-12 | 2014-11-04 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
US8946218B2 (en) | 2010-05-12 | 2015-02-03 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
US8962656B2 (en) | 2010-06-01 | 2015-02-24 | Boehringer Ingelheim International Gmbh | CCR2 antagonists |
US9018212B2 (en) | 2010-05-25 | 2015-04-28 | Boehringer Ingelheim International Gmbh | Pyridazine carboxamides as CCR2 receptor antagonists |
US9108958B2 (en) | 2011-07-15 | 2015-08-18 | Boehringer Ingelheim International Gmbh | Selective CCR2 antagonists |
US10213428B2 (en) | 2015-07-02 | 2019-02-26 | Centrexion Therapeutics Corporation | (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
MY191407A (en) | 2008-01-04 | 2022-06-27 | Intellikine Llc | Certain chemical entities, compositions and methods |
JP5731978B2 (ja) | 2008-09-26 | 2015-06-10 | インテリカイン, エルエルシー | 複素環キナーゼ阻害剤 |
WO2010129816A2 (en) | 2009-05-07 | 2010-11-11 | Intellikine, Inc. | Heterocyclic compounds and uses thereof |
US8338441B2 (en) | 2009-05-15 | 2012-12-25 | Gilead Sciences, Inc. | Inhibitors of human immunodeficiency virus replication |
EP2513086B1 (en) * | 2009-12-17 | 2015-04-29 | Boehringer Ingelheim International GmbH | Novel antagonists for ccr2 and uses thereof |
EP2571357B1 (en) | 2010-05-21 | 2016-07-06 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
EP2637669A4 (en) | 2010-11-10 | 2014-04-02 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and their use |
DK2663309T3 (en) | 2011-01-10 | 2017-06-19 | Infinity Pharmaceuticals Inc | METHODS FOR PRODUCING ISOQUINOLINONES AND SOLID FORMS OF ISOQUINOLINONES |
EP2721025B1 (en) | 2011-06-16 | 2015-11-25 | Boehringer Ingelheim International Gmbh | New selective ccr2 antagonists |
EP2734520B1 (en) | 2011-07-19 | 2016-09-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
CN103946226A (zh) | 2011-07-19 | 2014-07-23 | 无限药品股份有限公司 | 杂环化合物及其应用 |
SG11201400310WA (en) | 2011-08-29 | 2014-06-27 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
CA2852160A1 (en) | 2011-10-28 | 2013-05-02 | Galderma Research & Development | New leukocyte infiltrate markers for rosacea and uses thereof |
BR112014012056B1 (pt) | 2011-11-18 | 2021-12-14 | Heptares Therapeutics Limited | Compostos agonistas do receptor m1 muscarínico, composição farmacêutica compreendendo os ditos compostos e uso dos mesmos para tratar um distúrbio cognitivo ou psicótico ou para tratamento ou diminuição da severidade da dor aguda, crônica, neuropática ou inflamatória |
US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
JP2015529651A (ja) * | 2012-08-01 | 2015-10-08 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | α7ニコチン性アセチルコリン受容体モジュレーターおよびそれらの使用−I |
UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
CA2893962C (en) | 2012-12-06 | 2021-04-06 | Enlivex Therapeutics Ltd | Therapeutic apoptotic cell preparations, method for producing same and uses thereof |
CN103102261A (zh) * | 2013-02-06 | 2013-05-15 | 上海药明康德新药开发有限公司 | 一种螺[2.5]辛烷-5-羧酸的合成方法 |
US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
BR112016007467B1 (pt) | 2013-10-04 | 2022-09-20 | Infinity Pharmaceuticals, Inc | Compostos heterocíclicos e usos dos mesmos |
JOP20200052A1 (ar) * | 2013-12-19 | 2017-06-16 | Bayer Pharma AG | بيبريدينيل تتراهيدرو كوينولينات مستبدلة واستخدامها كمعضدات مستقبل أدريني ألفا- 2c |
JP6701088B2 (ja) | 2014-03-19 | 2020-05-27 | インフィニティー ファーマシューティカルズ, インコーポレイテッド | Pi3k−ガンマ媒介障害の治療で使用するための複素環式化合物 |
WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
EP3613435A1 (en) | 2015-01-28 | 2020-02-26 | Universite De Bordeaux | Chemokine receptor cxcr4 inhibitors for treating and/or preventing chronic obstructive pulmonary disease |
EP3350183A1 (en) | 2015-09-14 | 2018-07-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
GB201519194D0 (en) * | 2015-10-30 | 2015-12-16 | Heptares Therapeutics Ltd | CGRP receptor antagonists |
WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
HRP20211960T1 (hr) | 2016-03-22 | 2022-03-18 | Merck Sharp & Dohme Corp. | Alosterični modulatori nikotinskih acetilcolinskih receptora |
US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
WO2017223422A1 (en) | 2016-06-24 | 2017-12-28 | Infinity Pharmaceuticals, Inc. | Combination therapies |
GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
CN108017599B (zh) * | 2016-11-04 | 2020-03-03 | 上海爱科百发生物医药技术有限公司 | [3-(胺甲基)-氧杂环丁烷-3-基]氨基甲酸对甲氧基苄酯对氯苯甲酸盐合成方法 |
GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
WO2022271982A1 (en) * | 2021-06-23 | 2022-12-29 | Synaptive Therapeutics, Llc | Substituted phenethylamine for treating inflammation and psychological disorders |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007026959A2 (en) * | 2005-08-31 | 2007-03-08 | Otsuka Pharmaceutical Co., Ltd. | Derivatives of 4-piperazin-1-yl-4-benz0 [b] thiophene suitable for the treatment of cns disorders |
US20110183957A1 (en) * | 2008-08-04 | 2011-07-28 | John Wityak | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
US20120004252A1 (en) * | 2009-12-17 | 2012-01-05 | Boehringer Ingelheim International Gmbh | New ccr2 receptor antagonists and uses thereof |
US8110575B2 (en) * | 2007-11-22 | 2012-02-07 | Boehringer Ingelheim International Gmbh | Compounds |
US20120108572A1 (en) * | 2008-09-02 | 2012-05-03 | Boehringer Ingelheim International Gmbh | Novel benzamides, production thereof, and use thereof as medicaments |
Family Cites Families (117)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4032526A (en) | 1975-10-02 | 1977-06-28 | American Cyanamid Company | 1,2-dimethyl-3 or 5-piperazinyl-pyrazolium salts |
US4426382A (en) | 1980-02-13 | 1984-01-17 | Sankyo Company Limited | 4-Amino-6,7-dimethoxy-2-piperazinylquinazoline derivatives, their preparation and use |
US4621305A (en) | 1984-08-22 | 1986-11-04 | General Motors Corporation | Header connector and attachment |
DE3517617A1 (de) | 1985-05-15 | 1986-11-20 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Neue pyridaziniumverbindungen, verfahren zu deren herstellung und diese enthaltende fungizide und algizide mittel |
DE3931432A1 (de) * | 1989-09-21 | 1991-04-04 | Hoechst Ag | Pyrimidin-4,6-dicarbonsaeurediamide, verfahren zu deren herstellung sowie verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
US5096916A (en) * | 1990-05-07 | 1992-03-17 | Aegis Technology, Inc. | Treatment of chronic obstructive pulmonary disease (copd) by inhalation of an imidazoline |
CA2146019A1 (en) | 1992-10-23 | 1994-05-11 | Howard B. Broughton | Dopamine receptor subtype ligands |
JP3166376B2 (ja) | 1993-02-03 | 2001-05-14 | 松下電器産業株式会社 | 熱利用装置 |
TW531537B (en) * | 1995-12-27 | 2003-05-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives |
US5629325A (en) | 1996-06-06 | 1997-05-13 | Abbott Laboratories | 3-pyridyloxymethyl heterocyclic ether compounds useful in controlling chemical synaptic transmission |
