EP4 agonists as therapeutic compounds

Patent metadata

Field	Value
Publication number	US-9926262-B2
Application number	US-201515316786-A
Country	US
Kind code	B2
Filing date	Jun 5, 2015
Priority date	Jun 6, 2014
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

Described herein are compounds that are EP 4 agonists and antagonists which are useful for treating a variety of pathological conditions associated with activity of EP 4 receptors.

First claim

What is claimed:

1. A compound having the following structure:

or a pharmaceutically acceptable salt or diastereomer or enantiomer thereof, wherein:
the dashed line is a single or a double bond;
Y is H or CH 3 ;
X is zero, one or two substituents on the cycloalkane or cycloalkene ring, said substituents chosen from the group consisting of C 1 -C 6 alkyl, hydroxyalkyl, aryl, halogen, cycloalkene, CF 3 , C(O)R, COCF 3 , SO 2 N(R) 2 , SO 2 NH 2 , NO 2 , and CN;
n is selected from the group consisting of 0, 1, 2, 3, or 4;
R is C 1 -C 6 alkyl;
R 6 is CO 2 H, CH 3 , CO 2 R 2 , CH 2 OR 2 , CONR 2 R 3 or tetrazol-5-yl;
R 7 is selected from the group consisting of H, CF 3 , OCH 3 ; and
R 8 is selected form the group consisting of H and OCH 3 .

2. The compound of claim 1 , wherein R 6 is CO 2 H and n is selected from the group consisting of 0, 1 and 2.

3. The compound of claim 1 , wherein n is selected from the group consisting of 0, 1 and 2 and the dashed line represents a double bond.

4. The compound of claim 3 , wherein R 7 and R 8 are OCH 3 .

5. The compound of claim 3 , wherein R 7 is CF 3 and R 8 is H.

6. The compound of claim 1 wherein n is selected from the group consisting of 1 and 2.

7. The compound of claim 1 wherein the dashed line represents a single bond.

8. The compound of claim 1 wherein n is selected from the group consisting of 3 and 4.

9. The compound of claim 1 wherein R 7 and R 8 are OCH 3 .

10. The compound of claim 1 selected from the group consisting of:

and pharmaceutically acceptable salts, diastereomers, and enantiomers thereof.

11. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

12. A method of treating glaucoma, the method comprising administering an effective amount of the compound of claim 1 to an individual in need thereof.

Assignees

• Allergan Inc

Inventors

• Old David W
• Hein christopher d

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P27/06

  Antiglaucoma agents or miotics · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title

• C07C2601/08

  the ring being saturated · CPC title

• C07C2601/14

  The ring being saturated · CPC title