Granted Patent B2

US 8,802,637 · App. 14/042,408 · Granted Aug 12, 2014

Inventors: Yuanwei Chen (North Haven, CT); Huawei Cheng (Shanghai, CN); Shengbin Li (Shanghai, CN); Yuelin Wu (Shanghai, CN); Yan Feng (Shanghai, CN); Binhua Lv (Shanghai, CN); Binhua Xu (Shanghai, CN); Brian Seed (Boston, MA); Michael J. Hadd (San Diego, CA); Yanli Song (Shanghai, CN); Jiyan Du (Shanghai, CN); Congna Wang (Shanghai, CN); Jacques Y. Roberge (Shanghai, CN)

Assignee: Theracos, Inc.

Abstract

Claims (24)

1. A compound of Formula IA:

wherein

V is oxygen;

W is C 1 -C 6 alkylene;

X is oxygen;

Y is a member selected from the group consisting of C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 10 cycloalkyl and (C 1 -C 4 alkyloxy)C 1 -C 3 alkyl; and

R 1 is chloro.

2. A compound of claim 1 , wherein Y is C 3 -C 6 cycloalkyl.

3. A compound of claim 1 , selected from the group consisting of:

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(2-methoxyethoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(3-(4-(2-(allyloxy)ethoxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(prop-2-ynyloxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(1-(prop-2-ynyloxy)propan-2-yloxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(cyclopentyloxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(2,2,2-trifluoroethoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2,4-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(2-fluoroethoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-(2,2-difluoroethoxy)ethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclobutoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; and

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxypropoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol.

4. A compound represented by the formula:

5. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of any of claims 1 to 3 .

6. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and the compound of claim 4 .

7. A method of treating type 2 diabetes, said method comprising administering to a subject in need thereof a therapeutically effective amount of a compound of claim 4 or a composition of claim 6 .

Assignments (8)

Continuity (5)