HRP20200770T1 - Spojevi tiazolkarboksamida i piridinkarboksamida korisni kao inhibitori pim kinaze - Google Patents
Spojevi tiazolkarboksamida i piridinkarboksamida korisni kao inhibitori pim kinaze Download PDFInfo
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- HRP20200770T1 HRP20200770T1 HRP20200770TT HRP20200770T HRP20200770T1 HR P20200770 T1 HRP20200770 T1 HR P20200770T1 HR P20200770T T HRP20200770T T HR P20200770TT HR P20200770 T HRP20200770 T HR P20200770T HR P20200770 T1 HRP20200770 T1 HR P20200770T1
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- amino
- hydroxy
- cyclopenta
- carboxamide
- dihydro
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- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 55
- 150000003839 salts Chemical class 0.000 claims 48
- 125000001475 halogen functional group Chemical group 0.000 claims 28
- 206010028980 Neoplasm Diseases 0.000 claims 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 201000011510 cancer Diseases 0.000 claims 22
- 125000001424 substituent group Chemical group 0.000 claims 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 15
- -1 (3R,4R)-3-amino-4-hydroxypiperidinyl Chemical group 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 7
- 238000000034 method Methods 0.000 claims 6
- 206010028537 myelofibrosis Diseases 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 5
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 208000026278 immune system disease Diseases 0.000 claims 5
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 4
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 4
- 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 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 101100310920 Caenorhabditis elegans sra-2 gene Proteins 0.000 claims 3
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 3
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 3
- 208000034578 Multiple myelomas Diseases 0.000 claims 3
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims 3
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 3
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 3
- 101150054691 PIM3 gene Proteins 0.000 claims 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 3
- 101150056413 Pim1 gene Proteins 0.000 claims 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 208000017733 acquired polycythemia vera Diseases 0.000 claims 3
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 3
- 201000002528 pancreatic cancer Diseases 0.000 claims 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 3
- 208000037244 polycythemia vera Diseases 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 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 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
- 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 2
- XMZYXYKJEUAFLQ-UVARLRKDSA-N 3-amino-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=NC(C=2C(=CC=CC=2F)F)=C(F)C=C1N XMZYXYKJEUAFLQ-UVARLRKDSA-N 0.000 claims 2
- 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 2
- 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 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
- 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 2
- 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 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 101100310926 Caenorhabditis elegans sra-3 gene Proteins 0.000 claims 2
- 101100310927 Caenorhabditis elegans sra-4 gene Proteins 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 102100038417 Cytoplasmic FMR1-interacting protein 1 Human genes 0.000 claims 2
- 101710181791 Cytoplasmic FMR1-interacting protein 1 Proteins 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 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
- 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 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
- 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 2
- 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 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 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 208000003476 primary myelofibrosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 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
