# US 8,772,302 B2 · GPR 119 agonists

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- Number: US 8,772,302 B2
- Document ID: US8772302B2
- Status: Granted
- Kind: B2
- Application number: 13/377,995
- Filed: 2010-06-17
- Published: 2012-05-17
- Granted: 2014-07-08
- Earliest claimed: 2009-06-18
- Assignees: Cadila Healthcare Limited
- Applicants: Harikishore Pingali; Pandurang Zaware; Mukul Jain
- Inventors: Harikishore Pingali; Pandurang Zaware; Mukul Jain
- Web page: https://patentgrep.com/patent/US8772302B2

## CPC

- C07D 411/12: linked by a chain containing hetero atoms as chain links
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 411/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel GPR 119 agonists of the general Formula (I), their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, stereoisomers, and polymorphs. The invention also relates to processes for the preparation of the compounds of the invention, pharmaceutical compositions containing the compounds and to methods for treating one or both of diabetes and obesity using the compounds of the invention. The present invention is directed to G-protein coupled receptor (GPCR) agonists that are useful for the treatment of obesity, diabetes and related metabolic disorders.

## Claims

### Claim 1

A compound having the structure of Formula (I),
or its pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, stereoisomers, wherein
R1 represents optionally substituted groups selected from linear or branched (C1-C6)alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl or the groups C(O)OR3, C(O)R3, and SO2R3, wherein R3 represents H, or optionally substituted groups selected from linear or branched (C1-C6)alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups;
‘Z’ when present represents an optionally substituted single or fused group selected from aryl, heteroaryl, heterocyclyl, cycloalkyl groups; ‘Y’ represents either a bond or groups selected from oxygen, —NH, S, SO, SO2 or NR4, wherein R4 represents, linear or branched (C1-C6)alkyl; ‘X’ and ‘W’ may be same or different & independently represents C or N; ‘m’ ‘n’ and ‘p’ independently represents an integer ranging from 0 to 4; and R2 may be optionally present and when present represents an oxo group.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent and all other symbols are as defined in claim 1.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein ‘Z’ represents optionally substituted single or fused group selected from aryl, heteroaryl, heterocyclyl, cycloalkyl groups and all other symbols are as defined in claim 1.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein ‘Y’ represents a bond and all other symbols are as defined in claim 1.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein ‘Y’ is selected from oxygen, —NH, S, SO, SO2 or NR4, wherein R4 represents, linear or branched (C1-C6)alkyl groups and all other symbols are as defined in claim 1.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, ‘Y’ represents a bond and all other symbols are as defined in claim 1.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, Y′ is selected from oxygen, —NH, S, SO, SO2 or NR4 wherein R4 represents, linear or branched (C1-C6)alkyl groups and all other symbols are as defined in claim 1.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R1 represents optionally substituted groups selected from linear or branched (C1-C6)alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein R1 represents the groups C(O)OR3, C(O)R3, and SO2R3 wherein R3 represents optionally substituted groups selected from H, linear or branched (C1-C6)alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, R1 represents optionally substituted groups selected from linear or branched (C1-C6)alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, R1 represents the groups C(O)OR3, C(O)R3, and SO2R3 wherein R3 represents optionally substituted groups selected from H, linear or branched (C1-C6)alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 12 (depends on 1)

The compound according to claim 1, wherein ‘Z’ represents optionally substituted single or fused group selected from aryl, heteroaryl, heterocyclyl, cycloalkyl groups, and R1 represents optionally substituted groups selected from linear or branched (C1-C6)alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 13 (depends on 1)

The compound according to claim 1, wherein ‘Z’ represents optionally substituted single or fused group selected from aryl, heteroaryl, heterocyclyl, cycloalkyl groups and R1 represents the groups C(O)OR3, C(O)R3, and SO2R3 wherein R3 represents H, optionally substituted groups selected from linear or branched (C1-C6)alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 14 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, ‘Y’ is a bond and R1 represents optionally substituted groups selected from linear or branched (C1-C6)alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 15 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, ‘Y’ is a bond and R1 represents the groups C(O)OR3, C(O)R3, and SO2R3 wherein R3 represents optionally substituted groups selected from H, linear or branched (C1-C6)alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 16 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, ‘Y’ is selected from oxygen, —NH, S, SO, SO2 or NR4 wherein R4 represents, linear or branched (C1-C6)alkyl groups and R1 represents optionally substituted groups selected from linear or branched (C1-C6)alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 17 (depends on 1)

The compound according to claim 1, wherein ‘Z’ is absent, ‘Y’ is selected from oxygen, —NH, S, SO, SO2 or NR4, wherein R4 represents, linear or branched (C1-C6)alkyl groups and R1 represents the groups C(O)OR3, C(O)R3, and SO2R3 wherein R3 represents H, optionally substituted groups selected from linear or branched (C1-C6)alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 18 (depends on 1)

The compound according to claim 1, wherein ‘Y’ is a bond and R1 represents the groups C(O)OR3, C(O)R3, and SO2R3 wherein R3 represents optionally substituted groups selected from H, linear or branched (C1-C6)alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 19 (depends on 1)

The compound according to claim 1, wherein ‘Y’ is selected from oxygen, —NH, S, SO, SO2 or NR4, wherein R4 represents, linear or branched (C1-C6)alkyl groups and R1 represents optionally substituted groups selected from linear or branched (C1-C6)alkyl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroaralkyl groups and all other symbols are as defined in claim 1.

