JP2017525700A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017525700A5 JP2017525700A5 JP2017508553A JP2017508553A JP2017525700A5 JP 2017525700 A5 JP2017525700 A5 JP 2017525700A5 JP 2017508553 A JP2017508553 A JP 2017508553A JP 2017508553 A JP2017508553 A JP 2017508553A JP 2017525700 A5 JP2017525700 A5 JP 2017525700A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazole
- pyrazol
- phenyl
- halo
- 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 113
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- -1 polymorph Chemical class 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 24
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 21
- 150000001204 N-oxides Chemical class 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 108010054200 NR2B NMDA receptor Proteins 0.000 claims description 6
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 6
- 208000024714 major depressive disease Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 208000020925 Bipolar disease Diseases 0.000 claims description 3
- GPZNPXAPAFLRLB-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1)C(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1)C(F)F GPZNPXAPAFLRLB-UHFFFAOYSA-N 0.000 claims description 3
- WXIFVEVHNGMUHP-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1)OC(F)F WXIFVEVHNGMUHP-UHFFFAOYSA-N 0.000 claims description 3
- TYWLMLPPMXWFPX-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NN(C=1)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NN(C=1)C)OC(F)F TYWLMLPPMXWFPX-UHFFFAOYSA-N 0.000 claims description 3
- WQIJWPZIOIFLHO-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NNC=1)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NNC=1)OC(F)F WQIJWPZIOIFLHO-UHFFFAOYSA-N 0.000 claims description 3
- PLNFUYPBLOEXJI-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NNC=1C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NNC=1C)OC(F)F PLNFUYPBLOEXJI-UHFFFAOYSA-N 0.000 claims description 3
- IZRNPSABLKZTLN-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NNC=1CC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1C=NNC=1CC)OC(F)F IZRNPSABLKZTLN-UHFFFAOYSA-N 0.000 claims description 3
- BHOUUDZNGWHFHC-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1N(N=CC=1)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC=1N(N=CC=1)C)OC(F)F BHOUUDZNGWHFHC-UHFFFAOYSA-N 0.000 claims description 3
- RQQJZPUPHSLLRR-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1 Chemical compound FC(C)(F)C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1 RQQJZPUPHSLLRR-UHFFFAOYSA-N 0.000 claims description 3
- SBFDBMKEWKLRSB-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F SBFDBMKEWKLRSB-UHFFFAOYSA-N 0.000 claims description 3
- LHMLJRCNGQZNHL-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F LHMLJRCNGQZNHL-UHFFFAOYSA-N 0.000 claims description 3
- 208000019022 Mood disease Diseases 0.000 claims description 3
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
- 150000000659 7-membered carbocyclic compounds Chemical class 0.000 claims description 2
- ISRPGJCSMGGLSW-UHFFFAOYSA-N BrC1=CC=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound BrC1=CC=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C ISRPGJCSMGGLSW-UHFFFAOYSA-N 0.000 claims description 2
- YZCWRAFJWAFRHN-UHFFFAOYSA-N BrC1=CC=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C Chemical compound BrC1=CC=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C YZCWRAFJWAFRHN-UHFFFAOYSA-N 0.000 claims description 2
