JP2018522859A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018522859A5 JP2018522859A5 JP2017566643A JP2017566643A JP2018522859A5 JP 2018522859 A5 JP2018522859 A5 JP 2018522859A5 JP 2017566643 A JP2017566643 A JP 2017566643A JP 2017566643 A JP2017566643 A JP 2017566643A JP 2018522859 A5 JP2018522859 A5 JP 2018522859A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyridine
- pyrazolo
- carbonitrile
- isopropylamino
- 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
Links
- -1 pyrrolo [2,3-b] pyridinyl Chemical group 0.000 claims 288
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 49
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000004076 pyridyl group Chemical group 0.000 claims 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000002757 morpholinyl group Chemical group 0.000 claims 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000003566 oxetanyl group Chemical group 0.000 claims 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 6
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 6
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 6
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims 6
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 4
- ZVSYSFPBYMUXLC-UHFFFAOYSA-N 4-[1-[6-(6-aminopyrazolo[3,4-d]pyrimidin-1-yl)-4-(propan-2-ylamino)pyridin-3-yl]triazol-4-yl]-2-methylbutan-2-ol Chemical compound NC1=NC=C2C(=N1)N(N=C2)C1=CC(=C(C=N1)N1N=NC(=C1)CCC(C)(O)C)NC(C)C ZVSYSFPBYMUXLC-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 3
- YDYCDZAGEVISQN-UHFFFAOYSA-N 1-[4-(propan-2-ylamino)-5-[1-(pyridin-3-ylmethyl)imidazol-4-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=CN(C=1)CC=1C=NC=CC=1)N1N=CC=2C1=NC=C(C=2)C#N YDYCDZAGEVISQN-UHFFFAOYSA-N 0.000 claims 3
- UAKXTRKWNJDLPB-UHFFFAOYSA-N 1-[5-[1-(cyclobutylmethyl)imidazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1(CCC1)CN1C=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C UAKXTRKWNJDLPB-UHFFFAOYSA-N 0.000 claims 3
- UEWIETUNZIVFLI-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound N#CC1=CN=C2NN=CC2=C1 UEWIETUNZIVFLI-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 229960004979 fampridine Drugs 0.000 claims 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims 3
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 3
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 3
- 125000006308 propyl amino group Chemical group 0.000 claims 3
- 125000003944 tolyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- WDKWTXHBEQGLDD-MOPGFXCFSA-N (3S,4R)-4-[4-[4-(propan-2-ylamino)-6-pyrrolo[2,3-d]pyrimidin-7-ylpyridin-3-yl]triazol-1-yl]piperidin-3-ol Chemical compound C(C)(C)NC1=C(C=NC(=C1)N1C=CC2=C1N=CN=C2)C=1N=NN(C=1)[C@H]1[C@H](CNCC1)O WDKWTXHBEQGLDD-MOPGFXCFSA-N 0.000 claims 2
- RWZHPKWFPPNOAS-UHFFFAOYSA-N 1-[4-(cyclopropylamino)-5-[1-(2-morpholin-4-ylethyl)triazol-4-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1(CC1)NC1=CC(=NC=C1C=1N=NN(C=1)CCN1CCOCC1)N1N=CC=2C1=NC=C(C=2)C#N RWZHPKWFPPNOAS-UHFFFAOYSA-N 0.000 claims 2
- NFXCQYWCKQXKNH-UHFFFAOYSA-N 1-[4-(ethylamino)-5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)NC1=CC(=NC=C1N1N=NC(=C1)CCC(C)(C)O)N1N=CC=2C1=NC=C(C=2)C#N NFXCQYWCKQXKNH-UHFFFAOYSA-N 0.000 claims 2
- WFXUFTVYIODYSW-UHFFFAOYSA-N 1-[4-(propan-2-ylamino)-5-(1-propan-2-yltriazol-4-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)N1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C WFXUFTVYIODYSW-UHFFFAOYSA-N 0.000 claims 2
- BIVUPILKVLGWCD-UHFFFAOYSA-N 1-[4-(propan-2-ylamino)-5-(4-pyridin-4-yltriazol-1-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1N1N=NC(=C1)C1=CC=NC=C1)N1N=CC=2C1=NC=C(C=2)C#N BIVUPILKVLGWCD-UHFFFAOYSA-N 0.000 claims 2
- ZICCFWLRNRLUAR-UHFFFAOYSA-N 1-[4-(propan-2-ylamino)-5-[1-(2-pyridin-3-ylethyl)triazol-4-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)CCC=1C=NC=CC=1)N1N=CC=2C1=NC=C(C=2)C#N ZICCFWLRNRLUAR-UHFFFAOYSA-N 0.000 claims 2
- VNMBWKIBKVDUQH-UHFFFAOYSA-N 1-[4-(propan-2-ylamino)-5-[1-(3,3,3-trifluoro-2-hydroxypropyl)triazol-4-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)CC(C(F)(F)F)O)N1N=CC=2C1=NC=C(C=2)C#N VNMBWKIBKVDUQH-UHFFFAOYSA-N 0.000 claims 2
- XWBDFMDMJONMGG-UHFFFAOYSA-N 1-[4-(propan-2-ylamino)-5-[1-(3,3,3-trifluoropropyl)triazol-4-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)CCC(F)(F)F)N1N=CC=2C1=NC=C(C=2)C#N XWBDFMDMJONMGG-UHFFFAOYSA-N 0.000 claims 2
- HNMRNLZZMIYBDI-UHFFFAOYSA-N 1-[4-(propan-2-ylamino)-5-[1-(pyridin-2-ylmethyl)imidazol-4-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=CN(C=1)CC1=NC=CC=C1)N1N=CC=2C1=NC=C(C=2)C#N HNMRNLZZMIYBDI-UHFFFAOYSA-N 0.000 claims 2
- FXDLVCIMARHHGW-HNNXBMFYSA-N 1-[4-(propan-2-ylamino)-5-[3-[(3S)-pyrrolidin-3-yl]-1,2-oxazol-5-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C1=CC(=NO1)[C@@H]1CNCC1)N1N=CC=2C1=NC=C(C=2)C#N FXDLVCIMARHHGW-HNNXBMFYSA-N 0.000 claims 2
- ZXJRCPSBIZZWNF-UHFFFAOYSA-N 1-[4-[(3,3-difluorocyclopentyl)amino]-5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound FC1(CC(CC1)NC1=CC(=NC=C1N1N=NC(=C1)CCC(C)(C)O)N1N=CC=2C1=NC=C(C=2)C#N)F ZXJRCPSBIZZWNF-UHFFFAOYSA-N 0.000 claims 2
- ILTURIUIZYWDGR-UHFFFAOYSA-N 1-[4-[(3-fluorocyclopentyl)amino]-5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound FC1CC(CC1)NC1=CC(=NC=C1N1N=NC(=C1)CCC(C)(C)O)N1N=CC=2C1=NC=C(C=2)C#N ILTURIUIZYWDGR-UHFFFAOYSA-N 0.000 claims 2
