JP2016505021A5 - - Google Patents
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- Publication number
- JP2016505021A5 JP2016505021A5 JP2015552897A JP2015552897A JP2016505021A5 JP 2016505021 A5 JP2016505021 A5 JP 2016505021A5 JP 2015552897 A JP2015552897 A JP 2015552897A JP 2015552897 A JP2015552897 A JP 2015552897A JP 2016505021 A5 JP2016505021 A5 JP 2016505021A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- acceptable salt
- amino
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 131
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 17
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 103
- 150000003839 salts Chemical class 0.000 claims 93
- 125000001424 substituent group Chemical group 0.000 claims 38
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 29
- 229910052799 carbon Inorganic materials 0.000 claims 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 24
- 125000004432 carbon atom Chemical group C* 0.000 claims 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 13
- 206010028980 Neoplasm Diseases 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 201000011510 cancer Diseases 0.000 claims 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- -1 2,6-difluorophenyl Chemical group 0.000 claims 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 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 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 206010028537 myelofibrosis Diseases 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims 3
- 101150054691 PIM3 gene Proteins 0.000 claims 3
- 101150056413 Pim1 gene Proteins 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- WRTSMHBZVNBYRK-UHFFFAOYSA-N 3-amino-n-[4-(3-aminocyclohexyl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1C1CCCC(N)C1 WRTSMHBZVNBYRK-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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 208000017733 acquired polycythemia vera Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 208000037244 polycythemia vera Diseases 0.000 claims 2
- 208000003476 primary myelofibrosis Diseases 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- JUMHXVDASNXZCK-UHFFFAOYSA-N 3-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)-5-methylpyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC(C)=C1N1CC(C)C(O)C(N)C1 JUMHXVDASNXZCK-UHFFFAOYSA-N 0.000 claims 1
- NKUFQFKOCYCIBU-UHFFFAOYSA-N 3-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)pyridin-3-yl]-7-ethoxy-1,8-naphthyridine-2-carboxamide Chemical compound N=1C2=NC(OCC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CC(C)C(O)C(N)C1 NKUFQFKOCYCIBU-UHFFFAOYSA-N 0.000 claims 1
- GOMYQKXTHKSISF-UHFFFAOYSA-N 3-amino-n-[4-(3-amino-4-hydroxy-5-methylpiperidin-1-yl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CC(C)C(O)C(N)C1 GOMYQKXTHKSISF-UHFFFAOYSA-N 0.000 claims 1
- CDIASNJIOWVCSV-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=C2OCCC2=C1N1CCCC(N)C1 CDIASNJIOWVCSV-UHFFFAOYSA-N 0.000 claims 1
- QSUWTJZUEPZOOX-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-5-cyanopyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC(C#N)=C1N1CCCC(N)C1 QSUWTJZUEPZOOX-UHFFFAOYSA-N 0.000 claims 1
- PCBLQWCMPHDPQE-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-5-methylpyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC(C)=C1N1CCCC(N)C1 PCBLQWCMPHDPQE-UHFFFAOYSA-N 0.000 claims 1
- QQULFRBGXNZCES-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=C2C(O)CCC2=C1N1CCCC(N)C1 QQULFRBGXNZCES-UHFFFAOYSA-N 0.000 claims 1
- NLNNGHVRIKEROZ-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(1-fluoroethyl)quinoline-2-carboxamide Chemical compound N=1C2=CC(C(F)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 NLNNGHVRIKEROZ-UHFFFAOYSA-N 0.000 claims 1
- KHJUSTSHPOREIS-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(1-hydroxyethyl)quinoline-2-carboxamide Chemical compound N=1C2=CC(C(O)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 KHJUSTSHPOREIS-UHFFFAOYSA-N 0.000 claims 1
- HOJRGISHIKWYJZ-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(2,6-difluorophenyl)quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C=3C(=CC=CC=3F)F)=CC=C2C=C1N HOJRGISHIKWYJZ-UHFFFAOYSA-N 0.000 claims 1
