CA3066859A1 - Derives de pyrrolopyridine substitues - Google Patents
Derives de pyrrolopyridine substituesInfo
- Publication number
- CA3066859A1 CA3066859A1 CA3066859A CA3066859A CA3066859A1 CA 3066859 A1 CA3066859 A1 CA 3066859A1 CA 3066859 A CA3066859 A CA 3066859A CA 3066859 A CA3066859 A CA 3066859A CA 3066859 A1 CA3066859 A1 CA 3066859A1
- Authority
- CA
- Canada
- Prior art keywords
- pyrrolo
- pyridin
- alkyl
- oxy
- urea
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 310
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 73
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 70
- 238000011282 treatment Methods 0.000 claims abstract description 57
- 208000035475 disorder Diseases 0.000 claims abstract description 55
- 238000011321 prophylaxis Methods 0.000 claims abstract description 33
- 201000011510 cancer Diseases 0.000 claims abstract description 30
- 239000004480 active ingredient Substances 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 230000011664 signaling Effects 0.000 claims abstract description 16
- 230000028993 immune response Effects 0.000 claims abstract description 14
- 230000001594 aberrant effect Effects 0.000 claims abstract description 11
- 230000003143 atherosclerotic effect Effects 0.000 claims abstract description 8
- 208000019553 vascular disease Diseases 0.000 claims abstract description 7
- 208000036142 Viral infection Diseases 0.000 claims abstract description 6
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 6
- 230000009385 viral infection Effects 0.000 claims abstract description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 5
- 206010040047 Sepsis Diseases 0.000 claims abstract description 5
- 230000035558 fertility Effects 0.000 claims abstract description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
- 206010020718 hyperplasia Diseases 0.000 claims abstract description 4
- -1 cyano, hydroxy Chemical group 0.000 claims description 616
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 373
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 207
- 239000004202 carbamide Substances 0.000 claims description 186
- 125000006413 ring segment Chemical group 0.000 claims description 145
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 137
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 130
- 150000002367 halogens Chemical class 0.000 claims description 128
- 229910052736 halogen Inorganic materials 0.000 claims description 122
- 125000001424 substituent group Chemical group 0.000 claims description 120
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 239000001257 hydrogen Substances 0.000 claims description 95
- 150000003839 salts Chemical class 0.000 claims description 86
- 125000002950 monocyclic group Chemical group 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 239000012453 solvate Substances 0.000 claims description 51
- 125000005059 halophenyl group Chemical group 0.000 claims description 45
- 125000004043 oxo group Chemical group O=* 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 42
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 38
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 239000011737 fluorine Substances 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 25
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
- 239000005864 Sulphur Substances 0.000 claims description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 229940076838 Immune checkpoint inhibitor Drugs 0.000 claims description 3
- 108091008026 Inhibitory immune checkpoint proteins Proteins 0.000 claims description 3
- 102000037984 Inhibitory immune checkpoint proteins Human genes 0.000 claims description 3
- HJZVHUQSQGITAM-UHFFFAOYSA-N butanamide Chemical compound CC[CH]C(N)=O HJZVHUQSQGITAM-UHFFFAOYSA-N 0.000 claims description 3
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims description 3
