Eli Lilly and Company

Eddie V Tao

James A Aikins

John Robert Rizzo

John P Gardner

Billy G Jackson

Gilbert S Staten

J Jeffry Howbert

James R Beck

Richard Waltz Harper

Brent Jeffrey Rieder

Jeffrey Thomas Vicenzi

William David Miller

Gerald A Poore

John Brennan

7.beta.-Amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are provided via cyclization of cis-3-(substituted amino)-1-(2-substituted 2-oxoethyl)-4-substituted azetidinones. The 7.beta.-amino-3-hydroxy-1-carba (1-dethia)-3-cephem-4-carboxylic acid esters are useful chiral intermediates to .beta.-lactam antibiotics.

Azetidinone intermediates to carbacephalosporins and process

This invention provides certain sulfonamide derivatives, their pharmaceutical formulations, and their use in the treatment of susceptible neoplasms in mammals.

Anti-tumor method and compounds

7.beta.-Amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are provided via cyclization of cis-3-(substituted amino)-1-(2-substituted 2-oxoethyl)-4-substituted azetidinones. The 7.beta.-amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are useful chiral intermediates to .beta.-lactam antibiotics.

This invention provides a novel process for the synthesis of bicyclic aromatic sulfonic acids employing reacting a bicyclic aromatic compound with sulfur trioxide-N,N-dimethylformamide complex in the presence of a water miscible, non-reactive solvent. The resulting sulfonic acid may be converted into the corresponding sulfonyl halide by the reaction with a thionyl halide. This invention further provides a novel process for the synthesis of bicyclic aromatic sulfonamides employing the reaction conditions described supra followed by an ammonolysis or amination.

Synthesis of bicyclic aromatic sulfonic acids sulfonyl chlorides and

Disclosed is a process using hydrolysis and hydrogenation for converting enamino .beta.-lactams to their saturated alkyl ester acid salts, key intermediates to 1-carbacephalosporins. Also disclosed are intermediates resulting from the process.

Intermediates to 1-carbacephalosporins and process for preparation

The present invention provides 5-cyano-4,5-dihydro-3,4-dicarboxypyrazoles and a process for preparing such compounds which comprises reacting a dialkyl fumarate with diazoacetonitrile.

Process for preparing 5-cyano-4, 5-dihydro-3,4-dicarboxypyrazole

This invention provides an improvement in the process for preparing C-20-amino-substituted derivatives of the macrolide antibiotics of the tylosin type by reductively aminating the C-20 aldehyde group in the parent antibiotic. The improvement comprises using formic acid as the reducing agent. The new process is less expensive and more amenable to scale-up than previously used processes, but is still selective.

Process for preparing macrolide derivatives

5-cyano-4,5-dihydro-3,4-dicarboxypyrazole derivatives

The present invention provides a process for selectively alkylating pyrazoles comprising reacting a 3(5)-cyano-1H-pyrazole-4-carboxylic acid ester with a C.sub.4 -C.sub.8 alkene, or a C.sub.5 -C.sub.6 cycloalkene substituted at the 1-position with a C.sub.1 -C.sub.4 alkyl group, and a strong acid in a solvent which contains a strong electron withdrawing group. Also provided are new 3(5)-cyano-1H-pyrazole-4-carboxylic acid ester useful as starting materials in the process of the invention.

Alkylation of 3(5)-cyano-1H-pyrazole-4-carboxylic acid esters

The herbicide 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide is prepared in high yield and high purity in a two-step process without isolation of the intermediate.

Process for preparing herbicidal

The herbicide 1-(5-t-butylisoxazol-3-yl)-3,3-dimethylurea is prepared in high yield and high purity by a multiple-step process without the isolation of intermediate products.

Process for preparing an isoxazolylurea

4-Acyl-2-methylamino-4,5-dihydro-1,3,4-thiadiazoles are herbicides active against pigweed and foxtail.

Herbicidal 2-methylamino thiadiazolines

4,5-Dihydro-4-acyl-1,3,4-thiadiazol-2-ylureas are herbicides active against pigweed and foxtail.

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Indianapolis, IN, United States of America

Eddie V Tao