JP2006504690A - Ｃｎｓ及びその他の障害の治療に有用なジアザ二環式化合物 - Google Patents

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Publication number

JP2006504690A

JP2006504690A JP2004535749A JP2004535749A JP2006504690A JP 2006504690 A JP2006504690 A JP 2006504690A JP 2004535749 A JP2004535749 A JP 2004535749A JP 2004535749 A JP2004535749 A JP 2004535749A JP 2006504690 A JP2006504690 A JP 2006504690A

Authority

JP

Japan

Prior art keywords

bicyclo

diaza

pyridin

phenyl

octane

Prior art date

2002-09-10

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.)

Withdrawn

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 251
• 238000000034 method Methods 0.000 claims abstract description 115
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
• 208000035475 disorder Diseases 0.000 claims abstract description 16
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 14
• 208000024891 symptom Diseases 0.000 claims abstract description 9
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 8
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 108
• -1 (2-methyl-5-trifluoromethyl-pyridin-3-yl) -1,4-diaza-bicyclo [3.1.1] heptane Chemical compound 0.000 claims description 102
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 229910052740 iodine Inorganic materials 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 229960002715 nicotine Drugs 0.000 claims description 16
• 206010012289 Dementia Diseases 0.000 claims description 14
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 208000028698 Cognitive impairment Diseases 0.000 claims description 12
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 12
• 208000002193 Pain Diseases 0.000 claims description 12
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 12
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 12
• 208000010877 cognitive disease Diseases 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 230000009529 traumatic brain injury Effects 0.000 claims description 12
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 10
• 206010010904 Convulsion Diseases 0.000 claims description 10
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 10
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 10
• 229940079593 drug Drugs 0.000 claims description 10
• 206010013663 drug dependence Diseases 0.000 claims description 10
• 206010015037 epilepsy Diseases 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 9
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 9
• 150000007656 barbituric acids Chemical class 0.000 claims description 9
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 208000011117 substance-related disease Diseases 0.000 claims description 8
• QXAXZLYCXYTILW-UHFFFAOYSA-N ethyl 5-(1,4-diazabicyclo[3.2.1]octan-4-yl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(N2C3CCN(C3)CC2)=C1 QXAXZLYCXYTILW-UHFFFAOYSA-N 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 6
• CZZCFUXFYKHSCR-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.2.1]octan-4-yl)quinoline Chemical compound C1=CC=CC2=CC(N3C4CN(CC3)CC4)=CN=C21 CZZCFUXFYKHSCR-UHFFFAOYSA-N 0.000 claims description 6
• PZLXMKKMMUZJGW-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.3.1]nonan-4-yl)quinoline Chemical compound C1=CC=CC2=CC(N3CCN4CC3CCC4)=CN=C21 PZLXMKKMMUZJGW-UHFFFAOYSA-N 0.000 claims description 6
• PAKIRKMGOXJXPJ-UHFFFAOYSA-N 4-(3-bromophenyl)-1,4-diazabicyclo[3.2.1]octane Chemical compound BrC1=CC=CC(N2C3CCN(C3)CC2)=C1 PAKIRKMGOXJXPJ-UHFFFAOYSA-N 0.000 claims description 6
