NO326558B1 - Benzimidazol- og pyridylimidazol-derivater som ligander for GABA-reseptorer, fremstilling av slike forbindelser, farmasoytiske preparater inneholdende slike, metode for a endre signalet-transducing aktivitet til slike GABA(A)reseptorer og for a demonstrere tilstedevaerelse av GABA(A) in vitro basert pa slike forbindelser samt anvendelse av slike forbindelser for fremstilling av medikament for behandling av sykdom og forbedring av hukommelse. - Google Patents
Benzimidazol- og pyridylimidazol-derivater som ligander for GABA-reseptorer, fremstilling av slike forbindelser, farmasoytiske preparater inneholdende slike, metode for a endre signalet-transducing aktivitet til slike GABA(A)reseptorer og for a demonstrere tilstedevaerelse av GABA(A) in vitro basert pa slike forbindelser samt anvendelse av slike forbindelser for fremstilling av medikament for behandling av sykdom og forbedring av hukommelse. Download PDFInfo
- Publication number
- NO326558B1 NO326558B1 NO20032834A NO20032834A NO326558B1 NO 326558 B1 NO326558 B1 NO 326558B1 NO 20032834 A NO20032834 A NO 20032834A NO 20032834 A NO20032834 A NO 20032834A NO 326558 B1 NO326558 B1 NO 326558B1
- Authority
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- Norway
- Prior art keywords
- alkyl
- methyl
- imidazol
- ethyl
- cycloalkyl
- Prior art date
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- 229940079593 drug Drugs 0.000 title description 22
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 title description 16
- 238000004519 manufacturing process Methods 0.000 title description 16
- 229960003692 gamma aminobutyric acid Drugs 0.000 title description 15
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- FFLKHPQXHSKFLS-UHFFFAOYSA-N 2-[1-[(3-ethylimidazo[4,5-c]pyridin-2-yl)methyl]imidazol-2-yl]-1,3-thiazole Chemical compound N=1C2=CC=NC=C2N(CC)C=1CN1C=CN=C1C1=NC=CS1 FFLKHPQXHSKFLS-UHFFFAOYSA-N 0.000 claims description 5
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- OLKZVUPGOXOTCR-UHFFFAOYSA-N 1-ethyl-2-[[2-(3-fluorophenyl)pyrazol-3-yl]methyl]benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2N(CC)C=1CC1=CC=NN1C1=CC=CC(F)=C1 OLKZVUPGOXOTCR-UHFFFAOYSA-N 0.000 claims description 3
- MVFHGAAPNQTZIT-UHFFFAOYSA-N 2-[1-[[3-ethyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]methyl]imidazol-2-yl]-1,3-thiazole Chemical compound N=1C2=CC(C(F)(F)F)=NC=C2N(CC)C=1CN1C=CN=C1C1=NC=CS1 MVFHGAAPNQTZIT-UHFFFAOYSA-N 0.000 claims description 3
- ZKLJSRJSHPCLMK-UHFFFAOYSA-N 2-[5-[(1-ethylimidazo[4,5-c]pyridin-2-yl)methyl]pyrazol-1-yl]-1,3-thiazole Chemical compound N=1C2=CN=CC=C2N(CC)C=1CC1=CC=NN1C1=NC=CS1 ZKLJSRJSHPCLMK-UHFFFAOYSA-N 0.000 claims description 3
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- WFBDVXRXFDBCPQ-UHFFFAOYSA-N 1-[1-ethyl-2-[[2-(3-fluorophenyl)pyrazol-3-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CC1=CC=NN1C1=CC=CC(F)=C1 WFBDVXRXFDBCPQ-UHFFFAOYSA-N 0.000 claims description 2
