JP2016505020A5

JP2016505020A5 -

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Publication number: JP2016505020A5
Authority: JP; Japan
Prior art keywords: amino; carboxamide; pyridin; hydroxy; difluorophenyl
Prior art date: 2014-01-14
Legal status : Granted

Application number

JP2015552896A

Other languages

English (en)

Japanese (ja)

Other versions

JP6554037B2 (ja

JP2016505020A (ja

Filing date

2014-01-14

Publication date

2017-02-02

2014-01-14 Application filed filed Critical

2014-01-14 Priority claimed from PCT/US2014/011486 external-priority patent/WO2014113388A1/en

2016-02-18 Publication of JP2016505020A publication Critical patent/JP2016505020A/ja

2017-02-02 Publication of JP2016505020A5 publication Critical patent/JP2016505020A5/ja

2019-07-31 Application granted granted Critical

2019-07-31 Publication of JP6554037B2 publication Critical patent/JP6554037B2/ja

Status Active legal-status Critical Current

2034-01-14 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 263
150000003839 salts Chemical class 0.000 claims description 118
239000000203 mixture Substances 0.000 claims description 76
125000000217 alkyl group Chemical group 0.000 claims description 66
-1 C 3-10 Shikuroa Kill Chemical group 0.000 claims description 61
125000001424 substituent group Chemical group 0.000 claims description 50
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
229910052799 carbon Inorganic materials 0.000 claims description 31
125000005843 halogen group Chemical group 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
239000003814 drug Substances 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
201000010099 disease Diseases 0.000 claims description 18
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
206010028980 Neoplasm Diseases 0.000 claims description 13
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
201000011510 cancer Diseases 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 10
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
101100297651 Mus musculus Pim2 gene Proteins 0.000 claims description 9
101150054691 PIM3 gene Proteins 0.000 claims description 9
101150056413 Pim1 gene Proteins 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
102000004190 Enzymes Human genes 0.000 claims description 5
108090000790 Enzymes Proteins 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 5
230000001225 therapeutic effect Effects 0.000 claims description 4
OAQFUYMWTJFWOQ-JFZPUFSHSA-N 3-amino-n-[(7s)-4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N OAQFUYMWTJFWOQ-JFZPUFSHSA-N 0.000 claims description 3
IXRDFQZZACBZIT-IVQKZFDZSA-N 5-amino-n-[(7s)-4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 IXRDFQZZACBZIT-IVQKZFDZSA-N 0.000 claims description 3
TYYHRLYFYASBPQ-ZBEGNZNMSA-N 5-amino-n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 TYYHRLYFYASBPQ-ZBEGNZNMSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000005605 benzo group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
HDXYGJYVVNHCFA-SGTLLEGYSA-N 3-amino-n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)pyrazine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=CN=C1N HDXYGJYVVNHCFA-SGTLLEGYSA-N 0.000 claims description 2
HCJGVVIWCFDORS-LBPRGKRZSA-N 5-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C(C=1CCCNC=1N=C1)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 HCJGVVIWCFDORS-LBPRGKRZSA-N 0.000 claims description 2
208000023328 Basedow disease Diseases 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
201000004624 Dermatitis Diseases 0.000 claims description 2
206010013554 Diverticulum Diseases 0.000 claims description 2
206010018364 Glomerulonephritis Diseases 0.000 claims description 2
208000015023 Graves' disease Diseases 0.000 claims description 2
208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims description 2
206010033645 Pancreatitis Diseases 0.000 claims description 2
201000004681 Psoriasis Diseases 0.000 claims description 2
201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
206010039710 Scleroderma Diseases 0.000 claims description 2
208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
201000009594 Systemic Scleroderma Diseases 0.000 claims description 2
206010042953 Systemic sclerosis Diseases 0.000 claims description 2
