Claims
- 1. A compound of formula I: ##STR101## wherein R.sup.1 is (a) --COR.sup.3,
- (b) --COCH.sub.2 Cl,
- (c) --COCHCl.sub.2,
- (d) --COCH.sub.2 F,
- (e) --COCHF.sub.2,
- (f) --CO.sub.2 CH.sub.3,
- (g) --SO.sub.2 CH.sub.3,
- (h) --COCH.sub.2 OH,
- (i) --CSR.sup.3,
- (j) --CSNH.sub.2, or
- (k) --CSNHCH.sub.3 ;
- wherein X.sup.1 and X.sup.2 are independently
- (a) H,
- (b) F, or
- (c) Cl;
- wherein Q is
- (a) 1,3,4-thiadiazol-2-yl: ##STR102## (b) 1,2,4-thiadiazol-3-yl: ##STR103## (c) 1,2,4-thiadiazol-5-yl: ##STR104## (d) 1,2,5-thiadiazol-3-yl: ##STR105## (e) 1,3,4-oxadiazol-2-yl: ##STR106## (f) 1,2,4-oxadiazol-3-yl: ##STR107## (g) 1,2,4-oxadiazol-5-yl ##STR108## wherein R.sup.2 is (a) R.sup.3 --
- (b) R.sup.4 CO.sub.2 (CH.sub.2).sub.n --,
- (c) NC(CH.sub.2).sub.n --,
- (d) R.sup.3 OCO(CH.sub.2).sub.n --,
- (e) R.sup.3 R.sup.5 NCO(CH.sub.2).sub.n --,
- (f) R.sup.3 R.sup.5 N(CH.sub.2).sub.n --,
- (g) R.sup.4 CONR.sup.5 (CH.sub.2).sub.n --,
- (h) CF.sub.3 (CH.sub.2).sub.n --,
- (i) CF.sub.2 H(CH.sub.2).sub.n --,
- (j) R.sup.4 CO(CH.sub.2).sub.n --,
- (k) F(CH.sub.2).sub.n --,
- (l) Cl(CH.sub.2).sub.n --,
- (m) Br(CH.sub.2).sub.n --,
- (n) R.sup.3 O(CH.sub.2).sub.n --,
- (o) R.sup.3 S(CH.sub.2).sub.n --,
- (p) R.sup.3 SO(CH.sub.2).sub.n --,
- (q) R.sup.3 SO.sub.2 (CH.sub.2).sub.n --,
- (r) R.sup.3 SO.sub.2 NR.sup.5 (CH.sub.2).sub.n --,
- (s) R.sup.3 R.sup.4 C(OH)(CH.sub.2).sub.n --,
- (t) R.sup.3 R.sup.4 C(NHR.sup.5)(CH.sub.2).sub.n --,
- (u) HO.sub.2 C(CH.sub.2).sub.n --,
- (v) O.sub.2 N(CH.sub.2).sub.n --,
- (w) C.sub.2 -C.sub.6 alkenyl,
- (x) C.sub.2 -C.sub.6 alkynyl,
- (y) --CCl.sub.3,
- (z) R.sup.3 ON.dbd.CR.sup.3 (CH.sub.2).sub.n --,
- (aa) NCNR.sup.5 (CH.sub.2).sub.n --,
- (bb) R.sup.3 ONR.sup.5 (CH.sub.2).sub.n --, or
- (cc) R.sup.3 OC(O)NR.sup.5 (CH.sub.2).sub.n --;
- wherein n is 0, 1, 2, 3, 4 or 5;
- wherein p is 1, 2 or 3;
- wherein R.sup.3 is
- (a) H,
- (b) C.sub.1 -C.sub.5 alkyl, or
- (c) cyclopropyl-;
- wherein R.sup.4 is
- (a) H,
- (b) C.sub.1 -C.sub.5 alkyl-,
- (c) cyclopropyl-,
- (d) R.sup.3 O(CH.sub.2).sub.p --, or (e) R.sup.3 CO.sub.2 (CH.sub.2).sub.p --;
- wherein R.sup.5 is
- (a) H, or
- (b) C.sub.1 -C.sub.3 alkyl;
- or a pharmaceutically acceptable salt thereof;
- with the following proviso:
- at least one of X.sup.1 and X.sup.2 is F or Cl.