- PTFROJBEVATOHH-UHFFFAOYSA-N 1-[3-ethyl-2-[[2-(1,3-thiazol-2-yl)imidazol-1-yl]methyl]imidazo[4,5-c]pyridin-6-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=NC=C2N(CC)C=1CN1C=CN=C1C1=NC=CS1 PTFROJBEVATOHH-UHFFFAOYSA-N 0.000 claims description 2
- ZMABKGMICHTDJC-UHFFFAOYSA-N 1-ethyl-2-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2N(CC)C=1CN1C=CN=C1C1=CC=CC(F)=C1 ZMABKGMICHTDJC-UHFFFAOYSA-N 0.000 claims description 2
- VNVOBDKJVOVZLO-UHFFFAOYSA-N 2-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-1-ethylimidazo[4,5-b]pyridine Chemical compound N=1C2=NC=CC=C2N(CC)C=1CN1C=CN=C1C1=CC(F)=CC=C1F VNVOBDKJVOVZLO-UHFFFAOYSA-N 0.000 claims description 2
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- IXZBSHQGWNORDK-UHFFFAOYSA-N 3-ethyl-2-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-6-propylimidazo[4,5-c]pyridine Chemical compound CCN1C=2C=NC(CCC)=CC=2N=C1CN1C=CN=C1C1=CC=CC(F)=N1 IXZBSHQGWNORDK-UHFFFAOYSA-N 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- ZZMSNZWUSAITCF-UHFFFAOYSA-N 1-(2-fluoroethyl)-2-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]benzimidazole Chemical compound N=1C2=CC=CC=C2N(CCF)C=1CN1C=CN=C1C1=CC=CC(F)=C1 ZZMSNZWUSAITCF-UHFFFAOYSA-N 0.000 claims 1
- UKRPNWBANYKVSX-UHFFFAOYSA-N 1-(2-fluoroethyl)-2-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]imidazo[4,5-c]pyridine Chemical compound N=1C2=CN=CC=C2N(CCF)C=1CN1C=CN=C1C1=CC=CC(F)=C1 UKRPNWBANYKVSX-UHFFFAOYSA-N 0.000 claims 1
- IJOAYYJZBYIARP-UHFFFAOYSA-N 1-(2-fluoroethyl)-2-[[2-(3-fluorophenyl)pyrazol-3-yl]methyl]benzimidazole Chemical compound N=1C2=CC=CC=C2N(CCF)C=1CC1=CC=NN1C1=CC=CC(F)=C1 IJOAYYJZBYIARP-UHFFFAOYSA-N 0.000 claims 1
- ZZUNHNUWVYUZMP-UHFFFAOYSA-N 1-[1-ethyl-2-[(2-pyrimidin-2-ylimidazol-1-yl)methyl]benzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CN1C=CN=C1C1=NC=CC=N1 ZZUNHNUWVYUZMP-UHFFFAOYSA-N 0.000 claims 1
- LJWYAKSHNZORNZ-UHFFFAOYSA-N 1-[1-ethyl-2-[[2-(1,3-thiazol-2-yl)imidazol-1-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CN1C=CN=C1C1=NC=CS1 LJWYAKSHNZORNZ-UHFFFAOYSA-N 0.000 claims 1
- BBKUOUQUFKRNFF-UHFFFAOYSA-N 1-[1-ethyl-2-[[2-(3-fluorophenyl)imidazol-1-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CN1C=CN=C1C1=CC=CC(F)=C1 BBKUOUQUFKRNFF-UHFFFAOYSA-N 0.000 claims 1
- LKBUUOKSQAWVTD-UHFFFAOYSA-N 1-[1-ethyl-2-[[2-(3-fluorophenyl)pyrazol-3-yl]methyl]benzimidazol-5-yl]propan-1-one Chemical compound N=1C2=CC(C(=O)CC)=CC=C2N(CC)C=1CC1=CC=NN1C1=CC=CC(F)=C1 LKBUUOKSQAWVTD-UHFFFAOYSA-N 0.000 claims 1
- YJSBPSNRTASDNU-UHFFFAOYSA-N 1-[1-ethyl-2-[[2-(3-fluoropyridin-2-yl)imidazol-1-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CN1C=CN=C1C1=NC=CC=C1F YJSBPSNRTASDNU-UHFFFAOYSA-N 0.000 claims 1
