Antimicrobial compounds and methods of making and using the same

Claim 1: A compound characterized in that it has the formula: (1), (2), (3), (4) or (5), where Z is selected from the group consisting of O, NR4, S (O) n, NR4CO , CONR4, or NR4CONR4, where -GHJ is alternatively selected from (6), where each H and J are independently selected, CBA-, -DEF, and -GHJ are chemical portions, where A, D, and G are independently selected from the group consisting of: (a) a single bond, (b) - (C1-8alkyl) -, (e) - (C2-8alkenyl) -, (d) - (C2-8alkynyl) -, where i) 0-4 atoms Carbon in any of (b) - (d) immediately above are optionally replaced by a portion selected from the group consisting of -O-, -S (O) p-, -NR6-, - (C = O) -, - S (O) pNR6-, -NR6S (O) p-, and -NR6S (O) pNR6-, ii) any one of (b) - (d) immediately above is optionally substituted with one or more R5 groups, and iii) any one of (b) - (d) immediately above is optionally substituted with groups - (C1-8 alkyl) -R5; (e) -O-, (f) -NR6-, (g) -S (O) p-, (h) -C (O) -, (i) -C (O) O-, (j) - OC (O) -, k) -OC (O) O-, (l) -C (O) NR6-, (m) -NR6CO-, (n) -NR6C (O) NR6-, (o) -C (= NR6) -, (p) (= NR6) O-, (q) -OC (= NR6) -, (r) -C (= NR6) NR6-, (s) -NR6C (= NR6) -, (t) -C (= S) -, (u) -C (= S) NR6-, (v) -NR6C (= S) -, (w) -C (O) S-, (x) -SC (O) -, (y) -OC (= S) -, (z) -C (= S) O-, (aa) -NR6 (CNR6) NR6-, (bb) -CR6R6C (O) -, ( cc) -C (O) NR6 (CR6R6) -, (dd) a saturated heterocycle, 3-14 membered unsaturated or aromatic containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (ee) a 3-14 membered saturated, unsaturated or aromatic carbocycle, and (ff) - (CR6R6) t -, where (dd) or (ee) is optionally substituted with one or more R5 groups; B, E, and H are independently selected from the group consisting of: (a) a single bond, (b) a 3-14 membered saturated, unsaturated, or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (c) a 3-14 membered saturated, unsaturated or aromatic carbocycle, where (b) or (e) is optionally substituted with one or more R5 groups; (d) - (C1-8alkyl) -, (e) - (C2-8alkenyl) -, (f) - (C2-8alkynyl) -, where i) 0-4 carbon atoms in any of (d ) - (f) immediately above, are optionally replaced by a portion selected from the group consisting of -O-, -S (O) p-, -NR6-, - (C = O) -, -C (= NR6) - , -S (O) pNR6-, -NR6S (O) p-, and -NR6S (O) pNR6-, ii) any one of (d) - (f) immediately above, is optionally substituted with one or more R5 groups, and iii) any of (d) - (f) immediately above, is optionally substituted with - (C1-8-alkyl) -R5 groups; and (g) - (CR6R6) t-, C, F, and J are independently selected from the group consisting of: (a) hydrogen, (c) F, (d) Cl, (e) Br, (f) I, (g) -CF3, (h) -CN, (i) -N3, (j) -NO2, ( k) -NR6 (CR6R6) tR8, (l) -OR8, (m) -S (O) p (CR6R6) tR8, (n) -C (O) (CR6R6) tR8, (o) -OC (O) (CR6R6) tR8, (p) -SC (O) (CR6R6) tR8, (q) -C (O) O (CR6R6) tR8, (r) -NR6C (O) (CR6R6) tR8, (s) -C (O) NR6 (CR6R6) tR8, (t) -C (= NR6) (CR6R6) tR8, (u) -C (= NNR6R6) (CR6R6) tR8, (v) -C (= NNR6C (O) R6) (CR6R6) tR8, (w) -C (= NOR8) (CR6R6) tR8, (x) -NR6C (O) O (CR6R6) tR8, (y) -OC (O) NR6 (CR6R6) tR8, (z) -NR6C (O) NR6 (CR6R6) tR8, (aa) -NR6S (O) p (CR6R6) tR8, (bb) -S (O) pNR6 (CR6R6) tR8, (cc) -NR6S (O) pNR6 (CR6R6) tR8, (dd) -NR6R8, (ee) -NR6 (CR6R6) R8, (ff) -OH, (gg) -NR8R8, (hh) -OCH3, (ii) -S (O) pR8, (jj) -NC (O) R8, (kk) -NR6C (NR6) NR6R8, (ll) a C1- alkyl group 8, (mm) a C2-8 alkenyl group, (nn) a C2-8 alkynyl group, (oo) a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (pp) a saturated carbocycle, 3-14 membered unsaturated or aromatic, (qq) - (CR6R6) tNR6 (CR6R6) tR8, (rr) -N [(CR6R6) tR8] [C = O (CR6R6) tR8], (ss) - (CR6R6) tN [(CR6R6) tR8] [(CR6R6) tR8], (tt) - (CR6R6) tNR6 (C = O) (CR6R6) tR8, (uu) -haloalkyl, (vv) -C (O) (CR6) [ (CR6R6) tR8] R8, (ww) - (CR6R6) tC (O) NR8R8, (xx) - (CR6R6) tC (O) O (CR6R6) tR8, (yy) -NR6C (O) CR8R8R8, (zz) -N [(CR6R6) tR8] C (O) R8, and (aaa) -S (O) pNR8R8; where (ll) to (pp) are optionally substituted with one or more R7 groups; R5 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) - NO2, j) -NR6R6, (k) -OR8, (l) -NR6 (CNR6) NR6R6, (m) -C1-8alkyl, (n) -C1-8alkenyl, (o) -C1-8alkynyl , (p) - (C1-8-alkyl) - (a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) - (C1-alkyl -8) - (a 3-14 