JPWO2019243850A5 - - Google Patents
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- Publication number
- JPWO2019243850A5 JPWO2019243850A5 JP2020571700A JP2020571700A JPWO2019243850A5 JP WO2019243850 A5 JPWO2019243850 A5 JP WO2019243850A5 JP 2020571700 A JP2020571700 A JP 2020571700A JP 2020571700 A JP2020571700 A JP 2020571700A JP WO2019243850 A5 JPWO2019243850 A5 JP WO2019243850A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxadiazole
- azabicyclo
- octane
- diazaspiro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 R4 is an H Chemical group 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 58
- 229910052757 nitrogen Inorganic materials 0.000 claims description 54
- 150000002430 hydrocarbons Chemical group 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 125000002950 monocyclic group Chemical group 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000002619 bicyclic group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 16
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- YNMZZHPSYMOGCI-UHFFFAOYSA-N undecan-3-one Chemical compound CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 claims description 6
- GACQWNAPVBCFQM-UHFFFAOYSA-N O=CN1C2(CCC2)CC1 Chemical compound O=CN1C2(CCC2)CC1 GACQWNAPVBCFQM-UHFFFAOYSA-N 0.000 claims description 5
- VVQIDZOAUIQOKY-UHFFFAOYSA-N 8-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1=NOC(=N1)N1CCC(CCC1)N1CCC2(CNC(O2)=O)CC1 VVQIDZOAUIQOKY-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 208000028698 Cognitive impairment Diseases 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 230000003551 muscarinic effect Effects 0.000 claims description 3
- 239000000018 receptor agonist Substances 0.000 claims description 3
- 229940044601 receptor agonist Drugs 0.000 claims description 3
- KBGJSKZARWJVRK-BHWOMJMDSA-N (5S)-5-ethyl-1-[1-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]piperidin-4-yl]pyrrolidin-2-one Chemical compound C(C)[C@H]1CCC(N1C1CCN(CC1)C1CCN(CCC1)C1=NC(=NO1)C)=O KBGJSKZARWJVRK-BHWOMJMDSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- RXBQCPFNLGINPW-UHFFFAOYSA-N 1'-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]spiro[1H-indole-3,4'-piperidine]-2-one Chemical compound CC1=NOC(=N1)N1CCC(CCC1)N1CCC2(CC1)C(NC1=CC=CC=C12)=O RXBQCPFNLGINPW-UHFFFAOYSA-N 0.000 claims description 2
- WHALLMCIWBGPLM-UHFFFAOYSA-N 1-(cyclopropylmethyl)-8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound C1(CC1)CC1NC(CC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O WHALLMCIWBGPLM-UHFFFAOYSA-N 0.000 claims description 2
- WYFHOGNDYHEHBV-UHFFFAOYSA-N 1-benzyl-8-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound C(C1=CC=CC=C1)C1NC(CC11CCN(CC1)C1CCN(CCC1)C1=NC(=NO1)C)=O WYFHOGNDYHEHBV-UHFFFAOYSA-N 0.000 claims description 2
- NBQJTNRPHKHLCM-UHFFFAOYSA-N 1-cyclopropyl-8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound C1(CC1)C1NC(CC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O NBQJTNRPHKHLCM-UHFFFAOYSA-N 0.000 claims description 2
- XJLDYKIEURAVBW-UHFFFAOYSA-N 3-decanone Chemical compound CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 claims description 2
