JP4872068B2 - ピラゾロ［３，４−ｂ］ピリジン化合物およびホスホジエステラーゼ阻害剤としてのその使用 - Google Patents

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Publication number

JP4872068B2

JP4872068B2 JP2005502565A JP2005502565A JP4872068B2 JP 4872068 B2 JP4872068 B2 JP 4872068B2 JP 2005502565 A JP2005502565 A JP 2005502565A JP 2005502565 A JP2005502565 A JP 2005502565A JP 4872068 B2 JP4872068 B2 JP 4872068B2

Authority

JP

Japan

Prior art keywords

ethyl

pyrazolo

tetrahydro

pyridin

pyran

Prior art date

2002-12-23

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.)

Expired - Fee Related

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• 239000002571 phosphodiesterase inhibitor Substances 0.000 title description 2
• 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title description 2
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 478
• 150000001875 compounds Chemical class 0.000 claims description 342
• 229910052799 carbon Inorganic materials 0.000 claims description 197
• 150000003839 salts Chemical class 0.000 claims description 186
• -1 hydroxyimino Chemical group 0.000 claims description 178
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
• 125000001424 substituent group Chemical group 0.000 claims description 119
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 116
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 114
• 229910052739 hydrogen Inorganic materials 0.000 claims description 110
• 239000000203 mixture Substances 0.000 claims description 105
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
• 125000003545 alkoxy group Chemical group 0.000 claims description 91
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 84
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 82
• 125000000623 heterocyclic group Chemical group 0.000 claims description 81
• 125000001153 fluoro group Chemical group F* 0.000 claims description 69
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 65
• 230000036961 partial effect Effects 0.000 claims description 61
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 56
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
• 229910052760 oxygen Inorganic materials 0.000 claims description 54
• 229910052717 sulfur Inorganic materials 0.000 claims description 53
• 150000001721 carbon Chemical group 0.000 claims description 51
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 48
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 47
• 229910052757 nitrogen Inorganic materials 0.000 claims description 40
• 239000008194 pharmaceutical composition Substances 0.000 claims description 39
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 33
• 239000002245 particle Substances 0.000 claims description 33
• 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 description 31
• 239000003814 drug Substances 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 30
• 229910005965 SO 2 Inorganic materials 0.000 claims description 29
• 239000000126 substance Substances 0.000 claims description 28
• 125000006413 ring segment Chemical group 0.000 claims description 27
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 25
• 241000124008 Mammalia Species 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 19
• 230000002265 prevention Effects 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• 241000282412 Homo Species 0.000 claims description 17
• 208000006673 asthma Diseases 0.000 claims description 16
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 14
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 14
• 125000002541 furyl group Chemical group 0.000 claims description 13
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 13
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 11
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 11
• 201000010105 allergic rhinitis Diseases 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
• SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 230000002757 inflammatory effect Effects 0.000 claims description 10
• 208000026935 allergic disease Diseases 0.000 claims description 9
• 208000027866 inflammatory disease Diseases 0.000 claims description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
• 125000000468 ketone group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 208000028698 Cognitive impairment Diseases 0.000 claims description 7
• 208000010877 cognitive disease Diseases 0.000 claims description 7
• 229930194542 Keto Natural products 0.000 claims description 6
• 206010040070 Septic Shock Diseases 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 229910052727 yttrium Inorganic materials 0.000 claims description 6
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 208000012902 Nervous system disease Diseases 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• DZSUIHQGHLXFNA-UHFFFAOYSA-N 1-ethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DZSUIHQGHLXFNA-UHFFFAOYSA-N 0.000 claims description 4
