US 11,773,077 B2
Compounds containing carbon-carbon linker as GPR120 agonists
Rajiv Sharma, Fremont, CA (US); Sanjay Kumar, Mumbai (IN); Vishal Mahajan, Thane (IN); Komal Bajaj, Mumbai (IN); and Pallavi Godse, Pune (IN)
Assigned to PIRAMAL ENTERPRISES LIMITED, Mumbai (IN)
Filed by PIRAMAL ENTERPRISES LIMITED, Mumbai (IN)
Filed on Nov. 2, 2020, as Appl. No. 17/87,144.
Application 17/087,144 is a division of application No. 15/548,628, granted, now 10,941,133, previously published as PCT/IN2016/000035, filed on Feb. 2, 2016.
Claims priority of provisional application 62/112,285, filed on Feb. 5, 2015.
Prior Publication US 2021/0053938 A1, Feb. 25, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/10 (2006.01); A61P 3/00 (2006.01); A61P 29/00 (2006.01); A61K 31/192 (2006.01); C07D 333/24 (2006.01); C07D 333/60 (2006.01); C07D 409/10 (2006.01); C07D 277/60 (2006.01); C07D 213/64 (2006.01); C07D 307/79 (2006.01); C07C 57/62 (2006.01); A61K 45/06 (2006.01); A61K 31/381 (2006.01); A61K 31/428 (2006.01); A61K 31/4418 (2006.01); C07D 339/06 (2006.01); C07D 277/66 (2006.01); C07D 333/08 (2006.01)
CPC C07D 401/10 (2013.01) [A61K 31/192 (2013.01); A61K 31/381 (2013.01); A61K 31/428 (2013.01); A61K 31/4418 (2013.01); A61K 45/06 (2013.01); A61P 3/00 (2018.01); A61P 29/00 (2018.01); C07C 57/62 (2013.01); C07D 213/64 (2013.01); C07D 277/60 (2013.01); C07D 277/66 (2013.01); C07D 307/79 (2013.01); C07D 333/08 (2013.01); C07D 333/24 (2013.01); C07D 333/60 (2013.01); C07D 339/06 (2013.01); C07D 409/10 (2013.01); C07C 2601/04 (2017.05); C07C 2601/14 (2017.05); C07C 2601/16 (2017.05); C07C 2602/06 (2017.05); C07C 2602/10 (2017.05)] 23 Claims
 
1. A compound of formula (I);

OG Complex Work Unit Chemistry
wherein,
Ring A is selected from the group consisting of a 3- to 10-membered cycloalkyl, a 5- to 12-membered heterocycloalkyl, (C6-C10)aryl, and a 5- to 12-membered heteroaryl, wherein the heterocycloalkyl and the heteroaryl contain 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S;
Ring B and Ring C are independently selected from a (C6-C10)aryl or a 5- to 12-membered heteroaryl containing 1, 2 or 3 heteroatoms independently selected from the group consisting of N, O and S;
X is selected from

OG Complex Work Unit Chemistry
wherein custom character represents a point of attachment;
R is hydrogen or a (C1-C6)alkyl;
R1, R2, and R3 at each occurrence are independently selected from the group consisting of hydrogen, a halogen, a (C1-C6)alkyl, a halo(C1-C6)alkyl, a 3- to 10-membered cycloalkyl and 5- to 12-membered heterocycloalkyl; or two R1 are combined together with Ring A to form a 3- to 6-membered cycloalkyl or a 5- to 12-membered heterocycloalkyl;
R4 and R7 are independently selected from hydrogen or a (C1-C6)alkyl;
R5 and R6 are independently selected from the group consisting of hydrogen, a halogen and a (C1-C6)alkyl; and
m, n and p are each integer independently selected from 1, 2 and 3;
wherein,
the (C1-C6)alkyl is unsubstituted or substituted with one or more groups independently selected from the group consisting of halogen, hydroxy, cyano, nitro, (C1-C6)alkyl, halo(C1-C6)alkyl, —O(C1-C6)alkyl, (C3-C8)cycloalkyl, (C6-C10)aryl, heterocycloalkyl, and heteroaryl;
the cycloalkyl is a 3- to 10-membered ring, which is unsubstituted or substituted with one or more groups independently selected from the group consisting of (C1-C6)alkyl, halogen, hydroxy, —O—(C1-C6)alkyl, (C3-C10)cycloalkyl, (C6-C10)aryl, heterocycloalkyl, heteroaryl, amino, and cyano;
the heteroaryl is a 5- to 12-membered ring, which is unsubstituted or substituted with one or more groups independently selected from the group consisting of (C1-C6)alkyl, halogen, hydroxy, —O—(C1-C6)alkyl, (C3-C10)cycloalkyl, (C6-C10)aryl, heterocycloalkyl, heteroaryl, amino, and cyano;
the heterocycloalkyl is a 5- to 12-membered ring, which is unsubstituted or substituted with one or more groups independently selected from the group consisting of (C1-C6)alkyl, halogen, hydroxy, —O—(C1-C6)alkyl, (C3-C10)cycloalkyl, (C6-C10)aryl, heterocycloalkyl, heteroaryl, amino, and cyano;
the halogen is selected from chlorine, bromine, iodine, and fluorine; or
a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof.