IP Library Granted Patent US 9,200,007
Granted Patent B2
US 9,200,007 · App. 13/388,164 · Granted Dec 1, 2015

Tricyclic heterocyclic compounds as phosphoinositide 3-kinase inhibitors

Inventors: Stephen Joseph Shuttleworth (Hampshire, GB); Alexander Richard Liam Cecil (Hampshire, GB); Thomas James Hill (Hampshire, GB); Franck Alexandre Silva (Hampshire, GB)
Assignee: Karus Therapeutics Limited
C07D495/14C07D491/147C07D519/00
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Quick Facts
Patent No.
US 9,200,007
App. No.
13/388,164
Granted
Dec 1, 2015
Kind
B2
Abstract

Compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein: W is O, N—H, N-(C 1 -C 10 alkyl) or S; each X is independently CH or N; R 1 is a 5 to 7-membered saturated or unsaturated, optionally substituted heterocycle containing at least 1 heteroatom selected from N or O; R 2 is (LQ) m Y; and each R 3 is independently H, C 1 -C 10 alkyl, aryl or heteroaryl, are surprisingly found to be inhibitors of PI3K-p110δ, and therefore have utility in therapy.

Claims (17)

1. A compound represented by formula I:

or a pharmaceutically acceptable salt thereof, wherein:

W is O;

Xis CH;

R 2 is (LQ) m Y;

m is 1;

L is: C 1 alkylene;

Q is selected from the group consisting of: heteroarylene, —NR 3 —, —C(O)—, —NR 4 R 5 —, and —C(O)NR 4 R 5 , where R 4 and R 5 together with the nitrogen to which they are attached form a 5 to 7-membered heterocycle linker;

Y is selected from the group consisting of: H, C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, —OR 3 , —N(R 3 ) 2 , —SO 2 —R 3 , —SO 2 —N(R 3 ) 2 , halogen, —CN, and —C(halogen) b R 3 ( 3−b ),

b is from 1 to 3; and

R 3 is independently selected for each occurrence from H or C 1 -C 10 alkyl.

2. The compound according to claim 1 , wherein both of the R 3 groups that are attached to the 6,5-ring system in formula I are H.

3. The compound according to claim 1 , wherein Q is —NR 4 R 5 wherein R 4 and R 5 together with the nitrogen to which they are attached form a 5 to 7-membered heterocycle linker having an additional heteroatom O; and Y is H.

4. A compound selected from the structures shown below:

or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a compound according to claim 1 , and a pharmaceutically acceptable excipient.

6. The compound according to claim 1 , wherein Q is selected from —NR 3 —and —NR 4 R 5 —.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 5, 2022
From: KARUS THERAPEUTICS LIMITED
To: CONVALIFE (SHANGHAI) CO. LIMITED
Reel/Frame 061315/0660 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2012
From: SHUTTLEWORTH, STEPHEN JOSEPH; CECIL, ALEXANDER RICHARD LIAM; HILL, THOMAS JAMES; SILVA, FRANCK ALEXANDRE
To: KARUS THERAPEUTICS LIMITED
Reel/Frame 028055/0122 →
Priority Claims (2)
GB 0914594.7 · Aug 20, 2009 · national
GB 1005584.6 · Apr 1, 2010 · national
Continuity (1)
Related Publication 20120178737A1 · Jul 12, 2012