JP2003523342A5 - - Google Patents
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- Publication number
- JP2003523342A5 JP2003523342A5 JP2001560205A JP2001560205A JP2003523342A5 JP 2003523342 A5 JP2003523342 A5 JP 2003523342A5 JP 2001560205 A JP2001560205 A JP 2001560205A JP 2001560205 A JP2001560205 A JP 2001560205A JP 2003523342 A5 JP2003523342 A5 JP 2003523342A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- oct
- carboxamide
- thiophene
- furan
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 33
- 125000003118 aryl group Chemical group 0.000 claims 17
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- 239000001301 oxygen Substances 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000004434 sulfur atom Chemical group 0.000 claims 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims 9
- -1 salts enantiomers Chemical class 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 150000003857 carboxamides Chemical class 0.000 claims 4
- 230000006735 deficit Effects 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical group NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group 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
- OTNOXWBLYHUWLZ-UHFFFAOYSA-N 3-(3-acetamidophenyl)-n-(1-azabicyclo[2.2.2]octan-3-yl)benzamide Chemical compound CC(=O)NC1=CC=CC(C=2C=C(C=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 OTNOXWBLYHUWLZ-UHFFFAOYSA-N 0.000 claims 1
- OTNOXWBLYHUWLZ-NRFANRHFSA-N 3-(3-acetamidophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]benzamide Chemical compound CC(=O)NC1=CC=CC(C=2C=C(C=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 OTNOXWBLYHUWLZ-NRFANRHFSA-N 0.000 claims 1
- MEXOEXAUFQFSTA-UHFFFAOYSA-N 5-(3-acetamidophenyl)-n-(1-azabicyclo[2.2.2]octan-3-yl)furan-2-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2OC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 MEXOEXAUFQFSTA-UHFFFAOYSA-N 0.000 claims 1
- ONRPCVPDQHMEQB-UHFFFAOYSA-N 5-(3-acetamidophenyl)-n-(1-azabicyclo[2.2.2]octan-3-yl)thiophene-2-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 ONRPCVPDQHMEQB-UHFFFAOYSA-N 0.000 claims 1
- MEXOEXAUFQFSTA-KRWDZBQOSA-N 5-(3-acetamidophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furan-2-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 MEXOEXAUFQFSTA-KRWDZBQOSA-N 0.000 claims 1
- ONRPCVPDQHMEQB-KRWDZBQOSA-N 5-(3-acetamidophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thiophene-2-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 ONRPCVPDQHMEQB-KRWDZBQOSA-N 0.000 claims 1
- MVAUXTNBWFARSQ-HNNXBMFYSA-N 5-(3-aminophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furan-2-carboxamide Chemical compound NC1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 MVAUXTNBWFARSQ-HNNXBMFYSA-N 0.000 claims 1
- HPLGXOSWRUEUNI-HNNXBMFYSA-N 5-(3-aminophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thiophene-2-carboxamide Chemical compound NC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 HPLGXOSWRUEUNI-HNNXBMFYSA-N 0.000 claims 1
- XQIJQYLQZPHQDF-UHFFFAOYSA-N 5-(3-aminophenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(N)=C1 XQIJQYLQZPHQDF-UHFFFAOYSA-N 0.000 claims 1
- VZXAJUCWNRKHTL-UHFFFAOYSA-N 5-(4-fluorophenyl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=C(F)C=C1 VZXAJUCWNRKHTL-UHFFFAOYSA-N 0.000 claims 1
- JZJSJLYCLODZGT-UHFFFAOYSA-N 5-[3-(aminomethyl)phenyl]-n-(1-azabicyclo[2.2.2]octan-3-yl)thiophene-2-carboxamide Chemical compound NCC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 JZJSJLYCLODZGT-UHFFFAOYSA-N 0.000 claims 1
