JP2017524019A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017524019A5 JP2017524019A5 JP2017508504A JP2017508504A JP2017524019A5 JP 2017524019 A5 JP2017524019 A5 JP 2017524019A5 JP 2017508504 A JP2017508504 A JP 2017508504A JP 2017508504 A JP2017508504 A JP 2017508504A JP 2017524019 A5 JP2017524019 A5 JP 2017524019A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- ylmethyl
- triazole
- imidazol
- chloro
- 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
- 125000005843 halogen group Chemical group 0.000 claims description 131
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 150000001204 N-oxides Chemical class 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 23
- 208000035475 disorder Diseases 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- -1 3,5-dicyclopropyl- [1,2,4] triazol-1-ylmethyl Chemical group 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 108010054200 NR2B NMDA receptor Proteins 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- OSODAZMEELVOGC-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)OC(F)F OSODAZMEELVOGC-UHFFFAOYSA-N 0.000 claims description 5
- UJRJRHMCPMPBNM-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C UJRJRHMCPMPBNM-UHFFFAOYSA-N 0.000 claims description 5
- NTXPVEQQFPXEPU-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)OC(F)F NTXPVEQQFPXEPU-UHFFFAOYSA-N 0.000 claims description 5
- RPRRSXXASCSWCX-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC)OC(F)F RPRRSXXASCSWCX-UHFFFAOYSA-N 0.000 claims description 5
- BRINTJVXMVTOJY-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)N)OC(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)N)OC(F)F BRINTJVXMVTOJY-UHFFFAOYSA-N 0.000 claims description 5
- OBJSITFIPOKILU-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C)F Chemical compound FC(OC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C)F OBJSITFIPOKILU-UHFFFAOYSA-N 0.000 claims description 5
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 5
- 208000024714 major depressive disease Diseases 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000000926 neurological effect Effects 0.000 claims description 4
- ABOXKYVSSWHNON-UHFFFAOYSA-N C(C)(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl Chemical compound C(C)(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl ABOXKYVSSWHNON-UHFFFAOYSA-N 0.000 claims description 3
- NXVWMYHMJCGROD-UHFFFAOYSA-N C(C)(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)OC(F)F Chemical compound C(C)(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)OC(F)F NXVWMYHMJCGROD-UHFFFAOYSA-N 0.000 claims description 3
- KHTCVPAURHYMJW-UHFFFAOYSA-N C(C)(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl Chemical compound C(C)(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl KHTCVPAURHYMJW-UHFFFAOYSA-N 0.000 claims description 3
- DZEGAUUMJVVSNN-UHFFFAOYSA-N C(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F Chemical compound C(C)(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F DZEGAUUMJVVSNN-UHFFFAOYSA-N 0.000 claims description 3
- ZUBNWKBIEHKLQD-UHFFFAOYSA-N C(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F Chemical compound C(C)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F ZUBNWKBIEHKLQD-UHFFFAOYSA-N 0.000 claims description 3
- FABOZFZSWJBLAK-UHFFFAOYSA-N C(CCC)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl Chemical compound C(CCC)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl FABOZFZSWJBLAK-UHFFFAOYSA-N 0.000 claims description 3
- VTFRNZQXDOHSFI-UHFFFAOYSA-N C(CCC)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)Cl Chemical compound C(CCC)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)Cl VTFRNZQXDOHSFI-UHFFFAOYSA-N 0.000 claims description 3
- CEAOOXKEMXDLAB-UHFFFAOYSA-N C(CCC)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl Chemical compound C(CCC)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl CEAOOXKEMXDLAB-UHFFFAOYSA-N 0.000 claims description 3
- BCMMYCCUZMUCKE-UHFFFAOYSA-N C1(CC1)C=1C=C(C=CC=1)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound C1(CC1)C=1C=C(C=CC=1)N1N=NC(=C1)CN1C(=NC=C1)C BCMMYCCUZMUCKE-UHFFFAOYSA-N 0.000 claims description 3
