BR112020026437A2 - compostos farmacêuticos - Google Patents

Info

Publication number

BR112020026437A2

BR112020026437A2 BR112020026437-7A BR112020026437A BR112020026437A2 BR 112020026437 A2 BR112020026437 A2 BR 112020026437A2 BR 112020026437 A BR112020026437 A BR 112020026437A BR 112020026437 A2 BR112020026437 A2 BR 112020026437A2

Authority

BR

Brazil

Prior art keywords

methyl

oxadiazol

azabicyclo

octan

diazaspiro

Prior art date

2018-06-22

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 227
• 238000011282 treatment Methods 0.000 claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• -1 3-methyl-1,2,4-oxadiazol-5-yl Chemical group 0.000 claims description 210
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 97
• 229910052757 nitrogen Inorganic materials 0.000 claims description 67
• 150000003839 salts Chemical class 0.000 claims description 53
• 125000005842 heteroatom Chemical group 0.000 claims description 49
• 229910052760 oxygen Inorganic materials 0.000 claims description 46
• 125000002950 monocyclic group Chemical group 0.000 claims description 39
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• 208000002193 Pain Diseases 0.000 claims description 31
• 208000010877 cognitive disease Diseases 0.000 claims description 29
• 125000002619 bicyclic group Chemical group 0.000 claims description 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 208000024827 Alzheimer disease Diseases 0.000 claims description 22
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• 230000000694 effects Effects 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 17
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 13
• AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 claims description 13
• 208000004296 neuralgia Diseases 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 11
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 11
• 125000004043 oxo group Chemical group O=* 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 229930195734 saturated hydrocarbon Natural products 0.000 claims description 8
• 208000028017 Psychotic disease Diseases 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-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 6
• 230000001154 acute effect Effects 0.000 claims description 6
• 239000011737 fluorine Chemical group 0.000 claims description 6
• 208000021722 neuropathic pain Diseases 0.000 claims description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
• DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 5
• 206010065390 Inflammatory pain Diseases 0.000 claims description 5
• 229940121743 Muscarinic receptor agonist Drugs 0.000 claims description 5
• 208000005298 acute pain Diseases 0.000 claims description 5
• 239000000472 muscarinic agonist Substances 0.000 claims description 5
• 230000002981 neuropathic effect Effects 0.000 claims description 5
• 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 4
• 208000000094 Chronic Pain Diseases 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 230000001684 chronic effect Effects 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• KYZUPCHZMJVTAL-UHFFFAOYSA-N 9-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-2,9-diazaspiro[4.6]undecan-3-one Chemical compound CC1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CC(NC2)=O)CCC1 KYZUPCHZMJVTAL-UHFFFAOYSA-N 0.000 claims description 3
• 125000003118 aryl group Chemical group 0.000 claims description 3
• HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 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
• JQWZYXHQBRTBAW-UHFFFAOYSA-N 1-[6-(3-methyl-1,2,4-oxadiazol-5-yl)-6-azaspiro[3.4]octan-2-yl]-4-phenylpiperidine-4-carbonitrile Chemical compound CC1=NOC(=N1)N1CC2(CC(C2)N2CCC(CC2)(C#N)C2=CC=CC=C2)CC1 JQWZYXHQBRTBAW-UHFFFAOYSA-N 0.000 claims description 2
• CSSUCKGOCFKHJA-UHFFFAOYSA-N 1-[8-(3-methyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-N-[1-(trifluoromethyl)cyclobutyl]piperidine-4-carboxamide Chemical compound CC1=NOC(=N1)N1C2CC(CC1CC2)N1CCC(CC1)C(=O)NC1(CCC1)C(F)(F)F CSSUCKGOCFKHJA-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
• OAXGFDAGBSBICD-UHFFFAOYSA-N 1-benzyl-8-[6-(3-methyl-1,2,4-oxadiazol-5-yl)-6-azaspiro[3.4]octan-2-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound C(C1=CC=CC=C1)C1NC(CC11CCN(CC1)C1CC2(C1)CN(CC2)C1=NC(=NO1)C)=O OAXGFDAGBSBICD-UHFFFAOYSA-N 0.000 claims description 2
• BEUHTYMPYUINKD-UHFFFAOYSA-N 1-benzyl-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 C(C1=CC=CC=C1)C1NC(CC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O BEUHTYMPYUINKD-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
• 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
• 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
• 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
• 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
• PLBMQHUKQZSGCD-UHFFFAOYSA-N 4-benzyl-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 C(C1=CC=CC=C1)C1NC(OC11CCN(CC1)C1CC2CCC(C1)N2C1=NC(=NO1)C)=O PLBMQHUKQZSGCD-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
• 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
• NNAABNZFEGLVOG-UHFFFAOYSA-N 8-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-2-azabicyclo[2.2.2]octan-5-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound CC1=NOC(=N1)N1C2CC(C(C1)CC2)N1CCC2(CC(NC2)=O)CC1 NNAABNZFEGLVOG-UHFFFAOYSA-N 0.000 claims description 2
• HBSVAVNRDXYOLC-UHFFFAOYSA-N 8-[6-(3-methyl-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 CC1=NOC(=N1)N1C2CC(CC(C1)C2)N1CCC2(CNC(O2)=O)CC1 HBSVAVNRDXYOLC-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
• SZEPHDYLPNODKO-UHFFFAOYSA-N 8-[8-(3-ethyl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound C(C)C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CC(NC2)=O)CC1 SZEPHDYLPNODKO-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
• NBNUFEDTUCUSKA-UHFFFAOYSA-N 8-[8-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)-8-azabicyclo[3.2.1]octan-3-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound C(C)(C)C1=NOC(=N1)N1C2CC(CC1CC2)N1CCC2(CC(NC2)=O)CC1 NBNUFEDTUCUSKA-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
• JKZAZGQYIADGMN-UHFFFAOYSA-N 8-[9-(3-methyl-1,2,4-oxadiazol-5-yl)-9-azabicyclo[3.3.1]nonan-3-yl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound CC1=NOC(=N1)N1C2CC(CC1CCC2)N1CCC2(CNC(O2)=O)CC1 JKZAZGQYIADGMN-UHFFFAOYSA-N 0.000 claims description 2
• ZQAICIPASYXVRE-UHFFFAOYSA-N 8-[9-(3-methyl-1,2,4-oxadiazol-5-yl)-9-azabicyclo[3.3.1]nonan-3-yl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound CC1=NOC(=N1)N1C2CC(CC1CCC2)N1CCC2(CC(NC2)=O)CC1 ZQAICIPASYXVRE-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
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