- ILTURIUIZYWDGR-MSOLQXFVSA-N 1-[4-[[(1S,3R)-3-fluorocyclopentyl]amino]-5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound F[C@H]1C[C@H](CC1)NC1=CC(=NC=C1N1N=NC(=C1)CCC(C)(C)O)N1N=CC=2C1=NC=C(C=2)C#N ILTURIUIZYWDGR-MSOLQXFVSA-N 0.000 claims 2
- WCFWKNTYYISRNT-ZDUSSCGKSA-N 1-[4-[[(2S)-1-hydroxypropan-2-yl]amino]-5-(1-propyltriazol-4-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC[C@H](C)NC1=CC(=NC=C1C=1N=NN(C=1)CCC)N1N=CC=2C1=NC=C(C=2)C#N WCFWKNTYYISRNT-ZDUSSCGKSA-N 0.000 claims 2
- AFKCXNDYRDTDFL-ZDUSSCGKSA-N 1-[4-[[(2S)-1-hydroxypropan-2-yl]amino]-5-(4-propyltriazol-1-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC[C@H](C)NC1=CC(=NC=C1N1N=NC(=C1)CCC)N1N=CC=2C1=NC=C(C=2)C#N AFKCXNDYRDTDFL-ZDUSSCGKSA-N 0.000 claims 2
- HDPGEKCXDTWNJW-UHFFFAOYSA-N 1-[4-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-(1-propyltriazol-4-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound FC(CN1N=CC(=C1)NC1=CC(=NC=C1C=1N=NN(C=1)CCC)N1N=CC=2C1=NC=C(C=2)C#N)F HDPGEKCXDTWNJW-UHFFFAOYSA-N 0.000 claims 2
- NGZZECNYMIIQDH-UHFFFAOYSA-N 1-[4-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-(4-propyltriazol-1-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound FC(CN1N=CC(=C1)NC1=CC(=NC=C1N1N=NC(=C1)CCC)N1N=CC=2C1=NC=C(C=2)C#N)F NGZZECNYMIIQDH-UHFFFAOYSA-N 0.000 claims 2
- QYWVVTPNRHZJIA-UHFFFAOYSA-N 1-[5-(1-benzylimidazol-4-yl)-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C1=CC=CC=C1)N1C=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C QYWVVTPNRHZJIA-UHFFFAOYSA-N 0.000 claims 2
- GZLLTCBFIZUKFY-UHFFFAOYSA-N 1-[5-(1-cyclopropylpyrazol-4-yl)-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1(CC1)N1N=CC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C GZLLTCBFIZUKFY-UHFFFAOYSA-N 0.000 claims 2
- QDFAFMOTRUAWKR-UHFFFAOYSA-N 1-[5-(1-methyltriazol-4-yl)-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)C)N1N=CC=2C1=NC=C(C=2)C#N QDFAFMOTRUAWKR-UHFFFAOYSA-N 0.000 claims 2
- OUHVERMVYFZTOV-UHFFFAOYSA-N 1-[5-(1-phenyltriazol-4-yl)-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)C1=CC=CC=C1)N1N=CC=2C1=NC=C(C=2)C#N OUHVERMVYFZTOV-UHFFFAOYSA-N 0.000 claims 2
- QKCBKWKHRLVYNM-UHFFFAOYSA-N 1-[5-(1H-imidazol-5-yl)-4-(propan-2-ylamino)pyridin-2-yl]indazole-5-carbonitrile Chemical compound N1C=NC(=C1)C=1C(=CC(=NC=1)N1N=CC2=CC(=CC=C12)C#N)NC(C)C QKCBKWKHRLVYNM-UHFFFAOYSA-N 0.000 claims 2
- GESPJMQHCGMXFX-UHFFFAOYSA-N 1-[5-(4-benzylpyrazol-1-yl)-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C1=CC=CC=C1)C=1C=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C GESPJMQHCGMXFX-UHFFFAOYSA-N 0.000 claims 2
- HLUBXJPMMWMTCU-UHFFFAOYSA-N 1-[5-(4-butyltriazol-1-yl)-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(CCC)C=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C HLUBXJPMMWMTCU-UHFFFAOYSA-N 0.000 claims 2
- PCNBXGOWAZIQJW-UHFFFAOYSA-N 1-[5-[1-(1-acetylazetidin-3-yl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(=O)N1CC(C1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C PCNBXGOWAZIQJW-UHFFFAOYSA-N 0.000 claims 2
- QUUWSBJXAAYZSG-UHFFFAOYSA-N 1-[5-[1-(1-methylsulfonylpiperidin-4-yl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)C1CCN(CC1)S(=O)(=O)C)N1N=CC=2C1=NC=C(C=2)C#N QUUWSBJXAAYZSG-UHFFFAOYSA-N 0.000 claims 2
- VGEDKLMAYHYXNY-UHFFFAOYSA-N 1-[5-[1-(1-phenylethyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)C(C)C1=CC=CC=C1)N1N=CC=2C1=NC=C(C=2)C#N VGEDKLMAYHYXNY-UHFFFAOYSA-N 0.000 claims 2
- YLYBNASRFJCAHV-UHFFFAOYSA-N 1-[5-[1-(2-fluorophenyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound FC1=C(C=CC=C1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C YLYBNASRFJCAHV-UHFFFAOYSA-N 0.000 claims 2
- AUUDQVSCLJRITL-UHFFFAOYSA-N 1-[5-[1-(2-hydroxy-3-methylbutyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)C(C)C AUUDQVSCLJRITL-UHFFFAOYSA-N 0.000 claims 2
- ZKNNTZMYAGDKCS-UHFFFAOYSA-N 1-[5-[1-(2-hydroxyethyl)pyrazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OCCN1N=CC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C ZKNNTZMYAGDKCS-UHFFFAOYSA-N 0.000 claims 2
- KOBQCUBYLXIFBT-UHFFFAOYSA-N 1-[5-[1-(2-hydroxyethyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OCCN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C KOBQCUBYLXIFBT-UHFFFAOYSA-N 0.000 claims 2
- GOICDGNZHFRGGP-UHFFFAOYSA-N 1-[5-[1-(2-methylpropyl)imidazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C(C)C)N1C=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C GOICDGNZHFRGGP-UHFFFAOYSA-N 0.000 claims 2
- OBXIRKJVYBHDAX-UHFFFAOYSA-N 1-[5-[1-(2-methylpropyl)pyrazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C(C)C)N1N=CC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C OBXIRKJVYBHDAX-UHFFFAOYSA-N 0.000 claims 2
- XXYRXDJPGWEELQ-UHFFFAOYSA-N 1-[5-[1-(2-oxopropyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)CC(C)=O)N1N=CC=2C1=NC=C(C=2)C#N XXYRXDJPGWEELQ-UHFFFAOYSA-N 0.000 claims 2
- FFZRTARGPDRNMH-UHFFFAOYSA-N 1-[5-[1-(3-aminopropyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound NCCCN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C FFZRTARGPDRNMH-UHFFFAOYSA-N 0.000 claims 2
- UGKFZUXNAKECGJ-UHFFFAOYSA-N 1-[5-[1-(3-hydroxy-3-methylbutyl)imidazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCN1C=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)(C)C UGKFZUXNAKECGJ-UHFFFAOYSA-N 0.000 claims 2
