IP Library Granted Patent US 9,988,379
Granted Patent B2
US 9,988,379 · App. 14/441,591 · Granted Jun 5, 2018

GPR40 receptor agonist, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent

Inventors: Sung Bae Lee (Daejeon, KR); Seung Yup Paek (Daejeon, KR); Sook Kyung Yoon (Daejeon, KR); Seung Hyun Yoon (Daejeon, KR); Jeung Soon Choi (Daejeon, KR)
Assignee: LG CHEM, LTD.
C07D471/04C07D209/08C07D209/12C07D209/30C07D231/56C07D235/26C07D249/18C07D261/20C07D401/04C07D401/06C07D403/06C07D405/06C07D405/12C07D409/04C07D413/12C07D413/14C07D417/06
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Quick Facts
Patent No.
US 9,988,379
App. No.
14/441,591
Granted
Jun 5, 2018
Kind
B2
Abstract

The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

Claims (259)

1. A compound of Formula (1), or a pharmaceutically acceptable salt or stereoisomer thereof:

wherein,

Q represents O, or NH,

R1 represents H, alkyl, heteroalkyl, heterocycle, or heterocycle-alkyl,

R2 represents H, alkyl, heteroalkyl, or halogen,

R3 represents H, alkyl, or halogen,

R4 represents H, alkyl, or halogen, or represents O, when R4 is connected with R5,

R5 represents alkoxy, CN, heterocycle, or C≡C-Me, or

R4 and R5 can be connected together to form 5- or 6-membered ring,

R6 represents H, or alkyl, or

R5 and R6 can be connected together to form 3-membered ring,

wherein the structure of

 is selected from the following structures:

wherein, E represents H, alkyl or halogen, and G represents alkyl, heteroalkyl or halogen,

wherein if the structure is

 R2 is absent.

2. A compound, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein the compound is selected from the group consisting of the following compounds

3-{4-[(1-isopropyl-1H-indol-6-ylmethyl)-amino-phenyl}-propanoic acid,

3-{4-[(1-benzyl-1H-indol-6-ylmethyl)-amino]-phenyl}-propanoic acid,

3-{4-[(1-thiophen-3-yl-1H-indol-6-ylmethyl)-amino]-phenyl}-propanoic acid,

3-{4-[(1-phenethyl-1H-indol-6-ylmethyl)-aminol]-phenyl}-propanoic acid,

3-{4-[(1-benzyl-3-chloro-1H-indol-6-ylmethyl)-amino]-phenyl}-propanoic acid,

3-{4-[(1-benzyl-2,3-dichloro-1H-indol-6-ylmethyl)-amino]-phenyl}-propanoic acid,

3-{4-[(1-benzyl-7-chloro-1H-indol-6-ylmethyl)-amino]-phenyl}-propanoic acid,

3-{4-[(7-chloro-1-thiophen-3-yl-1H-indol-6-ylmethyl)-amino]-phenyl}-propanoic acid,

3-(4-{[7-chloro-1-(4-fluoro-phenyl)-1H-indol-6-ylmethyl]-amino}-phenyl)-propanoic acid,

3-(4-{[1-(4-fluoro-phenyl)-1H-indol-6-ylmethyl]-amino}-phenyl)-propanoic acid,

3-{4-[(7-chloro-1-cyclohexyl methyl-1H-indol-6-ylmethyl)-amino]-phenyl}-propanoic acid,

[6-(1-benzyl-3-chloro-1H-indol-6-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid,

3-[4-(1-thiophen-3-yl-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

3-{4-[1-(4-fluoro-phenyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-propanoic acid,

3-[4-(1-benzyl-7-methyl-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

3-[4-(7-methyl-1-thiophen-3-yl-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

3-{4-[1-(4-fluoro-2-methyl-phenyl)-1H-indol-6-ylmethoxy]-phenyl}-propanoic acid,

3-[4-(1-benzyl-7-chloro-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

3-[4-(1-cyclohexyl methyl-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

3-[4-(3-benzyl-1-methyl-1H-indol-5-ylmethoxy)-phenyl]-propanoic acid,

3-[4-(1-methyl-3-o-tolyl-1H-indol-5-ylmethoxy)-phenyl]-propanoic acid,

3-{4-[3-chloro-1-(4-fluoro-2-methyl-phenyl)-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

3-{4-[5-fluoro-1-(4-fluoro-2-methyl-phenyl)-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

{6-[1-(4-fluoro-2-methyl-phenyl)-1H-indol-6-ylmethoxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid,