- HDXYGJYVVNHCFA-KPZWWZAWSA-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)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-KPZWWZAWSA-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
- 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
- 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
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- 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
- AQLUVVSTLFBCLR-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-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-YEJXKQKISA-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
- 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 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
- LNUIPBPFIMOFSC-KOORAMRASA-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-(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-KOORAMRASA-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
- 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 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
- 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 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
- 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 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
- 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
- SYRYFOBYXIAVSI-UHFFFAOYSA-N n-[4-(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)N2CC(N)C(O)C(C)C2)=CC=C1F SYRYFOBYXIAVSI-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
- 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
- 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
- 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
- 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
- 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
- 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 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
- JABVLTOXBTYBLO-RSXQAXDFSA-N n-[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(CCC2O)C2=NC=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 JABVLTOXBTYBLO-RSXQAXDFSA-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
- BTEZDBVENXOPTN-VBIGTEDFSA-N n-[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(=C3CCC(O)C3=NC=2)N2C[C@@H](C[C@H](N)C2)C(F)(F)F)=CC=C1F BTEZDBVENXOPTN-VBIGTEDFSA-N 0.000 claims 1
- BTEZDBVENXOPTN-UHFFFAOYSA-N n-[4-[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(=C3CCC(O)C3=NC=2)N2CC(CC(N)C2)C(F)(F)F)=CC=C1F BTEZDBVENXOPTN-UHFFFAOYSA-N 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
Classifications
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- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
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Claims (49)
1. Spoj formule (I):
[image]
ili njegova farmaceutski prihvatljiva sol, pri čemu:
X je C;
A, B i D su prstenovi;
veza
[image]
predstavlja C=C vezu;
prsten A je formule (A-1) ili (A-2):
[image]
gdje su E1 i E2 prstenovi;
prsten B je prema formuli (B-2):
[image]
gdje je n odabrano od 0, 1, 2 i 3;
prsten D je piperidinski prsten, koji je supstituiran sa k supstitutima neovisno izabranim iz RD, pri čemu je k 0,1, 2 ili 3;
prsten E1 je fenil opcionalno supstituiran s 1, 2 ili 3, supstituenta neovisno izabranih od RE;
prsten E2 je fenil opcionalno supstituiran sa 1, 2 ili 3, supstituenta neovisno izabranih od RE;
G3 je N ili CR3;
R1 je izabran od H, F i NH2;
R2 je izabran od H, halo i CN;
R3 je izabran od H, halo i CN;
R4 je izabran od H, F i NH2;
svaki RB je neovisno izabran od CyB, halo, C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C1-6 haloalkil, CN, N02, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, C(=NRe1)NRc1Rd1, NRc1C(=NRe1)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)ORa1, NRc1C(O)NRc1Rd1, NRc1S(O)Rb1, NRc1S(O)2Rb1, NRc1S(O)2NRc1Rd1, S(O)Rb1, S(O)NRc1Rd1, S(O)2Rb1, S(O)2NRc1Rd1 i okso; pri čemu spomenuti C1-6 alkil, C2-6 alkenil, i C2-6 alkinil supstituenti od RB su svaki opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od CyB, halo, CN, NO2, ORa1, SRa1, C(O)Rb1, C(O)NRc1Rd1, C(O)ORa1, OC(O)Rb1, OC(O)NRc1Rd1, C(=NRe1)NRc1Rd1, NRc1C(=NRe1)NRc1Rd1, NRc1Rd1, NRc1C(O)Rb1, NRc1C(O)ORa1, NRc1C(O)NRc1Rd1, NRc1S(O)Rb1, NRc1S(O)2Rb1, NRc1S(O)2NRc1Rd1, S(O)Rb1, S(O)NRc1Rd1, S(O)2Rb1 i S(O)2NRc1Rd1
