Abstract: A process for producing optically active 16-substituted prostaglandins and new 16-substituted prostaglandins produced thereby which are useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy.

Abstract: The stereospecific alkylation of a novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described using a range of lithium-, copper or magnesium-containing organometallic reagents. This reaction provides a 5-endo-protected hydroxyl-bicyclo[2,2,1]-heptan-2-one system from which prostaglandin compounds of the F series having a protecting group at the 9-position hydroxyl group may readily be obtained by a sequence of reactions.

Abstract: A catalyst comprising a uranium compound, an alkali metal ion, and a halide, is effective to convert conjugated dienes in carboxylic acid media to diacyloxy olefins.

Abstract: C-homoestratrienes of the formula ##STR1## wherein ##STR2## R.sub.1 and R.sub.2 are the same or different, and each is hydrogen, acyl, alkyl, cycloalkyl or tetrahydropyranyl; andR.sub.3 is hydrogen, ethynyl or chloroethynyl; possess very good estrogenic properties.

Abstract: This invention relates to pharmacologically active compounds of the formula: ##STR1## wherein Z is trans--CH.dbd.CH, C.tbd.C; or CH.sub.2 --CH.sub.2 ;M is H or lower alkyl;n is an integer of from 2 to 5;X is alkyl;W is H or OR, wherein R is H, acyl, or alkyl;each Y is H, OH or alkoxy;and to novel intermediates and processes useful in the production thereof.

Abstract: Phenolic age resistors such as 4-(3,5-ditertiary butyl-4-hydroxyphenyl)-2-butyl 2-methyl-4-thia-6-octanoyloxyhexanoate are used as antioxidants in diene rubbers, such as butadiene-styrene types and in polyolefins, such as polypropylene.

Abstract: Halobenzenes are manufactured by (a) a one-vessel reaction of anilines with halogenating agents to give haloanilines, followed by reaction of the mixture thus obtained with alkanols and nitrosylating agents in the presence of water and acid at not less than 35.degree. C. or (b) the corresponding reaction of a haloaniline which has been manufactured in the above manner or by some other method and has been isolated from its reaction mixture. The products are starting materials for the manufacture of drugs, dyes and pesticides.

Abstract: Cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a carboxylic acyl group, R.sup.2 represents hydrogen or alkyl of 1 through 12 carbon atoms, and n represents an integer from 4 through 8, are new compounds possessing pharmacological properties, more particularly the production of hypertension and inhibition of gastric acid secretion. They are also useful in the preparation of 10-hydroxyprostaglandins.

Abstract: A catalyst comprising a titanium compound, an alkali metal ion, and a halide, is effective for the conversion of conjugated diolefins to diacyloxy olefins.

Abstract: Conjugated dienes or monoolefins are converted to diesters in a process utilizing a catalyst system comprising an alkali metal compound and a sulfur source comprising elemental sulfur or a sulfur halide, optionally with a halide source, in carboxylic acid media.

Abstract: Disclosed is an improved process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS -hydroxy-cyclopent-2-enone corresponding to the formula ##STR1## wherein m is an integer from 2 to 4. The compounds prepared by this process are useful as precursors in the preparation of carbinol PGE.sub.1 analogues having utility as bronchodilators and inhibitors of gastric secretion.

Abstract: A plant protecting composition with pesticidal effects contains an effective amount of at least one compound of the formula ##STR1## wherein R is a C.sub.1-20 alkyl group or a phenyl or phenyl-C.sub.1-3 alkylene group having optionally one or more C.sub.1-3 alkyl or halogen substituents on the phenyl ring, and a diluent in an amount necessary to make up the final weight of the composition. To kill plant pests, the composition is applied to growing plants either prior to or after emergence.

Abstract: 1-Azolyl-4-hydroxy-1-phenoxy-butane derivatives of the formula ##STR1## in which R is hydrogen, --CO--R.sup.1 or --SO.sub.2 --R.sup.2,R.sup.1 is cycloalkyl, alkylamino, dialkylamino, alkenyl, alkynyl, or optionally substituted alkyl, phenyl, phenoxyalkyl, phenylalkyl or phenylamino,R.sup.2 is alkyl or optionally substituted phenyl,A is --CO--or CH(OH),X is H or --OR,X.sup.1 is alkyl or optionally substituted phenyl,Y is CH or N,Z is halogen, alkyl, halogenoalkyl, cycloalkyl, alkoxy, alkylthio, alkoxycarbonyl, amino, cyano, nitro, or optionally substituted phenyl, phenoxy or phenylalkyl, andN is 0, 1, 2, 3, 4 or 5,Or a salt thereof, which possess fungicidal and bactericidal properties.

Abstract: Propanoic acid derivatives of the formula: ##STR1## where R.sup.1 is a C.sub.1-8 alkyl group optionally substituted by hydroxyl or --COOH and R.sup.2 is hydrogen or a protecting group, are useful as anti-thrombotic agents.

