WO2018049200A1 - Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer - Google Patents
Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer Download PDFInfo
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- WO2018049200A1 WO2018049200A1 PCT/US2017/050737 US2017050737W WO2018049200A1 WO 2018049200 A1 WO2018049200 A1 WO 2018049200A1 US 2017050737 W US2017050737 W US 2017050737W WO 2018049200 A1 WO2018049200 A1 WO 2018049200A1
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- alkyl
- cycloalkyl
- alkenyl
- alkynyl
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 67
- 201000011510 cancer Diseases 0.000 title claims abstract description 20
- 238000011282 treatment Methods 0.000 title description 25
- 101100177670 Caenorhabditis elegans hpk-1 gene Proteins 0.000 title description 2
- 150000005229 pyrazolopyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- 238000000034 method Methods 0.000 claims abstract description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 102100028199 Mitogen-activated protein kinase kinase kinase kinase 1 Human genes 0.000 claims abstract description 28
- 101001059991 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 1 Proteins 0.000 claims abstract description 26
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 230000000694 effects Effects 0.000 claims abstract description 14
- 208000035475 disorder Diseases 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 688
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 512
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 503
- 125000001424 substituent group Chemical group 0.000 claims description 427
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 403
- 125000003118 aryl group Chemical group 0.000 claims description 359
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 346
- 125000001188 haloalkyl group Chemical group 0.000 claims description 276
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 272
- 125000002947 alkylene group Chemical group 0.000 claims description 218
- -1 aminosulfonylamino Chemical group 0.000 claims description 179
- 125000005843 halogen group Chemical group 0.000 claims description 153
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 101
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 94
- 229910052799 carbon Inorganic materials 0.000 claims description 92
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 88
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 81
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 80
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 49
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 47
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 42
- 125000004429 atom Chemical group 0.000 claims description 39
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 35
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 229910052701 rubidium Inorganic materials 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 125000003003 spiro group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 14
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 208000020816 lung neoplasm Diseases 0.000 claims description 6
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
- AQIAIZBHFAKICS-UHFFFAOYSA-N methylaminomethyl Chemical compound [CH2]NC AQIAIZBHFAKICS-UHFFFAOYSA-N 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 12
- DKZQBBQDMRTBDM-UHFFFAOYSA-N 5-(2-fluoro-6-methyl-4-piperidin-2-ylphenyl)-3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine Chemical compound FC1=C(C(=CC(=C1)C1NCCCC1)C)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C DKZQBBQDMRTBDM-UHFFFAOYSA-N 0.000 claims 2
- QURIJRMKDDRSDB-UHFFFAOYSA-N 5-(2-fluoro-6-methyl-4-pyrrolidin-2-ylphenyl)-3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine Chemical compound FC1=C(C(=CC(=C1)C1NCCC1)C)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C QURIJRMKDDRSDB-UHFFFAOYSA-N 0.000 claims 2
- GENQXCBRPQSLGR-UHFFFAOYSA-N N-[5-[2,6-difluoro-4-[(propan-2-ylamino)methyl]phenyl]-1H-pyrazolo[3,4-c]pyridin-3-yl]-3-methoxybenzamide Chemical compound FC1=C(C(=CC(=C1)CNC(C)C)F)C=1C=C2C(=CN=1)NN=C2NC(C1=CC(=CC=C1)OC)=O GENQXCBRPQSLGR-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims 2
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- WVNNAESMGJFXKC-UHFFFAOYSA-N (1-methylpiperidin-4-yl) N-[3-fluoro-5-methoxy-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]carbamate Chemical compound COC1=CC(NC(=O)OC2CCN(C)CC2)=CC(F)=C1C1=CC2=C(NN=C2C2=CN(C)N=C2)C=N1 WVNNAESMGJFXKC-UHFFFAOYSA-N 0.000 claims 1
