JP2003526686A5 - - Google Patents
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- 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- Withdrawn
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- 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
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- 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
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- 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
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| 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)
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| AU (2) | AU2001245452B2 (https=) |
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| IL (2) | IL151249A0 (https=) |
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| PL (1) | PL202873B1 (https=) |
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| WO (1) | WO2001068186A2 (https=) |
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| AU2002352878B2 (en) | 2001-11-27 | 2007-11-22 | Merck Sharp & Dohme Corp. | 2-Aminoquinoline compounds |
| WO2003064399A1 (fr) * | 2002-01-28 | 2003-08-07 | Ube Industries, Ltd. | Procede de production de derive de quinazolin-4-one |
| BR0307375A (pt) * | 2002-02-05 | 2004-12-07 | Wyeth Corp | Processo para a sìntese de ácidos n-acil-2-amino-4-alcóxi-5-nitro-benzóicos |
| 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 |
| US7576074B2 (en) | 2002-07-15 | 2009-08-18 | Rice Kenneth D | Receptor-type kinase modulators and methods of use |
| CA2529611C (en) | 2002-12-20 | 2009-12-15 | Pfizer Products Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
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| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
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| WO2006074147A2 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
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| JP5688877B2 (ja) | 2005-11-11 | 2015-03-25 | 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 | 癌疾患の治療用キナゾリン誘導体 |
| DE102006029446A1 (de) * | 2006-06-21 | 2007-12-27 | Bayer Schering Pharma Ag | Neue 3-substituierte-Chinoline als Kinase-Inhibitoren |
| DE102006029445A1 (de) * | 2006-06-21 | 2007-12-27 | Bayer Schering Pharma Ag | Neue 3-Cyano-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 |
| NZ779754A (en) | 2009-01-16 | 2023-04-28 | Exelixis Inc | Malate salt of n-(4-{ [6,7-bis(methyloxy)quinolin-4-yl] oxy} phenyl)-n’-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide, and crystalline forms thereof 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 |
| PT2451445T (pt) | 2009-07-06 | 2019-07-10 | Boehringer Ingelheim Int | Processo para secagem de bibw2992, dos seus sais e de formulações farmacêuticas sólidas compreendendo este ingrediente ativo |
| UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
| AU2010363329A1 (en) | 2010-11-07 | 2013-05-09 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| 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 |
| ES2898765T3 (es) * | 2015-04-10 | 2022-03-08 | Araxes Pharma Llc | Compuestos de quinazolina sustituidos y métodos de uso de los mismos |
| WO2017058805A1 (en) | 2015-09-28 | 2017-04-06 | 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 |
| EP3356347A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| WO2017058728A1 (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 |
| US11136308B2 (en) | 2017-01-26 | 2021-10-05 | Araxes Pharma Llc | Substituted quinazoline and quinazolinone 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 |
| JP7327802B2 (ja) | 2017-01-26 | 2023-08-16 | アラクセス ファーマ エルエルシー | 縮合ヘテロ－ヘテロ二環式化合物およびその使用方法 |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| CN110869357A (zh) | 2017-05-25 | 2020-03-06 | 亚瑞克西斯制药公司 | 化合物及其用于治疗癌症的使用方法 |
| WO2018218069A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| US10745385B2 (en) | 2017-05-25 | 2020-08-18 | Araxes Pharma Llc | Covalent inhibitors of KRAS |
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| US6002008A (en) * | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| UA73073C2 (uk) * | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| HUP0203162A3 (en) * | 1999-08-12 | 2006-07-28 | Wyeth Holdings Corp Madison | Nsaid and efgr kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
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- 2001-03-06 KR KR1020027012074A patent/KR100817423B1/ko not_active Expired - Fee Related
- 2001-03-06 HK HK03101049.6A patent/HK1048775B/en not_active IP Right Cessation
- 2001-03-06 EA EA200200976A patent/EA200200976A1/ru unknown
- 2001-03-06 PL PL363072A patent/PL202873B1/pl not_active IP Right Cessation
- 2001-03-06 IL IL15124901A patent/IL151249A0/xx active IP Right Grant
- 2001-03-06 KR KR1020077027115A patent/KR20080009294A/ko not_active Ceased
- 2001-03-06 EP EP01918367A patent/EP1263503B1/en not_active Expired - Lifetime
- 2001-03-06 HU HU0300547A patent/HUP0300547A2/hu unknown
- 2001-03-06 MX MXPA02008836A patent/MXPA02008836A/es active IP Right Grant
- 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 AT AT01918367T patent/ATE308364T1/de not_active IP Right Cessation
- 2001-03-06 DE DE60114580T patent/DE60114580T2/de not_active Expired - Lifetime
- 2001-03-06 JP JP2001566747A patent/JP2003526686A/ja not_active Withdrawn
- 2001-03-06 BR BR0109165-4A patent/BR0109165A/pt not_active Application Discontinuation
- 2001-03-06 DK DK01918367T patent/DK1263503T3/da active
- 2001-03-06 AU AU4545201A patent/AU4545201A/xx active Pending
- 2001-03-06 NZ NZ521117A patent/NZ521117A/en unknown
- 2001-03-06 WO PCT/US2001/007068 patent/WO2001068186A2/en not_active Ceased
- 2001-03-06 CA CA002402742A patent/CA2402742C/en not_active Expired - Fee Related
- 2001-03-12 AR ARP010101143A patent/AR035482A1/es not_active Application Discontinuation
- 2001-03-12 TW TW090105702A patent/TWI262805B/zh active
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2002
- 2002-08-14 IL IL151249A patent/IL151249A/en not_active IP Right Cessation
- 2002-09-12 NO NO20024356A patent/NO20024356L/no unknown
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