JP2003512374A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003512374A5 JP2003512374A5 JP2001531833A JP2001531833A JP2003512374A5 JP 2003512374 A5 JP2003512374 A5 JP 2003512374A5 JP 2001531833 A JP2001531833 A JP 2001531833A JP 2001531833 A JP2001531833 A JP 2001531833A JP 2003512374 A5 JP2003512374 A5 JP 2003512374A5
- Authority
- JP
- Japan
- Prior art keywords
- propenamide
- aza
- bicyclo
- 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
- 150000001875 compounds Chemical class 0.000 description 20
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 208000024827 Alzheimer disease Diseases 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 229960002715 nicotine Drugs 0.000 description 6
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 6
- 0 CSC1(*)C(CC2)CCN2C1 Chemical compound CSC1(*)C(CC2)CCN2C1 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 4
- 208000000044 Amnesia Diseases 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 4
- 208000020925 Bipolar disease Diseases 0.000 description 4
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 4
- 208000028698 Cognitive impairment Diseases 0.000 description 4
- 206010009900 Colitis ulcerative Diseases 0.000 description 4
- 206010012289 Dementia Diseases 0.000 description 4
- 208000023105 Huntington disease Diseases 0.000 description 4
- 208000001456 Jet Lag Syndrome Diseases 0.000 description 4
- 206010026749 Mania Diseases 0.000 description 4
- 208000026139 Memory disease Diseases 0.000 description 4
- 206010057852 Nicotine dependence Diseases 0.000 description 4
- 208000018737 Parkinson disease Diseases 0.000 description 4
- 208000025569 Tobacco Use disease Diseases 0.000 description 4
- 208000000323 Tourette Syndrome Diseases 0.000 description 4
- 208000016620 Tourette disease Diseases 0.000 description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 4
- 208000028683 bipolar I disease Diseases 0.000 description 4
- 230000001713 cholinergic effect Effects 0.000 description 4
- 208000010877 cognitive disease Diseases 0.000 description 4
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 4
- 201000003723 learning disability Diseases 0.000 description 4
- 230000006984 memory degeneration Effects 0.000 description 4
- 208000023060 memory loss Diseases 0.000 description 4
- 230000004770 neurodegeneration Effects 0.000 description 4
- 208000015122 neurodegenerative disease Diseases 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 201000000980 schizophrenia Diseases 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 210000000225 synapse Anatomy 0.000 description 4
- -1 —CO 2 R 5 Chemical group 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 208000020358 Learning disease Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 230000005586 smoking cessation Effects 0.000 description 2
- 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 description 1
- DFRCDJNMANEUOX-JXMROGBWSA-N (e)-n-(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(NC3C4CCN(CC4)C3)=O)=NC2=C1 DFRCDJNMANEUOX-JXMROGBWSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- PESOSIYLBKVXMY-BJMVGYQFSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-pyridin-4-ylsulfanylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C\SC1=CC=NC=C1 PESOSIYLBKVXMY-BJMVGYQFSA-N 0.000 description 1
- GJKBMIXSYCLYRG-RUDMXATFSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-pyrimidin-2-ylsulfanylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C\SC1=NC=CC=N1 GJKBMIXSYCLYRG-RUDMXATFSA-N 0.000 description 1
- WNQKTIKCUDTAKX-WEVVVXLNSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-thiophen-2-ylsulfanylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C\SC1=CC=CS1 WNQKTIKCUDTAKX-WEVVVXLNSA-N 0.000 description 1
- OVBCUYMXSLVZNW-RNVIBTMRSA-N (e)-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-RNVIBTMRSA-N 0.000 description 1
- DFRCDJNMANEUOX-RNVIBTMRSA-N (e)-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-RNVIBTMRSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- VRAGHHQHEMRZLW-NEXMIYJRSA-N (e)-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-NEXMIYJRSA-N 0.000 description 1
