Abstract: N-Acetyl-para-aminophenyl N'-acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenyl. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.

Abstract: An improved method of preparing 3-(4-pyridinyl)-2-cyclohexen-1-one oxime from ethyl 5-oxo-2-[(4-pyridinyl)-carbonyl]hexanoate is a one pot sequence which comprises first heating ethyl 5-oxo-2-[(4-pyridinyl)carbonyl]hexanoate with excess sulfuric acid, neutralizing the excess acid, extracting the resulting 3-(4-pyridinyl)-2-cyclohexen-1-one with isopropyl alcohol, draining off the heavier aqueous layer, adding hydroxylamine hydrochloride to the isopropyl alcohol solution of said 2-cyclohexen-1-one, stirring the mixture at reflux, basifying the mixture and evaporating it to dryness, and isolating 3-(4-pyridinyl)-2-cyclohexen-1-one oxime from the residue. The oxime is an intermediate for preparing 3-(4-pyridinyl)aniline, in turn, an intermediate for preparing rosoxacin, an antibacterial agent.

Abstract: Compounds useful as cardiotonic agents are 1-R-3-Q-5-PY-2(1H)-pyridinones (I) where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, Q is amino (preferred), lower-alkylamino, di-(lower-alkyl)amino or NHAc, Ac is lower-alkanoyl or lower-carbalkoxy, and PY is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents. The corresponding compounds where Q is nitro, carbamyl, cyano, halo or hydrogen are useful as intermediates and those where Q is hydrogen or cyano also are useful as cardiotonic agents. Said compounds are prepared: by reacting .alpha.-PY-.beta.-(R.sub.1 R.sub.2 N)acrolein (II) with malonamide to produce 1,2-dihydro-2-oxo-5-PY-nicotinamide (Ia) and reacting Ia with a reagent capable of converting carbamyl to amino to produce 3-amino-5-PY-2(1H)-pyridinone (Ib); by reacting II or .alpha.-PY-malonaldehyde (II') with .alpha.

Abstract: 3-(Hydroxy or hydroxymethyl)-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof is useful as a cardiotonic agent. 3-Hydroxy-5-(4-pyridinyl)-2(1H)-pyridinone is prepared by autoclaving a mixture of an alkali lower-alkoxide, loweralkanol and 3-halo-5-(4-pyridinyl)-2(1H)-pyridinone and acidifying the cooled reaction mixture. 3-Hydroxymethyl-5-(4-pyridinyl)-2(1H)-pyridinone is prepared by reacting 5-(4-pyridinyl)-2(1H)-pyridinone with excess formaldehyde at an acidic pH. Said 3-(hydroxy or hydroxymethyl)-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically-acceptable acid-addition salt thereof is disclosed as the active ingredient in cardiotonic compositions for increasing cardiac contractility and in the method for increasing cardiac contractility in a patient requiring such treatment.

Abstract: A process for preparing 1,2-dihydro-2-oxo-5-(pyridinyl) nicotinonitriles by reacting .alpha.-(pyridinyl)-.beta.-[di-(lower-alkyl)amino]acrolein with malononitrile in a lower-alkanol. The products are useful as cardiotonic agents and, also, as intermediates for preparing corresponding 3-amino-5-(pyridinyl-2(1H)-pyridinones, in turn, useful as cardiotonic agents.

Abstract: N-{3- and 4-[R.sub.1 -(phenyl)-C(.dbd.X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 3- or 4-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3- or 4-lithiophenyl-lower-alkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)-lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.

Abstract: 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '''-11(ax)-R.sub.3 -11(eq)-[CH.sub.2 CH.sub.2 CO(CH.sub.2).sub.n -(2- and 3-furyl)]-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared either by heating, with formic acid in an organic solvent or with certain ammonium formates, certain lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '''-3-[CO(CH.sub.2).sub.n -(2- and 3-furyl]-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carb oxylates or by reaction of a lower-alkyl .beta.-[3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '''-11(ax)-R.sub.3 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11(eq)-yl]propionate with 2- or 3-furylacetic acid in the presence of a strong base.

Abstract: 1:1 and 1:2 molar salts of 1,2-ethanediamine and nalidixic acid are prepared by reacting 1,2-ethanediamine with one or two molar equivalents of nalidixic acid. Also shown are aqueous solutions of the 1:1 equimolar salt and their preparation from the corresponding 1:2 molar salt.

Abstract: 4,5-Dihalopyrrol-2-yl oxyphenyl ketones, prepared either by Friedel-Crafts condensation of a 4,5-dihalopyrrole-2-carboxylic acid halide with an appropriate hydroxy or lower-alkoxy-substituted benzene or by condensation of a hydroxy or lower-alkoxy-substituted benzaldehyde with pyrrole in the presence of sodium hydride followed by halogenation, with elemental chlorine or bromine, of the resulting pyrrol-2-yl oxyphenyl ketone, useful as antibacterial and antifungal agents.

Abstract: Phytoresponsive and antimicrobial compositions containing, as the active ingredient, a 4,5-dihalopyrrole-2-carbonitrile and methods of combatting microorganisms and plant growth comprising applying an effective antimicrobial or phytotoxic quantity of the active ingredient to a surface to be disinfected or to undesirable plant growth.

Abstract: Aminocyclitol antibiotics of the streptamine, deoxystreptamine or dideoxystreptamine type are prepared by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and a non-nitrogen containing cyclitol with a mutant of an aminocyclitol antibiotic producing organism.

Abstract: Aminocyclitol analogs of gentamicin C.sub.1, C.sub.2 and C.sub.1a and the corresponding compounds acylated on the 1-, 3- and 2'-amino groups with an .omega.-amino-.alpha.-hydroxy-lower-alkanoyl group are prepared by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and an added aminocyclitol with a mutant of Micromonospora purpurea and acylating the product with an ester of an .omega.-(N-benzyloxycarbonyl)amino-.alpha.-hydroxy-lower-alkanoic acid followed by catalytic hydrogenolysis of the benzyloxycarbonyl group.

Abstract: Phenyl-lower-alkylamines having anti-inflammatory activity are prepared either by reductive alkylation of an amine with a phenyl-lower-alkanaldehyde; by condensation of a phenyl-lower-alkanaldehyde with a secondary amine, conversion of the resulting phenylvinylamine to the corresponding iminium salt, and reduction of the latter with an alkali metal borohydride; or by reaction of a phenyl-lower-alkanoyl halide with an amine and reduction of the resulting amide with a reagent effective to reduce an amide to an amine.

Abstract: 4,5-Dihalopyrrole-2-carboxamide derivatives, prepared by reaction of a corresponding 4,5-dihalopyrrole-2-carboxylic acid halide or a corresponding 4,5-dihalopyrrol-2-yl trihalomethyl ketone with an appropriate amine, have antibacterial and herbicidal activities.

Abstract: 4,5-Dihalopyrrol-2-yl di- and trihalomethyl ketones, prepared by reaction of pyrrole with a di- or trihaloacetyl halide or with a di- or trihaloacetic anhydride and halogenation of the resulting pyrrol-2-yl di- or trihalomethyl ketone, useful as antibacterial, herbicidal and insecticidal agents.

Abstract: Phytoresponsive and antimicrobial compositions containing, as the active ingredient, a 4,5-dihalopyrrole-2-carbonitrile and methods of combatting microorganisms and plant growth comprising applying an effective antimicrobial or phytotoxic quantity of the active ingredient to a surface to be disinfected or to undesirable plant growth.