Phenyl carbamate compound and a composition for preventing or treating a psychiatric disorder comprising the same
Inventors
Assignees
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Publication Number
US-9907776-B2
Publication Date
2018-03-06
Expiration Date
Abstract
The present invention relates to a composition for preventing or treating a psychiatric disorder comprising a phenyl carbamate compound and a method for preventing or treating a psychiatric disorder therewith. The present invention provides anti-anxiety activity and protections against seizure and bipolar disorder, such that it may be effectively used for preventing or treating various psychiatric disorders related to mood disorder or resulting convulsion.
Core Innovation
The invention concerns a method for treating a psychiatric disorder selected from depressive disorder, bipolar disorder, and anxiety disorder by administering a pharmaceutically effective amount of a composition comprising a compound represented by formula 1 or a pharmaceutically acceptable salt thereof to a subject in need thereof. The compound in formula 1 contains ring substituents where R1, R2, R3, R4, and R5 are each independently selected from hydrogen and halogen, with R6 and R7 constrained as specified, R8 as C1-C5 alkyl, and A1 selected from hydrogen, C1-C5 alkyl, C3-C8 cycloalkyl, C6-C10 aryl, C1-C3 alkyl, and bridged C6-C8 bicycloalkane.
The disclosed scope further includes substituted hydroxy carbamate and carbamate compounds, including hydroxypropyl, hydroxybutyl, hydroxyhexyl, and hydroxy-3-methyl-butyl forms, with chlorophenyl and halophenyl substitution patterns such as 2-chloro, 2,3-dichloro, 2,4-dichloro, 2,6-dichloro, 2-fluorophenyl, and 2-iodophenyl. The disclosed examples include stereochemically specified (S,S), (R,R), (S,R), and (R,S) forms, regioisomeric mono-carbamate variants, and N-substituted carbamates such as isopropyl, cyclopropyl, cyclohexyl, benzyl, and NH2 forms.
The examples further describe preparations using the substantially same method as Example 1 or Example 15 with bis(trimethylsilanyloxy) or bis-trimethylsilanyloxy precursors, and report representative characterization information such as 1H NMR data and isolated yields. The documented material includes specific products such as (S)-1-hydroxy-3-methyl-butyl-2-carbamate and (R)-1-hydroxypropyl-2-carbamate, together with structure images and preparation examples.
Claims Coverage
The claim coverage centers on administration of a formula 1 compound or salt for treating depressive disorder, bipolar disorder, and anxiety disorder, with further restrictions on ring halogens, enumerated substituted carbamate embodiments, stereochemical form, and salt formation using specified acids or ions. In total, the claim set includes five main inventive features beyond the base treatment method.
Treating psychiatric disorder with formula 1 compound
A method for treating a psychiatric disorder selected from depressive disorder, bipolar disorder, and anxiety disorder by administering a pharmaceutically effective amount of a composition comprising a compound represented by formula 1 or a pharmaceutically acceptable salt thereof to a subject in need thereof, wherein R1-R5 are each independently hydrogen or halogen; R6 and R7 are constrained as specified; A1 is selected from hydrogen, C1-C5 alkyl, C3-C8 cycloalkyl, C6-C10 aryl, C1-C3 alkyl, and bridged C6-C8 bicycloalkane; and R8 is C1-C5 alkyl.
Halogen substituents limited for R1-R5
R1, R2, R3, R4, and R5 are each independently selected from hydrogen, chlorine, fluorine, or iodine.
Selected substituted carbamate compounds within formula 1 scope
The method selects the compound from specified substituted carbamates having different phenyl halogenation patterns and hydroxypropyl, hydroxybutyl, hydroxyhexyl, or hydroxy-3-methyl-butyl carbamate and N-substituted variants.
Stereochemical form of the compound
The compound is in the form of racemate, enantiomer, diastereomer, a mixture of enantiomer, or a mixture of diastereomer.
Pharmaceutically acceptable salt formation from specified reactants
The pharmaceutically acceptable salt is produced by reacting the compound with an inorganic acid, an organic acid, an amino acid, sulfonic acid, an alkali metal, or ammonium ion.
The claim coverage centers on administration of a formula 1 compound or salt for treating depressive disorder, bipolar disorder, and anxiety disorder, with further restrictions on ring halogens, enumerated substituted carbamate embodiments, stereochemical form, and salt formation using specified acids or ions.
Stated Advantages
Enhanced anti-anxiety activity.
Protection against seizure.
Protection against bipolar disorder.
Provides anti-anxiety and anti-depression activity for the synthesized carbamate-containing compounds.
Neurotoxicity assessment is included via rotarod testing.
Seizure-related and kindling models are included to support the psychiatric, anti-anxiety, and anti-depression utility.
Behavioral anxiety evaluation is included using the light-dark choice test.
Documented Applications
Treatment of depressive disorder, bipolar disorder, and anxiety disorder by administering a composition containing Formula 1 phenyl carbamate derivatives or pharmaceutically acceptable salts.
Seizure-related protection is documented as an outcome associated with the compounds.
Bipolar disorder protection is documented as an outcome associated with the compounds.
Treating a psychiatric disorder selected from depressive disorder, bipolar disorder, and anxiety disorder using compositions containing compounds represented by formula 1 or pharmaceutically acceptable salts.
Anti-anxiety utility is evaluated using the light-dark choice test in conjunction with seizure and kindling model testing.
Anti-depression utility is supported in the described experimental evaluations of synthesized carbamate-containing compounds.
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