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Biaryl Derivatives As Gpr120 Agonists

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

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Patent Information

Application #
Filing Date
21 January 2016
Publication Number
28/2016
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
ipo@knspartners.com
Parent Application

Applicants

LG LIFE SCIENCES LTD.
LG Gwanghwamun Bldg. 58 , Saemunan-ro (Sinmunno 2-ga), Jongno-gu, Seoul 110-783

Inventors

1. KIM, Young Kwan
R&D Park, LG Life Sciences Ltd., 188, Munji-ro, Yuseong-gu, Daejeon 305-738
2. PARK ,Sang Yun
R&D Park, LG Life Sciences Ltd., 188, Munji-ro, Yuseong-gu, Daejeon 305-738
3. JOO, Hyun Woo
R&D Park, LG Life Sciences Ltd., 188, Munji-ro, Yuseong-gu, Daejeon 305-738
4. CHOI, Eun Sil
R&D Park, LG Life Sciences Ltd., 188, Munji-ro, Yuseonggu, Daejeon 305-738

Specification

DESCRIPTION HENCE NOT PASTED

Claims
[Claim 1] Biaryl derivatives of Formula 1, or pharmaceutically acceptable salts or
isomers thereof: [Formula 1]
A and B represent independently phenyl or pyridine, any one of RrD- and R2-E- cannot exist, D and E represent inde¬pendently carbon, nitrogen, oxygen or sulfur, or represent direct bond, and any one of Ri and R2 cannot exist, or Ri and R2 represent inde¬pendently hydrogen, halogen, optionally substituted C,-C6-alkyl, C3-C|0 -cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3~C|0-heterocycloarkyl, C, -Qralkyl-QrCio-cycloalkyl, C[-Cf)-aIkyl-CrCio-rieterocycloalkyl, aryl, CrC6-alkylaryl, heteroaryl orCi-C6-a3kyl-C5-C6-heteroai7l, and when D and E represent nitrogen or carbon, R: and R2 can represent two or three optionally substituted C,-C6-alkyl, C3-C|0-cycloalkyl, C2-C6 -alkenyl, C2-C6~alkynyl, CrC6-aUcyl-C3-Ci(rcycloalkyl, aryl or C,-C6 -alkylaryl which may be the same or different,
G represents -J-(CR5R6)P, wherein J represents oxygen or sulfur, R5 and
Rf, represent independently hydrogen, halogen, optionally substituted
alkyl or cycloalkyl, hydroxyl or amine, and R5 and R6 which are sub¬
stituted at the same or different carbon may be connected to form op¬
tionally substituted cycloalkyl or cycloheteroalkyl,
R3 and R4 cannot independently exist depending on the number of m or
n, or represent independently hydrogen, halogen or optionally sub¬
stituted Ci-C6-alkyl or Ci-C6-alkoxy,
R7 represents hydrogen, alkyl or cycloalkyl,
m and n represent independently an integer of 0 to 5, and
p represents an integer of 1 to 6.
[Claim 2] The biaryl derivatives, or pharmaceutically acceptable salts or isomers
thereof according to Claim 1, selected from the following compounds: 4-[4-(6-phenoxy-2-pyridyl)phenoxy]bulyric acid;

4-[2,6-difluoro-4~(6-isopropylsulfanyl-2-pyridyI)phenoxy]bulyric acid; 4-[2,6-difluoro-4-(6-phenoxy-2-pyridyl)phenoxy]butyric acid; 4-[2-chloro-4-(6-isopropylsuIfanyl-2-pyridyl)phenoxy]butyric acid; 4-[2-fluoro-4-(6-isopropylsulfanyl-2-pyridyl)phenoxy]butyric acid; 4-[4-(6-cyclopentylsulfanyl-2-pyridyl)-2,6-difluoro-phenoxy]butyric acid;
4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2-melhoxy-phenoxy]-butyric acid;
4-[2,6-difluoro-4-(2-isopropylsulfanyl-4-pyridyl)phenoxy]butyric acid; 4-[4-[6-(cycIopentoxy)-2-pyridylJ-2,6-difluoro-phenoxyjbutyric acid; 4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2,6-dimethyl-phenoxy]-butyri c acid;
4-[4-[3-(cyclopentoxy)phenyl]-2,6-difluoro-phcnoxy]bulyric acid; 4-[2,6-difluoro-4-(6-pyrrolidin-l-yl-2-pyridyI)phenoxy]butyric acid; 4-[4-(2-5,(?c-butylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenoxy]-butyric acid;
4-[4-[3-(cyclopentoxy)phenyl]-2,3-difluoro-phenoxy]butyric acid; 4-[2,6-difluoro-4-[6-(l-piperidyl)-2-pyridyl]phenoxy]butyric acid; 4-[4-(6-anilino-2-pyridyl)-2,6-difluoro-phenoxy]butyric acid; 4-[2,6-difluoro-4-[6-(N-methylanilino)-2-pyndyl]phenoxy]butyric acid; 4-[4-[6-(cyclopentylamino)-2-pyridy]j-2,6-difluoro-phenoxy]bulyric acid;
4-[4-r6-(cyclopropylmethylsulfanyl)-2-pyridyl]-2,6-difluoro-phcnoxy]b utyric acid;
4-[4-(6-cyclobutylsulfanyl-2-pyridyl)-2,6-difluoro-phenoxy]butyric acid;
4-[2,6-difluoro-4-(6-propylsulfanyl-2-pyridyl)phenoxy]bulyric acid; 4-[2,6-difluoro-4-(6-isopropoxy-2-pyridyl)phenoxy]butyric acid; 4-[2,6-difluoro-4-(6-prapoxy-2-pyridyl)phenoxy]butyric acid; 4-[4-[6-(cyclopropylmethoxy)-2-pyridyl]-2,6-difluoro-phenoxy]butyric acid;
4-[4-[6-(cyclobutoxy)-2~pyridyl]-2,6-difluoro-phenoxy]butyric acid; 4-[4-[6-(cyclobutoxy)-2-pyridyl]-2-methyl-phenoxy]butyric acid; 4~[4-[6-(cyclobutoxy)-2-pyridyl]-2-(trifluoromcthyl)phenoxy]butyric acid;
4-[4-(2-cyclobutylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy]pentanoic acid; 4-[4-[6-(cyclobutoxy)-2-pyridyl]-2,6-difluoro-phenoxy]pentanoic acid;

