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 | ||
| JP2013510386A JP5871909B2 (ja) | 2010-09-02 | 2011-09-01 | 複素環化合物及びその用途 |
| PCT/JP2011/070419 WO2012029991A1 (en) | 2010-09-02 | 2011-09-01 | Fused triazoles for the treatment or prophylaxis of mild cognitive impairment |
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 (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011007756A1 (ja) * | 2009-07-13 | 2011-01-20 | 武田薬品工業株式会社 | 複素環化合物及びその用途 |
| US8822699B2 (en) * | 2010-09-02 | 2014-09-02 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| 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 |
| PL3294743T3 (pl) * | 2015-05-12 | 2020-03-31 | Fmc Corporation | Podstawione arylem związki bicykliczne jako środki chwastobójcze |
| US20210079182A1 (en) * | 2019-09-12 | 2021-03-18 | Dupont Electronics, Inc. | Polyimide films and electronic devices |
| WO2023114456A1 (en) * | 2021-12-17 | 2023-06-22 | Athira Pharma, Inc. | Uses of bicyclic compounds for the treatment of diseases |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003523345A (ja) | 2000-02-17 | 2003-08-05 | ブリストル−マイヤーズ スクイブ ファーマ カンパニー | Ａβタンパク質産生の阻害剤としてのスクシノイルアミノ炭素環および複素環 |
| US7244739B2 (en) | 2003-05-14 | 2007-07-17 | Torreypines Therapeutics, Inc. | Compounds and uses thereof in modulating amyloid beta |
| SI1678172T1 (sl) * | 2003-10-15 | 2010-04-30 | Targacept Inc | AzabicikliŽŤne spojine za lajšanje boleŽŤine in zdravljenje motenj centralnega ĹľivŽŤnega sistema |
| US7667041B2 (en) | 2004-05-26 | 2010-02-23 | Eisai R&D Management Co., Ltd. | Cinnamide compound |
| ATE458729T1 (de) | 2004-10-26 | 2010-03-15 | Eisai R&D Man Co Ltd | Amorphe form einer zimtsäureamidverbindung |
| EP1976527A4 (en) | 2006-01-11 | 2009-04-22 | Merck & Co Inc | CONDENSED TRIAZOL TACHYKININE RECEPTOR ANTAGONISTS |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| PL1992618T3 (pl) * | 2006-03-09 | 2012-06-29 | Eisai R&D Man Co Ltd | Policykliczna pochodna cynamidowa |
| TW200808800A (en) | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
| EP2119719A1 (en) | 2006-12-26 | 2009-11-18 | Daiichi Sankyo Company, Limited | Thiazepine derivative |
| WO2008077649A1 (en) | 2006-12-26 | 2008-07-03 | Gilead Sciences, Inc. | Pyrido(3,2-d)pyrimidines useful for treating viral infectons |
| CA2677296A1 (en) | 2007-02-08 | 2008-08-14 | Merck & Co., Inc. | Therapeutic agents |
| CA2707712A1 (en) | 2007-12-06 | 2009-06-11 | Schering Corporation | Gamma secretase modulators |
| 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 |
| EP2401276B1 (en) * | 2009-02-26 | 2013-06-05 | Eisai R&D Management Co., Ltd. | Nitrogen-containing fused heterocyclic compounds and their use as beta amyloid production inhibitors |
| 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 |
| WO2011007756A1 (ja) | 2009-07-13 | 2011-01-20 | 武田薬品工業株式会社 | 複素環化合物及びその用途 |
| NZ597505A (en) | 2009-07-15 | 2013-05-31 | 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 |
| US9145399B2 (en) | 2010-01-15 | 2015-09-29 | Janssen Pharmaceuticals, Inc. | Substituted bicyclic triazole derivatives as gamma secretase modulators |
| US8822699B2 (en) * | 2010-09-02 | 2014-09-02 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
-
2011
- 2011-09-01 US US13/223,455 patent/US8822699B2/en not_active Expired - Fee Related
- 2011-09-01 MA MA35785A patent/MA34556B1/fr unknown
- 2011-09-01 CA CA2809779A patent/CA2809779A1/en not_active Abandoned
- 2011-09-01 EA EA201390333A patent/EA201390333A1/ru unknown
- 2011-09-01 PH PH1/2013/500403A patent/PH12013500403A1/en unknown
- 2011-09-01 KR KR1020137008170A patent/KR20130139895A/ko not_active Withdrawn
- 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 UY UY0001033586A patent/UY33586A/es unknown
- 2011-09-01 EP EP11791058.8A patent/EP2611805A1/en not_active Withdrawn
- 2011-09-01 JP JP2013510386A patent/JP5871909B2/ja not_active Expired - Fee Related
- 2011-09-01 PE PE2013000360A patent/PE20131305A1/es not_active Application Discontinuation
- 2011-09-01 WO PCT/JP2011/070419 patent/WO2012029991A1/en not_active Ceased
- 2011-09-01 MX MX2013002511A patent/MX2013002511A/es not_active Application Discontinuation
- 2011-09-01 CN CN2011800518621A patent/CN103249733A/zh active Pending
- 2011-09-01 SG SG2013012604A patent/SG187917A1/en unknown
- 2011-09-01 AR ARP110103195A patent/AR082865A1/es 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
-
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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