JP2006505530A - アルファ−７ニコチン受容体作用剤およびスタチンの組み合わせ - Google Patents
アルファ−７ニコチン受容体作用剤およびスタチンの組み合わせ Download PDFInfo
- Publication number
- JP2006505530A JP2006505530A JP2004532517A JP2004532517A JP2006505530A JP 2006505530 A JP2006505530 A JP 2006505530A JP 2004532517 A JP2004532517 A JP 2004532517A JP 2004532517 A JP2004532517 A JP 2004532517A JP 2006505530 A JP2006505530 A JP 2006505530A
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- oct
- carboxamide
- octane
- thiophene
- 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.)
- Abandoned
Links
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 title claims abstract description 24
- 229940122656 Alpha-7 nicotinic receptor agonist Drugs 0.000 title 1
- 239000000556 agonist Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 33
- OCKIPDMKGPYYJS-UHFFFAOYSA-N azd0328 Chemical compound C1N(CC2)CCC2C21OC1=NC=CC=C1C2 OCKIPDMKGPYYJS-UHFFFAOYSA-N 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000003003 spiro group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 14
- 230000001149 cognitive effect Effects 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 9
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 9
- 208000016620 Tourette disease Diseases 0.000 claims description 9
- 230000036506 anxiety Effects 0.000 claims description 9
- 230000006949 cholinergic function Effects 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 201000000980 schizophrenia Diseases 0.000 claims description 9
- 230000005586 smoking cessation Effects 0.000 claims description 9
- TYAGAVRSOFABFO-UHFFFAOYSA-N spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound O1C(=O)NCC11C(CC2)CCN2C1 TYAGAVRSOFABFO-UHFFFAOYSA-N 0.000 claims description 9
- 230000036592 analgesia Effects 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000004112 neuroprotection Effects 0.000 claims description 8
- 229960000672 rosuvastatin Drugs 0.000 claims description 8
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims description 8
- NZONTOQHVFUZMV-ONEGZZNKSA-N (e)-n-(1-azabicyclo[2.2.2]octan-3-yl)-3-thiophen-2-ylprop-2-enamide Chemical compound C1N(CC2)CCC2C1NC(=O)\C=C\C1=CC=CS1 NZONTOQHVFUZMV-ONEGZZNKSA-N 0.000 claims description 5
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 5
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229960004844 lovastatin Drugs 0.000 claims description 4
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 4
- VWBQYTRBTXKKOG-IYNICTALSA-M pravastatin sodium Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 VWBQYTRBTXKKOG-IYNICTALSA-M 0.000 claims description 4
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 3
- 229960005110 cerivastatin Drugs 0.000 claims description 3
- IPNOSOBDTLDLNU-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-[3-(dimethylamino)phenyl]thiophene-2-carboxamide Chemical compound CN(C)C1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 IPNOSOBDTLDLNU-UHFFFAOYSA-N 0.000 claims description 3
- 229960001495 pravastatin sodium Drugs 0.000 claims description 3
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 3
- 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 description 2
- 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 description 2
- RZLDNRFXACJVKG-UHFFFAOYSA-N 4'-(4-methylpiperazin-1-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1CN(C)CCN1C1=CC=NC2=C1CC1(C3CCN(CC3)C1)O2 RZLDNRFXACJVKG-UHFFFAOYSA-N 0.000 claims description 2
- ZOWUTKIQMJXBEL-UHFFFAOYSA-N 4'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2C11OC(N=CC=C2Cl)=C2C1 ZOWUTKIQMJXBEL-UHFFFAOYSA-N 0.000 claims description 2
- MSFAUXUCGUHBEE-UHFFFAOYSA-N 4'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[3,2-c]pyridine] Chemical compound C1N(CC2)CCC2C11OC(C=CN=C2Cl)=C2C1 MSFAUXUCGUHBEE-UHFFFAOYSA-N 0.000 claims description 2
- NTBQKVIPXCOUHL-UHFFFAOYSA-N 4'-phenylsulfanylspiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound O1C2(C3CCN(CC3)C2)CC2=C1N=CC=C2SC1=CC=CC=C1 NTBQKVIPXCOUHL-UHFFFAOYSA-N 0.000 claims description 2
- SFXUCWSKMBXLML-UHFFFAOYSA-N 5'-(furan-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C=1N=C2OC3(C4CCN(CC4)C3)CC2=CC=1C1=CC=CO1 SFXUCWSKMBXLML-UHFFFAOYSA-N 0.000 claims description 2