- QUXRRGHMYGOPOY-UHFFFAOYSA-N C1(CC1)C=1C=C(C=CC=1)N1N=NC(=C1)CN1C(=NC=C1)CCO Chemical compound C1(CC1)C=1C=C(C=CC=1)N1N=NC(=C1)CN1C(=NC=C1)CCO QUXRRGHMYGOPOY-UHFFFAOYSA-N 0.000 claims description 3
- RZJJYMUPIPAFHM-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=C(C=C(C=C1)Cl)Cl Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=C(C=C(C=C1)Cl)Cl RZJJYMUPIPAFHM-UHFFFAOYSA-N 0.000 claims description 3
- VYUWAHTYQGQTNF-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=C(C=C(C=C1)F)OC Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=C(C=C(C=C1)F)OC VYUWAHTYQGQTNF-UHFFFAOYSA-N 0.000 claims description 3
- UZACFXZVMOVAMD-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)C)F Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)C)F UZACFXZVMOVAMD-UHFFFAOYSA-N 0.000 claims description 3
- IEGRHOUALWXAMI-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl IEGRHOUALWXAMI-UHFFFAOYSA-N 0.000 claims description 3
- BTLPJWLNOBZJLX-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C BTLPJWLNOBZJLX-UHFFFAOYSA-N 0.000 claims description 3
- XRNXEVVICQRAAE-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C(F)F Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C(F)F XRNXEVVICQRAAE-UHFFFAOYSA-N 0.000 claims description 3
- IECCSHSCJSNUFX-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)C(F)(F)F Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)C(F)(F)F IECCSHSCJSNUFX-UHFFFAOYSA-N 0.000 claims description 3
- BINRGTLWUGYJBP-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F BINRGTLWUGYJBP-UHFFFAOYSA-N 0.000 claims description 3
- NMIQLTRGPMQQII-UHFFFAOYSA-N C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)C(F)(F)F Chemical compound C1(CC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)C(F)(F)F NMIQLTRGPMQQII-UHFFFAOYSA-N 0.000 claims description 3
- QSKZBFJMOFMZSF-UHFFFAOYSA-N CC1=NC=CN1CC1=CN(N=N1)C1=CC(C(F)F)=C(F)C=C1 Chemical compound CC1=NC=CN1CC1=CN(N=N1)C1=CC(C(F)F)=C(F)C=C1 QSKZBFJMOFMZSF-UHFFFAOYSA-N 0.000 claims description 3
- VFTFBBYRZOXORC-UHFFFAOYSA-N CC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)C(F)(F)F Chemical compound CC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)C(F)(F)F VFTFBBYRZOXORC-UHFFFAOYSA-N 0.000 claims description 3
- PSNQKKDWPZLWKY-UHFFFAOYSA-N CC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F Chemical compound CC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)OC(F)(F)F PSNQKKDWPZLWKY-UHFFFAOYSA-N 0.000 claims description 3
- BLCNKRJMNGQWJU-UHFFFAOYSA-N CC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)C(F)(F)F Chemical compound CC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)C(F)(F)F BLCNKRJMNGQWJU-UHFFFAOYSA-N 0.000 claims description 3
- PNOCWPPPUIQTEQ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)C Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)C PNOCWPPPUIQTEQ-UHFFFAOYSA-N 0.000 claims description 3
- PEDNWEQKMIWGBJ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)C(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)C(F)F PEDNWEQKMIWGBJ-UHFFFAOYSA-N 0.000 claims description 3
- DRHMCKZRSIYNSH-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C(F)(F)F DRHMCKZRSIYNSH-UHFFFAOYSA-N 0.000 claims description 3
- QLHBDCCSPGVPTO-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C(F)F QLHBDCCSPGVPTO-UHFFFAOYSA-N 0.000 claims description 3
- FMTUKULXLDFHHK-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)F FMTUKULXLDFHHK-UHFFFAOYSA-N 0.000 claims description 3
- LCRLHAYDJUFDBS-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)C Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)C LCRLHAYDJUFDBS-UHFFFAOYSA-N 0.000 claims description 3
- UULWSVSDBXUUNT-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)C(F)(F)F UULWSVSDBXUUNT-UHFFFAOYSA-N 0.000 claims description 3
- JLSQSDCBSROECG-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)C(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)C(F)F JLSQSDCBSROECG-UHFFFAOYSA-N 0.000 claims description 3
- BJBDOPNIPHEBTL-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)F BJBDOPNIPHEBTL-UHFFFAOYSA-N 0.000 claims description 3
- BHASKRVNSLNZGW-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)OC(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1)OC(F)F BHASKRVNSLNZGW-UHFFFAOYSA-N 0.000 claims description 3