- VWBQEDULJDAARQ-UHFFFAOYSA-N 1-[1-ethyl-2-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CN1C=CN=C1C1=CC=CC(F)=N1 VWBQEDULJDAARQ-UHFFFAOYSA-N 0.000 claims 1
- UZPWHODHBYSZEQ-UHFFFAOYSA-N 1-[2-[[2-(2,5-difluorophenyl)imidazol-1-yl]methyl]-1-ethylbenzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CN1C=CN=C1C1=CC(F)=CC=C1F UZPWHODHBYSZEQ-UHFFFAOYSA-N 0.000 claims 1
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- MDMGBTJJBVZEBP-UHFFFAOYSA-N 1-[2-[[2-(3-chlorophenyl)pyrazol-3-yl]methyl]-1-ethylbenzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CC)C=1CC1=CC=NN1C1=CC=CC(Cl)=C1 MDMGBTJJBVZEBP-UHFFFAOYSA-N 0.000 claims 1
- UJQPVVFPDBQMKD-UHFFFAOYSA-N 1-[2-[[2-(6-fluoropyridin-2-yl)imidazol-1-yl]methyl]-1-propylbenzimidazol-5-yl]ethanone Chemical compound N=1C2=CC(C(C)=O)=CC=C2N(CCC)C=1CN1C=CN=C1C1=CC=CC(F)=N1 UJQPVVFPDBQMKD-UHFFFAOYSA-N 0.000 claims 1
- BRZSDAIWYDQUBY-UHFFFAOYSA-N 1-[3-ethyl-2-[[2-(1,3-thiazol-2-yl)imidazol-1-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound N=1C2=CC=C(C(C)=O)C=C2N(CC)C=1CN1C=CN=C1C1=NC=CS1 BRZSDAIWYDQUBY-UHFFFAOYSA-N 0.000 claims 1
- XUPWISAJTJAUGE-UHFFFAOYSA-N 1-ethyl-2-[(2-pyrimidin-2-ylimidazol-1-yl)methyl]-5-(trifluoromethyl)benzimidazole Chemical compound N=1C2=CC(C(F)(F)F)=CC=C2N(CC)C=1CN1C=CN=C1C1=NC=CC=N1 XUPWISAJTJAUGE-UHFFFAOYSA-N 0.000 claims 1
- BUXLFCBLQLLIBQ-UHFFFAOYSA-N 1-ethyl-2-[(2-pyrimidin-2-ylimidazol-1-yl)methyl]-6-(trifluoromethyl)benzimidazole Chemical compound N=1C2=CC=C(C(F)(F)F)C=C2N(CC)C=1CN1C=CN=C1C1=NC=CC=N1 BUXLFCBLQLLIBQ-UHFFFAOYSA-N 0.000 claims 1
- SPSNJLQCESZOGW-UHFFFAOYSA-N 1-ethyl-2-[(2-pyrimidin-2-ylimidazol-1-yl)methyl]-6-(trifluoromethyl)imidazo[4,5-c]pyridine Chemical compound N=1C2=CN=C(C(F)(F)F)C=C2N(CC)C=1CN1C=CN=C1C1=NC=CC=N1 SPSNJLQCESZOGW-UHFFFAOYSA-N 0.000 claims 1
- UFGKVFAPGHBCEI-UHFFFAOYSA-N 1-ethyl-2-[(2-pyrimidin-2-ylimidazol-1-yl)methyl]benzimidazole Chemical compound N=1C2=CC=CC=C2N(CC)C=1CN1C=CN=C1C1=NC=CC=N1 UFGKVFAPGHBCEI-UHFFFAOYSA-N 0.000 claims 1
- IHTSENJDUARLFO-UHFFFAOYSA-N 1-ethyl-2-[(2-pyrimidin-2-ylimidazol-1-yl)methyl]benzimidazole-5-carbonitrile Chemical compound N=1C2=CC(C#N)=CC=C2N(CC)C=1CN1C=CN=C1C1=NC=CC=N1 IHTSENJDUARLFO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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PCT/US2001/050038 WO2002050062A2 (en) | 2000-12-21 | 2001-12-21 | Benzimidazole and pyridylimidazole derivatives as ligands for gaba receptors |
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TWI248936B (en) * | 2001-03-21 | 2006-02-11 | Merck Sharp & Dohme | Imidazo-pyrimidine derivatives as ligands for GABA receptors |
IL159811A0 (en) | 2001-07-13 | 2004-06-20 | Neurogen Corp | Heteroaryl substituted fused bicyclic heteroaryl compounds as gabaa receptor ligands |