- JZJSJLYCLODZGT-INIZCTEOSA-N 5-[3-(aminomethyl)phenyl]-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thiophene-2-carboxamide Chemical compound NCC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 JZJSJLYCLODZGT-INIZCTEOSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- HVMOWCDQBWRDAO-UHFFFAOYSA-N N12CC(C(CC1)CC2)NC(=O)C2=CSC=C2C2=CC=CC=C2 Chemical compound N12CC(C(CC1)CC2)NC(=O)C2=CSC=C2C2=CC=CC=C2 HVMOWCDQBWRDAO-UHFFFAOYSA-N 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000003935 attention Effects 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000001713 cholinergic effect Effects 0.000 claims 1
- 230000007278 cognition impairment Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- 230000006984 memory degeneration Effects 0.000 claims 1
- 208000023060 memory loss Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- KIFFOBXBQBZBPM-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(2-methoxyphenyl)benzamide Chemical compound COC1=CC=CC=C1C1=CC=CC(C(=O)NC2C3CCN(CC3)C2)=C1 KIFFOBXBQBZBPM-UHFFFAOYSA-N 0.000 claims 1
- WTUHRGRJMXKQOM-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(3,5-dichlorophenyl)benzamide Chemical compound ClC1=CC(Cl)=CC(C=2C=C(C=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 WTUHRGRJMXKQOM-UHFFFAOYSA-N 0.000 claims 1
- BHVNSJHUVOVCMX-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(3-fluorophenyl)benzamide Chemical compound FC1=CC=CC(C=2C=C(C=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 BHVNSJHUVOVCMX-UHFFFAOYSA-N 0.000 claims 1
- UVLJDZIZYSDTKE-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(3-methoxyphenyl)benzamide Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 UVLJDZIZYSDTKE-UHFFFAOYSA-N 0.000 claims 1
- VTRZFLGHZHXPNK-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(3-methylphenyl)benzamide Chemical compound CC1=CC=CC(C=2C=C(C=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 VTRZFLGHZHXPNK-UHFFFAOYSA-N 0.000 claims 1
- CLUDFFGNGQDYJV-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(4-fluorophenyl)benzamide Chemical compound C1=CC(F)=CC=C1C1=CC=CC(C(=O)NC2C3CCN(CC3)C2)=C1 CLUDFFGNGQDYJV-UHFFFAOYSA-N 0.000 claims 1
- DAWFSECLBKZUHN-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-bromobenzamide Chemical compound BrC1=CC=CC(C(=O)NC2C3CCN(CC3)C2)=C1 DAWFSECLBKZUHN-UHFFFAOYSA-N 0.000 claims 1
- RWRRNEWYRHYZAK-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-iodobenzamide Chemical compound IC1=CC=CC(C(=O)NC2C3CCN(CC3)C2)=C1 RWRRNEWYRHYZAK-UHFFFAOYSA-N 0.000 claims 1
- CAGKKXJJWGYHAV-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-naphthalen-2-ylbenzamide Chemical compound C1=CC=CC2=CC(C=3C=CC=C(C=3)C(NC3C4CCN(CC4)C3)=O)=CC=C21 CAGKKXJJWGYHAV-UHFFFAOYSA-N 0.000 claims 1
- MQDUBMOSAYRTMJ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-phenylbenzamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 MQDUBMOSAYRTMJ-UHFFFAOYSA-N 0.000 claims 1
- GLNKFTQXNCWCSJ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-pyridin-3-ylbenzamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(C=1)=CC=CC=1C1=CC=CN=C1 GLNKFTQXNCWCSJ-UHFFFAOYSA-N 0.000 claims 1
- NWJHCFDCWWUKAS-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-thiophen-2-ylbenzamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(C=1)=CC=CC=1C1=CC=CS1 NWJHCFDCWWUKAS-UHFFFAOYSA-N 0.000 claims 1
- CENIOWYLMHMVTC-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-3-thiophen-3-ylbenzamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(C=1)=CC=CC=1C=1C=CSC=1 CENIOWYLMHMVTC-UHFFFAOYSA-N 0.000 claims 1
- BXVSCDNQMVRJHW-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-4-bromobenzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1C(CC2)CCN2C1 BXVSCDNQMVRJHW-UHFFFAOYSA-N 0.000 claims 1
- OFMXVWXJUWNVGE-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-4-bromothiophene-2-carboxamide Chemical compound BrC1=CSC(C(=O)NC2C3CCN(CC3)C2)=C1 OFMXVWXJUWNVGE-UHFFFAOYSA-N 0.000 claims 1
