JP7480128B2 - Ｇａｂａａ ａ５受容体モジュレーターとしての二環式誘導体 - Google Patents

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Publication number

JP7480128B2

JP7480128B2 JP2021516369A JP2021516369A JP7480128B2 JP 7480128 B2 JP7480128 B2 JP 7480128B2 JP 2021516369 A JP2021516369 A JP 2021516369A JP 2021516369 A JP2021516369 A JP 2021516369A JP 7480128 B2 JP7480128 B2 JP 7480128B2

Authority

JP

Japan

Prior art keywords

methyl

fluorophenyl

methoxy

tetrahydro

triazol

Prior art date

2018-09-28

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.)

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• 125000002619 bicyclic group Chemical group 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims description 169
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 144
• 125000000217 alkyl group Chemical group 0.000 claims description 112
• 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 74
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 69
• 208000010877 cognitive disease Diseases 0.000 claims description 57
• 125000003545 alkoxy group Chemical group 0.000 claims description 44
• 125000000623 heterocyclic group Chemical group 0.000 claims description 44
• 201000010099 disease Diseases 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 239000001257 hydrogen Substances 0.000 claims description 42
• 238000011282 treatment Methods 0.000 claims description 42
• 239000004480 active ingredient Substances 0.000 claims description 39
• 239000008194 pharmaceutical composition Substances 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 36
• 125000001072 heteroaryl group Chemical group 0.000 claims description 32
• 208000035475 disorder Diseases 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 26
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• 201000000980 schizophrenia Diseases 0.000 claims description 23
• 208000024827 Alzheimer disease Diseases 0.000 claims description 22
• 239000000203 mixture Substances 0.000 claims description 22
• 206010012289 Dementia Diseases 0.000 claims description 21
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
• 208000024714 major depressive disease Diseases 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 201000010374 Down Syndrome Diseases 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 206010044688 Trisomy 21 Diseases 0.000 claims description 17
• 230000006999 cognitive decline Effects 0.000 claims description 17
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 17
• 230000002265 prevention Effects 0.000 claims description 17
• 208000037820 vascular cognitive impairment Diseases 0.000 claims description 17
• 210000003169 central nervous system Anatomy 0.000 claims description 16
• 208000028698 Cognitive impairment Diseases 0.000 claims description 15
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 239000000460 chlorine Substances 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 208000006011 Stroke Diseases 0.000 claims description 12
• 125000004043 oxo group Chemical group O=* 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 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 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 206010027175 memory impairment Diseases 0.000 claims description 11
• 208000019022 Mood disease Diseases 0.000 claims description 10
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 9
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
• 208000027626 Neurocognitive disease Diseases 0.000 claims description 9
• 239000012453 solvate Substances 0.000 claims description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
• 208000026139 Memory disease Diseases 0.000 claims description 8
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 8
