# US 10,246,451 B2 · Propionic acid derivatives and methods of use thereof

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- Number: US 10,246,451 B2
- Document ID: US10246451B2
- Status: Granted
- Kind: B2
- Application number: 15/497,416
- Filed: 2017-04-26
- Published: 2018-11-01
- Granted: 2019-04-02
- Earliest claimed: 2017-04-26
- Assignees: Aviara Pharmaceuticals, Inc.
- Applicants: Ronald J. Biediger; Michele A. Benish; Robert V. Market; Michael M. Savage; Brandon M. Young
- Inventors: Ronald J. Biediger; Michele A. Benish; Robert V. Market; Michael M. Savage; Brandon M. Young
- Web page: https://patentgrep.com/patent/US10246451B2

## CPC

- C07D 417/12: linked by a chain containing hetero atoms as chain links
- A61P 35/00: Antineoplastic agents
- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Provided herein are compounds and pharmaceutical compositions of formula I where R1, R2, R3, R4, R5, X and R6 are as described herein. Also provided pharmaceutically acceptable salts or stereoisomer(s) of these compounds. In addition methods are provided for antagonizing the action of an α4-integrin to treat various pathophysiological conditions.

## Claims

### Claim 1

A compound of formula I having a chemical structure of
wherein
R1 and R2 are independently hydrogen, halogen, C1-4 alkyl, C3-6 cycloalkyl, or arylalkyl;
R3 is hydroxyl or oxido paired with a pharmaceutically acceptable cation;
R4 is hydroxyl, C1-4 alkyoxy, or oxido paired with a pharmaceutically acceptable cation;
R5 is aryl, heteroaryl or arylalkyl which is substituted with one or more of C1-4 alkyl, alkoxy, aryloxy, halogen, haloalkoxy, —CF3, hydroxyl, —OCF3, aryl, —OCF2H, —OCF2CF2H, —O(C3-6 cycloalkyl), —OCH2CF3, thioalkoxy, dialkylamino, C3-6 cycloalkyl, haloalkyl;
X is CH2, O, or CF2;
R6 is C1-4 alkyl, aryl, heteroaryl which is substituted with one or more of C1-4 alkyl, alkoxy, aryloxy, halogen, haloalkoxy, —CF3, hydroxyl, —OCF3, aryl, —OCF2H, —OCF2CF2H, —O(C3-6 cycloalkyl), —OCH2CF3, thioalkoxy, dialkylamino, C3-6 cycloalkyl, haloalkyl; or
a pharmaceutically acceptable salt form or stereoisomer(s) thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R4 is hydroxyl, methoxy, ethoxy or t-butoxy or oxido paired with a pharmaceutically acceptable cation.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R3 is hydroxyl or oxido paired with a pharmaceutically acceptable cation.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound of formula I is a compound of formula IA having a chemical structure of
wherein, R1, R2, R3, R4, R5, and R6 are as defined in claim 1; or a pharmaceutically acceptable salt or stereoisomer(s) thereof.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound of formula I is a compound of formula IB having a chemical structure of
wherein, R1, R2, R3, R4, R5, and R6 are as defined in claim 1; or a pharmaceutically acceptable salt or stereoisomer(s) thereof.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound of formula I is a compound of formula IC having a chemical structure of
wherein, R1, R2, R3, R4, R5, and R6 are the same as defined in claim 1; or a pharmaceutically acceptable salt or stereoisomers thereof.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the pharmaceutically acceptable salt is the mono or disodium sodium salt.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the stereoisomer is of the (S)-configuration.

### Claim 9 (depends on 1)

A pharmaceutical composition, comprising at least one compound of claim 1 and one or more pharmaceutically acceptable carriers.

### Claim 10

A compound of formula II having the chemical structure of
wherein
R1 and R2 are independently hydrogen or methyl;
R4 is hydroxyl, C1-4 alkyoxy, or oxido paired with a pharmaceutically acceptable cation;
R5 is, aryl, heteroaryl or arylalkyl which is substituted with one or more of C1-4 alkyl, alkoxy, aryloxy, halogen, haloalkoxy, —CF3, hydroxyl, —OCF3, aryl, —OCF2H, —OCF2CF2H, —O(C3-6 cycloalkyl), —OCH2CF3, thioalkoxy, dialkylamino, C3-6 cycloalkyl, haloalkyl;
X is CH2, O, or CF2; and
R6 is C1-4 alkyl, aryl, heteroaryl which is substituted with one or more of C1-4 alkyl, alkoxy, aryloxy, halogen, haloalkoxy, —CF3, hydroxyl, —OCF3, aryl, —OCF2H, —OCF2CF2H, —O(C3-6 cycloalkyl), —OCH2CF3, thioalkoxy, dialkylamino, C3-6 cycloalkyl, haloalkyl; or
a pharmaceutically acceptable salt or stereoisomer(s) thereof.

### Claim 11 (depends on 10)

The compound of claim 10, wherein the compound of formula II is a compound of formula II A having a chemical structure of
wherein, R1, R2, R4, R5, and R6 are the same as defined in claim 10; or a pharmaceutically acceptable salt or stereoisomer(s) thereof.

### Claim 12 (depends on 10)

The compound of claim 10, wherein the compound of formula II is a compound of formula II B having a chemical structure of
wherein R1, R2, R4, R5, and R6 are the same as defined in claim 10; or a pharmaceutically acceptable salt or stereoisomer(s) thereof.

### Claim 13 (depends on 10)

The compound of claim 10, wherein the compound of formula II is a compound of formula II C having a chemical structure of
wherein, R1, R2, R4, R5, and R6 are the same as defined in claim 10; or a pharmaceutically acceptable salt or stereoisomer(s) thereof.

