HRP20171670T1 - Spojevi i sastavi za moduliranje egfr-aktiviteta - Google Patents
Spojevi i sastavi za moduliranje egfr-aktiviteta Download PDFInfo
- Publication number
- HRP20171670T1 HRP20171670T1 HRP20171670TT HRP20171670T HRP20171670T1 HR P20171670 T1 HRP20171670 T1 HR P20171670T1 HR P20171670T T HRP20171670T T HR P20171670TT HR P20171670 T HRP20171670 T HR P20171670T HR P20171670 T1 HRP20171670 T1 HR P20171670T1
- Authority
- HR
- Croatia
- Prior art keywords
- enoyl
- methyl
- azepan
- benzodiazol
- carboxamide
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 39
- 108060006698 EGF receptor Proteins 0.000 title claims 10
- 239000000203 mixture Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 26
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 23
- 125000005842 heteroatom Chemical group 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 20
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 15
- -1 (4-acetylpiperazin-1-yl)methyl Chemical group 0.000 claims 14
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 102000001301 EGF receptor Human genes 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 125000003368 amide group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 229910052698 phosphorus Inorganic materials 0.000 claims 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 230000035772 mutation Effects 0.000 claims 3
- CXICEXOWGOQDAE-UHFFFAOYSA-N n-[5-methyl-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(=O)NC1=NC2=CC(C)=CC=C2N1C1CCCN(C(=O)C=C)C1 CXICEXOWGOQDAE-UHFFFAOYSA-N 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- DKAMBEHAQOUWDB-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methoxypyridine-4-carboxamide Chemical compound c1cnc(OC)cc1C(=O)Nc1nc2cccc(C)c2n1C1CCCCN(C(=O)\C=C\CN(C)C)C1 DKAMBEHAQOUWDB-XYOKQWHBSA-N 0.000 claims 2
- XBOWFZGBAMQXDI-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methyl-1,3-thiazole-5-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cnc(C)s2)nc2cccc(C)c12 XBOWFZGBAMQXDI-XYOKQWHBSA-N 0.000 claims 2
- FVHNFXBVALQEPW-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnnc2)nc2cccc(C)c12 FVHNFXBVALQEPW-YRNVUSSQSA-N 0.000 claims 2
- ADZYAMHZRTVCHD-ZAOIQFLMSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(methylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CNC)CCCC[C@H]1n1c(NC(=O)c2ccnc(C)c2)nc2cccc(Cl)c12 ADZYAMHZRTVCHD-ZAOIQFLMSA-N 0.000 claims 2
- MYOGKUHDJSGFJS-UHFFFAOYSA-N N-[7-chloro-1-[1-[4-(3-hydroxypyrrolidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(Cl)c2n1C1CCCCN(C1)C(=O)C=CCN1CCC(O)C1 MYOGKUHDJSGFJS-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- XILZLQGBIXBPPH-WUTDNEBXSA-N n-[1-[(3r)-1-[(e)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-(trifluoromethyl)pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(C)C=CC=C2N=C1NC(=O)C1=CC=NC(C(F)(F)F)=C1 XILZLQGBIXBPPH-WUTDNEBXSA-N 0.000 claims 2
- UQLIJVPLMFPORY-NBILRRPASA-N n-[7-chloro-1-[(3r)-1-[(e)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC(C)=NC(C)=C1 UQLIJVPLMFPORY-NBILRRPASA-N 0.000 claims 2
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 claims 2
- 125000005936 piperidyl group Chemical group 0.000 claims 2
- GEBGCSXVYUDDPU-UHFFFAOYSA-N pyridazine-4-carboxamide Chemical compound NC(=O)C1=CC=NN=C1 GEBGCSXVYUDDPU-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- VAPKETCXHSBIDS-UHFFFAOYSA-N 2,3-difluoro-N-[5-[(3-methoxypyrrolidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound COC1CCN(CC2=CC(C)=C3N(C4CCCCN(C4)C(=O)C=C)C(NC(=O)C4=C(F)C(F)=CC=C4)=NC3=C2)C1 VAPKETCXHSBIDS-UHFFFAOYSA-N 0.000 claims 1
- VAPKETCXHSBIDS-FGZHOGPDSA-N 2,3-difluoro-N-[5-[[(3R)-3-methoxypyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound CO[C@@H]1CCN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cccc(F)c4F)nc3c2)C1 VAPKETCXHSBIDS-FGZHOGPDSA-N 0.000 claims 1
- XGUZPQIZIJVNGA-UHFFFAOYSA-N 2,6-dimethyl-N-[7-methyl-1-(1-prop-2-enoylazepan-3-yl)-5-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(cc(C)n1)C(=O)Nc1nc2cc(CN3CCCC3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C XGUZPQIZIJVNGA-UHFFFAOYSA-N 0.000 claims 1
- XGUZPQIZIJVNGA-RUZDIDTESA-N 2,6-dimethyl-N-[7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]-5-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(cc(C)n1)C(=O)Nc1nc2cc(CN3CCCC3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C XGUZPQIZIJVNGA-RUZDIDTESA-N 0.000 claims 1
- JPSOAVPPXNAJMW-UHFFFAOYSA-N 2,6-dimethyl-N-[7-methyl-5-[(4-methyl-3-oxopiperazin-1-yl)methyl]-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound CN1CCN(Cc2cc(C)c3n(C4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)CC1=O JPSOAVPPXNAJMW-UHFFFAOYSA-N 0.000 claims 1
- JPSOAVPPXNAJMW-RUZDIDTESA-N 2,6-dimethyl-N-[7-methyl-5-[(4-methyl-3-oxopiperazin-1-yl)methyl]-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound CN1CCN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)CC1=O JPSOAVPPXNAJMW-RUZDIDTESA-N 0.000 claims 1
- JCZBWKAZYQYRIU-HXUWFJFHSA-N 2-(difluoromethoxy)-N-[1-[(3R)-1-[4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-4-carboxamide Chemical compound CN(C)CC=CC(=O)N1CCCC[C@H](C1)n1c(NC(=O)c2ccnc(OC(F)F)c2)nc2cccc(C)c12 JCZBWKAZYQYRIU-HXUWFJFHSA-N 0.000 claims 1
- JCZBWKAZYQYRIU-UHFFFAOYSA-N 2-(difluoromethoxy)-N-[1-[1-[4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-4-carboxamide Chemical compound CN(C)CC=CC(=O)N1CCCCC(C1)n1c(NC(=O)c2ccnc(OC(F)F)c2)nc2cccc(C)c12 JCZBWKAZYQYRIU-UHFFFAOYSA-N 0.000 claims 1
- XNULEMJFNNYJRI-UKTHLTGXSA-N 2-(dimethylamino)-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnc(c2)N(C)C)nc2cccc(C)c12 XNULEMJFNNYJRI-UKTHLTGXSA-N 0.000 claims 1
- ZSJIGZLOUYDHMZ-UHFFFAOYSA-N 2-[[2-benzamido-3-(1-prop-2-enoylazepan-3-yl)benzimidazole-4-carbonyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)c1cccc2nc(NC(=O)c3ccccc3)n(C3CCCCN(C3)C(=O)C=C)c12 ZSJIGZLOUYDHMZ-UHFFFAOYSA-N 0.000 claims 1
- YGOQUBIOOKZEOE-UHFFFAOYSA-N 2-benzamido-N-(2-methylsulfonylethyl)-3-(1-prop-2-enoylazepan-3-yl)benzimidazole-4-carboxamide Chemical compound C(C=C)(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC=C2)C(=O)NCCS(=O)(=O)C)NC(C2=CC=CC=C2)=O YGOQUBIOOKZEOE-UHFFFAOYSA-N 0.000 claims 1
- CKSOJBKTVCPVPI-BQHJZSHBSA-N 2-chloro-N-[1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-(trifluoromethoxy)pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1n1c(NC(=O)c2cc(Cl)nc(OC(F)(F)F)c2)nc2cccc(C)c12 CKSOJBKTVCPVPI-BQHJZSHBSA-N 0.000 claims 1
- PWIYPRPUGZDXNO-HXUWFJFHSA-N 2-chloro-N-[1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-methoxypyridine-4-carboxamide Chemical compound ClC1=NC(=CC(=C1)C(=O)NC1=NC2=C(N1[C@H]1CN(CCCC1)C(C=CCN(C)C)=O)C(=CC=C2)C)OC PWIYPRPUGZDXNO-HXUWFJFHSA-N 0.000 claims 1
- QMOMMXJIWOGYPC-NBILRRPASA-N 2-chloro-N-[1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1n1c(NC(=O)c2cc(C)nc(Cl)c2)nc2cccc(C)c12 QMOMMXJIWOGYPC-NBILRRPASA-N 0.000 claims 1
- FFEFIDSYHUZDII-WUTDNEBXSA-N 2-chloro-N-[1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1n1c(NC(=O)c2ccnc(Cl)c2)nc2cccc(C)c12 FFEFIDSYHUZDII-WUTDNEBXSA-N 0.000 claims 1
- CKSOJBKTVCPVPI-UHFFFAOYSA-N 2-chloro-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-(trifluoromethoxy)pyridine-4-carboxamide Chemical compound ClC1=NC(=CC(=C1)C(=O)NC1=NC2=C(N1C1CN(CCCC1)C(C=CCN(C)C)=O)C(=CC=C2)C)OC(F)(F)F CKSOJBKTVCPVPI-UHFFFAOYSA-N 0.000 claims 1
- PWIYPRPUGZDXNO-UHFFFAOYSA-N 2-chloro-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-methoxypyridine-4-carboxamide Chemical compound ClC1=NC(=CC(=C1)C(=O)NC1=NC2=C(N1C1CN(CCCC1)C(C=CCN(C)C)=O)C(=CC=C2)C)OC PWIYPRPUGZDXNO-UHFFFAOYSA-N 0.000 claims 1
- QMOMMXJIWOGYPC-UHFFFAOYSA-N 2-chloro-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-methylpyridine-4-carboxamide Chemical compound ClC1=NC(=CC(=C1)C(=O)NC1=NC2=C(N1C1CN(CCCC1)C(C=CCN(C)C)=O)C(=CC=C2)C)C QMOMMXJIWOGYPC-UHFFFAOYSA-N 0.000 claims 1
- FFEFIDSYHUZDII-UHFFFAOYSA-N 2-chloro-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-4-carboxamide Chemical compound ClC1=NC=CC(=C1)C(=O)NC1=NC2=C(N1C1CN(CCCC1)C(C=CCN(C)C)=O)C(=CC=C2)C FFEFIDSYHUZDII-UHFFFAOYSA-N 0.000 claims 1
- DIFZQFMEJWRSBD-UHFFFAOYSA-N 2-methyl-N-[7-methyl-1-(1-prop-2-enoylazepan-3-yl)-5-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCCC3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C DIFZQFMEJWRSBD-UHFFFAOYSA-N 0.000 claims 1
- AWBUREOGISEZHO-UHFFFAOYSA-N 2-methyl-N-[7-methyl-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(C)c2n1C1CCCN(C1)C(=O)C=C AWBUREOGISEZHO-UHFFFAOYSA-N 0.000 claims 1
- GHBHACNOWPELTF-ZXXUSRDYSA-N 2-methyl-N-[7-methyl-1-[(3R)-1-[(E)-4-pyrrolidin-1-ylbut-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound c1cnc(C)cc1C(=O)Nc1nc2cccc(C)c2n1[C@@H]1CCCCN(C(=O)\C=C\CN2CCCC2)C1 GHBHACNOWPELTF-ZXXUSRDYSA-N 0.000 claims 1
- DIFZQFMEJWRSBD-XMMPIXPASA-N 2-methyl-N-[7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]-5-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCCC3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C DIFZQFMEJWRSBD-XMMPIXPASA-N 0.000 claims 1
- AWBUREOGISEZHO-GOSISDBHSA-N 2-methyl-N-[7-methyl-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(C)c2n1[C@@H]1CCCN(C1)C(=O)C=C AWBUREOGISEZHO-GOSISDBHSA-N 0.000 claims 1
- GHBHACNOWPELTF-XYOKQWHBSA-N 2-methyl-N-[7-methyl-1-[1-[(E)-4-pyrrolidin-1-ylbut-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound c1cnc(C)cc1C(=O)Nc1nc2cccc(C)c2n1C1CCCCN(C(=O)\C=C\CN2CCCC2)C1 GHBHACNOWPELTF-XYOKQWHBSA-N 0.000 claims 1
- BXJXSACPNOQRDE-UHFFFAOYSA-N 2-methyl-N-[7-methyl-5-(piperidin-1-ylmethyl)-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCCCC3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C BXJXSACPNOQRDE-UHFFFAOYSA-N 0.000 claims 1
- BXJXSACPNOQRDE-RUZDIDTESA-N 2-methyl-N-[7-methyl-5-(piperidin-1-ylmethyl)-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]pyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCCCC3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C BXJXSACPNOQRDE-RUZDIDTESA-N 0.000 claims 1
- YLKJKTOAJBOQDF-UHFFFAOYSA-N 2-tert-butyl-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-4-carboxamide Chemical compound C(C)(C)(C)C1=NC=CC(=C1)C(=O)NC1=NC2=C(N1C1CN(CCCC1)C(C=CCN(C)C)=O)C(=CC=C2)C YLKJKTOAJBOQDF-UHFFFAOYSA-N 0.000 claims 1
- ONDJFMNJVBEGPW-UHFFFAOYSA-N 3-[[2-benzamido-3-(1-prop-2-enoylazepan-3-yl)benzimidazole-4-carbonyl]amino]propanoic acid Chemical compound OC(=O)CCNC(=O)c1cccc2nc(NC(=O)c3ccccc3)n(C3CCCCN(C3)C(=O)C=C)c12 ONDJFMNJVBEGPW-UHFFFAOYSA-N 0.000 claims 1
- OHGYDKHVHBTNDD-YRNVUSSQSA-N 3-chloro-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2,4-difluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc(F)c(Cl)c2F)nc2cccc(C)c12 OHGYDKHVHBTNDD-YRNVUSSQSA-N 0.000 claims 1
- FRSVCMDERZHSGJ-UHFFFAOYSA-N 3-chloro-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-fluorobenzamide Chemical compound ClC=1C(=C(C(=O)NC2=NC3=C(N2C2CN(CCCC2)C(C=CCN(C)C)=O)C(=CC=C3)C)C=CC1)F FRSVCMDERZHSGJ-UHFFFAOYSA-N 0.000 claims 1
- ZIICYJNHFUOOCE-UHFFFAOYSA-N 3-chloro-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]benzamide Chemical compound ClC=1C=C(C(=O)NC2=NC3=C(N2C2CN(CCCC2)C(C=CCN(C)C)=O)C(=CC=C3)C)C=CC1 ZIICYJNHFUOOCE-UHFFFAOYSA-N 0.000 claims 1
- XZXQHLJRMWPJTP-RIYZIHGNSA-N 3-cyano-N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]benzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccc(c2)C#N)nc2cccc(C)c12 XZXQHLJRMWPJTP-RIYZIHGNSA-N 0.000 claims 1
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- YQPUHXUUOKRRSL-SXOMAYOGSA-N N-[1-[(3R)-1-[(E)-but-2-enoyl]azepan-3-yl]-5-[[(3S)-3-methoxypyrrolidin-1-yl]methyl]-7-methylbenzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C(C=CC)(=O)N1C[C@@H](CCCC1)N1C(=NC2=C1C(=CC(=C2)CN2C[C@H](CC2)OC)C)NC(=O)C2=CC(=NC(=C2)C)C YQPUHXUUOKRRSL-SXOMAYOGSA-N 0.000 claims 1
- IACXGBQFWATELN-SGHRQYOTSA-N N-[1-[(3R)-1-[(E)-but-2-enoyl]azepan-3-yl]-5-[[(3S)-3-methoxypyrrolidin-1-yl]methyl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C1[C@@H](OC)CCN1Cc1ccc2n([C@@H]3CCCCN(C3)C(=O)\C=C\C)c(NC(=O)c3cc(C)nc(C)c3)nc2c1 IACXGBQFWATELN-SGHRQYOTSA-N 0.000 claims 1
