JPWO2020065597A5 - - Google Patents
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- Publication number
- JPWO2020065597A5 JPWO2020065597A5 JP2021516369A JP2021516369A JPWO2020065597A5 JP WO2020065597 A5 JPWO2020065597 A5 JP WO2020065597A5 JP 2021516369 A JP2021516369 A JP 2021516369A JP 2021516369 A JP2021516369 A JP 2021516369A JP WO2020065597 A5 JPWO2020065597 A5 JP WO2020065597A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- fluorophenyl
- methoxy
- triazol
- tetrahydro
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 208000010877 cognitive disease Diseases 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 4
- 201000010374 Down Syndrome Diseases 0.000 claims 4
- 230000006999 cognitive decline Effects 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 208000024714 major depressive disease Diseases 0.000 claims 4
- 206010027175 memory impairment Diseases 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 208000037820 vascular cognitive impairment Diseases 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 208000027626 Neurocognitive disease Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000027520 Somatoform disease Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 230000007278 cognition impairment Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 239000002664 nootropic agent Substances 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 208000027753 pain disease Diseases 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- QLKWIZYDNATRKP-UHFFFAOYSA-N 2-fluoro-1-[2-[[5-(4-fluorophenyl)-3-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=NN1C)C1=CC=C(C=C1)F QLKWIZYDNATRKP-UHFFFAOYSA-N 0.000 claims 1
- SLOOXBXYFZZFMA-UHFFFAOYSA-N 4-[2-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]-7,8-dihydro-5H-1,6-naphthyridine-6-carbonyl]-1-methylpyrrolidin-2-one Chemical compound FC1=CC=C(C=C1)C1=NOC(=C1COC1=NC=2CCN(CC=2C=C1)C(=O)C1CC(N(C1)C)=O)C SLOOXBXYFZZFMA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DVVPHPORYSWGRG-UHFFFAOYSA-N CC1=C(COC2=NC(CCN(C3)C(CCS(C)(=O)=O)=O)=C3C=C2)C(C(C=C2)=CC=C2F)=NO1 Chemical compound CC1=C(COC2=NC(CCN(C3)C(CCS(C)(=O)=O)=O)=C3C=C2)C(C(C=C2)=CC=C2F)=NO1 DVVPHPORYSWGRG-UHFFFAOYSA-N 0.000 claims 1
- GTVLCHCOKLXHLY-UHFFFAOYSA-N CC1=C(COC2=NC(CCN(C3)C(CS(C)(=O)=O)=O)=C3C=C2)C(C(C=C2)=CC=C2F)=NO1 Chemical compound CC1=C(COC2=NC(CCN(C3)C(CS(C)(=O)=O)=O)=C3C=C2)C(C(C=C2)=CC=C2F)=NO1 GTVLCHCOKLXHLY-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP1800333 | 2018-09-28 | ||
| HU1800333A HU231223B1 (hu) | 2018-09-28 | 2018-09-28 | GABAA A5 receptor modulátor hatású biciklusos vegyületek |
| PCT/IB2019/058208 WO2020065597A1 (en) | 2018-09-28 | 2019-09-27 | Bicyclic derivatives as gabaa α5 receptor modulators |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2022502366A JP2022502366A (ja) | 2022-01-11 |
| JP2022502366A5 JP2022502366A5 (https=) | 2022-09-21 |
| JPWO2020065597A5 true JPWO2020065597A5 (https=) | 2022-09-21 |
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| JP (1) | JP7480128B2 (https=) |
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| US20240043418A1 (en) * | 2020-03-26 | 2024-02-08 | Richter Gedeon Nyrt. | 1,3-dihydro-2h-pyrrolo[3,4-c]pyridine derivatives as gabaa a5 receptor modulators |
| TWI901650B (zh) * | 2020-03-26 | 2025-10-21 | 匈牙利商羅特格登公司 | 啶及吡啶并〔３，４－ｃ〕嗒衍生物 |
| HU231691B1 (hu) * | 2021-09-29 | 2025-10-28 | Richter Gedeon Nyrt | GABAA ALFA5 receptor modulátor hatású biciklusos aminszármazékok |
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| IT1237793B (it) * | 1989-12-21 | 1993-06-17 | Zambon Spa | Composti attivi come inibitori dell'enzima hmg-coa reduttasi |
| EP0986562B1 (en) | 1997-05-08 | 2002-08-07 | MERCK SHARP & DOHME LTD. | Substituted 1,2,4-triazolo 3,4-a]phthalazine derivatives as gaba alpha 5 ligands |
| GB9813576D0 (en) | 1998-06-24 | 1998-08-19 | Merck Sharp & Dohme | Therapeutic agents |
| GB0017518D0 (en) | 2000-07-17 | 2000-08-30 | Merck Sharp & Dohme | Therapeutic agents |
| JP4148672B2 (ja) | 2000-11-17 | 2008-09-10 | 武田薬品工業株式会社 | イソオキサゾール誘導体 |
