Back to results
US 4,948,801 AGranted
Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents
AssigneeE. I. Du Pont de Nemours and Company
InventorsRandall K. Carlson, Chung-Ho Park, Walter A. Gregory
Life of this patent
Estimating the term…
Abstract
Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4-(4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl{acetamide, possess useful antibacterial activity.
Claims26
An aryl benzene oxazolidinone of the formula ##STR90## wherein, for the l, and mixtures of the d and l stereoisomers of the compound
- Ar is ##STR91## X independently is H, --NO.sub.2, --S(O).sub.n R.sub.1, --S(O).sub.2 --N.dbd.S(O).sub.p R.sub.2 R.sub.3, ##STR92## of 1 to 8 carbons optionally substituted with halogen, OH, .dbd.O other than at alpha position, S(O).sub.n R.sub.24, or NR.sub.5 R.sub.6, alkenyl of 2-5 carbons or cycloalkyl of 3-8 carbons;
- R.sub.1 is C.sub.1 -C.sub.4 alkyl, optionally substituted with halogen, OH, CN, NR.sub.5 R.sub.6 or CO.sub.2 R.sub.8 ;
- C.sub.2 -C.sub.4 alkenyl;
- --NR.sub.9 R.sub.10 ;
- --N.sub.3 ;
- ##STR93## --NG.sub.2 ;
- --NR.sub.9 G--.sup.- NGM.sup.+ ;
- R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.2 alkyl;
- R.sub.4 is alkyl of 1-4 carbons, optionally substituted with halogen;
- R.sub.5 and R.sub.6 are independently H, alkyl of 1-8 carbons, cycloalkyl of 3-8 carbons, --(CH.sub.2).sub.t OR.sub.8, --(CH.sub.2).sub.t R.sub.11 R.sub.11a, or --O(CH.sub.2).sub.t NR.sub.11 R.sub.11a;
- R.sub.7 is --NR.sub.5 R.sub.6, --OR.sub.5 or ##STR94## R.sub.8 is H or alkyl of 1-4 carbons;
- R.sub.9 is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.8 cycloalkyl;
- R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 cycloalkyl, --OR.sub.8 or NR.sub.11 R.sub.11A ;
- R.sub.11 and R.sub.11A are independently H or C.sub.1 -C.sub.4 alkyl;
- G is Cl, Br or I;
- Y independently is H, F, Cl, Br, OR.sub.8, alkyl of 1-3 carbons, or NO.sub.2 ;
- or ##STR95## is:
- ##STR96## M is a physiologically acceptable cation;
- n is 0, 1 or 2;
- p is 0 or 1;
- r is 4 or 5;
- t is 1, 2 or 3;
- B is --NH.sub.2, ##STR97## --N--S(O).sub.u R.sub.14, or N.sub.3 ;
- R.sub.12 is H, C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.8 cycloalkyl;
- R.sub.13 is H;
- C.sub.1 -C.sub.4 alkyl optionally substituted with halogen, C.sub.2 -C.sub.4 alkenyl;
- C.sub.3 -C.sub.4 cycloalkyl;
- phenyl;
- --CH.sub.2 OR.sub.15 ;
- --CH(OR.sub.16)OR.sub.17 ;
- --CH.sub.2 S(O).sub.v R.sub.14 ;
- ##STR98## --OR.sub.18 ;
- --SR.sub.14 ;
- --CH.sub.2 N.sub.3 ;
- an aminoalkyl group derived from an .alpha.-amino acid selected from the group consisting of glycine, L-alanine, L-cysteine, L-proline, and D-alanine;
- --NR.sub.19 R.sub.20 ;
- or --C(CH.sub.2)R.sub.21 R.sub.22 ;
- R.sub.14 is C.sub.1 -C.sub.4 alkyl, optionally substituted with halogen;
- R.sub.15 is H or C.sub.1 -C.sub.4 alkyl, optionally substituted with halogen;
- R.sub.16 and R.sub.17 are independently C.sub.1 -C.sub.4 alkyl or, taken together are --(CH.sub.2).sub.m --;
- R.sub.18 is C.sub.1 -C.sub.4 alkyl or C.sub.7 -C.sub.11 aralkyl;
- R.sub.19 and R.sub.20 are independently H or C.sub.1 -C.sub.2 alkyl;
- R.sub.21 and R.sub.22 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl;
- u is 1 or 2;
- v is 0, 1 or 2;
- m is 2 or 3;
- s is 2, 3, 4 or 5;
- R.sub.23 is H, alkyl of 1-8 carbons optionally substituted with halogen. cycloalkyl of 3-8 carbons, alkyl of 1-4 carbons substituted with one or more of --S(O).sub.n R.sub.24, --OR.sub.8, ##STR99## or --NR.sub.5 R.sub.6 ;
- or alkenyl of 2-5 carbons optionally substituted with CHO or CO.sub.2 R.sub.8 ;
- R.sub.24 is alkyl of 1-4 carbons or cycloalkyl of 3-8 carbons;
- and
- R.sub.25 is R.sub.6 or NR.sub.5 R.sub.6 ;
- or a pharmaceutically suitable salt thereof.
50 more elements
A method of treating a bacterial infection in a mammal comprising:
- administering to the mammal an antibacterial amount of a compound of selected from the group consisting of:
- (a) (l)-N-[3-(4-(4'-pyridyl)phenyl-2-oxooxazolidin-5-ylmethyl]acetamide, hydrochloride;
- (b) (l)-N-[3-(4-(3'-pyridyl)phenyl-2-oxooxazolidin-5-ylmethyl]acetamide, hydrochloride;
- or
- (c) (l)-N-[3-(4-4'-methyl-3'-pyridyl)phenyl-2-oxooxazolidin-5-ylmethyl]acetami de.
2 more elements
Dependencies are inferred from the claim text.