ES2283860T3 - Agonistas deñ recptor nicotinico alfa-7 y estaninas combinados. - Google Patents
Agonistas deñ recptor nicotinico alfa-7 y estaninas combinados. Download PDFInfo
- Publication number
- ES2283860T3 ES2283860T3 ES03791540T ES03791540T ES2283860T3 ES 2283860 T3 ES2283860 T3 ES 2283860T3 ES 03791540 T ES03791540 T ES 03791540T ES 03791540 T ES03791540 T ES 03791540T ES 2283860 T3 ES2283860 T3 ES 2283860T3
- Authority
- ES
- Spain
- Prior art keywords
- azabicyclo
- oct
- carboxamide
- octan
- 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.)
- Expired - Lifetime
Links
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims abstract description 23
- 239000000556 agonist Substances 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 238000011321 prophylaxis Methods 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000003003 spiro group Chemical group 0.000 claims description 47
- RCFDIXKVOHJQPP-UHFFFAOYSA-N furo[2,3-b]pyridine Chemical compound C1=CN=C2OC=CC2=C1 RCFDIXKVOHJQPP-UHFFFAOYSA-N 0.000 claims description 44
- 208000024827 Alzheimer disease Diseases 0.000 claims description 23
- -1 phenylaminocarbonylamino Chemical group 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 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 11
- 230000001149 cognitive effect Effects 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 208000016620 Tourette disease 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
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000002829 reductive effect 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
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 7
- 230000036592 analgesia Effects 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 230000004112 neuroprotection Effects 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 230000007170 pathology Effects 0.000 claims description 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 230000000391 smoking effect Effects 0.000 claims description 5
- 229940083542 sodium Drugs 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 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 4
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 4
- 229960005110 cerivastatin Drugs 0.000 claims description 4
- 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 4
- 230000001713 cholinergic effect Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 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 4
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound 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 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims description 4
- 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 3
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 3
- 229960003765 fluvastatin Drugs 0.000 claims description 3
- 229960004844 lovastatin Drugs 0.000 claims description 3
- 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 3
- KMILHXLZVLODQX-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-pyridin-2-ylfuran-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(O1)=CC=C1C1=CC=CC=N1 KMILHXLZVLODQX-UHFFFAOYSA-N 0.000 claims description 3
- 229960002965 pravastatin 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
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 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
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
- 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
- WFHTYWNCRQLNFY-UHFFFAOYSA-N 5-(3-chlorophenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(Cl)=C1 WFHTYWNCRQLNFY-UHFFFAOYSA-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
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-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
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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Classifications
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- A61K31/435—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
- 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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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- 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
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- 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
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0202598 | 2002-09-02 | ||
