IP Library Granted Patent US 7,709,528
Granted Patent B2
US 7,709,528 · App. 11/439,827 · Granted May 4, 2010

Compounds, their preparation and use

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Quick Facts
Patent No.
US 7,709,528
App. No.
11/439,827
Granted
May 4, 2010
Kind
B2
Abstract

Novel compounds of the general formula (I), the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Proliferator-Activated Receptors (PPAR), in particular the PPARδ suptype.

Claims (170)

1. A compound of the general formula (I):

wherein X 1 is aryl optionally substituted with one or more substituents selected from

halogen, hydroxy, cyano, amino or carboxy; or

C 1-6 -alkyl, C 3-6 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, aryl, aralkyl, C 1-6 -alkoxy, C 3-6 -cycloalkoxy, aryloxy, aralkoxy, C 1-6 -alkylthio, arylthio, C 3-6 -cycloalkylthio, C 1-6 -alkylcarbonyl, arylcarbonyl, C 1-6 -alkylsulfonyl, arylsulfonyl, C 1-6 -alkyl-sulfonyloxy, arylsulfonyloxy, C 1-6 -alkylamido, arylamido, C 1-6 -alkyl-aminocarbonyl, C 1-6 -alkylamino, C 1-6 -dialkylamino or C 3-6 -cycloalkylamino each of which is optionally substituted with one or more halogens; and

X 2 is arylene optionally substituted with one or more substituents selected from

halogen, hydroxy, cyano, amino or carboxy; or

C 1-6 -alkyl, C 3-6 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 1-6 -alkoxy, C 3-6 -cycloalkoxy, C 1-6 -alkylthio, C 3-6 -cycloalkylthio, C 1-6 -alkylamino, C 1-6 -dialkylamino or C 3-6 -cycloalkylamino each of which is optionally substituted with one or more halogens; and

X 3 is aryl optionally substituted with one or more substituents selected from

halogen, hydroxy, cyano, amino or carboxy; or

C 1-6 -alkyl, C 3-6 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 1-6 -alkoxy, C 3-6 -cycloalkoxy, C 1-6 -alkylthio, C 3-6 -cycloalkylthio, C 1-6 -alkylcarbonyl, C 1-6 -alkyl-sulfonyl, C 1-6 -alkylsulfonyloxy, C 1-6 -alkylamido, C 1-6 -alkylaminocarbonyl, C 1-6 -alkylamino, C 1-6 -dialkylamino or C 3-6 -cycloalkylamino each of which is optionally substituted with one or more halogens; and

Ar is arylene which is optionally substituted with one or more substituents selected from

halogen, hydroxy or cyano; or

C 1-6 -alkyl, C 3-6 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, aryl, aralkyl, C 1-6 -alkoxy, C 3-6 -cycloalkoxy, aryloxy, aralkoxy, C 1-6 -alkylthio, arylthio or C 3-6 -cycloalkylthio each of which is optionally substituted with one or more halogens; and

Y 1 is O or S; and

Y 2 is O or S; and

Z is —(CH 2 ) n — wherein n is 1, 2 or 3; and

R 1 is hydrogen, halogen or a substituent selected from

C 1-6 -alkyl, C 3-6 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, aralkyl, heteroaralkyl, C 1-6 -alkoxy, C 3-6 -cycloalkoxy, aryloxy, aralkoxy, heteroaralkoxy, C 1-6 -alkylthio, arylthio or C 3-6 -cycloalkylthio each of which is optionally substituted with one or more halogens; and

R 2 is hydrogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 4-6 -alkenynyl or aryl; or

a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, tautomeric form, stereoisomer, mixture of stereoisomers or racemic mixture thereof.

2. A compound according to claim 1 , wherein X 1 is aryl optionally substituted with one or more substituents selected from

halogen; or

C 1-6 -alkyl, aryl, C 1-6 -alkoxy, C 1-6 -alkylsulfonyl or C 1-6 -alkylsulfonyloxy each of which is optionally substituted with one or more halogens.

3. A compound according to claim 2 , wherein X 1 is phenyl optionally substituted with one or more substituents selected from

halogen; or

C 1-6 -alkyl, aryl, C 1-6 -alkoxy, C 1-6 -alkylsulfonyl or C 1-6 -alkylsulfonyloxy each of which is optionally substituted with one or more halogens.

4. A compound according to claim 3 , wherein X 1 is phenyl optionally substituted with one or more substituents selected from halogen, C 1-6 -alkyl, aryl or perhalomethyl.

