RU2638116C2 - Пиразоло[3,4-с]пиридины и способы их применения - Google Patents

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Publication number

RU2638116C2

RU2638116C2 RU2014106966A RU2014106966A RU2638116C2 RU 2638116 C2 RU2638116 C2 RU 2638116C2 RU 2014106966 A RU2014106966 A RU 2014106966A RU 2014106966 A RU2014106966 A RU 2014106966A RU 2638116 C2 RU2638116 C2 RU 2638116C2

Authority

RU

Russia

Prior art keywords

pyridin

pyrazolo

pyrazol

piperidin

methyl

Prior art date

2011-08-12

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• 238000000034 method Methods 0.000 title abstract description 179
• 150000005231 pyrazolo[3,4-c]pyridines Chemical class 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 313
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• 230000001404 mediated effect Effects 0.000 claims abstract description 10
• -1 (piperidin-4-yl) ethyl Chemical group 0.000 claims description 262
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
• 239000008194 pharmaceutical composition Substances 0.000 claims description 30
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 22
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
• 239000003085 diluting agent Substances 0.000 claims description 13
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 12
• 101150065749 Churc1 gene Proteins 0.000 claims description 12
• 102100038239 Protein Churchill Human genes 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 102000001253 Protein Kinase Human genes 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 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 7
• 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 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000003566 oxetanyl group Chemical group 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000003725 azepanyl group Chemical group 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
• DEZJKGVJDMAGPI-UHFFFAOYSA-N 4-(piperidin-4-ylmethyl)morpholine Chemical compound C1COCCN1CC1CCNCC1 DEZJKGVJDMAGPI-UHFFFAOYSA-N 0.000 claims description 4
• 108060006633 protein kinase Proteins 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
• IKFWWTFURAIGPU-HNNXBMFYSA-N (3s)-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)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 IKFWWTFURAIGPU-HNNXBMFYSA-N 0.000 claims description 3
• QKRLKEOSBXNMGP-UHFFFAOYSA-N 5-(oxan-3-yl)-3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CCOCC1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 QKRLKEOSBXNMGP-UHFFFAOYSA-N 0.000 claims description 3
• BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 claims description 3
• FWMVELRLCYRLLJ-HOTGVXAUSA-N (1s,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-HOTGVXAUSA-N 0.000 claims description 2
• UKAGZEMTXTYYHX-MRXNPFEDSA-N (3r)-1-[3-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]phenyl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@H](N)CCC2)=C1 UKAGZEMTXTYYHX-MRXNPFEDSA-N 0.000 claims description 2
• RCULPSICDMRUIS-CQSZACIVSA-N (3r)-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-CQSZACIVSA-N 0.000 claims description 2
• XRSAFTMMIVQIDX-CQSZACIVSA-N (3r)-1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-ol Chemical compound C1[C@H](O)CCCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br XRSAFTMMIVQIDX-CQSZACIVSA-N 0.000 claims description 2
• 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
• SNWCKNPCXZGTJB-CYBMUJFWSA-N (3r)-1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-ol Chemical compound C1[C@H](O)CCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br SNWCKNPCXZGTJB-CYBMUJFWSA-N 0.000 claims description 2
• ORMLAAJINVYSDT-CQSZACIVSA-N (3r)-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-CQSZACIVSA-N 0.000 claims description 2
