IP Library › Granted Patent US 9,447,044
Granted Patent B2
US 9,447,044 · App. 14/440,495 · Granted Sep 20, 2016

Thioaryl derivatives as GPR120 agonists

Inventors: Young Kwan Kim (Daejeon, KR); Myoung Yeol Kim (Daejeon, KR); Sang Yun Park (Daejeon, KR); Ok Ku Park (Daejeon, KR); Vasily Artemov (Daejeon, KR); Sang Dae Lee (Daejeon, KR); Hyun Woo Joo (Daejeon, KR); Eun Sil Choi (Daejeon, KR)
Assignee: LG LIFE SCIENCES LTD.
C07D213/70A61K31/44C07D213/80C07D241/18
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Quick Facts
Patent No.
US 9,447,044
App. No.
14/440,495
Granted
Sep 20, 2016
Kind
B2
Abstract

The present invention relates to thioaryl derivatives of Formula 1 as defined in the specification, a method for preparing the same, a pharmaceutical composition comprising the same and use thereof. The thioaryl derivatives of Formula 1 according to the present invention promote GLP-1 formation in the gastrointestinal tract and improve insulin resistance in macrophages, pancreas cells, etc. due to anti-inflammatory action, and can accordingly be effectively used for preventing or treating diabetes, complications of diabetes, inflammation, obesity, non-alcoholic fatty liver, steatohepatitis or osteoporosis.

Claims (214)

1. A compound of the following Formula 1, or a pharmaceutically acceptable salt or R or S isomer thereof:

wherein,

A, B, D, E, F, G, H and I represent independently carbon or nitrogen,

R1 represents optionally substituted alkyl, cycloalkyl, heterocycloalkyl, alkylcycloalkyl, alkylaryl, heteroaryl or alkylheteroaryl,

R2 and R3 represent independently hydrogen, halogen, or optionally substituted alkyl, cycloalkyl, heterocycloalkyl, alkoxy, cycloalkoxy, aryloxy, heteroaryloxy, aminoalkyl, aminocycloalkyl, aminoaryl, alkylamine, cycloalkylamine, aminoheteroaryl, thioalkyl, thioaryl or thioheteroaryl,

R4, R5, R6 and R7 represent independently hydrogen, fluoro, alkyl or cycloalkyl;

alternatively, R4 and R6 are connected together to form cycloalkyl, R5 and R7 are connected together to form cycloalkyl, or one of R4 and R5 is connected with J to form cycloalkyl, heteroaryl or heterocycloalkyl,

J does not exist, or represents CH 2 , CH, NH or O,

K represents CH 2 ,

M represents CH 2 , NH, N-alkyl, O or S, and n represents an integer of 0 to 4.

2. The compound, or a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 , selected from the following compounds of Formulas 1-1 and 1-2:

wherein,

R1 represents C 1 -C 6 -alkyl, C 3 -C 10 -cycloalkyl, C 1 -C 6 -alkyl-C 3 -C 10 -cycloalkyl, C 1 -C 6 -alkyl-C 3 -C 10 -heterocycloalkyl, C 1 -C 6 -alkylaryl or C 1 -C 6 -alkyl-C 5 -C 6 -heteroaryl,

each of R2 represents independently hydrogen, halogen or optionally substituted C 1 -C 6 -alkyl, C 3 -C 10 -cyclo-C 1 -C 6 -alkyl, heterocycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 10 -cycloalkoxy, aryloxy, heteroaryloxy, amino-C 1 -C 6 -alkyl, amino-C 3 -C 10 -cycloalkyl, aminoaryl, di(C 1 -C 6 -alkyl)amine, C 3 -C 10 -cycloalkylamine, aminoheteroaryl, thio-C 1 -C 6 -alkyl, thioaryl or thioheteroaryl,

n represents an integer of 0 to 3, and

D, E, F, G, H, I, J, K, M, R3, R4, R5, R6 and R7 are as defined in claim 1 .

3. The compound, or a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 , selected from the following compounds of Formulas 1-3 to 1-7:

wherein,

each of R3 represents independently hydrogen, halogen or optionally substituted C 1 -C 6 -alkyl, C 3 -C 10 -cyclo-C 1 -C 6 -alkyl, heterocycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 10 1 -cycloalkoxy, aryloxy, heteroaryloxy, amino-C 1 -C 6 -alkyl, amino-C 3 -C 10 -cycloalkyl, aminoaryl, di(C 1 -C 6 -alkyl)amine, C 3 -C 10 -cycloalkylamine, aminoheteroaryl, thio-C 1 -C 6 -alkyl, thioaryl or thioheteroaryl,

R6 and R7 represent independently hydrogen, fluoro or C 1 -C 6 alkyl, and

n, A, B, D, E, F, G, H, I, J, K, M, R1 and R2 are as defined in claim 1 .

