JP2003526686A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003526686A5 JP2003526686A5 JP2001566747A JP2001566747A JP2003526686A5 JP 2003526686 A5 JP2003526686 A5 JP 2003526686A5 JP 2001566747 A JP2001566747 A JP 2001566747A JP 2001566747 A JP2001566747 A JP 2001566747A JP 2003526686 A5 JP2003526686 A5 JP 2003526686A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- phenylamino
- carbonitrile
- cyano
- quinoline
- 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.)
- Withdrawn
Links
- 125000004432 carbon atom Chemical group C* 0.000 description 60
- 239000008194 pharmaceutical composition Substances 0.000 description 21
- -1 nitro, carboxy Chemical group 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- IYVDPTGYWDFGTF-VOTSOKGWSA-N (e)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-3-chloroprop-2-enamide Chemical compound C12=CC(NC(=O)/C=C/Cl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 IYVDPTGYWDFGTF-VOTSOKGWSA-N 0.000 description 2
- IYVDPTGYWDFGTF-SREVYHEPSA-N (z)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-3-chloroprop-2-enamide Chemical compound C12=CC(NC(=O)\C=C/Cl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 IYVDPTGYWDFGTF-SREVYHEPSA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- RUGCZQOSGFAGFE-UHFFFAOYSA-N 4-(3,4-dibromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 RUGCZQOSGFAGFE-UHFFFAOYSA-N 0.000 description 2
- XFOAIBYWZWBMSL-UHFFFAOYSA-N 4-(3-hydroxy-2-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(O)=C1C XFOAIBYWZWBMSL-UHFFFAOYSA-N 0.000 description 2
- GEUFKSXFZJFSDI-UHFFFAOYSA-N 4-[3-(hydroxymethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CO)=C1 GEUFKSXFZJFSDI-UHFFFAOYSA-N 0.000 description 2
- AJSYUAVIQGKJFW-UHFFFAOYSA-N 6-amino-4-(3,4-dibromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 AJSYUAVIQGKJFW-UHFFFAOYSA-N 0.000 description 2
- IMBMTYREOJZAAW-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 IMBMTYREOJZAAW-UHFFFAOYSA-N 0.000 description 2
- GFPFGXYUPCOMGW-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC(N)=CC2=C1NC1=CC=CC(Br)=C1 GFPFGXYUPCOMGW-UHFFFAOYSA-N 0.000 description 2
- UPINFBFRHUFCMT-UHFFFAOYSA-N 6-amino-4-(3-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(F)=C1 UPINFBFRHUFCMT-UHFFFAOYSA-N 0.000 description 2
- NNUBNOJEKVJYEQ-UHFFFAOYSA-N 6-amino-4-[3-(dimethylamino)anilino]quinoline-3-carbonitrile Chemical compound CN(C)C1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 NNUBNOJEKVJYEQ-UHFFFAOYSA-N 0.000 description 2
- JSRLAMXXELZKLJ-UHFFFAOYSA-N 6-amino-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 JSRLAMXXELZKLJ-UHFFFAOYSA-N 0.000 description 2
- ATKJDNWWCUYWGP-UHFFFAOYSA-N 6-amino-4-[4-(dimethylamino)anilino]quinoline-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1NC1=C(C#N)C=NC2=CC=C(N)C=C12 ATKJDNWWCUYWGP-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- UMAUXDSUHUAKMF-UHFFFAOYSA-N chembl111586 Chemical compound C=12C=C(O)C(O)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 UMAUXDSUHUAKMF-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004970 halomethyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- LUNOJOWDCVLIRF-UHFFFAOYSA-N n-[3-cyano-4-(3,4-dibromoanilino)quinolin-6-yl]prop-2-enamide Chemical compound C1=C(Br)C(Br)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 LUNOJOWDCVLIRF-UHFFFAOYSA-N 0.000 description 2
- RRPOWKSQIHLYPG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-methylprop-2-enamide Chemical compound C12=CC(NC(=O)C(=C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 RRPOWKSQIHLYPG-UHFFFAOYSA-N 0.000 description 2
- GRPHFCRERCRTMQ-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 GRPHFCRERCRTMQ-UHFFFAOYSA-N 0.000 description 2
- YWUDVJHTWSRLEL-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-hydroxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCO)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 YWUDVJHTWSRLEL-UHFFFAOYSA-N 0.000 description 2
- MXBVVVDUUIDCNR-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCOC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 MXBVVVDUUIDCNR-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VTUZXOFBDITYJD-RMKNXTFCSA-N (e)-n-[4-(3-bromoanilino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 VTUZXOFBDITYJD-RMKNXTFCSA-N 0.000 description 1
- NASQXHHMCASBFI-QPJJXVBHSA-N (e)-n-[4-(3-bromoanilino)-3-cyano-7-ethoxyquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C=12C=C(NC(=O)\C=C\CN3CCOCC3)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 NASQXHHMCASBFI-QPJJXVBHSA-N 0.000 description 1
- SNKBFOKVNBZMBE-VMPITWQZSA-N (e)-n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 SNKBFOKVNBZMBE-VMPITWQZSA-N 0.000 description 1
- XXOLFZCJKCTSFL-ZZXKWVIFSA-N (e)-n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C=12C=C(NC(=O)\C=C\CN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 XXOLFZCJKCTSFL-ZZXKWVIFSA-N 0.000 description 1
- MPNMKIMGGUGYMJ-VMPITWQZSA-N (e)-n-[4-(3-bromoanilino)-3-cyano-8-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C(OC)=CC(NC(=O)\C=C\CN(C)C)=CC2=C1NC1=CC=CC(Br)=C1 MPNMKIMGGUGYMJ-VMPITWQZSA-N 0.000 description 1
- QROTXBMVKQDLPG-ZZXKWVIFSA-N (e)-n-[4-(3-bromoanilino)-3-cyano-8-methoxyquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C=1C2=C(NC=3C=C(Br)C=CC=3)C(C#N)=CN=C2C(OC)=CC=1NC(=O)\C=C\CN1CCOCC1 QROTXBMVKQDLPG-ZZXKWVIFSA-N 0.000 description 1
- ABDIOQXDBJMGHB-QPJJXVBHSA-N (e)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)/C=C/CN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 ABDIOQXDBJMGHB-QPJJXVBHSA-N 0.000 description 1
- CFVOLTWOOMEMAM-DUXPYHPUSA-N (e)-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]but-2-enamide Chemical compound C12=CC(NC(=O)/C=C/C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 CFVOLTWOOMEMAM-DUXPYHPUSA-N 0.000 description 1
- BYEZGHDYNSABOZ-VOTSOKGWSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(OC)C(NC(=O)/C=C/CN(CC)CC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 BYEZGHDYNSABOZ-VOTSOKGWSA-N 0.000 description 1
- OEDJWFCIVDMVRU-SNAWJCMRSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 OEDJWFCIVDMVRU-SNAWJCMRSA-N 0.000 description 1
- KXQYGHZAGFHMDJ-ARJAWSKDSA-N (z)-n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)\C=C/CN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 KXQYGHZAGFHMDJ-ARJAWSKDSA-N 0.000 description 1
- RIQABCQFNMRXGD-IHWYPQMZSA-N (z)-n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-enamide Chemical compound C12=CC(NC(=O)\C=C/COC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 RIQABCQFNMRXGD-IHWYPQMZSA-N 0.000 description 1
- BEQNFTJAPYVQLR-UHFFFAOYSA-N 2-(3-methylsulfanylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound CSC1=CC=CC(NC=2C(=CC3=CC(=CC=C3N=2)[N+]([O-])=O)C#N)=C1 BEQNFTJAPYVQLR-UHFFFAOYSA-N 0.000 description 1
- SGCYGYMSLXKPIT-UHFFFAOYSA-N 2-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CC2=CC=CC=C2N=C1OCCCN1CCOCC1 SGCYGYMSLXKPIT-UHFFFAOYSA-N 0.000 description 1
- RTJPSNFGGWVYTF-UHFFFAOYSA-N 2-(4-bromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CC2=CC([N+](=O)[O-])=CC=C2N=C1NC1=CC=C(Br)C=C1 RTJPSNFGGWVYTF-UHFFFAOYSA-N 0.000 description 1
- XGQFVVQUVDLUAW-UHFFFAOYSA-N 3-[(3-cyano-6,7-dimethoxyquinolin-4-yl)amino]-2-methylbenzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C(O)=O)=C1C XGQFVVQUVDLUAW-UHFFFAOYSA-N 0.000 description 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 1
- TZNVNORLQOCTMY-UHFFFAOYSA-N 4-(2,4-dihydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C=C1O TZNVNORLQOCTMY-UHFFFAOYSA-N 0.000 description 1
- FNAOGFPOADZWDT-UHFFFAOYSA-N 4-(2-amino-4,5-dimethylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(C)=C(C)C=C1N FNAOGFPOADZWDT-UHFFFAOYSA-N 0.000 description 1
- GGSWVTQHMOCNJI-UHFFFAOYSA-N 4-(2-chloro-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C=C1Cl GGSWVTQHMOCNJI-UHFFFAOYSA-N 0.000 description 1
