The Upjohn Co.

Barney J Magerlein

Howard A Whaley

Bengt Samuelsson

This invention concerns 2-oxoazetidine analogs (monobactams) having antimicrobial activity, novel processes and novel intermediates useful to make monobactams. The compounds of this invention include compounds of the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein: R.sub.1 is an acyl group derived from a carboxylic acid;

Carbonate substituted monobactams as antibiotics

Novel antibacterially-active esters of antibiotic nodusmicin. Activity is demonstrated against Staphylococcus aureus, Streptococcus pyogenes, and Sarcina lutea. Thus, these esters can be used in various known environments, using well-known procedures, to eradicate or control susceptible microbes.

Antibiotic nodusmicins

Antibiotic nodusmicin derivatives

Novel antibacterially-active analogs of the antibiotics nodusmicin and nargenicin A.sub.1. These compounds are prepared by selectively blocking active hydroxyl groups at the 9, 11 and 18 positions of nodusmicin, and the 11 and 18 positions of nargenicin A.sub.1. Antibacterially-active compounds can be used in various environments to control or eradicate susceptible bacteria. The techniques for such use are well known in the art.

Nargenicin derivatives

Esters of antibiotic nodusmicin

6-Deoxyneamine, 6-deoxy-5-epineamine, their 5-0-glycosyl derivatives, 6-deoxy-5-oxoneamine and the derivatives therefrom are useful as antibacterial agents and/or as intermediates in the synthesis of antibacterially active 6-deoxyneamines.

6-Deoxyneamines

Bicyclic lactone intermediates useful for preparing prostaglandin E.sub.2 -type, F.sub.2 -type, A.sub.2 -type, and B.sub.2 -type compounds with one or two methyl or ethyl substituents at the C-16 position are disclosed. These prostaglandin-type compounds are useful for the same pharmacological purposes as the corresponding prostaglandins.

Bicyclic lactone intermediates

The disclosure includes novel compounds which differ from the known prostaglandins PGF.sub.2.alpha., PGF.sub.2.beta., PGE.sub.2, PGA.sub.2, and PGB.sub.2 in that the carbon-carbon double bond in the carboxyl-terminated chain of the novel compounds is in the 4,5-position rather than in the 5,6-position, and in that there is a phenoxy or substituted phenoxy group in the other chain of the novel compounds. These novel compounds are useful for a variety of pharmacological purposes, including abortion, labor induction, and reduction of gastric secretion.

cis-4,5-Didehydro-16-phenoxy-PGE.sub.1 compounds

6-Deoxyneamine, 6-deoxy-5-epineamine, their 5-O-glycosyl derivatives, 6-deoxy-5-oxoneamine and the derivatives therefrom are useful as antibacterial agents and/or as intermediates in the synthesis of antibacterially active 6-deoxyneamines.

6-Deoxyneamines aminoglycoside compounds

Cis-4,5-didehydro-16-phenoxy-PGA.sub.1 compounds

The disclosure includes novel compounds which differ from the known prostaglandins PGF.sub.2.alpha., PGF.sub.2.beta., PGE.sub.2, PGA.sub.2, and PGB.sub.2 in that the carbon-carbon double bond in the carboxyl-terminated chain of the novel compounds is in the 4,5-position rather than in the 5,6-position, and in that there is a phenyl or substituted phenyl group in the other chain of the novel compounds. These novel compounds are useful for a variety of pharmacological purposes, including abortion, labor induction, and reduction of gastric secretion.

Growing community of inventors

Portage, MI, United States of America

Barney J Magerlein