JPWO2020249791A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2020249791A5 JPWO2020249791A5 JP2021573717A JP2021573717A JPWO2020249791A5 JP WO2020249791 A5 JPWO2020249791 A5 JP WO2020249791A5 JP 2021573717 A JP2021573717 A JP 2021573717A JP 2021573717 A JP2021573717 A JP 2021573717A JP WO2020249791 A5 JPWO2020249791 A5 JP WO2020249791A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- phenyl
- pyridin
- methyl
- fluoro
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 33
- 150000001204 N-oxides Chemical class 0.000 description 32
- 239000012453 solvate Substances 0.000 description 31
- 230000000155 isotopic effect Effects 0.000 description 29
- -1 3-(difluoromethyl)phenyl Chemical group 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 27
- 208000035475 disorder Diseases 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 201000010099 disease Diseases 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 15
- 125000001475 halogen functional group Chemical group 0.000 description 15
- 108010054200 NR2B NMDA receptor Proteins 0.000 description 14
- 230000001404 mediated effect Effects 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 6
- 125000003566 oxetanyl group Chemical group 0.000 description 6
- 208000020925 Bipolar disease Diseases 0.000 description 5
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 description 5
- 208000024714 major depressive disease Diseases 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- 208000019022 Mood disease Diseases 0.000 description 3
- 206010015037 epilepsy Diseases 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
- 206010003805 Autism Diseases 0.000 description 2
- 208000020706 Autistic disease Diseases 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 2
- SYSUPFRXXQKIIG-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O SYSUPFRXXQKIIG-UHFFFAOYSA-N 0.000 description 2
- MSIPANRJKLKGLT-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O MSIPANRJKLKGLT-UHFFFAOYSA-N 0.000 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 description 2
- 208000028698 Cognitive impairment Diseases 0.000 description 2
- 208000012661 Dyskinesia Diseases 0.000 description 2
- UTLVLFRRQFRZGE-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(C)=O)F UTLVLFRRQFRZGE-UHFFFAOYSA-N 0.000 description 2
- FSYHIYSKOOXFCK-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)F FSYHIYSKOOXFCK-UHFFFAOYSA-N 0.000 description 2
- SZCRYWADIHNAQD-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)CC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)CC)F SZCRYWADIHNAQD-UHFFFAOYSA-N 0.000 description 2
- BBBHJMAWFLJLCO-GFCCVEGCSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CN(C(O1)=O)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CN(C(O1)=O)C)F BBBHJMAWFLJLCO-GFCCVEGCSA-N 0.000 description 2
- UWVUKDQGMGXDNN-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)F UWVUKDQGMGXDNN-UHFFFAOYSA-N 0.000 description 2
- QYYNKVYGLUDTQJ-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O QYYNKVYGLUDTQJ-UHFFFAOYSA-N 0.000 description 2
- 206010019196 Head injury Diseases 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- 208000020358 Learning disease Diseases 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 208000037581 Persistent Infection Diseases 0.000 description 2
- 201000009916 Postpartum depression Diseases 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 208000029560 autism spectrum disease Diseases 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 206010014599 encephalitis Diseases 0.000 description 2
- 201000003723 learning disability Diseases 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 208000012672 seasonal affective disease Diseases 0.000 description 2
- 208000020431 spinal cord injury Diseases 0.000 description 2
- NLUJYDHYQOADTC-UHFFFAOYSA-N C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)F Chemical compound C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)F NLUJYDHYQOADTC-UHFFFAOYSA-N 0.000 description 1
- MYQFRWQGSZJHJP-UHFFFAOYSA-N C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F Chemical compound C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F MYQFRWQGSZJHJP-UHFFFAOYSA-N 0.000 description 1
- NPACWOUALBOFCX-UHFFFAOYSA-N C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F Chemical compound C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F NPACWOUALBOFCX-UHFFFAOYSA-N 0.000 description 1
