JPWO2021247969A5

JPWO2021247969A5 -

Download PDF

Info

Publication number: JPWO2021247969A5
Authority: JP; Japan
Prior art keywords: carboxamide; pyrazole; ethynyl; pyrrolidin; methylamino
Prior art date: 2024-06-11
Legal status : Pending

Application number

JP2022574753A

Other languages

English (en)

Japanese (ja)

Other versions

JP2023529867A (ja

Publication date

2024-06-11

2021-06-04 Application filed filed Critical

2021-06-04 Priority claimed from PCT/US2021/035854 external-priority patent/WO2021247969A1/en

2023-07-12 Publication of JP2023529867A publication Critical patent/JP2023529867A/ja

2024-06-11 Publication of JPWO2021247969A5 publication Critical patent/JPWO2021247969A5/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims 32
150000003839 salts Chemical class 0.000 claims 30
239000012453 solvate Substances 0.000 claims 30
239000008194 pharmaceutical composition Substances 0.000 claims 8
229910052739 hydrogen Inorganic materials 0.000 claims 7
239000001257 hydrogen Substances 0.000 claims 7
239000000546 pharmaceutical excipient Substances 0.000 claims 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
YXVDEILMUVTDMK-JKSUJKDBSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O YXVDEILMUVTDMK-JKSUJKDBSA-N 0.000 claims 3
AVUXLVYBASDKOX-ZWKOTPCHSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O AVUXLVYBASDKOX-ZWKOTPCHSA-N 0.000 claims 3
CKIQALRXIOELNJ-LSDHHAIUSA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)F)=C2N=C1 CKIQALRXIOELNJ-LSDHHAIUSA-N 0.000 claims 3
JMGHVRJQMLUCCL-ZWKOTPCHSA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O JMGHVRJQMLUCCL-ZWKOTPCHSA-N 0.000 claims 3
LNKQASWXMPBRRP-DLBZAZTESA-N 3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N=C1 LNKQASWXMPBRRP-DLBZAZTESA-N 0.000 claims 3
GJCDSJWYTCQGKW-UONOGXRCSA-N 3-[2-[1-(difluoromethyl)-4,6-difluoro-2-methylbenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C(F)=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C(F)F GJCDSJWYTCQGKW-UONOGXRCSA-N 0.000 claims 3
UVLXZGYOYDQFBQ-DLBZAZTESA-N 5-amino-3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound COC[C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O UVLXZGYOYDQFBQ-DLBZAZTESA-N 0.000 claims 3
125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
UADWEMGWENQIDS-ZFWWWQNUSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5S)-5-methyl-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)N1C(C=C)=O UADWEMGWENQIDS-ZFWWWQNUSA-N 0.000 claims 2
GNPYYYOKDKYGEC-JKSUJKDBSA-N 3-[2-(4-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=CC2=C3N=CN2C)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O GNPYYYOKDKYGEC-JKSUJKDBSA-N 0.000 claims 2
206010028980 Neoplasm Diseases 0.000 claims 2
125000003342 alkenyl group Chemical group 0.000 claims 2
125000003277 amino group Chemical group 0.000 claims 2
201000011510 cancer Diseases 0.000 claims 2
125000000753 cycloalkyl group Chemical group 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
229910052736 halogen Chemical group 0.000 claims 2
150000002367 halogens Chemical group 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
125000000547 substituted alkyl group Chemical group 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
ZKZGZCFEKNRYSA-DLBZAZTESA-N 1-[(3S,5R)-1-but-2-ynoyl-5-(methoxymethyl)pyrrolidin-3-yl]-3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC#CC(N(C1)[C@@H](COC)C[C@@H]1N(C(NC)=C1C(N)=O)N=C1C#CC(C(F)=CC1=C2N=CN1C1CC1)=C2F)=O ZKZGZCFEKNRYSA-DLBZAZTESA-N 0.000 claims 1
VZOZRQIHUFPDBK-RBUKOAKNSA-N 1-[(3S,5R)-1-but-2-ynoyl-5-(methoxymethyl)pyrrolidin-3-yl]-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC#CC(N(C1)[C@@H](COC)C[C@@H]1N(C(NC)=C1C(N)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C=N2)=O VZOZRQIHUFPDBK-RBUKOAKNSA-N 0.000 claims 1
QGPYBDXQEZSDLQ-JKSUJKDBSA-N 1-[(3S,5R)-1-but-2-ynoyl-5-(methoxymethyl)pyrrolidin-3-yl]-3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C#CC)=O)C(NC)=C2C(N)=O)=C2F)F)=C2N=C1 QGPYBDXQEZSDLQ-JKSUJKDBSA-N 0.000 claims 1
BMIQQNUHSMLSMV-LSDHHAIUSA-N 1-[(3S,5R)-5-(difluoromethoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-3-[2-(1-ethyl-6,7-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C(F)=C(C(C#CC2=NN([C@@H](C[C@@H]3COC(F)F)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 BMIQQNUHSMLSMV-LSDHHAIUSA-N 0.000 claims 1
XACWXXLICZWPLV-ZWKOTPCHSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-(2-pyrazolo[1,5-a]pyridin-5-ylethynyl)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=CC=NN3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XACWXXLICZWPLV-ZWKOTPCHSA-N 0.000 claims 1
NKCYFERFXDDHAP-ZWKOTPCHSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-(2-pyrazolo[1,5-a]pyridin-6-ylethynyl)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN3N=CC=C3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O NKCYFERFXDDHAP-ZWKOTPCHSA-N 0.000 claims 1
UZFIYJNSXFHDSZ-JKSUJKDBSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-(2-pyrazolo[1,5-a]pyrimidin-5-ylethynyl)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=NC3=CC=NN3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O UZFIYJNSXFHDSZ-JKSUJKDBSA-N 0.000 claims 1
UYQZZFJMQSNGJL-RBUKOAKNSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-(2-quinolin-7-ylethynyl)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC=C(C=CC=N3)C3=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O UYQZZFJMQSNGJL-RBUKOAKNSA-N 0.000 claims 1
XVHPYFFEDHYKME-DLBZAZTESA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-(2-quinoxalin-6-ylethynyl)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC=C3N=CC=NC3=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XVHPYFFEDHYKME-DLBZAZTESA-N 0.000 claims 1
AJQGJOSWZUAVFV-DLBZAZTESA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(1-methylbenzimidazol-5-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O AJQGJOSWZUAVFV-DLBZAZTESA-N 0.000 claims 1
FKFHAASXVPYXKN-DLBZAZTESA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(1-methylindazol-4-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=C(C=NN3C)C3=CC=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O FKFHAASXVPYXKN-DLBZAZTESA-N 0.000 claims 1
KHZYZEALOLWYDE-ZWKOTPCHSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(1-methylindazol-5-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC=C3N(C)N=CC3=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O KHZYZEALOLWYDE-ZWKOTPCHSA-N 0.000 claims 1
DXVWDCOHXAEMCI-DLBZAZTESA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(2-methyl-3H-benzimidazol-5-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N1 DXVWDCOHXAEMCI-DLBZAZTESA-N 0.000 claims 1
RJOHEJZPBSGJPH-ZWKOTPCHSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(2-methylindazol-5-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=CN(C)N=C3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O RJOHEJZPBSGJPH-ZWKOTPCHSA-N 0.000 claims 1
ACJBVRAIKXKXGG-VQTJNVASSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(2-methylquinolin-7-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC1=NC2=CC(C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=CC=C2C=C1 ACJBVRAIKXKXGG-VQTJNVASSA-N 0.000 claims 1
WQTFRFULRFIUTD-ZWKOTPCHSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(2-methylquinoxalin-6-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC(C=NC1=C2)=NC1=CC=C2C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O WQTFRFULRFIUTD-ZWKOTPCHSA-N 0.000 claims 1
ABHDQFMHHLWDMK-DLBZAZTESA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(3-methyl-1,2-benzoxazol-6-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC1=NOC2=C1C=CC(C#CC1=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C1C(N)=O)=C2 ABHDQFMHHLWDMK-DLBZAZTESA-N 0.000 claims 1