• 239000002475 cognitive enhancer Substances 0.000 claims description 8
• 150000004677 hydrates Chemical class 0.000 claims description 8
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 208000000044 Amnesia Diseases 0.000 claims description 7
• 208000027520 Somatoform disease Diseases 0.000 claims description 7
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 7
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 7
• 208000027753 pain disease Diseases 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• 208000011117 substance-related disease Diseases 0.000 claims description 7
• YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 230000007278 cognition impairment Effects 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 230000006984 memory degeneration Effects 0.000 claims description 6
• 208000023060 memory loss Diseases 0.000 claims description 6
• 229940016409 methylsulfonylmethane Drugs 0.000 claims description 6
• HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 6
• 208000007848 Alcoholism Diseases 0.000 claims description 5
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
• 206010016845 Foetal alcohol syndrome Diseases 0.000 claims description 5
• 208000003019 Neurofibromatosis 1 Diseases 0.000 claims description 5
• 208000024834 Neurofibromatosis type 1 Diseases 0.000 claims description 5
• 201000007930 alcohol dependence Diseases 0.000 claims description 5
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 5
• 230000003435 bronchoconstrictive effect Effects 0.000 claims description 5
• 230000006735 deficit Effects 0.000 claims description 5
• 208000026934 fetal alcohol spectrum disease Diseases 0.000 claims description 5
• 201000007794 fetal alcohol syndrome Diseases 0.000 claims description 5
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims description 5
• FVRQRXRVKLGUHG-UHFFFAOYSA-N C1=C(F)C=CC(C=2C(=C(ON=2)C)COC2=NC3=C(C=C2)CN(C(=O)C)CC3)=C1 Chemical compound C1=C(F)C=CC(C=2C(=C(ON=2)C)COC2=NC3=C(C=C2)CN(C(=O)C)CC3)=C1 FVRQRXRVKLGUHG-UHFFFAOYSA-N 0.000 claims description 4
• 201000009906 Meningitis Diseases 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• OHPFIURCPBDDFH-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-N-(1-methyl-5-oxopyrrolidin-3-yl)-7,8-dihydro-5H-1,6-naphthyridine-6-carboxamide Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)NC1CN(C(C1)=O)C)C OHPFIURCPBDDFH-UHFFFAOYSA-N 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• IETUCUOGOZWGJB-UHFFFAOYSA-N (3-chlorophenyl)-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]methanone Chemical compound ClC=1C=C(C(=O)N2CC=3C=CC(=NC=3CC2)OCC2=C(N=NN2C2=CC=C(C=C2)F)C)C=CC=1 IETUCUOGOZWGJB-UHFFFAOYSA-N 0.000 claims description 2
• SLMHAZCGGGWHRX-HXUWFJFHSA-N (5R)-5-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]-1-methylpyrrolidin-2-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)[C@H]1CCC(N1C)=O)C SLMHAZCGGGWHRX-HXUWFJFHSA-N 0.000 claims description 2
• SLMHAZCGGGWHRX-FQEVSTJZSA-N (5S)-5-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]-1-methylpyrrolidin-2-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)[C@@H]1CCC(N1C)=O)C SLMHAZCGGGWHRX-FQEVSTJZSA-N 0.000 claims description 2
• QVZBIXVWFBZNIS-UHFFFAOYSA-N 1-[2-[[3-(4-chlorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1COC1=CC=C2C(=N1)CN(C2)C(C)=O)C QVZBIXVWFBZNIS-UHFFFAOYSA-N 0.000 claims description 2
• KHWRDWIIDJAFHQ-UHFFFAOYSA-N 1-[2-[[3-(4-chlorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]-2-methoxyethanone Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(COC)=O)C KHWRDWIIDJAFHQ-UHFFFAOYSA-N 0.000 claims description 2
• JTUIPEJYCSUDQQ-UHFFFAOYSA-N 1-[2-[[3-(4-chlorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]ethanone Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(C)=O)C JTUIPEJYCSUDQQ-UHFFFAOYSA-N 0.000 claims description 2
