JP2003512374A - キヌクリジンアクリルアミド - Google Patents
キヌクリジンアクリルアミドInfo
- Publication number
- JP2003512374A JP2003512374A JP2001531833A JP2001531833A JP2003512374A JP 2003512374 A JP2003512374 A JP 2003512374A JP 2001531833 A JP2001531833 A JP 2001531833A JP 2001531833 A JP2001531833 A JP 2001531833A JP 2003512374 A JP2003512374 A JP 2003512374A
- Authority
- JP
- Japan
- Prior art keywords
- aza
- bicyclo
- propenamide
- oct
- disease
- 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
Links
- BRJQKJLCLZBQCK-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane;prop-2-enamide Chemical compound NC(=O)C=C.C1CC2CCN1CC2 BRJQKJLCLZBQCK-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 238000000034 method Methods 0.000 claims abstract description 45
- -1 -COTwoRFive Chemical group 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 230000002265 prevention Effects 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 201000010099 disease Diseases 0.000 claims description 18
- 229960002715 nicotine Drugs 0.000 claims description 14
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- 230000006735 deficit Effects 0.000 claims description 11
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- 208000018737 Parkinson disease Diseases 0.000 claims description 8
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 8
- 208000016620 Tourette disease Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 230000002829 reductive effect Effects 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 208000000044 Amnesia Diseases 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
- 208000020925 Bipolar disease Diseases 0.000 claims description 7
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 7
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
- 208000023105 Huntington disease Diseases 0.000 claims description 7
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 7
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 7
- 201000002832 Lewy body dementia Diseases 0.000 claims description 7
- 206010026749 Mania Diseases 0.000 claims description 7
- 208000026139 Memory disease Diseases 0.000 claims description 7
- 206010057852 Nicotine dependence Diseases 0.000 claims description 7
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 7
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 7
- 208000028683 bipolar I disease Diseases 0.000 claims description 7
- 230000001713 cholinergic effect Effects 0.000 claims description 7
- 208000010877 cognitive disease Diseases 0.000 claims description 7
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 7
- 201000003723 learning disability Diseases 0.000 claims description 7
- 230000006984 memory degeneration Effects 0.000 claims description 7
- 208000023060 memory loss Diseases 0.000 claims description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 210000000225 synapse Anatomy 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- KZSCMMXQCHXNIV-PPOCWRSBSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-pyridin-2-ylsulfanylprop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C\SC1=CC=CC=N1 KZSCMMXQCHXNIV-PPOCWRSBSA-N 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000005586 smoking cessation Effects 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- ICLMIHKBDLBDCI-LHXVZLOVSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-([1,3]thiazolo[4,5-b]pyridin-2-ylsulfanyl)prop-2-enamide Chemical compound C1=CC=C2SC(S/C=C/C(N[C@@H]3C4CCN(CC4)C3)=O)=NC2=N1 ICLMIHKBDLBDCI-LHXVZLOVSA-N 0.000 claims description 4
- GJKBMIXSYCLYRG-REPPVQDKSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-pyrimidin-2-ylsulfanylprop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C/SC1=NC=CC=N1 GJKBMIXSYCLYRG-REPPVQDKSA-N 0.000 claims description 4
- ISFXODZDHSDPLN-KFRNIWOLSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(1-methylimidazol-2-yl)sulfanylprop-2-enamide Chemical compound CN1C=CN=C1S\C=C\C(=O)N[C@@H]1C(CC2)CCN2C1 ISFXODZDHSDPLN-KFRNIWOLSA-N 0.000 claims description 3
- OCAWQQJWTRIKGZ-AEBAWRHJSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(1h-imidazol-2-ylsulfanyl)prop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C\SC1=NC=CN1 OCAWQQJWTRIKGZ-AEBAWRHJSA-N 0.000 claims description 3
- LTYPMDPWOZGHRI-ZHZWZMEUSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(2-methoxyphenyl)sulfanylprop-2-enamide Chemical compound COC1=CC=CC=C1S\C=C\C(=O)N[C@@H]1C(CC2)CCN2C1 LTYPMDPWOZGHRI-ZHZWZMEUSA-N 0.000 claims description 3
- JQEIDFKXAIOCOT-PPYMECGQSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(3-fluorophenyl)sulfanylprop-2-enamide Chemical compound FC1=CC=CC(S\C=C\C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 JQEIDFKXAIOCOT-PPYMECGQSA-N 0.000 claims description 3
- KDTOXPBRVFGSBE-JCVNQNCUSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(3-methoxyphenyl)sulfanylprop-2-enamide Chemical compound COC1=CC=CC(S\C=C\C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 KDTOXPBRVFGSBE-JCVNQNCUSA-N 0.000 claims description 3
- KTQRXHIDICAXBQ-VSGCLNPGSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(4-fluorophenyl)sulfanylprop-2-enamide Chemical compound C1=CC(F)=CC=C1S\C=C\C(=O)N[C@@H]1C(CC2)CCN2C1 KTQRXHIDICAXBQ-VSGCLNPGSA-N 0.000 claims description 3
- SCMNIXVFVRESKS-KXKDPZRNSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(4-methoxyphenyl)sulfanylprop-2-enamide Chemical compound C1=CC(OC)=CC=C1S\C=C\C(=O)N[C@@H]1C(CC2)CCN2C1 SCMNIXVFVRESKS-KXKDPZRNSA-N 0.000 claims description 3
- JWTLOTLUZAUDNW-ZPMKCOPCSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]prop-2-enamide Chemical compound S1C(C)=NN=C1S\C=C\C(=O)N[C@@H]1C(CC2)CCN2C1 JWTLOTLUZAUDNW-ZPMKCOPCSA-N 0.000 claims description 3
- PESOSIYLBKVXMY-SEIPJRMCSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-pyridin-4-ylsulfanylprop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C\SC1=CC=NC=C1 PESOSIYLBKVXMY-SEIPJRMCSA-N 0.000 claims description 3
- WNQKTIKCUDTAKX-LHXVZLOVSA-N (e)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-thiophen-2-ylsulfanylprop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C\SC1=CC=CS1 WNQKTIKCUDTAKX-LHXVZLOVSA-N 0.000 claims description 3
- OVBCUYMXSLVZNW-YHAOYDPOSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(1,3-benzothiazol-2-ylsulfanyl)prop-2-enamide Chemical compound C1=CC=C2SC(S\C=C/C(N[C@@H]3C4CCN(CC4)C3)=O)=NC2=C1 OVBCUYMXSLVZNW-YHAOYDPOSA-N 0.000 claims description 3
- DFRCDJNMANEUOX-YHAOYDPOSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(1,3-benzoxazol-2-ylsulfanyl)prop-2-enamide Chemical compound C1=CC=C2OC(S\C=C/C(N[C@@H]3C4CCN(CC4)C3)=O)=NC2=C1 DFRCDJNMANEUOX-YHAOYDPOSA-N 0.000 claims description 3
- UAHBYMCLKLVWDR-UFVHFEBBSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(1,3-thiazol-2-ylsulfanyl)prop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C/SC1=NC=CS1 UAHBYMCLKLVWDR-UFVHFEBBSA-N 0.000 claims description 3
- ISFXODZDHSDPLN-REPPVQDKSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(1-methylimidazol-2-yl)sulfanylprop-2-enamide Chemical compound CN1C=CN=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 ISFXODZDHSDPLN-REPPVQDKSA-N 0.000 claims description 3
- LTYPMDPWOZGHRI-MSKHEQNASA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(2-methoxyphenyl)sulfanylprop-2-enamide Chemical compound COC1=CC=CC=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 LTYPMDPWOZGHRI-MSKHEQNASA-N 0.000 claims description 3
- VRAGHHQHEMRZLW-QGOGUYACSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(2-methylfuran-3-yl)sulfanylprop-2-enamide Chemical compound O1C=CC(S\C=C/C(=O)N[C@@H]2C3CCN(CC3)C2)=C1C VRAGHHQHEMRZLW-QGOGUYACSA-N 0.000 claims description 3
- KDQHLQDGSUEZLO-QIENPNARSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(2-methylphenyl)sulfanylprop-2-enamide Chemical compound CC1=CC=CC=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 KDQHLQDGSUEZLO-QIENPNARSA-N 0.000 claims description 3
- JQEIDFKXAIOCOT-AJHXJQRKSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(3-fluorophenyl)sulfanylprop-2-enamide Chemical compound FC1=CC=CC(S\C=C/C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 JQEIDFKXAIOCOT-AJHXJQRKSA-N 0.000 claims description 3
- KDTOXPBRVFGSBE-BJIFSAINSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(3-methoxyphenyl)sulfanylprop-2-enamide Chemical compound COC1=CC=CC(S\C=C/C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 KDTOXPBRVFGSBE-BJIFSAINSA-N 0.000 claims description 3
- WLZQYKJPCDLBLY-BJIFSAINSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(3-methylphenyl)sulfanylprop-2-enamide Chemical compound CC1=CC=CC(S\C=C/C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 WLZQYKJPCDLBLY-BJIFSAINSA-N 0.000 claims description 3
- UEOWRBUHJNVLTL-XMELGKRDSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(4-chlorophenyl)sulfanylprop-2-enamide Chemical compound C1=CC(Cl)=CC=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 UEOWRBUHJNVLTL-XMELGKRDSA-N 0.000 claims description 3
- KTQRXHIDICAXBQ-XMELGKRDSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(4-fluorophenyl)sulfanylprop-2-enamide Chemical compound C1=CC(F)=CC=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 KTQRXHIDICAXBQ-XMELGKRDSA-N 0.000 claims description 3
- SCMNIXVFVRESKS-CLOOOTJHSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(4-methoxyphenyl)sulfanylprop-2-enamide Chemical compound C1=CC(OC)=CC=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 SCMNIXVFVRESKS-CLOOOTJHSA-N 0.000 claims description 3
- HFGGWDUKVDQHAF-CLOOOTJHSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(4-methylphenyl)sulfanylprop-2-enamide Chemical compound C1=CC(C)=CC=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 HFGGWDUKVDQHAF-CLOOOTJHSA-N 0.000 claims description 3
- JWTLOTLUZAUDNW-IBHLPDHGSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]prop-2-enamide Chemical compound S1C(C)=NN=C1S\C=C/C(=O)N[C@@H]1C(CC2)CCN2C1 JWTLOTLUZAUDNW-IBHLPDHGSA-N 0.000 claims description 3
- VRUSTLVHEAFHJV-KVNDZABWSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-phenylsulfanylbut-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)/C=C(/C)SC1=CC=CC=C1 VRUSTLVHEAFHJV-KVNDZABWSA-N 0.000 claims description 3
- KZSCMMXQCHXNIV-HKBVPSITSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-pyridin-2-ylsulfanylprop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C/SC1=CC=CC=N1 KZSCMMXQCHXNIV-HKBVPSITSA-N 0.000 claims description 3
- PESOSIYLBKVXMY-MFNCVGGLSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-pyridin-4-ylsulfanylprop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C/SC1=CC=NC=C1 PESOSIYLBKVXMY-MFNCVGGLSA-N 0.000 claims description 3