• HVORADNDQMNGIL-UHFFFAOYSA-N 1-ethyl-5-[5-(3-methyloxetan-3-yl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2(C)COC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 HVORADNDQMNGIL-UHFFFAOYSA-N 0.000 claims description 4
• RAROYFBUEHDELU-UHFFFAOYSA-N 1-ethyl-5-[5-(methylsulfonylmethyl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CS(C)(=O)=O)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 RAROYFBUEHDELU-UHFFFAOYSA-N 0.000 claims description 4
• SRLUNZCKDYANNB-UHFFFAOYSA-N 1-ethyl-5-[5-(morpholin-4-ylmethyl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CN2CCOCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SRLUNZCKDYANNB-UHFFFAOYSA-N 0.000 claims description 4
• PNIDTSWGLZJDPB-UHFFFAOYSA-N 1-ethyl-5-[5-[(4-methylpiperazin-1-yl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CN2CCN(C)CC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 PNIDTSWGLZJDPB-UHFFFAOYSA-N 0.000 claims description 4
• GCPAVLWQQFFTOS-UHFFFAOYSA-N 1-ethyl-5-[5-[(5-methyl-1,2-oxazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC2=NOC(C)=C2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GCPAVLWQQFFTOS-UHFFFAOYSA-N 0.000 claims description 4
• DGUMUMKJVDPEIP-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(oxan-4-yl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2CCOCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DGUMUMKJVDPEIP-UHFFFAOYSA-N 0.000 claims description 4
• YSAHVJSLXAIKQP-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(oxan-4-ylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC2CCOCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 YSAHVJSLXAIKQP-UHFFFAOYSA-N 0.000 claims description 4
• FHDAFFDIINYJBH-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(oxolan-2-yl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2OCCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 FHDAFFDIINYJBH-UHFFFAOYSA-N 0.000 claims description 4
• GKWYHRDQRBFOLN-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-1-piperidin-1-ylethanone Chemical compound N=1C(CC(=O)N2CCCCC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GKWYHRDQRBFOLN-UHFFFAOYSA-N 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 4
• OCEFXDCLHOSCLT-UHFFFAOYSA-N 5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C(C)(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OCEFXDCLHOSCLT-UHFFFAOYSA-N 0.000 claims description 4
• YCDYDLCULLEOFK-UHFFFAOYSA-N 5-[3-[[4-(dimethylamino)phenyl]methyl]-1,2,4-oxadiazol-5-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CC=2C=CC(=CC=2)N(C)C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 YCDYDLCULLEOFK-UHFFFAOYSA-N 0.000 claims description 4
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
• 208000011231 Crohn disease Diseases 0.000 claims description 4
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• 208000025966 Neurological disease Diseases 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
• 201000008937 atopic dermatitis Diseases 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 230000036407 pain Effects 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 3
• WVSSDMGQAQMULY-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-1-pyrrolidin-1-ylethanone Chemical compound N=1C(CC(=O)N2CCCC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 WVSSDMGQAQMULY-UHFFFAOYSA-N 0.000 claims description 3
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 3
• 206010018367 Glomerulonephritis chronic Diseases 0.000 claims description 3
• 206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 206010063837 Reperfusion injury Diseases 0.000 claims description 3
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
• 208000024780 Urticaria Diseases 0.000 claims description 3
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 3
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 3
• 208000003401 eosinophilic granuloma Diseases 0.000 claims description 3
• 229960004979 fampridine Drugs 0.000 claims description 3
• 230000002107 myocardial effect Effects 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 230000036303 septic shock Effects 0.000 claims description 3
• KTVRYLLWSAKBQE-CYBMUJFWSA-N (4s)-4-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]-1,3-thiazolidin-2-one Chemical compound N=1N=C([C@@H]2NC(=O)SC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KTVRYLLWSAKBQE-CYBMUJFWSA-N 0.000 claims description 2
• GBWYDLGKUQJVRJ-UHFFFAOYSA-N 1-(2,6-dimethylmorpholin-4-yl)-2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]ethanone Chemical compound N=1C(CC(=O)N2CC(C)OC(C)C2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GBWYDLGKUQJVRJ-UHFFFAOYSA-N 0.000 claims description 2
• DUNGKDJJZCXWQL-UHFFFAOYSA-N 1-(3,5-dimethylpiperidin-1-yl)-2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]ethanone Chemical compound N=1C(CC(=O)N2CC(C)CC(C)C2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DUNGKDJJZCXWQL-UHFFFAOYSA-N 0.000 claims description 2
• CVAXMIYRADIZRM-UHFFFAOYSA-N 1-[4-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]piperidin-1-yl]ethanone Chemical compound N=1N=C(C2CCN(CC2)C(C)=O)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 CVAXMIYRADIZRM-UHFFFAOYSA-N 0.000 claims description 2
• XXXVUGIOAOGYII-UHFFFAOYSA-N 1-[4-[[1-ethyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]piperidin-1-yl]ethanone Chemical compound N=1C(C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(C)=O)CC1 XXXVUGIOAOGYII-UHFFFAOYSA-N 0.000 claims description 2
• IPTKTNMATNAITF-UHFFFAOYSA-N 1-[4-[[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]methyl]piperidin-1-yl]-3-methylbutan-1-one Chemical compound N=1C(CC2CCN(CC2)C(=O)CC(C)C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 IPTKTNMATNAITF-UHFFFAOYSA-N 0.000 claims description 2
• SLIPVLITWWRAIZ-UHFFFAOYSA-N 1-[4-[[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]methyl]piperidin-1-yl]ethanone Chemical compound N=1C(CC2CCN(CC2)C(C)=O)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SLIPVLITWWRAIZ-UHFFFAOYSA-N 0.000 claims description 2
• OUDLMNIFLFDCMK-UHFFFAOYSA-N 1-[4-[[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]methyl]piperidin-1-yl]ethanone Chemical compound N=1N=C(CC2CCN(CC2)C(C)=O)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OUDLMNIFLFDCMK-UHFFFAOYSA-N 0.000 claims description 2
• KTPLCBJGWLNBRN-UHFFFAOYSA-N 1-[[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]methyl]piperidin-2-one Chemical compound N=1C(CN2C(CCCC2)=O)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KTPLCBJGWLNBRN-UHFFFAOYSA-N 0.000 claims description 2
• QLTPSIKFIHKEQK-UHFFFAOYSA-N 1-[[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]methyl]pyrrolidin-2-one Chemical compound N=1C(CN2C(CCC2)=O)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 QLTPSIKFIHKEQK-UHFFFAOYSA-N 0.000 claims description 2
• BFMIITZYRGFIBF-UHFFFAOYSA-N 1-ethyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 BFMIITZYRGFIBF-UHFFFAOYSA-N 0.000 claims description 2
• SFKHPTKCXNEMGR-UHFFFAOYSA-N 1-ethyl-5-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C)COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SFKHPTKCXNEMGR-UHFFFAOYSA-N 0.000 claims description 2
• PGSWRAIJIPEFDZ-UHFFFAOYSA-N 1-ethyl-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound O1C(CC)=NC(C=2C(=C3C=NN(CC)C3=NC=2)NC2CCOCC2)=N1 PGSWRAIJIPEFDZ-UHFFFAOYSA-N 0.000 claims description 2
• ZSRYLGURRJAFGU-UHFFFAOYSA-N 1-ethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(2-methylpropyl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(NCC(C)C)C=1C1=NN=C(C)O1 ZSRYLGURRJAFGU-UHFFFAOYSA-N 0.000 claims description 2
• YYQPNWDAHYNNDH-UHFFFAOYSA-N 1-ethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(oxan-3-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCOC1 YYQPNWDAHYNNDH-UHFFFAOYSA-N 0.000 claims description 2
• WCWOENKXBJFQNM-UHFFFAOYSA-N 1-ethyl-5-(5-methyl-1h-1,2,4-triazol-3-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1NC(C)=NC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 WCWOENKXBJFQNM-UHFFFAOYSA-N 0.000 claims description 2
• VIWLAEHLDMIWGY-FOIQADDNSA-N 1-ethyl-5-[(4s,5r)-5-methyl-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound O([C@H](C)[C@@H](N=1)C=2C=CC=CC=2)C=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 VIWLAEHLDMIWGY-FOIQADDNSA-N 0.000 claims description 2
• YOUJFSVWVNNWFH-UHFFFAOYSA-N 1-ethyl-5-[3-(1-morpholin-4-ylethyl)-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C(C)N2CCOCC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 YOUJFSVWVNNWFH-UHFFFAOYSA-N 0.000 claims description 2
• ZENDFWOFRUOXDJ-UHFFFAOYSA-N 1-ethyl-5-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C=2C=CC(F)=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZENDFWOFRUOXDJ-UHFFFAOYSA-N 0.000 claims description 2
• NLVVJERIEVFTLG-UHFFFAOYSA-N 1-ethyl-5-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(COC)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 NLVVJERIEVFTLG-UHFFFAOYSA-N 0.000 claims description 2
• LZZPQXOGXCQUGJ-UHFFFAOYSA-N 1-ethyl-5-[3-[(1-methylsulfonylpiperidin-4-yl)methyl]-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CC2CCN(CC2)S(C)(=O)=O)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 LZZPQXOGXCQUGJ-UHFFFAOYSA-N 0.000 claims description 2
• QSCOVJBADWLZIS-UHFFFAOYSA-N 1-ethyl-5-[3-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CC=2C=CC(OC)=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 QSCOVJBADWLZIS-UHFFFAOYSA-N 0.000 claims description 2
• WQBQOJHYKSRNFC-UHFFFAOYSA-N 1-ethyl-5-[3-[(4-methylpiperazin-1-yl)methyl]-1,2,4-oxadiazol-5-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CN2CCN(C)CC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 WQBQOJHYKSRNFC-UHFFFAOYSA-N 0.000 claims description 2
• UKUHYPRBRUTILD-UHFFFAOYSA-N 1-ethyl-5-[5-(1-methylcyclobutyl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2(C)CCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 UKUHYPRBRUTILD-UHFFFAOYSA-N 0.000 claims description 2
• SVFAAQULAJXNMV-UHFFFAOYSA-N 1-ethyl-5-[5-(1-methylpiperidin-2-yl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2N(CCCC2)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SVFAAQULAJXNMV-UHFFFAOYSA-N 0.000 claims description 2
• ZOIGVSZGKZCAPP-UHFFFAOYSA-N 1-ethyl-5-[5-(2-methylpyrazol-3-yl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C=2N(N=CC=2)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZOIGVSZGKZCAPP-UHFFFAOYSA-N 0.000 claims description 2
• FJDWKHFMSDWSNO-UHFFFAOYSA-N 1-ethyl-5-[5-(3-methyl-1,2-oxazol-5-yl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C=2ON=C(C)C=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 FJDWKHFMSDWSNO-UHFFFAOYSA-N 0.000 claims description 2
• CIXIMQTZWBJKBO-UHFFFAOYSA-N 1-ethyl-5-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C=2C=CC(C)=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 CIXIMQTZWBJKBO-UHFFFAOYSA-N 0.000 claims description 2
• SCETZZAUHVGRGV-UHFFFAOYSA-N 1-ethyl-5-[5-(furan-2-ylmethyl)-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2OC=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SCETZZAUHVGRGV-UHFFFAOYSA-N 0.000 claims description 2
• PYOBRTUFQYLIKV-UHFFFAOYSA-N 1-ethyl-5-[5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2N=C(C)SC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 PYOBRTUFQYLIKV-UHFFFAOYSA-N 0.000 claims description 2
• QHXXOWPCEDLXIO-UHFFFAOYSA-N 1-ethyl-5-[5-[(2-methylpropan-2-yl)oxymethyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(COC(C)(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 QHXXOWPCEDLXIO-UHFFFAOYSA-N 0.000 claims description 2
• VHALEQDDVFAXIO-UHFFFAOYSA-N 1-ethyl-5-[5-[(3-methyl-1,2-oxazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2ON=C(C)C=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 VHALEQDDVFAXIO-UHFFFAOYSA-N 0.000 claims description 2
• QOJFGHZYONTWMP-UHFFFAOYSA-N 1-ethyl-5-[5-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazol-3-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC(CC=2C=CC(OC)=CC=2)=NC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 QOJFGHZYONTWMP-UHFFFAOYSA-N 0.000 claims description 2
• CLEILMJNGPWTDV-UHFFFAOYSA-N 1-ethyl-5-[5-[(4-methoxyphenyl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2C=CC(OC)=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 CLEILMJNGPWTDV-UHFFFAOYSA-N 0.000 claims description 2
• CAWWLBXDODKJNS-UHFFFAOYSA-N 1-ethyl-5-[5-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2C(=NON=2)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 CAWWLBXDODKJNS-UHFFFAOYSA-N 0.000 claims description 2
• ZVCQBYDWSXMYFM-UHFFFAOYSA-N 1-ethyl-5-[5-[(4-methylphenyl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2C=CC(C)=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZVCQBYDWSXMYFM-UHFFFAOYSA-N 0.000 claims description 2
• XCIURLZFQRSZFL-UHFFFAOYSA-N 1-ethyl-5-[5-[(5-methyl-1h-1,2,4-triazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2NN=C(C)N=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 XCIURLZFQRSZFL-UHFFFAOYSA-N 0.000 claims description 2
• ONWXJMCAIRWEKW-UHFFFAOYSA-N 1-ethyl-6-methyl-n-(oxan-4-yl)-5-[5-(oxan-4-yl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2CCOCC2)OC=1C1=C(C)N=C2N(CC)N=CC2=C1NC1CCOCC1 ONWXJMCAIRWEKW-UHFFFAOYSA-N 0.000 claims description 2
• JBLZLAGODLTVIT-UHFFFAOYSA-N 1-ethyl-n-(2-methylpropyl)-5-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(NCC(C)C)C=1C1=NN=C(C(C)C)O1 JBLZLAGODLTVIT-UHFFFAOYSA-N 0.000 claims description 2
• IRFSMVACBPZXQK-UHFFFAOYSA-N 1-ethyl-n-(2-methylpropyl)-5-[5-(methylsulfonylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical class C=1N=C2N(CC)N=CC2=C(NCC(C)C)C=1C1=NN=C(CS(C)(=O)=O)O1 IRFSMVACBPZXQK-UHFFFAOYSA-N 0.000 claims description 2
• KADJAHICEJKIPX-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KADJAHICEJKIPX-UHFFFAOYSA-N 0.000 claims description 2
• GTDFYDJUUKTZAZ-IBGZPJMESA-N 1-ethyl-n-(oxan-4-yl)-5-[(4r)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C([C@H](N=1)C=2C=CC=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GTDFYDJUUKTZAZ-IBGZPJMESA-N 0.000 claims description 2
• GTDFYDJUUKTZAZ-LJQANCHMSA-N 1-ethyl-n-(oxan-4-yl)-5-[(4s)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C([C@@H](N=1)C=2C=CC=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GTDFYDJUUKTZAZ-LJQANCHMSA-N 0.000 claims description 2
• ZSQPYAOFXSYYPS-IBGZPJMESA-N 1-ethyl-n-(oxan-4-yl)-5-[(5r)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound O([C@@H](CN=1)C=2C=CC=CC=2)C=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZSQPYAOFXSYYPS-IBGZPJMESA-N 0.000 claims description 2
