JP2020503294A5 - - Google Patents
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- Publication number
- JP2020503294A5 JP2020503294A5 JP2019531734A JP2019531734A JP2020503294A5 JP 2020503294 A5 JP2020503294 A5 JP 2020503294A5 JP 2019531734 A JP2019531734 A JP 2019531734A JP 2019531734 A JP2019531734 A JP 2019531734A JP 2020503294 A5 JP2020503294 A5 JP 2020503294A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- thiazine
- tautomer
- compound
- amino
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 83
- -1 2-propynyloxy Chemical group 0.000 claims 50
- 150000003839 salts Chemical class 0.000 claims 39
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 26
- QKFOHTNLZOIEHZ-UHFFFAOYSA-N 2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC=N1 QKFOHTNLZOIEHZ-UHFFFAOYSA-N 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 24
- 229920002554 vinyl polymer Polymers 0.000 claims 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- MSAMBWOENRGFFS-UHFFFAOYSA-N 4H-1,3-thiazine-6-carboxylic acid Chemical compound OC(=O)C1=CCN=CS1 MSAMBWOENRGFFS-UHFFFAOYSA-N 0.000 claims 8
- 206010012289 Dementia Diseases 0.000 claims 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- OCOWEWOMRYUXLY-NZEFLHGSSA-N (4aR,7aS)-7a-[5-[(Z)-2-[5-(2,2-difluoroethoxy)pyrazin-2-yl]-2-fluoroethenyl]-2-fluorophenyl]-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine Chemical compound NC1=N[C@]2(CN(C[C@H]2CS1)C1=NC=C(F)C=N1)C1=C(F)C=CC(\C=C(/F)C2=CN=C(OCC(F)F)C=N2)=C1 OCOWEWOMRYUXLY-NZEFLHGSSA-N 0.000 claims 2
- ZOLASYMXTWTSAU-AIELCWNPSA-N 6-[(Z)-2-[3-[(4aR,7aS)-2-amino-6-(5-fluoro-4-methoxy-6-methylpyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-1-fluoroethenyl]pyridine-3-carbonitrile Chemical compound COC1=C(F)C(C)=NC(=N1)N1C[C@H]2CSC(N)=N[C@]2(C1)C1=C(F)C=CC(\C=C(/F)C2=CC=C(C=N2)C#N)=C1 ZOLASYMXTWTSAU-AIELCWNPSA-N 0.000 claims 2
- ATYAWJWVHNUXQF-DAISNLPVSA-N 6-[(Z)-2-[3-[(4aR,7aS)-2-amino-6-(5-fluoro-4-methoxypyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-1-fluoroethenyl]pyridine-3-carbonitrile Chemical compound COC1=C(F)C=NC(=N1)N1C[C@H]2CSC(N)=N[C@]2(C1)C1=C(F)C=CC(\C=C(/F)C2=CC=C(C=N2)C#N)=C1 ATYAWJWVHNUXQF-DAISNLPVSA-N 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims 2
- 206010002022 amyloidosis Diseases 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 230000007505 plaque formation Effects 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 206010048327 Supranuclear palsy Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- WADGHWKXQZVKFK-UHFFFAOYSA-N thiazin-2-amine Chemical compound NN1SC=CC=C1 WADGHWKXQZVKFK-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662434719P | 2016-12-15 | 2016-12-15 | |
| US62/434,719 | 2016-12-15 | ||
| US201762570429P | 2017-10-10 | 2017-10-10 | |
| US62/570,429 | 2017-10-10 | ||
| PCT/US2017/066180 WO2018112084A1 (en) | 2016-12-15 | 2017-12-13 | Bicyclic thiazine and oxazine derivatives as beta-secretase inhibitors and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020503294A JP2020503294A (ja) | 2020-01-30 |
| JP2020503294A5 true JP2020503294A5 (OSRAM) | 2021-01-28 |
| JP7148518B2 JP7148518B2 (ja) | 2022-10-05 |
