JP2019523233A5

JP2019523233A5 -

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Publication number: JP2019523233A5
Authority: JP; Japan
Prior art keywords: thieno; methyl; pyridazin; dimethyl; amine
Prior art date: 2017-06-22
Legal status : Granted

Application number

JP2018566971A

Other languages

English (en)

Japanese (ja)

Other versions

JP7038414B2 (ja

JP2019523233A (ja

Filing date

2017-06-22

Publication date

2020-07-30

2017-06-22 Application filed filed Critical

2017-06-22 Priority claimed from PCT/US2017/038711 external-priority patent/WO2017223290A1/en

2019-08-22 Publication of JP2019523233A publication Critical patent/JP2019523233A/ja

2020-07-30 Publication of JP2019523233A5 publication Critical patent/JP2019523233A5/ja

2022-03-18 Application granted granted Critical

2022-03-18 Publication of JP7038414B2 publication Critical patent/JP7038414B2/ja

Status Active legal-status Critical Current

2037-06-22 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 89
125000000623 heterocyclic group Chemical group 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
-1 hydroxy, phenyl Chemical group 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 31
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000000753 cycloalkyl group Chemical group 0.000 claims description 28
125000005842 heteroatom Chemical group 0.000 claims description 26
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 22
125000005843 halogen group Chemical group 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
208000035475 disorder Diseases 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 15
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 14
241000124008 Mammalia Species 0.000 claims description 12
230000004064 dysfunction Effects 0.000 claims description 12
208000020016 psychiatric disease Diseases 0.000 claims description 12
208000028017 Psychotic disease Diseases 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
208000010877 cognitive disease Diseases 0.000 claims description 7
201000000980 schizophrenia Diseases 0.000 claims description 7
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 5
230000003542 behavioural effect Effects 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 4
208000020925 Bipolar disease Diseases 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
208000019022 Mood disease Diseases 0.000 claims description 4
208000016285 Movement disease Diseases 0.000 claims description 4
YNPFUSWQWFQSLD-UHFFFAOYSA-N N-[(3-fluoro-4-methoxyphenyl)methyl]-12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound FC=1C=C(CNC2=NC=NC3=C2SC=2N=NC(=C(C=23)C)C)C=CC=1OC YNPFUSWQWFQSLD-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
230000036506 anxiety Effects 0.000 claims description 4
RIJPDMIRRQNWGX-UHFFFAOYSA-N N-[2-(4-methoxyphenyl)cyclopropyl]-12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound COC1=CC=C(C=C1)C1C(C1)NC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C RIJPDMIRRQNWGX-UHFFFAOYSA-N 0.000 claims description 3
IDAKPHHDTCRQMK-UHFFFAOYSA-N N-[[4-(2-fluoropyridin-3-yl)phenyl]methyl]-12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound FC1=NC=CC=C1C1=CC=C(CNC2=NC=NC3=C2SC=2N=NC(=C(C=23)C)C)C=C1 IDAKPHHDTCRQMK-UHFFFAOYSA-N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
ZWNZWHFKGJDMCH-LIJFRPJRSA-N 1,1,1,3,3,3-hexadeuterio-2-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]phenyl]propan-2-ol Chemical compound [2H]C(C(C([2H])([2H])[2H])(O)C1=CC=C(C=C1)CNC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C)([2H])[2H] ZWNZWHFKGJDMCH-LIJFRPJRSA-N 0.000 claims description 2
