JP2016532656A5

JP2016532656A5 -

Download PDF

Info

Publication number: JP2016532656A5
Authority: JP; Japan
Prior art keywords: chloro; prop; piperazin; quinazolin; fluoro
Prior art date: 2014-10-10
Legal status : Granted

Application number

JP2016521333A

Other languages

English (en)

Japanese (ja)

Other versions

JP6559123B2 (ja

JP2016532656A (ja

Filing date

2014-10-10

Publication date

2017-11-09

2014-10-09 Priority claimed from JOP/2014/0289A external-priority patent/JO3805B1/ar

2014-10-10 Application filed filed Critical

2014-10-10 Priority claimed from PCT/US2014/060036 external-priority patent/WO2015054572A1/en

2016-10-20 Publication of JP2016532656A publication Critical patent/JP2016532656A/ja

2017-11-09 Publication of JP2016532656A5 publication Critical patent/JP2016532656A5/ja

2019-08-14 Application granted granted Critical

2019-08-14 Publication of JP6559123B2 publication Critical patent/JP6559123B2/ja

Status Active legal-status Critical Current

2034-10-10 Anticipated expiration legal-status Critical

Links

150000001875 compounds Chemical class 0.000 claims description 117
-1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 103
125000000217 alkyl group Chemical group 0.000 claims description 49
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 23
125000001072 heteroaryl group Chemical group 0.000 claims description 21
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
125000002837 carbocyclic group Chemical group 0.000 claims description 10
125000004966 cyanoalkyl group Chemical group 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
206010028980 Neoplasm Diseases 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
201000011510 cancer Diseases 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 2
125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 65
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 33
125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
YNMBXEWTXSZTHP-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)F)N1CCN(CC1)C(C=C)=O YNMBXEWTXSZTHP-UHFFFAOYSA-N 0.000 claims 2
DCUNRLLJHAWKRZ-UHFFFAOYSA-N 5-methyl-1h-indazole Chemical compound CC1=CC=C2NN=CC2=C1 DCUNRLLJHAWKRZ-UHFFFAOYSA-N 0.000 claims 2
ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 claims 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
125000004464 hydroxyphenyl group Chemical group 0.000 claims 2
QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 claims 2
JIIBSIMXAXZDEL-INIZCTEOSA-N (2R)-4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound C(C=C)(=O)N1[C@H](CN(CC1)C1=NC=NC2=CC(=C(C=C12)C1=CC=C(C=C1)Cl)Cl)C#N JIIBSIMXAXZDEL-INIZCTEOSA-N 0.000 claims 1
JIIBSIMXAXZDEL-MRXNPFEDSA-N (2S)-4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound Clc1ccc(cc1)-c1cc2c(ncnc2cc1Cl)N1CCN([C@@H](C1)C#N)C(=O)C=C JIIBSIMXAXZDEL-MRXNPFEDSA-N 0.000 claims 1
FRSSAEVAURADPX-IBGZPJMESA-N (2S)-4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazine-2-carboxamide Chemical compound NC(=O)[C@@H]1CN(CCN1C(=O)C=C)c1ncnc2cc(Cl)c(cc12)-c1ccc(Cl)cc1 FRSSAEVAURADPX-IBGZPJMESA-N 0.000 claims 1
QKASFJNWWCTSGP-RMKNXTFCSA-N (E)-1-[4-(6-chloro-7-phenylquinazolin-4-yl)piperazin-1-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=CC=C1)N1CCN(CC1)C(\C=C\CN(C)C)=O QKASFJNWWCTSGP-RMKNXTFCSA-N 0.000 claims 1
VGKOBAAKSQZNCD-VMPITWQZSA-N (E)-1-[4-[6-chloro-7-(2-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound CN(C)C\C=C\C(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(Cl)C=C12)C1=C(F)C=CC=C1 VGKOBAAKSQZNCD-VMPITWQZSA-N 0.000 claims 1
REYPQWDSLONYOF-QPJJXVBHSA-N (E)-1-[4-[6-chloro-8-fluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1O)F)F)N1CCN(CC1)C(\C=C\CN(C)C)=O REYPQWDSLONYOF-QPJJXVBHSA-N 0.000 claims 1
LPYMUYXNZNCYEE-VMPITWQZSA-N (E)-1-[4-[6-chloro-8-fluoro-7-(2-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1)F)F)N1CCN(CC1)C(\C=C\CN(C)C)=O LPYMUYXNZNCYEE-VMPITWQZSA-N 0.000 claims 1
DQBWLZZZBFAZMQ-VMPITWQZSA-N (E)-1-[4-[6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)N1CCN(CC1)C(\C=C\CN(C)C)=O DQBWLZZZBFAZMQ-VMPITWQZSA-N 0.000 claims 1
IMOLPJTUMWEJAN-NSCUHMNNSA-N (E)-1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]-4-hydroxybut-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)N1CCN(CC1)C(\C=C\CO)=O IMOLPJTUMWEJAN-NSCUHMNNSA-N 0.000 claims 1
NIGLWQWHTJDRJH-VMPITWQZSA-N (E)-1-[4-[7-chloro-6-(2-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(\C=C\CN(C)C)=O)C1=C(C=CC=C1)Cl NIGLWQWHTJDRJH-VMPITWQZSA-N 0.000 claims 1
RZPUJQSVHYOXNU-GZTJUZNOSA-N (E)-2-[4-[6-chloro-7-(2-fluorophenyl)quinazolin-4-yl]piperazine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)F)N1CCN(CC1)C(=O)\C(\C#N)=C\C(C)C RZPUJQSVHYOXNU-GZTJUZNOSA-N 0.000 claims 1
ACCCQSRYERZRNL-GHRIWEEISA-N (E)-2-[4-[6-chloro-7-(2-fluorophenyl)quinazolin-4-yl]piperazine-1-carbonyl]-5-hydroxy-4,4-dimethylpent-2-enenitrile Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)F)N1CCN(CC1)C(=O)\C(\C#N)=C\C(CO)(C)C ACCCQSRYERZRNL-GHRIWEEISA-N 0.000 claims 1
KQDAQPDKNQDMST-RIYZIHGNSA-N (E)-2-[4-[6-chloro-8-fluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazine-1-carbonyl]-3-(1,3-thiazol-5-yl)prop-2-enenitrile Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1O)F)F)N1CCN(CC1)C(=O)\C(\C#N)=C\C1=CN=CS1 KQDAQPDKNQDMST-RIYZIHGNSA-N 0.000 claims 1
HDHVYWZGKMVUEE-FOWTUZBSSA-N (E)-2-[4-[6-chloro-8-fluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazine-1-carbonyl]-3-pyridin-2-ylprop-2-enenitrile Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1O)F)F)N1CCN(CC1)C(=O)\C(\C#N)=C\C1=NC=CC=C1 HDHVYWZGKMVUEE-FOWTUZBSSA-N 0.000 claims 1
FZIMVEXNZMVGNL-XNTDXEJSSA-N (E)-2-[4-[6-chloro-8-fluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1O)F)F)N1CCN(CC1)C(=O)\C(\C#N)=C\C(C)C FZIMVEXNZMVGNL-XNTDXEJSSA-N 0.000 claims 1
VDTBGHRLBSOPJH-KPKJPENVSA-N (E)-4-(dimethylamino)-1-[4-[8-fluoro-6,7-bis(2-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]but-2-en-1-one Chemical compound CN(C/C=C/C(=O)N1CCN(CC1)C1=NC=NC2=C(C(=C(C=C12)C1=C(C=CC=C1)F)C1=C(C=CC=C1)F)F)C VDTBGHRLBSOPJH-KPKJPENVSA-N 0.000 claims 1
ZOKDLNHHGMBAMY-NSCUHMNNSA-N (E)-4-amino-1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]but-2-en-1-one Chemical compound NC/C=C/C(=O)N1CCN(CC1)C1=NC=NC2=C(C(=C(C=C12)Cl)C1=C2C=NNC2=CC=C1C)F ZOKDLNHHGMBAMY-NSCUHMNNSA-N 0.000 claims 1
SVWRZGYZVNEDSK-UPHRSURJSA-N (Z)-4-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-oxobut-2-enenitrile Chemical compound FC1=CC(F)=C(C=C1)C1=C(Cl)C=C2C(=C1)N=CN=C2N1CCN(CC1)C(=O)\C=C/C#N SVWRZGYZVNEDSK-UPHRSURJSA-N 0.000 claims 1
IFKLZUNLNWQOAI-MRXNPFEDSA-N 1-[(2R)-4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-2-(hydroxymethyl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1C[C@@H](N(CC1)C(C=C)=O)CO)C1=CC=C(C=C1)Cl IFKLZUNLNWQOAI-MRXNPFEDSA-N 0.000 claims 1
IFKLZUNLNWQOAI-INIZCTEOSA-N 1-[(2S)-4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-2-(hydroxymethyl)piperazin-1-yl]prop-2-en-1-one Chemical compound OC[C@@H]1CN(CCN1C(=O)C=C)c1ncnc2cc(Cl)c(cc12)-c1ccc(Cl)cc1 IFKLZUNLNWQOAI-INIZCTEOSA-N 0.000 claims 1