- VPYIGPZDJRFBDM-QMASLXIKSA-N N-[1-[(3R)-1-[(E)-but-2-enoyl]azepan-3-yl]-7-chloro-6-(2-pyrrolidin-1-ylethoxy)benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/C)CCCC[C@H]1n1c(NC(=O)c2cc(C)nc(C)c2)nc2ccc(OCCN3CCCC3)c(Cl)c12 VPYIGPZDJRFBDM-QMASLXIKSA-N 0.000 claims 1
- AAQCNKXELQZHGC-DHXBXMGCSA-N N-[1-[(3R)-1-[(E)-but-2-enoyl]azepan-3-yl]-7-chloro-6-(2-pyrrolidin-1-ylethoxy)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/C)CCCC[C@H]1n1c(NC(=O)c2ccnc(C)c2)nc2ccc(OCCN3CCCC3)c(Cl)c12 AAQCNKXELQZHGC-DHXBXMGCSA-N 0.000 claims 1
- CEZGMYMLBLEGSJ-RUZDIDTESA-N N-[1-[(3R)-1-[(E)-but-2-enoyl]azepan-3-yl]-7-methyl-5-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C(C=CC)(=O)N1C[C@@H](CCCC1)N1C(=NC2=C1C(=CC(=C2)CN2CCCC2)C)NC(=O)C2=CC(=NC=C2)C CEZGMYMLBLEGSJ-RUZDIDTESA-N 0.000 claims 1
- RASLADSOFKKIEV-VUFXHXBKSA-N N-[1-[(3R)-1-[(E)-but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C1N(C(=O)/C=C/C)CCCC[C@H]1n1c(NC(=O)c2cccc(c2)C(F)(F)F)nc2cccc(C)c12 RASLADSOFKKIEV-VUFXHXBKSA-N 0.000 claims 1
- DNYNXYQNLLSFOE-JOCHJYFZSA-N N-[1-[(3R)-1-[2-(diethylaminomethyl)prop-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound CCN(CC)CC(=C)C(=O)N1CCCC[C@H](C1)n1c(NC(=O)c2ccnnc2)nc2cccc(C)c12 DNYNXYQNLLSFOE-JOCHJYFZSA-N 0.000 claims 1
- PNCBXMHNZVNRIP-LJQANCHMSA-N N-[1-[(3R)-1-ethenylsulfonylazepan-3-yl]-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound Cc1cccc2nc(NC(=O)c3cccc(c3)C(F)(F)F)n([C@@H]3CCCCN(C3)S(=O)(=O)C=C)c12 PNCBXMHNZVNRIP-LJQANCHMSA-N 0.000 claims 1
- QRGBOWJSOSLXPT-HSZRJFAPSA-N N-[1-[(3R)-1-prop-2-enoylazepan-3-yl]-7-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2cccc(CN3CCCC3)c2n1[C@@H]1CCCCN(C1)C(=O)C=C QRGBOWJSOSLXPT-HSZRJFAPSA-N 0.000 claims 1
- GFLOVYJTWAULRS-GOSISDBHSA-N N-[1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2ccccc2n1[C@@H]1CCCCN(C1)C(=O)C=C GFLOVYJTWAULRS-GOSISDBHSA-N 0.000 claims 1
- ZLUYWPBOVFZNTG-JOCHJYFZSA-N N-[1-[(3R)-1-prop-2-enoylpiperidin-3-yl]-5-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2cc(CN3CCCC3)ccc2n1[C@@H]1CCCN(C1)C(=O)C=C ZLUYWPBOVFZNTG-JOCHJYFZSA-N 0.000 claims 1
- XILZLQGBIXBPPH-OEMHODTASA-N N-[1-[(3S)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-(trifluoromethyl)pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@@H]1n1c(NC(=O)c2ccnc(c2)C(F)(F)F)nc2cccc(C)c12 XILZLQGBIXBPPH-OEMHODTASA-N 0.000 claims 1
- XBOWFZGBAMQXDI-BEBFYNPSSA-N N-[1-[(3S)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methyl-1,3-thiazole-5-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@@H]1n1c(NC(=O)c2cnc(C)s2)nc2cccc(C)c12 XBOWFZGBAMQXDI-BEBFYNPSSA-N 0.000 claims 1
- JCGHAROUDQMHTB-VWMRQFFHSA-N N-[1-[(6R)-4-[(E)-4-(dimethylamino)but-2-enoyl]-1,4-oxazepan-6-yl]-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCOC[C@@H]1n1c(NC(=O)c2cccc(c2)C(F)(F)F)nc2cccc(C)c12 JCGHAROUDQMHTB-VWMRQFFHSA-N 0.000 claims 1
- JCGHAROUDQMHTB-LTSKSLEPSA-N N-[1-[(6S)-4-[(E)-4-(dimethylamino)but-2-enoyl]-1,4-oxazepan-6-yl]-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CN(C/C=C/C(=O)N1CCOC[C@H](C1)N1C(=NC2=C1C(=CC=C2)C)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C JCGHAROUDQMHTB-LTSKSLEPSA-N 0.000 claims 1
- YHDWGFOLMJTHEQ-UHFFFAOYSA-N N-[1-[1-(2,3-dihydro-1,4-dioxine-5-carbonyl)azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound Cc1cccc2nc(NC(=O)c3ccnnc3)n(C3CCCCN(C3)C(=O)C3=COCCO3)c12 YHDWGFOLMJTHEQ-UHFFFAOYSA-N 0.000 claims 1
- UNSMIKMRYBHCTJ-UXBLZVDNSA-N N-[1-[1-[(E)-4-(3-fluoropyrrolidin-1-yl)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound c1cnc(C)cc1C(=O)Nc1nc2cccc(C)c2n1C1CCCCN(C(=O)\C=C\CN2CCC(F)C2)C1 UNSMIKMRYBHCTJ-UXBLZVDNSA-N 0.000 claims 1
- HIMHGXXCHNKURH-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methoxybenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1CCCN(C(=O)\C=C\CN(C)C)CC1n1c2c(OC)cccc2nc1NC(=O)c1ccnc(C)c1 HIMHGXXCHNKURH-XYOKQWHBSA-N 0.000 claims 1
- SGHHQLYODQIGBE-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methoxybenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C1CCCN(C(=O)\C=C\CN(C)C)CC1n1c2c(OC)cccc2nc1NC(=O)c1ccnnc1 SGHHQLYODQIGBE-YRNVUSSQSA-N 0.000 claims 1
- UEMAUQKNKVZWGA-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-1,3-oxazole-5-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cnco2)nc2cccc(C)c12 UEMAUQKNKVZWGA-YRNVUSSQSA-N 0.000 claims 1
- NOOQFELRWIDMBW-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-1-methyl-2-oxopyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccn(C)c(=O)c2)nc2cccc(C)c12 NOOQFELRWIDMBW-XYOKQWHBSA-N 0.000 claims 1
- FYAQLKIYMBLKPU-RIYZIHGNSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2,3-difluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccc(F)c2F)nc2cccc(C)c12 FYAQLKIYMBLKPU-RIYZIHGNSA-N 0.000 claims 1
- DSULVSKPGRWASO-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2,4-difluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc(F)cc2F)nc2cccc(C)c12 DSULVSKPGRWASO-YRNVUSSQSA-N 0.000 claims 1
- IHOMWAXTZMKLAT-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2,5-difluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cc(F)ccc2F)nc2cccc(C)c12 IHOMWAXTZMKLAT-YRNVUSSQSA-N 0.000 claims 1
- UKXVGRNSIJPYFK-UKTHLTGXSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CN(C/C=C/C(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC=C2)C)NC(=O)C2=CC(=NC(=C2)C)C)C UKXVGRNSIJPYFK-UKTHLTGXSA-N 0.000 claims 1
- USMSYRDXXCLQHO-MHWRWJLKSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-(2-methylphenyl)pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnc(c2)-c2ccccc2C)nc2cccc(C)c12 USMSYRDXXCLQHO-MHWRWJLKSA-N 0.000 claims 1
- ATSXIJDXOMIZTI-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-(tetrazol-1-yl)pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnc(c2)-n2cnnn2)nc2cccc(C)c12 ATSXIJDXOMIZTI-YRNVUSSQSA-N 0.000 claims 1
- PGYWBZCXKPBUBH-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-(trifluoromethoxy)pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnc(OC(F)(F)F)c2)nc2cccc(C)c12 PGYWBZCXKPBUBH-YRNVUSSQSA-N 0.000 claims 1
- GYZCDPYMSMUVHN-UKTHLTGXSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-ethoxypyridine-4-carboxamide Chemical compound c1cnc(OCC)cc1C(=O)Nc1nc2cccc(C)c2n1C1CCCCN(C(=O)\C=C\CN(C)C)C1 GYZCDPYMSMUVHN-UKTHLTGXSA-N 0.000 claims 1
- AFFJJEGJEXRNBA-OQLLNIDSSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-fluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccccc2F)nc2cccc(C)c12 AFFJJEGJEXRNBA-OQLLNIDSSA-N 0.000 claims 1
- GKZIUACFJYRISP-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-fluoropyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnc(F)c2)nc2cccc(C)c12 GKZIUACFJYRISP-YRNVUSSQSA-N 0.000 claims 1
- HDWZUQAWVKGKTM-NTEUORMPSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methylpyridine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccnc2C)nc2cccc(C)c12 HDWZUQAWVKGKTM-NTEUORMPSA-N 0.000 claims 1
- XHIMNFOJDWPMIP-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methylpyrimidine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnc(C)n2)nc2cccc(C)c12 XHIMNFOJDWPMIP-XYOKQWHBSA-N 0.000 claims 1
- BYXGLOPXVVKRIC-MHWRWJLKSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-phenylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnc(c2)-c2ccccc2)nc2cccc(C)c12 BYXGLOPXVVKRIC-MHWRWJLKSA-N 0.000 claims 1
- RLXMESZVIKJLTR-GXDHUFHOSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-piperidin-1-ylpyridine-4-carboxamide Chemical compound CN(C/C=C/C(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC=C2)C)NC(=O)C2=CC(=NC=C2)N2CCCCC2)C RLXMESZVIKJLTR-GXDHUFHOSA-N 0.000 claims 1
- WHRFEMBJCGIWOS-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3,4,5-trifluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cc(F)c(F)c(F)c2)nc2cccc(C)c12 WHRFEMBJCGIWOS-YRNVUSSQSA-N 0.000 claims 1
- MKMLLHCYCWEQHJ-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3,4-difluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc(F)c(F)c2)nc2cccc(C)c12 MKMLLHCYCWEQHJ-YRNVUSSQSA-N 0.000 claims 1
- FSUUFTQMRQPLJR-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3,5-difluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cc(F)cc(F)c2)nc2cccc(C)c12 FSUUFTQMRQPLJR-YRNVUSSQSA-N 0.000 claims 1
- BYUZDVSTUSMHRQ-RIYZIHGNSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-(tetrazol-1-yl)benzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccc(c2)-n2cnnn2)nc2cccc(C)c12 BYUZDVSTUSMHRQ-RIYZIHGNSA-N 0.000 claims 1
- GJBHMDHRKGITMA-RIYZIHGNSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccc(c2)C(F)(F)F)nc2cccc(C)c12 GJBHMDHRKGITMA-RIYZIHGNSA-N 0.000 claims 1
- ZSDCMXZKSXLQMT-RIYZIHGNSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-fluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccc(F)c2)nc2cccc(C)c12 ZSDCMXZKSXLQMT-RIYZIHGNSA-N 0.000 claims 1
- XRUZQTKXYYXBMW-OQLLNIDSSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-methoxybenzamide Chemical compound c1c(OC)cccc1C(=O)Nc1nc2cccc(C)c2n1C1CCCCN(C(=O)\C=C\CN(C)C)C1 XRUZQTKXYYXBMW-OQLLNIDSSA-N 0.000 claims 1
- TUOPFUOBVSJLEI-OQLLNIDSSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-methylbenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccc(C)c2)nc2cccc(C)c12 TUOPFUOBVSJLEI-OQLLNIDSSA-N 0.000 claims 1
- DACFGOIDGQNAAI-OQLLNIDSSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-methylsulfonylbenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccc(c2)S(C)(=O)=O)nc2cccc(C)c12 DACFGOIDGQNAAI-OQLLNIDSSA-N 0.000 claims 1
- JCYSNWNPNGSDJZ-UKTHLTGXSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-4,5-dimethylfuran-2-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cc(C)c(C)o2)nc2cccc(C)c12 JCYSNWNPNGSDJZ-UKTHLTGXSA-N 0.000 claims 1
- SVDMUEPXEKHWQC-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-4-fluorobenzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc(F)cc2)nc2cccc(C)c12 SVDMUEPXEKHWQC-YRNVUSSQSA-N 0.000 claims 1
- OJURJQCEQQSVOQ-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-5-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cncc(c2)C(F)(F)F)nc2cccc(C)c12 OJURJQCEQQSVOQ-YRNVUSSQSA-N 0.000 claims 1
- MQCDWGMMDAPGKB-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-5-fluoropyridine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cncc(F)c2)nc2cccc(C)c12 MQCDWGMMDAPGKB-YRNVUSSQSA-N 0.000 claims 1
- KIEXMVITNVJBEJ-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-5-methoxypyridine-3-carboxamide Chemical compound c1c(OC)cncc1C(=O)Nc1nc2cccc(C)c2n1C1CCCCN(C(=O)\C=C\CN(C)C)C1 KIEXMVITNVJBEJ-XYOKQWHBSA-N 0.000 claims 1
- IXTGHDWXMXJODY-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-5-methylpyridine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cncc(C)c2)nc2cccc(C)c12 IXTGHDWXMXJODY-XYOKQWHBSA-N 0.000 claims 1
- JSZQMPWCKLNMSX-UKTHLTGXSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-5-pyrrol-1-ylpyridine-3-carboxamide Chemical compound CN(C/C=C/C(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC=C2)C)NC(=O)C=2C=NC=C(C2)N2C=CC=C2)C JSZQMPWCKLNMSX-UKTHLTGXSA-N 0.000 claims 1
- YXQYYLNZEWUXMD-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc(nc2)C(F)(F)F)nc2cccc(C)c12 YXQYYLNZEWUXMD-YRNVUSSQSA-N 0.000 claims 1
- ORDHNWHVCPQQRX-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-methoxypyridine-3-carboxamide Chemical compound c1nc(OC)ccc1C(=O)Nc1nc2cccc(C)c2n1C1CCCCN(C(=O)\C=C\CN(C)C)C1 ORDHNWHVCPQQRX-XYOKQWHBSA-N 0.000 claims 1
- CVQCRGYFEVUAFL-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-methylpyridazine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cnnc(C)c2)nc2cccc(C)c12 CVQCRGYFEVUAFL-XYOKQWHBSA-N 0.000 claims 1
- CUUIZWDRZDSZDF-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-6-methylpyridine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc(C)nc2)nc2cccc(C)c12 CUUIZWDRZDSZDF-XYOKQWHBSA-N 0.000 claims 1
- TUOYPHBELCPBEP-MHWRWJLKSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]benzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccccc2)nc2cccc(C)c12 TUOYPHBELCPBEP-MHWRWJLKSA-N 0.000 claims 1
