AR080559A1 - DERIVATIVES OF IMIDAZOPIRIMIDINAS, ITS USE AS ANTIMICROBIALS AND METHODS TO PREPARE AND USE THEM - Google Patents

DERIVATIVES OF IMIDAZOPIRIMIDINAS, ITS USE AS ANTIMICROBIALS AND METHODS TO PREPARE AND USE THEM

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AR080559A1
AR080559A1 ARP100103805A ARP100103805A AR080559A1 AR 080559 A1 AR080559 A1 AR 080559A1 AR P100103805 A ARP100103805 A AR P100103805A AR P100103805 A ARP100103805 A AR P100103805A AR 080559 A1 AR080559 A1 AR 080559A1
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Argentina
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cr6r6
unsaturated
saturated
aromatic
group
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ARP100103805A
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Spanish (es)
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Erin M Duffy
Ashoke Bahattacharjee
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Rib X Pharmaceuticals Inc
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Publication of AR080559A1 publication Critical patent/AR080559A1/en

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    • A61K31/5375—1,4-Oxazines, e.g. morpholine
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Abstract

La presente se refiere, al campo de los compuestos antimicrobianos y a los métodos para prepararlos y utilizarlos. Estos compuestos son utiles para tratar, prevenir y reducir el riesgo de infecciones microbianas en humanos y animales. Reivindicacion 1: Un compuesto caracterizado porque tiene la formula (1), (2), (3) o (4) donde -G-H-J se selecciona, alternativamente, de -G(H-J)(H-J), donde cada H y J se selecciona independientemente de, C-B-A-, -D-E-F, y -G-H-J son porciones químicas, donde A, D y G se seleccionan, independientemente, del grupo formado por: (a) un enlace simple, (b) alquilo C1-8, (c) alquenilo C2-8, (d) alquinilo C2-8, donde i) 0-4 átomos de carbono en cualquiera de (b)-(d) inmediatamente arriba, está opcionalmente reemplazado por una porcion seleccionada del grupo formado por -O-, S(O)p, -NR6-, -(C=O)-, -S(O)pNR6-, -NR6S(O)p-, y -NR6S(O)pNR6-, ii) cualquiera de (b)-(d) inmediatamente arriba, está opcionalmente sustituida con uno o más grupos R5, y iii) cualquiera de (b)-(d) inmediatamente arriba, está opcionalmente sustituida con grupos alquilo C 1-8-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) -C(=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)t-, (dd) un heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo formado por nitrogeno, oxígeno y azufre, o (ee) un carbociclo saturado, insaturado o aromático de 3-14, y (ff) -(CR6R6)t-, donde (dd) o (ee) está opcionalmente sustituido con uno o más grupos R5; B, E, y H se seleccionan independientemente del grupo formado por: (a) un enlace simple, (b) un heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo formado por nitrogeno, oxígeno y azufre, (c) un carbociclo saturado, insaturado o aromático de 3-14 miembros, donde (b) o (c) está opcionalmente sustituido con uno o más grupos (d) alquilo C1-8, (e) alquenilo C2-8, (f) alquinilo C2-8, donde i) 0-4 átomos de carbono en cualquiera de (d)-(f) inmediatamente arriba, está opcionalmente reemplazado por una porcion seleccionada del grupo formado por -O-, -S(O)p-, -NR6-, -(C=O)-, -C(=NR6)-, -S(O)pNR6-, -NR6S(O)p-, y -NR6S(O)pNR6-, ii) cualquiera de (d)-(f) inmediatamente arriba está opcionalmente sustituido con uno o más grupos R5, y iii) cualquiera de (d)-(f) inmediatamente arriba está opcionalmente sustituido con grupos alquilo C1-8-R5; y (g) -(CR6R6)t-, C, F, y J están independientemente seleccionados del grupo formado por: (a) hidrogeno, (c) F, (d) CI, (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) un grupo alquilo C1-8, (mm) alquenilo C2-8, (nn) alquinilo C2-8, (oo) un heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre, (pp) un carbociclo saturado, insaturado o aromático de 3-14 miembros, (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) -haloalquilo, (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, y (aaa) -S(O)pNR8R8; donde (ll) a (pp) están opcionalmente sustituidos con uno o más grupos R7; R5 se selecciona de (a) hidrogeno, (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) alquilo C1-8, (n) alquenilo C1-8, (o) alquinilo C1-8, (p) -alquilo C1-8-(un heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre), (q) -alquilo C1-8-(carbociclo saturado, insaturado o aromático de 3-14 miembros), (r) -haloalquilo, (s) -SR6, (t) heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre, y (u) carbociclo saturado, insaturado o aromático de 3-14 