Phenyl alkyl carbamate derivative compound and pharmaceutical composition containing the same
Inventors
Assignees
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Publication Number
US-9029589-B2
Publication Date
2015-05-12
Expiration Date
Abstract
A phenyl alkyl carbamate derivative compound and a pharmaceutical composition containing the compound are provided. More specifically, the phenyl alkyl carbamate derivative compound and a pharmaceutically acceptable salt thereof, a composition for muscle relaxation containing the phenyl alkyl carbamate derivative compounds and/or pharmaceutically acceptable salt thereof as an active ingredient, and a method of muscle relaxation comprising administering a pharmaceutically effective amount of the phenyl alkyl carbamate derivative compound and/or a pharmaceutically acceptable salt thereof to a subject in need of to a subject in need of, are provided.
Core Innovation
The invention relates to compounds represented by Chemical Formula 1 or pharmaceutically acceptable salts thereof. The compounds are defined by substituent-selection variables in which X is a halogen, n is an integer from 1 to 5, R1 is hydrogen or a C1-C4 linear or branched alkyl group, and A and B are each selected from hydrogen, a C1-C4 linear or branched alkyl, a C2-C4 alkoxy alky ether group, and a carbamoyl derivative represented by R2 and R3. The compound family includes pharmaceutically acceptable salts and stereochemical forms including racemate, enantiomer, diastereomer, and mixtures thereof.
The definition includes mutual-exclusion rules between A and B, where when one of A and B is hydrogen, the other is neither hydrogen nor the carbamoyl derivative. Further, when R1 is hydrogen and one of A and B is a carbamoyl derivative, the other of A and B is a C1-C4 linear or branched alkyl or a C2-C4 alkoxy alky ether group. R2 and R3 are the same as or different from each other and are independently selected from hydrogen, a C1-C4 linear or branched alkyl group, a C3-C8 cycloalkyl group, and a benzyl group.
The documented content provides preparation and characterization examples for carbamate and carbamoyloxy derivatives within the Chemical Formula 1 space, including chiral halophenyl and methoxyalkyl variants. The examples vary aryl halogen substitution, linker length, stereochemistry, and carbamate N-substituent selection, and they are presented with 1H NMR data, isolated yields, and chemical structure depictions.
Claims Coverage
The independent claims cover a compound, a pharmaceutical composition, a method of muscle relaxation, and a method of treating or preventing a muscle spasm associated disease. Across these claims, the coverage centers on the Chemical Formula 1 scaffold defined by X, n, R1, A, B, and R2/R3, together with explicit conditional rules between hydrogen and carbamoyl derivative selections.
Chemical Formula 1 compound with conditional substituent selection rules
A compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof, wherein X is a halogen, n is an integer from 1 to 5, R1 is hydrogen or a C1-C4 linear or branched alkyl group, A is selected from hydrogen, a C1-C4 linear or branched alkyl, a C2-C4 alkoxy alky ether group, and a carbamoyl derivative represented by R2 and R3, and B is selected from hydrogen, a C1-C4 linear or branched alkyl, a C2-C4 alkoxy alky ether group, and a carbamoyl derivative represented by R2 and R3, with R2 and R3 independently selected from hydrogen, a C1-C4 linear or branched alkyl group, a C3-C8 cycloalkyl group, and a benzyl group, and wherein when one of A and B is hydrogen, the other is neither hydrogen nor the carbamoyl derivative, and when R1 is hydrogen and one of A and B is a carbamoyl derivative, the other of A and B is a C1-C4 linear or branched alkyl or a C2-C4 alkoxy alky ether group.
Pharmaceutical composition for muscle relaxation or muscle spasm associated disease
A pharmaceutical composition for muscle relaxation or treating or preventing a muscle spasm associated disease, containing the compound represented by Chemical Formula 1, a pharmaceutically acceptable salt thereof, a racemate thereof, an enantiomer thereof, a diastereomer thereof, a mixture of enantiomer thereof, or a mixture of diastereomer thereof, as an active ingredient, with the same Chemical Formula 1 substituent-selection variables and conditional rules.
Method of muscle relaxation by administering Chemical Formula 1 compound
A method of muscle relaxation comprising administering a therapeutically effective amount of the compound represented by Chemical Formula 1, a pharmaceutically acceptable salt thereof, a racemate thereof, an enantiomer thereof, a diastereomer thereof, a mixture of enantiomer thereof, or a mixture of diastereomer thereof, to a subject in need of muscle relaxation or treating or preventing a muscle spasm associated disease, with the same Chemical Formula 1 substituent-selection variables and conditional rules.
Method of treating or preventing muscle spasm associated disease
A method of treating or preventing a muscle spasm associated disease comprising administering a therapeutically effective amount of the compound represented by Chemical Formula 1, a pharmaceutically acceptable salt thereof, a racemate thereof, an enantiomer thereof, a diastereomer thereof, a mixture of enantiomer thereof, or a mixture of diastereomer thereof, to a subject in need of muscle relaxation or treating or preventing a muscle spasm associated disease, with the same Chemical Formula 1 substituent-selection variables and conditional rules.
The independent claims define a Chemical Formula 1 compound family with halogen X, integer n, R1, and conditional A/B selection rules involving hydrogen and carbamoyl derivatives, and extend that compound family to pharmaceutical compositions and methods for muscle relaxation and for treating or preventing muscle spasm associated disease.
Stated Advantages
Considerably excellent muscle relaxation.
Very low toxicity.
Documented Applications
Muscle relaxation.
Treating or preventing a muscle spasm associated disease.
Muscle spasm associated disease selected from vascular disorders of the spinal cord, spastic spinal paralysis, cervical spondylosis, cerebral palsy, sequelae of injuries, and spinocerebellar degeneration.
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