- 2. The compound of claim 1
- wherein R.sup.1 is
- (a) --COR.sup.3, or
- (b) --CSR.sup.3 ;
- wherein X.sup.1 and X.sup.2 are independently
- (a) H, or
- (b) F;
- wherein Q is the moiety of formula II or IV;
- wherein R.sup.2 is
- (a) R.sup.3,
- (b) R.sup.3 CO.sub.2 (CH.sub.2).sub.n --,
- (c) NC(CH.sub.2).sub.n --,
- (d) R.sup.3 OCO(CH.sub.2).sub.n --,
- (e) R.sup.3 R.sup.5 NCO(CH.sub.2).sub.n --,
- (f) R.sup.3 R.sup.5 N(CH.sub.2).sub.n --,
- (g) R.sup.4 CONR.sup.5 (CH.sub.2).sub.n --,
- (h) CF.sub.3 (CH.sub.2).sub.n --,
- (i) R.sup.4 CO(CH.sub.2).sub.n --,
- (j) F(CH.sub.2).sub.n --,
- (k) Cl(CH.sub.2).sub.n --,
- (l) R.sup.3 O(CH.sub.2).sub.n --,
- (m) R.sup.3 S(CH.sub.2).sub.n --,
- (n) R.sup.3 SO(CH.sub.2).sub.n --,
- (o) R.sup.3 SO.sub.2 (CH.sub.2).sub.n --,
- (p) R.sup.3 SO.sub.2 NR.sup.5 (CH.sub.2).sub.n --,
- (q) O.sub.2 N(CH.sub.2).sub.n --, or
- (r) R.sup.3 R.sup.4 C(NHR.sup.5)(CH.sub.2).sub.n --;
- (o) R.sup.3 SO.sub.2 NR.sup.3 (CH.sub.2).sub.n --,
- (p) R.sup.3 R.sup.4 C(OH)(CH.sub.2).sub.n --, or
- (q) C.sub.2 -C.sub.6 alkenyl;
- wherein n is 0, 1, or 2;
- wherein R.sup.4 is
- (a) H,
- (b) C.sub.1 -C.sub.3 alkyl, or
- (c) cyclopropyl.
- 3. The compound of claim 2
- wherein R.sup.2 is
- (a) R.sup.3,
- (b) NC(CH.sub.2).sub.n --,
- (c) R.sup.3 NHCO(CH.sub.2).sub.n --,
- (d) R.sup.4 CO(CH.sub.2).sub.n --,
- (e) F(CH-.sub.2).sub.n --,
- (g) Cl(CH.sub.2).sub.n --,
- (h) R.sup.3 O(CH.sub.2).sub.n --,
- (i) R.sup.3 S(CH.sub.2).sub.n --,
- (j) R.sup.3 NH(CH.sub.2).sub.n --, or
- (k) R.sup.4 CONH(CH.sub.2).sub.n --.
- 4. The compound of claim 3 wherein Q is the moiety of formula II.
- 5. The compound of claim 1 selected from the group consisting of:
- 1. (S)-N-[[3-[4(5-Cyano-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]-methyl]acetamide;
- 2. (S)-5-[4-[5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazole-2-carboxamide;
- 3. (S)-N-[[3-[3-Fluoro-4(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 4. (S)-N-[[3-[4-(5-Ethyl-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 5. (S)-N-[[3-[3-Fluoro-4-(5-propyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 6. (S)-N-[[3-[4-[5-(Aminomethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 7. S)-N-[[3-[3-Fluoro-4-[5-[[(methylsulfonyl)amino]methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 8. (S)-N-[[3-[3-Fluoro-4-(5-fluoromethyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 9. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 10. (S)-N-[[3-[4-(5-Acetoxymethyl-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 11. (S)-N-[[3-[3-Fluoro-4-(5-hydroxymethyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 12. (S)-N-[[3-[3-Fluoro-4-[5-(methoxymethyl)-1,3,4-thiadiazol -2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 13. (S)-N-[[3-[4-[5-(Cyanomethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 14. (S)-5-[4-[5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazole-2-acetamide;
- 15. (S)-N-[[3-[3-Fluoro-4-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 16. (S)-N-[[3-[3-Fluoro-4-[5-(3-oxobutyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 17. (5S)-N-[[3-[3-Fluoro-4-[5-(3-hydroxybutyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo5-oxazolidinyl]methyl]acetamide;
- 18. (S)-Methyl 5-[4-[5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazole-2-propanoate;
- 19. (S)-5-[4-[5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazole-2-propanamide;
- 20. (S)-N-[[3-[4-[5-(2-Cyanoethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 21. (S)-N-[[3-[3-Fluoro-4-[5-[(methylthio)methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 22. (S)-N-[[3-[3-Fluoro-4-[5-[(methylsulfmyl)methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 23. (S)-N-[[3-[3-Fluoro-4-[5-[2-(methylthio)ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 24. (S)-N-[[3-[3-Fluoro-4-[5-[2-(methylsulfmyl)ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 25. (S)-Ethyl 5-[4-[5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazole-2-acetate;
- 26. (S)-N-[[3-[3-Fluoro-4-[5-(2-hydroxyethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 27. (S)-Ethyl 5-[4-[5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazole-2-carboxylate;
- 28. (5S)-N-[[3-[3-Fluoro-4-[5-(2-hydroxypropyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 29. (S)-N-[[3-[4-(4,5-Dihydro-5-oxo-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 30. (S)-N-[[3-[4-(5-Amino-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 31. (S)-N-[[3-[3-Fluoro-4-[5-(methylthio)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 32. (S)-N-[[3-[3-Fluoro-4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanamide;