• NONGHSWFEQAXFW-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-2-methylsulfonylethanone Chemical compound FC1=CC=C(C=C1)C1=NOC(=C1COC1=CC=C2C(=N1)CN(C2)C(CS(=O)(=O)C)=O)C NONGHSWFEQAXFW-UHFFFAOYSA-N 0.000 claims description 2
• QISFVWCTFGVVSH-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound FC1=CC=C(C=C1)C1=NOC(=C1COC1=CC=C2C(=N1)CN(C2)C(C)=O)C QISFVWCTFGVVSH-UHFFFAOYSA-N 0.000 claims description 2
• DBCZYWJNMCGCKR-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-2,2-dimethylpropan-1-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=CC=C2C(=N1)CN(C2)C(C(C)(C)C)=O)C DBCZYWJNMCGCKR-UHFFFAOYSA-N 0.000 claims description 2
• ATKOTHLPBKBASC-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-2-methylpropan-1-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=CC=C2C(=N1)CN(C2)C(C(C)C)=O)C ATKOTHLPBKBASC-UHFFFAOYSA-N 0.000 claims description 2
• BAFQGTJJFBRHCA-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-3-methylbutan-1-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=CC=C2C(=N1)CN(C2)C(CC(C)C)=O)C BAFQGTJJFBRHCA-UHFFFAOYSA-N 0.000 claims description 2
• IGANKKXNZYWZFN-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=CC=C2C(=N1)CN(C2)C(C)=O)C IGANKKXNZYWZFN-UHFFFAOYSA-N 0.000 claims description 2
• KUNZDYIIZBFFIE-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]propan-1-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=CC=C2C(=N1)CN(C2)C(CC)=O)C KUNZDYIIZBFFIE-UHFFFAOYSA-N 0.000 claims description 2
• PIABAEATXPVRNL-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-6,8-dihydro-5H-1,7-naphthyridin-7-yl]ethanone Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CN(CCC=2C=C1)C(C)=O)C PIABAEATXPVRNL-UHFFFAOYSA-N 0.000 claims description 2
• SWXWAFWNZQBDGH-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]-2-methylpropan-1-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(C(C)C)=O)C SWXWAFWNZQBDGH-UHFFFAOYSA-N 0.000 claims description 2
• SKQKKNRYYXFJQN-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]ethanone Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(C)=O)C SKQKKNRYYXFJQN-UHFFFAOYSA-N 0.000 claims description 2
• TWPMNPAALDJMPK-UHFFFAOYSA-N 1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]propan-1-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(CC)=O)C TWPMNPAALDJMPK-UHFFFAOYSA-N 0.000 claims description 2
• VLQZKWVCWZLURG-UHFFFAOYSA-N 1-[2-[[5-(4-chlorophenyl)-3-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound ClC1=CC=C(C=C1)C=1N=NN(C=1COC1=CC=C2C(=N1)CN(C2)C(C)=O)C VLQZKWVCWZLURG-UHFFFAOYSA-N 0.000 claims description 2
• UAVWCBFZNAQLCB-UHFFFAOYSA-N 1-[2-[[5-(4-fluorophenyl)-3-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-2-methylpropan-1-one Chemical compound FC1=CC=C(C=C1)C=1N=NN(C=1COC1=CC=C2C(=N1)CN(C2)C(C(C)C)=O)C UAVWCBFZNAQLCB-UHFFFAOYSA-N 0.000 claims description 2
• CCPWUXXPRTWCKO-UHFFFAOYSA-N 1-[2-[[5-(4-fluorophenyl)-3-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound FC1=CC=C(C=C1)C=1N=NN(C=1COC1=CC=C2C(=N1)CN(C2)C(C)=O)C CCPWUXXPRTWCKO-UHFFFAOYSA-N 0.000 claims description 2
• HSGRHLUXHXTARS-UHFFFAOYSA-N 1-[2-[[5-(4-fluorophenyl)-3-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]propan-1-one Chemical compound FC1=CC=C(C=C1)C=1N=NN(C=1COC1=CC=C2C(=N1)CN(C2)C(CC)=O)C HSGRHLUXHXTARS-UHFFFAOYSA-N 0.000 claims description 2
• FZYMSCLXDBCKOR-UHFFFAOYSA-N 1-ethyl-4-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]pyrrolidin-2-one Chemical compound C(C)N1C(CC(C1)C(=O)N1CC=2C=CC(=NC=2CC1)OCC1=C(N=NN1C1=CC=C(C=C1)F)C)=O FZYMSCLXDBCKOR-UHFFFAOYSA-N 0.000 claims description 2
