JP2016503785A5 - - Google Patents
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- JP2016503785A5 JP2016503785A5 JP2015548807A JP2015548807A JP2016503785A5 JP 2016503785 A5 JP2016503785 A5 JP 2016503785A5 JP 2015548807 A JP2015548807 A JP 2015548807A JP 2015548807 A JP2015548807 A JP 2015548807A JP 2016503785 A5 JP2016503785 A5 JP 2016503785A5
- Authority
- JP
- Japan
- Prior art keywords
- tautomer
- compound
- fluoro
- alkyl
- pharmaceutically acceptable
- 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 35
- 125000001153 fluoro group Chemical group F* 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- QKFOHTNLZOIEHZ-UHFFFAOYSA-N 2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC=N1 QKFOHTNLZOIEHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- YUFWDCBIDOXDCY-VAHXTSCQSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,4,6-trifluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC(F)=CC=2F)F)CC1 YUFWDCBIDOXDCY-VAHXTSCQSA-N 0.000 claims 1
- RHJJDGACVHKXNA-JJMVLAAESA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC(F)=CC=2)F)CC1 RHJJDGACVHKXNA-JJMVLAAESA-N 0.000 claims 1
- WAKCJWZQPHOJBN-JJMVLAAESA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,5-difluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC=C(F)C=2)F)CC1 WAKCJWZQPHOJBN-JJMVLAAESA-N 0.000 claims 1
- CEUHNOFRRAIAQB-WNMQOVRZSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2,6-difluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC=CC=2F)F)CC1 CEUHNOFRRAIAQB-WNMQOVRZSA-N 0.000 claims 1
- JRBPZKILTJVDPX-MJEQTWJJSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2-fluoro-4-methylphenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound FC1=CC(C)=CC=C1[C@@]1(N=C(N)SC2)[C@H]2C[C@H](C2CC2)OC1 JRBPZKILTJVDPX-MJEQTWJJSA-N 0.000 claims 1
- FHXGFQTXPUMEKT-PEYYIBSZSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(2-fluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C(=CC=CC=2)F)CC1 FHXGFQTXPUMEKT-PEYYIBSZSA-N 0.000 claims 1
- FTTYFEBEIFPZEG-JGGQBBKZSA-N (4ar,6r,8as)-6-cyclopropyl-8a-(4-fluorophenyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C=CC(F)=CC=2)CC1 FTTYFEBEIFPZEG-JGGQBBKZSA-N 0.000 claims 1
- DXFOXQOXOOZOFO-SQWLQELKSA-N (4ar,6r,8as)-6-cyclopropyl-8a-phenyl-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(SC[C@@H]3C2)N)C=2C=CC=CC=2)CC1 DXFOXQOXOOZOFO-SQWLQELKSA-N 0.000 claims 1
- HENOYKTZLIYYIJ-URNHKWKMSA-N (4r,4ar,6r,8as)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4-methyl-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(N)S[C@@H]([C@@H]3C2)C)C=2C(=CC(F)=CC=2)F)CC1 HENOYKTZLIYYIJ-URNHKWKMSA-N 0.000 claims 1
- ZOKDMAYUPFRZKD-DPAVQSFQSA-N (4s,4ar,6r,8as)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4-(fluoromethyl)-4a,5,6,8-tetrahydro-4h-pyrano[3,4-d][1,3]thiazin-2-amine Chemical compound C1([C@@H]2OC[C@@]3(N=C(S[C@H](CF)[C@@H]3C2)N)C=2C(=CC(F)=CC=2)F)CC1 ZOKDMAYUPFRZKD-DPAVQSFQSA-N 0.000 claims 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- -1 3-fluoro-4-methylphenyl Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
- 102100021257 Beta-secretase 1 Human genes 0.000 claims 1
- 102100021277 Beta-secretase 2 Human genes 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 claims 1
- 101000894883 Homo sapiens Beta-secretase 2 Proteins 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261739053P | 2012-12-19 | 2012-12-19 | |