4. The compound, or a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 , selected from the following compounds:

3-[3,5-difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-isopropylsulfanyl-5-methyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[4-(2-isopropylsulfanyl-5-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[3-fluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[2-fluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[3,5-difluoro-4-(2-isopropylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-ethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

3-[3,5-difluoro-4-(2-isobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

4-[4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-butyric acid;

3-[3,5-difluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-t-butylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

3-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

3-{3 ,5-difluoro-4-[2-(2,2,2-trifluoro-ethylsulfanyl)-pyridin-3-ylmethoxy]-phenyl}-propionic acid;

3-[4-(2-sec-butylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

3-[3,5-difluoro-4-(3-isopropylsulfanyl-pyrazin-2-ylmethoxy)-phenyl]-propionic acid;

4-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-butyric acid;

3-[4-(2-cyclohexylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

3-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

3-[3,5-difluoro-4-(2-isopropylsulfanyl-pyrimidin-4-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[4-(2-butylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

3-{3,5-difluoro-4-[243,3,3-trifluoro-propylsulfanyl)-pyridin-3-ylmethoxy]-phenyl}-propionic acid;

3-14-[2-(2,2-dimethyl-propylsulfanyl)-pyridin-3-ylmethoxy]-3,5-difluoro-phenyll-propionic acid;

3-[4-(6-cyclopentylsulfanyl)-pyridin-2-ylmethoxy]-phenyl]-propionic acid;

3-[4-(6-cyclopentylsulfanyl)-pyridin-2-ylmethoxy]-3,5-difluoro-phenyll-propionic acid;

3-[4-(6-cyclohexylsulfanyl)-pyridin-2-ylmethoxy]-3,5-difluoro-phenyll-propionic acid;

3-[4-(6-ethyl-2-isopropylsulfanyl)-pyridin-3-ylmethoxy]-3,5-difluoro-phenyl]-propionic acid;

3-[3,5-difluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid;

3-[4-(6-sec-butylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-propionic acid;

2-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid;

3-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

3-[4-(2-sec-butylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

3-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

3-[3,5-difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[4-(2-sec-butylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-2-methyl-propionic acid;

3-[3,5-difluoro-4-(2-isopropylsulfanyl-6-methoxy-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-2-methyl-propionic acid;

3-[4-(2-cyclopentylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyfl-propionic acid;

3-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-2-methyl-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-2-methyl-propionic acid;

3-[4-(6-sec-butylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-2-methyl-propionic acid;

3-[3,5-difluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-2-methyl-propionic acid;

3-[3,5-difluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[3-fluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[4-(6-sec-butylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

3-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

3-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

3-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-2-methyl-propionic acid;

3-[4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-3-methoxy-phenyl]-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-methoxy-phenyl]-propionic acid;

[6-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-2,3-dihydro-benzofuran-3-A-acetic acid;

3-[3-fluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[4-(2-butylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-2-methyl-propionic acid;

2-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid;

2-[3,5-difluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3,5-difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cycloprppane carboxylic acid;

2-[4-(2-butylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid;

[6-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid;

[6-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid;

3-[4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2,2-dimethyl-propionic acid;

3-[4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2,2-dimethyl-propionic acid;

3-[3,5-difluoro-4-(4-isopropylsulfanyl-2-methyl-pyrimidin-5-ylmethoxy)-phenyl]-propionic acid;

3-[4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-3-methoxy-phenyl]-propionic acid;

3-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-methoxy-phenyl]-propionic acid;

[6-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid;

2-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid;

3-[4-(2-cyclopentylsulfanyl-6-methoxy-pyridin-3-ylmethoxy)-3,5-difluoro-phenyTh propionic acid;

3-[3-chloro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

343-chloro-4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyl]-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyThpropionic acid;

[(S)-6-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid;

[(R)-6-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid;

2-[3-fluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid;

2-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid;

2-[4-(6-cyclobutyl sulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid;

2-[2-chloro-4-(2-isopropyl sulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[2-chloro-4-(6-chlorobutylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

3-[3-chloro-4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

343-chloro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[3-chloro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[3-chloro-4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[3-chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-2-methyl-propionic acid;

3-[3-chloro-4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acid;

2-[3-chloro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(6-cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(2-cyclop entylsulfanyl-pyridin-3-ylmethoxy) -phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[2-chloro-4-(6-chloropentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[3-chloro-4-(2-isopropylsulfanyl-6-methoxy-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-benzyl]-cyclopropane carboxylic acid;

[6-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-5,7-difluoro-2,3-dihydro-benzofuran-3-yl]-acetic acid;

2-[2,3-dimethyl-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid;

2-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyl]-cyclopropane carboxylic acid;

2-[4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-2,3-dimethyl-phenyl]-cyclopropane carboxylic acid;

2-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-benzyl]-cyclopropane carboxylic acid;

2-[3,5-difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-benzyl]-cyclopropane carboxylic acid;

2-[3,5-difluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-benzyl]-cyclopropane carboxylic acid;

[6-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-7-methyl-benzofuran-3-yl]-acetic acid;

2-[3-fluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (less polar);

{2-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropyl -acetic acid;

{2-[3-fluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropyll-acetic acid;

[6-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-5,7-difluoro-benzofuran-3-yl]-acetic acid;

[6-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-5,7-difluoro-2,3-dihydro-benzofuran-3-yl]-acetic acid;

2-[3-chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (less polar);

2-[3-chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyThcyclopropane carboxylic acid (more polar);