JONQXARUZMFDMA-UHFFFAOYSA-N 1-[2-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]phenyl]cyclopropane-1-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C=CC=C1)C1(CC1)C#N JONQXARUZMFDMA-UHFFFAOYSA-N 0.000 claims 1
AGSDVWSMKBITHV-UHFFFAOYSA-N 1-[3-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-4-fluorophenyl]cyclopropane-1-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C=1C=C(C=CC=1F)C1(CC1)C#N AGSDVWSMKBITHV-UHFFFAOYSA-N 0.000 claims 1
OAKNVDIGUBBNCK-UHFFFAOYSA-N 1-[4-(6-chloro-2-methoxy-7-phenylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1C1=CC=CC=C1)OC)N1CCN(CC1)C(C=C)=O OAKNVDIGUBBNCK-UHFFFAOYSA-N 0.000 claims 1
CEFRQJDZWPCQQP-UHFFFAOYSA-N 1-[4-(6-chloro-2-methyl-7-phenylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1C1=CC=CC=C1)C)N1CCN(CC1)C(C=C)=O CEFRQJDZWPCQQP-UHFFFAOYSA-N 0.000 claims 1
QSLWYNJTXZGWSB-UHFFFAOYSA-N 1-[4-(6-chloro-7-naphthalen-1-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=CC2=CC=CC=C12)N1CCN(CC1)C(C=C)=O QSLWYNJTXZGWSB-UHFFFAOYSA-N 0.000 claims 1
REXOZNLXIGVHSQ-UHFFFAOYSA-N 1-[4-(6-chloro-7-phenylquinolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=CC=NC2=CC=1C1=CC=CC=C1)N1CCN(CC1)C(C=C)=O REXOZNLXIGVHSQ-UHFFFAOYSA-N 0.000 claims 1
LBKJYIJVHAUCQZ-UHFFFAOYSA-N 1-[4-(6-chloro-7-piperidin-1-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2N=CN=C(N3CCN(CC3)C(=O)C=C)C2=C1)N1CCCCC1 LBKJYIJVHAUCQZ-UHFFFAOYSA-N 0.000 claims 1
MKJFJWZQRYDKCL-UHFFFAOYSA-N 1-[4-(6-chloro-7-pyridin-2-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=NC=CC=C1)N1CCN(CC1)C(C=C)=O MKJFJWZQRYDKCL-UHFFFAOYSA-N 0.000 claims 1
LNYQRNIFKHWDBC-UHFFFAOYSA-N 1-[4-(6-chloro-7-pyridin-3-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2N=CN=C(N3CCN(CC3)C(=O)C=C)C2=C1)C1=CN=CC=C1 LNYQRNIFKHWDBC-UHFFFAOYSA-N 0.000 claims 1
WQFZLGPSWWBEQU-UHFFFAOYSA-N 1-[4-(6-chloro-7-quinazolin-8-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC1C=1C=CC=C2C=NC=NC12)N1CCN(CC1)C(C=C)=O WQFZLGPSWWBEQU-UHFFFAOYSA-N 0.000 claims 1
QUTHCVSAOWLVEI-UHFFFAOYSA-N 1-[4-(6-chloro-7-quinolin-4-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=NC2=CC=CC=C12)N1CCN(CC1)C(C=C)=O QUTHCVSAOWLVEI-UHFFFAOYSA-N 0.000 claims 1
PCOOMHAOSSAFSA-UHFFFAOYSA-N 1-[4-(6-chloro-7-quinolin-5-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C2C=CC=NC2=CC=C1)N1CCN(CC1)C(C=C)=O PCOOMHAOSSAFSA-UHFFFAOYSA-N 0.000 claims 1
GOMAQQZCOVNYNI-UHFFFAOYSA-N 1-[4-(6-chloro-7-thiophen-2-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C=1SC=CC=1)N1CCN(CC1)C(C=C)=O GOMAQQZCOVNYNI-UHFFFAOYSA-N 0.000 claims 1
QWISGKNZGQOAJG-UHFFFAOYSA-N 1-[4-(6-ethyl-7-phenylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound C(C)C=1C=C2C(=NC=NC2=CC=1C1=CC=CC=C1)N1CCN(CC1)C(C=C)=O QWISGKNZGQOAJG-UHFFFAOYSA-N 0.000 claims 1
QCNFSVAJKRKWFW-UHFFFAOYSA-N 1-[4-(7-chloro-6-morpholin-4-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)N1CCOCC1 QCNFSVAJKRKWFW-UHFFFAOYSA-N 0.000 claims 1
JFWXDEIZSVTXMO-UHFFFAOYSA-N 1-[4-(7-chloro-6-phenylisoquinolin-1-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C=CN=C(C2=C1)N1CCN(CC1)C(C=C)=O)C1=CC=CC=C1 JFWXDEIZSVTXMO-UHFFFAOYSA-N 0.000 claims 1
ZPPGBGCDKOFVIA-UHFFFAOYSA-N 1-[4-(7-chloro-6-phenylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound Clc1cc2ncnc(N3CCN(CC3)C(=O)C=C)c2cc1-c1ccccc1 ZPPGBGCDKOFVIA-UHFFFAOYSA-N 0.000 claims 1
UJHGFLSPKCXWDS-UHFFFAOYSA-N 1-[4-(7-chloro-6-pyridin-3-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C=1C=NC=CC=1 UJHGFLSPKCXWDS-UHFFFAOYSA-N 0.000 claims 1
YQAQQFKSOLAQFT-UHFFFAOYSA-N 1-[4-(7-chloro-6-pyridin-4-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=C1)N=CN=C2N1CCN(CC1)C(=O)C=C)C1=CC=NC=C1 YQAQQFKSOLAQFT-UHFFFAOYSA-N 0.000 claims 1
VDZZZNHNNCUOMP-UHFFFAOYSA-N 1-[4-(7-chloro-6-thiophen-2-ylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C=1SC=CC=1 VDZZZNHNNCUOMP-UHFFFAOYSA-N 0.000 claims 1
USWJXUMSFMWEPQ-UHFFFAOYSA-N 1-[4-[2-amino-7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Nc1nc(N2CCN(CC2)C(=O)C=C)c2cc(c(Cl)cc2n1)-c1ccc(Cl)cc1 USWJXUMSFMWEPQ-UHFFFAOYSA-N 0.000 claims 1
LCQKRNAPYQFDFW-UHFFFAOYSA-N 1-[4-[5-(2-chlorophenyl)-4a,7a-dihydrothieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=CC=C1)C1=CSC2N=CN=C(C21)N1CCN(CC1)C(C=C)=O LCQKRNAPYQFDFW-UHFFFAOYSA-N 0.000 claims 1
UKBLZUDQPGVFEN-UHFFFAOYSA-N 1-[4-[5-(2-chlorophenyl)-7,7a-dihydro-4aH-pyrrolo[2,3-d]pyrimidin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=CC=C1)C1=CNC2N=CN=C(C21)N1CCN(CC1)C(C=C)=O UKBLZUDQPGVFEN-UHFFFAOYSA-N 0.000 claims 1
YAOXGOQNIDBBIA-UHFFFAOYSA-N 1-[4-[6,8-dichloro-7-(2-methoxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC2=CC=CC=C12)OC)Cl)N1CCN(CC1)C(C=C)=O YAOXGOQNIDBBIA-UHFFFAOYSA-N 0.000 claims 1
YDUYZFMHUOIQCH-UHFFFAOYSA-N 1-[4-[6-(2-chlorophenyl)-7-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=CC=C1)C=1C=C2C(=NC=NC2=CC=1F)N1CCN(CC1)C(C=C)=O YDUYZFMHUOIQCH-UHFFFAOYSA-N 0.000 claims 1
KBPOZSHJOYBGJO-UHFFFAOYSA-N 1-[4-[6-(4-bromophenyl)-7-chloroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound BrC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=CC=1Cl)N1CCN(CC1)C(C=C)=O KBPOZSHJOYBGJO-UHFFFAOYSA-N 0.000 claims 1
PVVYUDCPISEZPW-UHFFFAOYSA-N 1-[4-[6-(4-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=CC=1)N1CCN(CC1)C(C=C)=O PVVYUDCPISEZPW-UHFFFAOYSA-N 0.000 claims 1
NIKZHNQHYNRRTH-UHFFFAOYSA-N 1-[4-[6-(trifluoromethyl)-7-[2-(trifluoromethyl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC(C=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)C(F)(F)F)N1CCN(CC1)C(C=C)=O)(F)F NIKZHNQHYNRRTH-UHFFFAOYSA-N 0.000 claims 1
FIVMEWZHXYVFSM-UHFFFAOYSA-N 1-[4-[6-chloro-2-(methylamino)-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1C1=C2C=NNC2=CC=C1C)NC)N1CCN(CC1)C(C=C)=O FIVMEWZHXYVFSM-UHFFFAOYSA-N 0.000 claims 1
HTYWTFMIOROXAZ-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethoxy]-8-fluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C(C=CC=C1O)F)F)OCCN(C)C)N1CCN(CC1)C(C=C)=O HTYWTFMIOROXAZ-UHFFFAOYSA-N 0.000 claims 1
YGBHSZUSILDDFX-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethoxy]-8-fluoro-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)OCCN(C)C)N1CCN(CC1)C(C=C)=O YGBHSZUSILDDFX-UHFFFAOYSA-N 0.000 claims 1
QDBNFRCUYRSZRX-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethyl-methylamino]-8-fluoro-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)N(C)CCN(C)C)N1CCN(CC1)C(C=C)=O QDBNFRCUYRSZRX-UHFFFAOYSA-N 0.000 claims 1
LEZSBJPQYYYXLL-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethyl-methylamino]-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)N(C)CCN(C)C)N1CCN(CC1)C(C=C)=O LEZSBJPQYYYXLL-UHFFFAOYSA-N 0.000 claims 1
JOJJUMPADFNQKT-UHFFFAOYSA-N 1-[4-[6-chloro-2-[3-(dimethylamino)propoxy]-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1C1=C2C=NNC2=CC=C1C)OCCCN(C)C)N1CCN(CC1)C(C=C)=O JOJJUMPADFNQKT-UHFFFAOYSA-N 0.000 claims 1
YGAKEXBYIBLQJP-UHFFFAOYSA-N 1-[4-[6-chloro-2-[3-(dimethylamino)propoxy]-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)OCCCN(C)C)N1CCN(CC1)C(C=C)=O YGAKEXBYIBLQJP-UHFFFAOYSA-N 0.000 claims 1