- IPXFYLMXKDCHJJ-UHFFFAOYSA-N 1-[5-[1-(3-hydroxyphenyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC=1C=C(C=CC=1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C IPXFYLMXKDCHJJ-UHFFFAOYSA-N 0.000 claims 2
- GGRAWYSSBLFZLF-UHFFFAOYSA-N 1-[5-[1-(4-fluorophenyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C GGRAWYSSBLFZLF-UHFFFAOYSA-N 0.000 claims 2
- MWVLHMHOLKMYMH-UHFFFAOYSA-N 1-[5-[1-(5-hydroxypentyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OCCCCCN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C MWVLHMHOLKMYMH-UHFFFAOYSA-N 0.000 claims 2
- DEMIRDKJAZCIKQ-UHFFFAOYSA-N 1-[5-[1-(cyclopropylmethyl)imidazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1(CC1)CN1C=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C DEMIRDKJAZCIKQ-UHFFFAOYSA-N 0.000 claims 2
- IWFABHLRWIUEBE-UHFFFAOYSA-N 1-[5-[1-(oxetan-3-ylmethyl)pyrazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1C=NN(C=1)CC1COC1)N1N=CC=2C1=NC=C(C=2)C#N IWFABHLRWIUEBE-UHFFFAOYSA-N 0.000 claims 2
- OCVYNVMYNRHDQO-HSZRJFAPSA-N 1-[5-[1-[(1S)-2-hydroxy-1-phenylethyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC[C@H](C1=CC=CC=C1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C OCVYNVMYNRHDQO-HSZRJFAPSA-N 0.000 claims 2
- BBJXHULXANBCKM-UHFFFAOYSA-N 1-[5-[1-[(2-methyl-1,3-benzothiazol-5-yl)methyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)CC=1C=CC2=C(N=C(S2)C)C=1)N1N=CC=2C1=NC=C(C=2)C#N BBJXHULXANBCKM-UHFFFAOYSA-N 0.000 claims 2
- KABVKRYOIRXXRB-CYBMUJFWSA-N 1-[5-[1-[(2R)-2-hydroxypropyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound O[C@@H](CN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)C KABVKRYOIRXXRB-CYBMUJFWSA-N 0.000 claims 2
- UHXFMQJYIGYPGA-HSZRJFAPSA-N 1-[5-[1-[(2S)-2-hydroxy-2-phenylethyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound O[C@H](CN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)C1=CC=CC=C1 UHXFMQJYIGYPGA-HSZRJFAPSA-N 0.000 claims 2
- HWUDIBHSVZRJER-AWEZNQCLSA-N 1-[5-[1-[(2S)-2-hydroxypropyl]imidazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound O[C@H](CN1C=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)C HWUDIBHSVZRJER-AWEZNQCLSA-N 0.000 claims 2
- QCYBEIUZSYEGNW-FXAWDEMLSA-N 1-[5-[1-[(3S,4R)-3-fluoropiperidin-4-yl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound CC(C)NC1=CC(=NC=C1C1=CN(N=N1)[C@@H]1CCNC[C@@H]1F)N1N=CC2=C1N=CC(=C2)C#N QCYBEIUZSYEGNW-FXAWDEMLSA-N 0.000 claims 2
- BFKKIDHWWRDAPL-UHFFFAOYSA-N 1-[5-[1-[1-(5-methyl-1,3,4-oxadiazol-2-yl)azetidin-3-yl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)C1CN(C1)C=1OC(=NN=1)C)N1N=CC=2C1=NC=C(C=2)C#N BFKKIDHWWRDAPL-UHFFFAOYSA-N 0.000 claims 2
- NXTYKRONDSTYMX-UHFFFAOYSA-N 1-[5-[1-[1-(cyclopropanecarbonyl)azetidin-3-yl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C1(CC1)C(=O)N1CC(C1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C NXTYKRONDSTYMX-UHFFFAOYSA-N 0.000 claims 2
- YXEFNKLNAGUSLQ-UHFFFAOYSA-N 1-[5-[1-[2-(dimethylamino)ethyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound CN(CCN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)C YXEFNKLNAGUSLQ-UHFFFAOYSA-N 0.000 claims 2
- ZCSYBNDQNSLHCV-UHFFFAOYSA-N 1-[5-[1-[2-hydroxy-3-(4-methoxyphenoxy)propyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CN1N=NC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)COC1=CC=C(C=C1)OC ZCSYBNDQNSLHCV-UHFFFAOYSA-N 0.000 claims 2
- WENVBILCCSYPQW-UHFFFAOYSA-N 1-[5-[3-(1-acetylpiperidin-4-yl)-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(=O)N1CCC(CC1)C1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C WENVBILCCSYPQW-UHFFFAOYSA-N 0.000 claims 2
- RHEFUXIXJKSSIC-UHFFFAOYSA-N 1-[5-[3-(3-hydroxy-3-methylbutyl)-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCC1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)(C)C RHEFUXIXJKSSIC-UHFFFAOYSA-N 0.000 claims 2
- IRRKGXSFAZPFGG-UHFFFAOYSA-N 1-[5-[3-(4,4-difluoropiperidin-2-yl)-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound FC1(CC(NCC1)C1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)F IRRKGXSFAZPFGG-UHFFFAOYSA-N 0.000 claims 2
- OGWLTFFSPCXDEN-UHFFFAOYSA-N 1-[5-[3-(6,6-dimethylmorpholin-3-yl)-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound CC1(OCC(NC1)C1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)C OGWLTFFSPCXDEN-UHFFFAOYSA-N 0.000 claims 2
- GYAGPBWJEYTPBJ-UHFFFAOYSA-N 1-[5-[3-(8-acetyl-8-azabicyclo[3.2.1]octan-3-yl)-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(=O)N1C2CC(CC1CC2)C1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C GYAGPBWJEYTPBJ-UHFFFAOYSA-N 0.000 claims 2
- WRWNPDTZJNLWHL-UHFFFAOYSA-N 1-[5-[3-(azetidin-3-yl)-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound N1CC(C1)C1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C WRWNPDTZJNLWHL-UHFFFAOYSA-N 0.000 claims 2
- PGGIIIXXQAYLBU-UHFFFAOYSA-N 1-[5-[3-(oxan-4-yl)-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C1=CC(=NO1)C1CCOCC1)N1N=CC=2C1=NC=C(C=2)C#N PGGIIIXXQAYLBU-UHFFFAOYSA-N 0.000 claims 2
- XFKBTLSDEIJMNJ-SFHVURJKSA-N 1-[5-[3-[(2S)-piperidin-2-yl]-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C1=CC(=NO1)[C@H]1NCCCC1)N1N=CC=2C1=NC=C(C=2)C#N XFKBTLSDEIJMNJ-SFHVURJKSA-N 0.000 claims 2
