IP Library Granted Patent US 12,246,028
Granted Patent B2
US 12,246,028 · App. 17/295,522 · Granted Mar 11, 2025

Use of dantrolene and dantrolene prodrugs to treat radiation exposure

Inventor: Adrian Hepner (Woodcliff Lake, NJ)
Assignee: EAGLE RESEARCH LABS LIMITED
A61K31/675A61K9/0019A61K31/4178A61P39/00
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,246,028
App. No.
17/295,522
Granted
Mar 11, 2025
Kind
B2
Abstract

The disclosure is directed to methods of using dantrolene, dantrolene prodrugs, or pharmaceutically acceptable salts thereof, to treat radiation exposure.

Claims (42)

1. A method of treating a human subject that has been or will be exposed to radiation comprising administering to the human subject a pharmaceutical composition comprising a therapeutically effective amount of a compound of formula I, a compound of formula II, or a pharmaceutically acceptable salt thereof, or a combination thereof

wherein R is —P(O)(OH) 2 or —P(O)(OR 1 )(OR 2 );

R 1 is H, —C 1-26 alkyl, aryl, —C 1-6 alkC(O)O—C 1-26 alkyl, —C 1 alkOC(O)C 1-26 alkyl, or —C 1 alkOC(O)OC 1-26 alkyl; and

R 2 is —C 1-26 alkyl, aryl, C 1-6 alkC(O)O—C 1-26 alkyl, —C 1 alkOC (O)C 1-26 alkyl, or —C 1 alkOC(O)OC 1-26 alkyl;

R 3 is H, —C(O)—Z—N(R 4 )(R 5 ), —C(O)Z—C(O)—OH, or —C(O)—NH—Y—CH 2 —OC(O)—Z—C(O)—OH; Z is —C 1-6 alk; Y is arylene; R 4 is H or —C 1-6 alkyl; R 5 is H or —C 1-6 alkyl; or R 4 and R 5 , together with the nitrogen to which they are attached, form a heterocycloalkyl;

or a pharmaceutically acceptable salt thereof.

2. The method of claim 1 , wherein R is —P(O)(OH) 2 .

3. The method of claim 1 , wherein R is —P(O)(OR 1 )(OR 2 ).

4. The method of claim 3 , wherein R 1 is H.

5. The method of claim 3 , wherein R 1 is —C 1-26 alkyl.

6. The method of claim 3 , wherein R 1 is aryl.

7. The method of claim 3 , wherein R 1 is —C 1-6 alkC(O)O—C 1-26 alkyl.

8. The method of claim 3 , wherein R 1 is —C 1 alkOC(O)C 1-26 alkyl.

9. The method of claim 3 , wherein R 1 is —C 1 alkOC(O)OC 1-26 alkyl.

10. The method of claim 4 , wherein R 2 is —C 1-26 alkyl or aryl.

11. The method of claim 4 , wherein R 2 is —C 1-6 alkC (O)O—C 1-26 alkyl.

12. The method of claim 4 , wherein R 2 is —C 1 alkOC(O)C 1-26 alkyl.

13. The method of claim 4 , wherein R 2 is —C 1 alkOC(O)OC 1-26 alkyl.

14. The method of claim 1 , wherein the compound of formula I, and/or formula II is in the form of a pharmaceutically acceptable salt.

15. The method of claim 1 , wherein the human subject is administered a pharmaceutical composition comprising a compound of formula I or a pharmaceutically acceptable salt thereof.

16. The method of claim 1 , wherein the human subject is administered a pharmaceutical composition comprising a compound of formula II or a pharmaceutically acceptable salt thereof.

17. The method of claim 1 , wherein the human subject has been or will be exposed to a radiation dose of between 0.3 Gy and 50 Gy.

18. The method of claim 1 , wherein the human subject has been or will be exposed to a radiation dose of at least 0.7 Gy.

19. The method of claim 1 , wherein the human subject has been or will be exposed to a radiation dose of at least 6 Gy, at least 10 Gy, or at least 50 Gy.

20. The method of claim 1 , wherein the radiation is X-ray radiation, gamma ray radiation, neutron radiation, or a combination thereof.

21. The method of claim 1 , wherein the radiation exposure is chemoradiation exposure.

22. The method of claim 1 , wherein the radiation exposure is nuclear power plant leakage exposure.

23. The method of claim 1 , wherein the radiation exposure is nuclear weapon exposure.

24. The method of claim 1 , wherein the pharmaceutical composition is administered to the human subject 24 hours or less after the human subject has been exposed to the radiation.

25. The method of claim 1 , wherein the therapeutically effective amount is 1 mg/kg to about 30 mg/kg of the compound of formula I, the compound of formula II, or a pharmaceutically acceptable salt thereof, or a combination thereof.

26. The method of claim 1 , wherein the pharmaceutical composition is administered to the human subject prior to the human subject being exposed to the radiation.

27. The method of claim 1 , wherein the pharmaceutical composition is administered intravenously, subcutaneously, intramuscularly, intraosseously, or transdermally.

28. The method of claim 1 , wherein the pharmaceutical composition comprises the compound of formula I, the compound of formula II, or a pharmaceutically acceptable salt thereof, or a combination thereof, mannitol, a polysorbate, a povidone, an optional pH adjustor, and water.

29. The method of claim 1 , wherein the treatment lowers the mortality of the human subject as a result of the radiation exposure, as compared to a control human subject that did not receive the treatment.

30. The method of claim 1 , wherein the treatment improves at least one hematological parameter of the human subject, as compared to a control human subject that did not receive the treatment.