- QPTDZAFWPVKAMJ-NTUHNPAUSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]furan-2-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccco2)nc2cccc(C)c12 QPTDZAFWPVKAMJ-NTUHNPAUSA-N 0.000 claims 1
- APKSRUPPNSCHKI-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]imidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc3nccn3c2)nc2cccc(C)c12 APKSRUPPNSCHKI-YRNVUSSQSA-N 0.000 claims 1
- OXDJMOTUYOGIJL-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]imidazo[1,5-a]pyridine-7-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccn3cncc3c2)nc2cccc(C)c12 OXDJMOTUYOGIJL-YRNVUSSQSA-N 0.000 claims 1
- VGAXREMYPKZLOI-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]imidazo[2,1-b][1,3]thiazole-6-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cn3ccsc3n2)nc2cccc(C)c12 VGAXREMYPKZLOI-YRNVUSSQSA-N 0.000 claims 1
- WCWAMXPHBBKSGC-OQLLNIDSSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]naphthalene-2-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccc3ccccc3c2)nc2cccc(C)c12 WCWAMXPHBBKSGC-OQLLNIDSSA-N 0.000 claims 1
- SYDJVOHRPVPNHQ-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyrazine-2-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cnccn2)nc2cccc(C)c12 SYDJVOHRPVPNHQ-YRNVUSSQSA-N 0.000 claims 1
- WAOKHJBWRKYTQU-MDWZMJQESA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridazine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccnn2)nc2cccc(C)c12 WAOKHJBWRKYTQU-MDWZMJQESA-N 0.000 claims 1
- MULQDQYOJVSAFA-NTEUORMPSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-2-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccccn2)nc2cccc(C)c12 MULQDQYOJVSAFA-NTEUORMPSA-N 0.000 claims 1
- CVKOKVWKAYIKJY-MDWZMJQESA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-3-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cccnc2)nc2cccc(C)c12 CVKOKVWKAYIKJY-MDWZMJQESA-N 0.000 claims 1
- JBFVKDQUMPUGNX-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccncc2)nc2cccc(C)c12 JBFVKDQUMPUGNX-YRNVUSSQSA-N 0.000 claims 1
- CMEVOUPTBUMXQB-KPKJPENVSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyrimidine-2-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ncccn2)nc2cccc(C)c12 CMEVOUPTBUMXQB-KPKJPENVSA-N 0.000 claims 1
- SSPRHDVETPIMAW-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyrimidine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccncn2)nc2cccc(C)c12 SSPRHDVETPIMAW-YRNVUSSQSA-N 0.000 claims 1
- OZOIDJVOCAPKCA-XYOKQWHBSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-propan-2-yloxybenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound CN(C/C=C/C(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC=C2)OC(C)C)NC(=O)C2=CN=NC=C2)C OZOIDJVOCAPKCA-XYOKQWHBSA-N 0.000 claims 1
- NQVMBKYFRATBKG-WEVVVXLNSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]piperidin-3-yl]-5-(hydroxymethyl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CN(C/C=C/C(=O)N1CC(CCC1)N1C(=NC2=C1C=CC(=C2)CO)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C NQVMBKYFRATBKG-WEVVVXLNSA-N 0.000 claims 1
- VLWBXJCVGMEFIZ-YRNVUSSQSA-N N-[1-[1-[(E)-4-(dimethylamino)but-2-enoyl]piperidin-3-yl]-7-methylbenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC1n1c(NC(=O)c2ccnc(C)c2)nc2cccc(C)c12 VLWBXJCVGMEFIZ-YRNVUSSQSA-N 0.000 claims 1
- QVAIFDVUUPRQOP-UHFFFAOYSA-N N-[1-[1-[(E)-but-2-enoyl]azepan-3-yl]-5-[(3-fluoropyrrolidin-1-yl)methyl]-7-methylbenzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C(C=CC)(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC(=C2)CN2CC(CC2)F)C)NC(=O)C2=CC(=NC(=C2)C)C QVAIFDVUUPRQOP-UHFFFAOYSA-N 0.000 claims 1
- YQPUHXUUOKRRSL-UHFFFAOYSA-N N-[1-[1-[(E)-but-2-enoyl]azepan-3-yl]-5-[(3-methoxypyrrolidin-1-yl)methyl]-7-methylbenzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C(C=CC)(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC(=C2)CN2CC(CC2)OC)C)NC(=O)C2=CC(=NC(=C2)C)C YQPUHXUUOKRRSL-UHFFFAOYSA-N 0.000 claims 1
- BPAGEFGEKNLNMG-UHFFFAOYSA-N N-[1-[1-[(E)-but-2-enoyl]azepan-3-yl]-5-[(3-methoxypyrrolidin-1-yl)methyl]-7-methylbenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C(C=CC)(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC(=C2)CN2CC(CC2)OC)C)NC(=O)C2=CC(=NC=C2)C BPAGEFGEKNLNMG-UHFFFAOYSA-N 0.000 claims 1
- IACXGBQFWATELN-CPEHPBMISA-N N-[1-[1-[(E)-but-2-enoyl]azepan-3-yl]-5-[[(3S)-3-methoxypyrrolidin-1-yl]methyl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C1[C@@H](OC)CCN1Cc1ccc2n(C3CCCCN(C3)C(=O)\C=C\C)c(NC(=O)c3cc(C)nc(C)c3)nc2c1 IACXGBQFWATELN-CPEHPBMISA-N 0.000 claims 1
- CEZGMYMLBLEGSJ-RUDMXATFSA-N N-[1-[1-[(E)-but-2-enoyl]azepan-3-yl]-7-methyl-5-(pyrrolidin-1-ylmethyl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/C)CCCCC1n1c(NC(=O)c2ccnc(C)c2)nc2cc(CN3CCCC3)cc(C)c12 CEZGMYMLBLEGSJ-RUDMXATFSA-N 0.000 claims 1
- RASLADSOFKKIEV-FPYGCLRLSA-N N-[1-[1-[(E)-but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C1N(C(=O)/C=C/C)CCCCC1n1c(NC(=O)c2cccc(c2)C(F)(F)F)nc2cccc(C)c12 RASLADSOFKKIEV-FPYGCLRLSA-N 0.000 claims 1
- DNYNXYQNLLSFOE-UHFFFAOYSA-N N-[1-[1-[2-(diethylaminomethyl)prop-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C(C)N(CC)CC(C(=O)N1CC(CCCC1)N1C(=NC2=C1C(=CC=C2)C)NC(=O)C2=CN=NC=C2)=C DNYNXYQNLLSFOE-UHFFFAOYSA-N 0.000 claims 1
- DFKURWXKYBHDMJ-UHFFFAOYSA-N N-[1-[1-[4-(azetidin-1-yl)but-2-enoyl]azepan-3-yl]-7-chlorobenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(Cl)c2n1C1CCCCN(C1)C(=O)C=CCN1CCC1 DFKURWXKYBHDMJ-UHFFFAOYSA-N 0.000 claims 1
- OFLKSFJTTRHGBF-UHFFFAOYSA-N N-[1-[1-[4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-(trifluoromethyl)benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CN(C)CC=CC(=O)N1CCCCC(C1)n1c(NC(=O)c2cc(C)nc(C)c2)nc2cccc(c12)C(F)(F)F OFLKSFJTTRHGBF-UHFFFAOYSA-N 0.000 claims 1
- FPZWUEGIYYDTRG-UHFFFAOYSA-N N-[1-[1-[4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-(trifluoromethyl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound CN(C)CC=CC(=O)N1CCCCC(C1)n1c(NC(=O)c2ccnc(C)c2)nc2cccc(c12)C(F)(F)F FPZWUEGIYYDTRG-UHFFFAOYSA-N 0.000 claims 1
- FNGWXUSKVKNLMN-UHFFFAOYSA-N N-[1-[1-[4-(tert-butylamino)but-2-enoyl]azepan-3-yl]-7-chlorobenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(Cl)c2n1C1CCCCN(C1)C(=O)C=CCNC(C)(C)C FNGWXUSKVKNLMN-UHFFFAOYSA-N 0.000 claims 1
- ULJPGJAUFNXESQ-MDWZMJQESA-N N-[1-[4-[(E)-4-(dimethylamino)but-2-enoyl]-1,4-oxazepan-6-yl]-7-(3-methyl-1,2,4-oxadiazol-5-yl)benzimidazol-2-yl]benzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCOCC1n1c(NC(=O)c2ccccc2)nc2cccc(-c3nc(C)no3)c12 ULJPGJAUFNXESQ-MDWZMJQESA-N 0.000 claims 1
- JCGHAROUDQMHTB-IZZDOVSWSA-N N-[1-[4-[(E)-4-(dimethylamino)but-2-enoyl]-1,4-oxazepan-6-yl]-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCOCC1n1c(NC(=O)c2cccc(c2)C(F)(F)F)nc2cccc(C)c12 JCGHAROUDQMHTB-IZZDOVSWSA-N 0.000 claims 1
- WEEGOPBNFPYWGI-UHFFFAOYSA-N N-[3-(1-prop-2-enoylpiperidin-3-yl)imidazo[4,5-c]pyridin-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2ccncc2n1C1CCCN(C1)C(=O)C=C WEEGOPBNFPYWGI-UHFFFAOYSA-N 0.000 claims 1
- RKOYEQKCONUVPY-UHFFFAOYSA-N N-[5-(2-methoxyethoxymethyl)-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound COCCOCC1=CC2=C(N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C2CN(CCC2)C(C=C)=O)C=C1 RKOYEQKCONUVPY-UHFFFAOYSA-N 0.000 claims 1
- RKOYEQKCONUVPY-OAQYLSRUSA-N N-[5-(2-methoxyethoxymethyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound COCCOCc1ccc2n([C@@H]3CCCN(C3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 RKOYEQKCONUVPY-OAQYLSRUSA-N 0.000 claims 1
- NWGARZULJOZBBU-UHFFFAOYSA-N N-[5-(2-methoxyethoxymethyl)-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound COCCOCc1cc(C)c2n(C3CCCCN(C3)C(=O)C=C)c(NC(=O)c3ccccc3)nc2c1 NWGARZULJOZBBU-UHFFFAOYSA-N 0.000 claims 1
- NWGARZULJOZBBU-HSZRJFAPSA-N N-[5-(2-methoxyethoxymethyl)-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound COCCOCC1=CC2=C(N(C(=N2)NC(C2=CC=CC=C2)=O)[C@H]2CN(CCCC2)C(C=C)=O)C(=C1)C NWGARZULJOZBBU-HSZRJFAPSA-N 0.000 claims 1
- ZDCBOKLRJQMVAI-UHFFFAOYSA-N N-[5-(azetidin-1-ylmethyl)-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCC3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C ZDCBOKLRJQMVAI-UHFFFAOYSA-N 0.000 claims 1
- ZDCBOKLRJQMVAI-HSZRJFAPSA-N N-[5-(azetidin-1-ylmethyl)-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCC3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C ZDCBOKLRJQMVAI-HSZRJFAPSA-N 0.000 claims 1
- YWUWVJIKGDPRGG-UHFFFAOYSA-N N-[5-(ethoxymethyl)-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CCOCc1ccc2n(C3CCCN(C3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 YWUWVJIKGDPRGG-UHFFFAOYSA-N 0.000 claims 1
- WWYSQRIOKVGKQY-UHFFFAOYSA-N N-[5-(hydroxymethyl)-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound OCc1ccc2n(C3CCCN(C3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 WWYSQRIOKVGKQY-UHFFFAOYSA-N 0.000 claims 1
- WMSYQNNTHDNIEI-UHFFFAOYSA-N N-[5-(methoxymethyl)-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound COCC1=CC2=C(N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C2CN(CCC2)C(C=C)=O)C=C1 WMSYQNNTHDNIEI-UHFFFAOYSA-N 0.000 claims 1
- DJPOWQSJECOBBO-JOCHJYFZSA-N N-[5-(morpholin-4-ylmethyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2cc(CN3CCOCC3)ccc2n1[C@@H]1CCCN(C1)C(=O)C=C DJPOWQSJECOBBO-JOCHJYFZSA-N 0.000 claims 1
- GXWPARSFAAUDFY-HSZRJFAPSA-N N-[5-(piperidin-1-ylmethyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2cc(CN3CCCCC3)ccc2n1[C@@H]1CCCN(C1)C(=O)C=C GXWPARSFAAUDFY-HSZRJFAPSA-N 0.000 claims 1
- UEZFOSUZIDDJER-UHFFFAOYSA-N N-[5-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCS(=O)(=O)CC3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C UEZFOSUZIDDJER-UHFFFAOYSA-N 0.000 claims 1
- UEZFOSUZIDDJER-XMMPIXPASA-N N-[5-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCS(=O)(=O)CC3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C UEZFOSUZIDDJER-XMMPIXPASA-N 0.000 claims 1
- NFXHWQPAWCTQTR-UHFFFAOYSA-N N-[5-[(3,3-difluoroazetidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CC(F)(F)C3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C NFXHWQPAWCTQTR-UHFFFAOYSA-N 0.000 claims 1
- NFXHWQPAWCTQTR-JOCHJYFZSA-N N-[5-[(3,3-difluoroazetidin-1-yl)methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CC(F)(F)C3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C NFXHWQPAWCTQTR-JOCHJYFZSA-N 0.000 claims 1
- WRDHQKAVSCXLAN-UHFFFAOYSA-N N-[5-[(3,3-difluoropyrrolidin-1-yl)methyl]-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2cc(CN3CCC(F)(F)C3)ccc2n1C1CCCN(C1)C(=O)C=C WRDHQKAVSCXLAN-UHFFFAOYSA-N 0.000 claims 1
- WRDHQKAVSCXLAN-OAQYLSRUSA-N N-[5-[(3,3-difluoropyrrolidin-1-yl)methyl]-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC1(CN(CC1)CC1=CC2=C(N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)[C@H]2CN(CCC2)C(C=C)=O)C=C1)F WRDHQKAVSCXLAN-OAQYLSRUSA-N 0.000 claims 1
- IMFKETJITRYFOH-UHFFFAOYSA-N N-[5-[(3,3-difluoropyrrolidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCC(F)(F)C3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C IMFKETJITRYFOH-UHFFFAOYSA-N 0.000 claims 1
- IMFKETJITRYFOH-HSZRJFAPSA-N N-[5-[(3,3-difluoropyrrolidin-1-yl)methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCC(F)(F)C3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C IMFKETJITRYFOH-HSZRJFAPSA-N 0.000 claims 1
- ISCTYGXDJFYISL-UHFFFAOYSA-N N-[5-[(3,4-dihydroxypyrrolidin-1-yl)methyl]-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound OC1CN(CC1O)CC1=CC2=C(N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C2CN(CCC2)C(C=C)=O)C=C1 ISCTYGXDJFYISL-UHFFFAOYSA-N 0.000 claims 1
- WCIYIWDPEBHZME-UHFFFAOYSA-N N-[5-[(3-fluoroazetidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound FC1CN(C1)CC1=CC2=C(N(C(=N2)NC(=O)C2=CC(=NC=C2)C)C2CN(CCCC2)C(C=C)=O)C(=C1)C WCIYIWDPEBHZME-UHFFFAOYSA-N 0.000 claims 1
- WCIYIWDPEBHZME-HSZRJFAPSA-N N-[5-[(3-fluoroazetidin-1-yl)methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CC(F)C3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C WCIYIWDPEBHZME-HSZRJFAPSA-N 0.000 claims 1
- ZUCBRUJRWIBMLX-UHFFFAOYSA-N N-[5-[(3-fluoropyrrolidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound Cc1cc(cc(C)n1)C(=O)Nc1nc2cc(CN3CCC(F)C3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C ZUCBRUJRWIBMLX-UHFFFAOYSA-N 0.000 claims 1
