JP6133291B2 - ピラゾロ［３，４−ｃ］ピリジン化合物と使用方法 - Google Patents

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Publication number

JP6133291B2

JP6133291B2 JP2014524387A JP2014524387A JP6133291B2 JP 6133291 B2 JP6133291 B2 JP 6133291B2 JP 2014524387 A JP2014524387 A JP 2014524387A JP 2014524387 A JP2014524387 A JP 2014524387A JP 6133291 B2 JP6133291 B2 JP 6133291B2

Authority

JP

Japan

Prior art keywords

pyridin

pyrazolo

pyrazol

pyridine

methyl

Prior art date

2011-08-12

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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• 238000000034 method Methods 0.000 title description 190
• 150000005231 pyrazolo[3,4-c]pyridines Chemical class 0.000 title description 4
• -1 (piperidin-4-yl) ethyl Chemical group 0.000 claims description 380
• 150000001875 compounds Chemical class 0.000 claims description 210
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 57
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 125000001072 heteroaryl group Chemical group 0.000 claims description 42
• 201000010099 disease Diseases 0.000 claims description 41
• 206010028980 Neoplasm Diseases 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 40
• 239000008194 pharmaceutical composition Substances 0.000 claims description 33
• 238000011282 treatment Methods 0.000 claims description 33
• 201000011510 cancer Diseases 0.000 claims description 32
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 30
• 239000003814 drug Substances 0.000 claims description 30
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
• 239000002246 antineoplastic agent Substances 0.000 claims description 25
• 229940127089 cytotoxic agent Drugs 0.000 claims description 25
• 108091000080 Phosphotransferase Proteins 0.000 claims description 23
• 102000020233 phosphotransferase Human genes 0.000 claims description 23
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 16
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000004193 piperazinyl group Chemical group 0.000 claims description 10
• 125000002393 azetidinyl group Chemical group 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 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 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 9
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
• 125000003566 oxetanyl group Chemical group 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 230000027455 binding Effects 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 229910052740 iodine Inorganic materials 0.000 claims description 8
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000003725 azepanyl group Chemical group 0.000 claims description 7
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 7
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
• 206010061218 Inflammation Diseases 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• 239000000314 lubricant Substances 0.000 claims description 6
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
• 208000012902 Nervous system disease Diseases 0.000 claims description 5
• 208000025966 Neurological disease Diseases 0.000 claims description 5
• 208000036142 Viral infection Diseases 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 230000007368 endocrine function Effects 0.000 claims description 5
• 208000026278 immune system disease Diseases 0.000 claims description 5
• 230000007102 metabolic function Effects 0.000 claims description 5
• 230000009385 viral infection Effects 0.000 claims description 5
• JUXYREUMIHGZST-UHFFFAOYSA-N 1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azepan-4-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCC(N)CCC2)=N1 JUXYREUMIHGZST-UHFFFAOYSA-N 0.000 claims description 4
• FWMVELRLCYRLLJ-CVEARBPZSA-N (1s,3r)-1-n-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]cyclohexane-1,3-diamine Chemical compound C1[C@H](N)CCC[C@@H]1NC1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 FWMVELRLCYRLLJ-CVEARBPZSA-N 0.000 claims description 3
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
• OJUHXQHKLKXSGG-CYBMUJFWSA-N (3r)-1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br OJUHXQHKLKXSGG-CYBMUJFWSA-N 0.000 claims description 2