WO2003060475A2 (en) | 2002-01-10 | 2003-07-24 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted 2-(4-benzyl-piperazin-1-ylmethyl)- and 2-(4-benzyl-diazepan-1-ylmethyl)-1h-benzoimidazole analogues |
EP1465888A2 (en) | 2002-01-10 | 2004-10-13 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
CA2485093A1 (en) * | 2002-05-02 | 2003-11-13 | Neurogen Corporation | Substituted imidazole derivatives: gabaa receptor ligands |
AU2003301864A1 (en) * | 2002-05-08 | 2004-06-07 | Neurogen Corporation | Substituted imidazolylmethyl pyridine and pyrazine derivatives and their use as gabaa receptor ligands |
JP2006502974A (ja) * | 2002-05-17 | 2006-01-26 | ニューロジェン コーポレイション | 置換環縮合イミダゾール誘導体:gabaa受容体リガンド |
US20040063938A1 (en) * | 2002-09-30 | 2004-04-01 | Pfizer Inc | Process for preparing haloalkyl pyrimidines |
CN100579579C (zh) * | 2002-10-01 | 2010-01-13 | 诺华疫苗和诊断公司 | 抗癌及抗感染性疾病组合物及其使用方法 |
CA2495708A1 (en) * | 2002-11-08 | 2004-05-21 | Neurogen Corporation | 4-imidazol-1-ylmethyl-pyrimidine derivatives as ligands for gabaa receptors |
US20060084682A1 (en) * | 2002-12-13 | 2006-04-20 | Heerding Dirk A | Thrombopoietin mimetics |
US7381825B2 (en) | 2003-03-17 | 2008-06-03 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
SE0301699D0 (sv) * | 2003-06-10 | 2003-06-10 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
CA2537331A1 (en) | 2003-07-25 | 2005-02-10 | Neurogen Corporation | Imidazo-pyrimidines and triazolo-pyrimidines: benzodiazepine receptor ligands |
CN100457756C (zh) * | 2003-07-25 | 2009-02-04 | 神经能质公司 | 咪唑-嘧啶类及三唑-嘧啶类:苯并二氮平受体配体 |
EP1880998A1 (en) * | 2003-07-25 | 2008-01-23 | Neurogen Corporation | Imidazo-pyrimidines and triazolo-pyrimidines: benzodiazepine receptor ligands |
ATE472534T1 (de) | 2003-09-22 | 2010-07-15 | S | Benzimidazolderivate: herstellung und pharmazeutische anwendungen |
HUP0304101A3 (en) * | 2003-12-22 | 2008-10-28 | Sanofi Aventis | Pyrazole derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates |
WO2005121132A1 (ja) * | 2004-06-11 | 2005-12-22 | Shionogi & Co., Ltd. | 抗hcv作用を有する縮合ヘテロ環化合物 |
KR101022082B1 (ko) | 2005-10-11 | 2011-03-17 | 에프. 호프만-라 로슈 아게 | 아이소옥사졸 유도체 |
JP5015172B2 (ja) | 2005-12-23 | 2012-08-29 | エフ.ホフマン−ラ ロシュ アーゲー | アリール−イソオキサゾロ−4−イル−オキサジアゾール誘導体 |
PL1968973T3 (pl) | 2005-12-27 | 2012-03-30 | Hoffmann La Roche | Pochodne aryloizoksazol-4-iloimidazolu |
RU2426732C2 (ru) | 2006-01-17 | 2011-08-20 | Ф. Хоффманн-Ля Рош Аг | АРИЛ-ИЗОКСАЗОЛ-4-ИЛ-ИМИДАЗО[1,2-a]ПИРИДИН, ПРИГОДНЫЙ ДЛЯ ЛЕЧЕНИЯ БОЛЕЗНИ АЛЬЦГЕЙМЕРА ЧЕРЕЗ ПОСРЕДСТВО GABA-РЕЦЕПТОРОВ |
AU2007267183B2 (en) | 2006-05-31 | 2011-10-20 | F. Hoffmann-La Roche Ag | Aryl-4-ethynyl-isoxazole derivatives |
TW200808772A (en) * | 2006-06-13 | 2008-02-16 | Astrazeneca Ab | Therapeutic compounds |
WO2008016123A1 (fr) * | 2006-08-03 | 2008-02-07 | Takeda Pharmaceutical Company Limited | INHIBITEUR DE LA GSK-3β |