miembros; alternativamente, dos grupos R5 se toman juntos para formar un carbociclo donde (m) a (r) y (t) a (u) están opcionalmente sustituidos con uno o más R8; R6 se selecciona de (a) hidrogeno, (b) alquilo C1-8 o alternativamente dos grupos R6 se toman juntos para formar un carbociclo, (c) -haloalquilo, (d) un heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre, y (e) carbociclo saturado, insaturado o aromático de 3-14 miembros; donde (b) a (e) están opcionalmente sustituido con uno o más R8; R7 se selecciona de (a) hidrogeno, (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) alquilo C1-8, (n) alquenilo C1-8, (o) alquinilo C1-8, (p) -alquilo C1-8-(heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre), (q) alquilo C1-8-(carbociclo saturado, insaturado o aromático de 3-14 miembros), (r) haloalquilo-, (s) -NR6R8, (t) -OR8, (u) -(CR6R6)tNR6R8, (v) -CR6R8R8, (w) -SR6, (x) heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre, (y) carbociclo saturado, insaturado o aromático de 3-14 miembros, (z) -(CR6R6)tC(O)NR8R8, (aa) -S(O)pR8, (bb) -NR6C(O)NR6R6, (cc) -NR6C(O)R6, (dd) -C(=NR6)NR6R6; donde (m) a (q) y (x) a (y) están opcionalmente sustituidos con una o más R9; R8 se selecciona de (a) hidrogeno, (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) alquilo C1-8, (n) alquenilo C1-8, (o) alquinilo C1-8, (p) -alquilo C1-8-(heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre), (q) alquilo C1-8-(carbociclo saturado, insaturado o aromático de 3-14 miembros), (r) heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre, (s) carbociclo saturado, insaturado o aromático de 3-14 miembros, (t) -haloalquilo, (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)pR9, (dd) -(CR6R6)tC(O)NR6R9, (ee) -(CR6R6)tOR9, y (ff) -(CR6R6)tNR6R9; donde (m) a (s) están opcionalmente sustituido con uno o más R9; R9 se selecciona de (a) hidrogeno, (b) F, (c) CI, (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) alquilo C1-8, (o) alquenilo C1-8, (p) alquinilo C1-8, (q) heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre, (r) carbociclo saturado, insaturado o aromático de 3-14 miembros, (s) -haloalquilo, (t) -(CR6R6)tOR6, (u) -O(CR6R6)tNR6R10, (v) -C(O)R6, (w) -SR6, (x) -C(O)OR10, (y) -S(O)pR6, (z) -alquilo C1-8-(heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre), (aa) alquilo C1-8-(carbociclo saturado, insaturado o aromático de 3-14 miembros), (bb) -O(CR6R6)tOR6, (cc) -C(=NR6)NR6R6, (dd) -ONR6R6, (ee) -NR6C(O)NR6R6, (ff) -O(CR6R6)tOR6, (gg) -NR6C(O)R6, y (hh) -(CR6R6)tNR6R10; donde (n) a (r) y (z) a (aa) están opcionalmente sustituidos con uno o más R10; R10 se selecciona de (a) hidrogeno, (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) -C(O)(CR6R6)tNR6R6, (n) alquilo C1-8, (o) alquenilo C1-8, (p) alquinilo C1-8, (q) heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre, (r) carbociclo saturado, insaturado o aromático de 3-14 miembros, (s) -haloalquilo, (t) -(CR6R6)tOR6, (u) -O(CR6R6)tNR6R6, (v) -C(O)R6, (w) -SR6, (x) -C(O)OR6, (y) -S(O)pR6, (z) -alquilo C1-8-(heterociclo saturado, insaturado o aromático de 3-14 miembros que contiene uno o más heteroátomos seleccionados del grupo que consiste en nitrogeno, oxígeno y azufre), (aa) alquilo C1-8-(carbociclo saturado, insaturado o aromático de 3-14 miembros), (bb) -O(CR6R6)tOR6, (cc) -C(=NR6)NR6R6, (dd) -ONR6R6, (ee) -NR6C(O)NR6R6, (ff) -O(CR6R6)tOR6, (gg) -NR6C(O)R6, y (hh) -(CR6R6)tNR6R6; opcionalmente, donde ya sea el grupo -D-E-F o el grupo -G-H-J está ausente, pero ambos -D-E-F y -G-H-J no están simultáneamente ausentes; p es 0, 1s 2, y t es 0, 1, 2, o 3, o una sal, éster, tautomero o profármaco del mismo.This refers to the field of antimicrobial compounds and the methods for preparing and using them. These compounds are useful for treating, preventing and reducing the risk of microbial infections in humans and animals. Claim 1: A compound characterized in that it has the formula (1), (2), (3) or (4) wherein -GHJ is selected, alternatively, from -G (HJ) (HJ), where each H and J is selected regardless of, 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) C1-8 alkyl, (c) C2-8 alkenyl, (d) C2-8 alkynyl, where i) 0-4 carbon atoms in any of (b) - (d) immediately above, is 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 of (b) - (d) immediately above, is optionally substituted with one or more R5 groups, and iii) any of (b) - (d) immediately above, is optionally substituted with C 1-8-R5 alkyl groups; (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) -C (= 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) t-, (dd) a 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, or ( ee) a saturated, unsaturated or aromatic carbocycle of 3-14, 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 saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (c) a saturated, unsaturated or aromatic carbocycle of 3-14 members, where (b) or (c) is optionally substituted with one or more groups (d) C1-8 alkyl, (e) C2-8 alkenyl , (f) C2-8 alkynyl, where i) 0-4 carbon atoms in any of (d) - (f) immediately above, is 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 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-R5 alkyl groups; and (g) - (CR6R6) t-, C, F, and J are independently selected from the group consisting of: (a) hydrogen, (c) F, (d) CI, (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 C1-8 alkyl group, (mm) C2-8 alkenyl, (nn) C2-8 alkynyl, (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 3-14 membered saturated, unsaturated or aromatic carbocycle, ( qq) - (CR6R6) tNR6 (CR6R6) tR8, (rr) -N [(CR6R6) tR8] [C = O (CR6R6) tR8], (ss) - (CR6R6) tN [(CR6R6) tR8] [(CR6R 6) 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) C1-8 alkyl, (n) C1-8 alkenyl, (o) C1-8 alkynyl, (p ) -C1-8 alkyl- (a saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) -C1-8 alkyl- (carbocycle saturated, unsaturated or aromatic 3-14 members), (r) -haloalkyl, (s) -SR6, (t) saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and (u) saturated, unsaturated or aromatic carbocycle of 3-14 members; alternatively, two R5 groups are taken together to form a carbocycle where (m) to (r) and (t) to (u) are optionally substituted with one or more R8; R6 is selected from (a) hydrogen, (b) C1-8 alkyl or alternatively two R6 groups are taken together to form a carbocycle, (c) -haloalkyl, (d) a saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and (e) saturated, unsaturated or aromatic carbocycle of 3-14 members; 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) C1-8 alkyl, (n) C1-8 alkenyl, (o) C1-8 alkynyl, ( p) -C1-8 alkyl- (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) C1-8 alkyl (saturated carbocycle) , unsaturated or aromatic 3-14 members), (r) haloalkyl-, (s) -NR6R8, (t) -OR8, (u) - (CR6R6) tNR6R8, (v) -CR6R8R8, (w) -SR6, (x) 3-14 membered saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (y) 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, (dd) -C (= NR6) NR6R6 ; where (m) a (q) and (x) a (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) C1-8 alkyl, (n) C1-8 alkenyl, (o) C1-8 alkynyl, ( p) -C1-8 alkyl- (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (q) C1-8 alkyl (saturated carbocycle) , unsaturated or aromatic 3-14 members), (r) saturated, unsaturated or aromatic 3-14 member heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (s) saturated, unsaturated carbocycle or 3-14 membered aromatic, (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) pR9, (dd) - (CR6R6) tC (O) NR6R9, (ee) - (CR6R6) tOR9, and (ff) - (CR6R6) tNR6R9; where (m) a (s) are optionally substituted with one or more R9; R9 is selected from (a) hydrogen, (b) F, (c) CI, (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) alkenyl C1-8, (p) C1-8 alkynyl, (q) 3-14 saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r) saturated carbocycle, 3-14 unsaturated or aromatic, (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R10, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR10, (y) -S (O) pR6, (z) -C 1-8 alkyl- (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (aa) C1-8- alkyl (saturated, unsaturated or aromatic carbocycle of 3-14 members), (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) a (r) and (z) a (aa) are optionally substituted with one or more R10; R10 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) -C (O) (CR6R6) tNR6R6, (n) C1-8 alkyl, (o) alkenyl C1-8, (p) C1-8 alkynyl, (q) 3-14 saturated, unsaturated or aromatic heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, (r) saturated carbocycle, 3-14 unsaturated or aromatic, (s) -haloalkyl, (t) - (CR6R6) tOR6, (u) -O (CR6R6) tNR6R6, (v) -C (O) R6, (w) -SR6, (x) -C (O) OR6, (y) -S (O) pR6, (z) -C 1-8 alkyl- (saturated, unsaturated or aromatic 3-14 membered heterocycle containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur), (aa) C1-8- alkyl (saturated, unsaturated or aromatic carbocycle of 3-14 members), (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 the -D-E-F group or the -G-H-J group is absent, but both -D-E-F and -G-H-J are not simultaneously absent; p is 0, 1s 2, and t is 0, 1, 2, or 3, or a salt, ester, tautomer or prodrug thereof.

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