• BVCAGJZNPVSGFU-OAHLLOKOSA-N (3r)-1-[6-[5-(5-fluoropyridin-3-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=C(F)C=NC=2)=N1 BVCAGJZNPVSGFU-OAHLLOKOSA-N 0.000 claims description 2
• ORMLAAJINVYSDT-AWEZNQCLSA-N (3s)-1-[3-chloro-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Cl ORMLAAJINVYSDT-AWEZNQCLSA-N 0.000 claims description 2
• RDFCHPVWLJDNIJ-AWEZNQCLSA-N (3s)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 RDFCHPVWLJDNIJ-AWEZNQCLSA-N 0.000 claims description 2
• BVCAGJZNPVSGFU-HNNXBMFYSA-N (3s)-1-[6-[5-(5-fluoropyridin-3-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=C(F)C=NC=2)=N1 BVCAGJZNPVSGFU-HNNXBMFYSA-N 0.000 claims description 2
• HYWSOTQNDXXXJB-MRXNPFEDSA-N (4r)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]azepan-4-amine Chemical compound C1C[C@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 HYWSOTQNDXXXJB-MRXNPFEDSA-N 0.000 claims description 2
• IMMJLZKQVTXHAY-UHFFFAOYSA-N 1-[5-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CN=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 IMMJLZKQVTXHAY-UHFFFAOYSA-N 0.000 claims description 2
• JYVYFFTYRRBLNY-UHFFFAOYSA-N 1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-3-(trifluoromethyl)pyrrolidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(N)(CC2)C(F)(F)F)=N1 JYVYFFTYRRBLNY-UHFFFAOYSA-N 0.000 claims description 2
• GZYQOEDEZRBOFO-UHFFFAOYSA-N 1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azepan-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(N)CCCC2)=N1 GZYQOEDEZRBOFO-UHFFFAOYSA-N 0.000 claims description 2
• HTIXDHPEQICXCW-UHFFFAOYSA-N 2-[4-[3-(6-fluoropyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazol-1-yl]acetamide Chemical compound C1=NN(CC(=O)N)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(F)=N1 HTIXDHPEQICXCW-UHFFFAOYSA-N 0.000 claims description 2
• VUOHFWGWDSKYMI-UHFFFAOYSA-N 2-[4-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 VUOHFWGWDSKYMI-UHFFFAOYSA-N 0.000 claims description 2
• FYVJFDOSAQFXEE-UHFFFAOYSA-N 3,5-dipyridin-3-yl-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=CN=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 FYVJFDOSAQFXEE-UHFFFAOYSA-N 0.000 claims description 2
• YPOSWHJKDVSBFG-UHFFFAOYSA-N 3-(1-piperidin-4-ylpyrazol-3-yl)-5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CNCCC1N1N=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)C=C1 YPOSWHJKDVSBFG-UHFFFAOYSA-N 0.000 claims description 2
• HKDNCYDMZJZYGM-UHFFFAOYSA-N 3-(2-fluoro-5-methoxyphenyl)-5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound COC1=CC=C(F)C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)=C1 HKDNCYDMZJZYGM-UHFFFAOYSA-N 0.000 claims description 2
• LEWYARJFFZCABK-KBPBESRZSA-N 3-[6-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-2-yl]-5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C(N=1)=CC=CC=1C(C1=C2)=NNC1=CN=C2C=1C=NN(C)C=1 LEWYARJFFZCABK-KBPBESRZSA-N 0.000 claims description 2
• MLCXAWAHXUAMQD-UHFFFAOYSA-N 4-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperazin-2-one Chemical compound C1CNC(=O)CN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 MLCXAWAHXUAMQD-UHFFFAOYSA-N 0.000 claims description 2
• KQTDCSHMLHQAHE-UHFFFAOYSA-N 4-amino-n-methyl-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)(N)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 KQTDCSHMLHQAHE-UHFFFAOYSA-N 0.000 claims description 2
• XJYVGYJMUZECDN-CQSZACIVSA-N 5-(1-methylpyrazol-4-yl)-3-[6-[(3r)-piperidin-3-yl]oxypyridin-2-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(O[C@H]2CNCCC2)=N1 XJYVGYJMUZECDN-CQSZACIVSA-N 0.000 claims description 2
• RZHKFUHFPSNNES-UHFFFAOYSA-N 6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-n-(piperidin-4-ylmethyl)pyridin-2-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(NCC2CCNCC2)=N1 RZHKFUHFPSNNES-UHFFFAOYSA-N 0.000 claims description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
• OAFGYLXZSSMPQW-CQSZACIVSA-N [(3r)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-yl]methanamine Chemical compound C1[C@@H](CN)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 OAFGYLXZSSMPQW-CQSZACIVSA-N 0.000 claims description 2
• OAFGYLXZSSMPQW-AWEZNQCLSA-N [(3s)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-yl]methanamine Chemical compound C1[C@H](CN)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 OAFGYLXZSSMPQW-AWEZNQCLSA-N 0.000 claims description 2