- HEROWVQMOQJATR-UHFFFAOYSA-N N-[5-[(3-fluoropyrrolidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCC(F)C3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C HEROWVQMOQJATR-UHFFFAOYSA-N 0.000 claims 1
- QZZOCBHDQPVZJE-UHFFFAOYSA-N N-[5-[(3-hydroxypyrrolidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CCC(O)C3)cc(C)c2n1C1CCCCN(C1)C(=O)C=C QZZOCBHDQPVZJE-UHFFFAOYSA-N 0.000 claims 1
- HTTRONHMUOYQTM-UHFFFAOYSA-N N-[5-[(3-methoxyazetidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound COC1CN(Cc2cc(C)c3n(C4CCCCN(C4)C(=O)C=C)c(NC(=O)c4ccnc(C)c4)nc3c2)C1 HTTRONHMUOYQTM-UHFFFAOYSA-N 0.000 claims 1
- HTTRONHMUOYQTM-HSZRJFAPSA-N N-[5-[(3-methoxyazetidin-1-yl)methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound COC1CN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4ccnc(C)c4)nc3c2)C1 HTTRONHMUOYQTM-HSZRJFAPSA-N 0.000 claims 1
- KNUNIZRVOHRYRL-UHFFFAOYSA-N N-[5-[(3-methoxypyrrolidin-1-yl)methyl]-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound COC1CCN(Cc2ccc3n(C4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)C1 KNUNIZRVOHRYRL-UHFFFAOYSA-N 0.000 claims 1
- KAAPLRXUOPJYAU-UHFFFAOYSA-N N-[5-[(3-methoxypyrrolidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound COC1CCN(Cc2cc(C)c3n(C4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)C1 KAAPLRXUOPJYAU-UHFFFAOYSA-N 0.000 claims 1
- QTXDMJQIQDMXPP-UHFFFAOYSA-N N-[5-[(3-methoxypyrrolidin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound COC1CCN(Cc2cc(C)c3n(C4CCCCN(C4)C(=O)C=C)c(NC(=O)c4ccnc(C)c4)nc3c2)C1 QTXDMJQIQDMXPP-UHFFFAOYSA-N 0.000 claims 1
- MTUFXPOTXOPSHV-UHFFFAOYSA-N N-[5-[(4-acetylpiperazin-1-yl)methyl]-7-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CC(=O)N1CCN(Cc2cc(C)c3n(C4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)CC1 MTUFXPOTXOPSHV-UHFFFAOYSA-N 0.000 claims 1
- MTUFXPOTXOPSHV-HHHXNRCGSA-N N-[5-[(4-acetylpiperazin-1-yl)methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CC(=O)N1CCN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)CC1 MTUFXPOTXOPSHV-HHHXNRCGSA-N 0.000 claims 1
- ZUCBRUJRWIBMLX-JWQCQUIFSA-N N-[5-[[(3R)-3-fluoropyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound Cc1cc(cc(C)n1)C(=O)Nc1nc2cc(CN3CC[C@@H](F)C3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C ZUCBRUJRWIBMLX-JWQCQUIFSA-N 0.000 claims 1
- HEROWVQMOQJATR-DNQXCXABSA-N N-[5-[[(3R)-3-fluoropyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CC[C@@H](F)C3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C HEROWVQMOQJATR-DNQXCXABSA-N 0.000 claims 1
- KAAPLRXUOPJYAU-CLJLJLNGSA-N N-[5-[[(3R)-3-methoxypyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CO[C@@H]1CCN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)C1 KAAPLRXUOPJYAU-CLJLJLNGSA-N 0.000 claims 1
- QTXDMJQIQDMXPP-JWQCQUIFSA-N N-[5-[[(3R)-3-methoxypyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound CO[C@@H]1CCN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4ccnc(C)c4)nc3c2)C1 QTXDMJQIQDMXPP-JWQCQUIFSA-N 0.000 claims 1
- ISCTYGXDJFYISL-AGILITTLSA-N N-[5-[[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]methyl]-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound O[C@@H]1CN(Cc2ccc3n([C@@H]4CCCN(C4)C(=O)C=C)c(NC(=O)c4cccc(c4)C(F)(F)F)nc3c2)C[C@H]1O ISCTYGXDJFYISL-AGILITTLSA-N 0.000 claims 1
- ZUCBRUJRWIBMLX-LOSJGSFVSA-N N-[5-[[(3S)-3-fluoropyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound Cc1cc(cc(C)n1)C(=O)Nc1nc2cc(CN3CC[C@H](F)C3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C ZUCBRUJRWIBMLX-LOSJGSFVSA-N 0.000 claims 1
- HEROWVQMOQJATR-BJKOFHAPSA-N N-[5-[[(3S)-3-fluoropyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cc(CN3CC[C@H](F)C3)cc(C)c2n1[C@@H]1CCCCN(C1)C(=O)C=C HEROWVQMOQJATR-BJKOFHAPSA-N 0.000 claims 1
- QZZOCBHDQPVZJE-RPWUZVMVSA-N N-[5-[[(3S)-3-hydroxypyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound O[C@@H]1CN(CC1)CC1=CC2=C(N(C(=N2)NC(=O)C2=CC(=NC=C2)C)[C@H]2CN(CCCC2)C(C=C)=O)C(=C1)C QZZOCBHDQPVZJE-RPWUZVMVSA-N 0.000 claims 1
- KNUNIZRVOHRYRL-RPBOFIJWSA-N N-[5-[[(3S)-3-methoxypyrrolidin-1-yl]methyl]-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CO[C@H]1CCN(Cc2ccc3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)C1 KNUNIZRVOHRYRL-RPBOFIJWSA-N 0.000 claims 1
- KAAPLRXUOPJYAU-FTJBHMTQSA-N N-[5-[[(3S)-3-methoxypyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CO[C@H]1CCN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4cc(C)nc(C)c4)nc3c2)C1 KAAPLRXUOPJYAU-FTJBHMTQSA-N 0.000 claims 1
- QTXDMJQIQDMXPP-RPBOFIJWSA-N N-[5-[[(3S)-3-methoxypyrrolidin-1-yl]methyl]-7-methyl-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound CO[C@H]1CCN(Cc2cc(C)c3n([C@@H]4CCCCN(C4)C(=O)C=C)c(NC(=O)c4ccnc(C)c4)nc3c2)C1 QTXDMJQIQDMXPP-RPBOFIJWSA-N 0.000 claims 1
- MWUUNVOAGXGSPR-UHFFFAOYSA-N N-[5-[[acetyl(methyl)amino]methyl]-1-(1-prop-2-enoylpiperidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CN(C(C)=O)CC1=CC2=C(N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C2CN(CCC2)C(C=C)=O)C=C1 MWUUNVOAGXGSPR-UHFFFAOYSA-N 0.000 claims 1
- MWUUNVOAGXGSPR-OAQYLSRUSA-N N-[5-[[acetyl(methyl)amino]methyl]-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CN(Cc1ccc2n([C@@H]3CCCN(C3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1)C(C)=O MWUUNVOAGXGSPR-OAQYLSRUSA-N 0.000 claims 1
- PNPASOJCMMKWKC-UHFFFAOYSA-N N-[5-acetyl-1-(1-prop-2-enoylpiperidin-3-yl)-6,7-dihydro-4H-imidazo[4,5-c]pyridin-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C(C)(=O)N1CC2=C(CC1)N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C2CN(CCC2)C(C=C)=O PNPASOJCMMKWKC-UHFFFAOYSA-N 0.000 claims 1
- SZFSPANTIJCIGE-UHFFFAOYSA-N N-[5-acetyl-3-(1-prop-2-enoylpiperidin-3-yl)-6,7-dihydro-4H-imidazo[4,5-c]pyridin-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CC(=O)N1CCc2nc(NC(=O)c3cccc(c3)C(F)(F)F)n(C3CCCN(C3)C(=O)C=C)c2C1 SZFSPANTIJCIGE-UHFFFAOYSA-N 0.000 claims 1
- RCSCITPXZCYWJL-UHFFFAOYSA-N N-[5-methyl-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC2=C(N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C2CN(CCCC2)C(C=C)=O)C=C1 RCSCITPXZCYWJL-UHFFFAOYSA-N 0.000 claims 1
- FNFCVOITONFTEF-UHFFFAOYSA-N N-[5-methyl-1-(1-prop-2-enoylazepan-4-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound Cc1ccc2n(C3CCCN(CC3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 FNFCVOITONFTEF-UHFFFAOYSA-N 0.000 claims 1
- ONHORUSKCPCHSG-UHFFFAOYSA-N N-[5-methyl-1-(1-prop-2-enoylazetidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound Cc1ccc2n(C3CN(C3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 ONHORUSKCPCHSG-UHFFFAOYSA-N 0.000 claims 1
- HZMZQDASGBQWAM-UHFFFAOYSA-N N-[5-methyl-1-(1-prop-2-enoylpiperidin-4-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound Cc1ccc2n(C3CCN(CC3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 HZMZQDASGBQWAM-UHFFFAOYSA-N 0.000 claims 1
- DKAMNULQDZQMQN-UHFFFAOYSA-N N-[5-methyl-1-(1-prop-2-enoylpyrrolidin-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound Cc1ccc2n(C3CCN(C3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 DKAMNULQDZQMQN-UHFFFAOYSA-N 0.000 claims 1
- CXICEXOWGOQDAE-GOSISDBHSA-N N-[5-methyl-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound Cc1ccc2n([C@@H]3CCCN(C3)C(=O)C=C)c(NC(=O)c3cccc(c3)C(F)(F)F)nc2c1 CXICEXOWGOQDAE-GOSISDBHSA-N 0.000 claims 1
- XOSSNNRERUSOQC-UHFFFAOYSA-N N-[5-methyl-3-(1-prop-2-enoylpiperidin-3-yl)-6,7-dihydro-4H-imidazo[4,5-c]pyridin-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CN1CCc2nc(NC(=O)c3cccc(c3)C(F)(F)F)n(C3CCCN(C3)C(=O)C=C)c2C1 XOSSNNRERUSOQC-UHFFFAOYSA-N 0.000 claims 1
- YXRRNDMVVAPPFE-UHFFFAOYSA-N N-[5-methylsulfonyl-1-(1-prop-2-enoylpiperidin-3-yl)-6,7-dihydro-4H-imidazo[4,5-c]pyridin-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)N1CC2=C(CC1)N(C(=N2)NC(C2=CC(=CC=C2)C(F)(F)F)=O)C2CN(CCC2)C(C=C)=O YXRRNDMVVAPPFE-UHFFFAOYSA-N 0.000 claims 1
- ZWSNPROTUPXEDM-UHFFFAOYSA-N N-[5-methylsulfonyl-3-(1-prop-2-enoylpiperidin-3-yl)-6,7-dihydro-4H-imidazo[4,5-c]pyridin-2-yl]-3-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)N1CCc2nc(NC(=O)c3cccc(c3)C(F)(F)F)n(C3CCCN(C3)C(=O)C=C)c2C1 ZWSNPROTUPXEDM-UHFFFAOYSA-N 0.000 claims 1
- HDRKTANXQYEREL-OAQYLSRUSA-N N-[6-chloro-1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-5-methoxybenzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound ClC=1C(=CC2=C(N(C(=N2)NC(=O)C2=CC(=NC(=C2)C)C)[C@H]2CN(CCCC2)C(C=CCN(C)C)=O)C1)OC HDRKTANXQYEREL-OAQYLSRUSA-N 0.000 claims 1
- DQKSGAAGSNRDFB-FHVRUZERSA-N N-[6-chloro-1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-5-methoxybenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound c12cc(Cl)c(OC)cc2nc(NC(=O)c2cc(C)ncc2)n1[C@H]1CN(C(=O)\C=C\CN(C)C)CCCC1 DQKSGAAGSNRDFB-FHVRUZERSA-N 0.000 claims 1
- DQKSGAAGSNRDFB-UHFFFAOYSA-N N-[6-chloro-1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-5-methoxybenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC=1C(=CC2=C(N(C(=N2)NC(=O)C2=CC(=NC=C2)C)C2CN(CCCC2)C(C=CCN(C)C)=O)C1)OC DQKSGAAGSNRDFB-UHFFFAOYSA-N 0.000 claims 1
- XYWMUFQTSSGGFC-UHFFFAOYSA-N N-[7-(1,1-dioxo-1,4-thiazinane-4-carbonyl)-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound C=CC(=O)N1CCCCC(C1)n1c(NC(=O)c2ccccc2)nc2cccc(C(=O)N3CCS(=O)(=O)CC3)c12 XYWMUFQTSSGGFC-UHFFFAOYSA-N 0.000 claims 1
- CRBGNDYPTYLSKS-UHFFFAOYSA-N N-[7-(2-methoxyethoxymethyl)-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound COCCOCc1cccc2nc(NC(=O)c3ccccc3)n(C3CCCCN(C3)C(=O)C=C)c12 CRBGNDYPTYLSKS-UHFFFAOYSA-N 0.000 claims 1
- CRBGNDYPTYLSKS-JOCHJYFZSA-N N-[7-(2-methoxyethoxymethyl)-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound COCCOCc1cccc2nc(NC(=O)c3ccccc3)n([C@@H]3CCCCN(C3)C(=O)C=C)c12 CRBGNDYPTYLSKS-JOCHJYFZSA-N 0.000 claims 1
- LNZJCWDRTPCPDM-UHFFFAOYSA-N N-[7-(3,4-dihydroxypyrrolidine-1-carbonyl)-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound OC1CN(CC1O)C(=O)c1cccc2nc(NC(=O)c3ccccc3)n(C3CCCCN(C3)C(=O)C=C)c12 LNZJCWDRTPCPDM-UHFFFAOYSA-N 0.000 claims 1
- ULFZPYBZZZYMKW-UHFFFAOYSA-N N-[7-(3-methyl-1,2,4-oxadiazol-5-yl)-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound Cc1noc(n1)-c1cccc2nc(NC(=O)c3ccccc3)n(C3CCCCN(C3)C(=O)C=C)c12 ULFZPYBZZZYMKW-UHFFFAOYSA-N 0.000 claims 1
- UATYZQVACZUKKO-UHFFFAOYSA-N N-[7-(3-methyl-1,2,4-oxadiazol-5-yl)-1-(4-prop-2-enoyl-1,4-oxazepan-6-yl)benzimidazol-2-yl]benzamide Chemical compound CC1=NOC(=N1)C1=CC=CC2=C1N(C(=N2)NC(C2=CC=CC=C2)=O)C2CN(CCOC2)C(C=C)=O UATYZQVACZUKKO-UHFFFAOYSA-N 0.000 claims 1
- TVNKONPXYIAVOL-UHFFFAOYSA-N N-[7-(hydroxymethyl)-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound OCC1=CC=CC2=C1N(C(=N2)NC(C2=CC=CC=C2)=O)C2CN(CCCC2)C(C=C)=O TVNKONPXYIAVOL-UHFFFAOYSA-N 0.000 claims 1
- TVNKONPXYIAVOL-LJQANCHMSA-N N-[7-(hydroxymethyl)-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound OCC1=C2N([C@@H]3CCCCN(C3)C(=O)C=C)C(NC(=O)C3=CC=CC=C3)=NC2=CC=C1 TVNKONPXYIAVOL-LJQANCHMSA-N 0.000 claims 1
- RCQBYARZCJDYHW-UHFFFAOYSA-N N-[7-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound C=CC(=O)N1CCCCC(C1)n1c(NC(=O)c2ccccc2)nc2cccc(CN3CCS(=O)(=O)CC3)c12 RCQBYARZCJDYHW-UHFFFAOYSA-N 0.000 claims 1
- RCQBYARZCJDYHW-HSZRJFAPSA-N N-[7-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound C=CC(=O)N1CCCC[C@H](C1)n1c(NC(=O)c2ccccc2)nc2cccc(CN3CCS(=O)(=O)CC3)c12 RCQBYARZCJDYHW-HSZRJFAPSA-N 0.000 claims 1
- USDBLRVAOQKJGH-UHFFFAOYSA-N N-[7-[(3-hydroxypyrrolidin-1-yl)methyl]-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound OC1CCN(Cc2cccc3nc(NC(=O)c4ccccc4)n(C4CCCCN(C4)C(=O)C=C)c23)C1 USDBLRVAOQKJGH-UHFFFAOYSA-N 0.000 claims 1
- USDBLRVAOQKJGH-WTQRLHSKSA-N N-[7-[(3-hydroxypyrrolidin-1-yl)methyl]-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound OC1CCN(Cc2cccc3nc(NC(=O)c4ccccc4)n([C@@H]4CCCCN(C4)C(=O)C=C)c23)C1 USDBLRVAOQKJGH-WTQRLHSKSA-N 0.000 claims 1
- LNZJCWDRTPCPDM-QENMJEOYSA-N N-[7-[(3R,4R)-3,4-dihydroxypyrrolidine-1-carbonyl]-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound O[C@@H]1CN(C[C@H]1O)C(=O)c1cccc2nc(NC(=O)c3ccccc3)n(C3CCCCN(C3)C(=O)C=C)c12 LNZJCWDRTPCPDM-QENMJEOYSA-N 0.000 claims 1