206010047115 Vasculitis Diseases 0.000 claims description 2
206010047642 Vitiligo Diseases 0.000 claims description 2
125000003725 azepanyl group Chemical group 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
BTEZDBVENXOPTN-ZCCHDVMBSA-N n-[(7r)-4-[(3s,5r)-3-amino-5-(trifluoromethyl)piperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(C(C)(O)C)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@@H](O)C3=NC=2)N2C[C@@H](C[C@H](N)C2)C(F)(F)F)=CC=C1F BTEZDBVENXOPTN-ZCCHDVMBSA-N 0.000 claims description 2
SYRYFOBYXIAVSI-YRSOCCHOSA-N n-[(7s)-4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(4-ethoxy-2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(OCC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)[C@H](O)[C@@H](C)C2)=CC=C1F SYRYFOBYXIAVSI-YRSOCCHOSA-N 0.000 claims description 2
PTORCEYGCGXHDH-SUVRLHETSA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 PTORCEYGCGXHDH-SUVRLHETSA-N 0.000 claims description 2
MPJKOTQQZQIJEJ-VTNXTBQGSA-N n-[4-[(3r,5s)-3-amino-4-hydroxy-4,5-dimethylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)C(O)(C)[C@@H](C)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MPJKOTQQZQIJEJ-VTNXTBQGSA-N 0.000 claims description 2
201000008482 osteoarthritis Diseases 0.000 claims description 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 10
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 10
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 7
125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 6
206010028537 myelofibrosis Diseases 0.000 claims 6
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 4
125000004966 cyanoalkyl group Chemical group 0.000 claims 4
206010061598 Immunodeficiency Diseases 0.000 claims 3
208000029462 Immunodeficiency disease Diseases 0.000 claims 3
125000001072 heteroaryl group Chemical group 0.000 claims 3
230000007813 immunodeficiency Effects 0.000 claims 3
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
SEEZPBNCJXQXFM-BUXKBTBVSA-N 3-amino-n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N SEEZPBNCJXQXFM-BUXKBTBVSA-N 0.000 claims 2
FWNRHQYQQFAYQE-NHYWBVRUSA-N 5-amino-n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluoro-3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(F)C(C=2SC(N)=C(C(=O)NC=3C(=C4CC[C@H](O)C4=NC=3)N3C[C@@H](N)CCC3)N=2)=C1F FWNRHQYQQFAYQE-NHYWBVRUSA-N 0.000 claims 2
JEGQLROZFGAUST-MCFWBGNESA-N 5-amino-n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-7-methyl-5,6-dihydrocyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C([C@@]1(O)C)CC(C=2N3C[C@@H](N)CCC3)=C1N=CC=2NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F JEGQLROZFGAUST-MCFWBGNESA-N 0.000 claims 2
JQUUCHJMNGAHNJ-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-4-hydroxy-4,5-dimethylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)C(O)(C)C(C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 JQUUCHJMNGAHNJ-UHFFFAOYSA-N 0.000 claims 2
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
208000014767 Myeloproliferative disease Diseases 0.000 claims 2
208000017733 acquired polycythemia vera Diseases 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 2
125000004414 alkyl thio group Chemical group 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
JABVLTOXBTYBLO-SGTLLEGYSA-N n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 JABVLTOXBTYBLO-SGTLLEGYSA-N 0.000 claims 2
PNQOXLQCMKOTQB-DJJJIMSYSA-N n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)CCC2)F)=C1F PNQOXLQCMKOTQB-DJJJIMSYSA-N 0.000 claims 2
UMFBDHBNGQVFJS-POUZXFSBSA-N n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfinylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(S(=O)C)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)CCC2)=CC=C1F UMFBDHBNGQVFJS-POUZXFSBSA-N 0.000 claims 2
AQLUVVSTLFBCLR-ZSEKCTLFSA-N n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfonylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(S(=O)(=O)C)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)CCC2)=CC=C1F AQLUVVSTLFBCLR-ZSEKCTLFSA-N 0.000 claims 2
SYKQOKZJNJIFQW-RBZFPXEDSA-N n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 SYKQOKZJNJIFQW-RBZFPXEDSA-N 0.000 claims 2
KFQBECHGODKRQL-CKNLXJGOSA-N n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)C[C@@H](C)C2)F)=C1F KFQBECHGODKRQL-CKNLXJGOSA-N 0.000 claims 2
FGAYEUCGPZBWTN-KVLCXJTPSA-N n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfinylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)S(C)=O)F)=N1 FGAYEUCGPZBWTN-KVLCXJTPSA-N 0.000 claims 2
MWCBNNDXJFKDBJ-YPENRWOSSA-N n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MWCBNNDXJFKDBJ-YPENRWOSSA-N 0.000 claims 2
OBHKKOJROOHSBD-WREIHNQOSA-N n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(COC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)C[C@@H](C)C2)=CC=C1F OBHKKOJROOHSBD-WREIHNQOSA-N 0.000 claims 2
208000037244 polycythemia vera Diseases 0.000 claims 2
206010039073 rheumatoid arthritis Diseases 0.000 claims 2
125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
YTXCEWLNVRYZKJ-UHFFFAOYSA-N 2-(2,6-difluoro-3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1OC)F)C=1SC=C(N1)C(=O)N YTXCEWLNVRYZKJ-UHFFFAOYSA-N 0.000 claims 1
OAQFUYMWTJFWOQ-BAVRXEHCSA-N 3-amino-n-[(7r)-4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N OAQFUYMWTJFWOQ-BAVRXEHCSA-N 0.000 claims 1
SEEZPBNCJXQXFM-HXPMCKFVSA-N 3-amino-n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N SEEZPBNCJXQXFM-HXPMCKFVSA-N 0.000 claims 1
XMZYXYKJEUAFLQ-MTJIALIYSA-N 3-amino-n-[(7r)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N XMZYXYKJEUAFLQ-MTJIALIYSA-N 0.000 claims 1
WPIMZMAFOWOVGM-UHFFFAOYSA-N 3-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N WPIMZMAFOWOVGM-UHFFFAOYSA-N 0.000 claims 1
OAQFUYMWTJFWOQ-UHFFFAOYSA-N 3-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N OAQFUYMWTJFWOQ-UHFFFAOYSA-N 0.000 claims 1
KSZHWDBEWHUOIH-UHFFFAOYSA-N 3-amino-n-[4-(3-amino-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N KSZHWDBEWHUOIH-UHFFFAOYSA-N 0.000 claims 1
XMZYXYKJEUAFLQ-UHFFFAOYSA-N 3-amino-n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N XMZYXYKJEUAFLQ-UHFFFAOYSA-N 0.000 claims 1
YSPJORFAUNCTRT-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCO2)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N YSPJORFAUNCTRT-UHFFFAOYSA-N 0.000 claims 1
KCVZUSUTNUFEER-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C(C=1CCCNC=1N=C1)=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N KCVZUSUTNUFEER-UHFFFAOYSA-N 0.000 claims 1
SEEZPBNCJXQXFM-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N SEEZPBNCJXQXFM-UHFFFAOYSA-N 0.000 claims 1
HDXYGJYVVNHCFA-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)pyrazine-2-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=CN=C1N HDXYGJYVVNHCFA-UHFFFAOYSA-N 0.000 claims 1
WPIMZMAFOWOVGM-OVRCFYHRSA-N 3-amino-n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N WPIMZMAFOWOVGM-OVRCFYHRSA-N 0.000 claims 1
YSPJORFAUNCTRT-LBPRGKRZSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CCO2)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N YSPJORFAUNCTRT-LBPRGKRZSA-N 0.000 claims 1
KCVZUSUTNUFEER-ZDUSSCGKSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C(C=1CCCNC=1N=C1)=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N KCVZUSUTNUFEER-ZDUSSCGKSA-N 0.000 claims 1
KSZHWDBEWHUOIH-OLZOCXBDSA-N 3-amino-n-[4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N KSZHWDBEWHUOIH-OLZOCXBDSA-N 0.000 claims 1
XMZYXYKJEUAFLQ-OBIPXCIUSA-N 3-amino-n-[4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N XMZYXYKJEUAFLQ-OBIPXCIUSA-N 0.000 claims 1
125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
IXRDFQZZACBZIT-SVXCRXAKSA-N 5-amino-n-[(7r)-4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 IXRDFQZZACBZIT-SVXCRXAKSA-N 0.000 claims 1
QLLAOUOYSHXDOH-STQMWFEESA-N 5-amino-n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-cyano-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@H]2C#N)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 QLLAOUOYSHXDOH-STQMWFEESA-N 0.000 claims 1
FWNRHQYQQFAYQE-XHDPSFHLSA-N 5-amino-n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluoro-3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(F)C(C=2SC(N)=C(C(=O)NC=3C(=C4CC[C@@H](O)C4=NC=3)N3C[C@@H](N)CCC3)N=2)=C1F FWNRHQYQQFAYQE-XHDPSFHLSA-N 0.000 claims 1
TYYHRLYFYASBPQ-MEDUHNTESA-N 5-amino-n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 TYYHRLYFYASBPQ-MEDUHNTESA-N 0.000 claims 1