- VVWPJQJYFBFVJH-UHFFFAOYSA-N 4-(2-hydroxy-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C=C1O VVWPJQJYFBFVJH-UHFFFAOYSA-N 0.000 description 1
- QUSXJYUXWFSQPQ-UHFFFAOYSA-N 4-(2-hydroxy-5-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(C)=CC=C1O QUSXJYUXWFSQPQ-UHFFFAOYSA-N 0.000 description 1
- GCNKUJAIEDINLA-UHFFFAOYSA-N 4-(2-hydroxy-6-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=C(C)C=CC=C1O GCNKUJAIEDINLA-UHFFFAOYSA-N 0.000 description 1
- LNBBTBLPDKHCPQ-UHFFFAOYSA-N 4-(3,4-dichloroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(Cl)C(Cl)=C1 LNBBTBLPDKHCPQ-UHFFFAOYSA-N 0.000 description 1
- WYUJPMJLGOVLKG-UHFFFAOYSA-N 4-(3,4-difluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 WYUJPMJLGOVLKG-UHFFFAOYSA-N 0.000 description 1
- PPNMPEHEXLGGID-UHFFFAOYSA-N 4-(3,4-dimethoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 PPNMPEHEXLGGID-UHFFFAOYSA-N 0.000 description 1
- MBEJRIMUDFCZSL-UHFFFAOYSA-N 4-(3,5-dibromo-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(Br)=C(O)C(Br)=C1 MBEJRIMUDFCZSL-UHFFFAOYSA-N 0.000 description 1
- YJBYKRFNOYCMSK-UHFFFAOYSA-N 4-(3,5-dichloro-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(Cl)=C(O)C(Cl)=C1 YJBYKRFNOYCMSK-UHFFFAOYSA-N 0.000 description 1
- XBFPRUXDYAQIOC-UHFFFAOYSA-N 4-(3-acetylanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C(C)=O)=C1 XBFPRUXDYAQIOC-UHFFFAOYSA-N 0.000 description 1
- MZQKSJFIOAVZJR-UHFFFAOYSA-N 4-(3-aminoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(N)=C1 MZQKSJFIOAVZJR-UHFFFAOYSA-N 0.000 description 1
- PVGQFSJIEXPGDS-UHFFFAOYSA-N 4-(3-azidoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(N=[N+]=[N-])=C1 PVGQFSJIEXPGDS-UHFFFAOYSA-N 0.000 description 1
- WLEQBEYGUJEPBI-UHFFFAOYSA-N 4-(3-bromo-4-fluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 WLEQBEYGUJEPBI-UHFFFAOYSA-N 0.000 description 1
- JCGYXRCAGZQKRK-UHFFFAOYSA-N 4-(3-bromo-4-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 JCGYXRCAGZQKRK-UHFFFAOYSA-N 0.000 description 1
- BOXDQGATHFGEIB-UHFFFAOYSA-N 4-(3-bromo-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(Br)=C1 BOXDQGATHFGEIB-UHFFFAOYSA-N 0.000 description 1
- UHTFOMCCUZQBMM-UHFFFAOYSA-N 4-(3-bromoanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=CC(Br)=C1 UHTFOMCCUZQBMM-UHFFFAOYSA-N 0.000 description 1
- VXMFIYMOOZZNJO-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=CC(Br)=C1 VXMFIYMOOZZNJO-UHFFFAOYSA-N 0.000 description 1
- NVHCPPNJEXAXNA-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-bis(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 NVHCPPNJEXAXNA-UHFFFAOYSA-N 0.000 description 1
- TUZMSVARIRHFNQ-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-bis(methoxymethoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCOC)C(OCOC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 TUZMSVARIRHFNQ-UHFFFAOYSA-N 0.000 description 1
- PADYONKQSSWAFW-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dibutoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCCCC)C(OCCCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 PADYONKQSSWAFW-UHFFFAOYSA-N 0.000 description 1
- ZXILYRWRAKLTOG-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 ZXILYRWRAKLTOG-UHFFFAOYSA-N 0.000 description 1
- CQKFTSMPIIYOBX-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 CQKFTSMPIIYOBX-UHFFFAOYSA-N 0.000 description 1
- LRIHFKGXXJKDDD-UHFFFAOYSA-N 4-(3-bromoanilino)-6,7-dipropoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCCC)C(OCCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 LRIHFKGXXJKDDD-UHFFFAOYSA-N 0.000 description 1
- BWXDTMBEXXDSQD-UHFFFAOYSA-N 4-(3-bromoanilino)-6-(3-pyrrolidin-1-ylpropylamino)quinoline-3-carbonitrile Chemical compound BrC1=CC=CC(NC=2C3=CC(NCCCN4CCCC4)=CC=C3N=CC=2C#N)=C1 BWXDTMBEXXDSQD-UHFFFAOYSA-N 0.000 description 1
- MCIICVWNGVSLPW-UHFFFAOYSA-N 4-(3-bromoanilino)-6-(dimethylamino)quinoline-3-carbonitrile;hydrochloride Chemical compound Cl.C12=CC(N(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 MCIICVWNGVSLPW-UHFFFAOYSA-N 0.000 description 1
- IKOYWGLBVGPRAG-UHFFFAOYSA-N 4-(3-bromoanilino)-6-ethoxy-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OC)C(OCC)=CC2=C1NC1=CC=CC(Br)=C1 IKOYWGLBVGPRAG-UHFFFAOYSA-N 0.000 description 1
- IYPAMCYSGUYVAN-UHFFFAOYSA-N 4-(3-bromoanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=CC(Br)=C1 IYPAMCYSGUYVAN-UHFFFAOYSA-N 0.000 description 1
- SNLXBZYKYWEIOV-UHFFFAOYSA-N 4-(3-bromoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 SNLXBZYKYWEIOV-UHFFFAOYSA-N 0.000 description 1
- WCNVEOXERDZIOX-UHFFFAOYSA-N 4-(3-bromoanilino)-7-ethoxy-6-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 WCNVEOXERDZIOX-UHFFFAOYSA-N 0.000 description 1
- QHDFGPMRPDDNDN-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 QHDFGPMRPDDNDN-UHFFFAOYSA-N 0.000 description 1
- BISJVYCVPJVRKJ-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 BISJVYCVPJVRKJ-UHFFFAOYSA-N 0.000 description 1
- NUBVTRDETNNCGY-UHFFFAOYSA-N 4-(3-bromoanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=CC(Br)=C1 NUBVTRDETNNCGY-UHFFFAOYSA-N 0.000 description 1
- OESIRSGDGHCWFH-UHFFFAOYSA-N 4-(3-bromoanilino)-8-[(dimethylamino)methyl]-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(CN(C)C)=CC([N+]([O-])=O)=CC2=C1NC1=CC=CC(Br)=C1 OESIRSGDGHCWFH-UHFFFAOYSA-N 0.000 description 1
- PYGUWPNNELOZLP-UHFFFAOYSA-N 4-(3-bromoanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC(Br)=C1 PYGUWPNNELOZLP-UHFFFAOYSA-N 0.000 description 1
- AFOMMVJBDXYOAA-UHFFFAOYSA-N 4-(3-bromoanilino)-8-methyl-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(C)=CC([N+]([O-])=O)=CC2=C1NC1=CC=CC(Br)=C1 AFOMMVJBDXYOAA-UHFFFAOYSA-N 0.000 description 1
- JPDTVCOEUUQNSS-UHFFFAOYSA-N 4-(3-bromophenoxy)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1OC1=CC=CC(Br)=C1 JPDTVCOEUUQNSS-UHFFFAOYSA-N 0.000 description 1
- GLDODVVYHDNXHG-UHFFFAOYSA-N 4-(3-chloro-2-thiophen-3-yloxyanilino)-6-nitroquinoline-3-carbonitrile Chemical compound ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)[N+](=O)[O-])C#N)OC=1C=CSC=1 GLDODVVYHDNXHG-UHFFFAOYSA-N 0.000 description 1
- VJTVBWNBERHDKM-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 VJTVBWNBERHDKM-UHFFFAOYSA-N 0.000 description 1
- OPYYYPKXOUKXEH-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 OPYYYPKXOUKXEH-UHFFFAOYSA-N 0.000 description 1
- IJAFEDNMGMKIIZ-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 IJAFEDNMGMKIIZ-UHFFFAOYSA-N 0.000 description 1
- DUDXBCAIXIMAKI-UHFFFAOYSA-N 4-(3-chloro-4-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C(Cl)=C1 DUDXBCAIXIMAKI-UHFFFAOYSA-N 0.000 description 1
- OTTMSKLASSZGJD-UHFFFAOYSA-N 4-(3-chloro-4-methoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 OTTMSKLASSZGJD-UHFFFAOYSA-N 0.000 description 1
- OSNTXNDDUYHOPC-UHFFFAOYSA-N 4-(3-chloro-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(Cl)=C1 OSNTXNDDUYHOPC-UHFFFAOYSA-N 0.000 description 1
- PSZDFZSOCJHJRP-UHFFFAOYSA-N 4-(3-chloro-4-phenylsulfanylanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1SC1=CC=CC=C1 PSZDFZSOCJHJRP-UHFFFAOYSA-N 0.000 description 1
- FDTYUDRPBMYHKE-UHFFFAOYSA-N 4-(3-chloro-4-phenylsulfanylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1SC1=CC=CC=C1 FDTYUDRPBMYHKE-UHFFFAOYSA-N 0.000 description 1
- XEYIOOPOGZOAEP-UHFFFAOYSA-N 4-(3-chloroanilino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Cl)=C1 XEYIOOPOGZOAEP-UHFFFAOYSA-N 0.000 description 1
- HLBGGOYPNRIHFH-UHFFFAOYSA-N 4-(3-chloroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Cl)=C1 HLBGGOYPNRIHFH-UHFFFAOYSA-N 0.000 description 1
- FNRKKHMPSZQHEJ-UHFFFAOYSA-N 4-(3-chloroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 FNRKKHMPSZQHEJ-UHFFFAOYSA-N 0.000 description 1
- CCECSDRSBLPTHW-UHFFFAOYSA-N 4-(3-cyanoanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C#N)=C1 CCECSDRSBLPTHW-UHFFFAOYSA-N 0.000 description 1
- QEPNPWOGJRAAOQ-UHFFFAOYSA-N 4-(3-cyanoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 QEPNPWOGJRAAOQ-UHFFFAOYSA-N 0.000 description 1
