Substituted oxazine and thiazine oxazolidinone antimicrobials
DC
First Claim
1. A compound of structural Formula I:
- or pharmaceutically acceptable salts thereof wherein;
X is O;
R is (a) hydrogen,(b) C1 -C8 alkyl optionally substituted with one or more of the following;
F, Cl, hydroxy, C1 -C8 alkoxy, C1 -C8 acyloxy or --O--CH2 --Ph,(c) C3 -C6 cycloalkyl,(d) amino,(e) C1 -C8 alkylamino,(f) C1 -C8 dialkylamino or(g) C1 -C8 alkoxy;
R1 is H, CH3, CN, CO2 H, CO2 R or (CH2)mu R11 (m is 1 or
2);
R2 is independently H, F or Cl;
R3 is H except when R1 is CH3 then R3 can be H or CH3 ;
R10 is independently H, C1 -C4 alkyl (optionally substituted with chloro, fluoro, hydroxy,C1 -C8 alkoxy, amino, C1 -C8 alkylamino, or C1 -C8 dialkylamino) or p-toluenesulfonyl;
R11 is hydrogen, OH, OR, OCOR, NH2, NHCOR or N(R10)2 ; and
n is 0, 1 or 2.
1 Assignment
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Abstract
A compound of structural Formula I: ##STR1## or pharmaceutically acceptable salts thereof wherein: X is O, S, SO, SO2, SNR10 or S(O)NR10 ;
R is (a) hydrogen,
(b) C1 -C8 alkyl optionally substituted with one or more of the following: F, Cl, hydroxy, C1 -C8 alkoxy, C1 -C8 acyloxy or --O--CH2 --Ph,
(c) C3 -C6 cycloalkyl,
(d) amino,
(e) C1 -C8 alkylamino,
(f) C1 -C8 dialkylamino or
(g) C1 -C8 alkoxy;
R1 is H, except when X is O then R1 can be H, CH3, CN, CO2 H, CO2 R or (CH2)m R11 (m is 1 or 2);
R2 is independently H, F or Cl;
R3 is H except when X is O and R1 is CH3 then R3 can be H or CH3 ;
R10 is independently H, C1 -C4 alkyl (optionally substituted with chloro, fluoro, hydroxy, C1 -C8 alkoxy, amino, C1 -C8 alkylamino, or C1 -C8 dialkylamino) or p-toluenesulfonyl;
R11 is hydrogen, OH, OR, OCOR, NH2, NHCOR or N(R10)2 ; and n is 0, 1 or 2. The oxazine and thiazine oxazolidinone derivatives 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.
190 Citations
12 Claims
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1. A compound of structural Formula I:
-
or pharmaceutically acceptable salts thereof wherein; X is O; R is (a) hydrogen, (b) C1 -C8 alkyl optionally substituted with one or more of the following;
F, Cl, hydroxy, C1 -C8 alkoxy, C1 -C8 acyloxy or --O--CH2 --Ph,(c) C3 -C6 cycloalkyl, (d) amino, (e) C1 -C8 alkylamino, (f) C1 -C8 dialkylamino or (g) C1 -C8 alkoxy; R1 is H, CH3, CN, CO2 H, CO2 R or (CH2)mu R11 (m is 1 or
2);R2 is independently H, F or Cl; R3 is H except when R1 is CH3 then R3 can be H or CH3 ; R10 is independently H, C1 -C4 alkyl (optionally substituted with chloro, fluoro, hydroxy, C1 -C8 alkoxy, amino, C1 -C8 alkylamino, or C1 -C8 dialkylamino) or p-toluenesulfonyl; R11 is hydrogen, OH, OR, OCOR, NH2, NHCOR or N(R10)2 ; and
n is 0, 1 or 2. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)
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Specification
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- Resources
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Current AssigneePharmacia & Upjohn Company (Pfizer Inc.)
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Original AssigneePharmacia & Upjohn Company (Pfizer Inc.)
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InventorsHutchinson, Douglas K., Brickner, Steven J., Barbachyn, Michael R.
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Primary Examiner(s)Shah, Mukund J.
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Assistant Examiner(s)BUCKNUM, MICHAE
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Application NumberUS08/617,877Time in Patent Office623 DaysField of Search544/137, 514/236.8, 514/235.5US Class Current514/235.5CPC Class CodesC07D 263/20 attached in position 2C07D 413/10 linked by a carbon chain co...C07D 417/10 linked by a carbon chain co...