• QVACRZZJGYNCTJ-UHFFFAOYSA-N [1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-4-yl]methanamine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCC(CN)CC2)=N1 QVACRZZJGYNCTJ-UHFFFAOYSA-N 0.000 claims description 2
• OUQSBZMPAZAVIV-UHFFFAOYSA-N n'-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]ethane-1,2-diamine Chemical compound NCCNC1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 OUQSBZMPAZAVIV-UHFFFAOYSA-N 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims 5
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 3
• BJJPPPDXUHMCKM-UHFFFAOYSA-N [1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-1,4-diazepan-6-yl]methanol Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(CO)CNCC2)=N1 BJJPPPDXUHMCKM-UHFFFAOYSA-N 0.000 claims 2
• FWMVELRLCYRLLJ-JKSUJKDBSA-N (1r,3s)-1-n-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]cyclohexane-1,3-diamine Chemical compound C1[C@@H](N)CCC[C@H]1NC1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 FWMVELRLCYRLLJ-JKSUJKDBSA-N 0.000 claims 1
• SIUHZXBMKPIEBR-CQSZACIVSA-N (3r)-1-[3-bromo-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2C[C@H](N)CCC2)=N1 SIUHZXBMKPIEBR-CQSZACIVSA-N 0.000 claims 1
• FPAAQGFYCYLQTR-CYBMUJFWSA-N (3r)-1-[3-bromo-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2C[C@H](O)CCC2)=N1 FPAAQGFYCYLQTR-CYBMUJFWSA-N 0.000 claims 1
• YWLVRWOOKKXPLZ-MRXNPFEDSA-N (3r)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC[C@@H](N)C1 YWLVRWOOKKXPLZ-MRXNPFEDSA-N 0.000 claims 1
• UTZIYQNSLAYKSK-OAHLLOKOSA-N (3r)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CC[C@@H](N)C1 UTZIYQNSLAYKSK-OAHLLOKOSA-N 0.000 claims 1
• QQLMYTBQUSPVAD-OAHLLOKOSA-N (3r)-1-[3-methyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-ol Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCC[C@@H](O)C1 QQLMYTBQUSPVAD-OAHLLOKOSA-N 0.000 claims 1
• INCYFYOAJSQBCO-CYBMUJFWSA-N (3r)-1-[4-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyrimidin-2-yl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=NC(N2C[C@H](N)CCC2)=N1 INCYFYOAJSQBCO-CYBMUJFWSA-N 0.000 claims 1
• CRTGBXQFOHCYKB-CYBMUJFWSA-N (3r)-1-[6-(5-imidazol-1-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)N2C=NC=C2)=N1 CRTGBXQFOHCYKB-CYBMUJFWSA-N 0.000 claims 1
• SGNDEKTYVWRLGA-MRXNPFEDSA-N (3r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-3-methylpyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C)C(N2C[C@H](N)CCC2)=N1 SGNDEKTYVWRLGA-MRXNPFEDSA-N 0.000 claims 1
• IUPXPASTCFUQOD-JOCHJYFZSA-N (3r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-3-methylpiperidin-3-ol Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@](C)(O)CCC2)=N1 IUPXPASTCFUQOD-JOCHJYFZSA-N 0.000 claims 1
• XOFPWIBJTONLMF-MRXNPFEDSA-N (3r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-n-methylpiperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@H](CCC2)NC)=N1 XOFPWIBJTONLMF-MRXNPFEDSA-N 0.000 claims 1
• KBYQJTFOVSYTAY-OAHLLOKOSA-N (3r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@H](N)CCC2)=N1 KBYQJTFOVSYTAY-OAHLLOKOSA-N 0.000 claims 1
• BUCZZJIVGARTQA-HZPDHXFCSA-N (3r,4r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-4-fluoropiperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@H](N)[C@H](F)CC2)=N1 BUCZZJIVGARTQA-HZPDHXFCSA-N 0.000 claims 1
• RCULPSICDMRUIS-AWEZNQCLSA-N (3s)-1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br RCULPSICDMRUIS-AWEZNQCLSA-N 0.000 claims 1
• SIUHZXBMKPIEBR-AWEZNQCLSA-N (3s)-1-[3-bromo-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2C[C@@H](N)CCC2)=N1 SIUHZXBMKPIEBR-AWEZNQCLSA-N 0.000 claims 1
• GFRXZJASIHLAME-ZDUSSCGKSA-N (3s)-1-[3-bromo-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2C[C@@H](N)CCC2)=N1 GFRXZJASIHLAME-ZDUSSCGKSA-N 0.000 claims 1
• FPAAQGFYCYLQTR-ZDUSSCGKSA-N (3s)-1-[3-bromo-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2C[C@@H](O)CCC2)=N1 FPAAQGFYCYLQTR-ZDUSSCGKSA-N 0.000 claims 1
• YRXJFWBWHWPJIZ-KRWDZBQOSA-N (3s)-1-[3-cyclopropyl-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C(N=C1N2C[C@@H](N)CCC2)=CC=C1C1CC1 YRXJFWBWHWPJIZ-KRWDZBQOSA-N 0.000 claims 1
• LNLNEGVDDONWAH-KRWDZBQOSA-N (3s)-1-[3-ethenyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1C=C LNLNEGVDDONWAH-KRWDZBQOSA-N 0.000 claims 1