• RZOFBCHTTCAGOJ-UHFFFAOYSA-N 4-(3-bromophenyl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound BrC1=CC=CC(N2C3CCCN(C3)CC2)=C1 RZOFBCHTTCAGOJ-UHFFFAOYSA-N 0.000 claims description 6
• GDOBURXBSBYLHW-UHFFFAOYSA-N 4-(3-bromophenyl)-1,4-diazabicyclo[3.3.2]decane Chemical compound BrC1=CC=CC(N2C3CCCN(CC3)CC2)=C1 GDOBURXBSBYLHW-UHFFFAOYSA-N 0.000 claims description 6
• NXJSCIXIOSMADJ-UHFFFAOYSA-N 4-(5-bromopyridin-2-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound N1=CC(Br)=CC=C1N1C(C2)CCN2CC1 NXJSCIXIOSMADJ-UHFFFAOYSA-N 0.000 claims description 6
• SKAKTVWAPJKIFF-UHFFFAOYSA-N 4-(5-bromopyridin-2-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound N1=CC(Br)=CC=C1N1C(C2)CCCN2CC1 SKAKTVWAPJKIFF-UHFFFAOYSA-N 0.000 claims description 6
• HRXDHWAFQTYSJI-UHFFFAOYSA-N 4-(5-bromopyridin-2-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound N1=CC(Br)=CC=C1N1C(CC2)CCCN2CC1 HRXDHWAFQTYSJI-UHFFFAOYSA-N 0.000 claims description 6
• DJSVJNXUPNCAES-UHFFFAOYSA-N 4-(5-bromopyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound BrC1=CN=CC(N2C3CCN(C3)CC2)=C1 DJSVJNXUPNCAES-UHFFFAOYSA-N 0.000 claims description 6
• ZAEYVDKQJXYNRA-UHFFFAOYSA-N 4-(5-bromopyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound BrC1=CN=CC(N2C3CCCN(C3)CC2)=C1 ZAEYVDKQJXYNRA-UHFFFAOYSA-N 0.000 claims description 6
• FBULCFGEGXTZTF-UHFFFAOYSA-N 4-(5-bromopyridin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound BrC1=CN=CC(N2C3CCCN(CC3)CC2)=C1 FBULCFGEGXTZTF-UHFFFAOYSA-N 0.000 claims description 6
• GOZFRBCNVGUKQZ-UHFFFAOYSA-N 4-(5-chloropyridin-2-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound N1=CC(Cl)=CC=C1N1C(C2)CCN2CC1 GOZFRBCNVGUKQZ-UHFFFAOYSA-N 0.000 claims description 6
• GQGPJKVWIGYSNG-UHFFFAOYSA-N 4-(5-chloropyridin-2-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound N1=CC(Cl)=CC=C1N1C(C2)CCCN2CC1 GQGPJKVWIGYSNG-UHFFFAOYSA-N 0.000 claims description 6
• GULGZYQNYCLMGE-UHFFFAOYSA-N 4-(5-chloropyridin-2-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound N1=CC(Cl)=CC=C1N1C(CC2)CCCN2CC1 GULGZYQNYCLMGE-UHFFFAOYSA-N 0.000 claims description 6
• WRAIIFJOHGJMOG-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CN=CC(N2C3CCN(C3)CC2)=C1 WRAIIFJOHGJMOG-UHFFFAOYSA-N 0.000 claims description 6
• OLMRKBMRQCMXCC-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound ClC1=CN=CC(N2C3CCCN(C3)CC2)=C1 OLMRKBMRQCMXCC-UHFFFAOYSA-N 0.000 claims description 6
• XMXXTGPJVYOTQG-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound ClC1=CN=CC(N2C3CCCN(CC3)CC2)=C1 XMXXTGPJVYOTQG-UHFFFAOYSA-N 0.000 claims description 6
• VILSVHLWVFBVRH-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CN=CC(N2C3CCN(C3)CC2)=C1 VILSVHLWVFBVRH-UHFFFAOYSA-N 0.000 claims description 6
• GEKYPDQKOYYENZ-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CN=CC(N2C3CCCN(C3)CC2)=C1 GEKYPDQKOYYENZ-UHFFFAOYSA-N 0.000 claims description 6
• LJWBVWXRRPTZIS-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound COC1=CN=CC(N2C3CCCN(CC3)CC2)=C1 LJWBVWXRRPTZIS-UHFFFAOYSA-N 0.000 claims description 6
• GRHSJEMXXKQNDA-UHFFFAOYSA-N 4-(5-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C(N=NC=1)=CC=1C1=CC=CC=C1 GRHSJEMXXKQNDA-UHFFFAOYSA-N 0.000 claims description 6
• JYQOMKIANCALIC-UHFFFAOYSA-N 4-(5-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1CCC2CN1CCN2C(N=NC=1)=CC=1C1=CC=CC=C1 JYQOMKIANCALIC-UHFFFAOYSA-N 0.000 claims description 6
• UAAHGEQBWIXENF-UHFFFAOYSA-N 4-(5-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound C1CCC2CCN1CCN2C(N=NC=1)=CC=1C1=CC=CC=C1 UAAHGEQBWIXENF-UHFFFAOYSA-N 0.000 claims description 6
