PT1545537E - Agonistas do receptor alfa-7 nicotínico e estatinas em combinação - Google Patents
Agonistas do receptor alfa-7 nicotínico e estatinas em combinação Download PDFInfo
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- PT1545537E PT1545537E PT03791540T PT03791540T PT1545537E PT 1545537 E PT1545537 E PT 1545537E PT 03791540 T PT03791540 T PT 03791540T PT 03791540 T PT03791540 T PT 03791540T PT 1545537 E PT1545537 E PT 1545537E
- Authority
- PT
- Portugal
- Prior art keywords
- azabicyclo
- oct
- carboxamide
- octane
- furo
- Prior art date
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- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 title claims abstract description 23
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 title abstract description 12
- 239000000018 receptor agonist Substances 0.000 title description 2
- 229940044601 receptor agonist Drugs 0.000 title description 2
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 title 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title 1
- 239000000556 agonist Substances 0.000 claims abstract description 22
- 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
- -1 phenylaminocarbonylamino Chemical group 0.000 claims description 92
- RCFDIXKVOHJQPP-UHFFFAOYSA-N furo[2,3-b]pyridine Chemical compound C1=CN=C2OC=CC2=C1 RCFDIXKVOHJQPP-UHFFFAOYSA-N 0.000 claims description 48
- 125000003003 spiro group Chemical group 0.000 claims description 31
- 208000024827 Alzheimer disease Diseases 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- OCKIPDMKGPYYJS-UHFFFAOYSA-N azd0328 Chemical compound C1N(CC2)CCC2C21OC1=NC=CC=C1C2 OCKIPDMKGPYYJS-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 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
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 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
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 7
- 208000016620 Tourette disease Diseases 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 230000006949 cholinergic function Effects 0.000 claims description 7
- 230000001149 cognitive effect Effects 0.000 claims description 7
- 230000004112 neuroprotection Effects 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 230000000391 smoking effect Effects 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- 230000036592 analgesia Effects 0.000 claims description 6
- 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 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
- 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
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 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
- 229960005110 cerivastatin 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
- HBCSLZXVQIRVKW-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)formamide Chemical compound C1CC2C(NC=O)CN1CC2 HBCSLZXVQIRVKW-UHFFFAOYSA-N 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
- 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
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- XGFFLSZDZDPBAB-UHFFFAOYSA-N 4-phenylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2C=CC=CC=2)=C1 XGFFLSZDZDPBAB-UHFFFAOYSA-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
- RQJWFHRUPTYLOV-UHFFFAOYSA-N 5-(3-methylphenyl)furan-2-carboxamide Chemical compound CC1=CC=CC(C=2OC(=CC=2)C(N)=O)=C1 RQJWFHRUPTYLOV-UHFFFAOYSA-N 0.000 claims description 2
- ZAXSHDQOFNHDIM-UHFFFAOYSA-N 5-bromospiro[1,2-dihydroindole-3,1'-cyclopropane] Chemical compound C12=CC(Br)=CC=C2NCC21CC2 ZAXSHDQOFNHDIM-UHFFFAOYSA-N 0.000 claims description 2
- OYSOOLCZEMWVQN-UHFFFAOYSA-N 5-phenylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC=C1 OYSOOLCZEMWVQN-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
- 150000003857 carboxamides Chemical class 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
- HOQIASNSOZAUEZ-UHFFFAOYSA-N furo[2,3-b]quinoline Chemical compound C1=CC=C2N=C(OC=C3)C3=CC2=C1 HOQIASNSOZAUEZ-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
- 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
- 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
- HRHDJQHTJTVUMB-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-(3-nitrophenyl)furan-2-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2OC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 HRHDJQHTJTVUMB-UHFFFAOYSA-N 0.000 claims description 2