- HQQFCWPHPRSGTH-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC)C Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC)C HQQFCWPHPRSGTH-UHFFFAOYSA-N 0.000 claims description 3
- CIAAWOPCBYSYLC-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC)C(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC)C(F)F CIAAWOPCBYSYLC-UHFFFAOYSA-N 0.000 claims description 3
- QFNOXQXTBCOOIT-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCF)OC(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCF)OC(F)F QFNOXQXTBCOOIT-UHFFFAOYSA-N 0.000 claims description 3
- QGHUYWCWQWJAPH-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCO)C Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCO)C QGHUYWCWQWJAPH-UHFFFAOYSA-N 0.000 claims description 3
- SDYVDXMMCZXDQX-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCO)OC(F)F Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCO)OC(F)F SDYVDXMMCZXDQX-UHFFFAOYSA-N 0.000 claims description 3
- VYRSMGXIQJIWHO-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound ClC1=C(C=CC(=C1)Cl)N1N=NC(=C1)CN1C(=NC=C1)C VYRSMGXIQJIWHO-UHFFFAOYSA-N 0.000 claims description 3
- OCWFBNMIXTWOIS-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C OCWFBNMIXTWOIS-UHFFFAOYSA-N 0.000 claims description 3
- FMXPLHPTIXIQOD-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(=O)C1=CC=C(C=C1)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(=O)C1=CC=C(C=C1)C FMXPLHPTIXIQOD-UHFFFAOYSA-N 0.000 claims description 3
- NRWRQBPXPZXDGL-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C(C)C NRWRQBPXPZXDGL-UHFFFAOYSA-N 0.000 claims description 3
- UCXUHYULIWVCHH-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C1CC1 UCXUHYULIWVCHH-UHFFFAOYSA-N 0.000 claims description 3
- UHCWOUZOICIRGT-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CC UHCWOUZOICIRGT-UHFFFAOYSA-N 0.000 claims description 3
- AYJDATHUPMMOSP-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCC Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCC AYJDATHUPMMOSP-UHFFFAOYSA-N 0.000 claims description 3
- ZZKGILMYXMDXEH-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)C ZZKGILMYXMDXEH-UHFFFAOYSA-N 0.000 claims description 3
- AJGOWAAIQPCIPM-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)C(C)C Chemical compound ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)C(C)C AJGOWAAIQPCIPM-UHFFFAOYSA-N 0.000 claims description 3
- ACNAPZHYUZOZJN-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)CC Chemical compound ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)CC ACNAPZHYUZOZJN-UHFFFAOYSA-N 0.000 claims description 3
- VBCLULJZISPDRO-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)CCC Chemical compound ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)CCC VBCLULJZISPDRO-UHFFFAOYSA-N 0.000 claims description 3
- PNPKQVICELDSLM-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)CCF Chemical compound ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC=C1)CCF PNPKQVICELDSLM-UHFFFAOYSA-N 0.000 claims description 3
- RIWYADOJEYZZRZ-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C RIWYADOJEYZZRZ-UHFFFAOYSA-N 0.000 claims description 3
- LSZVDBKEFVBAEY-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C1CC1 Chemical compound ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C1CC1 LSZVDBKEFVBAEY-UHFFFAOYSA-N 0.000 claims description 3
- JFZBXZHTGAUVGD-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CC Chemical compound ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CC JFZBXZHTGAUVGD-UHFFFAOYSA-N 0.000 claims description 3
- WMFPPBDLJCGXMI-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCC Chemical compound ClC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCC WMFPPBDLJCGXMI-UHFFFAOYSA-N 0.000 claims description 3
- IVDHBJSENGBWTH-UHFFFAOYSA-N ClC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl Chemical compound ClC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl IVDHBJSENGBWTH-UHFFFAOYSA-N 0.000 claims description 3
- UJPVZTKYGGHGLB-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound FC(C)(F)C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C UJPVZTKYGGHGLB-UHFFFAOYSA-N 0.000 claims description 3