- 33. (S)-3-[4-[5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,2,4-thiadiazole-5-carboxamide;
- 34. (S)-N-[[3-[3-Fluoro-4-(1,2,4-thiadiazol-5-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 35. (S)-N-[[3-[3-Fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 36. (S)-N-[[3-[3-Fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 37. (S)-3-[4-[5-[(Acetylaniino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,2,4-oxadiazole-5-carboxamide;
- 38. (S)-N-[[3-[4-(5-Cyano-1,2,4-oxadiazol-3-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 39. (S)-N-[[3-[3-Fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 40. (S)-N-[[3-[3-Fluoro-4-(1,2,4-oxadiazol-5-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 41. (S)-N-[[3-[3-Fluoro-4-[5-(formylamino)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 42. (S)-N-[[3-[4-[5-(2-Chloroethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 43. (S)-N-[[3-[3-Fluoro-4-[5-(1-propenyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamnide;
- 44. (S)-N-[[3-[4-[5-(2-Aminoethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 45. (S)-N-[[3-[4-[5-[2-(Acetylamino)ethyl]-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 46. (S)-N-[[3-[3-Fluoro-4-[5-[2-[(methylsulfonyl)amino]ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 47. (5S)-N-[[3-[3-Fluoro-4-[5-(methylsulfmyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 48. (S)-N-[[3-[3-Fluoro-4-[5-(1-methylethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 49. (S)-N-[[5-[4-[5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazol-2-yl]methyl]acetamide;
- 50. (S)-N-[[3-[3-Fluoro-4-[5-(3-hydroxypropyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 51. [S-(R*,R*)]-N-[[3-[3-Fluoro-4-[5-(1-hydroxyethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 52. [S-(R*,S*)]-N-[[3-[3-Fluoro-4-[5-(1-hydroxyethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 53. (S)-N-[[3-[3-Fluoro-4-[5-(2-nitroethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 54. (S)-N-[[3-[3-Fluoro-4-[5-(3-nitropropyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 55. [S-(R*,R*)]-N-[[3-[4-[5-(1-Aminoethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 56. [S-(R*,S*)]-N-[[3-[4-[5-(1-Aminoethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 57. (S)-N-[[3-[4-[5-(3-Aminopropyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 58. (S)-N-[3-[5-[4-[5-[(Acetylanino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazol-2-yl]propyl]acetamide;
- 59. (S)-N-[[3-[4-(5-Acetyl-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 60. (S)-N-[[3-[4-[5-(3-Chloropropyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 61. (S)-N-[[3-[4-[5-(3-Cyanopropyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 62. (S)-N-[[3-[3-Fluoro-4-[5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 63. (S)-N-[[3-[3-Fluoro-4-[5-[3-(hydroxyimino)butyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 64. (S)-N-[[3-[3-Fluoro-4-[5-[2-(hydroxyimino)ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 65. (S)-N-[[3-[3-Fluoro-4-[5-[3-(methoxyimino)butyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 66. (S)-N-[[5-[4-[5-[(Acetyloxyacetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazol-2-yl]methyl]acetamide;
- 67. (S)-N-[[5-[4-[5-[(Hydroxyacetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazol-2-yl]methyl]acetamide;
- 68. (S)-N-[5-[4-[5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazol-2-yl]-2-(acetyloxy)acetamide;
- 69. (S)-N-[[3-[3-Fluoro-4-[5-[(methylsulfonyl)methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 70. (S)-N-[[3-[3-Fluoro-4-[5-[2-(methylsulfonyl)ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 71. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanamide;
- 72. (S)-N-[[3-[3-Fluoro-4-[5-(2-methoxyethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]propanamide;
- 73. (S)-N-[[3-[3-Fluoro-4-[5-(2-methoxyethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 74. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide;
- 75. (S)-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thiourea;
- 76. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanethioamide;
- 77. N-[((5S)-3-{4-[5-(aminomethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]ethanethioamide;
- 78. 2-({[5-(4-{(5S)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1,3,4-thiadiazol-2-yl]methyl}amino)-2-oxoethyl acetate; and
- 79. N-{[5-(4-{(5S)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1,3,4-thiadiazol-2-yl]methyl}-2-hydroxyacetamide.
