US 11,261,186 B2Granted

Biaryl derivative as GPR120 agonist

AssigneeLG Chem, Ltd.

InventorsYoung Kwan Kim, Sang Yun Park, Hyun Woo Joo, Eun Sil Choi, Seung Yup Paek, Seung Wan Kang, Byung Gyu Kim, Chang Seok Lee, Sung Wook Kim, Sang Dae Lee

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Abstract

Compounds having the chemical formula 1, a method for producing the compounds of chemical formula 1, a pharmaceutical composition comprising same, and use thereof as a GPR120 agonist for prevention or treatment of inflammation or metabolic diseases such as diabetes, complications from diabetes, obesity, non-alcoholic fatty liver disease, fatty liver disease, and osteoporosis.

Claims2

Dependent claims

A compound selected from the group consisting of:

2-[1-[4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[2-(cyclobutoxy)-6-methyl-pyrimidin-4-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclopropylmethoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[6-(cyclopropylmethoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-(6-ethoxypyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isopropoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-methoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-propoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isobutoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-butoxypyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclopentoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(4-ethoxypyrimidin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isopropoxypyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-propoxypyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isobutoxypyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(4-ethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isopropoxy-6-methyl-pyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-methyl-6-propoxy-pyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isobutoxy-6-methyl-pyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-pyrrolidin-1-ylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(isopropylamino)pyrazin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(diethylamino)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(isobutylamino)pyrazin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclopentylamino)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(dimethylamino)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(isobutylamino)pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclobutoxy)-5-methyl-pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-phenylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-cyclopentylpyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isobutylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isobutylpyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-butylpyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isopentylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-5-fluoro-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)-5-fluoro-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-cyclobutylpyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-5,6-dimethyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
4-[2-chloro-4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-6-fluoro-phenoxy]butanoic acid,
4-[2-chloro-4-[2-(cyclobutoxy)-6-methyl-pyrimidin-4-yl]-6-fluoro-phenoxy]butanoic acid,
4-[2-chloro-4-[4-(cyclopropylmethoxy)-6-methyl-pyrimidin-2-yl]-6-fluoro-phenoxy]butanoic acid,
4-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenoxy]butanoic acid,
5-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]hexanoic acid,
5-[4-(2-cyclobutoxy-6-methyl-pyrimidin-4-yl)-2,6-difluoro-phenyl]-hexanoic acid,
5-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-hexanoic acid,
4-[4-(4-cyclobutoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[4-(2-cyclobutoxy-pyrimidin-4-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(4-cyclobutoxy-pyrimidin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(2-cyclobutoxy-pyrimidin-4-yl)-6-fluoro-phenoxy]-butyric acid,
4-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(6-cyclobutoxy-pyrazin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(6-cyclopropylmethoxy-pyrazin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[4-(4-cyclopropylmethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[4-(6-cyclopropylmethoxy-pyrazin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[2-chloro-6-fluoro-4-(6-isopropoxy-pyrazin-2-yl)-phenoxy]-butyric acid,
4-[2-chloro-4-(6-ethoxy-pyrazin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[4-(cyclobutoxy)pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[4-(cyclopropylmethoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[4-(cyclopropylmethoxy)pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[6-(cyclopropylmethoxy)pyrazin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
2-{1-[2,6-difluoro-4-(6-propoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-isobutoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-cyclopentoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-butoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-propoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-isopropoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-ethoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-isobutoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-isobutylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-cyclopentylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-isopropylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-diethylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
3-[6-(6-cyclobutoxy-pyrazin-2-yl)-thiochroman-2-yl]-propionic acid,
2-[1-[4-[4-(4-chlorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-chlorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-pyrrolidin-3-yl]acetic acid,
2-[1-[4-[4-phenoxy-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-fluorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-pyridin-3-yloxy-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(4-fluorophenoxy)pyrazin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-methoxyphenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(4-fluorophenoxy)-6-methyl-pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(p-tolyloxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(3,4-difluorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(4-cyclobutoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(4-cyclopropylmethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(6-cyclopropylmethoxy-pyrazin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(6-cyclobutoxy-pyrazin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[2-chloro-4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-6-fluoro-phenoxymethyl]-cyclopropane carboxylic acid,
{1-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclopropylmethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(6-cyclobutoxy-pyrazin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yll}-acetic acid,
{1-[4-(4-cyclobutoxy-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(6-cyclopropylmethoxy-pyrazin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(6-methoxy-pyrazin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(6-ethoxy-pyrazin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(6-isopropoxy-pyrazin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-isopropoxy-6-methyl-pyrimidin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-isobutoxy-6-methyl-pyrimidin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-methyl-6-propoxy-pyrimidin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-ethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclobutoxy-5-fluoro-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclopropylmethoxy-5-fluoro-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(5-fluoro-4-isobutoxy-pyrimidin-2-yl)-phenyl]-piperidin-4-yl}-acetic acid,
{1-[2,6-difluoro-4-(5-fluoro-4-propoxy-pyrimidin-2-yl)-phenyl]-piperidin-4-yl}-acetic acid,
(1-{2,6-difluoro-4-[4-(3-methyl-butoxy)-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
(1-{2,6-difluoro-4-[4-(3-methoxy-propoxy)-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
(1-{2,6-difluoro-4-[4-(3-methoxy-propoxy)-6-methyl-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
(1-{2,6-difluoro-4-[4-(2-methoxy-ethoxy)-6-methyl-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
2-[1-[2,6-difluoro-4-[4-[(6-methyl-3-pyridyl)oxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(4-ethylphenoxy)pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(3-fluorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(3,4-fluorophenoxy)-6-methyl-pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(2-pyridyloxy)pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-[4-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-[3-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-methyl-6-[4-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-methyl-6-[3-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
{1-[4-(4-cyclobutoxy-6-trifluoromethyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-piperidin-4-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-propoxy-6-trifluoromethyl-pyrimidin-2-yl)-phenyl]-piperidin-4-yl}-acetic acid, and
(1-{2,6-difluoro-4-[4-(4-fluoro-phenoxy)-6-trifluoromethyl-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
or a pharmaceutically acceptable salt or stereoisomer thereof.

