ES2835729T3 - Terapias de combinación para el tratamiento de cáncer - Google Patents

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Publication number

ES2835729T3

ES2835729T3 ES15771461T ES15771461T ES2835729T3 ES 2835729 T3 ES2835729 T3 ES 2835729T3 ES 15771461 T ES15771461 T ES 15771461T ES 15771461 T ES15771461 T ES 15771461T ES 2835729 T3 ES2835729 T3 ES 2835729T3

Authority

ES

Spain

Prior art keywords

piperazin

prop

quinazolin

chloro

doro

Prior art date

2014-09-18

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.)

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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 81
• 201000011510 cancer Diseases 0.000 title claims abstract description 50
• 238000011282 treatment Methods 0.000 title claims description 68
• 238000002648 combination therapy Methods 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 317
• -1 alkylaminylalkyl Chemical group 0.000 claims abstract description 256
• 102200006538 rs121913530 Human genes 0.000 claims abstract description 141
• 238000000034 method Methods 0.000 claims abstract description 138
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 120
• 101000584612 Homo sapiens GTPase KRas Proteins 0.000 claims abstract description 111
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 106
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 98
• 102100030708 GTPase KRas Human genes 0.000 claims abstract description 90
• 101000584633 Homo sapiens GTPase HRas Proteins 0.000 claims abstract description 88
• 239000003112 inhibitor Substances 0.000 claims abstract description 86
• 102100029974 GTPase HRas Human genes 0.000 claims abstract description 71
• 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 71
• 102100039788 GTPase NRas Human genes 0.000 claims abstract description 69
• 101000744505 Homo sapiens GTPase NRas Proteins 0.000 claims abstract description 69
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 69
• 108060006698 EGF receptor Proteins 0.000 claims abstract description 65
• 102000001301 EGF receptor Human genes 0.000 claims abstract description 64
• 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 61
• 125000003118 aryl group Chemical group 0.000 claims abstract description 56
• 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 55
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 52
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 44
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 37
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 36
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 32
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
• 102200124918 rs121913250 Human genes 0.000 claims abstract description 23
• 239000000651 prodrug Substances 0.000 claims abstract description 19
• 229940002612 prodrug Drugs 0.000 claims abstract description 19
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 13
• 125000004474 heteroalkylene group Chemical group 0.000 claims abstract description 13
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000006588 heterocycloalkylene group Chemical group 0.000 claims abstract description 12
• 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims abstract description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
• 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims abstract description 8
• 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 8
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 8
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 7
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 6
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims abstract description 6
• 125000006356 alkylene carbonyl group Chemical group 0.000 claims abstract description 4
• 125000003277 amino group Chemical group 0.000 claims abstract description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 3