- PLWCWVLZUBYBEW-UHFFFAOYSA-N 4-(3-ethynylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 PLWCWVLZUBYBEW-UHFFFAOYSA-N 0.000 description 1
- OLNMDVMEJYNZBA-UHFFFAOYSA-N 4-(3-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(F)=C1 OLNMDVMEJYNZBA-UHFFFAOYSA-N 0.000 description 1
- ZFLQLVUBCSNBJL-UHFFFAOYSA-N 4-(3-fluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(F)=C1 ZFLQLVUBCSNBJL-UHFFFAOYSA-N 0.000 description 1
- WAJLIMOCEJPQKH-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 WAJLIMOCEJPQKH-UHFFFAOYSA-N 0.000 description 1
- ORXRAXFKEQIAIH-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyanilino)-8-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=C(OC)C=C([N+]([O-])=O)C=C12 ORXRAXFKEQIAIH-UHFFFAOYSA-N 0.000 description 1
- GOYDWBWGOZQPPQ-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=C(OC)C=CC=C12 GOYDWBWGOZQPPQ-UHFFFAOYSA-N 0.000 description 1
- ADYHMPMHENUUSX-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=C(C)C(O)=C1 ADYHMPMHENUUSX-UHFFFAOYSA-N 0.000 description 1
- HDYIFTHEJLLDHZ-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 HDYIFTHEJLLDHZ-UHFFFAOYSA-N 0.000 description 1
- RMENKSJNOQJIGF-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(O)=C1 RMENKSJNOQJIGF-UHFFFAOYSA-N 0.000 description 1
- DPAMNPPLTWUUOW-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6-methoxy-7-(2-morpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 DPAMNPPLTWUUOW-UHFFFAOYSA-N 0.000 description 1
- CCGQJNCMOBQUDD-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=CC(C#N)=C1NC1=CC=C(C)C(O)=C1 CCGQJNCMOBQUDD-UHFFFAOYSA-N 0.000 description 1
- OYLCGAMUHLRDOV-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(O)=C1 OYLCGAMUHLRDOV-UHFFFAOYSA-N 0.000 description 1
- ILIFRLHRZPLVLV-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(C)C(O)=C1 ILIFRLHRZPLVLV-UHFFFAOYSA-N 0.000 description 1
- RFRODPJRPJJUKI-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-8-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC([N+]([O-])=O)=CC2=C1NC1=CC=C(C)C(O)=C1 RFRODPJRPJJUKI-UHFFFAOYSA-N 0.000 description 1
- QPFBREGJTDLPBW-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=C(C)C(O)=C1 QPFBREGJTDLPBW-UHFFFAOYSA-N 0.000 description 1
- IKUBPVIBISSEJV-UHFFFAOYSA-N 4-(3-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(O)=C1 IKUBPVIBISSEJV-UHFFFAOYSA-N 0.000 description 1
- DLQVSGGYBADFFQ-UHFFFAOYSA-N 4-(3-iodoanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 DLQVSGGYBADFFQ-UHFFFAOYSA-N 0.000 description 1
- CFEACTBBVRNDBB-UHFFFAOYSA-N 4-(3-methoxyanilino)-6-nitroquinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 CFEACTBBVRNDBB-UHFFFAOYSA-N 0.000 description 1
- FMAZODAHMSMUNK-UHFFFAOYSA-N 4-(3-methylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 FMAZODAHMSMUNK-UHFFFAOYSA-N 0.000 description 1
- UFBPAPKMTIFMAC-UHFFFAOYSA-N 4-(4-bromo-3-hydroxyanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=C(Br)C(O)=C1 UFBPAPKMTIFMAC-UHFFFAOYSA-N 0.000 description 1
- DNGLYZBHHHXJDG-UHFFFAOYSA-N 4-(4-bromophenyl)sulfanyl-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1SC1=CC=C(Br)C=C1 DNGLYZBHHHXJDG-UHFFFAOYSA-N 0.000 description 1
- KBQXQEITHBAZNL-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC(O)=C(Cl)C=C1F KBQXQEITHBAZNL-UHFFFAOYSA-N 0.000 description 1
- NXQUVEFCIXDBGX-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F NXQUVEFCIXDBGX-UHFFFAOYSA-N 0.000 description 1
- AHEZGLOWOWBLAP-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(2-morpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCOCC3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F AHEZGLOWOWBLAP-UHFFFAOYSA-N 0.000 description 1
- RDVLPEPWSGCECJ-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F RDVLPEPWSGCECJ-UHFFFAOYSA-N 0.000 description 1
- CPMQZDLBPYFFLC-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=CC(C#N)=C1NC1=CC(O)=C(Cl)C=C1F CPMQZDLBPYFFLC-UHFFFAOYSA-N 0.000 description 1
- ISCIEBIOIJWXOX-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-7-[2-(dimethylamino)ethoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN(C)C)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F ISCIEBIOIJWXOX-UHFFFAOYSA-N 0.000 description 1
- WUTUYQSMZJUIDT-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-7-[3-(dimethylamino)propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN(C)C)C(OC)=CC2=C1NC1=CC(O)=C(Cl)C=C1F WUTUYQSMZJUIDT-UHFFFAOYSA-N 0.000 description 1
- AWVIKPDIAVKVTD-UHFFFAOYSA-N 4-(4-chloro-2-fluoro-5-hydroxyanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC(O)=C(Cl)C=C1F AWVIKPDIAVKVTD-UHFFFAOYSA-N 0.000 description 1
- HXFOGGVVVXAAAY-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=C(Cl)C=C1F HXFOGGVVVXAAAY-UHFFFAOYSA-N 0.000 description 1
- DCCQITVOSPOELC-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F DCCQITVOSPOELC-UHFFFAOYSA-N 0.000 description 1
- AGDGNPMRBLYEBN-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7-dihydroxyquinoline-3-carbonitrile Chemical compound C=12C=C(O)C(O)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F AGDGNPMRBLYEBN-UHFFFAOYSA-N 0.000 description 1
- AZGVCABJHURYHG-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F AZGVCABJHURYHG-UHFFFAOYSA-N 0.000 description 1
- UCTHWZMWNQJTQN-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F UCTHWZMWNQJTQN-UHFFFAOYSA-N 0.000 description 1
- QDMNXRDMMAATAQ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-phenylmethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCC=3C=CC=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F QDMNXRDMMAATAQ-UHFFFAOYSA-N 0.000 description 1
- WGZXUJZAMNFXSU-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C12=CC(OC)=CC=C2N=CC(C#N)=C1NC1=CC=C(Cl)C=C1F WGZXUJZAMNFXSU-UHFFFAOYSA-N 0.000 description 1
- ZRBPCTDCKOQMBZ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCCl)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F ZRBPCTDCKOQMBZ-UHFFFAOYSA-N 0.000 description 1
- JSZSIBBREFGLGJ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-ethoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OCC)=CC=C2C=1NC1=CC=C(Cl)C=C1F JSZSIBBREFGLGJ-UHFFFAOYSA-N 0.000 description 1
- NBFFJZSLOQTJKX-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-hydroxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(O)=CC=C2C=1NC1=CC=C(Cl)C=C1F NBFFJZSLOQTJKX-UHFFFAOYSA-N 0.000 description 1
- UFUCDVGCMNVASM-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F UFUCDVGCMNVASM-UHFFFAOYSA-N 0.000 description 1
- RWPARJNAESKYRJ-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F RWPARJNAESKYRJ-UHFFFAOYSA-N 0.000 description 1
- NIFSUEUBPCVATA-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(Cl)C=C1F NIFSUEUBPCVATA-UHFFFAOYSA-N 0.000 description 1
- VUELXWCNULTVCB-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-8-methoxy-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC([N+]([O-])=O)=CC2=C1NC1=CC=C(Cl)C=C1F VUELXWCNULTVCB-UHFFFAOYSA-N 0.000 description 1
- VHNUHNWRNYABHC-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=C(Cl)C=C1F VHNUHNWRNYABHC-UHFFFAOYSA-N 0.000 description 1
- INWVUMKNCRPNHB-UHFFFAOYSA-N 4-(4-chloro-2-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1C INWVUMKNCRPNHB-UHFFFAOYSA-N 0.000 description 1
- HLURNMSMPHQXLV-UHFFFAOYSA-N 4-(4-ethylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=CC(CC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 HLURNMSMPHQXLV-UHFFFAOYSA-N 0.000 description 1
- PICBGXSASXFIAL-UHFFFAOYSA-N 4-(4-fluoroanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1 PICBGXSASXFIAL-UHFFFAOYSA-N 0.000 description 1
- NAPDTERTUWQXNR-UHFFFAOYSA-N 4-(4-hydroxy-2-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(O)C=C1C NAPDTERTUWQXNR-UHFFFAOYSA-N 0.000 description 1
- ACACRWSZUZUTEJ-UHFFFAOYSA-N 4-(4-hydroxy-2-methylanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=C(O)C=C1C ACACRWSZUZUTEJ-UHFFFAOYSA-N 0.000 description 1
- OQUDHJHVQGCUOJ-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(C)=C(O)C(C)=C1 OQUDHJHVQGCUOJ-UHFFFAOYSA-N 0.000 description 1