JEGQLROZFGAUST-FNODVLLQSA-N 5-amino-n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-7-methyl-5,6-dihydrocyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C([C@]1(O)C)CC(C=2N3C[C@@H](N)CCC3)=C1N=CC=2NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F JEGQLROZFGAUST-FNODVLLQSA-N 0.000 claims 1
BCORPBSEYREPDR-YVEFUNNKSA-N 5-amino-n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-methoxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C([C@H]1OC)CC(C=2N3C[C@@H](N)CCC3)=C1N=CC=2NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F BCORPBSEYREPDR-YVEFUNNKSA-N 0.000 claims 1
ORPHXBGOTIFKKC-OHUAYANFSA-N 5-amino-n-[(7r)-4-[(3s,5r)-3-amino-5-(trifluoromethyl)piperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)C[C@@H](C(F)(F)F)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 ORPHXBGOTIFKKC-OHUAYANFSA-N 0.000 claims 1
JVGPIWKYHDULEI-BWACUDIHSA-N 5-amino-n-[(7r)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 JVGPIWKYHDULEI-BWACUDIHSA-N 0.000 claims 1
QLLAOUOYSHXDOH-OLZOCXBDSA-N 5-amino-n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-cyano-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@@H]2C#N)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 QLLAOUOYSHXDOH-OLZOCXBDSA-N 0.000 claims 1
BCORPBSEYREPDR-SJCJKPOMSA-N 5-amino-n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-methoxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C([C@@H]1OC)CC(C=2N3C[C@@H](N)CCC3)=C1N=CC=2NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F BCORPBSEYREPDR-SJCJKPOMSA-N 0.000 claims 1
ORPHXBGOTIFKKC-GDLVEWKHSA-N 5-amino-n-[(7s)-4-[(3s,5r)-3-amino-5-(trifluoromethyl)piperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)C[C@@H](C(F)(F)F)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 ORPHXBGOTIFKKC-GDLVEWKHSA-N 0.000 claims 1
PTIVAFQAZIXXLU-WQGACYEGSA-N 5-amino-n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluoro-3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(F)C(C=2SC(N)=C(C(=O)NC=3C(=C4CC[C@H](O)C4=NC=3)N3C[C@@H](N)C[C@@H](C)C3)N=2)=C1F PTIVAFQAZIXXLU-WQGACYEGSA-N 0.000 claims 1
JVGPIWKYHDULEI-PEBVRCNWSA-N 5-amino-n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 JVGPIWKYHDULEI-PEBVRCNWSA-N 0.000 claims 1
WKBLTFVUFARPFI-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-3-methylpiperidin-1-yl)-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(C)(N)CCCN1C1=C(CCC2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 WKBLTFVUFARPFI-UHFFFAOYSA-N 0.000 claims 1
ZBOCFNGWKOTVSG-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 ZBOCFNGWKOTVSG-UHFFFAOYSA-N 0.000 claims 1
ORFRNKIDIAATJE-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCC2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 ORFRNKIDIAATJE-UHFFFAOYSA-N 0.000 claims 1
IXRDFQZZACBZIT-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 IXRDFQZZACBZIT-UHFFFAOYSA-N 0.000 claims 1
VSCVRXUYBNPNAU-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 VSCVRXUYBNPNAU-UHFFFAOYSA-N 0.000 claims 1
PTIVAFQAZIXXLU-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluoro-3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(F)C(C=2SC(N)=C(C(=O)NC=3C(=C4CCC(O)C4=NC=3)N3CC(N)CC(C)C3)N=2)=C1F PTIVAFQAZIXXLU-UHFFFAOYSA-N 0.000 claims 1
JVGPIWKYHDULEI-UHFFFAOYSA-N 5-amino-n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 JVGPIWKYHDULEI-UHFFFAOYSA-N 0.000 claims 1
UALNXUQNOUVKIK-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-1h-pyrazolo[3,4-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C=1C=NNC=1N=C1)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 UALNXUQNOUVKIK-UHFFFAOYSA-N 0.000 claims 1
KZKWLRNRFFHPOL-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-1h-pyrrolo[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C=1C=CNC=1N=C1)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 KZKWLRNRFFHPOL-UHFFFAOYSA-N 0.000 claims 1
QRULZYNFRCRHRR-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCO2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 QRULZYNFRCRHRR-UHFFFAOYSA-N 0.000 claims 1
HCJGVVIWCFDORS-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C=1CCCNC=1N=C1)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 HCJGVVIWCFDORS-UHFFFAOYSA-N 0.000 claims 1
JPDZVHFTGRPLCA-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 JPDZVHFTGRPLCA-UHFFFAOYSA-N 0.000 claims 1