(S)-3-[4-(1-benzyl-7-methyl-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(4-fluoro-2-methyl-phenyl)-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(4-methanesulfonyl-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(4-methoxy-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[7-methyl-1-(4-trifluoromethyl-benzyl)-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(3-methoxymethyl-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-indol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(4-fluoro-2-methyl-phenyl)-1H-indol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(2,6-difluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-benzyl-2-(2-methoxy-ethyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(3-methanesulfonylmethyl-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[7-methyl-1-(2-methyl-benzyl)-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(2-fluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(2-chloro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(2,6-dimethyl-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-7-chloro-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-5-fluoro-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(3-fluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[7-methyl-1-(3-trifluoromethyl-benzyl)-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[7-methyl-1-(5-methyl-pyrazin-2-ylmethyl)-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(4-methanesulfonylmethyl-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl }-hex-4-ynoic acid,

(S)-3-{4-[1-(6-chloro-pyridin-3-ylmethyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(2-benzyl-2H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-5-fluoro-7-methyl-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(4-fluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(3,4-difluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(3,5-difluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(2,4-difluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

3-[4-(1-benzyl-1H-indol-4-ylmethoxy)-2-fluoro-phenyl]-propanoic acid,

3-[4-(1-benzyl-7-methyl-1H-indol-6-ylmethoxy)-2-fluoro-phenyl]-propanoic acid,

(S)-3-[4-(7-methyl-1-thiazol-4-ylmethyl-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[7-methyl-1-(2-methyl-thiazol-4-ylmethyl)-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(2-benzyl-2H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(7-methyl-1-pyrazin-2-ylmethyl-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(7-methyl-1-pyrimidin-4-ylmethyl-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-3-fluoro-7-methyl-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[7-methyl-1-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(7-methyl-1-pyrimidin-2-ylmethyl-1H-indol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

3-[4-(1-benzyl-1H-indazol-6-ylmethoxy)-phenyl]-3-(4,5-dihydro-isoxazol-3-yl)-propanoic acid,

(S)-3-{4-[1-(4-fluoro-benzyl)-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[2-(4-fluoro-benzyl)-2H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-pyrimidin-2-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(2-pyrimidin-2-ylmethyl-2H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-pyrazin-2-ylmethyl-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(4-fluoro-benzyl)-1H-indazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[2-(4-fluoro-benzyl)-2H-indazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(5-methyl-pyrazin-2-ylmethyl)-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[2-(5-methyl-pyrazin-2-ylmethyl)-2H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-pyrimidin-4-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(2-pyrimidin-4-ylmethyl-2H-indazol-6-ylmethoxy]-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(5-methyl-pyrazin-2-ylmethyl)-1H-indazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[2-(5-methyl-pyrazin-2-ylmethyl)-2H-indazol-4-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-pyridin-3-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(2-pyridin-3-ylmethyl-2H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[7-methyl-1-(6-methyl-pyridin-3-ylmethyl)-1H-indol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-7-methyl-1H-indol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-{4-[1-(4-fluoro-benzyl)-7-methyl-1H-indol-6-ylmethoxy]-phenyl}-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(1-benzyl-1H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-{4-[1-(4-fluoro-benzyl)-1H-indazol-6-ylmethoxy]-phenyl}-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(1-isobutyl-1H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(2-isobutyl-2H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-isoxazol-3-yl-3-[4-(7-methyl-1-pyrazin-2-ylmethyl-1H-indol-6-ylmethoxy)-phenyl]-propanoic acid,

(S)-3-[4-(1-benzyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-isoxazol-3-yl-3-{4-[7-methyl-1-(5-methyl-pyrazin-2-ylmethyl)-1H-indol-6-ylmethoxy]-phenyl}-propanoic acid,

(S)-3-{4-[1-(6-methyl-pyridin-3-ylmethyl)-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-indazol-4-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-{4-[1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy]-phenyl}-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(1-isopropyl-1H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(1-cyclopropylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(1-isobutyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(2-isopropyl-2H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

[6-(1-isopropyl-1H-indazol-6-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid,

(S)-3-isoxazol-3-yl-3-[4-(1-methyl-1H-indazol-6-ylmethoxy)-phenyl]-propanoic acid,

(S)-3-[4-(1H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-[4-(1-cyclopentylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-3-isoxazol-3-yl-propanoic acid,

(S)-3-isoxazol-3-yl-3-[4-(1-pyrazin-2-ylmethyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy)-phenyl]-propanoic acid,

[6-(1-benzyl-1H-indazol-6-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid,

3-[4-(1-benzyl-1H-indazol-6-ylmethoxy)-2-fluoro-phenyl]-propanoic acid,

3-[4-(1-cyclopentylmethyl-1H-indazol-6-ylmethoxy)-2-fluoro-phenyl]-propanoic acid,

