IP Library Granted Patent US 12,433,872
Granted Patent B2
US 12,433,872 · App. 17/286,058 · Granted Oct 7, 2025

Treatment of

Inventors: David W. Boykin (Atlanta, GA); Dennis E. Kyle (Athens, GA); Christopher A. Rice (Athens, GA); Abdelbasset A. Farahat (Atlanta, GA)
Assignee: GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
A61K31/4184A01N43/52A01N43/54A61K31/155A61K31/4174A61K31/4196A61K31/496A61K31/506A61K31/661A61K31/7036A61K31/785A61K38/12A61P33/04C07D235/18C07D235/20C07D403/04C07D403/14
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Quick Facts
Patent No.
US 12,433,872
App. No.
17/286,058
Granted
Oct 7, 2025
Kind
B2
Abstract

Compounds, compositions, and methods for the treatment of infections caused by Acanthamoeba or Balamuthia mandrillaris trophozoites and/or cysts and for the disinfection of solids and/or liquids, such as medical and personal care items, for example contact lenses, that may harbor Acanthamoeba trophozoites and/or cysts are provided.

Claims (41)

1. A compound of Formula 2 or Formula 3:

or a pharmaceutically acceptable salt thereof;

wherein:

R 3 and R 4 are independently selected from hydrogen, halo, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkyl, wherein at least one of R 3 and R 4 is not hydrogen;

R 5 is selected from halo, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkyl;

R 6 and R 7 are independently selected from hydrogen, halo, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkyl, wherein at least one of R 6 and R 7 is not hydrogen;

R 8 is selected from halo, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkyl;

R 9 and R 10 are independently selected from hydrogen, halo, C 1 -C 4 alkoxy, and C 1 -C 4 haloalkyl, wherein at least one of R 9 and R 10 is not hydrogen;

R X and R Y are independently selected at each occurrence from halo, C 1-4 alkoxy, and C 1 -C 4 haloalkyl;

o and p are independently selected 0, 1, 2, and 3; and

R A and R B are independently C 1 -C 6 alkyl.

2. The compound of claim 1 , wherein one of R 3 and R 4 is a halogen.

3. The compound of claim 1 , wherein two of R 3 and R 4 , R 5 , R 6 and R 7 are selected from a halogen.

4. The compound of claim 1 , wherein two of R 3 , R 4 , R 8 , R 9 and R 10 are selected from a halogen.

5. The compound of claim 1 , wherein one of R 3 , R 4 , R 8 , and R 9 is selected from C 1 -C 4 alkoxy.

6. The compound of claim 1 , wherein R A and R B are isopropyl.

7. The compound of claim 1 , wherein the compound is selected from:

or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.

9. A method for treating an eye infection caused by one or more Acanthamoeba species in a host in need thereof comprising administering an effective amount of a compound of claim 1 , optionally in a pharmaceutically acceptable carrier.

10. The method of claim 9 wherein the eye infection is Acanthamoeba keratitis.

11. The method of claim 9 , further comprising administering an effective amount of an additional therapeutic agent selected from alexidine, chlorhexidine, polyhexamethylene biguanide (PHMB), propamidine isethionate, hexamidine isethionate, natamycin, neomycin, ketoconazole, itraconazole, polymyxin B, gramicidin, voriconazole, miconazole nitrate, pentamidine, octamidine, fluconazole, miltefosine, and combinations thereof.

12. The method of claim 9 , wherein the one or more Acanthamoeba species are present as both cysts and trophozoites.

13. The method of claim 9 , wherein the host is treated with the compound for at least 1 day, at least 3 days, at least 5 days, at least 10 days, at least 20 days, at least 30 days, at least 40 days, or at least 50 days.

14. The method of claim 9 wherein the host is a human.

15. A method for disinfecting one or more Acanthamoeba species from a solid, liquid or gel object comprising administering an effective amount of a compound of claim 1 , optionally in a pharmaceutically acceptable carrier.

16. The method of claim 15 , wherein the object is selected from an application, a dressing, contact lens, an optical implant, a contact lens solution, an ocular solution and rewetting eye drops.

17. A method for treating an infection caused by Balamuthia mandrillaris in a host in need thereof comprising administering an effective amount of a compound of claim 1 , optionally in a pharmaceutically acceptable carrier.

18. The method of claim 17 , wherein the infection caused by Balamuthia mandrillaris is granulomatous amoebic encephalitis.

19. The method of claim 17 , wherein the Balamuthia mandrillaris is present as both cysts and trophozoites.

20. A disinfecting solution comprising an effective amount of a compound of claim 1 in an aqueous carrier.

21. A contact lens care solution comprising an effective amount of a compound of claim 1 in a suitable aqueous carrier.

22. A method for treating an infection caused by one or more Acanthamoeba species in a host in need thereof comprising administering an effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.