- LSEFDRAJFXMNQH-KRWDZBQOSA-N 1-[5-[3-[(3S)-1-acetylpyrrolidin-3-yl]-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(=O)N1C[C@H](CC1)C1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C LSEFDRAJFXMNQH-KRWDZBQOSA-N 0.000 claims 2
- OPZGOIIFIKCGNP-UHFFFAOYSA-N 1-[5-[4-(1-acetylazetidin-3-yl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(=O)N1CC(C1)C=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C OPZGOIIFIKCGNP-UHFFFAOYSA-N 0.000 claims 2
- AITZXVLIDDMWAO-UHFFFAOYSA-N 1-[5-[4-(1-methylsulfonylpiperidin-4-yl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1N1N=NC(=C1)C1CCN(CC1)S(=O)(=O)C)N1N=CC=2C1=NC=C(C=2)C#N AITZXVLIDDMWAO-UHFFFAOYSA-N 0.000 claims 2
- WOWSRCBFYWSBCH-UHFFFAOYSA-N 1-[5-[4-(2-hydroxy-2-methylbutyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)(CC)C WOWSRCBFYWSBCH-UHFFFAOYSA-N 0.000 claims 2
- BNCKJPPMQIMLAL-UHFFFAOYSA-N 1-[5-[4-(2-hydroxybutyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)CC BNCKJPPMQIMLAL-UHFFFAOYSA-N 0.000 claims 2
- SFUBJXVEVCGZIJ-UHFFFAOYSA-N 1-[5-[4-(2-hydroxyethyl)pyrazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OCCC=1C=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C SFUBJXVEVCGZIJ-UHFFFAOYSA-N 0.000 claims 2
- GDXLYQWXZNXNDM-UHFFFAOYSA-N 1-[5-[4-(2-hydroxyethyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OCCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C GDXLYQWXZNXNDM-UHFFFAOYSA-N 0.000 claims 2
- UGDBUTSCGFDAAN-UHFFFAOYSA-N 1-[5-[4-(2-hydroxypropan-2-yl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(C)(C)C=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C UGDBUTSCGFDAAN-UHFFFAOYSA-N 0.000 claims 2
- HRZKBJFQSQYJPJ-UHFFFAOYSA-N 1-[5-[4-(2-oxopropyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1N1N=NC(=C1)CC(C)=O)N1N=CC=2C1=NC=C(C=2)C#N HRZKBJFQSQYJPJ-UHFFFAOYSA-N 0.000 claims 2
- UYEYUIJZWTVIAP-UHFFFAOYSA-N 1-[5-[4-(2-phenylethyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1N1N=NC(=C1)CCC1=CC=CC=C1)N1N=CC=2C1=NC=C(C=2)C#N UYEYUIJZWTVIAP-UHFFFAOYSA-N 0.000 claims 2
- CQFUXLDLZJTFNZ-UHFFFAOYSA-N 1-[5-[4-(3-aminopropyl)pyrazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound NCCCC=1C=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C CQFUXLDLZJTFNZ-UHFFFAOYSA-N 0.000 claims 2
- DOQRUHZTCTUYTQ-UHFFFAOYSA-N 1-[5-[4-(3-fluoro-3-methylbutyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-d]pyrimidin-6-amine Chemical compound FC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC(=NC=2)N)NC(C)C)(C)C DOQRUHZTCTUYTQ-UHFFFAOYSA-N 0.000 claims 2
- FIOZNXBIZWGUHJ-UHFFFAOYSA-N 1-[5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]-4-(3,3,3-trifluoropropylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NCCC(F)(F)F)(C)C FIOZNXBIZWGUHJ-UHFFFAOYSA-N 0.000 claims 2
- QUQQYGRTGFLKDR-UHFFFAOYSA-N 1-[5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]-4-(oxetan-3-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC1COC1)(C)C QUQQYGRTGFLKDR-UHFFFAOYSA-N 0.000 claims 2
- JXMPVWXEDGELMJ-UHFFFAOYSA-N 1-[5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)(C)C JXMPVWXEDGELMJ-UHFFFAOYSA-N 0.000 claims 2
- DHBSJTRSMVNKQS-UHFFFAOYSA-N 1-[5-[4-(3-hydroxypropyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OCCCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C DHBSJTRSMVNKQS-UHFFFAOYSA-N 0.000 claims 2
- DRITYCPYJCNBLU-UHFFFAOYSA-N 1-[5-[4-(3-methylbutyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(CC(C)C)C=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C DRITYCPYJCNBLU-UHFFFAOYSA-N 0.000 claims 2
- ZPXBUAUZXWENBV-UHFFFAOYSA-N 1-[5-[4-(aminomethyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound NCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C ZPXBUAUZXWENBV-UHFFFAOYSA-N 0.000 claims 2
- UBUOCHKAAOWCSG-UHFFFAOYSA-N 1-[5-[4-(diethylaminomethyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)N(CC)CC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C UBUOCHKAAOWCSG-UHFFFAOYSA-N 0.000 claims 2
- ZKBYGRZJWHEKKH-UHFFFAOYSA-N 1-[5-[4-(methoxymethyl)triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1N1N=NC(=C1)COC)N1N=CC=2C1=NC=C(C=2)C#N ZKBYGRZJWHEKKH-UHFFFAOYSA-N 0.000 claims 2
- RMUWYPKKDUJJSH-HSZRJFAPSA-N 1-[5-[4-[(2R)-2-hydroxy-2-phenylethyl]triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound O[C@H](CC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)C1=CC=CC=C1 RMUWYPKKDUJJSH-HSZRJFAPSA-N 0.000 claims 2
- RHROAFKGAHMNEG-JOCHJYFZSA-N 1-[5-[4-[(3R)-3,4-dihydroxy-3-methylbutyl]triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound O[C@](CCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)(CO)C RHROAFKGAHMNEG-JOCHJYFZSA-N 0.000 claims 2
- LWNOJPJHKZHEHA-UHFFFAOYSA-N 1-[5-[4-[(dimethylamino)methyl]triazol-1-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound CN(C)CC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C LWNOJPJHKZHEHA-UHFFFAOYSA-N 0.000 claims 2
- FSOWYLCXURDNLF-UHFFFAOYSA-N 1-[5-[5-(3-hydroxy-3-methylbutyl)-1,2-oxazol-3-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCC1=CC(=NO1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)(C)C FSOWYLCXURDNLF-UHFFFAOYSA-N 0.000 claims 2