| SE0202598A SE0202598D0 (sv) | 2002-09-02 | 2002-09-02 | Alpha-7 Nicotinic receptor agonists and statins in combination |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2283860T3 true ES2283860T3 (es) | 2007-11-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ES03791540T Expired - Lifetime ES2283860T3 (es) | 2002-09-02 | 2003-09-01 | Agonistas deñ recptor nicotinico alfa-7 y estaninas combinados. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20050256146A1 (https=) |
| EP (1) | EP1545537B9 (https=) |
| JP (1) | JP2006505530A (https=) |
| AT (1) | ATE358485T1 (https=) |
| AU (1) | AU2003256203A1 (https=) |
| DE (1) | DE60313004T2 (https=) |
| DK (1) | DK1545537T3 (https=) |
| ES (1) | ES2283860T3 (https=) |
| PT (1) | PT1545537E (https=) |
| SE (1) | SE0202598D0 (https=) |
| SI (1) | SI1545537T1 (https=) |
| WO (1) | WO2004019947A1 (https=) |
Families Citing this family (26)
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| 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 |
| MX2010014203A (es) | 2008-06-20 | 2011-02-22 | Astrazeneca Ab | Derivados de dibenzotiazepina y sus usos - 424. |
| FR2958850B1 (fr) * | 2010-04-14 | 2012-07-06 | Centre Nat Rech Scient | Medicaments pour la prevention ou le traitement des addictions aux drogues |
| AR081402A1 (es) | 2010-05-17 | 2012-08-29 | Envivo Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il) benzo(b)tiofeno-2-carboxamida monohidrato |
| WO2012007500A2 (de) * | 2010-07-15 | 2012-01-19 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| AU2012231275A1 (en) * | 2011-03-18 | 2013-10-17 | Genzyme Corporation | Glucosylceramide synthase inhibitors |
| 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 |
| 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 |
| 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 |
| WO2014122474A1 (en) | 2013-02-07 | 2014-08-14 | Takeda Pharmaceutical Company Limited | Piperidin-1 -yl and azepin-1 -yl carboxylates as muscarinic m4 receptor agonists |
| HK1219722A1 (zh) | 2013-06-21 | 2017-04-13 | Takeda Pharmaceutical Company Limited | 1-磺酰基派啶衍生物作为前动力蛋白受体的调节剂 |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| 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 |
| GB202414193D0 (en) | 2024-09-27 | 2024-11-13 | Addex Pharmaceuticals Sa | Novel compounds |
| GB202414197D0 (en) | 2024-09-27 | 2024-11-13 | Addex Pharmaceuticals Sa | Novel compounds |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP3708962B2 (ja) * | 1994-08-24 | 2005-10-19 | アストラゼネカ・アクチエボラーグ | 治療に有用なスピロ−アザ二環式化合物 |
| 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 |
| WO2002017358A2 (en) * | 2000-08-21 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted heteroaryl moieties for treatment of disease (nicotinic acetylcholine receptor antagonists) |
| 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 |
| KR20050085535A (ko) * | 2002-12-11 | 2005-08-29 | 파마시아 앤드 업존 캄파니 엘엘씨 | 알파 7 니코틴성 아세틸콜린 수용체 아고니스트와 다른화합물의 조합물을 사용한 질환의 치료 방법 |
| NZ550534A (en) * | 2004-03-25 | 2009-07-31 | Memory Pharm Corp | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
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2002
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2003
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- 2003-09-01 EP EP03791540A patent/EP1545537B9/en not_active Expired - Lifetime
- 2003-09-01 DK DK03791540T patent/DK1545537T3/da active
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- 2003-09-01 SI SI200330803T patent/SI1545537T1/sl unknown
- 2003-09-01 AT AT03791540T patent/ATE358485T1/de not_active IP Right Cessation
- 2003-09-01 DE DE60313004T patent/DE60313004T2/de not_active Expired - Fee Related
- 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 PT PT03791540T patent/PT1545537E/pt unknown
- 2003-09-01 WO PCT/SE2003/001352 patent/WO2004019947A1/en not_active Ceased
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2008
- 2008-08-06 US US12/186,915 patent/US20090192180A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE358485T1 (de) | 2007-04-15 |
| HK1077193A1 (en) | 2006-02-10 |
| AU2003256203A1 (en) | 2004-03-19 |
| WO2004019947A1 (en) | 2004-03-11 |
| JP2006505530A (ja) | 2006-02-16 |
| PT1545537E (pt) | 2007-06-20 |
| DE60313004T2 (de) | 2008-01-03 |
| US20090192180A1 (en) | 2009-07-30 |
| EP1545537B1 (en) | 2007-04-04 |
| SE0202598D0 (sv) | 2002-09-02 |
| SI1545537T1 (sl) | 2007-08-31 |
| EP1545537A1 (en) | 2005-06-29 |
| DK1545537T3 (da) | 2007-07-02 |
| US20050256146A1 (en) | 2005-11-17 |
| EP1545537B9 (en) | 2008-08-20 |
| DE60313004D1 (de) | 2007-05-16 |
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