DEGFWGBKIMEELB-ZWKOTPCHSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(3-methylimidazo[1,2-a]pyridin-7-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC1=CN=C2N1C=CC(C#CC1=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C1C(N)=O)=C2 DEGFWGBKIMEELB-ZWKOTPCHSA-N 0.000 claims 1
UDHDFPLTBQYURI-JKSUJKDBSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(3-methylimidazo[4,5-b]pyridin-6-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN=C3N(C)C=NC3=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O UDHDFPLTBQYURI-JKSUJKDBSA-N 0.000 claims 1
AGHUQJMUUGJNLP-VQTJNVASSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(3-methylquinolin-7-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC(C=NC1=C2)=CC1=CC=C2C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O AGHUQJMUUGJNLP-VQTJNVASSA-N 0.000 claims 1
FJRGGMFKGSHHGM-ZWKOTPCHSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(3-methylquinoxalin-6-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC1=NC2=CC(C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=CC=C2N=C1 FJRGGMFKGSHHGM-ZWKOTPCHSA-N 0.000 claims 1
VQMRXWKIIYVQSD-UONOGXRCSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(4,6,7-trifluoro-1,2-dimethylbenzimidazol-5-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC1=NC(C(F)=C(C(F)=C2F)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C VQMRXWKIIYVQSD-UONOGXRCSA-N 0.000 claims 1
WINDMQSPHPPQJO-QWHCGFSZSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(4,6,7-trifluoro-1-methylbenzimidazol-5-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C(C2=C3N=CN2C)F)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O WINDMQSPHPPQJO-QWHCGFSZSA-N 0.000 claims 1
MPFDAQWCTWBFLJ-RBUKOAKNSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-(4-methylquinolin-7-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CC1=CC=NC2=CC(C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=CC=C12 MPFDAQWCTWBFLJ-RBUKOAKNSA-N 0.000 claims 1
FDWJKXIVKOJSLA-JKSUJKDBSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-([1,2,4]triazolo[1,5-a]pyridin-6-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN3N=CN=C3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O FDWJKXIVKOJSLA-JKSUJKDBSA-N 0.000 claims 1
OFLLSRCVEDDUHN-JKSUJKDBSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-([1,2,4]triazolo[1,5-a]pyridin-7-yl)ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=NN3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O OFLLSRCVEDDUHN-JKSUJKDBSA-N 0.000 claims 1
QEXITIDOFPTTAE-JKSUJKDBSA-N 1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)-3-[2-[1-methyl-2-(trifluoromethyl)benzimidazol-5-yl]ethynyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C)C(C(F)(F)F)=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O QEXITIDOFPTTAE-JKSUJKDBSA-N 0.000 claims 1
ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 claims 1
WKETUWYQDQNAQH-DLBZAZTESA-N 3-(2-imidazo[1,2-a]pyridin-2-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN(C=CC=C3)C3=N2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O WKETUWYQDQNAQH-DLBZAZTESA-N 0.000 claims 1
PQIBSIWXVPRNNY-DLBZAZTESA-N 3-(2-imidazo[1,2-a]pyridin-6-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CN3C2=NC=C3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O PQIBSIWXVPRNNY-DLBZAZTESA-N 0.000 claims 1
LADNBJIYDVWLGM-DLBZAZTESA-N 3-(2-imidazo[1,2-a]pyridin-7-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=CN3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O LADNBJIYDVWLGM-DLBZAZTESA-N 0.000 claims 1
DIJSKWHWBYWONW-JKSUJKDBSA-N 3-(2-imidazo[1,2-a]pyrimidin-6-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=N2)=CN3C2=NC=C3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O DIJSKWHWBYWONW-JKSUJKDBSA-N 0.000 claims 1
DEGILBYUYQINRT-JKSUJKDBSA-N 3-(2-imidazo[1,2-a]pyrimidin-7-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=NC3=NC=CN3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O DEGILBYUYQINRT-JKSUJKDBSA-N 0.000 claims 1
RZNAXYUGUXXPAV-JKSUJKDBSA-N 3-(2-imidazo[1,2-b]pyridazin-7-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=CN3N=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O RZNAXYUGUXXPAV-JKSUJKDBSA-N 0.000 claims 1
UCHVOQKCAKUZBL-ZWKOTPCHSA-N 3-(2-imidazo[1,5-a]pyridin-5-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC=CC3=CN=CN23)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O UCHVOQKCAKUZBL-ZWKOTPCHSA-N 0.000 claims 1
IBYNVHNRVPMWIV-DLBZAZTESA-N 3-(2-imidazo[1,5-a]pyridin-8-ylethynyl)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC=CN3C2=CN=C3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O IBYNVHNRVPMWIV-DLBZAZTESA-N 0.000 claims 1
XIJAKPJNPDLMBX-DLBZAZTESA-N 3-[2-(1,2-benzoxazol-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC(ON=C3)=C3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XIJAKPJNPDLMBX-DLBZAZTESA-N 0.000 claims 1
KNPLSRBVKFTLQU-ZWKOTPCHSA-N 3-[2-(1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C KNPLSRBVKFTLQU-ZWKOTPCHSA-N 0.000 claims 1
CHCRNUSFDLTSCW-INIZCTEOSA-N 3-[2-(1,2-dimethylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C=C2)C#CC3=NN([C@@H](CC4)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C CHCRNUSFDLTSCW-INIZCTEOSA-N 0.000 claims 1
IBCKMRJCCPITPY-LSDHHAIUSA-N 3-[2-(1,3-benzothiazol-2-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=NC(C=CC=C3)=C3S2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O IBCKMRJCCPITPY-LSDHHAIUSA-N 0.000 claims 1
FUZNVRYIAQGISL-JKSUJKDBSA-N 3-[2-(1,3-benzothiazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2SC=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O FUZNVRYIAQGISL-JKSUJKDBSA-N 0.000 claims 1
USLBANZRGOCXNQ-LSDHHAIUSA-N 3-[2-(1,3-benzoxazol-2-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=NC(C=CC=C3)=C3O2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O USLBANZRGOCXNQ-LSDHHAIUSA-N 0.000 claims 1
UMOJTWYHHZLUJK-JKSUJKDBSA-N 3-[2-(1,3-benzoxazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2OC=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O UMOJTWYHHZLUJK-JKSUJKDBSA-N 0.000 claims 1
CMLGMHOHAVCIOC-VQTJNVASSA-N 3-[2-(1-cyclobutyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C1CCC1 CMLGMHOHAVCIOC-VQTJNVASSA-N 0.000 claims 1
BCOJIDFRCFXQSL-RBUKOAKNSA-N 3-[2-(1-cyclobutyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CCC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O BCOJIDFRCFXQSL-RBUKOAKNSA-N 0.000 claims 1
WIQBEPAALNQBFG-VQTJNVASSA-N 3-[2-(1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C1CC1 WIQBEPAALNQBFG-VQTJNVASSA-N 0.000 claims 1
JFWRDVIUATYCSH-LSDHHAIUSA-N 3-[2-(1-cyclopropyl-4,6,7-trifluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C(C2=C3N=CN2C2CC2)F)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O JFWRDVIUATYCSH-LSDHHAIUSA-N 0.000 claims 1
CPKKLYYWTPHRRC-LSDHHAIUSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](C[C@@H]1COC(F)F)CN1C(C=C)=O CPKKLYYWTPHRRC-LSDHHAIUSA-N 0.000 claims 1
AAGZOCRBEWSLEE-SCLBCKFNSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](C[C@@H]1C(F)F)CN1C(C=C)=O AAGZOCRBEWSLEE-SCLBCKFNSA-N 0.000 claims 1
SEQVICNYQVJBMG-CABCVRRESA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(fluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](C[C@@H]1CF)CN1C(C=C)=O SEQVICNYQVJBMG-CABCVRRESA-N 0.000 claims 1
ZWFKEDXXBMXEDN-LSDHHAIUSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](C[C@@H]1CO)CN1C(C=C)=O ZWFKEDXXBMXEDN-LSDHHAIUSA-N 0.000 claims 1
XGHVKVRDULNGPH-JKSUJKDBSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-ynoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C#C)=O XGHVKVRDULNGPH-JKSUJKDBSA-N 0.000 claims 1