4-[[5-(2-cycIobutylsulfanyl-3-pyridyl)-2-pyridyl]oxy]pentanoic acid; 4- {2,6-difluoro-4-[2-(3-methy l-butylsulfanyl)-pyridin-3-y 1] -phenoxy} -butyric acid;
4- {2,6-difluoro-4-[2-(2-fluoro-ethoxy )-pyridin-3-y l]-phenoxy} -butyric acid;
2-[l-[[4-(2-cyclobutylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy]methyl ] cyclopropyl] acetic acid;
2-[l-[[4-[3-(cyclobutoxy)phenyl]-2,6-difluoro-phenoxy]methyl]cyclopr opyl] acetic acid;
4-[[6-[3-(cyclobutoxy)phenyl]-3-pyridyl]oxy]butyric acid; 4-[[6~[3-(cyclopentoxy)phenyl]-3-pyridyl]oxy]butyric acid; 4-(2'-phenoxy-biphenyl-4-yloxy)-butyric acid; 4-[4-(2-isopropylsulfanyl-pyridin-3-yl)-phenoxy]-butyric acid; 4-(3,5-difluoro-2'-phenoxy-biphenyl-4-yloxy)-butyric acid; 4-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-phenoxy]-butyric acid; 4-[2,6-difLuoro-4-(2-isopropylsulfanyl-pyridin-3-yl)-phenoxy]-butyric acid;
4-[2,6-difluoro-4-(2-phenoxy-pyridin-3-yl)-phenoxy]-butyric acid; 4-[2,6-difluoro-4-(2-isopropoxy-pyridin-3-yl)-phenoxy]-butyric acid; 4-[4-(2-cyclopentyloxy-pyridin-3-yl)-2,6-difluora-phenoxy]-butyric acid;
4-[4-(2-cyclopentylsulfanyI-pyridin-3-yl)-2,6"diiluoro-phenoxyj-butyri c acid;
4-[4-(2-cyclopropylmcthoxy-pyridin-3-yl)-2,6-difluoro-phcnoxy]-butyr ic acid;
4-[4-(2~cyclopropylmethylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenoxy] -butyric acid;
4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-phenoxy]-butyric acid; 4-[4~(2-cyclopropylmethylsulfanyl-pyridin-3-yl)-phenoxy]-butyric acid;
4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenoxy]-butyric acid;
4-[4~(2-propylsulfanyl-pyridin-3-yl)-phenoxy]-butyric acid; 4-(3,5-difluoro-2'"isopropoxy-biphenyl-4-yloxy)-butyric acid; 4-(2'-cyclobutoxy-3,5-difluoro-biphenyl-4-yloxy)-butyric acid; 4-(2'-cyclopropylmethoxy-3,5-difiuoro-biphcnyl'4-yloxy)-butyric acid; 4-(2'-cyclopentyloxy-3,5-difluoro-biphenyl-4-yloxy)-butyric acid; 4-(2'-cyclopentyloxy-biphenyl-4-yloxy)-butyric acid;