• KSMBRINTVBRFFH-KRWDZBQOSA-N (3s)-1-[3-ethenyl-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C=C)C(N2C[C@@H](N)CCC2)=N1 KSMBRINTVBRFFH-KRWDZBQOSA-N 0.000 claims 1
• KTVHKYSCYWWSBH-INIZCTEOSA-N (3s)-1-[3-ethenyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C=C)C(N2C[C@@H](N)CCC2)=N1 KTVHKYSCYWWSBH-INIZCTEOSA-N 0.000 claims 1
• MCRHVULASBRJTF-KRWDZBQOSA-N (3s)-1-[3-ethyl-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound CCC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(CC)N=C2)N=C1N1CCC[C@H](N)C1 MCRHVULASBRJTF-KRWDZBQOSA-N 0.000 claims 1
• FECWDXPJMOSNMV-INIZCTEOSA-N (3s)-1-[3-ethyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound CCC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCC[C@H](N)C1 FECWDXPJMOSNMV-INIZCTEOSA-N 0.000 claims 1
• YWLVRWOOKKXPLZ-INIZCTEOSA-N (3s)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC[C@H](N)C1 YWLVRWOOKKXPLZ-INIZCTEOSA-N 0.000 claims 1
• UTZIYQNSLAYKSK-HNNXBMFYSA-N (3s)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CC[C@H](N)C1 UTZIYQNSLAYKSK-HNNXBMFYSA-N 0.000 claims 1
• XWOSSDMMJDYDBX-HNNXBMFYSA-N (3s)-1-[3-methyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCC[C@H](N)C1 XWOSSDMMJDYDBX-HNNXBMFYSA-N 0.000 claims 1
• QQLMYTBQUSPVAD-HNNXBMFYSA-N (3s)-1-[3-methyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-ol Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCC[C@H](O)C1 QQLMYTBQUSPVAD-HNNXBMFYSA-N 0.000 claims 1
• FEMLZOWSASZDMK-KRWDZBQOSA-N (3s)-1-[3-prop-1-en-2-yl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound CC(=C)C1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC[C@H](N)C1 FEMLZOWSASZDMK-KRWDZBQOSA-N 0.000 claims 1
• VGJWLOJQVWBUSL-KRWDZBQOSA-N (3s)-1-[3-propan-2-yl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound CC(C)C1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC[C@H](N)C1 VGJWLOJQVWBUSL-KRWDZBQOSA-N 0.000 claims 1
• INCYFYOAJSQBCO-ZDUSSCGKSA-N (3s)-1-[4-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyrimidin-2-yl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=NC(N2C[C@@H](N)CCC2)=N1 INCYFYOAJSQBCO-ZDUSSCGKSA-N 0.000 claims 1
• WIBSDSHYWJBRSJ-AWEZNQCLSA-N (3s)-1-[5-chloro-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=NC(N2C[C@@H](N)CCC2)=CC=C1Cl WIBSDSHYWJBRSJ-AWEZNQCLSA-N 0.000 claims 1
• CRTGBXQFOHCYKB-ZDUSSCGKSA-N (3s)-1-[6-(5-imidazol-1-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)N2C=NC=C2)=N1 CRTGBXQFOHCYKB-ZDUSSCGKSA-N 0.000 claims 1
• UIQIHRNBPQGQQH-AWEZNQCLSA-N (3s)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)-3-(trifluoromethyl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1C(F)(F)F UIQIHRNBPQGQQH-AWEZNQCLSA-N 0.000 claims 1
• SGNDEKTYVWRLGA-INIZCTEOSA-N (3s)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-3-methylpyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C)C(N2C[C@@H](N)CCC2)=N1 SGNDEKTYVWRLGA-INIZCTEOSA-N 0.000 claims 1
• BQBYYZXHZGVJMR-KRWDZBQOSA-N (3s)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-3-prop-1-en-2-ylpyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C(C)=C)C(N2C[C@@H](N)CCC2)=N1 BQBYYZXHZGVJMR-KRWDZBQOSA-N 0.000 claims 1
• RBCUQLJADFRREM-KRWDZBQOSA-N (3s)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-3-propan-2-ylpyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C(C)C)C(N2C[C@@H](N)CCC2)=N1 RBCUQLJADFRREM-KRWDZBQOSA-N 0.000 claims 1
• IUPXPASTCFUQOD-QFIPXVFZSA-N (3s)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-3-methylpiperidin-3-ol Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@](C)(O)CCC2)=N1 IUPXPASTCFUQOD-QFIPXVFZSA-N 0.000 claims 1
• XOFPWIBJTONLMF-INIZCTEOSA-N (3s)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-n-methylpiperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@H](CCC2)NC)=N1 XOFPWIBJTONLMF-INIZCTEOSA-N 0.000 claims 1
• KBYQJTFOVSYTAY-HNNXBMFYSA-N (3s)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@H](N)CCC2)=N1 KBYQJTFOVSYTAY-HNNXBMFYSA-N 0.000 claims 1
• XNXVZMDFPQJZOY-INIZCTEOSA-N (3s)-1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-3-prop-1-en-2-ylpyridin-2-yl]piperidin-3-amine Chemical compound CC(=C)C1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCC[C@H](N)C1 XNXVZMDFPQJZOY-INIZCTEOSA-N 0.000 claims 1
• OBGMBNNSDGIRFJ-INIZCTEOSA-N (3s)-1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-3-propan-2-ylpyridin-2-yl]piperidin-3-amine Chemical compound CC(C)C1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCC[C@H](N)C1 OBGMBNNSDGIRFJ-INIZCTEOSA-N 0.000 claims 1
