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
- 230000000698 schizophrenic effect Effects 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
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- 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
- 0 *N1C(CC(C2)C3)C*3CC2*1 Chemical compound *N1C(CC(C2)C3)C*3CC2*1 0.000 description 1
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| PCT/CN2010/000889 WO2010145208A1 (en) | 2009-06-19 | 2010-06-18 | Diazahomoadamantane derivatives and methods of use thereof |
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| WO2012024615A1 (en) * | 2010-08-20 | 2012-02-23 | 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 |
| US10301294B2 (en) | 2013-03-13 | 2019-05-28 | 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 |
| WO2016100184A1 (en) | 2014-12-16 | 2016-06-23 | Forum Pharmaceuticals, Inc. | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| MX2017016231A (es) | 2015-06-10 | 2018-11-29 | Axovant Sciences Gmbh | Compuestos de aminobencisoxazol como agonistas de receptores a7-nicotínicos de acetilcolina. |
| WO2017027600A1 (en) | 2015-08-12 | 2017-02-16 | Forum Pharmaceuticals, Inc. | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF α7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| EA201800367A1 (ru) | 2015-12-10 | 2019-02-28 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения болезни хантингтона |
| EP3634953B1 (en) | 2017-06-05 | 2024-01-03 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
| MX2019015580A (es) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics Inc | Metodos para tratar la enfermedad de huntington. |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| WO2019155468A1 (en) * | 2018-02-08 | 2019-08-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Heteroaryl compounds, pharmaceutical compositions thereof, and their therapeutic use |
| EA202092001A1 (ru) | 2018-03-27 | 2021-01-29 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Соединения для лечения болезни гентингтона |
| WO2020005877A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| HRP20240935T1 (hr) | 2018-06-27 | 2024-11-22 | Ptc Therapeutics, Inc. | Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| JP7649257B2 (ja) | 2019-05-13 | 2025-03-19 | ピーティーシー セラピューティクス， インコーポレイテッド | ハンチントン病を処置するための化合物 |
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| US4557865A (en) * | 1984-05-07 | 1985-12-10 | Pennwalt Corporation | Substituted 4-azatricyclo[4.3.1.13,8 ]undecane compounds |
| EE03566B1 (et) * | 1995-11-02 | 2001-12-17 | Neurosearch A/S | Kondenseerunud tropaanderivaadid, nende valmistamine ja kasutamine |
| TR200100462T2 (tr) * | 1998-08-18 | 2001-09-21 | Ucb, S.A. | Muskarinik agonistleri ve antagonistleri |
| CN1332726A (zh) * | 1998-11-02 | 2002-01-23 | 卫福有限公司 | 吡咯烷化合物及其药物用途 |
| BR0210391A (pt) * | 2001-06-12 | 2004-06-15 | Elan Pharm Inc | Composto, métodos de tratar um paciente que tenha ou de prevenir um paciente de contrair uma doença ou condição e de preparar um composto, e, uso de um composto |
| US20050065178A1 (en) * | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| ATE363484T1 (de) * | 2003-09-26 | 2007-06-15 | 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 |
| MX2009010175A (es) * | 2007-03-23 | 2009-10-12 | Abbott Lab | Derivados de acetamida y carboxamida de aza-adamantano y metodos de uso de los mismos. |
| ATE509931T1 (de) * | 2007-03-23 | 2011-06-15 | Abbott Lab | Azaadamantanester- und carbamatderivate sowie anwendungsverfahren dafür |
| 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) |
| WO2011030349A1 (en) * | 2009-09-14 | 2011-03-17 | Suven Life Sciences Limited | L -dihydro-2-oxoquinoline compounds a 5-ht4 receptor ligands |
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- 2010-06-18 MX MX2011014019A patent/MX2011014019A/es active IP Right Grant
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- 2010-06-18 RU RU2015110025/04A patent/RU2015110025A/ru not_active Application Discontinuation
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- 2010-06-18 SG SG2011094141A patent/SG176921A1/en unknown
- 2010-06-18 EP EP10788604.6A patent/EP2443122B1/en not_active Not-in-force
- 2010-06-18 BR BRPI1015043A patent/BRPI1015043A2/pt not_active IP Right Cessation
- 2010-06-18 AU AU2010262643A patent/AU2010262643B2/en not_active Ceased
- 2010-06-18 KR KR1020127001339A patent/KR20120044978A/ko not_active Withdrawn
- 2010-06-18 CN CN2010800368013A patent/CN102459268A/zh active Pending
- 2010-06-18 US US12/818,764 patent/US8846661B2/en not_active Expired - Fee Related
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