QLLAOUOYSHXDOH-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-7-cyano-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2C#N)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 QLLAOUOYSHXDOH-UHFFFAOYSA-N 0.000 claims 1
FWNRHQYQQFAYQE-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluoro-3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(F)C(C=2SC(N)=C(C(=O)NC=3C(=C4CCC(O)C4=NC=3)N3CC(N)CCC3)N=2)=C1F FWNRHQYQQFAYQE-UHFFFAOYSA-N 0.000 claims 1
TYYHRLYFYASBPQ-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 TYYHRLYFYASBPQ-UHFFFAOYSA-N 0.000 claims 1
JEGQLROZFGAUST-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-7-methyl-5,6-dihydrocyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1(O)CCC(C=2N3CC(N)CCC3)=C1N=CC=2NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F JEGQLROZFGAUST-UHFFFAOYSA-N 0.000 claims 1
BCORPBSEYREPDR-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-7-methoxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1CCC(C=2N3CC(N)CCC3)=C1N=CC=2NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F BCORPBSEYREPDR-UHFFFAOYSA-N 0.000 claims 1
MJEBWYJQVMJELN-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)-7-oxo-5,6-dihydrocyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2=O)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 MJEBWYJQVMJELN-UHFFFAOYSA-N 0.000 claims 1
MRMZLBBRKXPFJB-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)quinolin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C1=CC=CC=C1N=C1)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 MRMZLBBRKXPFJB-UHFFFAOYSA-N 0.000 claims 1
URNVZDFYVLSEAS-UHFFFAOYSA-N 5-amino-n-[4-(3-aminopiperidin-1-yl)thieno[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C=1C=CSC=1N=C1)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 URNVZDFYVLSEAS-UHFFFAOYSA-N 0.000 claims 1
WKBLTFVUFARPFI-XMMPIXPASA-N 5-amino-n-[4-[(3r)-3-amino-3-methylpiperidin-1-yl]-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@](C)(N)CCCN1C1=C(CCC2)C2=NC=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 WKBLTFVUFARPFI-XMMPIXPASA-N 0.000 claims 1
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BDWXZXTXHZHDOH-DKNLBFRPSA-N n-[(7r)-4-[(3r,4r,5s)-3-amino-5-cyclopropyl-4-hydroxypiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1([C@H]2CN(C[C@H]([C@@H]2O)N)C=2C(=CN=C3[C@H](O)CCC3=2)NC(=O)C=2N=C(C(F)=CC=2)C=2C(=CC=CC=2F)F)CC1 BDWXZXTXHZHDOH-DKNLBFRPSA-N 0.000 claims 1
MPJKOTQQZQIJEJ-RQENFTAQSA-N n-[(7r)-4-[(3r,4s,5s)-3-amino-4-hydroxy-4,5-dimethylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@](O)(C)[C@@H](C)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MPJKOTQQZQIJEJ-RQENFTAQSA-N 0.000 claims 1
JABVLTOXBTYBLO-KPZWWZAWSA-N n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 JABVLTOXBTYBLO-KPZWWZAWSA-N 0.000 claims 1
PNQOXLQCMKOTQB-ORAYPTAESA-N n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CC[C@@H](O)C3=NC=2)N2C[C@@H](N)CCC2)F)=C1F PNQOXLQCMKOTQB-ORAYPTAESA-N 0.000 claims 1
NSKSRXXALKXRBF-YEJXKQKISA-N n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfanylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@@H](O)C3=NC=2)N2C[C@@H](N)CCC2)=CC=C1F NSKSRXXALKXRBF-YEJXKQKISA-N 0.000 claims 1
UMFBDHBNGQVFJS-NHODNIPZSA-N n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfinylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(S(=O)C)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@@H](O)C3=NC=2)N2C[C@@H](N)CCC2)=CC=C1F UMFBDHBNGQVFJS-NHODNIPZSA-N 0.000 claims 1
SYKQOKZJNJIFQW-RNODOKPDSA-N n-[(7r)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 SYKQOKZJNJIFQW-RNODOKPDSA-N 0.000 claims 1
KFQBECHGODKRQL-LAPQFRIASA-N n-[(7r)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CC[C@@H](O)C3=NC=2)N2C[C@@H](N)C[C@@H](C)C2)F)=C1F KFQBECHGODKRQL-LAPQFRIASA-N 0.000 claims 1
FGAYEUCGPZBWTN-MIZAGWQBSA-N n-[(7r)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfinylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)S(C)=O)F)=N1 FGAYEUCGPZBWTN-MIZAGWQBSA-N 0.000 claims 1
MWCBNNDXJFKDBJ-HKZYLEAXSA-N n-[(7r)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MWCBNNDXJFKDBJ-HKZYLEAXSA-N 0.000 claims 1
AFSHCISYYIAZAH-KKAKJJSRSA-N n-[(7r)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)C(C)(C)O)F)=N1 AFSHCISYYIAZAH-KKAKJJSRSA-N 0.000 claims 1