### Claim 14

A compound that is:
ethyl 3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoate,
ethyl (S)-3-(3-benzylphenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl 3-(3-(2-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl 3-(3-(3-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl 3-(3-(4-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(4-(2-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methoxyphenoxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methoxyphenoxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(p-tolyloxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(5-(2-methylbenzyl)thiophen-2-yl)propanoate,
ethyl (S)-3-(3-(difluoro(o-tolyl)methyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methoxyphenoxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methoxyphenoxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(0-tolyloxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(p-tolyloxy)phenyl)propanoate,
ethyl (S)-3-(4-benzylphenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(4-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(2-ethylbenzyl)phenyl)phenyl)-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-methylbenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-(trifluoromethyl)benzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-(trifluoromethyl)benzyl)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-(trifluoromethyl)benzyl)phenyl)propanoate,
ethyl (S)-3-(3-(2-(difluoromethoxy)benzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methoxybenzyl)phenyl)propanoate,
ethyl (S)-3-(3-(2-fluorobenzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(2,6-dimethylbenzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(5-fluoro-2-methyl benzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(5-(2-methylbenzyl)thiophen-2-yl)propanoate,
ethyl (S)-3-(5-benzylthiophen-2-yl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(0-tolyloxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(m-tolyloxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(ptolyloxy)phenyl)propanoate,
ethyl (S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methoxyphenoxy)phenyl)propanoate,
ethyl (S)-3-(3-(2-chlorophenoxy)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(2,4-difluorophenoxy)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
ethyl (S)-3-(3-(2,6-dimethylphenoxy)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoic acid,
(S)-3-(3-benzylphenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
3-(3-(2-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
3-(3-(3-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
3-(3-(4-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(4-(2-chlorobenzyl)phenyl)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,5-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methoxyphenoxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methoxyphenoxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(ptolyloxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(5-(2-methylbenzyl)thiophen-2-yl)propanoic acid,
(S)-3-(3-(difluoro(o-tolyl)methyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methoxyphenoxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methoxyphenoxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(0-tolyloxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(p-tolyloxy)phenyl)propanoic acid,
(S)-3-(4-benzylphenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(4-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(2-ethylbenzyl)phenyl)phenyl)-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-methylbenzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-(trifluoromethyl)benzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-(trifluoromethyl)benzyl)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-(trifluoromethyl)benzyl)phenyl)propanoic acid,
(S)-3-(3-(2-(difluoromethoxy)benzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methoxybenzyl)phenyl)propanoic acid,
(S)-3-(3-(2-fluorobenzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(2,6-dimethylbenzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(5-fluoro-2-methylbenzyl)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(5-(2-methylbenzyl)thiophen-2-yl)propanoic acid,
(S)-3-(5-benzylthiophen-2-yl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(o-tolyloxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(m-tolyloxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(p-tolyloxy)phenyl)propanoic acid,
(S)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methoxyphenoxy)phenyl)propanoic acid,
(S)-3-(3-(2-chlorophenoxy)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(2,4-difluorophenoxy)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
(S)-3-(3-(2,6-dimethylphenoxy)phenyl)-3-(3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoic acid,
sodium 3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoate,
sodium (S)-3-(3-benzylphenyl)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium 3-(3-(2-chlorobenzyl)phenyl)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium 3-(3-(3-chlorobenzyl)phenyl)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium 3-(3-(4-chlorobenzyl)phenyl)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium 3-(4-(2-chlorobenzyl)phenyl)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propante,
sodium (S)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1,5-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1,6-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methoxyphenoxy)phenyl)propanoate,
sodium (S)-3-(3-(1,6-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methoxyphenoxy)phenyl)propanoate,
sodium (S)-3-(3-(1,6-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(p-tolyloxy)phenyl)propanoate,
sodium (S)-3-(3-(1,6-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1,6-dimethyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(5-(2-methylbenzyl)thiophen-2-yl)propanoate,
sodium (S)-3-(3-(difluoro(o-tolyl)methyl)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido),
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(0-tolyloxy)phenyl)propanoate,
sodium (S)-3-(3-(2-methoxyphenoxy)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(2-chlorophenoxy)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(5-fluoro-2-methylbenzyl)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-phenoxyphenyl)propanoate,
sodium (S)-3-(4-(2-methoxyphenoxy)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihyropriddin-3-yl)ureido)propanoate,
sodium (S)-3-(4-(3-methoxyphenoxy)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(0-tolyloxy)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(p-tolyloxy)phenyl)propanoate,
sodium (S)-3-(4-benzylphenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(2-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(3-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(4-(4-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(2-ethylbenzyl)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-methylbenzyl)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(mtolyloxy)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(ptolyloxy)phenyl)propanoate,
sodium (S)-3-(3-(2,4-difluorophenoxy)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(2,6-dimethylphenoxy)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(2-(trifluoromethyl)benzyl)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(3-(trifluoromethyl)benzyl)phenyl)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(3-(4-(trifluoromethyl)benzyl)phenyl)propanoate,
sodium (S)-3-(3-(2-(difluoromethoxy)benzyl)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(2-methoxybenzyl)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(2-fluorobenzyl)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(2,6-dimethylbenzyl)phenyl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate,
sodium (S)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)-3-(5-(2-methylbenzyl)thiophen-2-yl)propanoate,
sodium (S)-3-(5-benzylthiophen-2-yl)-3-(3-(1-methyl-4-oxido-2-oxo-1,2-dihydropyridin-3-yl)ureido)propanoate.