- IVWBIVZBYRCUFO-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC(Cl)=CC=C1O IVWBIVZBYRCUFO-UHFFFAOYSA-N 0.000 description 1
- PAOLEDZAKLCSFE-UHFFFAOYSA-N 4-(5-chloro-2-methoxyanilino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound COC1=CC=C(Cl)C=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 PAOLEDZAKLCSFE-UHFFFAOYSA-N 0.000 description 1
- UATCEBVVGUUBAF-UHFFFAOYSA-N 4-[(2-aminophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=CC=C1N UATCEBVVGUUBAF-UHFFFAOYSA-N 0.000 description 1
- UNVQEGYJIRTKEA-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=C(F)C(F)=C1 UNVQEGYJIRTKEA-UHFFFAOYSA-N 0.000 description 1
- ZXRTVLOBTDWRJL-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=C(OC)C(OC)=C1 ZXRTVLOBTDWRJL-UHFFFAOYSA-N 0.000 description 1
- MOMWLTJRHZNPRC-UHFFFAOYSA-N 4-[(3-bromophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=CC(Br)=C1 MOMWLTJRHZNPRC-UHFFFAOYSA-N 0.000 description 1
- JVPPPJVZGREELP-UHFFFAOYSA-N 4-[2-(2-hydroxyethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1CCO JVPPPJVZGREELP-UHFFFAOYSA-N 0.000 description 1
- XHHYAWSDIXRRAO-UHFFFAOYSA-N 4-[3-(chloromethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CCl)=C1 XHHYAWSDIXRRAO-UHFFFAOYSA-N 0.000 description 1
- OVFOWMBZHBTKLD-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=C(OC)C2=C1NC1=CC=CC(N(C)C)=C1 OVFOWMBZHBTKLD-UHFFFAOYSA-N 0.000 description 1
- LMPUEJSCCKBFOV-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1NC1=CC=CC(N(C)C)=C1 LMPUEJSCCKBFOV-UHFFFAOYSA-N 0.000 description 1
- OLPCFXOXZCAXNQ-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(N(C)C)=C1 OLPCFXOXZCAXNQ-UHFFFAOYSA-N 0.000 description 1
- LFDLSQQIFSWTPB-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-6-nitroquinoline-3-carbonitrile Chemical compound CN(C)C1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 LFDLSQQIFSWTPB-UHFFFAOYSA-N 0.000 description 1
- OGLPBSWSMKAWCR-UHFFFAOYSA-N 4-[3-(dimethylamino)anilino]-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC(N(C)C)=C1 OGLPBSWSMKAWCR-UHFFFAOYSA-N 0.000 description 1
- VEWKMHYYBJASDM-UHFFFAOYSA-N 4-[3-(hydroxymethyl)-2-methylanilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CO)=C1C VEWKMHYYBJASDM-UHFFFAOYSA-N 0.000 description 1
- ZTHKSSJRIANSFO-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(CCO)C=C1 ZTHKSSJRIANSFO-UHFFFAOYSA-N 0.000 description 1
- JPFSELHYKCHNJV-UHFFFAOYSA-N 4-[4-(dimethylamino)anilino]-6-nitroquinoline-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1NC1=C(C#N)C=NC2=CC=C([N+]([O-])=O)C=C12 JPFSELHYKCHNJV-UHFFFAOYSA-N 0.000 description 1
- VSEAWQWXSBESSQ-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)anilino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C(C(F)(F)F)=C1 VSEAWQWXSBESSQ-UHFFFAOYSA-N 0.000 description 1
- OFWSZEIPLOQZGP-UHFFFAOYSA-N 4-[[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]amino]-2-methylidene-4-oxobutanoic acid Chemical compound C12=CC(NC(=O)CC(=C)C(=O)O)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 OFWSZEIPLOQZGP-UHFFFAOYSA-N 0.000 description 1
- SHNLPCUCDONAQF-UHFFFAOYSA-N 4-anilino-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1 SHNLPCUCDONAQF-UHFFFAOYSA-N 0.000 description 1
- YYARKMZWFMYHGW-UHFFFAOYSA-N 4-bromo-n-[4-(3-bromo-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCBr)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 YYARKMZWFMYHGW-UHFFFAOYSA-N 0.000 description 1
- PFKFSVRPRVNSCG-UHFFFAOYSA-N 4-bromo-n-[4-(3-bromoanilino)-3-cyano-7-ethoxyquinolin-6-yl]but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCBr)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 PFKFSVRPRVNSCG-UHFFFAOYSA-N 0.000 description 1
- VNLBRJPOWOLBFT-UHFFFAOYSA-N 4-bromo-n-[4-(3-bromoanilino)-3-cyano-8-methoxyquinolin-6-yl]but-2-enamide Chemical compound N#CC1=CN=C2C(OC)=CC(NC(=O)C=CCBr)=CC2=C1NC1=CC=CC(Br)=C1 VNLBRJPOWOLBFT-UHFFFAOYSA-N 0.000 description 1
- LQFDQJDIWFMWHN-UHFFFAOYSA-N 4-morpholin-4-ylbut-2-enoic acid Chemical compound OC(=O)C=CCN1CCOCC1 LQFDQJDIWFMWHN-UHFFFAOYSA-N 0.000 description 1
- YIUAOQMDEABCMH-UHFFFAOYSA-N 6,7-diethoxy-4-(3-fluoroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(F)=C1 YIUAOQMDEABCMH-UHFFFAOYSA-N 0.000 description 1
- BTUDPTQPRPWGQY-UHFFFAOYSA-N 6,7-diethoxy-4-(4-fluoro-2-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1C BTUDPTQPRPWGQY-UHFFFAOYSA-N 0.000 description 1
- OGVXUORKCBXMAD-UHFFFAOYSA-N 6,7-diethoxy-4-(4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C=C1 OGVXUORKCBXMAD-UHFFFAOYSA-N 0.000 description 1
- KLJORPXEIAZGDJ-UHFFFAOYSA-N 6,7-diethoxy-4-(n-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1N(C)C1=CC=CC=C1 KLJORPXEIAZGDJ-UHFFFAOYSA-N 0.000 description 1
- YXCSSHCCXLUHDG-UHFFFAOYSA-N 6,7-dimethoxy-4-(2-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1C YXCSSHCCXLUHDG-UHFFFAOYSA-N 0.000 description 1
- QBPFCLKAEGQCJR-UHFFFAOYSA-N 6,7-dimethoxy-4-(2-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC=C1SC QBPFCLKAEGQCJR-UHFFFAOYSA-N 0.000 description 1
- ZSJDOQUXSFYFRM-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(SC)=C1 ZSJDOQUXSFYFRM-UHFFFAOYSA-N 0.000 description 1
- WEOXCMIQDJTOOP-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-nitroanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC([N+]([O-])=O)=C1 WEOXCMIQDJTOOP-UHFFFAOYSA-N 0.000 description 1
- VVHLRJCWFVPVSW-UHFFFAOYSA-N 6,7-dimethoxy-4-(3-phenoxyanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC(C=1)=CC=CC=1OC1=CC=CC=C1 VVHLRJCWFVPVSW-UHFFFAOYSA-N 0.000 description 1
- PLZHSFDPFHDSRA-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-methoxy-2-methylanilino)quinoline-3-carbonitrile Chemical compound CC1=CC(OC)=CC=C1NC1=C(C#N)C=NC2=CC(OC)=C(OC)C=C12 PLZHSFDPFHDSRA-UHFFFAOYSA-N 0.000 description 1
- JXLUYPNXIHHINO-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C=C1 JXLUYPNXIHHINO-UHFFFAOYSA-N 0.000 description 1
- DRHDIJVDQNOQEI-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(SC)C=C1 DRHDIJVDQNOQEI-UHFFFAOYSA-N 0.000 description 1
- GSVIQADQNZROAL-UHFFFAOYSA-N 6,7-dimethoxy-4-(4-phenoxyanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC(C=C1)=CC=C1OC1=CC=CC=C1 GSVIQADQNZROAL-UHFFFAOYSA-N 0.000 description 1
- LYWXXIOBMCQLNJ-UHFFFAOYSA-N 6,7-dimethoxy-4-(pyridin-3-ylamino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CN=C1 LYWXXIOBMCQLNJ-UHFFFAOYSA-N 0.000 description 1
- NPVUUFCFLLPVCM-UHFFFAOYSA-N 6,7-dimethoxy-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(C(F)(F)F)=C1 NPVUUFCFLLPVCM-UHFFFAOYSA-N 0.000 description 1
- WHMRDYJJAXPWGX-UHFFFAOYSA-N 6,7-dimethoxy-4-[4-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(C(F)(F)F)C=C1 WHMRDYJJAXPWGX-UHFFFAOYSA-N 0.000 description 1
- MTPYYINKVPVYNQ-UHFFFAOYSA-N 6-(dimethylamino)-4-(3-methoxyanilino)quinoline-3-carbonitrile;hydrochloride Chemical compound Cl.COC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)N(C)C)=C1 MTPYYINKVPVYNQ-UHFFFAOYSA-N 0.000 description 1
- LEACUGBTKYYIDG-UHFFFAOYSA-N 6-amino-4-(3,4-difluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 LEACUGBTKYYIDG-UHFFFAOYSA-N 0.000 description 1
- WMIBAZLHGIVWSU-UHFFFAOYSA-N 6-amino-4-(3-bromo-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 WMIBAZLHGIVWSU-UHFFFAOYSA-N 0.000 description 1
- CLGJOTLYNXUVES-UHFFFAOYSA-N 6-amino-4-(3-bromo-4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 CLGJOTLYNXUVES-UHFFFAOYSA-N 0.000 description 1
- DXWBLHXTKOUIHA-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-7-ethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 DXWBLHXTKOUIHA-UHFFFAOYSA-N 0.000 description 1
- PFVDWAYDYKHDEH-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)-8-[(dimethylamino)methyl]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(CN(C)C)=CC(N)=CC2=C1NC1=CC=CC(Br)=C1 PFVDWAYDYKHDEH-UHFFFAOYSA-N 0.000 description 1
- ZRTXZWXHWPAXFT-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 ZRTXZWXHWPAXFT-UHFFFAOYSA-N 0.000 description 1