- ANQAUDCJANAJOF-UHFFFAOYSA-N BrC=1C=C(C=CC=1)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound BrC=1C=C(C=CC=1)C=1C=NN(C=1)CC1=CC(=NN1C)C ANQAUDCJANAJOF-UHFFFAOYSA-N 0.000 claims description 2
- TWITWMGSBLVJJS-UHFFFAOYSA-N BrC=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NN(C=C1)C Chemical compound BrC=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NN(C=C1)C TWITWMGSBLVJJS-UHFFFAOYSA-N 0.000 claims description 2
- NHIDZRFOLGDIRM-UHFFFAOYSA-N CN1N=C(C=C1)CN1N=CC(=C1)C1=CC(=CC=C1)C(F)(F)F Chemical compound CN1N=C(C=C1)CN1N=CC(=C1)C1=CC(=CC=C1)C(F)(F)F NHIDZRFOLGDIRM-UHFFFAOYSA-N 0.000 claims description 2
- CPBUZCHPDATVEU-UHFFFAOYSA-N CN1N=C(C=C1)CN1N=CC(=C1)C1=CC(=CC=C1)OC(F)(F)F Chemical compound CN1N=C(C=C1)CN1N=CC(=C1)C1=CC(=CC=C1)OC(F)(F)F CPBUZCHPDATVEU-UHFFFAOYSA-N 0.000 claims description 2
- MYVGSZBCKCBYMQ-UHFFFAOYSA-N CN1N=C(C=C1)CN1N=CC(=C1)C1=NC=CC=C1 Chemical compound CN1N=C(C=C1)CN1N=CC(=C1)C1=NC=CC=C1 MYVGSZBCKCBYMQ-UHFFFAOYSA-N 0.000 claims description 2
- IOTYDSRQXWYEOM-UHFFFAOYSA-N CN1N=C(C=C1CN1N=CC(=C1)C1=CC(=CC=C1)OC(F)(F)F)C Chemical compound CN1N=C(C=C1CN1N=CC(=C1)C1=CC(=CC=C1)OC(F)(F)F)C IOTYDSRQXWYEOM-UHFFFAOYSA-N 0.000 claims description 2
- XYCBFPMJNPHKTB-UHFFFAOYSA-N CN1N=C(C=C1CN1N=CC(=C1)C1=CC=C(C=C1)C(F)(F)F)C Chemical compound CN1N=C(C=C1CN1N=CC(=C1)C1=CC=C(C=C1)C(F)(F)F)C XYCBFPMJNPHKTB-UHFFFAOYSA-N 0.000 claims description 2
- TXJIMPPHALVHGH-UHFFFAOYSA-N CN1N=C(C=C1CN1N=CC(=C1)C1=CC=CC=C1)C Chemical compound CN1N=C(C=C1CN1N=CC(=C1)C1=CC=CC=C1)C TXJIMPPHALVHGH-UHFFFAOYSA-N 0.000 claims description 2
- IVQOSXHMIKOTIP-UHFFFAOYSA-N CN1N=CC=C1CN1N=CC(=C1)C1=CC=CC=C1 Chemical compound CN1N=CC=C1CN1N=CC(=C1)C1=CC=CC=C1 IVQOSXHMIKOTIP-UHFFFAOYSA-N 0.000 claims description 2
- RNBFGQKOKMISQP-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1)C)OC(F)F RNBFGQKOKMISQP-UHFFFAOYSA-N 0.000 claims description 2
- CJTATZNAJJRQJR-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C(F)(F)F CJTATZNAJJRQJR-UHFFFAOYSA-N 0.000 claims description 2
- RTURIZKUGANKMN-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C(F)F RTURIZKUGANKMN-UHFFFAOYSA-N 0.000 claims description 2
- ZCZZFZFZUWEHRG-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)OC(F)F ZCZZFZFZUWEHRG-UHFFFAOYSA-N 0.000 claims description 2
- PWOOSCZWCWFZKZ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CN=CN1CC)C(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CN=CN1CC)C(F)F PWOOSCZWCWFZKZ-UHFFFAOYSA-N 0.000 claims description 2
- VCIYUUWUQVIFEO-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C(CC)CC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C(CC)CC)OC(F)F VCIYUUWUQVIFEO-UHFFFAOYSA-N 0.000 claims description 2
- FDYFJXNCCIBNPD-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C(F)(F)F FDYFJXNCCIBNPD-UHFFFAOYSA-N 0.000 claims description 2
- LVYDQZJCZSJMBO-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C(F)F LVYDQZJCZSJMBO-UHFFFAOYSA-N 0.000 claims description 2
- CRYKKCVVHRIZJU-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)OC(F)F CRYKKCVVHRIZJU-UHFFFAOYSA-N 0.000 claims description 2
- LRTTWINCSMBJMM-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C1CCCC1)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C1CCCC1)OC(F)F LRTTWINCSMBJMM-UHFFFAOYSA-N 0.000 claims description 2
- PCHBMVPVCPSMLD-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)CC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)CC)OC(F)F PCHBMVPVCPSMLD-UHFFFAOYSA-N 0.000 claims description 2
- PTYPZHOITALPCT-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC(=C1)CC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC(=C1)CC)OC(F)F PTYPZHOITALPCT-UHFFFAOYSA-N 0.000 claims description 2