- AXSKSICPXIOGPW-UHFFFAOYSA-N 1-(4-bromophenyl)-4-[5-(2-fluoro-6-methoxyphenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl]piperazin-2-one Chemical compound BrC1=CC=C(C=C1)N1C(CN(CC1)C1=NNC2=CN=C(C=C21)C1=C(C=CC=C1OC)F)=O AXSKSICPXIOGPW-UHFFFAOYSA-N 0.000 claims 1
- CDEVXMMNURAYIY-UHFFFAOYSA-N 1-[3,5-difluoro-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]-3-(2-methoxyethyl)urea Chemical compound FC=1C=C(C=C(C=1C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F)NC(=O)NCCOC CDEVXMMNURAYIY-UHFFFAOYSA-N 0.000 claims 1
- QOWZSRWPCOUJIX-UHFFFAOYSA-N 1-[3-fluoro-5-methyl-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]-N-(1,3-oxazol-4-ylmethyl)methanamine Chemical compound FC=1C=C(CNCC=2N=COC=2)C=C(C=1C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)C QOWZSRWPCOUJIX-UHFFFAOYSA-N 0.000 claims 1
- DHVITDUDDAYZLF-UHFFFAOYSA-N 1-[3-fluoro-5-methyl-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]-N-[(1-methylimidazol-4-yl)methyl]methanamine Chemical compound FC=1C=C(CNCC=2N=CN(C=2)C)C=C(C=1C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)C DHVITDUDDAYZLF-UHFFFAOYSA-N 0.000 claims 1
- BSHHFNIPFYZERQ-UHFFFAOYSA-N 1-[4-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]-3-fluoro-5-methylphenyl]-N-methylmethanamine Chemical compound C1(CC1)N1N=CC(=C1)C1=NNC2=CN=C(C=C21)C1=C(C=C(C=C1C)CNC)F BSHHFNIPFYZERQ-UHFFFAOYSA-N 0.000 claims 1
- JBEJHSXRGBIFKX-UHFFFAOYSA-N 1-[4-[6-[5-[2-(difluoromethoxy)-6-fluoro-4-(methylaminomethyl)phenyl]-1H-pyrazolo[3,4-c]pyridin-3-yl]pyridin-3-yl]piperazin-1-yl]ethanone Chemical compound FC(OC1=C(C(=CC(=C1)CNC)F)C=1C=C2C(=CN=1)NN=C2C1=CC=C(C=N1)N1CCN(CC1)C(C)=O)F JBEJHSXRGBIFKX-UHFFFAOYSA-N 0.000 claims 1
- ROCDIFUZZVNCTQ-UHFFFAOYSA-N 1-[4-fluoro-2-methyl-3-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]-N-[(1-methylcyclopropyl)methyl]methanamine Chemical compound FC1=C(C(=C(CNCC2(CC2)C)C=C1)C)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C ROCDIFUZZVNCTQ-UHFFFAOYSA-N 0.000 claims 1
- VYBAQTYKELUCMD-UHFFFAOYSA-N 1-[[3-fluoro-5-methyl-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]methylamino]-2-methylpropan-2-ol Chemical compound FC=1C=C(CNCC(C)(O)C)C=C(C=1C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)C VYBAQTYKELUCMD-UHFFFAOYSA-N 0.000 claims 1
- PKVVZRAZTWIPFD-UHFFFAOYSA-N 2,2,2-trifluoro-N-[[3-fluoro-5-methyl-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]methyl]ethanamine Chemical compound FC(CNCC1=CC(=C(C(=C1)C)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F)(F)F PKVVZRAZTWIPFD-UHFFFAOYSA-N 0.000 claims 1
- BGTKJCTZMIAWAP-UHFFFAOYSA-N 2,4-difluoro-N-methyl-3-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]aniline Chemical compound FC1=C(NC)C=CC(=C1C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F BGTKJCTZMIAWAP-UHFFFAOYSA-N 0.000 claims 1
- ZLOVBOKITZTEJC-UHFFFAOYSA-N 2-(3,3-dimethylazetidin-1-yl)-N-[3-fluoro-5-methoxy-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetamide Chemical compound CC1(CN(C1)CC(=O)NC1=CC(=C(C(=C1)OC)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F)C ZLOVBOKITZTEJC-UHFFFAOYSA-N 0.000 claims 1
- MQGKLYLWTYRWDR-UHFFFAOYSA-N 2-(7-azabicyclo[2.2.1]heptan-7-yl)-N-[3,5-difluoro-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetamide Chemical compound C12CCC(CC1)N2CC(=O)NC1=CC(=C(C(=C1)F)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F MQGKLYLWTYRWDR-UHFFFAOYSA-N 0.000 claims 1
- SSDBLGYGPLNIAC-UHFFFAOYSA-N 2-(7-azabicyclo[2.2.1]heptan-7-yl)-N-[3-fluoro-5-methyl-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetamide Chemical compound C12CCC(CC1)N2CC(=O)NC1=CC(=C(C(=C1)C)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F SSDBLGYGPLNIAC-UHFFFAOYSA-N 0.000 claims 1
- MVJWXRCFUFDDKB-UHFFFAOYSA-N 2-(azetidin-1-yl)-N-[2,3,5-trifluoro-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetamide Chemical compound N1(CCC1)CC(=O)NC1=C(C(=C(C(=C1)F)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F)F MVJWXRCFUFDDKB-UHFFFAOYSA-N 0.000 claims 1
- VEZZGEASXAGWKE-UHFFFAOYSA-N 2-(azetidin-1-yl)-N-[3-(difluoromethoxy)-5-fluoro-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetamide Chemical compound N1(CCC1)CC(=O)NC1=CC(=C(C(=C1)F)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)OC(F)F VEZZGEASXAGWKE-UHFFFAOYSA-N 0.000 claims 1
- ALYWIXIMVWOXMA-UHFFFAOYSA-N 2-(dimethylamino)-N-[3-fluoro-5-methyl-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetamide Chemical compound CN(CC(=O)NC1=CC(=C(C(=C1)C)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F)C ALYWIXIMVWOXMA-UHFFFAOYSA-N 0.000 claims 1