SEQVICNYQVJBMG-GJZGRUSLSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5S)-5-(fluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](C[C@H]1CF)CN1C(C=C)=O SEQVICNYQVJBMG-GJZGRUSLSA-N 0.000 claims 1
TUHMCETYQIRJBG-UHFFFAOYSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[1-(2-fluoroprop-2-enoyl)azetidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1C(C1)CN1C(C(F)=C)=O TUHMCETYQIRJBG-UHFFFAOYSA-N 0.000 claims 1
SOLQXBBADDHYFX-DLBZAZTESA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(2-hydroxyethylamino)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound COC[C@@H](C[C@@H](C1)N(C(NCCO)=C2C(N)=O)N=C2C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)N1C(C=C)=O SOLQXBBADDHYFX-DLBZAZTESA-N 0.000 claims 1
YZBZMQJUSIJALW-UHFFFAOYSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1C(C1)CN1C(C=C)=O YZBZMQJUSIJALW-UHFFFAOYSA-N 0.000 claims 1
JAQMOXUYSVWIST-AWEZNQCLSA-N 3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)=NN1[C@@H](CC1)CN1C(C=C)=O JAQMOXUYSVWIST-AWEZNQCLSA-N 0.000 claims 1
KIFSBJONYUTYIU-DLBZAZTESA-N 3-[2-(1-cyclopropyl-5-fluoroindazol-4-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=C(C=NN3C4CC4)C3=CC=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O KIFSBJONYUTYIU-DLBZAZTESA-N 0.000 claims 1
RUFUBNATAVLBGP-DLBZAZTESA-N 3-[2-(1-cyclopropyl-6,7-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2F)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O RUFUBNATAVLBGP-DLBZAZTESA-N 0.000 claims 1
NTOOXIFYZXCYFQ-HNNXBMFYSA-N 3-[2-(1-cyclopropyl-6,7-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2F)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](CC1)CN1C(C=C)=O NTOOXIFYZXCYFQ-HNNXBMFYSA-N 0.000 claims 1
DICHAOGUFHBCKM-BBRMVZONSA-N 3-[2-(1-cyclopropyl-6,7-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5S)-5-methyl-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2F)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O DICHAOGUFHBCKM-BBRMVZONSA-N 0.000 claims 1
QCQXUYMJTMOUSF-LEWJYISDSA-N 3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-1-(4-hydroxy-4-methylpent-2-ynoyl)-5-(methoxymethyl)pyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C)(C#CC(N(C1)[C@@H](COC)C[C@@H]1N(C(NC)=C1C(N)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C(C)=N2)=O)O QCQXUYMJTMOUSF-LEWJYISDSA-N 0.000 claims 1
UUKSGMDDVQPWPS-RBUKOAKNSA-N 3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C1CC1 UUKSGMDDVQPWPS-RBUKOAKNSA-N 0.000 claims 1
NVNGOGDTGIMPCK-JVJLVOBOSA-N 3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O NVNGOGDTGIMPCK-JVJLVOBOSA-N 0.000 claims 1
NVNGOGDTGIMPCK-VELBRHGASA-N 3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O NVNGOGDTGIMPCK-VELBRHGASA-N 0.000 claims 1
DIHFQQNXHRWFFS-VQTJNVASSA-N 3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-5-(2-hydroxyethylamino)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NCCO)=C3C(N)=O)=C2N1C1CC1 DIHFQQNXHRWFFS-VQTJNVASSA-N 0.000 claims 1
SVJHVOFEYUKMNI-VQTJNVASSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-1-(4-hydroxy-4-methylpent-2-ynoyl)-5-(methoxymethyl)pyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C)(C#CC(N(C1)[C@@H](COC)C[C@@H]1N(C(NC)=C1C(N)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C=N2)=O)O SVJHVOFEYUKMNI-VQTJNVASSA-N 0.000 claims 1
YSAOFZDTLGGDEG-HTAPYJJXSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(2-hydroxypropan-2-yl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C)([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O YSAOFZDTLGGDEG-HTAPYJJXSA-N 0.000 claims 1
ROEFADWCMVOWSM-DLBZAZTESA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC(F)F)CN1C(C=C)=O ROEFADWCMVOWSM-DLBZAZTESA-N 0.000 claims 1
INBQCIFHVSFWPQ-MGPUTAFESA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1C(F)F)CN1C(C=C)=O INBQCIFHVSFWPQ-MGPUTAFESA-N 0.000 claims 1
MRJWMSPFJQJBCK-SJORKVTESA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(fluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1CF)CN1C(C=C)=O MRJWMSPFJQJBCK-SJORKVTESA-N 0.000 claims 1
JHIHZBNPZKIACO-DLBZAZTESA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1CO)CN1C(C=C)=O JHIHZBNPZKIACO-DLBZAZTESA-N 0.000 claims 1
JKXVPURIKAFFJM-DLBZAZTESA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-ynoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1CO)CN1C(C#C)=O JKXVPURIKAFFJM-DLBZAZTESA-N 0.000 claims 1
XNZZGBMSIXOGGX-ZWKOTPCHSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-ynoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C#C)=O XNZZGBMSIXOGGX-ZWKOTPCHSA-N 0.000 claims 1
BACCMKVNYWFGQL-DAESXHAQSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O BACCMKVNYWFGQL-DAESXHAQSA-N 0.000 claims 1
BACCMKVNYWFGQL-XXHMAFKTSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O BACCMKVNYWFGQL-XXHMAFKTSA-N 0.000 claims 1
MRJWMSPFJQJBCK-IRXDYDNUSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5S)-5-(fluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@H]1CF)CN1C(C=C)=O MRJWMSPFJQJBCK-IRXDYDNUSA-N 0.000 claims 1
WETLPPYMPKZHGU-UHFFFAOYSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[1-(2-fluoroprop-2-enoyl)azetidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1C(C1)CN1C(C(F)=C)=O WETLPPYMPKZHGU-UHFFFAOYSA-N 0.000 claims 1
XSGWZZPXQUKMCX-SNAWJCMRSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[1-[(E)-4-(dimethylamino)but-2-enoyl]azetidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1C(C1)CN1C(/C=C/CN(C)C)=O XSGWZZPXQUKMCX-SNAWJCMRSA-N 0.000 claims 1
KZUMFXREGHMRRU-RBUKOAKNSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(2-hydroxyethylamino)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound COC[C@@H](C[C@@H](C1)N(C(NCCO)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O KZUMFXREGHMRRU-RBUKOAKNSA-N 0.000 claims 1
RMOQJGWYLWHCGV-RBUKOAKNSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(ethylamino)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O RMOQJGWYLWHCGV-RBUKOAKNSA-N 0.000 claims 1
WWRGQWQGIMMMQQ-UHFFFAOYSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(1-prop-2-enoylazetidin-3-yl)methyl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1CC(C1)CN1C(C=C)=O WWRGQWQGIMMMQQ-UHFFFAOYSA-N 0.000 claims 1
UDPQCKRTEJNLJB-INIZCTEOSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](CC1)CN1C(C=C)=O UDPQCKRTEJNLJB-INIZCTEOSA-N 0.000 claims 1
QPXMGYRMEUEPGD-INIZCTEOSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-ynoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](CC1)CN1C(C#C)=O QPXMGYRMEUEPGD-INIZCTEOSA-N 0.000 claims 1
VQTWPNLKVTURHJ-PBHICJAKSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-5-methyl-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O VQTWPNLKVTURHJ-PBHICJAKSA-N 0.000 claims 1
VQTWPNLKVTURHJ-YOEHRIQHSA-N 3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5S)-5-methyl-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O VQTWPNLKVTURHJ-YOEHRIQHSA-N 0.000 claims 1
XZWWCRJOEPEAFT-VQTJNVASSA-N 3-[2-(1-cyclopropyl-6-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C(C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O)=C1)=CC2=C1N=CN2C1CC1 XZWWCRJOEPEAFT-VQTJNVASSA-N 0.000 claims 1
MGEIWEFMSYFMLF-ZWKOTPCHSA-N 3-[2-(1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC(F)F)CN1C(C=C)=O MGEIWEFMSYFMLF-ZWKOTPCHSA-N 0.000 claims 1
HWKIHHZEILUDBX-MSOLQXFVSA-N 3-[2-(1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(fluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1CF)CN1C(C=C)=O HWKIHHZEILUDBX-MSOLQXFVSA-N 0.000 claims 1
CJVVXRNKGDZSSX-RBUKOAKNSA-N 3-[2-(1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O CJVVXRNKGDZSSX-RBUKOAKNSA-N 0.000 claims 1
ARZIWERQWDZKCX-RBUKOAKNSA-N 3-[2-(1-cyclopropylindazol-4-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=C(C=NN3C4CC4)C3=CC=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O ARZIWERQWDZKCX-RBUKOAKNSA-N 0.000 claims 1