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
- 230000001093 anti-cancer Effects 0.000 claims description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 29
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 20
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- IAVJONIVZGKLBQ-IAGOWNOFSA-N 1-[4-[(3-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluorophenyl]-3-[(3S,4S)-4-pyrrolidin-1-yloxolan-3-yl]urea Chemical compound ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)N[C@@H]1COC[C@H]1N1CCCC1)F IAVJONIVZGKLBQ-IAGOWNOFSA-N 0.000 claims 1
- SUDYMOPPTOKIHR-UHFFFAOYSA-N BrC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)N1C(CC1)C)F Chemical compound BrC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)N1C(CC1)C)F SUDYMOPPTOKIHR-UHFFFAOYSA-N 0.000 claims 1
- HUJSRAYZZSKWLN-UHFFFAOYSA-N ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)N1CCC1)F Chemical compound ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)N1CCC1)F HUJSRAYZZSKWLN-UHFFFAOYSA-N 0.000 claims 1
- BHMYWAKFNMJJNT-UHFFFAOYSA-N ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)NC(COC)(C)C)F Chemical compound ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)NC(COC)(C)C)F BHMYWAKFNMJJNT-UHFFFAOYSA-N 0.000 claims 1
- QSWLEHWTXKXQQN-UHFFFAOYSA-N ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)NC1C(OCC1)(C)C)F Chemical compound ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)NC1C(OCC1)(C)C)F QSWLEHWTXKXQQN-UHFFFAOYSA-N 0.000 claims 1
- BZRUWNRYRUGTON-UHFFFAOYSA-N ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)NC1COC2(CCC2)C1)F Chemical compound ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(=O)NC1COC2(CCC2)C1)F BZRUWNRYRUGTON-UHFFFAOYSA-N 0.000 claims 1
- IRJUEYDKCNVONL-UHFFFAOYSA-N ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(N(C)C)=O)F Chemical compound ClC1=CNC2=NC=CC(=C21)OC1=C(C=C(C=C1F)NC(N(C)C)=O)F IRJUEYDKCNVONL-UHFFFAOYSA-N 0.000 claims 1
- IPDKYDUNXPNWHD-UHFFFAOYSA-N FC1=C(C=CC(=C1F)OC1=C2C(=NC=C1)NC=C2C(F)(F)F)NC(=O)NCCN1CCOCC1 Chemical compound FC1=C(C=CC(=C1F)OC1=C2C(=NC=C1)NC=C2C(F)(F)F)NC(=O)NCCN1CCOCC1 IPDKYDUNXPNWHD-UHFFFAOYSA-N 0.000 claims 1
- GCKFHHMEJFRZBT-UHFFFAOYSA-N FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2C(CC)CC)F)NC(=O)NCCOC Chemical compound FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2C(CC)CC)F)NC(=O)NCCOC GCKFHHMEJFRZBT-UHFFFAOYSA-N 0.000 claims 1
- KBCZJGVKMQEUIJ-UHFFFAOYSA-N FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2C(F)(F)F)F)NC(=O)NCC1(COC1)C Chemical compound FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2C(F)(F)F)F)NC(=O)NCC1(COC1)C KBCZJGVKMQEUIJ-UHFFFAOYSA-N 0.000 claims 1
- IBUWLTKPIUMLLO-UHFFFAOYSA-N FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2C(F)(F)F)F)NC(=O)NCCCS(=O)(=O)N Chemical compound FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2C(F)(F)F)F)NC(=O)NCCCS(=O)(=O)N IBUWLTKPIUMLLO-UHFFFAOYSA-N 0.000 claims 1
- UPRQWUSJUUYXRR-UHFFFAOYSA-N FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2CC(C)C)F)NC(=O)NCCOC Chemical compound FC=1C=C(C=C(C=1OC1=C2C(=NC=C1)NC=C2CC(C)C)F)NC(=O)NCCOC UPRQWUSJUUYXRR-UHFFFAOYSA-N 0.000 claims 1
- 102100028199 Mitogen-activated protein kinase kinase kinase kinase 1 Human genes 0.000 abstract description 43
- 101001059991 Homo sapiens Mitogen-activated protein kinase kinase kinase kinase 1 Proteins 0.000 abstract description 35
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- 230000001225 therapeutic effect Effects 0.000 abstract description 7
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- 229940121649 protein inhibitor Drugs 0.000 abstract description 3
- 239000012268 protein inhibitor Substances 0.000 abstract description 3
- 230000001613 neoplastic effect Effects 0.000 abstract description 2
- 150000005255 pyrrolopyridines Chemical class 0.000 abstract description 2
