Granted Patent B2

US 7,666,864 · App. 12/411,220 · Granted Feb 23, 2010

Abstract

Claims (136)

1. A compound of structural formula (I):

having a nitroimidazole ring,

or a pharmaceutically acceptable salt thereof;

wherein

R 1 is hydrogen, (C 1 -C 6 )alkyl, aryl, heteroaryl, or heterocycloalkyl;

n is 0, 1, or 2;

X 1 and X 2 are independently H, CF 3 , Cl, OCF 3 or F;

G is —OH, -substituted or unsubstituted triazole, heteroaryl or —NHCOR 2 ;

R 2 is (C 1 -C 6 )alkyl, cycloalkyl, aryl, or heteroaryl; and

L is a bond, or a linker group selected from one or any combination of two to five of the following groups:

1) (C 1 -C 6 )alkylene,

2) (C 3 -C 8 )cycloalkylene,

3) arylene,

4) heteroarylene,

5) heterocycloalkylene containing one to three heteroatoms,

6) —C(═O)—,

7) —O—,

8) —S(O) n —, wherein n is number 0, 1, or 2,

9) —N(R 3 )—,

10) —C(R 4 )═C(R 5 )—,

wherein the carbon or nitrogen atoms of the linker group are unsubstituted or substituted by one to three substituents,

R 3 is hydrogen, (C 1 -C 6 )alkyl, aryl, heteroaryl, or heterocycloalkyl, and

R 4 and R 5 are hydrogen, (C 1 -C 6 )alkyl, aryl, heteroaryl, or heterocycloalkyl, or R 4 and R 5 can join together to form a bond.

2. The compound of claim 1 , wherein L is a bond or a group selected from one or a combination of two to three structural elements selected from the group consisting of:

wherein R 10 , R 11 , R 12 is H, hydroxyl, amino, alkyl, alkylamino, alkoxy, aryl, or heteroaryl that are unsubstituted or substituted, R 13 is H, hydroxyl, amino, alkyl, alkylamino, alkoxy, aryl, or heteroaryl that are unsubstituted or substituted, or R 13 in conjunction with the nitroimidazole ring can form a spiro cyclic structure, m and n are independently 0, 1 or 2, Z is O, S, or CR 14 R 15 , wherein R 14 and R 15 are independently H, alkyl, aryl or heteroaryl group, and G is —OH, -substituted or unsubstituted triazole, heteroaryl, -heteroaryl, or —NHCOR 2 .

3. The compound of claim 2 , wherein the spiro cyclic structure is

4. A compound of structural formula (II):

or a pharmaceutically acceptable salt thereof,

wherein A 1 through A 6 are each independently selected from the group consisting of a bond, a heteroatom, unsubstituted carbon, and substituted carbon, L 1 and L 2 are independently selected from the group consisting of a bond,

G is —OH, -substituted or unsubstituted triazole, or —NHCOCH 3 .

5. The compound of claim 4 , wherein L 2 is a bond.

6. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of claim 1 in combination with a pharmaceutically acceptable carrier.

7. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of claim 2 in combination with a pharmaceutically acceptable carrier.

8. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of claim 4 in combination with a pharmaceutically acceptable carrier.

9. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of claim 6 in combination with a pharmaceutically acceptable carrier.

10. A method of treating a bacterial infection in a subject in need of such treatment comprising administering a pharmaceutical composition of claim 7 to the subject.

11. A method of treating a bacterial infection in a subject in need of such treatment comprising administering a pharmaceutical composition of claim 8 to the subject.

12. A method of treating a bacterial infection in a subject in need of such treatment comprising administering a pharmaceutical composition of claim 9 to the subject.

13. A method of treating a bacterial infection in a subject in need of such treatment comprising administering a pharmaceutical composition of claim 10 to the subject.