31. The method of claim 1 , wherein the treatment is effective for treating hematopoietic syndrome occurring in the human subject as a result of the radiation exposure.

32. The method of claim 1 , wherein the treatment is effective for treating gastrointestinal syndrome occurring in the human subject as a result of the radiation exposure.

33. The method of claim 1 , wherein the treatment is effective for treating cardiovascular syndrome occurring in the human subject as a result of the radiation exposure.

34. The method of claim 1 , wherein the treatment is effective for treating central nervous system syndrome occurring in the human subject as a result of the radiation exposure.

35. The method of claim 1 , wherein the treatment is effective for treating anorexia, nausea, vomiting, cramps, or diarrhea occurring in the human subject as a result of the radiation exposure.

36. The method of claim 1 , wherein the treatment is effective for treating cognitive changes or behavior changes occurring in the human subject as a result of the radiation exposure.

37. The method of claim 1 , wherein the pharmaceutical composition comprises a ditromethamine salt of Formula I-A:

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2026
From: EAGLE RESEARCH LABS LIMITED
To: EAGLE PHARMACEUTICALS, INC.
Reel/Frame 075323/0174 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 20, 2026
From: EAGLE PHARMACEUTICALS, INC.
To: COSETTE PHARMACEUTICALS, INC.
Reel/Frame 076014/0635 →
RELEASE OF SECURITY INTEREST Recorded Apr 1, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EAGLE RESEARCH LABS LIMITED
Reel/Frame 070698/0830 →
SECURITY INTEREST Recorded Nov 1, 2022
From: EAGLE RESEARCH LABS LIMITED
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 061615/0096 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2021
From: HEPNER, ADRIAN
To: EAGLE PHARMACEUTICALS, INC.
Reel/Frame 056298/0790 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2021
From: EAGLE PHARMACEUTICALS, INC.
To: EAGLE RESEARCH LABS LIMITED
Reel/Frame 057278/0481 →
Continuity (2)
Provisional Application 62772001 · Nov 27, 2018
Related Publication 20220023319A1 · Jan 27, 2022
References Cited (25)
US 4163058A · Stella et al. · 1979 [cited by applicant]
US 11352347B2 · Wescott · 2022 [cited by examiner]
US 20090093531A1 · Malkawi · 2009 [cited by applicant]
US 20150231093A1 · Miller · 2015 [cited by examiner]
US 20200239455A1 · Wescott · 2020 [cited by examiner]
US 20220324850A1 · Wescott · 2022 [cited by examiner]
EP 0693481A1 · 1996 [cited by applicant]
JP H08183777A · 1996 [cited by applicant]
JP 2011500570A · 2011 [cited by applicant]
WO WO2019079721A1 · 2019 [cited by examiner]
Emin Büyükokuroǧlu, Mehmet, et al. Cell Biochem Funct. Jun. 2003;21(2):127-31. (Year: 2003). [cited by examiner]
I Garau, Miquel Macià, et al. Rep. Pract. Oncol Radiother. Jul. 2011;16(4):123-30. (Year: 2011). [cited by examiner]
Ryanodex® (dantrolene sodium) for injectable suspension, for intravenous use; Dailymed; Ref. ID: 3597641; Nat'l Library of Medicine; Jul. 2014; p. 2-11. [cited by applicant]
Yamashita Hisao; “emission of light radiation radiation damage”; Radioisotopes; Japan Isotope Association Radioisotopes; vol. 13 No. 3; May 1964; p. 244-260 ( [cited by applicant]
Varia et al.; “Phenytoin Prodrugs III: Water-Soluble Prodrugs for Oral and/or Parenteral Use”; Journal of Pharmaceutical Sciences; vol. 73 No. 8; Aug. 1984; p. 1068-1073. [cited by applicant]
Bundgaard et al.; “Pro-Drugs as Drug Delivery Systems VIII. Bioreversible Derivatization of Hydantoins by N-Hydroxymethylation”; Int'l Journal of Pharmaceutics; vol. 5; 1980; p. 67-77. [cited by applicant]
Russia Patent Application No. 2021117883; Office Action; dated Apr. 18, 2023; 17 pages. [cited by applicant]
Harkevičh D. A. Farmakologia [Pharmacology], Moscow, “Medicina”, 1987, pp. 47-48. [cited by applicant]
Belikov V. G. Farmacevtičeskaâ himiâ [Pharmaceutical Chemistry], textbook, 4th ed., Moscow, “MEDpress-inform”, 2007, p. 622 and pp. 27-29. [cited by applicant]
Maškovskij M. D. Lekarstvennye sredstva [Drugs], vol. 1, Moscow, “Medicina”, 1993, p. 8. [cited by applicant]
Maškovskij M. D. Lekarstvennye sredstva [Drugs], 14th ed., vol. 1, Moscow, “Medicina”, 2002, pp. 8-9. [cited by applicant]
Žulenko V. N., Gorškov G. I. Farmakologiâ [Pharmacology], Moscow, KolosS, 2008, pp. 34-35. [cited by applicant]
Pharmaceutical Technology: Technology of dosage forms: Textbook for students of higher education institutions], 2nd ed., Moscow, Publishing Center “Akademiâ”, 2006, p. 6. [cited by applicant]
Daniela Jornada et al., “The Prodrug Approach: A successful tool for improving drug solubility”, Molecules, Dec. 29, 2015, vol. 21, No. 1, p. 42. [cited by applicant]
Mehmet Emin Buyukokuroglu et al., “Dantrolene protects erythrocytes against oxidative stress during whole-body irradiation in rats, Radioprotive Effect of Dantrolene”, Cell Biochemistry and Function, Jun. 1, 2003, vol. … [cited by applicant]