Abstract: 2-[4-(Polyhalo-2-hydroxy-2-propyl)anilino]-2-oxazolin-4-ones and the thiazolin-4-ones corresponding thereto, having useful anti-hypertensive properties, are disclosed herein. The compounds are prepared by reaction of the appropriate 4-(polyhalo-2-hydroxy-2-propyl)aniline with a .beta.-chloroethanoyl isocyanate or isothiocyanate and then cyclization of the resultant intermediate.

Abstract: Disclosed is an improved process for separating 5-[1-hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl]salicylamide into its two diastereoisomeric racemates; a process for converting either diastereoisomer into the other; and the use of one specified diastereoisomer as a superior antiarrhythmic agent.

Abstract: 1-benzhydryl-2-cyanoazetidine is a novel intermediate for the synthesis of N-diphenylalkyl-2-benzyl azacyclic compounds.

Abstract: 1,3,5(10),6,8,14-19 Nor-pregnahexaene-20-ones exhibit anti-mitotic activity with minimal or no hormonal activity. They are particularly useful in the treatment and control of psoriasis when applied topically, a preferred anti-psoriatic compound being 16.alpha.-methyl-1,3,5(10),6,8,14-19-nor-pregnahexaene-3,17.alpha.,21-trio l-20-one 21-acetate.

Abstract: The preparation of novel 2'-unsubstituted derivatives of 4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols, useful as antibacterial agents, is described.

Abstract: Novel macrocyclic (monocyclic and bicyclic) compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.

Abstract: Selective blocking of some amino groups in a polyamino organic compound having at least one pair of available neighboring hydroxyl and amino groups is effected by first preparing in situ transition metal salt complexes of available neighboring amino and hydroxyl group pairs in said polyamino organic compound, followed by introduction of blocking groups on the non-complexed amino groups and, finally, removing the transition metal cations from the selectively N-blocked polyamino organic compound complex to obtain a polyamino organic compound having selectively blocked amino groups.This process is particularly valuable when carrying out aminocyclitol-aminoglycoside transformations utilizing transition metal salt complexes of cupric acetate, nickel (II) acetate, cobalt (II) acetate or mixtures thereof.

Abstract: Novel 3,20-dioxo-7.alpha.-halogeno-1,4-pregnadienes are described and their use as anti-inflammatory agents. Preferred are 7.alpha.-bromo- and 7.alpha.-chloro- derivatives, particularly 7.alpha.-bromo- and 7.alpha.-chloro-1,4-pregnadienes-11.beta.,17.alpha.,21-triol-3,20-dione 17,21-dihydrocarboncarboxylates, the 16-methyl and 16-methylene derivatives thereof being particularly valuable as topical anti-inflammatory agents.

Abstract: This invention relates to the preparation of novel 1-epi-aminoglycosides, useful as antibacterial agents, and also relates to the process for the preparation of known as well as novel 1-N-substituted aminoglycoside antibacterial agents.

Abstract: Described are 3-oxo-7.alpha.-halogeno-17.alpha.-1,4-pregnadiene-21,17.beta.-carbolactone s and compounds related thereto, i.e. 2',3'.alpha.-tetrahydrofuran-2'-spiro-17(7.alpha.-halogeno-1,4-androstadie ne-3-ones) and (17R)-spiro-[7.alpha.-halogeno-1,4-androstadiene-17,1'-cyclobutane]-3,2'-d iones, all of which are valuable as aldosterone antagonists. Also described are the corresponding 7.beta.-hydroxy derivatives useful as intermediates.

Abstract: The process for removing a secondary hydroxyl group from an organic compound having at least one secondary hydroxyl group and having any amino groups protected, comprises the reaction of a reactive ester of said secondary hydroxyl group selected from the group consisting of an O-alkylthioester and an O-alkylselenoester with at least one mole of an organotin hydride, preferably tri-n-butylstannane, in an inert, aprotic solvent at a temperature of at least about 100.degree. C and under an inert atmosphere.The process is particularly useful in removing secondary alcohols in aminoglycoside antibiotics to produce deoxy derivatives thereof having antibacterial activity.Also described are novel O-sec.-alkylthiobenzoate, O-sec.-alkyl-S-methylxanthate, N-(sec.-alkoxythiocarbonyl)-imidazole esters, and di-O-alkylthiocarbonates having at least one secondary O-alkyl group, useful intermediates of the claimed process.