5. A compound according to claim 4 , wherein X 1 is phenyl optionally substituted with one or more substituents selected from phenyl or trifluoromethyl.

6. A compound according to claim 5 , wherein X 1 is phenyl.

7. A compound according to claim 1 , wherein X 2 is arylene optionally substituted with one or more substituents selected from

halogen; or

C 1-6 -alkyl or C 1-6 -alkoxy each of which is optionally substituted with one or more halogens.

8. A compound according to claim 7 , wherein X 2 is phenylene optionally substituted with one or more substituents selected from

halogen; or

C 1-6 -alkyl or C 1-6 -alkoxy each of which is optionally substituted with one or more halogens.

9. A compound according to claim 8 , wherein X 2 is phenylene optionally substituted with one or more halogens.

10. A compound according to claim 9 , wherein X 2 is phenylene.

11. A compound according to claim 1 , wherein X 3 is aryl optionally substituted with one or more substituents selected from

halogen; or

C 1-6 -alkyl, C 1-6 -alkoxy, C 1-6 -alkylsulfonyl or C 1-6 -alkylsulfonyloxy each of which is optionally substituted with one or more halogens.

12. A compound according to claim 11 , wherein X 3 is phenyl optionally substituted with one or more substituents selected from

halogen; or

C 1-6 -alkyl, C 1-6 -alkoxy, C 1-6 -alkylsulfonyl or C 1-6 -alkylsulfonyloxy each of which is optionally substituted with one or more halogens.

13. A compound according to claim 12 , wherein X 3 is phenyl optionally substituted with one or more halogens.

14. A compound according to claim 12 , wherein X 3 is phenyl optionally substituted with one or more substituents selected from C 1-6 -alkyl or perhalomethyl.

15. A compound according to claim 12 , wherein X 3 is phenyl.

16. A compound according to claim 1 , wherein Ar is phenylene which is optionally substituted with one or more substituents selected from

halogen, hydroxy or cyano; or

C 1-6 -alkyl, C 3-6 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, aryl, aralkyl, C 1-6 -alkoxy, C 3-6 -cycloalkoxy, aryloxy, aralkoxy, C 1-6 -alkylthio, arylthio or C 3-6 -cycloalkylthio each of which is optionally substituted with one or more halogens.

17. A compound according to claim 16 , wherein Ar is phenylene which is optionally substituted with one or more substituents selected from

halogen; or

C 1-6 -alkyl, C 1-6 -alkoxy, aryloxy or aralkoxy each of which is optionally substituted with one or more halogens.

18. A compound according to claim 17 , wherein Ar is phenylene which is optionally substituted with methyl.

19. A compound according to claim 18 , wherein Ar is phenylene.

20. A compound according to claim 1 , wherein Y 1 is S.

21. A compound according to claim 1 , wherein Y 2 is O.

22. A compound according to claim 1 , wherein n is 1.

23. A compound according to claim 1 , wherein R 1 is hydrogen or a substituent selected from C 1-6 -alkyl, aralkyl, C 1-6 -alkoxy, aryloxy, aralkoxy each of which is optionally substituted with one or more halogens.

24. A compound according to claim 23 , wherein R 1 is hydrogen or a substituent selected from C 1-6 -alkyl or C 1-6 -alkoxy each of which is optionally substituted with one or more halogens.

25. A compound according to claim 24 , wherein R 1 is hydrogen.

26. A compound according to claim 1 , wherein R 2 is hydrogen.

27. A compound according to claim 1 , wherein R 2 is methyl or ethyl.

28. A compound according to claim 1 , which is selected from the following:

(E/Z) {4-[3-Biphenyl-4-yl-3-(4-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid, and

(E/Z) {4-[3-(4-Bromo-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid; or

a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, tautomeric form, stereoisomer, mixture of stereoisomers, or racemic mixture thereof.

29. A compound according to claim 1 , which is selected from the following:

{4-[3-(4-Bromo-phenyl)-3-[1, 1′; 4′,1″]terphenyl-4″-yl-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

or a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, tautomeric form, stereoisomer, mixture of stereoisomers or racemic mixture thereof.