- JPWFUIINMCFKKV-UHFFFAOYSA-N C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)F Chemical compound C(C)S(=O)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)F JPWFUIINMCFKKV-UHFFFAOYSA-N 0.000 description 1
- XPBOEVDLIFYMPJ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)C)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)C)C)=O XPBOEVDLIFYMPJ-UHFFFAOYSA-N 0.000 description 1
- XYVDZVMCWBTNOK-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)=O XYVDZVMCWBTNOK-UHFFFAOYSA-N 0.000 description 1
- KQYRCHMEPNTALM-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C(F)(F)F)F)=O KQYRCHMEPNTALM-UHFFFAOYSA-N 0.000 description 1
- RUIQNPYVXJEBBO-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)C)F)=O RUIQNPYVXJEBBO-UHFFFAOYSA-N 0.000 description 1
- DKSRHIGGKQGFBZ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C(=CC=C1)F)F)=O DKSRHIGGKQGFBZ-UHFFFAOYSA-N 0.000 description 1
- CXWNLRKVPTZAMW-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C=C(C=C1)F)C)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C=C(C=C1)F)C)=O CXWNLRKVPTZAMW-UHFFFAOYSA-N 0.000 description 1
- BKMSBHCHOBFHGI-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C=CC=C1)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=C(C=CC=C1)F)=O BKMSBHCHOBFHGI-UHFFFAOYSA-N 0.000 description 1
- TZTMNVHRZSLKCQ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O TZTMNVHRZSLKCQ-UHFFFAOYSA-N 0.000 description 1
- COUYIQFXIIUNGR-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)O COUYIQFXIIUNGR-UHFFFAOYSA-N 0.000 description 1
- RDMKAVGODKFRCD-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)OC Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)OC RDMKAVGODKFRCD-UHFFFAOYSA-N 0.000 description 1
- UGHHTLPIQFPNBL-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)(F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)(F)F)=O UGHHTLPIQFPNBL-UHFFFAOYSA-N 0.000 description 1
- RUVUDGCSGMUVFA-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)(F)F Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)(F)F RUVUDGCSGMUVFA-UHFFFAOYSA-N 0.000 description 1
- ASJPGPWGKYXRHZ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)O ASJPGPWGKYXRHZ-UHFFFAOYSA-N 0.000 description 1
- BMSTZSWGGAVTSJ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)=O BMSTZSWGGAVTSJ-UHFFFAOYSA-N 0.000 description 1
- DORUZFRYHXMRIH-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)O DORUZFRYHXMRIH-UHFFFAOYSA-N 0.000 description 1
- WZCQRGOCNRDUEG-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)F)=O WZCQRGOCNRDUEG-UHFFFAOYSA-N 0.000 description 1
- VABLJPYHCWGFNZ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)(F)F Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)(F)F VABLJPYHCWGFNZ-UHFFFAOYSA-N 0.000 description 1
- KUYKYLKYCKTZIJ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)=O KUYKYLKYCKTZIJ-UHFFFAOYSA-N 0.000 description 1
- HUZHGPHZVLDUJJ-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC(=C1)F)F)=O HUZHGPHZVLDUJJ-UHFFFAOYSA-N 0.000 description 1
- HRYZFRAPQIQORL-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O HRYZFRAPQIQORL-UHFFFAOYSA-N 0.000 description 1
- SFJFOHCEBZDZKY-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)O SFJFOHCEBZDZKY-UHFFFAOYSA-N 0.000 description 1
- CZDIUGAQGLIXLH-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)F)=O CZDIUGAQGLIXLH-UHFFFAOYSA-N 0.000 description 1
- MKIAULBDGNMNHF-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)F)=O MKIAULBDGNMNHF-UHFFFAOYSA-N 0.000 description 1
- FZGLSOQFRNSFNA-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)OC(F)(F)F)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)OC(F)(F)F)=O FZGLSOQFRNSFNA-UHFFFAOYSA-N 0.000 description 1
- DCMZZBWQUIWHRK-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C=1C=C(C=CC=1)C)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C=1C=C(C=CC=1)C)=O DCMZZBWQUIWHRK-UHFFFAOYSA-N 0.000 description 1
- APVZQUTYSOZGDT-UHFFFAOYSA-N C1(CC1)C(CN1N=CC2=NC=C(C=C21)C=1SC(=CC=1)C)=O Chemical compound C1(CC1)C(CN1N=CC2=NC=C(C=C21)C=1SC(=CC=1)C)=O APVZQUTYSOZGDT-UHFFFAOYSA-N 0.000 description 1
- LYKDAZQLVJEPLB-UHFFFAOYSA-N C1(CC1)N1C(OC(C1)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O Chemical compound C1(CC1)N1C(OC(C1)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O LYKDAZQLVJEPLB-UHFFFAOYSA-N 0.000 description 1