4-(2'-isopropoxy-biphenyl-4-yloxy)~-butyric acid;
4-(2'-cyclopropylmethoxy-biphenyl-4-yloxy)-butyric acid;
4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2,6-difluoro-phcnoxy]-2-meth
yl-butyric acid;
2-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2,6~difluoro-phenoxymethyl3-
cyclopropanecai'boxylic acid;
4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2,5-difluoro-phenoxy]-butyric
acid;
4-[4-(6-cyclobutylsLilfanyl-pyridin-2-yl)-2)5-difluoro-phenoxy]-butyric
acid;
4-[4-(2-r^rr-butylsuli:anyl-pyridin~3-yl)-2,6-difluoro-phenoxy]-butyric
acid;
6"[2,6-difluoro-4-(2-propylsulfanyl-3-pyridyl)phcnoxy]hexanoic acid;
4-{2,6-difluoro-4-[6-(2-methyl-propenyl)-pyridin-2-yl]-phenoxy}-buty
ric acid;
4-[2,6-difluoro-4-(6-isobutyl-pyridin-2-yl)-phenoxy]-butyric acid;
4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-3,5-difluoro-phenoxy]-butyric
acid;
4-{2,6-difluoro-4-[2-(tetrahydro-pyran-4-yloxy)-pyridin-3-yI]-phenoxy
}-butyric acid;
4-{2,6-difiuoro-4-[2-(tetrahydro-iuran-3-yIoxy)-pyridin-3-yIJ-phenoxy
}-butyric acid;
4-[4-(2-cyclobutoxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-bulyric acid;
4-{2,6-difluoro-4-[2-(2-mctrioxy-etrioxy)-pyndiii-3-yi]-phenoxy}-bulyr
ic acid;
4-[2,6-difluoro-4-(2-pyrrolidin-l-yl-3-pyridyl)phenoxy3butanoic acid;
4-[4-[2-(cyclopentylamino)-3-pyridyl]-2,6-difluoro-phenoxyjbutanoic
acid;
4-[4-[2-(cyclopropylm.ethylamino)-3-pyridyl]-2,6-difluoro-phenoxyjbut
aiioic acid;
4-[4-[6-(cyclopropylmethyiamino)-2-pyndyl]-2,6-diiluoro-phenoxy]but
anoic acid;
4-[2,6-difluoro-4-[2-(isopropylamino)-3-pyridyl]phenoxy]butanoic
acid;
4-[4-[2-(cyclopropylamino)-3-pyridyl]-2,6-difluoro-phciioxy]butanoic
acid;
4-[2,6-difluoro-4-[6-(isopropylamino)-2-pyridyl]phenoxy]butanoic
acid;

4-[4-[2-(cyclopentylamino)phenyl]-2,6-difluoro-phenoxy]butanoic acid;
4-[4-[3-(cyclopentylamino)phenyl]-2,6-difIuoro-phenoxy]butanoic acid;
4-[2)6-difluoro-4-[2-(propyiamino)phenyl3phenoxy]butanoic acid; 4-[4-[2-(cyclopropylmethylamino)phenyl]-2,6-difluoro-phenoxy]butan oic acid;
4-[2,6-difluoro-4-[2-(isopropylamino)phenyl]phenoxy]butanoic acid; 4~[4-[2-(cyclopenlylamino)phenyl3phenoxy]butanoicacid; 4-[4-[2-(cyclopropylmethylamino)phenylJphenoxyjbutanoic acid; 4-[4-[2"(propylamino)phenyl]phenoxy]butanoic acid; 4-[4-[2-(isopropylamino)phenyl3phenoxy]butanoic acid;
4-[4-[2-(cyclobutylainino)phenyl]phenoxy]butanoic acid; 4-[4-[2-(cyclobutylamino)phenyl]-2,6-difluoro-phenoxy]butanoic acid; 4-[4-[3~(cyclopropylmethylamino)phenyl3-2,6-difiuoro-phenoxy]butan oic acid;
4-[2,6-difluoro-4-[3-(isopropylamino)phenyl]phenoxy]butanoic acid; 4-[2,6-difluoro-4-(3-pyiTolidin-l-ylphenyl)phenoxy]butanoic acid; 4-[4-[3-(cyclobutylamino)phenyl]-2,6-difiuoro-phenoxy]butanoic acid; 4-[2,6-difluoro-4-[3-(propylamino)phenyl]phenoxy]butanoic acid; 4-[4-[5-chloro-2-(cyclopentylamino)phenyl]-2,6-diiluo]-o-phenoxy]buta noic acid;
4-[4-[2-(cyclopentylamino)-5-fluoro-phenyl]-2,6-difluoro-phenoxylbut anoic acid;
4-[4-(3-cyclopentylphenyl)-2,6-difiuoro-phenoxy]butanoic acid; 4-[4-[3-(cyclopentylmethyl)phenyl3-2,6-difluoro-phenoxy]butanoic acid;
4-[4-[2-(cyclopentylmethyl)pbenyl]-2,6-difluoro-phenoxy]butanoic acid;
4-[4-[6-(cyclopentylmethyl)-2-pyridyI]-2,6-difluoro-phenoxy]butanoic acid;
4-[4-[2-(cyclobutylmethyl)pheiiyl3-2,6-difluoro-phenoxyjbutaiioic acid: 4-[4-[3-(cyclobutylmethyl)phenyl]-2,6-difluoro-phenoxy]bulanoic acid; 4-[446-(cyclobutylmcthyl)-2-pyridyl]-2,6-difluoro-phenoxy]butanoic acid;
4-[4-(2-cyclopentylphenyl)-2,6-difluoro-phenoxy]butanoic acid; 4-[4-(6-cyclopentyl-2-pyridyl)-2,6-difluoro-phenoxy]bulanoic acid; 4-[2)6-difluoro-4-(2-isobutyl-3-pyridyl)phenoxy]butanoic acid;