• LYXMIPMPXXMDMV-MRXNPFEDSA-N (3r)-1-[5-(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=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)C=N1 LYXMIPMPXXMDMV-MRXNPFEDSA-N 0.000 claims description 2
• CSYZJSGDIIBSMR-OAHLLOKOSA-N (3r)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-ol Chemical compound C1[C@H](O)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 CSYZJSGDIIBSMR-OAHLLOKOSA-N 0.000 claims description 2
• UZSKGLPUMSUOBY-CQSZACIVSA-N (3r)-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-CQSZACIVSA-N 0.000 claims description 2
• NVIMRDPIWGJULC-CYBMUJFWSA-N (3r)-1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]pyrrolidin-3-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2C[C@H](N)CC2)=N1 NVIMRDPIWGJULC-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
• 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 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
• IZVRVJUQKJASMV-HNNXBMFYSA-N (3s)-1-[5-(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=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)C=N1 IZVRVJUQKJASMV-HNNXBMFYSA-N 0.000 claims description 2
• CSYZJSGDIIBSMR-HNNXBMFYSA-N (3s)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-ol Chemical compound C1[C@@H](O)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 CSYZJSGDIIBSMR-HNNXBMFYSA-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
• 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 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
• 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 description 2
• HYWSOTQNDXXXJB-INIZCTEOSA-N (4s)-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-INIZCTEOSA-N 0.000 claims description 2
• 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 description 2
• SVDDJOORCKWBEF-UHFFFAOYSA-N 1-[3-chloro-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Cl SVDDJOORCKWBEF-UHFFFAOYSA-N 0.000 claims description 2
• MTVXTVPKTZLIOC-UHFFFAOYSA-N 1-[3-methyl-6-(5-pyridin-3-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)C=2C=NC=CC=2)N=C1N1CCC(N)CC1 MTVXTVPKTZLIOC-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• RKQKFCKHAXUXEH-UHFFFAOYSA-N 1-[5-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl]azepan-4-amine Chemical compound C1CC(N)CCCN1C1=CN=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 RKQKFCKHAXUXEH-UHFFFAOYSA-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
• HYWSOTQNDXXXJB-UHFFFAOYSA-N 1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]azepan-4-amine Chemical compound C1CC(N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 HYWSOTQNDXXXJB-UHFFFAOYSA-N 0.000 claims description 2
• DFLCJIYQRLLZKS-UHFFFAOYSA-N 1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 DFLCJIYQRLLZKS-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
• 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 2
• OZNVWRLWXYBLRC-UHFFFAOYSA-N 1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-4-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCC(N)CC2)=N1 OZNVWRLWXYBLRC-UHFFFAOYSA-N 0.000 claims description 2
• OLGXFUTXHMRQII-UHFFFAOYSA-N 1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-4-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCC(O)CC2)=N1 OLGXFUTXHMRQII-UHFFFAOYSA-N 0.000 claims description 2
• WPAGZAPRFWIYJS-UHFFFAOYSA-N 1-methyl-4-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]piperazin-2-one Chemical compound C1C(=O)N(C)CCN1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 WPAGZAPRFWIYJS-UHFFFAOYSA-N 0.000 claims description 2
• AORRDGZBZSCFCE-UHFFFAOYSA-N 2-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1N(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)CCC11CCNCC1 AORRDGZBZSCFCE-UHFFFAOYSA-N 0.000 claims description 2
• XACXGGOSZXZXQY-MRXNPFEDSA-N 2-[(3r)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-yl]ethanamine Chemical compound C1[C@@H](CCN)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 XACXGGOSZXZXQY-MRXNPFEDSA-N 0.000 claims description 2
