JP2012520324A5 - - Google Patents
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- JP2012520324A5 JP2012520324A5 JP2011554237A JP2011554237A JP2012520324A5 JP 2012520324 A5 JP2012520324 A5 JP 2012520324A5 JP 2011554237 A JP2011554237 A JP 2011554237A JP 2011554237 A JP2011554237 A JP 2011554237A JP 2012520324 A5 JP2012520324 A5 JP 2012520324A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- halo
- cycloalkyl
- heteroaryl
- 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.)
- Granted
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 73
- 125000001072 heteroaryl group Chemical group 0.000 claims 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims 49
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 46
- 125000003118 aryl group Chemical group 0.000 claims 45
- 125000001424 substituent group Chemical group 0.000 claims 40
- 229910052736 halogen Inorganic materials 0.000 claims 38
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 36
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 22
- -1 halo (C1-C6) Alkyl Chemical group 0.000 claims 20
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 125000001246 bromo group Chemical group Br* 0.000 claims 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 239000011593 sulfur Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000003367 polycyclic group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
- XXOQJWXDRPURJK-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1-benzoxepine Chemical compound O1CCCCC2=CC=CC=C21 XXOQJWXDRPURJK-UHFFFAOYSA-N 0.000 claims 1
- GKNLVRYWFYXZFU-UHFFFAOYSA-N 2,3-dihydro-1h-phenalene Chemical compound C1=CC(CCC2)=C3C2=CC=CC3=C1 GKNLVRYWFYXZFU-UHFFFAOYSA-N 0.000 claims 1
- HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 claims 1
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 claims 1
- HEOQXHNKRXRCTO-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulene Chemical compound C1CCCCC2=CC=CC=C21 HEOQXHNKRXRCTO-UHFFFAOYSA-N 0.000 claims 1
- 208000024667 ABeta amyloidosis, Dutch type Diseases 0.000 claims 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000006999 cognitive decline Effects 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000036536 dutch type ABeta amyloidosis Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005549 heteroarylene group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21014609P | 2009-03-13 | 2009-03-13 | |
| US61/210,146 | 2009-03-13 | ||
| US30754210P | 2010-02-24 | 2010-02-24 | |
| US61/307,542 | 2010-02-24 | ||
| PCT/US2010/027173 WO2010105179A2 (en) | 2009-03-13 | 2010-03-12 | Inhibitors of beta-secretase |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015080118A Division JP2015147792A (ja) | 2009-03-13 | 2015-04-09 | β−セクレターゼ阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012520324A JP2012520324A (ja) | 2012-09-06 |
| JP2012520324A5 true JP2012520324A5 (https=) | 2013-04-25 |
| JP5731414B2 JP5731414B2 (ja) | 2015-06-10 |
Family
ID=42664888
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011554237A Expired - Fee Related JP5731414B2 (ja) | 2009-03-13 | 2010-03-12 | β−セクレターゼ阻害剤 |
| JP2015080118A Pending JP2015147792A (ja) | 2009-03-13 | 2015-04-09 | β−セクレターゼ阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015080118A Pending JP2015147792A (ja) | 2009-03-13 | 2015-04-09 | β−セクレターゼ阻害剤 |
Country Status (28)
| Country | Link |
|---|---|
| US (3) | US8633212B2 (https=) |
| EP (2) | EP2406240B1 (https=) |
| JP (2) | JP5731414B2 (https=) |
| KR (2) | KR20120001756A (https=) |
| CN (1) | CN102348698B (https=) |
| AP (1) | AP2866A (https=) |
| AR (1) | AR075854A1 (https=) |
| AU (1) | AU2010223937B2 (https=) |
| BR (1) | BRPI1009333B8 (https=) |
| CA (1) | CA2753730C (https=) |
| CO (1) | CO6450683A2 (https=) |
| DK (1) | DK2406240T3 (https=) |
| EA (1) | EA020875B1 (https=) |
| EC (1) | ECSP11011398A (https=) |
| ES (1) | ES2571057T3 (https=) |
| GE (1) | GEP20135964B (https=) |
| IL (1) | IL214226A (https=) |
| MA (1) | MA33240B1 (https=) |
| MX (1) | MX2011009571A (https=) |