svaki RD je neovisno izabran od CyD, halo, C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C1-6 haloalkil, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, C(=NRe2)NRc2Rd2, NRc2C(=NRe2)NRc2Rd2, NRc2Rfd2, NRc2C(O)b2, NRc2C(O)ORa2, NRc2C(O)NRc2Rd2, NRc2S(O)Rb2, NRc2S(O)2Rb2, NRc2S(O)2NRc2Rd2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2, S(O)2NRc2Rd2 i okso; pri čemu spomenuti C1-6 alkil, C2-6 alkenil, i C2-6 alkinil supstituenti od RD su svaki opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od CyD, halo, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, OC(O)Rb2, OC(O)NRc2Rd2, C(=NRe2)NRc2Rd2, NRc2C(=NRe2)NRc2Rd2, NRc2Rd2, NRc2C(O)Rb2, NRc2C(O)ORa2, NRc2C(O)NRc2Rd2, NRc2S(O)Rb2, NRc2S(O)2Rb2, NRc2S(O)2NRc2Rd2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2 i S(O)2NRc2Rd2; svaki RE je neovisno izabran od CyE, halo, C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C1-6 haloalkil, CN, NO2, ORa3, SRa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, C(=NRe3)NRc3Rd3, NRc3C(=NRe3)NRc3Rd3, NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)ORa3, NRc3C(O)NRc3Rd3, NRc3S(O)Rb3, NRc3S(O)2Rb3, NRc3S(O)2NRc3Rd3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3, S(O)2NRc3Rd3 i okso; pri čemu spomenuti C1-6 alkil, C2-6 alkenil, i C2-6 alkinil od RE su svaki opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od CyE, halo, CN, NO2, ORa3, SRa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, OC(O)Rb3, OC(O)NRc3Rd3, C(=NRe3)NRc3Rd3, NRc3C(=NRe3)NRc3Rd3, NRc3Rd3, NRc3C(O)Rb3, NRc3C(O)ORa3, NRc3C(O)NRc3Rd3, NRc3S(O)Rb3, NRc3S(O)2Rb3, NRc3S(O)2NRc3Rd3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3 i S(O)2NRc3Rd3;
CyB, CyD i CyE su svaki neovisno izabrani od C6-10 aril, C3-10 cikloalkil, 5-10 -članih heteroaril i 4-10 -članih heterocikloalkil, od kojih je svaki opcionalno supstituiran s 1, 2, 3, 4 ili 5 supstituenata neovisno izabranih od halo, C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C1-6 haloalkil, C6-10 aril, C3-10 cikloalkil, 5-10 -članih heteroaril, 4-10 -članih heterocikloalkil, CN, NO2, ORa4, SRa4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, NRc4Rd4, NRc4C(O)R14, NRc4C(O)ORa4, NRc4C(O)NRc4Rd4, C(=NRe4)Rb4, C(=NRe4)NRc4Rd4, NRc4C(=NRe4)NRc4Rd4, NRc4S(O)Rb4, NRc4S(O)2Rb4, NRc4S(O)2NRc4Rd4, S(O)Rb4, S(O)NRc4Rd4, S(O)2Rb4, i S(O)2NRc4Rd4, pri čemu spomenuti C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C3-10 cikloalkil, 5-10 -člani heteroaril, i 4-10 -člani heterocikloalkil supstituenti od CyB, CyD ili CyE su svaki opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od halo, C1-4 haloalkil, CN, NO2, ORa4, SRa4, C(O)Rb4, C(O)NRc4Rd4, C(O)ORa4, OC(O)Rb4, OC(O)NRc4Rd4, C(=NRe4)NRc4Rd4, NRc4C(=NRe4)NRc4Rd4, NRc4Rd4, NRc4C(O)Rb4, NRc4C(O)ORa4, NRc4C(O)NRc4Rd4, NRc4S(O)Rb4, NRc4S(O)2Rb4, NRc4S(O)2NRc4Rd4, S(O)Rb4, S(O)NRc4Rd4, S(O)2Rb4 i S(O)2NRc4Rd4;
svaki Ra1, Rb1, Rc1, Rd1, Ra2, Rb2, Rc2, Rd2, Ra3, Rb3, Rc3, Rd3, Ra4, Rb4, Rc4 i Rd4 je neovisno izabran od H, C1-6 alkil, C1-4 haloalkil, C2-6 alkenil, C2-6 alkinil, C6-10 aril, C3-10 cikloalkil, 5-10 -članih heteroaril, 4-10 -članih heterocikloalkil, C6-10 aril-C1-4 alkil, C3-10 cikloalkil-C1-4 alkil, (5-10 -članih heteroaril)-C1-4 alkil ili (4-10 -članih heterocikloalkil)-C1-4 alkil, pri čemu spomenuti C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C6-10 aril, C3-10 cikloalkil, 5-10 -člani heteroaril, 4-10 -člani heterocikloalkil, C6-10 aril-C1-4 alkil, C3-10 cikloalkil-C1-4 alkil, (5-10 -člani heteroaril)-C1-4 alkil i (4-10 -člani heterocikloalkil)-C1-4 alkil je opcionalno supstituiran s 1, 2, 3, 4, ili 5 supstituenta neovisno izabranih od C1-4 alkil, C1-4 haloalkil, halo, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)R15, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5;
