Desferrithiocin polyether analogues
AssigneeUniversity of Florida Research Foundation, Inc.
InventorRaymond J. Bergeron, JR.
Life of this patent
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Abstract
Compounds represented by structural formulas described herein, such as Structural Formula (I): or a pharmaceutically acceptable salt thereof are useful in treating conditions such as metal overload, oxidative stress, and neoplastic and preneoplastic conditions.
Claims25
A compound represented by a structural formula selected from Structural Formulas (I), (II), and (III):
- wherein:
- R1 is —H or an acyl group;
- R2 is —[(CH2)n—O]x—[(CH2)n—O]y—R′;
- R3, R4 and R5 are each independently —H, an alkyl group, or —OR11;
- R6, R7, and R8 are each independently —H or an alkyl group;
- R9 is —OR12 or —N(OH)R13;
- R10 is —H or an alkyl group;
- R11 is —H, an alkyl group or an acyl group;
- R12 is —H or an alkyl group;
- R13 is an alkyl group;
- R14 is an alkyl group;
- R′ is an alkyl group;
- m is an integer from 1 to 8;
- each n is independently an integer from 1 to 8;
- x is an integer from 1 to 8;
- y is an integer from 0 to 8;
- Z is —C(O)R14,
- or a salt thereof.
A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and a compound represented by a structural formula selected from Structural Formulas (I), (II), and (III):
- wherein:
- R1 is —H or an acyl group;
- R2 is —[(CH2)n—O]x—[(CH2)n—O]y—R′;
- R3, R4 and R5 are each independently —H, an alkyl group, or —OR11;
- R6, R7, and R8 are each independently —H or an alkyl group;
- R9 is —OR12 or —N(OH)R13;
- R10 is —H or an alkyl group;
- R11 is —H, an alkyl group or an acyl group;
- R12 is —H or an alkyl group;
- R13 is an alkyl group;
- R14 is an alkyl group;
- R′ is an alkyl group;
- m is an integer from 1 to 8;
- each n is independently an integer from 1 to 8;
- x is an integer from 1 to 8;
- y is an integer from 0 to 8;
- Z is —C(O)R14,
- or a pharmaceutically acceptable salt thereof.
A method of treating a pathological condition responsive to chelation or sequestration of a trivalent metal in a subject, comprising administering to the subject a therapeutically or prophylactically effective amount of a compound represented by a structural formula selected from Structural Formulas (I), (II), and (III):
- wherein:
- R1 is —H or an acyl group;
- R2 is —[(CH2)n—O]x—[(CH2)n—O]y—R′;
- R3, R4 and R5 are each independently —H, an alkyl group, or —OR11;
- R6, R7, and R8 are each independently —H or an alkyl group;
- R9 is —OR12 or —N(OH)R13;
- R10 is —H or an alkyl group;
- R11 is —H, an alkyl group or an acyl group;
- R12 is —H or an alkyl group;
- R13 is an alkyl group;
- R14 is an alkyl group;
- R′ is an alkyl group;
- m is an integer from 1 to 8;
- each n is independently an integer from 1 to 8;
- x is an integer from 1 to 8;
- y is an integer from 0 to 8;
- Z is —C(O)R14,
- or a pharmaceutically acceptable salt thereof.
A method of reducing oxidative stress in a subject in need of treatment therefor, comprising administering to the subject a therapeutically effective amount of a compound represented by a structural formula selected from Structural Formulas (I), (II), and (III):
- wherein:
- R1 is —H or an acyl group;
- R2 is —[(CH2)n—O]x—[(CH2)n—O]y—R′;
- R3, R4 and R5 are each independently —H, an alkyl group, or —OR11;
- R6, R7, and R8 are each independently —H or an alkyl group;
- R9 is —OR12 or —N(OH)R13;
- R10 is —H or an alkyl group;
- R11 is —H, an alkyl group or an acyl group;
- R12 is —H or an alkyl group;
- R13 is an alkyl group;
- R14 is an alkyl group;
- R′ is an alkyl group;
- m is an integer from 1 to 8;
- each n is independently an integer from 1 to 8;
- x is an integer from 1 to 8;
- y is an integer from 0 to 8;
- Z is —C(O)R14,
- or a pharmaceutically acceptable salt thereof.
A method of treating a subject who is suffering from neoplastic disease or a preneoplastic condition, comprising administering to the subject a therapeutically effective amount of a compound represented by a structural formula selected from Structural Formulas (I), (II), and (III):
- wherein:
- R1 is —H or an acyl group;
- R2 is —[(CH2)n—O]x—[(CH2)n—O]y—R′;
- R3, R4 and R5 are each independently —H, an alkyl group, or —OR11;
- R6, R7, and R8 are each independently —H or an alkyl group;
- R9 is —OR12 or —N(OH)R13;
- R10 is —H or an alkyl group;
- R11 is —H, an alkyl group or an acyl group;
- R12 is —H or an alkyl group;
- R13 is an alkyl group;
- R14 is an alkyl group;
- R′ is an alkyl group;
- m is an integer from 1 to 8;
- each n is independently an integer from 1 to 8;
- x is an integer from 1 to 8;
- y is an integer from 0 to 8;
- Z is —C(O)R14,
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.