• UZSKGLPUMSUOBY-AWEZNQCLSA-N (3s)-1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@H](N)CCC2)=N1 UZSKGLPUMSUOBY-AWEZNQCLSA-N 0.000 claims 1
• UCDTVUPIWRMUQR-AWEZNQCLSA-N (3s)-3-amino-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-2-one Chemical compound O=C1[C@@H](N)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 UCDTVUPIWRMUQR-AWEZNQCLSA-N 0.000 claims 1
• PIKYKNBWDFZDPW-NRFANRHFSA-N (3s)-3-methyl-1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@](C)(O)CCC2)=N1 PIKYKNBWDFZDPW-NRFANRHFSA-N 0.000 claims 1
• BHBWYOGZMWLUSZ-KGLIPLIRSA-N (3s,5r)-1-[3-bromo-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-5-fluoropiperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2C[C@H](F)C[C@H](N)C2)=N1 BHBWYOGZMWLUSZ-KGLIPLIRSA-N 0.000 claims 1
• ZIEHPJPLHNKHPZ-OLZOCXBDSA-N (3s,5r)-1-[3-bromo-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-5-fluoropiperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2C[C@H](F)C[C@H](N)C2)=N1 ZIEHPJPLHNKHPZ-OLZOCXBDSA-N 0.000 claims 1
• PPCHVHGYGZYEPP-CVEARBPZSA-N (3s,5r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]-3-methylpyridin-2-yl]-5-fluoropiperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C)C(N2C[C@H](F)C[C@H](N)C2)=N1 PPCHVHGYGZYEPP-CVEARBPZSA-N 0.000 claims 1
• HOPGMCWYVDUYNO-CABCVRRESA-N (3s,5r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-5-fluoropiperidin-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@H](F)C[C@H](N)C2)=N1 HOPGMCWYVDUYNO-CABCVRRESA-N 0.000 claims 1
• LGXKCOCTCFMWHJ-CABCVRRESA-N (3s,5r)-5-fluoro-1-[3-methyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1C[C@@H](N)C[C@@H](F)C1 LGXKCOCTCFMWHJ-CABCVRRESA-N 0.000 claims 1
• WEEKHEMGSDJQLC-CABCVRRESA-N (3s,5r)-5-fluoro-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)C[C@@H](F)CN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 WEEKHEMGSDJQLC-CABCVRRESA-N 0.000 claims 1
• WYNXSGCLOVESGX-KGLIPLIRSA-N (3s,5r)-5-fluoro-1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@H](F)C[C@H](N)C2)=N1 WYNXSGCLOVESGX-KGLIPLIRSA-N 0.000 claims 1
• SBESMDFHOZSXSF-UHFFFAOYSA-N (4-aminopiperidin-1-yl)-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]methanone Chemical compound C1CC(N)CCN1C(=O)C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 SBESMDFHOZSXSF-UHFFFAOYSA-N 0.000 claims 1
• JIENEKDVIAAQIC-OAHLLOKOSA-N (4r)-1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]azepan-4-amine Chemical compound C1C[C@H](N)CCCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br JIENEKDVIAAQIC-OAHLLOKOSA-N 0.000 claims 1
• XEMLZMNENJBYBP-QGZVFWFLSA-N (4r)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]azepan-4-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC[C@@H](N)CC1 XEMLZMNENJBYBP-QGZVFWFLSA-N 0.000 claims 1
• DYEWIERMHIZZLA-MRXNPFEDSA-N (4r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azepan-4-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC[C@H](N)CCC2)=N1 DYEWIERMHIZZLA-MRXNPFEDSA-N 0.000 claims 1
• JUXYREUMIHGZST-OAHLLOKOSA-N (4r)-1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azepan-4-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC[C@H](N)CCC2)=N1 JUXYREUMIHGZST-OAHLLOKOSA-N 0.000 claims 1
• JIENEKDVIAAQIC-HNNXBMFYSA-N (4s)-1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]azepan-4-amine Chemical compound C1C[C@@H](N)CCCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br JIENEKDVIAAQIC-HNNXBMFYSA-N 0.000 claims 1
• XEMLZMNENJBYBP-KRWDZBQOSA-N (4s)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]azepan-4-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC[C@H](N)CC1 XEMLZMNENJBYBP-KRWDZBQOSA-N 0.000 claims 1
• BLMDGEGSPQPBNP-OAHLLOKOSA-N (6r)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-1,4-diazepan-6-ol Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@H](O)CNCC2)=N1 BLMDGEGSPQPBNP-OAHLLOKOSA-N 0.000 claims 1
• BLMDGEGSPQPBNP-HNNXBMFYSA-N (6s)-1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-1,4-diazepan-6-ol Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@H](O)CNCC2)=N1 BLMDGEGSPQPBNP-HNNXBMFYSA-N 0.000 claims 1