14. A compound selected from the group consisting of:

(a) (S,S)—N-{3-[3-Fluoro-4-(4-{2-[4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-phenoxy]-acetyl}-piperazin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(b) (S,S)—N-(3-{3-Fluoro-4-[4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-benzyloxy]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(c) (S,S)—N-(3-{3-Fluoro-4-[3-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-benzyloxy]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(d) (S,S)—N-(3-{3-Fluoro-4-[5-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-2-yloxy]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(e) (S,S)—N-(3-{3-Fluoro-4-[4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-phenoxy]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(f) (S,S)—N-[3-(3-Fluoro-4-{1-[4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-benzyl]-1H-[1,2,3]triazol-4-ylmethoxy}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

(g) (S,S)—N-(3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(h) (S,S)—N-(3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(i) (S,S)—N-(3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-4-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(j) N-(3-{3-Fluoro-4-[5-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(k) (S,S)—N-(3-{3-Fluoro-4-[5-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-2-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(l) (S,S)—N-(3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(m) (S,S)—N-(3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridazin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(n) (S,S)—N-(3-{3-Fluoro-4-[4-morpholin-4-yl-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(o) (S,S)—N-(3-{3-Fluoro-4-[4-methoxy-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(p) (S,S)—N-(3-{4-[4-Dimethylamino-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(q) (S,S)-5-{4-[5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-nicotinic acid methyl ester;

(r) (S,S)-5-{4-[5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-nicotinic acid;

(s) (S,S)—N-(3-{3-Fluoro-4-[4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-2-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(t) (S,S)—N-(3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-4-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(u) (S,S)—N-(3-{3-Fluoro-4-[5-methyl-6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(v) (S,S)—N-(3-{3-Fluoro-4-[2-methyl-6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(w) N-(3-{3-Fluoro-4-[5-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-pyridin-2-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(x) (S,S)—N-(3-{3-Fluoro-4-[4-(4-methoxy-benzyloxy)-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(y) (S,S)—N-(3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-6-oxo-1,6-dihydro-pyrimidin-5-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(z) (S,S)—N-(3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-4-trifluoromethyl-pyrimidin-5-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(aa) (S,S)—N-{3-[2,6-Difluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(bb) N-{3-[4-(6-Nitro-imidazo[2,1-b]-2(3H)-8-aza-spiro[4,5]dec-8-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5 (S)-ylmethyl}-acetamide;

(cc) (S,R)-3-[2-Fluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-biphenyl-4-yl]-5-hydroxymethyl-oxazolidin-2-one;

(dd) (S,S)-3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(ee) (S,R)-3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(ff) (S,S)—N-{3-[2-Fluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(gg) (S,S)—N-[3-(3-Fluoro-4-{4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-acetyl]-piperazin-1-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

(hh) N-(3-{3-Fluoro-4-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(ii) (S,R)-3-[2-Fluoro-4′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-biphen-4-yl]-5-[1,2,3]triazol-1-ylmethyl-oxazolidin-2-one;

(jj) (S,R)-3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-3-yl]-phenyl}-5-[1,2,3]triazol-1-ylmethyl-oxazolidin-2-one;

(kk) N-{3-[2-Fluoro-4′-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(ll) N-{3-[2-Fluoro-3′-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(mm) N-{3-[2′-Chloro-2-fluoro-4′-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(nn) N-{3-[3′-Chloro-2-fluoro-4′-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(oo) N-{3-[3′-Cyano-2-fluoro-4′-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(pp) N-(3-{2-Fluoro-4′-[(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-amino]-biphenyl-4-yl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(qq) (S,S)—N-(3-{3-Fluoro-4-[3-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-propenyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(rr) (E)-N-(3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxy)-vinyl]-phenyl}-2-oxo-oxazolidin-5(S)-ylmethyl)-acetamide;

(ss) N-(3-{3-Fluoro-4-[1-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxymethyl)-vinyl]-phenyl}-2-oxo-oxazolidin-5(S)-ylmethyl)-acetamide;

(tt) N-(3-{3-Fluoro-4-[2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-acetyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(uu) N-(3-{3-Fluoro-4-[1-hydroxy-1-hydroxymethyl-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-ethyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(vv) (S,S)—N-(3-{3-Fluoro-4-[3-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-prop-1-ynyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(ww) (S,S)—N-{3-[2,2′-Difluoro-5′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(xx) (S,S)—N-{3-[2-Fluoro-3′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-loxymethyl)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(yy) N-{3-[3-Fluoro-4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide; and

(zz) N-(((5S)-3-(3-Fluoro-4-(2-((2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methoxy)pyrimidin-5-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide, and

their pharmaceutically acceptable salts.

