Abstract: Racemic or optically-active prostaglandin E.sub.1 is synthesized from racemic or optically-active precursors in good yield at the various steps from 3.alpha., 6,7,7.alpha.-tetrahydro-4-methyl-2-oxo-1.beta.-indaneheptanoic acid methyl ester proceeding through 2.alpha.-(2-carboxyethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneheptan oic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-formylethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopent aneheptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-oxoethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentane heptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, and 3.beta.-hydroxy-2.alpha.-(3-oxo-1-octenyl)-5-oxo-1.beta.-cyclopentanehepta noic acid methyl ester, 5-cyclic ethylene acetal.

Abstract: The invention is concerned with novel 16-aryloxy-, 16-alkoxy-, 16-arylthio- and 16-alkylthio-8-aza-9-dioxothia-11,12-seco-prostaglandins and processes for their preparation. These novel compounds are useful as pharmaceuticals since they can be used in animals for estrus synchronization and treatment of infertility due to persistence of luteal function.

Abstract: Racemic or optically-active prostaglandin E.sub.1 is synthesized from racemic or optically-active precursors in good yield at the various steps from 3.alpha.,6,7,7.alpha.-tetrahydro-4-methyl-2-oxo-1.beta.-indaneheptanoic acid methyl ester proceeding through 2.alpha.-(2-carboxyethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneheptan oic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-formylethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopent aneheptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-oxoethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentane heptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, and 3.beta.-hydroxy-2.alpha.-(3-oxo-1-octenyl)-5-oxo-1.beta.-cyclopentanehepta noic acid methyl ester, 5-cyclic ethylene acetal.

Abstract: This invention relates to 11,12-secoprostaglandins and processes for their manufacture. These compounds have prostaglandin-like biological activity and are particularly useful as renal vasodilators, for the treatment of hypertension, and for the prevention of thrombus formation.

Abstract: This invention relates to 8,10-diaza-9-oxo(and thioxo)-11,12-secoprostaglandins and processes for their manufacture. These compounds have prostaglandin-like biological activity and are particularly useful as renal vasodilators, and for the prevention of thrombus formation.

Abstract: (.+-.)-Prostaglandin E.sub.1 is totally synthesized with a high degree of stereoselectivity and in good yield at the various steps from 6-methoxy-3-indanol by a sequence of reactions proceeding through 6-methoxy-3-indeneheptanoic acid ester, 2,6-dioxo-4,5,6,7-tetrahydro-7-methyl-3-indanheptanoic acid ester 2-cyclic ethylene acetal, cis-3,4,5,7a-tetrahydro-7-methyl-2-oxoindanheptanoic acid ester, trans-trans 3-acetyl-2-(2-carboxy-ethyl)-5-oxocyclopentane heptanoic acid ester 5-cyclic-ethylene acetal, 3-acetoxy-2-formyl-5-oxocyclopentaneheptanoic acid ester 5-cyclic ethylene acetal, and 15-dehydro (.+-.)-prostaglandin E.sub.1. The end compound has the biological activity of naturally occurring prostaglandin E.sub.1.

Abstract: This invention relates to 8-aza-11,12-secoprostaglandins and processes for their manufacture. These compounds have prostaglandin-like biological activity and are particularly useful as renal vasodilators.

Abstract: The new 1-alkyl-4-(10-oxo or -hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds are prepared from the corresponding 10-desoxy compounds having a double bond at the 10,11-position by a process involving bromination, dehydrobomination of the resulting dibromo compound, followed by enamine formation and hydrolysis to give the desired 10-oxo compound. The compounds prepared in this manner are active as antihistamines and as appetite stimulants.

Abstract: The disclosure relates to novel precursors for the synthesis of prostaglandin E.sub.1 and the production of said precursors.

Abstract: Tetrafluoro derivatives of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-propylamine and 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-.DELTA.-5-.gamma.-propylamine, useful as antidepressants, are prepared from the known 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-10,11-dione by fluorination at the 10,11- position using sulfur tetrafluoride followed by introduction of the amino propylidine or the amino propyl substituent at the 5- position by reaction of the 5-keto or 5-halo-10,10,11,11-tetrafluoro derivative with the appropriate Grignard reagent.