23. The method of claim 22 wherein the infection is Acanthamoeba keratitis.

24. The method of claim 22 , wherein the one or more Acanthamoeba species are present as both cysts and trophozoites.

25. The method of claim 22 , wherein the host is treated with the compound for at least 1 day, at least 3 days, at least 5 days, at least 10 days, at least 20 days, at least 30 days, at least 40 days, or at least 50 days.

26. The method of claim 22 , wherein the host is a human.

27. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

28. A method for treating an infection caused by Balamuthia mandrillaris or a Acanthamoeba species in a host comprising administering an effective amount of a compound from the group consisting of:

or a pharmaceutically acceptable salt thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2021
From: BOYKIN, DAVID W.; FARAHAT, ABDELBASSET A.
To: GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.
Reel/Frame 057877/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2021
From: KYLE, DENNIS E.; RICE, CHRISTOPHER A.
To: UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; UNIVERSITY OF SOUTH FLORIDA
Reel/Frame 057877/0864 →
Continuity (2)
Provisional Application 62746940 · Oct 17, 2018
Related Publication 20220096441A1 · Mar 31, 2022
References Cited (38)
US 20100249175A1 · Wilson et al. · 2010 [cited by applicant]
US 20180243333A1 · Brown et al. · 2018 [cited by applicant]
WO 2017094204 · 2017 [cited by applicant]
Brown, Nathan, Bioisosterism in Medicinal Chemistry, SN 9783527330157 (2012) (Year: 2012). [cited by examiner]
Rice et al., Antimicrob Agents Chemother. Apr. 2015;59(4):2037-44 (Year:2015). [cited by examiner]
Hu et al. Bioorg Med Chem Lett. Jul. 1, 2009;19(13):3374-3377 & 4626-4629 (Year: 2009). [cited by examiner]
Kobrina et al., 1988 Russ. Chem. Rev. 57 62 (Year: 1988). [cited by examiner]
Parija et al., Trop Parasitol. 2015;5(1):23-28 (Year: 2015). [cited by examiner]
EP19873034.3 , “Partial Supplementary European Search Report”, Jun. 15, 2022, 11 pages. [cited by applicant]
Hu et al., “Optimization of the Central Linker of Dicationic Bis-Benzimidazole Anti-MRSA And Anti-VRE Agents”, Bioorganic & Medicinal Chemistry Letters, vol. 19, No. 13, May 20, 2009, pp. 3374-3377. [cited by applicant]
Hu et al., “Synthesis and Structure-Activity Relationship Of Dicationic Diaryl Ethers as Novel Potent Anti-MRSA And Anti-VRE Agents”, Bioorganic & Medicinal Chemistry Letters, vol. 19, No. 16, Jun. 25, 2009, pp. 4626-46… [cited by applicant]
Brocius et al., “Acanthamoeba: An Overview of the Challenges to the Development of a Consensus Methodology of Disinfection Efficacy Testing for Contact Lens Care Products”, Eye & Contact Lens Science & Clinical Practice… [cited by applicant]
Cabello-Vilchez , “Granulomatous Meningoencephalitis Balamuthia Mandrillaris in Peru: Infection of the Skin and Central Nervous System”, SMG ebooks titled Encephalitis, Feb. 16, 2017, 23 pages. [cited by applicant]
Clarke et al., “The Pathophysiology of Acanthamoeba Keratitis”, Trends in Parasitology, vol. 22, No. 4, Apr. 2006, pp. 175-180. [cited by applicant]
Elder et al., “A Clinicopathologic Study of In Vitro Sensitivity Testing and Acanthamoeba Keratitis”, Investigative Ophthalmology & Visual Science, vol. 35, No. 3, Mar. 1994, pp. 1059-1064. [cited by applicant]
Fuerst et al., “Phylogenetic Analysis and the Evolution of the 18S rRNA Gene Typing System of Acanthamoeba”, Journal of Eukaryotic Microbiology, vol. 62, No. 1, Jan.-Feb. 2015, pp. 69-84. [cited by applicant]
Kappagoda et al., “Symposium on Antimicrobial Therapy Antiparasitic Therapy”, Mayo Clinic Proceedings, vol. 86, No. 6, Jun. 2011, pp. 561-583. [cited by applicant]
Khan , “Pathogenesis of Acanthamoeba Infections”, Microbial Pathogenesis, vol. 34, No. 6, Jun. 2003, pp. 277-285. [cited by applicant]