membered saturated, unsaturated or aromatic carbocycle), (r) -haloalkyl, (s) -SR6, (t) -a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and (u) - a 3-14 membered saturated, unsaturated, or aromatic carbocycle; alternatively, two R5 groups are taken together to form a carbocycle, where (m) through (r) and (t) through (u) are optionally substituted with one or more R8; R6 is selected from (a) hydrogen, (b) -C1-8alkyl or alternatively, two R6 groups are taken together to form a carbocycle, (e) -haloalkyl, (d) -a saturated, unsaturated or aromatic heterocycle of 3 -14 members containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and (e) -a 3-14 membered saturated, unsaturated or aromatic carbocycle; where (b) to (e) are optionally substituted with one or more R8; R7 is selected from (a) hydrogen, (b) F, (c) CI, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R6, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) -C1-8alkyl, (n) -C1-8alkenyl, (o) -C1-alkynyl 8, (p) - (C1-8 alkyl) - (a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) - (alkyl C1-8) - (a 3-14 membered saturated, unsaturated or aromatic carbocycle), (r) -haloalkyl, (s) -NR6R8, (t) -OR8, (u) - (CR6R6) tNR6R8, (v) -CR6R8R8, (w) -SR6, (x) -a saturated, unsaturated or aromatic heterocycle 3-14 membered containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (y) -a 3-14 membered saturated, unsaturated or aromatic carbocycle, (z) - (CR6R6) tC (O) NR8R8, (aa) -S (O) pR8, (bb) -NR6C (O) NR6R6, (cc) -NR6C (O) R6, and (dd) -C (NR6) NR6R6; where (m) to (q) and (x) to (y) are optionally substituted with one or more R9; R8 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) N3, (i) - NO2, (j) -NR6R9, (k) -OR9, (l) -NR6 (CNR6) NR6R6, (m) -C1-8alkyl, (n) -C1-8alkenyl, (o) -C1-8alkynyl , (p) - (C1-8-alkyl) - (a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) - (C1-alkyl -8) - (a 3-14 membered saturated, unsaturated or aromatic carbocycle), (r) -a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (s) -a 3-14 membered saturated, unsaturated or aromatic carbocycle, (t) -haloalkyl, (u) -C (O) (CR6R6) tR9, (v) -SR6, (w) -OC (O) (CR6R6) tR9, (x) -NR6C (O) NR6R9, (y ) -NR6C (O) R9, (z) -NR6 (CNR9) (NR6R6), (aa) -ONR6 (CNR6) NR6R6, (bb) -C (= NR9) NR6R6, (cc) -S (O) p , R9, (dd) - (CR6R6) tC (O) NR6R9, (ee) - (CR6R6) tOR9, and (ff) - (CR6R6) tNR6R9; where (m) to (s) are optionally substituted with one or more R9; R9 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R10, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) -C (O) (CR6R6) tNR6R6, (n) C1-8 alkyl, (o) - C 1-8 alkenyl, (p) -C 1-8 alkynyl, (q) -a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r) -a 3-14 membered saturated, unsaturated or aromatic carbocycle, (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R10, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR10, (y) -S (O) pR6, (z) - (C1-8 alkyl) - (a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (aa) - (C1-8 alkyl) - (- a 3-14 membered saturated, unsaturated or aromatic carbocycle), (bb) -O (CR6R6) tOR6, (cc) -C (= NR6) NR6R6, (dd) -ONR6R6 , (ee) -NR6C (O) NR6R6, (ff) -O (CR6R6) tOR6, (gg) -NR6C (O) R6, and (hh) - (CR6R6) tNR6R10; where (n) through (r) and (z) through (aa) are optionally substituted with one or more R10; R10 is selected from (a) hydrogen, (b) F, (c) Cl, (d) Br, (e) I, (f) -CF3, (g) -CN, (h) -N3, (i) -NO2, (j) -NR6R6, (k) -OR6, (l) -NR6 (CNR6) NR6R6, (m) -C (O) (CR6R6) tNR6R6, (n) C1-8 alkyl, (o) - C 1-8 alkenyl, (p) -C 1-8 alkynyl, (q) -a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r) -a 3-14 membered saturated, unsaturated or aromatic carbocycle, (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R6, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR6, (y) -S (O) pR6, (z) - (C1-8 alkyl) - (- a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (aa ) - (C1-8 alkyl) - (- a 3-14 membered saturated, unsaturated or aromatic carbocycle), (bb) -O (CR6R6) tOR6, (cc) -C (= NR6) NR6R6, (dd) - ONR6R6, (ee) -NR6C (O) NR6R6, (ff) -O (CR6R6) tOR6, (gg) -NR6C (O) R6, and (hh) - (CR6R6) tNR6R6; optionally, where either of -DEF or -GHJ is hydrogen; p is 0, 1, or 2, and t is 0, 1, 2, or 3, or a pharmaceutically acceptable salt, ester, tautomer, or prodrug thereof.