Modulators of CRTH2 activity

• US 7,205,329 B2
• Filed: 07/18/2005
• Issued: 04/17/2007
• Est. Priority Date: 05/30/2003
• Status: Expired due to Fees

• Current Assignee: Ironwood Pharmaceuticals, Inc.
• Original Assignee: Microbia, Inc. (DSM-Firmenich AG)
• Inventors: Currie, Mark G., Cali, Brian M., Milne, G. Todd, Talley, John Jeffrey, Chien, Yueh-Tyng, Zimmerman, Craig, Chen, Barbara, Yang, Jing Jing
• Primary Examiner(s): Saeed; Kamal A.
• Assistant Examiner(s): CHU, YONG LIANG
• Application Number:
  US11/183,626
• Publication Number:
  US 20060135591A1
• Time in Patent Office: 638 Days
• Field of Search: None
• US Class Current: 514/415
• CPC Class Codes: C07D 209/42 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 409/06 linked by a carbon chain containing only aliphatic carbon atoms

Abstract

Modulators of the CRTH2 receptor and their use in the treatment of various disorders, including asthma are described.

Claims

1. A compound having the formula:

2. The compound of claim 1 wherein m is 1.

3. The compound of claim 1 wherein m is 2.

4. The compound of claim 1 wherein m is 3.

5. The compound of claim 1 wherein R₃ is F;

Cl;

—

CN;

—

OH;

—

SH;

a C₂–

C₃ alkyl, optionally independently substituted with one or more F or Cl;

—

OR_3A;

—

SR_3A;

—

SOR_3A;

or —

S(O)₂R_3A, wherein R_3A is a C₁–

C₃ alkyl, optionally independently substituted with one or more F or Cl.

6. The compound of claim 5 wherein R₃ is F;

Cl;

—

CN;

—

OH;

—

SH;

or a C₂–

C₃ alkyl, optionally independently substituted with one or more F or Cl.

7. The compound of claim 5 wherein R₃ is —

OR_3A;

—

SR_3A;

—

SOR_3A;

or —

S(O)₂R_3A, wherein R_3A is a C₁–

C₃ alkyl, optionally independently substituted with one or more F or Cl.

8. The compound of claim 1 wherein R is H.

9. The compound of claim 1 wherein R is a C₁–

C₃ alkyl, optionally independently substituted with one or more halogen.

10. The compound of claim 1 wherein R₄ is H, F or Cl.

11. The compound of claim 1 wherein R₅ is F or Cl.

12. The compound of claim 1 wherein R is H, or a C₁–

C₃ alkyl, optionally independently substituted with one or more F or Cl.

13. The compound of claim 1 wherein R₁ is H;

a C₁–

C₆ alkyl, optionally independently substituted with one or more —

OH, —

NH₂, F or Cl;

or a C₂–

C₆ alkenyl optionally independently substituted with one or more —

OH, —

NH₂, F or Cl.

14. The compound of claim 1 wherein R₂ is H;

a C₁–

C₆ alkyl, optionally independently substituted with one or more F or Cl;

or a C₂–

C₆ alkenyl optionally independently substituted with one or more F or Cl.

15. The compound of claim 1 wherein any halogen is selected from F and Cl.

16. The compound of claim 1 wherein R₃ is selected from:

F, Cl, Br, OH, —

OCH₃, —

OCH₂CH₃, —

OCF₂H, —

OCF₃,—

OCF₂CF₃, —

OCF₂CF₂H, —

CH₃, —

CF₂H, —

CF₃, —

SCH₃, —

SCF₂H, —

SCF₃, —

SCF₂CF₃, —

SCF₂CF₂H, and —

CN.

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