• XACXGGOSZXZXQY-INIZCTEOSA-N 2-[(3s)-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-yl]ethanamine Chemical compound C1[C@H](CCN)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 XACXGGOSZXZXQY-INIZCTEOSA-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
• ZYYNCEXTLNUHQD-UHFFFAOYSA-N 2-methyl-1-[4-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyrazol-1-yl]propan-2-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CN(CC(C)(C)O)N=C1 ZYYNCEXTLNUHQD-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
• OCPZKWYVZWFRTG-UHFFFAOYSA-N 3-(2-fluoro-5-methylphenyl)-5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound CC1=CC=C(F)C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)=C1 OCPZKWYVZWFRTG-UHFFFAOYSA-N 0.000 claims description 2
• GNQRKXIKAGBFEM-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC=C1F GNQRKXIKAGBFEM-UHFFFAOYSA-N 0.000 claims description 2
• QQOLDSPBJKOAGB-UHFFFAOYSA-N 3-(6-piperidin-1-ylpyridin-2-yl)-5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CCCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 QQOLDSPBJKOAGB-UHFFFAOYSA-N 0.000 claims description 2
• NHOCHPHSKZCGPO-UHFFFAOYSA-N 3-[1-(piperidin-4-ylmethyl)pyrazol-4-yl]-5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)C=NN1CC1CCNCC1 NHOCHPHSKZCGPO-UHFFFAOYSA-N 0.000 claims description 2
• CZLPPAMVDRHPPR-UHFFFAOYSA-N 3-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyridin-2-amine Chemical compound NC1=NC=CC=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 CZLPPAMVDRHPPR-UHFFFAOYSA-N 0.000 claims description 2
• PUECOGCCEUXMDA-UHFFFAOYSA-N 3-[6-(1,4-diazepan-1-yl)pyridin-2-yl]-5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CCNCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 PUECOGCCEUXMDA-UHFFFAOYSA-N 0.000 claims description 2
• HIYIDCSIHKTRBL-UHFFFAOYSA-N 3-piperazin-1-yl-5-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)benzonitrile Chemical compound C=1C(C#N)=CC(N2CCNCC2)=CC=1C(C1=C2)=NNC1=CN=C2C1=CC=CN=C1 HIYIDCSIHKTRBL-UHFFFAOYSA-N 0.000 claims description 2
• BFKALRIDPJGPRZ-UHFFFAOYSA-N 4-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]morpholine Chemical compound C1COCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 BFKALRIDPJGPRZ-UHFFFAOYSA-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
• DDJSMJOXPLNBBR-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 DDJSMJOXPLNBBR-UHFFFAOYSA-N 0.000 claims description 2
• DPCSEKLXKDUSOY-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-3-(6-piperidin-4-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(C2CCNCC2)=N1 DPCSEKLXKDUSOY-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
• LDNKOJMEWRTTJB-UHFFFAOYSA-N 5-(5-fluoropyridin-3-yl)-3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine Chemical compound FC1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2N=C(C=CC=2)N2CCNCC2)=C1 LDNKOJMEWRTTJB-UHFFFAOYSA-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
• NBPQNKAZCNUSIZ-CQSZACIVSA-N [(3r)-1-[5-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl]pyrrolidin-3-yl]methanamine Chemical compound C1[C@@H](CN)CCN1C1=CN=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 NBPQNKAZCNUSIZ-CQSZACIVSA-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
• XXPWKKUKPXAQSQ-UHFFFAOYSA-N [1-[5-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl]piperidin-4-yl]methanamine Chemical compound C1CC(CN)CCN1C1=CN=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 XXPWKKUKPXAQSQ-UHFFFAOYSA-N 0.000 claims description 2
• MLTZMNOMUOFGPI-UHFFFAOYSA-N [1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-4-yl]methanamine Chemical compound C1CC(CN)CCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 MLTZMNOMUOFGPI-UHFFFAOYSA-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
