Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-04-23
1999-03-16
McKane, Joseph K.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514376, 540200, 540362, 540364, 548232, 548950, 548952, 548953, A61K 3142, A61K 31395, C07D20504, C07D26314
Patent
active
058830936
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase of international application PCT/US/95/10992.
BACKGROUND OF THE INVENTION
The subject invention discloses new and usefull phenyloxazolidinone compounds having either a pyrrolidinyl or azetidinyl moiety. 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 multi-substituted pyrrolidinyl or azetidinyl moiety. The instant compounds are unique and have useful antibacterial activity.
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/US89/03548 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 usefull 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.
SUMMARY OF THE INVENTION
In one aspect the subject invention is a compound of structural Formula I: ##STR1## or pharmaceutically acceptable salts thereof wherein: Q is selected from the structures i, ii, iii, iv and v: ##STR2## R.sup.1 is (a) H or F, following: fluorine, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 acyloxy; or more F, Cl, C.sub.1-6 alkoxy or phenyl; each R.sup.2 is independently selected from hydroxy, C.sub.1 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.3 acyloxy, C.sub.1 -C.sub.3 alkyoxy or N(C.sub.1 -C.sub.4 alkyl).sub.2, following: F, Cl, hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy, following: F, Cl, --CN, hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy, C.sub.1 -C.sub.8 alkoxycarbonyl, phenyl, following: hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy, phenyl on the carboxamide nitrogen, halogen, CN, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.4 alkyl optionally substituted with one or more of F or C.sub.1 -C.sub.3 alkoxy; following: F, Cl, --CN, hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy, C.sub.1 -C.sub.8 alkoxycarbonyl, phenyl, following: hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy, amino, C.sub.1 -C.sub.4 acylamino, amino-C.sub.1 -C.sub.4 acylamino, Cl, hydroxy, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 acyloxy, amino, C.sub.1 -C.sub.4 acylamino, C.sub.1 -C.sub.4 alkoxycarbonylamino, phenyl on the carboxamide nitrogen C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, phenyl, C.sub.1 -C.sub.4 alkoxy, -C.sub.4 alkoxy,
In one aspect the subject invention is a compound of structural Formula i: ##STR3##
In another aspect the subject invention is composed of structural Formula ii: ##STR4##
In another aspect the subject invention is composed of structural Formula iii: ##STR5##
In yet another aspect, the subject invention is a compound of structural Formula iv: ##STR6##
In yet another aspect, the subject invention is a
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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).
Barbachyn Michael R.
Brickner Steven J.
Hutchinson Douglas K.
Munesada Kiyotaka
Taniguchi Mikio
Corneglio Donald L.
McKane Joseph K.
Pharmacia & Upjohn Company
Yang Lucy X.
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