### Claim 20 (depends on 1)

The compound of Formula (I) according to claim 1, wherein ‘Z’ represents a heteroaryl group.

### Claim 21 (depends on 1)

The compound of Formula (I) according to claim 1, wherein ‘Y’ represents either a bond or oxygen atom.

### Claim 22 (depends on 1)

The compound of Formula (I) according to claim 1, wherein R1 represents a heteroaryl group or the group C(O)OR3.

### Claim 23 (depends on 1)

The compound of Formula (I) according to claim 1, wherein R3 is selected from H, linear or branched (C1-C6)alkyl, aryl, aralkyl group.

### Claim 24 (depends on 1)

The compound of Formula (I) according to claim 1, wherein the substituents on ‘Z’ or ‘R1’ are independently selected from hydroxyl, oxo, halo, thio, nitro, amino, cyano, formyl, or substituted or unsubstituted groups selected from amidino, alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, alkoxy, alkenoxy, cycloalkoxy, aryl, aryloxy, aralkyl, aralkoxy, heterocylyl, heteroaryl, heterocyclylalkyl, heteroaralkyl, heteroaryloxy, heteroaralkoxy, heterocyclyloxy, heterocyclylalkoxy, heterocyclylalkoxyacyl, acyl, acyloxy, acylamino, monosubstituted or disubstituted amino, arylamino, aralkylamino, carboxylic acid and its derivatives such as esters and amides, carbonylamino, hydroxyalkyl, aminoalkyl, alkoxyalkyl, aryloxyalkyl, aralkoxyalkyl, alkylthio, thioalkyl, arylthio, alkylsulfonylamino, alkylsulfonyloxy, alkoxycarbonylamino, aryloxycarbonylamino, aralkyloxycarbonylamino, aminocarbonylamino, alkylaminocarbonylamino, alkoxyamino, hydroxylamino, sulfenyl derivatives, sulfonyl derivatives, sulfonic acid and its derivatives, wherein each of these groups may independently be present one or more times either on ‘Z’ or ‘R1’.

### Claim 25 (depends on 1)

The compound of Formula (I) according to claim 1, wherein the substituents on ‘Z’ or ‘R1’ are independently selected from halo, thio, nitro, amino, cyano, or substituted or unsubstituted groups selected from alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, aralkyl, sulfenyl derivatives, sulfonyl derivatives, sulfonic acid and its derivatives, wherein each of these groups may independently be present one or more times either on ‘Z’ or ‘R1’.

