Sterling Drug Inc.

Andrew W Zalay

Malcolm R Bell

Karl O Gelotte

George Y Lesher

Compounds useful as antibacterial agents are 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylic acids (I), wherein: (a) BN is dimethylamino where R is methyl, ethyl, n-propyl, n-butyl, n-pentyl or n-octyl; (b) BN is diethylamino where R is n-propyl; or, (c) BN is 4-methyl-1-piperazinyl where R is ethyl. These compounds are prepared by reacting lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) with a mineral acid and an alkali nitrite in aqueous medium to produce the corresponding diazonium salt of said 7-aminoquinoline, reacting said diazonium salt with an amine of the formula BNH in the presence of an acid-acceptor to produce lower-alkyl 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylate and hydrolyzing said 3-quinolinecarboxylate to produce the corresponding 3-carboxylic acid (I). The intermediate lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) are prepared in several steps by conventional means starting with m-aniline.

1-Alkyl-1,4-dihydro-4-oxo-7-triazenyl-3-quinolinecarboxylic acids

3-(4- OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.

Preparation of 3-(pyridinyl)-2-cyclohexene-1-ones

3-(4- OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)-pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.

Preparation of 3-(pyridinyl)-2-cyclohexen-1-ones

Conversion of 3-(pyridinyl)-2-cyclohexen-1-one to 3-(pyridinyl)anilines

3-(4 OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)-pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.

3-(Pyridinyl)-2-cyclohexen-1-ones

This invention relates to novel 1-[4-(R.sub.1 R.sub.2 N-C.sub.n H.sub.2n -O)phenyl]-5-R.sub.4 -2-(4-R.sub.3 -phenyl)indoles having antifertility and hypocholesterolemic activities and to novel intermediates for their preparation.

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Albany, NY, United States of America

Andrew W Zalay