- LXVPQTIWYGXBLL-UHFFFAOYSA-N 1-[5-[5-(3-hydroxy-3-methylbutyl)-4,5-dihydro-1,2-oxazol-3-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCC1CC(=NO1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C)(C)C LXVPQTIWYGXBLL-UHFFFAOYSA-N 0.000 claims 2
- DUCXLWBEJQZKDI-UHFFFAOYSA-N 1-[5-[5-(morpholine-4-carbonyl)-1,3,4-oxadiazol-2-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1OC(=NN=1)C(=O)N1CCOCC1)N1N=CC=2C1=NC=C(C=2)C#N DUCXLWBEJQZKDI-UHFFFAOYSA-N 0.000 claims 2
- NRGDEORDTOJJIU-NRFANRHFSA-N 1-[5-[5-[(2S)-1-methylsulfonylpiperidin-2-yl]-1,2-oxazol-3-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C1=NOC(=C1)[C@H]1N(CCCC1)S(=O)(=O)C)N1N=CC=2C1=NC=C(C=2)C#N NRGDEORDTOJJIU-NRFANRHFSA-N 0.000 claims 2
- CVGBIZKPZLMEAP-IBGZPJMESA-N 1-[5-[5-[(3S)-morpholin-3-yl]-1,2-oxazol-3-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C1=NOC(=C1)[C@H]1NCCOC1)N1N=CC=2C1=NC=C(C=2)C#N CVGBIZKPZLMEAP-IBGZPJMESA-N 0.000 claims 2
- OQPANNITXUVIRV-UHFFFAOYSA-N 1-[6-(5-cyanopyrazolo[3,4-b]pyridin-1-yl)-4-(propan-2-ylamino)pyridin-3-yl]triazole-4-carboxamide Chemical compound C(#N)C=1C=C2C(=NC=1)N(N=C2)C1=CC(=C(C=N1)N1N=NC(=C1)C(=O)N)NC(C)C OQPANNITXUVIRV-UHFFFAOYSA-N 0.000 claims 2
- FOEMNUAURRCULJ-UHFFFAOYSA-N 2-(5-chloropyrazolo[3,4-b]pyridin-1-yl)-N-cyclopropyl-5-(1-propyltriazol-4-yl)pyridin-4-amine Chemical compound ClC=1C=C2C(=NC=1)N(N=C2)C1=NC=C(C(=C1)NC1CC1)C=1N=NN(C=1)CCC FOEMNUAURRCULJ-UHFFFAOYSA-N 0.000 claims 2
- RKRYCXRYSCMHIY-UHFFFAOYSA-N 2-(5-chloropyrazolo[3,4-b]pyridin-1-yl)-N-propan-2-yl-5-(1-propyltriazol-4-yl)pyridin-4-amine Chemical compound ClC=1C=C2C(=NC=1)N(N=C2)C1=NC=C(C(=C1)NC(C)C)C=1N=NN(C=1)CCC RKRYCXRYSCMHIY-UHFFFAOYSA-N 0.000 claims 2
- YSRAWZXKTUHGOV-UHFFFAOYSA-N 2-(5-chloropyrazolo[3,4-b]pyridin-1-yl)-N-propan-2-yl-5-(4-propyltriazol-1-yl)pyridin-4-amine Chemical compound ClC=1C=C2C(=NC=1)N(N=C2)C1=NC=C(C(=C1)NC(C)C)N1N=NC(=C1)CCC YSRAWZXKTUHGOV-UHFFFAOYSA-N 0.000 claims 2
- UNJUAEHMTHJIFW-UHFFFAOYSA-N 2-[4-[4-(propan-2-ylamino)-6-pyrrolo[2,3-d]pyrimidin-7-ylpyridin-3-yl]triazol-1-yl]ethanol Chemical compound C(C)(C)NC1=C(C=NC(=C1)N1C=CC2=C1N=CN=C2)C=1N=NN(C=1)CCO UNJUAEHMTHJIFW-UHFFFAOYSA-N 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- URGQYYJBXVGVPL-UHFFFAOYSA-N 3-[5-(1-ethyltriazol-4-yl)-4-(propan-2-ylamino)pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound C(C)N1N=NC(=C1)C=1C(=CC(=NC=1)N1C=NC=2C1=NC=C(C=2)C#N)NC(C)C URGQYYJBXVGVPL-UHFFFAOYSA-N 0.000 claims 2
- XAMSBTIOKLQVOL-UHFFFAOYSA-N 3-[5-[1-(1-acetylazetidin-3-yl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound C(C)(=O)N1CC(C1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1C=NC=2C1=NC=C(C=2)C#N)NC(C)C XAMSBTIOKLQVOL-UHFFFAOYSA-N 0.000 claims 2
- IGSZKLCLZXDOBR-UHFFFAOYSA-N 3-[5-[1-(1-phenylethyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)C(C)C1=CC=CC=C1)N1C=NC=2C1=NC=C(C=2)C#N IGSZKLCLZXDOBR-UHFFFAOYSA-N 0.000 claims 2
- HEOIRVDJQNNTDJ-ZDUSSCGKSA-N 3-[5-[1-[(2S)-2-hydroxypropyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound O[C@H](CN1N=NC(=C1)C=1C(=CC(=NC=1)N1C=NC=2C1=NC=C(C=2)C#N)NC(C)C)C HEOIRVDJQNNTDJ-ZDUSSCGKSA-N 0.000 claims 2
- IVTKZLIVZAQJIK-RTBURBONSA-N 3-[5-[1-[(3R,4S)-4-hydroxyoxolan-3-yl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound O[C@H]1[C@@H](COC1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1C=NC=2C1=NC=C(C=2)C#N)NC(C)C IVTKZLIVZAQJIK-RTBURBONSA-N 0.000 claims 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
- HLJTUCUISGMZIO-UHFFFAOYSA-N 5-[1-(2-morpholin-4-ylethyl)triazol-4-yl]-N-propan-2-yl-2-pyrrolo[2,3-d]pyrimidin-7-ylpyridin-4-amine Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)CCN1CCOCC1)N1C=CC2=C1N=CN=C2 HLJTUCUISGMZIO-UHFFFAOYSA-N 0.000 claims 2
- XJGDEKMFWMXXHW-UHFFFAOYSA-N 5-[1-(5-aminopentyl)triazol-4-yl]-N-propan-2-yl-2-pyrrolo[2,3-d]pyrimidin-7-ylpyridin-4-amine Chemical compound NCCCCCN1N=NC(=C1)C=1C(=CC(=NC=1)N1C=CC2=C1N=CN=C2)NC(C)C XJGDEKMFWMXXHW-UHFFFAOYSA-N 0.000 claims 2
- HVPPHRWBRGGVQB-UHFFFAOYSA-N 6-amino-1-[4-(oxan-4-ylamino)-5-(1-propyltriazol-4-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound NC1=C(C=C2C(=N1)N(N=C2)C1=NC=C(C(=C1)NC1CCOCC1)C=1N=NN(C=1)CCC)C#N HVPPHRWBRGGVQB-UHFFFAOYSA-N 0.000 claims 2
- JZDYDRZGPNWULK-UHFFFAOYSA-N 6-amino-1-[4-(oxetan-3-ylamino)-5-(4-propyltriazol-1-yl)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound NC1=C(C=C2C(=N1)N(N=C2)C1=NC=C(C(=C1)NC1COC1)N1N=NC(=C1)CCC)C#N JZDYDRZGPNWULK-UHFFFAOYSA-N 0.000 claims 2
- HOFDGKVZXXNSSV-UHFFFAOYSA-N 6-amino-1-[5-(1-cyclohexyltriazol-4-yl)-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound NC1=C(C=C2C(=N1)N(N=C2)C1=NC=C(C(=C1)NC(C)C)C=1N=NN(C=1)C1CCCCC1)C#N HOFDGKVZXXNSSV-UHFFFAOYSA-N 0.000 claims 2
- WMTGADPRTSHTMZ-UHFFFAOYSA-N 6-amino-1-[5-[1-(3-fluoropropyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound NC1=C(C=C2C(=N1)N(N=C2)C1=NC=C(C(=C1)NC(C)C)C=1N=NN(C=1)CCCF)C#N WMTGADPRTSHTMZ-UHFFFAOYSA-N 0.000 claims 2
- XPSNYPBQNKJMQL-UHFFFAOYSA-N 9-[4-(propan-2-ylamino)-5-(4-propyltriazol-1-yl)pyridin-2-yl]purin-2-amine Chemical compound C(C)(C)NC1=CC(=NC=C1N1N=NC(=C1)CCC)N1C2=NC(=NC=C2N=C1)N XPSNYPBQNKJMQL-UHFFFAOYSA-N 0.000 claims 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
- XEKBTDYAALTYQR-UHFFFAOYSA-N CC(C)NC(C=C(N1N=CC2=CC(C#N)=CN=C12)N=C1)=C1C1=CN(C(C(CCC2)O)N2C(O)=O)N=N1 Chemical compound CC(C)NC(C=C(N1N=CC2=CC(C#N)=CN=C12)N=C1)=C1C1=CN(C(C(CCC2)O)N2C(O)=O)N=N1 XEKBTDYAALTYQR-UHFFFAOYSA-N 0.000 claims 2
