Capsaicinoid prodrug compounds and their use in treating medical conditions
Inventors
Campbell, James N. • Duncan, Scott M.
Assignees
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Publication Number
US-11820727-B1
Publication Date
2023-11-21
Expiration Date
Abstract
The invention provides capsaicinoid prodrug compounds, pharmaceutical compositions, and their use in the treatment of medical conditions, such as pain, and in agonizing TRPV1 activity.
Core Innovation
The disclosed subject matter provides compounds represented by Formula I, Formula II, and Formula V, together with pharmaceutically acceptable salts thereof. The compounds are defined through variable substituent groups and ring parameters, including R1, R2, R3, R4, R5, R2A, R2B, X, Y, Ring A, m, and n, with specified allowed identities, optional substitution counts, and ring-forming linkages. The structures include capsaicinoid prodrug compounds and table-enumerated compounds, with example structures shown across Table 1, Table 1A, and related tables.
The disclosure also describes shared scaffold features that include amide or carbonyl-containing motifs, nitrogen-containing ring systems, bicyclic or bridged amine motifs, and substituted heteroaryl, aryl, heterocyclic, and carbocyclic ring systems. In the capsaicinoid prodrug embodiments, the compounds are described as providing controllable release rate of capsaicin in aqueous environments, and specific prodrug variants are categorized as carbamate, ester/carbonate, amino oxoacetate, and phosphoramidate. The table-based embodiments include individually enumerated structures with R* variations and pharmaceutically acceptable salt forms.
The disclosed embodiments further include pharmaceutical compositions including an aqueous solution for injection. The document also states TRPV1 agonizing activity and pain-related use language for the compounds, while other portions are limited to explicit table enumeration of specific compounds rather than a broader generic chemical class.
Claims Coverage
The consolidated claims coverage includes multiple independent claim groupings: structurally defined compounds of Formula I or Formula II, a Formula V compound definition, and table-enumerated compounds from Table 1 and Table 1A, together with pharmaceutically acceptable salts. In total, the consolidated set reflects several inventive feature groupings centered on structural definition and table-based compound selection.
Compounds of Formula I or Formula II
A compound of Formula I or Formula II, or a pharmaceutically acceptable salt thereof, defined by substituent groups and ring constraints including R1, R2, R3, R4, Ring A, m, and n, with specified allowed identities, optional substitution counts, ring-forming linkages, and cis or trans double bond options.
Capsaicinoid prodrug compound of Formula I or Formula II
A capsaicinoid prodrug compound of Formula I or Formula II, or a pharmaceutically acceptable salt thereof, with Ring A defined by the specified heterocyclic or carbocyclic options and structural constraints on R groups and ring formation.
Formula I or Formula II compound definition with R1–R4, m and n constraints
A compound of Formula I or Formula II, or a pharmaceutically acceptable salt thereof, with R1–R4 defined by allowed substituents and ring-forming linkages, and with Formula II further restricting Ring A and n.
Formula I or Formula II capsaicinoid prodrug compound
A compound of Formula I or Formula II, or a pharmaceutically acceptable salt, with R1–R4, Ring A, and parameters m and n defining the structure and with the cis/trans double bond allowance for R4.
Table-enumerated compounds from Table 1 or Table 1A
A compound in Table 1 or Table 1A, or a pharmaceutically acceptable salt thereof, with claim scope limited to the explicitly listed table entries and their R* variants.
Activating TRPV1 by exposing TRPV1 to an effective amount
A method for activating TRPV1 by exposing TRPV1 to an effective amount of a compound as defined by the claimed Formula I or Formula II compound.
Treating or preventing pain by administering a therapeutically effective amount
A method for treating or preventing pain in a subject by administering a therapeutically effective amount of the claimed compound.
Table-based compound selection from Table 1 or Table 1A
A compound defined as one of the compounds in Table 1 or Table 1A, with the selection limited to the enumerated entries.
Pharmaceutically acceptable salt coverage
The claimed subject matter includes the compound and a pharmaceutically acceptable salt thereof.
R* substituent mapping within tables
Table entries defined using R* columns for the enumerated compounds in Table 1 and Table 1A.
The claims focus on structurally defined compound sets and table-enumerated compounds, with repeated coverage for pharmaceutically acceptable salts. The consolidated inventive scope also includes method-of-use claims related to TRPV1 agonizing activity and pain treatment or prevention, as explicitly stated in the input items.
Stated Advantages
Provides a controllable release rate of capsaicin in aqueous environments.
Treats or prevents pain, including osteoarthritis and joint pain.
Providing TRPV1 agonizing activity by exposing TRPV1 to an effective amount of the prodrug.
Reducing pain duration or pain magnitude.
Documented Applications
Treating or preventing pain, including post-operative pain, chronic pain, arthritic pain, neuropathic pain, nociceptive pain, osteoarthritis, rheumatoid arthritis, and joint pain.
Agonizing TRPV1 by administering or exposing a subject or TRPV1 to the compounds of Formulas I–V.
Treating topical itch.
Reducing temporary pain and improving efficacy using cooling articles in connection with administration contexts.
Intrathecal administration and pain contexts involving dorsal root ganglia and trigeminal ganglion.
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