Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-08-04
1999-06-08
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548231, 548255, 5482632, 5483355, 5483381, 5483741, 5483751, 548469, 548561, 546113, 546117, C07D41310, A61K 3142
Patent
active
059105046
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The subject invention discloses new and useful phenyloxazolidinone compounds having a nitrogen containing hetero-aromatic ring substitution attached through one of the nitrogen atoms. More particularly a 5-member nitrogen containing aromatic ring having from 1 to 4 nitrogen atoms one of which binds to the phenyloxazolidinone. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms such as Bacteroides spp. and Clostridia spp. species, and acid-fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.
INFORMATION DISCLOSURE
The present compounds are related by their phenyloxazolidinone ring structure to the compounds disclosed in the publications below except that the subject compounds have a nitrogen containing hetero-aromatic ring substitution attached to the phenyloxazolidinone by one of the nitrogen atoms. This attachment point facilitates a different but easier synthesis than a corresponding carbon--carbon bond structure and therefore presents an advantage over such compounds. The instant compounds are unique and have useful antibacterial activity.
WO93/23384 application discloses oxazolidinones containing a substituted diazine moiety and their uses as antimicrobials.
WO93/09103 application discloses substituted aryl and heteroaryl-phenyl-oxazolidinones useful as antibacterial agents. In one aspect, it discloses 5-member nitrogen hetero-aromatic rings attached to a phenyloxazolidinone although there is no synthesis disclosed which would permit attachment through the nitrogen atom (see, Chart C (y, w, ee and ff)).
WO90/02744 application discloses 5'indolinyl-5.beta.-amidomethyloxazolidinones, 3-(fused-ring substituted)phenyl-5.beta.-amidomethyloxazolidinones, and 3-(nitrogen substituted)phenyl-5.beta.-amidomethyloxazolidinones which are useful as antibacterial agents.
Other references disclosing various oxazolidinones include U.S. Pat. Nos. 4,801,600, 4,921,869, Gregory W. A., et al., J. Med. Chem., 32, 1673-81 (1989); Gregory W. A., et al., J. Med. Chem., 33, 2569-78 (1990); Wang C., et al., Tetrahedron, 45, 1323-26 (1989); and Brittelli, et al., J. Med. Chem., 35, 1156 (1992).
European Patent Publication 352,781 discloses phenyl and pyridyl substituted phenyl oxazolidinones.
European Patent Publication 316,594 discloses 3-substituted styryl oxazolidinones.
European Patent Publication 312,000 discloses phenylmethyl and pyridinylmethyl substituted phenyl oxazolidinones.
U.S. Pat. No. 5,254,577 discloses nitrogen hetero-aromatic rings attached to phenyloxazolidinone but not by the hetero-aromatic nitrogen (see, Col. 19 and 43).
SUMMARY OF THE INVENTION
In one aspect the subject invention is a compound of structural Formula I: ##STR2## or pharmaceutically acceptable salts thereof wherein: Q is a hetero-aromatic 5-member ring bound to the aromatic ring of I at the nitrogen of the structures i, ii, iii, iv, v, vi, vii, viii, or ix: ##STR3## or alternatively Q can be a benzoannulated hetero-aromatic 5-member ring bound to the aromatic ring of I at the nitrogen of the structures x, xi, xii, xiii, xiv, xv, xvi or xviii: ##STR4## R.sup.1 is independently H, OCH.sub.3, F, or Cl; R.sup.2 is following: F, Cl, hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy; cycloalkyl, optionally substituted with one or more of (a)-(m), or groups listed under (a)-(n); and cycloalkyl, optionally substituted with one or more of fluorine, chlorine, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 acyl, C.sub.1 -C.sub.4 acyloxy, or O.sub.2 CCH.sub.2 N(CH.sub.3).sub.2, or C.sub.1 -C.sub.4 straight or branched chain alkyl, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 acyl, C.sub.1 -C.sub.4 acyloxy, or O.sub.2 CCH.sub.2 N(CH.sub.3).sub.2.
DETAILED DESCRIPTION OF THE INVENTION
The present invention discloses novel substituted 5-member nitrogen heterocyclic
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Gregory W. A., et al., J. Med. Chem., 32, 1673-81 (1989).
Gregory W. A., et al., J. Med. Chem., 33, 2569-78 (1990).
Wang C., et al., Tetrahedron, 45, 1323-26 (1989).
Brittelli, et al., J. Med. Chem., 35, 1156 (1992).
Corneglio Donald L.
Daus Donald G.
Pharmacia & Upjohn
Yang Lucy X.
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