Lehmer et al., “Cutaneous Balamuthia Mandrillaris Infection as a Precursor to Balamuthia Amoebic Encephalitis (BAE) in a Healthy 84-Year-Old Californian”, Dermatology Online Journal , vol. 23, No. 7, Jul. 2017, pp. 1-10. [cited by applicant]
Lemgruber et al., “The Fine Structure of the Acanthamoeba Polyphaga Cyst Wall”, FEMS Microbiology Letters, vol. 305, No. 2, Apr. 2010, pp. 170-176. [cited by applicant]
Lorenzo-Morales et al., “An Update on Acanthamoeba Keratitis: Diagnosis, Pathogenesis and Treatment”, Parasite, vol. 22, No. 10, 2015, pp. 1-20. [cited by applicant]
Martinez et al., “Successful Treatment of Balamuthia Mandrillaris Amoebic Infection With Extensive Neurological and Cutaneous Involvement”, Clinical Infectious Diseases, vol. 51, No. 2, Jul. 15, 2010, pp. e7-e11. [cited by applicant]
Martin-Navarro et al., “The Potential Pathogenicity of Chlorhexidine-Sensitive Acanthamoeba Strains Isolated From Contact Lens Cases from Asymptomatic Individuals in Tenerife, Canary Islands, Spain”, Journal of Medical … [cited by applicant]
Matin et al., “Balamuthia Mandrillaris Interactions With Human Brain Microvascular Endothelial Cells in Vitro”, Journal of Medical Microbiology, vol. 56, Aug. 2007, pp. 1110-1115. [cited by applicant]
McBride et al., “Development of Colorimetric Microtiter Plate Assay for Assessment of Antimicrobials against Acanthamoeba”, Journal of Clinical Microbiology, vol. 43, No. 2, Feb. 2005, pp. 629-634. [cited by applicant]
Neelam et al., “Pathobiology and Immunobiology of Acanthamoeba Keratitis: Insights from Animal Models”, The Yale Journal of Biology and Medicine, vol. 90, No. 2, Jun. 23, 2017, pp. 261-268. [cited by applicant]
Oldenburg et al., “Microbiological cure times in Acanthamoeba Keratitis”, Eye, vol. 25, No. 9, Sep. 2011, pp. 1155-1160. [cited by applicant]
Padzik et al., “Tannic Acid-Modified Silver Nanoparticles as a Novel Therapeutic Agent Against Acanthamoeba”, Parasitology Research, vol. 117, Aug. 15, 2018, pp. 3519-3525. [cited by applicant]
Application No. PCT/US2019/056761 , International Search Report and Written Opinion, Mailed On Dec. 30, 2019, 17 pages. [cited by applicant]
Perez-Santonja et al., “Persistently Culture Positive Acanthamoeba Keratitis: in Vivo Resistance and in Vitro Sensitivity”, Ophthalmology, vol. 110, No. 8, Aug. 2003, pp. 1593-1660. [cited by applicant]
Rice et al., “Bis-Benzimidazole Hits against Naegleria fowleri Discovered with New High-Throughput Screens”, Antimicrobial Agents and Chemotherapy, vol. 59, No. 4, 2015, pp. 2037-2044. [cited by applicant]
Shehab et al., “Balamuthia Mandrillaris Granulomatous Amebic Encephalitis With Renal Dissemination in a Previously Healthy Child: Case Report and Review of the Pediatric Literature”, Journal of the Pediatric Infectious … [cited by applicant]
Siddiqui et al., “Balamuthia Mandrillaris Resistance to Hostile Conditions”, Journal of Medical Microbiology, vol. 57, Apr. 2008, pp. 428-431. [cited by applicant]
Siddiqui et al., “Balamuthia Mandrillaris: Morphology, Biology, and Virulence”, Tropical Parasitology, vol. 5, No. 1, Jan.-Jun. 2015, pp. 15-22. [cited by applicant]
Siddiqui et al., “Biology and Pathogenesis of Acanthamoeba”, Parasites & Vectors, vol. 5, Jan. 10, 2012, pp. 1-13. [cited by applicant]
Thomson et al., “Characterization of Sterol Biosynthesis and Validation of 14α-Demethylase as a Drug Target in Acanthamoeba”, Scientific Reports, vol. 7, No. 1, Aug. 15, 2017, pp. 1-9. [cited by applicant]
Verani et al., “National Outbreak of Acanthamoeba Keratitis Associated With Use of a Contact Lens Solution, United States”, Emerging Infectious Diseases, vol. 15, No. 8, Aug. 2009, pp. 1236-1242. [cited by applicant]
Msvesvara et al., “Pathogenic and Opportunistic Free-Living Amoebae: [cited by applicant]