• GVDPDUFGZDFRIT-UHFFFAOYSA-N 4-(5-phenylpyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C(C=1)=CN=CC=1C1=CC=CC=C1 GVDPDUFGZDFRIT-UHFFFAOYSA-N 0.000 claims description 6
• ODYHRRHIWGYYMQ-UHFFFAOYSA-N 4-(5-phenylpyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1CCC2CN1CCN2C(C=1)=CN=CC=1C1=CC=CC=C1 ODYHRRHIWGYYMQ-UHFFFAOYSA-N 0.000 claims description 6
• LISJKWUCPNWEOC-UHFFFAOYSA-N 4-(5-phenylpyridin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound C1CCC2CCN1CCN2C(C=1)=CN=CC=1C1=CC=CC=C1 LISJKWUCPNWEOC-UHFFFAOYSA-N 0.000 claims description 6
• QNESBMMNVFEIPH-UHFFFAOYSA-N 4-(6-methoxypyridin-2-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC(N2C3CCCN(C3)CC2)=N1 QNESBMMNVFEIPH-UHFFFAOYSA-N 0.000 claims description 6
• PKPKKSFSJOKEJY-UHFFFAOYSA-N 4-(6-methoxypyridin-2-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound COC1=CC=CC(N2C3CCCN(CC3)CC2)=N1 PKPKKSFSJOKEJY-UHFFFAOYSA-N 0.000 claims description 6
• XQAWFXFXLGDFBI-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound C1=NC(C)=CC=C1N1C(C2)CCN2CC1 XQAWFXFXLGDFBI-UHFFFAOYSA-N 0.000 claims description 6
• CTBCKNFETQBXOR-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=NC(C)=CC=C1N1C(C2)CCCN2CC1 CTBCKNFETQBXOR-UHFFFAOYSA-N 0.000 claims description 6
• QFJTUXBLRBWTEJ-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=NC(C)=CC=C1N1C(CC2)CCCN2CC1 QFJTUXBLRBWTEJ-UHFFFAOYSA-N 0.000 claims description 6
• VXERHFMAUHEXOE-UHFFFAOYSA-N 4-(6-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C(N=N1)=CC=C1C1=CC=CC=C1 VXERHFMAUHEXOE-UHFFFAOYSA-N 0.000 claims description 6
• REGSTBYCKNWZFL-UHFFFAOYSA-N 4-(6-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound C1CCC2CCN1CCN2C(N=N1)=CC=C1C1=CC=CC=C1 REGSTBYCKNWZFL-UHFFFAOYSA-N 0.000 claims description 6
• UJFVVKWTZCAPRO-UHFFFAOYSA-N 4-[2-methyl-5-(trifluoromethyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound CC1=NC=C(C(F)(F)F)C=C1N1C(C2)CCN2CC1 UJFVVKWTZCAPRO-UHFFFAOYSA-N 0.000 claims description 6
• GBTRBLAHLCTJDQ-UHFFFAOYSA-N 4-[2-methyl-5-(trifluoromethyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound CC1=NC=C(C(F)(F)F)C=C1N1C(C2)CCCN2CC1 GBTRBLAHLCTJDQ-UHFFFAOYSA-N 0.000 claims description 6
• QLCTVCKMVZULBL-UHFFFAOYSA-N 4-[2-methyl-5-(trifluoromethyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound CC1=NC=C(C(F)(F)F)C=C1N1C(CC2)CCCN2CC1 QLCTVCKMVZULBL-UHFFFAOYSA-N 0.000 claims description 6
• GSCSOEMPXNZDHB-UHFFFAOYSA-N 4-[3-(trifluoromethyl)pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC(F)(F)C1=CC=CN=C1N1C(C2)CCN2CC1 GSCSOEMPXNZDHB-UHFFFAOYSA-N 0.000 claims description 6
• RTTNCLLPAICZHA-UHFFFAOYSA-N 4-[3-(trifluoromethyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound FC(F)(F)C1=CC=CN=C1N1C(C2)CCCN2CC1 RTTNCLLPAICZHA-UHFFFAOYSA-N 0.000 claims description 6
• GQKWBHVDNMGZDG-UHFFFAOYSA-N 4-[3-(trifluoromethyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound FC(F)(F)C1=CC=CN=C1N1C(CC2)CCCN2CC1 GQKWBHVDNMGZDG-UHFFFAOYSA-N 0.000 claims description 6
• HUUQVDMXFJWIFG-UHFFFAOYSA-N 4-[5-(2,4-dichlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 HUUQVDMXFJWIFG-UHFFFAOYSA-N 0.000 claims description 6
• PSRVJROVCNRGDD-UHFFFAOYSA-N 4-[5-(2,4-dichlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound ClC1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 PSRVJROVCNRGDD-UHFFFAOYSA-N 0.000 claims description 6