- WNQKTIKCUDTAKX-LRAPTIAOSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-thiophen-2-ylsulfanylprop-2-enamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C/SC1=CC=CS1 WNQKTIKCUDTAKX-LRAPTIAOSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- OVBCUYMXSLVZNW-JXMROGBWSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(1,3-benzothiazol-2-ylsulfanyl)prop-2-enamide Chemical compound C1=CC=C2SC(S/C=C/C(NC3C4CCN(CC4)C3)=O)=NC2=C1 OVBCUYMXSLVZNW-JXMROGBWSA-N 0.000 claims description 2
- ISFXODZDHSDPLN-RUDMXATFSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(1-methylimidazol-2-yl)sulfanylprop-2-enamide Chemical compound CN1C=CN=C1S\C=C\C(=O)NC1C(CC2)CCN2C1 ISFXODZDHSDPLN-RUDMXATFSA-N 0.000 claims description 2
- OCAWQQJWTRIKGZ-FPYGCLRLSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(1h-imidazol-2-ylsulfanyl)prop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C\SC1=NC=CN1 OCAWQQJWTRIKGZ-FPYGCLRLSA-N 0.000 claims description 2
- LTYPMDPWOZGHRI-DHZHZOJOSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(2-methoxyphenyl)sulfanylprop-2-enamide Chemical compound COC1=CC=CC=C1S\C=C\C(=O)NC1C(CC2)CCN2C1 LTYPMDPWOZGHRI-DHZHZOJOSA-N 0.000 claims description 2
- VRAGHHQHEMRZLW-WEVVVXLNSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(2-methylfuran-3-yl)sulfanylprop-2-enamide Chemical compound O1C=CC(S\C=C\C(=O)NC2C3CCN(CC3)C2)=C1C VRAGHHQHEMRZLW-WEVVVXLNSA-N 0.000 claims description 2
- KDQHLQDGSUEZLO-DHZHZOJOSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(2-methylphenyl)sulfanylprop-2-enamide Chemical compound CC1=CC=CC=C1S\C=C\C(=O)NC1C(CC2)CCN2C1 KDQHLQDGSUEZLO-DHZHZOJOSA-N 0.000 claims description 2
- JQEIDFKXAIOCOT-RMKNXTFCSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(3-fluorophenyl)sulfanylprop-2-enamide Chemical compound FC1=CC=CC(S\C=C\C(=O)NC2C3CCN(CC3)C2)=C1 JQEIDFKXAIOCOT-RMKNXTFCSA-N 0.000 claims description 2
- KDTOXPBRVFGSBE-JXMROGBWSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(3-methoxyphenyl)sulfanylprop-2-enamide Chemical compound COC1=CC=CC(S\C=C\C(=O)NC2C3CCN(CC3)C2)=C1 KDTOXPBRVFGSBE-JXMROGBWSA-N 0.000 claims description 2
- WLZQYKJPCDLBLY-JXMROGBWSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(3-methylphenyl)sulfanylprop-2-enamide Chemical compound CC1=CC=CC(S\C=C\C(=O)NC2C3CCN(CC3)C2)=C1 WLZQYKJPCDLBLY-JXMROGBWSA-N 0.000 claims description 2
- KTQRXHIDICAXBQ-JXMROGBWSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(4-fluorophenyl)sulfanylprop-2-enamide Chemical compound C1=CC(F)=CC=C1S\C=C\C(=O)NC1C(CC2)CCN2C1 KTQRXHIDICAXBQ-JXMROGBWSA-N 0.000 claims description 2
- SCMNIXVFVRESKS-DHZHZOJOSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(4-methoxyphenyl)sulfanylprop-2-enamide Chemical compound C1=CC(OC)=CC=C1S\C=C\C(=O)NC1C(CC2)CCN2C1 SCMNIXVFVRESKS-DHZHZOJOSA-N 0.000 claims description 2
- HFGGWDUKVDQHAF-DHZHZOJOSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(4-methylphenyl)sulfanylprop-2-enamide Chemical compound C1=CC(C)=CC=C1S\C=C\C(=O)NC1C(CC2)CCN2C1 HFGGWDUKVDQHAF-DHZHZOJOSA-N 0.000 claims description 2
- JWTLOTLUZAUDNW-QPJJXVBHSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]prop-2-enamide Chemical compound S1C(C)=NN=C1S\C=C\C(=O)NC1C(CC2)CCN2C1 JWTLOTLUZAUDNW-QPJJXVBHSA-N 0.000 claims description 2
- KZSCMMXQCHXNIV-UXBLZVDNSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-pyridin-2-ylsulfanylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C\SC1=CC=CC=N1 KZSCMMXQCHXNIV-UXBLZVDNSA-N 0.000 claims description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9903760-8 | 1999-10-18 | ||
| SE9903760A SE9903760D0 (sv) | 1999-10-18 | 1999-10-18 | New compounds |
| PCT/SE2000/001993 WO2001029034A1 (en) | 1999-10-18 | 2000-10-13 | Quinuclidine acrylamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003512374A true JP2003512374A (ja) | 2003-04-02 |