- LLHVBBNWHPGSMK-UHFFFAOYSA-N N-[7-[(dimethylamino)methyl]-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound CN(C)Cc1cccc2nc(NC(=O)c3ccccc3)n(C3CCCCN(C3)C(=O)C=C)c12 LLHVBBNWHPGSMK-UHFFFAOYSA-N 0.000 claims 1
- LLHVBBNWHPGSMK-OAQYLSRUSA-N N-[7-[(dimethylamino)methyl]-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound CN(C)Cc1cccc2nc(NC(=O)c3ccccc3)n([C@@H]3CCCCN(C3)C(=O)C=C)c12 LLHVBBNWHPGSMK-OAQYLSRUSA-N 0.000 claims 1
- UMRZZUZQYYJNMU-UHFFFAOYSA-N N-[7-[[methyl(2-methylsulfonylethyl)amino]methyl]-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]benzamide Chemical compound CS(=O)(=O)CCN(C)CC1=CC=CC2=C1N(C(=N2)NC(C2=CC=CC=C2)=O)C2CN(CCCC2)C(C=C)=O UMRZZUZQYYJNMU-UHFFFAOYSA-N 0.000 claims 1
- UMRZZUZQYYJNMU-HSZRJFAPSA-N N-[7-[[methyl(2-methylsulfonylethyl)amino]methyl]-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]benzamide Chemical compound CN(CCS(C)(=O)=O)Cc1cccc2nc(NC(=O)c3ccccc3)n([C@@H]3CCCCN(C3)C(=O)C=C)c12 UMRZZUZQYYJNMU-HSZRJFAPSA-N 0.000 claims 1
- FIEVDKPXHAPDIU-UHFFFAOYSA-N N-[7-chloro-1-(1-prop-2-enoylazepan-3-yl)-6-(2-pyrrolidin-1-ylethoxy)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2ccc(OCCN3CCCC3)c(Cl)c2n1C1CCCCN(C1)C(=O)C=C FIEVDKPXHAPDIU-UHFFFAOYSA-N 0.000 claims 1
- DFRYGKYFVIKKJW-UHFFFAOYSA-N N-[7-chloro-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC1=CC=CC2=C1N(C(=N2)NC(=O)C2=CC(=NC=C2)C)C2CN(CCCC2)C(C=C)=O DFRYGKYFVIKKJW-UHFFFAOYSA-N 0.000 claims 1
- YOIIPCMYRPWPGE-UHFFFAOYSA-N N-[7-chloro-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2cccc(Cl)c2n1C1CCCCN(C1)C(=O)C=C YOIIPCMYRPWPGE-UHFFFAOYSA-N 0.000 claims 1
- CSLAFQYBPUOBGG-UHFFFAOYSA-N N-[7-chloro-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound N1=NC=C(C=C1)C(=O)NC1=NC2=C(N1C1CN(CCCC1)C(C=C)=O)C(=CC=C2)Cl CSLAFQYBPUOBGG-UHFFFAOYSA-N 0.000 claims 1
- QUQHOJKEEPBPLR-OAQYLSRUSA-N N-[7-chloro-1-[(3R)-1-(1-methyl-3,6-dihydro-2H-pyridine-5-carbonyl)azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound CN1CCC=C(C1)C(=O)N1CCCC[C@H](C1)n1c(NC(=O)c2ccnc(C)c2)nc2cccc(Cl)c12 QUQHOJKEEPBPLR-OAQYLSRUSA-N 0.000 claims 1
- BDSUUHOITPZXKI-MVHVFESUSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(3,3-difluoroazetidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound c1cnc(C)cc1C(=O)Nc1nc2cccc(Cl)c2n1[C@@H]1CCCCN(C(=O)\C=C\CN2CC(F)(F)C2)C1 BDSUUHOITPZXKI-MVHVFESUSA-N 0.000 claims 1
- CLFJEZPQICJJGR-OAQYLSRUSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(3-methoxyazetidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC1=CC=CC2=C1N(C(=N2)NC(=O)C2=CC(=NC=C2)C)[C@H]2CN(CCCC2)C(C=CCN2CC(C2)OC)=O CLFJEZPQICJJGR-OAQYLSRUSA-N 0.000 claims 1
- UFACVKOFSXJDSC-AEVNEEFTSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(cyclopropylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound c1cnc(C)cc1C(=O)Nc1nc2cccc(Cl)c2n1[C@@H]1CCCCN(C(=O)\C=C\CNC2CC2)C1 UFACVKOFSXJDSC-AEVNEEFTSA-N 0.000 claims 1
- CRDFVOTYNXFDQN-FHVRUZERSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-6-methoxybenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound c12c(Cl)c(OC)ccc2nc(NC(=O)c2cc(C)ncc2)n1[C@H]1CN(C(=O)\C=C\CN(C)C)CCCC1 CRDFVOTYNXFDQN-FHVRUZERSA-N 0.000 claims 1
- DBJRDZVCSVJNRC-JHTBKMLMSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-6-methoxybenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound c12c(Cl)c(OC)ccc2nc(NC(=O)c2cnncc2)n1[C@H]1CN(C(=O)\C=C\CN(C)C)CCCC1 DBJRDZVCSVJNRC-JHTBKMLMSA-N 0.000 claims 1
- RWFZOCMKERWXEI-XYJBSGBBSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-dimethylphosphoryl-6-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1n1c(NC(=O)c2cc(C)nc(c2)P(C)(C)=O)nc2cccc(Cl)c12 RWFZOCMKERWXEI-XYJBSGBBSA-N 0.000 claims 1
- VWWHXDGCALREQG-GPVYEGESSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-dimethylphosphorylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1n1c(NC(=O)c2ccnc(c2)P(C)(C)=O)nc2cccc(Cl)c12 VWWHXDGCALREQG-GPVYEGESSA-N 0.000 claims 1
- OUTZPQYRZCOSPM-WGLAMXGCSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1n1c(NC(=O)c2ccnnc2)nc2cccc(Cl)c12 OUTZPQYRZCOSPM-WGLAMXGCSA-N 0.000 claims 1
- MHPJPOLMCIELFS-WUTDNEBXSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-(methylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CNC)CCCC[C@H]1n1c(NC(=O)c2cc(C)nc(C)c2)nc2cccc(Cl)c12 MHPJPOLMCIELFS-WUTDNEBXSA-N 0.000 claims 1
- QGLHPLZXXVMLMK-VMLCMGRWSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-[(1-methylcyclopropyl)amino]but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound c1cnc(C)cc1C(=O)Nc1nc2cccc(Cl)c2n1[C@@H]1CCCCN(C(=O)\C=C\CNC2(C)CC2)C1 QGLHPLZXXVMLMK-VMLCMGRWSA-N 0.000 claims 1
- KRTVHCKDMWKKDG-WOJBJXKFSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-[(3R)-3-fluoropyrrolidin-1-yl]but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound ClC1=CC=CC2=C1N(C(=N2)NC(=O)C2=CN=NC=C2)[C@H]2CN(CCCC2)C(C=CCN2C[C@@H](CC2)F)=O KRTVHCKDMWKKDG-WOJBJXKFSA-N 0.000 claims 1
- MYOGKUHDJSGFJS-QAHJZJTHSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-[(3S)-3-hydroxypyrrolidin-1-yl]but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound c1cnc(C)cc1C(=O)Nc1nc2cccc(Cl)c2n1[C@@H]1CCCCN(C(=O)\C=C\CN2CC[C@H](O)C2)C1 MYOGKUHDJSGFJS-QAHJZJTHSA-N 0.000 claims 1
- BOEUTRHRULKMHJ-CLOLKSBNSA-N N-[7-chloro-1-[(3R)-1-[(E)-4-pyrrolidin-1-ylbut-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C([C@@H](CCCC1)n2c(nc3cccc(Cl)c32)NC(=O)c2cnncc2)N1C(=O)\C=C\CN1CCCC1 BOEUTRHRULKMHJ-CLOLKSBNSA-N 0.000 claims 1
- CNYNRRKRUYZSPN-OAQYLSRUSA-N N-[7-chloro-1-[(3R)-1-[4-(3,3-difluoropyrrolidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC1=CC=CC2=C1N(C(=N2)NC(=O)C2=CC(=NC=C2)C)[C@H]2CN(CCCC2)C(C=CCN2CC(CC2)(F)F)=O CNYNRRKRUYZSPN-OAQYLSRUSA-N 0.000 claims 1
- KLIVTQBEOLTVBI-OAQYLSRUSA-N N-[7-chloro-1-[(3R)-1-[4-(3-fluoroazetidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(Cl)c2n1[C@@H]1CCCCN(C1)C(=O)C=CCN1CC(F)C1 KLIVTQBEOLTVBI-OAQYLSRUSA-N 0.000 claims 1
- UPVDHDIMXUMGRO-HXUWFJFHSA-N N-[7-chloro-1-[(3R)-1-[4-(3-hydroxyazetidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(Cl)c2n1[C@@H]1CCCCN(C1)C(=O)C=CCN1CC(O)C1 UPVDHDIMXUMGRO-HXUWFJFHSA-N 0.000 claims 1
- MYOGKUHDJSGFJS-FGZHOGPDSA-N N-[7-chloro-1-[(3R)-1-[4-[(3R)-3-hydroxypyrrolidin-1-yl]but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC1=CC=CC2=C1N(C(=N2)NC(=O)C2=CC(=NC=C2)C)[C@H]2CN(CCCC2)C(C=CCN2C[C@@H](CC2)O)=O MYOGKUHDJSGFJS-FGZHOGPDSA-N 0.000 claims 1
- XWBLXDSMHGSRQO-DHIUTWEWSA-N N-[7-chloro-1-[(3R)-1-[4-[(3R)-3-methoxypyrrolidin-1-yl]but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound CO[C@@H]1CCN(CC=CC(=O)N2CCCC[C@H](C2)n2c(NC(=O)c3ccnc(C)c3)nc3cccc(Cl)c23)C1 XWBLXDSMHGSRQO-DHIUTWEWSA-N 0.000 claims 1
- FIEVDKPXHAPDIU-JOCHJYFZSA-N N-[7-chloro-1-[(3R)-1-prop-2-enoylazepan-3-yl]-6-(2-pyrrolidin-1-ylethoxy)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2ccc(OCCN3CCCC3)c(Cl)c2n1[C@@H]1CCCCN(C1)C(=O)C=C FIEVDKPXHAPDIU-JOCHJYFZSA-N 0.000 claims 1
- DFRYGKYFVIKKJW-QGZVFWFLSA-N N-[7-chloro-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC1=CC=CC2=C1N(C(=N2)NC(=O)C2=CC(=NC=C2)C)[C@H]2CN(CCCC2)C(C=C)=O DFRYGKYFVIKKJW-QGZVFWFLSA-N 0.000 claims 1
- YOIIPCMYRPWPGE-QGZVFWFLSA-N N-[7-chloro-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)c1cccc(c1)C(=O)Nc1nc2cccc(Cl)c2n1[C@@H]1CCCCN(C1)C(=O)C=C YOIIPCMYRPWPGE-QGZVFWFLSA-N 0.000 claims 1
- CSLAFQYBPUOBGG-OAHLLOKOSA-N N-[7-chloro-1-[(3R)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound Clc1cccc2nc(NC(=O)c3ccnnc3)n([C@@H]3CCCCN(C3)C(=O)C=C)c12 CSLAFQYBPUOBGG-OAHLLOKOSA-N 0.000 claims 1
- UQLIJVPLMFPORY-HSRJRILOSA-N N-[7-chloro-1-[(3S)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@@H]1n1c(NC(=O)c2cc(C)nc(C)c2)nc2cccc(Cl)c12 UQLIJVPLMFPORY-HSRJRILOSA-N 0.000 claims 1
- RWFZOCMKERWXEI-TZTLJZABSA-N N-[7-chloro-1-[(3S)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-dimethylphosphoryl-6-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@@H]1n1c(NC(=O)c2cc(C)nc(c2)P(C)(C)=O)nc2cccc(Cl)c12 RWFZOCMKERWXEI-TZTLJZABSA-N 0.000 claims 1
- VWWHXDGCALREQG-MEJUDOHFSA-N N-[7-chloro-1-[(3S)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-dimethylphosphorylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@@H]1n1c(NC(=O)c2ccnc(c2)P(C)(C)=O)nc2cccc(Cl)c12 VWWHXDGCALREQG-MEJUDOHFSA-N 0.000 claims 1
- IOMMMLWIABWRKL-OEMHODTASA-N N-[7-chloro-1-[(3S)-1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@@H]1n1c(NC(=O)c2ccnc(C)c2)nc2cccc(Cl)c12 IOMMMLWIABWRKL-OEMHODTASA-N 0.000 claims 1
- QAXFTPKMOPHUFW-UHFFFAOYSA-N N-[7-chloro-1-[1-(1-methyl-3,6-dihydro-2H-pyridine-4-carbonyl)azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound CN1CCC(=CC1)C(=O)N1CCCCC(C1)n1c(NC(=O)c2ccnc(C)c2)nc2cccc(Cl)c12 QAXFTPKMOPHUFW-UHFFFAOYSA-N 0.000 claims 1
- QUQHOJKEEPBPLR-UHFFFAOYSA-N N-[7-chloro-1-[1-(1-methyl-3,6-dihydro-2H-pyridine-5-carbonyl)azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound CN1CCC=C(C1)C(=O)N1CCCCC(C1)n1c(NC(=O)c2ccnc(C)c2)nc2cccc(Cl)c12 QUQHOJKEEPBPLR-UHFFFAOYSA-N 0.000 claims 1
- GJGPWVYIYZTHOA-UHFFFAOYSA-N N-[7-chloro-1-[1-(4-pyrrolidin-1-ylbut-2-enoyl)azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound Cc1cc(ccn1)C(=O)Nc1nc2cccc(Cl)c2n1C1CCCCN(C1)C(=O)C=CCN1CCCC1 GJGPWVYIYZTHOA-UHFFFAOYSA-N 0.000 claims 1
- BDSUUHOITPZXKI-UHFFFAOYSA-N N-[7-chloro-1-[1-[(E)-4-(3,3-difluoroazetidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC1=CC=CC2=C1N(C(=N2)NC(=O)C2=CC(=NC=C2)C)C2CN(CCCC2)C(C=CCN2CC(C2)(F)F)=O BDSUUHOITPZXKI-UHFFFAOYSA-N 0.000 claims 1
- KRTVHCKDMWKKDG-XBXARRHUSA-N N-[7-chloro-1-[1-[(E)-4-(3-fluoropyrrolidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C1C(F)CCN1C\C=C\C(=O)N1CCCCC(n2c(nc3cccc(Cl)c32)NC(=O)c2ccnnc2)C1 KRTVHCKDMWKKDG-XBXARRHUSA-N 0.000 claims 1
- CLFJEZPQICJJGR-UXBLZVDNSA-N N-[7-chloro-1-[1-[(E)-4-(3-methoxyazetidin-1-yl)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1C(OC)CN1C\C=C\C(=O)N1CCCCC(n2c(nc3cccc(Cl)c32)NC(=O)c2ccnc(C)c2)C1 CLFJEZPQICJJGR-UXBLZVDNSA-N 0.000 claims 1
- CRDFVOTYNXFDQN-UHFFFAOYSA-N N-[7-chloro-1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-6-methoxybenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound ClC1=C(C=CC2=C1N(C(=N2)NC(=O)C2=CC(=NC=C2)C)C2CN(CCCC2)C(C=CCN(C)C)=O)OC CRDFVOTYNXFDQN-UHFFFAOYSA-N 0.000 claims 1
- DBJRDZVCSVJNRC-UHFFFAOYSA-N N-[7-chloro-1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-6-methoxybenzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound ClC1=C(C=CC2=C1N(C(=N2)NC(=O)C2=CN=NC=C2)C2CN(CCCC2)C(C=CCN(C)C)=O)OC DBJRDZVCSVJNRC-UHFFFAOYSA-N 0.000 claims 1
- RWFZOCMKERWXEI-UKTHLTGXSA-N N-[7-chloro-1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-dimethylphosphoryl-6-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2cc(C)nc(c2)P(C)(C)=O)nc2cccc(Cl)c12 RWFZOCMKERWXEI-UKTHLTGXSA-N 0.000 claims 1
- OUTZPQYRZCOSPM-UXBLZVDNSA-N N-[7-chloro-1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1n1c(NC(=O)c2ccnnc2)nc2cccc(Cl)c12 OUTZPQYRZCOSPM-UXBLZVDNSA-N 0.000 claims 1
- BOEUTRHRULKMHJ-UXBLZVDNSA-N N-[7-chloro-1-[1-[(E)-4-pyrrolidin-1-ylbut-2-enoyl]azepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C1C(n2c(nc3cccc(Cl)c32)NC(=O)c2cnncc2)CCCCN1C(=O)\C=C\CN1CCCC1 BOEUTRHRULKMHJ-UXBLZVDNSA-N 0.000 claims 1
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- PNCBXMHNZVNRIP-UHFFFAOYSA-N n-[1-(1-ethenylsulfonylazepan-3-yl)-7-methylbenzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C1CCCN(S(=O)(=O)C=C)CC1N1C=2C(C)=CC=CC=2N=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 PNCBXMHNZVNRIP-UHFFFAOYSA-N 0.000 claims 1
- SKLAQDNYYXAFGK-QWDXWUACSA-N n-[1-[(3r)-1-[(e)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(C)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 SKLAQDNYYXAFGK-QWDXWUACSA-N 0.000 claims 1
- XILZLQGBIXBPPH-YRNVUSSQSA-N n-[1-[1-[(e)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-(trifluoromethyl)pyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1N1C2=C(C)C=CC=C2N=C1NC(=O)C1=CC=NC(C(F)(F)F)=C1 XILZLQGBIXBPPH-YRNVUSSQSA-N 0.000 claims 1
