JP2012530084A5 - - Google Patents
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- JP2012530084A5 JP2012530084A5 JP2012515322A JP2012515322A JP2012530084A5 JP 2012530084 A5 JP2012530084 A5 JP 2012530084A5 JP 2012515322 A JP2012515322 A JP 2012515322A JP 2012515322 A JP2012515322 A JP 2012515322A JP 2012530084 A5 JP2012530084 A5 JP 2012530084A5
- Authority
- JP
- Japan
- Prior art keywords
- diazatricyclo
- undecane
- pyridin
- heteroaryl
- monocyclic
- 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.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000001188 haloalkyl group Chemical group 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 208000002193 Pain Diseases 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- -1 1,3-thiazolyl Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 150000002430 hydrocarbons Chemical class 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000004454 Hyperalgesia Diseases 0.000 claims 2
- 208000005298 acute pain Diseases 0.000 claims 2
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims 2
- 239000003693 atypical antipsychotic agent Substances 0.000 claims 2
- 229940127236 atypical antipsychotics Drugs 0.000 claims 2
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 108010052671 nicotinic receptor alpha4beta2 Proteins 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- UFEPSYPWWUXPPQ-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound C1=C(Cl)C(F)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 UFEPSYPWWUXPPQ-UHFFFAOYSA-N 0.000 claims 1
- APMHSXJCMXBHJY-UHFFFAOYSA-N (3-chlorophenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound ClC1=CC=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 APMHSXJCMXBHJY-UHFFFAOYSA-N 0.000 claims 1
- GVOXZLAEIZBSPH-UHFFFAOYSA-N (5-chloro-2-fluorophenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound FC1=CC=C(Cl)C=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 GVOXZLAEIZBSPH-UHFFFAOYSA-N 0.000 claims 1
- ZAJVRLDMHXFICV-UHFFFAOYSA-N (5-chloro-2-methoxyphenyl)-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)methanone Chemical compound COC1=CC=C(Cl)C=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 ZAJVRLDMHXFICV-UHFFFAOYSA-N 0.000 claims 1
- XRRUCMXUIAATKQ-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(1,2,3,4-tetrahydronaphthalen-2-yl)methanone Chemical compound C1CC2=CC=CC=C2CC1C(=O)N1CC(C2)CN3CC1CC2C3 XRRUCMXUIAATKQ-UHFFFAOYSA-N 0.000 claims 1
- YNRCDWSRGVZPCH-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(1H-indazol-3-yl)methanone Chemical compound N=1NC2=CC=CC=C2C=1C(=O)N1CC(C2)CN3CC1CC2C3 YNRCDWSRGVZPCH-UHFFFAOYSA-N 0.000 claims 1
- PCPNXIMJIARXAV-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(1H-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)N1CC(C2)CN3CC1CC2C3 PCPNXIMJIARXAV-UHFFFAOYSA-N 0.000 claims 1
- KLCDVRMTMVKZCC-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(1H-pyrrol-2-yl)methanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CN1 KLCDVRMTMVKZCC-UHFFFAOYSA-N 0.000 claims 1
- ONZFIUXTTRXGFK-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(furan-2-yl)methanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CO1 ONZFIUXTTRXGFK-UHFFFAOYSA-N 0.000 claims 1
- CEKNKWVIDWJMBP-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(phenyl)methanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CC=C1 CEKNKWVIDWJMBP-UHFFFAOYSA-N 0.000 claims 1
- IFFHDIHUAJIEKP-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(pyridin-2-yl)methanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CC=N1 IFFHDIHUAJIEKP-UHFFFAOYSA-N 0.000 claims 1
- FUJXILCZCPMXSN-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(pyridin-3-yl)methanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CN=C1 FUJXILCZCPMXSN-UHFFFAOYSA-N 0.000 claims 1
- DXALTJUIQNYPOE-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(quinolin-2-yl)methanone Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)N1CC(C2)CN3CC1CC2C3 DXALTJUIQNYPOE-UHFFFAOYSA-N 0.000 claims 1
- QZFQDVLIAQNSLM-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(thieno[2,3-c]pyridin-5-yl)methanone Chemical compound C=1C=2C=CSC=2C=NC=1C(=O)N1CC(C2)CN3CC1CC2C3 QZFQDVLIAQNSLM-UHFFFAOYSA-N 0.000 claims 1