30. A compound according to claim 1 , which is selected from the following:

(E) {4-[3-Biphenyl-4-yl-3-(2-fluoro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-fluoro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(2-chloro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-chloro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(2-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(2-iodo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-iodo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(2-methoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-methoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(2-trifluoromethoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-trifluoromethoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(2-methyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-methyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(2-trifluoromethyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(2-trifluoromethyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-fluoro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-fluoro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-chloro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-chloro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-iodo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-iodo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-methoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-methoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-trifluoromethoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-trifluoromethoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-methyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-methyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(3-trifluoromethyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(3-trifluoromethyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-fluoro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-fluoro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-chloro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-chloro-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E/Z) {4-[3-Biphenyl-4-yl-3-(4-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-bromo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-iodo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-iodo-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-methoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-methoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-trifluoromethoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-trifluoromethoxy-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-methyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-methyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-Biphenyl-4-yl-3-(4-trifluoromethyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(Z) {4-[3-Biphenyl-4-yl-3-(4-trifluoromethyl-phenyl)-allylsulfanyl]-phenoxy}-acetic acid;

(E) {4-[3-(4-Fluoro-phenyl)-3-(2′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Fluoro-phenyl)-3-(2′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E/Z) {4-[3-(4-Fluoro-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Fluoro-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Fluoro-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Fluoro-phenyl)-3-(4′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Fluoro-phenyl)-3-(4′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Fluoro-phenyl)-3-(3′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Fluoro-phenyl)-3-(3′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Fluoro-phenyl)-3-(4′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Fluoro-phenyl)-3-(4′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Fluoro-phenyl)-3-(3′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Fluoro-phenyl)-3-(3′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Fluoro-phenyl)-3-(4′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Fluoro-phenyl)-3-(4′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Chloro-phenyl)-3-(2′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Chloro-phenyl)-3-(2′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E/Z) {4-[3-(4-Chloro-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Chloro-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Chloro-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Chloro-phenyl)-3-(4′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Chloro-phenyl)-3-(4′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Chloro-phenyl)-3-(3′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Chloro-phenyl)-3-(3′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Chloro-phenyl)-3-(4′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Chloro-phenyl)-3-(4′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Chloro-phenyl)-3-(3′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Chloro-phenyl)-3-(3′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Chloro-phenyl)-3-(4′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Chloro-phenyl)-3-(4′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Bromo-phenyl)-3-(2′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Bromo-phenyl)-3-(2′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E/Z) {4-[3-(4-Bromo-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Bromo-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Bromo-phenyl)-3-(3′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Bromo-phenyl)-3-(4′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Bromo-phenyl)-3-(4′-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Bromo-phenyl)-3-(3′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Bromo-phenyl)-3-(3′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Bromo-phenyl)-3-(4′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Bromo-phenyl)-3-(4′-chloro-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Bromo-phenyl)-3-(3′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(Z) {4-[3-(4-Bromo-phenyl)-3-(3′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid;

(E) {4-[3-(4-Bromo-phenyl)-3-(4′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid; and

(Z) {4-[3-(4-Bromo-phenyl)-3-(4′-methoxy-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid; or

a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, tautomeric form, stereoisomer, mixture of stereoisomers or racemic mixture thereof.

31. A compound according to claim 1 , which is a PPARδ agonist.

32. A compound according to claim 31 , which is a selective PPARδ agonist.

33. A pharmaceutical composition comprising, as an active ingredient, at least one compound according to claim 1 , together with one or more pharmaceutically acceptable carriers or excipients.

34. A pharmaceutical composition according to claim 33 in unit dosage form, comprising from about 0.05 mg to about 1000 mg to about 200 mg per day of compound according to claim 1 .

35. A pharmaceutical composition according to any one of the claim 33 for oral, nasal, transdermal, pulmonal, or parenteral administration.

Assignments (6)
NOTICE OF RELEASE OF SECURITY INTEREST IN PATENTS FOR REEL/FRAME 030982/0793 Recorded Apr 7, 2014
From: M&F TTP HOLDINGS LLC
To: HIGH POINT PHARMACEUTICALS, LLC
Reel/Frame 032621/0867 →
SECURITY AGREEMENT Recorded Aug 9, 2013
From: HIGH POINT PHARMACEUTICALS, LLC
To: M&F TTP HOLDINGS LLC C/O MACANDREWS & FORBES HOLDINGS INC.
Reel/Frame 030982/0793 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2009
From: TRANSTECH PHARMA, INC.
To: HIGH POINT PHARMACEUTICALS, LLC
Reel/Frame 022584/0953 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2009
From: NOVO NORDISK A/S
To: TRANSTECH PHARMA, INC.
Reel/Frame 022562/0346 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2008
From: TRANSTECH PHARMA, INC.
To: HIGH POINT PHARMACEUTICALS, LLC
Reel/Frame 021754/0886 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2008
From: NOVO NORDISK A/S
To: TRANSTECH PHARMA, INC.
Reel/Frame 021018/0022 →