133 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/539,310Filed 23 Dec 2015
Priority: KR 10-2014-018839924 Dec 2014
Published: US 2017/0349594 A17 Dec 2017
Granted: 1 Mar 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification56 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61K 31/4725
Non-condensed isoquinolines, e.g. papaverine: containing further heterocyclic rings
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/00
Drugs for disorders of the metabolism

Family

US 2017/0349594 A1Pre-grant publication · published 7 Dec 2017
US 11,261,186 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound selected from the group consisting of:

2-[1-[4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[2-(cyclobutoxy)-6-methyl-pyrimidin-4-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclopropylmethoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[6-(cyclopropylmethoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]azetidin-3-yl]acetic acid,
2-[1-[4-(6-ethoxypyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isopropoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-methoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-propoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isobutoxypyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-butoxypyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclopentoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(4-ethoxypyrimidin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isopropoxypyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-propoxypyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isobutoxypyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(4-ethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isopropoxy-6-methyl-pyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-methyl-6-propoxy-pyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isobutoxy-6-methyl-pyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-pyrrolidin-1-ylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(isopropylamino)pyrazin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(diethylamino)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(isobutylamino)pyrazin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclopentylamino)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(dimethylamino)pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(isobutylamino)pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[6-(cyclobutoxy)-5-methyl-pyrazin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-phenylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-cyclopentylpyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isobutylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(4-isobutylpyrimidin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-butylpyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-(6-isopentylpyrazin-2-yl)phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-5-fluoro-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclopropylmethoxy)-5-fluoro-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-(6-cyclobutylpyrazin-2-yl)-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(cyclobutoxy)-5,6-dimethyl-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
4-[2-chloro-4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-6-fluoro-phenoxy]butanoic acid,
4-[2-chloro-4-[2-(cyclobutoxy)-6-methyl-pyrimidin-4-yl]-6-fluoro-phenoxy]butanoic acid,
4-[2-chloro-4-[4-(cyclopropylmethoxy)-6-methyl-pyrimidin-2-yl]-6-fluoro-phenoxy]butanoic acid,
4-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenoxy]butanoic acid,
5-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-phenyl]hexanoic acid,
5-[4-(2-cyclobutoxy-6-methyl-pyrimidin-4-yl)-2,6-difluoro-phenyl]-hexanoic acid,
5-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-hexanoic acid,
4-[4-(4-cyclobutoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[4-(2-cyclobutoxy-pyrimidin-4-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(4-cyclobutoxy-pyrimidin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(2-cyclobutoxy-pyrimidin-4-yl)-6-fluoro-phenoxy]-butyric acid,
4-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(6-cyclobutoxy-pyrazin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[2-chloro-4-(6-cyclopropylmethoxy-pyrazin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[4-(4-cyclopropylmethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[4-(6-cyclopropylmethoxy-pyrazin-2-yl)-2,6-difluoro-phenoxy]-butyric acid,
4-[2-chloro-6-fluoro-4-(6-isopropoxy-pyrazin-2-yl)-phenoxy]-butyric acid,
4-[2-chloro-4-(6-ethoxy-pyrazin-2-yl)-6-fluoro-phenoxy]-butyric acid,
4-[4-[4-(cyclobutoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[4-(cyclobutoxy)pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[6-(cyclobutoxy)pyrazin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[4-(cyclopropylmethoxy)-6-methyl-pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[4-(cyclopropylmethoxy)pyrimidin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
4-[4-[6-(cyclopropylmethoxy)pyrazin-2-yl]-2,6-difluoro-N-methyl-anilino]butanoic acid,