- YGFFDFKDCIJMIG-UHFFFAOYSA-N 5'-bromospiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2C11OC2=NC=C(Br)C=C2C1 YGFFDFKDCIJMIG-UHFFFAOYSA-N 0.000 claims description 2
- CCZBJDYTALPUEY-UHFFFAOYSA-N 5'-ethenylspiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2C11OC2=NC=C(C=C)C=C2C1 CCZBJDYTALPUEY-UHFFFAOYSA-N 0.000 claims description 2
- KIEVYOWPVBDHPS-UHFFFAOYSA-N 5'-methylspiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2C11OC2=NC=C(C)C=C2C1 KIEVYOWPVBDHPS-UHFFFAOYSA-N 0.000 claims description 2
- BZDGMIQPHKJRLZ-UHFFFAOYSA-N 5'-nitrospiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2C11OC2=NC=C([N+](=O)[O-])C=C2C1 BZDGMIQPHKJRLZ-UHFFFAOYSA-N 0.000 claims description 2
- GIRLVGYIIVFTLI-UHFFFAOYSA-N 5'-phenylspiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C=1N=C2OC3(C4CCN(CC4)C3)CC2=CC=1C1=CC=CC=C1 GIRLVGYIIVFTLI-UHFFFAOYSA-N 0.000 claims description 2
- QKBVBFGEWWSUMM-UHFFFAOYSA-N 5'-pyridin-3-ylspiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C=1N=C2OC3(C4CCN(CC4)C3)CC2=CC=1C1=CC=CN=C1 QKBVBFGEWWSUMM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- MVAUXTNBWFARSQ-UHFFFAOYSA-N 5-(3-aminophenyl)-n-(1-azabicyclo[2.2.2]octan-3-yl)furan-2-carboxamide Chemical compound NC1=CC=CC(C=2OC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 MVAUXTNBWFARSQ-UHFFFAOYSA-N 0.000 claims description 2
- HPLGXOSWRUEUNI-UHFFFAOYSA-N 5-(3-aminophenyl)-n-(1-azabicyclo[2.2.2]octan-3-yl)thiophene-2-carboxamide Chemical compound NC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 HPLGXOSWRUEUNI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- BXVZWALJVTXQLT-UHFFFAOYSA-N 6'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2C21CC1=CC=C(Cl)N=C1O2 BXVZWALJVTXQLT-UHFFFAOYSA-N 0.000 claims description 2
- NSHWJYWNNQRBQV-UHFFFAOYSA-N 6'-fluorospiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1N(CC2)CCC2C21CC1=CC=C(F)N=C1O2 NSHWJYWNNQRBQV-UHFFFAOYSA-N 0.000 claims description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 2
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 2
- 229960005370 atorvastatin Drugs 0.000 claims description 2
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims description 2
- 229960003765 fluvastatin Drugs 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 2
- QCQYEPKJPBDDCO-UHFFFAOYSA-N n'-spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine]-4'-ylethane-1,2-diamine Chemical compound C1N(CC2)CCC2C11OC(N=CC=C2NCCN)=C2C1 QCQYEPKJPBDDCO-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- QEIXYTUTAQBVGQ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-4-phenylthiophene-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(SC=1)=CC=1C1=CC=CC=C1 QEIXYTUTAQBVGQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
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- 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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Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
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| PCT/SE2003/001352 WO2004019947A1 (en) | 2002-09-02 | 2003-09-01 | Alpha-7 nicotinic receptor agonists and statins in combination |
Publications (2)
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| JP2006505530A true JP2006505530A (ja) | 2006-02-16 |
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| EP (1) | EP1545537B9 (enExample) |
| JP (1) | JP2006505530A (enExample) |
| AT (1) | ATE358485T1 (enExample) |
| AU (1) | AU2003256203A1 (enExample) |
| DE (1) | DE60313004T2 (enExample) |
| DK (1) | DK1545537T3 (enExample) |
| ES (1) | ES2283860T3 (enExample) |
| PT (1) | PT1545537E (enExample) |
| SE (1) | SE0202598D0 (enExample) |
| SI (1) | SI1545537T1 (enExample) |
| WO (1) | WO2004019947A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013535434A (ja) * | 2010-07-15 | 2013-09-12 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 有害生物防除剤としての新規複素環式化合物 |
| WO2013161871A1 (ja) * | 2012-04-25 | 2013-10-31 | 興和株式会社 | Ｔｌｒ阻害作用を有するチオフェン誘導体 |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| WO2009017454A1 (en) * | 2007-07-30 | 2009-02-05 | Astrazeneca Ab | New therapeutic combination of a gsk3 inhibitor and an a7-nicotinic agonist 960 |
| HRP20130234T1 (hr) | 2008-06-20 | 2013-04-30 | Astrazeneca Ab | Derivat dibenzotiazepina i njegova uporaba |