US6437138B1 (en) | 1996-06-06 | 2002-08-20 | Abbott Laboratories | 3-pyridyloxymethyl heterocyclic ether compounds useful in controlling chemical synaptic transmission |
US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
US6979686B1 (en) | 2001-12-07 | 2005-12-27 | Pharmacia Corporation | Substituted pyrazoles as p38 kinase inhibitors |
BR9813279B1 (pt) | 1997-10-27 | 2010-11-16 | derivado de homopiperazina, composição farmacêutica, e, uso do derivado de homopiperazina. | |
EP1131318B1 (en) | 1998-11-20 | 2004-03-24 | G.D. Searle LLC | Process for making 5-substituted pyrazoles using dithietanes |
US6248755B1 (en) | 1999-04-06 | 2001-06-19 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
ATE299865T1 (de) | 1999-05-04 | 2005-08-15 | Schering Corp | Piperazinderivate verwendbar als ccr5 antagonisten |
AU2001229501A1 (en) | 2000-01-24 | 2001-07-31 | Isis Pharmaceuticals, Inc. | Antisense modulation of inducible nitric oxide synthase expression |
GB0004153D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
US20020045613A1 (en) | 2000-04-27 | 2002-04-18 | Heinz Pauls | 1-aroyl-piperidinyl benzamidines |
OA12274A (en) | 2000-05-22 | 2006-05-09 | Aventis Pharma Inc | Arylmethylamine derivatives for use as tryptase inhibitors. |
EP1468998A1 (de) | 2000-10-12 | 2004-10-20 | Boehringer Ingelheim Pharma GmbH & Co. KG | Kristallines Monohydrat von Tiotropiumbromid und Verfahren zu dessen Herstellung. |
AR035700A1 (es) | 2001-05-08 | 2004-06-23 | Astrazeneca Ab | Derivados de arilheteroalquilamina, composicion farmaceutica, usos de estos derivados para la fabricacion de medicamentos, metodos de tratamiento, y proceso para la preparacion de estos derivados |
ES2271280T3 (es) | 2001-06-22 | 2007-04-16 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | Anticolinergico cristalino, procedimiento para su preparacion y su uso para la produccion de un medicamento. |
AU2002363236A1 (en) | 2001-10-30 | 2003-05-12 | Millennium Pharmaceuticals, Inc. | Compounds, pharmaceutical compositions and methods of use therefor |
US6806279B2 (en) | 2001-12-17 | 2004-10-19 | Sunesis Pharmaceuticals, Inc. | Small-molecule inhibitors of interleukin-2 |
IL162859A0 (en) | 2002-02-05 | 2005-11-20 | Novo Nordisk As | Novel aryl-and heteroarylpiperazines |
HUP0200849A2 (hu) | 2002-03-06 | 2004-08-30 | Sanofi-Synthelabo | N-aminoacetil-2-ciano-pirrolidin-származékok, e vegyületeket tartalmazó gyógyszerkészítmények és eljárás előállításukra |
US20030195192A1 (en) | 2002-04-05 | 2003-10-16 | Fortuna Haviv | Nicotinamides having antiangiogenic activity |
CA2476586C (en) | 2002-03-13 | 2011-11-01 | Janssen Pharmaceutica N.V. | Sulfonyl-derivatives as novel inhibitors of histone deacetylase |
US20040014744A1 (en) | 2002-04-05 | 2004-01-22 | Fortuna Haviv | Substituted pyridines having antiangiogenic activity |
EP1498125A4 (en) | 2002-04-24 | 2008-08-20 | Takeda Pharmaceutical | USE OF ANTI-CCR ANTAGONISM COMPOUNDS |
WO2003092586A2 (en) | 2002-04-29 | 2003-11-13 | Merck & Co., Inc. | Tetrahydropyranyl cyclopentyl tetrahydropyridopyridine modulators of chemokine receptor activity |
JP2005538958A (ja) | 2002-06-05 | 2005-12-22 | ファルマシア・コーポレーション | p38キナーゼ阻害薬としてのピラゾール誘導体 |
WO2004024710A1 (en) | 2002-09-13 | 2004-03-25 | Glaxo Group Limited | Urea compounds active as vanilloid receptor antagonists for the treatment of pain |
SE0203304D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Coumpounds |
