IP Library › Granted Patent US 12,383,547
Granted Patent B2
US 12,383,547 · App. 18/003,644 · Granted Aug 12, 2025

Methods of treatment for a kidney disease

Inventors: Jill M. Pulley (Nashville, TN); Jana K. Shirey-Rice (Brentwood, TN); Rebecca N. Jerome (Nashville, TN); Frederic T. Billings, IV (Nashville, TN); Nicole M. Zaleski (Nashville, TN)
Assignee: Vanderbilt University
A61K31/47A61P13/12
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Quick Facts
Patent No.
US 12,383,547
App. No.
18/003,644
Granted
Aug 12, 2025
Kind
B2
Abstract

Disclosed herein are methods for preventing, treating, or reducing the severity of a cardiac surgery-associated acute kidney injury and extracorporeal membrane oxygenation-associated acute kidney injury in a subject. The methods include administering to the subject a therapeutically effective amount of a leukotriene receptor antagonist compound.

Claims (99)

1. A method of treating or reducing the severity of a cardiac surgery-associated acute kidney injury (CSA-AKI) in a subject in need thereof, the method comprising administering to the subject a therapeutically effective amount of a compound of Formula I:

or a pharmaceutically acceptable ester or salt thereof, where:

R 1 is H, halogen, —CF 3 , —CN, —NO 2 , or N 3 ;

R 2 is lower alkyl, lower alkenyl, lower alkynyl, —CF 3 , —CH 2 F, —CHF 2 , CH 2 CF 3 , substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, substituted or unsubstituted 2-phenethyl, or two R 2 groups joined to the same carbon to form a carbocyclic ring of up to 8 members;

R 3 is H or R 2 ;

R 4 is halogen, —NO 2 , —CN, —OR 3 , —SR 3 , NR 3 R 3 , NR 3 C(O)R 7 , or R 3 ;

R 5 is H, halogen, —NO 2 , —N 3 , —CN, —SR 2 , —NR 3 R 3 , —OR 3 , lower alkyl, or —C(O)R 3 ;

R 6 is —(CH 2 ) s —C(R 7 R 7 )—(CH 2 ) s —R 6 or —CH 2 C(O)NR 12 R 12 ;

R 7 is H or C 1 -C 4 alkyl;

R 8 is the radical W—R 9 ;

R 9 contains up to 20 carbon atoms and is (1) an alkyl group or (2) an alkylcarbonyl group of an organic acyclic or monocyclic carboxylic acid;

R 11 is lower alkyl, —C(O)R 14 , unsubstituted phenyl, or unsubstituted benzyl;

R 12 is H or R 11 ;

R 13 is lower alkyl, lower alkenyl, lower alkynyl, —CF 3 or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 14 is H or R 13 ;

R 16 is H, C 1 -C 4 alkyl, or OH;

R 17 is lower alkyl, lower alkenyl, lower alkynyl, or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 18 is lower alkyl, lower alkenyl, lower alkynyl, —CF3 or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 19 is lower alkyl, lower alkenyl, lower alkynyl, —CF 3 or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 21 is H or R 17 ; —R 22 is R 4 , CHR 7 OR 3 , or CHR 7 SR 2 ;

m is 0-8;

m′ is 2 or 3;

n and n′ are independently 0 or 1,

p and p′ are independently 0-8;

m+n+p is 1-10 when r is 1 and X 2 is O, S, S(O), or S(O) 2 ;

m+n+p is 0-10 when r is 1 and X 2 is CR 3 R 8 ;

m+n+p is 0-10 when r is 0;

m′+n′+p′ is 2-10;

r and r′ are independently 0 or 1;

s is 0-3;

Q 1 is —C(O)OR 3 , 1H (or 2H)-tetrazol-5-yl, —C(O)OR G , —C(O)NHS(O) 2 R 13 , —CN, —C(O)NR 12 R 12 , NR 21 S(O) 2 R 13 , —NR 12 C(O)NR 12 R 12 , —NR 21 C(O)R 18 , —OC(O)NR 12 R 12 , —C(O)R 19 , —S(O)R 18 , —S(O) 2 R 18 , —S(O) 2 NR 12 R 12 , —NO 2 , —NR 21 C(O)OR 17 , —C(NR 12 R 12 )=NR 12 , —C(R 13 )=NOH;

