JP2013536798A5 - - Google Patents
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- JP2013536798A5 JP2013536798A5 JP2013510386A JP2013510386A JP2013536798A5 JP 2013536798 A5 JP2013536798 A5 JP 2013536798A5 JP 2013510386 A JP2013510386 A JP 2013510386A JP 2013510386 A JP2013510386 A JP 2013510386A JP 2013536798 A5 JP2013536798 A5 JP 2013536798A5
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- JP
- Japan
- Prior art keywords
- salt
- optionally substituted
- ring
- compound according
- group
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- TYZSJCRDLQKNAA-AREMUKBSSA-N 2-[(8r)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C([C@@](CCC3)(OC=3C=C(F)C(F)=C(F)C=3)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 TYZSJCRDLQKNAA-AREMUKBSSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 4
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims 3
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 150000002916 oxazoles Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- WWFFQXDRJZKGDS-RUZDIDTESA-N 2-[(8r)-3-[6-methoxy-5-(4-methylimidazol-1-yl)pyridin-2-yl]-8-(3,4,5-trifluorophenoxy)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=NC(C=2N3C([C@@](CCC3)(OC=3C=C(F)C(F)=C(F)C=3)C(C)(C)O)=NN=2)=CC=C1N1C=NC(C)=C1 WWFFQXDRJZKGDS-RUZDIDTESA-N 0.000 claims 1
- RIXAYKFZSRGVTI-UHFFFAOYSA-N 2-[3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[3-(trifluoromethyl)phenoxy]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C(C(CCC3)(OC=3C=C(C=CC=3)C(F)(F)F)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 RIXAYKFZSRGVTI-UHFFFAOYSA-N 0.000 claims 1
- CSZXOHDAQYOWJT-UHFFFAOYSA-N 2-[3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[4-(trifluoromethyl)phenoxy]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C(C(CCC3)(OC=3C=CC(=CC=3)C(F)(F)F)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 CSZXOHDAQYOWJT-UHFFFAOYSA-N 0.000 claims 1
- JGEYZKXMPJLLDD-UHFFFAOYSA-N 2-[8-(3,5-difluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C(C(CCC3)(OC=3C=C(F)C=C(F)C=3)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 JGEYZKXMPJLLDD-UHFFFAOYSA-N 0.000 claims 1
- FUNFAPKBEIRFLV-UHFFFAOYSA-N 2-[8-(4-chloro-3-fluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C(C(CCC3)(OC=3C=C(F)C(Cl)=CC=3)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 FUNFAPKBEIRFLV-UHFFFAOYSA-N 0.000 claims 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical group C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 229940043274 prophylactic drug Drugs 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229940126585 therapeutic drug Drugs 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 229940124648 γ-Secretase Modulator Drugs 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- -1 1,3-oxazol-5-yl Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HRCWSQSTNBIFCT-UHFFFAOYSA-N 2-(3,4,5-trifluoro-2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC(F)=C(F)C(F)=C1O HRCWSQSTNBIFCT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- LKVYMQOKFNCQTH-UHFFFAOYSA-N ethyl 2-(3,4-difluorophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(F)C(F)=C1 LKVYMQOKFNCQTH-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- OLOCUUHMAFKYKI-UHFFFAOYSA-N 1-(3,4,5-trifluoro-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(F)=C(F)C(F)=C1O OLOCUUHMAFKYKI-UHFFFAOYSA-N 0.000 description 1
- ZRTWIJKGTUGZJY-UHFFFAOYSA-N 3,4,5-trifluorophenol Chemical compound OC1=CC(F)=C(F)C(F)=C1 ZRTWIJKGTUGZJY-UHFFFAOYSA-N 0.000 description 1
- NUWBHUIKWPEOAY-UHFFFAOYSA-N 3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide Chemical compound COC1=CC(C(=O)NN)=CC=C1C1=CN=C(C)O1 NUWBHUIKWPEOAY-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 description 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QPQQKUFWIVLPGV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid Chemical compound OC(=O)C1=CC=CN2C=NN=C12 QPQQKUFWIVLPGV-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- RHVBMDYGDUESFI-AREMUKBSSA-N ethyl (8r)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate Chemical compound C([C@@](C1=NN=2)(C(=O)OCC)OC=3C=C(F)C(F)=C(F)C=3)CCN1C=2C(C=C1OC)=CC=C1C1=CN=C(C)O1 RHVBMDYGDUESFI-AREMUKBSSA-N 0.000 description 1
