US2015133438A1PendingUtilityA1

Heterocyclic Substituted Hexahydropyrano[3,4-d][1,3]Thiazin-2-Amine Compounds

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Assignee: PFIZERPriority: May 4, 2012Filed: Jan 9, 2015Published: May 14, 2015
Est. expiryMay 4, 2032(~5.8 yrs left)· nominal 20-yr term from priority
Inventors:Michael Aaron BrodneyChristopher Ryan ButlerElizabeth Mary BeckJennifer Elizabeth DavorenBrian Thomas O'Neill
A61P 3/10A61P 43/00A61P 3/04A61P 27/16A61P 25/34A61P 25/16A61P 25/08C07D 513/04A61P 25/36A61P 25/18A61P 25/28A61P 25/06A61P 25/22A61P 25/32A61P 25/24A61P 27/02A61P 25/20A61K 31/542
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Claims

Abstract

Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

Claims

exact text as granted — not AI-modified
1 - 25 . (canceled) 
     
     
         26 . A compound selected from the group consisting of
 (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-4-methyl-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-thiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methylpyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-[1-(propan-2-yl)-1H-pyrazol-3-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methyl-1,3-oxazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4,5-dimethyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2-oxazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-6-(1-cyclopropyl-1H-pyrazol-3-yl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-[4-(trifluoromethyl)-1,3-oxazol-2-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-difluorophenyl)-4-methyl-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine; and   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   or a tautomer thereof.   
     
     
         27 . A pharmaceutically acceptable salt of a compound selected from the group consisting of
 (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-4-methyl-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-thiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methylpyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-[1-(propan-2-yl)-1H-pyrazol-3-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methyl-1,3-oxazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4,5-dimethyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2-oxazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-6-(1-cyclopropyl-1H-pyrazol-3-yl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-[4-(trifluoromethyl)-1,3-oxazol-2-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-difluorophenyl)-4-methyl-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine; and   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   or a tautomer thereof.   
     
     
         28 . A pharmaceutical composition comprising a therapeutically effective amount of a compound selected from the group consisting of
 (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-4-methyl-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-thiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methylpyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-[1-(propan-2-yl)-1H-pyrazol-3-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methyl-1,3-oxazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4,5-dimethyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2-oxazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-6-(1-cyclopropyl-1H-pyrazol-3-yl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-[4-(trifluoromethyl)-1,3-oxazol-2-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-difluorophenyl)-4-methyl-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine; and   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   or a tautomer thereof, and a pharmaceutically acceptable vehicle, diluent or carrier.   
     
     
         29 . A pharmaceutical composition comprising a therapeutically effective amount of a pharmaceutically acceptable salt of a compound selected from the group consisting of
 (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-4-methyl-6-(1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1-methyl-1H-pyrazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methyl-1,3-thiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methylpyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-[1-(propan-2-yl)-1H-pyrazol-3-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(2-methyl-1,3-oxazol-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(4,5-dimethyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(3-methyl-1,2-oxazol-5-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-Difluorophenyl)-6-(5-methyl-1,3,4-oxadiazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-4-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-6-(1-cyclopropyl-1H-pyrazol-3-yl)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-[4-(trifluoromethyl)-1,3-oxazol-2-yl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(pyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   4aR,6R,8aS)-8a-(2,4-difluorophenyl)-4-methyl-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoropyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine; and   (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-methylpyrimidin-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine;   
       or a tautomer thereof, and a pharmaceutically acceptable vehicle, diluent or carrier.

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