5-deutero-2,4-thiazolidinedione derivatives and compositions comprising and methods of using the same
AssigneeDeuteRx, LLC
InventorSheila DeWitt
Life of this patent
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Abstract
The invention provides 5-deuterium-enriched 2,4-thiazolidinediones (e.g., 5-[4-[2-(5-ethyl-2-pyridyl)-2-oxoethoxy]benzyl]-5-deutero-thiazolidine-2,4-dione), deuterated derivatives thereof, stereoisomers thereof, pharmaceutically acceptable salt forms thereof, and methods of treatment using the same.
Claims40
A deuterium-enriched compound of formula I:
- and pharmaceutically acceptable salts and stereoisomers thereof, wherein:
- R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 are independently selected from H and D;
- Z is H or D, provided that the abundance of deuterium in Z is at least 30%;
- ring A is phenyl or a monocyclic heteroaryl having 1-3 heteroatoms selected from N, O, or S;
- and ring A is substituted with 1-2 RA;
- RA, at each occurrence, is independently selected from:
- H, D, halo, C1-6 alkyl optionally substituted with 1-3 halo, and C1-6 alkoxy optionally substituted with 1-3 halo;
- R11 is selected from:
- halo, OH, OD, and C1-6 alkyl optionally substituted with 1-2 groups independently selected from OH, OD, and halo;
- alternatively, R10 and R11 are taken together with the carbon to which they are attached to form a carbonyl;
- alternatively, when CR10R11 is C(O) or CH2, then ring A is substituted with 1 RB;
- RB is selected from:
- CH3C(O)—, CH3CH(OR)—, and —CH2CO2H;
- R is selected from H, D, and C1-8 acyl;
- and
- a hydrogen atom present anywhere in the compound of Formula I is optionally replaced by D.
2-4. (canceled)
6-7. (canceled)
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A deuterium-enriched compound represented by formula IV or a stereoisomer or pharmaceutically acceptable salt form thereof:
- wherein:
- R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R12, R13, R14, and R15 are independently selected from H and D;
- Z is H or D, provided that the abundance of deuterium in Z is at least 30%;
- RA is C1-6 alkyl optionally substituted with 1-3 halo;
- R11 is selected from:
- H, D, halo, OH, OD, and, C1-6 alkyl optionally substituted with 1-2 groups independently selected from OH, OD, and halo;
- alternatively, R10 and R11 are taken together with the carbon to which they are attached to form a carbonyl;
- and
- a hydrogen atom present anywhere in the compound of Formula IV is optionally replaced by D.
30-37. (canceled)
A deuterium-enriched compound represented by formula VII or a stereoisomer or pharmaceutically acceptable salt form thereof:
- wherein:
- R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R12, R13 and R14 are independently selected from H and D;
- Z is H or D, provided that the abundance of deuterium in Z is at least 30%;
- CR10R11 is C(O) or CH2;
- RB is selected from:
- CH3C(O)—, CH3CH(OR)—, and —CH2CO2H;
- R is selected from H, D, and acyl;
- and
- a hydrogen atom present anywhere in the compound of Formula VII is optionally replaced by D.
39-47. (canceled)
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Dependencies are inferred from the claim text.