- KENMKJYDXKXPKL-UHFFFAOYSA-N ethyl 2-(3,4,5-trifluoro-2-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC(F)=C(F)C(F)=C1O KENMKJYDXKXPKL-UHFFFAOYSA-N 0.000 description 1
- RHVBMDYGDUESFI-UHFFFAOYSA-N ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate Chemical compound N=1N=C2C(C(=O)OCC)(OC=3C=C(F)C(F)=C(F)C=3)CCCN2C=1C(C=C1OC)=CC=C1C1=CN=C(C)O1 RHVBMDYGDUESFI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000002462 tachykinin receptor antagonist Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013510386A JP5871909B2 (ja) | 2010-09-02 | 2011-09-01 | 複素環化合物及びその用途 |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010197064 | 2010-09-02 | ||
| JP2010197064 | 2010-09-02 | ||
| JP2011143548 | 2011-06-28 | ||
| JP2011143548 | 2011-06-28 | ||
| PCT/JP2011/070419 WO2012029991A1 (en) | 2010-09-02 | 2011-09-01 | Fused triazoles for the treatment or prophylaxis of mild cognitive impairment |
| JP2013510386A JP5871909B2 (ja) | 2010-09-02 | 2011-09-01 | 複素環化合物及びその用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013536798A JP2013536798A (ja) | 2013-09-26 |
| JP2013536798A5 true JP2013536798A5 (enExample) | 2014-10-16 |
| JP5871909B2 JP5871909B2 (ja) | 2016-03-01 |
Family
ID=45094181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013510386A Expired - Fee Related JP5871909B2 (ja) | 2010-09-02 | 2011-09-01 | 複素環化合物及びその用途 |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US8822699B2 (enExample) |
| EP (1) | EP2611805A1 (enExample) |
| JP (1) | JP5871909B2 (enExample) |
| KR (1) | KR20130139895A (enExample) |
| CN (1) | CN103249733A (enExample) |
| AR (1) | AR082865A1 (enExample) |
| AU (1) | AU2011296887A1 (enExample) |
| BR (1) | BR112013004746A2 (enExample) |
| CA (1) | CA2809779A1 (enExample) |
| CL (1) | CL2013000575A1 (enExample) |
| DO (1) | DOP2013000051A (enExample) |
| EA (1) | EA201390333A1 (enExample) |
| EC (1) | ECSP13012535A (enExample) |
| MA (1) | MA34556B1 (enExample) |
| MX (1) | MX2013002511A (enExample) |
| PE (1) | PE20131305A1 (enExample) |
| PH (1) | PH12013500403A1 (enExample) |
| SG (1) | SG187917A1 (enExample) |
| TW (1) | TW201213327A (enExample) |
| UY (1) | UY33586A (enExample) |
| WO (1) | WO2012029991A1 (enExample) |
| ZA (1) | ZA201301929B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120142672A1 (en) * | 2009-07-13 | 2012-06-07 | Tatsuki Koike | Heterocyclic compound and use thereof |
| UY33586A (es) * | 2010-09-02 | 2012-03-30 | Takeda Pharmaceutical | Compuesto heterocíclico y sus usos |
| EP2687528A1 (en) * | 2012-07-17 | 2014-01-22 | Ares Trading S.A. | Fused triazole derivatives as gamma secretase modulators |
| RU2563254C2 (ru) * | 2013-07-08 | 2015-09-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Способ получения производных 7-(гетеро)арил-4,5,6,7-тетрагидро[1,2,3]триазоло[1,5-a]пиридина |
| RU2750293C2 (ru) * | 2015-05-12 | 2021-06-25 | ЭфЭмСи Корпорейшн | Арилзамещенные бициклические соединения в качестве гербицидов |
| MY202326A (en) * | 2017-09-14 | 2024-04-24 | Daiichi Sankyo Co Ltd | Compound having cyclic structure |
| US20210079182A1 (en) * | 2019-09-12 | 2021-03-18 | Dupont Electronics, Inc. | Polyimide films and electronic devices |
| IL313039A (en) * | 2021-12-17 | 2024-07-01 | Athira Pharma Inc | Uses of bicyclic compounds for the treatment of diseases |
| CN118047687A (zh) * | 2024-01-29 | 2024-05-17 | 湖州澄博生物科技有限公司 | 一种用于对20（s）喜树碱结构进行修饰的化合物及其合成方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1261610A2 (en) | 2000-02-17 | 2002-12-04 | Bristol-Myers Squibb Pharma Company | Succinoylamino carbocycles and heterocycles as inhibitors of a-beta protein production |
| CN102584813B (zh) | 2003-05-14 | 2016-07-06 | Ngc药物公司 | 化合物及其在调节淀粉样蛋白β中的用途 |
| CA2539811A1 (en) * | 2003-10-15 | 2005-04-28 | Targacept, Inc. | Azabicycyclic compounds for relieving pain and treating central nervous system disorders |
| EP2261218B1 (en) | 2004-05-26 | 2013-04-03 | Eisai R&D Management Co., Ltd. | Imidazole compound for use as an intermediate in the production of cinnamide compounds |
| KR20070083781A (ko) | 2004-10-26 | 2007-08-24 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 신나미드 화합물의 비정질체 |