- LYKDAZQLVJEPLB-AWEZNQCLSA-N C1(CC1)N1C(O[C@@H](C1)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O Chemical compound C1(CC1)N1C(O[C@@H](C1)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O LYKDAZQLVJEPLB-AWEZNQCLSA-N 0.000 description 1
- LYKDAZQLVJEPLB-CQSZACIVSA-N C1(CC1)N1C(O[C@H](C1)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O Chemical compound C1(CC1)N1C(O[C@H](C1)CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)=O LYKDAZQLVJEPLB-CQSZACIVSA-N 0.000 description 1
- DORUZFRYHXMRIH-GOSISDBHSA-N C1(CC1)[C@@H](CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)O Chemical compound C1(CC1)[C@@H](CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)O DORUZFRYHXMRIH-GOSISDBHSA-N 0.000 description 1
- DORUZFRYHXMRIH-SFHVURJKSA-N C1(CC1)[C@H](CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)O Chemical compound C1(CC1)[C@H](CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)O DORUZFRYHXMRIH-SFHVURJKSA-N 0.000 description 1
- CPUHAKFGGGZWHQ-UHFFFAOYSA-N C1(CCC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)=O Chemical compound C1(CCC1)C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)=O CPUHAKFGGGZWHQ-UHFFFAOYSA-N 0.000 description 1
- JGEPFDXEWYWOBC-UHFFFAOYSA-N CC(C(CN1N=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)=O)C Chemical compound CC(C(CN1N=CC2=NC=C(C=C21)C1=C(C(=C(C=C1)F)F)F)=O)C JGEPFDXEWYWOBC-UHFFFAOYSA-N 0.000 description 1
- PURJFKNTTATIHB-UHFFFAOYSA-N CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O)C Chemical compound CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)=O)C PURJFKNTTATIHB-UHFFFAOYSA-N 0.000 description 1
- IYQFIDWWEYJRTF-UHFFFAOYSA-N CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)O)C Chemical compound CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C(=C1)F)F)F)O)C IYQFIDWWEYJRTF-UHFFFAOYSA-N 0.000 description 1
- JHKVSPDDDMCHQI-UHFFFAOYSA-N CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)C Chemical compound CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)=O)C JHKVSPDDDMCHQI-UHFFFAOYSA-N 0.000 description 1
- KIXISOYPVHERPH-UHFFFAOYSA-N CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)O)C Chemical compound CC(C(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)O)C KIXISOYPVHERPH-UHFFFAOYSA-N 0.000 description 1
- OCTVCUQPJKIJST-UHFFFAOYSA-N CC(C(CN1N=CC2=NC=C(C=C21)C1=CC=CC=C1)=O)C Chemical compound CC(C(CN1N=CC2=NC=C(C=C21)C1=CC=CC=C1)=O)C OCTVCUQPJKIJST-UHFFFAOYSA-N 0.000 description 1
- LNPXTXOBVGCZST-UHFFFAOYSA-N CC(C(CN1N=CC2=NC=C(C=C21)C1=CC=CC=C1)O)C Chemical compound CC(C(CN1N=CC2=NC=C(C=C21)C1=CC=CC=C1)O)C LNPXTXOBVGCZST-UHFFFAOYSA-N 0.000 description 1
- CHEFVBYITJKUHD-UHFFFAOYSA-N COCCC(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)O Chemical compound COCCC(CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F)O CHEFVBYITJKUHD-UHFFFAOYSA-N 0.000 description 1
- BHMWCAUYVVREAP-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1)C(F)(F)F BHMWCAUYVVREAP-UHFFFAOYSA-N 0.000 description 1
- GVJSJHQVFQQJMU-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C)=O)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C)=O)OC(F)F GVJSJHQVFQQJMU-UHFFFAOYSA-N 0.000 description 1
- LOHSNPIDKAZSRJ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)OC(F)F LOHSNPIDKAZSRJ-UHFFFAOYSA-N 0.000 description 1
- JDGJJGCTNIYXJN-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)O)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)O)OC(F)F JDGJJGCTNIYXJN-UHFFFAOYSA-N 0.000 description 1
- IATVLQQLFSUUCG-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O)OC(F)F IATVLQQLFSUUCG-UHFFFAOYSA-N 0.000 description 1
- LILHALSNDPSNDY-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CS(=O)CC)OC(F)F Chemical compound ClC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CS(=O)CC)OC(F)F LILHALSNDPSNDY-UHFFFAOYSA-N 0.000 description 1
- WUSLKFGIYUSGMK-UHFFFAOYSA-N ClC1=CC=C(S1)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1 Chemical compound ClC1=CC=C(S1)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1 WUSLKFGIYUSGMK-UHFFFAOYSA-N 0.000 description 1
- LNCXMMDTMYKLOF-UHFFFAOYSA-N ClC1=CC=C(S1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound ClC1=CC=C(S1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O LNCXMMDTMYKLOF-UHFFFAOYSA-N 0.000 description 1
- PVGABXXKRBTEPM-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1)F Chemical compound ClC=1C(=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1)F PVGABXXKRBTEPM-UHFFFAOYSA-N 0.000 description 1
- NPMPYZNZWFULIZ-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1 Chemical compound ClC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1CC1 NPMPYZNZWFULIZ-UHFFFAOYSA-N 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- ZXYBQUSDXHDYCL-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC(C)(F)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O ZXYBQUSDXHDYCL-UHFFFAOYSA-N 0.000 description 1
- LBOTYKXZZNWRBK-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)O Chemical compound FC(C)(F)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)O LBOTYKXZZNWRBK-UHFFFAOYSA-N 0.000 description 1
- SENLTLKXUNUGDY-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC(C)(F)C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O SENLTLKXUNUGDY-UHFFFAOYSA-N 0.000 description 1
- LCBMPFWFDYYKQK-UHFFFAOYSA-N FC(C)(F)C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O Chemical compound FC(C)(F)C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O LCBMPFWFDYYKQK-UHFFFAOYSA-N 0.000 description 1
- AKFLQCNHYSLEDD-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)F Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)F AKFLQCNHYSLEDD-UHFFFAOYSA-N 0.000 description 1
- RDCXEMXWAHZHIP-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)F Chemical compound FC(C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)F RDCXEMXWAHZHIP-UHFFFAOYSA-N 0.000 description 1
- CIJXJNZXXFOKNY-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=CSC=C1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=CSC=C1)F CIJXJNZXXFOKNY-UHFFFAOYSA-N 0.000 description 1
- MFTUEXIRZGHNOX-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=NC=C(C=C1)F)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=NC=C(C=C1)F)F MFTUEXIRZGHNOX-UHFFFAOYSA-N 0.000 description 1
- RYKIVRWNAJAMIW-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=NC=C(C=C1F)F)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=NC=C(C=C1F)F)F RYKIVRWNAJAMIW-UHFFFAOYSA-N 0.000 description 1
- UMEDDEJOJJGXAK-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=NC=CC=C1F)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C1=NC=CC=C1F)F UMEDDEJOJJGXAK-UHFFFAOYSA-N 0.000 description 1
- MUBKUGJDYMOLRI-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C=1C=NC=CC=1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C=1C=NC=CC=1)F MUBKUGJDYMOLRI-UHFFFAOYSA-N 0.000 description 1
- ZMMBKVDEBOKZNM-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C=1SC=CC=1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(=O)C=1SC=CC=1)F ZMMBKVDEBOKZNM-UHFFFAOYSA-N 0.000 description 1
- FTTSFYMDYPJMDB-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)O)F FTTSFYMDYPJMDB-UHFFFAOYSA-N 0.000 description 1
- HUZZVUXOIABWEG-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1(COC1)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1(COC1)C)F HUZZVUXOIABWEG-UHFFFAOYSA-N 0.000 description 1
- STOXIGUABSMDGQ-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1C(N(CC1)C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1C(N(CC1)C)=O)F STOXIGUABSMDGQ-UHFFFAOYSA-N 0.000 description 1
- CZZDKBQHDNHQLD-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CC(N(C1)C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CC(N(C1)C)=O)F CZZDKBQHDNHQLD-UHFFFAOYSA-N 0.000 description 1
- HVZIABNDESTIOL-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CCC(N1C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CCC(N1C)=O)F HVZIABNDESTIOL-UHFFFAOYSA-N 0.000 description 1
- JSGHOXMKEVBEAJ-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CN(C(O1)=O)CC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CN(C(O1)=O)CC)F JSGHOXMKEVBEAJ-UHFFFAOYSA-N 0.000 description 1
- WMPSKRABGGMLFO-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O)F WMPSKRABGGMLFO-UHFFFAOYSA-N 0.000 description 1
- YDQRXNJGHNNTES-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1COCC1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1COCC1)F YDQRXNJGHNNTES-UHFFFAOYSA-N 0.000 description 1
- AUDCRMZAPLUASE-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1N(C(OC1)=O)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1N(C(OC1)=O)C)F AUDCRMZAPLUASE-UHFFFAOYSA-N 0.000 description 1