Abstract: This invention relates to the preparation of optically active d-2-aminobutanol by catalytic asymmetric reduction of appropriate dehydro precursors to produce selectively the desired isomer. The same substrates can also be used to prepare the dl-mixture using optically inactive catalysts. The novel substituted-4-ethyl-4-oxazolin-2-one and substituted-4-ethyl-2-oxazolidinone compounds of this invention are useful as intermediates in the production of the antituberculosis drug ethambutol (Myambutol.RTM.).

Abstract: Novel mesomorphic substances, constituting, in certain temperature ranges, nematic or smectic liquid crystals, are compounds of the formula ##STR1## wherein Y is H or CN;R is alkyl or alkoxy of 1 to 10 carbon atoms;R' is alkyl of 1 to 10 carbon atoms or ##STR2## and X is Br, Cl or CN.

Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.

Abstract: The preparation of (.+-.)-9-[.alpha.-(2.alpha.,3.beta.-dihydroxy-4.alpha.-(hydroxymethyl) cyclopentyl)]-6-substituted purines: ##STR1## and (.+-.)-3-[.alpha.-(2.alpha., 3.beta.-dihydroxy-4.alpha.-(hydroxymethyl)cyclopentyl)]-7-substituted-v-tr iazolo[4,5d]pyrimidines: ##STR2## and their derivatives wherein R is amino, mercapto, methylmercapto, hydroxy, halogen, or substituted amino: ##STR3## wherein R' and R" may be the same or different and are of hydrogen, methyl, ethyl, propyl or phenyl. The preparation of the single intermediate from which either of these series of compounds may be synthesized is also disclosed. The compounds exhibit antiviral and antitumor activity.

Abstract: Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-.alpha.-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.

Abstract: Enamides are prepared by hydrogenating oximes having at least one hydrogen atom at the .alpha.-position in the presence of a carboxylic anhydride using a ruthenium catalyst. These enamides are important to obtain amino group-containing compounds by reduction or polymerization.

Abstract: A carboxylic acid, such as acetic acid, is prepared from a hydrocarbyl alcohol, such as methanol, in carbonylation processes comprising the use of an iodide, carbon monoxide and a nickel catalyst in the presence of a tin promoter.

Abstract: Novel optically active compounds of 4-protected hydroxy-cyclopent-2-en-1-ones of the formula ##STR1## wherein R is a splittable protective group for an alcoholic hydroxyl group, and a process for preparing the 4-protected hydroxycyclopent-2-en-1-ones by oxidizing monohydroxy-protected derivatives of cyclopent-1-ene-3,5-diol expressed by the following formula ##STR2## wherein R is the same as defined above. Optically active 4-hydroxycyclopent-2-en-1-one which is an optically active isomer of the compound of formula (2); or optically active cyclopent-1-en-3,5-diol (R-isomer) and a novel diacyl derivative of the diol, a novel monoacylmonosilyl-derivative of the diol and a novel monoacylmonotetrahydropyranol-derivative of the diol, which are intermediates for the protective derivative of formula (1). Processes are also provided for preparing the protective derivatives of formula (1) by converting these intermediates by esterification, hydrolysis, enzymatic processes, etc.

Abstract: Compounds of the formula ##STR1## wherein R is hydrogen, ##STR2## R.sub.1 and R.sub.2 are independently selected from hydrogen, lower alkyl, and cycloalkyl or R.sub.1 and R.sub.2 taken together with the nitrogen atom to which they are attached form a ring of the formula ##STR3## N IS 0 OR AN INTEGER FROM 1 TO 3; M IS AN INTEGER FROM 1 TO 3; R.sub.3 and R.sub.4 are independently selected from hydrogen and lower alkyl; X is hydrogen, halogen, lower alkyl, lower alkoxy, or nitro; and their salts; are disclosed. These compounds possess useful antiinflammatory properties.

Abstract: The present invention relates to novel 9-deoxy-9-methylene-p-substituted phenyl esters. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding 9-deoxy-9-methylene-PGF-type acids.

Abstract: A process for the preparation of a substituted 1-phenyl-2,2,2-trihalo-ethanol ester of the formula ##STR1## in which R is alkyl, halogenoalkyl, alkoxy, cycloalkyl or optionally substituted phenyl, benzyl, phenoxy, or phenylsulfonyl,X is halogenoalkyl with 1-3 carbon atoms and 1-3 halogen atoms,Y is halogen, cyano, nitro, alkyl, alkoxy, alkylmercapto, sulfoalkoxy or optionally substituted methylenedioxy, andn is an integer from 0 to 3,Comprising reacting a compound of the formula ##STR2## WITH A HALOGENATED ALDEHYDE OF THE FORMULAX CHOin the presence of a Friedel-Crafts catalyst at a temperature of about -70 to +100.degree. C thereby to form a complex alcoholate, and reacting the complex alcoholate with an acid halide of the formula ##STR3## OR WITH A CORRESPONDING ACID ANHYDRIDE AT A TEMPERATURE OF ABOUT -70 TO +100.degree. C.