QNDAMYVBIWPDCM-UHFFFAOYSA-N 1-[4-[6-chloro-3-ethynyl-7-(2-fluorophenyl)quinolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC=C1)C1=C(Cl)C=C2C(=C1)N=CC(C#C)=C2N1CCN(CC1)C(=O)C=C QNDAMYVBIWPDCM-UHFFFAOYSA-N 0.000 claims 1
NKTUSZJFMROTTG-UHFFFAOYSA-N 1-[4-[6-chloro-5-(2-chlorophenyl)-1H-indazol-3-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NNC2=C1)N1CCN(CC1)C(C=C)=O)C1=C(C=CC=C1)Cl NKTUSZJFMROTTG-UHFFFAOYSA-N 0.000 claims 1
PRQGKPXTVNFULA-UHFFFAOYSA-N 1-[4-[6-chloro-5-fluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Oc1cccc(F)c1-c1cc2ncnc(N3CCN(CC3)C(=O)C=C)c2c(F)c1Cl PRQGKPXTVNFULA-UHFFFAOYSA-N 0.000 claims 1
DTOGBQCJAPEFTN-UHFFFAOYSA-N 1-[4-[6-chloro-7-(1,2,3,4-tetrahydroquinolin-5-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C2CCCNC2=CC=C1)N1CCN(CC1)C(C=C)=O DTOGBQCJAPEFTN-UHFFFAOYSA-N 0.000 claims 1
VHBQYQDQURWJRD-UHFFFAOYSA-N 1-[4-[6-chloro-7-(1-methylindazol-3-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=NN(C2=CC=CC=C12)C)N1CCN(CC1)C(C=C)=O VHBQYQDQURWJRD-UHFFFAOYSA-N 0.000 claims 1
FTNPFWBZTIRYTO-UHFFFAOYSA-N 1-[4-[6-chloro-7-(1H-indazol-5-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C=1C=C2C=NNC2=CC=1)N1CCN(CC1)C(C=C)=O FTNPFWBZTIRYTO-UHFFFAOYSA-N 0.000 claims 1
KZOKCMMDKLSEML-UHFFFAOYSA-N 1-[4-[6-chloro-7-(1H-indazol-7-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C=1C=CC=C2C=NNC=12)N1CCN(CC1)C(C=C)=O KZOKCMMDKLSEML-UHFFFAOYSA-N 0.000 claims 1
XSTXHFFXTAFSNX-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,3-dihydro-1,4-benzodioxin-5-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2N=CN=C(N3CCN(CC3)C(=O)C=C)C2=C1)C1=CC=CC2=C1OCCO2 XSTXHFFXTAFSNX-UHFFFAOYSA-N 0.000 claims 1
GDOJQXONAXYAHV-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-dichlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C=C1)Cl)Cl)N1CCN(CC1)C(C=C)=O GDOJQXONAXYAHV-UHFFFAOYSA-N 0.000 claims 1
SAQFOJAOJBQOHA-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluoro-5-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C(=C1)O)F)F)N1CCN(CC1)C(C=C)=O SAQFOJAOJBQOHA-UHFFFAOYSA-N 0.000 claims 1
NOHXGDXXLQUYNN-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluorophenyl)-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=C(C=C1)F)F)F)N1CCN(CC1)C(C=C)=O NOHXGDXXLQUYNN-UHFFFAOYSA-N 0.000 claims 1
ZQCRLVOLDJTCNL-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluorophenyl)-8-hydroxyquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Oc1c(c(Cl)cc2c(ncnc12)N1CCN(CC1)C(=O)C=C)-c1ccc(F)cc1F ZQCRLVOLDJTCNL-UHFFFAOYSA-N 0.000 claims 1
TWYZWUWWASKLHM-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluorophenyl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=CN=NC2=CC=1C1=C(C=C(C=C1)F)F)N1CCN(CC1)C(C=C)=O TWYZWUWWASKLHM-UHFFFAOYSA-N 0.000 claims 1
LYESZICKUICZAC-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]-2-ethynylpiperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C=C1)F)F)N1CC(N(CC1)C(C=C)=O)C#C LYESZICKUICZAC-UHFFFAOYSA-N 0.000 claims 1
UPGQAEWXYBUNCX-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-hydroxybut-2-yn-1-one Chemical compound OCC#CC(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(Cl)C=C12)C1=C(F)C=C(F)C=C1 UPGQAEWXYBUNCX-UHFFFAOYSA-N 0.000 claims 1
JJDGZJUMIJUXLS-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C=C1)F)F)N1CCN(CC1)C(C=C)=O JJDGZJUMIJUXLS-UHFFFAOYSA-N 0.000 claims 1
QRGJYDRMVSXRKT-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,5-dichlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC(=C1)Cl)Cl)N1CCN(CC1)C(C=C)=O QRGJYDRMVSXRKT-UHFFFAOYSA-N 0.000 claims 1
DPWYQQARBFEKJI-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,5-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC(=C1)F)F)N1CCN(CC1)C(C=C)=O DPWYQQARBFEKJI-UHFFFAOYSA-N 0.000 claims 1
OLHVYQAUBZBXBI-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,6-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1F)F)N1CCN(CC1)C(C=C)=O OLHVYQAUBZBXBI-UHFFFAOYSA-N 0.000 claims 1
MAXRNAGCBBEQSE-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-chloro-6-methylphenyl)-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1C)Cl)F)N1CCN(CC1)C(C=C)=O MAXRNAGCBBEQSE-UHFFFAOYSA-N 0.000 claims 1
MTCHPZKBNNXDSP-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)Cl)N1CCN(CC1)C(C=C)=O MTCHPZKBNNXDSP-UHFFFAOYSA-N 0.000 claims 1
CGGBNQSAHGYEEW-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-cyclopropylphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)C1CC1)N1CCN(CC1)C(C=C)=O CGGBNQSAHGYEEW-UHFFFAOYSA-N 0.000 claims 1
MJRWXBIMCOZNDG-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-ethynylphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)C#C)N1CCN(CC1)C(C=C)=O MJRWXBIMCOZNDG-UHFFFAOYSA-N 0.000 claims 1
QSAFZMROROICDI-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-fluoro-6-hydroxyphenyl)-8-methoxyquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1O)F)OC)N1CCN(CC1)C(C=C)=O QSAFZMROROICDI-UHFFFAOYSA-N 0.000 claims 1
XJNKYVOSKDTGNY-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-fluoro-6-hydroxyphenyl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC1=CC=CC(F)=C1C1=C(Cl)C=C2C(=C1)N=NC=C2N1CCN(CC1)C(=O)C=C XJNKYVOSKDTGNY-UHFFFAOYSA-N 0.000 claims 1
PNYUIQVHHOUMPY-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1O)F)N1CCN(CC1)C(C=C)=O PNYUIQVHHOUMPY-UHFFFAOYSA-N 0.000 claims 1
RDLWXWUVTLPGBV-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-fluoro-6-methoxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1OC)F)N1CCN(CC1)C(C=C)=O RDLWXWUVTLPGBV-UHFFFAOYSA-N 0.000 claims 1
PPRMFFNQNYSASM-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-fluorophenyl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=CN=NC2=CC=1C1=C(C=CC=C1)F)N1CCN(CC1)C(C=C)=O PPRMFFNQNYSASM-UHFFFAOYSA-N 0.000 claims 1
NUBHUDUXMHBKFO-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=2CCCCC1=2)O)N1CCN(CC1)C(C=C)=O NUBHUDUXMHBKFO-UHFFFAOYSA-N 0.000 claims 1
AJCKDTGGCTYFTR-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-hydroxynaphthalen-1-yl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=CN=NC2=CC=1C1=C(C=CC2=CC=CC=C12)O)N1CCN(CC1)C(C=C)=O AJCKDTGGCTYFTR-UHFFFAOYSA-N 0.000 claims 1
KLCPIJNAJOAJJK-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-hydroxyphenyl)quinazolin-4-yl]-2-methylpiperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)O)N1CC(N(CC1)C(C=C)=O)C KLCPIJNAJOAJJK-UHFFFAOYSA-N 0.000 claims 1
XUYKRGJKJJLHSO-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-methoxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC2=CC=CC=C12)OC)N1CCN(CC1)C(C=C)=O XUYKRGJKJJLHSO-UHFFFAOYSA-N 0.000 claims 1
CMDAVGAYVSXPPI-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3,6-difluoro-2-hydroxyphenyl)-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC1=C(C(F)=CC=C1F)C1=C(Cl)C=C2C(=NC=NC2=C1F)N1CCN(CC1)C(=O)C=C CMDAVGAYVSXPPI-UHFFFAOYSA-N 0.000 claims 1
LRSBGKBLVWYZAU-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC(=CC=C1)Cl)N1CCN(CC1)C(C=C)=O LRSBGKBLVWYZAU-UHFFFAOYSA-N 0.000 claims 1
YWIAFWQZQRDGCZ-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC(=CC=C1)F)N1CCN(CC1)C(C=C)=O YWIAFWQZQRDGCZ-UHFFFAOYSA-N 0.000 claims 1
NANCENFEOSVPDN-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3-hydroxynaphthalen-1-yl)-8-methoxyquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)OC)N1CCN(CC1)C(C=C)=O NANCENFEOSVPDN-UHFFFAOYSA-N 0.000 claims 1
JRYNAXYXBIOLTP-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC(=CC2=CC=CC=C12)O)N1CCN(CC1)C(C=C)=O JRYNAXYXBIOLTP-UHFFFAOYSA-N 0.000 claims 1
GNILIFWTNWRJQE-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC(=CC=C1)O)N1CCN(CC1)C(C=C)=O GNILIFWTNWRJQE-UHFFFAOYSA-N 0.000 claims 1
OBDYEUMTPLGJJO-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3-methoxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC(=CC2=CC=CC=C12)OC)N1CCN(CC1)C(C=C)=O OBDYEUMTPLGJJO-UHFFFAOYSA-N 0.000 claims 1
OVWRNKUEWKZFEE-UHFFFAOYSA-N 1-[4-[6-chloro-7-(4-chloro-2-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C=C1)Cl)F)N1CCN(CC1)C(C=C)=O OVWRNKUEWKZFEE-UHFFFAOYSA-N 0.000 claims 1
HOEOWSJVDZYHRF-UHFFFAOYSA-N 1-[4-[6-chloro-7-(4-chloro-2-hydroxyphenyl)isoquinolin-1-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC1=C(C=CC(Cl)=C1)C1=C(Cl)C=C2C=CN=C(N3CCN(CC3)C(=O)C=C)C2=C1 HOEOWSJVDZYHRF-UHFFFAOYSA-N 0.000 claims 1
FXRQIENUNKJYLX-UHFFFAOYSA-N 1-[4-[6-chloro-7-(4-chloro-2-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C=C1)Cl)O)N1CCN(CC1)C(C=C)=O FXRQIENUNKJYLX-UHFFFAOYSA-N 0.000 claims 1
FYJIGFIDDKMMEW-UHFFFAOYSA-N 1-[4-[6-chloro-7-(4-chlorophenyl)isoquinolin-1-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C=CN=C(C2=CC=1C1=CC=C(C=C1)Cl)N1CCN(CC1)C(C=C)=O FYJIGFIDDKMMEW-UHFFFAOYSA-N 0.000 claims 1
DFEZCFPYGAAROG-UHFFFAOYSA-N 1-[4-[6-chloro-7-(4-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=C(C=C1)Cl)N1CCN(CC1)C(C=C)=O DFEZCFPYGAAROG-UHFFFAOYSA-N 0.000 claims 1
CVYFMLRCXKOPIY-UHFFFAOYSA-N 1-[4-[6-chloro-7-(4-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=C(C=C1)F)N1CCN(CC1)C(C=C)=O CVYFMLRCXKOPIY-UHFFFAOYSA-N 0.000 claims 1
XEHOOVBSSXZCHD-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5,6,7,8-tetrahydronaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=CC=2CCCCC1=2)N1CCN(CC1)C(C=C)=O XEHOOVBSSXZCHD-UHFFFAOYSA-N 0.000 claims 1
YKWIGTCLBDPDJQ-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5,6-dimethyl-1H-indazol-7-yl)-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound CC1=CC2=C(NN=C2)C(=C1C)C1=C(Cl)C=C2C(=NC=NC2=C1F)N1CCN(CC1)C(=O)C=C YKWIGTCLBDPDJQ-UHFFFAOYSA-N 0.000 claims 1
MVMPKXSISRRKBY-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-chloro-1H-indazol-7-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C=1C=C(C=C2C=NNC=12)Cl)N1CCN(CC1)C(C=C)=O MVMPKXSISRRKBY-UHFFFAOYSA-N 0.000 claims 1
IMKWJMQQVWCVJF-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-chloro-2-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC(=C1)Cl)F)N1CCN(CC1)C(C=C)=O IMKWJMQQVWCVJF-UHFFFAOYSA-N 0.000 claims 1
REDGHFHIRSCTTC-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-fluoro-2-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC(=C1)F)O)N1CCN(CC1)C(C=C)=O REDGHFHIRSCTTC-UHFFFAOYSA-N 0.000 claims 1
MCPXKPOTEYNDPT-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-methoxy-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C2C=NNC2=CC=C1OC)N1CCN(CC1)C(C=C)=O MCPXKPOTEYNDPT-UHFFFAOYSA-N 0.000 claims 1
RUNNTCOZWWNTIP-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-methyl-1H-indazol-4-yl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Cc1ccc2[nH]ncc2c1-c1cc2nncc(N3CCN(CC3)C(=O)C=C)c2cc1Cl RUNNTCOZWWNTIP-UHFFFAOYSA-N 0.000 claims 1
LVJNMZYXVYJJDZ-UHFFFAOYSA-N 1-[4-[6-chloro-7-(6-chloro-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C2C=NNC2=CC(=C1)Cl)N1CCN(CC1)C(C=C)=O LVJNMZYXVYJJDZ-UHFFFAOYSA-N 0.000 claims 1
CGJURDBMOPNKHP-UHFFFAOYSA-N 1-[4-[6-chloro-7-(6-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound CC1=CC2=C(C=NN2)C(=C1)C1=C(Cl)C=C2C(=C1)N=CN=C2N1CCN(CC1)C(=O)C=C CGJURDBMOPNKHP-UHFFFAOYSA-N 0.000 claims 1
PFDBJNUZRXGTAR-UHFFFAOYSA-N 1-[4-[6-chloro-7-(6-methyl-1H-indazol-7-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C=1C(=CC=C2C=NNC=12)C)N1CCN(CC1)C(C=C)=O PFDBJNUZRXGTAR-UHFFFAOYSA-N 0.000 claims 1
VZKMGVIKFOHCJC-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(1,3-thiazol-5-yl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)C1=CN=CS1)N1CCN(CC1)C(C=C)=O VZKMGVIKFOHCJC-UHFFFAOYSA-N 0.000 claims 1
QKRGGXZBKYPGIH-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(1-methylcyclopropyl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)C1(CC1)C)N1CCN(CC1)C(C=C)=O QKRGGXZBKYPGIH-UHFFFAOYSA-N 0.000 claims 1
RUMMUILTEBXPCR-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(1H-pyrazol-4-yl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound N1N=CC(=C1)C1=C(C=CC=C1)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl RUMMUILTEBXPCR-UHFFFAOYSA-N 0.000 claims 1
BGIOAJNOPPPBHB-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(hydroxymethyl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)CO)N1CCN(CC1)C(C=C)=O BGIOAJNOPPPBHB-UHFFFAOYSA-N 0.000 claims 1
GMUQUXNKNCSOJM-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(trifluoromethyl)phenyl]cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=CN=NC2=CC=1C1=C(C=CC=C1)C(F)(F)F)N1CCN(CC1)C(C=C)=O GMUQUXNKNCSOJM-UHFFFAOYSA-N 0.000 claims 1
JVAOFSJEYPKTSP-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(trifluoromethyl)phenyl]quinazolin-4-yl]-2-methylpiperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)C(F)(F)F)N1CC(N(CC1)C(C=C)=O)C JVAOFSJEYPKTSP-UHFFFAOYSA-N 0.000 claims 1
FSYCXERZSLCXBW-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(trifluoromethyl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)C(F)(F)F)N1CCN(CC1)C(C=C)=O FSYCXERZSLCXBW-UHFFFAOYSA-N 0.000 claims 1
AAEKVEINEZICAS-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-[(dimethylamino)methyl]-6-fluorophenyl]-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1F)CN(C)C)F)N1CCN(CC1)C(C=C)=O AAEKVEINEZICAS-UHFFFAOYSA-N 0.000 claims 1
LKNAEWXCWLLJML-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-fluoro-5-(2-hydroxypropan-2-yl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC(=C1)C(C)(C)O)F)N1CCN(CC1)C(C=C)=O LKNAEWXCWLLJML-UHFFFAOYSA-N 0.000 claims 1
FWYWFFYCMGFDIK-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-fluoro-5-(trifluoromethoxy)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC(=C1)OC(F)(F)F)F)N1CCN(CC1)C(C=C)=O FWYWFFYCMGFDIK-UHFFFAOYSA-N 0.000 claims 1
ZLELLBCRLPCOFT-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-methyl-5-(methylamino)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC(=C1)NC)C)N1CCN(CC1)C(C=C)=O ZLELLBCRLPCOFT-UHFFFAOYSA-N 0.000 claims 1
QTJOFFMPHKBEQJ-UHFFFAOYSA-N 1-[4-[6-chloro-7-[3-(1H-pyrazol-5-yl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound N1N=CC=C1C=1C=C(C=CC=1)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl QTJOFFMPHKBEQJ-UHFFFAOYSA-N 0.000 claims 1
MCJQRNXHTQCQQB-UHFFFAOYSA-N 1-[4-[6-chloro-7-[3-(difluoromethyl)naphthalen-1-yl]-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC(F)C1=CC2=C(C=CC=C2)C(=C1)C1=C(Cl)C=C2C(=NC=NC2=C1F)N1CCN(CC1)C(=O)C=C MCJQRNXHTQCQQB-UHFFFAOYSA-N 0.000 claims 1
MEYJMMLRYJABBW-UHFFFAOYSA-N 1-[4-[6-chloro-7-[4-hydroxy-2-(trifluoromethyl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C=C1)O)C(F)(F)F)N1CCN(CC1)C(C=C)=O MEYJMMLRYJABBW-UHFFFAOYSA-N 0.000 claims 1
YXRHLRXGGREZKI-UHFFFAOYSA-N 1-[4-[6-chloro-7-[5-(difluoromethyl)-2-fluorophenyl]-8-fluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC(=C1)C(F)F)F)F)N1CCN(CC1)C(C=C)=O YXRHLRXGGREZKI-UHFFFAOYSA-N 0.000 claims 1
XVWAUODEBBYQAK-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-2-(2-hydroxyethylamino)-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)NCCO)N1CCN(CC1)C(C=C)=O XVWAUODEBBYQAK-UHFFFAOYSA-N 0.000 claims 1
QUYKZLZICATLES-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-2-(methylamino)-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)NC)N1CCN(CC1)C(C=C)=O QUYKZLZICATLES-UHFFFAOYSA-N 0.000 claims 1
DLYXGTXMBXYNAW-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(2-fluorophenyl)quinazolin-4-yl]-2-ethynylpiperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1)F)F)N1CC(N(CC1)C(C=C)=O)C#C DLYXGTXMBXYNAW-UHFFFAOYSA-N 0.000 claims 1
RTHLFZDWPYVCCE-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(2-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1)F)F)N1CCN(CC1)C(C=C)=O RTHLFZDWPYVCCE-UHFFFAOYSA-N 0.000 claims 1
YJWJJXIBHVCPHU-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(2-methoxy-6-methylphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1C)OC)F)N1CCN(CC1)C(C=C)=O YJWJJXIBHVCPHU-UHFFFAOYSA-N 0.000 claims 1
RPXCNCRDXKTEHQ-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)-2-(methylamino)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound CNC1=NC2=C(F)C(=C(Cl)C=C2C(=N1)N1CCN(CC1)C(=O)C=C)C1=CC(O)=CC2=C1C=CC=C2 RPXCNCRDXKTEHQ-UHFFFAOYSA-N 0.000 claims 1
NRZSFXBVYWTKEW-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)-2-[(1-methylpyrrolidin-3-yl)amino]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)NC1CN(CC1)C)N1CCN(CC1)C(C=C)=O NRZSFXBVYWTKEW-UHFFFAOYSA-N 0.000 claims 1
MWXSVVVDZNMBKY-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]-2-(hydroxymethyl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)N1CC(N(CC1)C(C=C)=O)CO MWXSVVVDZNMBKY-UHFFFAOYSA-N 0.000 claims 1
QJJHZXDTCSGYQM-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]-2-[(dimethylamino)methyl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)N1CC(N(CC1)C(C=C)=O)CN(C)C QJJHZXDTCSGYQM-UHFFFAOYSA-N 0.000 claims 1
JIPIHCUZVBBERR-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)N1CCN(CC1)C(C=C)=O JIPIHCUZVBBERR-UHFFFAOYSA-N 0.000 claims 1
RTDBXHABGLDADS-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-fluoro-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C2C=NNC2=CC=C1F)F)N1CCN(CC1)C(C=C)=O RTDBXHABGLDADS-UHFFFAOYSA-N 0.000 claims 1
LUQQDERCFJFBBQ-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-(1,3-thiazol-5-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Cc1ccc2[nH]ncc2c1-c1c(Cl)cc2c(nc(nc2c1F)-c1cncs1)N1CCN(CC1)C(=O)C=C LUQQDERCFJFBBQ-UHFFFAOYSA-N 0.000 claims 1
KJOSGVXPZYUQIR-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-(1-methylpyrazol-4-yl)oxyquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)OC=1C=NN(C=1)C)N1CCN(CC1)C(C=C)=O KJOSGVXPZYUQIR-UHFFFAOYSA-N 0.000 claims 1
PFQFOPLDZBTYCC-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-(1H-pyrazol-5-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)C1=CC=NN1)N1CCN(CC1)C(C=C)=O PFQFOPLDZBTYCC-UHFFFAOYSA-N 0.000 claims 1
HHFMAIRRWYCXLS-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-(2-morpholin-4-ylethoxy)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)OCCN1CCOCC1)N1CCN(CC1)C(C=C)=O HHFMAIRRWYCXLS-UHFFFAOYSA-N 0.000 claims 1
PQEAOXGIWOXHRW-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-(2-pyrrolidin-1-ylethoxy)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)OCCN1CCCC1)N1CCN(CC1)C(C=C)=O PQEAOXGIWOXHRW-UHFFFAOYSA-N 0.000 claims 1
HKNSISVRNYUYFR-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-[(1-methylpiperidin-4-yl)amino]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)NC1CCN(CC1)C)N1CCN(CC1)C(C=C)=O HKNSISVRNYUYFR-UHFFFAOYSA-N 0.000 claims 1
PHELBDYDPSAWJB-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-[(1-methylpyrrolidin-3-yl)amino]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)NC1CN(CC1)C)N1CCN(CC1)C(C=C)=O PHELBDYDPSAWJB-UHFFFAOYSA-N 0.000 claims 1
YKSFNPHAFKOVIT-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-[2-(4-methylpiperazin-1-yl)ethoxy]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)OCCN1CCN(CC1)C)N1CCN(CC1)C(C=C)=O YKSFNPHAFKOVIT-UHFFFAOYSA-N 0.000 claims 1
LZEAGRNJGRQMAA-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(6-fluoro-1H-indazol-7-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C=1C(=CC=C2C=NNC=12)F)F)N1CCN(CC1)C(C=C)=O LZEAGRNJGRQMAA-UHFFFAOYSA-N 0.000 claims 1
BCFVCUHDMXEJOF-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(6-methyl-1H-indazol-7-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C=1C(=CC=C2C=NNC=12)C)F)N1CCN(CC1)C(C=C)=O BCFVCUHDMXEJOF-UHFFFAOYSA-N 0.000 claims 1
IXWAUFLCOHGFEX-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-[2-(2-hydroxypropan-2-yl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1)C(C)(C)O)F)N1CCN(CC1)C(C=C)=O IXWAUFLCOHGFEX-UHFFFAOYSA-N 0.000 claims 1
BPLQGLVADWUFLY-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-[2-(trifluoromethyl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1)C(F)(F)F)F)N1CCN(CC1)C(C=C)=O BPLQGLVADWUFLY-UHFFFAOYSA-N 0.000 claims 1
IVVWPYMATKEUQO-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-[2-fluoro-5-(1H-imidazol-5-yl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC(=C1)C=1N=CNC=1)F)F)N1CCN(CC1)C(C=C)=O IVVWPYMATKEUQO-UHFFFAOYSA-N 0.000 claims 1
YWUACZJSIZFOMW-UHFFFAOYSA-N 1-[4-[6-chloro-8-methoxy-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C2C=NNC2=CC=C1C)OC)N1CCN(CC1)C(C=C)=O YWUACZJSIZFOMW-UHFFFAOYSA-N 0.000 claims 1
QUGAPSNKNWDTOU-UHFFFAOYSA-N 1-[4-[7-(1,3-benzoxazol-7-yl)-6-chloroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound O1C=NC2=C1C(=CC=C2)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl QUGAPSNKNWDTOU-UHFFFAOYSA-N 0.000 claims 1
DFTSOTGDOFGJTF-UHFFFAOYSA-N 1-[4-[7-(1H-benzimidazol-4-yl)-6-chloroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound N1C=NC2=C1C=CC=C2C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl DFTSOTGDOFGJTF-UHFFFAOYSA-N 0.000 claims 1
KRAFXPZCSRNNAM-UHFFFAOYSA-N 1-[4-[7-(2,4-difluorophenyl)-6,8-difluoroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Fc1ccc(c(F)c1)-c1c(F)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C KRAFXPZCSRNNAM-UHFFFAOYSA-N 0.000 claims 1
GXLLVQPUXRMPLE-UHFFFAOYSA-N 1-[4-[7-(2,4-difluorophenyl)-6-(trifluoromethyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C=CC(=C1)F)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C(F)(F)F GXLLVQPUXRMPLE-UHFFFAOYSA-N 0.000 claims 1
DOVGHQNGQPGQHU-UHFFFAOYSA-N 1-[4-[7-(2,4-difluorophenyl)-8-fluoro-6-methylquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Cc1cc2c(ncnc2c(F)c1-c1ccc(F)cc1F)N1CCN(CC1)C(=O)C=C DOVGHQNGQPGQHU-UHFFFAOYSA-N 0.000 claims 1
OQYUPEIJIZGKLP-UHFFFAOYSA-N 1-[4-[7-(2-amino-1,3-benzoxazol-5-yl)-6-chloroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound NC=1OC2=C(N=1)C=C(C=C2)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl OQYUPEIJIZGKLP-UHFFFAOYSA-N 0.000 claims 1
URDILORWFOILAY-UHFFFAOYSA-N 1-[4-[7-(2-amino-5-methylpyrimidin-4-yl)-6-chloroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound NC1=NC=C(C(=N1)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl)C URDILORWFOILAY-UHFFFAOYSA-N 0.000 claims 1
ABZMUQANXKWHBX-UHFFFAOYSA-N 1-[4-[7-(2-chloro-5-hydroxyphenyl)-6-(trifluoromethyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C(C=C1)O)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C(F)(F)F ABZMUQANXKWHBX-UHFFFAOYSA-N 0.000 claims 1
PXBGIHXERTUJEA-UHFFFAOYSA-N 1-[4-[7-(2-fluoro-6-hydroxyphenyl)-6-(trifluoromethyl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Oc1cccc(F)c1-c1cc2nncc(N3CCN(CC3)C(=O)C=C)c2cc1C(F)(F)F PXBGIHXERTUJEA-UHFFFAOYSA-N 0.000 claims 1
RVKPORQTCUUODU-UHFFFAOYSA-N 1-[4-[7-(2-fluoro-6-hydroxyphenyl)-6-(trifluoromethyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC1=C(C(=CC=C1)O)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C(F)(F)F RVKPORQTCUUODU-UHFFFAOYSA-N 0.000 claims 1
NIGMLNOVECNYFO-UHFFFAOYSA-N 1-[4-[7-(2-fluorophenyl)-6-hydroxyquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Oc1cc2c(ncnc2cc1-c1ccccc1F)N1CCN(CC1)C(=O)C=C NIGMLNOVECNYFO-UHFFFAOYSA-N 0.000 claims 1
KPYCUKBFUITQPF-UHFFFAOYSA-N 1-[4-[7-(2-hydroxynaphthalen-1-yl)-6-(trifluoromethyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC1=C(C2=CC=CC=C2C=C1)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C(F)(F)F KPYCUKBFUITQPF-UHFFFAOYSA-N 0.000 claims 1
GUCNCDWEKSLEBC-UHFFFAOYSA-N 1-[4-[7-(3-amino-1,2-benzoxazol-4-yl)-6-chloroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound NC1=NOC2=C1C(=CC=C2)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl GUCNCDWEKSLEBC-UHFFFAOYSA-N 0.000 claims 1
PWRBWYHNAXAARN-UHFFFAOYSA-N 1-[4-[7-(3-hydroxynaphthalen-1-yl)-6-(trifluoromethyl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC=1C=C(C2=CC=CC=C2C=1)C1=C(C=C2C(=CN=NC2=C1)N1CCN(CC1)C(C=C)=O)C(F)(F)F PWRBWYHNAXAARN-UHFFFAOYSA-N 0.000 claims 1
HAJUVCFSXQGBQD-UHFFFAOYSA-N 1-[4-[7-(5-methyl-1H-indazol-4-yl)-6-(trifluoromethyl)cinnolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound CC=1C(=C2C=NNC2=CC=1)C1=C(C=C2C(=CN=NC2=C1)N1CCN(CC1)C(C=C)=O)C(F)(F)F HAJUVCFSXQGBQD-UHFFFAOYSA-N 0.000 claims 1
SYRYMOQJYDVNEO-UHFFFAOYSA-N 1-[4-[7-(5-methyl-1H-indazol-4-yl)-6-(trifluoromethyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound CC=1C(=C2C=NNC2=CC=1)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C(F)(F)F SYRYMOQJYDVNEO-UHFFFAOYSA-N 0.000 claims 1
WNLHCLQLOCQUOP-UHFFFAOYSA-N 1-[4-[7-[2-(trifluoromethyl)phenyl]quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC(C1=C(C=CC=C1)C1=CC=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)(F)F WNLHCLQLOCQUOP-UHFFFAOYSA-N 0.000 claims 1
BVCJWYJYLNZYJX-UHFFFAOYSA-N 1-[4-[7-chloro-6-(2,5-dichlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=CC(=C(Cl)C=C1)C1=C(Cl)C=C2N=CN=C(N3CCN(CC3)C(=O)C=C)C2=C1 BVCJWYJYLNZYJX-UHFFFAOYSA-N 0.000 claims 1
OMBGOMDFEOQGAD-UHFFFAOYSA-N 1-[4-[7-chloro-6-(2-chloro-5-fluorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C1=C(C=CC(=C1)F)Cl OMBGOMDFEOQGAD-UHFFFAOYSA-N 0.000 claims 1
RSVUKPRLFYMBPZ-UHFFFAOYSA-N 1-[4-[7-chloro-6-(2-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Clc1ccccc1-c1cc2c(ncnc2cc1Cl)N1CCN(CC1)C(=O)C=C RSVUKPRLFYMBPZ-UHFFFAOYSA-N 0.000 claims 1
UATGUDBUCPYXNM-UHFFFAOYSA-N 1-[4-[7-chloro-6-(2-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC1=C(C=CC=C1)C1=C(Cl)C=C2N=CN=C(N3CCN(CC3)C(=O)C=C)C2=C1 UATGUDBUCPYXNM-UHFFFAOYSA-N 0.000 claims 1
YSMYGXLFWKFBSE-UHFFFAOYSA-N 1-[4-[7-chloro-6-(3,4-dichlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C1=CC(=C(C=C1)Cl)Cl YSMYGXLFWKFBSE-UHFFFAOYSA-N 0.000 claims 1
QUBHXBPPKHCBJO-UHFFFAOYSA-N 1-[4-[7-chloro-6-(3-chlorophenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C1=CC(=CC=C1)Cl QUBHXBPPKHCBJO-UHFFFAOYSA-N 0.000 claims 1
IJJHOCZHFKNJNJ-UHFFFAOYSA-N 1-[4-[7-chloro-6-(3-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C1=CC(=CC=C1)O IJJHOCZHFKNJNJ-UHFFFAOYSA-N 0.000 claims 1
VPODTNMHLSACQK-UHFFFAOYSA-N 1-[4-[7-chloro-6-(4-chloro-2-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC1=C(C=CC(Cl)=C1)C1=C(Cl)C=C2N=CN=C(N3CCN(CC3)C(=O)C=C)C2=C1 VPODTNMHLSACQK-UHFFFAOYSA-N 0.000 claims 1
FHWRZQDMIREABM-UHFFFAOYSA-N 1-[4-[7-chloro-6-(4-chlorophenyl)-2-methoxyquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound COc1nc(N2CCN(CC2)C(=O)C=C)c2cc(c(Cl)cc2n1)-c1ccc(Cl)cc1 FHWRZQDMIREABM-UHFFFAOYSA-N 0.000 claims 1
UDKAYUJMKNQOOF-UHFFFAOYSA-N 1-[4-[7-chloro-6-(4-chlorophenyl)-2-methylquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Cc1nc(N2CCN(CC2)C(=O)C=C)c2cc(c(Cl)cc2n1)-c1ccc(Cl)cc1 UDKAYUJMKNQOOF-UHFFFAOYSA-N 0.000 claims 1
CQXAQQOFPAPOKT-UHFFFAOYSA-N 1-[4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-2-(2-hydroxyethyl)piperazin-1-yl]prop-2-en-1-one Chemical compound OCCC1CN(CCN1C(=O)C=C)c1ncnc2cc(Cl)c(cc12)-c1ccc(Cl)cc1 CQXAQQOFPAPOKT-UHFFFAOYSA-N 0.000 claims 1
DHBIGKJOXCGDPD-UHFFFAOYSA-N 1-[4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-2-[(dimethylamino)methyl]piperazin-1-yl]prop-2-en-1-one Chemical compound CN(C)CC1CN(CCN1C(=O)C=C)c1ncnc2cc(Cl)c(cc12)-c1ccc(Cl)cc1 DHBIGKJOXCGDPD-UHFFFAOYSA-N 0.000 claims 1
BVNXGHZFCUJIBG-UHFFFAOYSA-N 1-[4-[7-chloro-6-(4-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C1=CC=C(C=C1)O BVNXGHZFCUJIBG-UHFFFAOYSA-N 0.000 claims 1
PXPJDNUBFUAITJ-UHFFFAOYSA-N 1-[4-[7-cyclopropyl-6-(4-cyclopropylphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound C1(CC1)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)C1=CC=C(C=C1)C1CC1 PXPJDNUBFUAITJ-UHFFFAOYSA-N 0.000 claims 1
ACAVOXZNLGUVFO-UHFFFAOYSA-N 1-[4-[8-fluoro-7-(2-fluorophenyl)-6-(trifluoromethyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Fc1ccccc1-c1c(F)c2ncnc(N3CCN(CC3)C(=O)C=C)c2cc1C(F)(F)F ACAVOXZNLGUVFO-UHFFFAOYSA-N 0.000 claims 1
QKOBJQWOZRHSHK-UHFFFAOYSA-N 1-[4-[[6-chloro-5-(2-chlorophenyl)-1H-indazol-3-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound Clc1ccccc1-c1cc2c(NC3CCN(CC3)C(=O)C=C)n[nH]c2cc1Cl QKOBJQWOZRHSHK-UHFFFAOYSA-N 0.000 claims 1
HEOGLXRQJWSWSS-UHFFFAOYSA-N 1-[4-[[7-chloro-6-(2-chlorophenyl)quinazolin-4-yl]amino]piperidin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)NC1CCN(CC1)C(C=C)=O)C1=C(C=CC=C1)Cl HEOGLXRQJWSWSS-UHFFFAOYSA-N 0.000 claims 1
SCRXBLNEMXWBGH-UHFFFAOYSA-N 1-prop-2-enoyl-4-quinazolin-4-ylpiperazine-2-carbonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC=CC=C12)C#N SCRXBLNEMXWBGH-UHFFFAOYSA-N 0.000 claims 1
CCLFMWKMBLVHQE-UHFFFAOYSA-N 2-[2-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]phenyl]acetonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C=CC=C1)CC#N CCLFMWKMBLVHQE-UHFFFAOYSA-N 0.000 claims 1
WESPEBFRBSHGNW-UHFFFAOYSA-N 2-[4-(6-chloro-7-phenylquinazolin-4-yl)-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=CC=CC=C1)CC#N WESPEBFRBSHGNW-UHFFFAOYSA-N 0.000 claims 1
RLHHVJVCKJQCAH-UHFFFAOYSA-N 2-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C=C(C=C1)F)F)CC#N RLHHVJVCKJQCAH-UHFFFAOYSA-N 0.000 claims 1
SJIOQBWCURFASK-UHFFFAOYSA-N 2-[4-[6-chloro-7-(2-chlorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C=CC=C1)Cl)CC#N SJIOQBWCURFASK-UHFFFAOYSA-N 0.000 claims 1
RYIUTLAVNDPKBW-UHFFFAOYSA-N 2-[4-[6-chloro-7-(2-ethylphenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C=CC=C1)CC)CC#N RYIUTLAVNDPKBW-UHFFFAOYSA-N 0.000 claims 1
CNSHQUXCOFGLIQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-(4-chlorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=CC=C(C=C1)Cl)CC#N CNSHQUXCOFGLIQ-UHFFFAOYSA-N 0.000 claims 1
KIVGPONNZNNPNN-UHFFFAOYSA-N 2-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=C(C(=C(C=C12)Cl)C1=C2C=NNC2=CC=C1C)F)CC#N KIVGPONNZNNPNN-UHFFFAOYSA-N 0.000 claims 1
KZOIGRMCBGIUJH-UHFFFAOYSA-N 2-[4-[6-chloro-8-fluoro-7-[2-(trifluoromethyl)phenyl]quinazolin-4-yl]-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=C(C(=C(C=C12)Cl)C1=C(C=CC=C1)C(F)(F)F)F)CC#N KZOIGRMCBGIUJH-UHFFFAOYSA-N 0.000 claims 1
VDJPXWHCVCRKNH-UHFFFAOYSA-N 2-[4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazin-2-yl]acetonitrile Chemical compound Clc1ccc(cc1)-c1cc2c(ncnc2cc1Cl)N1CCN(C(CC#N)C1)C(=O)C=C VDJPXWHCVCRKNH-UHFFFAOYSA-N 0.000 claims 1
AYCKHIMPCUTHOI-UHFFFAOYSA-N 2-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-3-fluorobenzamide Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C(=O)N)C=CC=C1F AYCKHIMPCUTHOI-UHFFFAOYSA-N 0.000 claims 1
MOFVIXHUPWXSOT-UHFFFAOYSA-N 2-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-4-fluorobenzamide Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C(=O)N)C=CC(=C1)F MOFVIXHUPWXSOT-UHFFFAOYSA-N 0.000 claims 1
TXUHBVSABGFSLY-UHFFFAOYSA-N 2-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-5-fluorobenzamide Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C(=O)N)C=C(C=C1)F TXUHBVSABGFSLY-UHFFFAOYSA-N 0.000 claims 1
OEYRXRCUFNXZKZ-UHFFFAOYSA-N 2-[7-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-6-yl]benzonitrile Chemical compound ClC1=C(C=C2C(=C1)N=CN=C2N1CCN(CC1)C(=O)C=C)C1=C(C=CC=C1)C#N OEYRXRCUFNXZKZ-UHFFFAOYSA-N 0.000 claims 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims 1
YBMGETHIZZIDAY-UHFFFAOYSA-N 3-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-1H-pyridin-2-one Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C=1C(NC=CC=1)=O YBMGETHIZZIDAY-UHFFFAOYSA-N 0.000 claims 1
XZPJSAZLBFIPCP-UHFFFAOYSA-N 3-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-2-fluoro-N,N-dimethylbenzamide Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C=1C(=C(C(=O)N(C)C)C=CC=1)F XZPJSAZLBFIPCP-UHFFFAOYSA-N 0.000 claims 1
BHFZNIORCYUIJN-UHFFFAOYSA-N 3-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-4-fluorobenzamide Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C=1C=C(C(=O)N)C=CC=1F BHFZNIORCYUIJN-UHFFFAOYSA-N 0.000 claims 1
FEORHTOGMHDMJB-UHFFFAOYSA-N 3-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]benzonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C=1C=C(C#N)C=CC=1 FEORHTOGMHDMJB-UHFFFAOYSA-N 0.000 claims 1
FWOPJXVQGMZKEP-UHFFFAOYSA-N 3-methyl-2h-indazole Chemical compound C1=CC=CC2=C(C)NN=C21 FWOPJXVQGMZKEP-UHFFFAOYSA-N 0.000 claims 1
YFRRPYCNBGGWIN-UHFFFAOYSA-N 4-(6-bromo-7-chloroquinazolin-4-yl)-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)Br)Cl)C#N YFRRPYCNBGGWIN-UHFFFAOYSA-N 0.000 claims 1
RUNKODQBPBTQDU-UHFFFAOYSA-N 4-(6-chloroisoquinolin-1-yl)-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound Clc1ccc2c(nccc2c1)N1CCN(C(C1)C#N)C(=O)C=C RUNKODQBPBTQDU-UHFFFAOYSA-N 0.000 claims 1
BMXASPNZGJNNQC-UHFFFAOYSA-N 4-(7-chloro-6-cyclopropylquinazolin-4-yl)-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound Clc1cc2ncnc(N3CCN(C(C3)C#N)C(=O)C=C)c2cc1C1CC1 BMXASPNZGJNNQC-UHFFFAOYSA-N 0.000 claims 1
GUTURVWWHABZHG-UHFFFAOYSA-N 4-(7-chloro-6-phenylquinazolin-4-yl)-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)C1=CC=CC=C1)Cl)C#N GUTURVWWHABZHG-UHFFFAOYSA-N 0.000 claims 1
BALSYFMHNYIXPE-UHFFFAOYSA-N 4-(7-chloro-6-thiophen-2-ylquinazolin-4-yl)-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)C=1SC=CC=1)Cl)C#N BALSYFMHNYIXPE-UHFFFAOYSA-N 0.000 claims 1
YCENLHYJVFJRFQ-UHFFFAOYSA-N 4-(7-chloroquinazolin-4-yl)-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=CC=C12)Cl)C#N YCENLHYJVFJRFQ-UHFFFAOYSA-N 0.000 claims 1
WDSRBSCRAAMXJM-UHFFFAOYSA-N 4-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-1,3-dihydroindol-2-one Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C2CC(NC2=CC=C1)=O WDSRBSCRAAMXJM-UHFFFAOYSA-N 0.000 claims 1
URZDPZUKASTBEH-UHFFFAOYSA-N 4-[6-chloro-7-(2-hydroxyphenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=C(C=CC=C1)O)C#N URZDPZUKASTBEH-UHFFFAOYSA-N 0.000 claims 1
LNFFCAOMIHCZSQ-UHFFFAOYSA-N 4-[7-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-6-yl]benzonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)C1=CC=C(C#N)C=C1)Cl LNFFCAOMIHCZSQ-UHFFFAOYSA-N 0.000 claims 1
JIIBSIMXAXZDEL-UHFFFAOYSA-N 4-[7-chloro-6-(4-chlorophenyl)quinazolin-4-yl]-1-prop-2-enoylpiperazine-2-carbonitrile Chemical compound Clc1ccc(cc1)-c1cc2c(ncnc2cc1Cl)N1CCN(C(C1)C#N)C(=O)C=C JIIBSIMXAXZDEL-UHFFFAOYSA-N 0.000 claims 1
VFWDUIQHGFCQCC-UHFFFAOYSA-N 4-chloro-1-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]pyridin-2-one Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)N1C(C=C(C=C1)Cl)=O VFWDUIQHGFCQCC-UHFFFAOYSA-N 0.000 claims 1
ALSOZZIBQRTXJW-UHFFFAOYSA-N 5-chloro-1-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]pyridin-2-one Chemical compound Clc1ccc(=O)n(c1)-c1cc2ncnc(N3CCN(CC3)C(=O)C=C)c2cc1Cl ALSOZZIBQRTXJW-UHFFFAOYSA-N 0.000 claims 1
KSYCXNAFPJVWGI-UHFFFAOYSA-N 6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)-7-[2-(trifluoromethyl)phenyl]quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=CC(=C(C=C12)Cl)C1=C(C=CC=C1)C(F)(F)F)C#N KSYCXNAFPJVWGI-UHFFFAOYSA-N 0.000 claims 1
AFZFGUVAZBYPEZ-VMPITWQZSA-N 6-chloro-4-[4-[(E)-4-(dimethylamino)but-2-enoyl]piperazin-1-yl]-8-fluoro-7-(3-hydroxynaphthalen-1-yl)quinoline-3-carbonitrile Chemical compound ClC=1C=C2C(=C(C=NC2=C(C=1C1=CC(=CC2=CC=CC=C12)O)F)C#N)N1CCN(CC1)C(\C=C\CN(C)C)=O AFZFGUVAZBYPEZ-VMPITWQZSA-N 0.000 claims 1
SYSYFCOOZJVCME-UHFFFAOYSA-N 6-chloro-7-(2,4-difluorophenyl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=CC(=C(C=C12)Cl)C1=C(C=C(C=C1)F)F)C#N SYSYFCOOZJVCME-UHFFFAOYSA-N 0.000 claims 1
FUWLOSODTFHBHF-UHFFFAOYSA-N 6-chloro-7-(2-fluoro-5-hydroxyphenyl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=CC(=C(C=C12)Cl)C1=C(C=CC(=C1)O)F)C#N FUWLOSODTFHBHF-UHFFFAOYSA-N 0.000 claims 1
JMJQHWIEHAOQSF-UHFFFAOYSA-N 6-chloro-7-(2-fluorophenyl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound FC1=CC=CC=C1C1=C(Cl)C=C2C(=C1)N=CC(C#N)=C2N1CCN(CC1)C(=O)C=C JMJQHWIEHAOQSF-UHFFFAOYSA-N 0.000 claims 1
BQKNNURHWKWWQE-UHFFFAOYSA-N 6-chloro-7-(2-hydroxynaphthalen-1-yl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=CC(=C(C=C12)Cl)C1=C(C=CC2=CC=CC=C12)O)C#N BQKNNURHWKWWQE-UHFFFAOYSA-N 0.000 claims 1
BPSLWCGTKVZQNA-UHFFFAOYSA-N 6-chloro-7-(2-hydroxyphenyl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=CC(=C(C=C12)Cl)C1=C(C=CC=C1)O)C#N BPSLWCGTKVZQNA-UHFFFAOYSA-N 0.000 claims 1
QJHUWZSJXFIMQD-UHFFFAOYSA-N 6-chloro-7-naphthalen-1-yl-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=CC(=C(C=C12)Cl)C1=CC=CC2=CC=CC=C12)C#N QJHUWZSJXFIMQD-UHFFFAOYSA-N 0.000 claims 1
MZYMZAOOTFYHBO-UHFFFAOYSA-N 6-chloro-8-fluoro-4-(4-prop-2-enoylpiperazin-1-yl)-7-[2-(trifluoromethyl)phenyl]quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=C(C(=C(C=C12)Cl)C1=C(C=CC=C1)C(F)(F)F)F)C#N MZYMZAOOTFYHBO-UHFFFAOYSA-N 0.000 claims 1
QHPMKPFWCVZEQT-UHFFFAOYSA-N 6-chloro-8-fluoro-7-(2-fluorophenyl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=C(C(=C(C=C12)Cl)C1=C(C=CC=C1)F)F)C#N QHPMKPFWCVZEQT-UHFFFAOYSA-N 0.000 claims 1
MURTXXKMDMYPGX-UHFFFAOYSA-N 6-chloro-8-fluoro-7-(2-hydroxynaphthalen-1-yl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=C(C(=C(C=C12)Cl)C1=C(C=CC2=CC=CC=C12)O)F)C#N MURTXXKMDMYPGX-UHFFFAOYSA-N 0.000 claims 1
FOUMXRPICAFSOF-UHFFFAOYSA-N 6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)-4-(4-prop-2-enoylpiperazin-1-yl)quinazoline-2-carbonitrile Chemical compound Oc1cc(-c2c(Cl)cc3c(nc(nc3c2F)C#N)N2CCN(CC2)C(=O)C=C)c2ccccc2c1 FOUMXRPICAFSOF-UHFFFAOYSA-N 0.000 claims 1
XGPQIZWCDCOEFA-UHFFFAOYSA-N 6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-yl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=C(C(=C(C=C12)Cl)C1=CC(=CC2=CC=CC=C12)O)F)C#N XGPQIZWCDCOEFA-UHFFFAOYSA-N 0.000 claims 1
LWVFMOZSMLVQQW-UHFFFAOYSA-N 6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-4-(3-methyl-4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1C(CN(CC1)C1=C(C=NC2=C(C(=C(C=C12)Cl)C1=C2C=NNC2=CC=C1C)F)C#N)C LWVFMOZSMLVQQW-UHFFFAOYSA-N 0.000 claims 1
LAHYQIYHLLKGOK-UHFFFAOYSA-N 6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=C(C(=C(C=C12)Cl)C1=C2C=NNC2=CC=C1C)F)C#N LAHYQIYHLLKGOK-UHFFFAOYSA-N 0.000 claims 1
KSUVZAZSFKTSOT-UHFFFAOYSA-N 6-chloro-8-fluoro-7-(6-methyl-1H-indazol-7-yl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=C(C=NC2=C(C(=C(C=C12)Cl)C=1C(=CC=C2C=NNC=12)C)F)C#N KSUVZAZSFKTSOT-UHFFFAOYSA-N 0.000 claims 1
ZSWSOVPABXFQPU-UHFFFAOYSA-N 7-(2-fluorophenyl)-4-(4-prop-2-enoylpiperazin-1-yl)quinazoline-6-carbonitrile Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)C#N)C1=C(C=CC=C1)F ZSWSOVPABXFQPU-UHFFFAOYSA-N 0.000 claims 1
QOFYCVARXOINFK-UHFFFAOYSA-N 7-chloro-4-(3-cyano-4-prop-2-enoylpiperazin-1-yl)quinazoline-6-carbonitrile Chemical compound Clc1cc2ncnc(N3CCN(C(C3)C#N)C(=O)C=C)c2cc1C#N QOFYCVARXOINFK-UHFFFAOYSA-N 0.000 claims 1
OKGVORORUZXCBC-UHFFFAOYSA-N 7-chloro-6-(2,4-difluorophenyl)-1-(1-prop-2-enoylpiperidin-4-yl)quinoxalin-2-one Chemical compound Fc1ccc(c(F)c1)-c1cc2ncc(=O)n(C3CCN(CC3)C(=O)C=C)c2cc1Cl OKGVORORUZXCBC-UHFFFAOYSA-N 0.000 claims 1
VUXXXBJEMCUMER-UHFFFAOYSA-N 7-chloro-6-(4-chlorophenyl)-4-(4-ethenylsulfonylpiperazin-1-yl)quinazoline Chemical compound Clc1ccc(cc1)-c1cc2c(ncnc2cc1Cl)N1CCN(CC1)S(=O)(=O)C=C VUXXXBJEMCUMER-UHFFFAOYSA-N 0.000 claims 1
PBIAALISGKFZKF-UHFFFAOYSA-N 7-chloro-6-(4-chlorophenyl)-4-(4-prop-2-enoylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound Clc1ccc(cc1)-c1cc2c(N3CCN(CC3)C(=O)C=C)c(cnc2cc1Cl)C#N PBIAALISGKFZKF-UHFFFAOYSA-N 0.000 claims 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
241000975394 Evechinus chloroticus Species 0.000 claims 1
UNUZYLQBNYXVFL-UHFFFAOYSA-N N-[1-(6-chloro-7-phenylquinazolin-4-yl)piperidin-4-yl]prop-2-enamide Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=CC=C1)N1CCC(CC1)NC(C=C)=O UNUZYLQBNYXVFL-UHFFFAOYSA-N 0.000 claims 1
CEILIMZRNOROED-UHFFFAOYSA-N N-[1-[7-chloro-6-(2-chlorophenyl)quinazolin-4-yl]azetidin-3-yl]prop-2-enamide Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)N1CC(C1)NC(C=C)=O)C1=C(C=CC=C1)Cl CEILIMZRNOROED-UHFFFAOYSA-N 0.000 claims 1
MNHCDQAHJAMWHG-UHFFFAOYSA-N N-[3-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-4-fluorophenyl]acetamide Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C=1C=C(C=CC=1F)NC(C)=O MNHCDQAHJAMWHG-UHFFFAOYSA-N 0.000 claims 1
WLAJLBBYHKTRIU-UHFFFAOYSA-N N-[4-[6-chloro-4-(4-prop-2-enoylpiperazin-1-yl)quinazolin-7-yl]-5-methylpyrimidin-2-yl]prop-2-enamide Chemical compound C(C=C)(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(C=C12)Cl)C1=NC(=NC=C1C)NC(C=C)=O WLAJLBBYHKTRIU-UHFFFAOYSA-N 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
LWMDZEGKAFJEBE-AATRIKPKSA-N ethyl (E)-4-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-oxobut-2-enoate Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=C(C=C1)F)F)N1CCN(CC1)C(/C=C/C(=O)OCC)=O LWMDZEGKAFJEBE-AATRIKPKSA-N 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
230000035772 mutation Effects 0.000 description 8
102200124918 rs121913250 Human genes 0.000 description 8
102100029974 GTPase HRas Human genes 0.000 description 7
101000584633 Homo sapiens GTPase HRas Proteins 0.000 description 7
102100030708 GTPase KRas Human genes 0.000 description 6
101000584612 Homo sapiens GTPase KRas Proteins 0.000 description 6
125000006728 (C1-C6) alkynyl group Chemical group 0.000 description 4
102200006538 rs121913530 Human genes 0.000 description 4
244000007835 Cyamopsis tetragonoloba Species 0.000 description 3
206010009944 Colon cancer Diseases 0.000 description 2
208000001333 Colorectal Neoplasms Diseases 0.000 description 2
206010058467 Lung neoplasm malignant Diseases 0.000 description 2
102000008300 Mutant Proteins Human genes 0.000 description 2
108010021466 Mutant Proteins Proteins 0.000 description 2
206010061902 Pancreatic neoplasm Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
201000005787 hematologic cancer Diseases 0.000 description 2
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
201000005202 lung cancer Diseases 0.000 description 2
208000020816 lung neoplasm Diseases 0.000 description 2
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
201000002528 pancreatic cancer Diseases 0.000 description 2
208000008443 pancreatic carcinoma Diseases 0.000 description 2
208000015768 polyposis Diseases 0.000 description 2
102200006614 rs104894229 Human genes 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
102100039788 GTPase NRas Human genes 0.000 description 1
101000744505 Homo sapiens GTPase NRas Proteins 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
230000003833 cell viability Effects 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002372 labelling Methods 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
230000035755 proliferation Effects 0.000 description 1

JP2016521333A 2013-10-10 2014-10-10 Ｋｒａｓｇ１２ｃの阻害剤 Active JP6559123B2 (ja)