IP Library Granted Patent US 11,583,533
Granted Patent B2
US 11,583,533 · App. 17/143,384 · Granted Feb 21, 2023

Topical pharmaceutical compositions comprising 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile

Inventors: Katherine Chu (San Francisco, CA); Jyoti Wadhwa (San Mateo, CA); Jason Carbol (Petaluma, CA); Pasit Phiasivongsa (Hillsborough, CA); Claire Langrish (Redwood City, CA); Dolca Thomas (San Francisco, CA)
Assignee: Principia Biopharma Inc.
A61K31/519A61K9/06A61K47/02A61K47/10A61K47/12A61K47/14A61K47/26A61K47/32A61K47/34A61K47/44
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 11,583,533
App. No.
17/143,384
Granted
Feb 21, 2023
Kind
B2
Abstract

Disclosed herein are topical pharmaceutical compositions, e.g., for application to the skin of a subject, comprising (R)-2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile (Compound (I)), methods of making the same, and methods of using the same, e.g., for the treatment of various dermatological disorders.

Claims (50)

1. A pharmaceutical composition comprising:

at least one compound chosen from 2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile and pharmaceutically acceptable salts thereof; and

about 0.1% to about 20% by weight of medium chain triglycerides;

about 0.1% to about 20% by weight of polyethoxylated sorbitan and oleic acid;

about 0.1% to about 20% by weight of glycerin;

about 0.1% to about 45% by weight of propylene glycol;

about 0.01% to about 0.5% by weight of methylparaben;

about 0.01% to about 0.2% by weight of propylparaben;

about 0.1% to about 4% by weight of a crosslinked polyacrylic acid polymer;

an amount of 10% (w/w) sodium hydroxide solution sufficient to adjust the pH of the pharmaceutical composition to a value in the range of about 4 to about 6; and

Q.S. to 100% with purified water,

wherein the pharmaceutical composition is in the form of a gel.

2. The pharmaceutical composition of claim 1 , wherein the at least one compound is suspended in the gel.

3. The pharmaceutical composition of claim 1 , wherein the pharmaceutical composition comprises about 0.1% to about 10% by weight of the at least one compound.

4. The pharmaceutical composition of claim 3 , wherein the pharmaceutical composition comprises about 0.5% to about 10% by weight of the at least one compound.

5. The pharmaceutical composition of claim 1 wherein at least about 95% by weight of the at least one compound is (R)-2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile.

6. The pharmaceutical composition of claim 1 , wherein at least about 95% by weight of the at least one compound is an (E) isomer.

7. The pharmaceutical composition of claim 5 , wherein the at least one compound is substantially amorphous.

8. The pharmaceutical composition of claim 5 , wherein the at least one compound is micronized.

9. The pharmaceutical composition of claim 1 , wherein the at least one compound is crystalline.

10. The pharmaceutical composition of claim 9 , wherein the at least one compound is crystalline Form (I).

11. The pharmaceutical composition of claim 9 , wherein the at least one compound is crystalline Form (II).

12. A method of treating a dermatological disorder in a mammal in need thereof, the method comprising topically administering to at least a portion of the skin of the subject of the mammal at least one topical pharmaceutical composition of claim 1 .

13. A pharmaceutical composition comprising:

at least one compound chosen from 2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile and pharmaceutically acceptable salts thereof;

at least one pH dependent gelling agent;

at least one emollient or humectant;

at least one preservative;

at least one lubricity agent;

at least one wetting agent; and

wherein the pharmaceutical composition is in the form of a gel.

14. The pharmaceutical composition of claim 13 , wherein the pharmaceutical composition comprises about 0.1% to about 4% by weight of the at least one pH dependent gelling agent.

15. The pharmaceutical composition of claim 13 , wherein the at least one pH dependent gelling agent is a crosslinked polyacrylic acid polymer.

16. The pharmaceutical composition of claim 13 , wherein the at least one compound is suspended in the gel.

17. The pharmaceutical composition of claim 13 , wherein the pharmaceutical composition comprises about 0.1% to about 65% by weight of the at least one emollient or humectant.

18. The pharmaceutical composition of claim 13 , wherein the at least one emollient or humectant is chosen from glycerin, propylene glycol, and combinations thereof.

19. The pharmaceutical composition of claim 13 , wherein the pharmaceutical composition comprises about 0.01% to about 0.7% by weight of the at least one preservative.

20. The pharmaceutical composition of claim 16 , wherein the at least one preservative is chosen from methylparaben, propylparaben, and combinations thereof.

21. The pharmaceutical composition of claim 13 , wherein the pharmaceutical composition comprises about 0.1% to about 20% by weight of the at least one lubricity agent.

22. The pharmaceutical composition of claim 13 , wherein the at least one lubricity agent is chosen from medium chain triglycerides.

23. The pharmaceutical composition of claim 13 , wherein the pharmaceutical composition comprises about 0.1% to about 20% by weight of the at least one wetting agent.

24. The pharmaceutical composition of claim 13 , wherein the at least one wetting agent is polyethoxylated sorbitan and oleic acid.

25. The pharmaceutical composition of claim 13 , wherein at least about 95% by weight of the at least one compound is (R)-2-(3-(4-amino-3-(2-fluoro phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4,4-dimethylpent enenitrile.

26. The pharmaceutical composition of claim 13 , wherein at least about 95% by weight of the at least one compound is an (E) isomer.

27. The pharmaceutical composition of claim 26 , wherein the at least one compound is substantially amorphous.

28. The pharmaceutical composition of claim 27 , wherein the at least one compound is micronized.

29. The pharmaceutical composition of claim 13 , wherein the at least one compound is crystalline.

30. The pharmaceutical composition of claim 29 , wherein the at least one compound is crystalline Form (I).

31. The pharmaceutical composition of claim 29 , wherein the at least one compound is crystalline Form (II).

32. A method of treating a dermatological disorder in a mammal in need thereof, the method comprising topically administering to at least a portion of the skin of the subject of the mammal at least one topical pharmaceutical composition of claim 13 .

Assignments (2)
ASSIGNEE CHANGE OF ADDRESS Recorded Sep 16, 2025
From: PRINCIPIA BIOPHARMA INC.
To: PRINCIPIA BIOPHARMA INC.
Reel/Frame 072881/0270 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 20, 2022
From: CHU, KATHERINE; WADHWA, JYOTI; CARBOL, JASON; PHIASIVONGSA, PASIT; LANGRISH, CLAIRE; THOMAS, DOLCA
To: PRINCIPIA BIOPHARMA INC.
Reel/Frame 062158/0881 →
Continuity (3)
Provisional Application 63003536 · Apr 1, 2020
Provisional Application 62958616 · Jan 8, 2020
Related Publication 20210205313A1 · Jul 8, 2021