Abstract: The new 1-alkyl-4-(10-oxo or -hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine compounds are prepared from the corresponding 10-desoxy compounds having a double bond at the 10,11-position by a process involving bromination, dehydrobromination of the resulting dibromo compound, followed by enamine formation and hydrolysis to give the desired 10-oxo compound. The compounds prepared in this manner are active as antihistamines and as appetite stimulants.

Abstract: Deuterated functional group-containing hydrocarbons prepared by treating the non-labelled substrate in the liquid state with deuterium gas in the presence of a Group VII or VIII metal catalyst with heating between ambient to 300.degree. C. The labelled compounds are especially useful in reaction mechanism studies, as tracers in separation process studies, in the investigation of the physical properties of labelled compounds and in other specialized research work.

Abstract: Disclosed is a novel stereospecific synthesis of Prostaglandin E.sub.1.

Abstract: This invention concerns 2,3,5,6-dibenzobicyclo-[5.1.0]octanes which may be substituted at the 4-position by either halogen, ketonic oxygen or hydroxyl. These compounds are prepared from 5H-dibenzo[a,d]cyclohepten-5-one by reaction with ethyl trichloroacetate in the presence of sodium methoxide to give 8,8-dichloro-2,3,5,6-dibenzobicyclo[5.1.0]octan-4-one which is reduced to the corresponding 4-hydroxy compound. The resulting 4-hydroxy compound is dehalogenated and converted to the corresponding 4-chloro or 4-keto compound. The 4-substituted compounds are useful in preparing other compounds of our invention.4-Dialkylaminopropylidenedibenzobicyclo[5.1.0]-octane compounds and 4-dialkylaminopropyldibenzobicyclo[5.1.0]octane compounds, useful as antidepressant agents, are prepared from, respectively, dibenzobicyclo[5.1.0]-octan-4-one by reaction with a dialkylaminopropyl Grignard reagent followed by dehydration of the resulting carbinol or by reaction of a 4-halo-2,3,5,6-dibenzobicyclo[5.1.

Abstract: The new 1-alkyl-4-(10-oxo or -hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds are prepared from the corresponding 10-desoxy compounds having a double bond at the 10,11-position by a process involving bromination, dehydrobromination of the resulting dibromo compound, followed by enamine formation and hydrolysis to give the desired 10-oxo compound. The compounds prepared in this manner are active as antihistamines and as appetite stimulants.

Abstract: Novel 4-phenyl-4-substituted-5-oxo-7-aryl-heptanoic acids are prefaced by either of two synthetic processes. The first method involves the reaction of a 4-phenyl-4-substituted-5-oxo-hexanoic acid with an arylcarboxyaldehyde. The second method involves reaction of an arylcarboxaldehyde with an appropriate ketone, treatment of the product with an acrylic acid ester, followed by hydrolysis of the resulting ester. The compounds of the invention are prostaglandin antagonists and are particularly useful as topical anti-inflammatory agents.

Abstract: (.+-.)-Prostaglandin E.sub.1 is totally synthesized with a high degree of stereoselectivity and in good yield at the various steps from 6-methoxy-3-indanol by a sequence of reactions proceeding through 6-methoxy-3-indeneheptanoic acid ester, 2,6-dioxo-4,5,6,7-tetrahydro-7-methyl-3-indanheptanoic acid ester 2-cyclic ethylene acetal, cis-3,4,5,7a-tetrahydro-7-methyl-2-oxoindanheptanoic acid ester, trans-trans 3-acetyl-2-(2-carboxy-ethyl)-5-oxocyclopentane heptanoic acid ester 5-cyclic-ethylene acetal, 3-acetoxy-2-formyl-5-oxocyclopentaneheptanoic acid ester 5-cyclic ethylene acetal, and 15-dehydro (.+-.)-prostaglandin E.sub.1. The end compound has the biological activity of naturally occurring prostaglandin E.sub.1.

Abstract: 6 .alpha.-Carboxy-5.alpha. (1-hydroxyethyl)-2-cyclohexene-1-heptanoic acid, .gamma. - lactone, and lower alkyl and aralkyl esters thereof, are useful intermediates for the production of Prostaglandin E.sub.1.