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1. WO2020117525 - SYNTHÈSE D'ANTIDOTES À ACTION ANTINEUROTOXIQUE À BASE D'OXIME

Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

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Claims:

1. A method of forming bis-quaternary pyridinium oximes comprising:

supplying benzoic anhydride having the following structure:


reacting said benzoic anhydride with trioxane to form a dibenzoyloxymethyl ether having the following structure:


supplying a substituted pyridine having the following structure:


wherein Ri and R2 may be independently selected from the group consisting of consisting of hydrogen, alkyl, -CH=NOH or -CONH2;

combining said dibenzoyloxymethyl ether with said substituted pyridine and forming a salt having the following structure:


reacting said salt with a substituted pyridine having the following structure:


and forming a bis-pyridinium aldoxime salt of the following structure:


wherein R3 and R4 may be independently selected from the group consisting of consisting of hydrogen, alkyl, -CH=NOH or -CONH2 and X comprises Cl- or OSO2CH3.

2. The method of claim 1 wherein Ri is hydrogen, R2 is -CH=NOH, and R3 and R4 are both -CH=NOH, and X is OSO2CH3.

3. The method of claim 1 wherein Ri= -CH=NOH, R2 is hydrogen, R3 is hydrogen and R4 is -CH=NOH, and X is OSO2CH3.

4. The method of claim 1 wherein Ri and R3 are hydrogen, and R2 and R4 are - CH=NOH, and X is OSO2CH3.

5. The method of claim 1 wherein said benzoic anhydride contains one or more of an electron withdrawing group (EWG) on the aromatic rings according to the following structure:


6. The method of claim 5 wherein said EWG is selected from the group consisting of an organic trihalide, sulfonate, a nitro group, an ammonium group, an aldehyde, a ketone, carboxylic acid, acyl chloride, benzoate esters, amide group, or a halide.

7. The method of claim 1 wherein said bis-pyridinium aldoxime salt:


is dispersed in a pharmaceutically acceptable carrier to therapeutically treat intoxication of a phosphorous containing cholinesterase inhibitor by a person or animal.

8. A therapeutic method of treating a person or animal for intoxication with a phosphorous containing cholinesterase inhibitor, comprising administering to a person or animal a bis-pyridinium aldoxime salt formed by the following method:

supplying benzoic anhydride having the following structure:


reacting said benzoic anhydride with trioxane to form a dibenzoyloxymethyl ether having the following structure:


supplying a substituted pyridine having the following structure:


wherein Ri and R2 may be independently selected from the group consisting of consisting of hydrogen, alkyl, -CH=NOH or -CONH2;

combining said dibenzoyloxymethyl ether with said substituted pyridine and forming a salt having the following structure:


reacting said salt with a substituted pyridine having the following structure:


and forming a bis-pyridinium aldoxime salt of the following structure:


wherein R3 and R4 may be independently selected from the group consisting of consisting of hydrogen, alkyl, -CH=NOH or -CONH2 and X comprises Cl- or OSO2CH3.