Labile quaternary ammonium salts as transient derivatives

C - Chemistry – Metallurgy – 07 – D

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260/474, 260/492

C07D 233/64 (2006.01) C07D 213/55 (2006.01) C07D 213/80 (2006.01) C07D 213/82 (2006.01) C07D 487/08 (2006.01) C07D 521/00 (2006.01)

Patent

CA 1045628

ABSTRACT OF THE DISCLOSURE Labile quaternary ammonium salts of the following formula (I) and (II) are provided: (I) Image (II) Image wherein Image represents a tertiary aliphatic amine; wherein Image represents an aro- matic amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C1-C8 open chain or cyclo alkyl group, a C1-C8 alkoxy- alkyl group, a C1-C8 acyloxyalkyl group, a C1-C8 haloalkyl group, a C1-C8 carboxyalkyl group, an aryl group, and a substituted aryl group, whose substi- tuents are selected from the group consisting of a halogen atom, and O-lower alkyl (C1-C4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R1 which may be the same of different, represents any member defined by R above with the proviso that R1 cannot be a hydrogen atom; and wherein X- represents a member selected from the group consisting of a halogen atom or any other equivalent anion; with the further proviso that Image and Image respec- tively cannot represent trimethylamine and pyri- dine or quinoline when R represents a hydrogen atom and R1 represents a methyl group or a phenyl group. The compounds described above are characterized by their extreme solubility and resistance to oxidation, dealkylation, and protonation prior to chemical an or enzymatic hydrolysis. Upon chemical and/or enzymatic hydrolysis, these com- pounds will "cleave," thus releasing their active constituent or constituents, according to the following general scheme(s): Image In other words, the title compounds hydrolyze (chemically or enzymatically) releasing a tertiary amine or aromatic amine derivative, and aldehyde, a carboxy- lic acid and a hydrogen halide (HX) per the above the reaction scheme.

229912

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