- QKMAARUYRGVIJH-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1OCCC1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1OCCC1)F QKMAARUYRGVIJH-UHFFFAOYSA-N 0.000 description 1
- STOXIGUABSMDGQ-GFCCVEGCSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1C(N(CC1)C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1C(N(CC1)C)=O)F STOXIGUABSMDGQ-GFCCVEGCSA-N 0.000 description 1
- CZZDKBQHDNHQLD-LLVKDONJSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CC(N(C1)C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CC(N(C1)C)=O)F CZZDKBQHDNHQLD-LLVKDONJSA-N 0.000 description 1
- BBBHJMAWFLJLCO-LBPRGKRZSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CN(C(O1)=O)C)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CN(C(O1)=O)C)F BBBHJMAWFLJLCO-LBPRGKRZSA-N 0.000 description 1
- JSGHOXMKEVBEAJ-ZDUSSCGKSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CN(C(O1)=O)CC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CN(C(O1)=O)CC)F JSGHOXMKEVBEAJ-ZDUSSCGKSA-N 0.000 description 1
- WMPSKRABGGMLFO-NSHDSACASA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CNC(O1)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@@H]1CNC(O1)=O)F WMPSKRABGGMLFO-NSHDSACASA-N 0.000 description 1
- STOXIGUABSMDGQ-LBPRGKRZSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1C(N(CC1)C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1C(N(CC1)C)=O)F STOXIGUABSMDGQ-LBPRGKRZSA-N 0.000 description 1
- CZZDKBQHDNHQLD-NSHDSACASA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CC(N(C1)C)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CC(N(C1)C)=O)F CZZDKBQHDNHQLD-NSHDSACASA-N 0.000 description 1
- JSGHOXMKEVBEAJ-CYBMUJFWSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CN(C(O1)=O)CC)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CN(C(O1)=O)CC)F JSGHOXMKEVBEAJ-CYBMUJFWSA-N 0.000 description 1
- WMPSKRABGGMLFO-LLVKDONJSA-N FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CNC(O1)=O)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2C[C@H]1CNC(O1)=O)F WMPSKRABGGMLFO-LLVKDONJSA-N 0.000 description 1
- UNPZZAHFBVZXMZ-UHFFFAOYSA-N FC(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)(CC)F Chemical compound FC(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)C(F)F)(CC)F UNPZZAHFBVZXMZ-UHFFFAOYSA-N 0.000 description 1
- AWFZLCMUYSEHHG-UHFFFAOYSA-N FC(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)(CC)F Chemical compound FC(CN1N=CC2=NC=C(C=C21)C1=CC(=C(C=C1)F)OC(F)F)(CC)F AWFZLCMUYSEHHG-UHFFFAOYSA-N 0.000 description 1
- BWRYTXBFYRHPCL-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(C)=O)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(C)=O)F BWRYTXBFYRHPCL-UHFFFAOYSA-N 0.000 description 1
- NHQTVRSYULLLDL-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)O)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)O)F NHQTVRSYULLLDL-UHFFFAOYSA-N 0.000 description 1
- BQFCFMHVYVHLSD-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1C(N(CC1)C)=O)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1C(N(CC1)C)=O)F BQFCFMHVYVHLSD-UHFFFAOYSA-N 0.000 description 1
- OCHLMENFNSFEHM-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CC(N(C1)C)=O)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CC(N(C1)C)=O)F OCHLMENFNSFEHM-UHFFFAOYSA-N 0.000 description 1
- QOJJPXFPSNHHIK-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CCC(N1C)=O)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CCC(N1C)=O)F QOJJPXFPSNHHIK-UHFFFAOYSA-N 0.000 description 1
- PLIKQBUDMNOUHC-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CN(C(O1)=O)C)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CN(C(O1)=O)C)F PLIKQBUDMNOUHC-UHFFFAOYSA-N 0.000 description 1
- DLQVAAZJKCLEJA-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1CNC(O1)=O)F DLQVAAZJKCLEJA-UHFFFAOYSA-N 0.000 description 1
- BPBAJRMKKWNRAA-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1N(C(OC1)=O)C)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1N(C(OC1)=O)C)F BPBAJRMKKWNRAA-UHFFFAOYSA-N 0.000 description 1
- HJUAVKRXFICRGY-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1OCCC1)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC1OCCC1)F HJUAVKRXFICRGY-UHFFFAOYSA-N 0.000 description 1
- MMCWMUIFDBSIJB-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)(=O)CC)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)(=O)CC)F MMCWMUIFDBSIJB-UHFFFAOYSA-N 0.000 description 1