Abstract: An asymmetric synthesis of optically active prostaglandin F.sub.2.alpha. from cyclopentadiene including intermediates in this synthesis.

Abstract: A process for the synthesis of perfume products, Vitamin E and intermediates described herein involving a coupling reaction. For instance, a process for the synthesis of dehydrophytol and Vitamin E comprising forming a C.sub.15 acetylene from hexahydropseudoionone and then coupling said acetylene with 1-acetoxy-4-chloro-3-methylbut-2-ene to form a C.sub.20 acetoxy-enyne. The latter is readily subjected to partial hydrogenation and saponification in that order to form a dehydrophytol, a useful intermediate for the synthesis of Vitamin E and other products.

Abstract: Fungus and mold growth in crops and organic matter are inhibited by the use of bis-carboxylic acid esters and compositions thereof. In a preferred embodiment, crops and animal feedstuffs are preserved during storage by applying a microbiocidal amount of a mono-, di or trioxymethylene, or lower alkylidene bis-alkanoate, or a mixture thereof.

Abstract: Carboxylic acids may be esterified by reaction with esters in the presence of a catalytic amount of a tin halide catalyst, the reaction being effected at temperatures ranging from about 0.degree. to about 150.degree. C.

Abstract: A process for producing optically active 16-substituted prostaglandins and new 16-substituted prostaglandins produced thereby which are useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy.

Abstract: Prostaglandin analogues of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, R.sup.1 represents a straight- or branched-chain alkyl group containing from 4 to 10 carbon atoms, and R.sup.2 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms and cyclodextrin clathrates of such acids and esters and, when R.sup.2 represents a hydrogen atom, non-toxic salts thereof, the bonds attaching the epidithio radical to the carbon atoms in the 9- and 11-positions in the grouping of formula VA being either botn in .alpha.-configuration or both in .beta.-configuration are disclosed.These compounds exhibit characteristic prostaglandin properties.

Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.

Abstract: This invention provides intermediates which are essential for a new chemical method which converts terrein, a fungal metabolite, to an intermediate which is known to be useful for the preparation of prostaglandins of the C series and analogs of other prostaglandins.

Abstract: The invention provides 3-(2-formyl-3-hydroxy-5-oxocyclopent-1-enyl)-p ropanoic acid and derivatives thereof having anti-thrombotic activity coupled with low toxicity. Also provided is a method for preparing such compounds by subjecting a 3-[3-hydroxy-5-oxo-2-(.beta.-styryl)cyclopent-1-enyl]-propanoic acid or derivative thereof to oxidative cleavage.

Abstract: A conjugated diolefin is reacted with a carboxylic acid, a carboxylic acid anhydride, or a mixture thereof, in the presence of oxygen and a catalyst comprising a compound of bismuth, an alkali metal compound and a source of nitrate ion.

Abstract: .omega.-TRISNORPROSTAGLANDINS HAVING AT THE 17-POSITION TWO HYDROGEN ATOMS AND ONE SUBSTITUENT OF THE FORMULA:(CH.sub.2).sub.n --O--(CH.sub.2).sub.m CH.sub.3wherein n is an integer of from 0 to 1, m is an integer of from 0 to 4; and having at the 15-position one hydrogen substituent or alkyl substituent of from 1 to 3 carbon atoms. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins, but exhibit a greater tissue specificity of action.

Abstract: A conjugated diolefin is reacted with at least one compound selected from the group consisting of a carboxylic acid and a carboxylic acid anhydride in the presence of oxygen and a catalyst comprising a rare earth metal compound, an alkali metal compound and a halide compound.

Abstract: This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.

Abstract: Cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a carboxylic acyl group, and either (I) R.sup.2 represents a group of the formula:--CR.sup.3 R.sup.4 R.sup.5 II(wherein R.sup.3 and R.sup.4 represent hydrogen or alkyl, and R.sup.5 represents hydrogen, or alkyl, alkoxy, cycloalkyl or adamantyl, or R.sup.5 represents alkyl substituted by alkoxy, or by cycloalkyl or by adamantyl, or the group --CR.sup.3 R.sup.4 R.sup.5 together forms a cycloalkyl or adamantyl group), X represents trans-vinylene or ethylene and Y represents carbonyl or a group of the formula: ##STR2## wherein R.sup.6 represents hydrogen or alkyl, and R.sup.7 represents hydrogen or a carboxylic acyl group, or else(ii) R.sup.2 represents a group of the formula:--A-Z-R.sup.8 IV(wherein A represents alkylene, Z represents a direct bond or oxygen or sulphur, and R.sup.