ili bilo koji Rc1 i Rd1 vezani za isti N atom, zajedno s N atomom za koji su vezani, formiraju 4-, 5-, 6-ili 7-članu heterocikloalkil grupu opcionalno supstituiranu s 1, 2 ili 3 supstituenta neovisno izabranih od C1-6 alkil, C3-7 cikloalkil, 3-7 -članih heterocikloalkil, C6-10 aril, 5-6 -članih heteroaril, C1-6 haloalkil, halo, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5, pri čemu su C1-6 alkil, C3-7 cikloalkil, 4-7 -člani heterocikloalkil, C6-10 aril i 5-6 -člani heteroaril opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od halo, C1-4 alkil, C1-4 haloalkil, C1-4 cijanoalkil, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5;
ili bilo koji Rc2 i Rd2 vezani za isti N atom, zajedno s N atomom za koji su vezani, formiraju 4-, 5-, 6-ili 7-članu heterocikloalkil grupu opcionalno supstituiranu s 1, 2 ili 3 supstituenta neovisno izabranih od C1-6 alkil, C3-7 cikloalkil, 4-7 -članih heterocikloalkil, C6-10 aril, i 5-6 -članih heteroaril, C1-6 haloalkil, halo, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5, pri čemu spomenuti C1-6 alkil, C3-7 cikloalkil, 4-7 -člani heterocikloalkil, C6-10 aril i 5-6 -člani heteroaril su opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od halo, C1-4 alkil, C1-4 haloalkil, C1-4 cijanoalkil, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5;
ili bilo koji Rc3 i Rd3 vezani za isti N atom, zajedno s N atomom za koji su vezani, formiraju 4-, 5-, 6-ili 7-članu heterocikloalkil grupu opcionalno supstituiranu s 1, 2 ili 3 supstituenta neovisno izabranih od C1-6 alkil, C3-7 cikloalkil, 4-7 -članih heterocikloalkil, C6-10 aril, 5-6 -članih heteroaril, C1-6 haloalkil, halo, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5, pri čemu spomenuti C1-6 alkil, C3-7 cikloalkil, 4-7 -člani heterocikloalkil, C6-10 aril, i 5-6 -člani heteroaril su opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od halo, C1-4 alkil, C1-4 haloalkil, C1-4 cijanoalkil, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5;
ili bilo koji Rc4 i Rd4 vezani za isti N atom, zajedno s N atomom za koji su vezani, formiraju 4-, 5-, 6-ili 7-članu heterocikloalkil grupu opcionalno supstituiranu s 1, 2 ili 3 supstituenta neovisno izabranih od C1-6 alkil, C3-7 cikloalkil, 3-7 -članih heterocikloalkil, C6-10 aril, 5-6 -članih heteroaril, C1-6 haloalkil, halo, CN, ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5, pri čemu spomenuti C1-6 alkil, C3-7 cikloalkil, 3-7 -člani heterocikloalkil, C6-10 aril, i 5-6 -člani heteroaril su opcionalno supstituirani s 1, 2 ili 3 supstituenta neovisno izabranih od halo, C1-4 alkil, C1-4 haloalkil, C1-4 cijanoalkil, CN ORa5, SRa5, C(O)Rb5, C(O)NRc5Rd5, C(O)ORa5, OC(O)Rb5, OC(O)NRc5Rd5, NRc5Rd5, NRc5C(O)Rb5, NRc5C(O)NRc5Rd5, NRc5C(O)ORa5, C(=NRe5)NRc5Rd5, NRc5C(=NRe5)NRc5Rd5, S(O)Rb5, S(O)NRc5Rd5, S(O)2Rb5, NRc5S(O)2Rb5, NRc5S(O)2NRc5Rd5 i S(O)2NRc5Rd5;
svaki Ra5, Rb5, Rc5 i Rd5 je neovisno izabran od H, C1-4 alkil, C1-4 haloalkil, C2-4 alkenil i C2-4 alkinil, pri čemu spomenuti C1-4 alkil, C2-4 alkenil, i C2-4 alkinil, je opcionalno supstituiran s 1, 2 ili 3 supstituenta neovisno izabranih od OH, CN, amino, halo, C1-4 alkil, C1-4 alkoksi, C1-4 alkiltio, C1-4 alkilamino, di(C1-4 alkil)amino, C1-4 haloalkil, i C1-4 haloalkoksi;
ili bilo koji Rc5 i Rd5 vezani za isti N atom, zajedno s N atomom za koji su vezani, formiraju 3-, 4-, 5-, 6-, ili 7-članu heterocikloalkil grupu opcionalno supstituiranu s 1, 2 ili 3 supstituenta neovisno izabranih od OH, CN, amino, halo, C1-6 alkil, C1-4 alkoksi, C1-4 alkiltio, C1-4 alkilamino, di(C1-4 alkil)amino, C1-4 haloalkil i C1-4 haloalkoksi; i
svaki Re1, Re2, Re3, Re4 i Re5 je neovisno izabran od H, C1-4 alkil i CN.
2. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, pri čemu je prsten B prema formuli (B-3):
[image]
gdje je m 0, 1 ili 2.
3. Spoj prema zahtjevu 1 ili 2, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) n je 0; ili
b) n je 1.
4. Spoj prema zahtjevu 2, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) m je 0; ili
b) m je 1.
5. Spoj prema bilo kojem zahtjevu 1 do 4, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) svaki RB je neovisno izabran od halo, C1-6 alkil, C1-6 haloalkil, CN, ORa1 i okso; ili
b) svaki RB je neovisno izabran od halo, C1-6 alkil, C1-6 haloalkil, CN, i ORa1; ili
c) svaki RB je neovisno izabran od CN, OH, metoksi i okso; ili
d) svaki RB je neovisno izabran od CN, OH i metoksi.