- LQHFJUAAYCMTBI-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)CC)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)CC)F LQHFJUAAYCMTBI-UHFFFAOYSA-N 0.000 description 1
- RQBJIEMJDUOIRN-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)C Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)C RQBJIEMJDUOIRN-UHFFFAOYSA-N 0.000 description 1
- PIDUKQXJBXMPBI-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)C(F)(F)F Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)C(F)(F)F PIDUKQXJBXMPBI-UHFFFAOYSA-N 0.000 description 1
- PPYDKQUNIATYBR-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)O)C Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)O)C PPYDKQUNIATYBR-UHFFFAOYSA-N 0.000 description 1
- PGOBHAGGIQRHCO-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C)=O)C Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C)=O)C PGOBHAGGIQRHCO-UHFFFAOYSA-N 0.000 description 1
- NQJHDORISBQNMY-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)C Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)C NQJHDORISBQNMY-UHFFFAOYSA-N 0.000 description 1
- BWTUYRVATHXEKK-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)C(F)(F)F Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O)C(F)(F)F BWTUYRVATHXEKK-UHFFFAOYSA-N 0.000 description 1
- QUFGPTDVGNCXBV-UHFFFAOYSA-N FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CCOC)C Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=NN2CCOC)C QUFGPTDVGNCXBV-UHFFFAOYSA-N 0.000 description 1
- BPRHQSAFRRDBOC-UHFFFAOYSA-N FC1=C(C=CC(=C1F)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC1=C(C=CC(=C1F)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O BPRHQSAFRRDBOC-UHFFFAOYSA-N 0.000 description 1
- RDTCHFLFXLWNHF-UHFFFAOYSA-N FC1=C(C=CC=C1C(F)(F)F)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O Chemical compound FC1=C(C=CC=C1C(F)(F)F)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O RDTCHFLFXLWNHF-UHFFFAOYSA-N 0.000 description 1
- VDQBVJQPRINNFQ-UHFFFAOYSA-N FC1=C(C=CC=C1C(F)(F)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC1=C(C=CC=C1C(F)(F)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O VDQBVJQPRINNFQ-UHFFFAOYSA-N 0.000 description 1
- KQSVOUDHXGBAQZ-UHFFFAOYSA-N FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O Chemical compound FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O KQSVOUDHXGBAQZ-UHFFFAOYSA-N 0.000 description 1
- HJTCJLPEVNRECW-UHFFFAOYSA-N FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC1=C(C=CC=C1F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O HJTCJLPEVNRECW-UHFFFAOYSA-N 0.000 description 1
- FJUKOVPCEGCCNP-UHFFFAOYSA-N FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)C Chemical compound FC1=CC(=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O)C FJUKOVPCEGCCNP-UHFFFAOYSA-N 0.000 description 1
- JNCCGBYPFUHAIU-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O JNCCGBYPFUHAIU-UHFFFAOYSA-N 0.000 description 1
- FDFADOFVFLRHDR-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O FDFADOFVFLRHDR-UHFFFAOYSA-N 0.000 description 1
- KOQLWVZREPZTMU-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O KOQLWVZREPZTMU-UHFFFAOYSA-N 0.000 description 1
- LSRGZMYMQITKAI-UHFFFAOYSA-N FC=1C=C(C=C(C=1F)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC=1C=C(C=C(C=1F)F)C=1C=C2C(=NC=1)C=NN2CC(CC)=O LSRGZMYMQITKAI-UHFFFAOYSA-N 0.000 description 1
- OQHFXKDCEOXHOW-UHFFFAOYSA-N FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O OQHFXKDCEOXHOW-UHFFFAOYSA-N 0.000 description 1
- PEKIJAOTZOZRRW-UHFFFAOYSA-N FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=NN2CC(CC)=O PEKIJAOTZOZRRW-UHFFFAOYSA-N 0.000 description 1
- BDZFOMYBQYCTBP-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C(=NN2CC(CC)=O)F Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C(=NN2CC(CC)=O)F BDZFOMYBQYCTBP-UHFFFAOYSA-N 0.000 description 1
- BFKIWDQIZRLIDS-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C(=NN2CC(CC)O)F Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C(=NN2CC(CC)O)F BFKIWDQIZRLIDS-UHFFFAOYSA-N 0.000 description 1
- DQDYVYXUUXJTBX-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(C(C)C)=O DQDYVYXUUXJTBX-UHFFFAOYSA-N 0.000 description 1
- ICDBMQZAHCTZMC-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)O Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CC(CC)O ICDBMQZAHCTZMC-UHFFFAOYSA-N 0.000 description 1