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims abstract description 3
• 150000003936 benzamides Chemical class 0.000 claims abstract description 3
• 150000001558 benzoic acid derivatives Chemical class 0.000 claims abstract description 3
• 125000004992 haloalkylamino group Chemical group 0.000 claims abstract description 3
• 125000005241 heteroarylamino group Chemical group 0.000 claims abstract description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 3
• HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 168
• 125000005843 halogen group Chemical group 0.000 claims description 69
• 229910052799 carbon Inorganic materials 0.000 claims description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 25
• 239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 25
• 229960001433 erlotinib Drugs 0.000 claims description 25
• 239000000460 chlorine Substances 0.000 claims description 23
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 229940124597 therapeutic agent Drugs 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 208000020816 lung neoplasm Diseases 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
• 201000005202 lung cancer Diseases 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• ULXXDDBFHOBEHA-CWDCEQMOSA-N afatinib Chemical compound N1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 ULXXDDBFHOBEHA-CWDCEQMOSA-N 0.000 claims description 7
• 229960001686 afatinib Drugs 0.000 claims description 7
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 5
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
• 201000002528 pancreatic cancer Diseases 0.000 claims description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
• BRYCUMKDWMEGMK-UHFFFAOYSA-N piperazine-2-carboxamide Chemical compound NC(=O)C1CNCCN1 BRYCUMKDWMEGMK-UHFFFAOYSA-N 0.000 claims description 5
• 239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 230000012010 growth Effects 0.000 claims description 4
• 229940084651 iressa Drugs 0.000 claims description 4
• FXGJYEBAJZLAJX-UHFFFAOYSA-N piperazine-2-carbonitrile Chemical compound N#CC1CNCCN1 FXGJYEBAJZLAJX-UHFFFAOYSA-N 0.000 claims description 3
• 208000015768 polyposis Diseases 0.000 claims description 3
• 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 description 2
• 101150117869 Hras gene Proteins 0.000 claims description 2
• 230000002489 hematologic effect Effects 0.000 claims description 2
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 146
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 31
• 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims 29
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 26
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 4
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 4
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
• RHKZHZQORKKGRU-UHFFFAOYSA-N 4-[2-oxo-2-[4-(1-prop-2-enoylazetidin-3-yl)piperazin-1-yl]ethyl]-1,3-dihydroquinoxalin-2-one Chemical compound C1N(C(=O)C=C)CC1N1CCN(C(=O)CN2C3=CC=CC=C3NC(=O)C2)CC1 RHKZHZQORKKGRU-UHFFFAOYSA-N 0.000 claims 2
• 102100031673 Corneodesmosin Human genes 0.000 claims 2
• 101710139375 Corneodesmosin Proteins 0.000 claims 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
• VRUMFIWLEQVXAB-ONEGZZNKSA-N (E)-1-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-(dimethylamino)but-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\CN(C)C)=O VRUMFIWLEQVXAB-ONEGZZNKSA-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
• WRVGKLHLVPRANC-SNAWJCMRSA-N (E)-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]-4-(dimethylamino)but-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)C1=CN=CS1)N1CCN(CC1)C(\C=C\CN(C)C)=O WRVGKLHLVPRANC-SNAWJCMRSA-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