- MIBJKUUVELZNJP-UHFFFAOYSA-N 3-methyl-5-[2-(4-pyrazol-1-ylpiperidin-1-yl)-6-azaspiro[3.4]octan-6-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1CC2(CC(C2)N2CCC(CC2)N2N=CC=C2)CC1 MIBJKUUVELZNJP-UHFFFAOYSA-N 0.000 claims description 2
- KLWSNZQBPQFATF-UHFFFAOYSA-N 3-methyl-5-[3-(4-pyrazol-1-ylpiperidin-1-yl)-6-azabicyclo[3.2.1]octan-6-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1C2CC(CC(C1)C2)N1CCC(CC1)N1N=CC=C1 KLWSNZQBPQFATF-UHFFFAOYSA-N 0.000 claims description 2
- JOAOVJYHNMBLLD-UHFFFAOYSA-N 3-methyl-5-[3-(4-pyrazol-1-ylpiperidin-1-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1C2CC(CC1CC2)N1CCC(CC1)N1N=CC=C1 JOAOVJYHNMBLLD-UHFFFAOYSA-N 0.000 claims description 2
- XCTRZAFYYZWZKS-UHFFFAOYSA-N 3-methyl-5-[4-(4-pyrazol-1-ylpiperidin-1-yl)azepan-1-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1CCC(CCC1)N1CCC(CC1)N1N=CC=C1 XCTRZAFYYZWZKS-UHFFFAOYSA-N 0.000 claims description 2
- REKRVKAPQNABCS-UHFFFAOYSA-N 3-methyl-5-[4-(4-pyrazol-1-ylpiperidin-1-yl)piperidin-1-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1CCC(CC1)N1CCC(CC1)N1N=CC=C1 REKRVKAPQNABCS-UHFFFAOYSA-N 0.000 claims description 2
- PGLVGCOKZJKJMW-UHFFFAOYSA-N 3-methyl-5-[5-(4-pyrazol-1-ylpiperidin-1-yl)-2-azabicyclo[2.2.2]octan-2-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1C2CC(C(C1)CC2)N1CCC(CC1)N1N=CC=C1 PGLVGCOKZJKJMW-UHFFFAOYSA-N 0.000 claims description 2
- IKOCEWLCJSEBOG-UHFFFAOYSA-N 3-methyl-5-[6-(4-pyrazol-1-ylpiperidin-1-yl)-2-azaspiro[3.3]heptan-2-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1CC2(C1)CC(C2)N1CCC(CC1)N1N=CC=C1 IKOCEWLCJSEBOG-UHFFFAOYSA-N 0.000 claims description 2
- HNZLSDUORCLLFS-UHFFFAOYSA-N 3-methyl-5-[6-(4-pyrazol-1-ylpiperidin-1-yl)-2-azaspiro[3.4]octan-2-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1CC2(C1)CC(CC2)N1CCC(CC1)N1N=CC=C1 HNZLSDUORCLLFS-UHFFFAOYSA-N 0.000 claims description 2
- XGQADXPKVKUZHI-UHFFFAOYSA-N 3-methyl-5-[6-(4-pyrazol-1-ylpiperidin-1-yl)-3-azabicyclo[3.1.1]heptan-3-yl]-1,2,4-oxadiazole Chemical compound CC1=NOC(=N1)N1CC2C(C(C1)C2)N1CCC(CC1)N1N=CC=C1 XGQADXPKVKUZHI-UHFFFAOYSA-N 0.000 claims description 2
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims description 2
- RPBGOCYDBHJHNN-UHFFFAOYSA-N 4-(cyclopropylmethyl)-8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1(CC1)CC1NC(OC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O RPBGOCYDBHJHNN-UHFFFAOYSA-N 0.000 claims description 2
- NNDVXPYWQABDIC-UHFFFAOYSA-N 4-benzyl-8-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-2-azaspiro[3.3]heptan-6-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C(C1=CC=CC=C1)C1NC(OC11CCN(CC1)C1CC2(CN(C2)C2=NC(=NO2)C)C1)=O NNDVXPYWQABDIC-UHFFFAOYSA-N 0.000 claims description 2
- QIDVIFBZGIVZES-UHFFFAOYSA-N 4-cyclopropyl-8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1(CC1)C1NC(OC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O QIDVIFBZGIVZES-UHFFFAOYSA-N 0.000 claims description 2
- QAIHPKHMUQRGFR-UHFFFAOYSA-N 4-ethyl-8-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C(C)C1NC(OC11CCN(CC1)C1CCN(CCC1)C1=NC(=NO1)C)=O QAIHPKHMUQRGFR-UHFFFAOYSA-N 0.000 claims description 2
- ZXEKVMZBVBTWRU-UHFFFAOYSA-N 4-methyl-8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1NC(OC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O ZXEKVMZBVBTWRU-UHFFFAOYSA-N 0.000 claims description 2