4-[4-(2-cyclopentyl-3-pyridyl)-2,6-difluoro~phenoxy]butanoic acid; 4-[4-r2-(cyclopentylmethyl)-3-pyridyl]-2,6-difluoro-phenoxy]butanoic acid;
4-[2,6-difluoro-4-(2-pyrrol-l-yl-3-pyridyl)phenoxy]butanoic acid; 4-[2,6~difluoro-4-[2-(4-methylpyrazol-l-yl)-3-pyridyl]phenoxy]butanoi c acid;
4-[2,6-difluoro-4-(2-morpholino-3-pyridyl)phenoxy]butanoic acid; 4-[2,6-difluoro-4-[2-(tetrahydropyran-4-ylmethylamino)-3-pyridyl]phe noxy] butanoic acid;
4-[2,6-difluoro-4-[2-(l-piperidyl)-3-pyridyI]phenoxy]butanoic acid; (4S)-4-[4-(2-cyclobutylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy]penta noic acid;
(4R)-4-[4-(2-cyclobutylsulfanyl-3-pyridyl)-2,6-difluoro-phcnoxy]penia noic acid;
(4R)-4-[4-[3-(cyclobutoxy)phenyl]-2,6-difluoro-phenoxy]pentanoic acid;
(4R)-4-[4-(2-cyclopentylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy]pent anoic acid;
(4R)-4-[2,6-ditluoro-4-(3-phenoxyphenyl)phenoxy]pentanoic acid; 4-(3'~cydobutoxy-biphenyl-4-ylsulfanyl)-butyric acid; 4~t3'-isopropoxy-biphenyl-4-ylsuiranyl)-butyric acid; [i-(3,5-difluoro-3'-isopropoxy-biphenyi-4-y]sulfanylmcthyi)-cycloprop yl]-acetic acid;
4-(3'-cyclopcntyloxy-3,5-difluoro-biphcnyl-4-ylsulfanyl)-butyric acid; 4-[4-(2-cyclopentyloxy-pyridin~3-yl)-phenylsulfanyl]-butyric acid; 4-[4-(2-cyclopropylmethoxy-pyridin-3-y l)-phenylsulfany 1]-butyric acid;
4-(3'-phenoxy-biphenyl-4-ylsuIfanyl)-butyric acid; 4-(3'-cyclopentyloxy-biphenyl-4-ylsulfanyl)-butyric acid; 4-(3'-propoxy-biphenyl-4-ylsulfanyl)-butyric acid; 4-[4-(6-cyclobutoxy-pyridin-2-yl)-phenylsulfanylJ-butyric acid; 4-[4-(6-cyclopentyloxy-pyridin-2-yl)-phenylsulfanyl]-butyric acid; 4-[4-(6-isopropoxy-pyridin-2-yl)-phenylsulfanyl]-butyric acid; 4-[4-(2-isopropoxy-pyridin-3-yl)-phenylsulfanyl]-butyric acid; 4-[4-(6-propoxy-pyridin-2-yl)-phenylsulfanyl]-butyric acid; 4-[4-(6-cyclopentylsuIfanyl-pyridin-2-yl)-phenylsulfanyl]-butyric acid; 4-(3'-cyclobutoxy-3,5-difluoro-biphenyl-4-ylsulfanyl)-butyric acid; 4-(3,5-difluoro-3l-isopropoxy-biphenyl-4-ylsulfanyl)-butyric acid;

4-[2,6-difluoro-4-(6-propoxy-pyridin-2-yl)-phenylsulfanyl]-butyric acid;
4-[2,6-difluoro-4-(6-isopropoxy-pyridin-2-yl)-phenyIsLilfanyl]-butyric acid;
4-[2,6-difluoro-4-(2-isopropoxy-pyridin-3-yl)-phenylsulfanyi]-butyric acid;
4-[2,6-difluoro-4-(2-propoxy-pyridin-3-yl)~phenylsulfany]]-butyric acid;
4-[2,6-difluoro-4-(6-isopropylsulfanyi-pyridin-2-yl)-phenyIsulfanyl]-bu
tyric acid;
4-[2,6-difluoro-4-(6-propylsulfanyl-pyridin-2-yl)-phenylsulfanyI]-butyr
ic acid;
4-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2,6-difluoi-o-pheiiylsulfanyl]-b
utyric acid;
4-[4-(2-cyclobutoxy-pyridin-3-yl)-phenylsulfanyl]-butyric acid;
4-[4-(2-cyclobutoxy-pyridin-3-yl)-2,6-difluoro-phenylsu]fanyl]-but.yric
acid;
4-[4-(2-cyclopentyloxy-pyridin-3-yl)-2,6-difluoro-phenylsulfanylj-buty
ric acid;
4-[2,6-dinuoro-4-(2-isopropylsulfanyl-pyridin-3-yl)-phenylsuIfanyl]-bu
tyric acid;
4-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenylsuli'anyl]-
butyric acid;
4_[4_(2-isopropylsulfaiiyl-pyridin-3-yl)-phenyIsulfanyl]-butyricacid;
4-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-phenyIsulfanyi]-butyric acid;
4-[2-fluoro-4-(6-isopropoxy-pyridin-2-yl)-phenylsulfanyl]-butyric acid;
4-[4-(2-cyclopentyloxy-pyi'idin-3-yl)-2-fluoro-phenylsulfany3]-butyric
acid;
4-[4-(2-cyclobutylsuIfanyl-pyridin-3-yl)-2-fluoro-phenylsulfanyl]-butyr
ic acid;
4-[4-(2-cyclobutylsulianyl-pyridin-3-yl)-phenylsuiranylj-butyricacid;
4-[4-(6-cyclobutoxy-pyridin-2-yl)-2,6-difluoro-phenylsulfanyl]-butyric
acid;
4-[4-(6-cyclopentyloxy-pyridin-2-yl)-2,6-difluoro-phenylsulfanyl]-buty
ric acid;
4-[4-(6-cyclobutylsulfanyl-pyridin-2-yl)-phenylsulfanyl]-butyric acid;
4-[4-(6-cyclopropylmethoxy-pyridin-2-yl)-2,6-difluoro-phenylsulfanyl]
-butyric acid;