• JWLYIHFOXTXJLT-UHFFFAOYSA-N 4-[5-(2,4-dichlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound ClC1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 JWLYIHFOXTXJLT-UHFFFAOYSA-N 0.000 claims description 6
• DOWIGBPKOCELEM-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC1=CC=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 DOWIGBPKOCELEM-UHFFFAOYSA-N 0.000 claims description 6
• PRGQZMAPNBHVTO-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound FC1=CC=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 PRGQZMAPNBHVTO-UHFFFAOYSA-N 0.000 claims description 6
• YRXCFAOQHQRJKQ-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound FC1=CC=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 YRXCFAOQHQRJKQ-UHFFFAOYSA-N 0.000 claims description 6
• CLAJZAITPOWRSR-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 CLAJZAITPOWRSR-UHFFFAOYSA-N 0.000 claims description 6
• CZYIWVGHQDJXMU-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound COC1=CC=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 CZYIWVGHQDJXMU-UHFFFAOYSA-N 0.000 claims description 6
• BIRJSUWWHHMYQV-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound CC1=CC=CC=C1C1=CC=C(N2C3CCN(C3)CC2)N=C1 BIRJSUWWHHMYQV-UHFFFAOYSA-N 0.000 claims description 6
• FIPBHJQOBJCWDX-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound CC1=CC=CC=C1C1=CC=C(N2C3CCCN(C3)CC2)N=C1 FIPBHJQOBJCWDX-UHFFFAOYSA-N 0.000 claims description 6
• ZUZDHQAUCVXXEC-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound CC1=CC=CC=C1C1=CC=C(N2C3CCCN(CC3)CC2)N=C1 ZUZDHQAUCVXXEC-UHFFFAOYSA-N 0.000 claims description 6
• RULOXOPFFKXVRW-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound CC1=CC=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 RULOXOPFFKXVRW-UHFFFAOYSA-N 0.000 claims description 6
• WVIRFUXCBFMHBB-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound CC1=CC=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 WVIRFUXCBFMHBB-UHFFFAOYSA-N 0.000 claims description 6
• DPFGXFYAPOQRBA-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound CC1=CC=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 DPFGXFYAPOQRBA-UHFFFAOYSA-N 0.000 claims description 6
• PHCGMSZMSRENMQ-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CC=CC(C=2C=NC(=CC=2)N2C3CCN(C3)CC2)=C1 PHCGMSZMSRENMQ-UHFFFAOYSA-N 0.000 claims description 6
• STHVAVJZHYRAIC-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound ClC1=CC=CC(C=2C=NC(=CC=2)N2C3CCCN(C3)CC2)=C1 STHVAVJZHYRAIC-UHFFFAOYSA-N 0.000 claims description 6
• TVTFWHNURZHZOA-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound ClC1=CC=CC(C=2C=NC(=CC=2)N2C3CCCN(CC3)CC2)=C1 TVTFWHNURZHZOA-UHFFFAOYSA-N 0.000 claims description 6
• LOZAXNVJUXOXKM-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CC=CC(C=2C=C(C=NC=2)N2C3CCN(C3)CC2)=C1 LOZAXNVJUXOXKM-UHFFFAOYSA-N 0.000 claims description 6
• UZUBGVRWZKGHGY-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound ClC1=CC=CC(C=2C=C(C=NC=2)N2C3CCCN(C3)CC2)=C1 UZUBGVRWZKGHGY-UHFFFAOYSA-N 0.000 claims description 6
• OWEDYSYZJDEVOH-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound ClC1=CC=CC(C=2C=C(C=NC=2)N2C3CCCN(CC3)CC2)=C1 OWEDYSYZJDEVOH-UHFFFAOYSA-N 0.000 claims description 6
• VWGICUSWTVBFJS-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC1=CC=CC(C=2C=NC(=CC=2)N2C3CCN(C3)CC2)=C1 VWGICUSWTVBFJS-UHFFFAOYSA-N 0.000 claims description 6
• BDEPCXUCJDOPEX-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound FC1=CC=CC(C=2C=NC(=CC=2)N2C3CCCN(C3)CC2)=C1 BDEPCXUCJDOPEX-UHFFFAOYSA-N 0.000 claims description 6
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