• HKNJIBMZTAAGJT-CXUHLZMHSA-N (E)-2-[4-[6-chloro-7-(2-fluorophenyl)quinazolin-4-yl]piperazine-1-carbonyl]-3-(1,3-thiazol-5-yl)prop-2-enenitrile Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)F)N1CCN(CC1)C(=O)\C(\C#N)=C\C1=CN=CS1 HKNJIBMZTAAGJT-CXUHLZMHSA-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
• ZZNPXDDHHWWYBP-ONEGZZNKSA-N (E)-4-[4-[6-chloro-7-(2,4-difluorophenyl)quinazolin-4-yl]piperazin-1-yl]-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)N1CCN(CC1)C1=NC=NC2=CC(=C(Cl)C=C12)C1=C(F)C=C(F)C=C1 ZZNPXDDHHWWYBP-ONEGZZNKSA-N 0.000 claims 1
• MBDUZRZBPSTXLX-ZZXKWVIFSA-N (E)-4-amino-1-[4-[6-chloro-8-fluoro-7-(3-hydroxynaphthalen-1-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=CC(=CC2=CC=CC=C12)O)F MBDUZRZBPSTXLX-ZZXKWVIFSA-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
• ZEKSHWKIFFYNKZ-ONEGZZNKSA-N (e)-1-[3-[4-[2-(4,5-dichloro-2-hydroxyanilino)acetyl]piperazin-1-yl]azetidin-1-yl]-4-(dimethylamino)but-2-en-1-one Chemical compound C1N(C(=O)/C=C/CN(C)C)CC1N1CCN(C(=O)CNC=2C(=CC(Cl)=C(Cl)C=2)O)CC1 ZEKSHWKIFFYNKZ-ONEGZZNKSA-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
• GKBAZCWAJNWDPF-UHFFFAOYSA-N 1-[3-[4-(2-indol-1-ylacetyl)piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound C1N(C(=O)C=C)CC1N1CCN(C(=O)CN2C3=CC=CC=C3C=C2)CC1 GKBAZCWAJNWDPF-UHFFFAOYSA-N 0.000 claims 1
• ZQZRQDMJHKSXDN-UHFFFAOYSA-N 1-[3-[4-(2-naphthalen-1-ylacetyl)piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound C1N(C(=O)C=C)CC1N1CCN(C(=O)CC=2C3=CC=CC=C3C=CC=2)CC1 ZQZRQDMJHKSXDN-UHFFFAOYSA-N 0.000 claims 1
• TZUGYMHFCZPDHQ-UHFFFAOYSA-N 1-[3-[4-[1-(4-chloro-5-ethyl-2-methoxyphenyl)piperidin-3-yl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(CC)=CC(N2CC(CCC2)N2CCN(CC2)C2CN(C2)C(=O)C=C)=C1OC TZUGYMHFCZPDHQ-UHFFFAOYSA-N 0.000 claims 1
• CCVPMRHFFGAGPH-UHFFFAOYSA-N 1-[3-[4-[2-(1h-indol-3-yl)acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound C1N(C(=O)C=C)CC1N1CCN(C(=O)CC=2C3=CC=CC=C3NC=2)CC1 CCVPMRHFFGAGPH-UHFFFAOYSA-N 0.000 claims 1
• VPPBJLPIFWRWHR-UHFFFAOYSA-N 1-[3-[4-[2-(2-hydroxy-5-methylsulfonylanilino)acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound CS(=O)(=O)C1=CC=C(O)C(NCC(=O)N2CCN(CC2)C2CN(C2)C(=O)C=C)=C1 VPPBJLPIFWRWHR-UHFFFAOYSA-N 0.000 claims 1
• OLDQNCJIAJVSKM-UHFFFAOYSA-N 1-[3-[4-[2-(3-chloro-5-hydroxyanilino)acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound OC1=CC(Cl)=CC(NCC(=O)N2CCN(CC2)C2CN(C2)C(=O)C=C)=C1 OLDQNCJIAJVSKM-UHFFFAOYSA-N 0.000 claims 1
• OALXBYNPDBOOSG-UHFFFAOYSA-N 1-[3-[4-[2-(4,5-dichloro-2-hydroxyanilino)acetyl]piperazin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound OC1=CC(Cl)=C(Cl)C=C1NCC(=O)N1CCN(C2CN(CC2)C(=O)C=C)CC1 OALXBYNPDBOOSG-UHFFFAOYSA-N 0.000 claims 1
• NCNFUYOVFARQBL-UHFFFAOYSA-N 1-[3-[4-[2-(4-chloro-2-hydroxy-5-methylanilino)acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(C)=CC(NCC(=O)N2CCN(CC2)C2CN(C2)C(=O)C=C)=C1O NCNFUYOVFARQBL-UHFFFAOYSA-N 0.000 claims 1
• NDTJVWLTVWEDAK-UHFFFAOYSA-N 1-[3-[4-[2-(4-chloro-2-hydroxy-5-methylanilino)acetyl]piperazin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(C)=CC(NCC(=O)N2CCN(CC2)C2CN(CC2)C(=O)C=C)=C1O NDTJVWLTVWEDAK-UHFFFAOYSA-N 0.000 claims 1
• FFYHGJYLYJNGCK-UHFFFAOYSA-N 1-[3-[4-[2-(4-chloro-5-ethyl-2-hydroxyanilino)acetyl]piperazin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(CC)=CC(NCC(=O)N2CCN(CC2)C2CN(CC2)C(=O)C=C)=C1O FFYHGJYLYJNGCK-UHFFFAOYSA-N 0.000 claims 1
• ODOJAKHVEMMOOU-UHFFFAOYSA-N 1-[3-[4-[2-(5-bromo-4-chloro-2-hydroxyanilino)acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound OC1=CC(Cl)=C(Br)C=C1NCC(=O)N1CCN(C2CN(C2)C(=O)C=C)CC1 ODOJAKHVEMMOOU-UHFFFAOYSA-N 0.000 claims 1
• XAXTZLXDPJAMSR-UHFFFAOYSA-N 1-[3-[4-[2-(5-chloro-2-hydroxy-4-methylanilino)acetyl]piperazin-1-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(C)=CC(O)=C1NCC(=O)N1CCN(C2CN(CC2)C(=O)C=C)CC1 XAXTZLXDPJAMSR-UHFFFAOYSA-N 0.000 claims 1
• YAODGLYRYXEJEL-UHFFFAOYSA-N 1-[3-[4-[2-(5-chloro-2-hydroxyanilino)acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound OC1=CC=C(Cl)C=C1NCC(=O)N1CCN(C2CN(C2)C(=O)C=C)CC1 YAODGLYRYXEJEL-UHFFFAOYSA-N 0.000 claims 1