Q 2 is OH;

W is O, S, or NR 3 ;

X 2 and X 3 are independently O, S, S(O), S(O) 2 , or CR 3 R 16 ; with the proviso that at least one is S or SO 2 ;

Y is —CR 3 =CR 3 —

Z 1 and Z 2 are independently -HET(R 3 )(R 5 )—;

HET is the diradical of a benzene, a pyridine, a furan, or a thiophene; and,

wherein the compound decreases urinary leukotrienes.

2. The method of claim 1 , wherein the compound is administered in the form of a composition wherein the composition comprises a pharmaceutically acceptable carrier.

3. The method of claim 2 , wherein the composition comprises about 5 mg to about 250 mg of the compound.

4. The method of claim 1 , wherein the compound is montelukast or a pharmaceutically acceptable salt of montelukast.

5. The method of claim 4 , wherein the pharmaceutically acceptable salt of montelukast is montelukast sodium.

6. The method of claim 1 , wherein the subject is administered the compound perioperatively, the subject is administered the compound perioperatively through at least postoperative day 7, the subject is administered the compound postoperatively, and/or the compound is administered to the subject at least 3 days preoperatively.

7. The method of claim 1 , wherein the compound is administered orally or intravenously at least once per day.

8. The method of claim 1 , wherein the subject has a single nucleotide polymorphism (SNP) in the gene CYSTLR1.

9. The method of claim 8 , wherein the SNP is rs139639671 or I123T.

10. The method of claim 1 , wherein the subject has been identified as having an elevated level of serum creatinine, plasma creatinine, or urine creatinine, compared to baseline creatinine levels in the subject or a healthy control subject.

11. The method of claim 1 , wherein urinary cysteinyl leukotriene levels are decreased in the subject following administration of the compound.

12. The method of claim 1 , wherein one or more of urinary LTC 4 , LTD 4 , and LTE 4 levels are decreased in the subject following administration of the compound.

13. A method of treating or reducing the severity of an extracorporeal membrane oxygenation-associated acute kidney injury (ECMO-AKI) in a subject in need thereof, the method comprising administering to the subject a therapeutically effective amount of a compound of Formula I:

or a pharmaceutically acceptable ester or salt thereof, where:

R 1 is H, halogen, —CF 3 , —CN, —NO 2 , or N 3 ;

R 2 is lower alkyl, lower alkenyl, lower alkynyl, —CF 3 , —CH 2 F, —CHF 2 , CH 2 CF 3 , substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, substituted or unsubstituted 2-phenethyl, or two R 2 groups joined to the same carbon to form a carbocyclic ring of up to 8 members;

R 3 is H or R 2 ;

R 4 is halogen, —NO 2 , —CN, —OR 3 , —SR 3 , NR 3 R 3 , NR 3 C(O)R 7 , or R 3 ;

R 5 is H, halogen, —NO 2 , —N 3 , —CN, —SR 2 , —NR 3 R 3 , —OR 3 , lower alkyl, or —C(O)R 3 ;

R 6 is —(CH 2 ) s —C(R 7 R 7 )—(CH 2 ) s —R 8 or —CH 2 C(O)NR 12 R 12 ;

R 7 is H or C 1 -C 4 alkyl;

R 8 is the radical W—R 9 ;

R 9 contains up to 20 carbon atoms and is (1) an alkyl group or (2) an alkylcarbonyl group of an organic acyclic or monocyclic carboxylic acid;

R 11 is lower alkyl, —C(O)R 14 , unsubstituted phenyl, or unsubstituted benzyl;

R 12 is H or R 11 ;

R 13 is lower alkyl, lower alkenyl, lower alkynyl, —CF 3 or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 14 is H or R 13 ;

R 16 is H, C 1 -C 4 alkyl, or OH;

