Granted Patent B2

US 12,528,809 · App. 17/997,293 · Granted Jan 20, 2026

Inventors: Ricky Wayne Couch (Durham, NC); Wenning Dai (West Chester, PA); Senthil Davison (Raleigh, NC); Israil Pendrak (Collegeville, PA); Glenn Robert Williams (Pearland, TX)

Assignee: GlaxoSmithKline Intellectual Property Development Limited

C07D471/16C07B2200/13

Abstract

Claims (42)

1 . A crystalline form of gepotidacin, which is selected from the group consisting of gepotidacin mesylate anhydrate, gepotidacin mesylate monohydrate, gepotidacin mesylate dihydrate and gepotidacin anhydrate.

2 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate dihydrate.

3 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate dihydrate characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three or at least four diffraction angles, when measured using Cu K α radiation, selected from the group consisting of about 9.0, 11.5, 13.4, 14.3, 14.9, 15.5, 17.6, 18.6, and 20.7 degrees 2θ.

4 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate dihydrate characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 1 .

5 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate dihydrate characterized by the following unit cell parameters:

a=6.9255(5)Å; b=15.4500(12)Å; c=25.7918(19)Å; α=β=γ=90°;

V=2759.7(4)Å 3 ; Z′=1;

Space group P2 1 2 1 2 1 ;

Molecules/unit cell 4;

Density (calculated) 1.398 g/cm 3 ;

wherein Z′ is the number of molecules per asymmetric unit.

6 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate anhydrate.

7 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate anhydrate characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three or at least four diffraction angles, when measured using Cu K α radiation, selected from the group consisting of about 7.1, 9.7, 12.1, 14.2, 15.2, 17.3, and 20.2 degrees 2θ.

8 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate anhydrate characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 5 .

9 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate anhydrate characterized by the following unit cell parameters:

a=12.3921(7)Å; b=7.0262(4)Å; c=14.6536(9)Å; α=γ=90°;

β=95.0077(13)°; V=1271.01(13)Å3; Z′=1

Space group P2 1 ;

Molecules/unit cell 2;

Density (calculated) 1.423 g/cm 3 ;

wherein Z′ is the number of molecules per asymmetric unit.

10 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate monohydrate.

11 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate monohydrate characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three or at least four diffraction angles, when measured using Cu Ka radiation, selected from the group consisting of about 5.6, 7.1, 8.8, 11.2, 13.0, 13.7, 20.1, 21.6, and 23.3 degrees 2θ.

12 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin mesylate monohydrate characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 9 .

13 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin anhydrate characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three or at least four diffraction angles, when measured using Cu K α radiation, selected from the group consisting of about 8.8, 10.8, 11.7, 12.8, 13.2, 14.4, 16.3, 19.9, 20.8, and 25.0 degrees 2θ.

14 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin anhydrate.

15 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin anhydrate characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 13 .

16 . The crystalline form according to claim 1 , wherein the crystalline form is gepotidacin anhydrate characterized by the following unit cell parameters:

a=8.44022(16)Å; b=6.42442(12)Å; c=20.2774(5)Å; α=γ=90°;

β=96.778(2)°; V=1091.83(4)Å 3 ; Z′=1

Space group P2 1 ;

Molecules/unit cell 2;

Density (calculated) 1.364 g/cm 3 ;

wherein Z′ is the number of molecules per asymmetric unit.

17 . A pharmaceutical composition comprising the crystalline form according to claim 1 and a pharmaceutically acceptable carrier.

18 . The pharmaceutical composition according to claim 17 , wherein the pharmaceutical composition is for oral administration.

19 . The pharmaceutical composition according to claim 18 , wherein the pharmaceutical composition is a tablet or capsule.

20 . A method of preparing a pharmaceutical composition comprising gepotidacin, which method comprises mixing the crystalline form according to claim 1 and a pharmaceutically acceptable carrier.

21 . A method of treating a bacterial infection in a human in need thereof comprising administering to said human an effective amount of the crystalline form according to claim 1 .

22 . The method according to claim 21 , wherein the bacterial infection is uncomplicated urinary tract infection or infection by Neisseria gonorrhoeae.

23 . A method for preparing gepotidacin mesylate dihydrate comprising crystallizing gepotidacin mesylate in a solvent mixture of water and an organic solvent.

24 . The method according to claim 23 , wherein the organic solvent is 2-propanol.

Assignments (2)

Continuity (2)

References Cited (12)