• XBGYWCSWCWVUNG-UHFFFAOYSA-N 2,2,2-trifluoro-1-[2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]ethanone Chemical compound FC(C(=O)N1CC=2C=CC(=NC=2CC1)OCC=1C(=NOC=1C)C1=CC=C(C=C1)F)(F)F XBGYWCSWCWVUNG-UHFFFAOYSA-N 0.000 claims description 2
• PUMMNXDEKAECQR-UHFFFAOYSA-N 2,2,2-trifluoro-1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound CC1=C(N(N=N1)C2=CC=C(C=C2)F)COC3=NC4=C(CN(C4)C(=O)C(F)(F)F)C=C3 PUMMNXDEKAECQR-UHFFFAOYSA-N 0.000 claims description 2
• WUHASFQSYJWPQZ-UHFFFAOYSA-N 2,2-difluoro-1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound CC1=C(N(N=N1)C2=CC=C(C=C2)F)COC3=NC4=C(CN(C4)C(=O)C(F)F)C=C3 WUHASFQSYJWPQZ-UHFFFAOYSA-N 0.000 claims description 2
• NHAVPZBYCXDYLA-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]-N,N-dimethyl-7,8-dihydro-5H-1,6-naphthyridine-6-carboxamide Chemical compound FC1=CC=C(C=C1)C1=NOC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)N(C)C)C NHAVPZBYCXDYLA-UHFFFAOYSA-N 0.000 claims description 2
• ZUGSNHSKYZRTGC-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]-N-(oxolan-3-yl)-7,8-dihydro-5H-1,6-naphthyridine-6-carboxamide Chemical compound FC1=CC=C(C=C1)C1=NOC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)NC1COCC1)C ZUGSNHSKYZRTGC-UHFFFAOYSA-N 0.000 claims description 2
• COUPFRKMXMSVIF-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-N,N-dimethyl-7,8-dihydro-5H-1,6-naphthyridine-6-carboxamide Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)N(C)C)C COUPFRKMXMSVIF-UHFFFAOYSA-N 0.000 claims description 2
• BFBQNXDBCFYSQA-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-N-(oxolan-3-yl)-7,8-dihydro-5H-1,6-naphthyridine-6-carboxamide Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)NC1COCC1)C BFBQNXDBCFYSQA-UHFFFAOYSA-N 0.000 claims description 2
• VJZODEQRIGYXDS-UHFFFAOYSA-N 2-fluoro-1-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethanone Chemical compound FCC(=O)N1CC2=NC(=CC=C2C1)OCC1=C(N=NN1C1=CC=C(C=C1)F)C VJZODEQRIGYXDS-UHFFFAOYSA-N 0.000 claims description 2
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• CEPWICKCWXPROW-UHFFFAOYSA-N 4-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]-1-methylpyrrolidin-2-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)C1CC(N(C1)C)=O)C CEPWICKCWXPROW-UHFFFAOYSA-N 0.000 claims description 2
• BOXIMVULKPABHC-UHFFFAOYSA-N 4-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]-1-propan-2-ylpyrrolidin-2-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)C1CC(N(C1)C(C)C)=O)C BOXIMVULKPABHC-UHFFFAOYSA-N 0.000 claims description 2
• YLVWLVGKOYHREW-UHFFFAOYSA-N 5-[2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]-1-methylpiperidin-2-one Chemical compound FC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)C1CCC(N(C1)C)=O)C YLVWLVGKOYHREW-UHFFFAOYSA-N 0.000 claims description 2
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• WOPJUQQSVPZRIB-UHFFFAOYSA-N N-(2-chlorophenyl)-2-[[3-(4-fluorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carboxamide Chemical compound ClC1=C(C=CC=C1)NC(=O)N1CC=2C=CC(=NC=2CC1)OCC1=C(N=NN1C1=CC=C(C=C1)F)C WOPJUQQSVPZRIB-UHFFFAOYSA-N 0.000 claims description 2
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• QOLCYFCYKXOVDP-UHFFFAOYSA-N [2-[[3-(4-chlorophenyl)-5-methyltriazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridin-6-yl]-pyridin-4-ylmethanone Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)C1=CC=NC=C1)C QOLCYFCYKXOVDP-UHFFFAOYSA-N 0.000 claims description 2
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• LCNUIOCHHIHEGG-UHFFFAOYSA-N [2-[[5-(4-fluorophenyl)-3-methyltriazol-4-yl]methoxy]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]-(oxolan-2-yl)methanone Chemical compound FC1=CC=C(C=C1)C=1N=NN(C=1COC1=CC=C2C(=N1)CN(C2)C(=O)C1OCCC1)C LCNUIOCHHIHEGG-UHFFFAOYSA-N 0.000 claims description 2
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