Eli Lilly and Company

Rexnord Gmbh

David A Hall

Nicholas J Bach

Edmund C Kornfeld

John R Marjancik

John Michael Morin, Jr

Robert J Ternansky

Wayne A Spitzer

Richard E Heiney

Paul W Landis

Donnis M Berry

Richard M Justice, Jr

A self lubricating replacement bearing assembly for supporting a rotating axle shaft within an axle housing containing axle lubricant. The rotating axle shaft includes an annular worn portion and an annular unworn portion. The bearing assembly is comprised of an annular sleeve member positioned in sealing engagement with the axle housing, and a plurality of bearing elements radially positioned on the inside annular surface of the annular sleeve member and positioned to engage the unworn portion or the axle shaft, and a single lip seal member fitted to the inner annular surface of the sleeve member and engageable with the rotating shaft to seal the rotating shaft within the axle housing and to retain the axle lubricant within the bearing assembly.

Replacement bearing for worn shafts

A process for preparing 3-4-cis-.beta.,.beta.-(4)-substituted and 3-4-trans,.beta.,.alpha.-(4)-substituted azetidinones is provided. Also provided are novel 4,4-disubstituted azetidinones.

Process for preparing 4-substituted azetidinones

The present invention relates to electrochemical reduction of a 3-chlorobenzo[b]thiophene to the corresponding 3-hydrobenzo[b]thiophene compound.

Electrochemical reduction of 3-chlorobenzo[b]thiophenes

N-substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamino)-4-oxo-azetidines, which are useful as intermediates in 1-oxa .beta.-lactam antibiotics, are synthesized by electrolytic reduction of 7-(S)-acylamino-3-hydroxymethyl-3-cephem-4-carboxylic acid compounds.

N-substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamino)-4-oxo-azetidines

Compounds of the formula ##STR1## in which Y is hydrogen or hydroxyl, useful as intermediates in the production of antibiotics, are prepared by reacting a sulfinic acid of the formula ##STR2## with an oxidizing agent.

Process for preparing oxazolinoazetidinones

This invention encompasses 7-(S)-acylamino-3-acetoxymethyl-3-cephem-4-carboxylic acid sulfones and the epimerization process for making them. The epimerization process employs an organic nitrogen base reagent having a pKa between about 9.0 to about 11.5. The compounds of this invention are intermediates in the synthesis of 1-oxa-.beta.-lactam antibiotics.

7-(S)-Acylaminocephalosporin sulfones and process

7-(S)-Acylamino-3-hydroxymethyl-3-cephem sulfones are disclosed. These compounds are intermediates in the synthesis of 1-oxa .beta.-lactam antibiotics.

Desacetylcephalosporin sulfones

An azetidin-2-one-4-sulfinic acid represented by the formula ##STR1## is reacted with Pb(OAc).sub.4 in liquid SO.sub.2 containing CuII ion to provide isomeric cyclization products of the formulas ##STR2## wherein R is e.g. benzyl, phenoxymethyl, benzyloxy, diphenylmethoxy, and R.sub.1 is a carboxy-protecting group. The products of the process are useful intermediates for 1-oxa-.beta.-lactam antibacterials.

Process for 1-oxa-.beta.-lactams

N-Substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamido)-4-oxo-azetidines

Cephem compounds having only a hydrogen at the 3-position are prepared by electrolytic reduction of 3-chloro or 3-sulfonyloxy cephems.

Process for 3-hydrogen cephems

Deesterification of cephalosporin p-nitrobenzyl esters by electrolytic reduction.

Electrolytic reduction of cephalosporin p-nitrobenzyl esters

Dihydrobenzopyranoxanthenones of the formula ##STR1## are electrolytically reduced to their corresponding hexahydrobenzopyranoxanthenones at a mercury cathode in the presence of a proton source and in the presence of an electrolyte selected from the group consisting of alkali metal salts, quaternary ammonium salts having a total of about 10 to about 28 carbon atoms in the cation moiety, and tertiary amine salts having a total of about 7 to about 21 carbon atoms in the cation moiety.

Electrolytic reduction of dihydrobenzopyranoxanthenones

7-Acylamino-7-methoxycephalosporins substituted in the 3-position with an acetoxymethyl, halomethyl or 3-thio-substituted-methyl substituent are reduced electrolytically to provide the corresponding 3-exomethylenecepham compound. For example, 7-(2-thienylacetamido)-7-methoxy-3-acetoxymethyl-3-cephem-4-carboxylic acid is electrolytically reduced to provide 7-(2-thienylacetamido)-7-methoxy-3-exomethylenecepham-4-carboxylic acid and a lesser amount of the corresponding 3-methylcephalosporin compound.

Electrolytic process for 7-methoxy-3-exomethylenecepham compounds

Descarboxylysergic acid prepared from 2,3-dihydro-8.beta.-hydroxy-6-methyl-9-ergolene or from penniclavine has oxytocic, serotonin antagonist, prolactin inhibition and muscle contracting activities.

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Indianapolis, IN, United States of America

David A Hall