- 229940000425 combination drug Drugs 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 175
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 123
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 114
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 104
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 101
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- 238000004587 chromatography analysis Methods 0.000 description 57
- 238000005160 1H NMR spectroscopy Methods 0.000 description 52
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- 238000000746 purification Methods 0.000 description 41
- 238000000034 method Methods 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 38
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- 238000003786 synthesis reaction Methods 0.000 description 31
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 30
- 229940093499 ethyl acetate Drugs 0.000 description 29
- 235000019439 ethyl acetate Nutrition 0.000 description 29
- 150000001412 amines Chemical class 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
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- 239000000243 solution Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 21
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- 125000005842 heteroatom Chemical group 0.000 description 14
- 238000010626 work up procedure Methods 0.000 description 14
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- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
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- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 229960004449 vismodegib Drugs 0.000 description 1
- BPQMGSKTAYIVFO-UHFFFAOYSA-N vismodegib Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1=CC=C(Cl)C(C=2N=CC=CC=2)=C1 BPQMGSKTAYIVFO-UHFFFAOYSA-N 0.000 description 1
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
- 229960000237 vorinostat Drugs 0.000 description 1
- 229960001771 vorozole Drugs 0.000 description 1
- XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
- 201000005102 vulva cancer Diseases 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229950009268 zinostatin Drugs 0.000 description 1
- FYQZGCBXYVWXSP-STTFAQHVSA-N zinostatin stimalamer Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1OC1C/2=C/C#C[C@H]3O[C@@]3([C@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(C)C=CC2=C(C)C=C(OC)C=C12 FYQZGCBXYVWXSP-STTFAQHVSA-N 0.000 description 1
- 229950009233 zinostatin stimalamer Drugs 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne des dérivés de pyrrolopyridine substitués par des protéines inhibitrices de formule (I) dans laquelle X, Y, R1, R2, R3 et R4 sont tels que définis dans la description, des compositions pharmaceutiques et des combinaisons comprenant les composés selon l'invention, et l'utilisation prophylactique et thérapeutique des composés de l'invention, respectivement, l'utilisation desdits composés pour la fabrication de compositions pharmaceutiques pour le traitement ou la prophylaxie de maladies, en particulier pour des troubles néoplasiques, respectivement, un cancer ou des états pathologiques avec des réponses immunitaires dérégulées ou d'autres troubles associés à la signalisation aberrante de MAP4K1, en tant qu'agent unique ou en association avec d'autres principes actifs. La présente invention concerne en outre l'utilisation, respectivement, l'utilisation desdits composés pour la fabrication de compositions pharmaceutiques pour le traitement ou la prophylaxie d'inhibiteurs de protéines dans des hyperplasies bénignes, des troubles athérosclérotiques, la septicémie, les troubles auto-immuns, les troubles vasculaires, les infections virales, dans les troubles neurodégénératifs, dans les troubles inflammatoires, dans les troubles athérosclérotiques et dans la régulation de la fertilité chez l'homme
