JP2006504690A5 - - Google Patents
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- JP2006504690A5 JP2006504690A5 JP2004535749A JP2004535749A JP2006504690A5 JP 2006504690 A5 JP2006504690 A5 JP 2006504690A5 JP 2004535749 A JP2004535749 A JP 2004535749A JP 2004535749 A JP2004535749 A JP 2004535749A JP 2006504690 A5 JP2006504690 A5 JP 2006504690A5
- Authority
- JP
- Japan
- Prior art keywords
- diaza
- bicyclo
- pyridin
- phenyl
- decane
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 14
- -1 (5-bromo-pyridin-3-yl) -1,4-diaza-bicyclo [3.2.1] octane Chemical compound 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- HMRNFWXWPOKOJT-UHFFFAOYSA-N 4-(6-methoxypyridin-2-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CC=CC(N2C3CCN(C3)CC2)=N1 HMRNFWXWPOKOJT-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- FMLGWRTUSSURJM-UHFFFAOYSA-N 4-(6-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1CCC2CN1CCN2C(N=N1)=CC=C1C1=CC=CC=C1 FMLGWRTUSSURJM-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- GIPKYCKNDKUZIJ-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CC=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 GIPKYCKNDKUZIJ-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- NWQBKZPHCONCJD-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound FC1=CC=CC(C=2C=NC(=CC=2)N2C3CCCN(CC3)CC2)=C1 NWQBKZPHCONCJD-UHFFFAOYSA-N 0.000 claims 3
- SGYKUBRQFGDPGE-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CC=CC(C=2C=C(C=NC=2)N2C3CCN(C3)CC2)=C1 SGYKUBRQFGDPGE-UHFFFAOYSA-N 0.000 claims 3
- PZEQKMGBTHWMCG-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC(C=2C=C(C=NC=2)N2C3CCCN(C3)CC2)=C1 PZEQKMGBTHWMCG-UHFFFAOYSA-N 0.000 claims 3
- KOEMCGGITQTPGG-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound COC1=CC=CC(C=2C=C(C=NC=2)N2C3CCCN(CC3)CC2)=C1 KOEMCGGITQTPGG-UHFFFAOYSA-N 0.000 claims 3
- IDLJJGGZDVBDSV-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(N2C3CCN(C3)CC2)N=C1 IDLJJGGZDVBDSV-UHFFFAOYSA-N 0.000 claims 3
- DEDHFECZOZINJE-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(N2C3CCCN(C3)CC2)N=C1 DEDHFECZOZINJE-UHFFFAOYSA-N 0.000 claims 3
- QQBOBWKKYBWQDP-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(N2C3CCCN(CC3)CC2)N=C1 QQBOBWKKYBWQDP-UHFFFAOYSA-N 0.000 claims 3
- ZUQLXECGKJQGGY-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 ZUQLXECGKJQGGY-UHFFFAOYSA-N 0.000 claims 3
- GNYSTCYGKBWDSS-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 GNYSTCYGKBWDSS-UHFFFAOYSA-N 0.000 claims 3
- CSGLMXWLMUVABY-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 CSGLMXWLMUVABY-UHFFFAOYSA-N 0.000 claims 3
- CAKWVYFZQPIFNQ-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound C1=CC(F)=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 CAKWVYFZQPIFNQ-UHFFFAOYSA-N 0.000 claims 3
- QFWWZJTZMALTNZ-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(F)=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 QFWWZJTZMALTNZ-UHFFFAOYSA-N 0.000 claims 3
- PTJYCIBCCKPWGP-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(F)=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 PTJYCIBCCKPWGP-UHFFFAOYSA-N 0.000 claims 3
- AQCCUDJASAFKCI-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound C1=CC(OC)=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 AQCCUDJASAFKCI-UHFFFAOYSA-N 0.000 claims 3
- QSOQQHIPRGWAHW-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(OC)=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 QSOQQHIPRGWAHW-UHFFFAOYSA-N 0.000 claims 3
- PATOATUNXZUKGT-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(OC)=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 PATOATUNXZUKGT-UHFFFAOYSA-N 0.000 claims 3
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- 229960002715 nicotine Drugs 0.000 claims 1
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| US40969402P | 2002-09-10 | 2002-09-10 | |
| PCT/IB2003/003795 WO2004024729A1 (en) | 2002-09-10 | 2003-08-29 | Diazabicyclic compounds useful in the treatment of cns and other disorders |
Publications (2)
| Publication Number | Publication Date |
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| JP2006504690A JP2006504690A (ja) | 2006-02-09 |
| JP2006504690A5 true JP2006504690A5 (https=) | 2006-10-05 |
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| US (1) | US7442694B2 (https=) |
| EP (1) | EP1551843A1 (https=) |
| JP (1) | JP2006504690A (https=) |
| AU (1) | AU2003255993A1 (https=) |
| BR (1) | BR0314201A (https=) |
| CA (1) | CA2498291C (https=) |
| MX (1) | MXPA05002621A (https=) |