6. Spoj prema bilo kojem zahtjevu 1 do 5, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) prsten B je nesupstituiran ili supstituiran s 1 supstituentom izabranim od RB; ili
b) prsten B je nesupstituiran.
7. Spoj prema bilo kojem zahtjevu 1 do 6, ili njegova farmaceutski prihvatljiva sol, pri čemu atom azota iz prstena D formira vezu s ostatkom molekula.
8. Spoj prema bilo kojem zahtjevu 1 do 7, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) svaki RD je neovisno izabran od halo, C1-6 alkil, C2-6 alkenil, C2-6 alkinil, C1-6 haloalkil, CN, NO2, ORa2, SRa2, C(O)Rb2, C(O)NRc2Rd2, C(O)ORa2, NRc2Rd2, S(O)Rb2, S(O)NRc2Rd2, S(O)2Rb2, i S(O)2NRc2Rd2; ili
b) svaki RD je neovisno izabran od C1-6 alkil, ORa2, i NRc2Rd2.
9. Spoj prema bilo kojem zahtjevu 1 do 7, ili njegova farmaceutski prihvatljiva sol, pri čemu svaki RD je neovisno izabran od metil, OH, i NH2.
10. Spoj prema zahtjevu 9, ili njegova farmaceutski prihvatljiva sol, pri čemu je prsten D piperidin-1-il prsten supstituiran u položaju 3 s amino grupom.
11. Spoj prema zahtjevu 10, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) konfiguracija atoma ugljika u položaju 3 piperidin-1-il prstena koji formira prsten D je (S); ili
b) konfiguracija atoma ugljika u položaju 3 piperidin-1-il prstena koji formira prsten D je (R).
12. Spoj prema bilo kojem zahtjevu 1 do 6, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) prsten D je(3S)-aminopiperidin-1-il, (3R,4R)-3-amino-4-hidroksipiperidinil, (3R,4S)-3-amino-4-hidroksipiperidinil, (3R,4R,5R)-3-amino-4-hidroksi-5-metilpiperidinil, (3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidinil, (3R,4S,5R)-3-amino-4-hidroksi-5-metilpiperidinil ili (3R,4S,5S)-3-amino-4-hidroksi-5-metilpiperidinil;
ili
b) prsten D je (3R)-aminopiperidin-1-il, (3S,4S)-3-amino-4-hidroksipiperidinil, (3S,4R)-3-amino-4-hidroksipiperidinil, (3S,4R,5R)-3-amino-4-hidroksi-5-metilpiperidinil, (3S,4R,5S)-3-amino-4-hidroksi-5-metilpiperidinil, (3S,4S,5R)-3-amino-4-hidroksi-5-metilpiperidinil ili (3S,4S,5S)-3-amino-4-hidroksi-5-metilpiperidinil.
13. Spoj prema bilo kojem zahtjevu 1 do 12, ili njegova farmaceutski prihvatljiva sol, pri čemu: -
a) prsten D je grupa izabrana od formula (D-3)-(D-19):
[image]
[image]
ili
b) prsten D je grupa formule (D-3):
[image]
ili
c) prsten D je grupa formule (D-4):
[image]
ili
d) prsten D je grupa formule (D-5):
[image]
14. Spoj prema bilo kojem zahtjevu 1 do 13, ili njegova farmaceutski prihvatljiva sol, pri čemu je prsten A prema formuli (A-1):
[image]
15. Spoj prema zahtjevu 14, ili njegova farmaceutski prihvatljiva sol, pri čemu je R1 izabran od H i NH2.
16. Spoj prema zahtjevu 14 ili 15, ili njegova farmaceutski prihvatljiva sol, pri čemu je prsten E1 fenil koji je 2,6-disupstituiran sa supstituentima neovisno izabranim od RE.
17. Spoj prema bilo kojem zahtjevu 1 do 16, ili njegova farmaceutski prihvatljiva sol, pri čemu je svaki RE neovisno izabran od halo, C1-6 alkil, C1-6 haloalkil, CN, ORa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, NRc3Rd3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3, i S(O)2NRc3Rd3.
18. Spoj prema zahtjevu 17, ili njegova farmaceutski prihvatljiva sol, pri čemu je svaki REneovisno izabran od halo.
19. Spoj prema zahtjevu 18, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) prsten E1 je fenil koji je 2,6-dihalo-supstituiran; ili
b) prsten E1 je 2,6-difluorofenil.
20. Spoj prema bilo kojem zahtjevu 1 do 13, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) G3 je CR3; ili
b) G3 je N.
