Sterling Drug Inc.

Alexander R Surrey

George Y Lesher

Joseph C Collins

Karl O Gelotte

N-(Dichloroacetyl)-N'-(mono- or di-chlorobenzoyl)-1,8-octanediamines (I), acetaldehyde dehydrogenase inhibitors, indicating their usefulness as aids in treating alcoholism, are prepared by reacting a mono-acid-addition salt of 1,8-ocetanediamine with one molar equivalent quantity of a lower-alkyl dichloroacetate to produce N-(dichloroacetyl)-1,8-octanediamine and then reacting it with a mono- or di-chlorobenzoylating agent to produce I. Also shown is the process of reacting a mono-acid-addition salt of 1,6-hexanediamine with one molar equivalent quantity of a lower-alkyl dichloroacetate to produce N-(dichloroacetyl)-1,6-hexanediamine.

N-(Dichloroacetyl) diamine compounds and process of preparing same

3-R-3-(Ac.sub.2 NH)-9-R'-9-(Ac.sub.1 NH)-1,5-dioxaspiro[5.5]undecane (I), where R and R' are each hydrogen or lower-alkyl, Ac.sub.1 is lower-alkanoyl or 4-Q.sub.1 -benzoyl and Ac.sub.2 is 4-Q.sub.2 -benzoyl where Q.sub.1 and Q.sub.2 each is lower-alkoxy or polyhalo-lower-alkoxy, are antifertility agents. The compounds are prepared by di-acylating 3-R-9-R'-1,5-dioxaspiro[5.5]undecan-3,9-diamine (II) or mono-acylating 9-(Ac.sub.1 NH)-3-R-9-R'-1,5-dioxaspiro[5.5]undecan-3-amine (IV). IV and II are prepared by oxidizing 4-(Ac.sub.1 NH)-4-R'-cyclohexanol (VI) to produce 4-(Ac.sub.1 NH)-4-R'-cyclohexanone (VII), reacting VII with 2-NO.sub.2 -2-R-1,3-propanediol to produce 3-R-3-NO.sub.2 -9-(Ac.sub.1 NH)-9-R'-1,5-dioxaspiro[5.5]undecane (VIII), reducing VIII to produce the corresponding 3-amine (IV) and hydrolyzing IV to the corresponding 3,9-diamine (II). Methods of preparing VI are shown.

4-[-(Alkoxy or polyhaloalkoxy)-benzamido]cyclohexanones

Alkylenediamine derivatives substituted on each nitrogen atom by 4-(4'-nitrophenoxy)benzyl or 4-(4'-aminophenoxy)benzyl, optionally substituted additionally on each nitrogen by lower-alkyl, phenylcarbamyl or dihaloacetyl and optionally interrupted in alkylene by cycloalkylene, phenylene, alkylated-phenylene, pyridylene, furylene and thiazolylene. The compounds, which have antibacterial activity, are prepared stepwise by reacting an alkylenediamine with two molar equivalents of 4-(4'-nitrophenoxy)benzaldehyde and reducing the resulting bis(benzal)alkanediamines.

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Albany, NY, United States of America

Alexander R Surrey