OBHKKOJROOHSBD-KKAKJJSRSA-N n-[(7r)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(COC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@@H](O)C3=NC=2)N2C[C@@H](N)C[C@@H](C)C2)=CC=C1F OBHKKOJROOHSBD-KKAKJJSRSA-N 0.000 claims 1
MPJKOTQQZQIJEJ-DFSYOWCLSA-N n-[(7s)-4-[(3r,4r,5s)-3-amino-4-hydroxy-4,5-dimethylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@@](O)(C)[C@@H](C)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MPJKOTQQZQIJEJ-DFSYOWCLSA-N 0.000 claims 1
PTORCEYGCGXHDH-VRUBJZAOSA-N n-[(7s)-4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 PTORCEYGCGXHDH-VRUBJZAOSA-N 0.000 claims 1
SOJDITPDUYYHSK-YRSOCCHOSA-N n-[(7s)-4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(COC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)[C@H](O)[C@@H](C)C2)=CC=C1F SOJDITPDUYYHSK-YRSOCCHOSA-N 0.000 claims 1
BDWXZXTXHZHDOH-IORJTTJJSA-N n-[(7s)-4-[(3r,4r,5s)-3-amino-5-cyclopropyl-4-hydroxypiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1([C@H]2CN(C[C@H]([C@@H]2O)N)C=2C(=CN=C3[C@@H](O)CCC3=2)NC(=O)C=2N=C(C(F)=CC=2)C=2C(=CC=CC=2F)F)CC1 BDWXZXTXHZHDOH-IORJTTJJSA-N 0.000 claims 1
MPJKOTQQZQIJEJ-WNZUUVSCSA-N n-[(7s)-4-[(3r,4s,5s)-3-amino-4-hydroxy-4,5-dimethylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@](O)(C)[C@@H](C)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MPJKOTQQZQIJEJ-WNZUUVSCSA-N 0.000 claims 1
NSKSRXXALKXRBF-ZSEKCTLFSA-N n-[(7s)-4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfanylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](N)CCC2)=CC=C1F NSKSRXXALKXRBF-ZSEKCTLFSA-N 0.000 claims 1
BTEZDBVENXOPTN-GTQRCTGISA-N n-[(7s)-4-[(3s,5r)-3-amino-5-(trifluoromethyl)piperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(C(C)(O)C)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CC[C@H](O)C3=NC=2)N2C[C@@H](C[C@H](N)C2)C(F)(F)F)=CC=C1F BTEZDBVENXOPTN-GTQRCTGISA-N 0.000 claims 1
AFSHCISYYIAZAH-WREIHNQOSA-N n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)C(C)(C)O)F)=N1 AFSHCISYYIAZAH-WREIHNQOSA-N 0.000 claims 1
LNUIPBPFIMOFSC-CMWAXATJSA-N n-[(7s)-4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(oxan-3-yloxy)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CC[C@@H]2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(OC3COCCC3)=CC=2F)F)=N1 LNUIPBPFIMOFSC-CMWAXATJSA-N 0.000 claims 1
MPJKOTQQZQIJEJ-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-4,5-dimethylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)(C)C(C)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MPJKOTQQZQIJEJ-UHFFFAOYSA-N 0.000 claims 1
CAHFZEXEWKZBHJ-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CCOC3=NC=2)N2CC(N)C(O)C(C)C2)F)=C1F CAHFZEXEWKZBHJ-UHFFFAOYSA-N 0.000 claims 1
BXHUOGUHECQWGM-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 BXHUOGUHECQWGM-UHFFFAOYSA-N 0.000 claims 1
MZNQWRYZMSYAQV-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-[2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)C(C)(C)O)F)=N1 MZNQWRYZMSYAQV-UHFFFAOYSA-N 0.000 claims 1
AKXXNKBYDFPDRQ-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-[2,6-difluoro-4-(oxan-3-yloxy)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(OC3COCCC3)=CC=2F)F)=N1 AKXXNKBYDFPDRQ-UHFFFAOYSA-N 0.000 claims 1
ZYORJOGFVHRSMM-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCC2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 ZYORJOGFVHRSMM-UHFFFAOYSA-N 0.000 claims 1
PTORCEYGCGXHDH-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)C(O)C(C)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 PTORCEYGCGXHDH-UHFFFAOYSA-N 0.000 claims 1
SOJDITPDUYYHSK-UHFFFAOYSA-N n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(COC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2CC(N)C(O)C(C)C2)=CC=C1F SOJDITPDUYYHSK-UHFFFAOYSA-N 0.000 claims 1
BDWXZXTXHZHDOH-UHFFFAOYSA-N n-[4-(3-amino-5-cyclopropyl-4-hydroxypiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound OC1C(N)CN(C=2C(=CN=C3C(O)CCC3=2)NC(=O)C=2N=C(C(F)=CC=2)C=2C(=CC=CC=2F)F)CC1C1CC1 BDWXZXTXHZHDOH-UHFFFAOYSA-N 0.000 claims 1
QBDACFMRIUXBBP-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CCOC3=NC=2)N2CC(N)CC(C)C2)F)=C1F QBDACFMRIUXBBP-UHFFFAOYSA-N 0.000 claims 1
CXVCGOXRMUMGCU-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 CXVCGOXRMUMGCU-UHFFFAOYSA-N 0.000 claims 1