4-[4-(6-cycIobutyIsulf;anyl-pyridin-2-yl)-2,6-difluoro--phenylsulfanyl3-b utyric acid;
4-[4-(6-cyclopcntylsulfanyl-pyridin-2-yl)-2,6-difluoro-phenyIsulfanyl]-butyric acid;
4-(2'-cyclopentylamino-3-fluoro-biphenyl-4-ylsulfanyl)-butyric acid; 4-(2'-cyclopentylamino-3,5-difluoro-biphenyI-4-ylsulfanyl)~butyric acid;
4-[2'-tcyclopropylmethyl-amino)-3,5-difluoro-biphenyl-4-ylsulfanylJ-b utyric acid;
4-[2-fIuoro-4~(2-isopropylsulfanyl-pyridin-3-yl)-phenyIsulfanylj-butyri c acid;
4-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-2-fluoro-phenylsulfanyl]-but yric acid;
4-(3,5-difluoro-2'-isopropylamino-biphenyl-4~ylsulfanyl)-butyric acid; 4-(3,5-difluoro-2'-propylamino-biphenyl-4-ylsulfanyl)-butyric acid; 4-[4-(2-cyclopropylmethoxy-pyridin~3-yl)-2)6-difluoro-pheiiylsuli'any]] -butyric acid;
4-[2,6-difluoro-4-(2-propylsulfanyl-pyridin-3-yl)-phenylsulfanyl]-butyr ic acid;
4-[4-(6-cyc]obutylsulfanyl-pyridin-2-yl)-2-fluoro-phenylsulfanylj-butyr ic acid;
4-[4-(2-cyclopentylamino-pyridin-3-yl)-2-nuoro-phenylsulfanyI]-bulyri c acid;
4~[2-fluoro-4-(2-isopropoxy-pyridin-3-yl)-phenylsulfanyl3-butyric acid; 4-[4-(2-cyclobutoxy-pyridin-3-yl)-2-fluoro-phenylsulfanyl]-butyric acid;
4-[2-fluoro-4-(2-pyrrolidin-l-yl-pyridin-3-yl)-phenylsulfanyl]-butyric acid;
4-[2-fluoro-4-(2-isopropylamino-pyridin-3-yl)-pheiiylsuifanyl]-butyric acid;
4-t2'-cycIopentylamino-3,5'-difluoro-biphenyl-4-ylsulfanyl)-butync acid;
4-(2'-cyclopentylamino-5'-fluoro-biphenyl-4~ylsulfanyl)-butyric acid; 4-(2'-cyclopentyloxy-5'-methyl-biphenyl-4-ylsulfanyl)-butyric acid; 4-(2'-cyclopentyloxy-4'~methoxy-biphenyl-4-ylsulfanyl)-butyric acid; 4-(2'-cyclopentyloxy-5'-fluoro-biphenyl-4-ylsulfanyl)-butyric acid; 4-(2'~cyclopentyloxy-3,5'-difiuoro-biphenyl-4-ylsulfanyl)-butyric acid; 4-[4-(2-cyclopentyloxy-5-methyl-pyridin-3-yi)-phenylsulfanyl]-butyric

