JP2006507241A5 - - Google Patents
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- Publication number
- JP2006507241A5 JP2006507241A5 JP2004529002A JP2004529002A JP2006507241A5 JP 2006507241 A5 JP2006507241 A5 JP 2006507241A5 JP 2004529002 A JP2004529002 A JP 2004529002A JP 2004529002 A JP2004529002 A JP 2004529002A JP 2006507241 A5 JP2006507241 A5 JP 2006507241A5
- Authority
- JP
- Japan
- Prior art keywords
- methanone
- diazabicyclo
- furan
- thiophen
- pyridyl
- 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.)
- Pending
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- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- -1 1,4-diazabicyclo [3.2.2] non-4-yl Chemical group 0.000 claims 6
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 4
- GNPQLYUSJOCBMA-UHFFFAOYSA-N (5-bromofuran-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound O1C(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 GNPQLYUSJOCBMA-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 230000006735 deficit Effects 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- OGZLAVDBQCWTRH-UHFFFAOYSA-N (3-bromophenyl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound BrC1=CC=CC(C(=O)N2C3CCN(CC3)CC2)=C1 OGZLAVDBQCWTRH-UHFFFAOYSA-N 0.000 claims 1
- CSIFTQTVMGTFIA-UHFFFAOYSA-N (4-bromophenyl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 CSIFTQTVMGTFIA-UHFFFAOYSA-N 0.000 claims 1
- PFARLMJTRBXTQP-UHFFFAOYSA-N (4-bromothiophen-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound BrC1=CSC(C(=O)N2C3CCN(CC3)CC2)=C1 PFARLMJTRBXTQP-UHFFFAOYSA-N 0.000 claims 1
- PFOHKMLFVACSFW-UHFFFAOYSA-N (5-bromothiophen-2-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound S1C(Br)=CC=C1C(=O)N1C(CC2)CCN2CC1 PFOHKMLFVACSFW-UHFFFAOYSA-N 0.000 claims 1
- DNQWTTQUOXMVJD-UHFFFAOYSA-N (5-bromothiophen-3-yl)-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound S1C(Br)=CC(C(=O)N2C3CCN(CC3)CC2)=C1 DNQWTTQUOXMVJD-UHFFFAOYSA-N 0.000 claims 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims 1
- UVZLCLJQMZJFJL-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-iodophenyl)methanone Chemical compound IC1=CC=CC(C(=O)N2C3CCN(CC3)CC2)=C1 UVZLCLJQMZJFJL-UHFFFAOYSA-N 0.000 claims 1
- IXKRDKNQHUOVKG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-phenylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 IXKRDKNQHUOVKG-UHFFFAOYSA-N 0.000 claims 1
- UCMQCNNZHLFWQP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CC=N1 UCMQCNNZHLFWQP-UHFFFAOYSA-N 0.000 claims 1
- CDSCDKTXQWLABR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CN=C1 CDSCDKTXQWLABR-UHFFFAOYSA-N 0.000 claims 1
- GENNWRVZHQPVBO-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-pyridin-4-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=NC=C1 GENNWRVZHQPVBO-UHFFFAOYSA-N 0.000 claims 1
- LFQXLDRICKOWGM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-thiophen-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CS1 LFQXLDRICKOWGM-UHFFFAOYSA-N 0.000 claims 1
- FUDFPUYWRXFOOH-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(3-thiophen-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C=1C=CSC=1 FUDFPUYWRXFOOH-UHFFFAOYSA-N 0.000 claims 1
- HAXPXNGBJPFDGV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1C(=O)N1C(CC2)CCN2CC1 HAXPXNGBJPFDGV-UHFFFAOYSA-N 0.000 claims 1
- WTSKNUGIAJZTMU-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 WTSKNUGIAJZTMU-UHFFFAOYSA-N 0.000 claims 1
