Phenylcarbamate compound and muscle relaxant containing the same
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Publication Number
US-9018253-B2
Publication Date
2015-04-28
Expiration Date
Abstract
A novel phenylcarbamate compound and a pharmaceutical composition containing the same are provided. More specifically, a novel phenylcarbamate compound, a composition for muscle relaxation containing the phenylcarbamate compound as an active ingredient, and a method of muscle relaxation comprising administering a therapeutically effective amount of the phenylcarbamate compound, are provided.
Core Innovation
The disclosure concerns substituted phenyl carbamate compounds having halogenated phenyl groups such as 2-chlorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2-fluorophenyl, 2-iodophenyl, and 2,3-dichlorophenyl, together with hydroxypropyl, hydroxybutyl, hydroxyhexyl, and hydroxy-3-methyl-butyl substituent patterns. The compounds include racemate, enantiomer, diastereomer, and mixtures of enantiomers or diastereomers, together with pharmaceutically acceptable salts and defined N-substitution patterns including N-methyl, N-propyl, N-isopropyl, N-cyclopropyl, N-cyclohexyl, N-benzyl, and a bicyclo group.
The document further specifies stereochemically defined carbamate versions, including (S)/(R) combinations for the hydroxypropyl and carbamate portions and related racemates and cross combinations. The disclosed examples report isolation, 1H NMR characterization, and preparation examples for particular stereoisomeric and N-substituted carbamate structures, including regioisomeric and monocarbamate compounds.
The method aspects use a therapeutically effective amount of a selected compound or a pharmaceutically acceptable salt thereof to induce muscle relaxation in a subject in need. Another method aspect administers the same type of selected compound to treat a disease associated with muscle spasm, with the disease scope explicitly listing herniation of intervertebral disk, vascular disorders of the spinal cord, spastic spinal paralysis, cervical spondylosis, cerebral palsy, sequelae of injuries, and spinocerebellar degeneration.
Claims Coverage
The consolidated claim coverage includes five independent claim categories. The inventive features center on a closed set of substituted carbamate compounds and salts with defined aryl substitution, hydroxyalkyl substitution, stereochemical forms, and N-substitution patterns, plus two therapeutic method claims and one claim to a specific compound.
Selected substituted carbamate compounds with defined stereochemical forms
A compound selected from a defined group of substituted carbamates having 1-(2-chlorophenyl), 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2-fluorophenyl, 2-iodophenyl, and 2,3-dichlorophenyl aryl variants, with hydroxypropyl, hydroxybutyl, hydroxyhexyl, and hydroxy-3-methyl-butyl patterns and specified N-substitution variants, wherein the compound is present as racemate, enantiomer, diastereomer, or mixtures thereof, or a pharmaceutically acceptable salt thereof.
Stereochemically defined substituted carbamate compounds with defined phenyl halogen and N-substitution
A compound or a pharmaceutically acceptable salt thereof selected from a defined group of stereochemically defined carbamate derivatives featuring (S)/(R) configurations for the hydroxypropyl and carbamate portions, including racemates and cross combinations, with aryl halogen variants such as 2-chlorophenyl, 2-fluorophenyl, and 2-iodophenyl, and N-substitution variants including N-methyl, N-propyl, N-isopropyl, N-cyclopropyl, N-cyclohexyl, N-benzyl, and a bicyclo group.
Muscle relaxation method by administering a therapeutically effective amount
A method of muscle relaxation comprising administering to a subject in need of muscle relaxation a therapeutically effective amount of a compound or a pharmaceutically acceptable salt thereof selected from the group of stereochemically defined carbamate compounds.
Treating disease associated with muscle spasm using a therapeutically effective amount
A method of treating a disease associated with muscle spasm comprising administering to a subject in need of the treatment a therapeutically effective amount of a compound or a pharmaceutically acceptable salt thereof selected from a group of stereochemically defined carbamate compounds, wherein the disease is selected from herniation of intervertebral disk, vascular disorders of the spinal cord, spastic spinal paralysis, cervical spondylosis, cerebral palsy, sequelae of injuries, and spinocerebellar degeneration.
Single defined compound as a pharmaceutically acceptable salt
The compound 1-(2-chlorophenyl)-(S)-1-hydroxypropyl-(S)-2-carbamate or a pharmaceutically acceptable salt thereof.
Across the independent claims, coverage is anchored in a defined set of substituted carbamate structures with specified aryl halogen patterns, hydroxyalkyl substituent patterns, stereochemical forms, and N-substitution variants. The therapeutic claims apply the selected compounds to muscle relaxation and to treatment of diseases associated with muscle spasm.
Stated Advantages
Muscle relaxation activity is demonstrated in animal testing with ED50 values presented in a results table.
Excellent muscle relaxation activity.
Very low toxicity.
Documented Applications
Animal testing of phenyl carbamate compounds for muscle relaxation activity using Rotarod, grip strength, and wire hang assays.
Muscle relaxation, via administering the compounds to a subject in need of muscle relaxation.
Treatment and prevention of diseases associated with muscle spasm, including herniation of intervertebral disk, vascular disorders of the spinal cord, spastic spinal paralysis, cervical spondylosis, cerebral palsy, sequelae of injuries, and spinocerebellar degeneration.
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