- ONOPFFFCOXKFMF-UHFFFAOYSA-N 5-(8-azabicyclo[3.2.1]octan-8-yl)-3-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound C1C2CCC(N2C=2ON=C(N=2)C(F)(F)F)CC1 ONOPFFFCOXKFMF-UHFFFAOYSA-N 0.000 claims description 2
- XRAPKCLPZGZIHP-UHFFFAOYSA-N 8-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound CC1=NOC(=N1)N1CCC(CCC1)N1CCC2(CC(NC2)=O)CC1 XRAPKCLPZGZIHP-UHFFFAOYSA-N 0.000 claims description 2
- BZAKURPZDHSZIX-UHFFFAOYSA-N 8-[1-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]azepan-4-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound FC(C1=NOC(=N1)N1CCC(CCC1)N1CCC2(CNC(O2)=O)CC1)(F)F BZAKURPZDHSZIX-UHFFFAOYSA-N 0.000 claims description 2
- NFOCDEOOKHQVLO-UHFFFAOYSA-N 8-[1-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]azepan-4-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound FC(C1=NOC(=N1)N1CCC(CCC1)N1CCC2(CC(NC2)=O)CC1)(F)F NFOCDEOOKHQVLO-UHFFFAOYSA-N 0.000 claims description 2
- AXDPXNOJVNVYQR-UHFFFAOYSA-N 8-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-2-azabicyclo[2.2.2]octan-5-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1=NOC(=N1)N1C2CC(C(C1)CC2)N1CCC2(CNC(O2)=O)CC1 AXDPXNOJVNVYQR-UHFFFAOYSA-N 0.000 claims description 2
- LRGNHEIWPSKWLZ-UHFFFAOYSA-N 8-[6-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]-6-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound FC(C1=NOC(=N1)N1C2CC(CC(C1)C2)N1CCC2(CNC(O2)=O)CC1)(F)F LRGNHEIWPSKWLZ-UHFFFAOYSA-N 0.000 claims description 2
- PWZFXTGMJHMZPI-UHFFFAOYSA-N 8-[8-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C1(CC1)C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CNC(O2)=O)CC1 PWZFXTGMJHMZPI-UHFFFAOYSA-N 0.000 claims description 2
- TWYWAXDQGCCUFI-UHFFFAOYSA-N 8-[8-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound C1(CC1)C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CC(NC2)=O)CC1 TWYWAXDQGCCUFI-UHFFFAOYSA-N 0.000 claims description 2
- SPIHTFMRNLJGDD-UHFFFAOYSA-N 8-[8-(3-ethyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C(C)C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CNC(O2)=O)CC1 SPIHTFMRNLJGDD-UHFFFAOYSA-N 0.000 claims description 2
- MTTOBLPLLNDSAE-UHFFFAOYSA-N 8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CNC(O2)=O)CC1 MTTOBLPLLNDSAE-UHFFFAOYSA-N 0.000 claims description 2
- RIHLYAITXJUFMQ-UHFFFAOYSA-N 8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-propan-2-yl-2,8-diazaspiro[4.5]decan-3-one Chemical compound C(C)(C)C1NC(CC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O RIHLYAITXJUFMQ-UHFFFAOYSA-N 0.000 claims description 2
- CEFMINOVHRWRIS-UHFFFAOYSA-N 8-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-4-propan-2-yl-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C(C)(C)C1NC(OC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O CEFMINOVHRWRIS-UHFFFAOYSA-N 0.000 claims description 2
- RLIRQTWMWGCPHL-UHFFFAOYSA-N 8-[8-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound C(C)(C)C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CNC(O2)=O)CC1 RLIRQTWMWGCPHL-UHFFFAOYSA-N 0.000 claims description 2