[6-(1-cyclopentylmethyl-1H-indazol-6-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid,

[5-(1-benzyl-1H-indazol-6-ylmethoxy)-indan-1-yl]-acetic acid,

[6-(1-benzyl-1H-indazol-6-ylmethoxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-acetic acid,

(S)-3-[4-(1-benzyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(2-benzyl-2H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[6-(2-benzyl-2H-indazol-6-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid,

(S)-3-[4-(1-isobutyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

3-[4-(1-benzyl-1H-indazol-6-ylmethoxy)-phenyl]-butyric acid,

[5-(1-benzyl-1H-indazol-5-ylmethoxy)-indan-1-yl]-acetic acid,

[6-(1-benzyl-1H-indazol-5-ylmethoxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-acetic acid,

[7-(1-benzyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

[6-(1-benzyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid,

(S)-3-[4-(1-benzyl-5-fluoro-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-indol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-benzotriazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-1H-benzoimidazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-7-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(2-benzyl-7-methyl-2H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[6-(1-benzyl-7-methyl-1H-indazol-5-ylmethoxy)-2,3-dihydro-benzofuran-3-yl]-acetic acid,

[6-(1-benzyl-7-methyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

(S)-3-[4-(1-isobutyl-7-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[7-(1-isobutyl-7-methyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

(S)-3-[4-(1-isobutyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[7-(1-isobutyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

(S)-3-[4-(1-phenethyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[7-(1-phenethyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

(S)-3-{4-[1-(3-methyl-butyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

7-[1-(3-methyl-butyl)-1H-indazol-5-ylmethoxy]-chroman-4-yl}-acetic acid,

(S)-3-[4-(1-cyclohexyl methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[7-(1-cyclohexyl methyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

(S)-3-[4-(2-isobutyl-7-methyl-2H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-pyridine-2-ylmethyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[7-(1-pyridine-2-ylmethyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

(S)-3-[4-(1-benzyl-1H-pyrrolo[2,3-b]pyridin-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-1H-pyrrolo[2,3-b]pyridin-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[7-(1-benzyl-7-methyl-1H-indol-6-ylmethoxy)-chroman-4-yl]-acetic acid,

[7-(2-benzyl-7-methyl-2H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

(S)-3-[4-(1-pyridin-3-ylmethyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

[7-(1-pyridin-3-ylmethyl-1H-indazol-5-ylmethoxy)-chroman-4-yl]-acetic acid,

7-[1-(2-ethoxy-ethyl)-1H-indazol-5-ylmethoxy]-chroman-4-yl}-acetic acid,

(S)-3-[4-(5-fluoro-1-isobutyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(tetrahydrofuran-2-ylmethyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(3-methanesulfonyl-propyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(tetrahydrofuran-3-ylmethyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[2-(tetrahydrofuran-3-ylmethyl)-2H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

3-[4-(1-benzyl-1H-indazol-5-ylmethoxy)-phenyl]-3-methoxy-propanoic acid,

(S)-3-[4-(1-isobutyl-1H-pyrazolo[3,4-b]pyridin-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(2-ethoxy-ethyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

3-[4-(1-benzyl-1H-indazol-5-ylmethoxy)-phenyl]-butyric acid,

3-[4-(1-benzyl-1H-indazol-5-ylmethoxy)-phenyl]-pentanoic acid,

(S)-3-{4-[2-(2-ethoxy-ethyl)-2H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-benzyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

3-[4-(1-benzyl-1H-indazol-5-ylmethoxy)-phenyl]-3-cyano-propanoic acid,

(S)-3-[4-(1-cyclopentylmethyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopentyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopropylmethyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-isobutyl-3H-benzotriazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