- BQEMIVBQABRGAT-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC(=C1)CCC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC(=C1)CCC)OC(F)F BQEMIVBQABRGAT-UHFFFAOYSA-N 0.000 claims description 2
- FMPLJMMZEDLVOK-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C(=NNC=1C)C)C(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C(=NNC=1C)C)C(F)F FMPLJMMZEDLVOK-UHFFFAOYSA-N 0.000 claims description 2
- CRTYJRKVIQBRIW-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C(=NNC=1C)C)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C(=NNC=1C)C)OC(F)F CRTYJRKVIQBRIW-UHFFFAOYSA-N 0.000 claims description 2
- WXLDTHJZQFCOMH-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C=NN(C=1)CC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C=NN(C=1)CC)OC(F)F WXLDTHJZQFCOMH-UHFFFAOYSA-N 0.000 claims description 2
- OGSQOKYLXLIXRK-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C=NNC=1)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CCC=1C=NNC=1)OC(F)F OGSQOKYLXLIXRK-UHFFFAOYSA-N 0.000 claims description 2
- IBXQVTJYUTXWOZ-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C IBXQVTJYUTXWOZ-UHFFFAOYSA-N 0.000 claims description 2
- LBYWWSCGWDYKNX-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=CN=CN1CC Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=CN=CN1CC LBYWWSCGWDYKNX-UHFFFAOYSA-N 0.000 claims description 2
- WBSISSQHVCKNDV-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C WBSISSQHVCKNDV-UHFFFAOYSA-N 0.000 claims description 2
- ONBFZEJYXQDCRE-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1 Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1 ONBFZEJYXQDCRE-UHFFFAOYSA-N 0.000 claims description 2
- HXXKCCOYYFKOHT-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CC=1C=NN(C=1)C Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CC=1C=NN(C=1)C HXXKCCOYYFKOHT-UHFFFAOYSA-N 0.000 claims description 2
- OZKOQOLBOJMIRC-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CC=1N(N=CC=1)C Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CC=1N(N=CC=1)C OZKOQOLBOJMIRC-UHFFFAOYSA-N 0.000 claims description 2
- WQTXJFYTZBONCP-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CC=1N=C2N(C=CC=C2)C=1 Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CC=1N=C2N(C=CC=C2)C=1 WQTXJFYTZBONCP-UHFFFAOYSA-N 0.000 claims description 2
- FKNGDDYLLFMSCD-UHFFFAOYSA-N ClC1=CC=C(C=C1)C=1C=NN(C=1)CCC=1C(=NNC=1C)C Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1)CCC=1C(=NNC=1C)C FKNGDDYLLFMSCD-UHFFFAOYSA-N 0.000 claims description 2
- XXULOVVPELJMEY-UHFFFAOYSA-N ClC=1C=C(C=C(C=1)C(F)F)C=1C=NN(C=1)CC1=NNC=C1 Chemical compound ClC=1C=C(C=C(C=1)C(F)F)C=1C=NN(C=1)CC1=NNC=C1 XXULOVVPELJMEY-UHFFFAOYSA-N 0.000 claims description 2
- FDBPKEPRZDXSQA-UHFFFAOYSA-N ClC=1C=C(C=C(C=1)OC(F)F)C=1C=NN(C=1)CC1=NNC=C1 Chemical compound ClC=1C=C(C=C(C=1)OC(F)F)C=1C=NN(C=1)CC1=NNC=C1 FDBPKEPRZDXSQA-UHFFFAOYSA-N 0.000 claims description 2
- GUJNOPVPJRXDCB-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C=1C=NN(C=1)C=1N(N=CC=1)C Chemical compound ClC=1C=C(C=CC=1Cl)C=1C=NN(C=1)C=1N(N=CC=1)C GUJNOPVPJRXDCB-UHFFFAOYSA-N 0.000 claims description 2
- HRKHYYJXFPDNFI-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)C=1C=NN(C=1)C=1N(N=CC=1)C Chemical compound ClC=1C=C(C=CC=1F)C=1C=NN(C=1)C=1N(N=CC=1)C HRKHYYJXFPDNFI-UHFFFAOYSA-N 0.000 claims description 2
- YUBYOLBZTMVIAV-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1 Chemical compound FC(C)(F)C=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1 YUBYOLBZTMVIAV-UHFFFAOYSA-N 0.000 claims description 2