| JP2003261545A (ja) | 2001-12-28 | 2003-09-19 | Takeda Chem Ind Ltd | 神経栄養因子産生・分泌促進剤 |
| EP1888594A2 (en) | 2005-05-16 | 2008-02-20 | Wisys Technology Foundation, Inc. | Gabaergic agents to treat memory deficits |
| US7790745B2 (en) | 2005-10-21 | 2010-09-07 | Bristol-Myers Squibb Company | Tetrahydroisoquinoline LXR Modulators |
| TW200812982A (en) | 2006-05-24 | 2008-03-16 | Lilly Co Eli | Compounds and methods for modulating FXR |
| KR20100038102A (ko) | 2007-06-13 | 2010-04-12 | 글락소스미스클라인 엘엘씨 | 파네소이드 ｘ 수용체 작용제 |
| KR101175859B1 (ko) | 2007-12-04 | 2012-08-24 | 에프. 호프만-라 로슈 아게 | 이속사졸로-피라진 유도체 |
| KR101237576B1 (ko) | 2007-12-04 | 2013-03-04 | 에프. 호프만-라 로슈 아게 | 아이속사졸로-피리딘 유도체 |
| US7943619B2 (en) | 2007-12-04 | 2011-05-17 | Hoffmann-La Roche Inc. | Isoxazolo-pyridazine derivatives |
| US8389550B2 (en) * | 2009-02-25 | 2013-03-05 | Hoffmann-La Roche Inc. | Isoxazoles / O-pyridines with ethyl and ethenyl linker |
| US8222246B2 (en) | 2009-04-02 | 2012-07-17 | Hoffmann-La Roche Inc. | Substituted isoxazoles |
| JP5460858B2 (ja) | 2009-05-05 | 2014-04-02 | エフ．ホフマン−ラ ロシュ アーゲー | イソオキサゾール−ピラゾール誘導体 |
| BRPI1013766A2 (pt) | 2009-05-07 | 2016-04-05 | Hoffmann La Roche | "derivados de isoxazol-piridina como moduladores de gaba" |
| GB2474120B (en) | 2009-10-01 | 2011-12-21 | Amira Pharmaceuticals Inc | Compounds as Lysophosphatidic acid receptor antagonists |
| GB201016088D0 (en) | 2010-09-24 | 2010-11-10 | Phase Focus Ltd | Improvements in imaging |
| MX341471B (es) | 2010-11-05 | 2016-08-22 | Hoffmann La Roche | Uso de compuestos farmaceuticos activos para el tratamiento de estados patologicos del sistema nervioso central. |
| KR20130100348A (ko) | 2010-11-09 | 2013-09-10 | 에프. 호프만-라 로슈 아게 | Gaba 수용체에 대한 리간드로서의 트라이아졸 유도체 |
| US8742097B2 (en) | 2010-11-09 | 2014-06-03 | Hoffmann-La Roche Inc. | Triazole compounds I |
| AU2011329233A1 (en) | 2010-11-15 | 2013-05-23 | Abbvie Deutschland Gmbh & Co Kg | NAMPT and ROCK inhibitors |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| US8604062B2 (en) | 2011-10-20 | 2013-12-10 | Hoffman-La Roche Inc. | Process for the preparation of isoxazolyl-methoxy nicotinic acids |
| BR112014013136B1 (pt) | 2011-11-30 | 2020-05-26 | F. Hoffmann-La Roche Ag | Novos derivados de dihidroisoquinolina-1-ona biciclicos |
| WO2014001281A1 (en) | 2012-06-26 | 2014-01-03 | Aniona Aps | A phenyl triazole derivative and its use for modulating the gabaa receptor complex |
| WO2014001278A1 (en) * | 2012-06-26 | 2014-01-03 | Aniona Aps | A phenyl triazole derivative and its use for modulating the gabaa receptor complex |
| WO2016107832A1 (en) | 2014-12-30 | 2016-07-07 | F. Hoffmann-La Roche Ag | Novel tetrahydropyridopyrimidines and tetrahydropyridopyridines for the treatment and prophylaxis of hepatitis b virus infection |
| WO2017133521A1 (zh) | 2016-02-01 | 2017-08-10 | 山东轩竹医药科技有限公司 | Fxr受体激动剂 |
| BR112019006571A2 (pt) | 2016-12-08 | 2019-07-02 | F. Hoffmann-La Roche Ag | derivados de éter de isoxazolila como gaba a alfa5 pam |
-
2018
- 2018-09-28 HU HU1800333A patent/HU231223B1/hu unknown
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2019
- 2019-09-27 TW TW108135172A patent/TWI868079B/zh active
- 2019-09-27 US US17/279,654 patent/US12370182B2/en active Active
- 2019-09-27 EP EP19779613.9A patent/EP3856342B1/en active Active
- 2019-09-27 CN CN201980063431.3A patent/CN112805063B/zh active Active
- 2019-09-27 BR BR112021005837-0A patent/BR112021005837A2/pt unknown
- 2019-09-27 WO PCT/IB2019/058208 patent/WO2020065597A1/en not_active Ceased
- 2019-09-27 EA EA202190857A patent/EA202190857A1/ru unknown
- 2019-09-27 MX MX2021003670A patent/MX2021003670A/es unknown
- 2019-09-27 KR KR1020217012783A patent/KR20210086631A/ko not_active Ceased
- 2019-09-27 CA CA3113072A patent/CA3113072A1/en active Pending
- 2019-09-27 AU AU2019346147A patent/AU2019346147B2/en active Active
- 2019-09-27 AR ARP190102762A patent/AR116549A1/es unknown
- 2019-09-27 UA UAA202102250A patent/UA130217C2/uk unknown
- 2019-09-27 JP JP2021516369A patent/JP7480128B2/ja active Active
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