| JP2003512374A5 JP2003512374A5 (enExample) | 2007-11-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001531833A Pending JP2003512374A (ja) | 1999-10-18 | 2000-10-13 | キヌクリジンアクリルアミド |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6642246B1 (enExample) |
| EP (1) | EP1235826B1 (enExample) |
| JP (1) | JP2003512374A (enExample) |
| AT (1) | ATE248837T1 (enExample) |
| AU (1) | AU1069001A (enExample) |
| CO (1) | CO5271691A1 (enExample) |
| DE (1) | DE60005054T2 (enExample) |
| DK (1) | DK1235826T3 (enExample) |
| ES (1) | ES2204711T3 (enExample) |
| HK (1) | HK1048313B (enExample) |
| MY (1) | MY136240A (enExample) |
| PT (1) | PT1235826E (enExample) |
| SE (1) | SE9903760D0 (enExample) |
| WO (1) | WO2001029034A1 (enExample) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6492386B2 (en) * | 2000-08-18 | 2002-12-10 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| JP2004506735A (ja) * | 2000-08-18 | 2004-03-04 | ファルマシア・アンド・アップジョン・カンパニー | 疾患治療用キヌクリジン置換アリール化合物 |
| AU2001282873A1 (en) | 2000-08-18 | 2002-03-04 | Pharmacia And Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| PE20021019A1 (es) | 2001-04-19 | 2002-11-13 | Upjohn Co | Grupos azabiciclicos sustituidos |
| WO2003018585A1 (en) | 2001-08-24 | 2003-03-06 | Pharmacia & Upjohn Company | Substituted-heteroaryl-7-aza[2.2.1]bicycloheptanes for the treatment of disease |
| AU2002339810A1 (en) * | 2001-10-16 | 2003-04-28 | Astrazeneca Ab | Azabicyclic compounds for the treatment of fibromyalgia syndrome |
| EP1442037A1 (en) * | 2001-11-09 | 2004-08-04 | PHARMACIA & UPJOHN COMPANY | Azabicyclic-phenyl-fused-heterocyclic compounds and their use as alpha7 nachr ligands |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| EP1480977A2 (en) | 2002-02-15 | 2004-12-01 | PHARMACIA & UPJOHN COMPANY | Substituted aryl compounds for treatment of disease |
| CA2476681A1 (en) | 2002-02-19 | 2003-08-28 | Bruce N. Rogers | Fused bicyclic-n-bridged-heteroaromatic carboxamides for the treatment of disease |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| SK288115B6 (sk) | 2002-09-25 | 2013-09-03 | Memory Pharmaceuticals Corporation | Indazoles, pharmaceutical compositions comprising them and their use |
| JP4824578B2 (ja) * | 2003-12-22 | 2011-11-30 | メモリー・ファーマシューティカルズ・コーポレイション | インドール類、１，２−ベンズイソオキサゾール類、および１，２−ベンゾイソチアゾール類、ならびにそれらの製造と使用 |
| MXPA06010852A (es) | 2004-03-25 | 2007-01-16 | Memory Pharm Corp | Indazoles, benzotiazoles, benzoisotiazoles, bencisoxazoles y preparacion y usos de los mismos. |
| 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 |
| KR20070015607A (ko) | 2004-05-07 | 2007-02-05 | 메모리 파마슈티칼스 코포레이션 | 1ｈ-인다졸, 벤조티아졸, 1,2-벤조이속사졸,1,2-벤조이소티아졸, 및 크로몬 및 그의 제조법 및 용도 |
| PE20060437A1 (es) | 2004-06-18 | 2006-06-08 | Novartis Ag | COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| GB0424564D0 (en) | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
| CA2591817A1 (en) | 2004-12-22 | 2006-06-29 | Memory Pharmaceuticals Corporation | Nicotinic alpha-7 receptor ligands and preparation and uses thereof |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| US8431603B2 (en) * | 2008-04-15 | 2013-04-30 | Eisai R&D Management Co., Ltd. | 3-phenylpyrazolo[5,1-b]thiazole compounds |
| RS52703B (sr) | 2008-06-20 | 2013-08-30 | Astrazeneca Ab | Derivat dibenzotiazepina i njegova upotreba |
| EP2243476A1 (en) * | 2009-04-17 | 2010-10-27 | Centre National de la Recherche Scientifique | Compounds for the treatment of mitochondrial diseases |