- KDQHLQDGSUEZLO-SHQCLWGWSA-N (e)-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-SHQCLWGWSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- WLZQYKJPCDLBLY-JCVNQNCUSA-N (e)-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-JCVNQNCUSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- HFGGWDUKVDQHAF-KXKDPZRNSA-N (e)-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-KXKDPZRNSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- GJKBMIXSYCLYRG-KFRNIWOLSA-N (e)-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-KFRNIWOLSA-N 0.000 description 1
- 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 description 1
- OVBCUYMXSLVZNW-YFHOEESVSA-N (z)-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-YFHOEESVSA-N 0.000 description 1
- DFRCDJNMANEUOX-YFHOEESVSA-N (z)-n-(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(NC3C4CCN(CC4)C3)=O)=NC2=C1 DFRCDJNMANEUOX-YFHOEESVSA-N 0.000 description 1
- UAHBYMCLKLVWDR-CLTKARDFSA-N (z)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-(1,3-thiazol-2-ylsulfanyl)prop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C/SC1=NC=CS1 UAHBYMCLKLVWDR-CLTKARDFSA-N 0.000 description 1
- ISFXODZDHSDPLN-WTKPLQERSA-N (z)-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-WTKPLQERSA-N 0.000 description 1
- LTYPMDPWOZGHRI-FLIBITNWSA-N (z)-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-FLIBITNWSA-N 0.000 description 1
- VRAGHHQHEMRZLW-UITAMQMPSA-N (z)-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-UITAMQMPSA-N 0.000 description 1
- KDQHLQDGSUEZLO-FLIBITNWSA-N (z)-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-FLIBITNWSA-N 0.000 description 1
- JQEIDFKXAIOCOT-TWGQIWQCSA-N (z)-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-TWGQIWQCSA-N 0.000 description 1
- KDTOXPBRVFGSBE-YFHOEESVSA-N (z)-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-YFHOEESVSA-N 0.000 description 1
- WLZQYKJPCDLBLY-YFHOEESVSA-N (z)-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-YFHOEESVSA-N 0.000 description 1
- UEOWRBUHJNVLTL-YFHOEESVSA-N (z)-n-(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)NC1C(CC2)CCN2C1 UEOWRBUHJNVLTL-YFHOEESVSA-N 0.000 description 1
- KTQRXHIDICAXBQ-YFHOEESVSA-N (z)-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-YFHOEESVSA-N 0.000 description 1
- SCMNIXVFVRESKS-FLIBITNWSA-N (z)-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-FLIBITNWSA-N 0.000 description 1
- HFGGWDUKVDQHAF-FLIBITNWSA-N (z)-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-FLIBITNWSA-N 0.000 description 1
- ICLMIHKBDLBDCI-UITAMQMPSA-N (z)-n-(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(NC3C4CCN(CC4)C3)=O)=NC2=N1 ICLMIHKBDLBDCI-UITAMQMPSA-N 0.000 description 1
- JWTLOTLUZAUDNW-DAXSKMNVSA-N (z)-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-DAXSKMNVSA-N 0.000 description 1
- UFEDAHQDKOLAQK-YWEYNIOJSA-N (z)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-[4-(trifluoromethyl)pyrimidin-2-yl]sulfanylprop-2-enamide Chemical compound FC(F)(F)C1=CC=NC(S\C=C/C(=O)NC2C3CCN(CC3)C2)=N1 UFEDAHQDKOLAQK-YWEYNIOJSA-N 0.000 description 1
- VRUSTLVHEAFHJV-QBFSEMIESA-N (z)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-phenylsulfanylbut-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)/C=C(/C)SC1=CC=CC=C1 VRUSTLVHEAFHJV-QBFSEMIESA-N 0.000 description 1
- SLIFWZQWWAUARB-MKFZHGHUSA-N (z)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-phenylsulfanylprop-2-enamide;hydrochloride Chemical compound Cl.C1N(CC2)CCC2C1NC(=O)\C=C/SC1=CC=CC=C1 SLIFWZQWWAUARB-MKFZHGHUSA-N 0.000 description 1
- KZSCMMXQCHXNIV-POHAHGRESA-N (z)-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-POHAHGRESA-N 0.000 description 1
- PESOSIYLBKVXMY-YHYXMXQVSA-N (z)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-pyridin-4-ylsulfanylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C/SC1=CC=NC=C1 PESOSIYLBKVXMY-YHYXMXQVSA-N 0.000 description 1
- GJKBMIXSYCLYRG-WTKPLQERSA-N (z)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-pyrimidin-2-ylsulfanylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C/SC1=NC=CC=N1 GJKBMIXSYCLYRG-WTKPLQERSA-N 0.000 description 1
- WNQKTIKCUDTAKX-UITAMQMPSA-N (z)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-thiophen-2-ylsulfanylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C/SC1=CC=CS1 WNQKTIKCUDTAKX-UITAMQMPSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- UFEDAHQDKOLAQK-OHYQPGSNSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-[4-(trifluoromethyl)pyrimidin-2-yl]sulfanylprop-2-enamide Chemical compound FC(F)(F)C1=CC=NC(S\C=C/C(=O)N[C@@H]2C3CCN(CC3)C2)=N1 UFEDAHQDKOLAQK-OHYQPGSNSA-N 0.000 description 1
- 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 description 1