GB0229618D0 (en) | 2002-12-19 | 2003-01-22 | Cancer Rec Tech Ltd | Pyrazole compounds |
US20040147561A1 (en) | 2002-12-27 | 2004-07-29 | Wenge Zhong | Pyrid-2-one derivatives and methods of use |
WO2004074438A2 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
JP4027406B2 (ja) | 2003-03-12 | 2007-12-26 | クドス ファーマシューティカルズ リミテッド | フタラジノン誘導体 |
SI1615909T1 (sl) | 2003-04-23 | 2008-12-31 | Glaxo Group Ltd | Derivati piperazina in njihova uporaba za zdravljenje nevroloĺ kih in psihiatriäśnih bolezni |
FR2854158B1 (fr) | 2003-04-25 | 2006-11-17 | Sanofi Synthelabo | Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique |
AR045999A1 (es) | 2003-07-18 | 2005-11-23 | Glaxo Group Ltd | Compuesto de eter de piperidina, su uso para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para prepararlo |
BRPI0413048A (pt) | 2003-07-29 | 2006-10-17 | Novo Nordisk As | composto, composição farmacêutica, uso de um composto, e, método para o tratamento de distúrbios ou doenças relacionados com o receptor h3 da histamina |
CN102344398B (zh) | 2003-12-18 | 2015-02-25 | 因赛特公司 | 作为趋化因子受体调控剂的3-环烷基氨基吡咯烷衍生物 |
GB0403155D0 (en) * | 2004-02-12 | 2004-03-17 | Vernalis Res Ltd | Chemical compounds |
AU2005219438B2 (en) | 2004-03-03 | 2011-02-17 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
PE20060285A1 (es) | 2004-03-30 | 2006-05-08 | Aventis Pharma Inc | Piridonas sustituidas como inhibidores de pol(adp-ribosa)-polimerasa (parp) |
WO2005097751A2 (en) | 2004-03-31 | 2005-10-20 | Janssen Pharmaceutica, N.V. | Non-imidazole heterocyclic compounds as histamine h3-receptor ligands |
EP1750727A2 (en) | 2004-04-23 | 2007-02-14 | Exelixis, Inc. | Kinase modulators and methods of use |
EP1753740A2 (en) | 2004-05-21 | 2007-02-21 | Merck & Co., Inc. | Amino cyclopentyl heterocyclic and carbocyclic modulators of chemokine receptor activity |
MEP8409A (en) | 2004-06-02 | 2011-12-20 | Fused heterocyclic compound | |
FR2871157A1 (fr) | 2004-06-04 | 2005-12-09 | Aventis Pharma Sa | Produits biaryl aromatiques, compositions les contenant et utilisation |
JP2008504275A (ja) | 2004-06-24 | 2008-02-14 | インサイト・コーポレイション | N−置換ピペリジンおよびその医薬としての使用 |
KR101229416B1 (ko) | 2004-06-25 | 2013-02-05 | 얀센 파마슈티카 엔.브이. | 사차염 ccr2 길항제 |
KR100856155B1 (ko) | 2004-06-28 | 2008-09-03 | 인사이트 코포레이션 | 케모카인 수용체의 조절자로서의3-아미노사이클로펜탄카복스아마이드 |
BRPI0514632A (pt) * | 2004-08-26 | 2008-06-17 | Kudos Pharm Ltd | derivados de ftalazinona 4-heteroarilmetila substituìdos |
GB0419072D0 (en) * | 2004-08-26 | 2004-09-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
GB0420831D0 (en) | 2004-09-17 | 2004-10-20 | Glaxo Group Ltd | Novel compounds |
EP1807085B1 (en) | 2004-09-20 | 2013-08-21 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
GB0421525D0 (en) * | 2004-09-28 | 2004-10-27 | Novartis Ag | Inhibitors of protein kineses |
WO2006038734A1 (en) | 2004-10-08 | 2006-04-13 | Astellas Pharma Inc. | Pyridazinone derivatives cytokines inhibitors |
ES2543813T3 (es) | 2004-11-02 | 2015-08-24 | Northwestern University | Compuestos de piridazina para el tratamiento de enfermedades inflamatorias |
PA8653301A1 (es) | 2004-11-22 | 2006-11-09 | Incyte Corp Incyte Corp | Sales de la n-[2-({(3r)-1-[trans-4-hidroxi-4-(6-metoxipiridin-3-il) ciclohexil)pirrolidin |
DE102004061751A1 (de) | 2004-12-22 | 2006-07-06 | Bayer Healthcare Ag | Cyanoguanidin-substituierte Pyrazoline |
