Smithkline Corporation

Smith Kline & French Laboratories Limited

George L Dunn

John R Hoover

David A Berges

Novel cephalosporins with improved antibacterial and pharmacokinetic properties are disclosed. These compounds have a 2-alkoxyimino-2-(2-amino-4-thiazolyl)-acetamido group at position 7 and a sulfaminoalkyltetrazolythio group at position 3.

7-[2-Alkoxyimino-2-(amino-thiazole)acetami

New semisynthetic cephalosporins having antibacterial activity are described. The structures of the new compounds are characterized by having an .alpha.-oxyimino group in the 7-acetamidomoiety plus a carboxyalkyltetrazolylthiomethyl group at position 3.

7-Alpha-oxyiminoacylcephalosporins

Cephalosporin compounds substituted in the 7-position with a hydroxy-halo substituted .alpha.-aminophenylacetamido group and in the 3-position with a heterocyclicthiomethyl group are prepared by 7-acylation. The products are antibacterial agents.

7-Hydroxyhalophenylacetamido-3-heterocyclicthiomethyl cephalosporins

New semisynthetic cephalosporins are described whose structures are characterized by having an .alpha.-oxyimino group in the 7-acetamido moiety and a sulfosubstituted tetrazolylthiomethyl group at position 3. The compounds are active antibacterial agents especially against Gram negative organisms.

Derivatives of

7-[.alpha.-Amino-.alpha. -(acylamidophenyl)acetamido]-cephalosporins are prepared. They show improved antibacterial activity especially when they are administered orally.

.alpha.-Amino-.alpha.-(acylamidophenyl)acetamidocephalosporins

7-(p-Hydroxymethylphenylglycylamido)cephalosporins are prepared by acylating a 7-aminocephalosporin compound. The products have antibacterial activity.

P-Hydroxymethylphenylacetamidocephalosporins

Cephalosporin compounds substituted at the 7-position with free or substituted .alpha.-amino or hydroxy phenylacetamido and at the 3-position with a heterocyclic thiomethyl group are prepared by displacement of a 3-acetoxymethyl compound with a mercaptoheterocycle or by 7-acylation. The products are antibacterial agents.

3-Heterocyclic thiomethylcephalosporins

p-Hydroxymethylphenylglycine

Cephalosporin compounds substituted at the 7-position with free or substituted .alpha.-aminophenylacetamido and at the 3-position with a heterocyclic thiomethyl group are prepared by displacement of a 3-acetoxymethyl compound with a mercaptoheterocycle. The products are antibacterial agents.

3-Heterocyclic thiomethylcephalosporins as antibacterial agents

P-hydroxymethylphenylacetamidocephalosporins

7-[.alpha.-Amino-.alpha.-(acylamidophenyl)acetamido]-cephalosporins are prepared. They show improved antibacterial activity especially when they are administered orally.

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Wayne, PA, United States of America

George L Dunn