- DRHNHDZBMACOEW-UHFFFAOYSA-N 6-amino-4-(3-chloro-2-thiophen-3-yloxyanilino)quinoline-3-carbonitrile Chemical compound NC=1C=C2C(=C(C=NC2=CC=1)C#N)NC1=C(C(=CC=C1)Cl)OC=1C=CSC=1 DRHNHDZBMACOEW-UHFFFAOYSA-N 0.000 description 1
- MJOPKUFLFODTKP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 MJOPKUFLFODTKP-UHFFFAOYSA-N 0.000 description 1
- WMSREFWREGHLAP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 WMSREFWREGHLAP-UHFFFAOYSA-N 0.000 description 1
- IUHXMKMPNZOIIR-UHFFFAOYSA-N 6-amino-4-(3-chloroanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 IUHXMKMPNZOIIR-UHFFFAOYSA-N 0.000 description 1
- PDQUVNBKITWFNZ-UHFFFAOYSA-N 6-amino-4-(3-cyanoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 PDQUVNBKITWFNZ-UHFFFAOYSA-N 0.000 description 1
- MJPIXAAXFZASFT-UHFFFAOYSA-N 6-amino-4-(3-ethynylanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 MJPIXAAXFZASFT-UHFFFAOYSA-N 0.000 description 1
- BCAYGAKYRNJRSZ-UHFFFAOYSA-N 6-amino-4-(3-hydroxy-4-methoxyanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C#N)C=NC2=C(OC)C=C(N)C=C12 BCAYGAKYRNJRSZ-UHFFFAOYSA-N 0.000 description 1
- DWJCHBHBLILFOB-UHFFFAOYSA-N 6-amino-4-(3-hydroxy-4-methylanilino)-8-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC(N)=CC2=C1NC1=CC=C(C)C(O)=C1 DWJCHBHBLILFOB-UHFFFAOYSA-N 0.000 description 1
- JSCNIEOKVSQSKM-UHFFFAOYSA-N 6-amino-4-(3-iodoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(I)=C1 JSCNIEOKVSQSKM-UHFFFAOYSA-N 0.000 description 1
- OXXUZYBVAKGKQB-UHFFFAOYSA-N 6-amino-4-(3-methoxyanilino)quinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 OXXUZYBVAKGKQB-UHFFFAOYSA-N 0.000 description 1
- PNHLUCIDSVSCDW-UHFFFAOYSA-N 6-amino-4-(3-methylanilino)quinoline-3-carbonitrile Chemical compound CC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 PNHLUCIDSVSCDW-UHFFFAOYSA-N 0.000 description 1
- IHOAIURDVZHDEQ-UHFFFAOYSA-N 6-amino-4-(3-methylsulfanylanilino)quinoline-3-carbonitrile Chemical compound CSC1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 IHOAIURDVZHDEQ-UHFFFAOYSA-N 0.000 description 1
- BPRJKKPJMZUBDG-UHFFFAOYSA-N 6-amino-4-(3-propan-2-ylanilino)quinoline-3-carbonitrile Chemical compound CC(C)C1=CC=CC(NC=2C3=CC(N)=CC=C3N=CC=2C#N)=C1 BPRJKKPJMZUBDG-UHFFFAOYSA-N 0.000 description 1
- SIBQYOKZVKAXSA-UHFFFAOYSA-N 6-amino-4-(4-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C=C1 SIBQYOKZVKAXSA-UHFFFAOYSA-N 0.000 description 1
- VPGQEKLTHYYHRA-UHFFFAOYSA-N 6-amino-4-(4-chloro-2-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(Cl)C=C1F VPGQEKLTHYYHRA-UHFFFAOYSA-N 0.000 description 1
- YOOVBYGMAALDAY-UHFFFAOYSA-N 6-ethoxy-4-(3-hydroxy-4-methylanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OC)C(OCC)=CC2=C1NC1=CC=C(C)C(O)=C1 YOOVBYGMAALDAY-UHFFFAOYSA-N 0.000 description 1
- WPUZJCWFDMOJQH-UHFFFAOYSA-N 6-iodo-4-(3-methoxyanilino)quinoline-3-carbonitrile Chemical compound COC1=CC=CC(NC=2C3=CC(I)=CC=C3N=CC=2C#N)=C1 WPUZJCWFDMOJQH-UHFFFAOYSA-N 0.000 description 1
- WCOAJGXFODNEJR-UHFFFAOYSA-N 6-methoxy-4-(2-methylsulfanylanilino)-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC=CC=C1SC WCOAJGXFODNEJR-UHFFFAOYSA-N 0.000 description 1
- HZFKBQSCERCMGV-UHFFFAOYSA-N 6-nitro-4-(3-propan-2-ylanilino)quinoline-3-carbonitrile Chemical compound CC(C)C1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 HZFKBQSCERCMGV-UHFFFAOYSA-N 0.000 description 1
- CRYQEVRYEJPICG-UHFFFAOYSA-N 6-nitro-4-[3-(trifluoromethoxy)anilino]quinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(OC(F)(F)F)=C1 CRYQEVRYEJPICG-UHFFFAOYSA-N 0.000 description 1
- WUVXAOGFNCAWFT-UHFFFAOYSA-N 6-nitro-4-[3-(trifluoromethyl)anilino]quinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 WUVXAOGFNCAWFT-UHFFFAOYSA-N 0.000 description 1
- PVZCNRGQTKOEAH-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN(C)C)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 PVZCNRGQTKOEAH-UHFFFAOYSA-N 0.000 description 1
- ZUZYWMSAFACAAG-UHFFFAOYSA-N 7-ethoxy-4-(3-hydroxy-4-methylanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(C)C(O)=C1 ZUZYWMSAFACAAG-UHFFFAOYSA-N 0.000 description 1
- AVKRWJGYHFZIQI-UHFFFAOYSA-N 8-(3-bromoanilino)-[1,3]dioxolo[4,5-g]quinoline-7-carbonitrile Chemical compound BrC1=CC=CC(NC=2C3=CC=4OCOC=4C=C3N=CC=2C#N)=C1 AVKRWJGYHFZIQI-UHFFFAOYSA-N 0.000 description 1
- OMJZUXOYCMTLLW-UHFFFAOYSA-N 8-methoxy-4-(2,4,6-trifluoroanilino)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C(OC)=CC=CC2=C1NC1=C(F)C=C(F)C=C1F OMJZUXOYCMTLLW-UHFFFAOYSA-N 0.000 description 1
- KPUXOZCNQILALD-UHFFFAOYSA-N CCOC(C=C(C=C(C(NCC(C=C1)=CC(Cl)=C1Cl)=N1)C#N)C1=C1)=C1OCC Chemical compound CCOC(C=C(C=C(C(NCC(C=C1)=CC(Cl)=C1Cl)=N1)C#N)C1=C1)=C1OCC KPUXOZCNQILALD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WXZKIKQSGYISMT-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)NC(C=C)=O)C#N)OC=1C=CSC=1 Chemical compound ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)NC(C=C)=O)C#N)OC=1C=CSC=1 WXZKIKQSGYISMT-UHFFFAOYSA-N 0.000 description 1
- 208000035984 Colonic Polyps Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- WXYBQHVGNHSYBJ-UHFFFAOYSA-N N-(3-bromophenyl)-N-(3-cyano-6,7-dihydroxyquinolin-4-yl)acetamide Chemical compound N#CC=1C=NC2=CC(O)=C(O)C=C2C=1N(C(=O)C)C1=CC=CC(Br)=C1 WXYBQHVGNHSYBJ-UHFFFAOYSA-N 0.000 description 1
- CTDCXHMAQLCDPT-UHFFFAOYSA-N N-[4-(3-chloro-2-thiophen-3-yloxyanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound ClC=1C(=C(C=CC=1)NC1=C(C=NC2=CC=C(C=C12)NC(C#CC)=O)C#N)OC=1C=CSC=1 CTDCXHMAQLCDPT-UHFFFAOYSA-N 0.000 description 1
- WVUNYSQLFKLYNI-UHFFFAOYSA-N N-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide Chemical compound C=12C=C(NC(=O)C=CCN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 WVUNYSQLFKLYNI-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- ADTHOQASRLCLRF-UHFFFAOYSA-N n-[3-[(3-cyano-6,7-dimethoxyquinolin-4-yl)amino]phenyl]acetamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(NC(C)=O)=C1 ADTHOQASRLCLRF-UHFFFAOYSA-N 0.000 description 1
- NHMLTTGVAYCKEO-UHFFFAOYSA-N n-[3-cyano-4-(3,4-dibromoanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C(Br)=C1 NHMLTTGVAYCKEO-UHFFFAOYSA-N 0.000 description 1
- YPKIJBWMDLKPTG-UHFFFAOYSA-N n-[3-cyano-4-(3,4-difluoroanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(F)=C1 YPKIJBWMDLKPTG-UHFFFAOYSA-N 0.000 description 1
- SQGPYBQAQIKBQS-UHFFFAOYSA-N n-[3-cyano-4-(3,4-difluoroanilino)quinolin-6-yl]prop-2-enamide Chemical compound C1=C(F)C(F)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 SQGPYBQAQIKBQS-UHFFFAOYSA-N 0.000 description 1
- RLAZEQDNCUQRSX-UHFFFAOYSA-N n-[3-cyano-4-(3-cyanoanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound C1CCCCN1CC#CC(=O)NC(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC=CC(C#N)=C1 RLAZEQDNCUQRSX-UHFFFAOYSA-N 0.000 description 1
- VMWRFOQWNJQIMZ-UHFFFAOYSA-N n-[3-cyano-4-(3-cyanoanilino)quinolin-6-yl]prop-2-enamide Chemical compound C12=CC(NC(=O)C=C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#N)=C1 VMWRFOQWNJQIMZ-UHFFFAOYSA-N 0.000 description 1
- BBBFROLYSXGUOP-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound C1CCCCN1CC#CC(=O)NC(C=C12)=CC=C1N=CC(C#N)=C2NC1=CC=CC(C#C)=C1 BBBFROLYSXGUOP-UHFFFAOYSA-N 0.000 description 1
- WFMBJUVKYJBICW-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 WFMBJUVKYJBICW-UHFFFAOYSA-N 0.000 description 1
- WQTFCVASSZGLCT-UHFFFAOYSA-N n-[3-cyano-4-(3-ethynylanilino)quinolin-6-yl]prop-2-enamide Chemical compound C12=CC(NC(=O)C=C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C#C)=C1 WQTFCVASSZGLCT-UHFFFAOYSA-N 0.000 description 1
- XNWKTBYXWIDLCZ-UHFFFAOYSA-N n-[3-cyano-4-(3-fluoroanilino)quinolin-6-yl]prop-2-enamide Chemical compound FC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 XNWKTBYXWIDLCZ-UHFFFAOYSA-N 0.000 description 1
- RKKMOSSRGMBZAO-UHFFFAOYSA-N n-[3-cyano-4-(3-iodoanilino)quinolin-6-yl]prop-2-enamide Chemical compound IC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 RKKMOSSRGMBZAO-UHFFFAOYSA-N 0.000 description 1