KNMUWOPKASWTJD-RBUKOAKNSA-N 3-[2-(1-ethyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N=C1C KNMUWOPKASWTJD-RBUKOAKNSA-N 0.000 claims 1
LUVDROWXOHAZLX-ZWKOTPCHSA-N 3-[2-(1-ethyl-2-methylimidazo[4,5-b]pyridin-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C2=CC=C(C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)N=C2N=C1C LUVDROWXOHAZLX-ZWKOTPCHSA-N 0.000 claims 1
VIRVNOFBPOCALZ-UONOGXRCSA-N 3-[2-(1-ethyl-4,6,7-trifluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C(F)=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)F)=C2N=C1 VIRVNOFBPOCALZ-UONOGXRCSA-N 0.000 claims 1
BXINGPJVMSNYIJ-JKSUJKDBSA-N 3-[2-(1-ethyl-4,6-difluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)F)=C2N=C1C BXINGPJVMSNYIJ-JKSUJKDBSA-N 0.000 claims 1
PDJLXHSEBFIIOM-LEWJYISDSA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(3-morpholin-4-ylpropylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NCCCN3CCOCC3)=C2C(N)=O)=C2F)F)=C2N=C1 PDJLXHSEBFIIOM-LEWJYISDSA-N 0.000 claims 1
ZXUTXLBIHVKMPG-AWEZNQCLSA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(2-hydroxyethylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NCCO)=C2C(N)=O)=C2F)F)=C2N=C1 ZXUTXLBIHVKMPG-AWEZNQCLSA-N 0.000 claims 1
LQKXKJUYLJMARH-JKSUJKDBSA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(2-hydroxyethylamino)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NCCO)=C2C(N)=O)=C2F)F)=C2N=C1 LQKXKJUYLJMARH-JKSUJKDBSA-N 0.000 claims 1
OFLPFOKEKGAFTA-HNNXBMFYSA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(2-methoxyethylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NCCOC)=C2C(N)=O)=C2F)F)=C2N=C1 OFLPFOKEKGAFTA-HNNXBMFYSA-N 0.000 claims 1
DNUNSGXCKKBATC-DLBZAZTESA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(2-methoxyethylamino)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NCCOC)=C2C(N)=O)=C2F)F)=C2N=C1 DNUNSGXCKKBATC-DLBZAZTESA-N 0.000 claims 1
ZZPMJRQZWYFZHB-SFHVURJKSA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(2-morpholin-4-ylethylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NCCN3CCOCC3)=C2C(N)=O)=C2F)F)=C2N=C1 ZZPMJRQZWYFZHB-SFHVURJKSA-N 0.000 claims 1
HJFYGLCRDURSDH-IBGZPJMESA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(3-morpholin-4-ylpropylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NCCCN3CCOCC3)=C2C(N)=O)=C2F)F)=C2N=C1 HJFYGLCRDURSDH-IBGZPJMESA-N 0.000 claims 1
PELGEONVFCEALM-UONOGXRCSA-N 3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trifluoromethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC(F)(F)F)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)F)=C2N=C1 PELGEONVFCEALM-UONOGXRCSA-N 0.000 claims 1
YWAHMZYHQKXLOX-ZWKOTPCHSA-N 3-[2-(1-ethyl-4-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)=C2N=C1C YWAHMZYHQKXLOX-ZWKOTPCHSA-N 0.000 claims 1
APXDMRPWOZNGGD-DLBZAZTESA-N 3-[2-(1-ethyl-4-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)=C2N=C1 APXDMRPWOZNGGD-DLBZAZTESA-N 0.000 claims 1
CEWSFDNLBQHUKO-JKSUJKDBSA-N 3-[2-(1-ethyl-6,7-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C(F)=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 CEWSFDNLBQHUKO-JKSUJKDBSA-N 0.000 claims 1
WOKUPZYNIKKLEA-AWEZNQCLSA-N 3-[2-(1-ethyl-6,7-difluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C(F)=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 WOKUPZYNIKKLEA-AWEZNQCLSA-N 0.000 claims 1
XCHKSHSGVTUCHR-ZWKOTPCHSA-N 3-[2-(1-ethyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1C XCHKSHSGVTUCHR-ZWKOTPCHSA-N 0.000 claims 1
FPIKMDUNZISFAK-DLBZAZTESA-N 3-[2-(1-ethyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 FPIKMDUNZISFAK-DLBZAZTESA-N 0.000 claims 1
QXVZDOVNKCVXSE-HNNXBMFYSA-N 3-[2-(1-ethyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 QXVZDOVNKCVXSE-HNNXBMFYSA-N 0.000 claims 1
FITIIFZBRHVXDD-JKSUJKDBSA-N 3-[2-(1-ethyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trifluoromethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC(F)(F)F)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 FITIIFZBRHVXDD-JKSUJKDBSA-N 0.000 claims 1
RUUWTDVRBGAQCD-ZWKOTPCHSA-N 3-[2-(1-ethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N=C1 RUUWTDVRBGAQCD-ZWKOTPCHSA-N 0.000 claims 1
STBUQWNSOLJYNJ-RBUKOAKNSA-N 3-[2-(1-ethylindazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1N=CC2=CC(C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=CC=C12 STBUQWNSOLJYNJ-RBUKOAKNSA-N 0.000 claims 1
SMUWQHVFXRNAMW-RBUKOAKNSA-N 3-[2-(1-tert-butylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C)(C)N1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N=C1 SMUWQHVFXRNAMW-RBUKOAKNSA-N 0.000 claims 1
MCNHBMQHMRRNEW-JKSUJKDBSA-N 3-[2-(2-amino-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C)C(N)=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O MCNHBMQHMRRNEW-JKSUJKDBSA-N 0.000 claims 1
VZPYEWZNAAPDCK-DLBZAZTESA-N 3-[2-(2-cyclopropyl-1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)F)=C2N=C1C1CC1 VZPYEWZNAAPDCK-DLBZAZTESA-N 0.000 claims 1
KJYHRFIDMUBTCW-VQTJNVASSA-N 3-[2-(2-cyclopropyl-1-ethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N=C1C1CC1 KJYHRFIDMUBTCW-VQTJNVASSA-N 0.000 claims 1
RJWLUOVESRHIFY-RBUKOAKNSA-N 3-[2-(2-cyclopropyl-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C)C(C2CC2)=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O RJWLUOVESRHIFY-RBUKOAKNSA-N 0.000 claims 1
FVXWVQWCWBXGMR-ZWKOTPCHSA-N 3-[2-(2-cyclopropyl-3-methylimidazo[4,5-c]pyridin-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(N=C2)=CC3=C2N(C)C(C2CC2)=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O FVXWVQWCWBXGMR-ZWKOTPCHSA-N 0.000 claims 1
XWNFMMHLQIYIHQ-ZWKOTPCHSA-N 3-[2-(2-cyclopropyl-3H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2NC(C2CC2)=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XWNFMMHLQIYIHQ-ZWKOTPCHSA-N 0.000 claims 1
NMLYPQDTSRAZMD-JKSUJKDBSA-N 3-[2-(2-cyclopropyl-4,6-difluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=C(C4CC4)N2C)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O NMLYPQDTSRAZMD-JKSUJKDBSA-N 0.000 claims 1
HLOXUGHXEUVRLH-LSDHHAIUSA-N 3-[2-(2-cyclopropyl-4,6-difluoro-1H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=C(C4CC4)N2)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O HLOXUGHXEUVRLH-LSDHHAIUSA-N 0.000 claims 1
OHFQRADRDMYNLI-ZWKOTPCHSA-N 3-[2-(2-cyclopropyl-4-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=CC2=C3N=C(C4CC4)N2C)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O OHFQRADRDMYNLI-ZWKOTPCHSA-N 0.000 claims 1
QIXJLIJORJJKBS-ZWKOTPCHSA-N 3-[2-(2-cyclopropyl-6-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C)C(C2CC2)=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O QIXJLIJORJJKBS-ZWKOTPCHSA-N 0.000 claims 1
PLMGHFDXMHKUAK-RBUKOAKNSA-N 3-[2-(2-ethylindazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1N=C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)C2=C1 PLMGHFDXMHKUAK-RBUKOAKNSA-N 0.000 claims 1
XNUQDBZMBHAEKP-ZWKOTPCHSA-N 3-[2-(3,6-difluoroquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2N=CC(F)=CC2=C2)=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XNUQDBZMBHAEKP-ZWKOTPCHSA-N 0.000 claims 1
CCGFIHILANCAAS-LEWJYISDSA-N 3-[2-(3,6-dimethylquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C=NC1=C2)=CC1=CC(C)=C2C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O CCGFIHILANCAAS-LEWJYISDSA-N 0.000 claims 1
HKJZZXMAYVIABK-LSDHHAIUSA-N 3-[2-(3-chloro-6-fluoroimidazo[1,2-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CN23)=CC2=NC=C3Cl)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O HKJZZXMAYVIABK-LSDHHAIUSA-N 0.000 claims 1
QNKQITOTQIQCOD-ZWKOTPCHSA-N 3-[2-(3-chloro-6-fluoroquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2N=CC(Cl)=CC2=C2)=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O QNKQITOTQIQCOD-ZWKOTPCHSA-N 0.000 claims 1