Abstract: Olefins may be esterified by reaction with esters of saturated alcohols containing at least two carbon atoms in the presence of a catalytic amount of a tin halide catalyst, the reaction being effected at temperatures ranging from about 0.degree. to about 150.degree. C.

Abstract: This invention relates to the utility of compounds having the general formula ##STR1## WHEREIN R is selected from the group consisting of --H, --CH.sub.3, ##STR2## Said compounds are useful as plant growth regulators.

Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.

Abstract: The compounds of the invention have the formula ##STR1## wherein Y is a radical of the formula ##STR2## or of the formula ##STR3## WHEREIN (CH.sub.2) is a straight or branched chain alkyl radical, n is 1-6, m is 0 or 1 and R.sup.5 and R.sup.6 may be the same or different and may be hydrogen, alkyl, arylalkyl, and R.sup.5', R.sup.5 and R.sup.6 may be the same or different and may be the nitrogen to which they are attached may be pyrrolidino, piperidino or N'-alkyl piperazino;R.sup.1, r.sup.2, r.sup.3 or R.sup.4 may be the same or different and may be hydrogen; alkyl, trifluoromethyl; alkanoyl; haloalkanoyl; alkoxycarbonyl of the formula ##STR4## wherein R is an alkyl radical; alkoxyalkyl; aminoalkanoyl of the formula ##STR5## wherein R.sup.5 and R.sup.6 are as previously defined and p is 0-3; 2-, 3-, or 4-pyridylcarbonyl; phenyl; monosubstituted phenyl wherein the substituent is alkyl, alkoxy, hydroxy, nitro, amino, or dialkylamino; alkenoyl; or aroyl; radical of 1-6 carbon atoms;R.sup.7 and R.sup.

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: The present invention relates to new cyclopentane derivatives having the formula ##STR1## and to a process for their manufacture. The compounds can be used as medicaments due to their antiprostaglandin effect.

Abstract: The compounds 2-Aryl-3-amino-1-butanol derivatives of the formula ##STR1## wherein R represents hydrogen or acyl; R.sup.1 and R.sup.2 each independently represents hydrogen, phenyl lower alkyl, or lower alkoxy substituted phenyl lower alkyl, or both R.sup.1 and R.sup.2 are lower alkyl; and their pharmaceutically acceptable acid salts.The compounds are crystalline solids or liquids which, having two asymmetry centers, can be obtained in their stereoisomeric forms as racemic mixtures or in their optically active forms. The compounds have cardiovascular activity as coronary dilators.The compounds can be prepared by reacting an .alpha.-arylcrotonate with ammonia or with an amine followed by hydrogenation of the carbalkoxy group to give the corresponding butanol. The butanols are acylated in usual ways to give the compounds of formula (I) wherein R represents an acyl group.

Abstract: Optically active and racemic prostaglandin derivatives of the formula ##STR1## wherein R.sub.1 is --OR.sub.5 ; --NHSO.sub.2 CH.sub.3 ; or --O--CH.sub.2 --U--V; R.sub.5 is hydrogen, alkyl, aryl, or a heterocyclic group; U is a direct bond, carbonyl or carbonyloxy; and V is phenyl substituted by 1-3 phenyl, alkoxy of 1-2 carbon atoms, or halogen, preferably bromine;R.sub.2 is hydrogen or alkyl of 1-5 carbon atoms;R.sub.3 is alkyl, substituted or unsubstituted cycloalkyl, straight-chain or branched alkyl of 1-5 carbon atoms substituted by aryl or substituted aryl, when R.sub.1 is as above; or R.sub.3 is aryl or substituted aryl group when R.sub.1 is --OR.sub.5 ', --NHSO.sub.2 CH.sub.3, or --O--CH.sub.2 --U--V and R.sub.5 ' is aryl or a heterocyclic group and U and V are as above;R.sub.4 is hydrogen or an ether or acyl residue;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH--;D is a direct bond, oxygen, or sulfur;Z is carbonyl or >CH OR.sub.4 wherein OR.sub.

Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.

Abstract: Certain allylmercaptans, some of which are novel, can be used to make novel flavorant and fragrance compositions. A novel method for making the allylmercaptans is disclosed.

Abstract: A method for stereospecifically preparing chiral 2-substituted-4-hydroxy-2-cyclopenten-1-one which comprises asymmetrically reducing 2-substituted cyclopentane-1,3,4-trione to the corresponding 2-substituted-4(R)-hydroxy-cyclopentane-1,3-dione, enolizing the said dione to obtain the enol ester or enol ether configuration, reducing the enol ester or ether and recovering the desired compound. The chiral 2-substituted-4-hydroxy-2-cyclopenten-1-one are key intermediates in the preparation of prostaglandins.