• RRDRLECHRKMVSK-UHFFFAOYSA-N 1-[3-[4-[2-[(3-hydroxynaphthalen-2-yl)amino]acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound OC1=CC2=CC=CC=C2C=C1NCC(=O)N(CC1)CCN1C1CN(C(=O)C=C)C1 RRDRLECHRKMVSK-UHFFFAOYSA-N 0.000 claims 1
• LSOHFDAFNAEWQF-UHFFFAOYSA-N 1-[3-[4-[2-[(5-chloro-1,3-thiazol-2-yl)amino]acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound S1C(Cl)=CN=C1NCC(=O)N1CCN(C2CN(C2)C(=O)C=C)CC1 LSOHFDAFNAEWQF-UHFFFAOYSA-N 0.000 claims 1
• XIUHASHSNKNGFV-UHFFFAOYSA-N 1-[3-[4-[2-[(5-chloro-4-ethylpyridin-2-yl)amino]acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(CC)=CC(NCC(=O)N2CCN(CC2)C2CN(C2)C(=O)C=C)=N1 XIUHASHSNKNGFV-UHFFFAOYSA-N 0.000 claims 1
• LIFLNRABFIEWHB-UHFFFAOYSA-N 1-[3-[4-[2-[4-chloro-2-methoxy-5-(trifluoromethyl)anilino]acetyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC(Cl)=C(C(F)(F)F)C=C1NCC(=O)N1CCN(C2CN(C2)C(=O)C=C)CC1 LIFLNRABFIEWHB-UHFFFAOYSA-N 0.000 claims 1
• CBJZGALHLNGZFM-UHFFFAOYSA-N 1-[3-[4-[3-chloro-2-(2,5-dichlorophenyl)-5-hydroxybenzoyl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C(C=C1)Cl)C=1C(=CC(=CC=1Cl)O)C(=O)N1CCN(CC1)C1CN(C1)C(C=C)=O CBJZGALHLNGZFM-UHFFFAOYSA-N 0.000 claims 1
• CSKDZHYPUKSCDH-UHFFFAOYSA-N 1-[3-[4-[5-(4-chloro-5-ethyl-2-hydroxyphenyl)-1H-pyrazol-3-yl]piperazin-1-yl]azetidin-1-yl]prop-2-en-1-one Chemical compound C1=C(Cl)C(CC)=CC(C2=NNC(=C2)N2CCN(CC2)C2CN(C2)C(=O)C=C)=C1O CSKDZHYPUKSCDH-UHFFFAOYSA-N 0.000 claims 1
• RIDPDWKLXBCWEM-UHFFFAOYSA-N 1-[3-[[7-chloro-6-(2-chlorophenyl)quinazolin-4-yl]amino]azetidin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=C2C(=NC=NC2=C1)NC1CN(C1)C(C=C)=O)C1=C(C=CC=C1)Cl RIDPDWKLXBCWEM-UHFFFAOYSA-N 0.000 claims 1
• JHDLEYISSCEEHR-UHFFFAOYSA-N 1-[4-(6-chloro-7-cyclopropylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1CC1)N1CCN(CC1)C(C=C)=O JHDLEYISSCEEHR-UHFFFAOYSA-N 0.000 claims 1
• ZHAGHROAGSLRIU-UHFFFAOYSA-N 1-[4-(6-chloro-7-phenylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC1C1=CC=CC=C1)N1CCN(CC1)C(C=C)=O ZHAGHROAGSLRIU-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
• 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
• 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
• ULEACDBCHKQDLT-UHFFFAOYSA-N 1-[4-(6-cyclopropyl-7-phenylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound C1(CC1)C=1C=C2C(=NC=NC2=CC=1C1=CC=CC=C1)N1CCN(CC1)C(C=C)=O ULEACDBCHKQDLT-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
• 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
• RDTIKXDYEILVTH-UHFFFAOYSA-N 1-[4-(7-phenylquinazolin-4-yl)piperazin-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CCN(CC1)C1=NC=NC2=CC(=CC=C12)C1=CC=CC=C1 RDTIKXDYEILVTH-UHFFFAOYSA-N 0.000 claims 1
• UXVPKHUVXFZNPH-UHFFFAOYSA-N 1-[4-[1-[2-(4,5-dichloro-2-hydroxyanilino)acetyl]azetidin-3-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound OC1=CC(Cl)=C(Cl)C=C1NCC(=O)N1CC(N2CCN(CC2)C(=O)C=C)C1 UXVPKHUVXFZNPH-UHFFFAOYSA-N 0.000 claims 1
• RRHQJVAERADIFC-UHFFFAOYSA-N 1-[4-[2-amino-6-chloro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound NC1=NC2=CC(=C(C=C2C(=N1)N1CCN(CC1)C(C=C)=O)Cl)C1=C2C=NNC2=CC=C1C RRHQJVAERADIFC-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
• ZBFNACBPGBFOGQ-UHFFFAOYSA-N 1-[4-[6,8-difluoro-7-(2-fluoro-6-hydroxyphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C2C(=NC=NC2=C(C=1C1=C(C=CC=C1O)F)F)N1CCN(CC1)C(C=C)=O ZBFNACBPGBFOGQ-UHFFFAOYSA-N 0.000 claims 1
• YBYOMVRPPJJXOW-UHFFFAOYSA-N 1-[4-[6,8-difluoro-7-(6-methyl-1H-indazol-7-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C2C(=NC=NC2=C(C=1C=1C(=CC=C2C=NNC=12)C)F)N1CCN(CC1)C(C=C)=O YBYOMVRPPJJXOW-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
• GQMFMICSQSOXFX-UHFFFAOYSA-N 1-[4-[6-[2-(trifluoromethyl)phenyl]thieno[3,2-d]pyrimidin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound FC(C1=C(C=CC=C1)C1=CC=2N=CN=C(C=2S1)N1CCN(CC1)C(C=C)=O)(F)F GQMFMICSQSOXFX-UHFFFAOYSA-N 0.000 claims 1
