Phenoxy acetic acids and phenyl propionic acids as PPAR delta agonists

Patent metadata

Field	Value
Publication number	US-11420929-B2
Application number	US-202117196873-A
Country	US
Kind code	B2
Filing date	Mar 9, 2021
Priority date	Dec 22, 2005
Publication date	Aug 23, 2022
Grant date	Aug 23, 2022

Abstract

Phenoxy acetic acids and phenyl propionic acids and their use in improving mitochondrial energy output in a subject are provided herein. The present compounds are activators of PPARδ and may be useful for treating conditions mediated by the same.

First claim

The invention claimed is:

1. A process for the preparation of a compound of the following formula:

or a pharmaceutically acceptable salt thereof,
comprising saponification of a compound of formula (I):

or a salt thereof, wherein:
is a double bond, with either E or Z substitution;
X 1 is C 1-6 alkyl substituted with morpholino;
X 2 is phenylene;
X 3 is phenyl substituted with one or more halogens;
Ar is phenylene optionally substituted with methyl;
Y 1 is O;
Y 2 is O;
Z is CH 2 ;
R 1 is hydrogen; and
R 2 is C 1-6 alkyl.

2. The process of claim 1 , wherein X 1 is morpholin-4-ylmethyl.

3. The process of claim 2 , wherein R 2 is methyl or ethyl.

4. The process of claim 1 , wherein the compound of formula (I) is methyl (Z)-[4-[3-(4-fluorophenyl)-3-[4-[3-(morpholin-4-yl) propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate, or a salt thereof.

5. The process of claim 1 , wherein the compound of formula (I) is methyl (E)-[4-[3-(4-fluorophenyl)-3-[4-[3-(morpholin-4-yl) propynyl]phenyl]allyloxy]-2-methylphenoxy]acetate, or a salt thereof.

Assignees

• Vtv Therapeutics Llc

Inventors

• Sauerberg Per
• Pihera Pavel
• Polivka Zdenek
• Havranek Miroslav
• Pettersson Ingrid
• Mogensen John Patrick

Classifications

• A61K31/5377 Primary

  not condensed and containing further heterocyclic rings, e.g. timolol · CPC title

• A61K31/192

  having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid  {(cannabinoids A61K31/658)} · CPC title

• C07C69/736 Primary

  the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring · CPC title

• A61K31/4025

  not condensed and containing further heterocyclic rings, e.g. cromakalim · CPC title

• A61K31/381

  having five-membered rings · CPC title