- DDNUGAKPXYMUKR-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NN(C=1)C Chemical compound FC(C)(F)C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NN(C=1)C DDNUGAKPXYMUKR-UHFFFAOYSA-N 0.000 claims description 2
- MVGNHQREGRFEQQ-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NNC=1CC Chemical compound FC(C)(F)C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NNC=1CC MVGNHQREGRFEQQ-UHFFFAOYSA-N 0.000 claims description 2
- BGEGEEMDZPHRBZ-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C1=NN(C=C1)CC1=NNC(=C1)CN1N=CC(=C1)C1=CC(=C(C=C1)F)C(F)F)F Chemical compound FC(C=1C=C(C=CC=1F)C1=NN(C=C1)CC1=NNC(=C1)CN1N=CC(=C1)C1=CC(=C(C=C1)F)C(F)F)F BGEGEEMDZPHRBZ-UHFFFAOYSA-N 0.000 claims description 2
- MACPRACNPYALGP-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=CC(=NN1)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=CC(=NN1)C)F MACPRACNPYALGP-UHFFFAOYSA-N 0.000 claims description 2
- SOTBKNXFRAXTAE-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=CC(=NN1C)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=CC(=NN1C)C)F SOTBKNXFRAXTAE-UHFFFAOYSA-N 0.000 claims description 2
- POUMWMHGHUZSLS-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NN(C=C1)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NN(C=C1)C)F POUMWMHGHUZSLS-UHFFFAOYSA-N 0.000 claims description 2
- GBHOKNOTTNNQTQ-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NN(C=C1)CC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NN(C=C1)CC)F GBHOKNOTTNNQTQ-UHFFFAOYSA-N 0.000 claims description 2
- RQYYUIGRZDLILP-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC(=C1)CCC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC(=C1)CCC)F RQYYUIGRZDLILP-UHFFFAOYSA-N 0.000 claims description 2
- TVHCUYDPYVKDHI-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1CC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1CC)F TVHCUYDPYVKDHI-UHFFFAOYSA-N 0.000 claims description 2
- PAPFAZHJWWEGNJ-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C(=NNC=1C)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C(=NNC=1C)C)F PAPFAZHJWWEGNJ-UHFFFAOYSA-N 0.000 claims description 2
- DOQIJLDPMKRTSR-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NN(C=1)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NN(C=1)C)F DOQIJLDPMKRTSR-UHFFFAOYSA-N 0.000 claims description 2
- DFRNAZVJXDTBSV-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NNC=1C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NNC=1C)F DFRNAZVJXDTBSV-UHFFFAOYSA-N 0.000 claims description 2
- WJDFZNSBELJCKM-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NNC=1CC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NNC=1CC)F WJDFZNSBELJCKM-UHFFFAOYSA-N 0.000 claims description 2
- QWQROZAMNURWBT-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1N(N=CC=1)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1N(N=CC=1)C)F QWQROZAMNURWBT-UHFFFAOYSA-N 0.000 claims description 2
- SKQPTLPPMSYEQN-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CCC=1C(=NNC=1C)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CCC=1C(=NNC=1C)C)F SKQPTLPPMSYEQN-UHFFFAOYSA-N 0.000 claims description 2
- JPDCMOOBLLIEFK-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CCC=1C=NNC=1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CCC=1C=NNC=1)F JPDCMOOBLLIEFK-UHFFFAOYSA-N 0.000 claims description 2
- CIMZHFATSQYFET-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1)F Chemical compound FC(OC=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1)F CIMZHFATSQYFET-UHFFFAOYSA-N 0.000 claims description 2
- MQKNJFNIYSGNHY-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1Cl)C=1C=NN(C=1)CC=1C(=NNC=1C)C)F Chemical compound FC(OC=1C=C(C=CC=1Cl)C=1C=NN(C=1)CC=1C(=NNC=1C)C)F MQKNJFNIYSGNHY-UHFFFAOYSA-N 0.000 claims description 2
- IOOCAJSDFZHJMM-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1CC)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1CC)F IOOCAJSDFZHJMM-UHFFFAOYSA-N 0.000 claims description 2
- WTJLEJBVIDJMFC-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NN(C=1)C)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC=1C=NN(C=1)C)F WTJLEJBVIDJMFC-UHFFFAOYSA-N 0.000 claims description 2
- KYGBERMNMHOSMC-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NN(C=1)CC1=CC(=NN1C)C KYGBERMNMHOSMC-UHFFFAOYSA-N 0.000 claims description 2
- FBYLDXMRENBYNM-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NN(C=1)CC1=NN(C=C1)C Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NN(C=1)CC1=NN(C=C1)C FBYLDXMRENBYNM-UHFFFAOYSA-N 0.000 claims description 2
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims description 2
- 230000000926 neurological effect Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 208000013403 hyperactivity Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims 1
- 125000004965 chloroalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- 208000026106 cerebrovascular disease Diseases 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 2
- ZPLZKFHQDARNJQ-UHFFFAOYSA-N 1-methyl-3-[(4-phenylpyrazol-1-yl)methyl]pyrazole Chemical compound CN1N=C(C=C1)CN1N=CC(=C1)C1=CC=CC=C1 ZPLZKFHQDARNJQ-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- WTIFREIJFMTPOT-UHFFFAOYSA-N C1(CC1)C=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1 Chemical compound C1(CC1)C=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1 WTIFREIJFMTPOT-UHFFFAOYSA-N 0.000 description 1
- XOPZVFQOFXIGRI-UHFFFAOYSA-N CN1N=C(C=C1)CN1N=CC(=C1)C1=CC=C(C=C1)C(F)(F)F Chemical compound CN1N=C(C=C1)CN1N=CC(=C1)C1=CC=C(C=C1)C(F)(F)F XOPZVFQOFXIGRI-UHFFFAOYSA-N 0.000 description 1
- CJDZRSVYGKAPJM-UHFFFAOYSA-N CN1N=C(C=C1CN1N=CC(=C1)C1=CC(=CC=C1)C(F)(F)F)C Chemical compound CN1N=C(C=C1CN1N=CC(=C1)C1=CC(=CC=C1)C(F)(F)F)C CJDZRSVYGKAPJM-UHFFFAOYSA-N 0.000 description 1
- WMUAUDVHENODTB-UHFFFAOYSA-N CN1N=CC(=C1)CN1N=CC(=C1)C1=CC(=CC=C1)S(=O)(=O)C Chemical compound CN1N=CC(=C1)CN1N=CC(=C1)C1=CC(=CC=C1)S(=O)(=O)C WMUAUDVHENODTB-UHFFFAOYSA-N 0.000 description 1
- RAFYHYBKKVGIIK-UHFFFAOYSA-N CS(=O)(=O)C=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1 Chemical compound CS(=O)(=O)C=1C=C(C=CC=1)C=1C=NN(C=1)CC1=NNC=C1 RAFYHYBKKVGIIK-UHFFFAOYSA-N 0.000 description 1
- NVPPRZHNQAGZNI-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C NVPPRZHNQAGZNI-UHFFFAOYSA-N 0.000 description 1
- XYGIAPGACDFNDM-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)F XYGIAPGACDFNDM-UHFFFAOYSA-N 0.000 description 1
- AENUUQTUDHOBSJ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C AENUUQTUDHOBSJ-UHFFFAOYSA-N 0.000 description 1
- PXLCOAZGYOBHBQ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)F Chemical compound ClC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)F PXLCOAZGYOBHBQ-UHFFFAOYSA-N 0.000 description 1
- DOLSUXNRMMOQGK-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound ClC1=C(C=CC(=C1)Cl)C=1C=NN(C=1)CC1=CC(=NN1C)C DOLSUXNRMMOQGK-UHFFFAOYSA-N 0.000 description 1
- WVXIDDGREBYPIF-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C=1C=NN(C=1)CC1=NN(C=C1)C Chemical compound ClC1=C(C=CC(=C1)Cl)C=1C=NN(C=1)CC1=NN(C=C1)C WVXIDDGREBYPIF-UHFFFAOYSA-N 0.000 description 1
- CYBVKIGZLGUYOT-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound ClC=1C=C(C=CC=1Cl)C=1C=NN(C=1)CC1=CC(=NN1C)C CYBVKIGZLGUYOT-UHFFFAOYSA-N 0.000 description 1
- MWFSWLFIGXOGQC-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C=1C=NN(C=1)CC1=NN(C=C1)C Chemical compound ClC=1C=C(C=CC=1Cl)C=1C=NN(C=1)CC1=NN(C=C1)C MWFSWLFIGXOGQC-UHFFFAOYSA-N 0.000 description 1
- DDHFRTPLOOOEAP-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound ClC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=CC(=NN1C)C DDHFRTPLOOOEAP-UHFFFAOYSA-N 0.000 description 1
- PVABBWISXQDWEN-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NN(C=C1)C Chemical compound ClC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NN(C=C1)C PVABBWISXQDWEN-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- BWVRPGYKZYASIH-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C Chemical compound FC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)C BWVRPGYKZYASIH-UHFFFAOYSA-N 0.000 description 1
- OPNJBKUMFOXMHL-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C Chemical compound FC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)C OPNJBKUMFOXMHL-UHFFFAOYSA-N 0.000 description 1
- JUIQWZMUESSJRP-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1)C Chemical compound FC1=C(C=C(C=C1)C=1C=NN(C=1)CC1=NNC=C1)C JUIQWZMUESSJRP-UHFFFAOYSA-N 0.000 description 1
- UYFOFEJPPDSOCE-UHFFFAOYSA-N FC1=CC(=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)OC Chemical compound FC1=CC(=C(C=C1)C=1C=NN(C=1)CC1=CC(=NN1C)C)OC UYFOFEJPPDSOCE-UHFFFAOYSA-N 0.000 description 1
- MSGIBHWJHGBUEJ-UHFFFAOYSA-N FC1=CC(=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)OC Chemical compound FC1=CC(=C(C=C1)C=1C=NN(C=1)CC1=NN(C=C1)C)OC MSGIBHWJHGBUEJ-UHFFFAOYSA-N 0.000 description 1
- FOMRZINSAAHONZ-UHFFFAOYSA-N FC=1C=C(C=CC=1C)C=1C=NN(C=1)CC1=CC(=NN1C)C Chemical compound FC=1C=C(C=CC=1C)C=1C=NN(C=1)CC1=CC(=NN1C)C FOMRZINSAAHONZ-UHFFFAOYSA-N 0.000 description 1
- KUEVFLYYENSXRM-UHFFFAOYSA-N FC=1C=C(C=CC=1C)C=1C=NN(C=1)CC1=CC=NN1C Chemical compound FC=1C=C(C=CC=1C)C=1C=NN(C=1)CC1=CC=NN1C KUEVFLYYENSXRM-UHFFFAOYSA-N 0.000 description 1
- MGNZNJFHDRDPLZ-UHFFFAOYSA-N FS(F)(F)(F)(F)C1=CC(=CC=C1)C1=CN(CC2=NNC=C2)N=C1 Chemical compound FS(F)(F)(F)(F)C1=CC(=CC=C1)C1=CN(CC2=NNC=C2)N=C1 MGNZNJFHDRDPLZ-UHFFFAOYSA-N 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000020358 Learning disease Diseases 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 201000009916 Postpartum depression Diseases 0.000 description 1
- 208000027520 Somatoform disease Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 208000029560 autism spectrum disease Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 201000003723 learning disability Diseases 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462037815P | 2014-08-15 | 2014-08-15 | |
| US62/037,815 | 2014-08-15 | ||
| US201562146629P | 2015-04-13 | 2015-04-13 | |
| US62/146,629 | 2015-04-13 | ||
| PCT/US2015/045413 WO2016025918A1 (en) | 2014-08-15 | 2015-08-14 | Pyrazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017525700A JP2017525700A (ja) | 2017-09-07 |
| JP2017525700A5 true JP2017525700A5 (enExample) | 2018-09-20 |
| JP6618525B2 JP6618525B2 (ja) | 2019-12-11 |
Family
ID=54261065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017508553A Active JP6618525B2 (ja) | 2014-08-15 | 2015-08-14 | ピラゾール類 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US10155727B2 (enExample) |
| EP (1) | EP3180315B1 (enExample) |
| JP (1) | JP6618525B2 (enExample) |
| DK (1) | DK3180315T3 (enExample) |
| ES (1) | ES2791252T3 (enExample) |
| HU (1) | HUE049278T2 (enExample) |
| PL (1) | PL3180315T3 (enExample) |
| PT (1) | PT3180315T (enExample) |
| WO (1) | WO2016025918A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9981950B2 (en) | 2014-08-15 | 2018-05-29 | Janssen Pharmaceuticals, Inc. | Triazoles as NR2B receptor inhibitors |
| BR112018000468A2 (pt) | 2015-07-09 | 2018-09-18 | Janssen Pharmaceutica Nv | 4-azaindóis substituídos e seu uso como moduladores do receptor de glun2b |
| MA44008A (fr) | 2016-02-10 | 2018-12-19 | Janssen Pharmaceutica Nv | 1,2,3-triazoles substitués utilisés comme modulateurs de nmda sélectifs de nr2b |
| US10487055B2 (en) | 2016-06-01 | 2019-11-26 | Rhode Island Board Of Education | Diindole compounds useful in treatment of nervous system disorders |
| 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 |
| EP3774732A4 (en) * | 2018-04-04 | 2022-02-09 | Janssen Pharmaceutica NV | PYRIDINE AND SUBSTITUTED PYRIMIDINES AND THEIR USE AS GLUN2B RECEPTOR MODULATORS |
| MX2021015511A (es) | 2019-06-14 | 2022-01-31 | Janssen Pharmaceutica Nv | Carbamatos de pirazina y sus usos como moduladores del receptor glun2b. |
| CR20210580A (es) | 2019-06-14 | 2022-01-31 | Janssen Pharmaceutica Nv | Amidas depirazol-piridina sustituidos y su uso como moduladores del receptor glun2b |
| JP2022536773A (ja) | 2019-06-14 | 2022-08-18 | ヤンセン ファーマシューティカ エヌ．ベー． | 置換ピラゾロピラジン及びｇｌｕｎ２ｂ受容体調節因子としてのそれらの使用 |
| EP3982958A1 (en) | 2019-06-14 | 2022-04-20 | Janssen Pharmaceutica NV | Substituted heteroaromatic pyrazolo-pyridines and their use as glun2b receptor modulators |
| BR112021025132A2 (pt) | 2019-06-14 | 2022-01-25 | Janssen Pharmaceutica Nv | Carbamatos de piridina e seu uso como moduladores do receptor glun2b |
| PH12021552839A1 (en) | 2019-06-14 | 2022-10-03 | Janssen Pharmaceutica Nv | Substituted pyrazolo-pyridine amides and their use as glun2b receptor modulators |
| CN113993583A (zh) | 2019-06-14 | 2022-01-28 | 詹森药业有限公司 | 取代的吡唑并[4,3-b]吡啶及其作为GLUN2B受体调节剂的用途 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6610723B2 (en) | 2001-01-29 | 2003-08-26 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| KR20040111445A (ko) | 2002-03-28 | 2004-12-31 | 에자이 가부시키가이샤 | 신경퇴행성 질환 치료용 ｃ─Ｊｕｎ Ｎ─말단 키나아제억제제로서의 ７─아자인돌 |
| EP1720860A1 (en) | 2004-02-18 | 2006-11-15 | AstraZeneca AB | Triazole compounds and their use as metabotropic glutamate receptor antagonists |
| US20080269286A1 (en) | 2005-12-07 | 2008-10-30 | Clas Sonesson | Disubstituted Phenylpiperidines as Modulators of Cortical Catecholaminergic Neurotransmission |
| 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 |
| US9242933B2 (en) | 2007-05-25 | 2016-01-26 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds as positive modulators of metabotropic glutamate receptor 2 (mGlu2 receptor) |
| AR068813A1 (es) | 2007-08-30 | 2009-12-09 | Takeda Pharmaceutical | Derivados de pirazol sustituidos como antagonistas del receptor de androgenos (ar), un agente farmaceutico que los comprende y su uso en el tratamiento del cancer de prostata |
| EP2215073A4 (en) | 2007-10-31 | 2011-04-06 | Merck Sharp & Dohme | SLEEP MODULATION 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. |
| WO2009137338A1 (en) | 2008-05-06 | 2009-11-12 | Boehringer Ingelheim International Gmbh | Pyrazole compounds as ccr1 antagonists |
| NZ590688A (en) | 2008-08-05 | 2012-09-28 | Daiichi Sankyo Co Ltd | imidazo[4,5-b]pyridin-2-one derivatives |
| AU2009304293B2 (en) | 2008-10-16 | 2012-04-26 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| AU2009324894B2 (en) | 2008-11-25 | 2015-04-09 | University Of Rochester | MLK inhibitors and methods of use |