- TYPDWKBLNJSIHR-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-[3-(hydroxymethyl)phenyl]thiophene-2-carboxamide Chemical compound OCC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 TYPDWKBLNJSIHR-UHFFFAOYSA-N 0.000 claims description 2
- XXXRVCPQJSWEIQ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-phenylfuran-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(O1)=CC=C1C1=CC=CC=C1 XXXRVCPQJSWEIQ-UHFFFAOYSA-N 0.000 claims description 2
- XHIBZIFIARCBMN-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-pyridin-4-yl-2h-1,3-thiazole-3-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)N(C=1)CSC=1C1=CC=NC=C1 XHIBZIFIARCBMN-UHFFFAOYSA-N 0.000 claims description 2
- ZFFGQNHUUBRDTF-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-5-thiophen-2-ylfuran-2-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(O1)=CC=C1C1=CC=CS1 ZFFGQNHUUBRDTF-UHFFFAOYSA-N 0.000 claims description 2
- WTUHRGRJMXKQOM-IBGZPJMESA-N n-[(3r)-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)N[C@@H]2C3CCN(CC3)C2)=C1 WTUHRGRJMXKQOM-IBGZPJMESA-N 0.000 claims description 2
- CENIOWYLMHMVTC-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-thiophen-3-ylbenzamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1)=CC=CC=1C=1C=CSC=1 CENIOWYLMHMVTC-KRWDZBQOSA-N 0.000 claims description 2
- OIEAJUFPEQIZHL-HNNXBMFYSA-N n-[(3r)-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)N[C@@H]2C3CCN(CC3)C2)=C1 OIEAJUFPEQIZHL-HNNXBMFYSA-N 0.000 claims description 2
- GALYCJSQLYPAQX-INIZCTEOSA-N n-[(3r)-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)N[C@@H]2C3CCN(CC3)C2)=C1 GALYCJSQLYPAQX-INIZCTEOSA-N 0.000 claims description 2
- OWGIBYSBTRBKPD-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-[3-(dimethylamino)phenyl]furan-2-carboxamide Chemical compound CN(C)C1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 OWGIBYSBTRBKPD-KRWDZBQOSA-N 0.000 claims description 2
- DUMIUMCPYFQUAA-IBGZPJMESA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-naphthalen-2-ylfuran-2-carboxamide Chemical compound C1=CC=CC2=CC(C3=CC=C(O3)C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=C21 DUMIUMCPYFQUAA-IBGZPJMESA-N 0.000 claims description 2
- UUSSDOJBSVGPEU-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-2-ylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC=N1 UUSSDOJBSVGPEU-AWEZNQCLSA-N 0.000 claims description 2
- FPIGGZJRNAPCBW-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-3-ylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CN=C1 FPIGGZJRNAPCBW-AWEZNQCLSA-N 0.000 claims description 2
- FMOHTJWWZYDUKQ-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-4-ylfuran-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C1=CC=NC=C1 FMOHTJWWZYDUKQ-AWEZNQCLSA-N 0.000 claims description 2
- QDWJHUICASOKIN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=NC=C1 QDWJHUICASOKIN-AWEZNQCLSA-N 0.000 claims description 2
- LEUSUHAAYXEGAO-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC=C1 LEUSUHAAYXEGAO-OAHLLOKOSA-N 0.000 claims description 2
- UUSSDOJBSVGPEU-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-2-ylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC=N1 UUSSDOJBSVGPEU-CQSZACIVSA-N 0.000 claims description 2
- FPIGGZJRNAPCBW-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-3-ylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CN=C1 FPIGGZJRNAPCBW-CQSZACIVSA-N 0.000 claims description 2
- QDWJHUICASOKIN-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=NC=C1 QDWJHUICASOKIN-CQSZACIVSA-N 0.000 claims description 2
- 229960002855 simvastatin Drugs 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- OTNOXWBLYHUWLZ-UHFFFAOYSA-N 3-(3-acetamidophenyl)-n-(1-azabicyclo[2.2.2]octan-3-yl)benzamide Chemical compound CC(=O)NC1=CC=CC(C=2C=C(C=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 OTNOXWBLYHUWLZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- WPCSAIACUYFJIQ-UHFFFAOYSA-N 5-(2-methoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC=CC=C1C1=CC=C(C(N)=O)O1 WPCSAIACUYFJIQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MVAUXTNBWFARSQ-HNNXBMFYSA-N 5-(3-aminophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furan-2-carboxamide Chemical compound NC1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 MVAUXTNBWFARSQ-HNNXBMFYSA-N 0.000 claims 1