2-[3-chloro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyll-cyclopropane carboxylic acid (more polar);

2-[3-chloro-4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (more polar);

2-[3-chloro-4-(6-cyclopropylmethyl sulfanyl-pyridin-2-ylmethoxy) -phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (less polar);

2-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (less polar);

2-[3-fluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (less polar);

2-[3-chloro-4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (less polar);

2-[4-(6-cyclopentyl sulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (less polar);

2-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (less polar);

2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid (less polar);

2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[3,5-difluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyThcyclopropane carboxylic acid (more polar);

2-[3,5-difluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid (more polar);

3-[3-chloro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid;

3-[3-chloro-4-(6-cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid;

3-[3-chloro-4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid;

3-[3-fluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-propionic acid;

3-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-propionic acid;

3-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-propionic acid;

3-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-propionic acid;

3-[3-fluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid;

3-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-propionic acid;

3-[4-(6-cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyThpropionic acid;

2-[3,5-difluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(6-cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid (more polar);

3-[3-chloro-4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[3-chloro-4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[3-chloro-4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-phenylj -propionic acid;

3-[3-chloro-4-(2-isopropylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[3-chloro-4-(2-cyclopentylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

2-[3-fluoro-4-(2-isopropylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (more polar);

2-[3-fluoro-4-(2-propylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[3-fluoro-4-(6-isopropylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (more polar);

2-[4-(6-cyclopropylmethyl sulfanyl-pyridin-2-ylmethoxy)-3-fluoro-phenyl]-cyclopropane carboxylic acid (more polar);

3-{4-[(2-cyclopentylsulfanyl-pyridin-3-ylmethyl)-amino]-phenyl]-propionic acid;

3-{4-[(6-cyclopentylsulfanyl-pyridin-2-ylmethyl)-amino]-phenyl]-propionic acid;

3-[4-[(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2-fluoro-phenyl]-propionic acid;

2-[4-[(2-cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2-fluoro-phenyl]-cyclopropane carboxylic acid;

3-[4-[(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-2-fluoro-phenyl]-propionic acid;

3-[4(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-2-fluoro-phenyl]-propionic acid;

3-[4(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-2-fluoro-phenyl]-propionic acid;

3-[4-[(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-2-fluoro-phenyl]-propionic acid;

3-[4-[(6-cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-2-fluoro-phenyl]-propionic acid;

3-[4-[(2-cyclobutylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-[(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid;

3-[4-[(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid;

3-[4-[(6-cyclopropylmethylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid;

3-[4-[(2-cyclopentylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid; and

3-[4-[(2-isopropylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acid.

5. A pharmaceutical composition as GPR120 agonists, comprising the compound, a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 and a pharmaceutically acceptable carrier.

6. A pharmaceutical composition which is suitable for use in treating diabetes, complications of diabetes, inflammation, obesity, non-alcoholic fatty liver, steatohepatitis or osteoporosis, comprising the compound, a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 and a pharmaceutically acceptable carrier.

7. A composition which is suitable for use in lowering blood glucose level, comprising the compound, a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 and a pharmaceutically acceptable carrier.

8. A method for preparing a composition for treating diabetes, complications of diabetes, inflammation, obesity, non-alcoholic fatty liver, steatohepatitis or osteoporosis, which comprises the step of mixing the compound, a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 with a pharmaceutically acceptable carrier.

9. A method for treating a disease selected from the group consisting of diabetes, complications of diabetes, inflammation, obesity, non-alcoholic fatty liver, steatohepatitis or osteoporosis, comprising:

administering the compound, a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 and a pharmaceutically acceptable carrier to a subject suffering from the disease.

10. A method for lowering blood glucose level, comprising:

administering the compound, a pharmaceutically acceptable salt or R or S isomer thereof according to claim 1 and a pharmaceutically acceptable carrier to a subject in need of lowering blood glucose level.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NO. 13305857 PREVIOUSLY RECORDED AT REEL: 043257 FRAME: 0247. ASSIGNOR(S) HEREBY CONFIRMS THE MERGER AND CHANGE OF NAME . Recorded Sep 20, 2017
From: LG LIFE SCIENCES LTD.
To: LG CHEM, LTD.
Reel/Frame 043710/0909 →
MERGER Recorded Sep 2, 2017
From: LG LIFE SCIENCES LTD.
To: LG CHEM, LTD.
Reel/Frame 043475/0619 →
MERGER AND CHANGE OF NAME Recorded Aug 10, 2017
From: LG LIFE SCIENCES LTD.; LG CHEM, LTD.
To: LG CHEM, LTD.
Reel/Frame 043257/0247 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2015
From: KIM, YOUNG KWAN; KIM, MYOUNG YEOL; PARK, SANG YUN; PARK, OK KU; ARTEMOV, VASILY; LEE, SANG DAE; JOO, HYUN WOO; CHOI, EUN SIL
To: LG LIFE SCIENCES LTD.
Reel/Frame 035978/0683 →
Priority Claims (1)
KR 10-2012-0124502 · Nov 5, 2012 · national
Continuity (1)
Related Publication 20150291527A1 · Oct 15, 2015