US7919495B2 (en) | 2005-02-17 | 2011-04-05 | Astellas Pharma, Inc. | Pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound |
US20060235028A1 (en) | 2005-04-14 | 2006-10-19 | Li James J | Inhibitors of 11-beta hydroxysteroid dehydrogenase type I |
EP1877401A2 (en) | 2005-04-15 | 2008-01-16 | Elan Pharmaceuticals Inc. | Novel compounds useful for bradykinin b1 receptor antagonism |
AU2006236387A1 (en) | 2005-04-18 | 2006-10-26 | Neurogen Corporation | Subtituted heteroaryl CB1 antagonists |
BRPI0612796A2 (pt) | 2005-05-11 | 2010-11-30 | Nycomed Gmbh | combinação de um inibidor da pde4 e um derivado da tetraidrobiopterina |
ATE540948T1 (de) | 2005-05-20 | 2012-01-15 | Vertex Pharma | Pyrrolopyridine als proteinkinasehemmer |
ATE536344T1 (de) | 2005-07-04 | 2011-12-15 | High Point Pharmaceuticals Llc | Histamine h3 receptor antagonisten |
CA2606004A1 (en) | 2005-08-02 | 2007-02-08 | Neurogen Corporation | Dipiperazinyl ketones and related analogues |
GB0517184D0 (en) | 2005-08-22 | 2005-09-28 | Glaxo Group Ltd | Compounds |
TW200800999A (en) | 2005-09-06 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
NZ566862A (en) | 2005-09-27 | 2010-12-24 | Irm Llc | Diarylamine-containing compounds and compositions, and their use as modulators of C-kit receptors |
JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
US20100016289A1 (en) | 2005-11-01 | 2010-01-21 | Kevin Sprott | Compounds Useful as Antagonists of CCR2 |
WO2007053498A1 (en) | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of ccr2 |
CN101309915A (zh) | 2005-11-14 | 2008-11-19 | Irm责任有限公司 | 作为lxr调节剂的化合物和组合物 |
AU2006329007A1 (en) * | 2005-12-20 | 2007-06-28 | Novartis Ag | Nicotinic acid derivatives as modulators of metabotropic glutamate receptors |
WO2007084868A2 (en) | 2006-01-17 | 2007-07-26 | Kalypsys, Inc. | Treatment of disorders by activation of the unfolded protein response |
JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
AU2007221020B9 (en) | 2006-02-28 | 2013-04-04 | Dart Neuroscience (Cayman) Ltd. | Therapeutic compounds |
EP2024353A2 (en) | 2006-03-16 | 2009-02-18 | Pfizer Products Inc. | Pyrazole compounds |
AU2007238878A1 (en) | 2006-04-11 | 2007-10-25 | Merck Sharp & Dohme Corp. | Diaryl substituted alkanes |
US7807671B2 (en) | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
EP2015751A2 (en) | 2006-04-28 | 2009-01-21 | Northwestern University | Salts of pyridazine compounds |
BRPI0713328A2 (pt) | 2006-06-22 | 2012-10-30 | Biovitrum Ab | derivados de piridina e pirazina como inibidores de cinase mnk |
GB0617575D0 (en) | 2006-09-06 | 2006-10-18 | Syngenta Ltd | Herbicidal compounds and compositions |
EP2099454A4 (en) * | 2006-11-17 | 2010-11-10 | Abbott Lab | AMINOPYRROLIDINES AS CHEMOKINE RECEPTOR ANTAGONISTS |
PL2698062T3 (pl) | 2006-12-28 | 2015-12-31 | Abbvie Inc | Inhibitory polimerazy poli(adp-rybozy) |
US20100204230A1 (en) | 2007-02-12 | 2010-08-12 | Peter Blurton | Piperazine derivatives for treatment of ad and related conditions |
JP4785881B2 (ja) | 2007-02-27 | 2011-10-05 | 大塚製薬株式会社 | 医薬 |
FR2915552B1 (fr) | 2007-04-27 | 2009-11-06 | Technip France | Conduite tubulaire flexible pour le transport d'hydrocarbures gazeux. |
EP2155689B1 (en) | 2007-05-31 | 2015-07-08 | Boehringer Ingelheim International GmbH | Ccr2 receptor antagonists and uses thereof |
JP5431316B2 (ja) | 2007-07-02 | 2014-03-05 | エフ.ホフマン−ラ ロシュ アーゲー | Ccr2受容体アンタゴニストとしてのイミダゾール誘導体 |