- SKLAQDNYYXAFGK-XYOKQWHBSA-N n-[1-[1-[(e)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]-7-methylbenzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1N1C2=C(C)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 SKLAQDNYYXAFGK-XYOKQWHBSA-N 0.000 claims 1
- CXICEXOWGOQDAE-SFHVURJKSA-N n-[5-methyl-1-[(3s)-1-prop-2-enoylpiperidin-3-yl]benzimidazol-2-yl]-3-(trifluoromethyl)benzamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(=O)NC1=NC2=CC(C)=CC=C2N1[C@H]1CCCN(C(=O)C=C)C1 CXICEXOWGOQDAE-SFHVURJKSA-N 0.000 claims 1
- RJAHJLJPCWTHGE-UHFFFAOYSA-N n-[7-chloro-1-(1-prop-2-enoyl-1,4-diazepan-6-yl)benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=NC(C)=CC(C(=O)NC=2N(C3=C(Cl)C=CC=C3N=2)C2CN(CCNC2)C(=O)C=C)=C1 RJAHJLJPCWTHGE-UHFFFAOYSA-N 0.000 claims 1
- MNKAISMGRLQTPA-UHFFFAOYSA-N n-[7-chloro-1-(1-prop-2-enoylazepan-3-yl)-6-(2-pyrrolidin-1-ylethoxy)benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound CC1=NC(C)=CC(C(=O)NC=2N(C3=C(Cl)C(OCCN4CCCC4)=CC=C3N=2)C2CN(CCCC2)C(=O)C=C)=C1 MNKAISMGRLQTPA-UHFFFAOYSA-N 0.000 claims 1
- CMGSCQBXDPYNGB-ZHMUPQBKSA-N n-[7-chloro-1-[(3r)-1-[(e)-4-(dicyclopropylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=NC(C)=CC(C(=O)NC=2N(C3=C(Cl)C=CC=C3N=2)[C@H]2CN(CCCC2)C(=O)\C=C\CN(C2CC2)C2CC2)=C1 CMGSCQBXDPYNGB-ZHMUPQBKSA-N 0.000 claims 1
- GJGPWVYIYZTHOA-ICKBMGCOSA-N n-[7-chloro-1-[(3r)-1-[(e)-4-pyrrolidin-1-ylbut-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1=NC(C)=CC(C(=O)NC=2N(C3=C(Cl)C=CC=C3N=2)[C@H]2CN(CCCC2)C(=O)\C=C\CN2CCCC2)=C1 GJGPWVYIYZTHOA-ICKBMGCOSA-N 0.000 claims 1
- UQLIJVPLMFPORY-XYOKQWHBSA-N n-[7-chloro-1-[1-[(e)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2,6-dimethylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC(C)=NC(C)=C1 UQLIJVPLMFPORY-XYOKQWHBSA-N 0.000 claims 1
- IOMMMLWIABWRKL-YRNVUSSQSA-N n-[7-chloro-1-[1-[(e)-4-(dimethylamino)but-2-enoyl]azepan-3-yl]benzimidazol-2-yl]-2-methylpyridine-4-carboxamide Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCCC1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-YRNVUSSQSA-N 0.000 claims 1
- QEDYHISEDZQKOR-UHFFFAOYSA-N n-[7-chloro-6-methoxy-1-(1-prop-2-enoylazepan-3-yl)benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound C1CCCN(C(=O)C=C)CC1N1C2=C(Cl)C(OC)=CC=C2N=C1NC(=O)C1=CC=NN=C1 QEDYHISEDZQKOR-UHFFFAOYSA-N 0.000 claims 1
- QEDYHISEDZQKOR-OAHLLOKOSA-N n-[7-chloro-6-methoxy-1-[(3r)-1-prop-2-enoylazepan-3-yl]benzimidazol-2-yl]pyridazine-4-carboxamide Chemical compound N1([C@H]2CN(CCCC2)C(=O)C=C)C2=C(Cl)C(OC)=CC=C2N=C1NC(=O)C1=CC=NN=C1 QEDYHISEDZQKOR-OAHLLOKOSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- PBBSNONCFLLRFE-SNMYMPMCSA-N tert-butyl N-[(E)-4-[(3R)-3-[7-chloro-2-[(2-methylpyridine-4-carbonyl)amino]benzimidazol-1-yl]azepan-1-yl]-4-oxobut-2-enyl]-N-methylcarbamate Chemical compound C1N(C(=O)/C=C/CN(C)C(=O)OC(C)(C)C)CCCC[C@H]1n1c(NC(=O)c2ccnc(C)c2)nc2cccc(Cl)c12 PBBSNONCFLLRFE-SNMYMPMCSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
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- A61K31/4164—1,3-Diazoles
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
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- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Claims (26)
1. Spoj, naznačen time, da ima sljedeću Formulu (1), ili njegov tautomer:
[image]
(1)
u kojoj Prsten A je 6-10-člani monociklički ili biciklički aril; 5-10-člani heteroaril koji sadrži 1-4 heteroatoma odabrana od N, O i S; ili 4-12-člani monociklički ili biciklički heterociklil koji sadrži 1-4 heteroatoma odabrana od N, O i S, i prema potrebi supstituiran s okso;
Prsten B je fenil; 5-6 -člani heteroaril koji sadrži 1-3 heteroatoma odabrana od N, O i S; ili 5-6-člani heterociklil koji sadrži 1-2 heteroatoma odabrana od N, O i S, i prema potrebi supstituiran s okso;
E je NH ili CH2;
R1 i R1’ su neovisno vodik; halo; cijano; C1-6 alkil; C1-6 haloalkil; 5-6-člani heteroaril koji sadrži 1-4 heteroatoma odabrana od N, O i S; fenil, 5-6-člani heterociklil koji sadrži 1-2 heteroatoma odabrana od N, O, S i P, i prema potrebi supstituiran s okso;
- X1-C(O)OR3; -X1-O-C(O)R3; -X1-C(O)R3; -X1-C(O)NR4R5; -X1-C(O)NR4-X3-C(O)OR3;
-X1-C(O)NR4-X3-S(O)0-2 R6; -X1-NR4R5; -X1NR4-X2-C(O)R3; -X1-NR4-X2-C(O)OR3;
-X1-NR4-X2-C(O)NR4R5; -X1-NR4-X3-S(O)0-2R6; -X1-NR4S(O)2R6; -X1-OS(O)2R6;
-X1-OR3; -X1-O-X4-OR3; -X1-O-X4-S(O)0-2R6; -X1-O-X4-NR4R5; -X1-S(O)0-2R6;
-X1-S(O)0-2-X3-NR4R5; -X1-C(O)NR4-X3-P(O)R6aR6b; -X1-NR4-X1-P(O)R6aR6b;
-X1-O-X1-P(O)R6aR6b; -X1-P(O)R6a-X1-NR4R5; -X1-P(O)R6aR6b ili -X1-S(O)2NR4R5;
pri čemu je svaki fenil, heteroaril ili heterociklil u R2, nesupstituiran ili supstituiran s 1-3 skupine odabrane od OH, halo, C1-6 alkil, C1-6 haloalkil i C1-6 haloalkoksi;
R2 je odabran od sljedećih: vodik; halo; cijano; C1-6 alkil; C1-6 haloalkil; 5-6-člani heteroaril koji sadrži 1-4 heteroatoma odabrana od N, O i S; fenil, 5-6-člani heterociklil koji sadrži 1-2 heteroatoma odabrana od N, O, S i P, i prema potrebi supstituiran s okso;
- X1-C(O)OR3; -X1-O-C(O)R3; -X1-C(O)R3; -X1-C(O)NR4R5; -X1-C(O)NR4-X3-C(O)OR3;
-X1-C(O)NR4-X3-S(O)0-2 R6; -X1-NR4R5; -X1NR4-X2-C(O)R3; -X1-NR4-X2-C(O)OR3;
-X1-NR4-X2-C(O)NR4R5; -X1-NR4-X3-S(O)0-2R6; -X1-NR4S(O)2R6; -X1-OS(O)2R6;
-X1-OR3; -X1-O-X4-OR3; -X1-O-X4-S(O)0-2R6; -X1-O-X4-NR4R5; -X1-S(O)0-2R6;
-X1-S(O)0-2-X3-NR4R5; -X1-C(O)NR4-X3-P(O)R6aR6b; -X1-NR4-X1-P(O)R6aR6b;
-X1-O-X1-P(O)R6aR6b; -X1-P(O)R6a-X1-NR4R5; -X1-P(O)R6aR6b, -X1-S(O)2NR4R5 i
((4-acetilpiperazin-1-il)metil); pri čemu je svaki fenil, heteroaril ili heterociklil u R2, nesupstituiran ili supstituiran s 1-3-skupine odabrane od OH, halo, C1-6 alkil, C1-6 haloalkil i C1-6 haloalkoksi;
R3, R4 i R5 su neovisno vodik, C1-6 alkil ili C1-6 haloalkil; ili gdje R4 i R5 zajedno s N u NR4R5, mogu tvoriti 4-7-člani Prsten koji sadrži 1-2 heteroatoma odabrana od N, O, S i P, i prema potrebi supstituiran s 1-4 od R7-skupine;
R6 je C1-6 alkil ili C1-6 haloalkil;
R6a i R6b su neovisno hidroksi, C1-6 alkil, C1-6 haloalkil, C1-6 alkoksi, C1-6 haloalkoksi,
6-10-člani monociklički ili biciklički aril; 5-10-člani heteroaril koji sadrži 1-4 heteroatoma odabrana od N, O i S; ili 4-12-člani monociklički ili biciklički heterociklil koji sadrži 1-4 heteroatoma odabrana od N, O i S, i prema potrebi supstituiran s okso;
Z je:
[image]
ili
[image]
gdje Y je O ili NR19;
R8 je:
[image]
[image]
ili
R9 i R10 su neovisno vodik, halo, C1-6 alkil, C1-6 haloalkil, OH, cijano, C1-6 alkoksi,
C1-6 haloalkoksi;
R11a, R11b, R11c, R11d, R11e, R11f, R11g, R11h, R11i, R11j, R11k i R11l su neovisno vodik,
C1-6 alkil ili C1-6 haloalkil;
R12 i R13 su neovisno vodik, halo, cijano, C1-6 alkil ili C1-6 haloalkil;
R14 i R15 su neovisno vodik, C1-6 alkil, -L1-R23, -(CRaRb)2-3-Rc ili -L2-Rd; ili
R14 i R15 zajedno s N u NR14R15, mogu tvoriti 4-7-člani Prsten koji sadrži 1-2 heteroatoma odabrana od N, O, S i P, i prema potrebi supstituiran s 1-4 od R18-skupine;
R16 i R17 su neovisno vodik ili C1-6 alkil; ili R16 i R17 zajedno s ugljikom na kojega su priključeni, mogu tvoriti C3-6 cikloalkil;
X1 i X2 su neovisno veza ili C1-6 alkil;
X3 je C1-6 alkil;
X4 je C2-6 alkil;
R19 vodik, C1-6 alkil, COR20, COOR20, CONR20R21 ili S(O)2R20;
R20 je C1-6 alkil, C1-6 haloalkil ili cikloalkil;
R21 je vodik ili C1-6 alkil; ili R20 i R21 zajedno s N u NR20R21, mogu tvoriti 4-7-člani Prsten koji sadrži 1-2 heteroatoma odabrana od N, O, S i P, i prema potrebi supstituiran s 1-4 od R22-skupine;
R7, R18 i R22 su neovisno okso, halo, hidroksi, C1-6 alkil, C1-6 haloalkil, C1-6 alkoksi ili C1-6 haloalkoksi;
R23 je neovisno C3-7 cikloalkil, ili 4-10-člani heterociklil koji sadrži 1-3 heteroatoma odabrana od N, O i S, i prema potrebi je supstituiran s okso; i
R23 je nesupstituiran ili supstituiran sa sljedećima: C1-6 alkil, C1-6 haloalkil, -L3-Re ili -L4-Rf;
Rc i Re su neovisno halo, cijano, hidroksi, -OR24, -NRR25, -NR-CO2R24, -NR-SO2-R26,
-NR-COR26, -NR-C(O)-NRR25, -OC(O)-NRR25 ili C1-6 alkil supstituiran s halo, C1-6 alkoksi, hidroksi ili cijano;
Rd i Rf su neovisno -SO2NRR25, -CONRR25, -C(O)OR24, -SO2R26 ili C(O)R26;
R24 je C1-6 alkil, C1-6haloalkil, -L2-R23a ili -(CRaRb)2-3-N(RaRb)2;
R25 je vodik, C1-6 alkil, C1-6haloalkil, -L2-R23b ili -(CR2)2-3-N(RaRb)2;
R26 je C1-6 alkil, C1-6haloalkil, -L2-R23c ili -(CRaRb)1-3-N(RaRb)2;
R23a, R23b i R23c su neovisno odabrani od R23;
R, Ra i Rb su neovisno vodik ili C1-6 alkil;
L1, L2, L3 i L4 su neovisno veza ili -(CRaRb)1-3; i
n i m su neovisno 1-3; i p i q su 1-4;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da navedeni spoj ima sljedeću Formulu (2):
[image]
(2)
u kojoj Prsten A je 6-10-člani monociklički ili biciklički aril; 5-10-člani heteroaril koji sadrži 1-4 heteroatoma odabrana od N, O i S; ili 5-6-člani heterociklil koji sadrži 1-2 heteroatoma odabrana od N, O i S, i prema potrebi supstituiran s okso;
R1 i R1’ su neovisno vodik; halo; cijano; C1-6 alkil; C1-6 haloalkil; -X1-NR4R5; -X1-OR3;
-X1-S(O)0-2R6; -X1-P(O)R6aR6b; fenil nesupstituiran ili supstituiran sa C1-6 alkilom; ili
5-6-člani heteroaril koji sadrži 1-4 heteroatoma odabrana od N, O i S;
R2 je odabran od sljedećih: vodik, halo; cijano; C1-6 alkil; C1-6 haloalkil; -X1-C(O)OR3; -X1-C(O)R3; -X1-C(O)NR4R5; -X1-C(O)NR4-X3-C(O)OR3; -X1-C(O)NR4-X3-S(O)0-2R6; -X1-NR4R5;
-X1NR4-X2-C(O)R3; -X1-NR4-X3-S(O)0-2R6; -X1-OR3; -X1-O-X4-OR3; -X1-S(O)0-2R6;
-X1-O-X4-NR4R5; ili 5-6-člani heteroaril koji sadrži 1-4 heteroatoma odabrana od N, O i S, te je nesupstituiran ili supstituiran sa C1-6 alkilom;
R3, R4 i R5 su neovisno vodik, C1-6 alkil ili C1-6 haloalkil; ili gdje R4 i R5 zajedno s N u NR4R5, mogu tvoriti 4-7-člani Prsten koji sadrži 1-2 heteroatoma odabrana od N, O, S i P, i prema potrebi supstituiran s 1-4 od R7-skupine;
R6, R6a i R6b su C1-6 alkil;
Z je:
[image]
ili
[image]
;
uz uvjet da Z je 4-7-člani heterociklički prsten, kada Z je:
[image]
;
Y je O ili NR19;
R8 je:
[image]
[image]
ili
R9, R10, R11a, R11b, R11c, R11d, R11e, R11f, R11g, R11h, R11i, R11j, R11k i R11l su vodik;
R12, R13, R16 i R17 su neovisno vodik ili C1-6 alkil;
R14 i R15 su neovisno vodik; C1-6 alkil; -C(O)O-(C1-6 alkil); C3-7 cikloalkil nesupstituiran ili supstituiran sa C1-6 alkilom; ili
R14 i R15 zajedno s N u NR14R15, mogu tvoriti 4-7-člani Prsten koji sadrži 1-2 heteroatoma odabrana od N, O, S i P, i prema potrebi supstituiran s 1-4 od R18-skupine;
R7 i R18 su neovisno okso, halo, hidroksi, C1-6 alkil ili C1-6 alkoksi;
R19 je vodik, COR20 ili COOR20;
R20 je C1-6 alkil;
p je 1;
m i q su neovisno 1-2; i
Prsten B, X1, X2, X3 i X4 i n su isti kao što su definirani u zahtjevu 1.
3. Spoj prema zahtjevu 1 ili 2, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da navedeni spoj ima sljedeće Formule (2A), (2B), (2C), (2D), (3A), (3B) ili (3C):
[image]
(2A)
[image]
(2B)
[image]
(2C)
[image]
(2D)
[image]
(3A)
[image]
(3B)
[image]
(3C).
4. Spoj prema bilo kojem od zahtjeva 1-3, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da Prsten B zajedno s atomima na koje je priključen, tvori fuzionirani fenil, piridil ili piperidil, od kojih je svaki nesupstituiran ili supstituiran s (R2)m; i m i R2 su isti kao što su definirani u zahtjevu 1 ili 2.
5. Spoj prema bilo kojem od zahtjeva 1-4, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da:
Prsten A je fenil, piridil, pirimidinil, piridazinil, pirazinil, piridin-2-onil, oksazolil, furanil, tiazolil, imidazol[2,1-b]tiazolil, imidazo[1,2-a]piridinil, imidazo[1,5-a]piridinil ili naftil, od kojih je svaki nesupstituiran ili supstituiran s (R1)n i R1’;
R1, R1’ i n su isti kao što su definirani u zahtjevu 1 ili 2.
6. Spoj prema bilo kojem od zahtjeva 1-5, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da navedeni spoj ima sljedeću Formulu (4):
[image]
(4)
u kojoj su W1, W2, W3 i W4 neovisno CR1 ili N; i
R1, R1’, R2, R8, Y i m su isti kao što su definirani u zahtjevu 1 ili 2.
7. Spoj prema bilo kojem od zahtjeva 1-5, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da navedeni spoj ima sljedeću Formulu (5):
[image]
(5)
u kojoj su W1 i W2 neovisno CR1 ili N; i
R1, R1’, R2, R8 i m su isti kao što su definirani u zahtjevu 1 ili 2.