PCBFRNQVHONMQK-UHFFFAOYSA-N 1-[3-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]phenyl]cyclobutan-1-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC=1C=C(C=CC=1)C1(CCC1)O)C PCBFRNQVHONMQK-UHFFFAOYSA-N 0.000 claims description 2
WGQVOLVMJHNRSK-UHFFFAOYSA-N 1-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]phenyl]cyclobutan-1-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C1(CCC1)O)C WGQVOLVMJHNRSK-UHFFFAOYSA-N 0.000 claims description 2
DOELVVJGAUZNSI-UHFFFAOYSA-N 12,13-dimethyl-N-(1-phenylpyrrolidin-3-yl)-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NC1CN(CC1)C1=CC=CC=C1)C DOELVVJGAUZNSI-UHFFFAOYSA-N 0.000 claims description 2
SRIFPHBXTYUWFX-UHFFFAOYSA-N 12,13-dimethyl-N-(oxan-4-yl)-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NC1CCOCC1)C SRIFPHBXTYUWFX-UHFFFAOYSA-N 0.000 claims description 2
SMQPTPMSEXFUMM-UHFFFAOYSA-N 12,13-dimethyl-N-[(3-pyrazol-1-ylphenyl)methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC(=CC=C1)N1N=CC=C1)C SMQPTPMSEXFUMM-UHFFFAOYSA-N 0.000 claims description 2
HYZMBRDLNBACPG-UHFFFAOYSA-N 12,13-dimethyl-N-[(3-pyrimidin-2-ylphenyl)methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC(=CC=C1)C1=NC=CC=N1)C HYZMBRDLNBACPG-UHFFFAOYSA-N 0.000 claims description 2
RONWMLPNIYBCBQ-UHFFFAOYSA-N 12,13-dimethyl-N-[(4-piperazin-1-ylphenyl)methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)N1CCNCC1)C RONWMLPNIYBCBQ-UHFFFAOYSA-N 0.000 claims description 2
SULGJMLHVXHNNT-UHFFFAOYSA-N 12,13-dimethyl-N-[(4-pyrazol-1-ylphenyl)methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)N1N=CC=C1)C SULGJMLHVXHNNT-UHFFFAOYSA-N 0.000 claims description 2
KJYYIKBHSLJMCF-UHFFFAOYSA-N 12,13-dimethyl-N-[(4-pyridin-2-ylphenyl)methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C1=NC=CC=C1)C KJYYIKBHSLJMCF-UHFFFAOYSA-N 0.000 claims description 2
QUKZCPMOMWMICO-UHFFFAOYSA-N 12,13-dimethyl-N-[(4-thiophen-2-ylphenyl)methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C=1SC=CC=1)C QUKZCPMOMWMICO-UHFFFAOYSA-N 0.000 claims description 2
DSDVRFRSLJGMRG-UHFFFAOYSA-N 12,13-dimethyl-N-[1-(5-propan-2-yloxypyrimidin-2-yl)azetidin-3-yl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound C(C)(C)OC=1C=NC(=NC=1)N1CC(C1)NC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C DSDVRFRSLJGMRG-UHFFFAOYSA-N 0.000 claims description 2
RSNGKDVVMNOATG-UHFFFAOYSA-N 12,13-dimethyl-N-[[4-(1,3-thiazol-2-yl)phenyl]methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C=1SC=CN=1)C RSNGKDVVMNOATG-UHFFFAOYSA-N 0.000 claims description 2
DTTGQPFUBKDYKT-UHFFFAOYSA-N 12,13-dimethyl-N-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical class CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C1=NN(C=C1)C)C DTTGQPFUBKDYKT-UHFFFAOYSA-N 0.000 claims description 2
JBPHGRFDUIOCAK-UHFFFAOYSA-N 12,13-dimethyl-N-[[4-(1-methylpyrrol-2-yl)phenyl]methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical class CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C=1N(C=CC=1)C)C JBPHGRFDUIOCAK-UHFFFAOYSA-N 0.000 claims description 2
YRUQMYJCRHOYQJ-UHFFFAOYSA-N 12,13-dimethyl-N-[[4-(1H-pyrrol-2-yl)phenyl]methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C=1NC=CC=1)C YRUQMYJCRHOYQJ-UHFFFAOYSA-N 0.000 claims description 2
XYUVUUZUEKFIRX-UHFFFAOYSA-N 12,13-dimethyl-N-[[4-(2-methylpyrazol-3-yl)phenyl]methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical class CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C=1N(N=CC=1)C)C XYUVUUZUEKFIRX-UHFFFAOYSA-N 0.000 claims description 2
IQUCPSZPDLFQPO-UHFFFAOYSA-N 12,13-dimethyl-N-[[4-(4-methylpiperazin-1-yl)phenyl]methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical class CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)N1CCN(CC1)C)C IQUCPSZPDLFQPO-UHFFFAOYSA-N 0.000 claims description 2
