BR112019026955A2 - derivados de di-hidro-pirrolo-piridina - Google Patents

Info

Publication number

BR112019026955A2

BR112019026955A2 BR112019026955-0A BR112019026955A BR112019026955A2 BR 112019026955 A2 BR112019026955 A2 BR 112019026955A2 BR 112019026955 A BR112019026955 A BR 112019026955A BR 112019026955 A2 BR112019026955 A2 BR 112019026955A2

Authority

BR

Brazil

Prior art keywords

pyridin

optionally substituted

dihydro

pyrrolo

dimethyl

Prior art date

2017-06-22

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 281
• 150000003839 salts Chemical class 0.000 claims abstract description 100
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 86
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 85
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• 238000000034 method Methods 0.000 claims abstract description 56
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• 230000001404 mediated effect Effects 0.000 claims abstract description 18
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• 208000019116 sleep disease Diseases 0.000 claims abstract description 11
• 206010012335 Dependence Diseases 0.000 claims abstract description 9
• 208000020685 sleep-wake disease Diseases 0.000 claims abstract description 7
• -1 cyano, hydroxy Chemical group 0.000 claims description 196
• 125000001424 substituent group Chemical group 0.000 claims description 77
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 68
• 125000001072 heteroaryl group Chemical group 0.000 claims description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 52
• 150000002367 halogens Chemical class 0.000 claims description 52
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 239000001257 hydrogen Substances 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 29
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 24
• 125000004043 oxo group Chemical group O=* 0.000 claims description 23
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 22
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
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• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 15
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• 239000002253 acid Substances 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
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• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 11
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
• MTJZQOBIJDHSOB-KBPBESRZSA-N Cc1nc(N)c2CN(Cc2c1C)C(=O)C[C@@H]1C[C@H]1c1ccc(F)nc1 Chemical compound Cc1nc(N)c2CN(Cc2c1C)C(=O)C[C@@H]1C[C@H]1c1ccc(F)nc1 MTJZQOBIJDHSOB-KBPBESRZSA-N 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
• 208000023105 Huntington disease Diseases 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• AOULMVARWGZMTH-UHFFFAOYSA-N CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=NC=NS1)=O)C Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=NC=NS1)=O)C AOULMVARWGZMTH-UHFFFAOYSA-N 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 7
• 208000012661 Dyskinesia Diseases 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
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• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• WFAQJXWZEOHIPO-HOTGVXAUSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[(1S,2R)-2-pyridin-3-ylcyclopropyl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(C[C@H]1[C@@H](C1)C=1C=NC=CC=1)=O)C WFAQJXWZEOHIPO-HOTGVXAUSA-N 0.000 claims description 5
• RVNOMIUAUHPBGK-UHFFFAOYSA-N 2-(1-pyridin-3-ylazetidin-3-yl)-1-(4,6,7-trimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl)ethanone Chemical compound N1=CC(=CC=C1)N1CC(C1)CC(=O)N1CC=2C(=NC(=C(C=2C1)C)C)C RVNOMIUAUHPBGK-UHFFFAOYSA-N 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• LPYIUKYJYAMAFC-IRXDYDNUSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[(1S,2R)-2-(6-methylpyridin-3-yl)cyclopropyl]ethanone Chemical compound C1=C(N=CC(=C1)[C@H]1[C@@H](C1)CC(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1)C LPYIUKYJYAMAFC-IRXDYDNUSA-N 0.000 claims description 4
• JRKLWKSDYCTMSD-UHFFFAOYSA-N 2-[1-[2-(trifluoromethyl)pyridin-4-yl]azetidin-3-yl]-1-[1,6,7-trimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]ethanone Chemical compound N(C)C1=NC(=C(C=2C(C)N(CC1=2)C(=O)CC1CN(C2=CC(C(F)(F)F)=NC=C2)C1)C)C JRKLWKSDYCTMSD-UHFFFAOYSA-N 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 206010003805 Autism Diseases 0.000 claims description 4
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