• CEQYRHVPNYLAKA-UHFFFAOYSA-N 1-(3-amino-2,2-dimethylpropyl)-5-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-one Chemical compound C1=CC(=O)N(CC(C)(CN)C)C=C1C1=NNC2=CN=C(C=3C=NC=CC=3)C=C12 CEQYRHVPNYLAKA-UHFFFAOYSA-N 0.000 claims 1
• LSQVHSIKEZMLQX-UHFFFAOYSA-N 1-(piperidin-4-ylmethyl)-3-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)imidazolidin-2-one Chemical compound C1CN(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)C(=O)N1CC1CCNCC1 LSQVHSIKEZMLQX-UHFFFAOYSA-N 0.000 claims 1
• GIWBSVUHLIJMSE-UHFFFAOYSA-N 1-[3-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyridin-4-yl]azepan-4-amine Chemical compound C1CC(N)CCCN1C1=CC=NC=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC=C1F GIWBSVUHLIJMSE-UHFFFAOYSA-N 0.000 claims 1
• DFLOMAREWUSYDW-UHFFFAOYSA-N 1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br DFLOMAREWUSYDW-UHFFFAOYSA-N 0.000 claims 1
• IXDIFIPKASFTPV-UHFFFAOYSA-N 1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-4-ol Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC(O)CC1 IXDIFIPKASFTPV-UHFFFAOYSA-N 0.000 claims 1
• WLUGAYVZEOAUHP-UHFFFAOYSA-N 1-[3-methyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-4-amine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCC(N)CC1 WLUGAYVZEOAUHP-UHFFFAOYSA-N 0.000 claims 1
• HTAYWJMJSJNZEL-UHFFFAOYSA-N 1-[6-[3-(1-methylpyrazol-3-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]piperidin-4-amine Chemical compound CN1C=CC(C=2C3=CC(=NC=C3NN=2)C=2N=C(C=NC=2)N2CCC(N)CC2)=N1 HTAYWJMJSJNZEL-UHFFFAOYSA-N 0.000 claims 1
• WBAWFBZASDSEKA-UHFFFAOYSA-N 1-[6-[3-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]piperidin-4-amine Chemical compound C1=NN(C)C=C1C1=NNC2=CN=C(C=3N=C(C=NC=3)N3CCC(N)CC3)C=C12 WBAWFBZASDSEKA-UHFFFAOYSA-N 0.000 claims 1
• BXYXJSLIRCVQHH-UHFFFAOYSA-N 1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azepan-3-ol Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(O)CCCC2)=N1 BXYXJSLIRCVQHH-UHFFFAOYSA-N 0.000 claims 1
• XXEBBXOTFNCOMU-UHFFFAOYSA-N 1-[6-[5-[1-(2-fluoroethyl)pyrazol-4-yl]-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azepan-3-amine Chemical compound C1C(N)CCCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C2=CN(CCF)N=C2)=N1 XXEBBXOTFNCOMU-UHFFFAOYSA-N 0.000 claims 1
• ZHZPKKRZEWPEKA-UHFFFAOYSA-N 1-methyl-4-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyridin-2-one Chemical compound O=C1N(C)C=CC(C=2N=CC=3NN=C(C=3C=2)C=2N=C(C=CC=2)N2CCNCC2)=C1 ZHZPKKRZEWPEKA-UHFFFAOYSA-N 0.000 claims 1
• BSOSQKZSTMNSEC-UHFFFAOYSA-N 1-n-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]cyclohexane-1,3-diamine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(NC2CC(N)CCC2)=N1 BSOSQKZSTMNSEC-UHFFFAOYSA-N 0.000 claims 1
• XDYMUBVABLEPLQ-UHFFFAOYSA-N 2-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 XDYMUBVABLEPLQ-UHFFFAOYSA-N 0.000 claims 1
• FDUVDOYSKNJROE-UHFFFAOYSA-N 2-[1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-yl]ethanamine Chemical compound C1C(CCN)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 FDUVDOYSKNJROE-UHFFFAOYSA-N 0.000 claims 1
• SVYHADKWCWQANW-UHFFFAOYSA-N 2-[4-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazol-1-yl]acetonitrile Chemical compound C1=NN(CC#N)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 SVYHADKWCWQANW-UHFFFAOYSA-N 0.000 claims 1
• YKHRTOSUKCHRDX-UHFFFAOYSA-N 2-[4-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 YKHRTOSUKCHRDX-UHFFFAOYSA-N 0.000 claims 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
• QEOHCRBBBDTECB-UHFFFAOYSA-N 2-methyl-1-[4-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazol-1-yl]propan-2-ol Chemical compound C1=NN(CC(C)(O)C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 QEOHCRBBBDTECB-UHFFFAOYSA-N 0.000 claims 1
• UQJXXIUBMVASHR-UHFFFAOYSA-N 3-(4-aminopiperidine-1-carbonyl)-1-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyrrolidin-2-one Chemical compound C1CC(N)CCN1C(=O)C1C(=O)N(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)CC1 UQJXXIUBMVASHR-UHFFFAOYSA-N 0.000 claims 1
• QYONTMXDPFWFPN-UHFFFAOYSA-N 3-(5-bromo-6-piperazin-1-ylpyridin-2-yl)-5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2CCNCC2)=N1 QYONTMXDPFWFPN-UHFFFAOYSA-N 0.000 claims 1
• CHWFFBDEESOIBC-UHFFFAOYSA-N 3-(6-piperazin-1-ylpyridin-2-yl)-5-(1-propan-2-ylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C(C)C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 CHWFFBDEESOIBC-UHFFFAOYSA-N 0.000 claims 1