8. Spoj prema bilo kojem od zahtjeva 1-7, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da su R1 i R1’ neovisno vodik; halo; cijano; C1-6 alkil; C1-6 haloalkil;
-X1-NR4R5; -X1-OR3; -X1-S(O)0-2R6; fenil nesupstituiran ili supstituiran sa C1-6 alkilom; tetrazolil ili pirolil;
svaki X1 je veza ili CH2;
R3, R4 i R5 su neovisno vodik, C1-6 alkil ili C1-6 haloalkil; ili
gdje R4 i R5 zajedno s N u NR4R5, tvore piperidinil; i
R6 je isti kao što je definiran u zahtjevu 1 ili 2.
9. Spoj prema bilo kojem od zahtjeva 1-7, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da R1 je vodik, halo, cijano, C1-6 alkil, C1-6 haloalkil, tetrazolil, pirolil,
-X1-NR4R5, -X1-OR3, -X1-S(O)0-2R6 ili fenil nesupstituiran ili supstituiran sa C1-6 alkilom;
R1’ je vodik, halo ili C1-6 alkil;
R3, R4 i R5 su neovisno vodik, C1-6 alkil ili C1-6 haloalkil; ili
gdje R4 i R5 zajedno s N u NR4R5, tvore piperidinil;
X1 je veza ili CH2; i
R6 je isti kao što je definiran u zahtjevu 1 ili 2.
10. Spoj prema bilo kojem od zahtjeva 1-7 ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da su R1 i R1’ neovisno vodik; metil; t-butil; trifluorometil; metoksi; etoksi; trifluorometoksi; difluorometoksi; fluoro; kloro; cijano; dimetilamino; metilsulfonil; dimetilfosforil; tetrazolil; pirolil; fenil nesupstituiran ili supstituiran s metilom; ili piperidinil.
11. Spoj prema bilo kojem od zahtjeva 1-10, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da:
R2 je vodik; kloro; metil; trifluorometil; metoksi; izoproproksi; cijano; hidroksimetil; metoksimetil; etoksimetil; metilsulfonil; metilkarbonil; karboksi; metoksikarbonil; karbamoil; dimetilaminometil; pirolidinilmetil nesupstituiran ili supstituiran s 1-2 hidroksi, halo ili metoksi; morfolinometil; azeditinilmetil nesupstituiran ili supstituiran s 1-2 halo ili metoksi; piperidinilmetil; ((4-metil-3-okso-piperazin-1-il)metil); ((4-acetilpiperazin-1-il)metil); (1,1-dioksidotiomorfolin-4-karbonil); pirolidinilkarbonil nesupstituiran ili supstituiran s 1-2 hidroksi; pirolidiniletoksi;
(1,1-dioksidotiomorfolino)metil; ili 1,2,4-oksadiazolil nesupstituiran ili supstituiran sa
C1-6 alkilom;
alternativno, R2 je -CH2-N(CH3)-C(O)-CH3; -CH2-O-(CH2)2-OCH3;
-CH2-N(CH3)-(CH2)2-SO2(CH3); -C(O)NH-(CH2)1-2-C(O)-OCH3; -C(O)NH-(CH2)1-2-C(O)OH; ili
-C(O)NH-(CH2)2-SO2(CH3).
12. Spoj prema bilo kojem od zahtjeva 1-11, ili njegova farmaceutski prihvatljiva sol,
naznačen/a time, da R8 je:
[image]
[image]
[image]
ili
[image]
;
gdje su R14 i R15 neovisno vodik, C1-6 alkil ili C3-7 cikloalkil; ili R14 i R15 zajedno s N u NR14R15, mogu tvoriti azetidinil, piperidil, pirolidinil ili morfolinil;
pri čemu navedeni azetidinil ili pirolidinil, može biti prema potrebi supstituiran s
1-2 halo, metoksi ili hidroksila; i
R12, R13, R16, R17 i q su isti kao što su definirani u zahtjevu 1 ili 2.
13. Spoj prema bilo kojem od zahtjeva 1-12, ili njegova farmaceutski prihvatljiva sol, naznačen/a time, da je navedeni spoj odabran od sljedećih:
N-{7-kloro-1-[(3R)-1-[4-(pirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[-[4-(pirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[4-(3-fluoroazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[-[4-(3-fluoroazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-{4-[(3R)-3-fluoropirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[-{4-[3-fluoropirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-{4-[(3S)-3-fluoropirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[4-(3,3-difluoropirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-[4-(3,3-difluoropirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-{4-[(3R)-3-metoksipirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-{4-[3-metoksipirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-{4-[(3S)-3-metoksipirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-{4-[(3R)-3-hidroksipirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[-{4-[3-hidroksipirolidin-1-il]but-2-enoil}azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-[(3S)-3-hidroksipirolidin-1-il]but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[-[(2E)-4-[3-hidroksipirolidin-1-il]but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(pirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(pirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
2-metil-N-{7-metil-1-[(3R)-1-[(2E)-4-(pirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2-metil-N-{7-metil-1-[1-[(2E)-4-(pirolidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-[(3R)-3-fluoropirolidin-1-il]but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[(2E)-4-[3-fluoropirolidin-1-il]but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-[(3R)-3-fluoropirolidin-1-il]but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-[3-fluoropirolidin-1-il]but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-[4-(azetidin-1-il)but-2-enoil]azepan-3-il]-7-kloro-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[4-(azetidin-1-il)but-2-enoil]azepan-3-il]-7-kloro-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[4-(3-hidroksiazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-[4-(3-hidroksiazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(3-metoksiazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(3-metoksiazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(3,3-difluoroazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(3,3-difluoroazetidin-1-il)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{5-metil-1-[(3S)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-1-[-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-(trifluorometil)piridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-(trifluorometil)piridin-4-karboksamid;
N-{7-kloro-6-metoksi-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-6-metoksi-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-(etensulfonil)azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(etensulfonil)azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[(3R)-1-(prop-2-enoil)azepan-3-il]-7-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(prop-2-enoil)azepan-3-il]-7-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-1-[-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-6-metoksi-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-6-metoksi-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-fluorobenzamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]piperidin-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]piperidin-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-1,3-oksazol-5-karboksamid;
N-{1-[(6R)-4-[(2E)-4-(dimetilamino)but-2-enoil]-1,4-oksazepan-6-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[4-[(2E)-4-(dimetilamino)but-2-enoil]-1,4-oksazepan-6-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[(6S)-4-[(2E)-4-(dimetilamino)but-2-enoil]-1,4-oksazepan-6-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(prop-2-enoil)piperidin-3-il]-1H-imidazo[4,5-c]piridin-2-il}-3-(trifluorometil)benzamid;
N-{3-[1-(prop-2-enoil)piperidin-3-il]-3H-imidazo[4,5-c]piridin-2-il}-3-(trifluorometil)benzamid;
N-{7-metil-1-[-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)
benzamid;
N-{7-metil-1-[-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{1-[(3R)-1-(prop-2-enoil)azepan-3-il]-7-(trifluorometil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(prop-2-enoil)azepan-3-il]-7-(trifluorometil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)
benzamid;
N-{7-metil-1-[4-(prop-2-enoil)-1,4-oksazepan-6-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-kloro-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-kloro-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[(3R)-1-(but-2-inoil)azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(but-2-inoil)azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[(3R)-1-[(2E)-but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-[(2E)-but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3-fluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3,5-difluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)piridin-3-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)piridazin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-4-fluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2,3-difluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2,4-difluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2,5-difluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3,4-difluorobenzamid;
3-kloro-N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-fluorobenzamid;
3-kloro-N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2,4-difluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3,4,5-trifluorobenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)piridin-2-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)piridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)pirimidin-2-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)pirimidin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)pirazin-2-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)piridazin-3-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)benzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3-metilbenzamid;
3-cijano-N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)benzamid;
3-kloro-N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)benzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3-metoksibenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-6-metoksipiridin-3-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-6-(trifluorometil)piridin-3-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-6-metilpiridin-3-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-metoksipiridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-1-metil-2-okso-1,2-dihidropiridin-4-karboksamid;
2-(dimetilamino)-N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)piridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)imidazo[2,1-b][1,3]tiazol-6-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3-metansulfonilbenzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-3-(1H-1,2,3,4-tetrazol-1-il)benzamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-metilpirimidin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)imidazo[1,2-a]piridin-6-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)furan-2-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-(piperidin-1-il)piridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-fluoropiridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-4,5-dimetilfuran-2-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-(1H-1,2,3,4-tetrazol-1-il)piridin-4-karboksamid;
2-tert-butil-N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)piridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-metilpiridin-3-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)imidazo[1,5-a]piridin-7-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-metil-1,3-tiazol-5-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)-2-etoksipiridin-4-karboksamid;
N-(1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-7-metil-1H-1,3-benzodiazol-2-il)naftalen-2-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-(trifluorometil)piridin-3-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-(trifluorometil)piridin-3-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-metilpiridin-3-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-metilpiridin-3-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-fluoropiridin-3-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-fluoropiridin-3-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-(1H-pirol-1-il)piridin-3-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-(1H-pirol-1-il)piridin-3-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metoksipiridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metoksipiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
2-kloro-N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2-kloro-N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2-kloro-N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-metilpiridin-4-karboksamid;
2-kloro-N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-metilpiridin-4-karboksamid;
2-kloro-N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-metoksipiridin-4-karboksamid;
2-kloro-N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-metoksipiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-fenilpiridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-fenilpiridin-4-karboksamid;
6-kloro-N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-3-karboksamid;
6-kloro-N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-3-karboksamid;
5,6-dikloro-N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-3-karboksamid;
5,6-dikloro-N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-3-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-metoksipiridin-3-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-5-metoksipiridin-3-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-(2-metilfenil)piridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-(2-metilfenil)piridin-4-karboksamid;
6-metil-N-{7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
6-metil-N-{7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-metilpiridazin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-metilpiridazin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metoksi-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metoksi-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metoksi-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metoksi-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-(propan-2-iloksi)-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-(propan-2-iloksi)-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-(prop-2-enoil)azepan-3-il]-7-(propan-2-iloksi)-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[1-(prop-2-enoil)azepan-3-il]-7-(propan-2-iloksi)-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-[4-(dimetilamino)but-2-inoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[1-[4-(dimetilamino)but-2-inoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
(R)-N-(7-metil-1-(1-(2-metil-4,4-dioksido-5,6-dihidro-1,4-oksatidin-3-karbonil)azepan-3-il)-1H-benzo[d]imidazol-2-il)piridazin-4-karboksamid;
N-(7-metil-1-(1-(2-metil-4,4-dioksido-5,6-dihidro-1,4-oksatidin-3-karbonil)azepan-3-il)-1H-benzo[d]imidazol-2-il)piridazin-4-karboksamid;
N-{1-[(3R)-1-[(5,6-dihidro-1,4-dioksin-2-il)karbonil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[1-[(5,6-dihidro-1,4-dioksin-2-il)karbonil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[(3R)-1-[2-(piperidin-1-ilmetil)prop-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[1-[2-(piperidin-1-ilmetil)prop-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[(3R)-1-[2-(pirolidin-1-ilmetil)prop-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[1-[2-(pirolidin-1-ilmetil)prop-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-{2-[(dietilamino)metil]prop-2-enoil}azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[1-{2-[(dietilamino)metil]prop-2-enoil}azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[(3R)-1-[2-(morfolin-4-ilmetil)prop-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[1-[2-(morfolin-4-ilmetil)prop-2-enoil]azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{7-metil-1-[-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
metil-1-[1-(prop-2-enoil)azepan-3-il]-2-{[3-(trifuorometil)benzen]amido}-1H-1,3-benzodiazol-7-karboksilat;
N-{5-metil-1-[1-(prop-2-enoil)piperidin-4-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-1-[1-(prop-2-enoil)pirolidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-1-[1-(prop-2-enoil)azetidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(but-2-enoil)azetidin-3-il]-5-metil-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-(trifluorometoksi)piridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-(trifluorometoksi)piridin-4-karboksamid;
2-(difluorometoksi)-N-{1-[(3R)-1-[4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2-(difluorometoksi)-N-{1-[1-[4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2-kloro-N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-(trifluorometoksi)piridin-4-karboksamid;
2-kloro-N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-6-(trifluorometoksi)piridin-4-karboksamid;
N-{5-metil-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-metil-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-metil-1-[-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-1-[-(prop-2-enoil)azepan-4-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-metil-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{7-metil-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
2-metil-N-{7-metil-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2-metil-N-{7-metil-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
metil-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-2-{[3-(trifluorometil)benzen]amido}-1H-1,3-benzodiazol-5-karboksilat;
metil-1-[1-(prop-2-enoil)piperidin-3-il]-2-{[3-(trifluorometil)benzen]amido}-1H-1,3-benzodiazol-5-karboksilat;
N-{7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}benzamid;
N-{7-metil-1-[1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}benzamid;
N-[5-(morfolin-4-ilmetil)-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-[5-(morfolin-4-ilmetil)-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
2,6-dimetil-N-{7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2,6-dimetil-N-{7-metil-1-[1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
N-{7-[(3-hidroksipirolidin-1-il)metil]-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{7-[(3-hidroksipirolidin-1-il)metil]-1-[-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-(1-(1-akriloilazepan-3-il)-7-(1,1-dioksidotiomorfoline-4-karbonil)-1H-benzo[d]imidazol-2-il)benzamid;
N-(7-cijano-1-{1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il}-5-(hidroksimetil)-1H-1,3-benzodiazol-2-il)-3-(trifluorometil)benzamid;
N-{1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-(prop-2-enoil)piperidin-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-[5-(piperidin-1-ilmetil)-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-[5-(piperidin-1-ilmetil)-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-{5-[(N-metilacetamido)metil]-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-[(N-metilacetamido)metil]-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-(5-{[(3R,4R)-3,4-dihidroksipirolidin-1-il]metil}-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il)-3-(trifluorometil)benzamid;
N-(5-{[3,4-dihidroksipirolidin-1-il]metil}-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il)-3-(trifluorometil)benzamid;
N-[5-(hidroksimetil)-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-[5-(hidroksimetil)-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-[5-(metoksimetil)-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-[5-(metoksimetil)-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-[5-(etoksimetil)-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-[5-(etoksimetil)-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il]-3-(trifluorometil)benzamid;