• SNLHFLSASOSFDC-UHFFFAOYSA-N 1-[4-[6-chloro-2-(dimethylamino)-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)C)N1CCN(CC1)C(C=C)=O SNLHFLSASOSFDC-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
• PTXJDMXVACHADS-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethoxy]-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)OCCN(C)C)N1CCN(CC1)C(C=C)=O PTXJDMXVACHADS-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
• ZYACYFKGQCICQZ-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethoxy]-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)OCCN(C)C)N1CCN(CC1)C(C=C)=O ZYACYFKGQCICQZ-UHFFFAOYSA-N 0.000 claims 1
• DDQSHULYPQZLOJ-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethylamino]-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)NCCN(C)C)N1CCN(CC1)C(C=C)=O DDQSHULYPQZLOJ-UHFFFAOYSA-N 0.000 claims 1
• DUEJPBVJVIDISN-UHFFFAOYSA-N 1-[4-[6-chloro-2-[2-(dimethylamino)ethylamino]-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound CN(C)CCNc1nc(N2CCN(CC2)C(=O)C=C)c2cc(Cl)c(c(F)c2n1)-c1c(C)ccc2[nH]ncc12 DUEJPBVJVIDISN-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
• 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
• RZFPJFPNISUMEN-UHFFFAOYSA-N 1-[4-[6-chloro-7-(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)N1CCN(CC1)C(C=C)=O RZFPJFPNISUMEN-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
• FYFOBZOFCCEZEJ-UHFFFAOYSA-N 1-[4-[6-chloro-7-(1H-indazol-6-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC=C2C=NNC2=C1)N1CCN(CC1)C(C=C)=O FYFOBZOFCCEZEJ-UHFFFAOYSA-N 0.000 claims 1
• YBHMQZSGHYSORX-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,3-difluoro-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)F)N1CCN(CC1)C(C=C)=O YBHMQZSGHYSORX-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
• FOGZYJMDTLIWMK-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2,4-difluorophenyl)-8-methoxyquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound COc1c(c(Cl)cc2c(ncnc12)N1CCN(CC1)C(=O)C=C)-c1ccc(F)cc1F FOGZYJMDTLIWMK-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
• YRBPLAAVBYBUAC-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-chlorophenyl)isoquinolin-1-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Clc1ccccc1-c1cc2c(nccc2cc1Cl)N1CCN(CC1)C(=O)C=C YRBPLAAVBYBUAC-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
• CCPFUJIYLXNINY-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-ethylphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=C(C=CC=C1)CC)N1CCN(CC1)C(C=C)=O CCPFUJIYLXNINY-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
• SXCGRXYUSDEVBG-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-fluoro-6-hydroxyphenyl)-5-(trifluoromethyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Oc1cccc(F)c1-c1cc2ncnc(N3CCN(CC3)C(=O)C=C)c2c(c1Cl)C(F)(F)F SXCGRXYUSDEVBG-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
• 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 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
• QKHZXYXJUATISH-UHFFFAOYSA-N 1-[4-[6-chloro-7-(2-hydroxynaphthalen-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)O)N1CCN(CC1)C(C=C)=O QKHZXYXJUATISH-UHFFFAOYSA-N 0.000 claims 1
• REXFOHVYGYXWOA-UHFFFAOYSA-N 1-[4-[6-chloro-7-(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)O)N1CCN(CC1)C(C=C)=O REXFOHVYGYXWOA-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
• 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
• FRHROYDLABHFIC-UHFFFAOYSA-N 1-[4-[6-chloro-7-(3-ethylphenyl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=CC=1C1=CC(=CC=C1)CC)N1CCN(CC1)C(C=C)=O FRHROYDLABHFIC-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
• 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
• 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
• 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