US7977358B2 (en) | 2007-07-26 | 2011-07-12 | Hoffmann-La Roche Inc. | Pyrazol derivatives |
EP2042516A1 (en) | 2007-09-27 | 2009-04-01 | Protaffin Biotechnologie AG | Glycosaminoglycan-antagonising MCP-1 mutants and methods of using same |
BRPI0815572A2 (pt) | 2007-08-22 | 2015-02-18 | Irm Llc | Compostos e composições como inibidores de quinases |
JP2010540584A (ja) | 2007-10-01 | 2010-12-24 | エフ.ホフマン−ラ ロシュ アーゲー | Ccr受容体アンタゴニストとしてのn−複素環ビアリールカルボキサミド類 |
WO2009048238A2 (en) | 2007-10-12 | 2009-04-16 | Jong O Whang | Tying tool for shoelace |
US20090131417A1 (en) | 2007-11-20 | 2009-05-21 | Letavic Michael A | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
WO2009066084A1 (en) * | 2007-11-21 | 2009-05-28 | F. Hoffmann-La Roche Ag | 2 -morpholinopyrimidines and their use as pi3 kinase inhibitors |
WO2009065919A2 (de) * | 2007-11-22 | 2009-05-28 | Boehringer Ingelheim International Gmbh | Organische verbindungen |
CN102066359B (zh) | 2008-06-18 | 2013-08-21 | 弗·哈夫曼-拉罗切有限公司 | 杂芳基甲酰胺衍生物 |
GB0815369D0 (en) * | 2008-08-22 | 2008-10-01 | Summit Corp Plc | Compounds for treatment of duchenne muscular dystrophy |
EA020548B1 (ru) | 2008-12-19 | 2014-12-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Циклические пиримидин-4-карбоксамиды в качестве антагонистов рецептора ccr2, предназначенные для лечения воспаления, астмы и хозл |
EP2398796A4 (en) | 2009-02-23 | 2012-10-10 | Merck Canada Inc | HETEROCYCLIC DERIVATIVES AS INHIBITORS OF THE STEAROYL COENZYME A DELTA 9 DESATURASE |
EP2513086B1 (en) * | 2009-12-17 | 2015-04-29 | Boehringer Ingelheim International GmbH | Novel antagonists for ccr2 and uses thereof |
EP2569298B1 (en) | 2010-05-12 | 2015-11-25 | Boehringer Ingelheim International GmbH | Novel ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
US8946218B2 (en) | 2010-05-12 | 2015-02-03 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
JP5647339B2 (ja) | 2010-05-17 | 2014-12-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ccr2アンタゴニスト及びこれらの使用 |
US9018212B2 (en) | 2010-05-25 | 2015-04-28 | Boehringer Ingelheim International Gmbh | Pyridazine carboxamides as CCR2 receptor antagonists |
EP2576538B1 (en) | 2010-06-01 | 2015-10-28 | Boehringer Ingelheim International GmbH | New CCR2 antagonists |
EP2721025B1 (en) * | 2011-06-16 | 2015-11-25 | Boehringer Ingelheim International Gmbh | New selective ccr2 antagonists |
WO2013010839A1 (en) * | 2011-07-15 | 2013-01-24 | Boehringer Ingelheim International Gmbh | Novel and selective ccr2 antagonists |
-
2009
- 2009-12-17 EA EA201100942A patent/EA020548B1/ru not_active IP Right Cessation
- 2009-12-17 PE PE2011001236A patent/PE20120061A1/es not_active Application Discontinuation
- 2009-12-17 EP EP14177922.3A patent/EP2816040B1/en active Active
- 2009-12-17 JP JP2011541435A patent/JP2012512834A/ja not_active Withdrawn
- 2009-12-17 KR KR1020117014060A patent/KR101754698B1/ko active IP Right Grant
- 2009-12-17 SG SG2011045242A patent/SG172289A1/en unknown
- 2009-12-17 BR BRPI0923051-3A patent/BRPI0923051B1/pt active IP Right Grant
- 2009-12-17 WO PCT/EP2009/067378 patent/WO2010070032A1/en active Application Filing
- 2009-12-17 CA CA2747677A patent/CA2747677C/en active Active
- 2009-12-17 DK DK09775212.5T patent/DK2379525T3/en active
- 2009-12-17 AU AU2009327127A patent/AU2009327127C1/en not_active Ceased
- 2009-12-17 HU HUE09775212A patent/HUE025547T2/en unknown
- 2009-12-17 ES ES09775212T patent/ES2551557T3/es active Active