2-[4-(1-benzyl-1H-indazol-6-ylmethoxy)-phenyl]-cyclopropanecarboxylic acid,

(S)-3-[4-(1-isobutyl-7-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopentylmethyl-7-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-3-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopentyl-7-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopentyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopentylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(2-methanesulfonyl-ethyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(2-methoxy-ethyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(3-methoxy-propyl)-1H-indazol-5-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[1-(3-methyl-oxetan-3-ylmethyl)-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-3-methyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(2-isobutyl-3-methyl-2H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-isobutyl-benzo[d]isoxazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[1-(2,2-dimethyl-propyl)-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-6-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-3-methyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-isobutyl-1-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-3-methyl-1H-indazol-5-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-3-methoxymethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-fluoro-1-isobutyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-ethoxymethyl-1-isobutyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-chloro-1-isobutyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-3-isopropoxymethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-fluoro-1-isopropyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-bromo-1-methyl-1H-indazol-7-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-3-methoxymethyl-7-methyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-butyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-butyl-3-fluoro-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopropylmethyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-cyclopropylmethyl-3-fluoro-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-chloro-1-methyl-1H-indazol-7-ylmethoxy)-methyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-3-pyrazol-1-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-fluoro-1-methyl-1H-indazol-7-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-1H-pyrrolo[2,3-b]pyridin-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-butyl-3-methyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-butyl-1-methyl-1H-indazol-7-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-isobutyl-1-methyl-1H-indazol-7-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-7-methyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-isopropyl-1-methyl-1H-indazol-7-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-methyl-3-propyl-1H-indazol-7-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-7-methyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-3,7-dimethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-fluoro-1-isobutyl-7-methyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-ethyl-3-fluoro-7-methyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-7-methyl-3-morpholin-4-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(7-chloro-1-isobutyl-3-morpholin-4-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-7-methyl-3-pyrrolidin-1-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-7-methyl-3-piperidin-1-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-3-morpholin-4-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-7-methyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(7-methyl-1-propyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-fluoromethyl-1-isobutyl-7-methyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-7-methyl-1H-indazol-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(1-isopropyl-1H-pyrrolo[2,3-b]pyridin-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(3-fluoro-1-isobutyl-1H-pyrrolo[2,3-b]pyridin-4-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-[4-(7-methyl-1-pyridin-3-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[3-(3,3-difluoro-piperidin-1-ylmethyl)-1-isobutyl-7-methyl-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-[4-(1-isobutyl-7-methyl-3-pyrazol-1-ylmethyl-1H-indazol-6-ylmethoxy)-phenyl]-hex-4-ynoic acid,

(S)-3-{4-[3-((S)-3-fluoro-pyrrolidin-1-ylmethyl)-1-isobutyl-7-methyl-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[3-(3,3-difluoro-pyrrolidin-1-ylmethyl)-1-isobutyl-7-methyl-1H-indazol-6-ylmethoxy]-phenyl}-hex-4-ynoic acid,

(S)-3-{4-[3-(3,3-difluoro-pyrrolidin-1-ylmethyl)-1-isobutyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid, and

(S)-3-{4-[3-(3,3-difluoro-piperidin-1-ylmethyl)-1-isobutyl-1H-pyrrolo[2,3-b]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid.

3. The compound or the pharmaceutically acceptable salt or stereoisomer thereof according to claim 1 , wherein the compound is for the treatment of diabetes.

4. A pharmaceutical composition, comprising the compound, or the pharmaceutically acceptable salt or stereoisomer thereof according to claim 1 , and a pharmaceutically acceptable carrier.

5. An insulin secretagogue or hypoglycemic agent comprising as an active ingredient, the compound, or the pharmaceutically acceptable salt or stereoisomer thereof according to claim 1 .

6. A GPR40 receptor agonist comprising the compound, or the pharmaceutically acceptable salt or stereoisomer thereof according to claim 1 as an active ingredient.

7. A pharmaceutical composition for treating diseases or disorders selected from the group consisting of diabetes, high blood sugar, glucose tolerance, impaired fasting blood glucose, and diabetes complications, comprising the compound, or the pharmaceutically acceptable salt or stereoisomer thereof according to claim 1 as an active ingredient, and a pharmaceutically acceptable carrier.

8. The pharmaceutical composition according to claim 7 , wherein the diabetes complication is selected from hyperlipidemia, hypertension, retinopathy, renal failure, or obesity.

9. A method for treating a disease or disorder in a mammal, comprising administration of the compound, or the pharmaceutically acceptable salt or stereoisomer thereof according to claim 1 to the mammal,

wherein the disease or disorder is selected from the group consisting of diabetes, high blood sugar, glucose tolerance, impaired fasting blood glucose, and diabetes complications.

10. The method of claim 9 , wherein the disease or disorder is diabetes.

11. The method of claim 9 , wherein the disease or disorder is diabetes complication and the diabetes complication is selected from the group consisting of hyperlipidemia, hypertension, retinopathy, renal failure, and obesity.

Assignments (3)
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 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 9, 2015
From: LEE, SUNG BAE; PAEK, SEUNG YUP; YOON, SOOK KYUNG; YOON, SEUNG HYUN; CHOI, JEUNG SOON
To: LG LIFE SCIENCES LTD.
Reel/Frame 036048/0565 →
Priority Claims (1)
KR 10-2012-0127005 · Nov 9, 2012 · national
Continuity (1)
Related Publication 20150291584A1 · Oct 15, 2015