### Claim 26

A compound selected from the group consisting of:
cis-5-(4-((6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(4-((5-methyl-6-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)pyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans 5-(4-((5-methyl-6-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)pyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(4-((2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(4-((6-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(4-((6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(4-((2-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((2-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-tert-butyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-tert-butyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-tert-butyl 4-(4-((4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)methyl)thiazol-2-yl)piperidine-1-carboxylate;
trans-tert-butyl 4-(4-((4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)methyl)thiazol-2-yl)piperidine-1-carboxylate;
trans-tert-butyl 4-(2-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)ethoxy)piperidine-1-carboxylate;
cis-tert-butyl 4-(3-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)propyl)piperidine-1-carboxylate;
trans-tert-butyl 4-(3-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)propyl)piperidine-1-carboxylate;
cis-5-(4-(3-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)propoxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-(3-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)propoxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-tert-butyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-tert-butyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
tert-butyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathiolan-4-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-isobutyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-isobutyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(4-((6-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
cis-ethyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-ethyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-benzyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-benzyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-5-(4-((6-((1-benzylpiperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-((1-benzylpiperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2-oxide;
cis-ethyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-ethyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-5-(4-((5-methyl-6-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)pyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((5-methyl-6-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)pyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
cis-isobutyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-isobutyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-N-(2,4-dichlorophenyl)-4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxamide;
trans-N-(2,4-dichlorophenyl)-4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxamide;
cis-isopropyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-isopropyl 4-((5-methyl-6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-isopropyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-isopropyl 4-((5-methyl-6-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-tert-butyl 4-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)piperidine-1-carboxylate;
trans-tert-butyl 4-(4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)piperidine-1-carboxylate;
cis-5-(4-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
cis-tert-butyl 4-(4-((4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)methyl)thiazol-2-yl)piperidine-1-carboxylate;
trans-tert-butyl 4-(4-((4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)methyl)thiazol-2-yl)piperidine-1-carboxylate;
cis-tert-butyl 4-(2-methoxy-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)piperidine-1-carboxylate;
trans-tert-butyl 4-(2-methoxy-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)piperidine-1-carboxylate;
cis-5-(4-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
cis-5-(3-chloro-4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(3-chloro-4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2-oxide;
cis-tart-butyl 4-((6-(2-chloro-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-tert-butyl 4-((6-(2-chloro-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-isobutyl 4-((6-(2-chloro-4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-isobutyl 4-((6-(2-chloro-4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-isobutyl 4-((6-(2-chloro-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-isobutyl 4-((6-(2-chloro-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-isobutyl 4-((6-(2-methoxy-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-isobutyl 4-((6-(2-methoxy-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-tert-butyl 4-((6-(2-methoxy-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-tert-butyl 4-((6-(2-methoxy-4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)-3-methoxybenzyl)-1,3,2-dioxathiane 2-oxide;
trans-5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)-3-methoxybenzyl)-1,3,2-dioxathiane 2-oxide;
cis-tert-butyl 4-((5-methyl-6-((6-((2-oxido-1,3,2-dioxathian-5-yl)methyl)pyridin-3-yl)oxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-tert-butyl 4-((5-methyl-6-((6-((2-oxido-1,3,2-dioxathian-5-yl)methyl)pyridin-3-yl)oxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-tert-butyl 4-((6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
trans-tert-butyl 4-((6-(4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
cis-tert-butyl 4-(4-((4-(2-oxido-1,3,2-dioxathian-5-yl)phenoxy)methyl)phenoxy)piperidine-1-carboxylate;
cis-tert-butyl 4-(4-((4-((2-oxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)methyl)phenoxy)piperidine-1-carboxylate;
isobutyl 4-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
isobutyl 4-((6-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
5-(4-((6-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-((6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-((5-methyl-6-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)pyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-((6-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-((2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-((6-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-((2-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
tert-butyl 4-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
tert-butyl 4-(2-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)ethoxy)piperidine-1-carboxylate;
tert-butyl 4-(3-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)propyl)piperidine-1-carboxylate;
5-(4-(2-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)ethoxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-(2-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)ethoxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(4-(2-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)ethoxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
tert-butyl 4-((6-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
tert-butyl 4-((6-(4-(2,2-dioxido-1,3,2-dioxathiolan-4-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2,2-dioxide;
ethyl 4-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
benzyl 4-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
5-(4-((6-((1-benzylpiperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide;
ethyl 4-((6-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
5-(4-((5-methyl-6-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)pyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2,2-dioxide;
N-(2,4-dichlorophenyl)-4-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxamide;
isopropyl 4-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
isopropyl 4-((6-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
tert-butyl 4-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)piperidine-1-carboxylate;
5-(4-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2,2-dioxide;
tert-butyl 4-(4-((4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)methyl)thiazol-2-yl)piperidine-1-carboxylate;
5-(4-((1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2,2-dioxide;
5-(3-chloro-4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)benzyl)-1,3,2-dioxathiane 2,2-dioxide;
tert-butyl 4-((6-(2-chloro-4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
isobutyl 4-((6-(2-chloro-4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
isobutyl 4-((6-(2-chloro-4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
isobutyl 4-((6-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)-2-methoxyphenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
tert-butyl 4-((6-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)-2-methoxyphenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
5-(4-((6-((1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-5-methylpyrimidin-4-yl)oxy)-3-methoxybenzyl)-1,3,2-dioxathiane 2,2-dioxide;
tert-butyl 4-((6-((6-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)pyridin-3-yl)oxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
tert-butyl 4-((6-(4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)pyrimidin-4-yl)oxy)piperidine-1-carboxylate;
tert-butyl 4-(4-((4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)phenoxy)methyl)phenoxy)piperidine-1-carboxylate;
tert-butyl 4-(4-((4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)methyl)phenoxy)piperidine-1-carboxylate;
tert-butyl 4-(4-((2,2-dioxido-1,3,2-dioxathian-5-yl)methyl)-2-methoxyphenoxy)piperidine-1-carboxylate;
tert-butyl 4-(4-((4-(2,2-dioxido-1,3,2-dioxathian-5-yl)phenoxy)methyl)thiazol-2-yl)piperidine-1-carboxylate;
tert-butyl 4-((6-(4-((2,2-dioxido-1,3,2-dioxathiolan-4-yl)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate;
5-(4-(3-(1-(pyrimidin-2-yl)piperidin-4-yl)propoxy)phenyl)-1,3,2-dioxathiane 2,2-dioxide.

### Claim 27 (depends on 1)

A pharmaceutical composition comprising a compound of Formula (I) as defined in claim 1 and optionally one or more pharmaceutically acceptable carriers, excipients or diluents.

### Claim 28 (depends on 1)

A method for treating diabetes, comprising the step of providing the compound of formula (I) as defined in claim 1 or its suitable pharmaceutical compositions to a patient in need of such treatment.

### Claim 29 (depends on 1)

A process for preparing compounds of Formula (I) as defined in claim 1, the process comprising the steps of:
i) reacting a compound of Formula (V) with thionyl chloride in one or more suitable solvents to obtain compounds of Formula (Ia), wherein each of the terms are as defined in claim 1
ii) and converting the compound of Formula (Ia) to compounds of Formula (I) by oxidizing with suitable oxidizing agents, wherein all the terms are as defined in claim 1