- 6. The compound of claim 5 which is
- 1. (S)-N-[[3-[4-(5-Cyano-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 2. (S)-N-[[3-[3-Fluoro-4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 3. (S)-N-[[3-[4(5-Ethyl-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 4. (S)-N-[[3-[4-[5-(Aminomethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 5. (S)-N-[[3-[3-Fluoro-4-[5-[[(methylsulfonyl)amino]methyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 6. (S)-N-[[3-[3-Fluoro-4-(5-fluoromethyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 7. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 8. (S)-N-[[3-[4-(5-Acetoxymethyl-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 9. (S)-N-[[3-[3-Fluoro-4-(5-hydroxymethyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 10. (S)-N-[[3-[4-[5-(Cyanomethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 11. (S)-5-[4-[5-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1,3,4-thiadiazole-2-acetamide;
- 12. (S)-N-[[3-[3-Fluoro-4-[5-(3-oxobutyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 13. (S)-N-[[3-[4-[5-(2-Cyanoethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 14. (S)-N-[[3-[3-Fluoro-4-[5-[2-(methylsulfinyl)ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 15. (S)-N-[[3-[3-Fluoro-4-[5-(2-hydroxyethyl)-1,3,4-thiadiazo 1-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 16. (S)-N-[[3-[4-(4,5-Dihydro-5-oxo-1,3,4-thiadiazol-2-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 17. (S)-N-[[3-[3-Fluoro-4-[5-(methylthio)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 18. (S)-N-[[3-[3-Fluoro-4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanamide;
- 19. (5S)-N-[[3-[3-Fluoro-4-[5-(methylsulfinyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 20. (S)-N-[[3-[3-Fluoro-4-[5-(3-hydroxypropyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 21. [S-(R*,R*)]-N-[[3-[3-Fluoro-4-[5-(1-hydroxyethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
- 22. [S-(R*,S*)]-N-[[3-[3-Fluoro-4-[5-(1-hydroxyethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 23. (S)-N-[[3-[3-Fluoro-4-[5-(2-nitroethyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 24. (S)-N-[[3-[3-Fluoro-4-[5-(3-nitropropyl)-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 25. [S-(R*,R*)]-N-[[3-[4-[5-(1-Aminoethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 26. [S-(R*,S*)]-N-[[3-[4-[5-(1-Aminoethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 27. (S)-N-[[3-[4-[5-(3-Cyanopropyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 28. (S)-N-[[3-[3-Fluoro-4-[5-[3-(hydroxyimino)butyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 29. (S)-N-[[3-[3-Fluoro-4-[5-[2-(hydroxyimino)ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 30. (S)-N-[[3-[3-Fluoro-4-[5-[2-(methylsulfonyl)ethyl]-1,3,4-thiadiazol-2-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;
- 31. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanamide;
- 32. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide;
- 33. (S)-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thiourea;
- 34. (S)-N-[[3-[3-Fluoro-4-(1,3,4-thiadiazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanethioamide;
- 35. N-[((5S)-3-{4-[5-(aminomethyl)-1,3,4-thiadiazol-2-yl]-3-fluorophenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]ethanethioamide;
- 36. 2-({[5-(4-{(5S)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1,3,4-thiadiazol-2-yl]methyl}amino)-2-oxoethyl acetate; or
- 37. N-{[5-(4-{(5S)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)-1,3,4-thiadiazol-2-yl]methyl}-2-hydroxyacetamide.
CROSS-REFERENCE TO RELATED APPLICATION
This application claims the benefit of the following provisional applications: U.S. Ser. No. 60/052,907, filed Jul. 11, 1997; U.S. Ser. No. 60/064,746, filed Nov. 7, 1997, both under 35 USC 119(e)(i).
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