• ZSQPYAOFXSYYPS-LJQANCHMSA-N 1-ethyl-n-(oxan-4-yl)-5-[(5s)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound O([C@H](CN=1)C=2C=CC=CC=2)C=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZSQPYAOFXSYYPS-LJQANCHMSA-N 0.000 claims description 2
• INYBSZIXVLSUJA-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[3-(1-phenylethyl)-1,2,4-oxadiazol-5-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C(C)C=2C=CC=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 INYBSZIXVLSUJA-UHFFFAOYSA-N 0.000 claims description 2
• QTEALXSUGGKILU-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[3-(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)-1,2,4-oxadiazol-5-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CC=2N3CCCCC3=NN=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 QTEALXSUGGKILU-UHFFFAOYSA-N 0.000 claims description 2
• OZOSDNVRVSSAHB-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[3-(phenoxymethyl)-1,2,4-oxadiazol-5-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(COC=2C=CC=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OZOSDNVRVSSAHB-UHFFFAOYSA-N 0.000 claims description 2
• NTDMDFKUMUMHKX-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[3-[(4-phenylpiperazin-1-yl)methyl]-1,2,4-oxadiazol-5-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CN2CCN(CC2)C=2C=CC=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 NTDMDFKUMUMHKX-UHFFFAOYSA-N 0.000 claims description 2
• FLRXHDMDCAYWDN-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(1,2-oxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC2=NOC=C2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 FLRXHDMDCAYWDN-UHFFFAOYSA-N 0.000 claims description 2
• GNKXGXFQRFKSDH-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(1,2-thiazol-5-ylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2SN=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GNKXGXFQRFKSDH-UHFFFAOYSA-N 0.000 claims description 2
• KVLMMBNWVFAIBM-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(oxolan-3-yl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2COCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KVLMMBNWVFAIBM-UHFFFAOYSA-N 0.000 claims description 2
• OFGGQPJWUPTKAE-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(tetrazol-1-ylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CN2N=NN=C2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OFGGQPJWUPTKAE-UHFFFAOYSA-N 0.000 claims description 2
• IPDGXOGFGNWDLT-UHFFFAOYSA-N 1-ethyl-n-(oxan-4-yl)-5-[5-(triazol-1-ylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CN2N=NC=C2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 IPDGXOGFGNWDLT-UHFFFAOYSA-N 0.000 claims description 2
• ULHNQMLNEOFZJA-SNVBAGLBSA-N 1-ethyl-n-[(2r)-3-methylbutan-2-yl]-5-(5-methyl-1,3,4-oxadiazol-2-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@H](C)C(C)C)C=1C1=NN=C(C)O1 ULHNQMLNEOFZJA-SNVBAGLBSA-N 0.000 claims description 2
• JMWZIFXTBMKJSA-LLVKDONJSA-N 1-ethyl-n-[(2r)-3-methylbutan-2-yl]-5-[5-(methylsulfonylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@H](C)C(C)C)C=1C1=NN=C(CS(C)(=O)=O)O1 JMWZIFXTBMKJSA-LLVKDONJSA-N 0.000 claims description 2
• ULHNQMLNEOFZJA-JTQLQIEISA-N 1-ethyl-n-[(2s)-3-methylbutan-2-yl]-5-(5-methyl-1,3,4-oxadiazol-2-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C1=NN=C(C)O1 ULHNQMLNEOFZJA-JTQLQIEISA-N 0.000 claims description 2
• JMWZIFXTBMKJSA-NSHDSACASA-N 1-ethyl-n-[(2s)-3-methylbutan-2-yl]-5-[5-(methylsulfonylmethyl)-1,3,4-oxadiazol-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C1=NN=C(CS(C)(=O)=O)O1 JMWZIFXTBMKJSA-NSHDSACASA-N 0.000 claims description 2
• RNNZANZFUHPPCV-UHFFFAOYSA-N 1-ethyl-n-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1N(C)C1CCOCC1 RNNZANZFUHPPCV-UHFFFAOYSA-N 0.000 claims description 2
• AQJOVIWDIWNCPO-UHFFFAOYSA-N 2-[1-[[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]methyl]cyclopentyl]-n-methylacetamide Chemical compound N=1N=C(CC2(CC(=O)NC)CCCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 AQJOVIWDIWNCPO-UHFFFAOYSA-N 0.000 claims description 2
• QLBIYIQITIQXRW-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxylic acid Chemical compound N=1C(C(O)=O)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 QLBIYIQITIQXRW-UHFFFAOYSA-N 0.000 claims description 2
• VWXMYTAXNQPIMV-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-4,5-dihydro-1,3-oxazole-4-carboxylic acid Chemical compound N=1C(C(O)=O)COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 VWXMYTAXNQPIMV-UHFFFAOYSA-N 0.000 claims description 2
• ZCKSIJOJANDRPR-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-(1-phenylethyl)-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NC(C)C=2C=CC=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZCKSIJOJANDRPR-UHFFFAOYSA-N 0.000 claims description 2
• DWFDHPYYCYEJGN-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-(4-methylphenyl)-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NC=2C=CC(C)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DWFDHPYYCYEJGN-UHFFFAOYSA-N 0.000 claims description 2