• PODHLWZLRJFENZ-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-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=C1Cl)N1CCN(CC1)C(C=C)=O PODHLWZLRJFENZ-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
• JEWCPCYBBOTECL-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-methyl-1H-indazol-4-yl)-2-(oxan-3-yloxy)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1C1=C2C=NNC2=CC=C1C)OC1COCCC1)N1CCN(CC1)C(C=C)=O JEWCPCYBBOTECL-UHFFFAOYSA-N 0.000 claims 1
• UPLOMPWLYAAKBX-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-methyl-1H-indazol-4-yl)-2-(oxolan-3-ylamino)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1C1=C2C=NNC2=CC=C1C)NC1COCC1)N1CCN(CC1)C(C=C)=O UPLOMPWLYAAKBX-UHFFFAOYSA-N 0.000 claims 1
• QEIMECODLIIQNJ-UHFFFAOYSA-N 1-[4-[6-chloro-7-(5-methyl-1H-indazol-4-yl)-2-(oxolan-3-yloxy)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC(=NC2=CC=1C1=C2C=NNC2=CC=C1C)OC1COCC1)N1CCN(CC1)C(C=C)=O QEIMECODLIIQNJ-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
• HNVHAAINTQHOOZ-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-(cyclopropylmethyl)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)CC1CC1)N1CCN(CC1)C(C=C)=O HNVHAAINTQHOOZ-UHFFFAOYSA-N 0.000 claims 1
• METIIUQFRLQCJX-UHFFFAOYSA-N 1-[4-[6-chloro-7-[2-hydroxy-6-(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=C1C(F)(F)F)O)N1CCN(CC1)C(C=C)=O METIIUQFRLQCJX-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
• 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
• ATOYQYKFXJFKFX-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(1H-indol-3-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=CNC2=CC=CC=C12)F)N1CCN(CC1)C(C=C)=O ATOYQYKFXJFKFX-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
• NXUYNRCKHSKASC-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(3-fluoro-5-methyl-2H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Cc1ccc2[nH]nc(F)c2c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C NXUYNRCKHSKASC-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
• 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
• BREWRUVGBHVGHK-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(3-methyl-2H-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 BREWRUVGBHVGHK-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
• 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
• SLPPVAHXYUVHOV-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-(2,2,2-trifluoroethylamino)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)NCC(F)(F)F)N1CCN(CC1)C(C=C)=O SLPPVAHXYUVHOV-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
• IBYDWZFLXFYNQN-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)-2-[(1-methylpyrazol-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)NC=1C=NN(C=1)C)N1CCN(CC1)C(C=C)=O IBYDWZFLXFYNQN-UHFFFAOYSA-N 0.000 claims 1
• DTYFRQKCCGLLPU-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]-2-(hydroxymethyl)piperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)N1CC(N(CC1)C(C=C)=O)CO DTYFRQKCCGLLPU-UHFFFAOYSA-N 0.000 claims 1
• FAJBJPQCUPSGOU-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]-2-methylpiperazin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C2C(=NC=NC2=C(C=1C1=C2C=NNC2=CC=C1C)F)N1CC(N(CC1)C(C=C)=O)C FAJBJPQCUPSGOU-UHFFFAOYSA-N 0.000 claims 1
• MUBIBXAKNQTYTD-UHFFFAOYSA-N 1-[4-[6-chloro-8-fluoro-7-(5-methyl-1H-indazol-4-yl)quinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound Cc1ccc2[nH]ncc2c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C MUBIBXAKNQTYTD-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
• MWRMPFZEZDLKQD-UHFFFAOYSA-N 1-[4-[7-(1-benzothiophen-3-yl)-6-chloroquinazolin-4-yl]piperazin-1-yl]prop-2-en-1-one Chemical compound S1C=C(C2=C1C=CC=C2)C1=C(C=C2C(=NC=NC2=C1)N1CCN(CC1)C(C=C)=O)Cl MWRMPFZEZDLKQD-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
• 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
• 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
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