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17175861.8 | 2017-06-13 | ||
| EP17175861 | 2017-06-13 | ||
| PCT/EP2018/065036 WO2018228920A1 (fr) | 2017-06-13 | 2018-06-07 | Dérivés de pyrrolopyridine substitués |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3066859A1 true CA3066859A1 (fr) | 2018-12-20 |
Family
ID=59055146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3066859A Abandoned CA3066859A1 (fr) | 2017-06-13 | 2018-06-07 | Derives de pyrrolopyridine substitues |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP3638669A1 (fr) |
| CA (1) | CA3066859A1 (fr) |
| WO (1) | WO2018228920A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20211655A1 (es) | 2018-10-31 | 2021-08-24 | Gilead Sciences Inc | Compuestos de 6-azabencimidazol sustituidos como inhibidores de hpk1 |
| WO2020092528A1 (fr) | 2018-10-31 | 2020-05-07 | Gilead Sciences, Inc. | Composés 6-azabenzimidazole substitués ayant une activité inhibitrice de hpk1 |
| CA3129772A1 (fr) | 2019-03-26 | 2020-10-01 | Janssen Pharmaceutica Nv | Inhibiteurs bicycliques de hpk1 |
| US12492194B2 (en) | 2019-03-26 | 2025-12-09 | Janssen Pharmaceutica Nv | HPK1 inhibitors |
| TWI826690B (zh) | 2019-05-23 | 2023-12-21 | 美商基利科學股份有限公司 | 經取代之烯吲哚酮化物及其用途 |
| US20230210853A1 (en) * | 2020-05-08 | 2023-07-06 | Halia Therapeutics, Inc. | Targeted nek7 inhibition for modulation of the nlrp3 inflammasome |
| PH12022553024A1 (en) | 2020-05-08 | 2024-05-20 | Halia Therapeutics Inc | Inhibitors of nek7 kinase |
| US20240400551A1 (en) * | 2021-01-25 | 2024-12-05 | Halia Therapeutics, Inc. | Nek7 inhibitors |
| WO2022226182A1 (fr) * | 2021-04-22 | 2022-10-27 | Halia Therapeutics, Inc. | Inhibiteurs de nek7 |
| WO2022268520A1 (fr) * | 2021-06-21 | 2022-12-29 | Bayer Aktiengesellschaft | Utilisation de pyrrolidinones substituées ou de leurs sels pour augmenter la tolérance au stress des plantes |
| EP4373817B1 (fr) | 2021-07-20 | 2025-05-21 | Astrazeneca AB | Pyrazine-2-carboxamides substituées utilisées en tant qu'inhibiteurs de hpk1 pour le traitement du cancer |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10357510A1 (de) | 2003-12-09 | 2005-07-07 | Bayer Healthcare Ag | Heteroarylsubstituierte Benzole |
| US7439246B2 (en) * | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| WO2006014325A2 (fr) | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | Modulateurs de c-met et leur methode d'utilisation |
| EP1921078B1 (fr) * | 2005-08-05 | 2013-01-09 | Chugai Seiyaku Kabushiki Kaisha | Inhibiteur de multikinase |
| MX2008011220A (es) | 2006-03-07 | 2008-09-11 | Array Biopharma Inc | Compuestos de pirazol heterobiciclicos y metodos de uso. |
| JP6879740B2 (ja) | 2013-12-13 | 2021-06-02 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | リンパ形質細胞性リンパ腫を処置する方法 |
| AR104020A1 (es) | 2015-06-04 | 2017-06-21 | Kura Oncology Inc | Métodos y composiciones para inhibir la interacción de menina con proteínas mill |
| ES2872555T3 (es) | 2015-06-25 | 2021-11-02 | Univ Health Network | Inhibidores de HPK1 y métodos de uso de los mismos |
| US20180072718A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| IL292977A (en) | 2016-09-09 | 2022-07-01 | Incyte Corp | Pyrazolopyridine derivatives as modulators of hpk1 and their use in cancer therapy |
| AR109595A1 (es) | 2016-09-09 | 2018-12-26 | Incyte Corp | Compuestos de pirazolopirimidina y usos de estos como inhibidores de hpk1 |
| US10280164B2 (en) | 2016-09-09 | 2019-05-07 | Incyte Corporation | Pyrazolopyridone compounds and uses thereof |
-
2018
- 2018-06-07 CA CA3066859A patent/CA3066859A1/fr not_active Abandoned
- 2018-06-07 EP EP18728901.2A patent/EP3638669A1/fr not_active Withdrawn
- 2018-06-07 WO PCT/EP2018/065036 patent/WO2018228920A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP3638669A1 (fr) | 2020-04-22 |
| WO2018228920A1 (fr) | 2018-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20231207 |