JP2019530695A5 - - Google Patents
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- Publication number
- JP2019530695A5 JP2019530695A5 JP2019518219A JP2019518219A JP2019530695A5 JP 2019530695 A5 JP2019530695 A5 JP 2019530695A5 JP 2019518219 A JP2019518219 A JP 2019518219A JP 2019518219 A JP2019518219 A JP 2019518219A JP 2019530695 A5 JP2019530695 A5 JP 2019530695A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- imidazole
- pyridin
- phenyl
- oxo
- 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
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- -1 N (CH 3 ) 2 Chemical group 0.000 claims description 1015
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 934
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 425
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 195
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 184
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 120
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 150000002460 imidazoles Chemical class 0.000 claims description 98
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000012453 solvate Substances 0.000 claims description 43
- 150000001204 N-oxides Chemical class 0.000 claims description 40
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 27
- 125000004076 pyridyl group Chemical group 0.000 claims description 27
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 25
- 125000001544 thienyl group Chemical group 0.000 claims description 23
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 22
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 20
- 125000003566 oxetanyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
- FPGGLMIYNLQOID-UHFFFAOYSA-N 3h-pyridin-2-one Chemical compound O=C1CC=CC=N1 FPGGLMIYNLQOID-UHFFFAOYSA-N 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000002393 azetidinyl group Chemical group 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 12
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 7
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 6
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 102000034527 Retinoid X Receptors Human genes 0.000 claims description 4
- 108010038912 Retinoid X Receptors Proteins 0.000 claims description 4
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 4
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000000155 isotopic effect Effects 0.000 claims description 4
- 208000024714 major depressive disease Diseases 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- YYFAXNDGFHTVEQ-UHFFFAOYSA-N 6-[3-(dimethylamino)phenyl]-1-[(3-fluorophenyl)methyl]-3H-imidazo[4,5-b]pyridin-2-one Chemical compound CN(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(N2CC1=CC(=CC=C1)F)=O)C YYFAXNDGFHTVEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
- 206010003805 Autism Diseases 0.000 claims description 2
- 208000020706 Autistic disease Diseases 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- VDNCCWWMTPZKLW-UHFFFAOYSA-N CC(C(F)=C(C=C1)C(N=CC(CN2C=CN(C)C2)=C2)=C2F)=C1F Chemical compound CC(C(F)=C(C=C1)C(N=CC(CN2C=CN(C)C2)=C2)=C2F)=C1F VDNCCWWMTPZKLW-UHFFFAOYSA-N 0.000 claims description 2
- LUMWMOUZWYIEPS-UHFFFAOYSA-N CC(C(F)=C(C=C1)C(N=CC(CN2C=CNC2)=C2)=C2F)=C1F Chemical compound CC(C(F)=C(C=C1)C(N=CC(CN2C=CNC2)=C2)=C2F)=C1F LUMWMOUZWYIEPS-UHFFFAOYSA-N 0.000 claims description 2
- NDDWQZFAUIYOKC-UHFFFAOYSA-N CC(C(F)=C(C=C1)C2=CC(CN3C=CN(C)C3)=CC=N2)=C1F Chemical compound CC(C(F)=C(C=C1)C2=CC(CN3C=CN(C)C3)=CC=N2)=C1F NDDWQZFAUIYOKC-UHFFFAOYSA-N 0.000 claims description 2
- DIQRPXCHJWETIZ-UHFFFAOYSA-N CC(C(F)=C(C=C1)C2=CC(CN3C=CN(C)C3)=NC=N2)=C1F Chemical compound CC(C(F)=C(C=C1)C2=CC(CN3C=CN(C)C3)=NC=N2)=C1F DIQRPXCHJWETIZ-UHFFFAOYSA-N 0.000 claims description 2
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| WO2014124651A1 (en) | 2013-02-15 | 2014-08-21 | Københavns Universitet | Pyrrolidine-2-carboxylic acid derivatives as iglur antagonists |
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| US12006328B2 (en) | 2014-11-18 | 2024-06-11 | Emory University | Thieno[2,3-d]pyrimidin-4-one derivatives as NMDAR modulators and uses related thereto |
| MA41803A (fr) | 2015-03-24 | 2018-01-30 | Almirall Sa | Dérivés amino-indazoles utilisés comme inhibiteurs des canaux sodiques |
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-
2017
- 2017-10-03 TW TW106134127A patent/TW201819376A/zh unknown
- 2017-10-05 MX MX2019003980A patent/MX2019003980A/es unknown
- 2017-10-05 BR BR112019006691A patent/BR112019006691A2/pt not_active Application Discontinuation
- 2017-10-05 AR ARP170102779A patent/AR109810A1/es unknown
- 2017-10-05 AU AU2017340602A patent/AU2017340602A1/en not_active Abandoned
- 2017-10-05 US US15/725,500 patent/US10617676B2/en active Active
- 2017-10-05 KR KR1020197012678A patent/KR20190056435A/ko not_active Withdrawn
- 2017-10-05 MA MA046470A patent/MA46470A/fr unknown
- 2017-10-05 EA EA201990848A patent/EA201990848A1/ru unknown
- 2017-10-05 ES ES17859165T patent/ES2950881T3/es active Active
- 2017-10-05 EP EP17859165.7A patent/EP3523311B1/en active Active
- 2017-10-05 WO PCT/US2017/055278 patent/WO2018067786A1/en not_active Ceased
- 2017-10-05 CA CA3038820A patent/CA3038820A1/en active Pending
- 2017-10-05 CN CN201780075930.5A patent/CN110062761B/zh active Active
- 2017-10-05 JP JP2019518219A patent/JP7001682B2/ja active Active
- 2017-10-05 CN CN202210460371.2A patent/CN114989164B/zh active Active
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2019
- 2019-03-28 PH PH12019500676A patent/PH12019500676A1/en unknown
- 2019-04-01 IL IL265757A patent/IL265757A/en unknown
- 2019-04-02 CL CL2019000882A patent/CL2019000882A1/es unknown
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2020
- 2020-03-03 US US16/807,385 patent/US11207298B2/en active Active
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2021
- 2021-09-14 US US17/474,631 patent/US11759455B2/en active Active
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2023
- 2023-06-29 US US18/344,169 patent/US20230338341A1/en not_active Abandoned
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