• XKPHITFYRRNWMQ-UHFFFAOYSA-N 3-(6-piperazin-1-ylpyridin-2-yl)-5-(1-propylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CCC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 XKPHITFYRRNWMQ-UHFFFAOYSA-N 0.000 claims 1
• MTNRQWRDLVCYQT-UHFFFAOYSA-N 3-(6-piperazin-1-ylpyridin-2-yl)-5-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC(F)(F)F)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 MTNRQWRDLVCYQT-UHFFFAOYSA-N 0.000 claims 1
• IQOMPZFXVBSCPB-UHFFFAOYSA-N 3-(6-piperazin-1-ylpyridin-2-yl)-5-[5-(trifluoromethyl)pyridin-3-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound FC(F)(F)C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2N=C(C=CC=2)N2CCNCC2)=C1 IQOMPZFXVBSCPB-UHFFFAOYSA-N 0.000 claims 1
• AFDQNIGCDMCAHS-UHFFFAOYSA-N 3-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]-n-(piperidin-4-ylmethyl)pyridin-4-amine Chemical compound FC1=CC=CC=C1C1=NNC2=CN=C(C=3C(=CC=NC=3)NCC3CCNCC3)C=C12 AFDQNIGCDMCAHS-UHFFFAOYSA-N 0.000 claims 1
• ARNZQCZBCDADJH-UHFFFAOYSA-N 3-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 ARNZQCZBCDADJH-UHFFFAOYSA-N 0.000 claims 1
• IYWFOOCVEDOSQM-UHFFFAOYSA-N 3-[3-(6-piperidin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCCCC2)=N1 IYWFOOCVEDOSQM-UHFFFAOYSA-N 0.000 claims 1
• YOTFCVUNNCLPOT-GFCCVEGCSA-N 3-[3-[6-[(3r)-3-aminopiperidin-1-yl]pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridin-5-yl]-1,3-oxazolidin-2-one Chemical compound C1[C@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)N2C(OCC2)=O)=N1 YOTFCVUNNCLPOT-GFCCVEGCSA-N 0.000 claims 1
• YOTFCVUNNCLPOT-LBPRGKRZSA-N 3-[3-[6-[(3s)-3-aminopiperidin-1-yl]pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridin-5-yl]-1,3-oxazolidin-2-one Chemical compound C1[C@@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)N2C(OCC2)=O)=N1 YOTFCVUNNCLPOT-LBPRGKRZSA-N 0.000 claims 1
• BNXCQJKCLBQCJW-UHFFFAOYSA-N 3-[5-bromo-6-[3,3-dimethyl-4-(2-methylsulfonylethyl)piperazin-1-yl]pyridin-2-yl]-5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2CC(C)(C)N(CCS(C)(=O)=O)CC2)=N1 BNXCQJKCLBQCJW-UHFFFAOYSA-N 0.000 claims 1
• RSRCWMFXYSDZGP-UHFFFAOYSA-N 3-[5-methyl-6-(4-methylpiperazin-1-yl)pyridin-2-yl]-5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CN(C)CCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)=CC=C1C RSRCWMFXYSDZGP-UHFFFAOYSA-N 0.000 claims 1
• FTCGBSBOZWGTEI-UHFFFAOYSA-N 3-[6-(1,4-diazepan-1-yl)-4-methylpyridin-2-yl]-5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC(C)=CC(N2CCNCCC2)=N1 FTCGBSBOZWGTEI-UHFFFAOYSA-N 0.000 claims 1
• GKVMUEOQUFVJNA-UHFFFAOYSA-N 3-[6-(1,4-diazepan-1-yl)pyridin-2-yl]-5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCCC2)=N1 GKVMUEOQUFVJNA-UHFFFAOYSA-N 0.000 claims 1
• DLZIZKARHRLIHL-UHFFFAOYSA-N 3-[6-(1,4-diazepan-1-yl)pyridin-2-yl]-5-[1-(2-fluoroethyl)pyrazol-4-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CCF)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCCC2)=N1 DLZIZKARHRLIHL-UHFFFAOYSA-N 0.000 claims 1
• ASMXGGRPAPHNDN-UHFFFAOYSA-N 3-[6-(3,3-dimethylpiperazin-1-yl)pyridin-2-yl]-5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(C)(C)NCC2)=N1 ASMXGGRPAPHNDN-UHFFFAOYSA-N 0.000 claims 1
• UNMSQVAIBXEGPW-UHFFFAOYSA-N 3-[6-(6,6-difluoro-1,4-diazepan-1-yl)pyridin-2-yl]-5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(F)(F)CNCC2)=N1 UNMSQVAIBXEGPW-UHFFFAOYSA-N 0.000 claims 1
• XKFCTVWJFCKNBW-GASCZTMLSA-N 3-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyridin-2-yl]-5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@@H](C)N[C@@H](C)C2)=N1 XKFCTVWJFCKNBW-GASCZTMLSA-N 0.000 claims 1
• HCIXMOJLLZUZRM-UHFFFAOYSA-N 3-[6-[3,3-dimethyl-4-(2-methylsulfonylethyl)piperazin-1-yl]-5-methylpyridin-2-yl]-5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCN(CCS(C)(=O)=O)C(C)(C)C1 HCIXMOJLLZUZRM-UHFFFAOYSA-N 0.000 claims 1
• BAUZKJYZGGFFLL-UHFFFAOYSA-N 3-ethyl-5-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrimidin-4-one Chemical compound O=C1N(CC)C=NC=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 BAUZKJYZGGFFLL-UHFFFAOYSA-N 0.000 claims 1
• KIBZGUOKQUDIFC-UHFFFAOYSA-N 3-methyl-1-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]imidazolidine-2,4-dione Chemical compound O=C1N(C)C(=O)CN1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 KIBZGUOKQUDIFC-UHFFFAOYSA-N 0.000 claims 1