| JP2009523170A (ja) | 2006-01-11 | 2009-06-18 | メルク エンド カムパニー インコーポレーテッド | 縮合トリアゾールタキキニン受容体アンダニスト |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| GEP20115139B (en) | 2006-03-09 | 2011-01-10 | Eisai R&D Man Co Ltd | Polycyclic cinnamide derivative |
| TW200808800A (en) | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
| TW200835502A (en) | 2006-12-26 | 2008-09-01 | Daiichi Sankyo Co Ltd | Thiazepine derivatives |
| US8143394B2 (en) | 2006-12-26 | 2012-03-27 | Gilead Sciences, Inc. | Pyrido(3,2-d)pyrimidines useful for treating viral infections |
| WO2008097538A1 (en) | 2007-02-08 | 2008-08-14 | Merck & Co., Inc. | Therapeutic agents |
| MX2010006243A (es) | 2007-12-06 | 2010-08-31 | Schering Corp | Moduladores de gamma secretasa. |
| TW201030002A (en) * | 2009-01-16 | 2010-08-16 | Bristol Myers Squibb Co | Bicyclic compounds for the reduction of beta-amyloid production |
| JP2010197064A (ja) | 2009-02-23 | 2010-09-09 | Chugoku Electric Power Co Inc:The | 直下位置測定装置 |
| JP2012051806A (ja) * | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | イミダゾリルピラジン誘導体 |
| RU2515976C2 (ru) | 2009-02-26 | 2014-05-20 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Азотсодержащие конденсированные гетероциклические соединения и их применение в качестве ингибиторов продукции бета-амилоида |
| JP2012051807A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | アリールイミダゾール化合物 |
| WO2011002067A1 (ja) | 2009-07-02 | 2011-01-06 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US20120142672A1 (en) * | 2009-07-13 | 2012-06-07 | Tatsuki Koike | Heterocyclic compound and use thereof |
| WO2011006903A1 (en) | 2009-07-15 | 2011-01-20 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc | Substituted triazole and imidazole derivatives as gamma secretase modulators |
| US8637525B2 (en) | 2009-07-31 | 2014-01-28 | Bristol-Myers Squibb Company | Compounds for the reduction of beta-amyloid production |
| TWI468402B (zh) | 2009-07-31 | 2015-01-11 | 必治妥美雅史谷比公司 | 降低β－類澱粉生成之化合物 |
| WO2011016559A1 (ja) | 2009-08-07 | 2011-02-10 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| JP2011143548A (ja) | 2010-01-12 | 2011-07-28 | Panasonic Corp | スクリーン印刷機及びスクリーン印刷方法 |
| PH12012501381A1 (en) | 2010-01-15 | 2012-10-22 | Janssen Pharmaceuticals Inc | Novel substituted bicyclic triazole derivatives as gamma secretase modulators |
| UY33586A (es) * | 2010-09-02 | 2012-03-30 | Takeda Pharmaceutical | Compuesto heterocíclico y sus usos |
-
2011
- 2011-09-01 UY UY0001033586A patent/UY33586A/es unknown
- 2011-09-01 US US13/223,455 patent/US8822699B2/en not_active Expired - Fee Related
- 2011-09-01 CN CN2011800518621A patent/CN103249733A/zh active Pending
- 2011-09-01 MA MA35785A patent/MA34556B1/fr unknown
- 2011-09-01 SG SG2013012604A patent/SG187917A1/en unknown
- 2011-09-01 CA CA2809779A patent/CA2809779A1/en not_active Abandoned
- 2011-09-01 BR BR112013004746A patent/BR112013004746A2/pt not_active IP Right Cessation
- 2011-09-01 AU AU2011296887A patent/AU2011296887A1/en not_active Abandoned
- 2011-09-01 PH PH1/2013/500403A patent/PH12013500403A1/en unknown
- 2011-09-01 TW TW100131443A patent/TW201213327A/zh unknown
- 2011-09-01 US US13/819,239 patent/US8901309B2/en not_active Expired - Fee Related
- 2011-09-01 MX MX2013002511A patent/MX2013002511A/es not_active Application Discontinuation
- 2011-09-01 WO PCT/JP2011/070419 patent/WO2012029991A1/en not_active Ceased
- 2011-09-01 JP JP2013510386A patent/JP5871909B2/ja not_active Expired - Fee Related
- 2011-09-01 EP EP11791058.8A patent/EP2611805A1/en not_active Withdrawn
- 2011-09-01 EA EA201390333A patent/EA201390333A1/ru unknown
- 2011-09-01 PE PE2013000360A patent/PE20131305A1/es not_active Application Discontinuation
- 2011-09-01 KR KR1020137008170A patent/KR20130139895A/ko not_active Withdrawn
- 2011-09-01 AR ARP110103195A patent/AR082865A1/es unknown
-
2013
- 2013-02-28 CL CL2013000575A patent/CL2013000575A1/es unknown
- 2013-03-01 DO DO2013000051A patent/DOP2013000051A/es unknown
- 2013-03-14 ZA ZA2013/01929A patent/ZA201301929B/en unknown
- 2013-03-28 EC ECSP13012535 patent/ECSP13012535A/es unknown
-
2014
- 2014-08-08 US US14/454,993 patent/US20140350260A1/en not_active Abandoned
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