21. Spoj prema bilo kojem zahtjevu 1 do 13 i 20, ili njegova farmaceutski prihvatljiva sol, pri čemu prsten A je formula (A-2):
[image]
22. Spoj prema zahtjevu 21, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) G3 je CR3; ili
b) G3je N.
23. Spoj prema bilo kojem zahtjevu 1 do 13 i 20 do 22, ili njegova farmaceutski prihvatljiva sol, pri čemu je prsten A formula (A-2a):
[image]
24. Spoj prema bilo kojem od zahtjeva 20 do 23, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) R2 je H ili halogen; ili
b) R2je F.
25. Spoj prema bilo kojem od zahtjeva 20 do 24, ili njegova farmaceutski prihvatljiva sol, pri čemu R3je H.
26. Spoj prema bilo kojem od zahtjeva 20 do 25, ili njegova farmaceutski prihvatljiva sol, pri čemu R4je izabran od H i NH2.
27. Spoj prema bilo kojem od zahtjeva 20 do 26, ili njegova farmaceutski prihvatljiva sol, pri čemu je prsten E2fenil koji je 2,6-disupstituiran sa supstitutima neovisno izabranim od RE.
28. Spoj prema bilo kojem od zahtjeva 20 do 27, ili njegova farmaceutski prihvatljiva sol, pri čemu svaki RE je neovisno izabran od halo, C1-6 alkil, C1-6 haloalkil, CN, ORa3, C(O)Rb3, C(O)NRc3Rd3, C(O)ORa3, NRc3Rd3, S(O)Rb3, S(O)NRc3Rd3, S(O)2Rb3, i S(O)2NRc3Rd3.
29. Spoj prema zahtjevu 28, ili njegova farmaceutski prihvatljiva sol, pri čemu svaki RE je neovisno izabran od halo.
30. Spoj prema zahtjevu 29, ili njegova farmaceutski prihvatljiva sol, pri čemu:-
a) prsten E2 je fenil koji je 2,6-dihalo-supstituiran; ili
b) prsten E2 je 2,6-difluorofenil.
31. Spoj prema bilo kojem zahtjevu 1 do 30, pri čemu:-
a) Ra1, Rb1, Rc1, Rd1, Ra2, Rb2, Rc2, Rd2, Ra3, Rb3, Rc3 i Rd3 su svaki neovisno H ili C1-6 alkil; i/ili
b) Ra4 Rb4, Rc4 i Rd4 su svaki neovisno H ili C1-6 alkil; i/ili
c) Ra5, Rb5, Rc5 i Rd5 su svaki neovisno H ili C1-6 alkil.
32. Spoj prema bilo kojem zahtjevu 1 do 31, pri čemu:-
a) Re1,Re2, Re3, Re4 i Re5 su svaki neovisno H ili C1-6 alkil; ili
b) Re1, Re2, Re3, Re4 i Re5 su svaki H.
33. Spoj prema zahtjevu 1 :-
a) izabran od sljedećih spojeva, ili njihovih farmaceutski prihvatljivih soli:
N-{4-[3-aminopiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[3-aminopiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[3-aminopiperidin-1-il]-7-metoksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[3-aminopiperidin-1-il]-7-cijano-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[3-aminopiperidin-1-il]-7-hidroksi-7-metil-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[3-aminopiperidin-1-il]-7-okso-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[3-aminopiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[3-amino-4-hidroksipiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[3-amino-5-(trifluorometil)piperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
3-amino-N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[3-aminopiperidin-1-il]-7-okso-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(4-etoksi-2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
5-amino-N{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-[4-(3-amino-3-metilpiperidin-1-il)-6,7-dihidro-5H-ciklopenta[b]piridin-3-il]-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metiltio)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid; i
N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfonil)fenil]-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)pirazin-2-karboksamid;
N-{4-[3-amino-4-hidroksi-4,5-dimetilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid
N-{4-[3-amino-5-ciklopropil-4-hidroksipiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid
N-{4-[3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(tetrahidro-2H-piran-3-iloksi)fenil]-5-fluoropiridin-2-karboksamid
N-{4-[3-amino-5-(trifluorometil)piperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid;
ili
b) izabran od sljedećih spojeva, ili njihovih farmaceutski prihvatljivih soli:
N-(4-[(3S)-3-aminopiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-metoksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-metoksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-metoksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-cijano-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-cijano-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-cijano-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-7-metil-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-7-metil-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-7-metil-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-okso-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[(3R,4R)-3-amino-4-hidroksipiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N{4-[(3S,4S)-3-amino-4-hidroksipiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N{4-[(3R,4S)-3-amino-4-hidroksipiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S,4R)-3-amino-4-hidroksipiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N{4-[(3S,5R)-3-amino-5-(trifluorometil)piperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S,5R)-3-amino-5-(trifluorometil)piperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S,5R)-3-amino-5-(trifluorometil)piperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
