Creatine prodrugs, compositions and methods of use thereof
AssigneeFarmington Pharma Development
InventorWilliam F. Brubaker
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Abstract
The invention describes membrane permeable creatine prodrugs, pharmaceutical compositions comprising membrane permeable creatine prodrugs, and methods of treating diseases such as ischemia, heart failure, neurodegenerative disorders and genetic disorders affecting the creatine kinase system comprising administering creatine prodrugs or pharmaceutical compositions thereof. The invention also describes treating a genetic disease affecting the creatine kinase system, such as, for example, a creatine transporter disorder or a creatine synthesis disorder comprising administering creatine prodrugs or pharmaceutical compositions thereof.
Claims21
A compound of Formula (III), or a pharmaceutically acceptable salt, solvate, tautomer or stereoisomer thereof:
- wherein the compound of Formula (III) is:
- wherein:
- W is CH2OH or —C(O)OR7;
- R is —CH3 or —CD3;
- R7 is hydrogen, C1-12 alkyl, substituted C1-12 alkyl, C1-12 heteroalkyl, substituted C1-12 heteroalkyl, C3-12 cycloalkyl, substituted C3-12 cycloalkyl, C4-20 cycloalkylalkyl, substituted C4-20 cycloalkylalkyl, C4-20 heterocycloalkylalkyl, substituted C4-20 heterocycloalkylalkyl, C5-12 aryl, substituted C5-12 aryl, C5-12 heteroaryl, substituted C5-12 heteroaryl, C6-20 arylalkyl, substituted C6-20 arylalkyl, C6-20 heteroarylalkyl, substituted C6-20 heteroarylalkyl, —C(O)R5, —C(O)OR5, —C(O)(NR3R4), —C(R3R4)—C(O)OR22, —C(R3R4)—(O)C(O)R22, —C(R3R4)—(O)C(O)—OR22,
- n is an integer from 1 to 2;
- each R3 and R4 is independently hydrogen, C1-12 alkyl or substituted C1-12 alkyl;
- and
- R5 is hydrogen, C1-12 alkyl, substituted C1-12 alkyl, C1-12 heteroalkyl, substituted C1-12 heteroalkyl, C3-12 cycloalkyl, substituted C3-12 cycloalkyl, C4-20 cycloalkylalkyl, substituted C4-20 cycloalkylalkyl, C4-20 heterocycloalkylalkyl, substituted C4-20 heterocycloalkylalkyl, C5-12 aryl, substituted C5-12 aryl, C5-12 heteroaryl, substituted C5-12 heteroaryl, C6-20 arylalkyl, substituted C6-20 arylalkyl, C6-20 heteroarylalkyl or substituted C6-20 heteroarylalkyl;
- R23 is hydrogen, C1-12 alkyl, substituted C1-12 alkyl, C5-12 cycloalkyl, substituted C5-12 cycloalkyl, C5-12 aryl, and C5-12 substituted aryl, —C(O)—OR22 or —C(O)—R22;
- and
- R22 is C1-12 alkyl, substituted C1-12 alkyl, C1-12 heteroalkyl, substituted C1-12 heteroalkyl, C3-12 cycloalkyl, substituted C3-12 cycloalkyl, C4-20 cycloalkylalkyl, substituted C4-20 cycloalkylalkyl, C4-20 heterocycloalkylalkyl, substituted C4-20 heterocycloalkylalkyl, C5-12 aryl, substituted C5-12 aryl, C5-12 heteroaryl, substituted C5-12 heteroaryl, C6-20 arylalkyl, substituted C6-20 arylalkyl, C6-20 heteroarylalkyl or substituted C6-20 heteroarylalkyl.
Dependencies are inferred from the claim text.