Family
ID=60888746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019531734A Active JP7148518B2 (ja) | 2016-12-15 | 2017-12-13 | β－セクレターゼ阻害剤としての二環式チアジンおよびオキサジン誘導体ならびに使用方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11548903B2 (OSRAM) |
| EP (1) | EP3555106B1 (OSRAM) |
| JP (1) | JP7148518B2 (OSRAM) |
| AU (1) | AU2017376445B2 (OSRAM) |
| CA (1) | CA3047285A1 (OSRAM) |
| ES (1) | ES2910367T3 (OSRAM) |
| MA (1) | MA54101A (OSRAM) |
| MX (1) | MX394391B (OSRAM) |
| WO (1) | WO2018112084A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2011071135A1 (ja) † | 2009-12-11 | 2013-04-22 | 塩野義製薬株式会社 | オキサジン誘導体 |
| MX394391B (es) | 2016-12-15 | 2025-03-24 | Amgen Inc | Derivados de tiazina y oxazina biciclicos como inhibidores de beta-secretasa y metodos de uso. |
| AU2017376444B2 (en) | 2016-12-15 | 2021-09-30 | Amgen Inc. | Thiazine derivatives as beta-secretase inhibitors and methods of use |
| WO2018112086A1 (en) | 2016-12-15 | 2018-06-21 | Amgen Inc. | Cyclopropyl fused thiazine derivatives as beta-secretase inhibitors and methods of use |
| US11021493B2 (en) | 2016-12-15 | 2021-06-01 | Amgen Inc. | 1,4-thiazine dioxide and 1,2,4-thiadiazine dioxide derivatives as beta-secretase inhibitors and methods of use |
| AU2017376441B2 (en) * | 2016-12-15 | 2021-10-14 | Amgen Inc. | Oxazine derivatives as beta-secretase inhibitors and methods of use |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5441870A (en) | 1992-04-15 | 1995-08-15 | Athena Neurosciences, Inc. | Methods for monitoring cellular processing of β-amyloid precursor protein |
| SI9300303A (en) | 1993-06-08 | 1994-12-31 | Krka Tovarna Zdravil | Process for isolation of hypolipemic effective substance |
| AU6383396A (en) | 1995-06-07 | 1996-12-30 | Athena Neurosciences, Inc. | Beta-secretase, antibodies to beta-secretase, and assays for detecting beta-secretase inhibition |
| HK1042730B (zh) | 1998-09-24 | 2005-11-18 | 法玛西雅厄普约翰美国公司 | 阿尔茨海默氏疾病分泌酶 |
| KR101052122B1 (ko) | 2005-10-25 | 2011-07-26 | 시오노기세야쿠 가부시키가이샤 | 아미노디히드로티아진 유도체 |
| EP2151435A4 (en) | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| EP2147914B1 (en) | 2007-04-24 | 2014-06-04 | Shionogi&Co., Ltd. | Aminodihydrothiazine derivatives substituted with cyclic groups |
| US20100317850A1 (en) | 2008-01-18 | 2010-12-16 | Yuichi Suzuki | Condensed aminodihydrothiazine derivative |
| TWI431004B (zh) | 2008-05-02 | 2014-03-21 | Lilly Co Eli | Ｂａｃｅ抑制劑 |
| MX2010013256A (es) | 2008-06-13 | 2010-12-21 | Shionogi & Co | Derivado heterociclico que contiene azufre que tiene actividad inhibitoria de beta-secretasa. |
| AU2009277485B2 (en) | 2008-07-28 | 2013-05-02 | Eisai R&D Management Co., Ltd. | Spiroaminodihydrothiazine derivatives |
| WO2010013302A1 (ja) | 2008-07-28 | 2010-02-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スピロアミノジヒドロチアジン誘導体 |
| JP5666304B2 (ja) * | 2008-09-30 | 2015-02-12 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 新規な縮合アミノジヒドロチアジン誘導体 |
| AR077277A1 (es) | 2009-07-09 | 2011-08-17 | Lilly Co Eli | Compuestos de biciclo (1,3)tiazin-2-amina formulacion farmaceutica que lo comprende y su uso para la manufactura de un medicamento util para el tratamiento de la enfermedad de alzheimer |