2-{1-[2,6-difluoro-4-(6-propoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-isobutoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-cyclopentoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-butoxy-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-propoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-isopropoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-ethoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(4-isobutoxy-pyrimidin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-isobutylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-cyclopentylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-isopropylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
2-{1-[2,6-difluoro-4-(6-diethylamino-pyrazin-2-yl)phenyl]pyrrolidin-3-yl}acetic acid,
3-[6-(6-cyclobutoxy-pyrazin-2-yl)-thiochroman-2-yl]-propionic acid,
2-[1-[4-[4-(4-chlorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-chlorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-pyrrolidin-3-yl]acetic acid,
2-[1-[4-[4-phenoxy-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-fluorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-pyridin-3-yloxy-pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(4-fluorophenoxy)pyrazin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(4-methoxyphenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(4-fluorophenoxy)-6-methyl-pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(p-tolyloxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(3,4-difluorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(4-cyclobutoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(4-cyclopropylmethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(6-cyclopropylmethoxy-pyrazin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[4-(6-cyclobutoxy-pyrazin-2-yl)-2,6-difluoro-phenoxymethyl]-cyclopropane carboxylic acid,
2-[2-chloro-4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-6-fluoro-phenoxymethyl]-cyclopropane carboxylic acid,
{1-[4-(4-cyclobutoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclopropylmethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(6-cyclobutoxy-pyrazin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yll}-acetic acid,
{1-[4-(4-cyclobutoxy-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(6-cyclopropylmethoxy-pyrazin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclopropylmethoxy-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(6-methoxy-pyrazin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(6-ethoxy-pyrazin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(6-isopropoxy-pyrazin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-isopropoxy-6-methyl-pyrimidin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-isobutoxy-6-methyl-pyrimidin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-methyl-6-propoxy-pyrimidin-2-yl)-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-ethoxy-6-methyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclobutoxy-5-fluoro-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[4-(4-cyclopropylmethoxy-5-fluoro-pyrimidin-2-yl)-2,6-difluoro-phenyl]-pyrrolidin-3-yl}-acetic acid,
{1-[2,6-difluoro-4-(5-fluoro-4-isobutoxy-pyrimidin-2-yl)-phenyl]-piperidin-4-yl}-acetic acid,
{1-[2,6-difluoro-4-(5-fluoro-4-propoxy-pyrimidin-2-yl)-phenyl]-piperidin-4-yl}-acetic acid,
(1-{2,6-difluoro-4-[4-(3-methyl-butoxy)-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
(1-{2,6-difluoro-4-[4-(3-methoxy-propoxy)-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
(1-{2,6-difluoro-4-[4-(3-methoxy-propoxy)-6-methyl-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
(1-{2,6-difluoro-4-[4-(2-methoxy-ethoxy)-6-methyl-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
2-[1-[2,6-difluoro-4-[4-[(6-methyl-3-pyridyl)oxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[6-(4-ethylphenoxy)pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[4-[4-(3-fluorophenoxy)pyrimidin-2-yl]-2,6-difluoro-phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(3,4-fluorophenoxy)-6-methyl-pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-(2-pyridyloxy)pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-[4-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-[3-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-methyl-6-[4-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
2-[1-[2,6-difluoro-4-[4-methyl-6-[3-(trifluoromethyl)phenoxy]pyrimidin-2-yl]phenyl]-4-piperidyl]acetic acid,
{1-[4-(4-cyclobutoxy-6-trifluoromethyl-pyrimidin-2-yl)-2,6-difluoro-phenyl]-piperidin-4-yl}-acetic acid,
{1-[2,6-difluoro-4-(4-propoxy-6-trifluoromethyl-pyrimidin-2-yl)-phenyl]-piperidin-4-yl}-acetic acid, and
(1-{2,6-difluoro-4-[4-(4-fluoro-phenoxy)-6-trifluoromethyl-pyrimidin-2-yl]-phenyl}-piperidin-4-yl)-acetic acid,
or a pharmaceutically acceptable salt or stereoisomer thereof.

133 more elements

Facts

Application

15/539,310Filed 23 Dec 2015

Priority

KR 10-2014-018839924 Dec 2014

Published

US 2017/0349594 A17 Dec 2017

Granted

1 Mar 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification56 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61K 31/4725
Non-condensed isoquinolines, e.g. papaverine: containing further heterocyclic rings
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/00
Drugs for disorders of the metabolism