- QULVTNJBHGMPJK-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCO Chemical compound FC(C)(F)C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCO QULVTNJBHGMPJK-UHFFFAOYSA-N 0.000 claims description 3
- OCGOMHKIACWSMG-UHFFFAOYSA-N FC(C=1C=C(C=C(C=1)F)N1N=NC(=C1)CN1C(=NC=C1)C)F Chemical compound FC(C=1C=C(C=C(C=1)F)N1N=NC(=C1)CN1C(=NC=C1)C)F OCGOMHKIACWSMG-UHFFFAOYSA-N 0.000 claims description 3
- UEBVHKXENWPKIG-UHFFFAOYSA-N FC(C=1C=C(C=C(C=1)F)N1N=NC(=C1)CN1C(=NC=C1)CCF)F Chemical compound FC(C=1C=C(C=C(C=1)F)N1N=NC(=C1)CN1C(=NC=C1)CCF)F UEBVHKXENWPKIG-UHFFFAOYSA-N 0.000 claims description 3
- XEAHOSRXLJEYBK-UHFFFAOYSA-N FC(C=1C=C(C=C(C=1)F)N1N=NC(=C1)CN1C(=NC=C1)CCO)F Chemical compound FC(C=1C=C(C=C(C=1)F)N1N=NC(=C1)CN1C(=NC=C1)CCO)F XEAHOSRXLJEYBK-UHFFFAOYSA-N 0.000 claims description 3
- RHCWEINUWQCGDI-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)F Chemical compound FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)C(C)C)F RHCWEINUWQCGDI-UHFFFAOYSA-N 0.000 claims description 3
- PKKCOOQFVZMCHD-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CC)F Chemical compound FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CC)F PKKCOOQFVZMCHD-UHFFFAOYSA-N 0.000 claims description 3
- APCKLHZSVVXCSJ-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCC)F Chemical compound FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCC)F APCKLHZSVVXCSJ-UHFFFAOYSA-N 0.000 claims description 3
- ILHXDJNKXGVDCA-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCCC)F Chemical compound FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCCC)F ILHXDJNKXGVDCA-UHFFFAOYSA-N 0.000 claims description 3
- WAGGNWZFAHXBMP-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCO)F Chemical compound FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCO)F WAGGNWZFAHXBMP-UHFFFAOYSA-N 0.000 claims description 3
- CQYRYSJJBAIWRQ-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCO)F Chemical compound FC(OC=1C=C(C=CC=1F)N1N=NC(=C1)CN1C(=NC=C1)CCO)F CQYRYSJJBAIWRQ-UHFFFAOYSA-N 0.000 claims description 3
- SUUBNQYDSCYRFB-UHFFFAOYSA-N FC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C Chemical compound FC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)C SUUBNQYDSCYRFB-UHFFFAOYSA-N 0.000 claims description 3
- VAYNXGJHBAWNOK-UHFFFAOYSA-N FC1=CC(=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)OC Chemical compound FC1=CC(=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)C)OC VAYNXGJHBAWNOK-UHFFFAOYSA-N 0.000 claims description 3
- VNHDHBHZGUTBRW-UHFFFAOYSA-N FC=1C=C(C=CC=1C)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound FC=1C=C(C=CC=1C)N1N=NC(=C1)CN1C(=NC=C1)C VNHDHBHZGUTBRW-UHFFFAOYSA-N 0.000 claims description 3
- KLOSGRVATVPBIQ-UHFFFAOYSA-N FCCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)S(=O)(=O)C Chemical compound FCCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)S(=O)(=O)C KLOSGRVATVPBIQ-UHFFFAOYSA-N 0.000 claims description 3
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 3
- ZCROGTMUHYRBRR-UHFFFAOYSA-N NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)C(F)F Chemical compound NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)C(F)F ZCROGTMUHYRBRR-UHFFFAOYSA-N 0.000 claims description 3
- WKSZMTYLSCHZID-UHFFFAOYSA-N NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C(C)(F)F Chemical compound NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C(C)(F)F WKSZMTYLSCHZID-UHFFFAOYSA-N 0.000 claims description 3
- MVPGLWBEKNSVHN-UHFFFAOYSA-N OCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl Chemical compound OCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl MVPGLWBEKNSVHN-UHFFFAOYSA-N 0.000 claims description 3
- HRJGAGOKRFPCOH-UHFFFAOYSA-N OCCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl Chemical compound OCCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl HRJGAGOKRFPCOH-UHFFFAOYSA-N 0.000 claims description 3
- JOCVQBDURVHERC-UHFFFAOYSA-N OCCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)S(=O)(=O)C Chemical compound OCCC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC=C1)S(=O)(=O)C JOCVQBDURVHERC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- AQLRWJVRJUSCJS-UHFFFAOYSA-N 1-[[1-(4-chlorophenyl)triazol-4-yl]methyl]-3,5-dimethyl-1,2,4-triazole Chemical compound N1=C(C)N=C(C)N1CC1=CN(C=2C=CC(Cl)=CC=2)N=N1 AQLRWJVRJUSCJS-UHFFFAOYSA-N 0.000 claims description 2