- CIWLKILIJOLULJ-UHFFFAOYSA-N 2-[(3-cyanocyclopentyl)amino]-N-[5-(2-fluoro-6-methylphenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound C(#N)C1CC(CC1)NC1=C(C(=O)NC2=NNC3=CN=C(C=C32)C2=C(C=CC=C2C)F)C=CC(=C1)N1CCN(CC1)C CIWLKILIJOLULJ-UHFFFAOYSA-N 0.000 claims 1
- JAMRPXCAFCYKGU-UHFFFAOYSA-N 2-[3,5-difluoro-4-[3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetonitrile Chemical compound FC=1C=C(C=C(C=1C=1C=C2C(=CN=1)NN=C2C=1C=NC(=NC=1)N1CCN(CC1)C)F)CC#N JAMRPXCAFCYKGU-UHFFFAOYSA-N 0.000 claims 1
- PZYDDTSCPKCTNV-UHFFFAOYSA-N 2-[3-fluoro-2-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]acetonitrile Chemical compound FC=1C(=C(C=CC=1)CC#N)C=1C=C2C(=CN=1)NN=C2C1=CC=C(C=C1)N1CCN(CC1)C PZYDDTSCPKCTNV-UHFFFAOYSA-N 0.000 claims 1
- JHWIXXDIDOTBBQ-UHFFFAOYSA-N 2-[4-[5-[2,6-difluoro-4-(methylaminomethyl)phenyl]-1H-pyrazolo[3,4-c]pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=C(C(=CC(=C1)CNC)F)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C1=C(C#N)C=CC=C1 JHWIXXDIDOTBBQ-UHFFFAOYSA-N 0.000 claims 1
- PXQRBEYNXVYNPT-UHFFFAOYSA-N 2-[4-[5-[2,6-difluoro-4-(methylaminomethyl)phenyl]-1H-pyrazolo[3,4-c]pyridin-3-yl]pyrazol-1-yl]ethanol Chemical compound FC1=C(C(=CC(=C1)CNC)F)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)CCO PXQRBEYNXVYNPT-UHFFFAOYSA-N 0.000 claims 1
- VSDVDPIAXSUAFU-UHFFFAOYSA-N 2-[4-[5-[2-fluoro-6-methyl-4-(methylaminomethyl)phenyl]-1H-pyrazolo[3,4-c]pyridin-3-yl]pyrazol-1-yl]benzonitrile Chemical compound FC1=C(C(=CC(=C1)CNC)C)C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C1=C(C#N)C=CC=C1 VSDVDPIAXSUAFU-UHFFFAOYSA-N 0.000 claims 1
- LDSUHSMFESJXMN-UHFFFAOYSA-N 2-[[3,5-difluoro-4-[3-(1-methylpyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl]phenyl]methylamino]ethanol Chemical compound FC=1C=C(CNCCO)C=C(C=1C=1C=C2C(=CN=1)NN=C2C=1C=NN(C=1)C)F LDSUHSMFESJXMN-UHFFFAOYSA-N 0.000 claims 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims
Priority Applications (19)
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BR112019004586A BR112019004586A2 (en) | 2016-09-09 | 2017-09-08 | pyrazolopyridine derivatives as hpk1 modulators and their uses for cancer treatment |
EP17768937.9A EP3510032B1 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
KR1020237007905A KR20230038807A (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
AU2017322427A AU2017322427B2 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as HPK1 modulators and uses thereof for the treatment of cancer |
ES17768937T ES2927104T3 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as modulators of HPK1 and uses thereof for the treatment of cancer |
IL292977A IL292977A (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
CN202211268174.7A CN115819417A (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as HPK1 modulators and their use for the treatment of cancer |
CN201780068722.2A CN109923114B (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as HPK1 modulators and their use for the treatment of cancer |
UAA201903484A UA125650C2 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
EA201990665A EA201990665A1 (en) | 2016-09-09 | 2017-09-08 | HPK1 REGULATORS BASED ON PYRAZOLOPYRIDINE DERIVATIVES AND THEIR APPLICATION FOR TREATMENT OF CANCER |
CA3036358A CA3036358A1 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
KR1020197010179A KR102507967B1 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as HPK1 modulators and their use to treat cancer |
EP22177485.4A EP4119558A1 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine compounds and uses thereof |
MX2019002750A MX2019002750A (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer. |
JP2019513288A JP7076432B2 (en) | 2016-09-09 | 2017-09-08 | Pyrazolopyridine derivatives as HPK1 regulators and their use for the treatment of cancer |
IL265215A IL265215B (en) | 2016-09-09 | 2019-03-07 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
PH12019500521A PH12019500521A1 (en) | 2016-09-09 | 2019-03-11 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
AU2022202009A AU2022202009B2 (en) | 2016-09-09 | 2022-03-23 | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
JP2022080980A JP7432655B2 (en) | 2016-09-09 | 2022-05-17 | Pyrazolopyridine derivatives as HPK1 modulators and their use for the treatment of cancer |
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CN (2) | CN109923114B (en) |
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BR (1) | BR112019004586A2 (en) |
CA (1) | CA3036358A1 (en) |
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IL (2) | IL292977A (en) |
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MX (1) | MX2019002750A (en) |
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