IP Library Granted Patent US 12673048
Granted Patent B2
US 12673048 · App. 16/972,368 · Granted Jul 7, 2026

Method of administering a therapeutically effective amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Inventors: Marc Martinell Pedemonte (Mataró Barcelona, ES); Maria Pilar Pizcueta Lalanza (Mataró Barcelona, ES); Guillem Pina Laguna (Mataró Barcelona, ES); Uwe Meya (Mataró Barcelona, ES); Alan Bye (Horsham, GB)
Assignee: MINORYX THERAPEUTICS S.L.
A61K31/4439A61K9/0053
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Quick Facts
Patent No.
US 12673048
App. No.
16/972,368
Granted
Jul 7, 2026
Kind
B2
Abstract

The present disclosure provides methods of treating a disease or disorder in a patient comprising administering 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione (“Compound (1)”), or a pharmaceutically acceptable salt thereof, to the patient, wherein the patient achieves a threshold steady-state plasma concentration of Compound (1). The present disclosure also provides methods of administering a therapeutically effective amount of Compound (1), or a pharmaceutically acceptable salt thereof, to a patient. Compound (1) is a PPAR-γ agonist that is used to treat a variety of diseases and disorders including, but not limited to, nonalcoholic steatohepatitis and central nervous system diseases, e.g., X-linked adrenoleukodystrophy, Friedreich's Ataxia.

Claims (354)

1 . A method of administering a therapeutically effective amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione to treat a disease or disorder in a patient in need thereof, wherein the disease or disorder is chronic granulomatous disorder, a polycystic ovary syndrome, a thyroid carcinoma, a thyroid autoimmune disorder, a pituitary adenoma, atherosclerosis, a skin disease, or an inflammatory respiratory disease, the method comprising:

(a) administering an amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione, or a pharmaceutically acceptable salt thereof, to the patient per day;

(b) obtaining a plasma sample from the patient after at least four days of administering according to (a);

(c) determining the plasma concentration of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione in the plasma sample obtained in (b); and

(d) administering a recalculated amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione, or a pharmaceutically acceptable salt thereof, in milligrams, to the patient per day as determined according to the Equation 1:

recalculated

amount

in

mg

=

SD

×

(

CMT

PC

)

,

Equation

1

wherein:

SD is the amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione, or a pharmaceutically acceptable salt thereof, administered to the patient in (a) in mg;

CMT is the C min target in ng/mL;

C min target =(target AUC in ng h/mL×0.0341±20%)−1104±20%; and

PC is the plasma concentration in ng/mL of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione determined in (c), wherein the target AUC is about 100 μg h/mL to about 300 μg h/mL.

2 . The method of claim 1 , wherein the plasma sample is obtained from the patient after at least 7 days of administering according to (a).

3 . The method of claim 1 , wherein 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride is administered to the patient per day in (a) and (d).

4 . The method of claim 3 , wherein about 180 mg of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride is administered to the patient per day in (a) and the target AUC is about 200 ng·h/mL.

5 . The method of claim 3 , wherein a recalculated amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride is administered to the patient per day in (d).

6 . The method of claim 3 , wherein the 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride is administered to the patient in (a) and (d) as a suspension comprising about 15 mg of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride per mL.

7 . A method of administering a therapeutically effective amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione to treat a disease or disorder in a patient in need thereof, wherein the disease or disorder is chronic granulomatous disorder, a polycystic ovary syndrome, a thyroid carcinoma, a thyroid autoimmune disorder, a pituitary adenoma, atherosclerosis, a skin disease, or an inflammatory respiratory disease, the method comprising:

(a) administering 5 to 20 milliliters of an oral suspension of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride to the patient per day, wherein the oral suspension comprises 15 mg of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride per mL;

(b) obtaining a plasma sample from the patient following 5 days or more of administering according to (a);

(c) determining the C min ss of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione in the plasma sample obtained in (b); and

(d) administering a recalculated amount, in milliliters, of the oral suspension to the patient per day as determined according to the Equation 4:

Dose

V

1

=

Dose

p

r

e

-

V

1

×

C

min

T

A

R

C

min

V

1

,

Equation

4

wherein:

Dose V1 is the recalculated amount, in milliliters, of the oral suspension administered to the patient per day in (d);

Dose pre-V1 is the amount, in milliliters, of the oral suspension administered to the patient in (a);

C min V1 is the C min ss , in ng/mL, of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione determined in (c) taken 22 hours to 26 hours after the last administration; and

C min TAR is the targeted concentration in ng/mL of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione, wherein:

(A) C min TAR is calculated according to Equation 5A:

C min TAR =7700−(88.5×Dose pre-V1 )  Equation 5A

if the plasma sample in (b) was obtained 18 hours to 19.9 hours after the last administration of the oral suspension in (a);

(B) C min TAR is calculated according to Equation 5B:

C min TAR =7440−(103.4×Dose pre-V1 )  Equation 5B

if the plasma sample in (b) was obtained 20 hours to 21.9 hours after the last administration of the oral suspension in (a);

(C) C min TAR is 5716 if the plasma sample in (b) was obtained 22 hours to 25.9 hours after the last administration of the oral suspension in (a);

(D) C min TAR is calculated according to Equation 5D:

C min TAR =6740−(138.6×Dose pre-V1 )  Equation 5D

if the plasma sample in (b) was obtained 26 hours to 27.9 hours after the last administration of the oral suspension in (a); or

(E) C min TAR is calculated according to Equation 5E:

C min TAR =6520−(148.0×Dose pre-V1 )  Equation 5E

if the plasma sample in (b) was obtained 28 hours to 30 hours after the last administration of the oral suspension in (a).

