IP Library Granted Patent US 11,548,886
Granted Patent B2
US 11,548,886 · App. 16/998,660 · Granted Jan 10, 2023

Monocyclic compounds useful as GPR120 modulators

Inventors: Brian Raimundo (Boston, MA); Elena S. Koltun (Boston, MA); John Griffin (Boston, MA); Eric Stangeland (Boston, MA)
Assignee: Valo Health, Inc.
C07D417/14A61P1/16A61P3/10A61P25/16A61P25/28A61P29/00C07D401/04C07D401/14C07D417/04C07D471/04
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Quick Facts
Patent No.
US 11,548,886
App. No.
16/998,660
Granted
Jan 10, 2023
Kind
B2
Abstract

Provided herein are compounds, compositions including them, and methods of modulating GPR120 activity and treating diseases mediated by GPR120 by administering such compounds and compositions.

Claims (30)

1. A compound of formula II:

or a pharmaceutically acceptable salt thereof, wherein:

W is O;

each X independently is CH, CR 3 or N wherein R 3 is halogen, alkyl, alkoxy, or CN;

Y is SO 2 , CO, CH 2 , —C(CH 3 ) 2 —, or —CH(CH 3 )—;

Z is —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, or —C(CH 2 CH 2 )—;

R 1 is an unsubstituted alkyl, a substituted alkyl, an unsubstituted 3-7 membered cycloalkyl, a substituted 3-7 membered cycloalkyl, an unsubstituted heterocyclyl, a substituted heterocyclyl, unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl or a substituted heteroaryl; and

R 2 is H, halogen, CN, OCH 3 , OCF 3 , NHAc, an unsubstituted alkyl, a substituted alkyl, an unsubstituted amido, a substituted amido, an unsubstituted cycloalkyl, a substituted cycloalkyl, an unsubstituted heterocyclyl, a substituted heterocyclyl, an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl, or a substituted heteroaryl.

2. The compound of claim 1 , wherein R 1 is selected from the group of:

wherein, Ru is the point of attachment to W and R 12 and R 13 are independently H, CH 3 , CF 3 , or F.

3. The compound of claim 1 , wherein R 1 is selected from the group of:

wherein, R 11 is the point of attachment to W and R 15 is H, halogen, alkyl, CF 3 , OCH 3 , OCF 3 , or CN, and R 16 is H, halogen, alkyl, CF 3 , OCH 3 , OCF 3 , CN, NHCOR 14 , or N(CH 3 )COR 14 wherein R 14 is alkyl, cycloalkyl, aryl or heteroaryl.

4. The compound of claim 1 , wherein R 1 is selected from the group of:

wherein Ru is the point of attachment to W and R 15 and R 17 are independently H, halogen, alkyl, CF 3 , OCH 3 , OCF 3 , or CN.

5. A compound of formula III:

wherein:

W is O;

each X independently is CH, CR 3 or N wherein R 3 is halogen, alkyl, alkoxy, CN;

Y is SO 2 , CO, CH 2 , —C(CH 3 ) 2 —, or —CH(CH 3 )—;

Z is —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, or —C(CH 2 CH 2 )—;

R 1 is an unsubstituted alkyl, a substituted alkyl, an unsubstituted 3-7 membered cycloalkyl, a substituted 3-7 membered cycloalkyl, an unsubstituted heterocyclyl, a substituted heterocyclyl, an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl or a substituted heteroaryl; and

R 2 is H, halogen, CN, OCH 3 , OCF 3 , NHAc, an unsubstituted alkyl, a substituted alkyl, an unsubstituted amido, a substituted amido, an unsubstituted cycloalkyl, a substituted cycloalkyl, unsubstituted heterocyclyl, a substituted heterocyclyl, an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl, or a substituted heteroaryl.

6. The compound of claim 5 , wherein R 1 is selected from the group of:

wherein, R 11 is the point of attachment to W and R 12 and R 13 are independently H, CH 3 , CF 3 , or F.

7. The compound of claim 5 , wherein R 1 is selected from the group of:

wherein, R 11 is the point of attachment to W and R 15 is H, halogen, alkyl, CF 3 , OCH 3 , OCF 3 , or CN, and R 16 is H, halogen, alkyl, CF 3 , OCH 3 , OCF 3 , CN, NHCOR 14 , or N(CH 3 )COR 14 wherein R 14 is alkyl, cycloalkyl, aryl or heteroaryl.

8. The compound of claim 5 , wherein R 1 is selected from the group of:

wherein Ru is the point of attachment to W and R 15 and R 17 are independently H, halogen, alkyl, CF 3 , OCH 3 , OCF 3 , or CN.

9. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.

10. A pharmaceutical composition comprising the compound of claim 5 and a pharmaceutically acceptable excipient.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Oct 17, 2023
From: FIRST-CITIZENS BANK & TRUST COMPANY, AS AGENT
To: VALO HEALTH, INC.; VALO HEALTH, LLC
Reel/Frame 065255/0660 →
SECURITY INTEREST Recorded Jul 6, 2023
From: VALO HEALTH, LLC; VALO HEALTH, INC.
To: FIRST-CITIZENS BANK & TRUST COMPANY, AS AGENT
Reel/Frame 064207/0957 →
CHANGE OF NAME Recorded Sep 16, 2020
From: INTEGRAL HEALTH, INC.
To: VALO HEALTH, INC.
Reel/Frame 053787/0514 →
Continuity (3)
Continuation 16331916
Provisional Application 62393616 · Sep 12, 2016
Related Publication 20210101896A1 · Apr 8, 2021