JP2016532656A5 - - Google Patents
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- Publication number
- JP2016532656A5 JP2016532656A5 JP2016521333A JP2016521333A JP2016532656A5 JP 2016532656 A5 JP2016532656 A5 JP 2016532656A5 JP 2016521333 A JP2016521333 A JP 2016521333A JP 2016521333 A JP2016521333 A JP 2016521333A JP 2016532656 A5 JP2016532656 A5 JP 2016532656A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- prop
- piperazin
- quinazolin
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 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
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Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361889460P | 2013-10-10 | 2013-10-10 | |
| US61/889,460 | 2013-10-10 | ||
| US201462034619P | 2014-08-07 | 2014-08-07 | |
| US62/034,619 | 2014-08-07 | ||
| US201462052366P | 2014-09-18 | 2014-09-18 | |
| US62/052,366 | 2014-09-18 | ||
| JO289/2014 | 2014-10-09 | ||
| JOP/2014/0289A JO3805B1 (ar) | 2013-10-10 | 2014-10-09 | مثبطات كراس جي12سي |
| TW103135318 | 2014-10-09 | ||
| TW103135318A TWI659021B (zh) | 2013-10-10 | 2014-10-09 | Ｋｒａｓ ｇ１２ｃ之抑制劑 |
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