Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-05-14
1999-09-14
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514215, 5142242, 5142305, 514301, 514302, 514324, 546114, 546115, 540593, 540582, 540477, C07D49148, C07D49108, C07D49504, A61K 3142
Patent
active
059523247
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The subject invention discloses new and useful phenyloxazolidinone compounds characterized by having either a bicyclic thiazine or oxazine substituent. 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 those disclosed in the publications below except that the subject compounds have either a bicyclic thiazine or oxazine phenyl substituent. The instant compounds have useful antibacterial activity.
PCT/US94/08904 application discloses oxazolidinone antibacterial compounds having either a morpholine or thiomorpholine substituent.
PCT/US93/03570 application discloses oxazolidinones containing a substituted diazine moiety and their uses as antimicrobials.
PCT/US92/08267 application discloses substituted aryl and heteroaryl-phenyl-oxazolidinones useful as antibacterial agents.
PCT/US89/03648 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. Chm., 35, 1156 (1992).
European Patent Publication 352,781 disclose 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.
SUMMARY OF THE INVENTION
In one aspect the subject invention in a compound of structural Formula I: ##STR2##
More preferred compounds, a subset of those described by structural Formula I, are represented by structural Formula II: ##STR3## or pharmaceutically acceptable salts thereof wherein: X is (a) O, following: F, Cl, hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy,
In another aspect, the subject invention is directed toward a method for treating microbial infections in humans or other warm-blooded animals by administering to a patient in need thereof an effective amount of a compound of Formula I or II as described above. The compound can be administered in a pharmaceutical composition either orally, parenterally or topically. Preferably the compound is administered in an amount of from about 0.1 to about 100 mg/kg of body weight/day, more preferably, from about 3.0 to about 50 mg/kg of body weight/day.
DETAILED DESCRIPTION OF THE INVENTION
The present invention discloses novel substituted bicyclic oxazinyl- or thiazinylphenyloxazolidinones of structural Formula I and II as described above. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, particularly aerobic gram-positive bacteria, including multiply-resistant staphylococci and streptococci, as well as anaerobic organisms such as bacteroides and clostridia species, and acid-fast bacteria such as as Mycobacterium tuberculosis and other mycobacterial species.
"Alkyl" means carbon atom chains having the designated number of carbon atoms which can be either strait chained or branched.
"Alkyl" means the designated number of carbon atoms attached to an oxygen forming such groups as methoxy (--OCH.sub.3), ethyloxy, butyloxy, etc. and isomeric forms thereof.
"Acyloxy" means the designated number of carbon atoms to form an organic acid where the OH group has been deleted, such
REFERENCES:
patent: 4801600 (1989-01-01), Wang et al.
patent: 4921869 (1990-05-01), Wang et al.
patent: 5668286 (1997-09-01), Yamada et al.
Gregory, W.A., et al.; J. Med. Chem., 32:1673-1681 (1989).
Gregory, W.A., et al.; J. Med. Chem., 33, 2569-2578 (1990).
Park, C-H, et al.; J. Med. Chem., 35:1156-1165 (1992).
Wang, C-L, et al.; Tetrahedron, 45(5):1323-1326 (1989).
Barbachyn Michael R.
Cleek Gary L.
Gadwood Robert C.
Thomas Richard C.
Thomasco Lisa M.
Corneglio Donald L.
Gammill Martha A.
Kifle Bruck
Pharmacia & Upjohn Company
Raymond Richard L.
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