TUEOXUUKDUFHGP-ZWKOTPCHSA-N 3-[2-(3-cyano-4-methoxypyrazolo[1,5-a]pyridin-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN3N=CC(C#N)=C3C(OC)=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O TUEOXUUKDUFHGP-ZWKOTPCHSA-N 0.000 claims 1
WQOGEMGCNCWNET-JKSUJKDBSA-N 3-[2-(3-cyano-6-fluoroimidazo[1,2-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=C(C#N)N3C=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O WQOGEMGCNCWNET-JKSUJKDBSA-N 0.000 claims 1
OFWJYGOZLKQDBI-JKSUJKDBSA-N 3-[2-(3-cyanoimidazo[1,2-a]pyridin-2-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=C(C#N)N(C=CC=C3)C3=N2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O OFWJYGOZLKQDBI-JKSUJKDBSA-N 0.000 claims 1
LIIUIKNYISUZRH-DLBZAZTESA-N 3-[2-(3-cyanoimidazo[1,2-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=C(C#N)N3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O LIIUIKNYISUZRH-DLBZAZTESA-N 0.000 claims 1
MRBIAEBBYXGAFD-ZWKOTPCHSA-N 3-[2-(3-cyanopyrazolo[1,5-a]pyridin-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN3N=CC(C#N)=C3C=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O MRBIAEBBYXGAFD-ZWKOTPCHSA-N 0.000 claims 1
NYVQALGAAPBZJF-RBUKOAKNSA-N 3-[2-(3-cyclopropyl-4-methoxypyrazolo[1,5-a]pyridin-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN3N=CC(C4CC4)=C3C(OC)=C2)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O NYVQALGAAPBZJF-RBUKOAKNSA-N 0.000 claims 1
TWTRTOSKAIKWPX-ZWKOTPCHSA-N 3-[2-(3-cyclopropyl-6-fluoroimidazo[1,2-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=C(C4CC4)N3C=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O TWTRTOSKAIKWPX-ZWKOTPCHSA-N 0.000 claims 1
NBJZKMHQHBTAKY-ZWKOTPCHSA-N 3-[2-(3-ethyl-2-methylimidazo[4,5-b]pyridin-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN(C(C)=NC1=C2)C1=NC=C2C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O NBJZKMHQHBTAKY-ZWKOTPCHSA-N 0.000 claims 1
OAYONHGPMKJTRO-ZWKOTPCHSA-N 3-[2-(3-ethyl-2-methylimidazo[4,5-c]pyridin-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=NC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N=C1C OAYONHGPMKJTRO-ZWKOTPCHSA-N 0.000 claims 1
GJVNFVSGLDXXQM-DLBZAZTESA-N 3-[2-(3-ethyl-4-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C(F)=C(C=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N=C1 GJVNFVSGLDXXQM-DLBZAZTESA-N 0.000 claims 1
LMWBWNAEGINARC-LSDHHAIUSA-N 3-[2-(4,6-difluoro-1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C(F)=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C LMWBWNAEGINARC-LSDHHAIUSA-N 0.000 claims 1
VBMBWPBRGSVCAQ-UONOGXRCSA-N 3-[2-(4,6-difluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O VBMBWPBRGSVCAQ-UONOGXRCSA-N 0.000 claims 1
FVOSEKOKUMBNPV-QWHCGFSZSA-N 3-[2-(4,6-difluoro-1-methylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trifluoromethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C)=C3F)=NN1[C@@H](C[C@@H]1COC(F)(F)F)CN1C(C=C)=O FVOSEKOKUMBNPV-QWHCGFSZSA-N 0.000 claims 1
QQABEJRJNKRRGK-QWHCGFSZSA-N 3-[2-(4,6-difluoro-1-methylbenzotriazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=NN2C)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O QQABEJRJNKRRGK-QWHCGFSZSA-N 0.000 claims 1
GQRDHHCMHZQBFZ-UONOGXRCSA-N 3-[2-(4,6-difluoro-1-methylindazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C(C=NN2C)C2=C2)=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O GQRDHHCMHZQBFZ-UONOGXRCSA-N 0.000 claims 1
MMXUIMBONNODCI-QWHCGFSZSA-N 3-[2-(4,6-difluoro-1H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O MMXUIMBONNODCI-QWHCGFSZSA-N 0.000 claims 1
SHBVMUDTJVEXDV-UONOGXRCSA-N 3-[2-(4,6-difluoro-2-methyl-1H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C(F)=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1 SHBVMUDTJVEXDV-UONOGXRCSA-N 0.000 claims 1
WZFYCQCWJSYSKI-ZWKOTPCHSA-N 3-[2-(4-chloro-1-ethyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2Cl)=C2N=C1C WZFYCQCWJSYSKI-ZWKOTPCHSA-N 0.000 claims 1
IBRYCRYBSOGTPU-DLBZAZTESA-N 3-[2-(4-fluoro-1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C(F)=C(C=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C IBRYCRYBSOGTPU-DLBZAZTESA-N 0.000 claims 1
NBNFDVGATSDCHA-JKSUJKDBSA-N 3-[2-(6,7-difluoro-1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2F)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C NBNFDVGATSDCHA-JKSUJKDBSA-N 0.000 claims 1
DULRPEILVOCOQW-LSDHHAIUSA-N 3-[2-(6,7-difluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2F)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O DULRPEILVOCOQW-LSDHHAIUSA-N 0.000 claims 1
ZEYFFLLGALKDFC-ZDUSSCGKSA-N 3-[2-(6,7-difluoro-1-methylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2F)=CC3=C2N(C)C=N3)=NN1[C@@H](CC1)CN1C(C=C)=O ZEYFFLLGALKDFC-ZDUSSCGKSA-N 0.000 claims 1
DJUCGVTYCJCFOT-DLBZAZTESA-N 3-[2-(6-chloro-1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C DJUCGVTYCJCFOT-DLBZAZTESA-N 0.000 claims 1
OQCJELNAVAHQHR-LSDHHAIUSA-N 3-[2-(6-chloro-1,3-benzothiazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2SC=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O OQCJELNAVAHQHR-LSDHHAIUSA-N 0.000 claims 1
RTJYNZCAGICNJS-VQTJNVASSA-N 3-[2-(6-chloro-1-cyclobutyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C1CCC1 RTJYNZCAGICNJS-VQTJNVASSA-N 0.000 claims 1
CFYSWMCUODNMEJ-RBUKOAKNSA-N 3-[2-(6-chloro-1-cyclobutylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C2CCC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O CFYSWMCUODNMEJ-RBUKOAKNSA-N 0.000 claims 1
MBLAJFFNNJKLKQ-LEWJYISDSA-N 3-[2-(6-chloro-1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-1-(4-hydroxy-4-methylpent-2-ynoyl)-5-(methoxymethyl)pyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C)(C#CC(N(C1)[C@@H](COC)C[C@@H]1N(C(NC)=C1C(N)=O)N=C1C#CC(C(Cl)=C1)=CC2=C1N(C1CC1)C(C)=N2)=O)O MBLAJFFNNJKLKQ-LEWJYISDSA-N 0.000 claims 1
NVXZVFLCPNUYOA-JVJLVOBOSA-N 3-[2-(6-chloro-1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O NVXZVFLCPNUYOA-JVJLVOBOSA-N 0.000 claims 1
NVXZVFLCPNUYOA-VELBRHGASA-N 3-[2-(6-chloro-1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O NVXZVFLCPNUYOA-VELBRHGASA-N 0.000 claims 1
MUIWMWNHJHWIDT-VQTJNVASSA-N 3-[2-(6-chloro-1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-5-(2-hydroxyethylamino)-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NCCO)=C3C(N)=O)=C2N1C1CC1 MUIWMWNHJHWIDT-VQTJNVASSA-N 0.000 claims 1
BWKQAMDRRRBSIP-DLBZAZTESA-N 3-[2-(6-chloro-1-cyclopropyl-7-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2F)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O BWKQAMDRRRBSIP-DLBZAZTESA-N 0.000 claims 1
KNJRYSSPHYCJEF-VQTJNVASSA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-1-(4-hydroxy-4-methylpent-2-ynoyl)-5-(methoxymethyl)pyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C)(C#CC(N(C1)[C@@H](COC)C[C@@H]1N(C(NC)=C1C(N)=O)N=C1C#CC(C(Cl)=C1)=CC2=C1N(C1CC1)C=N2)=O)O KNJRYSSPHYCJEF-VQTJNVASSA-N 0.000 claims 1
LWEALIBLSIVXBT-MGPUTAFESA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1C(F)F)CN1C(C=C)=O LWEALIBLSIVXBT-MGPUTAFESA-N 0.000 claims 1
MFRVGMLILYPEDB-DLBZAZTESA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)=NN1[C@@H](C[C@@H]1CO)CN1C(C=C)=O MFRVGMLILYPEDB-DLBZAZTESA-N 0.000 claims 1
GWOKPXQZGQJVIR-DAESXHAQSA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O GWOKPXQZGQJVIR-DAESXHAQSA-N 0.000 claims 1
GWOKPXQZGQJVIR-XXHMAFKTSA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O GWOKPXQZGQJVIR-XXHMAFKTSA-N 0.000 claims 1
ADISYMRCXCFZDX-UHFFFAOYSA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)=NN1C(C1)CN1C(C=C)=O ADISYMRCXCFZDX-UHFFFAOYSA-N 0.000 claims 1
FDLDCVCCCAZAEU-PBHICJAKSA-N 3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-5-methyl-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O FDLDCVCCCAZAEU-PBHICJAKSA-N 0.000 claims 1