- 150000000659 7-membered carbocyclic compounds Chemical class 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000019901 Anxiety 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
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- NNARYJXWYNWMSY-UHFFFAOYSA-N C(C)(C)(C)C1=NC=NN1CC=1N=NN(C=1)C1=CC=C(C=C1)Cl Chemical compound C(C)(C)(C)C1=NC=NN1CC=1N=NN(C=1)C1=CC=C(C=C1)Cl NNARYJXWYNWMSY-UHFFFAOYSA-N 0.000 claims description 2
- WTTBNWBKWZDRPV-UHFFFAOYSA-N C(C)(C)(C)C1=NN(C=N1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl Chemical compound C(C)(C)(C)C1=NN(C=N1)CC=1N=NN(C=1)C1=CC=C(C=C1)Cl WTTBNWBKWZDRPV-UHFFFAOYSA-N 0.000 claims description 2
- KTZHEMRJQDFTCV-UHFFFAOYSA-N CC1=NN(C(=N1)C)CC=1N=NN(C=1)C1=CC=CC=C1 Chemical compound CC1=NN(C(=N1)C)CC=1N=NN(C=1)C1=CC=CC=C1 KTZHEMRJQDFTCV-UHFFFAOYSA-N 0.000 claims description 2
- FTODECXLANNKPC-UHFFFAOYSA-N CS(=O)(=O)C=1C=C(C=CC=1)N1N=NC(=C1)CN1C(=NC=C1)C Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)N1N=NC(=C1)CN1C(=NC=C1)C FTODECXLANNKPC-UHFFFAOYSA-N 0.000 claims description 2
- KOJCWZJFTKOHIH-UHFFFAOYSA-N ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCF)C Chemical compound ClC1=C(C=C(C=C1)N1N=NC(=C1)CN1C(=NC=C1)CCF)C KOJCWZJFTKOHIH-UHFFFAOYSA-N 0.000 claims description 2
- LMZPNUTXBLCHOF-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NN=C1)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1C(=NN=C1)C LMZPNUTXBLCHOF-UHFFFAOYSA-N 0.000 claims description 2
- TXAHJZVCNFFEJR-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C TXAHJZVCNFFEJR-UHFFFAOYSA-N 0.000 claims description 2
- PWVKLWNAGDSQLN-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C(C)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C(C)C PWVKLWNAGDSQLN-UHFFFAOYSA-N 0.000 claims description 2
- CAIRHTFTLPIFQU-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C(F)(F)F Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C(F)(F)F CAIRHTFTLPIFQU-UHFFFAOYSA-N 0.000 claims description 2
- FYLLXYYSVQPAKZ-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C1CC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C1CC1 FYLLXYYSVQPAKZ-UHFFFAOYSA-N 0.000 claims description 2
- CWHJIHOWGGKGEA-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C1CCC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C1CCC1 CWHJIHOWGGKGEA-UHFFFAOYSA-N 0.000 claims description 2
- AQRMSNKJMMOWNY-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C1CCCC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)C1CCCC1 AQRMSNKJMMOWNY-UHFFFAOYSA-N 0.000 claims description 2
- HRQZQCFVMLFYSB-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)CC Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)CC HRQZQCFVMLFYSB-UHFFFAOYSA-N 0.000 claims description 2
- RZCIDOWEQOSVFU-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)CCC Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1)CCC RZCIDOWEQOSVFU-UHFFFAOYSA-N 0.000 claims description 2
- BGVIDOSBQYMVSL-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1C)C1CCC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1C)C1CCC1 BGVIDOSBQYMVSL-UHFFFAOYSA-N 0.000 claims description 2
- KTERBHGAOPMQME-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1C1CCC1)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=C(N=C1C1CCC1)C KTERBHGAOPMQME-UHFFFAOYSA-N 0.000 claims description 2
- AMYCLBLRVRIJGO-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C AMYCLBLRVRIJGO-UHFFFAOYSA-N 0.000 claims description 2
- DSHSWXIKZMKFMX-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C(C)C Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C(C)C DSHSWXIKZMKFMX-UHFFFAOYSA-N 0.000 claims description 2
- OETSVHHBHCIQTP-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C1CC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C1CC1 OETSVHHBHCIQTP-UHFFFAOYSA-N 0.000 claims description 2
- QKBPERVPIARHRO-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C1CCC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C1CCC1 QKBPERVPIARHRO-UHFFFAOYSA-N 0.000 claims description 2
