Labile quaternary ammonium salts as prodrugs

Details Labile quaternary ammonium salts as prodrugs Labile quaternary ammonium salts as prodrugs

1978-11-22

1988-02-23

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546335, 546334, 546216, 546 79, 546197, 546315, 546221, 546281, 546127, 546238, 546156, 546225, 546224, 549 77, 549 74, 549 68, 560250, 560253, 560 1, 560187, 560226, 560229, 560122, 560123, 560124, 560228, 560110, 560 19, 560 74, 560 58, 558256, 544358, 544 42, 544178, 544 41, 540485, C07D21512, C07D21170, C07D33322, C07C 6702

Patent

active

047271515

ABSTRACT:
Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein N represents a tertiary aliphatic amine; wherein N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.1 cannot be a hydrogen atom; wherein X is --O-- or --S--; and wherein Y represents a member selected from the group consisting of a halogen atom or any other organic or inorganic monovalent equivalent anion; with the further proviso that N and N, respectively cannot represent trimethylamine and pyridine or quinoline when R represents a hydrogen atom and R.sub.1 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 and/or enzymatic hydrolysis. Upon chemical and/or enzymatic hydrolysis, these compounds will "cleave," thus releasing their active constituent or constituents, according to the following general scheme(s): ##STR2## In other words, the title compounds hydrolyze (chemically or enzymatically) releasing a tertiary amine or unsaturated amine derivative, an aldehyde, a carboxylic acid and a hydrogen halide (HX) per the above reaction scheme.

REFERENCES:
patent: 3873583 (1975-03-01), Walz et al.
Goodman et al., The Pharmacological Basis of Therapeutics, 6th Edition, MacMillan Publishing Co., Inc., New York, 1980, p. 28.

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