Merck + Co., Inc.

Merck Sharp + Dohme Corp.

Charles E. Frosst & Co.

Leonard M Weinstock

Sandor Karady

Roger J Tull

Joseph S Amato

Dennis M Mulvey

Ichiro Shinkai

Burton Kendall Wasson

George D Hartman

Arthur S Wildman, Jr

Thomas R Verhoeven

Meyer Sletzinger

Thomas M Liu

Anthony O King

Edward G Corley

Paul Sohar

Ann E DeCamp

Newton L Abramson

Robert S Hoerrner

Robert K Anderson

George M Love

William A Sklarz

Carl Bagner

Joel J Friedman

Henry S Kao

Richard E Shuman

Anti-ulcer agents having a methylsulfinyl bridge between a substituted pyridine moiety and a substituted benzimidazole moiety are prepared by oxidizing the corresponding compounds, having a methylthio bridge, with magnesium monoperoxyphthalate in a suitable solvent. The reaction may be run in an aromatic hydrocarbon solvent, wherein the product may crystallize out of the reaction solution and may be directly isolated by filtration.

Process for the preparation of antiulcer agents

A process for introducing a 1,2 double bond into a compound of the formula ##STR1## which comprises the process of (a) treating the compound of formula I with oxalyl chloride; (b) brominating the product of step (a) followed by in situ dehydrobromination; (c) deprotecting the product of step (b) to yield the .alpha. and .beta. isomers; (d) dehydrobrominating the product of step (c), which results in the introduction of a double bond at the 1,2 position.

Method for introducing a 1,2 double bond into azasteroids

10,11 Dihydro-11-exo-hydroxy-5-methyldibenzo[a,d]cyclohepten-5,10-imine is prepared in a four step synthesis which uses an electrochemical cyclization to form the 5,10-imine bridge in about a 50% yield.

Process for preparing

A novel acylation process using an alkali metal bromide and a dialkylaminopyridine to form a sterically hindered ester functionality from an alkanoyl chloride and an alcohol is disclosed.

Acylation process for the synthesis of HMG-CoA reductase inhibitors

This invention relates to a process for preparing .beta.-lactams by electrochemically deblocking N-substituting .beta.-lactams using anodic oxidation.

Process for deblocking N-substituted .beta.-lactams

A novel synthon useful in the conversion of penicillin is a compound of the formula ##STR1## wherein R.sub.3 is a number of the group consisting of trimethyl-silyl, t-butyl dimethyl silyl, trimethyl silyl, methyl, benzyl or nitrobenzyl, and R.sub.5 is the same or different member of the group R.sub.3 is prepared by the naphthalene sulfonyl azide exchange reaction with benzyl acetoacetate, p-nitrobenzylacetoacetate, or methylacetoacetate to obtain the corresponding 2-diazo compound which is then silylated in hexamethyl-disalazine.

Silyl, benzyl, p-nitrobenyl, or methyl esters of diazoacetate, a synthon

A process for preparing .alpha.-alkyl amino acids by enantioretentive .alpha.-alkylation of .alpha.-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.

Process for preparation of alpha-alkyl amino acids

A stereospecific conversion of penicillin to thienamycin, using diisopropylamine borane and magnesium trifluoroacetate to prepare the hydroxyethyl side chain and acetoacetate dianion equivalent disilylethyl to prepare the .beta.-ketoester side chain.

Stereospecific synthesis of thienamycin from penicillin

Substituted-1,2,5-thiadiazole-1-oxides, their preparation and pharmaceutical use as elastase inhibitors are disclosed.

Substituted-1,2,5-thiadiazole-1-oxide compounds, compositions and use

2-(3-Substituted amino-2-hydroxypropoxy)-3-substituted pyrazine compounds optionally having substituents in the 5 and/or 6 positions, possessing .beta.-adrenergic blocking properties are described. The products are prepared by reaction of a 2-chloro (or hydroxy) pyrazine with a 5-hydroxymethyl (or sulfonyloxymethyl) oxazolidine followed by acid hydrolysis.

2-(3-Substituted amino-2-hydroxypropoxy)-3-piperidino pyrazines for use

A method of preparing 2,4-difluoroaniline by reacting 2,4,5-trichloronitrobenzene with a fluorinating agent to form 2,4-difluoro-5-chloronitrobenzene which is then hydrogenated with hydrogen in the presence of a catalyst to form 2,4-difluoroaniline.

Method of preparing 2,4-difluoroaniline

An improved process for the preparation of thiazoles is disclosed. The process utilizes a substituted imine and sulfur dioxide heated in the presence of a catalyst. The thiazoles are known important chemical intermediates.

Process for the preparation of thiazoles

An improved process for preparing the antibiotic compound 7.beta.-(2-thienylacetamido)-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-car boxylic acid, from the N-blocked esters of the compound 7.beta.-(D-5-amino-5-carboxyvaleramido)-3-carbamoyloxymethyl-7-methoxy-3-c ephem-4-carboxylic acid (Cephamycin C), by conducting the transacylation of the latter in a homogenous solution containing N-trimethylsilyl loweralkyl carbamates.

Process for the preparation of cephamycin antibiotics

Improved method of preparing 5-(2,4-difluorophenyl)salicylic acid and derivatives which favors formation of the desired end product over other undesired isomers, comprising the steps of

Preparation of 5-(2,4-difluorophenyl)salicylic acid and derivatives

2-(3-Substituted amino-2-hydroxypropoxy)-3-substituted pyrazine compounds optionally having substituents in the 5 and/or 6 positions, possessing .beta.-adrenergic blocking properties are described. The products are prepared by reaction of a 2-chloro(or hydroxy)pyrazine with a 5-hydroxymethyl(or sulfonyloxymethyl)oxazolidine followed by acid hydrolysis.

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Belle Mead, NJ, United States of America

Leonard M Weinstock