• JQYFHQSINOODAY-DZGCQCFKSA-N CNc1nc(C)c(C)c2CN(Cc12)C(=O)C[C@@H]1C[C@H]1c1cncnc1 Chemical compound CNc1nc(C)c(C)c2CN(Cc12)C(=O)C[C@@H]1C[C@H]1c1cncnc1 JQYFHQSINOODAY-DZGCQCFKSA-N 0.000 claims description 4
• 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims description 4
• 206010019196 Head injury 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
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
• QCJULGMSVIUYLJ-UHFFFAOYSA-N 1-[4-(cyclopropylmethylamino)-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyrimidin-4-ylazetidin-3-yl)ethanone Chemical compound C1C(CNC2=NC(C)=C(C3=C2CN(C3)C(=O)CC2CN(C3=NC=NC=C3)C2)C)C1 QCJULGMSVIUYLJ-UHFFFAOYSA-N 0.000 claims description 3
• GWTJMQFIFVBLNA-GJZGRUSLSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[(1S,2R)-2-(6-fluoropyridin-3-yl)cyclopropyl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(C[C@H]1[C@@H](C1)C=1C=NC(=CC=1)F)=O)C GWTJMQFIFVBLNA-GJZGRUSLSA-N 0.000 claims description 3
• PRLFPWQBJHQKIV-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-[2-(trifluoromethyl)pyridin-4-yl]azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=CC(=NC=C1)C(F)(F)F)=O)C PRLFPWQBJHQKIV-UHFFFAOYSA-N 0.000 claims description 3
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• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
• WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
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• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 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 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 3
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 3
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• AHWWXPSVXHWBHK-UHFFFAOYSA-N 1-[4-(difluoromethyl)-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-[2-(difluoromethyl)pyridin-4-yl]azetidin-3-yl]ethanone Chemical compound FC(C1=NC(=C(C2=C1CN(C2)C(CC1CN(C1)C1=CC(=NC=C1)C(F)F)=O)C)C)F AHWWXPSVXHWBHK-UHFFFAOYSA-N 0.000 claims description 2
• IQVOZNJJMUSCOZ-UHFFFAOYSA-N 1-[4-[(dimethylamino)methyl]-6,7-dimethyl-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyridin-3-ylazetidin-3-yl)ethanone Chemical compound C(C1=NC(=C(C2=C1CN(C2)C(=O)CC1CN(C2=CN=CC=C2)C1)C)C)N(C)C IQVOZNJJMUSCOZ-UHFFFAOYSA-N 0.000 claims description 2
• RUCLNTFQDCNNAK-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(1-methylpyrazol-4-yl)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(1-pyridin-3-ylazetidin-3-yl)ethanone Chemical compound N=1N(C=C(C=1)C1=NC(=C(C2=C1CN(C2)C(=O)CC1CN(C2=CN=CC=C2)C1)C)C)C RUCLNTFQDCNNAK-UHFFFAOYSA-N 0.000 claims description 2
• IHVNXDZGSJJBPX-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-(5-fluoro-2,3-dihydro-1H-inden-2-yl)ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CC2=CC=C(C=C2C1)F)=O)C IHVNXDZGSJJBPX-UHFFFAOYSA-N 0.000 claims description 2
• SDUNTRZRXCNYAZ-RDJZCZTQSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[(1S,2R)-2-(4-fluorophenyl)cyclopropyl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(C[C@H]1[C@@H](C1)C1=CC=C(C=C1)F)=O)C SDUNTRZRXCNYAZ-RDJZCZTQSA-N 0.000 claims description 2
• YGKZQISZKPFFDV-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-(1,3,4-thiadiazol-2-yl)azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C=1SC=NN=1)=O)C YGKZQISZKPFFDV-UHFFFAOYSA-N 0.000 claims description 2
• ZNPQEOTVQBKCJE-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-(2-methylpyridin-4-yl)azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=CC(=NC=C1)C)=O)C ZNPQEOTVQBKCJE-UHFFFAOYSA-N 0.000 claims description 2
• WGGGULHBHYSVOD-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-[1-(6-fluoropyridin-3-yl)azetidin-3-yl]ethanone Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C=1C=NC(=CC=1)F)=O)C WGGGULHBHYSVOD-UHFFFAOYSA-N 0.000 claims description 2
• SDZQJMCXLDSQML-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-(1H-pyrazol-4-yl)propan-1-one Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CCC=1C=NNC=1)=O)C SDZQJMCXLDSQML-UHFFFAOYSA-N 0.000 claims description 2
• YHVZLWRQGISNQE-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=C(C=CC(=C1)CCC(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1)OC YHVZLWRQGISNQE-UHFFFAOYSA-N 0.000 claims description 2
• BGCZOPIJDNQQEC-UHFFFAOYSA-N 2-[1-[2-(difluoromethoxy)pyridin-4-yl]azetidin-3-yl]-1-[1,6,7-trimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]ethanone Chemical compound N1(C2=CC(OC(F)F)=NC=C2)CC(CC(=O)N2C(C3=C(C(=NC(=C3C)C)NC)C2)C)C1 BGCZOPIJDNQQEC-UHFFFAOYSA-N 0.000 claims description 2
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