| AR078521A1 (es) * | 2009-10-08 | 2011-11-16 | Eisai R&D Man Co Ltd | Compuesto pirazolotiazol |
| PT3029039T (pt) | 2010-05-17 | 2017-11-28 | Forum Pharmaceuticals Inc | Formulações farmacêuticas que compreendem formas cristalinas de cloridrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida mono-hidratado |
| 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 |
| EP2846796A4 (en) | 2012-05-08 | 2015-10-21 | Forum Pharmaceuticals Inc | METHODS OF MAINTAINING, PROCESSING OR ENHANCING COGNITIVE FUNCTION |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| JP6478923B2 (ja) | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| EA029430B1 (ru) | 2013-06-21 | 2018-03-30 | Такеда Фармасьютикл Компани Лимитед | Производные 1-сульфонилпиперидина в качестве модуляторов рецепторов прокинетицина |
| 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 |
| CN103923105B (zh) * | 2014-04-17 | 2016-08-24 | 北京大学 | 2-中氮茚甲酰胺类化合物及其制备和用途 |
| 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 |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08507300A (ja) * | 1993-03-05 | 1996-08-06 | グラクソ、ソシエタ、ペル、アツイオーニ | 興奮性アミノ酸の拮抗剤としてのインドール誘導体 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1255467B (it) * | 1992-07-29 | 1995-11-02 | Dompe Farmaceutici Spa | Ammidi acriliche farmacologicamente attive |
| PL321263A1 (en) * | 1995-01-10 | 1997-11-24 | Smithkline Beecham Spa | Derivatives of indole useful in treating osteoporosis |
| JPH11512443A (ja) * | 1995-09-22 | 1999-10-26 | ノボ ノルディスク アクティーゼルスカブ | 新規な置換アザ環式またはアザ二環式化合物 |
| PL330994A1 (en) * | 1996-07-09 | 1999-06-21 | Smithkline Beecham Spa | Indolic derivatives for use in treating osteoporosis |
-
1999
- 1999-10-18 SE SE9903760A patent/SE9903760D0/xx unknown
-
2000
- 2000-10-13 EP EP00971959A patent/EP1235826B1/en not_active Expired - Lifetime
- 2000-10-13 US US10/110,663 patent/US6642246B1/en not_active Expired - Fee Related
- 2000-10-13 DE DE60005054T patent/DE60005054T2/de not_active Expired - Lifetime
- 2000-10-13 AU AU10690/01A patent/AU1069001A/en not_active Abandoned
- 2000-10-13 JP JP2001531833A patent/JP2003512374A/ja active Pending
- 2000-10-13 AT AT00971959T patent/ATE248837T1/de active
- 2000-10-13 DK DK00971959T patent/DK1235826T3/da active
- 2000-10-13 ES ES00971959T patent/ES2204711T3/es not_active Expired - Lifetime
- 2000-10-13 WO PCT/SE2000/001993 patent/WO2001029034A1/en not_active Ceased
- 2000-10-13 PT PT00971959T patent/PT1235826E/pt unknown
- 2000-10-13 HK HK03100456.4A patent/HK1048313B/en not_active IP Right Cessation
- 2000-10-16 MY MYPI20004849A patent/MY136240A/en unknown
- 2000-10-17 CO CO00078738A patent/CO5271691A1/es not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08507300A (ja) * | 1993-03-05 | 1996-08-06 | グラクソ、ソシエタ、ペル、アツイオーニ | 興奮性アミノ酸の拮抗剤としてのインドール誘導体 |
Non-Patent Citations (1)
| Title |
|---|
| JPN6010057065, Ｋｏｓｔｏｃｈｋａ，Ｌ．Ｍ．，ｅｔ ａｌ, Ｋｈｉｍｉｋｏ−Ｆａｒｍａｔｓｅｖｔｉｃｈｅｓｋｉｉ Ｚｈｕｒｎａｌ, 1995, Ｖｏｌ．２９, ｐｐ ４０−４２ * |
Also Published As
| Publication number | Publication date |
|---|---|
| US6642246B1 (en) | 2003-11-04 |
| CO5271691A1 (es) | 2003-04-30 |
| HK1048313B (en) | 2003-12-24 |
| PT1235826E (pt) | 2004-01-30 |
| DE60005054D1 (de) | 2003-10-09 |
| EP1235826B1 (en) | 2003-09-03 |
| WO2001029034A1 (en) | 2001-04-26 |
| EP1235826A1 (en) | 2002-09-04 |
| AU1069001A (en) | 2001-04-30 |
| DE60005054T2 (de) | 2004-07-08 |
| DK1235826T3 (da) | 2003-11-24 |
| ES2204711T3 (es) | 2004-05-01 |
| MY136240A (en) | 2008-08-29 |
| HK1048313A1 (en) | 2003-03-28 |
| ATE248837T1 (de) | 2003-09-15 |
| SE9903760D0 (sv) | 1999-10-18 |
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