| JP2013523884A (ja) | 2010-04-14 | 2013-06-17 | アレイ バイオファーマ、インコーポレイテッド | ＪＡＫキナーゼの阻害剤としての５，７置換イミダゾ［１，２−ｃ］ピリミジン |
| 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 |
| TW201444820A (zh) | 2013-03-13 | 2014-12-01 | Abbvie Inc | 吡啶ｃｄｋ９激酶抑制劑 |
| US9981950B2 (en) | 2014-08-15 | 2018-05-29 | Janssen Pharmaceuticals, Inc. | Triazoles as NR2B receptor inhibitors |
| BR112018000468A2 (pt) | 2015-07-09 | 2018-09-18 | Janssen Pharmaceutica Nv | 4-azaindóis substituídos e seu uso como moduladores do receptor de glun2b |
| MA44008A (fr) | 2016-02-10 | 2018-12-19 | Janssen Pharmaceutica Nv | 1,2,3-triazoles substitués utilisés comme modulateurs de nmda sélectifs de nr2b |
| 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 WO PCT/US2015/045413 patent/WO2016025918A1/en not_active Ceased
- 2015-08-14 PL PL15775837T patent/PL3180315T3/pl unknown
- 2015-08-14 JP JP2017508553A patent/JP6618525B2/ja active Active
- 2015-08-14 HU HUE15775837A patent/HUE049278T2/hu unknown
- 2015-08-14 ES ES15775837T patent/ES2791252T3/es active Active
- 2015-08-14 US US15/503,875 patent/US10155727B2/en not_active Ceased
- 2015-08-14 US US17/124,879 patent/USRE49517E1/en active Active
- 2015-08-14 PT PT157758376T patent/PT3180315T/pt unknown
- 2015-08-14 EP EP15775837.6A patent/EP3180315B1/en active Active
- 2015-08-14 DK DK15775837.6T patent/DK3180315T3/da active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017524019A5 (enExample) | ||
| DK2531191T3 (en) | Sigma ligands for use in the prevention and / or treatment of post-operative pain | |
| RU2013130222A (ru) | Применение сигма-лигандов от боли при раке костей | |
| JP2014501732A5 (enExample) | ||
| IL263511A (en) | 1h-pyrazolo[4,3-b]pyridines as pde1 inhibitors | |
| JP2016519156A5 (enExample) | ||
| SI2855449T1 (en) | SULFONYL PIPERIDIN DERIVATIVES AND THEIR USE IN TREATMENT OF PROKINETICINAL DISEASE DISEASES | |
| RU2019123319A (ru) | Пиразолопиримидины и способы их применения | |
| JP2016530322A5 (enExample) | ||
| RU2016102149A (ru) | Применение сигма-лигандов для предотвращения и лечения боли, связанной с интерстициальным циститом/синдромом раздраженного мочевого пузыря (иц/срмп) | |
| JP2017528504A5 (enExample) | ||
| RU2017114355A (ru) | Производные нафтиридина в качестве антагонистов альфа v бета 6 интегрина для лечения, в частности, фиброзных заболеваний | |
| JP6618525B2 (ja) | ピラゾール類 | |
| CA2521201A1 (en) | Substituted pyrazoles for use in the prophylaxis or treatment of a disease which can be influenced by the binding of the substitued pyrazoles to 5ht receptors | |
| SI2638031T1 (en) | Pyrazole aminopyrimidine derivatives as LRRK2 modulators | |
| RU2018130547A (ru) | Производные пиразоло[1,5-а]пиразин-4-ила в качестве jак-ингибиторов | |
| JP2012516890A5 (enExample) | ||
| EA009732B1 (ru) | Диарильные и арилгетероарильные производные мочевины в качестве модуляторов 5-ht-рецептора серотонина, пригодные для профилактики и лечения связанных с ним заболеваний | |
| JP2011518801A (ja) | Ｎｋ３アンタゴニストとしてのイソキノリン誘導体 | |
| JP2013532709A5 (enExample) | ||
| RU2001106644A (ru) | Применение производных арил (или гетероарил) азолилкарбинолов в приготовлении лекарственного средства для лечения нарушений, опосредованных избытком вещества p | |
| WO2011147910A1 (en) | Pyrazole compounds as sigma receptor inhibitors | |
| RU2017120217A (ru) | 2-амино-5,5-дифтор-6-(фторметил)-6-фенил-3,4,5,6-тетрагидпропиридины в качестве ингибиторов bace1 | |
| JP2022536174A5 (enExample) | ||
| JP2017528506A5 (enExample) |