- YFNUMKDCWUSIRV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CC=C1 YFNUMKDCWUSIRV-UHFFFAOYSA-N 0.000 claims 1
- MZMRVHKSQCNPKT-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CC=N1 MZMRVHKSQCNPKT-UHFFFAOYSA-N 0.000 claims 1
- RJJNRYMNCLCVOG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CC=N1 RJJNRYMNCLCVOG-UHFFFAOYSA-N 0.000 claims 1
- ZNVCOLOEINQRSA-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CC=N1 ZNVCOLOEINQRSA-UHFFFAOYSA-N 0.000 claims 1
- QOXDDTRJHUWFSC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CN=C1 QOXDDTRJHUWFSC-UHFFFAOYSA-N 0.000 claims 1
- DHJJHUMTVYKNTK-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 DHJJHUMTVYKNTK-UHFFFAOYSA-N 0.000 claims 1
- MYRASTOHFZHWRQ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CN=C1 MYRASTOHFZHWRQ-UHFFFAOYSA-N 0.000 claims 1
- IDJXUTJMHGLAQD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=NC=C1 IDJXUTJMHGLAQD-UHFFFAOYSA-N 0.000 claims 1
- IRIRSSBNMMWXKV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=NC=C1 IRIRSSBNMMWXKV-UHFFFAOYSA-N 0.000 claims 1
- SFCOAMGARZGOFF-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-4-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=NC=C1 SFCOAMGARZGOFF-UHFFFAOYSA-N 0.000 claims 1
- PNHMVUPZQHFWJP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CS1 PNHMVUPZQHFWJP-UHFFFAOYSA-N 0.000 claims 1
- IQQWZDQMXJJYNM-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-2-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CS1 IQQWZDQMXJJYNM-UHFFFAOYSA-N 0.000 claims 1
- JTOZWWPPPIVSJG-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CS1 JTOZWWPPPIVSJG-UHFFFAOYSA-N 0.000 claims 1
- HSLQOYKHBCLWOB-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-3-ylphenyl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C=1C=CSC=1 HSLQOYKHBCLWOB-UHFFFAOYSA-N 0.000 claims 1
- SODJXZKVCLJFEE-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CC=C1 SODJXZKVCLJFEE-UHFFFAOYSA-N 0.000 claims 1
- LHGVLQATESRNBH-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-phenylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CC=C1 LHGVLQATESRNBH-UHFFFAOYSA-N 0.000 claims 1
- DXAUAUZCOKVAJC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CC=N1 DXAUAUZCOKVAJC-UHFFFAOYSA-N 0.000 claims 1
- DLHCGZZYPGPVCR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CC=N1 DLHCGZZYPGPVCR-UHFFFAOYSA-N 0.000 claims 1
- MVCSWWMDCPXUOW-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CC=N1 MVCSWWMDCPXUOW-UHFFFAOYSA-N 0.000 claims 1
- QPPBIBLFYOSNPS-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-2-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CC=N1 QPPBIBLFYOSNPS-UHFFFAOYSA-N 0.000 claims 1
- MRQVRJKCJRBPAD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CN=C1 MRQVRJKCJRBPAD-UHFFFAOYSA-N 0.000 claims 1
- MBWNIKDPLGYNBF-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CN=C1 MBWNIKDPLGYNBF-UHFFFAOYSA-N 0.000 claims 1
- ZXSSSLLUZQKGDV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CN=C1 ZXSSSLLUZQKGDV-UHFFFAOYSA-N 0.000 claims 1
- MKBBUDXINIFDPX-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CN=C1 MKBBUDXINIFDPX-UHFFFAOYSA-N 0.000 claims 1
- MWXBVPSLVKVWBA-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=NC=C1 MWXBVPSLVKVWBA-UHFFFAOYSA-N 0.000 claims 1
- MBEIHBWZBVTMFZ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=NC=C1 MBEIHBWZBVTMFZ-UHFFFAOYSA-N 0.000 claims 1
- KEJSEMWXIQEIDY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=NC=C1 KEJSEMWXIQEIDY-UHFFFAOYSA-N 0.000 claims 1
