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US 12,157,713 B2Granted
Conjugated oligoelectrolytes as antimicrobial agents
AssigneesNanyang Technological University, National University of Singapore
InventorsJamie Hinks, Cheng Zhou, Guillermo C. Bazan
Life of this patent
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Abstract
Disclosed herein are compounds of formula I, where said compounds displays antibacterial properties. Also disclosed herein is the use of said compounds to treat microbial infection. The compounds of formula I have the following structure: where n, m, p, q, X, R1 to R11 are as defined herein.
Claims16
A compound of formula I:
- wherein:
- n is 0 or 1;
- m, at each occurrence, independently represents is 1 to 12;
- p and q, at each occurrence, independently represents 0;
- R1, at each occurrence, independently represents a —(CH2)o—NR1′R2′ group or a —(CH2)o′—N+R1′R2′R3′ group, the latter group's charge being balanced by an X—;
- each R1′, R2, R3, R2′ and R3′ are independently a C1-12 alkyl group;
- o and o′ are 1 to 12;
- R4 to R5, at each occurrence, independently represents:
- (a) H;
- (b) halo;
- (c) CN;
- (d) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl (which latter three groups are unsubstituted or substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl (which latter three groups are unsubstituted or substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C1-4 alkyl and C1-4 alkoxy), Cy1 (which Cy1 group is unsubstituted or is substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C1-4 alkyl and C1-4 alkoxy), OR12a, S(O)rR12b, S(O)2NR12cR12d, NR12eS(O)2R12f, NR12gR12h, aryl and Het1);
- (e) Cy2 (which Cy2 group is unsubstituted or is substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C1-4 alkyl and C1-4 alkoxy), OR13a S(O)rR13b, S(O)2NR13cR13d, NR13eS(O)2R13f, NR13gR13h, aryl and Het2),
- (f) Heta (which Heta group is unsubstituted or substituted by one or more substituents selected from halo, nitro, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C1-4 alkyl and C1-4 alkoxy), OR14a, S(O)rR14b, S(O)2NR14cR14d, NR14eS(O)2R14f, NR14gR14h, aryl and Het3);
- (g) OR15a;
- (h) S(O)rR15b;
- (i) S(O)2NR15cR15d;
- (j) NR15eS(O)2R15f, and
- (k) NR15gR15h;
- R6 to R11, at each occurrence, independently represents:
- (i) H;
- R12a to R12h, R13a to R13h, R14a to R14h, R15a to R15h, independently represent, at each occurrence, H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from F, Cl, Br, nitro, ═O, C(O)OC1-4 alkyl, CN, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C1-4 alkyl and C1-4 alkoxy), OR16a, S(O)rR16b, S(O)2NR16cR16d, NR16eS(O)2R16f, NR16gR16h, aryl and Het4), C3-10 cycloalkyl, or C4-10 cycloalkenyl (which latter two groups are optionally substituted by one or more substituents selected from F, Cl, Br, OH, ═O, C1-6 alkyl and C1-6 alkoxy) or Hetb;
- R16a to R16h independently represent at each occurrence, H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl which latter three groups are optionally substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C1-4 alkyl and C1-4 alkoxy), C3-6 cycloalkyl, or C4-6 cycloalkenyl (which latter two groups are optionally substituted by one or more substituents selected from F, Cl, Br, OH, ═O, C1-4 alkyl and C1-4 alkoxy),
- Het1 to Het4,Heta, and Hetb independently represent a 4- to 14-membered heterocyclic groups containing one or more heteroatoms selected from O, S and N, which heterocyclic groups may comprise one, two or three rings and may be substituted by one or more substituents selected from ═O, or halo, C1-6 alkyl, which latter group is optionally substituted by one or more substituents selected from F, Cl, Br, —OR17a, —NR17bR17c, —C(O)OR17d and —C(O NR17eR17f,
- R17a to R17f independently represent at each occurrence, H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl which latter three groups are optionally substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C1-4 alkyl and C1-4 alkoxy), C3-6 cycloalkyl, or C4-6 cycloalkenyl (which latter two groups are optionally substituted by one or more substituents selected from F, Cl, Br, OH, ═O, C1-4 alkyl and C1-4 alkoxy),
- Cy1, Cy2, Cy1′ and Cy2′, at each occurrence, independently represents a 3- to 10-membered aromatic, fully saturated or partially unsaturated carbocyclic ring;
- each r independently represents 0, 1 or 2;
- and
- each X− is a pharmaceutically acceptable anion, or pharmaceutically acceptable salts and solvates thereof.
26 more elements
Dependencies are inferred from the claim text.