• WFYJYVQBIROZDM-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-(oxolan-2-ylmethyl)-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC2OCCC2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 WFYJYVQBIROZDM-UHFFFAOYSA-N 0.000 claims description 2
• RWIAMDUQGXFKKZ-MRXNPFEDSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(1r)-1-(4-methoxyphenyl)ethyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)N[C@H](C)C=2C=CC(OC)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 RWIAMDUQGXFKKZ-MRXNPFEDSA-N 0.000 claims description 2
• TZKCDELUXVOZMX-OAQYLSRUSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(1r)-1-phenylpropyl]-1,3-oxazole-4-carboxamide Chemical compound N([C@H](CC)C=1C=CC=CC=1)C(=O)C(N=1)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 TZKCDELUXVOZMX-OAQYLSRUSA-N 0.000 claims description 2
• KAVBNTHXLSERHF-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(2-methylphenyl)methyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C(=CC=CC=2)C)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KAVBNTHXLSERHF-UHFFFAOYSA-N 0.000 claims description 2
• KTENKTRLKSWEMI-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(3-methylphenyl)methyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=C(C)C=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KTENKTRLKSWEMI-UHFFFAOYSA-N 0.000 claims description 2
• AJXVWWVIYRYFMH-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(4-methoxyphenyl)methyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=CC(OC)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 AJXVWWVIYRYFMH-UHFFFAOYSA-N 0.000 claims description 2
• RJNJGQYSZACMHH-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(4-methylphenyl)methyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=CC(C)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 RJNJGQYSZACMHH-UHFFFAOYSA-N 0.000 claims description 2
• SHTHJKWJBAOADN-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[(4-methylsulfonylphenyl)methyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=CC(=CC=2)S(C)(=O)=O)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SHTHJKWJBAOADN-UHFFFAOYSA-N 0.000 claims description 2
• PICVCUJLOIUHAJ-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[2-(4-methylpiperazin-1-yl)ethyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCCN2CCN(C)CC2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 PICVCUJLOIUHAJ-UHFFFAOYSA-N 0.000 claims description 2
• OIJJLNQPGJDEEL-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-[[4-(methanesulfonamido)phenyl]methyl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=CC(NS(C)(=O)=O)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OIJJLNQPGJDEEL-UHFFFAOYSA-N 0.000 claims description 2
• YQIFWOAOYUFYQS-UHFFFAOYSA-N 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-propan-2-yl-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NC(C)C)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 YQIFWOAOYUFYQS-UHFFFAOYSA-N 0.000 claims description 2
• BUAIVVRCRAGIMA-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-1-(3-methylpiperidin-1-yl)ethanone Chemical compound N=1C(CC(=O)N2CC(C)CCC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 BUAIVVRCRAGIMA-UHFFFAOYSA-N 0.000 claims description 2
• OXFCPWRILGDWEI-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound N=1C(CC(=O)N2CCN(C)CC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OXFCPWRILGDWEI-UHFFFAOYSA-N 0.000 claims description 2
• ABNWLVUIJVFMAS-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-1-(4-methylpiperidin-1-yl)ethanone Chemical compound N=1C(CC(=O)N2CCC(C)CC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ABNWLVUIJVFMAS-UHFFFAOYSA-N 0.000 claims description 2
• UGWIJRPPULTWRE-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-n,n-dimethylacetamide Chemical compound N=1C(CC(=O)N(C)C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 UGWIJRPPULTWRE-UHFFFAOYSA-N 0.000 claims description 2
• SSUCTVUMPTWNCW-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-n-phenylacetamide Chemical compound N=1C(CC(=O)NC=2C=CC=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SSUCTVUMPTWNCW-UHFFFAOYSA-N 0.000 claims description 2
• HTWPFILTADDJSP-UHFFFAOYSA-N 2-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,2,4-oxadiazol-3-yl]-n-pyridin-3-ylacetamide Chemical compound N=1C(CC(=O)NC=2C=NC=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 HTWPFILTADDJSP-UHFFFAOYSA-N 0.000 claims description 2
• GDEJKZSPGSDUPN-UHFFFAOYSA-N 3-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]cyclopentan-1-one Chemical compound N=1N=C(C2CC(=O)CC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GDEJKZSPGSDUPN-UHFFFAOYSA-N 0.000 claims description 2
