US 9,540,362 B2Granted

Sphingosine-1-phosphate receptor agonists, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent

AssigneeLG Life Sciences Ltd.

InventorsSeung Yup Paek, Sung Bae Lee, Deok Seong Park, Won Hyung Lee

Life of this patent

Estimating the term…

Abstract

The present invention relates to novel compounds of Formula 1 as sphingosine-1-phosphate receptor agonists which can be effectively used for the treatment of autoimmune diseases, a method for preparing the same, and a pharmaceutical composition comprising the same as an active component. The compounds according to the present invention are effective on extensive autoimmune diseases and chronic inflammatory diseases including relapsing-remitting multiple sclerosis, and can also be used for treating or preventing immunoregulation disorders.

Claims12

Dependent claims

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

wherein
X represents C or N,
R1 represents optionally substituted alkyl,
wherein the optional substituent of the optionally substituted alkyl is one or more selected from halo(gen), cyano, hydroxyl, C1-C6-alkyloxy, oxo or sulfonyl unsubstituted or substituted by alkyl,
R2 represents H, optionally substituted alkyl, halogen, CN, CF3 or COCF3,
wherein the optional substituent of the optionally substituted alkyl is one or more selected from halo(gen), cyano, hydroxyl, C1-C6-alkyloxy, oxo or sulfonyl unsubstituted or substituted by alkyl,
W represents C, N, C-alkoxy, C-halogen or C—CN,
Q represents CH2O or
and
S is selected from the following residues:
wherein
m and n represent independently 0, 1, 2 or 3,
R3-R10 represent independently H, alkyl, halogen, halogenoalkyl or alkoxyalkyl,
R11 represents H,
and
R12 represents OH, NH2,

13 more elements

A compound, or pharmaceutically acceptable salt or stereoisomer thereof, wherein the compound is selected from the group consisting of:

3-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
1-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-azetidine-3-carboxylic acid;
1-{4-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-azetidine-3-carboxylic acid;
1-{4-[5-(3-cyano-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-azetidine-3-carboxylic acid;
1-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-azetidine-3-carboxylic acid;
1-(4-{5-[1-isopropyl-3-(2,2,2-trifluoro-acetyl)-1H-indol-5-yl]-[1,2,4]oxadiazol-3-yl}-3-methyl-benzyl)-azetidine-3-carboxylic acid;
1-{4-[5-(1-isobutyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-azetidine-3-carboxylic acid;
1-{4-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-1H-pyrazole-4-carboxylic acid;
1-{4-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-1H-pyrazole-4-carboxylic acid;
3-{4-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzylamino}-propanoic acid;
{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-acetic acid;
{4-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-acetic acid;
3-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-propanoic acid;
(R)-1-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-piperidine-3-carboxylic acid;
(S)-1-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-piperidine-3-carboxylic acid;
1-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-piperidine-4-carboxylic acid;
(S)-1-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-pyrrolidine-3-carboxylic acid;
({4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-methyl-amino)-acetic acid;
3-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzylamino}-propanoic acid;
3-{3-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-2-methyl-phenyl}-propanoic acid;
1-{3-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-azetidine-3-carboxylic acid;
{3-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzylamino}-acetic acid;
({3-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-methyl-amino)-acetic acid;
(1S,3R)-3-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzylamino}-cyclopentanecarboxylic acid;
3-({4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-methyl-amino)-propanoic acid;
1-{3-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-2-methyl-benzyl}-azetidine-3-carboxylic acid;
5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid;
3-{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid;
4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-ol;
2-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-ylamino}-ethanol;
(S)-2-amino-3-hydroxy-1-{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propan-1-on;
2-{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propan-1,3-diol;
N—{(S)-4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-yl}-methanesulfonamide;
N—{(S)-4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-yl}-acetamide;
N-{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-naphthalen-1-yl}-acetamide;
N-{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-naphthalen-1-yl}-methanesulfonamide;
N-{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-naphthalen-1-yl}-sulfamide;
3-hydroxy-pyrrolidine-1-carboxylic acid {5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-naphthalen-1-yl}-amide;
5-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
7-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
3-hydroxy-azetidine-1-carboxylic acid {5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-naphthalen-1-yl}-amide;
{5-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, fluoroacetate;
2-{5-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-ethanol;
5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-naphthalen-1-ylamine, hydrochloride;
1-{4-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-yl}-azetidin-3-ol;
2-{5-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-N-(2-hydroxy-ethyl)-acetamide;
2-{7-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-ethanol;
{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-naphthalen-1-yl}-(2-methanesulfonyl-ethyl)-amine, hydrochloride;
{7-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, hydrochloride;
N-(2-hydroxy-ethyl)-2-{7-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetamide;
3-{4-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(3-cyano-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{3-methyl-4-[5-(1-methyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propanoic acid;
5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-ol;
6-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
2-{6-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-ethanol;
{6-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, hydrochloride;
{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-yloxy}-acetic acid;
2-{6-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-N-(2-hydroxy-ethyl)-acetamide;
6-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
{6-[5-(3-cyano-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, hydrochloride;
{6-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, hydrochloride;
3-{4-[5-(7-chloro-2-methyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
1-isopropyl-5-[3-(1,2,3,4-tetrahydro-isoquinolin-5-yl)-[1,2,4]oxadiazol-5-yl]-1H-indol-3-carbonitrile, hydrochloride;
3-{4-[5-(2-cyclopentyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
{5-[5-(3-cyano-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, hydrochloride;
3-{4-[5-(1-benzyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(1-cyclopentyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(7-cyano-2-methyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(7-cyano-2-cyclopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(7-cyano-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(7-cyano-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(7-cyano-1-methyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{5-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, hydrochloride;
3-{6-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, hydrochloride;
3-{6-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, hydrochloride;
3-{4-[5-(7-methoxy-2-methyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(7-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
3-{4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
{5-[5-(1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,3-dihydro-isoindol-2-yl}-acetic acid;
3-{4-[5-(2-isopropyl-2H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
{5-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid;
3-{5-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid;
{6-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, trifluoroacetate;
3-{6-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, trifluoroacetate;
{5-[5-(2-isopropyl-2H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, trifluoroacetate;
3-{5-[5-(2-isopropyl-2H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, trifluoroacetate;
6-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
5-[5-(2-isopropyl-2H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
6-[5-(2-isopropyl-2H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
6-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
{6-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, trifluoroacetate;