8 . The method of claim 7 further comprising:

(i) obtaining a plasma sample from the patient following 5 days or more of administering the recalculated amount, in milliliters, of the oral suspension of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride to the patient per day in (d);

(ii) determining the C min calcd , in ng/mL, of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione in the plasma sample obtained in (i) according to Equation 6:

C

min

c

a

l

c

d

=

Dose

V

1

×

C

min

V

2

Dose

last

taken

;

Equation

6

wherein Dose last taken is the amount, in milliliters, of the last administered dose of the oral suspension taken by the patient;

(iii) determining the AUC Calcd , in μg·h/mL, of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione based on the C min Calcd determined in (ii), wherein:

(A) the AUC Calcd is calculated according to Equation 7A:

A

U

C

Calcd

=

C

min

calcd

+

(

88.5

×

Dose

last

taken

)

3

8

.

5

,

Equation

7

A

if the plasma sample in (i) was obtained between 18 hours to 19.9 hours after the last administration of the oral suspension;

(B) the AUC Calcd is calculated according to Equation 7B:

A

U

C

C

a

l

c

d

=

C

min

c

a

l

c

d

+

(

103.4

×

Dose

last

taken

)

3

7

.

2

,

Equation

7

B

if the plasma sample in (i) was obtained 20 hours to 21.9 hours after the last administration of the oral suspension;

(C) the AUC Calcd is calculated according to Equation 7C:

A

U

C

C

a

l

c

d

=

C

min

c

a

l

c

d

+

1104.1

3

4

.

1

,

Equation

7

C

if the plasma sample in (i) was obtained 22 hours to 25.9 hours after the last administration of the oral suspension;

(D) the AUC Calcd is calculated according to Equation 7D:

A

U

C

Calcd

=

C

min

c

a

l

c

d

+

(

1

3

8.6

×

Dose

last

taken

)

3

3

.

7

,

Equation

7

D

if the plasma sample in (i) was obtained 26 hours to 27.9 hours after the last administration of the oral suspension; or

(E) the AUC Calcd is calculated according to Equation 7E:

A

U

C

C

a

l

c

d

=

C

min

c

a

l

c

d

+

(

148

×

Dose

last

taken

)

32.6

,

Equation

7

E

if the plasma sample in (i) was obtained 28 hours to 30 hours after the last administration of the oral suspension; and

(iv) administering the same recalculated amount, in milliliters, of the oral suspension to the patient per day as in (i) for 5 days or more if the AUC Calcd is 150 to 240 μg h/mL and, optionally, repeating (i)-(iii); or

(v) administering a new recalculated amount, in milliliters, of the oral suspension to the patient per day in (i) if the AUC Calcd is less than 150 or more than 240 μg h/mL.

9 . A method of administering a therapeutically effective amount of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione to treat a disease or disorder in a patient in need thereof, wherein the disease or disorder is chronic granulomatous disorder, a polycystic ovary syndrome, a thyroid carcinoma, a thyroid autoimmune disorder, a pituitary adenoma, atherosclerosis, a skin disease, or an inflammatory respiratory disease, the method comprising:

(a) administering an initial dose of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride to the patient once per day for 5 or more days; and

(b) administering a recalculated dose of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride according to:

(i) Equation 8a:

D recal =D initial *( AUC Tar /AUC _0 t )  Equation 8a

wherein:

D recal is recalculated dose of the 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride administered to the patient in milligrams;

D initial is the initial dose of the 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride administered to the patient in milligrams;

AUC Tar is the targeted exposure of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione in the patient 24 hours after the last administration in (a) in ng h/ml; and

AUC_0t is the calculated exposure of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione in the patient 24 hours after the last administration in (a) in ng h/ml; and

(ii) Equation 8b:

AUC _0 t =(28.31+0.472*Δ T )* C +(34410+2234*Δ T )* D initial /150  Equation 8b

wherein:

AUC_0t is the calculated exposure of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione in the patient 24 hours after the last administration in (a) in ng h/ml;

D initial is the initial dose of the 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride administered to the patient in milligrams;

C is the plasma concentration of 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione in the patient in ng/ml, wherein the plasma sample is taken from the patient 24±6 hours after the last administration in (a); and

ΔT is the difference between the time the plasma sample is taken from the patient and 24 hours after the last administration in (a) in hours;

wherein the targeted exposure is 50,000 ng h/mL to 250,000 ng h/mL.

10 . The method of claim 9 , the targeted exposure is 100,000 ng·h/mL to 200,000 ng·h/mL.

11 . The method of claim 9 , the targeted exposure is 50,000 ng·h/mL to 100,000 ng·h/mL.

12 . The use of claim 1 , wherein the target AUC is about 50 μgh/mL to about 100 μgh/mL.