Abstract: 3-Oxo-6-unsubstituted-7.alpha.-halogeno-4-dehydro steroids, wherein said halogen is chlorine, bromine or iodine, are prepared by reaction of a 3-oxo-6,7-di-unsubstituted-4,6-bis-dehydro steroid with at least an equimolar quantity of the corresponding hydrogen halide in a non-reactive organic solvent at temperatures no higher than about 30.degree. C, and then are isolated by removal of said solvent and any excess acid at temperatures no higher than about 25.degree. C without subjecting said 3-oxo-6-unsubstituted-7.alpha.-halogeno-4-dehydro steroid to a basic medium.A preferred species of this process is that wherein the starting steroid is a 3,20-dioxo-9-unsubstituted-11-oxygenated-1,4,6-pregnatriene-17,21-diol or ester thereof, preferably a 17,21-di-lower alkanoate or a 17-benzoate 21-lower alkanoate ester thereof, whereby is prepared in good yields a 3,20-dioxo-7.alpha.-halogeno-1,4-pregnadiene-17.alpha.,21-diol or ester thereof, useful as topical anti-inflammatory agents.

Abstract: This invention relates to the preparation of novel 1-desamino-1-oxo-aminoglycosides and their use as intermediates in the preparation of novel 1-desamino-1-hydroxy and 1-desamino-1-epi-hydroxyaminoglycoside antibacterial agents.

Abstract: 1,2'-di-N-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols and 1,6'-di-N-alkyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols and their acid addition salts are valuable as antibacterial agents. Also disclosed are 2'-N-alkyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol antibacterial agents which are also useful as intermediates in the preparation of the 1,2'-di-N-alkyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols. Preferred compounds of this invention include 1,2'-di-N-ethylsisomicin and 1,6'-di-N-ethylsisomicin.

Abstract: 5-Deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols, useful antibacterial agents, are prepared by the reaction of the corresponding 5-O-thioformyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol having all amino functions and all primary and secondary hydroxyl groups protected, with an organotin hydride (preferably tri-n-butylstannane) in an inert aprotic solvent under an inert atmosphere at temperatures of at least about 100.degree. C, followed by removal of said hydroxyl and amino protecting groups.

Abstract: Described are 6'-N-alkyl derivatives of antibacterially active 4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols having a primary carbinamine at C-5' of which a preferred group are 6'-N-alkyl derivatives having 2 to 4 carbon atoms of 4-O-aminoglycosyl-6-O-garosaminyl-2-deoxystreptamines having a primary carbinamine at C-5', a particularly preferred compound being 6'-N-ethylsisomicin.The 6'-N-alkyl derivatives are prepared by the reaction of the corresponding 6'-N-unsubstituted aminoglycoside having protecting groups on all other amino functions with an aldehyde or a ketone, followed by the reaction in situ of the 6'-N-substituted intermediate thereby formed with a hydride reducing agent, then removal of any N-protecting groups.Pharmaceutical formulations comprising 6'-N-alkylaminoglycosides of the invention are described and the method for their use in treating bacterial infections.

Abstract: Everninomicin derivatives devoid of a nitro group and having antibacterial activity are prepared by electrochemically reducing the corresponding everninomicin having a nitro function or salts thereof in an aprotic anhydrous solvent in the absence of carbon dioxide. A preferred starting compound is everninomicin D whereby is produced a product mixture of antibacterial agents identified as desevernitrose everninomicin D, everninomicin D-3, and everninomicin D-7, respectively.

Abstract: 21-Halogeno-17.alpha.-acyloxy-20-keto-4-pregnenes having physiological properties are prepared by the reaction of a 17.alpha.,21-dihydroxy-20-keto-4-pregnene 17.alpha.,21-orthoester with a triphenylmethyl halide in an organic solvent, said halide being chloride or bromide.

Abstract: Aminoglycoside 66-40C, a minor product produced by the fermentation of Micromonospora inyoensis, is separated from said fermentation mixture, and is used as an intermediate in preparing the known antibiotic, sisomicin, as well as 6' -N-alkylsisomicins having antibacterial activity. Claimed are Aminoglycoside 66-40C as well as 6' -N-t-alkylsisomicins having a tertiary carbon bonded to the 6' -nitrogen.

Abstract: Everninomicin antibiotics having a nitro function, e.g. everninomicin B, everninomicin C, and everninomicin D, upon treatment with aluminum amalgam in aqueous alkanol are converted to a mixture of at least two reduction products having antibacterial activity, said reduction products being an everninomicin having a nitroso function and an everninomicin having a hydroxylamino function. The nitrosoeverninomicins are also prepared by treating the corresponding hydroxylaminoeverninomicin with an oxidizing reagent selected from the group consisting of aerial oxidation in alkaline solution, and an alkali metal hypobromite in an aprotic solvent. The everninomicin reduction products and salts thereof are described as well as nitrone derivatives of the hydroxylaminoeverninomicins and salts thereof, all of which possess antibacterial activity. A preferred compound is hydroxylaminoeverninomicin D, particularly the sodium salt thereof.