IP Library Granted Patent US 10,208,074
Granted Patent B2
US 10,208,074 · App. 15/928,335 · Granted Feb 19, 2019

Pyrazole compounds and method for making and using the compounds

Inventors: Ryan Kelley (Pacifica, CA); Hui Li (Santa Clara, CA); Thilo Heckrodt (San Francisco, CA); Yan Chen (Foster City, CA); Darren McMurtrie (Daly City, CA); Kin Tso (San Francisco, CA); Vanessa Taylor (San Francisco, CA); Rajinder Singh (Belmont, CA); Rose Yen (San Francisco, CA); Jack Maung (Daly City, CA)
Assignee: Rigel Pharmaceuticals, Inc.
C07F9/65586C07D405/04C07D405/14C07D413/04C07D417/04C07D417/14C07D471/04
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Quick Facts
Patent No.
US 10,208,074
App. No.
15/928,335
Granted
Feb 19, 2019
Kind
B2
Abstract

Disclosed embodiments concern novel interleukin receptor associated kinases (IRAK) inhibitors and compositions comprising such inhibitors. Also disclosed are methods of making and using the compounds and compositions. The disclosed compounds and/or compositions may be used to treat or prevent an IRAK-associated disease or condition.

Claims (25)

1. A compound having a formula

or a pharmaceutically acceptable salt thereof, wherein:

R 2 is alkyl or cycloalkyl;

each of R 4 , R 5 , R 6 , and R 7 independently is H or F;

R 8 and R 9 are each independently H or aliphatic;

R 10 is H, aliphatic, carboxyl ester, acyl, alkyl phosphate, alkyl phosphonate or aralkyl; and

R 14 is H or aliphatic.

2. The compound of claim 1 , wherein R 8 and R 9 are each independently H, haloalkyl, or alkyl.

3. The compound of claim 1 , wherein R 10 is H, alkyl, carboxyl ester, acyl, alkyl phosphate, alkyl phosphonate or aralkyl.

4. The compound of claim 1 , wherein:

R 8 and R 9 are each independently H, haloalkyl, or alkyl; and

R 10 is H, alkyl, alkyl phosphate, or alkyl phosphate.

5. The compound of claim 1 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

8. A composition, comprising a compound of claim 1 , and a pharmaceutically acceptable excipient.

9. The composition of claim 8 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

10. The composition of claim 8 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

11. The composition of claim 8 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

Assignments (3)
SECURITY INTEREST Recorded May 8, 2026
From: RIGEL PHARMACEUTICALS, INC.
To: MIDCAP FUNDING IV TRUST
Reel/Frame 075576/0880 →
SECURITY INTEREST Recorded Aug 25, 2022
From: RIGEL PHARMACEUTICALS, INC.
To: MIDCAP FINANCIAL TRUST
Reel/Frame 061327/0712 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 5, 2018
From: KELLEY, RYAN; LI, HUI; HECKRODT, THILO; CHEN, YAN; MCMURTRIE, DARREN; TAYLOR, VANESSA; SINGH, RAJINDER; YEN, ROSE; MAUNG, JACK; TSO, KIN
To: RIGEL PHARMACEUTICALS, INC.
Reel/Frame 045445/0216 →
Continuity (3)
Continuation 15136508 · Apr 22, 2016
Provisional Application 62151274 · Apr 22, 2015
Related Publication 20180208612A1 · Jul 26, 2018
Cited By (3)
US 12,357,623 US 12,384,775 US 12,441,723