WO2008051533A2 (en) * | 2006-10-25 | 2008-05-02 | Takeda Pharmaceutical Company Limited | Benzimidazole compounds |
JP5416103B2 (ja) | 2007-06-22 | 2014-02-12 | エフ.ホフマン−ラ ロシュ アーゲー | イソオキサゾール−イミダゾール誘導体 |
TW200911803A (en) * | 2007-07-16 | 2009-03-16 | Organon Nv | 6-phenyl-1H-imidazo [4,5-c] pyridine-4-carbonitrile derivatives |
BRPI0823262A2 (pt) * | 2007-08-10 | 2013-09-24 | Cortex Pharma Inc | mÉtodo de tratamento de depressço respiratària e uso de um composto na fabricaÇço de um medicamento para o tratamento de depressço respiratària |
US7943619B2 (en) | 2007-12-04 | 2011-05-17 | Hoffmann-La Roche Inc. | Isoxazolo-pyridazine derivatives |
KR101175859B1 (ko) | 2007-12-04 | 2012-08-24 | 에프. 호프만-라 로슈 아게 | 이속사졸로-피라진 유도체 |
US7902201B2 (en) | 2007-12-04 | 2011-03-08 | Hoffmann-La Roche Inc. | Isoxazolo-pyrazine derivatives |
TW201033201A (en) | 2009-02-19 | 2010-09-16 | Hoffmann La Roche | Isoxazole-isoxazole and isoxazole-isothiazole derivatives |
US8389550B2 (en) | 2009-02-25 | 2013-03-05 | Hoffmann-La Roche Inc. | Isoxazoles / O-pyridines with ethyl and ethenyl linker |
US8222246B2 (en) | 2009-04-02 | 2012-07-17 | Hoffmann-La Roche Inc. | Substituted isoxazoles |
US20100280019A1 (en) | 2009-04-30 | 2010-11-04 | Roland Jakob-Roetne | Isoxazoles |
US8410104B2 (en) | 2009-05-05 | 2013-04-02 | Hoffmann-La Roche Inc. | Pyridazines |
WO2010127976A1 (en) | 2009-05-05 | 2010-11-11 | F. Hoffmann-La Roche Ag | Isoxazole-pyridine derivatives |
JP5478716B2 (ja) | 2009-05-05 | 2014-04-23 | エフ.ホフマン−ラ ロシュ アーゲー | 認識障害の処置において使用するためのgabaa受容体逆アゴニストとしてのイソオキサゾール−チアゾール誘導体 |
MX2011011273A (es) | 2009-05-05 | 2011-11-04 | Hoffmann La Roche | Derivados de isoxazol-pirazol. |
KR101354416B1 (ko) | 2009-05-07 | 2014-02-19 | 에프. 호프만-라 로슈 아게 | 감마-아미노부티르산 조절제로서 이속사졸-피리딘 유도체 |
WO2012033149A1 (ja) * | 2010-09-10 | 2012-03-15 | 塩野義製薬株式会社 | Ampk活性化作用を有するヘテロ環縮合イミダゾール誘導体 |
US20130196990A1 (en) | 2010-10-06 | 2013-08-01 | Junya Qu | Benzimidazole Derivatives As PI3 Kinase Inhibitors |
AU2011328993B2 (en) | 2010-11-15 | 2017-03-02 | Agenebio, Inc. | Pyridazine derivatives, compositions and methods for treating cognitive impairment |
MX348131B (es) * | 2011-02-25 | 2017-05-26 | Merck Sharp & Dohme | Novedosos derivados de azabencimidazol ciclico utiles como agentes antidiabeticos. |
WO2012116440A1 (en) | 2011-03-03 | 2012-09-07 | Zalicus Pharmaceuticals Ltd. | Benzimidazole inhibitors of the sodium channel |
CN102653531B (zh) * | 2011-03-04 | 2014-08-13 | 上海爱普植物科技有限公司 | 一种马索亚内酯的合成方法 |
CA2855948C (en) * | 2011-08-11 | 2020-07-28 | Bayer Cropscience Ag | 1,2,4-triazolyl-substituted keto-enols |
US8785435B2 (en) | 2011-10-20 | 2014-07-22 | Hoffmann-La Roche Inc. | Solid forms |
GB201119538D0 (en) * | 2011-11-10 | 2011-12-21 | Viral Ltd | Pharmaceutical compounds |
CN104024234B (zh) | 2012-01-11 | 2016-09-28 | 拜耳知识产权有限责任公司 | 四唑-5-基-和三唑-5-基-芳基化合物及其作为除草剂的用途 |
