Granted Patent B2

US 12,673,953 · App. 18/197,979 · Granted Jul 7, 2026

Inventors: Kolbot By (San Ramon, CA); Katherine Chu (Cambridge, MA); Mohammad R. Masjedizadeh (San Jose, CA); Pasit Phiasivongsa (Hillsborough, CA); Jiang Zhu (San Ramon, CA)

Assignee: Principia Biopharma Inc.

C07D487/04

Abstract

Claims (22)

1 . A process for preparing an amorphous form of Compound (I):

wherein the process comprises:

dissolving 2-[3-[4-amino-3-(2-fluoro-4-phenoxyphenyl) pyrazolo [3,4-d]pyrimidin-1-yl] piperidine-1-carbonyl]-4-methy 1-4-[4-(oxetan-3-yl) piperazin-1-yl] pent-2-enenitrile (Compound (I)) in a first organic solvent to form an organic solution, wherein the first organic solvent comprises at least one of dichloromethane, ethyl acetate, carbon tetrachloride, chloroform, diethyl ether, diisopropyl ether, methyl tetrahydrofuran, and isopropyl acetate;

washing the organic solution with an aqueous acidic solution, wherein the organic solution comprises Compound (I);

removing the aqueous acidic solution;

performing a solvent exchange from the first organic solvent to a second organic solvent, wherein the second organic solvent comprises at least one of alkyl acetate, methyl tetrahydrofuran, toluene, methyl cyclopentyl ether, methyl tert-butyl ether, pentanone, acetone, acetonitrile, and alkyl propionate; and

obtaining an amorphous form of Compound (I) from the second organic solvent.

2 . The process according to claim 1 , wherein the process for obtaining the amorphous form of Compound (I) from the second organic solvent comprises:

washing the second organic solvent with an aqueous acidic solution, wherein the aqueous acidic solution comprises Compound (I);

removing the second organic solvent; and

obtaining the amorphous form of Compound (I) from the aqueous acidic solution.

3 . The process according to claim 2 , wherein the process for obtaining the amorphous form of Compound (I) from the aqueous acidic solution further comprises:

adding a base to the aqueous acidic solution to form an aqueous layer, wherein the aqueous layer comprises Compound (I);

extracting Compound (I) from the aqueous layer using a third organic solvent, wherein the third organic solvent comprises at least one of alkyl acetate, methyl tetrahydrofuran, toluene, methyl cyclopentyl ether, methyl tert-butyl ether, pentanone, acetone, acetonitrile, and alkyl propionate;

concentrating the organic layer; and

isolating the amorphous form of Compound (I) from the organic layer.

4 . The process according to claim 3 , wherein the process for isolating the amorphous form of Compound (I) from the organic layer further comprises adding an antisolvent to the organic layer, wherein the antisolvent comprises at least one of a hexane, a heptane, and an octane, to create a precipitate comprising Compound (I).

5 . The process according to claim 4 , wherein the antisolvent comprises at least one of n-hexane, n-heptane, and n-octane.

6 . The process according to claim 4 , wherein the process for isolating the amorphous form further comprises:

dissolving the precipitate comprising Compound (I) in a fourth organic solvent, wherein the fourth organic solvent comprises at least one of methanol, ethanol, acetone, acetonitrile, and methyl ethyl ketone, to form an organic solution; and

spray drying the organic solution to obtain the amorphous form of Compound (I).

7 . The process according to claim 6 , further comprising micronizing the amorphous form of Compound (I).

Assignments (2)

Continuity (4)

References Cited (400)