| WO (1) | WO2004024729A1 (https=) |
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| US7223753B2 (en) * | 2002-11-11 | 2007-05-29 | Neurosearch A/S | Diazabicyclic biaryl derivatives |
| CA2511970C (en) | 2003-01-14 | 2012-06-26 | Cytokinetics, Inc. | Urea derivatives useful in the treatment of heart failure |
| ATE450263T1 (de) | 2004-02-04 | 2009-12-15 | Neurosearch As | Diazabicyclische aryl-derivate als cholinerge rezeptor-modulatoren |
| JP5080970B2 (ja) | 2004-06-17 | 2012-11-21 | サイトキネティクス・インコーポレーテッド | 心疾患を治療するための置換尿素誘導体 |
| US7176222B2 (en) | 2004-07-27 | 2007-02-13 | Cytokinetics, Inc. | Syntheses of ureas |
| US7538223B2 (en) | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| TW200808321A (en) | 2005-12-15 | 2008-02-16 | Cytokinetics Inc | Certain chemical entities, compositions and methods |
| US7825120B2 (en) | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| EP1959962A2 (en) | 2005-12-16 | 2008-08-27 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| EP1962852B1 (en) | 2005-12-19 | 2017-01-25 | Cytokinetics, Inc. | Compounds, compositions and methods |
| WO2007138040A1 (en) * | 2006-05-30 | 2007-12-06 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidinyl derivative and its medical use |
| US20100286128A1 (en) * | 2007-08-17 | 2010-11-11 | Dan Peters | 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidinyl derivatives useful as nicotinic acetylcholine-receptor ligands |
| JP2010536726A (ja) * | 2007-08-17 | 2010-12-02 | ノイロサーチ アクティーゼルスカブ | ニコチン性アセチルコリン受容体リガンドとして有用な新規１，４−ジアザ−ビシクロ〔３．２．２〕ノニルヘテロアリール誘導体 |
| DE102007053771A1 (de) * | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
| US20100305108A1 (en) * | 2007-11-14 | 2010-12-02 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidine derivatives and their medical use |
| WO2009062987A1 (en) * | 2007-11-14 | 2009-05-22 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidine derivatives and their medical use |
| US8343960B2 (en) | 2007-11-14 | 2013-01-01 | Neurosearch A/S | 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidine derivatives and their medical use |
| JP2011513461A (ja) | 2008-03-11 | 2011-04-28 | ノイロサーチ アクティーゼルスカブ | ニコチン性アセチルコリン受容体モジュレーターとして有用な新規な１，４−ジアザ−ビシクロ［３．２．１］オクタン誘導体 |
| WO2010063784A1 (en) * | 2008-12-04 | 2010-06-10 | Neurosearch A/S | Novel diaza-bicyclononyl-phenyl derivatives and their medical use |
| US20140206667A1 (en) | 2012-11-14 | 2014-07-24 | Michela Gallagher | Methods and compositions for treating schizophrenia |
| EP4399517A4 (en) * | 2021-09-08 | 2025-10-15 | Achieve Life Sciences Inc | ANALYTICAL METHODS FOR EVALUATING THE PURITY OF CYTISINE |
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| US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
| IN166416B (https=) * | 1985-09-18 | 1990-05-05 | Pfizer | |
| ZA877471B (en) * | 1986-10-08 | 1988-04-05 | Bristol-Myers Company | 1-tertiary-alkyl-substituted naphthyridine-and quinoline-carboxylic acid antibacterial agents |
| DE3711193A1 (de) * | 1987-04-02 | 1988-10-13 | Bayer Ag | 5-substituierte chinolon- und naphthyridoncarbonsaeure-derivate |
| DE3910663A1 (de) * | 1989-04-03 | 1990-10-04 | Bayer Ag | 5-alkylchinoloncarbonsaeuren |
| DE4210941A1 (de) * | 1992-04-02 | 1993-10-07 | Bayer Ag | Neue 9-Fluor-7.oxo-7H-pyrido[1,2,3-d,e][1,4]benzoxacin-6-carbonsäuren und -ester |
| GB9803411D0 (en) * | 1998-02-18 | 1998-04-15 | Smithkline Beecham Plc | Novel compounds |
| WO2000006575A2 (en) * | 1998-07-28 | 2000-02-10 | Smithkline Beecham Plc | Azabicyclic compounds |
| FR2786770B1 (fr) * | 1998-12-04 | 2001-01-19 | Synthelabo | Derives de 1,4-diazabicyclo[3.2.2.]nonane, leur preparation et leur application en therapeutique |
| FR2804430B1 (fr) * | 2000-01-28 | 2002-03-22 | Sanofi Synthelabo | Derives de 4-heteroaryl-1,4-diazabicyclo[3.2.2] nonane, leur preparation et leur application en therapeutique |
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- 2003-08-29 BR BR0314201-9A patent/BR0314201A/pt not_active IP Right Cessation
- 2003-08-29 AU AU2003255993A patent/AU2003255993A1/en not_active Abandoned
- 2003-08-29 MX MXPA05002621A patent/MXPA05002621A/es unknown
- 2003-08-29 CA CA002498291A patent/CA2498291C/en not_active Expired - Fee Related
- 2003-08-29 JP JP2004535749A patent/JP2006504690A/ja not_active Withdrawn
- 2003-08-29 EP EP03795129A patent/EP1551843A1/en not_active Withdrawn
- 2003-09-08 US US10/657,738 patent/US7442694B2/en not_active Expired - Fee Related
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