Phenylalkyl sulfamate compound and muscle relaxant composition comprising the same
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Publication Number
US-9221783-B2
Publication Date
2015-12-29
Expiration Date
Abstract
The present invention relates to novel phenylalkyl sulfamate compounds, a method for preventing or treating a disease associated with muscle spasm. The present invention ensures the enhancement of muscle relaxation activity essential for alleviation of muscle spasm, such that it is promising for preventing or treating various diseases associated with muscle spasm.
Core Innovation
The invention is directed to compounds represented by formula 1 or pharmaceutically acceptable salts thereof, defined by substituent variables R1 through R9 and ring-position integers n and m. R1 and R2 are independently selected from hydrogen, C1-C5 alkyl, or C6-C10 aryl, or together form a C5-C6 cycloalkyl group; R3 through R7 are independently selected from hydrogen, halogen, C1-C5 alkyl, nitro group, and unsubstituted or C1-C3 alkyl-substituted amine group; and R8 and R9 are each independently hydrogen or C1-C3 alkyl.
The disclosed compounds include sulfamate-related dioxolane and dioxaspiro structures, with examples described as chlorobenzyl-, chlorophenyl-, fluorophenyl-, iodophenyl-, dichlorophenyl-, aminophenyl-, nitrophenyl-, methylphenyl-, methylaminophenyl-, and phenyl-substituted variants. The partial content focuses on structurally defined compound families and stereoisomeric forms, including dioxolane, dioxaspiro[4,4]nonane, and dioxaspiro[4,5]decane scaffolds.
The document also describes preparation examples for intermediates and title compounds, including methanol, carboxylate, pivalate, diol, and ester derivatives. The examples report isolated yields and 1H NMR characterization data for the prepared stereodefined compounds, while the background problem is not explicitly described in the provided content.
Claims Coverage
The provided claim coverage centers on one independent structural claim for formula 1 compounds and one independent method claim for muscle relaxation. In total, two inventive feature themes are present: the formula-defined compound class and its administration for muscle relaxation.
Formula 1 compound with defined substituent sets
A compound represented by formula 1 or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are each independently selected from hydrogen, C1-C5 alkyl group, and C6-C10 aryl group or together with the carbon atom to which they attach form C5-C6 cycloalkyl group; R3, R4, R5, R6 and R7 are each independently selected from hydrogen, halogen, C1-C5 alkyl group, nitro group and unsubstituted or C1-C3 alkyl-substituted amine group; R8 and R9 are each independently hydrogen or C1-C3 alkyl group; and n and m are each independently integer of 0-2.
Muscle relaxation by administering the claimed compound
A method for muscle relaxation comprising administering a pharmaceutically effective amount of the compound or pharmaceutically acceptable salt thereof according to claim 1 to a subject in need thereof.
Coverage is anchored by the formula 1 structural definition with variable substituent selections for R1-R9 and integers n and m, and by a separate method claim for muscle relaxation using the claimed compound or salt.
Stated Advantages
Muscle relaxation.
Muscle relaxation for preventing/treating muscle spasm and myotonia.
Improved or measurable outcomes via grip strength and rotarod residence time observations in mice.
Documented Applications
Method for muscle relaxation by administering a pharmaceutically effective amount of the compound or a pharmaceutically acceptable salt thereof to a subject in need thereof.
Preventing and treating muscle spasm and myotonia associated with disease states.
Pharmaceutical composition use with carriers and administration routes including parenteral administration, intramuscular, and intraperitoneal routes.
Muscle relaxation testing and associated muscle-relaxation evaluation in mice (ICR), including grip strength, wire hang, and fixed-speed rotarod with ED50 determination and statistical analysis.
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