US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
WO2013174895A1 (en) | 2012-05-24 | 2013-11-28 | Cellzome Limited | Heterocyclyl pyrimidine analogues as tyk2 inhibitors |
JP6230344B2 (ja) * | 2013-09-06 | 2017-11-15 | 株式会社東芝 | 蒸気タービンプラント |
WO2015052178A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
WO2015052173A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Tetrazole and triazole compounds and their use as herbicides |
JP6883988B2 (ja) | 2013-12-20 | 2021-06-09 | エージンバイオ, インコーポレイテッド | ベンゾジアゼピン誘導体、組成物、および認知障害を処置するための方法 |
JP2017504628A (ja) * | 2014-01-31 | 2017-02-09 | 小野薬品工業株式会社 | 縮合イミダゾール化合物 |
TWI675031B (zh) * | 2014-02-17 | 2019-10-21 | 德商拜耳作物科學股份有限公司 | 作為殺蟲劑之2-(雜環)芳基-取代之稠合雙環雜環衍生物 |
WO2016016421A1 (en) * | 2014-07-31 | 2016-02-04 | Institut Pasteur Korea | 2-amino-benzimidazole derivatives and their use as 5-lipoxygenase and/or prostaglandin e synthase inhibitors |
CA3210002A1 (en) | 2014-12-29 | 2016-07-07 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Small molecule inhibitors of lactate dehydrogenase and methods of use thereof |
UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
UY36548A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
EP3280716B1 (de) | 2015-04-08 | 2020-02-12 | Bayer CropScience AG | Imidazo[1,2-a]pyridin-2-yl-derivate als schädlingsbekämpfungsmittel und deren zwischenprodukte |
EA036844B1 (ru) | 2015-06-19 | 2020-12-28 | Эйджинбайо, Инк. | Производные бензодиазепина, композиции и способы для лечения когнитивного нарушения |
AU2016297558B2 (en) * | 2015-07-20 | 2021-03-25 | Genzyme Corporation | Colony stimulating factor-1 receptor (CSF-1R) inhibitors |
ES2882667T3 (es) | 2015-08-07 | 2021-12-02 | Bayer Cropscience Ag | Derivados heterocíclicos condensados sustituidos por 2-(het)arilo como pesticidas |
ES2894301T3 (es) | 2015-10-26 | 2022-02-14 | Bayer Cropscience Ag | Derivados de heterociclos bicíclicos condensados como pesticidas |
WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
CN107531679B (zh) * | 2016-03-18 | 2021-07-02 | 江苏恒瑞医药股份有限公司 | 芳香酰胺类衍生物、其制备方法及其在医药上的应用 |
WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
AR108257A1 (es) | 2016-05-02 | 2018-08-01 | Mei Pharma Inc | Formas polimórficas de 3-[2-butil-1-(2-dietilamino-etil)-1h-bencimidazol-5-il]-n-hidroxi-acrilamida y usos de las mismas |
EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
KR102435080B1 (ko) | 2016-07-19 | 2022-08-22 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체 |
EP3497102B1 (de) | 2016-08-15 | 2022-12-07 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
JP7098600B2 (ja) | 2016-08-16 | 2022-07-11 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 3H-イミダゾール[4,5-c]ピリジン誘導体を有機金属亜鉛-アミン塩基と反応させることによる2-(3,6-ジハロピリジン-2-イル)-3H-イミダゾール[4,5-c]ピリジン誘導体及び関連化合物の製造方法 |