| GB0912778D0 (en) * | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydro-oxazine derivatives |
| US20110065695A1 (en) | 2009-09-11 | 2011-03-17 | Jeremy Beauchamp | Use of aminodihydrothiazines for the treatment or prevention of diabetes |
| UA108363C2 (uk) | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
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| WO2011070781A1 (ja) | 2009-12-09 | 2011-06-16 | 塩野義製薬株式会社 | 置換アミノチアジン誘導体 |
| UA103272C2 (uk) | 2009-12-11 | 2013-09-25 | Ф. Хоффманн-Ля Рош Аг | 2-аміно-5,5-дифтор-5,6-дигідро-4h-оксазини як інгібітори bace1 і/або bace2 |
| JPWO2011071135A1 (ja) | 2009-12-11 | 2013-04-22 | 塩野義製薬株式会社 | オキサジン誘導体 |
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| CN106117193B (zh) | 2011-01-13 | 2019-09-13 | 诺华股份有限公司 | 新的杂环衍生物及其在神经性疾病治疗中的应用 |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
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| US9221839B2 (en) | 2011-04-07 | 2015-12-29 | Merck Sharp & Dohme Corp. | C5-C6 oxacyclic-fused thiadiazine dioxide compounds as BACE inhibitors, compositions, and their use |
| MX2013011947A (es) | 2011-04-13 | 2014-01-16 | Merck Sharp & Dohme | Iminotiazinas 5-sustituidas y sus monoxidos y dioxidos como inhibidores de la enzima que encinde la proteina precursora amiloide en el sitio beta, composiciones y su uso. |
| CN103649082A (zh) | 2011-04-26 | 2014-03-19 | 盐野义制药株式会社 | 吡啶衍生物和含有该吡啶衍生物的bace1抑制剂 |
| EP2517898A1 (de) | 2011-04-29 | 2012-10-31 | Lanxess Deutschland GmbH | Kieselsäurehaltige Kautschukmischungen mit schwefelhaltigen Additiven |
| US8785436B2 (en) | 2011-05-16 | 2014-07-22 | Hoffmann-La Roche Inc. | 1,3-oxazines as BACE 1 and/or BACE2 inhibitors |
| TW201302763A (zh) | 2011-05-24 | 2013-01-16 | 必治妥美雅史谷比公司 | 用於減少β－類澱粉產生之化合物 |
| US8604024B2 (en) | 2011-05-24 | 2013-12-10 | Bristol-Myers Squibb Company | Compounds for the reduction of beta-amyloid production |
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| EP2747769B1 (en) | 2011-08-22 | 2017-08-02 | Merck Sharp & Dohme Corp. | 2-spiro-substituted iminothiazines and their mono-and dioxides as bace inhibitors, compositions and their use |
| UY34278A (es) | 2011-08-25 | 2013-04-05 | Novartis Ag | Derivados novedosos de oxazina y su uso en el tratamiento de enfermedades |
| EP2751116B1 (en) | 2011-08-31 | 2016-10-12 | Pfizer Inc | Hexahydropyrano [3,4-d][1,3]thiazin-2-amine compounds |
| EP2827857A4 (en) | 2012-03-20 | 2016-03-30 | Elan Pharm Inc | SPIROCYCLIC DIHYDRO-THIAZINE AND INHIBITORS OF BACE DIHYDRO-OXAZINE AND COMPOSITIONS AND USES THEREOF |
| ES2585262T3 (es) | 2012-05-04 | 2016-10-04 | Pfizer Inc | Compuestos heterocíclicos de hexahidropiran[3,4-d][1,3]tiazin-2-amina sustituidos como inhibidores de PPA, BACE1 y BACE2 |
| WO2013182638A1 (en) | 2012-06-08 | 2013-12-12 | H. Lundbeck A/S | 2 -aminothiazinylheteroaryls as bace1 inhibitors for the treatment alzheimer's disease |
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| JP2015529239A (ja) | 2012-09-20 | 2015-10-05 | ファイザー・インク | アルキル置換ヘキサヒドロピラノ［３，４−ｄ］［１，３］チアジン−２−アミン化合物 |
