Conjugated oligoelectrolytes as antimicrobial agents

1. 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;

R 1 , at each occurrence, independently represents a —(CH 2 ) o —NR 1 ′R 2 ′ group or a —(CH 2 ) o ′—N + R 1 ′R 2 ′R 3 ′ group, the latter group's charge being balanced by an X — ;

each R 1 ′, R 2 , R 3 , R 2 ′ and R 3 ′ are independently a C 1-12 alkyl group;

o and o′ are 1 to 12;

R 4 to R 5 , at each occurrence, independently represents:

(a) H;

(b) halo;

(c) CN;

(d) C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl (which latter three groups are unsubstituted or substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl (which latter three groups are unsubstituted or substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C 1-4 alkyl and C 1-4 alkoxy), Cy 1 (which Cy 1 group is unsubstituted or is substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C 1-4 alkyl and C 1-4 alkoxy), OR 12a , S(O) r R 12b , S(O) 2 NR 12c R 12d , NR 12e S(O) 2 R 12f , NR 12g R 12h , aryl and Het 1 );

(e) Cy 2 (which Cy 2 group is unsubstituted or is substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C 1-4 alkyl and C 1-4 alkoxy), OR 13a S(O) r R 13b , S(O) 2 NR 13c R 13d , NR 13e S(O) 2 R 13f , NR 13g R 13h , aryl and Het 2 ),

(f) Het a (which Het a group is unsubstituted or substituted by one or more substituents selected from halo, nitro, CN, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C 1-4 alkyl and C 1-4 alkoxy), OR 14a , S(O) r R 14b , S(O) 2 NR 14c R 14d , NR 14e S(O) 2 R 14f , NR 14g R 14h , aryl and Het 3 );

(g) OR 15a ;

(h) S(O) r R 15b ;

(i) S(O) 2 NR 15c R 15d ;

(j) NR 15e S(O) 2 R 15f , and

(k) NR 15g R 15h ;

R 6 to R 11 , at each occurrence, independently represents:

(i) H;

R 12a to R 12h , R 13a to R 13h , R 14a to R 14h , R 15a to R 15h , independently represent, at each occurrence, H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from F, Cl, Br, nitro, ═O, C(O)OC 1-4 alkyl, CN, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C 1-4 alkyl and C 1-4 alkoxy), OR 16a , S(O) r R 16b , S(O) 2 NR 16c R 16d , NR 16e S(O) 2 R 16f , NR 16g R 16h , aryl and Het 4 ), C 3-10 cycloalkyl, or C 4-10 cycloalkenyl (which latter two groups are optionally substituted by one or more substituents selected from F, Cl, Br, OH, ═O, C 1-6 alkyl and C 1-6 alkoxy) or Het b ;

R 16a to R 16h independently represent at each occurrence, H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl which latter three groups are optionally substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C 1-4 alkyl and C 1-4 alkoxy), C 3-6 cycloalkyl, or C 4-6 cycloalkenyl (which latter two groups are optionally substituted by one or more substituents selected from F, Cl, Br, OH, ═O, C 1-4 alkyl and C 1-4 alkoxy),

Het 1 to Het 4 ,Het a , and Het b 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, C 1-6 alkyl, which latter group is optionally substituted by one or more substituents selected from F, Cl, Br, —OR 17a , —NR 17b R 17c , —C(O)OR 17d and —C(O NR 17e R 17f ,

R 17a to R 17f independently represent at each occurrence, H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl which latter three groups are optionally substituted by one or more substituents selected from F, Cl, Br, nitro, CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl (which latter three groups are optionally substituted by one or more substituents selected from OH, ═O, F, Cl, Br, C 1-4 alkyl and C 1-4 alkoxy), C 3-6 cycloalkyl, or C 4-6 cycloalkenyl (which latter two groups are optionally substituted by one or more substituents selected from F, Cl, Br, OH, ═O, C 1-4 alkyl and C 1-4 alkoxy),

Cy 1 , Cy 2 , Cy 1 ′ and Cy 2 ′, 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.

2. The compound according to claim 1 , wherein:

m is 4 to 8.

3. The compound according to claim 1 , wherein o, when present, is 2 to 4.

4. The compound according to claim 1 , wherein o′, when present, is 2 to 4.

5. The compound according to claim 1 , wherein each of R 2 to R 3 is methyl.

6. The compound according to claim 1 , wherein R 1 is a —(CH 2 ) o ′—N+R 1 ′R 2 ′R 3 ′ group.

7. The compound according to claim 1 , wherein R 1 ′, R 2 ′ and R 3 ′ is a C 1 to C 4 alkyl.

8. The compound according to claim 1 , wherein:

m is 4, 6 or 8;

each R 1 ′, R 2 , R 3 , R 2 ′ and R 3 ′ are independently a C 1-4 alkyl group; and o and o′ are 2 to 3.

9. The compound according to claim 1 , wherein the compound of formula I is selected from the group consisting of:

10. The compound according to claim 9 , wherein the compound of formula I is selected from the group consisting of:

11. The compound according to claim 1 , wherein each X—is a halide selected from the group consisting of Br—, Cl—, F—and I—.

12. A pharmaceutical formulation comprising a compound of formula I as defined in claim 1 and one or more of a pharmaceutically acceptable adjuvant, diluent or carrier.

13. A method of treating an infection, the method including the step of administering a therapeutically effective amount of a compound of formula I or a salt or solvate thereof as defined in claim 1 to a subject in need thereof.

14. The method according to claim 13 , wherein the compound of formula I is selected from the group consisting of:

15. A method of removing a biofilm from a solid substrate or preventing build-up of a biofilm on a solid substrate, or killing, inhibiting, or dispersing microbes inhabiting said biofilm in a system susceptible to biofilm formation, said biofilm being formed by at least one microorganism, the method comprising the step of contacting the system with an effective amount of a compound of formula I or a salt or solvate thereof as defined in claim 1 or a composition comprising a compound of formula I to remove the biofilm or prevent its formation.

16. A cosmetic or cleansing formulation, comprising a compound of formula I as defined in claim 1 and one or more of an adjuvant, diluent or carrier suitable for use in a cosmetic or cleansing formulation.