Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents

Claim 1

An aryl benzene oxazolidinone of the formula wherein, for the t, and mixtures of the d and ℓ stereoisomers of the compound Ar is an aromatic group 5 selected from the group consisting of a diazinyl group optionally substituted with X and Y, a triazinyl group optionally substituted with X and Y, and Z is O, S, or NRs; W is CH or N, or also can be S or 0 when Z is NRs; X independently is H, -N0 2 , -S(O) n R 1 , tetrazoyl, alkyl of 1 to 8 carbons optionally substituted with one or more halogen atoms, OH, = 0 other than at alpha position, S(O) n R 24 , or NR 5 R 6 , alkenyl of 2-5 carbons or cycloalkyl of 3-8 carbons; R, is C 1 -C 4 alkyl, optionally substituted with one or more halogen atoms, OH, CN, NR 5 R 6 or CO 2 R 8 ; C 2 -C 4 alkenyl; -NR 9 R 10 ; -N 3 ; -NG 2 ; NR 9 G-NGM + ; R 2 and R 3 are independently C 1 -C 2 alkyl or, taken together are -(CH 2 ) q -; R 4 is alkyl or 1-4 carbons, optionally substituted with one or more halogens; R s and R 6 are independently H, alkyl of 1-8 carbons, cycloalkyl of 3-8 carbons -(CH 2 ) t OR s , -(CH 2 )- t NR 11 R 11a , or -O(CH 2 ) t NR 11 R 11a ; or taken together are -(CH 2 ) 2 O(CH 2 ) 2 -, -(CH 2 ) t CH(COR 4 )-, or R 7 is -NR 5 R 6 , -ORs or NH Rs; R 8 is H or alkyl of 1-4 carbons; Rs is H, C 1 -C 4 alkyl or C 3 -C 8 cycloalkyl; R 10 is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 4 cycloalkyl, -OR 8 or -NR 11 R 11A ; R 11 and R 11A are independently H or C 1 -C 4 alkyl, or taken together, are -(CH 2 ) r -; G is Cl, Br or I; Y independently is H, F, Cl, Br, OR s , alkyl of 1-3 carbons, or N0 2 ; X and Y taken together (a) when Ar is or to form a fused six-membered carbocyclic ring, or (b) when Ar is to form M is a physiologically acceptable cation; n is 0, 1 or 2 p is 0 or 1; q is 3, 4 or 5; r is 4 or 5; t is 1, 2 or 3; B is -NH 2 ; or N 3 ; R 12 is H, C 1 -C 10 alkyl or C 3 -C 8 cycloalkyl; R, 3 is H; C 1 -C 4 alkyl optionally substituted with one or more halogen atoms; C2-C4 alkenyl; C3-C4 cycloalkyl; phenyl; -CH 2 OR 15 ; -CH(OR 16 )OR 17 ; -CH 2 S(O) v R 14 ; -OR 18 ; - SR 14 ; -CH 2 N 3 ; the aminoalkyl groups derived from a-amino acids such as glycine, L-alanine, L-cysteine, L-proline, and D-alanine; -NR 19 R 20 ; or -C(NH 2 )R 21 R 22 ; R 14 is C 1 -C 4 alkyl, optionally substituted with one or more halogen atoms; R 15 is H or C 1 -C 4 alkyl, optionally substituted with one or more halogen atoms; R 16 and R 17 are independently C 1 -C 4 alkyl or, taken together, are -(CH 2 ) m- ; R 1 8 is C 1 -C 4 alkyl or C 7 -C 11 aralkyl; R 19 and R 20 are independently H or C 1 -C 2 alkyl; R 2 , and R 22 are independently H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, phenyl or, taken together, are -(CH 2 ) s -; u is 1 or 2; v is 0, 1 or 2; m is 2 or 3; s is 2, 3, 4 or 5; R 23 is H, alkyl of 1-8 carbons optionally substituted with one or more halogens, cycloalkyl of 3-8 carbons, alkyl of 1-4 carbons substituted with one or more of -S(O) n R 24 , -OR 8 , or -NR s R s ; or alkenyl of 2-5 carbons optionally substituted with CHO or C0 2 R 8 ; R 24 is alkyl of 1-4 carbons or cycloalkyl of 3-8 carbons; and R 25 is R 6 or NR 5 R 6 ; or a pharmaceutically suitable salt thereof; provided that: 1) when B is NH 2 , then Ar is not phenyl optionally substituted with halogen or CF 3 .