Sulfamate derivative compounds for use in treating or alleviating pain
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Publication Number
US-10081615-B2
Publication Date
2018-09-25
Expiration Date
Abstract
The present invention relates to sulfamate derivative compounds and a composition for treating and/or alleviating pain containing the sulfamate derivative compounds or a pharmaceutically acceptable salt thereof as an active ingredient. More specifically the present invention relates to a pharmaceutical composition for treating or alleviating pain containing a sulfamate derivative compound and/or a pharmaceutically acceptable salt thereof as an active ingredient. Furthermore, the present invention relates to a method for treatment or alleviation of pain comprising administering a sulfamate derivative compound in a pharmaceutically effective amount to a subject in need of treatment or alleviation of pain.
Core Innovation
The disclosed subject matter provides sulfamate compounds represented by Chemical Formula 1 or pharmaceutically acceptable salts thereof. The compounds are defined by substituent options for X, R1, R2, R3 and R4, and by integers l, m and n each independently an integer of 0 to 4. The disclosed chemical scope includes multiple substitution patterns, stereochemical forms, and scaffold embodiments based on substituted spiro or dihydrospiro benzo[d][1,3]dioxepine or benzo[d][1,3]dioxin structures.
The document further covers pharmaceutical compositions comprising a pharmaceutically effective amount of the sulfamate compound represented by Chemical Formula 1. The sulfamate compound is used as an active ingredient in a pharmaceutical composition for alleviating or treating pain in a subject in need thereof, including neuropathic pain, cancer pain, postoperative pain, trigeminal neuralgia pain, idiopathic pain, diabetic neuropathic pain, migraine, nociceptive pain, psychogenic pain, inflammatory pain, and pathological pain.
A process is also disclosed for preparing a compound of Chemical Formula 1 by performing sulfamoylation of a compound of Chemical Formula 10 with a sulfamoylation reagent to produce the sulfamate compound of Chemical Formula 1. The preparation pathway also includes reduction, cyclization, and an acidic addition step between a phenol compound and an alcohol ester compound, leading toward Chemical Formula 10 and Chemical Formula 1.
Claims Coverage
The consolidated claim coverage includes three independent claims: one directed to sulfamate compounds of Chemical Formula 1 and pharmaceutically acceptable salts, one directed to a method of alleviating or treating pain by administering a pharmaceutical composition containing such a sulfamate compound, and one directed to a preparation process by sulfamoylation of a Chemical Formula 10 precursor. The independent claims collectively emphasize the defined Chemical Formula 1 structure, pain-treatment use, and sulfamoylation-based synthesis.
Defined sulfamate compounds of Chemical Formula 1
A compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof, wherein X is selected from hydrogen, hydroxyl, C1-C5 alkoxy, C1-C5 alkyl, C2-C5 alkenyl, C6-C10 aryl, C1-C5 alkoxycarbonyl, carboxyl, C2-C5 acyl, C1-C5 alkylthio, cyano, nitro, amine, C1-C5 alkylamine and halogen; R1 and R2 are each independently selected from hydrogen, C1-C5 alkyl, C2-C5 alkenyl and C6-C10 aryl, or together with the carbon atom to which they attach form a C3-C12 cycloalkyl group; R3 and R4 are each independently hydrogen or C1-C3 alkyl; and l, m and n are each independently an integer of 0 to 4.
Pain treatment by administering a sulfamate composition
A method of alleviating or treating pain in a subject in need thereof comprising administering a pharmaceutically effective amount of a pharmaceutical composition comprising a sulfamate compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
Sulfamoylation process to prepare Chemical Formula 1
A process of preparing a compound of Chemical Formula 1 comprising performing a sulfamoylation of a compound of Chemical Formula 10 by reacting the compound of Chemical Formula 10 with a sulfamoylation reagent to produce a sulfamate compound of Chemical Formula 1.
The claims cover Chemical Formula 1 sulfamate compounds and their pharmaceutically acceptable salts, a pain-alleviation or pain-treatment method using those compounds in a pharmaceutical composition, and a sulfamoylation-based process for producing Chemical Formula 1 from Chemical Formula 10, with the stated substituent ranges and integer parameters.
Stated Advantages
Alleviates or treats pain in a subject in need thereof.
Enhanced anti-pain activity.
Reduced side effects.
Documented Applications
Treating pain in a subject in need thereof, including neuropathic pain, cancer pain, postoperative pain, trigeminal neuralgia pain, idiopathic pain, diabetic neuropathic pain, migraine, nociceptive pain, psychogenic pain, inflammatory pain, and pathological pain.
Preparation of a sulfamate compound of Chemical Formula 1 by sulfamoylation of a compound of Chemical Formula 10 using a sulfamoylation reagent.
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