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10/02/08 - USPTO Class 514 | 73 views | #20080242723 | Prev - Next | About this Page

Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use

Title: Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use

Brief Patent Description - Full Patent Description - Patent Claims

The Patent Description & Claims data below is from USPTO Patent Application 20080242723, Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use.

1-

23. (canceled)

24. A method of treating spasticity or a symptom of spasticity in a patient, comprising administering to a patient in need of such treatment a therapeutically effective amount of at least one compound of Formula (I): stereoisomers thereof, pharmaceutically acceptable salts of any of the foregoing, and pharmaceutically acceptable solvates of any of the foregoing, wherein: R1 is selected from acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl; R2 and R3 are independently selected from hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl, or R2 and R3 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring; R4 is selected from hydrogen, C1-6 acyl, substituted C1-6 acyl, C1-6 alkyl, substituted C1-6 alkyl, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl; R5 is selected from hydrogen, hydroxy, mercapto, fluoro, chloro, bromo, oxo, and 4-chlorophenyl; and R6 and R7 are independently selected from hydrogen, C1-6 alkyl, substituted C1-6 alkyl, C1-6 alkoxy, substituted C1-6 alkoxy, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl.

25. A method of treating gastroesophageal reflux disease in a patient, comprising administering to a patient in need of such treatment a therapeutically effective amount of at least one compound of Formula (I): stereoisomers thereof, pharmaceutically acceptable salts of any of the foregoing, and pharmaceutically acceptable solvates of any of the foregoing, wherein: R1 is selected from acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl; R2 and R3 are independently selected from hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl, or R2 and R3 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring; R4 is selected from hydrogen, C1-6 acyl, substituted C1-6 acyl, C1-6 alkyl, substituted C1-6 alkyl, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl; R5 is selected from hydrogen, hydroxy, mercapto, fluoro, chloro, bromo, oxo, and 4-chlorophenyl; and R6 and R7 are independently selected from hydrogen, C1-6 alkyl, substituted C1-6 alkyl, C1-6 alkoxy, substituted C1-6 alkoxy, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl.

26. A method of treating drug addiction or abuse, alcohol addiction or abuse, or nicotine addiction or abuse in a patient, comprising administering to a patient in need of such treatment a therapeutically effective amount of at least one compound of Formula (I): stereoisomers thereof, pharmaceutically acceptable salts of any of the foregoing, and pharmaceutically acceptable solvates of any of the foregoing, wherein: R1 is selected from acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl; R2 and R3 are independently selected from hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl, or R2 and R3 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring; R4 is selected from hydrogen, C1-6 acyl, substituted C1-6 acyl, C1-6 alkyl, substituted C1-6 alkyl, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl; R5 is selected from hydrogen, hydroxy, mercapto, fluoro, chloro, bromo, oxo, and 4-chlorophenyl; and R6 and R7 are independently selected from hydrogen, C1-6 alkyl, substituted C1-6 alkyl, C1-6 alkoxy, substituted C1-6 alkoxy, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl.

27. A method of treating cough or emesis in a patient, comprising administering to a patient in need of such treatment a therapeutically effective amount of at least one compound of Formula (I): stereoisomers thereof, pharmaceutically acceptable salts of any of the foregoing, and pharmaceutically acceptable solvates of any of the foregoing, wherein: R1 is selected from acyl, substituted acyl, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl; R2 and R3 are independently selected from hydrogen, alkyl, substituted alkyl, alkoxycarbonyl, substituted alkoxycarbonyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, cycloalkyl, substituted cycloalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl, and substituted heteroarylalkyl, or R2 and R3 together with the carbon atom to which they are bonded form a cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, or substituted cycloheteroalkyl ring; R4 is selected from hydrogen, C1-6 acyl, substituted C1-6 acyl, C1-6 alkyl, substituted C1-6 alkyl, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl; R5 is selected from hydrogen, hydroxy, mercapto, fluoro, chloro, bromo, oxo, and 4-chlorophenyl; and R6 and R7 are independently selected from hydrogen, C1-6 alkyl, substituted C1-6 alkyl, C1-6 alkoxy, substituted C1-6 alkoxy, aryl, substituted aryl, C3-6 cycloalkyl, substituted C3-6 cycloalkyl, heteroaryl, substituted heteroaryl, C7-9 phenylalkyl, and substituted C7-9 phenylalkyl.

28. The method of any one of claims 24 to 27, wherein the compound of Formula (I) is administered as an oral dosage formulation.

29. The method of claim 28, wherein the oral dosage formulation is a sustained release oral dosage formulation.

30. The method of any one of claims 24 to 27, wherein the compound of Formula (I) is a prodrug of a 3-aminopropylsulfinic acid analog selected from: 3-aminopropylsulfinic acid; (3-amino-2-(4-chlorophenyl)propyl)sulfinic acid; (3-amino-2-hydroxypropyl)sulfinic acid; (2S)-(3-amino-2-hydroxypropyl)sulfinic acid; (2R)-(3-amino-2-hydroxypropyl)sulfinic acid; (3-amino-2-fluoropropyl)sulfinic acid; (2S)-(3-amino-2-fluoropropyl)sulfinic acid; (2R)-(3-amino-2-fluoropropyl)sulfinic acid; (3-amino-2-oxopropyl)sulfinic acid; and pharmaceutically acceptable salts thereof.

31. The method of any one of claims 24 to 27, wherein R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, cyclohexyl, and 3-pyridyl; R2 is selected from hydrogen, methyl, n-propyl, and isopropyl; R3 is hydrogen; and R5 is selected from hydrogen, hydroxy, fluoro, oxo, and 4-chlorophenyl; and each of R4, R6, and R7 is hydrogen.

Brief Patent Description - Full Patent Description - Patent Claims

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