• 150000001412 amines Chemical class 0.000 claims description 2
• QQEGBGHTXJUJDN-UHFFFAOYSA-N n'-[4-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]ethane-1,2-diamine Chemical compound C1=NC(NCCN)=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 QQEGBGHTXJUJDN-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
• BWIRYGQAWXKGTO-UHFFFAOYSA-N n-piperidin-4-yl-5-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-amine Chemical compound C1CNCCC1NC1=CN=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=C1 BWIRYGQAWXKGTO-UHFFFAOYSA-N 0.000 claims description 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 2
• 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 2
• 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
• PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical compound NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 claims 2
• NCUPLGKFMQIZFI-BZSJEYESSA-N (1r)-3-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]cyclohexan-1-amine Chemical compound C1[C@H](N)CCCC1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 NCUPLGKFMQIZFI-BZSJEYESSA-N 0.000 claims 1
• FWMVELRLCYRLLJ-HZPDHXFCSA-N (1r,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-HZPDHXFCSA-N 0.000 claims 1
• NCUPLGKFMQIZFI-WMCAAGNKSA-N (1s)-3-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]cyclohexan-1-amine Chemical compound C1[C@@H](N)CCCC1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 NCUPLGKFMQIZFI-WMCAAGNKSA-N 0.000 claims 1
• KSGJSAYVCSNIIB-JKSUJKDBSA-N (1s,3r)-3-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]oxycyclohexan-1-amine Chemical compound C1[C@@H](N)CCC[C@H]1OC1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 KSGJSAYVCSNIIB-JKSUJKDBSA-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
• FGJZMEQZWBNSNY-MRXNPFEDSA-N (3r)-1-[3-methyl-6-(5-pyridin-3-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)C=2C=NC=CC=2)N=C1N1CCC[C@@H](O)C1 FGJZMEQZWBNSNY-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
• PLZFUAHYVSHHBG-OAHLLOKOSA-N (3r)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-ol Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CC[C@@H](O)C1 PLZFUAHYVSHHBG-OAHLLOKOSA-N 0.000 claims 1
• CWZIRHXWUZBYHT-CQSZACIVSA-N (3r)-1-[4-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyrimidin-2-yl]piperidin-3-amine Chemical compound C1[C@H](N)CCCN1C1=NC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 CWZIRHXWUZBYHT-CQSZACIVSA-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
• AUGGRGUVEXOOJJ-CYBMUJFWSA-N (3r)-1-[6-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]piperidin-3-amine Chemical compound C1[C@H](N)CCCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=N1 AUGGRGUVEXOOJJ-CYBMUJFWSA-N 0.000 claims 1
• YSYVRFJJFUKXNR-GFCCVEGCSA-N (3r)-1-[6-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]pyrrolidin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=N1 YSYVRFJJFUKXNR-GFCCVEGCSA-N 0.000 claims 1
• XXUBBHDSOYKPNK-GFCCVEGCSA-N (3r)-1-[6-[5-(1,3-thiazol-5-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=2SC=NC=2)=N1 XXUBBHDSOYKPNK-GFCCVEGCSA-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
• BXYXJSLIRCVQHH-MRXNPFEDSA-N (3r)-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(N2C[C@H](O)CCCC2)=N1 BXYXJSLIRCVQHH-MRXNPFEDSA-N 0.000 claims 1
• SCICSUQDLRSZHW-CQSZACIVSA-N (3r)-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@H](O)CCC2)=N1 SCICSUQDLRSZHW-CQSZACIVSA-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
• XWSXADANHDIBHB-HZPDHXFCSA-N (3r,4r)-4-fluoro-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1C[C@@H](F)[C@H](N)CN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 XWSXADANHDIBHB-HZPDHXFCSA-N 0.000 claims 1
• BHBWYOGZMWLUSZ-ZIAGYGMSSA-N (3r,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-ZIAGYGMSSA-N 0.000 claims 1