- PZIWBLGELKZIOQ-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(thieno[3,2-b]pyridin-5-yl)methanone Chemical compound C=1C=C2SC=CC2=NC=1C(=O)N1CC(C2)CN3CC1CC2C3 PZIWBLGELKZIOQ-UHFFFAOYSA-N 0.000 claims 1
- GTWISGOTEDNEDS-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl(thiophen-2-yl)methanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CS1 GTWISGOTEDNEDS-UHFFFAOYSA-N 0.000 claims 1
- GCZBWMHAHNWILC-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(1-methylpyrrol-2-yl)methanone Chemical compound CN1C=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 GCZBWMHAHNWILC-UHFFFAOYSA-N 0.000 claims 1
- KUSBBTYCOSBTQH-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2,3-difluorophenyl)methanone Chemical compound FC1=CC=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1F KUSBBTYCOSBTQH-UHFFFAOYSA-N 0.000 claims 1
- CFAOLDAIGUJGHQ-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2,3-dimethylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1C CFAOLDAIGUJGHQ-UHFFFAOYSA-N 0.000 claims 1
- SWQXKWMAAILBPF-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2,4-difluorophenyl)methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 SWQXKWMAAILBPF-UHFFFAOYSA-N 0.000 claims 1
- CQXUWLSOJJLWGZ-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2,5-dimethylfuran-3-yl)methanone Chemical compound O1C(C)=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1C CQXUWLSOJJLWGZ-UHFFFAOYSA-N 0.000 claims 1
- IZUQKAOYIKFKRV-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2,5-dimethylphenyl)methanone Chemical compound CC1=CC=C(C)C(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 IZUQKAOYIKFKRV-UHFFFAOYSA-N 0.000 claims 1
- RWFPJTRYQPDMRK-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 RWFPJTRYQPDMRK-UHFFFAOYSA-N 0.000 claims 1
- UFDSVRIDRGHVGO-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2-hydroxyphenyl)methanone Chemical compound OC1=CC=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 UFDSVRIDRGHVGO-UHFFFAOYSA-N 0.000 claims 1
- KRKKJEJPMRKTQF-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2-methoxypyridin-3-yl)methanone Chemical compound COC1=NC=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 KRKKJEJPMRKTQF-UHFFFAOYSA-N 0.000 claims 1
- BPWSKNYQZWQJDU-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 BPWSKNYQZWQJDU-UHFFFAOYSA-N 0.000 claims 1
- YHWZDXDPTGGNCD-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(2-phenylpyrazol-3-yl)methanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=NN1C1=CC=CC=C1 YHWZDXDPTGGNCD-UHFFFAOYSA-N 0.000 claims 1
- YFJGHGINAYHYDD-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(3,4-difluorophenyl)methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 YFJGHGINAYHYDD-UHFFFAOYSA-N 0.000 claims 1
- YPKSWMNMPQVBAI-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 YPKSWMNMPQVBAI-UHFFFAOYSA-N 0.000 claims 1
- JDIMGWXPYSSYJB-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(3-methylfuran-2-yl)methanone Chemical compound C1=COC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1C JDIMGWXPYSSYJB-UHFFFAOYSA-N 0.000 claims 1
- UCTXCLORTHSTEI-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 UCTXCLORTHSTEI-UHFFFAOYSA-N 0.000 claims 1
- KHPXCMPGVLSQGL-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(4-ethoxyphenyl)methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 KHPXCMPGVLSQGL-UHFFFAOYSA-N 0.000 claims 1
- ZEZDFSCWDVNANX-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 ZEZDFSCWDVNANX-UHFFFAOYSA-N 0.000 claims 1
- DOHMMCTWKDFNOR-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(4-fluoro-3-methylphenyl)methanone Chemical compound C1=C(F)C(C)=CC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 DOHMMCTWKDFNOR-UHFFFAOYSA-N 0.000 claims 1
- SFGXHAYOZZIXGD-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(4-methylthiophen-2-yl)methanone Chemical compound CC1=CSC(C(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 SFGXHAYOZZIXGD-UHFFFAOYSA-N 0.000 claims 1
- QSYRECSJNCDMBN-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-(5-methylthiophen-2-yl)methanone Chemical compound S1C(C)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 QSYRECSJNCDMBN-UHFFFAOYSA-N 0.000 claims 1