AU2017328614B2 (en) | 2016-09-19 | 2022-01-13 | Bayer Aktiengesellschaft | Pyrazolo [1,5-a]pyridine derivatives and their use as pesticides |
JP6994504B2 (ja) | 2016-10-06 | 2022-01-14 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 有害生物防除剤としての2-(ヘタ)アリール置換された縮合二環式複素環誘導体 |
ES2910790T3 (es) | 2016-12-01 | 2022-05-13 | Syngenta Participations Ag | Proceso para la preparación de intermedios de derivados heterocíclicos con actividad plaguicida con sustituyentes que contienen azufre |
BR112019012821A2 (pt) | 2016-12-19 | 2019-11-26 | Agenebio Inc | derivados de benzodiazepina, composições e métodos para o tratamento do comprometimento cognitivo |
US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
TW201833107A (zh) | 2017-02-06 | 2018-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經2-(雜)芳基取代的稠合雜環衍生物 |
EP3615540B1 (de) | 2017-04-24 | 2022-04-27 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
AU2018344370C1 (en) | 2017-10-04 | 2023-04-27 | Bayer Aktiengesellschaft | Derivatives of heterocyclic compounds as pest control agents |
EP3305786A3 (de) | 2018-01-22 | 2018-07-25 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
JP2021514949A (ja) | 2018-02-21 | 2021-06-17 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としての縮合二環式ヘテロ環誘導体 |
KR20210005081A (ko) | 2018-04-20 | 2021-01-13 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 헤테로시클렌 유도체 |
JP7514534B2 (ja) | 2018-06-19 | 2024-07-11 | エージンバイオ, インコーポレイテッド | 認知障害を処置するためのベンゾジアゼピン誘導体、組成物および方法 |
WO2020011086A1 (zh) * | 2018-07-13 | 2020-01-16 | 四川科伦博泰生物医药股份有限公司 | 苯并二氮杂环类化合物、其制备方法及用途 |
EP3636645A1 (de) | 2018-10-11 | 2020-04-15 | Bayer Aktiengesellschaft | Verfahren zur herstellung schwefel-substituierter pyridinderivate |
KR20210133984A (ko) | 2019-02-26 | 2021-11-08 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 축합된 비시클릭 헤테로시클릭 유도체 |
US20230060425A1 (en) | 2019-02-26 | 2023-03-02 | Bayer Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
AR119140A1 (es) | 2019-06-13 | 2021-11-24 | Pi Industries Ltd | Compuestos heterocíclicos fusionados y su uso como agentes de control de plagas |
CN110407744A (zh) * | 2019-08-13 | 2019-11-05 | 上海毕得医药科技有限公司 | 一种1-(4-氨基吡啶-2-基)乙酮的合成方法 |
CN111072681B (zh) * | 2019-12-11 | 2020-11-06 | 郑州大学 | 一种靶向细胞膜表面gaba受体荧光探针及其制备方法和应用 |
JP2024500919A (ja) | 2020-12-23 | 2024-01-10 | ジェンザイム・コーポレーション | 重水素化コロニー刺激因子-1受容体(csf-1r)阻害剤 |
US20240132513A1 (en) | 2022-08-19 | 2024-04-25 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
CN115490646A (zh) * | 2022-10-10 | 2022-12-20 | 安徽昊帆生物有限公司 | 3-硝基-1,2,4-三氮唑的制备方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3150486A1 (de) * | 1981-12-19 | 1983-08-25 | Merck Patent Gmbh, 6100 Darmstadt | Imidazo(4,5-c)pyridine, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