- FDBRNTUVWGVIAY-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C1CCCC1 Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1C1CCCC1 FDBRNTUVWGVIAY-UHFFFAOYSA-N 0.000 claims description 2
- VKYQAXYBRHJTAL-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1CC Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1CC VKYQAXYBRHJTAL-UHFFFAOYSA-N 0.000 claims description 2
- IWNKFQATMQELSV-UHFFFAOYSA-N ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1CCC Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1)CN1N=CN=C1CCC IWNKFQATMQELSV-UHFFFAOYSA-N 0.000 claims description 2
- NBDNSJRTVZQEOU-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC2=C1C=CC=C2)C Chemical compound ClC=1C=C(C=CC=1Cl)N1N=NC(=C1)CN1C(=NC2=C1C=CC=C2)C NBDNSJRTVZQEOU-UHFFFAOYSA-N 0.000 claims description 2
- OMQQLDITRYIEHZ-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)N1N=NC(=C1)CC=1N(N=CC=1)C Chemical compound ClC=1C=C(C=CC=1F)N1N=NC(=C1)CC=1N(N=CC=1)C OMQQLDITRYIEHZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000028698 Cognitive impairment Diseases 0.000 claims description 2
- 206010010904 Convulsion Diseases 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- 208000012661 Dyskinesia Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000027776 Extrapyramidal disease Diseases 0.000 claims description 2
- 206010019196 Head injury Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000020358 Learning disease Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000019022 Mood disease Diseases 0.000 claims description 2
- 208000016285 Movement disease Diseases 0.000 claims description 2
- SRQPKXBAGJDKMJ-UHFFFAOYSA-N NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)C(F)F)F Chemical compound NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)C(F)F)F SRQPKXBAGJDKMJ-UHFFFAOYSA-N 0.000 claims description 2
- XNKTWVPPPLRTKJ-UHFFFAOYSA-N NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC(=C1)C(F)F)F Chemical compound NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=CC(=C1)C(F)F)F XNKTWVPPPLRTKJ-UHFFFAOYSA-N 0.000 claims description 2
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 claims description 2
- 208000012902 Nervous system disease Diseases 0.000 claims description 2
- UXSIIBKTGUUEGS-UHFFFAOYSA-N OCC1=NC(=NN1CC=1N=NN(C=1)C1=CC=CC=C1)C Chemical compound OCC1=NC(=NN1CC=1N=NN(C=1)C1=CC=CC=C1)C UXSIIBKTGUUEGS-UHFFFAOYSA-N 0.000 claims description 2
- BJVGWMGSBBDWKY-UHFFFAOYSA-N OCC1=NN(C(=N1)C)CC=1N=NN(C=1)C1=CC=CC=C1 Chemical compound OCC1=NN(C(=N1)C)CC=1N=NN(C=1)C1=CC=CC=C1 BJVGWMGSBBDWKY-UHFFFAOYSA-N 0.000 claims description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000037581 Persistent Infection Diseases 0.000 claims description 2
- 201000009916 Postpartum depression Diseases 0.000 claims description 2
- 208000027520 Somatoform disease Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 208000029560 autism spectrum disease Diseases 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 208000018300 basal ganglia disease Diseases 0.000 claims description 2
- 230000003542 behavioural effect Effects 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 206010014599 encephalitis Diseases 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 201000003723 learning disability Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 230000000626 neurodegenerative effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000012672 seasonal affective disease Diseases 0.000 claims description 2
- 208000020431 spinal cord injury Diseases 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000013403 hyperactivity Diseases 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- YUDVHEROTXDJBH-UHFFFAOYSA-N C1(CCC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl Chemical compound C1(CCC1)C=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)Cl)Cl YUDVHEROTXDJBH-UHFFFAOYSA-N 0.000 claims 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims 1
- UZRIQFGTVHJEPZ-UHFFFAOYSA-N NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C(F)F Chemical compound NC=1N(C=CN=1)CC=1N=NN(C=1)C1=CC(=C(C=C1)F)C(F)F UZRIQFGTVHJEPZ-UHFFFAOYSA-N 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 6
