US 4,382,089 A · Antibacterial amide compounds, compositions thereof and methods of using them

Abstract

Novel organic amide compounds which are N-[[(acylaminoacylamino or aminoacylamino9]-dihydro-oxo-3-quinolinylcarbonyl]penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding (acylaminoacylamino or aminoacylamino)-dihydro-oxo-3-quinolinecarboxylic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[(acylaminoacylamino or aminoacylamino) dihydro-oxo-3-quinolinycarbonyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Claims23

Dependent claims

A compound of the formula ##STR31## and pharmaceutically acceptable salts thereof;

wherein M is ##STR32## R is ##STR33## or R.sub.1 -[NR.sub.4 -acyl].sub.n ;
x is an integer from one to five, x' is zero, one or two;
R.sub.1 is hydrogen, lower alkyl, benzyl, or ##STR34## wherein R.sub.2 is hydrogen, amino or a lower alkyl group of from one to four carbon atoms, optionally substituted by from one to three chlorine or fluorine atoms;
R.sub.4 is hydrogen or lower alkyl;
N-acyl is an aminoacyl moiety derived from a carboxylic acid of from two to ten carbon atoms optionally substituted by from one to three of the following groups, formamido, lower alkylamido, hydroxyl, ##STR35## amino, carbamido, carbonyl oxygen, lower alkoxy, lower alkylthio, or sulfonic acid;
R.sub.3 is phenyl, 4-hydroxyphenyl, 2-thienyl or cyclohexa-1,4-dien-1-yl and n is an integer of from one to four.

3 more elements

Dependencies are inferred from the claim text.

Antibacterial amide compounds, compositions thereof and methods of using them

Life of this patent

Antibacterial amide compounds, compositions thereof and methods of using them

Life of this patent

Abstract

Claims23