SK282425B6 (sk) | 1995-04-21 | 2002-01-07 | Neurosearch A/S | Benzimidazolové zlúčeniny, farmaceutické zmesi obsahujúce tieto zlúčeniny a použitie týchto zlúčenín |
GB9702524D0 (en) * | 1997-02-07 | 1997-03-26 | Merck Sharp & Dohme | Therapeutic agents |
AU6444298A (en) | 1997-03-04 | 1998-09-22 | Medtronic, Inc. | Bioprothesis film strip for surgical stapler and method of attaching the same |
WO2000059905A1 (en) * | 1999-04-02 | 2000-10-12 | Neurogen Corporation | ARYL AND HETEROARYL FUSED AMINOALKYL-IMIDAZOLE DERIVATIVES: SELECTIVE MODULATORS OF GABAa RECEPTORS |
JP2003528802A (ja) | 1999-04-02 | 2003-09-30 | ニューロゲン コーポレイション | N−ベンゾイミダゾリルメチル−及びn−インドリルメチル−ベンズアミド並びにcrf調節物質としてのそれらの使用 |
CA2369544A1 (en) | 1999-04-02 | 2000-10-12 | Robert W. Desimone | Aryl and heteroaryl fused aminoalkyl-imidazole derivatives:selective modulators of bradykinin b2 receptors |
JP2002541146A (ja) | 1999-04-02 | 2002-12-03 | ニューロゲン コーポレイション | アリールおよびヘテロアリール融合のアミノアルキル−イミダゾール誘導体および糖尿病薬としてのその使用 |
US6512062B1 (en) * | 1999-04-08 | 2003-01-28 | The University Of North Carolina At Chapel Hill | Polymerization of non-fluorinated monomers in carbon dioxide |
IL146403A0 (en) * | 1999-06-22 | 2002-07-25 | Neurosearch As | Novel benzimidazole derivatives and pharmaceutical compositions comprising these compounds |
GB9921150D0 (en) * | 1999-09-07 | 1999-11-10 | Merck Sharp & Dohme | Therapeutic agents |
DE60039921D1 (de) | 2000-09-29 | 2008-09-25 | Neurogen Corp | Hochaffine kleinmolekülige c5a-rezeptor-modulatoren |
AU2001296799A1 (en) | 2000-10-06 | 2002-04-15 | Neurogen Corporation | Benzimidazole and indole derivatives as crf receptor modulators |
US7030150B2 (en) | 2001-05-11 | 2006-04-18 | Trimeris, Inc. | Benzimidazole compounds and antiviral uses thereof |
-
2001
- 2001-12-20 PA PA20018535601A patent/PA8535601A1/es unknown
- 2001-12-21 CZ CZ20031676A patent/CZ20031676A3/cs unknown
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- 2001-12-22 EG EG20011360A patent/EG24590A/xx active
-
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- 2003-06-11 BG BG107899A patent/BG107899A/bg unknown
- 2003-06-11 ZA ZA2003/04544A patent/ZA200304544B/en unknown
- 2003-06-13 HR HR20030483A patent/HRP20030483A9/xx not_active Application Discontinuation
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- 2003-06-20 IS IS6855A patent/IS6855A/is unknown
- 2003-06-20 NO NO20032834A patent/NO326558B1/no not_active IP Right Cessation
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- 2005-07-12 US US11/179,458 patent/US7300945B2/en not_active Expired - Fee Related
-
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- 2007-11-19 US US11/942,480 patent/US7642267B2/en not_active Expired - Fee Related
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2010
- 2010-01-05 US US12/652,435 patent/US20100267698A1/en not_active Abandoned
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