KFQBECHGODKRQL-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2CC(N)CC(C)C2)F)=C1F KFQBECHGODKRQL-UHFFFAOYSA-N 0.000 claims 1
FGAYEUCGPZBWTN-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfinylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)S(C)=O)F)=N1 FGAYEUCGPZBWTN-UHFFFAOYSA-N 0.000 claims 1
MWCBNNDXJFKDBJ-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 MWCBNNDXJFKDBJ-UHFFFAOYSA-N 0.000 claims 1
AFSHCISYYIAZAH-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)C(C)(C)O)F)=N1 AFSHCISYYIAZAH-UHFFFAOYSA-N 0.000 claims 1
OBHKKOJROOHSBD-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(COC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2CC(N)CC(C)C2)=CC=C1F OBHKKOJROOHSBD-UHFFFAOYSA-N 0.000 claims 1
LNUIPBPFIMOFSC-UHFFFAOYSA-N n-[4-(3-amino-5-methylpiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(oxan-3-yloxy)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1C(C)CC(N)CN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(OC3COCCC3)=CC=2F)F)=N1 LNUIPBPFIMOFSC-UHFFFAOYSA-N 0.000 claims 1
FZHGHJGMYLLVNY-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-1h-pyrazolo[3,4-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C=1C=NNC=1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 FZHGHJGMYLLVNY-UHFFFAOYSA-N 0.000 claims 1
DXKDDPZVTQBIHW-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-1h-pyrrolo[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C=1C=CNC=1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 DXKDDPZVTQBIHW-UHFFFAOYSA-N 0.000 claims 1
WDDLPAYTFOMBSK-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 WDDLPAYTFOMBSK-UHFFFAOYSA-N 0.000 claims 1
IWTLKAMIMFFAGO-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 IWTLKAMIMFFAGO-UHFFFAOYSA-N 0.000 claims 1
NHSUMDPNMBEPJB-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C(C=1CCCNC=1N=C1)=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 NHSUMDPNMBEPJB-UHFFFAOYSA-N 0.000 claims 1
VOBQOUPWPGMYQS-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 VOBQOUPWPGMYQS-UHFFFAOYSA-N 0.000 claims 1
YYWCHZZLVODBHP-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 YYWCHZZLVODBHP-UHFFFAOYSA-N 0.000 claims 1
JABVLTOXBTYBLO-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 JABVLTOXBTYBLO-UHFFFAOYSA-N 0.000 claims 1
PNQOXLQCMKOTQB-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2CC(N)CCC2)F)=C1F PNQOXLQCMKOTQB-UHFFFAOYSA-N 0.000 claims 1
NSKSRXXALKXRBF-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfanylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2CC(N)CCC2)=CC=C1F NSKSRXXALKXRBF-UHFFFAOYSA-N 0.000 claims 1
UMFBDHBNGQVFJS-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfinylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(S(=O)C)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2CC(N)CCC2)=CC=C1F UMFBDHBNGQVFJS-UHFFFAOYSA-N 0.000 claims 1
AQLUVVSTLFBCLR-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfonylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(S(=O)(=O)C)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2CC(N)CCC2)=CC=C1F AQLUVVSTLFBCLR-UHFFFAOYSA-N 0.000 claims 1
SYKQOKZJNJIFQW-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 SYKQOKZJNJIFQW-UHFFFAOYSA-N 0.000 claims 1
JXPXLBAOLQQTGJ-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)-7-oxo-5,6-dihydrocyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1C(N)CCCN1C1=C(CCC2=O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 JXPXLBAOLQQTGJ-UHFFFAOYSA-N 0.000 claims 1
MUEQZLBFVXWRSM-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)quinolin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C1=CC=CC=C1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 MUEQZLBFVXWRSM-UHFFFAOYSA-N 0.000 claims 1
GGXMPPMYRPBMPR-UHFFFAOYSA-N n-[4-(3-aminopiperidin-1-yl)thieno[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(N)CCCN1C(C=1C=CSC=1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 GGXMPPMYRPBMPR-UHFFFAOYSA-N 0.000 claims 1
CAHFZEXEWKZBHJ-OBZIZEEHSA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CCOC3=NC=2)N2C[C@@H](N)[C@H](O)[C@@H](C)C2)F)=C1F CAHFZEXEWKZBHJ-OBZIZEEHSA-N 0.000 claims 1
BXHUOGUHECQWGM-QHLKIINSSA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 BXHUOGUHECQWGM-QHLKIINSSA-N 0.000 claims 1
