US 8,772,302 B2Granted

GPR 119 agonists

AssigneeCadila Healthcare Limited

InventorsHarikishore Pingali, Pandurang Zaware, Mukul Jain

Life of this patent

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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.

Claims29

Dependent claims

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.

4 more elements

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.

123 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/377,995Filed 17 Jun 2010
Priority: IN 1458/MUM/200918 Jun 2009
Published: US 2012/0122905 A117 May 2012
Granted: 8 Jul 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 411/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 3/00
Drugs for disorders of the metabolism
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics

Family

US 2012/0122905 A1Pre-grant publication · published 17 May 2012
US 8,772,302 B2This patent

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

Timeline

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Abstract

Facts

Application

13/377,995Filed 17 Jun 2010

Priority

IN 1458/MUM/200918 Jun 2009

Published

US 2012/0122905 A117 May 2012

Granted

8 Jul 2014

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 411/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 3/00
Drugs for disorders of the metabolism
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics