IP Library › Granted Patent US 10,882,837

Granted Patent B2

US 10,882,837 · App. 16/475,900 · Granted Jan 5, 2021

Amide compounds and use thereof

Inventors: Cheng-Ho Chung (Taipei, TW); Shi-Liang Tseng (Taipei, TW); Yung-Ning Yang (Taipei, TW); Yen-Fu Chen (Taipei, TW)

Assignee: ALPHALA CO., LTD.

C07D307/79 A61P3/10 C07C233/92 C07D209/08 C07D213/90 C07D237/14 C07D239/34 C07D263/57 C07D271/06 C07D271/07 C07D271/10 C07D277/66 C07D401/12 C07D413/04

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Quick Facts

Patent No.: US 10,882,837
App. No.: 16/475,900
Granted: Jan 5, 2021
Kind: B2

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Abstract

Disclosed are compounds of formula (I) below and pharmaceutically acceptable salts thereof, in which each of variables R 1 , R 2 , L, and Z is defined herein. Also disclosed are methods for reducing the glycemic level and treating glucagon-associated disorders with a compound of formula (I) or a salt thereof and a pharmaceutical composition containing same.

Claims (222)

1. A compound of formula (I):

or a pharmaceutically acceptable salt thereof,

wherein

R 1 is

R 2 is —CH 2 CH 2 CO 2 R 5 or —CH 2 CH 2 SO 3 H;

L is —X—CH(R 6 )— or —CH(R 6 )—X—, X being NH or O; and

Z is C or N,

in which R 3 is C 1-6 alkyl, aryl, or heteroaryl, the C 1-6 alkyl being optionally substituted with one to three halo moieties and each of the aryl and heteroaryl being optionally substituted with one to three moieties selected from the group consisting of C 1-6 alkyl, C 3-10 cycloalkyl, aryl, halogen substituted C 1-6 alkyl, C 1-6 alkoxy, and halo; R 4 represents one to three moieties selected from the group consisting of H, halo, hydroxyl, cyano, amino, C 1-6 alkyl, C 1-6 alkoxy, halogen substituted C 1-6 alkyl, and C 3-10 cycloalkyl; R 5 is H, C 1-6 alkyl, C 3-10 cycloalkyl or halogen substituted C 1-6 alkyl; and R 6 is C 1-6 alkyl, C 3-10 cycloalkyl, or C 1-10 heterocycloalkyl, the C 1-6 alkyl being optionally substituted with one to three moieties selected from the group consisting of halo, hydroxyl, C 1-6 alkoxy, and aryl, and each of the C 3-10 cycloalkyl and C 1-10 heterocycloalkyl being optionally substituted with one to two moieties selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy, and halo.

2. The compound or salt of claim 1 , wherein R 1 is

3. The compound or salt of claim 2 , wherein L is —CH(R 6 )—X—, X being NH or O.

4. The compound or salt of claim 3 , wherein R 1 is

5. The compound or salt of claim 3 , wherein R 1 is

6. The compound or salt of claim 3 , wherein R 1 is

7. The compound or salt of claim 2 , wherein L is —X—CH(R 6 )—, X being NH or O.

8. The compound or salt of claim 2 , wherein R 3 is C 1-6 alkyl, optionally substituted phenyl or pyridinyl.

9. The compound or salt of claim 2 , wherein L is —CH(R 6 )—X—, and R 6 being C 1-6 alkyl.

10. The compound or salt of claim 1 , wherein R 1 is

R 3 being C 1-6 alkyl, optionally substituted phenyl or pyridinyl; L is —X—CH(R 6 )— or —CH(R 6 )—X—, R 6 being C 1-6 alkyl; and Z is C.

11. The compound or salt of claim 1 , wherein R 1 is

12. The compound or salt of claim 11 , wherein L is —CH(R 6 )—X—.

13. The compound or salt of claim 12 , wherein X is NH and Z is N.

14. The compound or salt of claim 12 , wherein R 6 is C 1-6 alkyl.

15. The compound or salt of claim 11 , wherein L is —X—CH(R 6 )— and Z is C.

16. The compound or salt of claim 15 , wherein R 6 is C 1-6 alkyl.

17. The compound or salt of claim 11 , wherein R 4 is H.

18. The compound or salt of claim 1 , wherein R 1 is

R 4 being H; and L is —X—CH(R 6 )— or —CH(R 6 )—X—, R 6 being C 1-6 alkyl.

19. The compound or salt of claim 1 , wherein R 3 is C 1-6 alkyl, aryl, or 6-membered heteroaryl, the C 1-6 alkyl being optionally substituted with one to three halo moieties and each of the aryl and 6-membered heteroaryl being optionally substituted with one to three moieties selected from the group consisting of methyl, trifluoromethyl, ethyl, propyl, isopropyl, butyl, tert-butyl, F and Cl.

20. The compound or salt of claim 1 , wherein R 6 is C 1-6 alkyl or C 3-10 cycloalkyl, the C 1-6 alkyl being optionally substituted with one to three moieties selected from the group consisting of fluoro, hydroxyl, methoxy, and phenyl.

21. The compound or salt of claim 1 , which is any one selected from the group consisting of:

3-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido) propanoic acid;

methyl 3-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoate;

ethyl 3-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoate;

3-(4-((2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoic acid;

3-(4-((3-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido) propanoic acid;

ethyl 3-(4-((1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido) propanoate;

3-(4-((1-(4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

3-(4-((1-(4-(5-(Trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido) propanoic acid;

3-(4-((3-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido) propanoic acid;

3-(4-((1-(4-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)phenyl)-3-methylbutyl)amino)benzamido)propanoic acid;

2-(4-((1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)ethane-1-sulfonic acid;

3-(4-((1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido) propanoic acid;

ethyl 3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(Pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido) propanoic acid;

ethyl 3-(4-((1-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(4-Fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methyl propyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido) propanoate;

3-(4-((1-(4-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido) propanoic acid;

ethyl 3-(4-((1-(4-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methylbutyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methylbutyl)amino)benzami do)propanoic acid;

ethyl 3-(4-((1-(4-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methyl propyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(tert-butyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methyl propyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methyl propyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methyl propyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-3-methylbutyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-3-methylbutyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methylbutyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-methylbutyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-((2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

ethyl 3-(4-(((1S)-2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

ethyl 3-(4-(((1R)-2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-(((1S)-2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

3-(4-(((1R)-2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

methyl 3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

(S)-ethyl 3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propylamino)benzamido)propanoate;

(R)-ethyl 3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propylamino)benzamido)propanoate;

(S)-3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propylamino)benzamido)propanoic acid;

(R)-3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propylamino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

ethyl (R)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

(S)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2yl)phenyl)pentyl)amino)benzamido)propanoic acid;

(R)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl 3-(4-(((1S)-2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

ethyl 3-(4-(((1R)-2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-(((1S)-2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

3-(4-(((1R)-2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

ethyl (R)-3-(4-((1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

(S)-3-(4-((1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

(R)-3-(4-((1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoate;

ethyl (R)-3-(4-((2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoate;

(S)-3-(4-((2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoic acid;

(R)-3-(4-((2-methyl-1-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((3-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

ethyl (R)-3-(4-((3-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoate;

(S)-3-(4-((3-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

(R)-3-(4-((3-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)amino)benzamido)propanoic acid;

methyl (S)-3-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoate;

(S)-2-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)ethane-1-sulfonic acid;

ethyl 3-(4-((1-(4-(5-(tert-butyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methyl propyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(tert-butyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methyl propyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(tert-butyl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(tert-butyl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(tert-butyl)-1,2,4-oxadiazol-3-yl)phenyl)-3-methylbutyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(tert-butyl)-1,2,4-oxadiazol-3-yl)phenyl)-3-methylbutyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido) propanoate;

3-(4-((1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((3-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-((3-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido) propanoic acid;

ethyl 3-(4-((2-methyl-1-(4-(5-(thiophen-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoate;

3-(4-((2-methyl-1-(4-(5-(thiophen-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoic acid;

3-(4-((1-(4-(5-(thiophen-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

3-(4-((3-methyl-1-(4-(5-(thiophen-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoic acid;

3-(4-((cyclopentyl(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)methyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((cyclohexyl(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)methyl)amino)benzamido)propanoate;

3-(4-((cyclohexyl(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)methyl)amino)benzamido) propanoic acid;

ethyl 3-(4-(((1S)-2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-(((1S)-2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl 3-(4-(((1R)-2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-(((1R)-2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl (R)-3-(4-((2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoate;

(R)-3-(4-((2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methylpropyl)amino)benzamido)propanoate;

3-(4-((1-(4-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)phenyl)-2-methylpropyl)amino)benzamido)propanoic acid;

3-(4-((2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido) propanoic acid;

ethyl (S)-3-(4-((2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoate;

(S)-3-(4-((2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoic acid;

ethyl 3-(4-(((1S)-2-methyl-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-(((1S)-2-methyl-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoic acid;

methyl 3-(4-((2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoate;

methyl 3-(4-((1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido) propanoate;

ethyl (S)-3-(4-((1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido) propanoate;

(S)-3-(4-((1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl (R)-3-(4-((1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido) propanoate;

(R)-3-(4-((1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido) propanoic acid;

ethyl (S)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoate;

(S)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl (R)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoate;

(R)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((3-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoate;

ethyl (R)-3-(4-((3-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoate;

(S)-3-(4-((3-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoic acid;

(R)-3-(4-((3-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoate;

ethyl (R)-3-(4-((1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoate;

(S)-3-(4-((1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

(R)-3-(4-((1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

methyl (S)-3-(4-((2-methyl-1-(4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)propyl)amino)benzamido)propanoate;

3-(4-(1-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)amino)pentyl)benzamido)propanoic acid;

3-(4-(2-methyl-1-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)amino)propyl)benzamido) propanoic acid;

ethyl 3-(4-(1-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)amino)pentyl)benzamido) propanoate;

ethyl 3-(4-(2-methyl-1-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)amino)propyl)benzamido)propanoate;

ethyl 3-(4-(2-methyl-1-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)amino)butyl)benzamido)propanoate;

3-(4-(2-methyl-1-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)amino)butyl)benzamido) propanoic acid;

ethyl 3-(4-(1-((4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)amino)-2-methylbutyl)benzamido)propanoate;

3-(4-(1-((4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)amino)-2-methylbutyl)benzamido)propanoic acid;

ethyl 3-(4-(1-((4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)amino)-2-methylpropyl)benzamido)propanoate;

3-(4-(1-((4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)amino)-2-methylpropyl)benzamido)propanoic acid;

3-(4-(2-methyl-1-((4-(5-phenyl-1,2,4-oxadiazol-3-yl)phenyl)amino)propyl)benzamido) propanoic acid;

(S)-ethyl 3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenylamino)propyl)benzamido)propanoate;

(R)-ethyl 3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenylamino)propyl)benzamido)propanoate;

(S)-3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenylamino)propyl)benzamido)propanoic acid;

(R)-3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenylamino)propyl)benzamido)propanoic acid;

ethyl 3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido) propanoate;

ethyl 3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido) propanoic acid;

3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido) propanoate;

ethyl (R)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido)propanoate;

(S)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido)propanoic acid;

(R)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido)propanoic acid;

ethyl (R)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)pentyl)amino)benzamido) propanoate;

(R)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl (R)-3-(4-(((4-(benzo[d]oxazol-2-yl)phenyl)(cyclopentyl)methyl)amino)benzamido)propanoate;

(R)-3-(4-(((4-(benzo[d]oxazol-2-yl)phenyl)(cyclopentyl)methyl)amino)benzamido)propanoic acid;

ethyl (R)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-3-methylbutyl)amino)benzamido) propanoate;

(R)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-3-methylbutyl)amino)benzamido) propanoic acid;

ethyl (S)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)pentyl)amino)benzamido) propanoate;

(S)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)pentyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-3-methylbutyl)amino)benzamido) propanoate;

(S)-3-(4-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-3-methylbutyl)amino)benzamido)propanoic acid;

ethyl 3-(4-(((1S)-1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylbutyl)amino)benzamido)propanoate;

3-(4-(((1S)-1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylbutyl)amino)benzamido)propanoic acid;

ethyl 3-(4-(((1R)-1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylbutyl)amino)benzamido)propanoate;

3-(4-(((1R)-1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylbutyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-(((4-(benzo[d]oxazol-2-yl)phenyl)(cyclopentyl)methyl)amino)benzamido)propanoate;

(S)-3-(4-(((4-(benzo[d]oxazol-2-yl)phenyl)(cyclopentyl)methyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(benzo[d]thiazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido) propanoate;

(S)-3-(4-((1-(4-(benzo[d]thiazol-2-yl)phenyl)-2-methylpropyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(6-((1-(4-(benzo[d]thiazol-2-yl)phenyl)-2-methylpropyl)amino)nicotinamido) propanoate;

(S)-3-(6-((1-(4-(benzo[d]thiazol-2-yl)phenyl)-2-methylpropyl)amino)nicotinamido)propanoic acid;

ethyl (S)-3-(6-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)nicotinamido) propanoate;

(S)-3-(6-((1-(4-(benzo[d]oxazol-2-yl)phenyl)-2-methylpropyl)amino)nicotinamido)propanoic acid;

ethyl (S)-3-(4-((3-methyl-1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)butyl)amino)benzamido)propanoate;

(S)-3-(4-((3-methyl-1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((2-methyl-1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)propyl)amino)benzamido)propanoate;

(S)-3-(4-((2-methyl-1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)propyl)amino)benzamido)propanoic acid;

ethyl 3-(4-(((1S)-2-methyl-1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)butyl)amino)benzamido)propanoate;

3-(4-(((1S)-2-methyl-1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)butyl)amino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)pentyl)amino)benzamido) propanoate;

(S)-3-(4-((1-(4-(3-phenyl-1,2,4-oxadiazol-5-yl)phenyl)pentyl)amino)benzamido) propanoic acid;

ethyl 3-(4-(1-(4-(benzo[d]thiazol-2-yl)phenyl)-2-methylpropoxy)benzamido)propanoate;

3-(4-(1-(4-(Benzo[d]thiazol-2-yl)phenyl)-2-methylpropoxy)benzamido)propanoic acid;

ethyl 3-(4-(1-(4-(benzo[d]oxazol-2-yl)phenoxy)-2-methylpropyl)benzamido)propanoate;

3-(4-(1-(4-(Benzo[d]oxazol-2-yl)phenoxy)-2-methylpropyl)benzamido)propanoic acid;

ethyl 3-(4-(1-(4-(benzo[d]thiazol-2-yl)phenoxy)-2-methylpropyl)benzamido)propanoate; and

3-(4-(1-(4-(Benzo[d]thiazol-2-yl)phenoxy)-2-methylpropyl)benzamido)propanoic acid.

22. The compound or salt of claim 21 , which is any one selected from the group consisting of:

methyl 3-(4-((2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propyl)amino)benzamido)propanoate;

methyl 3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

(S)-ethyl 3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propylamino)benzamido)propanoate;

(S)-3-(4-(2-methyl-1-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)propylamino)benzamido)propanoic acid;

ethyl (S)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido)propanoate;

(S)-3-(4-((1-(4-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)pentyl)amino)benzamido) propanoic acid;