N-{5-[(2-metoksietoksi)metil]-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-[(2-metoksietoksi)metil]-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-[(3,3-difluoropirolidin-1-il)metil]-1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{5-[(3,3-difluoropirolidin-1-il)metil]-1-[1-(prop-2-enoil)piperidin-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
2-metil-N-{7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
2-metil-N-{7-metil-1-[1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}piridin-4-karboksamid;
N-(5-{[(2-metansulfoniletil)(metil)amino]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)benzamid;
N-(5-{[(2-metansulfoniletil)(metil)amino]metil}-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)benzamid;
N-{5-[(2-metoksietoksi)metil]-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{5-[(2-metoksietoksi)metil]-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{7-[(dimetilamino)metil]-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{7-[(dimetilamino)metil]-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{7-[(2-metoksietoksi)metil]-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-{7-[(2-metoksietoksi)metil]-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}benzamid;
N-[7-(hidroksimetil)-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il]benzamid;
N-[7-(hidroksimetil)-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il]benzamid;
(R)-N-(1-(1-akriloilazepan-3-il)-7-((1,1-dioksidotiomorfolino)metil)-1H-benzo[d]
imidazol-2-il)benzamid;
N-(1-(-akriloilazepan-3-il)-7-((1,1-dioksidotiomorfolino)metil)-1H-benzo[d]imidazol-2-il)benzamid;
N-(7-{[(2-metansulfoniletil)(metil)amino]metil}-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)benzamid;
N-(7-{[(2-metansulfoniletil)(metil)amino]metil}-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)benzamid;
metil-3-({2-benzamido-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-7-il}formamido)propanoat;
metil-2-({2-benzamido-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-7-il} formamido)acetat;
3-({2-benzamido-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-7-il}formamido)propanska kiselina;
2-({2-benzamido-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-7-il}formamido)octena kiselina;
N-[7-(3-metil-1,2,4-oksadiazol-5-il)-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il]benzamid;
1-(1-akriloilazepan-3-il)-2-benzamido-N-(2-(metilsulfonil)etil)-1H-benzo[d]imidazol-7-karboksamid;
N-(7-{[(3R,4R)-3,4-dihidroksipirolidin-1-il]karbonil}-1-[1-(prop-2-enoil)azepan-3-il]-1 H-1,3-benzodiazol-2-il)benzamid;
N-(7-{[3,4-dihidroksipirolidin-1-il]karbonil}-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)benzamid;
N-[7-(3-metil-1,2,4-oksadiazol-5-il)-1-[4-(prop-2-enoil)-1,4-oksazepan-6-il]-1H-1,3-benzodiazol-2-il]benzamid;
N-(1-{4-[(2E)-4-(dimetilamino)but-2-enoil]-1,4-oksazepan-6-il}-7-(3-metil-1,2,4-oksadiazol-5-il)-1H-1,3-benzodiazol-2-il)benzamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]piperidin-3-il]-5-(hidroksimetil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]piperidin-3-il]-5-(hidroksimetil)-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
2-metil-N-[7-metil-5-(piperidin-1-ilmetil)-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il]piridin-4-karboksamid;
2-metil-N-[7-metil-5-(piperidin-1-ilmetil)-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il]piridin-4-karboksamid;
N-[5-(azetidin-1-ilmetil)-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il]-2-metilpiridin-4-karboksamid;
N-[5-(azetidin-1-ilmetil)-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il]-2-metilpiridin-4-karboksamid;
N-(5-{[(3S)-3-hidroksipirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N-(5-{[3-hidroksipirolidin-1-il]metil}-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N-(5-{[(3S)-3-fluoropirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-i1]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N-(5-{[3-fluoropirolidin-1-il]metil}-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N-(5-{[(3R)-3-fluoropirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N-(5-{[(3S)-3-metoksipirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N-(5-{[3-metoksipirolidin-1-il]metil}-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N-(5-{[(3R)-3-metoksipirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2-metilpiridin-4-karboksamid;
N- {5-[(3,3-difluoropirolidin-1-il)metil]-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{5-[(3,3-difluoropirolidin-1-il)metil]-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{5-[(3-fluoroazetidin-1-il)metil]-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{5-[(3-fluoroazetidin-1-il)metil]-7-metil-1-[-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{5-[(3,3-difluoroazetidin-1-il)metil]-7-metil-1-[(3R)-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{5-[(3,3-difluoroazetidin-1-il)metil]-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{5-[(3-metoksiazetidin-1-il)metil]-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il} -2-metilpiridin-4-karboksamid;
N-{5-[(3-metoksiazetidin-1-il)metil]-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
(R)-N-(1-(1-akriloilazepan-3-il)-5-((1,1-dioksidotiomorfolino)metil)-7-metil-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(1-(1-akriloilazepan-3-il)-5-((1,1-dioksidotiomorfolino)metil)-7-metil-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(5-{[(3S)-3-metoksipirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2,6-dimetilpiridin-4-karboksamid;
N-(5-{[3-metoksipirolidin-1-il]metil}-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2,6-dimetilpiridin-4-karboksamid;
N-(5-{[(3R)-3-metoksipirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodia zol-2-il)-2,6-dimetilpiridin-4-karboksamid;
N-(5-{[(3S)-3-fluoropirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2,6-dimetilpiridin-4-karboksamid;
N-(5-{[3-fluoropirolidin-1-il]metil}-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2,6-dimetilpiridin-4-karboksamid;
N-(5-{[(3R)-3-fluoropirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2,6-dimetilpiridin-4-karboksamid;
2,3-difluoro-N-(5-{[(3R)-3-metoksipirolidin-1-il]metil}-7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)benzamid;
2,3-difluoro-N-(5-{[3-metoksipirolidin-1-il]metil}-7-metil-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)benzamid;
6-metil-N-{7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
6-metil-N-{7-metil-1-[1-(prop-2-enoil)azepan-3-il]-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}piridazin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-but-2-enoil]azepan-3-il]-5-{[(3S)-3-metoksipirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{1-[1-[(2E)-but-2-enoil]azepan-3-il]-5-{[3-metoksipirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-but-2-enoil]azepan-3-il]-5-{[(3R)-3-metoksipirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[(2E)-but-2-enoil]azepan-3-il]-5-{[3-metoksipirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-but-2-enoil]azepan-3-il]-7-metil-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[(2E)-but-2-enoil]azepan-3-il]-7-metil-5-(pirolidin-1-ilmetil)-1H-1,3-benzodiazol-2-il}-2-metil-piridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-but-2-enoil]azepan-3-il]-5-{[(3S)-3-fluoropirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{1-[1-[(2E)-but-2-enoil]azepan-3-il]-5-{[3-fluoropirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-but-2-enoil]azepan-3-il]-5-{[(3S)-3-fluoropirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[(2E)-but-2-enoil]azepan-3-il]-5-[3-fluoropirolidin-1-il]metil}-7-metil-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
metil-1-[1-(prop-2-enoil)piperidin-3-il]-2-{[3-(trifluorometil)benzen]amido}-1H,4H,5H,6H,7H-imidazo[4,5-c]piridin-5-karboksilat;
N-{5-metansulfonil-1-[1-(prop-2-enoil)piperidin-3-il]-1H,4H,5H,6H,7H-imidazo[4,5-c]piridin-2-il}-3-(trifluorometil)benzamid;
N-{5-acetil-1-[1-(prop-2-enoil)piperidin-3-il]-1H,4H,5H,6H,7H-imidazo[4,5-c]piridin-2-il}-3-(trifluorometil)benzamid;
metil-3-[1-(prop-2-enoil)piperidin-3-il]-2-{[3-(trifluorometil)benzen]amido}-3H,4H,5H,6H,7H-imidazo[4,5-c]piridin-5-karboksilat;
N-{5-metansulfonil-3-[1-(prop-2-enoil)piperidin-3-il]-3H,4H,5H,6H,7H-imidazo
[4,5-c]piridin-2-il}-3-(trifluorometil)benzamid;
N-{5-acetil-3-[1-(prop-2-enoil)piperidin-3-il]-3H,4H,5H,6H,7H-imidazo[4,5-c]
piridin-2-il}-3-(trifluorometil)benzamid;
N-{5-metil-3-[1-(prop-2-enoil)piperidin-3-il]-3H,4H,5H,6H,7H-imidazo[4,5-c]
piridin-2-il}-3-(trifluorometil)benzamid;
N-{1-[(3R)-1-[(2E)-but-2-enoil]azepan-3-il]-5-{[(3S)-3-metoksipirolidin-1-il]metil}-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-{1-[1-[(2E)-but-2-enoil]azepan-3-il]-5-{[(3S)-3-metoksipirolidin-1-il]metil}-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-(5-{[(3S)-3-metoksipirolidin-1-il]metil}-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2,6-dimetilpiridin-4-karboksamid;
N-(5-{[3-metoksipirolidin-1-il]metil}-1-[1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il)-2,6-dimetilpiridin-4-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metoksi-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metoksi-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-6-metoksi-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{7-kloro-1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-6-metoksi-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{6-kloro-1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-5-metoksi-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{6-kloro-1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-5-metoksi-1H-1,3-benzodiazol-2-il}-2-metilpiridin-4-karboksamid;
N-{6-kloro-1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-5-metoksi-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
N-6-kloro-1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-5-metoksi-1H-1,3-benzodiazol-2-il}-2,6-dimetilpiridin-4-karboksamid;
1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-2-{[3-(trifluorometil)benzen]amido}-1H-1,3-benzodiazol-5-karboksilna kiselina;
1-[1-(prop-2-enoil)piperidin-3-il]-2-{[3-(trifluorometil)benzen]amido}-1H-1,3-benzodiazol-5-karboksilna kiselina;
1-[(3R)-1-(prop-2-enoil)piperidin-3-il]-2-C-[3-(trifluorometil)benzen]-1H-1,3-benzodiazol-2,5-dikarboksamid;
1-[1-(prop-2-enoil)piperidin-3-il]-2-C-[3-(trifluorometil)benzen]-1H-1,3-benzodiazol-2,5-dikarboksamid;
1-[1-(prop-2-enoil)azepan-3-il]-2-{[3-(trifluorometil)benzen]amido}-1H-1,3-benzodiazol-7-karboksilna kiselina;
N-{7-metil-1-[(6R)-4-(prop-2-enoil)-1,4-oksazepan-6-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{7-metil-1-[(6S)-4-(prop-2-enoil)-1,4-oksazepan-6-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid;
N-{1-[(3S)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-(trifluorometil)piridin-4-karboksamid;
N-{1-[(3S)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metil-1,3-tiazol-5-karboksamid;
N-{1-[(3R)-1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metil-1,3-tiazol-5-karboksamid;
N-{1-[1-[(2E)-4-(dimetilamino)but-2-enoil]azepan-3-il]-7-metil-1H-1,3-benzodiazol-2-il}-2-metil-1,3-tiazol-5-karboksamid;
N-{7-metil-1-[(3S)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid; i
N-{7-metil-1-[(3R)-1-(prop-2-enoil)azepan-3-il]-1H-1,3-benzodiazol-2-il}-3-(trifluorometil)benzamid; ili njegova farmaceutski prihvatljiva sol.
(R)-N-(7-kloro-1-(1-(1-metil-1,2,5,6-tetrahidropiridin-3-karbonil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(N-(7-kloro-1-(1-(1-metil-1,2,5,6-tetrahidropiridin-3-karbonil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(R)-N-(7-kloro-1-(1-(1-metil-1,2,3,6-tetrahidropiridin-4-karbonil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(7-kloro-1-(1-(1-metil-1,2,3,6-tetrahidropiridin-4-karbonil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(R,E)-N-(7-kloro-1-(1-(4-(dimetilamino)-4-metilpent-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(7-kloro-1-(1-(4-(dimetilamino)-4-metilpent-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
tert-butil-4-akriloil-6-(7-kloro-2-(2-metilizonikotinamido)-1H-benzo[d]imidazol-1-
il)-1,4-diazepan-1-karboksilat;
N-(1-(1-akriloil-1,4-diazepan-6-il)-7-kloro-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(1-(1-acetil-4-akriloil-1,4-diazepan-6-il)-7-kloro-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(R)-N-(1-(1-akriloilazepan-3-i1)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
N-(1-(1-akriloilazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
(R,E)-N-(7-kloro-1-(1-(4-(diciklopropilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]
imidazol-2-il)-2-metilizonikotinamid;
N-(7-kloro-1-(1-(4-(diciklopropilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]
imidazol-2-il)-2-metilizonikotinamid;
(R)-N-(1-(1-akriloilazepan-3-il)-7-metil-5-((4-metil-3-oksopiperazin-1-il)metil)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
N-(1-(1-akriloilazepan-3-il)-7-metil-5-((4-metil-3-oksopiperazin-1-il)metil)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
(R)-N-(5-((4-acetilpiperazin-1-il)metil)-1-(1-akriloilazepan-3-il)-7-metil-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
N-(5-((4-acetilpiperazin-1-il)metil)-1-(1-akriloilazepan-3-il)-7-metil-1H-benzo[d]
imidazol-2-il)-2,6-dimetilizonikotinamid;
(E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]
imidazol-2-il)-2-(dimetilfosforil)-6-metilizonikotinamid;
N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-(dimetilfosforil)-6-metilizonikotinamid;
(R,E)-tert-butil-4-(3-(7-kloro-2-(2-metilizonikotinamido)-1H-benzo[d]imidazol-1-il)azepan-1-il)-4-oksobut-2-enil(metil)karbamat;
tert-butil-4-(3-(7-kloro-2-(2-metilizonikotinamido)-1H-benzo[d]imidazol-1-il)azepan-1-il)-4-oksobut-2-enil(metil)karbamat;
(R,E)-N-(7-kloro-1-(1-(4-(metilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(7-kloro-1-(1-(4-(metilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(R,E)-N-(7-kloro-1-(1-(4-(metilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]
imidazol-2-il)-2,6-dimetilizonikotinamid;
N-(7-kloro-1-(1-(4-(metilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
(R,E)-N-(1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-7-(trifluorometil)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-7-(trifluorometil)-1H-benzo[d]imidazol-2-il)-2-metil-izonikotinamid;
(R,E)-N-(1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-7-(trifluorometil)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
N-(1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-7-(trifluorometil)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
(R,E)-N-(7-kloro-1-(1-(4-(ciklopropilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(7-kloro-1-(1-(4-(ciklopropilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(R,E)-N-(1-(1-(4-(tert-butilamino)but-2-enoil)azepan-3-il)-7-kloro-1H-benzo[d]
imidazol-2-il)-2-metilizonikotinamid;
N-(1-(1-(4-(tert-butilamino)but-2-enoil)azepan-3-il)-7-kloro-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(R,E)-N-(7-kloro-1-(1-(4-(1-metilciklopropilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(7-kloro-1-(1-(4-(1-metilciklopropilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(R)-N-(1-(1-akriloilazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]imidazol-2-il)-2-metil-izonikotinamid;
N-(1-(1-akriloilazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]
imidazol-2-il)-2-metilizonikotinamid;
(R,E)-N-(1-(1-but-2-enoilazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
N-(1-(1-but-2-enoilazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]imidazol-2-il)-2-metil-izonikotinamid;
(R,E)-N-(1-(1-but-2-enoilazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
N-(1-(1-but-2-enoilazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]
imidazol-2-il)-2,6-dimetilizonikotinamid;
(S,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]
imidazol-2-il)-2-metilizonikotinamid;
N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid;
(S,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]
imidazol-2-il)-2,6-dimetilizonikotinamid;
N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid;
(S,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-(dimetilfosforil)-6-metilizonikotinamid;
(R,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-(dimetilfosforil)-6-metilizonikotinamid;
(S,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]
imidazol-2-il)-2-(dimetilfosforil)izonikotinamid;N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-(dimetilfosforil)izonikotinamid; i
(R,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-(dimetilfosforil)izonikotinamid;
ili njegova farmaceutski prihvatljiva sol.
14. Spoj prema zahtjevu 1, naznačen time, da navedeni spoj je (R,E)-N-(7-kloro-1-(1-(4-(pirolidin-1-il)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid, ili njegova farmaceutski prihvatljiva sol.
15. Spoj prema zahtjevu 1, naznačen time, da navedeni spoj je (R,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid, ili njegova farmaceutski prihvatljiva sol.
16. Spoj prema zahtjevu 1, naznačen time, da navedeni spoj je (R,E)-N-(7-kloro-1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid, ili njegova farmaceutski prihvatljiva sol.
17. Spoj prema zahtjevu 1, naznačen time, da navedeni spoj je (R,E)-N-(1-(1-(4-(dimetilamino)but-2-enoil)azepan-3-il)-7-metil-1H-benzo[d]imidazol-2-il)-2-(trifluorometil)izonikotinamid, ili njegova farmaceutski prihvatljiva sol.
18. Spoj prema zahtjevu 1, naznačen time, da navedeni spoj je (R)-N-(1-(1-akriloazepan-3-il)-7-kloro-6-(2-(pirolidin-1-il)etoksi)-1H-benzo[d]imidazol-2-il)-2,6-dimetilizonikotinamid, ili njegova farmaceutski prihvatljiva sol.
19. Spoj prema zahtjevu 1, naznačen time, da navedeni spoj je (R,E)-N-(7-kloro-1-(1-(4-(metilamino)but-2-enoil)azepan-3-il)-1H-benzo[d]imidazol-2-il)-2-metilizonikotinamid, ili njegova farmaceutski prihvatljiva sol.
20. Spoj prema bilo kojem od zahtjeva 1 do 19, naznačen time, da navedeni spoj je u obliku soli koja je odabrana od sljedećih: klorovodična sol, mesilat, tosilat, bromid, maleat i nitrat.
21. Farmaceutski sastav, naznačen time, da obuhvaća spoj prema bilo kojem od zahtjeva 1 do 19, ili njegovu farmaceutski prihvatljivu sol, te farmaceutski prikladan nosač.
22. Kombinacija, naznačena time, da obuhvaća spoj prema bilo kojem od zahtjeva 1 do 19, ili njegovu farmaceutski prihvatljivu sol, i kemoterapeutsko sredstvo.
23. Spoj prema bilo kojem od zahtjeva 1 do 19, ili njegova farmacutski prihvatljiva sol, naznačen/a time, da se upotrebljava u liječenju.
24. Spoj prema bilo kojem od zahtjeva 1 do 19, ili njegova farmacutski prihvatljiva sol, naznačen/a time, da se upotrebljava u postupku liječenja stanja posredovanog putem receptora epidermalnog faktora rasta (EGFR), pri čemu je stanje posredovano putem EGFR, odabrano od sljedećih: rak ne-malih stanica pluća (NSCLC), rak glave i vrata, kolorektalni rak, rak dojke, rak gušterače, rak jajnika, rak želudca, gliom i rak prostate.
25. Spoj za uporabu prema zahtjevu 24, naznačen time, da se kod stanja posredovanog putem EGFR, radi o raku ne-malih stanica pluća (NSCLC).
26. Spoj za uporabu prema zahtjevu 24, naznačen time, da se kod EGFR, radi o mutantnom EGFR, a mutantni EGFR obuhvaća G719S, G719C, G719A, L858R, L861Q, mutaciju izbacivanja ekson 19 ili mutaciju umetanja ekson 20; te prema potrebi kada mutantni EGFR nadalje obuhvaća EGFR mutaciju otpornosti T790M, T854A ili D761Y.
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