R 17 is lower alkyl, lower alkenyl, lower alkynyl, or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 18 is lower alkyl, lower alkenyl, lower alkynyl, —CF3 or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 19 is lower alkyl, lower alkenyl, lower alkynyl, —CF 3 or substituted or unsubstituted phenyl, benzyl, or 2-phenethyl;

R 21 is H or R 17 —;

R 22 is R 4 , CHR 7 OR 3 , or CHR 7 SR 2 ;

m is 0-8;

m′ is 2 or 3;

n and n′ are independently 0 or 1,

p and p′ are independently 0-8;

m+n+p is 1-10 when r is 1 and X 2 is O, S, S(O), or S(O) 2 ;

m+n+p is 0-10 when r is 1 and X 2 is CR 3 R 8 ;

m+n+p is 0-10 when r is 0;

m′+n′+p′ is 2-10;

r and r′ are independently 0 or 1;

s is 0-3;

Q 1 is —C(O)OR 3 , 1H (or 2H)-tetrazol-5-yl, —C(O)OR G , —C(O)NHS(O) 2 R 13 , —CN, —C(O)NR 12 R 12 , NR 21 S(O) 2 R 13 , —NR 12 C(O)NR 12 R 12 , —NR 21 C(O)R 18 , —OC(O)NR 12 R 12 , —C(O)R 19 , —S(O)R 18 , —S(O) 2 R 18 , —S(O) 2 NR 12 R 12 , —NO 2 , —NR 21 C(O)OR 17 , —C(NR 12 R 12 )=NR 12 , —C(R 13 )=NOH;

Q 2 is OH;

W is O, S, or NR 3 ;

X 2 and X 3 are independently O, S, S(O), S(O) 2 , or CR 3 R 16 ; with the proviso that at least one is S or SO 2 ;

Y is —CR 3 =CR 3 —

Z 1 and Z 2 are independently -HET(R 3 )(R 5 )—;

HET is the diradical of a benzene, a pyridine, a furan, or a thiophene; and,

wherein the compound decreases urinary leukotrienes.

14. The method of claim 13 , wherein the compound is administered in the form of a composition wherein the composition comprises a pharmaceutically acceptable carrier.

15. The method of claim 13 , wherein the compound is montelukast or a pharmaceutically acceptable salt of montelukast.

16. The method of claim 15 , wherein the pharmaceutically acceptable salt of montelukast is montelukast sodium.

17. The method of claim 15 , wherein the composition comprises about 5 mg to about 250 mg of the compound.

18. The method of claim 13 , wherein the subject is administered the compound at least 2 hours prior to connecting an ECMO machine to the subject, or wherein the subject is administered the compound prior to and throughout the duration of being connected to the ECMO machine.

19. The method of claim 13 , wherein the compound is administered orally or intravenously at least once per day.

20. The method of claim 13 , wherein the subject has a single nucleotide polymorphism (SNP) in the gene CYSTLR1.

21. The method of claim 20 , wherein the SNP is rs139639671 or I123T.

22. The method of claim 13 , wherein the subject has been identified as having an elevated level of serum creatinine, plasma creatinine, or urine creatinine, compared to baseline creatinine levels in the subject or a healthy control subject.

23. The method of claim 13 , wherein urinary cysteinyl leukotriene levels are decreased in the subject following administration of the compound.

24. The method of claim 13 , wherein one or more of urinary LTC 4 , LTD 4 , and LTE 4 levels are decreased in the subject following administration of the compound.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jan 24, 2024
From: VANDERBILT UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 066368/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2022
From: PULLEY, JILL M.; SHIREY-RICE, JANA K.; JEROME, REBECCA N.; BILLINGS, FREDERIC T., IV; ZALESKI, NICOLE M.
To: VANDERBILT UNIVERSITY
Reel/Frame 062233/0030 →
Continuity (3)
Provisional Application 63048623 · Jul 6, 2020
Provisional Application 63047217 · Jul 1, 2020
Related Publication 20230310411A1 · Oct 5, 2023
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