• CTZLOSFKKPCJDH-LBPRGKRZSA-N (3s)-1-[3-(3-methyl-2h-pyrazolo[3,4-c]pyridin-5-yl)pyridin-4-yl]piperidin-3-amine Chemical compound C1=C2C(C)=NNC2=CN=C1C1=CN=CC=C1N1CCC[C@H](N)C1 CTZLOSFKKPCJDH-LBPRGKRZSA-N 0.000 claims 1
• SNWCKNPCXZGTJB-ZDUSSCGKSA-N (3s)-1-[3-bromo-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1C1=NC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=C1Br SNWCKNPCXZGTJB-ZDUSSCGKSA-N 0.000 claims 1
• PIKUIPAFOJTGMN-IBGZPJMESA-N (3s)-1-[3-butyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound CCCCC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CCC[C@H](N)C1 PIKUIPAFOJTGMN-IBGZPJMESA-N 0.000 claims 1
• DYZILEJNHNIIPT-KRWDZBQOSA-N (3s)-1-[3-cyclopropyl-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=C1C1CC1 DYZILEJNHNIIPT-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
• 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
• PLZFUAHYVSHHBG-HNNXBMFYSA-N (3s)-1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]pyrrolidin-3-ol Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N1CC[C@H](O)C1 PLZFUAHYVSHHBG-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
• WFRRHDGLYCBVIX-HNNXBMFYSA-N (3s)-1-[5-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyridin-3-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=C1 WFRRHDGLYCBVIX-HNNXBMFYSA-N 0.000 claims 1
• JAOCMDKJISHOCW-AWEZNQCLSA-N (3s)-1-[5-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyridin-3-yl]pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=C1 JAOCMDKJISHOCW-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
• AUGGRGUVEXOOJJ-ZDUSSCGKSA-N (3s)-1-[6-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=N1 AUGGRGUVEXOOJJ-ZDUSSCGKSA-N 0.000 claims 1
• YSYVRFJJFUKXNR-LBPRGKRZSA-N (3s)-1-[6-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=N1 YSYVRFJJFUKXNR-LBPRGKRZSA-N 0.000 claims 1
• XXUBBHDSOYKPNK-LBPRGKRZSA-N (3s)-1-[6-[5-(1,3-thiazol-5-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=2SC=NC=2)=N1 XXUBBHDSOYKPNK-LBPRGKRZSA-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
• 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
• 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
• PEQKUPNEEOUDLG-NSHDSACASA-N (3s)-1-[[5-(1h-pyrazol-4-yl)-2h-pyrazolo[3,4-c]pyridin-3-yl]methyl]piperidin-3-amine Chemical compound C1[C@@H](N)CCCN1CC1=NNC2=CN=C(C3=CNN=C3)C=C12 PEQKUPNEEOUDLG-NSHDSACASA-N 0.000 claims 1
• STVHGQTYZJFQHJ-QFIPXVFZSA-N (3s)-3-methyl-1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-3-amine Chemical compound C1[C@@](C)(N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 STVHGQTYZJFQHJ-QFIPXVFZSA-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
• 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
• 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
• RTXQHIFTFRSOGY-CQSZACIVSA-N (4r)-1-[6-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]azepan-4-amine Chemical compound C1C[C@H](N)CCCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=N1 RTXQHIFTFRSOGY-CQSZACIVSA-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
• 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
• RTXQHIFTFRSOGY-AWEZNQCLSA-N (4s)-1-[6-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]azepan-4-amine Chemical compound C1C[C@@H](N)CCCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=N1 RTXQHIFTFRSOGY-AWEZNQCLSA-N 0.000 claims 1
• DYEWIERMHIZZLA-INIZCTEOSA-N (4s)-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-INIZCTEOSA-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
• 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
• YOLDSXOVILIAPC-UHFFFAOYSA-N 1-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]piperazin-2-one Chemical compound O=C1CNCCN1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 YOLDSXOVILIAPC-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