• TYPVALHZTLRMMR-UHFFFAOYSA-N 4-[1-[3-bromo-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azetidin-3-yl]piperazin-2-one Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2CC(C2)N2CC(=O)NCC2)=N1 TYPVALHZTLRMMR-UHFFFAOYSA-N 0.000 claims 1
• DYAGKFLCPXLHPV-UHFFFAOYSA-N 4-[3-bromo-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]morpholine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2CCOCC2)=N1 DYAGKFLCPXLHPV-UHFFFAOYSA-N 0.000 claims 1
• VGXQLRWWQIUSGF-UHFFFAOYSA-N 4-[3-methyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]morpholine Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N1CCOCC1 VGXQLRWWQIUSGF-UHFFFAOYSA-N 0.000 claims 1
• NMOUXRDKGIZNGE-UHFFFAOYSA-N 4-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]-1,4-diazepan-2-one Chemical compound C1CCNC(=O)CN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 NMOUXRDKGIZNGE-UHFFFAOYSA-N 0.000 claims 1
• FORXCJRKNHYUBC-UHFFFAOYSA-N 4-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-4-ol Chemical compound C=1C=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=NC=1C1(O)CCNCC1 FORXCJRKNHYUBC-UHFFFAOYSA-N 0.000 claims 1
• FTLPJRYZRTWCHZ-UHFFFAOYSA-N 4-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]morpholine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCOCC2)=N1 FTLPJRYZRTWCHZ-UHFFFAOYSA-N 0.000 claims 1
• JYFODXOVZPQVRW-UHFFFAOYSA-N 4-amino-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)(N)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 JYFODXOVZPQVRW-UHFFFAOYSA-N 0.000 claims 1
• GWYKGOZFKXKMND-UHFFFAOYSA-N 5-(1-cyclobutylpyrazol-4-yl)-3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CCC1N1N=CC(C=2N=CC=3NN=C(C=3C=2)C=2N=C(C=CC=2)N2CCNCC2)=C1 GWYKGOZFKXKMND-UHFFFAOYSA-N 0.000 claims 1
• BMHDMTOGIQRECR-UHFFFAOYSA-N 5-(1-cyclopropylpyrazol-4-yl)-3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CC1N1N=CC(C=2N=CC=3NN=C(C=3C=2)C=2N=C(C=CC=2)N2CCNCC2)=C1 BMHDMTOGIQRECR-UHFFFAOYSA-N 0.000 claims 1
• XOYGKHCOPQURQV-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-(4-methoxypyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC(OC)=CC=N1 XOYGKHCOPQURQV-UHFFFAOYSA-N 0.000 claims 1
• DXJWSLRIHWJKCO-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-(4-prop-1-en-2-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC(C(C)=C)=CC=N1 DXJWSLRIHWJKCO-UHFFFAOYSA-N 0.000 claims 1
• XMTRMCWKMSOGQR-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-(5-methyl-6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(C)C(N2CCNCC2)=N1 XMTRMCWKMSOGQR-UHFFFAOYSA-N 0.000 claims 1
• LYQWUXCDSOKJRT-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-(6-piperazin-1-ylpyrazin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CN=CC(N2CCNCC2)=N1 LYQWUXCDSOKJRT-UHFFFAOYSA-N 0.000 claims 1
• VFXUYKQSTNDXRJ-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-[4-(trifluoromethyl)pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC(C(F)(F)F)=CC=N1 VFXUYKQSTNDXRJ-UHFFFAOYSA-N 0.000 claims 1
• WKPYUMZOLALQOY-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-[6-(4-methylpiperazin-1-yl)pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCN(C)CC2)=N1 WKPYUMZOLALQOY-UHFFFAOYSA-N 0.000 claims 1
• RVDMLVBMTHFTNU-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-[6-(6-fluoro-1,4-diazepan-1-yl)pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(F)CNCC2)=N1 RVDMLVBMTHFTNU-UHFFFAOYSA-N 0.000 claims 1
• OYBHRXWHGRKFFA-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-[6-[3-(trifluoromethyl)piperazin-1-yl]pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(NCC2)C(F)(F)F)=N1 OYBHRXWHGRKFFA-UHFFFAOYSA-N 0.000 claims 1
• BWJJFTLXLCDZOH-UHFFFAOYSA-N 5-(1-ethylpyrazol-4-yl)-3-[6-[4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCN(CC2)C2COC2)=N1 BWJJFTLXLCDZOH-UHFFFAOYSA-N 0.000 claims 1
• CNLSVCKBBPDJDM-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-3-(2-piperazin-1-ylpyrimidin-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=NC(N2CCNCC2)=N1 CNLSVCKBBPDJDM-UHFFFAOYSA-N 0.000 claims 1
• CDRIATLSWATULL-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-3-(2-piperidin-4-ylpyrimidin-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=NC(C2CCNCC2)=N1 CDRIATLSWATULL-UHFFFAOYSA-N 0.000 claims 1
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