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Publication Number
US-12275735-B2
Publication Date
2025-04-15
Expiration Date
Abstract
This invention relates to pharmaceutically acceptable ergoline analogues and salts thereof. In particular, though not exclusively, the invention relates to formulations and uses of the same as a medicament.
Core Innovation
The patent introduces pharmaceutically acceptable ergoline analogue compounds and medicament formulations and uses. The disclosure provides a general Formula (I) scaffold for ergoline analogue compounds with variable substituents X, Y, and Z, and states a constraint that X and Z are different. The document addresses the need to maintain biological activity in ergoline analogues in view of receptor docking and/or binding, and the problem of therapeutic activity for CNS conditions.
The Formula (I) compounds are characterized by substituent selections that define variants including X as methyl or isopropyl, Y as a bond, O, CONH, NH, N(C1-6 alkyl), or A-(CH2)n-B, and Z as H, O, NH2, alkyl, aryl, heteroaryl, heterocyclic, or sulfonyl-alkyl/aryl. The disclosure also includes pharmaceutically acceptable salts of the defined compounds and multiple specific exemplified compound structures consistent with Formula (I).
The document reports receptor activity for compound 019 consistent with 5-HT2A-mediated cAMP signaling, and some activity for compounds 018 and 019 across other 5-HT2 and related assays. It also includes in silico performance metrics, including synthetic accessibility and docking scores, and computational ADMET and physicochemical properties such as solubility estimates and property rule violations.
Claims Coverage
The independent claims define multiple Formula (I) compound subsets by specific selections of X, Y, and Z, and consistently cover pharmaceutically acceptable salts. Across the independent claims provided, there are six inventive feature groupings, with dependent claim coverage also extending to administration for depression, anxiety, or a pain condition.
Formula (I) compound with X=methyl, Y=N(C1-6 alkyl), and Z=OH
A compound of Formula (I) wherein X is methyl, Y is N(C1-6 alkyl) and Z is OH; or a pharmaceutically acceptable salt thereof.
Formula (I) compound with X=methyl, Y=NH, and Z=C3-C10 heteroaromatic or heterocyclic group
A compound of Formula (I) wherein X is methyl, Y is NH and Z is a C3-C10 heteroaromatic or heterocyclic group consisting of one, two or three heteroatoms independently selected from O and N; or a pharmaceutically acceptable salt thereof.
Formula (I) compound with X=methyl, Y=NH, and Z=SO2-C6-10 aryl
A compound of Formula (I) wherein X is methyl, Y is NH and Z is SO2–C6-10 aryl; or a pharmaceutically acceptable salt thereof.
Formula (I) compound with X=isopropyl, Y=bond, and Z=C5 alkyl
A compound of Formula (I) wherein X is isopropyl, Y is a bond and Z is C5 alkyl; or a pharmaceutically acceptable salt thereof.
Formula (I) compound with X=isopropyl and a selected Y–Z group
A compound of Formula (I) wherein X is isopropyl and Y–Z together form O–(CH2)3–N(CH3)2, NH–(CH2)2–OH, NH–(CH2)3–OCH3, NH–(CH2)2–NH–SO2CH3, or O–(CH2)2–NH–SO2CH3; or a pharmaceutically acceptable salt thereof.
Formula (I) compound with X=methyl and Y–Z as NH-(CH2)3-SO2CH3
A compound of Formula (I) wherein X is methyl and Y–Z together form NH–(CH2)3–SO2CH3; or a pharmaceutically acceptable salt thereof.
Formula (I) compound with X=isopropyl or methyl and selected Y–Z groups
A compound of Formula (I) wherein X is isopropyl or methyl and Y–Z together form NH-phenyl, pyridine, O-morpholine, NH-morpholine, NH–SO2-Phenyl, NCH3–SO2-Phenyl, CONH-Phenyl, 8-oxa-3-azabicyclo[3.2.1]octane, or 2-oxa-5-azabicyclo[2.2.1]heptane; or a pharmaceutically acceptable salt thereof.
Administration for depression, anxiety, or pain conditions
A method of administering the compound of the specified Formula (I) variant, or a pharmaceutically acceptable salt thereof, to a subject suffering from depression, anxiety, or a pain condition.
The independent claims focus on defined Formula (I) ergoline analogue compounds with constrained X, Y, and Z substituents, together with pharmaceutically acceptable salts. Claim coverage also includes administration to subjects suffering from depression, anxiety, or a pain condition.
Stated Advantages
The compounds are described as maintaining biological activity in ergoline analogues in view of receptor docking and/or binding.
The document states therapeutic activity for CNS conditions and receptor activity across serotonin receptor assays.
The document reports synthetic accessibility, docking scores, computational ADMET properties, solubility estimates, and property rule violations.
Documented Applications
Administering the compound, or a pharmaceutically acceptable salt, to a subject suffering from depression, anxiety, or a pain condition.
Therapeutic indications for CNS conditions including depression, anxiety, chronic pain, insomnia, migraines, neurogenesis-related disorders, and substance/eating/OC/BDD categories [procedural detail omitted for safety].
Serotonin receptor activity measurements in cAMP, IP1/inositol phosphate 1, Ca2+, and β-arrestin assays, including 5-HT2B and 5-HT2A consistency for cAMP signaling [procedural detail omitted for safety].
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