Granted Patent
B2
US 12,624,040 · App. 17/792,472 · Granted May 12, 2026
Compositions of substituted pyrazolopyrimidines and uses thereof
Assignee:
KSQ Therapeutics, Inc.
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Abstract
Pharmaceutical formulations comprising substituted pyrazolopyrimidines are disclosed herein. Also disclosed are amorphous solid dispersions comprising substituted pyrazolopyrimidines, processes for preparing these amorphous solid dispersions, pharmaceutical compositions comprising such dispersions, and methods of use thereof.
Claims (25)
1 . An amorphous solid dispersion, comprising a compound of Formula I:
or a pharmaceutically acceptable salt thereof,
wherein R is C 1-3 alkyl; and
X 1 and X 2 are independently selected from the group consisting of N and C, wherein the compound is in a solid substantially amorphous form and is dispersed in a polymer.
2 . The amorphous solid dispersion according to claim 1 , wherein the compound is 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-(4-(1-isopropyl-4-(trifluoromethyl)-1H-imidazol-2-yl) benzyl)-1H-pyrazolo[3,4-d]pyrimidine of Formula (II)
3 . The amorphous solid dispersion according to claim 1 , wherein the compound is 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-(4-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl) benzyl)-1H-pyrazolo[3,4-d]pyrimidine of Formula (III)
4 . The amorphous solid dispersion according to claim 1 , wherein the polymer is selected from the group consisting of polyvinyl pyrrolidone (PVP), polyvinyl alcohol (PVA), poly (ethylene glycol) (PEG), poly (ethylene oxide) (PEO), hydroxypropyl cellulose (HPC), hydroxypropyl methylcellulose (HPMC), copovidone, hydroxypropyl methylcellulose acetate succinate, methacrylic acid copolymer, polyacrylates and mixtures thereof.
5 . The amorphous solid dispersion according to claim 1 , wherein the polymer is selected from the group consisting of hydroxypropyl methylcellulose acetate succinate, hydroxypropyl methylcellulose, and methacrylic acid copolymer.
6 . The amorphous solid dispersion according to claim 5 , wherein the polymer is hydroxypropyl methylcellulose acetate succinate.
7 . The amorphous solid dispersion according to claim 5 , wherein the polymer is poly (methacrylic acid)-co-methyl methacrylate.
8 . The amorphous solid dispersion according to claim 2 , wherein the compound of Formula II is dispersed in hydroxypropyl methylcellulose acetate succinate.
9 . The amorphous solid dispersion according to claim 2 , wherein the compound of Formula II is dispersed in poly (methacrylic acid)-co-methyl methacrylate.
10 . The amorphous solid dispersion according to claim 3 , wherein the compound of Formula III is dispersed in hydroxypropyl methylcellulose acetate succinate.
11 . The amorphous solid dispersion according to claim 3 , wherein the compound of Formula III is dispersed in poly (methacrylic acid)-co-methyl methacrylate.
12 . The amorphous solid dispersion according to claim 4 , wherein the polymer is present in an amount of between about 40% and about 95% of the total weight of the solid dispersion.
13 . The amorphous solid dispersion according to claim 5 wherein the polymer is present in an amount of between about 40% and about 95% of the total weight of the solid dispersion.
14 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of the amorphous solid dispersion according to claim 1 .
15 . The pharmaceutical composition according to claim 14 , wherein said composition is in the form of a solid oral dosage form.
16 . A method of treating cancer, comprising administering to a patient in need thereof a therapeutically effective amount of the amorphous solid dispersion according to claim 1 .
17 . The amorphous solid dispersion according to claim 1 wherein said solid dispersion is prepared by hot-melt extrusion, lyophilization or spray-drying.
18 . A method of making a solid dispersion according to claim 1 , comprising:
a) mixing the compound of Formula I and the polymer in a solvent to provide a feeder solution; and
b) spray drying the feeder solution to provide the solid dispersion.
19 . The method according to claim 18 , wherein the compound of Formula I is provided as either the free base, salt, or solvate.
20 . The method according to claim 18 , wherein the solvent is selected from acetone, ethanol, methanol, or dichloromethane.
Assignments (4)
CHANGE OF ADDRESS
Recorded Sep 20, 2022
From: KSQ THERAPEUTICS, INC.
To: KSQ THERAPEUTICS, INC.
Reel/Frame 061479/0133 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Aug 26, 2022
From: LIU, HANLAN
To: KSQ THERAPEUTICS, INC.
Reel/Frame 060917/0323 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Aug 26, 2022
From: WENSLOW, ROBERT M., JR.
To: CRYSTAL PHARMATECH CO. LTD.
Reel/Frame 060917/0341 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Aug 26, 2022
From: CRYSTAL PHARMATECH CO. LTD.
To: KSQ THERAPEUTICS, INC.
Reel/Frame 061330/0704 →
Continuity (2)
Provisional Application
62961486
· Jan 15, 2020
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