- 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 1
- XPWHBVLUZBCMJY-UHFFFAOYSA-N 5-(3-fluorophenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(F)=C1 XPWHBVLUZBCMJY-UHFFFAOYSA-N 0.000 claims 1
- LQSYOLVFFWKQRW-UHFFFAOYSA-N 5-(3-hydroxyphenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(O)=C1 LQSYOLVFFWKQRW-UHFFFAOYSA-N 0.000 claims 1
- JZJSJLYCLODZGT-UHFFFAOYSA-N 5-[3-(aminomethyl)phenyl]-n-(1-azabicyclo[2.2.2]octan-3-yl)thiophene-2-carboxamide Chemical compound NCC1=CC=CC(C=2SC(=CC=2)C(=O)NC2C3CCN(CC3)C2)=C1 JZJSJLYCLODZGT-UHFFFAOYSA-N 0.000 claims 1
- GYDGAXNDWVXCID-UHFFFAOYSA-N 5-[3-(aminomethyl)phenyl]thiophene-2-carboxamide Chemical compound NCC1=CC=CC(C=2SC(=CC=2)C(N)=O)=C1 GYDGAXNDWVXCID-UHFFFAOYSA-N 0.000 claims 1
- UBPRKNMUSICIJU-UHFFFAOYSA-N 5-phenylthiophene-3-carboxamide Chemical compound NC(=O)C1=CSC(C=2C=CC=CC=2)=C1 UBPRKNMUSICIJU-UHFFFAOYSA-N 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
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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 |
| CN102131791B (zh) | 2008-06-20 | 2014-12-24 | 阿斯利康(瑞典)有限公司 | 二苯并硫杂氮杂*衍生物及其用途 |
| FR2958850B1 (fr) * | 2010-04-14 | 2012-07-06 | Centre Nat Rech Scient | Medicaments pour la prevention ou le traitement des addictions aux drogues |
| PE20170923A1 (es) | 2010-05-17 | 2017-07-12 | Forum Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida monohidratado |
| JP5996532B2 (ja) * | 2010-07-15 | 2016-09-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 有害生物防除剤としての新規複素環式化合物 |
| KR101987736B1 (ko) * | 2011-03-18 | 2019-06-11 | 젠자임 코포레이션 | 글루코실세라마이드 합성효소 억제제 |
| 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 |
| JPWO2013161871A1 (ja) * | 2012-04-25 | 2015-12-24 | 興和株式会社 | Ｔｌｒ阻害作用を有するチオフェン誘導体 |
| EP3461481A1 (en) | 2012-05-08 | 2019-04-03 | 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 |
| 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 |
| 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 |
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| ATE192157T1 (de) * | 1994-08-24 | 2000-05-15 | Astra Ab | Therapeutisch verwendbare spiro-azabicyclische verbindungen |
| 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 |
| AU2001282875A1 (en) * | 2000-08-21 | 2002-03-04 | Pharmacia And 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 |
| EP1735306A2 (en) * | 2004-03-25 | 2006-12-27 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
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2002
- 2002-09-02 SE SE0202598A patent/SE0202598D0/xx unknown
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2003
- 2003-09-01 US US10/525,783 patent/US20050256146A1/en not_active Abandoned
- 2003-09-01 SI SI200330803T patent/SI1545537T1/sl unknown
- 2003-09-01 DK DK03791540T patent/DK1545537T3/da active
- 2003-09-01 JP JP2004532517A patent/JP2006505530A/ja not_active Abandoned
- 2003-09-01 PT PT03791540T patent/PT1545537E/pt unknown
- 2003-09-01 AU AU2003256203A patent/AU2003256203A1/en not_active Abandoned
- 2003-09-01 AT AT03791540T patent/ATE358485T1/de not_active IP Right Cessation
- 2003-09-01 EP EP03791540A patent/EP1545537B9/en not_active Expired - Lifetime
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- 2003-09-01 ES ES03791540T patent/ES2283860T3/es not_active Expired - Lifetime
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2008
- 2008-08-06 US US12/186,915 patent/US20090192180A1/en not_active Abandoned
Also Published As
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|---|---|
| US20050256146A1 (en) | 2005-11-17 |
| DE60313004D1 (de) | 2007-05-16 |
| US20090192180A1 (en) | 2009-07-30 |
| EP1545537B9 (en) | 2008-08-20 |
| DE60313004T2 (de) | 2008-01-03 |
| WO2004019947A1 (en) | 2004-03-11 |
| AU2003256203A1 (en) | 2004-03-19 |
| EP1545537B1 (en) | 2007-04-04 |
| JP2006505530A (ja) | 2006-02-16 |
| HK1077193A1 (en) | 2006-02-10 |
| SE0202598D0 (sv) | 2002-09-02 |
| EP1545537A1 (en) | 2005-06-29 |
| DK1545537T3 (da) | 2007-07-02 |
| SI1545537T1 (sl) | 2007-08-31 |
| ATE358485T1 (de) | 2007-04-15 |
| ES2283860T3 (es) | 2007-11-01 |
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