- JRLJHLTZFBRDJM-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)triazole Chemical compound C1=C(Cl)C(Cl)=CC=C1N1N=NC=C1 JRLJHLTZFBRDJM-UHFFFAOYSA-N 0.000 description 1
- XCUYCJFGWDLGRI-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CC1=NNC=C1)F Chemical compound FC(C=1C=C(C=CC=1F)N1N=NC(=C1)CC1=NNC=C1)F XCUYCJFGWDLGRI-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462037831P | 2014-08-15 | 2014-08-15 | |
| US62/037,831 | 2014-08-15 | ||
| US201562146656P | 2015-04-13 | 2015-04-13 | |
| US62/146,656 | 2015-04-13 | ||
| PCT/US2015/045412 WO2016025917A1 (en) | 2014-08-15 | 2015-08-14 | Triazoles as nr2b receptor inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017524019A JP2017524019A (ja) | 2017-08-24 |
| JP2017524019A5 true JP2017524019A5 (enExample) | 2018-09-20 |
| JP6605020B2 JP6605020B2 (ja) | 2019-11-13 |
Family
ID=54266608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017508504A Active JP6605020B2 (ja) | 2014-08-15 | 2015-08-14 | Ｎｒ２ｂ受容体阻害剤としてのトリアゾール |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9981950B2 (enExample) |
| EP (1) | EP3180329B1 (enExample) |
| JP (1) | JP6605020B2 (enExample) |
| DK (1) | DK3180329T3 (enExample) |
| ES (1) | ES2791186T3 (enExample) |
| HU (1) | HUE049277T2 (enExample) |
| PL (1) | PL3180329T3 (enExample) |
| PT (1) | PT3180329T (enExample) |
| WO (1) | WO2016025917A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2791186T3 (es) | 2014-08-15 | 2020-11-03 | Janssen Pharmaceuticals Inc | Triazoles como inhibidores de receptores NR2B |
| USRE49517E1 (en) | 2014-08-15 | 2023-05-02 | Janssen Pharmaceuticals, Inc. | Pyrazoles |
| SMT202000134T1 (it) | 2015-07-09 | 2020-05-08 | Janssen Pharmaceutica Nv | 4-azaindoli sostituiti e loro uso come modulatori del recettore glun2b |
| KR20180108822A (ko) | 2016-02-10 | 2018-10-04 | 얀센 파마슈티카 엔.브이. | Nr2b-선택적 nmda 조절제로서 치환된 1,2,3-트라이아졸 |
| TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之１Ｈ－咪唑並［４，５－ｂ］吡啶－２（３Ｈ）－酮及其作為ＧＬＵＮ２Ｂ受體調節劑之用途 |
| WO2018111008A1 (ko) * | 2016-12-14 | 2018-06-21 | 에스케이바이오팜 주식회사 | 양극성 장애의 예방, 경감 또는 치료를 위한 카바메이트 화합물의 용도 |
| MA52244A (fr) | 2018-04-04 | 2021-02-17 | Janssen Pharmaceutica Nv | Pyridine et pyrimidines substituées et leur utilisation en tant que modulateurs du récepteur glun2b |
| MX2021015506A (es) | 2019-06-14 | 2022-02-10 | Janssen Pharmaceutica Nv | Amidas de pirazolo-piridina sustituidas y su uso como moduladores del receptor glun2b. |
| JP7667097B2 (ja) | 2019-06-14 | 2025-04-22 | ヤンセン ファーマシューティカ エヌ．ベー． | 置換ピラゾロ－ピリジンアミド及びｇｌｕｎ２ｂ受容体調節因子としてのその使用 |
| BR112021025136A2 (pt) | 2019-06-14 | 2022-01-25 | Janssen Pharmaceutica Nv | Pirazolo[4,3-b]piridinas substituídas e seu uso como moduladoras do receptor de glun2b |
| MX2021015508A (es) | 2019-06-14 | 2022-01-31 | Janssen Pharmaceutica Nv | Carbamatos de piridina y su uso como moduladores del receptor glun2b. |
| EP3983072A1 (en) | 2019-06-14 | 2022-04-20 | Janssen Pharmaceutica NV | Pyrazine carbamates and their use as glun2b receptor modulators |
| US11993587B2 (en) | 2019-06-14 | 2024-05-28 | Janssen Pharmaceutica Nv | Substituted pyrazolo-pyrazines and their use as GluN2B receptor modulators |
| PE20220806A1 (es) | 2019-06-14 | 2022-05-20 | Janssen Pharmaceutica Nv | Pirazolo piridinas heteroaromaticas sustituidas y su uso como moduladores del receptor glun2b |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6610723B2 (en) * | 2001-01-29 | 2003-08-26 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| AU2003214412A1 (en) | 2002-03-28 | 2003-10-13 | Eisai R & D Management Co., Ltd. | 7-azaindoles as inhibitors of c-jun n-terminal kinases for the treatment of neurodegenerative disorders |
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| JP2007523178A (ja) | 2004-02-18 | 2007-08-16 | アストラゼネカ アクチボラグ | 代謝型グルタメート受容体アンタゴニストとしてのトリアゾール化合物およびそれらの使用 |
| US7807704B2 (en) | 2006-03-30 | 2010-10-05 | Chemocentryx, Inc. | Bicyclic, nitrogen-containing compounds modulating CXCR4 and/or CCXCKR2 |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| NZ581127A (en) | 2007-05-25 | 2012-06-29 | Abbott Gmbh & Co Kg | Heterocyclic compounds as positive modulators of metabotropic glutamate receptor 2 (mglu2 receptor) |
| US20100227846A1 (en) | 2007-08-30 | 2010-09-09 | Takeda Pharmaceutical Company Limited | Substituted pyrazole derivative |