AGLHOSOYJBMYKI-UHFFFAOYSA-N 12,13-dimethyl-N-[[4-(oxetan-3-yl)phenyl]methyl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C1COC1)C AGLHOSOYJBMYKI-UHFFFAOYSA-N 0.000 claims description 2
NKENRWRKIWWKJZ-UHFFFAOYSA-N 12-chloro-N-[(3-fluoro-4-methoxyphenyl)methyl]-13-methyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexaen-6-amine Chemical compound ClC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC(=C(C=C1)OC)F)C NKENRWRKIWWKJZ-UHFFFAOYSA-N 0.000 claims description 2
IOKNMOWXFPZFSJ-UHFFFAOYSA-N 12-chloro-N-cyclobutyl-13-methyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexaen-6-amine Chemical compound ClC1=C(C2=C(N=N1)SC1=C2N=CN=C1NC1CCC1)C IOKNMOWXFPZFSJ-UHFFFAOYSA-N 0.000 claims description 2
HLDRXNVXRJPTSD-UHFFFAOYSA-N 12-methoxy-13-methyl-N-[1-[5-(trifluoromethyl)pyrimidin-2-yl]azetidin-3-yl]-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(13),2(7),3,5,9,11-hexaen-6-amine Chemical compound COC1=C(C2=C(N=N1)SC1=C2N=CN=C1NC1CN(C1)C1=NC=C(C=N1)C(F)(F)F)C HLDRXNVXRJPTSD-UHFFFAOYSA-N 0.000 claims description 2
GLVUDKZWPUQPQJ-UHFFFAOYSA-N 2-[1-[[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]phenyl]methyl]pyrrolidin-2-yl]propan-2-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)CN1C(CCC1)C(C)(C)O)C GLVUDKZWPUQPQJ-UHFFFAOYSA-N 0.000 claims description 2
CBKUUQRGJNXMLJ-UHFFFAOYSA-N 2-[2-chloro-4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]phenyl]propan-2-ol Chemical compound ClC1=C(C=CC(=C1)CNC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C)C(C)(C)O CBKUUQRGJNXMLJ-UHFFFAOYSA-N 0.000 claims description 2
FNQYJMPWMSQOAS-UHFFFAOYSA-N 2-[3-chloro-4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]phenyl]propan-2-ol Chemical compound ClC=1C=C(C=CC=1CNC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C)C(C)(C)O FNQYJMPWMSQOAS-UHFFFAOYSA-N 0.000 claims description 2
ITISENDFRDJXSD-UHFFFAOYSA-N 2-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]-2-fluorophenyl]propan-2-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC(=C(C=C1)C(C)(C)O)F)C ITISENDFRDJXSD-UHFFFAOYSA-N 0.000 claims description 2
KVSDFFQPEXJZHL-UHFFFAOYSA-N 2-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]-2-methylphenyl]propan-2-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC(=C(C=C1)C(C)(C)O)C)C KVSDFFQPEXJZHL-UHFFFAOYSA-N 0.000 claims description 2
ICDFXRSEUQGTLP-UHFFFAOYSA-N 2-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]-3-fluorophenyl]-2-methylpropan-1-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=C(C=C(C=C1)C(CO)(C)C)F)C ICDFXRSEUQGTLP-UHFFFAOYSA-N 0.000 claims description 2
PURHQKBEVDIBKZ-UHFFFAOYSA-N 2-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]-3-fluorophenyl]butan-2-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=C(C=C(C=C1)C(C)(CC)O)F)C PURHQKBEVDIBKZ-UHFFFAOYSA-N 0.000 claims description 2
WPQVTABMYNWREC-UHFFFAOYSA-N 2-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]-3-methylphenyl]propan-2-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=C(C=C(C=C1)C(C)(C)O)C)C WPQVTABMYNWREC-UHFFFAOYSA-N 0.000 claims description 2
BPLWRYNGXLPHCM-UHFFFAOYSA-N 2-[4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]phenyl]-2-methylpropan-1-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC1=CC=C(C=C1)C(CO)(C)C)C BPLWRYNGXLPHCM-UHFFFAOYSA-N 0.000 claims description 2
CPESWLHVCBJWLO-UHFFFAOYSA-N 2-[5-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]-2-fluorophenyl]propan-2-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC=1C=CC(=C(C=1)C(C)(C)O)F)C CPESWLHVCBJWLO-UHFFFAOYSA-N 0.000 claims description 2
CMNFQIALAQNMOD-UHFFFAOYSA-N 3-[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]-1-(4-fluorophenyl)cyclobutan-1-ol Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NC1CC(C1)(O)C1=CC=C(C=C1)F)C CMNFQIALAQNMOD-UHFFFAOYSA-N 0.000 claims description 2