| US61/739,053 | 2012-12-19 | ||
| PCT/IB2013/060633 WO2014097038A1 (en) | 2012-12-19 | 2013-12-04 | CARBOCYCLIC- AND HETEROCYCLIC-SUBSTITUTED HEXAHYDROPYRANO[3,4-d][1,3]THIAZIN-2-AMINE COMPOUNDS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016503785A JP2016503785A (ja) | 2016-02-08 |
| JP2016503785A5 true JP2016503785A5 (https=) | 2016-10-13 |
| JP6162820B2 JP6162820B2 (ja) | 2017-07-12 |
Family
ID=49917680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015548807A Expired - Fee Related JP6162820B2 (ja) | 2012-12-19 | 2013-12-04 | 炭素環式および複素環式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 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9403846B2 (https=) |
| EP (1) | EP2935282A1 (https=) |
| JP (1) | JP6162820B2 (https=) |
| CA (1) | CA2893333C (https=) |
| WO (1) | WO2014097038A1 (https=) |
Families Citing this family (14)
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| WO2014134341A1 (en) | 2013-03-01 | 2014-09-04 | Amgen Inc. | Perfluorinated 5,6-dihydro-4h-1,3-oxazin-2-amine compounds as beta-secretase inhibitors and methods of use |
| MX374512B (es) | 2013-03-08 | 2025-03-06 | Amgen Inc | Compuestos de 1,3-oxazin-2-amina fusionados con ciclopropilo perfluorado como inhibidores de beta-secretasa y métodos de uso. |
| CN106459088A (zh) | 2014-04-10 | 2017-02-22 | 辉瑞公司 | 2‑氨基‑6‑甲基‑4，4a，5，6‑四氢吡喃并[3，4‑d][1，3]噻嗪‑8a(8H)‑基‑1，3‑噻唑‑4‑基酰胺 |
| CN106795147B (zh) | 2014-08-08 | 2020-09-22 | 美国安进公司 | 作为β-分泌酶抑制剂的环丙基稠合噻嗪-2-胺化合物和使用方法 |
| WO2017024180A1 (en) | 2015-08-06 | 2017-02-09 | Amgen Inc. | Vinyl fluoride cyclopropyl fused thiazin-2-amine compounds as beta-secretase inhibitors and methods of use |
| JP2018534251A (ja) | 2015-09-24 | 2018-11-22 | ファイザー・インク | Ｂａｃｅ阻害剤として有用なｎ−［２−（３−アミノ−２，５−ジメチル−１，１−ジオキシド−５，６−ジヒドロ−２ｈ−１，２，４−チアジアジン−５−イル）−１，３−チアゾール−４−イル］アミド |
| WO2017051303A1 (en) | 2015-09-24 | 2017-03-30 | Pfizer Inc. | Tetrahydropyrano[3,4-d][1,3]oxazin derivatives and their use as bace inhibitors |
| JP2018531923A (ja) | 2015-09-24 | 2018-11-01 | ファイザー・インク | Ｎ−［２−（２−アミノ−６，６−二置換−４，４ａ，５，６−テトラヒドロピラノ［３，４−ｄ］［１，３］チアジン−８ａ（８Ｈ）−イル）−１，３−チアゾール−４−イル］アミド |
| CA3047290A1 (en) | 2016-12-15 | 2018-06-21 | 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 |
| 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. |
| EP3555085B1 (en) | 2016-12-15 | 2020-12-02 | Amgen Inc. | Cyclopropyl fused thiazine derivatives as beta-secretase inhibitors and methods of use |
| CA3047288A1 (en) | 2016-12-15 | 2018-06-21 | Amgen Inc. | Thiazine derivatives as beta-secretase inhibitors and methods of use |
| US20210393621A1 (en) | 2018-10-26 | 2021-12-23 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
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| EP2956458B1 (en) | 2013-02-13 | 2017-08-09 | Pfizer Inc | Heteroaryl-substituted hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds |
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-
2013
- 2013-12-04 US US14/653,549 patent/US9403846B2/en not_active Expired - Fee Related
- 2013-12-04 EP EP13817734.0A patent/EP2935282A1/en not_active Withdrawn
- 2013-12-04 WO PCT/IB2013/060633 patent/WO2014097038A1/en not_active Ceased
- 2013-12-04 JP JP2015548807A patent/JP6162820B2/ja not_active Expired - Fee Related
- 2013-12-04 CA CA2893333A patent/CA2893333C/en not_active Expired - Fee Related
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