MZNQWRYZMSYAQV-MFMWZZQQSA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-[2,6-difluoro-4-(2-hydroxypropan-2-yl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2F)C(C)(C)O)F)=N1 MZNQWRYZMSYAQV-MFMWZZQQSA-N 0.000 claims 1
AKXXNKBYDFPDRQ-YOHREDKESA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-[2,6-difluoro-4-(oxan-3-yloxy)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC(OC3COCCC3)=CC=2F)F)=N1 AKXXNKBYDFPDRQ-YOHREDKESA-N 0.000 claims 1
ZYORJOGFVHRSMM-QDOYXITCSA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)[C@H](O)[C@@H](C)CN1C1=C(CCC2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 ZYORJOGFVHRSMM-QDOYXITCSA-N 0.000 claims 1
SYRYFOBYXIAVSI-KWIPPLHCSA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(4-ethoxy-2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(OCC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2C[C@@H](N)[C@H](O)[C@@H](C)C2)=CC=C1F SYRYFOBYXIAVSI-KWIPPLHCSA-N 0.000 claims 1
SOJDITPDUYYHSK-KWIPPLHCSA-N n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(methoxymethyl)phenyl]-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(COC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2C[C@@H](N)[C@H](O)[C@@H](C)C2)=CC=C1F SOJDITPDUYYHSK-KWIPPLHCSA-N 0.000 claims 1
BDWXZXTXHZHDOH-HOTUFBFMSA-N n-[4-[(3r,4r,5s)-3-amino-5-cyclopropyl-4-hydroxypiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1([C@H]2CN(C[C@H]([C@@H]2O)N)C=2C(=CN=C3C(O)CCC3=2)NC(=O)C=2N=C(C(F)=CC=2)C=2C(=CC=CC=2F)F)CC1 BDWXZXTXHZHDOH-HOTUFBFMSA-N 0.000 claims 1
FZHGHJGMYLLVNY-NSHDSACASA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-1h-pyrazolo[3,4-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C(C=1C=NNC=1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 FZHGHJGMYLLVNY-NSHDSACASA-N 0.000 claims 1
DXKDDPZVTQBIHW-LBPRGKRZSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-1h-pyrrolo[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C(C=1C=CNC=1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 DXKDDPZVTQBIHW-LBPRGKRZSA-N 0.000 claims 1
WDDLPAYTFOMBSK-LBPRGKRZSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 WDDLPAYTFOMBSK-LBPRGKRZSA-N 0.000 claims 1
IWTLKAMIMFFAGO-ZDUSSCGKSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 IWTLKAMIMFFAGO-ZDUSSCGKSA-N 0.000 claims 1
VOBQOUPWPGMYQS-ZDUSSCGKSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CCC2)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 VOBQOUPWPGMYQS-ZDUSSCGKSA-N 0.000 claims 1
YYWCHZZLVODBHP-AWEZNQCLSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CCC2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 YYWCHZZLVODBHP-AWEZNQCLSA-N 0.000 claims 1
NSKSRXXALKXRBF-JRTLGTJJSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-6-(2,6-difluoro-4-methylsulfanylphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC(F)=C1C1=NC(C(=O)NC=2C(=C3CCC(O)C3=NC=2)N2C[C@@H](N)CCC2)=CC=C1F NSKSRXXALKXRBF-JRTLGTJJSA-N 0.000 claims 1
JXPXLBAOLQQTGJ-ZDUSSCGKSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]-7-oxo-5,6-dihydrocyclopenta[b]pyridin-3-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=C(CCC2=O)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 JXPXLBAOLQQTGJ-ZDUSSCGKSA-N 0.000 claims 1
MUEQZLBFVXWRSM-AWEZNQCLSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]quinolin-3-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C(C1=CC=CC=C1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 MUEQZLBFVXWRSM-AWEZNQCLSA-N 0.000 claims 1
GGXMPPMYRPBMPR-LBPRGKRZSA-N n-[4-[(3s)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1[C@@H](N)CCCN1C(C=1C=CSC=1N=C1)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 GGXMPPMYRPBMPR-LBPRGKRZSA-N 0.000 claims 1
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QBDACFMRIUXBBP-KGLIPLIRSA-N n-[4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound COC1=CC=C(F)C(C=2C(=CC=C(N=2)C(=O)NC=2C(=C3CCOC3=NC=2)N2C[C@@H](N)C[C@@H](C)C2)F)=C1F QBDACFMRIUXBBP-KGLIPLIRSA-N 0.000 claims 1
CXVCGOXRMUMGCU-KGLIPLIRSA-N n-[4-[(3s,5r)-3-amino-5-methylpiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxamide Chemical compound C1[C@H](C)C[C@H](N)CN1C1=C(CCO2)C2=NC=C1NC(=O)C1=CC=C(F)C(C=2C(=CC=CC=2F)F)=N1 CXVCGOXRMUMGCU-KGLIPLIRSA-N 0.000 claims 1
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JP2015552896A 2013-01-15 2014-01-14 Ｐｉｍキナーゼ阻害剤として有用なチアゾールカルボキサミドおよびピリジンカルボキサミド化合物 Active JP6554037B2 (ja)