CA2498291C - Diazabicyclic compounds useful in the treatment of cns and other disorders - Google Patents

Info

Publication number

CA2498291C

CA2498291C CA002498291A CA2498291A CA2498291C CA 2498291 C CA2498291 C CA 2498291C CA 002498291 A CA002498291 A CA 002498291A CA 2498291 A CA2498291 A CA 2498291A CA 2498291 C CA2498291 C CA 2498291C

Authority

CA

Canada

Prior art keywords

diaza

bicyclo

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.)

Expired - Fee Related

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• 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
• 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
• 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
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• 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
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• 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
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• 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
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• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 229910052731 fluorine Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
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• QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 7
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• 238000003556 assay Methods 0.000 description 7
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• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 7
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• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
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