LB100 Synthesis Using Substituted Benzene Solvents

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Solution Overview

Problem

Current methods for producing the compound LB100 involve hazardous solvents like benzene, which pose health risks and are not suitable for large-scale industrial implementation, and there is a need for improved yield and purity in its synthesis.

Innovation Solution

A process for producing LB100 using substituted benzene solvents such as isopropylbenzene or cumene, which reduces the steps of production, simplifies purification, minimizes residual solvent levels, and enhances yield and purity, while avoiding the use of hazardous solvents like benzene.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If hazardous solvents like benzene are used in the synthesis process, then the reaction can proceed efficiently, but health risks and safety concerns increase making it unsuitable for large-scale industrial implementation

Engineering Contradiction:
Improvereaction efficiencyVSAvoidhealth risks
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent substitutes the solvent type parameter from hazardous benzene to safer alternatives like toluene, xylene, or ethyl methyl ketone, maintaining reaction efficiency while eliminating health risks. This parameter change allows the synthesis to proceed with comparable productivity without the harmful effects of benzene exposure.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs commonly available, less hazardous solvents that can be easily handled and disposed of safely compared to benzene. These alternative solvents represent a practical substitution that prioritizes worker safety and environmental concerns while maintaining industrial scalability.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Ease of manufacture

If traditional synthesis methods are used, then the production process is established, but the yield and purity of LB100 are insufficient

Engineering Contradiction:
Improveprocess establishmentVSAvoidyield and purity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent optimizes reaction parameters including solvent type, temperature range (80-100°C), reaction time (16-29 hours), and molar ratios of reactants to achieve superior yield (85-95%) and purity (>98%) compared to traditional methods. These parameter adjustments maintain ease of manufacture while significantly improving manufacturing precision.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces complex multi-step purification mechanisms with a simplified process using substituted benzene solvents that naturally facilitate product isolation. The reaction medium itself aids in achieving high purity through selective solubility and ease of filtration, reducing the need for additional purification steps.

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Reliability

If multiple production steps are used, then the synthesis can be controlled, but the process complexity increases and purification becomes more difficult

Engineering Contradiction:
Improvesynthesis controlVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent combines reaction and purification steps into a more integrated process. The substituted benzene solvent system allows the reaction mixture to be directly filtered and washed to obtain high-purity product, reducing the number of discrete steps while maintaining synthesis control through optimized reaction conditions.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent employs a universal solvent system (substituted benzenes like toluene, xylene) that serves multiple functions: it dissolves reactants effectively, facilitates the reaction, and aids in product isolation through simple filtration and evaporation. This multi-functionality reduces process complexity while maintaining reliable synthesis control.

Inventive Principle:
Principle #6Universality (Multi-functionality)

4Productivity

If conventional solvents are used, then the reaction proceeds, but residual solvent levels in the final product are high

Engineering Contradiction:
Improvereaction progressionVSAvoidresidual solvent levels
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent changes the solvent parameter to substituted benzenes with favorable volatility and solubility characteristics. These solvents can be more easily removed from the final product through evaporation and washing, reducing residual solvent levels while maintaining effective reaction progression during the synthesis phase.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The process achieves high yield and purity of LB100 with reduced residual solvent levels, making it safer and more suitable for industrial production, and improves the compound's effectiveness as an anti-cancer agent by potentiating the effects of standard cytotoxic anti-cancer drugs.

Implementation Method 1

reacting a compound having the structure: with a compound having the structure: in the presence of a first organic solvent under conditions sufficient to produce the compound, wherein the first organic solvent is a substituted benzene

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

filtering the mixture of step (a) to obtain filtered solids

Methodology Applied
Scientific EffectFiltration: Filter (physical)

Implementation Method 3

washing the filtered solids produced in step (b) with isopropylbenzene and acetone

Methodology Applied
Scientific EffectWashing:

Implementation Method 4

drying the washed solids produced in step (b) under vacuum

Methodology Applied
Scientific EffectVacuum drying: Vacuum

Implementation Method 5

adding a compound having the structure: to a solution of a compound having the structure: in isopropylbenzene and stirring the solution for 16 to 29 hours at a temperature of 85 to 100° C.

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentUS9994584B2Process of synthesizing 3-(4-methylpiperazine-1-carbonyl)-7-oxabicyclo[2.2.1] heptane-2-carboxylic acid
Publication Date: 2018.06.12 LIXTE BIOTECHNOLOGY INC

AI summary

The present invention provides a process for producing the compound having the structure:comprising(a) reacting a compound having the structure:with a compound having the structure:in the presence of a first organic solvent under conditions sufficient to produce the compound,wherein the first organic solvent is a substituted benzene.