- SLIFWZQWWAUARB-SKEYYMKMSA-N (z)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-phenylsulfanylprop-2-enamide;hydrochloride Chemical compound Cl.N([C@@H]1C2CCN(CC2)C1)C(=O)\C=C/SC1=CC=CC=C1 SLIFWZQWWAUARB-SKEYYMKMSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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 JP2003512374A (ja) | 2003-04-02 |
| JP2003512374A5 true JP2003512374A5 (enExample) | 2007-11-08 |
Family
ID=20417402
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 |
|---|---|---|---|---|
| US6486172B2 (en) | 2000-08-18 | 2002-11-26 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| WO2002016358A2 (en) * | 2000-08-18 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl moieties for treatment of disease (nicotinic acetylcholine receptor ligands) |
| US6492386B2 (en) * | 2000-08-18 | 2002-12-10 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl compounds for treatment of disease |
| PE20021019A1 (es) | 2001-04-19 | 2002-11-13 | Upjohn Co | Grupos azabiciclicos sustituidos |
| US6562816B2 (en) | 2001-08-24 | 2003-05-13 | Pharmacia & Upjohn Company | Substituted-heteroaryl-7-aza[2.2.1]bicycloheptanes for the treatment of disease |
| US20040259909A1 (en) * | 2001-10-16 | 2004-12-23 | Mccarthy Dennis | Treatment of fibromyalgia syndrome |
| 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 |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| US6852716B2 (en) | 2002-02-15 | 2005-02-08 | Pfizer Inc | Substituted-aryl compounds for treatment of disease |
| US6858613B2 (en) | 2002-02-19 | 2005-02-22 | Pfizer Inc. | Fused bicyclic-N-bridged-heteroaromatic carboxamides for the treatment of disease |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| AU2003276919B2 (en) * | 2002-09-25 | 2013-05-16 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| PL1697378T3 (pl) | 2003-12-22 | 2008-04-30 | Memory Pharm Corp | Indole, 1h-indazole, 1,2-benzoizoksazole i 1,2-benzoizotiazole oraz ich wytwarzanie i zastosowania |
| US20050234095A1 (en) | 2004-03-25 | 2005-10-20 | Wenge Xie | 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 |
| US7632831B2 (en) | 2004-05-07 | 2009-12-15 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| 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 |
| JP2008525464A (ja) | 2004-12-22 | 2008-07-17 | メモリー・ファーマシューティカルズ・コーポレイション | α−７ニコチン性受容体リガンド並びにその製造及び使用 |
| 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 |
| GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| NZ588376A (en) * | 2008-04-15 | 2011-06-30 | Eisai R&D Man Co Ltd | 3-phenylpyrazolo[5,1-b]thiazole compound having antagonism against corticotropin-releasing factor (CRF) receptor |
| EP2307389B1 (en) | 2008-06-20 | 2013-01-23 | AstraZeneca AB | Dibenzothiazepine derivative and use thereof |
| 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 |
| CA2799744C (en) * | 2010-05-17 | 2020-01-28 | Envivo Pharmaceuticals, Inc. | A crystalline form of (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| US9585877B2 (en) | 2012-05-08 | 2017-03-07 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1255467B (it) * | 1992-07-29 | 1995-11-02 | Dompe Farmaceutici Spa | Ammidi acriliche farmacologicamente attive |
| GB9304500D0 (en) * | 1993-03-05 | 1993-04-21 | Glaxo Spa | Heterocyclic compounds |
| US5981525A (en) | 1995-01-10 | 1999-11-09 | Smithkline Beecham Corporation | Indole derivatives useful in the treatment of osteoporosis |
| EP0853621A1 (en) * | 1995-09-22 | 1998-07-22 | Novo Nordisk A/S | Novel substituted azacyclic or azabicyclic compounds |
| EP0914321B1 (en) * | 1996-07-09 | 2004-09-22 | Nikem Research S.R.L. | Indole derivatives for the treatment of osteoporosis |
-
1999
- 1999-10-18 SE SE9903760A patent/SE9903760D0/xx unknown
-
2000
- 2000-10-13 HK HK03100456.4A patent/HK1048313B/en not_active IP Right Cessation
- 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 US US10/110,663 patent/US6642246B1/en not_active Expired - Fee Related
- 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 EP EP00971959A patent/EP1235826B1/en not_active Expired - Lifetime
- 2000-10-13 DE DE60005054T patent/DE60005054T2/de not_active Expired - Lifetime
- 2000-10-13 PT PT00971959T patent/PT1235826E/pt unknown
- 2000-10-16 MY MYPI20004849A patent/MY136240A/en unknown
- 2000-10-17 CO CO00078738A patent/CO5271691A1/es not_active Application Discontinuation