- 2009-12-17 MX MX2011005150A patent/MX2011005150A/es active IP Right Grant
- 2009-12-17 MA MA33952A patent/MA33085B1/fr unknown
- 2009-12-17 US US13/140,591 patent/US20120053164A1/en not_active Abandoned
- 2009-12-17 CN CN200980150778.8A patent/CN102256963B/zh active Active
- 2009-12-17 CN CN201310682370.3A patent/CN103724328B/zh not_active Expired - Fee Related
- 2009-12-17 PL PL09775212T patent/PL2379525T3/pl unknown
- 2009-12-17 NZ NZ592723A patent/NZ592723A/xx unknown
- 2009-12-17 EP EP09775212.5A patent/EP2379525B1/en active Active
- 2009-12-18 TW TW098143774A patent/TWI478913B/zh not_active IP Right Cessation
- 2009-12-18 AR ARP090104997A patent/AR074814A1/es unknown
-
2011
- 2011-04-29 ZA ZA2011/03158A patent/ZA201103158B/en unknown
- 2011-05-01 IL IL212605A patent/IL212605A/en active IP Right Grant
- 2011-06-02 CL CL2011001322A patent/CL2011001322A1/es unknown
- 2011-06-17 TN TN2011000310A patent/TN2011000310A1/fr unknown
- 2011-06-23 CO CO11079269A patent/CO6382124A2/es active IP Right Grant
- 2011-06-24 EC EC2011011163A patent/ECSP11011163A/es unknown
- 2011-12-15 HK HK11113547.8A patent/HK1159099A1/zh not_active IP Right Cessation
-
2013
- 2013-07-24 US US13/949,696 patent/US8835440B2/en active Active
-
2014
- 2014-04-09 JP JP2014080374A patent/JP5686916B2/ja active Active
- 2014-07-29 US US14/445,137 patent/US9067951B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007026959A2 (en) * | 2005-08-31 | 2007-03-08 | Otsuka Pharmaceutical Co., Ltd. | Derivatives of 4-piperazin-1-yl-4-benz0 [b] thiophene suitable for the treatment of cns disorders |
US8110575B2 (en) * | 2007-11-22 | 2012-02-07 | Boehringer Ingelheim International Gmbh | Compounds |
US20110183957A1 (en) * | 2008-08-04 | 2011-07-28 | John Wityak | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
US20120108572A1 (en) * | 2008-09-02 | 2012-05-03 | Boehringer Ingelheim International Gmbh | Novel benzamides, production thereof, and use thereof as medicaments |
US20120004252A1 (en) * | 2009-12-17 | 2012-01-05 | Boehringer Ingelheim International Gmbh | New ccr2 receptor antagonists and uses thereof |
Non-Patent Citations (3)
Title |
---|
B.A. Chabner et al., Chemotherapy of Neoplastic Diseases, Neoplastic Agents in, GOODMAN & GILMAN'S: THE PHARMACOLOGICAL BASIS OF THERAPEUTICS 1315-1403, 1315 (L.L. Brunton et al., eds., 11th ed., 2006) * |
International Preliminary Report on Patentability, PCT/EP2009/067378 (Jun. 21, 2011) * |
J.H. Poupaert, Drug Design: Basic Principles and Applications, in 2 ENCYCLOPEDIA OF PHARMACEUTICAL TECHNOLOGY 1362-1369, 1367 (James Swarbrick ed., 3rd ed., 2007) * |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100204209A1 (en) * | 2007-05-31 | 2010-08-12 | Boehringer Ingelheim International Gmbh | CCR2 Receptor Antagonists and Uses Thereof |
US8653262B2 (en) | 2007-05-31 | 2014-02-18 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists and uses thereof |
US9067951B2 (en) | 2008-12-19 | 2015-06-30 | Boehringer Ingelheim International Gmbh | Process and intermediates for the production of CCR2 antagonists |
US8835440B2 (en) | 2008-12-19 | 2014-09-16 | Boehringer Ingelheim International Gmbh | Cyclic pyrimidin-4-carboxamides as CCR2 receptor antagonists for treatment of inflammation, asthma and COPD |
US20110053912A1 (en) * | 2009-03-30 | 2011-03-03 | Astellas Pharma Inc. | Pyrimidine compound |
US8524727B2 (en) * | 2009-03-30 | 2013-09-03 | Astellas Pharma Inc. | Pyrimidine compound |