- HNGITTXJRALLSW-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(2-cyano-6-fluorophenyl)quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C=3C(=CC=CC=3F)C#N)=CC=C2C=C1N HNGITTXJRALLSW-UHFFFAOYSA-N 0.000 claims 1
- WSVVRQHNTHXBJZ-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(2-cyanophenyl)quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C=3C(=CC=CC=3)C#N)=CC=C2C=C1N WSVVRQHNTHXBJZ-UHFFFAOYSA-N 0.000 claims 1
- USRTYRAHNYHTKH-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(cyanomethyl)quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(CC#N)=CC=C2C=C1N USRTYRAHNYHTKH-UHFFFAOYSA-N 0.000 claims 1
- UDDBBYAKVUDFNK-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(morpholin-4-ylmethyl)quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(CN3CCOCC3)=CC=C2C=C1N UDDBBYAKVUDFNK-UHFFFAOYSA-N 0.000 claims 1
- CECWJCILCAIQAC-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-(pyrrolidin-1-ylmethyl)quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(CN3CCCC3)=CC=C2C=C1N CECWJCILCAIQAC-UHFFFAOYSA-N 0.000 claims 1
- VQDNDMIJBAPVRG-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-[(dimethylamino)methyl]quinoline-2-carboxamide Chemical compound N=1C2=CC(CN(C)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 VQDNDMIJBAPVRG-UHFFFAOYSA-N 0.000 claims 1
- ZRNUNAHKAVZXIQ-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-[hydroxy(phenyl)methyl]quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C(O)C=3C=CC=CC=3)=CC=C2C=C1N ZRNUNAHKAVZXIQ-UHFFFAOYSA-N 0.000 claims 1
- IUWQFPCBLRECFE-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-ethoxy-1,8-naphthyridine-2-carboxamide Chemical compound N=1C2=NC(OCC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 IUWQFPCBLRECFE-UHFFFAOYSA-N 0.000 claims 1
- CTKJRRFLVNYGTD-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-ethyl-1,6-naphthyridine-2-carboxamide Chemical compound NC=1C=C2C=NC(CC)=CC2=NC=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 CTKJRRFLVNYGTD-UHFFFAOYSA-N 0.000 claims 1
- VPQMMXPQFSHBJT-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-ethyl-6-fluoroquinoline-2-carboxamide Chemical compound NC=1C=C2C=C(F)C(CC)=CC2=NC=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 VPQMMXPQFSHBJT-UHFFFAOYSA-N 0.000 claims 1
- HHGGKGRBPVOWBO-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 HHGGKGRBPVOWBO-UHFFFAOYSA-N 0.000 claims 1
- AMNYMLVTVLXRTN-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-piperidin-4-ylquinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C3CCNCC3)=CC=C2C=C1N AMNYMLVTVLXRTN-UHFFFAOYSA-N 0.000 claims 1
- FJYFIHVJKOMXRN-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]-7-propan-2-ylquinoline-2-carboxamide Chemical compound N=1C2=CC(C(C)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCCC(N)C1 FJYFIHVJKOMXRN-UHFFFAOYSA-N 0.000 claims 1
- LSPMPLWLIFDEJM-UHFFFAOYSA-N 3-amino-n-[4-(3-aminopiperidin-1-yl)pyridin-3-yl]quinoline-2-carboxamide Chemical compound C1C(N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC=CC=C2C=C1N LSPMPLWLIFDEJM-UHFFFAOYSA-N 0.000 claims 1
- JUMHXVDASNXZCK-FPULEUEGSA-N 3-amino-n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]-5-methylpyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC(C)=C1N1C[C@H](C)[C@@H](O)[C@H](N)C1 JUMHXVDASNXZCK-FPULEUEGSA-N 0.000 claims 1
- NKUFQFKOCYCIBU-PGICJIBASA-N 3-amino-n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]pyridin-3-yl]-7-ethoxy-1,8-naphthyridine-2-carboxamide Chemical compound N=1C2=NC(OCC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1C[C@H](C)[C@@H](O)[C@H](N)C1 NKUFQFKOCYCIBU-PGICJIBASA-N 0.000 claims 1
- GOMYQKXTHKSISF-OIAISFKWSA-N 3-amino-n-[4-[(3r,4r,5s)-3-amino-4-hydroxy-5-methylpiperidin-1-yl]pyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1C[C@H](C)[C@@H](O)[C@H](N)C1 GOMYQKXTHKSISF-OIAISFKWSA-N 0.000 claims 1
- CDIASNJIOWVCSV-INIZCTEOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]-2,3-dihydrofuro[2,3-b]pyridin-5-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=C2OCCC2=C1N1CCC[C@H](N)C1 CDIASNJIOWVCSV-INIZCTEOSA-N 0.000 claims 1