3-amino-N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-7-okso-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(4-etoksi-2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(4-etoksi-2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(4-etoksi-2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
5-amino-N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-2-(2,6-difluoro-3-metoksifenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluoro-3-metoksifenil)-5-fluoropiridin-2-karboksamid;
5-amino-N-[4-((3R)-3-amino-3-metilpiperidin-1-il)-6,7-dihidro-5H-ciklopenta[b]piridin-3-il]-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
5-amino-N-[4-((3S)-3-amino-3-metilpiperidin-1-il)-6,7-dihidro-5H-ciklopenta[b]piridin-3-il]-2-(2,6-difluorofenil)-1,3-tiazol-4-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metiltio)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metiltio)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metiltio)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfinil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfonil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfonil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metilsulfonil)fenil]-5-fluoropiridin-2-karboksamid;
3-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)pirazin-2-karboksamid;
3-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)pirazin-2-karboksamid;
3-amino-N-{4-[(3S)-3-aminopiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)pirazin-2-karboksamid;
N-{4-[(3R,5S)-3-amino-4-hidroksi-4,5-dimetilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-4,5-dimetilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4S,5S)-3-amino-4-hidroksi-4,5-dimetilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-4,5-dimetilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4S,5S)-3-amino-4-hidroksi-4,5-dimetilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(metoksimetil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-5-ciklopropil-4-hidroksipiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-5-ciklopropil-4-hidroksipiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3R,4R,5S)-3-amino-5-ciklopropil-4-hidroksipiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(tetrahidro-2H-piran-3-iloksi)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(tetrahidro-2H-piran-3-iloksi)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-metilpiperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(tetrahidro-2H-piran-3-iloksi)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-(trifluorometil)piperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid;
N-{4-[(3S,5R)-3-amino-5-(trifluorometil)piperidin-1-il]-(7R)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid; i
N-{4-[(3S,5R)-3-amino-5-(trifluorometil)piperidin-1-il]-(7S)-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-[2,6-difluoro-4-(1-hidroksi-1-metiletil)fenil]-5-fluoropiridin-2-karboksamid.
34. Spoj prema zahtjevu 1, pri čemu je spoj N-{4-[3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid ili njegova farmaceutski prihvatljiva sol.
35. Spoj prema zahtjevu 1, pri čemu je spoj N-{4-[(3R,4R,5S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid ili njegova farmaceutski prihvatljiva sol.
36. Spoj prema zahtjevu 1, pri čemu je spoj N-{4-[(3R,4R,5S,7R)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid ili njegova farmaceutski prihvatljiva sol.
37. Spoj prema zahtjevu 1, pri čemu je spoj N-{4-[(3R,4R,5S,7S)-3-amino-4-hidroksi-5-metilpiperidin-1-il]-7-hidroksi-6,7-dihidro-5H-ciklopenta[b]piridin-3-il}-6-(2,6-difluorofenil)-5-fluoropiridin-2-karboksamid ili njegova farmaceutski prihvatljiva sol.
38. Sastav koji sadrži spoj prema bilo kojem od zahtjeva 1 do 37, ili njegovu farmaceutski prihvatljivu sol, i najmanje jedan farmaceutski prihvatljiv nosač.
39. Postupak inhibiranja Pim1, Pim2, ili Pim3 enzima koji obuhvaća kontakt enzima in vitro sa spojem prema bilo kojem od zahtjeva 1 do 37, ili njegovom farmaceutski prihvatljivom soli.
40. Spoj prema bilo kojem od zahtjeva 1 do 37, ili njegova farmaceutski prihvatljiva sol, za upotrebu u postupku liječenja bolesti ili stanja koje je povezano s povišenom razinom izražavanja ili aktivnosti najmanje jednog od Pim1, Pim2 i Pim3.
41. Spoj prema bilo kojem od zahtjeva 1 do 37, ili njegova farmaceutski prihvatljiva sol, za upotrebu u postupku liječenja karcinoma.