acid;
4-(2'-cyclopentyloxy-3,5,5'-trifluoro-biphenyl-4-ylsulfanyl)-butyric
acid;
4-(2'-cyclopentyIoxy-3-fluoro-4'-methoxy-biphenyl-4-ylsulfanyl)-butyr
ic acid;
4-(2'-cyclopentyloxy-3,5-difluoro-4'-methoxy-biphenyl-4-ylsulfanyl)-b
utyric acid;
4~(3-fluoro-2'-isopropoxy-4'-methoxy"biphenyl-4-ylsulfanyl)-butyric
acid;
4-[4-(2-cyclopentyloxy-5-methyl-pyridin-3-yl)-2-fluoro-phenylsulfanyI
]~butyric acid;
4-[2-fluoro-4-(2-isopropoxy-5-methyl-pyridin-3-yl)-phenylsulfanyl]-bu
tyric acid;
4-(3,5,-difluoro-2'-isopropoxy-biphenyl-4-ylsulfanyl)-butyric acid;
4-[4-(2-cyclopentyloxy-6-meihyl-pyridin-3-yl)-2-fluoro-phcnylsulfanyl
]-butyric acid;
4-(3,3'-difluoro-2'-isopropoxy-5'-methyl-bipheiiyl-4-ylsulfanyl)"butyric
acid;
4-(3,3,-difluoro-5r-methyl-2'-propoxy-biphenyl-4-ylsulfanyl)-butyric
acid;
4-(3-fluoro-2',4r-dipropoxy-biphenyl-4-ylsulfanyl)-butyric acid;
4-(6'-cyclopentyloxy-3,2'-difluoro-3'-melhyl-biphenyl-4-ylsuIfanyl)-but
yric acid;
4-(2'-cyclopentyloxy-3,3'-difluoro-biphenyl-4-ylsulfanyl)-butyric acid;
4-(2'-cyclopentyloxy-3,3'-difl.uoro-5'-methyl-biphenyl-4-ylsulfanyl)-but
yric acid;
5-[4-(2-cyclobutylmethoxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-pentan
oic acid;
5-[4-(2-cyclopropoxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-pentanoic
acid;
4-[4-(2-cycIopentyloxy-5-methyl-pyridin-3-yl)-2,6-diiluoro-phenylsuir
anyl]-butyric acid;
4-[4-(2-cyclopentyloxy-pyridin-3-yl)-phenylsulfanyl]-pentanoic acid;
4-[4-(2-isopropoxy-pyridin-3-yl)-phenylsulfanyl]-pentanoic acid;
4-[4-(2-cyclopentyloxy-pyridin-3-yl)-2,6-difluoro-phenylsulfanyl]-penL
anoic acid;
4-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenylsulfanyl]-
penlanoic acid;

4-[4-[2"(2-dimethylammoethyloxy)-3~pyridyl]-2,6-ditluoro-phenoxy]b
utanoic acid;
4-[2,6-difluoro-4-(2-propylsulfanyl-pyridin-3-yl)-phenoxy]-butanoic
acid;
4-[4-(2-cyclopropylsulfanyl-pyridin-3-yI)-2,6-difluoro-phenoxy]-butan
oic acid;
4-[4-(2-ethylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenoxy]-butanoic
acid;
4-[4-(2-butylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenoxy]-butanoic
acid;
4-(2'-cyclopentylamino-biphenyl-4-ylsulfanyl)-butyric acid;
4-[4~(2-cyclopentyloxy-5-methyl-pyridin-3-yl)-2,6-difluoro-phenoxyi-
butyric acid;
4-[4-(6-isopropylsulfanyl-2-pyridyl)phenoxy]butanoic acid;
4-[2,6-difluoro-4-(3-phenoxyphenyl)phenoxy3butanoic acid;
4-[4-[6-[3-(dimethylamino)pyiTolidin-l-yl]-2-pyridyl]-2,6-difluoro-phe
noxy]butanoic acid;
5-[2,6-difluoro-4-(2-isopropoxy-pyridin-3-yl)-phenoxy]-pentanoic
acid;
5-[4-(2-cycIobutoxy-pyridin-3-y1)-2,6-difluoro-phenoxyj-pentanoic
acid;
4-[4-[2-(3,3-difluoropyrrolidin~l-yl)-3-pyridyl]-2,6-difluoro-phenoxy]b
utanoic acid;
4-[2,6-difluoro-4-[2-(4-methylpiperazin-l-yl)-3-pyridyl]phcnoxy]butan
oic acid;
4-[2,6-difluoro-4-[2-(5-methylisoxazol-3-yl)oxy-3-pyridyl]phenoxy]but
anoic acid;
4-[4-[2-[2-(aziridin-l-yl)ethoxy3-3-pyridyl]-2,6-difluoro-phenoxy]buta
noic acid;
4-[2,6-difiuoro-4-[2-(3-furyhnethoxy)-3-pyridyl]phenoxy]butanoic
acid;
4-[2,6-difluoro-4-[2-(2-furylmethoxy)-3-pyridyl]phenoxy]butanoic
acid;
4-[2,6-difluoro-4-[2-[(3-methyloxetan-3-yl)methoxy]-3-pyridyl]phcnox
y] butanoic acid;
4-[2,6-difluoro-4-[2-(tetrahydrofuran-3-ylmethoxy)~3-pyridyl]phenoxy]
butanoic acid;
4-[2,6-difluoro-4-[2-(tetrahydrofuran-2-ylmethoxy)-3-pyridyl]phenoxy]