15. A compound selected from the group consisting of:

(a) N—(((S)-3-(3-Fluoro-4-(5-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]-oxazin-6-yloxy)methyl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide;

(b) N—(((S)-3-(3-Fluoro-4-(2-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]-oxazin-6-yloxy)methyl)pyridin-4-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide;

(c) N—(((S)-3-(3-Fluoro-4-(4-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]-oxazin-6-yloxy)methyl)pyridin-2-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide;

(d) N—(((S)-3-(3-Fluoro-4-(6-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]-oxazin-6-yloxy)methyl)pyridin-2-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide;

(e) N—(((S)-3-(3-Fluoro-4-(6-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]-oxazin-6-yloxy)methyl)pyridazin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide;

(f) N—(((S)-3-(3-Fluoro-4-(5-(((S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]-oxazin-6-yloxy)methyl)pyrazin-2-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide;

(g) N-({(5S)-3-[3-Fluoro-4-(2-{4-[(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazol-2-yl)methyl]-1-piperazinyl}-5-pyrimidinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;

(h) (S,S)—N-(3-{2,3′-Difluoro-4′-{-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-biphenyl-4-yl]-2-oxo-oxazolidin-5-yl}methyl)acetamide;

(i) N-[((5S)-3-{3-Fluoro-4-[5-({[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl]oxy}methyl)-2-thienyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide;

(j) N-({(5S)-3-[3-Fluoro-4-(6-{4-[(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazol-2-yl)methyl]-1-piperazinyl}-3-pyridinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide;

(k) 3-{3-Fluoro-4-[5-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-2-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(l)3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridazin-3-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(m) 3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-3-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(n) N-(3-{3,5-Difluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(o) 3-{3-Fluoro-4-[2-methyl-6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(p) 3-{3,5-Difluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(q) 5-Hydroxymethyl-3-{4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-3-trifluoromethoxy-phenyl}-oxazolidin-2-one;

(r) 5-Hydroxymethyl-3-[6′-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-[2,3′]bipyridinyl-5-yl]-oxazolidin-2-one;

(s) 3-{4-[4-Dimethylamino-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyrimidin-5-yl]-3-fluoro-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(t) N-[3-(3-Fluoro-4-{5-[(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ylamino)-methyl]-pyridin-2-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

(u) N-[3-(3-Fluoro-4-{6-[(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ylamino)-methyl]-pyridin-3-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

(v) 5-Hydroxymethyl-3-{4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-3-yl]-3-trifluoromethoxy-phenyl}-oxazolidin-2-one;

(w) 3-[2-Fluoro-4′-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-biphenyl-4-yl]-5-hydroxymethyl-oxazolidin-2-one;

(x) N-{3-[2-Fluoro-4′-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(y) N-(3-{3-Fluoro-4-[6-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(z) N-[3-(3-Fluoro-4-{2-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]-pyrimidin-5-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

(aa) 3-(3-Fluoro-4-{2-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]-pyrimidin-5-yl}-phenyl)-5-hydroxymethyl-oxazolidin-2-one;

(bb) 3-{3-Fluoro-4-[6-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-pyridin-3-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one;

(cc) N-(3-{2-Fluoro-4′-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]-biphenyl-4-yl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide;

(dd) N-[3-(3-Fluoro-4-{6-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]-pyridin-3-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

(ee) Phosphoric acid mono-(3-{3-fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)ester;

(ff) 3-[3-Fluoro-4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-phenyl]-5-hydroxymethyl-oxazolidin-2-one;

(gg) N-{3-[3-Fluoro-4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(hh) 2-Allyl-2-(4-bromo-phenyl)-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole;

(ii) N-{3-[4′-(2-Allyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-2-fluoro-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide;

(jj) 3-[4-(2-Allyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-phenyl]-5-hydroxymethyl-oxazolidin-2-one;

(kk) 3-(3-Fluoro-4-{2-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-[1,4]diazepan-1-yl]-pyrimidin-5-yl}-phenyl)-5-hydroxymethyl-oxazolidin-2-one;

(ll) 3-(3-Fluoro-4-{6-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-[1,4]diazepan-1-yl]-pyridin-3-yl}-phenyl)-5-hydroxymethyl-oxazolidin-2-one;

(mm) N-[3-(3-Fluoro-4-{6-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-[1,4]diazepan-1-yl]-pyridin-3-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

(nn) 3-{3-Fluoro-4-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one; and

(oo) N-[3-(3-Fluoro-4-{2-[4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazin-1-yl]-thiazol-5-yl}-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide, and

their pharmaceutically acceptable salts.

Assignments (9)