- KCPCPWXZOXTGNY-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)CC Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=NN2CS(=O)CC KCPCPWXZOXTGNY-UHFFFAOYSA-N 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- GCTTXTXDPCLXNT-UHFFFAOYSA-N O1C(CC1)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F Chemical compound O1C(CC1)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F GCTTXTXDPCLXNT-UHFFFAOYSA-N 0.000 description 1
- VOVNRKCABOBKRC-UHFFFAOYSA-N O1C(CCC1)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F Chemical compound O1C(CCC1)CN1N=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F VOVNRKCABOBKRC-UHFFFAOYSA-N 0.000 description 1
- 208000006633 Tonic-Clonic Epilepsy Diseases 0.000 description 1
- BMMKPGVCTLTADE-UHFFFAOYSA-N butan-2-imine Chemical compound CCC(C)=N BMMKPGVCTLTADE-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962861674P | 2019-06-14 | 2019-06-14 | |
| US62/861,674 | 2019-06-14 | ||
| PCT/EP2020/066391 WO2020249791A1 (en) | 2019-06-14 | 2020-06-12 | SUBSTITUTED PYRAZOLO[4,3-b]PYRIDINES AND THEIR USE AS GLUN2B RECEPTOR MODULATORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022536174A JP2022536174A (ja) | 2022-08-12 |
| JP2022536174A5 JP2022536174A5 (https=) | 2023-06-20 |
| JPWO2020249791A5 true JPWO2020249791A5 (https=) | 2023-06-20 |
Family
ID=71120146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021573717A Pending JP2022536174A (ja) | 2019-06-14 | 2020-06-12 | 置換ピラゾロ［４，３－ｂ］ピリジニル及びＧＬＵＮ２Ｂ受容体調節因子としてのそれらの使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US11161846B2 (https=) |
| EP (1) | EP3983073A1 (https=) |
| JP (1) | JP2022536174A (https=) |
| KR (1) | KR20220020917A (https=) |
| CN (1) | CN113993583A (https=) |
| AU (1) | AU2020293642A1 (https=) |
| BR (1) | BR112021025136A2 (https=) |
| CA (1) | CA3143102A1 (https=) |
| MX (1) | MX2021015510A (https=) |
| WO (1) | WO2020249791A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN113993868A (zh) | 2019-06-14 | 2022-01-28 | 詹森药业有限公司 | 取代的吡唑并吡啶酰胺以及它们作为glun2b受体调节剂的用途 |
| AU2020293642A1 (en) | 2019-06-14 | 2022-01-20 | Janssen Pharmaceutica Nv | Substituted pyrazolo[4,3-b]pyridines and their use as GluN2B receptor modulators |
| MX2021015508A (es) | 2019-06-14 | 2022-01-31 | Janssen Pharmaceutica Nv | Carbamatos de piridina y su uso como moduladores del receptor glun2b. |
| KR20220024403A (ko) | 2019-06-14 | 2022-03-03 | 얀센 파마슈티카 엔.브이. | 치환된 피라졸로-피라진 및 이들의 glun2b 수용체 조절제로서의 용도 |
| CN113950357A (zh) | 2019-06-14 | 2022-01-18 | 詹森药业有限公司 | 吡嗪氨基甲酸酯及其作为GluN2B受体调节剂的用途 |
| SG11202112405VA (en) | 2019-06-14 | 2021-12-30 | Janssen Pharmaceutica Nv | Substituted heteroaromatic pyrazolo-pyridines and their use as glun2b receptor modulators |
| 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 |
| EP4669318A1 (en) * | 2023-02-23 | 2025-12-31 | The Rockefeller University | 1-ACYL-3-AMINOINDAZOLES FOR THE TREATMENT OF CYSTIC FIBROSIS |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9407447D0 (en) | 1994-04-14 | 1994-06-08 | Glaxo Group Ltd | Chemical compounds |
| CA2262502C (en) | 1996-07-31 | 2002-11-26 | Nikken Chemicals Co., Ltd. | 6-phenyltetrahydro-1,3-oxazin-2-one derivatives and pharmaceutical composition containing the same |
| US6610723B2 (en) | 2001-01-29 | 2003-08-26 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| EP1490364B1 (en) | 2002-03-28 | 2007-09-26 | 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 |
| EP1720860A1 (en) | 2004-02-18 | 2006-11-15 | AstraZeneca AB | Triazole compounds and their use as metabotropic glutamate receptor antagonists |
| US7820654B2 (en) | 2004-09-23 | 2010-10-26 | Dr. Reddy's Laboratories Ltd. | Pyrimidine compounds, process for their preparation and compositions containing them |
| 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 |
| TWI443090B (zh) | 2007-05-25 | 2014-07-01 | Abbvie Deutschland | 作為代謝性麩胺酸受體２（ｍｇｌｕ２ 受體）之正向調節劑之雜環化合物 |
| WO2009004430A1 (en) | 2007-06-29 | 2009-01-08 | Pfizer Inc. | N-benzyl oxazolidinones and related heterocycleic compounds as potentiators of glutamate receptors |
| CN101842357A (zh) | 2007-08-30 | 2010-09-22 | 武田药品工业株式会社 | 取代的吡唑衍生物 |
| EP2215073A4 (en) | 2007-10-31 | 2011-04-06 | Merck Sharp & Dohme | SLEEP MODULATION WITH NR2B RECEPTOR ANTAGONISTS |