- GNYPVAYFFCLQKE-UHFFFAOYSA-N CCCN1N=NC(C(C(NC(C)CO)=C2)=CN=C2C2=NC3=CC(C#N)=CN=C3N2)=C1 Chemical compound CCCN1N=NC(C(C(NC(C)CO)=C2)=CN=C2C2=NC3=CC(C#N)=CN=C3N2)=C1 GNYPVAYFFCLQKE-UHFFFAOYSA-N 0.000 claims 2
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 235000010650 Hyssopus officinalis Nutrition 0.000 claims 2
- 240000001812 Hyssopus officinalis Species 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-methyl-pyrrolidinone Natural products CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- POLZTUCLSKJSPF-UHFFFAOYSA-N [4-[1-[6-(5-cyanopyrazolo[3,4-b]pyridin-1-yl)-4-(propan-2-ylamino)pyridin-3-yl]triazol-4-yl]-2-methylbutan-2-yl] 2-(dimethylamino)acetate Chemical compound CN(CC(=O)OC(C)(CCC=1N=NN(C=1)C=1C=NC(=CC=1NC(C)C)N1N=CC=2C1=NC=C(C=2)C#N)C)C POLZTUCLSKJSPF-UHFFFAOYSA-N 0.000 claims 2
- ACCYPTJWYUDZSB-UHFFFAOYSA-N [4-[1-[6-(5-cyanopyrazolo[3,4-b]pyridin-1-yl)-4-(propan-2-ylamino)pyridin-3-yl]triazol-4-yl]-2-methylbutan-2-yl] cyclopropanecarboxylate Chemical compound C(#N)C=1C=C2C(=NC=1)N(N=C2)C1=CC(=C(C=N1)N1N=NC(=C1)CCC(C)(C)OC(=O)C1CC1)NC(C)C ACCYPTJWYUDZSB-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- AUELWJRRASQDKI-UHFFFAOYSA-N cyclohexyl carbamate Chemical compound NC(=O)OC1CCCCC1 AUELWJRRASQDKI-UHFFFAOYSA-N 0.000 claims 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- OGLDQQFLRLCWEB-UHFFFAOYSA-N methyl N-[[3-[6-(5-cyanopyrazolo[3,4-b]pyridin-1-yl)-4-(propan-2-ylamino)pyridin-3-yl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]carbamate Chemical compound C(#N)C=1C=C2C(=NC=1)N(N=C2)C1=CC(=C(C=N1)C1=NOC(C1)CNC(OC)=O)NC(C)C OGLDQQFLRLCWEB-UHFFFAOYSA-N 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 2
- 230000000737 periodic effect Effects 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- ZNPFFFMGECMNPQ-UHFFFAOYSA-N tert-butyl 4-[[4-[6-(5-cyanopyrazolo[3,4-b]pyridin-1-yl)-4-(propan-2-ylamino)pyridin-3-yl]triazol-1-yl]methyl]-4-hydroxypiperidine-1-carboxylate Chemical compound C(#N)C=1C=C2C(=NC=1)N(N=C2)C1=CC(=C(C=N1)C=1N=NN(C=1)CC1(CCN(CC1)C(=O)OC(C)(C)C)O)NC(C)C ZNPFFFMGECMNPQ-UHFFFAOYSA-N 0.000 claims 2
- 125000006712 (C1-C4) deuteroalkyl group Chemical group 0.000 claims 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- DNHVFNDOHJKATM-UHFFFAOYSA-N 1-(2,2,2-trifluoroethyl)pyrazole Chemical compound FC(F)(F)CN1C=CC=N1 DNHVFNDOHJKATM-UHFFFAOYSA-N 0.000 claims 1
- MUZWURBFVCHTIC-UHFFFAOYSA-N 1-(triazol-1-yl)propan-2-ol Chemical compound CC(O)CN1C=CN=N1 MUZWURBFVCHTIC-UHFFFAOYSA-N 0.000 claims 1
- HAYFLXKGUNUKNH-UHFFFAOYSA-N 1-[5-[1-(1-methylazetidin-3-yl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)C1CN(C1)C)N1N=CC=2C1=NC=C(C=2)C#N HAYFLXKGUNUKNH-UHFFFAOYSA-N 0.000 claims 1
- RZPGFZIWFQTDBE-UHFFFAOYSA-N 1-[5-[1-(2-morpholin-4-ylethyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrrolo[2,3-b]pyridine-5-carbonitrile Chemical compound C(C)(C)NC1=CC(=NC=C1C=1N=NN(C=1)CCN1CCOCC1)N1C=CC=2C1=NC=C(C=2)C#N RZPGFZIWFQTDBE-UHFFFAOYSA-N 0.000 claims 1
- PVLULMHGSZZBKB-OAQYLSRUSA-N 1-[5-[3-[(2R)-1-acetylpyrrolidin-2-yl]-1,2-oxazol-5-yl]-4-(propan-2-ylamino)pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound C(C)(=O)N1[C@H](CCC1)C1=NOC(=C1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)NC(C)C PVLULMHGSZZBKB-OAQYLSRUSA-N 0.000 claims 1
- RCVXJIXEMNQHOI-SFHVURJKSA-N 1-[5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]-4-[[(3S)-oxolan-3-yl]amino]pyridin-2-yl]pyrazolo[3,4-b]pyridine-5-carbonitrile Chemical compound OC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)N1N=CC=2C1=NC=C(C=2)C#N)N[C@@H]1COCC1)(C)C RCVXJIXEMNQHOI-SFHVURJKSA-N 0.000 claims 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 1
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 claims 1
- VAUFFDKLUVJZTG-UHFFFAOYSA-N 1-propyltriazole Chemical compound CCCN1C=CN=N1 VAUFFDKLUVJZTG-UHFFFAOYSA-N 0.000 claims 1
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 claims 1
- ASIBBVJMOKFYHG-LBPRGKRZSA-N 3-[4-(ethylamino)-5-[1-[(2S)-2-hydroxypropyl]triazol-4-yl]pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound C(C)NC1=CC(=NC=C1C=1N=NN(C=1)C[C@H](C)O)N1C=NC=2C1=NC=C(C=2)C#N ASIBBVJMOKFYHG-LBPRGKRZSA-N 0.000 claims 1
- LTLPQSZUHQNPKB-UHFFFAOYSA-N 3-[5-[1-(2-hydroxy-3-phenylpropyl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound OC(CN1N=NC(=C1)C=1C(=CC(=NC=1)N1C=NC=2C1=NC=C(C=2)C#N)NC(C)C)CC1=CC=CC=C1 LTLPQSZUHQNPKB-UHFFFAOYSA-N 0.000 claims 1
- LMXFVVSUILIJTN-WOJBJXKFSA-N 3-[5-[1-[(1R,2R)-2-hydroxycyclopentyl]triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound O[C@H]1[C@@H](CCC1)N1N=NC(=C1)C=1C(=CC(=NC=1)N1C=NC=2C1=NC=C(C=2)C#N)NC(C)C LMXFVVSUILIJTN-WOJBJXKFSA-N 0.000 claims 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- KTMQQKMLYDWDKL-UHFFFAOYSA-N 5-chloro-1h-pyrazolo[3,4-b]pyridine Chemical compound ClC1=CN=C2NN=CC2=C1 KTMQQKMLYDWDKL-UHFFFAOYSA-N 0.000 claims 1
- 208000026326 Adult-onset Still disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- SDPRMMMKEWXGSX-UHFFFAOYSA-N N-[1-(2,2-difluoroethyl)pyrazol-4-yl]-5-(4-propyltriazol-1-yl)-2-pyrazolo[3,4-d]pyrimidin-1-ylpyridin-4-amine Chemical compound FC(CN1N=CC(=C1)NC1=CC(=NC=C1N1N=NC(=C1)CCC)N1N=CC=2C1=NC=NC=2)F SDPRMMMKEWXGSX-UHFFFAOYSA-N 0.000 claims 1