- HDNGCJMRFKVVBA-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(CN(C2)C3)CC2CC3C1 HDNGCJMRFKVVBA-UHFFFAOYSA-N 0.000 claims 1
- QSJXHKFTZFDXSD-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecan-5-one Chemical group O=C1NC(C2)CN3CC1CC2C3 QSJXHKFTZFDXSD-UHFFFAOYSA-N 0.000 claims 1
- JMJUWQIOHYBWPM-UHFFFAOYSA-N 1,4-diazatricyclo[4.3.1.13,8]undecane Chemical compound C1N(C2)CC3CC2CNC1C3 JMJUWQIOHYBWPM-UHFFFAOYSA-N 0.000 claims 1
- ADVUOUWNIKBLTH-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-(2,5-dimethoxyphenyl)ethanone Chemical compound COC1=CC=C(OC)C(CC(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 ADVUOUWNIKBLTH-UHFFFAOYSA-N 0.000 claims 1
- MOCKOLWUTUXVSD-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-(2-fluorophenyl)ethanone Chemical compound FC1=CC=CC=C1CC(=O)N1C(CN(C2)C3)CC2CC3C1 MOCKOLWUTUXVSD-UHFFFAOYSA-N 0.000 claims 1
- GUIMUEYGRLWUGA-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1CC(=O)N1C(CN(C2)C3)CC2CC3C1 GUIMUEYGRLWUGA-UHFFFAOYSA-N 0.000 claims 1
- NYICTSAADDDOBB-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(CC(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 NYICTSAADDDOBB-UHFFFAOYSA-N 0.000 claims 1
- KSUCWFSMUCLSQZ-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-(3-methylphenyl)ethanone Chemical compound CC1=CC=CC(CC(=O)N2C3CC4CC(CN(C4)C3)C2)=C1 KSUCWFSMUCLSQZ-UHFFFAOYSA-N 0.000 claims 1
- VEDIHKHAUHTSBD-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-[2-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC=C1CC(=O)N1C(CN(C2)C3)CC2CC3C1 VEDIHKHAUHTSBD-UHFFFAOYSA-N 0.000 claims 1
- XRSVWIJDRKTJFX-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-[4-(dimethylamino)phenyl]ethanone Chemical compound C1=CC(N(C)C)=CC=C1CC(=O)N1C(CN(C2)C3)CC2CC3C1 XRSVWIJDRKTJFX-UHFFFAOYSA-N 0.000 claims 1
- HBYVZFDLBOFHAK-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-phenoxyethanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)COC1=CC=CC=C1 HBYVZFDLBOFHAK-UHFFFAOYSA-N 0.000 claims 1
- GEDLNOAXRZAKME-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-thiophen-2-ylethanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)CC1=CC=CS1 GEDLNOAXRZAKME-UHFFFAOYSA-N 0.000 claims 1
- DIUWEZWCUHHKBX-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-2-thiophen-3-ylethanone Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)CC=1C=CSC=1 DIUWEZWCUHHKBX-UHFFFAOYSA-N 0.000 claims 1
- NUODDFYENHDLFJ-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-3-phenylbutan-1-one Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)CC(C)C1=CC=CC=C1 NUODDFYENHDLFJ-UHFFFAOYSA-N 0.000 claims 1
- KAWVLRZQIHCMIR-UHFFFAOYSA-N 1-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-3-phenylpropan-1-one Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)CCC1=CC=CC=C1 KAWVLRZQIHCMIR-UHFFFAOYSA-N 0.000 claims 1
- BSHJNFRDMXVCBN-UHFFFAOYSA-N 1-{2-[5-(1,4-diazatricyclo[4.3.1.13,8]undec-4-yl)pyridin-3-yl]phenyl}ethanone Chemical compound CC(=O)C1=CC=CC=C1C1=CN=CC(N2C3CC4CC(CN(C4)C3)C2)=C1 BSHJNFRDMXVCBN-UHFFFAOYSA-N 0.000 claims 1
- HTIKEGIKZQYHTO-UHFFFAOYSA-N 2-(1,4-diazatricyclo[4.3.1.13,8]undecan-4-yl)-5-phenyl-1,3,4-oxadiazole Chemical compound C1C(C2)CC3CN2CC1CN3C(O1)=NN=C1C1=CC=CC=C1 HTIKEGIKZQYHTO-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- TWPWFUABIMXXNA-UHFFFAOYSA-N 3-(1,4-diazatricyclo[4.3.1.13,8]undecane-4-carbonyl)benzonitrile Chemical compound C1C(CN(C2)C3)CC2CC3N1C(=O)C1=CC=CC(C#N)=C1 TWPWFUABIMXXNA-UHFFFAOYSA-N 0.000 claims 1
- RJBVGJISFOPTFT-UHFFFAOYSA-N 3-[5-(1,4-diazatricyclo[4.3.1.13,8]undec-4-yl)pyridin-3-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C=C(C=NC=2)N2C3CC4CC(CN(C4)C3)C2)=C1 RJBVGJISFOPTFT-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
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- 230000005586 smoking cessation Effects 0.000 claims 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 208000004371 toothache Diseases 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims 1
- 208000009935 visceral pain Diseases 0.000 claims 1
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| CA2809028C (en) * | 2010-08-20 | 2019-04-09 | Research Triangle Institute | Nicotinic receptor compounds |
| CN103087001A (zh) * | 2011-11-03 | 2013-05-08 | 南京大学 | 香草酸的1，3，4-噁二唑衍生物及其制法和用途 |
| WO2014165090A1 (en) * | 2013-03-13 | 2014-10-09 | The Broad Institute, Inc. | Compounds for the treatment of tuberculosis |
| RU2552649C1 (ru) * | 2013-12-13 | 2015-06-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет тонких химических технологий имени М.В. Ломоносова" (МИТХТ им. М.В. Ломоносова) | Душистые 5-бензил-1,3-диазаадамантан-6-оны |
| WO2015103005A1 (en) * | 2014-01-03 | 2015-07-09 | Research Institute At Nationwide Children's Hospital | Amphiphilic amine compounds and their use as therapeutic agents and nanocarriers |
| EP3623371A1 (en) | 2014-12-16 | 2020-03-18 | Axovant Sciences GmbH | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| CN107847494A (zh) | 2015-06-10 | 2018-03-27 | 阿考温特科学股份有限公司 | 作为α7‑烟碱乙酰胆碱受体激动剂的氨基苯并异噁唑化合物 |
| JP2018523707A (ja) | 2015-08-12 | 2018-08-23 | アクソバント サイエンシズ ゲーエムベーハー | α７−ニコチン性アセチルコリン受容体のアゴニストとしてのジェミナル置換アミノベンゾイソオキサゾール化合物 |
| IL294124B2 (en) | 2015-12-10 | 2024-02-01 | Ptc Therapeutics Inc | Methods for treating huntington's disease |
| US11407753B2 (en) | 2017-06-05 | 2022-08-09 | Ptc Therapeutics, Inc. | Compounds for treating Huntington's disease |
| US11382918B2 (en) | 2017-06-28 | 2022-07-12 | Ptc Therapeutics, Inc. | Methods for treating Huntington's Disease |
| WO2019005993A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | METHODS OF TREATING HUNTINGTON'S DISEASE |
| EP3749666A1 (en) * | 2018-02-08 | 2020-12-16 | Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. | Heteroaryl compounds, pharmaceutical compositions thereof, and their therapeutic use |
| MX2020009957A (es) | 2018-03-27 | 2021-01-15 | Ptc Therapeutics Inc | Compuestos para el tratamiento de enfermedad de hungtinton. |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| PL3814357T3 (pl) | 2018-06-27 | 2024-09-16 | Ptc Therapeutics, Inc. | Związki heterocykliczne i heteroarylowe do leczenia choroby huntingtona |
| EP3814345B8 (en) | 2018-06-27 | 2024-10-30 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| WO2020231977A1 (en) | 2019-05-13 | 2020-11-19 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
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| US4557865A (en) * | 1984-05-07 | 1985-12-10 | Pennwalt Corporation | Substituted 4-azatricyclo[4.3.1.13,8 ]undecane compounds |
| NZ321970A (en) * | 1995-11-02 | 2000-02-28 | Neurosearch As | Fused tropane-derivatives as neurotransmitter reuptake inhibitors |
| US6093724A (en) * | 1998-08-18 | 2000-07-25 | Ucb, S.A. | Muscarinic agonists and antagonists |
| US6468998B1 (en) * | 1998-11-02 | 2002-10-22 | Mitsubishi Pharma Corporation | Pyrrolidine compounds and medicinal utilization thereof |
| EP1395257A1 (en) * | 2001-06-12 | 2004-03-10 | Elan Pharmaceuticals, Inc. | Macrocycles useful in the treatment of alzheimer's disease |
| US20050065178A1 (en) * | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| DE602004006767T2 (de) * | 2003-09-26 | 2008-02-07 | Astrazeneca Ab | Nichtamidnonane |
| US8314119B2 (en) | 2006-11-06 | 2012-11-20 | Abbvie Inc. | Azaadamantane derivatives and methods of use |
| TW200840569A (en) * | 2007-03-13 | 2008-10-16 | Targacept Inc | Sub-type selective amides of diazabicycloalkanes |
| EP2129672B1 (en) * | 2007-03-23 | 2011-05-18 | Abbott Laboratories | Azaadamantane ester and carbamate derivatives and methods of use thereof |
| CA2679885A1 (en) * | 2007-03-23 | 2008-10-02 | Abbott Laboratories | Aminomethyl azaadamantane derivatives and use thereof as selective modulators of the alpha7- neuronal nicotinic acetylcholine receptor (nnrs) |
| ATE538122T1 (de) * | 2007-03-23 | 2012-01-15 | Abbott Lab | Acetamid- und carboxamid-derivate von azaadamantan sowie verfahren zu ihrer verwendung |
| JP5540099B2 (ja) * | 2009-09-14 | 2014-07-02 | スベン ライフ サイエンシズ リミティド | ５−ｈｔ４受容体リガンドとしての１，２−ジヒドロ−２−オキソキノリン化合物 |
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- 2010-06-18 RU RU2015110025/04A patent/RU2015110025A/ru not_active Application Discontinuation
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- 2010-06-18 RU RU2012101784/04A patent/RU2549551C2/ru not_active IP Right Cessation
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