US11731981B2 (en) | 2009-12-17 | 2023-08-22 | Centrexion Therapeutics Corporation | CCR2 receptor antagonists and uses thereof |
US10196402B2 (en) | 2009-12-17 | 2019-02-05 | Centrexion Therapeutics Corporation | CCR2 receptor antagonists and uses thereof |
US8765949B2 (en) | 2009-12-17 | 2014-07-01 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists and uses thereof |
US11046706B2 (en) | 2009-12-17 | 2021-06-29 | Centrexion Therapeutics Corporation | CCR2 receptor antagonists and uses thereof |
US9670222B2 (en) | 2009-12-17 | 2017-06-06 | Centrexion Therapeutics Corporation | CCR2 receptor antagonists and uses thereof |
US8877745B2 (en) | 2010-05-12 | 2014-11-04 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
US8946218B2 (en) | 2010-05-12 | 2015-02-03 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
US8841313B2 (en) | 2010-05-17 | 2014-09-23 | Boehringer Ingelheim International Gmbh | CCR2 antagonists and uses thereof |
US9018212B2 (en) | 2010-05-25 | 2015-04-28 | Boehringer Ingelheim International Gmbh | Pyridazine carboxamides as CCR2 receptor antagonists |
US8962656B2 (en) | 2010-06-01 | 2015-02-24 | Boehringer Ingelheim International Gmbh | CCR2 antagonists |
US9108958B2 (en) | 2011-07-15 | 2015-08-18 | Boehringer Ingelheim International Gmbh | Selective CCR2 antagonists |
US10213428B2 (en) | 2015-07-02 | 2019-02-26 | Centrexion Therapeutics Corporation | (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate |
US10568885B2 (en) | 2015-07-02 | 2020-02-25 | Centrexion Therapeutics Corporation | (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-y1)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-citrate |
US11147814B2 (en) | 2015-07-02 | 2021-10-19 | Centrexion Therapeutics Corporation | (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p- tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9067951B2 (en) | Process and intermediates for the production of CCR2 antagonists | |
US11731981B2 (en) | CCR2 receptor antagonists and uses thereof | |
US8653262B2 (en) | CCR2 receptor antagonists and uses thereof | |
US8877745B2 (en) | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments | |
US9108958B2 (en) | Selective CCR2 antagonists | |
US20130150354A1 (en) | New selective ccr2 antagonists | |
US8946218B2 (en) | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments | |
US8841313B2 (en) | CCR2 antagonists and uses thereof | |
US8962656B2 (en) | CCR2 antagonists | |
US9018212B2 (en) | Pyridazine carboxamides as CCR2 receptor antagonists | |
US20130143905A1 (en) | Novel antagonists for ccr2 and uses thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: BOEHRINGER INGELHEIM INTERNATIONAL GMBH, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:EBEL, HEINER;FRATTINI, SARA;GIOVANNINI, RICCARDO;AND OTHERS;SIGNING DATES FROM 20110706 TO 20110725;REEL/FRAME:026725/0198 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO PAY ISSUE FEE |
|
AS | Assignment |
Owner name: CENTREXION THERAPEUTICS CORPORATION, MARYLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:BOEHRINGER INGELHEIM INTERNATIONAL GMBH;REEL/FRAME:039967/0644 Effective date: 20151111 |
|
AS | Assignment |
Owner name: AVENUE VENTURE OPPORTUNITIES FUND, L.P., AS AGENT, NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:CENTREXION THERAPEUTICS CORPORATION;REEL/FRAME:064256/0125 Effective date: 20230711 |