- VYLDYNHWUMJQMD-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C#CCN4CCCCC4)=CC=C3N=CC=2C#N)=C1 VYLDYNHWUMJQMD-UHFFFAOYSA-N 0.000 description 1
- HMNIDDVKONQLPW-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]but-2-ynamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C#CC)=CC=C3N=CC=2C#N)=C1 HMNIDDVKONQLPW-UHFFFAOYSA-N 0.000 description 1
- JEVROOVJYXQOEZ-UHFFFAOYSA-N n-[3-cyano-4-(3-methoxyanilino)quinolin-6-yl]prop-2-enamide Chemical compound COC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 JEVROOVJYXQOEZ-UHFFFAOYSA-N 0.000 description 1
- QMRGXXWQJSOWEE-UHFFFAOYSA-N n-[3-cyano-4-(3-methylanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C)=C1 QMRGXXWQJSOWEE-UHFFFAOYSA-N 0.000 description 1
- NOPOIBJRWQZCGR-UHFFFAOYSA-N n-[3-cyano-4-(3-methylanilino)quinolin-6-yl]prop-2-enamide Chemical compound CC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 NOPOIBJRWQZCGR-UHFFFAOYSA-N 0.000 description 1
- WUWIZNDWEZIYSB-UHFFFAOYSA-N n-[3-cyano-4-(3-propan-2-ylanilino)quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(C)C)=C1 WUWIZNDWEZIYSB-UHFFFAOYSA-N 0.000 description 1
- MQWPQDJSSWDVTQ-UHFFFAOYSA-N n-[3-cyano-4-(3-propan-2-ylanilino)quinolin-6-yl]prop-2-enamide Chemical compound CC(C)C1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 MQWPQDJSSWDVTQ-UHFFFAOYSA-N 0.000 description 1
- QSMHWFXKNHCJSQ-UHFFFAOYSA-N n-[3-cyano-4-[3-(dimethylamino)anilino]quinolin-6-yl]prop-2-enamide Chemical compound CN(C)C1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 QSMHWFXKNHCJSQ-UHFFFAOYSA-N 0.000 description 1
- VVNVIMKVRAEOEX-UHFFFAOYSA-N n-[3-cyano-4-[3-(trifluoromethyl)anilino]quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(C(F)(F)F)=C1 VVNVIMKVRAEOEX-UHFFFAOYSA-N 0.000 description 1
- JSPHYZXDFYTYMG-UHFFFAOYSA-N n-[3-cyano-4-[4-(dimethylamino)anilino]quinolin-6-yl]prop-2-enamide Chemical compound C1=CC(N(C)C)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 JSPHYZXDFYTYMG-UHFFFAOYSA-N 0.000 description 1
- XTFZKUOUYWCJSZ-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(OC)C(NC(=O)C=CCN(CC)CC)=CC2=C1NC1=CC=C(F)C(Br)=C1 XTFZKUOUYWCJSZ-UHFFFAOYSA-N 0.000 description 1
- IUYSZSPQSWJCLI-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN(C)C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 IUYSZSPQSWJCLI-UHFFFAOYSA-N 0.000 description 1
- KEQGHXFVKOQNQC-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Br)=C1 KEQGHXFVKOQNQC-UHFFFAOYSA-N 0.000 description 1
- AKTAELVLHHYTPP-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 AKTAELVLHHYTPP-UHFFFAOYSA-N 0.000 description 1
- OFGJOXKWOLGBRC-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 OFGJOXKWOLGBRC-UHFFFAOYSA-N 0.000 description 1
- HYAJGYAMFMLZDR-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Br)=C1 HYAJGYAMFMLZDR-UHFFFAOYSA-N 0.000 description 1
- SPXOEZKLWIVPKM-UHFFFAOYSA-N n-[4-(3-bromo-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C1=C(Br)C(F)=CC=C1NC(C1=C2)=C(C#N)C=NC1=CC=C2NC(=O)C=CCN1CCOCC1 SPXOEZKLWIVPKM-UHFFFAOYSA-N 0.000 description 1
- AHFLCVUUMDIYOY-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN(CC)CC)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 AHFLCVUUMDIYOY-UHFFFAOYSA-N 0.000 description 1
- RMFYQLUHNZPYCP-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(OC)C(NC(=O)C=CCN(CC)CC)=CC2=C1NC1=CC=CC(Br)=C1 RMFYQLUHNZPYCP-UHFFFAOYSA-N 0.000 description 1
- QWSSCGSSNDSGPP-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-chlorobut-2-enamide Chemical compound C=12C=C(NC(=O)C=CCCl)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 QWSSCGSSNDSGPP-UHFFFAOYSA-N 0.000 description 1
- PLQLHGCLAWKBJG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-ynamide Chemical compound C=12C=C(NC(=O)C#CC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 PLQLHGCLAWKBJG-UHFFFAOYSA-N 0.000 description 1
- HKLOKSUROGEMSK-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-7-methoxyquinolin-6-yl]prop-2-enamide Chemical compound C=12C=C(NC(=O)C=C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 HKLOKSUROGEMSK-UHFFFAOYSA-N 0.000 description 1
- KBJXOMLMGJAGKB-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-8-[(dimethylamino)methyl]quinolin-6-yl]acetamide Chemical compound N#CC1=CN=C2C(CN(C)C)=CC(NC(C)=O)=CC2=C1NC1=CC=CC(Br)=C1 KBJXOMLMGJAGKB-UHFFFAOYSA-N 0.000 description 1
- LERVYVZYFPUODM-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-8-[(dimethylamino)methyl]quinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC(CN(C)C)=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 LERVYVZYFPUODM-UHFFFAOYSA-N 0.000 description 1
- GJYOWCCGMOXTJG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-8-[(dimethylamino)methyl]quinolin-6-yl]prop-2-enamide Chemical compound N#CC1=CN=C2C(CN(C)C)=CC(NC(=O)C=C)=CC2=C1NC1=CC=CC(Br)=C1 GJYOWCCGMOXTJG-UHFFFAOYSA-N 0.000 description 1
- LYARTSGAGCRCAG-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyano-8-methoxyquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(CC)CC)=CC(OC)=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 LYARTSGAGCRCAG-UHFFFAOYSA-N 0.000 description 1
- CQFOPPHLPZNBKO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-(morpholin-4-ylmethyl)prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C(=C)CN4CCOCC4)=CC=C3N=CC=2C#N)=C1 CQFOPPHLPZNBKO-UHFFFAOYSA-N 0.000 description 1
- PTSZXFBVOGOHCV-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-2-chloroacetamide Chemical compound C12=CC(NC(=O)CCl)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 PTSZXFBVOGOHCV-UHFFFAOYSA-N 0.000 description 1
- HXFGGFIRXYTMPO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(4-ethylpiperazin-1-yl)but-2-ynamide Chemical compound C1CN(CC)CCN1CC#CC(=O)NC1=CC=C(N=CC(C#N)=C2NC=3C=C(Br)C=CC=3)C2=C1 HXFGGFIRXYTMPO-UHFFFAOYSA-N 0.000 description 1
- PMOGPFDGDJBBQR-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(4-methylpiperazin-1-yl)but-2-ynamide Chemical compound C1CN(C)CCN1CC#CC(=O)NC1=CC=C(N=CC(C#N)=C2NC=3C=C(Br)C=CC=3)C2=C1 PMOGPFDGDJBBQR-UHFFFAOYSA-N 0.000 description 1
- CZIMISMCFLYLPO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 CZIMISMCFLYLPO-UHFFFAOYSA-N 0.000 description 1
- UYTOXOMHJMCOKH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 UYTOXOMHJMCOKH-UHFFFAOYSA-N 0.000 description 1
- NYRBHASTRFCNHY-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(dipropylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CCC)CCC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 NYRBHASTRFCNHY-UHFFFAOYSA-N 0.000 description 1
- ZGHNGLGVQAETLS-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-(methylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCNC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 ZGHNGLGVQAETLS-UHFFFAOYSA-N 0.000 description 1
- OXGRVGJNLBMVAH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-[di(propan-2-yl)amino]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C(C)C)C(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 OXGRVGJNLBMVAH-UHFFFAOYSA-N 0.000 description 1
- JNBUZUCZWYMEFZ-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-[tert-butyl(dimethyl)silyl]oxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCO[Si](C)(C)C(C)(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 JNBUZUCZWYMEFZ-UHFFFAOYSA-N 0.000 description 1
- PRNLOFROAGASER-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-enamide Chemical compound C12=CC(NC(=O)C=CCOC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 PRNLOFROAGASER-UHFFFAOYSA-N 0.000 description 1
- SAYBFCUQRKDDCV-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-morpholin-4-ylbut-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCN4CCOCC4)=CC=C3N=CC=2C#N)=C1 SAYBFCUQRKDDCV-UHFFFAOYSA-N 0.000 description 1
- KPTBCNWYGZERPK-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]-4-piperidin-1-ylbut-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCN4CCCCC4)=CC=C3N=CC=2C#N)=C1 KPTBCNWYGZERPK-UHFFFAOYSA-N 0.000 description 1