YMWXMAYEECPQKT-ZWKOTPCHSA-N 3-[2-(6-chloro-1-ethyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N=C1C YMWXMAYEECPQKT-ZWKOTPCHSA-N 0.000 claims 1
RIQYAKHOZRRCDA-LSDHHAIUSA-N 3-[2-(6-chloro-1-ethyl-4-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2F)Cl)=C2N=C1 RIQYAKHOZRRCDA-LSDHHAIUSA-N 0.000 claims 1
FAUOIPORCFGVIY-JKSUJKDBSA-N 3-[2-(6-chloro-1-ethyl-7-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C(F)=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N=C1 FAUOIPORCFGVIY-JKSUJKDBSA-N 0.000 claims 1
SOGCCDZZQXWTJH-AWEZNQCLSA-N 3-[2-(6-chloro-1-ethyl-7-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C(F)=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N=C1 SOGCCDZZQXWTJH-AWEZNQCLSA-N 0.000 claims 1
VBTXGSLSEXEQLT-DLBZAZTESA-N 3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-1-(2-fluoroprop-2-enoyl)-5-(methoxymethyl)pyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C(F)=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N=C1 VBTXGSLSEXEQLT-DLBZAZTESA-N 0.000 claims 1
VIJVVOJHTFPJPH-JKSUJKDBSA-N 3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3CO)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N=C1 VIJVVOJHTFPJPH-JKSUJKDBSA-N 0.000 claims 1
DUUQOCLYDNPCBG-UHFFFAOYSA-N 3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN(C(C3)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N=C1 DUUQOCLYDNPCBG-UHFFFAOYSA-N 0.000 claims 1
LNKQASWXMPBRRP-CRNVDSNISA-N 3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trideuteriomethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound [2H]C([2H])([2H])OC[C@@H](C[C@@H](C1)N(C(NC)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(CC)C=N3)N1C(C=C)=O LNKQASWXMPBRRP-CRNVDSNISA-N 0.000 claims 1
XVLCSAMVDOLHFJ-JKSUJKDBSA-N 3-[2-(6-chloro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XVLCSAMVDOLHFJ-JKSUJKDBSA-N 0.000 claims 1
NJPNNPTWHBULDB-AWEZNQCLSA-N 3-[2-(6-chloro-1-methylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C)C=N3)=NN1[C@@H](CC1)CN1C(C=C)=O NJPNNPTWHBULDB-AWEZNQCLSA-N 0.000 claims 1
PDNJPJHAOGHGCI-JKSUJKDBSA-N 3-[2-(6-chloro-2-methyl-3H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1 PDNJPJHAOGHGCI-JKSUJKDBSA-N 0.000 claims 1
ANUDJTNEVLRYNY-LSDHHAIUSA-N 3-[2-(6-chloro-2-methyl-3H-benzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trifluoromethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC(F)(F)F)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1 ANUDJTNEVLRYNY-LSDHHAIUSA-N 0.000 claims 1
ARRBYQLVDYYFDQ-ZWKOTPCHSA-N 3-[2-(6-chloro-3-cyclopropylimidazo[1,2-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=C(C4CC4)N3C=C2Cl)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O ARRBYQLVDYYFDQ-ZWKOTPCHSA-N 0.000 claims 1
IVVVGTFSFCZGJI-ZWKOTPCHSA-N 3-[2-(6-chloro-3-fluoroquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2N=CC(F)=CC2=C2)=C2Cl)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O IVVVGTFSFCZGJI-ZWKOTPCHSA-N 0.000 claims 1
OJYGFXKDKKGLGB-RBUKOAKNSA-N 3-[2-(6-chloro-3-methylquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C=NC1=C2)=CC1=CC(Cl)=C2C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O OJYGFXKDKKGLGB-RBUKOAKNSA-N 0.000 claims 1
IKCSSINSHLMKLP-LSDHHAIUSA-N 3-[2-(6-chloro-3H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2NC=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O IKCSSINSHLMKLP-LSDHHAIUSA-N 0.000 claims 1
PEDFWHKSGAEPTL-LSDHHAIUSA-N 3-[2-(6-chloro-4-fluoro-1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C(F)=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C PEDFWHKSGAEPTL-LSDHHAIUSA-N 0.000 claims 1
XTWRFWOTHDBUQU-UONOGXRCSA-N 3-[2-(6-chloro-4-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=CC2=C3N=CN2C)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XTWRFWOTHDBUQU-UONOGXRCSA-N 0.000 claims 1
VJPGZSAYTGQYLS-DLBZAZTESA-N 3-[2-(6-chloro-4-methylcinnolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C1=C2)=CN=NC1=CC(C#CC1=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C1C(N)=O)=C2Cl VJPGZSAYTGQYLS-DLBZAZTESA-N 0.000 claims 1
FDIBFEPPINTENZ-ZWKOTPCHSA-N 3-[2-(6-chloro-4-methylquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C1=C2)=CC=NC1=CC(C#CC1=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C1C(N)=O)=C2Cl FDIBFEPPINTENZ-ZWKOTPCHSA-N 0.000 claims 1
VFIPIVUFXYXIPV-JKSUJKDBSA-N 3-[2-(6-chloro-7-fluoro-1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2F)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C VFIPIVUFXYXIPV-JKSUJKDBSA-N 0.000 claims 1
VBUFIHGJXRFSTO-LSDHHAIUSA-N 3-[2-(6-chloro-7-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2F)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O VBUFIHGJXRFSTO-LSDHHAIUSA-N 0.000 claims 1
XKDKEBGDXYZWBQ-ZDUSSCGKSA-N 3-[2-(6-chloro-7-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2F)=CC3=C2N(C)C=N3)=NN1[C@@H](CC1)CN1C(C=C)=O XKDKEBGDXYZWBQ-ZDUSSCGKSA-N 0.000 claims 1
MZMPUBWHLKICIE-VQTJNVASSA-N 3-[2-(6-cyano-1-ethyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)C#N)=C2N=C1C MZMPUBWHLKICIE-VQTJNVASSA-N 0.000 claims 1
UVZPZSOCKGEMLR-DLBZAZTESA-N 3-[2-(6-fluoro-1,2-dimethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C UVZPZSOCKGEMLR-DLBZAZTESA-N 0.000 claims 1
JDSKTZWCDULICQ-LSDHHAIUSA-N 3-[2-(6-fluoro-1,3-benzodioxol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2OCO3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O JDSKTZWCDULICQ-LSDHHAIUSA-N 0.000 claims 1
DSZBOWPUORURNC-LSDHHAIUSA-N 3-[2-(6-fluoro-1,3-benzothiazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2SC=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O DSZBOWPUORURNC-LSDHHAIUSA-N 0.000 claims 1
XJJPRVLMFWXVLO-LSDHHAIUSA-N 3-[2-(6-fluoro-1,3-benzoxazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2OC=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XJJPRVLMFWXVLO-LSDHHAIUSA-N 0.000 claims 1
HQEHAOKDYVCYNS-CABCVRRESA-N 3-[2-(6-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(fluoromethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1CF)CN1C(C=C)=O HQEHAOKDYVCYNS-CABCVRRESA-N 0.000 claims 1
WOPRZPUKVRDSQU-JKSUJKDBSA-N 3-[2-(6-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O WOPRZPUKVRDSQU-JKSUJKDBSA-N 0.000 claims 1
RWXYQPHVBHWWCP-AWEZNQCLSA-N 3-[2-(6-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C)C=N3)=NN1[C@@H](CC1)CN1C(C=C)=O RWXYQPHVBHWWCP-AWEZNQCLSA-N 0.000 claims 1
IAVMKJLFKZZQRT-LSDHHAIUSA-N 3-[2-(6-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trifluoromethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1COC(F)(F)F)CN1C(C=C)=O IAVMKJLFKZZQRT-LSDHHAIUSA-N 0.000 claims 1
VRWGJEGSNQCDOR-ZWKOTPCHSA-N 3-[2-(6-fluoro-1-propan-2-ylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C)N1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 VRWGJEGSNQCDOR-ZWKOTPCHSA-N 0.000 claims 1
APNNZPBEYIQDEV-JKSUJKDBSA-N 3-[2-(6-fluoro-2-methyl-3H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1 APNNZPBEYIQDEV-JKSUJKDBSA-N 0.000 claims 1
GVMUFZRBYHDFDD-RBUKOAKNSA-N 3-[2-(6-fluoro-3,4-dimethylquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C=NC1=C2)=C(C)C1=CC(F)=C2C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O GVMUFZRBYHDFDD-RBUKOAKNSA-N 0.000 claims 1
NXYHPLFMDBZINK-DLBZAZTESA-N 3-[2-(6-fluoro-3-methylimidazo[1,2-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=CN=C(C=C2C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)N1C=C2F NXYHPLFMDBZINK-DLBZAZTESA-N 0.000 claims 1
JPTJASOMZKLGSA-RBUKOAKNSA-N 3-[2-(6-fluoro-3-methylquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C=NC1=C2)=CC1=CC(F)=C2C#CC1=NN([C@@H](C[C@@H]2COC)CN2C(C=C)=O)C(NC)=C1C(N)=O JPTJASOMZKLGSA-RBUKOAKNSA-N 0.000 claims 1
BHUTULGJBNWVOB-LSDHHAIUSA-N 3-[2-(6-fluoro-3H-benzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2NC=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O BHUTULGJBNWVOB-LSDHHAIUSA-N 0.000 claims 1
ILUYQDKROTVMMP-UONOGXRCSA-N 3-[2-(6-fluoro-3H-benzimidazol-5-yl)ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trifluoromethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2NC=N3)=NN1[C@@H](C[C@@H]1COC(F)(F)F)CN1C(C=C)=O ILUYQDKROTVMMP-UONOGXRCSA-N 0.000 claims 1
FEBWMPHPIGIBDV-DLBZAZTESA-N 3-[2-(6-fluoro-4-methylcinnolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C1=C2)=CN=NC1=CC(C#CC1=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C1C(N)=O)=C2F FEBWMPHPIGIBDV-DLBZAZTESA-N 0.000 claims 1
KYQRBEARVHLKPS-ZWKOTPCHSA-N 3-[2-(6-fluoro-4-methylquinolin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC(C1=C2)=CC=NC1=CC(C#CC1=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C1C(N)=O)=C2F KYQRBEARVHLKPS-ZWKOTPCHSA-N 0.000 claims 1
KWVJQFMSGRDJSD-LSDHHAIUSA-N 3-[2-(6-fluoro-[1,2,4]triazolo[1,5-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=NN3C=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O KWVJQFMSGRDJSD-LSDHHAIUSA-N 0.000 claims 1
FRHFUGIDDKJTAF-JKSUJKDBSA-N 3-[2-(6-fluoroimidazo[1,2-a]pyridin-7-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CC3=NC=CN3C=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O FRHFUGIDDKJTAF-JKSUJKDBSA-N 0.000 claims 1
UZTLMUGZQHVVEE-DLBZAZTESA-N 3-[2-(7-chloro-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(CCC2)C2=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O UZTLMUGZQHVVEE-DLBZAZTESA-N 0.000 claims 1
JQTFDAPIIQYKPP-JKSUJKDBSA-N 3-[2-(7-fluoro-1-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2F)=CC3=C2N(C)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O JQTFDAPIIQYKPP-JKSUJKDBSA-N 0.000 claims 1
KAMHMKVWDVEIRG-DLBZAZTESA-N 3-[2-(7-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(CCC2)C2=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O KAMHMKVWDVEIRG-DLBZAZTESA-N 0.000 claims 1
VGOKJJPEWTXNRJ-LSDHHAIUSA-N 3-[2-(7-fluoro-[1,2,4]triazolo[1,5-a]pyridin-6-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC2=CN3N=CN=C3C=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O VGOKJJPEWTXNRJ-LSDHHAIUSA-N 0.000 claims 1
ODJYOEFFPIQYEF-ZWKOTPCHSA-N 3-[2-[1-(1-cyanocyclopropyl)-6-fluorobenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2(CC2)C#N)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O ODJYOEFFPIQYEF-ZWKOTPCHSA-N 0.000 claims 1
IALNALWYDYUGJH-QWHCGFSZSA-N 3-[2-[1-(difluoromethyl)-4,6-difluorobenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2C(F)F)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O IALNALWYDYUGJH-QWHCGFSZSA-N 0.000 claims 1
ZLZPPVNQZFBTLA-LSDHHAIUSA-N 3-[2-[1-(difluoromethyl)-6-fluorobenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C(F)F)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O ZLZPPVNQZFBTLA-LSDHHAIUSA-N 0.000 claims 1
GMZDDTMJKVDRHY-UONOGXRCSA-N 3-[2-[1-(difluoromethyl)-6-fluorobenzimidazol-5-yl]ethynyl]-5-(methylamino)-1-[(3S,5R)-1-prop-2-enoyl-5-(trifluoromethoxymethyl)pyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C(F)F)C=N3)=NN1[C@@H](C[C@@H]1COC(F)(F)F)CN1C(C=C)=O GMZDDTMJKVDRHY-UONOGXRCSA-N 0.000 claims 1
XYDXXTNWZWMSMD-JKSUJKDBSA-N 3-[2-[1-(difluoromethyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C(F)F)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XYDXXTNWZWMSMD-JKSUJKDBSA-N 0.000 claims 1
WHQPFFHFRYEZBV-MRUHUIDDSA-N 3-[2-[1-[(1S)-2,2-difluorocyclopropyl]-6-fluorobenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N([C@@H](C2)C2(F)F)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O WHQPFFHFRYEZBV-MRUHUIDDSA-N 0.000 claims 1
MLTUNIXDSBUBHZ-DLBZAZTESA-N 3-[2-[1-ethyl-2-(trifluoromethyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CCN1C(C=CC(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N=C1C(F)(F)F MLTUNIXDSBUBHZ-DLBZAZTESA-N 0.000 claims 1
WXEZWNQNQASMOD-ZWKOTPCHSA-N 3-[2-[2-(dimethylamino)-1-methylbenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N(C)C(N(C)C)=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O WXEZWNQNQASMOD-ZWKOTPCHSA-N 0.000 claims 1
ZXSFHLYONWYZIN-LSDHHAIUSA-N 3-[2-[3-(difluoromethyl)-6-fluorobenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N=CN3C(F)F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O ZXSFHLYONWYZIN-LSDHHAIUSA-N 0.000 claims 1
XLHRYRPMXHPYJX-ZWKOTPCHSA-N 3-[2-[3-(difluoromethyl)-6-fluoroquinolin-7-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2N=CC(C(F)F)=CC2=C2)=C2F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O XLHRYRPMXHPYJX-ZWKOTPCHSA-N 0.000 claims 1
VKJXUUOKHCEGBR-JKSUJKDBSA-N 3-[2-[3-(difluoromethyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C=C2)=CC3=C2N=CN3C(F)F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O VKJXUUOKHCEGBR-JKSUJKDBSA-N 0.000 claims 1
SDGZXWJNWZRYQT-UONOGXRCSA-N 3-[2-[4,6-difluoro-1-(2,2,2-trifluoroethyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=CN2CC(F)(F)F)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O SDGZXWJNWZRYQT-UONOGXRCSA-N 0.000 claims 1
DPVQVMJNSROJOW-NWDGAFQWSA-N 3-[2-[4,6-difluoro-2-(trifluoromethyl)-1H-benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=CC2=C3N=C(C(F)(F)F)N2)=C3F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O DPVQVMJNSROJOW-NWDGAFQWSA-N 0.000 claims 1
AEVRNKXPKHGHIF-LSDHHAIUSA-N 3-[2-[4,6-difluoro-2-methyl-1-(2,2,2-trifluoroethyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C(F)=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1CC(F)(F)F AEVRNKXPKHGHIF-LSDHHAIUSA-N 0.000 claims 1
HQNVFUSGCYVRAI-JKSUJKDBSA-N 3-[2-[6-chloro-1-(difluoromethyl)-2-methylbenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C(F)F HQNVFUSGCYVRAI-JKSUJKDBSA-N 0.000 claims 1
POAYFSILUSUTBH-LSDHHAIUSA-N 3-[2-[6-chloro-1-(difluoromethyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C(F)F)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O POAYFSILUSUTBH-LSDHHAIUSA-N 0.000 claims 1
HYQSGXBNMAGATE-DLBZAZTESA-N 3-[2-[6-chloro-1-(oxetan-3-yl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N(C2COC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O HYQSGXBNMAGATE-DLBZAZTESA-N 0.000 claims 1
JPGFRCSEFMTDID-GCKMJXCFSA-N 3-[2-[6-chloro-1-[(1R)-2,2-difluorocyclopropyl]benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N([C@H](C2)C2(F)F)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O JPGFRCSEFMTDID-GCKMJXCFSA-N 0.000 claims 1
JPGFRCSEFMTDID-MRUHUIDDSA-N 3-[2-[6-chloro-1-[(1S)-2,2-difluorocyclopropyl]benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N([C@@H](C2)C2(F)F)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O JPGFRCSEFMTDID-MRUHUIDDSA-N 0.000 claims 1
PDFQPVAJAQXBIO-ZWKOTPCHSA-N 3-[2-[6-chloro-2-methyl-1-(oxetan-3-yl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C1COC1 PDFQPVAJAQXBIO-ZWKOTPCHSA-N 0.000 claims 1
MMRCMEFLGJFQHT-JKSUJKDBSA-N 3-[2-[6-chloro-3-(difluoromethyl)-2-methylbenzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)Cl)=C2N1C(F)F MMRCMEFLGJFQHT-JKSUJKDBSA-N 0.000 claims 1
HAUPMVYJEXVCLP-LSDHHAIUSA-N 3-[2-[6-chloro-3-(difluoromethyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N=CN3C(F)F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O HAUPMVYJEXVCLP-LSDHHAIUSA-N 0.000 claims 1
BBEBPMDGLUZAAT-GCKMJXCFSA-N 3-[2-[6-chloro-3-[(1R)-2,2-difluorocyclopropyl]benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N=CN3[C@H](C2)C2(F)F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O BBEBPMDGLUZAAT-GCKMJXCFSA-N 0.000 claims 1
BBEBPMDGLUZAAT-MRUHUIDDSA-N 3-[2-[6-chloro-3-[(1S)-2,2-difluorocyclopropyl]benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(Cl)=C2)=CC3=C2N=CN3[C@@H](C2)C2(F)F)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O BBEBPMDGLUZAAT-MRUHUIDDSA-N 0.000 claims 1