- PIRMCKRHUWNHIJ-UHFFFAOYSA-N 8-[8-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound FC(C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CNC(O2)=O)CC1)(F)F PIRMCKRHUWNHIJ-UHFFFAOYSA-N 0.000 claims description 2
- OCACSRBOUZWLHI-UHFFFAOYSA-N 8-[8-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]-8-azabicyclo[3.2.1]octan-3-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound FC(C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CC(NC2)=O)CC1)(F)F OCACSRBOUZWLHI-UHFFFAOYSA-N 0.000 claims description 2
- ZQIHVCAOEDZERM-UHFFFAOYSA-N 9-(3-methyl-1,2,4-oxadiazol-5-yl)-7-(4-pyrazol-1-ylpiperidin-1-yl)-3-oxa-9-azabicyclo[3.3.1]nonane Chemical compound CC1=NOC(=N1)N1C2COCC1CC(C2)N1CCC(CC1)N1N=CC=C1 ZQIHVCAOEDZERM-UHFFFAOYSA-N 0.000 claims description 2
- HTUAKUCQILXEBR-UHFFFAOYSA-N 9-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]-1-oxa-3,9-diazaspiro[4.6]undecan-2-one Chemical compound CC1=NOC(=N1)N1CCC(CCC1)N1CCC2(CNC(O2)=O)CCC1 HTUAKUCQILXEBR-UHFFFAOYSA-N 0.000 claims description 2
- PPDPCGDPIJUVEF-UHFFFAOYSA-N 9-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]-2,9-diazaspiro[4.6]undecan-3-one Chemical compound CC1=NOC(=N1)N1CCC(CCC1)N1CCC2(CC(NC2)=O)CCC1 PPDPCGDPIJUVEF-UHFFFAOYSA-N 0.000 claims description 2
- NPHMSVBFYLYSCR-UHFFFAOYSA-N 9-[1-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]azepan-4-yl]-1-oxa-3,9-diazaspiro[4.6]undecan-2-one Chemical compound FC(C1=NOC(=N1)N1CCC(CCC1)N1CCC2(CNC(O2)=O)CCC1)(F)F NPHMSVBFYLYSCR-UHFFFAOYSA-N 0.000 claims description 2
- CXBFWSRCRSBFFY-UHFFFAOYSA-N 9-[1-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]azepan-4-yl]-2,9-diazaspiro[4.6]undecan-3-one Chemical compound FC(C1=NOC(=N1)N1CCC(CCC1)N1CCC2(CC(NC2)=O)CCC1)(F)F CXBFWSRCRSBFFY-UHFFFAOYSA-N 0.000 claims description 2
- RYBXCSUPAKBJPR-UHFFFAOYSA-N 9-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-2-azabicyclo[2.2.2]octan-5-yl]-1-oxa-3,9-diazaspiro[4.6]undecan-2-one Chemical compound CC1=NOC(=N1)N1C2CC(C(C1)CC2)N1CCC2(CNC(O2)=O)CCC1 RYBXCSUPAKBJPR-UHFFFAOYSA-N 0.000 claims description 2
- PUFQPKPLGSCLKV-UHFFFAOYSA-N 9-[6-(3-methyl-1,2,4-oxadiazol-5-yl)-6-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,9-diazaspiro[4.6]undecan-2-one Chemical compound CC1=NOC(=N1)N1C2CC(CC(C1)C2)N1CCC2(CNC(O2)=O)CCC1 PUFQPKPLGSCLKV-UHFFFAOYSA-N 0.000 claims description 2
- KXTZOGUEIMZHJD-UHFFFAOYSA-N 9-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-1-oxa-3,9-diazaspiro[4.6]undecan-2-one Chemical compound CC1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CNC(O2)=O)CCC1 KXTZOGUEIMZHJD-UHFFFAOYSA-N 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 206010065390 Inflammatory pain Diseases 0.000 claims description 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 2
- 201000002832 Lewy body dementia Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
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- MLFLWHHYWOXSMP-IFJNFQAOSA-N [(2R,4R)-4-fluoro-1-[1-[1-(3-methyl-1,2,4-oxadiazol-5-yl)azepan-4-yl]piperidin-4-yl]pyrrolidin-2-yl]methanol Chemical compound F[C@@H]1C[C@@H](N(C1)C1CCN(CC1)C1CCN(CCC1)C1=NC(=NO1)C)CO MLFLWHHYWOXSMP-IFJNFQAOSA-N 0.000 claims description 2
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| JP2025174614A JP2026002915A (ja) | 2018-06-22 | 2025-10-16 | ムスカリンｍ１および／またはｍ４受容体のアゴニストとしてのオキサジアゾール |