- QSUWTJZUEPZOOX-KRWDZBQOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]-5-cyanopyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC(C#N)=C1N1CCC[C@H](N)C1 QSUWTJZUEPZOOX-KRWDZBQOSA-N 0.000 claims 1
- PCBLQWCMPHDPQE-KRWDZBQOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]-5-methylpyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC(C)=C1N1CCC[C@H](N)C1 PCBLQWCMPHDPQE-KRWDZBQOSA-N 0.000 claims 1
- QQULFRBGXNZCES-BJQOMGFOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]-7-hydroxy-6,7-dihydro-5h-cyclopenta[b]pyridin-3-yl]-7-ethylquinoline-2-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2C=C(N)C=1C(=O)NC1=CN=C2C(O)CCC2=C1N1CCC[C@H](N)C1 QQULFRBGXNZCES-BJQOMGFOSA-N 0.000 claims 1
- NLNNGHVRIKEROZ-VYIIXAMBSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(1-fluoroethyl)quinoline-2-carboxamide Chemical compound N=1C2=CC(C(F)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCC[C@H](N)C1 NLNNGHVRIKEROZ-VYIIXAMBSA-N 0.000 claims 1
- KHJUSTSHPOREIS-VYIIXAMBSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(1-hydroxyethyl)quinoline-2-carboxamide Chemical compound N=1C2=CC(C(O)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCC[C@H](N)C1 KHJUSTSHPOREIS-VYIIXAMBSA-N 0.000 claims 1
- HOJRGISHIKWYJZ-KRWDZBQOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(2,6-difluorophenyl)quinoline-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C=3C(=CC=CC=3F)F)=CC=C2C=C1N HOJRGISHIKWYJZ-KRWDZBQOSA-N 0.000 claims 1
- HNGITTXJRALLSW-IBGZPJMESA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(2-cyano-6-fluorophenyl)quinoline-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C=3C(=CC=CC=3F)C#N)=CC=C2C=C1N HNGITTXJRALLSW-IBGZPJMESA-N 0.000 claims 1
- WSVVRQHNTHXBJZ-FQEVSTJZSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(2-cyanophenyl)quinoline-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C=3C(=CC=CC=3)C#N)=CC=C2C=C1N WSVVRQHNTHXBJZ-FQEVSTJZSA-N 0.000 claims 1
- NSMUWQGNLKGWFQ-INIZCTEOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(2-hydroxypropan-2-yl)quinoline-2-carboxamide Chemical compound N=1C2=CC(C(C)(O)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCC[C@H](N)C1 NSMUWQGNLKGWFQ-INIZCTEOSA-N 0.000 claims 1
- USRTYRAHNYHTKH-INIZCTEOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(cyanomethyl)quinoline-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(CC#N)=CC=C2C=C1N USRTYRAHNYHTKH-INIZCTEOSA-N 0.000 claims 1
- UDDBBYAKVUDFNK-IBGZPJMESA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(morpholin-4-ylmethyl)quinoline-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(CN3CCOCC3)=CC=C2C=C1N UDDBBYAKVUDFNK-IBGZPJMESA-N 0.000 claims 1
- CECWJCILCAIQAC-IBGZPJMESA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-(pyrrolidin-1-ylmethyl)quinoline-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(CN3CCCC3)=CC=C2C=C1N CECWJCILCAIQAC-IBGZPJMESA-N 0.000 claims 1
- VQDNDMIJBAPVRG-KRWDZBQOSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-[(dimethylamino)methyl]quinoline-2-carboxamide Chemical compound N=1C2=CC(CN(C)C)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCC[C@H](N)C1 VQDNDMIJBAPVRG-KRWDZBQOSA-N 0.000 claims 1
- ZRNUNAHKAVZXIQ-DQUNLGLBSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-[hydroxy(phenyl)methyl]quinoline-2-carboxamide Chemical compound C1[C@@H](N)CCCN1C1=CC=NC=C1NC(=O)C1=NC2=CC(C(O)C=3C=CC=CC=3)=CC=C2C=C1N ZRNUNAHKAVZXIQ-DQUNLGLBSA-N 0.000 claims 1
- IUWQFPCBLRECFE-AWEZNQCLSA-N 3-amino-n-[4-[(3s)-3-aminopiperidin-1-yl]pyridin-3-yl]-7-ethoxy-1,8-naphthyridine-2-carboxamide Chemical compound N=1C2=NC(OCC)=CC=C2C=C(N)C=1C(=O)NC1=CN=CC=C1N1CCC[C@H](N)C1 IUWQFPCBLRECFE-AWEZNQCLSA-N 0.000 claims 1
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2014
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- 2014-01-14 WO PCT/US2014/011487 patent/WO2014110574A1/en not_active Ceased
- 2014-01-14 US US14/155,134 patent/US9278950B2/en active Active
- 2014-01-14 JP JP2015552897A patent/JP6437452B2/ja active Active
- 2014-01-14 CA CA2897200A patent/CA2897200C/en active Active
- 2014-01-14 EP EP14702167.9A patent/EP2943485B1/en active Active
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2016
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