42. Spoj, ili njegova farmaceutski prihvatljiva sol, za upotrebu prema zahtjevu 41, pri čemu:-
a) karcinom je karcinom gdje je izražavanje ili aktivnost najmanje jednog od Pim1, Pim2 i Pim3 ushodno regulirana; i/ili
b) karcinom je karcinom gdje se aktivira onkogen; i/ili
c) karcinom je karcinom gdje se aktivira Myc ili BCL2; i/ili
d) karcinom je čvrsti tumor ili hematološki karcinom; i/ili
e) karcinom je karcinom prostate, karcinom debelog crijeva, karcinom jednjaka, karcinom endometrija, karcinom jajnika, karcinom materice, karcinom bubrega, karcinom jetre, karcinom gušterače, karcinom želuca, karcinom dojke, karcinom pluća, karcinom glave ili vrata, karcinom štitnjače, glioblastom, sarkom, karcinom mokraćnog mjehura, limfom, leukemija, akutna limfoblastna leukemija, akutna mijelogena leukemija, kronična limfocitna leukemija, kronična mijelogena leukemija, difuzni limfom velikih B stanica, limfom stanica plašta, ne-Hodgkinov limfom, Hodgkinov limfom ili multipli mijelom; ili
f) karcinom je karcinom prostate, karcinom gušterače, akutna mijelogena leukemija, difuzni limfom velikih B stanica ili multipli mijelom; ili
g) karcinom je karcinom prostate; ili
h) karcinom je karcinom gušterače; ili
i) karcinom je akutna mijelogena leukemija; ili
j) karcinom je difuzni limfom velikih B stanica; ili
k) karcinom je multipli mijelom.
43. Spoj prema bilo kojem od zahtjeva 1 do 37, ili njegova farmaceutski prihvatljiva sol, za upotrebu u:-
a) postupku liječenja mijeloproliferativnog poremećaja; ili
b) postupku liječenja mijeloproliferativnog poremećaja, pri čemu je mijeloproliferativni poremećaj policitemija vera, esencijalna trombocitemija, kronična mijelogena leukemija, mijelofibroza, primarna mijelofibroza, mijelofibroza s mijeloidnom metaplazijom, mijelofibroza nakon policitemije vere/esencijalne trombocitemije, mijelofibroza nakon esencijalne trombocitemije ili mijelofibroza nakon policitemije vere.
44. Spoj prema bilo kojem od zahtjeva 1 do 37, ili njegova farmaceutski prihvatljiva sol, za upotrebu u:-
a) postupku liječenja imunološkog poremećaja; ili
b) postupku liječenja imunološkog poremećaja, pri čemu je imunološki poremećaj autoimuna bolest; ili
c) postupku liječenja imunološkog poremećaja, pri čemu je imunološki poremećaj multipla skleroza, reumatoidni artritis, alergija, alergija na hranu, astma, lupus, upalna bolest crijeva ili ulcerozni kolitis, Crohnova bolest, sindrom iritabilnog crijeva, pankreatitis, divertikuloza, Gravesova bolest, dječji reumatoidni artritis, osteoartritis, psorijazni artritis, ankilozantni spondilitis, miastenija gravis, vaskulitis, autoimuni tireoiditis, dermatitis, psorijaza, skleroderma, sistemska skleroza, vitiligo, bolest “presatka protiv primatelja ”, Sjogrenov sindrom, glomerulonefritis, ili dijabetes melitus tip 1.
45. Spoj prema bilo kojem od zahtjeva 1 do 37, ili njegova farmaceutski prihvatljiva sol, za upotrebu u postupku liječenja ateroskleroze.
46. Spoj prema bilo kojem od zahtjeva 1 do 37, ili njegova farmaceutski prihvatljiva sol, za upotrebu u postupku smanjenja angiogeneze ili metastaza tumora.
47. Spoj prema zahtjevu 36, ili njegova farmaceutski prihvatljiva sol, za upotrebu u postupku liječenja karcinoma, pri čemu je karcinom akutna mijelogena leukemija.
48. Spoj prema zahtjevu 36, ili njegova farmaceutski prihvatljiva sol, za upotrebu u postupku liječenja karcinoma, pri čemu je karcinom difuzni limfom velikih B stanica.
49. Spoj prema zahtjevu 36, ili njegova farmaceutski prihvatljiva sol, za upotrebu u postupku liječenja karcinoma, pri čemu je karcinom mijelofibroza.
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