butanoic acid;
4-[4-(2-cyclobutylmethoxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-butyric
acid;
4-[4-(2-cyclopropoxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-butyric acid; 4-(4-{2-[3-(tert-butyl-dimethyl-silanyloxy)-cycIopentyloxy]-pyridin-3-yl}-2,6-difluorophenoxy)-butyric acid;
4-{2,6-difluoro-4-[2-(3-hydroxy-cyclopentyloxy)-pyridin-3-ylj-phenox
y}-butyric acid;
4-[4-(2-cyclohexyloxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-butyiic
acid;
4-[4-(2-cyclopentyimelhoxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-butyri
c acid;
4-[2,6-difluoro-4-(2~isobutoxy-pyridin-3-yl)~phcnoxy]-butyric acid;
4-{4-[2~(2,2-dimethy-propoxy)-pyridin-3~yl]-2,6-difluorO"phenoxy}-bu
tyric acid;
5-[4-(2-cyclopentyloxy-pyridin-3-yl)-2,6-difluoro-phenoxy]-pcntanoic
acid;
5-[4-(2-cyclobutylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy]pentanoic
acid;
5-t4-(2-cyclopentylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy3pcntanoic
acid;
5-[2,6-ditluoro-4-(2-isopropylsulfanyl-3-pyridyl)phenoxy]pentanoic
acid;
5-[2,6-difluoro-4-(2-propylsulfanyl-3-pyridyl)phcnoxy]pcntanoic acid;
5-[2,6-difluoro-4-(6~isopropylsulfanyl-2-pyridyl)phenoxy]pentanoic
acid;
5-[2,6-difluoro-4-(6-isopropoxy-2-pyridyl)phenoxy]pentanoic acid;
5-[4_[2-(cyclopropylmethoxy)-3-pyridyl]-2,6-difluoro-phenoxy]pentan
oic acid;
5~[2,6-difluoro-4-(2-tetrahydrofuraii-3-yloxy-3-pyridyl)phenoxy]pentan
oic acid;
5-[2,6-di±luoro-4-(2-tetrahydi'opyrari"4-yloxy~3-pyridyl)phenoxy]penta
noic acid;
4-[2,6-difluoro-4-(2-isopropoxy-pyridin-3-yl)-phenylsulfanyI]-pentanoi
c acid;
4-[4-(2-cycIopentylsuIfanyl"pyriditi-3-yl)-phenylsulfanyl]-pentanoic
acid;
4-{2-fluoro-4-[2-(tetrahydro-pyran-4-yloxy)-pyridin-3-yl]-phenylsulfan

yl) -butyric acid;
4-{2-fluoro-4-[2-(tetrahydrofuran-3-yloxy)-pyridin-3-yl]-phenylsulfany
1}-butyric acid;
4-[4-(2-cyclobutylmethoxy-pyridin-3-yl)-2-fluoro-phenylsulfanyl3-buty
ric acid;
4-{2,6-difluoro-4-[2-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl3-phcnylsulfa
nyl} -butyric acid;
4-[4-(2-cyclobutylmethoxy-pyridin-3-yl)-2,6-difluoro-phenylsulfanyl]-
butyric acid;
4-[4-(2-cydopentylamino-pyridin-3-yl)-2,6-difiuoro-phenylsulfanyIJ-b
utyric acid;
4-[2,6-diLluoro-4-(2-isopropylamino-pyridin-3-yl)-phenylsulfanyl|-buty
ric acid;
4-{4-[2-(cyclopropylmethyl-amino)-pyridin-3-yl]-2,6-difluoro-phenyls
ulfanyl}-butyric acid;
5-[4-(2-cyclopentyloxy-pyridin-3-yl)-2,6-difluoro-phenylsulfanyl]-pent
aiioic acid;
5-[2,6-difluoro-4-(2-isopropoxy-pyridin-3-yl)-phenyIsulfanyl]-pentanoi
c acid;
5-[4-(2-cyclopentyloxy-pyridin-3-yl)-phenylsulfanyl]-pentanoic acid;
5-[4-(2-isopropoxy-pyridin-3-yl)-phenylsulfanyl]-pentanoic acid;
5-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenylsulfanyl]-
pentanoic acid;
5-[2,6-difluoro-4-(2-propylsulfanyl-pyridin-3-yl)-phcnylsulfanyl]-penla
noic acid;
5-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-phenylsulfanyl]-pentanoic
acid;
5-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-phenylsulfanyl]-pentanoic
acid;
5-[4-(2-cyclobutylmethoxy-pyridin-3-yl)-2,6"difluoro-phenylsulfanyl]-
pentanoic acid;
5-[4-(2-cycIobutoxy-pyridin-3-yl)-2,6-ditluoro-phenylsulfanyl]-pentan
oic acid;
6-[4-(2-cyclopentyloxy-pyridin-3-yl)-2,6-difluoro-phenoxy3-hcxanoic
acid;
7-[4-(2-cycIopentyloxy-pyridin-3-yl)-2,6-difluoro-phenoxyj-heptanoic
acid;
5-[2-fluoro-4~(2-isopropoxy-pyridin-3-yl)-phenoxy]-pentanoic acid;