- RLJRNTDELRCHII-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=NC=C1 RLJRNTDELRCHII-UHFFFAOYSA-N 0.000 claims 1
- CFSYVLPMJBCKBT-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CS1 CFSYVLPMJBCKBT-UHFFFAOYSA-N 0.000 claims 1
- HYMMMRPPFFEINN-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CS1 HYMMMRPPFFEINN-UHFFFAOYSA-N 0.000 claims 1
- CLBALKICHJMDDY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CS1 CLBALKICHJMDDY-UHFFFAOYSA-N 0.000 claims 1
- FTMRKAUMDVXFDC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CS1 FTMRKAUMDVXFDC-UHFFFAOYSA-N 0.000 claims 1
- ADRZDHXTXVMBOR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C=1C=CSC=1 ADRZDHXTXVMBOR-UHFFFAOYSA-N 0.000 claims 1
- AJJFWAVQFNELFJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C=1C=CSC=1 AJJFWAVQFNELFJ-UHFFFAOYSA-N 0.000 claims 1
- JYSBTOLWQZATNJ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C=1C=CSC=1 JYSBTOLWQZATNJ-UHFFFAOYSA-N 0.000 claims 1
- YYSWQOGFUOIEAW-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C=1C=CSC=1 YYSWQOGFUOIEAW-UHFFFAOYSA-N 0.000 claims 1
- UYXQTYKMPHONOO-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[3-(furan-2-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C1=CC=CO1 UYXQTYKMPHONOO-UHFFFAOYSA-N 0.000 claims 1
- DLASHEKCTDFEAZ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[3-(furan-3-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CC=CC=1C=1C=COC=1 DLASHEKCTDFEAZ-UHFFFAOYSA-N 0.000 claims 1
- ZZMOMAZUUAPGBY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-2-yl)furan-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CO1 ZZMOMAZUUAPGBY-UHFFFAOYSA-N 0.000 claims 1
- DHQSIENQTWLGCD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-2-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C1=CC=CO1 DHQSIENQTWLGCD-UHFFFAOYSA-N 0.000 claims 1
- CEHAHHKXNFJLFU-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-2-yl)thiophen-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CO1 CEHAHHKXNFJLFU-UHFFFAOYSA-N 0.000 claims 1
- AUDBITKNIDHJPP-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-3-yl)furan-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C=1C=COC=1 AUDBITKNIDHJPP-UHFFFAOYSA-N 0.000 claims 1
- CVFFPZUTOZEQBY-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-3-yl)phenyl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=C1)=CC=C1C=1C=COC=1 CVFFPZUTOZEQBY-UHFFFAOYSA-N 0.000 claims 1
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- MIJYHLLUFJGZPR-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-3-yl)thiophen-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C=1C=COC=1 MIJYHLLUFJGZPR-UHFFFAOYSA-N 0.000 claims 1
- KPDXQGPZVDOPAC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-3-yl)thiophen-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C=1C=COC=1 KPDXQGPZVDOPAC-UHFFFAOYSA-N 0.000 claims 1
- PIXDIVGXUUHIPV-UHFFFAOYSA-N 4-thiophen-3-ylthiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC(C2=CSC=C2)=C1 PIXDIVGXUUHIPV-UHFFFAOYSA-N 0.000 claims 1
- WJTFHWXMITZNHS-UHFFFAOYSA-N 5-bromofuran-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)O1 WJTFHWXMITZNHS-UHFFFAOYSA-N 0.000 claims 1
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| SE521512C2 (sv) | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| MXPA05003317A (es) | 2002-09-25 | 2005-07-05 | Memory Pharm Corp | Indazoles, benzotiazoles y benzoisotiazoles asi como preparacion y usos de los mismos. |
