Organic compound (oxime) to combat chemical warfare agents
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Prepaire LabsPrepaire Labs develops an open platform for drug discovery and disease modeling, with a focus on personalized medicine through genetic insights. Its offerings include AI-powered analysis, an app store for scientific applications, and bioinformatics developer tools. The company's infrastructure supports advanced lab work, genome sequencing services, and biobanking to accelerate therapeutic innovation.
Prepaire Labs develops an open platform for drug discovery and disease modeling, with a focus on personalized medicine through genetic insights. Its offerings include AI-powered analysis, an app store for scientific applications, and bioinformatics developer tools. The company's infrastructure supports advanced lab work, genome sequencing services, and biobanking to accelerate therapeutic innovation.
Publication Number
US-12448356-B2
Publication Date
2025-10-21
Expiration Date
Abstract
Described herein are compounds that reactivate acetylcholinesterase and associated methods of treating organophosphate poisoning.
Core Innovation
The invention relates to oxime-based small molecules for treating organophosphate poisoning by reactivating acetylcholinesterase (AChE). It addresses the interaction between inhibited AChE and an organophosphate, including nerve agents, where oxime restoring is described as breaking the enzyme-organophosphate interaction to restore AChE function.
The disclosure provides chemical structures expressed through Formula (I) and related oxime scaffold formulas, including Formula (III), Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (IX), Formula (V) through (XI), as well as variants such as Formula (IA), Formula (II), Formula (IIA), and Formula (IIB). Substituent definitions include aryl options, oxime-containing motifs, and specified structural relationships involving variables such as R1, R2, R3, X, and ring-size ranges.
The invention also describes a treatment-design rationale using systems-level and AI-enabled treatment design concepts, including patient phenotyping, trajectories, and in-silico efficacy and safety. In-silico binding and affinity results are reported for representative compounds against AChE inhibited with organophosphates such as sarin and VX/Novichok-related agents, and the compounds are associated with pharmaceutical compositions and pharmaceutically acceptable salt forms.
Claims Coverage
The provided claims include independent coverage for treatment of organophosphate exposure and for compounds selected from disclosed structure sets. Across the claims, the inventive coverage centers on administering a defined Formula (III) oxime scaffold with specific substituent constraints, including pharmaceutically acceptable salts, and on administering compounds selected from specified structures.
Treating an organophosphate-exposed subject with a Formula (III) oxime compound
A method of treating a subject who has been exposed to an organophosphate by administering a compound of Formula (III), or a pharmaceutically acceptable salt thereof, wherein X is a bond or SO2, R1 is selected from H, alkyl, aryl, and cycloalkyl, and R2 is aryl.
A Formula (III) compound specified as Formula (IV) with aryl R1
The method of treating an organophosphate-exposed subject is characterized in that the compound of Formula (III) is specifically a compound of Formula (IV), or a pharmaceutically acceptable salt thereof, where R1 is aryl.
R2 aryl ring bearing (R3)m substituents with constrained substituent set
The method further specifies a substituent group where R2 is defined by an aryl ring bearing (R3)m, with each R3 independently selected from nitro, cyano, halo, haloalkyl, or alkyl and m limited to 0–5.
A compound selected from specified structures and pharmaceutically acceptable salts
A compound having a structure selected from a set of structures, or a pharmaceutically acceptable salt thereof.
Treating an organophosphate-exposed subject with a compound selected from specified structures
A method of treating a subject who has been exposed to an organophosphate by administering a compound having a structure selected from a set of structures, or a pharmaceutically acceptable salt thereof.
The claim set covers organophosphate poisoning treatment methods defined by administration of Formula (III) oxime compounds with specified structural constraints on X, R1, and R2, including refinements specifying Formula (IV) with aryl R1 and constraining the (R3)m substituent pattern on the R2 aryl ring. It additionally includes composition coverage for compounds selected from disclosed structure sets and corresponding treatment methods using those selected compounds.
Stated Advantages
Oximes restore acetylcholinesterase (AChE) function by breaking the enzyme-organophosphate interaction.
In-silico binding and affinity results indicate improved reactivation and binding versus 2-PAM, HI-6, and atropine.
Documented Applications
Treating a subject exposed to an organophosphate, including chemical nerve agents such as sarin, soman, tabun, VX, and VX/Novichok-related agents, by administering an oxime compound to reactivate AChE.
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