| WO2009058261A1 (en) | 2007-10-31 | 2009-05-07 | Merck & Co., Inc. | Modulation of sleep with nr2b receptor antagonists |
| MX2010009649A (es) * | 2008-03-27 | 2010-12-17 | Evotecv Neurosciences Gmbh | Metodos para tratar trastornos utilizando un antagonista selectivo del subtipo nr2b de nmda. |
| NZ590688A (en) | 2008-08-05 | 2012-09-28 | Daiichi Sankyo Co Ltd | imidazo[4,5-b]pyridin-2-one derivatives |
| US9643922B2 (en) * | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| US8697689B2 (en) | 2008-10-16 | 2014-04-15 | Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| CN102264743B (zh) | 2008-11-25 | 2015-02-11 | 罗彻斯特大学 | Mlk抑制剂及其使用方法 |
| EP2408753A4 (en) * | 2009-03-20 | 2012-11-07 | Univ Brandeis | COMPOUNDS AND METHOD FOR THE TREATMENT OF MICROBIAL STOMACH DARM INFECTIONS IN MAMMALS |
| WO2011156245A2 (en) | 2010-06-09 | 2011-12-15 | Merck Sharp & Dohme Corp. | Positive allosteric modulators of mglur2 |
| US9434743B2 (en) | 2012-03-02 | 2016-09-06 | Takeda Pharmaceutical Company Limited | Indazole derivatives |
| WO2014124651A1 (en) | 2013-02-15 | 2014-08-21 | Københavns Universitet | Pyrrolidine-2-carboxylic acid derivatives as iglur antagonists |
| JP2016516710A (ja) | 2013-03-13 | 2016-06-09 | アッヴィ・インコーポレイテッド | ピリジン系ｃｄｋ９キナーゼ阻害薬 |
| USRE49517E1 (en) | 2014-08-15 | 2023-05-02 | Janssen Pharmaceuticals, Inc. | Pyrazoles |
| ES2791186T3 (es) | 2014-08-15 | 2020-11-03 | Janssen Pharmaceuticals Inc | Triazoles como inhibidores de receptores NR2B |
| SMT202000134T1 (it) | 2015-07-09 | 2020-05-08 | Janssen Pharmaceutica Nv | 4-azaindoli sostituiti e loro uso come modulatori del recettore glun2b |
| KR20180108822A (ko) | 2016-02-10 | 2018-10-04 | 얀센 파마슈티카 엔.브이. | Nr2b-선택적 nmda 조절제로서 치환된 1,2,3-트라이아졸 |
| TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之１Ｈ－咪唑並［４，５－ｂ］吡啶－２（３Ｈ）－酮及其作為ＧＬＵＮ２Ｂ受體調節劑之用途 |
-
2015
- 2015-08-14 ES ES15777754T patent/ES2791186T3/es active Active
- 2015-08-14 JP JP2017508504A patent/JP6605020B2/ja active Active
- 2015-08-14 PL PL15777754T patent/PL3180329T3/pl unknown
- 2015-08-14 WO PCT/US2015/045412 patent/WO2016025917A1/en not_active Ceased
- 2015-08-14 DK DK15777754.1T patent/DK3180329T3/da active
- 2015-08-14 PT PT157777541T patent/PT3180329T/pt unknown
- 2015-08-14 HU HUE15777754A patent/HUE049277T2/hu unknown
- 2015-08-14 EP EP15777754.1A patent/EP3180329B1/en active Active
- 2015-08-14 US US15/503,864 patent/US9981950B2/en active Active
-
2018
- 2018-04-27 US US15/964,794 patent/US10323021B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017524019A5 (enExample) | ||
| JP2017525700A5 (enExample) | ||
| RU2017116197A (ru) | 2-амино-3,5-дифтор-3,6-диметил-6-фенил-3,4,5,6-тетрагидропиридины как ингибиторы васе1 для лечения болезни альцгеймера | |
| JP5667684B2 (ja) | 関節炎の治療方法 | |
| JP2014517050A5 (enExample) | ||
| JP2014502641A5 (enExample) | ||
| JP2017528504A5 (enExample) | ||
| RU2017120217A (ru) | 2-амино-5,5-дифтор-6-(фторметил)-6-фенил-3,4,5,6-тетрагидпропиридины в качестве ингибиторов bace1 | |
| RU2017116598A (ru) | Соединения и композиции для модуляции киназной активности мутантов egfr | |
| RU2013130222A (ru) | Применение сигма-лигандов от боли при раке костей | |
| JP2008531714A (ja) | 不安障害の治療用及び／又は予防用の医薬組成物 | |
| JP2018502906A5 (enExample) | ||
| JP2017506237A5 (enExample) | ||
| JP2008546751A5 (enExample) | ||
| RU2017116196A (ru) | 2-амино-6-(дифторметил)-5,5-дифтор-6-фенил-3,4,5,6-тетрагидропиридины как ингибиторы васе1 | |
| RU2013156367A (ru) | Применение сигма-лигандов при боли, связанной с диабетом 2 типа | |
| MX2023001468A (es) | Tratamiento de cancer de prostata. | |
| JP2019534310A5 (enExample) | ||
| RU2015116816A (ru) | Производное имидазола | |
| RU2016102149A (ru) | Применение сигма-лигандов для предотвращения и лечения боли, связанной с интерстициальным циститом/синдромом раздраженного мочевого пузыря (иц/срмп) | |
| SI2855449T1 (en) | SULFONYL PIPERIDIN DERIVATIVES AND THEIR USE IN TREATMENT OF PROKINETICINAL DISEASE DISEASES | |
| JP2013529206A5 (enExample) | ||
| RU2019123319A (ru) | Пиразолопиримидины и способы их применения | |
| JP2016523276A5 (enExample) | ||
| JP2017502063A5 (enExample) |