• YVACBLRXIPFIHT-UHFFFAOYSA-N 1-[3-bromo-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperidin-4-amine Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2CCC(N)CC2)=N1 YVACBLRXIPFIHT-UHFFFAOYSA-N 0.000 claims 1
• YOEKUPVJOQMNFT-UHFFFAOYSA-N 1-[4-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=CC=N1 YOEKUPVJOQMNFT-UHFFFAOYSA-N 0.000 claims 1
• WADPACGZXLGEBX-UHFFFAOYSA-N 1-[4-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCN(CC2)C(C)=O)=N1 WADPACGZXLGEBX-UHFFFAOYSA-N 0.000 claims 1
• WRIJBGTYVVMNCJ-UHFFFAOYSA-N 1-[5-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyridin-3-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2)F)=C1 WRIJBGTYVVMNCJ-UHFFFAOYSA-N 0.000 claims 1
• QHPFWCMCHADYGC-UHFFFAOYSA-N 1-[6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]piperazin-2-one Chemical compound O=C1CNCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=N1 QHPFWCMCHADYGC-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
• HZOJBOHWMHVQRH-UHFFFAOYSA-N 1-[6-[3-(2,6-difluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]pyrazin-2-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CN=CC(C=2N=CC=3NN=C(C=3C=2)C=2C(=CC=CC=2F)F)=N1 HZOJBOHWMHVQRH-UHFFFAOYSA-N 0.000 claims 1
• KBYQJTFOVSYTAY-UHFFFAOYSA-N 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(N2CC(N)CCC2)=N1 KBYQJTFOVSYTAY-UHFFFAOYSA-N 0.000 claims 1
• RMSIYXGOGFYIOA-UHFFFAOYSA-N 1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]-1,4-diazepane-6-carbonitrile Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(CNCC2)C#N)=N1 RMSIYXGOGFYIOA-UHFFFAOYSA-N 0.000 claims 1
• LNARXJIXHBVOBV-UHFFFAOYSA-N 1-[6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azepan-3-amine Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CC(N)CCCC2)=N1 LNARXJIXHBVOBV-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
• NPQARTQLSPTNNM-UHFFFAOYSA-N 1-methyl-4-(3-pyridin-2-yl-1h-pyrazolo[3,4-c]pyridin-5-yl)piperazin-2-one Chemical compound C1C(=O)N(C)CCN1C(N=C1)=CC2=C1NN=C2C1=CC=CC=N1 NPQARTQLSPTNNM-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
• WSTOCCFMTDTLNU-UHFFFAOYSA-N 2-(1,4-diazepan-1-yl)-6-[5-(1-ethylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridine-4-carbonitrile Chemical compound C1=NN(CC)C=C1C(N=C1)=CC2=C1NN=C2C1=CC(C#N)=CC(N2CCNCCC2)=N1 WSTOCCFMTDTLNU-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
• CVMZGYNIRYDZLL-UHFFFAOYSA-N 2-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]acetonitrile Chemical compound N=1NC=2C=NC(CC#N)=CC=2C=1C(N=1)=CC=CC=1N1CCNCC1 CVMZGYNIRYDZLL-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
• XWQXSGRZONTZPR-UHFFFAOYSA-N 2-methyl-1-[[6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]amino]propan-2-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=CC(NCC(C)(C)O)=N1 XWQXSGRZONTZPR-UHFFFAOYSA-N 0.000 claims 1
• FHAPDLVADXCIGY-AWEZNQCLSA-N 3-(2-fluorophenyl)-5-[4-[(3s)-piperidin-3-yl]oxypyridin-3-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound FC1=CC=CC=C1C1=NNC2=CN=C(C=3C(=CC=NC=3)O[C@@H]3CNCCC3)C=C12 FHAPDLVADXCIGY-AWEZNQCLSA-N 0.000 claims 1
• FCRIHMREFBZVTE-OAHLLOKOSA-N 3-(2-fluorophenyl)-5-[4-[[(3r)-piperidin-3-yl]methoxy]pyridin-3-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound FC1=CC=CC=C1C1=NNC2=CN=C(C=3C(=CC=NC=3)OC[C@H]3CNCCC3)C=C12 FCRIHMREFBZVTE-OAHLLOKOSA-N 0.000 claims 1
• BIPWYLAIPQYYIZ-CQSZACIVSA-N 3-(2-fluorophenyl)-5-[4-[[(3r)-pyrrolidin-3-yl]methoxy]pyridin-3-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound FC1=CC=CC=C1C1=NNC2=CN=C(C=3C(=CC=NC=3)OC[C@H]3CNCC3)C=C12 BIPWYLAIPQYYIZ-CQSZACIVSA-N 0.000 claims 1
• FCRIHMREFBZVTE-HNNXBMFYSA-N 3-(2-fluorophenyl)-5-[4-[[(3s)-piperidin-3-yl]methoxy]pyridin-3-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound FC1=CC=CC=C1C1=NNC2=CN=C(C=3C(=CC=NC=3)OC[C@@H]3CNCCC3)C=C12 FCRIHMREFBZVTE-HNNXBMFYSA-N 0.000 claims 1