| WO2009118187A1 (en) | 2008-03-27 | 2009-10-01 | Evotec Neurosciences Gmbh | Methods for treating disorders using nmda nr2b-subtype selective antagonist |
| JPWO2009157196A1 (ja) | 2008-06-25 | 2011-12-08 | 武田薬品工業株式会社 | アミド化合物 |
| 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 |
| RU2517181C2 (ru) | 2008-10-16 | 2014-05-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов |
| KR101048448B1 (ko) * | 2008-11-21 | 2011-07-11 | 한국화학연구원 | 신규 피라졸로[4,3-ｂ]피리딘 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약학적 조성물 |
| CA2744498C (en) | 2008-11-25 | 2017-10-24 | University Of Rochester | Mlk inhibitors and methods of use |
| US8969342B2 (en) | 2009-03-20 | 2015-03-03 | Brandeis University | Compounds and methods for treating mammalian gastrointestinal microbial infections |
| EP2579717A4 (en) | 2010-06-09 | 2013-12-11 | Merck Sharp & Dohme | POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 |
| JP2012188363A (ja) | 2011-03-09 | 2012-10-04 | Dainippon Sumitomo Pharma Co Ltd | アザベンゾイミダゾロン誘導体 |
| WO2013060029A1 (en) | 2011-10-28 | 2013-05-02 | Merck Sharp & Dohme Corp | Allosteric modulators of metabotropic glutamate receptors |
| WO2013130855A1 (en) | 2012-03-02 | 2013-09-06 | Takeda Pharmaceutical Company Limited | Indazole derivatives |
| MA37975B2 (fr) | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| 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 |
| SG11201506687RA (en) | 2013-03-15 | 2015-09-29 | Plexxikon Inc | Heterocyclic compounds and uses thereof |
| CA2915838C (en) * | 2013-06-21 | 2023-04-18 | Zenith Epigenetics Corp. | Bicyclic bromodomain inhibitors |
| CA2918242C (en) | 2013-07-31 | 2022-06-21 | Merck Patent Gmbh | Pyridines, pyrimidines, and pyrazines, as btk inhibitors and uses thereof |
| WO2016025917A1 (en) | 2014-08-15 | 2016-02-18 | Janssen Pharmaceuticals, Inc. | Triazoles as nr2b receptor inhibitors |
| ES2791252T3 (es) | 2014-08-15 | 2020-11-03 | Janssen Pharmaceuticals Inc | Pirazoles |
| 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 |
| HRP20200410T1 (hr) * | 2015-07-09 | 2020-08-21 | Janssen Pharmaceutica Nv | Supstituirani 4-azaindoli i njihova upotreba kao modulatora glun2b receptora |
| BR112018016329A2 (pt) | 2016-02-10 | 2018-12-18 | Janssen Pharmaceutica Nv | 1,2,3-triazóis substituídos como moduladores de nmda seletivos para 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 |
| IL271149B2 (en) | 2017-06-14 | 2024-05-01 | Trevena Inc | Compounds for modulating s1p1 activity and methods of using the same |
| WO2019193516A2 (en) | 2018-04-04 | 2019-10-10 | Janssen Pharmaceutica Nv | Substituted pyridine and pyrimidines and their use as glun2b receptor modulators |
| CN110294756A (zh) | 2019-06-04 | 2019-10-01 | 广州市原子高科同位素医药有限公司 | GluN2B亚基靶向型中枢神经系统正电子示踪剂及其制备 |
| KR20220024403A (ko) | 2019-06-14 | 2022-03-03 | 얀센 파마슈티카 엔.브이. | 치환된 피라졸로-피라진 및 이들의 glun2b 수용체 조절제로서의 용도 |
| AU2020293642A1 (en) | 2019-06-14 | 2022-01-20 | Janssen Pharmaceutica Nv | Substituted pyrazolo[4,3-b]pyridines and their use as GluN2B receptor modulators |
| CN113950357A (zh) | 2019-06-14 | 2022-01-18 | 詹森药业有限公司 | 吡嗪氨基甲酸酯及其作为GluN2B受体调节剂的用途 |
| SG11202112405VA (en) | 2019-06-14 | 2021-12-30 | Janssen Pharmaceutica Nv | Substituted heteroaromatic pyrazolo-pyridines and their use as glun2b receptor modulators |
| MX2021015508A (es) | 2019-06-14 | 2022-01-31 | Janssen Pharmaceutica Nv | Carbamatos de piridina y su uso como moduladores del receptor glun2b. |
| CN113993868A (zh) | 2019-06-14 | 2022-01-28 | 詹森药业有限公司 | 取代的吡唑并吡啶酰胺以及它们作为glun2b受体调节剂的用途 |
-
2020
- 2020-06-12 AU AU2020293642A patent/AU2020293642A1/en not_active Abandoned
- 2020-06-12 EP EP20734122.3A patent/EP3983073A1/en not_active Withdrawn
- 2020-06-12 BR BR112021025136A patent/BR112021025136A2/pt not_active Application Discontinuation
- 2020-06-12 KR KR1020227001094A patent/KR20220020917A/ko not_active Ceased
- 2020-06-12 US US16/899,836 patent/US11161846B2/en not_active Expired - Fee Related
- 2020-06-12 MX MX2021015510A patent/MX2021015510A/es unknown
- 2020-06-12 WO PCT/EP2020/066391 patent/WO2020249791A1/en not_active Ceased
- 2020-06-12 US US17/618,066 patent/US20220324860A1/en not_active Abandoned
- 2020-06-12 CN CN202080043665.4A patent/CN113993583A/zh active Pending
- 2020-06-12 CA CA3143102A patent/CA3143102A1/en active Pending
- 2020-06-12 JP JP2021573717A patent/JP2022536174A/ja active Pending