5-[4-(2-cyclopentylsulfanyl-pyridin-3-yl)-2-fluoro-phenoxy]-pentanoic
acid;
5-[4-(2-cyclobutylsulfanyl-pyridin-3-yl)-2-fluoro-phcnoxy]-pcntanoic
acid;
5-[4-(2-cyclopentyloxy-pyridin-3-yl)-2-fluoro-phenoxy]-pentanoic
acid;
4-[2,6-difluoro-4-(2-methoxy-pyridin-3-yl)-phenoxy]-butyric acid;
4-[4-(2-alIyloxy-pyridin-3-yI)-2,6-difluoro-phenoxy]-butyric acid;
4-[4-(2-but-2-yiiyloxy-pyridin~3-yl)-2,6-difluon>phenoxy]-butyric
acid;
6-[4-[2-(cyclobutoxy)-3-pyridyl]-2,6-difluoro-phenoxy]hexanoic acid;
6-[4-[2-(cyclobutylmethoxy)-3-pyridyl]-2,6-difiuoro-phenoxy]hexanoic
acid;
6-[4-[2-(cyclopropylmethoxy)-3-pyridyl]-2,6-difluoro-phenoxy3hexano
ic acid;
6-[4-(2-cyclobutylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy]hexanoic
acid;
6-[4-(2-cyclopentylsulfanyl-3-pyridyl)-2,6-difluoro-phenoxy]hexanoic
acid;
6-[4-(2-cyclopentyloxy-pyridin-3-yl)-2,6-difIuoro~phenylsulfanyl]-hexa
noic acid;
6-[4-(2-cycIopentylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenylsulfanyl]-
hexanoic acid;
6-[4-(2-cycIobutylsulfanyl-pyridin-3-yl)-2,6-difluoro-phenylsulfanyl]-h
exanoic acid; and
6-[2,6-difluoro-4-(2-propylsulfanyl-pyridin-3-yl)-phenylsulfanyl]-hexa
noic acid,
[Claim 3] A pharmaceutical composition as GPR120 agonists, comprising the
biaryl derivatives, pharmaceutic ally acceptable salts or isomers thereof
according to Claim 1 and a pharmaceutically acceptable carrier.
[Claim 4] A pharmaceutical composition for preventing or treating diabetes, com-
plications of diabetes, obesity, non-alcoholic fatty liver, sieatohepatitis,
osteoporosis or inflammation, comprising the biaryl derivatives, phar-maceutically acceptable salts or isomers thereof according to Claim 1
and a pharmaceutically acceptable carrier.
[Claim 5] A composition for lowering blood glucose level, comprising the biaryl
derivatives, pharmaceutically acceptable salts or isomers thereof
according to Claim 1 and a pharmaceutically acceptable carrier.

[Claim 6] A method for preparing a composition for preventing or treating
diabetes, complications of diabetes, obesity, non-alcoholic fatty liver, steatohepatitis, osteoporosis or inflammation, which comprises the step of mixing the biaryl derivatives, pharmaceutically acceptable salts or isomers thereof according to Claim 1 with a pharmaceutically ac¬ceptable carrier.

Documents

Application Documents

# Name Date
1 Form 5 [21-01-2016(online)].pdf 2016-01-21
2 Form 3 [21-01-2016(online)].pdf 2016-01-21
3 Form 18 [21-01-2016(online)].pdf 2016-01-21
4 Form 1 [21-01-2016(online)].pdf 2016-01-21
5 Description(Complete) [21-01-2016(online)].pdf 2016-01-21
6 201647002201.pdf 2016-01-24
7 ABSTRACT.pdf 2016-07-04
8 Form 3 [19-07-2016(online)].pdf 2016-07-19
9 201647002201-PA [23-08-2017(online)].pdf 2017-08-23
10 201647002201-ASSIGNMENT DOCUMENTS [23-08-2017(online)].pdf 2017-08-23
11 201647002201-8(i)-Substitution-Change Of Applicant - Form 6 [23-08-2017(online)].pdf 2017-08-23
12 Correspondence by Agent_Power of Attorney_Assignment_24-08-2017.pdf 2017-08-24
13 201647002201-RELEVANT DOCUMENTS [22-08-2018(online)].pdf 2018-08-22
14 201647002201-Changing Name-Nationality-Address For Service [22-08-2018(online)].pdf 2018-08-22
15 201647002201-FER.pdf 2018-08-29
16 201647002201-AbandonedLetter.pdf 2019-02-25
17 201647002201-Response to office action (Mandatory) [26-02-2019(online)].pdf 2019-02-26
18 correspondence by Agent_Request for reissuance of FER_11-03-2019.pdf 2019-03-11
19 201647002201-FORM 4 [05-08-2019(online)].pdf 2019-08-05
20 201647002201-RELEVANT DOCUMENTS [04-09-2019(online)].pdf 2019-09-04
21 201647002201-FORM-24 [04-09-2019(online)].pdf 2019-09-04
22 Correspondence by Agent_Review Petition on Form 24_13-09-2019.pdf 2019-09-13
23 201647002201-Correspondence to notify the Controller [27-11-2020(online)].pdf 2020-11-27
24 201647002201-Response to office action [01-08-2022(online)].pdf 2022-08-01

Search Strategy

1 201647002201Searchstrategy_10-08-2018.pdf