- KGUJQEYRHHBQRF-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]acetamide Chemical compound C12=CC(NC(=O)C)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 KGUJQEYRHHBQRF-UHFFFAOYSA-N 0.000 description 1
- PBDJWRUCRSLDEM-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 PBDJWRUCRSLDEM-UHFFFAOYSA-N 0.000 description 1
- JKBHSBZUZPGJAH-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]butanamide Chemical compound C12=CC(NC(=O)CCC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 JKBHSBZUZPGJAH-UHFFFAOYSA-N 0.000 description 1
- MSLIBSZZLAWHQM-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 MSLIBSZZLAWHQM-UHFFFAOYSA-N 0.000 description 1
- QAIWBHUZZZOVEO-UHFFFAOYSA-N n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]propanamide Chemical compound C12=CC(NC(=O)CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 QAIWBHUZZZOVEO-UHFFFAOYSA-N 0.000 description 1
- VHGGLPYMJXZJFI-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-4-methoxybut-2-enamide Chemical compound C12=CC(NC(=O)C=CCOC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 VHGGLPYMJXZJFI-UHFFFAOYSA-N 0.000 description 1
- FZGMFMLMNGWHRX-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-2-(morpholin-4-ylmethyl)prop-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=C(C#N)C=NC1=CC=C2NC(=O)C(=C)CN1CCOCC1 FZGMFMLMNGWHRX-UHFFFAOYSA-N 0.000 description 1
- WZKCFGBQMSKKQQ-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 WZKCFGBQMSKKQQ-UHFFFAOYSA-N 0.000 description 1
- VMBCEWCTCURUPS-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(diethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CC)CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 VMBCEWCTCURUPS-UHFFFAOYSA-N 0.000 description 1
- KXQYGHZAGFHMDJ-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C12=CC(NC(=O)C=CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 KXQYGHZAGFHMDJ-UHFFFAOYSA-N 0.000 description 1
- IRNUPYILYRKBDU-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-(dimethylamino)but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(C)C)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 IRNUPYILYRKBDU-UHFFFAOYSA-N 0.000 description 1
- QFBZIQWYXFSVHH-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-methoxybut-2-ynamide Chemical compound C12=CC(NC(=O)C#CCOC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 QFBZIQWYXFSVHH-UHFFFAOYSA-N 0.000 description 1
- USKFPOBBUSZDCR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=C(C#N)C=NC1=CC=C2NC(=O)C=CCN1CCOCC1 USKFPOBBUSZDCR-UHFFFAOYSA-N 0.000 description 1
- GPLSEURFJLQXHR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 GPLSEURFJLQXHR-UHFFFAOYSA-N 0.000 description 1
- CYCQVROTABWGKI-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 CYCQVROTABWGKI-UHFFFAOYSA-N 0.000 description 1
- SFXWFZYYIXZARH-UHFFFAOYSA-N n-[4-(3-chloroanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Cl)=C1 SFXWFZYYIXZARH-UHFFFAOYSA-N 0.000 description 1
- GASFMMJWWWYIBV-UHFFFAOYSA-N n-[4-(3-chloroanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound ClC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CC=2C#N)=C1 GASFMMJWWWYIBV-UHFFFAOYSA-N 0.000 description 1
- HZFFAOYHSJFYAC-UHFFFAOYSA-N n-[4-(4-bromoanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CC(C#N)=C1NC1=CC=C(Br)C=C1 HZFFAOYHSJFYAC-UHFFFAOYSA-N 0.000 description 1
- JQOCJKUVECLNAC-UHFFFAOYSA-N n-[4-(4-bromoanilino)-3-cyanoquinolin-6-yl]prop-2-enamide Chemical compound C1=CC(Br)=CC=C1NC1=C(C#N)C=NC2=CC=C(NC(=O)C=C)C=C12 JQOCJKUVECLNAC-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- WMOZUHUKRDBJEF-UHFFFAOYSA-N s-[[3-[(3-cyano-6,7-dimethoxyquinolin-4-yl)amino]phenyl]methyl] ethanethioate Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC(CSC(C)=O)=C1 WMOZUHUKRDBJEF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52419600A | 2000-03-13 | 2000-03-13 | |
| US09/524,196 | 2000-03-13 | ||
| PCT/US2001/007068 WO2001068186A2 (en) | 2000-03-13 | 2001-03-06 | Use of cyanoquinolines for treating or inhibiting colonic polyps |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003526686A JP2003526686A (ja) | 2003-09-09 |
| JP2003526686A5 true JP2003526686A5 (https=) | 2008-04-24 |
Family
ID=24088181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001566747A Withdrawn JP2003526686A (ja) | 2000-03-13 | 2001-03-06 | 結腸ポリープの治療または阻害するためのシアノキノリンの使用 |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP1263503B1 (https=) |
| JP (1) | JP2003526686A (https=) |
| KR (2) | KR100817423B1 (https=) |
| CN (1) | CN1190197C (https=) |
| AR (1) | AR035482A1 (https=) |
| AT (1) | ATE308364T1 (https=) |
| AU (2) | AU4545201A (https=) |
| BR (1) | BR0109165A (https=) |
| CA (1) | CA2402742C (https=) |
| DE (1) | DE60114580T2 (https=) |
| DK (1) | DK1263503T3 (https=) |
| EA (1) | EA200200976A1 (https=) |
| ES (1) | ES2248302T3 (https=) |
| HK (1) | HK1048775B (https=) |
| HU (1) | HUP0300547A2 (https=) |
| IL (2) | IL151249A0 (https=) |
| MX (1) | MXPA02008836A (https=) |
| NO (1) | NO20024356L (https=) |
| NZ (1) | NZ521117A (https=) |
| PL (1) | PL202873B1 (https=) |
| TW (1) | TWI262805B (https=) |
| WO (1) | WO2001068186A2 (https=) |
| ZA (1) | ZA200208178B (https=) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6576644B2 (en) | 2000-09-06 | 2003-06-10 | Bristol-Myers Squibb Co. | Quinoline inhibitors of cGMP phosphodiesterase |
| US7019012B2 (en) | 2000-12-20 | 2006-03-28 | Boehringer Ingelheim International Pharma Gmbh & Co. Kg | Quinazoline derivatives and pharmaceutical compositions containing them |
| CA2468015A1 (en) | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 2-aminoquinoline compounds |
| WO2003064399A1 (fr) * | 2002-01-28 | 2003-08-07 | Ube Industries, Ltd. | Procede de production de derive de quinazolin-4-one |
| CA2475141A1 (en) | 2002-02-05 | 2003-08-14 | Wyeth | Process for the synthesis of n-acyl-2-amino-4-alkoxy-5-nitrobenzoic acids |
| JP2005536462A (ja) * | 2002-04-30 | 2005-12-02 | ユン ジン ファーマスーチカル インダストリーズ カンパニー リミテッド | カスパーゼ−３阻害剤としてのキノリン誘導体、この製造方法及びこれを含む薬剤学的組成物 |
| DE10221018A1 (de) | 2002-05-11 | 2003-11-27 | Boehringer Ingelheim Pharma | Verwendung von Hemmern der EGFR-vermittelten Signaltransduktion zur Behandlung von gutartiger Prostatahyperplasie (BPH)/Prostatahypertrophie |
| EP2280003B1 (en) | 2002-07-15 | 2014-04-02 | Symphony Evolution, Inc. | Process for preparing receptor-type kinase modulators |
| OA13309A (en) | 2002-12-20 | 2007-04-13 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth. |
| US7109337B2 (en) | 2002-12-20 | 2006-09-19 | Pfizer Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| NZ544472A (en) | 2003-07-03 | 2009-04-30 | Myriad Genetics Inc | Compounds and therapeutical use thereof |
| PT2213661E (pt) | 2003-09-26 | 2011-12-15 | Exelixis Inc | Moduladores de c-met e métodos de uso |
| TW200529846A (en) | 2004-02-20 | 2005-09-16 | Wyeth Corp | 3-quinolinecarbonitrile protein kinase inhibitors |
| KR20070011458A (ko) | 2004-04-08 | 2007-01-24 | 탈자진 인코포레이티드 | 키나제의 벤조트리아진 억제제 |
| MXPA06013164A (es) | 2004-05-14 | 2007-02-13 | Pfizer Prod Inc | Derivados de pirimidina para el tratamiento de crecimiento de celulas anormal. |
| MXPA06013165A (es) | 2004-05-14 | 2007-02-13 | Pfizer Prod Inc | Derivados de pirimidina para el tratamiento de crecimiento de celulas anormal. |
| WO2005111024A1 (en) | 2004-05-14 | 2005-11-24 | Pfizer Products Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
| CA2592900A1 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| CN101180273A (zh) * | 2005-05-25 | 2008-05-14 | 惠氏公司 | 合成6-烷基氨基喹啉衍生物的方法 |
| CN103626742B (zh) | 2005-11-01 | 2017-04-26 | 塔格根公司 | 激酶的联-芳基间-嘧啶抑制剂 |
| CA2833706C (en) | 2005-11-11 | 2014-10-21 | Boehringer Ingelheim International Gmbh | Quinazoline derivatives for the treatment of cancer diseases |
| DE102006029445A1 (de) * | 2006-06-21 | 2007-12-27 | Bayer Schering Pharma Ag | Neue 3-Cyano-chinoline als Kinase-Inhibitoren |