| ES2285233T3 (es) | 2002-12-20 | 2007-11-16 | Niconovum Ab | Un material en particulas que contiene nicotina y celulosa microcristalina fisicamente y quimicamente estable. |
| MXPA05006861A (es) * | 2003-02-27 | 2005-12-12 | Neurosearch As | Derivados arildiazabiciclicos novedosos. |
| DE602004010299T2 (de) | 2003-12-22 | 2008-09-18 | Memory Pharmaceuticals Corp. | Indole, 1h-indazole, 1,2-benzisoxazole und 1,2-benzisothiazole und deren herstellung und anwendungen |
| CN100445285C (zh) * | 2003-12-22 | 2008-12-24 | 阿斯利康(瑞典)有限公司 | 烟碱性乙酰胆碱受体配体 |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| EP1713810B1 (en) * | 2004-02-04 | 2010-12-29 | NeuroSearch A/S | Diazabicyclic aryl derivatives as nicotinic acetylcholine receptor ligands |
| NZ550534A (en) | 2004-03-25 | 2009-07-31 | Memory Pharm Corp | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| WO2006001894A1 (en) | 2004-04-22 | 2006-01-05 | Memory Pharmaceutical Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| JP2007538011A (ja) | 2004-05-07 | 2007-12-27 | メモリー・ファーマシューティカルズ・コーポレイション | １ｈ−インダゾール、ベンゾチアゾール、１，２−ベンゾイソキサゾール、１，２−ベンゾイソチアゾール、およびクロモン、ならびにそれらの調製および使用 |
| EP1802616B1 (en) | 2004-10-15 | 2011-01-12 | NeuroSearch A/S | Novel azabicyclic aryl derivatives and their medical use |
| RU2418797C2 (ru) | 2004-12-22 | 2011-05-20 | Мемори Фармасьютиклз Корпорейшн | Лиганды никотинового рецептора альфа-7, их получение и применение |
| JP2009526777A (ja) * | 2006-02-14 | 2009-07-23 | 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作用薬としての３，９−ジアザビシクロ（３．３．１）ノナ−３−イル−アリールメタノン誘導体 |
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| 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 |
| TWI405763B (zh) * | 2006-11-02 | 2013-08-21 | Targacept Inc | 菸鹼乙醯膽鹼受體亞型選擇性之二氮雜雙環烷類醯胺 |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| CN101910170A (zh) * | 2007-10-22 | 2010-12-08 | 记忆药物公司 | 用于治疗疾病的烟碱性乙酰胆碱受体的(1,4-二氮杂双环[3.2.2]壬-6-烯-4-基)-杂环基-甲酮配体 |
| GB0724251D0 (en) | 2007-12-12 | 2008-02-06 | Univ Edinburgh | Therapeutic compounds and their use |
| GB0804685D0 (en) * | 2008-03-13 | 2008-04-16 | Univ Edinburgh | Therapeutic compounds and their use |
| MX2010014203A (es) | 2008-06-20 | 2011-02-22 | Astrazeneca Ab | Derivados de dibenzotiazepina y sus usos - 424. |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| EP2443113A1 (en) | 2009-06-15 | 2012-04-25 | The University Of Edinburgh | Amido-isothiazole compounds and their use as inhibitors of 11beta-hsd1 for the treatment of metabolic syndrome and related disorders |
| EP2477983B1 (en) | 2009-09-16 | 2015-04-15 | The University Of Edinburgh | (4-phenyl-piperidin-1-yl)-[5-1h-pyrazol-4yl)-thiophen-3-yl]-methanone compounds and their use |
| AU2011212925A1 (en) * | 2010-02-03 | 2012-09-06 | Meh Associates, Inc | Multiple substituted fluoromethanes as selective and bioactive isosteres |
| WO2011135276A1 (en) | 2010-04-29 | 2011-11-03 | The University Of Edinburgh | 3, 3 -disubstituted- ( 8 - aza - bicyclo [3.2.1] oct- 8 - yl) -[5- (1h - pyrazol - 4 -yl) -thiophen-3 -yl] methanones as inhibitors of 11 (beta) -hsd1 |
| AR081402A1 (es) | 2010-05-17 | 2012-08-29 | Envivo Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il) benzo(b)tiofeno-2-carboxamida monohidrato |
| WO2012007500A2 (de) * | 2010-07-15 | 2012-01-19 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| CA2872005A1 (en) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
