CA2402742C - Method of treating or inhibiting colonic polyps - Google Patents

Info

Publication number

CA2402742C

CA2402742C CA002402742A CA2402742A CA2402742C CA 2402742 C CA2402742 C CA 2402742C CA 002402742 A CA002402742 A CA 002402742A CA 2402742 A CA2402742 A CA 2402742A CA 2402742 C CA2402742 C CA 2402742C

Authority

CA

Canada

Prior art keywords

amino

carbon atoms

carbonitrile

phenylamino

quinoline

Prior art date

2000-03-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 208000035984 Colonic Polyps Diseases 0.000 title claims abstract description 11
• 238000000034 method Methods 0.000 title abstract description 38
• 230000002401 inhibitory effect Effects 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 110
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 289
• -1 nitro, carboxy Chemical group 0.000 claims description 118
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 90
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 26
• 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 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical compound CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
• 125000004970 halomethyl group Chemical group 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000005042 acyloxymethyl group Chemical group 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 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 claims description 7
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 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 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• 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 claims description 6
• 125000004423 acyloxy group Chemical group 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 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 claims description 4
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• JGTPCHRGCCPWCC-UHFFFAOYSA-N 4-(3-bromoanilino)-7-ethoxy-6-nitroquinoline-3-carbonitrile Chemical compound C=12C=C([N+]([O-])=O)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=CC(Br)=C1 JGTPCHRGCCPWCC-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 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 claims description 3
• VCNRVJKPJCKMIG-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-6-nitroquinoline-3-carbonitrile Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=CC(C#N)=C1NC1=CC=C(F)C(Cl)=C1 VCNRVJKPJCKMIG-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 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 claims description 3
• 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 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 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 claims description 2
• RAKHHLWOXRVOCS-NSCUHMNNSA-N (e)-n-[4-(3-chloro-4-fluoroanilino)-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=C(F)C(Cl)=C1 RAKHHLWOXRVOCS-NSCUHMNNSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
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• 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
• FHZKUQUEIDJHNY-UHFFFAOYSA-N 4-(3-methylsulfanylanilino)-6-nitroquinoline-3-carbonitrile Chemical compound CSC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C#N)[N+]([O-])=O)=C1 FHZKUQUEIDJHNY-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
• RGTKLWHHDZWEQQ-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylanilino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1NC1=CC(C)=C(O)C(C)=C1 RGTKLWHHDZWEQQ-UHFFFAOYSA-N 0.000 claims 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 claims 1
• KSTABQDMPVWBQA-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)methylamino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OCC)C(OCC)=CC2=NC=C(C#N)C=1NCC1=CC=C(Cl)C(Cl)=C1 KSTABQDMPVWBQA-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
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