RDDXIDPAWAFIMB-ZWKOTPCHSA-N 3-[2-[6-fluoro-1-(1-methylcyclopropyl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1(CC1)N1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)F)=C2N=C1 RDDXIDPAWAFIMB-ZWKOTPCHSA-N 0.000 claims 1
QVJYFTGSZWKZIH-DLBZAZTESA-N 3-[2-[6-fluoro-1-(oxetan-3-yl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CNC1=C(C(N)=O)C(C#CC(C(F)=C2)=CC3=C2N(C2COC2)C=N3)=NN1[C@@H](C[C@@H]1COC)CN1C(C=C)=O QVJYFTGSZWKZIH-DLBZAZTESA-N 0.000 claims 1
CGLYWWJPOIPHJW-ZWKOTPCHSA-N 3-[2-[6-fluoro-2-methyl-1-(oxetan-3-yl)benzimidazol-5-yl]ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]-5-(methylamino)pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(NC)=C3C(N)=O)=C2N1C1COC1 CGLYWWJPOIPHJW-ZWKOTPCHSA-N 0.000 claims 1
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
CARVLWVJOKOKBS-VQTJNVASSA-N 5-(cyclopropylamino)-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound COC[C@@H](C[C@@H](C1)N(C(NC2CC2)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O CARVLWVJOKOKBS-VQTJNVASSA-N 0.000 claims 1
OGBZBGBGROBIAX-INIZCTEOSA-N 5-(cyclopropylmethylamino)-3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NCC3CC3)=C2C(N)=O)=C2F)F)=C2N=C1 OGBZBGBGROBIAX-INIZCTEOSA-N 0.000 claims 1
XTBMLAZUZWGVHC-ZWKOTPCHSA-N 5-(cyclopropylmethylamino)-3-[2-(1-ethyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(NCC3CC3)=C2C(N)=O)=C2F)F)=C2N=C1 XTBMLAZUZWGVHC-ZWKOTPCHSA-N 0.000 claims 1
RBHOMWUEEOYCFT-HNNXBMFYSA-N 5-(methylamino)-3-[2-(2-methyl-3H-benzimidazol-5-yl)ethynyl]-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=CC(C#CC2=NN([C@@H](CC3)CN3C(C=C)=O)C(NC)=C2C(N)=O)=C2)=C2N1 RBHOMWUEEOYCFT-HNNXBMFYSA-N 0.000 claims 1
CIQJIMZSKPTOGS-UHFFFAOYSA-N 5-amino-3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound C=CC(N(C1)CC1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=CC1=C2N=CN1C1CC1)=C2F)=O CIQJIMZSKPTOGS-UHFFFAOYSA-N 0.000 claims 1
XKCBQRAQCGNMPE-ZDUSSCGKSA-N 5-amino-3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(CC1)C[C@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=CC1=C2N=CN1C1CC1)=C2F)=O XKCBQRAQCGNMPE-ZDUSSCGKSA-N 0.000 claims 1
OWBTYZQAAHQRBY-UONOGXRCSA-N 5-amino-3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(C1)[C@@H](COC(F)F)C[C@@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=CC1=C2N=CN1C1CC1)=C2F)=O OWBTYZQAAHQRBY-UONOGXRCSA-N 0.000 claims 1
IEKVJMZDAHGALL-UONOGXRCSA-N 5-amino-3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(C1)[C@@H](CO)C[C@@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=CC1=C2N=CN1C1CC1)=C2F)=O IEKVJMZDAHGALL-UONOGXRCSA-N 0.000 claims 1
RQRRIEHNUFFMTK-LSDHHAIUSA-N 5-amino-3-[2-(1-cyclopropyl-4,6-difluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound COC[C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(F)=CC2=C3N=CN2C2CC2)=C3F)N1C(C=C)=O RQRRIEHNUFFMTK-LSDHHAIUSA-N 0.000 claims 1
AAEMXTTVGTZKRV-ZWKOTPCHSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(F)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(N)=C3C(N)=O)=C2N1C1CC1 AAEMXTTVGTZKRV-ZWKOTPCHSA-N 0.000 claims 1
MAHHZLIDNVGOFE-GQNMWPQZSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O MAHHZLIDNVGOFE-GQNMWPQZSA-N 0.000 claims 1
MAHHZLIDNVGOFE-IBNJYYFUSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluoro-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O MAHHZLIDNVGOFE-IBNJYYFUSA-N 0.000 claims 1
PWLXZVHCRFYBGA-UHFFFAOYSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound C=CC(N(C1)CC1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C=N2)=O PWLXZVHCRFYBGA-UHFFFAOYSA-N 0.000 claims 1
RMGOGBCXOHEIIO-HNNXBMFYSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(CC1)C[C@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C=N2)=O RMGOGBCXOHEIIO-HNNXBMFYSA-N 0.000 claims 1
PSCOJQCSLIAMAT-JKSUJKDBSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(C1)[C@@H](COC(F)F)C[C@@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C=N2)=O PSCOJQCSLIAMAT-JKSUJKDBSA-N 0.000 claims 1
KHFSHDRTGQYFHM-JKSUJKDBSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(C1)[C@@H](CO)C[C@@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C=N2)=O KHFSHDRTGQYFHM-JKSUJKDBSA-N 0.000 claims 1
CJXGDFBEQAOKIF-DLBZAZTESA-N 5-amino-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound COC[C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O CJXGDFBEQAOKIF-DLBZAZTESA-N 0.000 claims 1
IXAATBAZKULNJD-JOTOCRJQSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O IXAATBAZKULNJD-JOTOCRJQSA-N 0.000 claims 1
IXAATBAZKULNJD-ZSOFBXJNSA-N 5-amino-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(F)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O IXAATBAZKULNJD-ZSOFBXJNSA-N 0.000 claims 1
BOAHBERXXMPZJR-DLBZAZTESA-N 5-amino-3-[2-(1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(difluoromethoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(C1)[C@@H](COC(F)F)C[C@@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C=C1)=CC2=C1N(C1CC1)C=N2)=O BOAHBERXXMPZJR-DLBZAZTESA-N 0.000 claims 1
PKNDKJNEEVTGNK-ZWKOTPCHSA-N 5-amino-3-[2-(6-chloro-1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CC1=NC(C=C(C(Cl)=C2)C#CC3=NN([C@@H](C[C@@H]4COC)CN4C(C=C)=O)C(N)=C3C(N)=O)=C2N1C1CC1 PKNDKJNEEVTGNK-ZWKOTPCHSA-N 0.000 claims 1
LVOILFBOYQALDI-GQNMWPQZSA-N 5-amino-3-[2-(6-chloro-1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O LVOILFBOYQALDI-GQNMWPQZSA-N 0.000 claims 1
LVOILFBOYQALDI-IBNJYYFUSA-N 5-amino-3-[2-(6-chloro-1-cyclopropyl-2-methylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C(C)=N3)N1C(C=C)=O)O LVOILFBOYQALDI-IBNJYYFUSA-N 0.000 claims 1
WYIBGKAYDAGNHE-UHFFFAOYSA-N 5-amino-3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound C=CC(N(C1)CC1N(C(N)=C1C(N)=O)N=C1C#CC(C(Cl)=C1)=CC2=C1N(C1CC1)C=N2)=O WYIBGKAYDAGNHE-UHFFFAOYSA-N 0.000 claims 1
SVWCAQDYZYEBFE-JKSUJKDBSA-N 5-amino-3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C=CC(N(C1)[C@@H](CO)C[C@@H]1N(C(N)=C1C(N)=O)N=C1C#CC(C(Cl)=C1)=CC2=C1N(C1CC1)C=N2)=O SVWCAQDYZYEBFE-JKSUJKDBSA-N 0.000 claims 1
FYQJFNXULHKAMB-JOTOCRJQSA-N 5-amino-3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1R)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O FYQJFNXULHKAMB-JOTOCRJQSA-N 0.000 claims 1
FYQJFNXULHKAMB-ZSOFBXJNSA-N 5-amino-3-[2-(6-chloro-1-cyclopropylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-[(1S)-1-hydroxyethyl]-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H]([C@@H](C[C@@H](C1)N(C(N)=C2C(N)=O)N=C2C#CC(C(Cl)=C2)=CC3=C2N(C2CC2)C=N3)N1C(C=C)=O)O FYQJFNXULHKAMB-ZSOFBXJNSA-N 0.000 claims 1
VPHAHCMMWSXQER-UHFFFAOYSA-N 5-amino-3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN(C(C3)CN3C(C=C)=O)C(N)=C2C(N)=O)=C2)Cl)=C2N=C1 VPHAHCMMWSXQER-UHFFFAOYSA-N 0.000 claims 1
CWPSVQJYYDWBAW-LSDHHAIUSA-N 5-amino-3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(hydroxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3CO)CN3C(C=C)=O)C(N)=C2C(N)=O)=C2)Cl)=C2N=C1 CWPSVQJYYDWBAW-LSDHHAIUSA-N 0.000 claims 1
DJLFOZQPWXUZNK-JKSUJKDBSA-N 5-amino-3-[2-(6-chloro-1-ethylbenzimidazol-5-yl)ethynyl]-1-[(3S,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]pyrazole-4-carboxamide Chemical compound CCN1C(C=C(C(C#CC2=NN([C@@H](C[C@@H]3COC)CN3C(C=C)=O)C(N)=C2C(N)=O)=C2)Cl)=C2N=C1 DJLFOZQPWXUZNK-JKSUJKDBSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
XOVKSVWIKOEARB-UHFFFAOYSA-N N-tert-butyl-3-[2-(1-cyclopropyl-6-fluorobenzimidazol-5-yl)ethynyl]-5-(methylamino)-1-(1-prop-2-enoylazetidin-3-yl)pyrazole-4-carboxamide Chemical compound CC(C)(C)NC(C1=C(NC)N(C(C2)CN2C(C=C)=O)N=C1C#CC(C(F)=C1)=CC2=C1N(C1CC1)C=N2)=O XOVKSVWIKOEARB-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1

JP2022574753A 2020-06-05 2021-06-04 線維芽細胞増殖因子受容体キナーゼの阻害剤 Pending JP2023529867A (ja)