| DE102006029446A1 (de) * | 2006-06-21 | 2007-12-27 | Bayer Schering Pharma Ag | Neue 3-substituierte-Chinoline als Kinase-Inhibitoren |
| AU2007299080B2 (en) | 2006-09-18 | 2013-04-18 | Boehringer Ingelheim International Gmbh | Method for treating cancer harboring EGFR mutations |
| DE102007024470A1 (de) | 2007-05-24 | 2008-11-27 | Bayer Schering Pharma Aktiengesellschaft | Neue Sulfoximin-substituierte Chinolin- bzw. Chinazolinderivate als Kinase-Inhibitoren |
| EP2072502A1 (de) | 2007-12-20 | 2009-06-24 | Bayer Schering Pharma Aktiengesellschaft | Sulfoximid-substituierte Chinolin- und Chinazolinderivate als Kinase-Inhibitoren |
| SG173014A1 (en) | 2009-01-16 | 2011-08-29 | Exelixis Inc | Malate salt of n- (4- { [ 6, 7-bis (methyloxy) quin0lin-4-yl] oxy}phenyl)-n' - (4 -fluorophenyl) cyclopropane-1,1-dicarboxamide, and crystalline forms therof for the treatment of cancer |
| CN102625799A (zh) * | 2009-06-25 | 2012-08-01 | 安姆根有限公司 | 杂环化合物及其用途 |
| PL2451445T3 (pl) | 2009-07-06 | 2019-09-30 | Boehringer Ingelheim International Gmbh | Sposób suszenia BIBW2992, jego soli i stałych preparatów farmaceutycznych zawierających tę substancję czynną |
| UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
| CA2816957A1 (en) | 2010-11-07 | 2012-05-10 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
| UY35464A (es) | 2013-03-15 | 2014-10-31 | Araxes Pharma Llc | Inhibidores covalentes de kras g12c. |
| TWI659021B (zh) | 2013-10-10 | 2019-05-11 | 亞瑞克西斯製藥公司 | Ｋｒａｓ ｇ１２ｃ之抑制劑 |
| US9242965B2 (en) | 2013-12-31 | 2016-01-26 | Boehringer Ingelheim International Gmbh | Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors |
| JP6533997B2 (ja) * | 2014-12-26 | 2019-06-26 | 株式会社ヤクルト本社 | Ｚｎｆ１４３阻害活性を有する化合物およびその利用 |
| JP2018513853A (ja) * | 2015-04-10 | 2018-05-31 | アラクセス ファーマ エルエルシー | 置換キナゾリン化合物およびその使用方法 |
| EP3356354A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058902A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| EP3356353A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058807A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| KR20180081596A (ko) | 2015-11-16 | 2018-07-16 | 아락세스 파마 엘엘씨 | 치환된 헤테로사이클릭 그룹을 포함하는 2-치환된 퀴나졸린 화합물 및 이의 사용 방법 |
| WO2018140514A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(6-(3-hydroxynaphthalen-1-yl)quinazolin-2-yl)azetidin-1-yl)prop-2-en-1-one derivatives and similar compounds as kras g12c inhibitors for the treatment of cancer |
| CN110382482A (zh) | 2017-01-26 | 2019-10-25 | 亚瑞克西斯制药公司 | 稠合的杂-杂二环化合物及其使用方法 |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| WO2018140513A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
| EP3573954A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| AU2018271990A1 (en) | 2017-05-25 | 2019-12-12 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
| US11639346B2 (en) | 2017-05-25 | 2023-05-02 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant KRAS, HRAS or NRAS |
| JP2020521741A (ja) | 2017-05-25 | 2020-07-27 | アラクセス ファーマ エルエルシー | がんの処置のための化合物およびその使用の方法 |
| MX2021000887A (es) | 2018-08-01 | 2021-03-31 | Araxes Pharma Llc | Compuestos espiroheterociclicos y metodos de uso de los mismos para el tratamiento de cancer. |
| WO2026017799A1 (en) * | 2024-07-18 | 2026-01-22 | Centre Hospitalier Universitaire Vaudois | Substituted 3-cyanoquinolines for the prevention and treatment of sexually transmitted diseases |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA73073C2 (uk) * | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| US6002008A (en) * | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| PL353267A1 (en) * | 1999-08-12 | 2003-11-03 | American Cyanamid Company | Nsaid and efgr kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
-
2001
- 2001-03-06 KR KR1020027012074A patent/KR100817423B1/ko not_active Expired - Fee Related
- 2001-03-06 PL PL363072A patent/PL202873B1/pl not_active IP Right Cessation
- 2001-03-06 HU HU0300547A patent/HUP0300547A2/hu unknown
- 2001-03-06 EA EA200200976A patent/EA200200976A1/ru unknown
- 2001-03-06 AT AT01918367T patent/ATE308364T1/de not_active IP Right Cessation
- 2001-03-06 CN CNB018093981A patent/CN1190197C/zh not_active Expired - Fee Related
- 2001-03-06 BR BR0109165-4A patent/BR0109165A/pt not_active Application Discontinuation
- 2001-03-06 EP EP01918367A patent/EP1263503B1/en not_active Expired - Lifetime
- 2001-03-06 AU AU4545201A patent/AU4545201A/xx active Pending
- 2001-03-06 JP JP2001566747A patent/JP2003526686A/ja not_active Withdrawn
- 2001-03-06 IL IL15124901A patent/IL151249A0/xx active IP Right Grant
- 2001-03-06 DK DK01918367T patent/DK1263503T3/da active
- 2001-03-06 ES ES01918367T patent/ES2248302T3/es not_active Expired - Lifetime
- 2001-03-06 AU AU2001245452A patent/AU2001245452B2/en not_active Ceased
- 2001-03-06 MX MXPA02008836A patent/MXPA02008836A/es active IP Right Grant
- 2001-03-06 DE DE60114580T patent/DE60114580T2/de not_active Expired - Lifetime
- 2001-03-06 NZ NZ521117A patent/NZ521117A/en unknown
- 2001-03-06 CA CA002402742A patent/CA2402742C/en not_active Expired - Fee Related
- 2001-03-06 KR KR1020077027115A patent/KR20080009294A/ko not_active Ceased
- 2001-03-06 HK HK03101049.6A patent/HK1048775B/en not_active IP Right Cessation
- 2001-03-06 WO PCT/US2001/007068 patent/WO2001068186A2/en not_active Ceased
- 2001-03-12 AR ARP010101143A patent/AR035482A1/es not_active Application Discontinuation
- 2001-03-12 TW TW090105702A patent/TWI262805B/zh active
-
2002
- 2002-08-14 IL IL151249A patent/IL151249A/en not_active IP Right Cessation
- 2002-09-12 NO NO20024356A patent/NO20024356L/no unknown
- 2002-10-10 ZA ZA200208178A patent/ZA200208178B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003526686A5 (https=) | ||
| ZA200208178B (en) | Use of cyanoquinolines for treating or inhibiting colonic polyps. | |
| RU99123060A (ru) | Замещенные 3-цианохинолины | |
| RU2006106267A (ru) | Применение комбинации ингибитора киназы рецептора эпидермального фактора роста и цитотоксических средств для лечения и ингибирования рака | |
| US6384051B1 (en) | Method of treating or inhibiting colonic polyps | |
| GEP20257770B (en) | Compounds for the treatment of kinase-dependent disorders | |
| KR100531969B1 (ko) | 치환된 3-시아노 퀴놀린, 이를 함유하는 약제학적 조성물 및 이의 제조방법 | |
| AU2001245452A1 (en) | Use of cyanoquinolines for treating or inhibiting colonic polyps | |
| CO5150185A1 (es) | N-[4-(3-cloro-4-fluoro-fenilamino)-7-(3-morfolin-4-il- propoxi)-quinazolin-6-il]-acrilamida, un inhibidor irreversible de las cinasas de la tirosina | |
| RU2002129353A (ru) | Терапевтические сочетания гипотензивного и антиангиогенного лекарственных средств | |
| JP2018511626A5 (https=) | ||
| MX338920B (es) | Proceso para la preparacion de compuestos de aminocrotonilo. | |
| RU2003114740A (ru) | Азотсодержащие ароматические производные | |
| JP2016512256A5 (https=) | ||
| RU2007137266A (ru) | Хиназолиноновые антагонисты кальциевых каналов т-типа | |
| RU2007134908A (ru) | Применение ингибитора активности киназы рецептора эпидермального фактора роста для лечения пациентов, невосприимчивых к гефитинибу | |
| JP2019524844A5 (https=) | ||
| RU2350618C2 (ru) | ПРОИЗВОДНЫЕ ХИНАЗОЛИНА В КАЧЕСТВЕ ИНГИБИТОРОВ Src ТИРОЗИНКИНАЗЫ | |
| JP2014532063A5 (https=) | ||
| RU2005114487A (ru) | Терапевтическое лечение | |
| US20170252335A1 (en) | Combination of Ceritinib with an EGFR Inhibitor | |
| RU2017143182A (ru) | Способы и композиции для ингибирования пути egf/egfr в комбинации с ингибиторами тирозинкиназы | |
| RU2004127869A (ru) | Новые лекарственные композиции на основе антихолинергических средств и ингибиторов egfr-киназы | |
| BRPI0407903A (pt) | protomicroemulsão, implemento de limpeza contendo a mesma, e método de uso do mesmo | |
| RU2007103703A (ru) | Комбинация, включающая ингибитор бррм (белка резистентности рака молочной железы) и 4-(4-метилпиперазин-1-илметил)-n-(4-метил-3-(4-пиридин-3-ил)пиримидин-2-иламино)фенил)-бензамид |