• XMWIMIZRHFZHMQ-UHFFFAOYSA-N 4-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]-1-methylpyrrolidin-2-one Chemical compound N=1N=C(C2CC(=O)N(C)C2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 XMWIMIZRHFZHMQ-UHFFFAOYSA-N 0.000 claims description 2
• UZMQEQHBNAVKFF-UHFFFAOYSA-N 4-[[1-ethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)pyrazolo[3,4-b]pyridin-4-yl]amino]cyclohexan-1-one Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCC(=O)CC1 UZMQEQHBNAVKFF-UHFFFAOYSA-N 0.000 claims description 2
• KMNGCWWUPFOFHD-UHFFFAOYSA-N 5-(3-benzyl-1,2,4-oxadiazol-5-yl)-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CC=2C=CC=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 KMNGCWWUPFOFHD-UHFFFAOYSA-N 0.000 claims description 2
• HQESRZJRDCZAJW-UHFFFAOYSA-N 5-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C)(C)COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 HQESRZJRDCZAJW-UHFFFAOYSA-N 0.000 claims description 2
• ZBLVKHPDYCQUTL-UHFFFAOYSA-N 5-(5-cyclobutyl-1,3,4-oxadiazol-2-yl)-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2CCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZBLVKHPDYCQUTL-UHFFFAOYSA-N 0.000 claims description 2
• OKMNSODAWTZSEO-UHFFFAOYSA-N 5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C2CC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OKMNSODAWTZSEO-UHFFFAOYSA-N 0.000 claims description 2
• ZUILTZKVQRVTQS-UHFFFAOYSA-N 5-(5-methyl-1,3,4-oxadiazol-2-yl)-n-(oxan-4-yl)-1-propylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CCC)N=CC2=C1NC1CCOCC1 ZUILTZKVQRVTQS-UHFFFAOYSA-N 0.000 claims description 2
• KPFQBBRCRBRWEM-UHFFFAOYSA-N 5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-ethyl-6-methyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C(C)(C)C)OC=1C1=C(C)N=C2N(CC)N=CC2=C1NC1CCOCC1 KPFQBBRCRBRWEM-UHFFFAOYSA-N 0.000 claims description 2
• VKQGBNSMXQRSRO-UHFFFAOYSA-N 5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-ethyl-n-(2-methylpropyl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(NCC(C)C)C=1C1=NN=C(C(C)(C)C)O1 VKQGBNSMXQRSRO-UHFFFAOYSA-N 0.000 claims description 2
• LALOIKAYDQEYOE-GFCCVEGCSA-N 5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-ethyl-n-[(2r)-3-methylbutan-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@H](C)C(C)C)C=1C1=NN=C(C(C)(C)C)O1 LALOIKAYDQEYOE-GFCCVEGCSA-N 0.000 claims description 2
• LALOIKAYDQEYOE-LBPRGKRZSA-N 5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-ethyl-n-[(2s)-3-methylbutan-2-yl]pyrazolo[3,4-b]pyridin-4-amine Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C1=NN=C(C(C)(C)C)O1 LALOIKAYDQEYOE-LBPRGKRZSA-N 0.000 claims description 2
• GIVYETHKGAMPFA-UHFFFAOYSA-N 5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-n-cyclohexyl-1-ethylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C(C)(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCCC1 GIVYETHKGAMPFA-UHFFFAOYSA-N 0.000 claims description 2
• RUYGFGSXZBWBBG-UHFFFAOYSA-N 5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-n-cyclopentyl-1-ethylpyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C(C)(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCCC1 RUYGFGSXZBWBBG-UHFFFAOYSA-N 0.000 claims description 2
• SUJVQNASPIOZNP-GOSISDBHSA-N 5-[(4r)-4-benzyl-4,5-dihydro-1,3-oxazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C([C@@H](CC=1C=CC=CC=1)N=1)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SUJVQNASPIOZNP-GOSISDBHSA-N 0.000 claims description 2
• SUJVQNASPIOZNP-SFHVURJKSA-N 5-[(4s)-4-benzyl-4,5-dihydro-1,3-oxazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound C([C@H](CC=1C=CC=CC=1)N=1)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SUJVQNASPIOZNP-SFHVURJKSA-N 0.000 claims description 2
• OLPSIMZFAWWPKP-UHFFFAOYSA-N 5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n,n-dimethyl-1,3,4-oxadiazol-2-amine Chemical compound N=1N=C(N(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OLPSIMZFAWWPKP-UHFFFAOYSA-N 0.000 claims description 2
• FXOHAYIMSCMWMA-UHFFFAOYSA-N 5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-propan-2-yl-1,3,4-oxadiazole-2-carboxamide Chemical compound N=1N=C(C(=O)NC(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 FXOHAYIMSCMWMA-UHFFFAOYSA-N 0.000 claims description 2
• NQHJSIZOOQJUKA-UHFFFAOYSA-N 5-[3-(cyclohexylmethyl)-1,2,4-oxadiazol-5-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CC2CCCCC2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 NQHJSIZOOQJUKA-UHFFFAOYSA-N 0.000 claims description 2
• JNDCKDRDFDNTCI-UHFFFAOYSA-N 5-[3-[(dimethylamino)methyl]-1,2,4-oxadiazol-5-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CN(C)C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 JNDCKDRDFDNTCI-UHFFFAOYSA-N 0.000 claims description 2
• DBRGUQUNHLXDKG-UHFFFAOYSA-N 5-[3-[1-(benzenesulfonyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(C2(CC2)S(=O)(=O)C=2C=CC=CC=2)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DBRGUQUNHLXDKG-UHFFFAOYSA-N 0.000 claims description 2