| NZ (1) | NZ594230A (https=) |
| PE (1) | PE20120219A1 (https=) |
| PT (1) | PT2406240E (https=) |
| SG (1) | SG173466A1 (https=) |
| TN (1) | TN2011000400A1 (https=) |
| TW (1) | TWI464153B (https=) |
| UY (1) | UY32490A (https=) |
| WO (1) | WO2010105179A2 (https=) |
| ZA (2) | ZA201106002B (https=) |
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| US8450308B2 (en) * | 2008-08-19 | 2013-05-28 | Vitae Pharmaceuticals, Inc. | Inhibitors of beta-secretase |
| CA2753730C (en) | 2009-03-13 | 2020-12-22 | Vitae Pharmaceuticals, Inc. | Inhibitors of beta-secretase |
| UA108363C2 (uk) | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
| CN102812005B (zh) * | 2010-02-24 | 2014-12-10 | 生命医药公司 | β-分泌酶抑制剂 |
| EP2643325A1 (en) | 2010-11-23 | 2013-10-02 | Amgen Inc. | Spiro-amino-imidazolone and spiro-amino-dihydro-pyrimidinone compounds as beta-secretase modulators and methods of use |
| US8415483B2 (en) * | 2010-12-22 | 2013-04-09 | Astrazeneca Ab | Compounds and their use as BACE inhibitors |
| GB201100181D0 (en) | 2011-01-06 | 2011-02-23 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101139D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| EP2673279A1 (en) | 2011-02-07 | 2013-12-18 | Amgen Inc. | 5-amino-oxazepine and 5-amino-thiazepane compounds as beta-secretase antagonists and methods of use |
| EP2675810A1 (en) | 2011-02-15 | 2013-12-25 | Amgen Inc. | Spiro-amino-imidazo-fused heterocyclic compounds as beta-secretase modulators and methods of use |
| WO2013044092A1 (en) | 2011-09-21 | 2013-03-28 | Amgen Inc. | Amino-oxazines and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
| EP2780321B1 (en) | 2011-10-10 | 2015-12-30 | Astrazeneca AB | Mono-fluoro beta-secretase inhibitors |
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| US9000182B2 (en) * | 2012-06-20 | 2015-04-07 | Astrazeneca Ab | 2H-imidazol-4-amine compounds and their use as BACE inhibitors |
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| US9000185B2 (en) * | 2012-06-20 | 2015-04-07 | Astrazeneca Ab | Cycloalkyl ether compounds and their use as BACE inhibitors |
| US10548882B2 (en) | 2012-06-21 | 2020-02-04 | Astrazeneca Ab | Camsylate salt |
| TW201422592A (zh) | 2012-08-27 | 2014-06-16 | Boehringer Ingelheim Int | β－分泌酶抑制劑 |
| WO2014051653A1 (en) | 2012-09-27 | 2014-04-03 | Portola Pharmaceuticals, Inc. | Bicyclic dihydropyridone kinase inhibitors |
| JP2015532282A (ja) | 2012-09-28 | 2015-11-09 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | β−セクレターゼの阻害剤 |
| WO2014078314A1 (en) | 2012-11-15 | 2014-05-22 | Amgen Inc. | Amino-oxazine and amino-dihydrothiazine compounds as beta-secretase modulators and methods of use |
| WO2014081558A1 (en) | 2012-11-21 | 2014-05-30 | Boehringer Ingelheim International Gmbh | PROCESS FOR MAKING N-SULFINYL a-AMINO AMIDES |
| US10550327B2 (en) | 2012-11-21 | 2020-02-04 | Merck Patent Gmbh | Polymerisable compounds and the use thereof in liquid-crystal displays |
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| US9353089B2 (en) | 2013-03-26 | 2016-05-31 | Saint Louis University | Compositions and methods for the treatment of malaria |
| TW201629025A (zh) * | 2014-10-07 | 2016-08-16 | 阿斯特捷利康公司 | 化合物及其作為ｂａｃｅ抑制劑之用途 |
| JP6319805B2 (ja) * | 2014-10-08 | 2018-05-09 | 田岡化学工業株式会社 | スピロビフルオレン骨格を有するジオール化合物およびその製造方法 |
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| US11505534B2 (en) | 2017-05-16 | 2022-11-22 | The University Of Chicago | Highly diastereoselective construction of the 4,5-spirocycle via palladium-catalyzed intramolecular alkenylation |
| JP6785965B2 (ja) * | 2017-06-14 | 2020-11-18 | 日本曹達株式会社 | オキサジアゾリン化合物および有害生物防除剤 |
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| WO2019168874A1 (en) | 2018-02-27 | 2019-09-06 | The Research Foundation For The State University Of New York | Difluoromethoxylation and trifluoromethoxylation compositions and methods for synthesizing same |
| CN108675923B (zh) * | 2018-06-27 | 2021-04-27 | 沅江华龙催化科技有限公司 | 一种由环酮化合物与2-芳基丙烯及二甲亚砜共同构建螺环化合物的方法 |
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