- 102100022691 NACHT, LRR and PYD domains-containing protein 3 Human genes 0.000 claims 1
- 101710126825 NACHT, LRR and PYD domains-containing protein 3 Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1877DE2015 | 2015-06-24 | ||
| IN1877/DEL/2015 | 2015-06-24 | ||
| PCT/US2016/038858 WO2016210034A1 (en) | 2015-06-24 | 2016-06-23 | Heteroaryl substituted aminopyridine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018522859A JP2018522859A (ja) | 2018-08-16 |
| JP2018522859A5 true JP2018522859A5 (https=) | 2019-07-18 |
| JP6843775B2 JP6843775B2 (ja) | 2021-03-17 |
Family
ID=56322320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017566643A Active JP6843775B2 (ja) | 2015-06-24 | 2016-06-23 | ヘテロアリール置換のアミノピリジン化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10294229B2 (https=) |
| EP (1) | EP3313840B1 (https=) |
| JP (1) | JP6843775B2 (https=) |
| CN (1) | CN107849039B (https=) |
| AR (1) | AR105113A1 (https=) |
| ES (1) | ES2745525T3 (https=) |
| TW (1) | TW201718571A (https=) |
| UY (1) | UY36748A (https=) |
| WO (1) | WO2016210034A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2822956T3 (es) * | 2015-06-24 | 2021-05-05 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituidos con heteroarilo |
| US10323036B2 (en) * | 2016-10-14 | 2019-06-18 | Nimbus Lakshmi, Inc. | TYK2 inhibitors and uses thereof |
| TW202340194A (zh) * | 2017-02-16 | 2023-10-16 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒𠯤衍生物 |
| PT3621960T (pt) | 2017-05-11 | 2021-09-16 | Bristol Myers Squibb Co | Tienopiridinas e benzotiofenos úteis como inibidores de irak4 |
| US11358948B2 (en) | 2017-09-22 | 2022-06-14 | Kymera Therapeutics, Inc. | CRBN ligands and uses thereof |
| WO2019060742A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc | AGENTS FOR DEGRADING PROTEINS AND USES THEREOF |
| TWI876442B (zh) | 2017-10-10 | 2025-03-11 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| WO2019140387A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| WO2019140380A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| TWI842978B (zh) | 2018-07-13 | 2024-05-21 | 美商基利科學股份有限公司 | 衍生物 |
| WO2020036830A1 (en) | 2018-08-13 | 2020-02-20 | Gilead Sciences, Inc. | Pyrrolo[1,2-b]pyridazine derivatives as irak4 inhibitors |
| TWI727392B (zh) * | 2018-08-13 | 2021-05-11 | 美商基利科學股份有限公司 | 噻二唑irak4抑制劑 |
| TWI797366B (zh) | 2018-08-13 | 2023-04-01 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒衍生物 |
| CA3119773A1 (en) | 2018-11-30 | 2020-06-04 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| CN109836376B (zh) * | 2019-04-10 | 2022-03-22 | 江苏汉阔生物有限公司 | 一种以2，3-吡啶二羧酸为原料制备2-氯代烟酸的方法 |
| PH12022500002A1 (en) | 2019-06-28 | 2023-04-03 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| WO2021011868A1 (en) | 2019-07-17 | 2021-01-21 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| EP3999508B1 (en) | 2019-07-18 | 2023-08-30 | Bristol-Myers Squibb Company | Tricyclic heteroaryl compounds useful as irak4 inhibitors |
| WO2021011727A1 (en) | 2019-07-18 | 2021-01-21 | Bristol-Myers Squibb Company | PYRAZOLO[3,4-d]PYRROLO[1,2-b]PYRIDAZINYL COMPOUNDS USEFUL AS IRAK4 INHIBITORS |
| US12304916B2 (en) | 2019-07-23 | 2025-05-20 | Bristol-Myers Squibb Company | Thienopyridinyl and thiazolopyridinyl compounds useful as IRAK4 inhibitors |
| WO2021026181A1 (en) | 2019-08-06 | 2021-02-11 | Bristol-Myers Squibb Company | Bicyclic heterocyclic compounds useful as irak4 inhibitors |
| ES3059914T3 (en) | 2019-08-13 | 2026-03-24 | Bristol Myers Squibb Co | Bicyclic heteroaryl compounds useful as irak4 inhibitors |
| US11578071B2 (en) | 2019-10-04 | 2023-02-14 | University Of Kentucky Research Foundation | Preparation of pyrazolo[3,4-B]pyridines as antimalarials |
| WO2021119159A1 (en) | 2019-12-10 | 2021-06-17 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| KR20220145325A (ko) | 2019-12-17 | 2022-10-28 | 카이메라 쎄라퓨틱스 인코포레이티드 | Irak 분해제 및 이의 용도 |
| EP4076524A4 (en) | 2019-12-17 | 2023-11-29 | Kymera Therapeutics, Inc. | IRAQ DEGRADERS AND USES THEREOF |
| CA3164924A1 (en) | 2019-12-18 | 2021-06-24 | Elanco Tiergesundheit Ag | Isoxazoline derivatives as pesticides |
| WO2021158495A1 (en) | 2020-02-03 | 2021-08-12 | Bristol-Myers Squibb Company | Benzo[5,6][1,4]dioxino[2,3-b]pyridine compounds useful as irak4 inhibitors |
| WO2021168197A1 (en) | 2020-02-19 | 2021-08-26 | Nurix Therapeutics, Inc. | Bifunctional degraders of interleukin-1 receptor-associated kinases and therapeutic use thereof |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| CN116867758A (zh) * | 2020-12-30 | 2023-10-10 | 凯麦拉医疗公司 | Irak降解剂和其用途 |
| US12171768B2 (en) | 2021-02-15 | 2024-12-24 | Kymera Therapeutics, Inc. | IRAK4 degraders and uses thereof |
| KR20240020735A (ko) | 2021-05-07 | 2024-02-15 | 카이메라 쎄라퓨틱스 인코포레이티드 | Cdk2 분해제 및 그 용도 |
| CN117813307A (zh) | 2021-08-18 | 2024-04-02 | 新锐思生物制药股份有限公司 | 白介素-1受体相关激酶的双官能降解物及其治疗用途 |
| CA3236265A1 (en) | 2021-10-29 | 2023-05-04 | William Leong | Irak4 degraders and synthesis thereof |
| CA3243560A1 (en) | 2022-01-31 | 2023-08-03 | Kymera Therapeutics, Inc. | Iraqi Degradation Agents and Their Uses |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2450769A1 (en) | 2001-06-15 | 2002-12-27 | Vertex Pharmaceuticals Incorporated | 5-(2-aminopyrimidin-4-yl) benzisoxazoles as protein kinase inhibitors |