• BIPWYLAIPQYYIZ-AWEZNQCLSA-N 3-(2-fluorophenyl)-5-[4-[[(3s)-pyrrolidin-3-yl]methoxy]pyridin-3-yl]-1h-pyrazolo[3,4-c]pyridine Chemical compound FC1=CC=CC=C1C1=NNC2=CN=C(C=3C(=CC=NC=3)OC[C@@H]3CNCC3)C=C12 BIPWYLAIPQYYIZ-AWEZNQCLSA-N 0.000 claims 1
• KIQQQEAQHXIBAY-UHFFFAOYSA-N 3-(3-piperazin-1-ylpyrrolidin-1-yl)-5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridine Chemical compound C1CN(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)CC1N1CCNCC1 KIQQQEAQHXIBAY-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
• BDVVVKKOYBBKGI-UHFFFAOYSA-N 3-(4-cyclopropylpyridin-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(C2CC2)=CC=N1 BDVVVKKOYBBKGI-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
• 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-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
• DSZFEVQABXJNBQ-UHFFFAOYSA-N 3-[5-bromo-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=C1Br DSZFEVQABXJNBQ-UHFFFAOYSA-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
• PUFGHIKHLWSUIZ-UHFFFAOYSA-N 3-[6-(4-fluoropiperidin-4-yl)pyridin-2-yl]-5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridine Chemical compound C=1C=CC(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)=NC=1C1(F)CCNCC1 PUFGHIKHLWSUIZ-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
• 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 1
• XMMVQPRRYGDBDW-LLVKDONJSA-N 3-[6-[(3r)-3-aminopiperidin-1-yl]pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridine-5-carbonitrile Chemical compound C1[C@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)C#N)=N1 XMMVQPRRYGDBDW-LLVKDONJSA-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
• PIKYKNBWDFZDPW-UHFFFAOYSA-N 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(N2CC(C)(O)CCC2)=N1 PIKYKNBWDFZDPW-UHFFFAOYSA-N 0.000 claims 1
• CMPNPEKMGBOQHI-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]-1,4-thiazinane 1,1-dioxide Chemical compound C1=NN(C)C=C1C(N=C1)=CC2=C1NN=C2C1=CC=C(Br)C(N2CC(C2)N2CCS(=O)(=O)CC2)=N1 CMPNPEKMGBOQHI-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
• ORKXPOXUBRTFPU-UHFFFAOYSA-N 4-[1-[3-methyl-6-(5-pyridin-3-yl-1h-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl]azetidin-3-yl]piperazin-2-one Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C=2C=NC=CC=2)N=C1N(C1)CC1N1CCNC(=O)C1 ORKXPOXUBRTFPU-UHFFFAOYSA-N 0.000 claims 1
• OKOMQMSMMLYLHW-UHFFFAOYSA-N 4-[1-[3-methyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrazolo[3,4-c]pyridin-3-yl]pyridin-2-yl]azetidin-3-yl]-1,4-thiazinane 1,1-dioxide Chemical compound CC1=CC=C(C=2C3=CC(=NC=C3NN=2)C2=CN(C)N=C2)N=C1N(C1)CC1N1CCS(=O)(=O)CC1 OKOMQMSMMLYLHW-UHFFFAOYSA-N 0.000 claims 1
• LGRXFCYSCRBBGL-UHFFFAOYSA-N 4-[3-(2-fluorophenyl)-1h-pyrazolo[3,4-c]pyridin-5-yl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1C(N=C1)=CC2=C1NN=C2C1=CC=CC=C1F LGRXFCYSCRBBGL-UHFFFAOYSA-N 0.000 claims 1
• QIMHWUWINRBUSR-UHFFFAOYSA-N 4-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]morpholine Chemical compound C1CNCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)N2CCOCC2)=N1 QIMHWUWINRBUSR-UHFFFAOYSA-N 0.000 claims 1
• FTQIZXVNFDCIQI-UHFFFAOYSA-N 4-[3-(6-piperazin-1-ylpyridin-2-yl)-1h-pyrazolo[3,4-c]pyridin-5-yl]piperazin-2-one Chemical compound C1CNC(=O)CN1C(N=C1)=CC2=C1NN=C2C1=CC=CC(N2CCNCC2)=N1 FTQIZXVNFDCIQI-UHFFFAOYSA-N 0.000 claims 1
• ZMYRWIRGLSTTDU-ZDUSSCGKSA-N 4-[3-[6-[(3s)-3-aminopiperidin-1-yl]pyridin-2-yl]-1h-pyrazolo[3,4-c]pyridin-5-yl]piperazin-2-one Chemical compound C1[C@@H](N)CCCN1C1=CC=CC(C=2C3=CC(=NC=C3NN=2)N2CC(=O)NCC2)=N1 ZMYRWIRGLSTTDU-ZDUSSCGKSA-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
• LHKJJKGBIJIARW-UHFFFAOYSA-N 4-[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=CC(N2CCOCC2)=N1 LHKJJKGBIJIARW-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
• 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
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