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| JP2025174614A Pending JP2026002915A (ja) | 2018-06-22 | 2025-10-16 | ムスカリンｍ１および／またはｍ４受容体のアゴニストとしてのオキサジアゾール |
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| AU2012338581B2 (en) | 2011-11-18 | 2016-12-08 | Nxera Pharma Uk Limited | Muscarinic M1 receptor agonists |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| GB201810245D0 (en) * | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| KR20220079921A (ko) * | 2019-10-09 | 2022-06-14 | 노파르티스 아게 | M4 작용제로서의 2-아자스피로[3.4]옥탄 유도체 |
| PE20221454A1 (es) | 2019-10-09 | 2022-09-21 | Novartis Ag | Derivados de 2-azaespiro[3.4]octano como agonistas de m4 |
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| AU2307899A (en) * | 1997-12-23 | 1999-07-12 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| US7786141B2 (en) | 2004-08-19 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Dihydrospiroindene modulators of muscarinic receptors |
| US7858635B2 (en) | 2005-12-22 | 2010-12-28 | Vertex Pharmaceuticals Incorporated | Spiro compounds as modulators of muscarinic receptors |
| NZ570497A (en) | 2006-02-22 | 2011-09-30 | Vertex Pharma | Spiro condensed 4,4'-quinilino-piperidines derivatives as modulators of muscarinic receptors |
| EP2051712A2 (en) | 2006-08-15 | 2009-04-29 | Vertex Pharmceuticals Incorporated | Modulators of muscarinic receptors |
| WO2008117229A1 (en) * | 2007-03-23 | 2008-10-02 | Ranbaxy Laboratories Limited | Muscarinic receptor antagonists |
| US20130184257A1 (en) | 2010-09-17 | 2013-07-18 | Thomas Daniel Aicher | Piperidinyl-substituted lactams as gpr119 modulators |
| BR112015006029B1 (pt) | 2012-09-18 | 2022-01-25 | Heptares Therapeutics Limited | Compostos aza bicíclicos como agonistas de receptor m1 muscarínicos, composição farmacêutica compreendendo ditos compostos e uso dos mesmos para tratar um distúrbio cognitivo ou distúrbio psicótico ou para tratar ou reduzir a gravidade de dores agudas, crônicas, neuropáticas ou inflamatórias |
| WO2014122474A1 (en) | 2013-02-07 | 2014-08-14 | Takeda Pharmaceutical Company Limited | Piperidin-1 -yl and azepin-1 -yl carboxylates as muscarinic m4 receptor agonists |
| KR102352388B1 (ko) * | 2014-02-06 | 2022-01-17 | 헵테얼즈 테라퓨틱스 리미티드 | 무스카린성 m1 수용체 및/또는 m4 수용체 작용제로서 바이사이클릭 아자 화합물 |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513743D0 (en) * | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201513742D0 (en) * | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| GB201810245D0 (en) * | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
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2018
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2019
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- 2019-06-24 WO PCT/GB2019/051778 patent/WO2019243850A1/en not_active Ceased
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- 2019-06-24 EP EP19734158.9A patent/EP3810607A1/en active Pending
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2020
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2023
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2025
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