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 2
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 2
208000020706 Autistic disease Diseases 0.000 claims description 2
206010012289 Dementia Diseases 0.000 claims description 2
208000012661 Dyskinesia Diseases 0.000 claims description 2
206010026749 Mania Diseases 0.000 claims description 2
208000026139 Memory disease Diseases 0.000 claims description 2
208000036626 Mental retardation Diseases 0.000 claims description 2
ABDFEPIADOKELH-UHFFFAOYSA-N N,N,12,13-tetramethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound CN(C1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C)C ABDFEPIADOKELH-UHFFFAOYSA-N 0.000 claims description 2
HEFXBBBRYHBAGO-UHFFFAOYSA-N N-(azetidin-3-yl)-12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound N1CC(C1)NC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C HEFXBBBRYHBAGO-UHFFFAOYSA-N 0.000 claims description 2
XQGMAMICKAAJGQ-UHFFFAOYSA-N N-[(3,4-dimethoxyphenyl)methyl]-12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-amine Chemical compound COC=1C=C(C=CC=1OC)CNC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C XQGMAMICKAAJGQ-UHFFFAOYSA-N 0.000 claims description 2
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SQBJVDMRKXOKFZ-UHFFFAOYSA-N N-cyclopentyl-4-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]benzamide Chemical compound C1(CCCC1)NC(C1=CC=C(C=C1)CNC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C)=O SQBJVDMRKXOKFZ-UHFFFAOYSA-N 0.000 description 1
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MTMRAINRRKYNEB-UHFFFAOYSA-N N-cyclopropyl-5-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]-2-fluorobenzamide Chemical compound C1(CC1)NC(C1=C(C=CC(=C1)CNC1=NC=NC2=C1SC=1N=NC(=C(C=12)C)C)F)=O MTMRAINRRKYNEB-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
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230000015572 biosynthetic process Effects 0.000 description 1
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210000002932 cholinergic neuron Anatomy 0.000 description 1
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125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
229940088598 enzyme Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
125000005553 heteroaryloxy group Chemical group 0.000 description 1
125000000592 heterocycloalkyl group Chemical group 0.000 description 1
210000001320 hippocampus Anatomy 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
DTPSLUVYVAOJRY-UHFFFAOYSA-N methyl 3-[[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]methyl]bicyclo[1.1.1]pentane-1-carboxylate Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NCC12CC(C1)(C2)C(=O)OC)C DTPSLUVYVAOJRY-UHFFFAOYSA-N 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
239000002243 precursor Substances 0.000 description 1
210000004129 prosencephalon Anatomy 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
ZPQVZKJKWBZSOK-UHFFFAOYSA-N tert-butyl 3-[(12,13-dimethyl-8-thia-3,5,10,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl)amino]azetidine-1-carboxylate Chemical compound CC1=C(C2=C(N=N1)SC1=C2N=CN=C1NC1CN(C1)C(=O)OC(C)(C)C)C ZPQVZKJKWBZSOK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
UYGIYVMPGNRKTG-UHFFFAOYSA-N thieno[2,3-c]pyridazine Chemical compound C1=NN=C2SC=CC2=C1 UYGIYVMPGNRKTG-UHFFFAOYSA-N 0.000 description 1
QIZMFTNGJPBSBT-UHFFFAOYSA-N thieno[3,2-d]pyrimidin-4-amine Chemical compound NC1=NC=NC2=C1SC=C2 QIZMFTNGJPBSBT-UHFFFAOYSA-N 0.000 description 1

JP2018566971A 2016-06-22 2017-06-22 ムスカリン性アセチルコリンレセプターｍ４のポジティブアロステリック調節因子 Active JP7038414B2 (ja)