• LHNFNEMUCQABFL-UHFFFAOYSA-N 5-[3-[[3-(dimethylamino)phenyl]methyl]-1,2,4-oxadiazol-5-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1C(CC=2C=C(C=CC=2)N(C)C)=NOC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 LHNFNEMUCQABFL-UHFFFAOYSA-N 0.000 claims description 2
• ZDPLHEWIDBTWAH-UHFFFAOYSA-N 5-[5-(2,4-dimethylphenyl)-1,3,4-oxadiazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C=2C(=CC(C)=CC=2)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZDPLHEWIDBTWAH-UHFFFAOYSA-N 0.000 claims description 2
• PTHWHMRTWQDAHZ-UHFFFAOYSA-N 5-[5-(3,4-dimethylphenyl)-1,3,4-oxadiazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(C=2C=C(C)C(C)=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 PTHWHMRTWQDAHZ-UHFFFAOYSA-N 0.000 claims description 2
• AWDJJMXJUOHGLC-UHFFFAOYSA-N 5-[5-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC2=C(N=C(C)S2)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 AWDJJMXJUOHGLC-UHFFFAOYSA-N 0.000 claims description 2
• OKJWZNZJHNQSCO-UHFFFAOYSA-N 5-[5-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC2=C(ON=C2C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OKJWZNZJHNQSCO-UHFFFAOYSA-N 0.000 claims description 2
• ZAHOLEOEWJBGGA-UHFFFAOYSA-N 5-[5-[(4-bromophenyl)methyl]-1,3,4-oxadiazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2C=CC(Br)=CC=2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZAHOLEOEWJBGGA-UHFFFAOYSA-N 0.000 claims description 2
• GRFVXDOWJCTYDC-UHFFFAOYSA-N 5-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]pyrrolidin-2-one Chemical compound N=1N=C(C2NC(=O)CC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 GRFVXDOWJCTYDC-UHFFFAOYSA-N 0.000 claims description 2
• BCUHHDAFOIMNQD-UHFFFAOYSA-N 5-[5-[[4-(dimethylamino)phenyl]methyl]-1,2,4-oxadiazol-3-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1OC(CC=2C=CC(=CC=2)N(C)C)=NC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 BCUHHDAFOIMNQD-UHFFFAOYSA-N 0.000 claims description 2
• DEQSWTLZDQUECF-UHFFFAOYSA-N 5-[5-[[4-(dimethylamino)phenyl]methyl]-1,3,4-oxadiazol-2-yl]-1-ethyl-n-(oxan-4-yl)pyrazolo[3,4-b]pyridin-4-amine Chemical compound N=1N=C(CC=2C=CC(=CC=2)N(C)C)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 DEQSWTLZDQUECF-UHFFFAOYSA-N 0.000 claims description 2
• OVLDWHWBGDZCNJ-UHFFFAOYSA-N 6-[5-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]piperidin-2-one Chemical compound N=1N=C(C2NC(=O)CCC2)OC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 OVLDWHWBGDZCNJ-UHFFFAOYSA-N 0.000 claims description 2
• VEMGUNYXQRGLJV-HAQNSBGRSA-N N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1N[C@H]1CC[C@H](O)CC1 Chemical compound N=1N=C(C)OC=1C1=CN=C2N(CC)N=CC2=C1N[C@H]1CC[C@H](O)CC1 VEMGUNYXQRGLJV-HAQNSBGRSA-N 0.000 claims description 2
• SRVLRNMDSOIISZ-UHFFFAOYSA-N [2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazol-4-yl]-morpholin-4-ylmethanone Chemical compound N=1C(C(=O)N2CCOCC2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SRVLRNMDSOIISZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• VYLUYTRLUDVGCX-UHFFFAOYSA-N methyl 2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxylate Chemical compound N=1C(C(=O)OC)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 VYLUYTRLUDVGCX-UHFFFAOYSA-N 0.000 claims description 2
• AIXPDYDGCSZQBP-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NC=2C(=CC=CC=2C)C)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 AIXPDYDGCSZQBP-UHFFFAOYSA-N 0.000 claims description 2
• SFIXCJOGEZAASK-UHFFFAOYSA-N n-[(2,3-dimethylphenyl)methyl]-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C(=C(C)C=CC=2)C)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 SFIXCJOGEZAASK-UHFFFAOYSA-N 0.000 claims description 2
• ZYNFSAGYDJYPGJ-UHFFFAOYSA-N n-[(3,4-dimethylphenyl)methyl]-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=C(C)C(C)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 ZYNFSAGYDJYPGJ-UHFFFAOYSA-N 0.000 claims description 2
• RCJQHFPRDJQVEQ-UHFFFAOYSA-N n-[(3,5-dimethylphenyl)methyl]-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=C(C)C=C(C)C=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 RCJQHFPRDJQVEQ-UHFFFAOYSA-N 0.000 claims description 2
• RBTTVRRQQXDYID-UHFFFAOYSA-N n-[(4-carbamoylphenyl)methyl]-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=CC(=CC=2)C(N)=O)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 RBTTVRRQQXDYID-UHFFFAOYSA-N 0.000 claims description 2
• XACFWVUQRSKQID-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)NCC=2C=CC(Cl)=CC=2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 XACFWVUQRSKQID-UHFFFAOYSA-N 0.000 claims description 2
• YJBFQYYQQLWGIV-UHFFFAOYSA-N n-[1-(aminomethyl)cyclohexyl]-2-[1-ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-n-methyl-1,3-oxazole-4-carboxamide Chemical compound N=1C(C(=O)N(C)C2(CN)CCCCC2)=COC=1C1=CN=C2N(CC)N=CC2=C1NC1CCOCC1 YJBFQYYQQLWGIV-UHFFFAOYSA-N 0.000 claims description 2
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