发明名称 Labile quaternary ammonium salts as prodrugs
摘要 Labile quaternary ammonium salts of the following formula (I) and (II) are provided: <IMAGE> (I) <IMAGE> (II) 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 C1-C8 open chain or cyclo alkyl group, a C1-C8 alkoxyalkyl group, a C1-C8 acyloxyalkyl group, a C1-C8 haloalkyl group, a C1-C8 carboxyalkyl group, a C2-C8 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 (C1-C4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R1 which may be the same or different, represents any member defined by R above with the proviso that R1 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 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 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): <IMAGE> +TR <IMAGE> <IMAGE> +TR <IMAGE> 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.
申请公布号 US4727151(A) 申请公布日期 1988.02.23
申请号 US19780962948 申请日期 1978.11.22
申请人 INTERX RESEARCH CORPORATION 发明人 BODOR, NICOLAE S.
分类号 C07D213/80;C07D213/82;C07D487/08;C07D521/00;(IPC1-7):C07D215/12;C07D211/70;C07D333/22;C07C67/02 主分类号 C07D213/80
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