- OOGWQHRFIFVTEZ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-4-iodobenzamide Chemical compound C1=CC(I)=CC=C1C(=O)NC1C(CC2)CCN2C1 OOGWQHRFIFVTEZ-UHFFFAOYSA-N 0.000 claims 1
- SORHTMNAVSNZNU-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-4-pyridin-2-ylthiophene-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(SC=1)=CC=1C1=CC=CC=N1 SORHTMNAVSNZNU-UHFFFAOYSA-N 0.000 claims 1
- CCJXUEWABMMONA-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-4-pyridin-3-ylthiophene-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(SC=1)=CC=1C1=CC=CN=C1 CCJXUEWABMMONA-UHFFFAOYSA-N 0.000 claims 1
- NDEVYBGGPPDEPG-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-4-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(SC=1)=CC=1C1=CC=NC=C1 NDEVYBGGPPDEPG-UHFFFAOYSA-N 0.000 claims 1
- LIPAWTBPKLAATH-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(1-benzofuran-2-yl)furan-2-carboxamide Chemical compound C1=CC=C2OC(C3=CC=C(O3)C(NC3C4CCN(CC4)C3)=O)=CC2=C1 LIPAWTBPKLAATH-UHFFFAOYSA-N 0.000 claims 1
- MUAPAJCASHAKDD-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(2-methoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC=CC=C1C1=CC=C(C(=O)NC2C3CCN(CC3)C2)O1 MUAPAJCASHAKDD-UHFFFAOYSA-N 0.000 claims 1
- XKKZIJRJJSXKPX-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3,5-dimethyl-1,2-oxazol-4-yl)furan-2-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(=O)NC2C3CCN(CC3)C2)O1 XKKZIJRJJSXKPX-UHFFFAOYSA-N 0.000 claims 1
- XGBYUOBPRHUNDX-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3,5-dimethyl-1,2-oxazol-4-yl)thiophene-2-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(=O)NC2C3CCN(CC3)C2)S1 XGBYUOBPRHUNDX-UHFFFAOYSA-N 0.000 claims 1
- CRXXTGJTHQIACI-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-chlorophenyl)furan-2-carboxamide Chemical compound ClC1=CC=CC(C=2OC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 CRXXTGJTHQIACI-UHFFFAOYSA-N 0.000 claims 1
- QTGLVGGNFKMBPR-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-chlorophenyl)thiophene-2-carboxamide Chemical compound ClC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 QTGLVGGNFKMBPR-UHFFFAOYSA-N 0.000 claims 1
- FZDZHQNLYQWDSJ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-cyanophenyl)thiophene-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(S1)=CC=C1C1=CC=CC(C#N)=C1 FZDZHQNLYQWDSJ-UHFFFAOYSA-N 0.000 claims 1
- PJOONCNDVDQBAH-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-ethoxyphenyl)thiophene-2-carboxamide Chemical compound CCOC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 PJOONCNDVDQBAH-UHFFFAOYSA-N 0.000 claims 1
- OIEAJUFPEQIZHL-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-fluorophenyl)furan-2-carboxamide Chemical compound FC1=CC=CC(C=2OC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 OIEAJUFPEQIZHL-UHFFFAOYSA-N 0.000 claims 1
- WUKDHJGFJBQDAY-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-fluorophenyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 WUKDHJGFJBQDAY-UHFFFAOYSA-N 0.000 claims 1
- UWKVRXHHKRDKTN-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-formylphenyl)thiophene-2-carboxamide Chemical compound O=CC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 UWKVRXHHKRDKTN-UHFFFAOYSA-N 0.000 claims 1
- LCGCTFJMVXHREJ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide Chemical compound OC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 LCGCTFJMVXHREJ-UHFFFAOYSA-N 0.000 claims 1
- FEKRXODBAGHYRA-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-methoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC=CC(C=2OC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 FEKRXODBAGHYRA-UHFFFAOYSA-N 0.000 claims 1
- GALYCJSQLYPAQX-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-methoxyphenyl)thiophene-2-carboxamide Chemical compound COC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 GALYCJSQLYPAQX-UHFFFAOYSA-N 0.000 claims 1