| FR2958850B1 (fr) * | 2010-04-14 | 2012-07-06 | Centre Nat Rech Scient | Medicaments pour la prevention ou le traitement des addictions aux drogues |
| DK3029039T3 (en) | 2010-05-17 | 2017-12-04 | Forum Pharmaceuticals Inc | PHARMACEUTICAL FORMS CONTAINING CRYSTALLINIC FORMS OF (R) -7-CHLOR-N- (QUINUCLIDIN-3-YL) BENZO (B) THIOPHEN-2-CARBOXAMIDE HYDROCHLORIDE MONOHYDRATE |
| MX368340B (es) * | 2011-03-18 | 2019-09-30 | Genzyme Corp | Inhibidores de glucosilceramida sintasa. |
| 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 |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| ES2694299T3 (es) | 2013-02-07 | 2018-12-19 | Heptares Therapeutics Limited | Carboxilatos de piperidin-1-ilo y azepin-1-ilo como agonistas del receptor muscarínico M4 |
| WO2014202999A1 (en) | 2013-06-21 | 2014-12-24 | Takeda Cambridge Limited | 1-sulfonyl piperidine derivatives as modulators of prokineticin receptors |
| 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 |
| US20210255202A1 (en) * | 2018-06-13 | 2021-08-19 | Michael R. D'Andrea | Methods and dosing regimens for preventing or delaying onset of alzheimer's disease and other forms of dementia and mild congnitive impairment |
| 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 (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100366331B1 (ko) * | 1994-08-24 | 2003-04-10 | 아스트라제네카 악티에볼라그 | 치료에유용한스피로-아자비시클릭화합물 |
| AR013184A1 (es) * | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
| SE9900100D0 (sv) * | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| SE9903996D0 (sv) * | 1999-11-03 | 1999-11-03 | Astra Ab | New compounds |
| US6500840B2 (en) * | 2000-08-21 | 2002-12-31 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease |
| US6569865B2 (en) * | 2001-06-01 | 2003-05-27 | Astrazeneca Ab | Spiro 1-azabicyclo[2.2.2]octane-3,2′(3′h)-furo[2,3-b]pyridine |
| US20050222122A1 (en) * | 2002-04-02 | 2005-10-06 | Sean Lilienfeld | Statin therapy for enhancing cognitive maintenance |
| PL377777A1 (pl) * | 2002-12-11 | 2006-02-20 | Pharmacia & Upjohn Company Llc | Leczenie chorób połączeniami agonistów receptora alfa 7-nikotynowego i innych związków |
| RU2417225C2 (ru) * | 2004-03-25 | 2011-04-27 | Мемори Фармасьютиклз Корпорейшн | Индазолы, бензотиазолы, бензоизотиазолы, бензизоксазолы и их получение и применение |
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2002
- 2002-09-02 SE SE0202598A patent/SE0202598D0/xx unknown
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2003
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- 2003-09-01 AU AU2003256203A patent/AU2003256203A1/en not_active Abandoned
- 2003-09-01 DK DK03791540T patent/DK1545537T3/da active
- 2003-09-01 PT PT03791540T patent/PT1545537E/pt unknown
- 2003-09-01 ES ES03791540T patent/ES2283860T3/es not_active Expired - Lifetime
- 2003-09-01 JP JP2004532517A patent/JP2006505530A/ja not_active Abandoned
- 2003-09-01 US US10/525,783 patent/US20050256146A1/en not_active Abandoned
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- 2003-09-01 SI SI200330803T patent/SI1545537T1/sl unknown
- 2003-09-01 WO PCT/SE2003/001352 patent/WO2004019947A1/en not_active Ceased
- 2003-09-01 EP EP03791540A patent/EP1545537B9/en not_active Expired - Lifetime
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2008
- 2008-08-06 US US12/186,915 patent/US20090192180A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013535434A (ja) * | 2010-07-15 | 2013-09-12 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 有害生物防除剤としての新規複素環式化合物 |
| WO2013161871A1 (ja) * | 2012-04-25 | 2013-10-31 | 興和株式会社 | Ｔｌｒ阻害作用を有するチオフェン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE358485T1 (de) | 2007-04-15 |
| SE0202598D0 (sv) | 2002-09-02 |
| DK1545537T3 (da) | 2007-07-02 |
| EP1545537A1 (en) | 2005-06-29 |
| ES2283860T3 (es) | 2007-11-01 |
| WO2004019947A1 (en) | 2004-03-11 |
| PT1545537E (pt) | 2007-06-20 |
| SI1545537T1 (sl) | 2007-08-31 |
| HK1077193A1 (en) | 2006-02-10 |
| EP1545537B1 (en) | 2007-04-04 |
| DE60313004T2 (de) | 2008-01-03 |
| US20090192180A1 (en) | 2009-07-30 |
| US20050256146A1 (en) | 2005-11-17 |
| AU2003256203A1 (en) | 2004-03-19 |
| EP1545537B9 (en) | 2008-08-20 |
| DE60313004D1 (de) | 2007-05-16 |
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