3-{6-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, trifluoroacetate;
{6-[5-(1-isopropyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid;
5-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
{6-[5-(2-isopropyl-2H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, trifluoroacetate;
3-{6-[5-(2-isopropyl-2H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, trifluoroacetate;
{5-[5-(1-isopropyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid;
({4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-methyl-amino)-acetic acid, trifluoroacetate;
5-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-1,2,3,4-tetrahydro-isoquinoline, hydrochloride;
{5-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, trifluoroacetate;
3-{5-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, trifluoroacetate;
{5-[5-(1-isopropyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid;
6-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinoline-2-sulfonic acid amide;
{6-[5-(1-isopropyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid;
1-{4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-azetidine-3-carboxylic acid;
5-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinoline-2-sulfonic acid amide;
{6-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, trifluoroacetate;
({4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-indan-1-yl}-methyl-amino)-acetic acid;
3-{6-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, trifluoroacetate;
(R)-2-{4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzylamino}-propanoic acid;
{4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzylamino}-acetic acid, trifluoroacetate;
(ethyl-{4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-amino)-acetic acid, trifluoroacetate;
(R)-2-({4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-benzyl}-methyl-amino)-propanoic acid;
({4-[5-(1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-methyl-amino)-acetic acid, trifluoroacetate;
{6-[5-(1-isopropyl-3-methyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid, trifluoroacetate;
({3-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-methyl-amino)-acetic acid, trifluoroacetate;
3-({3-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-methyl-amino)-propanoic acid, trifluoroacetate;
({3-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-2-methyl-benzyl}-methyl-amino)-acetic acid, trifluoroacetate;
3-{3-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-2-methyl-benzylamino}-propanoic acid, trifluoroacetate;
3-({3-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-2-methyl-benzyl}-methyl-amino)-propanoic acid, trifluoroacetate;
3-{4-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-propanoic acid;
({3-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-2-methyl-benzyl}-methyl-amino)-acetic acid, trifluoroacetate;
1-{3-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-2-methyl-benzyl}-azetidine-3-carboxylic acid;
[(2-{3-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl)-methyl-amino]-acetic acid, trifluoroacetate;
1-(2-{3-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl)-piperidine-4-carboxylic acid;
3-{6-[5-(3-cyclopropyl-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl}-propanoic acid, trifluoroacetate;
3-{4-[5-(3-chloro-1-isopropyl-1H-indazol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-butyric acid, trifluoroacetate;
3-{4-[5-(3-chloro-1-isopropyl-1H-indol-5-yl)-[1,2,4]oxadiazol-3-yl]-3-methyl-phenyl}-butyric acid, trifluoroacetate;
1-[4-(1-isopropyl-1H-indol-5-ylmethoxy)-benzyl]-azetidine-3-carboxylic acid;
3-[4-(1-isopropyl-1H-indol-5-ylmethoxy)-phenyl]-propanoic acid;
1-[4-(3-chloro-1-isopropyl-1H-indol-5-ylmethoxy)-3-methyl-benzyl]-azetidine-3-carboxylic acid;
[5-(1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid, trifluoroacetate;
[6-(1-isopropyl-1H-indazol-5-ylmethoxy)-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid, trifluoroacetate;
[6-(2-isopropyl-2H-indazol-5-ylmethoxy)-5-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid, trifluoroacetate;
[5-(2-isopropyl-2H-indazol-5-ylmethoxy)-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid, trifluoroacetate;
3-[4-(3-chloro-1-isopropyl-1H-indol-5-ylmethoxy)-2-fluoro-phenyl]-propanoic acid;
3-[5-(1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-1H-isoquinolin-2-yl]-propanoic acid, trifluoroacetate;
3-[6-(3-chloro-1-isopropyl-1H-indol-5-ylmethoxy)-naphthalen-2-yl]-propanoic acid;
1-[6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-naphthalen-2-ylmethyl]-azetidine-3-carboxylic acid;
{[6-(3-chloro-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-5-ylmethoxy)-naphthalen-2-ylmethyl]-methyl-amino}-acetic acid;
{[6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-naphthalen-2-ylmethyl]-methyl-amino}-acetic acid;
{[6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-1-methyl-3,4-dihydro-naphthalen-2-ylmethyl]-methyl-amino}-acetic acid;
1-[6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-1-methyl-3,4-dihydro-naphthalen-2-ylmethyl]-azetidine-3-carboxylic acid;
1-[6-(3-chloro-1-isopropyl-1H-pyrazolo[3,4-b]pyridin-5-ylmethoxy)-naphthalen-2-ylmethyl]-azetidine-3-carboxylic acid;
1-[6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-1-methyl-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid;
1-[6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-1-methyl-3,4-dihydro-naphthalen-2-ylmethyl]-azepane-4-carboxylic acid;
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-pyrrolidine-3-carboxylic acid;
(R)-1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-pyrrolidine-3-carboxylic acid;
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-3-methyl-pyrrolidine-3-carboxylic acid;
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid;
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-4-fluoro-piperidine-4-carboxylic acid;
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-3-carboxylic acid;
(S)-1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-3-carboxylic acid;
(R)-1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-3-carboxylic acid;
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-3-fluoro-piperidine-3-carboxylic acid;
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-pyrazolo[3,4-b]pyridin-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid;
1-[6-(1-sec-butyl-3-chloro-1H-pyrazolo[3,4-b]pyridin-5-ylmethoxy)-1-chloro-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid;
and
1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-3-fluoro-pyrrolidine-3-carboxylic acid.

158 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/764,116Filed 19 Feb 2014
Priority: KR 10-2013-001829320 Feb 2013
Published: US 2015/0376173 A131 Dec 2015
Granted: 10 Jan 2017
Term ends: Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…

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US 2015/0376173 A1Pre-grant publication · published 31 Dec 2015
US 9,540,362 B2This patent

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Abstract

Facts

Application

14/764,116Filed 19 Feb 2014

Priority

KR 10-2013-001829320 Feb 2013

Published

US 2015/0376173 A131 Dec 2015

Granted

10 Jan 2017

Term ends

Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…