IP Library Granted Patent US 9,561,228
Granted Patent B2
US 9,561,228 · App. 14/768,190 · Granted Feb 7, 2017

ERK inhibitors and uses thereof

Inventors: Nadia Haq (Waltham, MA); Deqiang Niu (Lexington, MA); Russell C. Petter (Stow, MA); Lixin Qiao (Andover, MA); Juswinder Singh (Ashland, MA); Zhendong Zhu (Westborough, MA)
Assignee: Celgene Avilomics Research, Inc.
A61K31/506A61K31/505A61K31/5377A61K31/541A61K31/675C07D239/48C07D401/12C07D401/14C07D403/12C07D405/12C07D495/04C07F9/65583
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Quick Facts
Patent No.
US 9,561,228
App. No.
14/768,190
Granted
Feb 7, 2017
Kind
B2
Abstract

Compounds, compositions thereof, and methods for inhibiting one or both ERK1 and ERK2 kinases are provided.

Claims (28)

1. A compound of formula II-a:

or a pharmaceutically acceptable salt thereof, wherein:

R 1 is selected from:

each R 2 is independently hydrogen, an optionally substituted C 1-6 aliphatic, halogen, or —OR;

Ring B is an optionally substituted group selected from a 3-7 membered saturated or partially unsaturated carbocyclic ring, a 5-6 membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 4-7 membered saturated or partially unsaturated heterocyclic ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, a 7-12 membered bicyclic saturated, partially unsaturated or aryl ring, a 7-12 membered bicyclic saturated or partially unsaturated heterocyclic ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an 8-12 membered bicyclic heteroaryl ring having 1-5 heteroatoms independently selected from nitrogen, oxygen, or sulfur;

each R 3 is independently selected from —R, —Cy, halogen, —OR, —SR, —CN, —NO 2 , —SO 2 NR, —SO 2 R, —SOR, —C(O)R, —C(O)OR, —OC(O)R, —OC(O)N(R) 2 , —C(O)N(R) 2 , —C(O)N(R)—OR—C(O)C(O)R, —P(O)(R) 2 , —NRC(O)OR, —NRC(O)R, —NRC(O)N(R) 2 , —NRSO 2 R, or —N(R) 2 ;

or two R 3 groups on the same carbon atom together form —C(O)—, —C(S)—, or —C(N—R)—;

each R is independently hydrogen or an optionally substituted group selected from C 1-6 aliphatic, phenyl, a 3-8 membered saturated or partially unsaturated carbocyclic ring, a 4-7 membered heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or a 5-6 membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; or

two R groups on the same nitrogen are taken together with the nitrogen atom to which they are attached to form a 4-7 membered heterocyclic ring having 0-2 additional heteroatoms independently selected from nitrogen, oxygen, or sulfur, or a 4-7 membered heteroaryl ring having 0-4 additional heteroatoms independently selected from nitrogen, oxygen, or sulfur;

Cy is an optionally substituted 5-6 membered monocyclic heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or an optionally substituted 4-7 membered saturated or partially unsaturated heterocyclic ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and

m and p are each independently 0-4.

2. The compound according claim 1 , wherein p is 0.

3. The compound according to claim 1 , wherein p is 1.

4. The compound according to claim 1 , wherein p is 2.

5. The compound according claim 1 , wherein m is 0.

6. The compound according to claim 1 , wherein m is 1.

7. The compound according to claim 1 , wherein m is 2.

8. The compound according to claim 1 , wherein R 1 is:

9. The compound according claim 1 , wherein at least one R 2 is optionally substituted C 1-6 aliphatic.

10. The compound according to claim 9 , wherein at least one R 2 is methyl.

11. The compound according to claim 1 , wherein at least one R 2 is halogen.

12. The compound according to claim 11 , wherein at least one R 2 is fluoro.

13. The compound according to claim 1 , wherein at least one R 3 is independently selected from —R, halogen, —OR, —SO 2 R, —C(O)R, —C(O)OR, —C(O)N(R) 2 , —C(O)N(R)—OR or —C(O)C(O)R.

14. The compound according to claim 1 , wherein two R 3 groups on the same carbon atom together form —C(O)—.

15. The compound according to claim 13 , wherein at least one R 3 is —R.

16. The compound according to claim 13 , wherein at least one R 3 is —OR.

17. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded May 3, 2023
From: CELGENE CAR LLC
To: BRISTOL-MYERS SQUIBB COMPANY
Reel/Frame 063526/0959 →
MERGER AND CHANGE OF NAME Recorded Feb 16, 2017
From: CELGENE AVILOMICS RESEARCH, INC.; CELGENE CAR LLC
To: CELGENE CAR LLC
Reel/Frame 041738/0041 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 29, 2015
From: HAQ, NADIA; NIU, DEQIANG; PETTER, RUSSELL C.; QIAO, LIXIN; SINGH, JUSWINDER; ZHU, ZHENDONG
To: CELGENE AVILOMICS RESEARCH, INC.
Reel/Frame 036681/0328 →
Continuity (3)
Provisional Application 61762408 · Feb 8, 2013
Provisional Application 61785126 · Mar 14, 2013
Related Publication 20160002176A1 · Jan 7, 2016