| WO2014062553A1 (en) | 2012-10-17 | 2014-04-24 | Merck Sharp & Dohme Corp. | Tricyclic substituted thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
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| JP2016501827A (ja) | 2012-10-24 | 2016-01-21 | 塩野義製薬株式会社 | Ｂａｃｅ１阻害作用を有するジヒドロオキサジンまたはオキサゼピン誘導体 |
| PT2912041T (pt) | 2012-10-26 | 2017-02-13 | Lilly Co Eli | Inibidores de bace |
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| WO2014098831A1 (en) | 2012-12-19 | 2014-06-26 | Bristol-Myers Squibb Company | 4,6-diarylaminothiazines as bace1 inhibitors and their use for the reduction of beta-amyloid production |
| EP2935282A1 (en) | 2012-12-19 | 2015-10-28 | Pfizer Inc. | CARBOCYCLIC- AND HETEROCYCLIC-SUBSTITUTED HEXAHYDROPYRANO[3,4-d][1,3]THIAZIN-2-AMINE COMPOUNDS |
| EP2934539B1 (en) | 2012-12-20 | 2019-03-27 | Merck Sharp & Dohme Corp. | C5, c6 oxacyclic-fused iminothiazine dioxide compounds as bace inhibitors |
| WO2014099788A1 (en) | 2012-12-21 | 2014-06-26 | Merck Sharp & Dohme Corp. | C5-spiro iminothiadiazine dioxides as bace inhibitors |
| KR20150124985A (ko) | 2013-03-08 | 2015-11-06 | 암젠 인크 | 베타-세크레타제 억제제로서 퍼플루오르화된 사이클로프로필 융합된 1,3-옥사진-2-아민 화합물 및 그의 사용 방법 |
| TWI593692B (zh) | 2013-03-12 | 2017-08-01 | 美國禮來大藥廠 | 四氫吡咯并噻嗪化合物 |
| AU2015301028B2 (en) | 2014-08-08 | 2019-09-26 | Amgen Inc. | Cyclopropyl fused thiazin-2-amine compounds as beta-secretase inhibitors and methods of use |
| EP3250035B1 (en) | 2015-04-21 | 2023-01-25 | Allgenesis Biotherapeutics Inc. | Compounds and their use as bace1 inhibitors |
| US10246429B2 (en) * | 2015-08-06 | 2019-04-02 | Amgen Inc. | Vinyl fluoride cyclopropyl fused thiazin-2-amine compounds as beta-secretase inhibitors and methods of use |
| AU2017376441B2 (en) | 2016-12-15 | 2021-10-14 | Amgen Inc. | Oxazine derivatives as beta-secretase inhibitors and methods of use |
| MX394391B (es) | 2016-12-15 | 2025-03-24 | Amgen Inc | Derivados de tiazina y oxazina biciclicos como inhibidores de beta-secretasa y metodos de uso. |
| AU2017376444B2 (en) | 2016-12-15 | 2021-09-30 | Amgen Inc. | Thiazine derivatives as beta-secretase inhibitors and methods of use |
| WO2018112086A1 (en) | 2016-12-15 | 2018-06-21 | Amgen Inc. | Cyclopropyl fused thiazine derivatives as beta-secretase inhibitors and methods of use |
| US11021493B2 (en) | 2016-12-15 | 2021-06-01 | Amgen Inc. | 1,4-thiazine dioxide and 1,2,4-thiadiazine dioxide derivatives as beta-secretase inhibitors and methods of use |
-
2017
- 2017-12-13 MX MX2019007100A patent/MX394391B/es unknown
- 2017-12-13 WO PCT/US2017/066180 patent/WO2018112084A1/en not_active Ceased
- 2017-12-13 AU AU2017376445A patent/AU2017376445B2/en active Active
- 2017-12-13 US US16/466,202 patent/US11548903B2/en active Active
- 2017-12-13 JP JP2019531734A patent/JP7148518B2/ja active Active
- 2017-12-13 EP EP17822986.0A patent/EP3555106B1/en active Active
- 2017-12-13 MA MA054101A patent/MA54101A/fr unknown
- 2017-12-13 ES ES17822986T patent/ES2910367T3/es active Active
- 2017-12-13 CA CA3047285A patent/CA3047285A1/en active Pending
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