- RFMVCNKMEMIOTJ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-methylphenyl)furan-2-carboxamide Chemical compound CC1=CC=CC(C=2OC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 RFMVCNKMEMIOTJ-UHFFFAOYSA-N 0.000 claims 1
- IUYIHWNTJKCXNG-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-morpholin-4-ylphenyl)thiophene-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(S1)=CC=C1C(C=1)=CC=CC=1N1CCOCC1 IUYIHWNTJKCXNG-UHFFFAOYSA-N 0.000 claims 1
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| US6500840B2 (en) | 2000-08-21 | 2002-12-31 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
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| PE20021019A1 (es) * | 2001-04-19 | 2002-11-13 | Upjohn Co | Grupos azabiciclicos sustituidos |
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| JP2005510523A (ja) | 2001-11-09 | 2005-04-21 | ファルマシア アンド アップジョン カンパニー リミティド ライアビリティー カンパニー | アザ二環式フェニル縮合複素環式化合物、及びα７ＮＡＣＨＲリガンドとしての当該化合物の使用 |
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| BR0307782A (pt) * | 2002-02-19 | 2005-01-04 | Upjohn Co | Compostos azabiciclo para o tratamento de doença |
| US6858613B2 (en) | 2002-02-19 | 2005-02-22 | Pfizer Inc. | Fused bicyclic-N-bridged-heteroaromatic carboxamides for the treatment of disease |
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| JP2005537297A (ja) | 2002-08-01 | 2005-12-08 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | アルファ−７ｎａｃｈｒ活性を有する１ｈ−ピラゾールおよび１ｈ−ピロール−アザビシクロ化合物 |
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| WO2005000250A2 (en) * | 2003-06-24 | 2005-01-06 | Johns Hopkins University | Imaging agents and methods of imaging alpha 7-nicotinic cholinergic receptor |
| DE10334724A1 (de) * | 2003-07-30 | 2005-02-24 | Bayer Healthcare Ag | N-Biarylamide |
| SG149052A1 (en) * | 2003-12-22 | 2009-01-29 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| BRPI0417933A (pt) * | 2003-12-22 | 2007-04-17 | Astrazeneca Ab | composto, métodos para o tratamento ou a profilaxia de uma doença ou condição, e de distúrbios, e para a indução da cessação do hábito de fumar, composição farmacêutica, e, uso de um composto |
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| BRPI0417933A (pt) * | 2003-12-22 | 2007-04-17 | Astrazeneca Ab | composto, métodos para o tratamento ou a profilaxia de uma doença ou condição, e de distúrbios, e para a indução da cessação do hábito de fumar, composição farmacêutica, e, uso de um composto |
| US7396830B2 (en) * | 2005-10-04 | 2008-07-08 | Bristol-Myers Squibb Company | Piperazine amidines as antiviral agents |
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2000
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- 2001-02-15 EP EP01904770A patent/EP1259508B1/en not_active Expired - Lifetime
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- 2001-02-15 SK SK1179-2002A patent/SK11792002A3/sk unknown
- 2001-02-15 HU HU0301069A patent/HUP0301069A3/hu unknown
- 2001-02-15 ES ES01904770T patent/ES2208556T3/es not_active Expired - Lifetime
- 2001-02-15 CN CNB018049362A patent/CN100345847C/zh not_active Expired - Fee Related
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- 2001-02-15 DK DK01904770T patent/DK1259508T3/da active
- 2001-02-15 AU AU32594/01A patent/AU782693B2/en not_active Ceased
- 2001-02-15 AT AT01904770T patent/ATE252099T1/de not_active IP Right Cessation
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- 2001-02-15 PT PT01904770T patent/PT1259508E/pt unknown
- 2001-02-15 DE DE60100996T patent/DE60100996T2/de not_active Expired - Fee Related
- 2001-02-15 RU RU2002118302/04A patent/RU2263114C2/ru active
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