| AUPR688101A0 (en) | 2001-08-08 | 2001-08-30 | Luminis Pty Limited | Protein domains and their ligands |
| GB0211019D0 (en) | 2002-05-14 | 2002-06-26 | Syngenta Ltd | Novel compounds |
| EP1518855B1 (en) | 2002-06-28 | 2011-10-26 | Astellas Pharma Inc. | Diaminopyrimidinecarboxa mide derivative |
| MXPA05007503A (es) | 2003-01-17 | 2005-09-21 | Warner Lambert Co | Heterociclicos 2-aminopiridina sustituidos como inhibidores de proliferacion celular. |
| WO2005007646A1 (en) | 2003-07-10 | 2005-01-27 | Neurogen Corporation | Substituted heterocyclic diarylamine analogues |
| GB0402653D0 (en) | 2004-02-06 | 2004-03-10 | Cyclacel Ltd | Compounds |
| US7521457B2 (en) | 2004-08-20 | 2009-04-21 | Boehringer Ingelheim International Gmbh | Pyrimidines as PLK inhibitors |
| FR2896503B1 (fr) | 2006-01-23 | 2012-07-13 | Aventis Pharma Sa | Nouveaux derives soufres d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| KR20100020454A (ko) | 2007-06-08 | 2010-02-22 | 바이엘 크롭사이언스 소시에떼아노님 | 살진균제 헤테로사이클릴-피리미디닐-아미노 유도체 |
| WO2009046416A1 (en) | 2007-10-05 | 2009-04-09 | Targegen Inc. | Anilinopyrimidines as jak kinase inhibitors |
| EP2361902A4 (en) | 2008-11-21 | 2012-04-25 | Astellas Pharma Inc | 4,6-DIAMINONICOTINSÄUREAMIDVERBINDUNG |
| WO2010061971A1 (ja) | 2008-11-28 | 2010-06-03 | 興和株式会社 | ピリジン－３－カルボキシアミド誘導体 |
| EP2440204B1 (en) | 2009-06-12 | 2013-12-18 | Bristol-Myers Squibb Company | Nicotinamide compounds useful as kinase modulators |
| EP2493863B1 (en) | 2009-10-30 | 2015-02-25 | Janssen Pharmaceutica NV | Phenoxy-substituted pyrimidines as opioid receptor modulators |
| KR20120130104A (ko) | 2010-02-01 | 2012-11-28 | 닛뽕 케미파 가부시키가이샤 | Ｇｐｒ119 작동약 |
| JP2014515029A (ja) | 2011-04-29 | 2014-06-26 | アイカーン・スクール・オブ・メディシン・アト・マウント・シナイ | キナーゼ阻害剤 |
| ES2575604T3 (es) | 2012-01-13 | 2016-06-29 | Bristol-Myers Squibb Company | Compuestos de piridilo sustituidos con tiazolilo o tiadiazolilo útiles como inhibidores cinasa |
| CN104169275B (zh) * | 2012-01-13 | 2017-06-09 | 百时美施贵宝公司 | 用作激酶抑制剂的三唑取代的吡啶化合物 |
| EP2802576B1 (en) * | 2012-01-13 | 2018-06-27 | Bristol-Myers Squibb Company | Heterocyclic-substituted pyridyl compounds useful as kinase inhibitors |
| WO2014058685A1 (en) * | 2012-10-08 | 2014-04-17 | Merck Sharp & Dohme Corp. | Inhibitors of irak4 activity |
| BR112015009850A2 (pt) | 2012-11-08 | 2017-07-11 | Bristol Myers Squibb Co | compostos de piridila substituídos por heteroarila úteis como moduladores de quinase |
| KR102233252B1 (ko) | 2012-11-08 | 2021-03-26 | 브리스톨-마이어스 스큅 컴퍼니 | ＩＬ-12, ＩＬ-23 및/또는 ＩＦＮα 반응의 조절제로서 유용한 알킬-아미드-치환된 피리딜 화합물 |
| JP6215338B2 (ja) | 2012-11-08 | 2017-10-18 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | キナーゼモジュレーターとして有用な二環式ヘテロ環置換ピリジル化合物 |
| TWI582077B (zh) | 2013-11-07 | 2017-05-11 | 必治妥美雅史谷比公司 | 作爲ＩＬ－１２、ＩＬ－２３及／或ＩＦＮα反應調節劑之經烷基－醯胺取代之吡啶化合物 |
| UY35935A (es) | 2014-01-03 | 2015-06-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de nicotinamida sustituida con heteroarilo como inhibidores de quinasa y moduladores de irak-4 |
| ES2822956T3 (es) * | 2015-06-24 | 2021-05-05 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituidos con heteroarilo |
-
2016
- 2016-06-23 EP EP16734538.8A patent/EP3313840B1/en active Active
- 2016-06-23 TW TW105119777A patent/TW201718571A/zh unknown
- 2016-06-23 AR ARP160101892A patent/AR105113A1/es unknown
- 2016-06-23 UY UY0001036748A patent/UY36748A/es not_active Application Discontinuation
- 2016-06-23 US US15/738,362 patent/US10294229B2/en active Active
- 2016-06-23 CN CN201680040987.7A patent/CN107849039B/zh active Active
- 2016-06-23 ES ES16734538T patent/ES2745525T3/es active Active
- 2016-06-23 JP JP2017566643A patent/JP6843775B2/ja active Active
- 2016-06-23 WO PCT/US2016/038858 patent/WO2016210034A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018522859A5 (https=) | ||
| RU2473549C2 (ru) | Пиримидиновые соединения, композиции и способы применения | |
| JP2017501202A5 (https=) | ||
| CN107849039B (zh) | 经杂芳基取代的氨基吡啶化合物 | |
| AU2017378943B2 (en) | FGFR4 inhibitor, preparation method therefor and pharmaceutical use thereof | |
| US8962596B2 (en) | 5,7-substituted-imidazo[1,2-C]pyrimidines as inhibitors of JAK kinases | |
| JP2020050682A (ja) | ドライアイおよび他の目に関連する疾患を治療するためのヤヌスキナーゼ阻害剤 | |
| AU2018346712B2 (en) | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD | |
| CN105143207B (zh) | 作为pde4抑制剂的取代的吡啶和取代的吡嗪化合物 | |
| JP2018524331A5 (https=) | ||
| JP2019504821A5 (https=) | ||
| TWI878423B (zh) | 環狀化合物及其使用方法 | |
| ES2807785T3 (es) | Compuestos de heteroarilamina bicíclicos como inhibidores de pi3k | |
| CN110300754A (zh) | 吡咯并[1,2-b]哒嗪衍生物 | |
| JP2013523884A5 (https=) | ||
| ME02595B (me) | Heterociklilamini kao inhibitori pi3k | |
| JP2014521711A5 (https=) | ||
| EA030376B1 (ru) | Азетидиновые производные пиперидин-4-ила как ингибиторы jak1 | |
| CN106061967A (zh) | 经杂芳基取代的烟酰胺化合物 | |
| JP2013515729A5 (https=) | ||
| AU2014207641A1 (en) | Substituted Pyrrolopyrimidine Compounds, compositions thereof, and methods of treatment therewith | |
| JP2022545364A5 (https=) | ||
| CN116262739A (zh) | 含氮芳基衍生物调节剂、其制备方法和应用 | |
| CN110225907A (zh) | 作为RORc调节剂的哒嗪衍生物 | |
| EA052528B1 (ru) | Циклические соединения и способы их применения |