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| MA37975B2 (fr) * | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| WO2014122474A1 (en) | 2013-02-07 | 2014-08-14 | Takeda Pharmaceutical Company Limited | Piperidin-1 -yl and azepin-1 -yl carboxylates as muscarinic m4 receptor agonists |
| HK1219722A1 (zh) | 2013-06-21 | 2017-04-13 | Takeda Pharmaceutical Company Limited | 1-磺酰基派啶衍生物作为前动力蛋白受体的调节剂 |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| GB201619514D0 (en) | 2016-11-18 | 2017-01-04 | Takeda Pharmaceuticals Co | Novel compounds |
| CN114040762A (zh) | 2019-02-04 | 2022-02-11 | 建新公司 | 使用葡糖神经酰胺合酶(gcs)的抑制剂治疗纤毛疾病 |
| TW202142236A (zh) | 2020-02-03 | 2021-11-16 | 美商健臻公司 | 用於治療與溶體儲積症相關的神經症狀之方法 |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
| KR20230043024A (ko) | 2020-07-24 | 2023-03-30 | 젠자임 코포레이션 | 벤글루스타트를 포함하는 제약 조성물 |
| GB202414193D0 (en) | 2024-09-27 | 2024-11-13 | Addex Pharmaceuticals Sa | Novel compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281423A (en) * | 1964-02-03 | 1966-10-25 | Merck & Co Inc | 1, 3-ethanopiperazines and process |
| US4895943A (en) * | 1988-10-25 | 1990-01-23 | Pfizer Inc. | Preparation of 1,4-diazabicyclo(3.2.2)nonane |
| US5679673A (en) * | 1992-09-24 | 1997-10-21 | The United States Of America, Represented By The Department Of Health And Human Services | Aralkyl bridged diazabicycloalkane derivatives for CNS disorders |
| FR2791678B1 (fr) * | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de 1,4-diazabicyclo [3.2.2] nonane-4-carboxylates et -carboxamides, leur preparation et leur application en therapeutique |
| FR2809732B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | DERIVES DE 4(-2-PHENYLTHIAZOL-5-yl)-1,4-DIAZABICYCLO-[3.2.2] NONANE, LEUR PREPARATION ET LEUR APPLICATION ENTHERAPEUTIQUE |
| FR2809731B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| MXPA05006861A (es) * | 2003-02-27 | 2005-12-12 | Neurosearch As | Derivados arildiazabiciclicos novedosos. |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| CN100445285C (zh) * | 2003-12-22 | 2008-12-24 | 阿斯利康(瑞典)有限公司 | 烟碱性乙酰胆碱受体配体 |
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2002
- 2002-08-14 SE SE0202430A patent/SE0202430D0/xx unknown
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2003
- 2003-08-13 MX MXPA05001583A patent/MXPA05001583A/es unknown
- 2003-08-13 AT AT03788214T patent/ATE417049T1/de not_active IP Right Cessation
- 2003-08-13 BR BR0313234-0A patent/BR0313234A/pt not_active IP Right Cessation
- 2003-08-13 JP JP2004529002A patent/JP2006507241A/ja active Pending
- 2003-08-13 NZ NZ537882A patent/NZ537882A/en unknown
- 2003-08-13 WO PCT/SE2003/001277 patent/WO2004016617A1/en not_active Ceased
- 2003-08-13 ES ES03788214T patent/ES2316848T3/es not_active Expired - Lifetime
- 2003-08-13 KR KR1020057002265A patent/KR20060002727A/ko not_active Ceased
- 2003-08-13 EP EP03788214A patent/EP1539765B1/en not_active Expired - Lifetime
- 2003-08-13 DE DE60325234T patent/DE60325234D1/de not_active Expired - Fee Related
- 2003-08-13 US US10/524,484 patent/US20050239774A1/en not_active Abandoned
- 2003-08-13 CA CA002493920A patent/CA2493920A1/en not_active Abandoned
- 2003-08-13 AU AU2003248592A patent/AU2003248592B2/en not_active Expired - Fee Related
- 2003-08-13 CN CNB038194791A patent/CN100343256C/zh not_active Expired - Fee Related
-
2005
- 2005-01-20 IL IL16641605A patent/IL166416A0/xx unknown
- 2005-02-10 ZA ZA200501226A patent/ZA200501226B/en unknown
- 2005-03-11 NO NO20051259A patent/NO20051259L/no not_active Application Discontinuation
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