0001] This application claims priority to Indian Provisional Application Number

201611012426, filed on April 8, 2016, which is hereby incorporated by reference in its entireties.

Field of Invention

[0002] The present invention relates to novel compounds that are useful in the treatment and prevention of metabolic disorders, including diabetes mellitus (type I and type II), and related disorders and also includes methods for making, pharmaceutical compositions containing, and therapeutic uses for such compounds.

Background of the Invention

[0003] Diabetes is a life-style related disease derived from multiple causative factors. It is characterized by elevated levels of plasma glucose (hyperglycemia) in the fasting state or after administration of glucose during an oral glucose tolerance test. There are two generally recognized forms of diabetes: type 1 and type 2 diabetes mellitus. In type 1 diabetes, or insulin-dependent diabetes mellitus (IDDM), patients produce little or no insulin, the hormone which regulates glucose utilization. In type 2 diabetes, or noninsulin-dependent diabetes mellitus (T2DM), insulin is still produced in the body, and patients demonstrate resistance to the effects of insulin in stimulating glucose and lipid metabolism in the main insulin-sensitive tissues, namely, muscle, liver and adipose tissue. These patients often have normal levels of insulin, and may have hyperinsulinemia (elevated plasma insulin levels), as they compensate for the reduced effectiveness of insulin by secreting increased amounts of insulin.

[0004] The treatment of T2DM generally begins weight loss, healthy diet and exercise program. Although these factors are important especially to dissolve the increased risk of cardiovascular disorders related to diabetes mellitus, they are not effective generally for the control of diabetes mellitus itself. There are many drugs useful for the treatment of diabetes mellitus, including insulin, metformin, sulfonylureas, acarbose, thiazolidinedione, GLP-1 analogue and DPP IV inhibitor. There are, however deficiencies associated with currently

available treatment, including hypoglycemic episodes, weight gain, loss in responsiveness to therapy over time, gastrointestinal problems, and edema.

[0005] Although a number of receptor classes exist in humans, by far the most abundant and therapeutically relevant is represented by the G protein-coupled receptor (GPCR) class, it is estimated that approximately 4% of the protein-coding genome encodes GPCRs. GPCRs are also known as seven-transmembrane domain receptors as they share a common structural motif, having seven sequences of between 22 to 24 hydrophobic amino acids that form seven alpha helices, each of which spans the membrane. Further, there has been renewed focus on pancreatic islet-based insulin secretion that is controlled by glucose-dependent insulin secretion (GDIS). In this regard, several orphan G-protein coupled receptors (GPCR's) have recently been identified that are preferentially expressed in the β-cell and are implicated in GDIS.

[0006] GPR119 is a cell-surface GPCR that is highly expressed in human (and rodent) islets as well as in insulin-secreting cell lines. Activation of GPR119 has been demonstrated to stimulate intracellular cAMP and lead to glucose dependent GLP-1 and insulin secretion (T.Soga et al Biochem. Biophys. Res.Commun. 2005,326). Synthetic GPR119 agonists augment the release of insulin from isolated static mouse islets only under conditions of elevated glucose, and improve glucose tolerance in diabetic mice and diet-induced obese (DIO) C57/B6 mice without causing hypoglycemia.

[0007] There still remains a need for alternative novel synthetic compounds which acts as

GPR119 agonists and are useful in the treatment and prevention of metabolic disorders, including diabetes mellitus (type I and type II), and related disorders.

Object of the Invention

[0008] An object of the present invention is to provide novel compounds which acts as

GPR119 agonist, composition containing such compounds and process for the preparation thereof.

Summary of the Invention

[0009] In one aspect, the present invention provides compounds of formula (I):

[0010] wherein,

[0011] Xi, X2, X3, X4 and X5 are each indepedently N, O, S or CH; and

[0012] X4 and X5 may optionally combine to form a five membered ring comprising one or more of heteroatoms each independently selected from N, O and S and the additional five membered ring may be further optionally substituted with one or more of group selected from F, CI, Br, I, CF3and Ci-6 alkyl;

[0013] Riand R2 is independently selected from the group comprising -H, -O, Ci-6 alkyl,

Ci-6alkoxy, -(CH2)n, amino, -CO, -CO H, - H(Alkyl), -N(Alkyl)2, - H-aralkyl, -CH20, -OCH(CH3), halogenCOOR3, -CO R3R4, R3COR4;

[0014] R3 and R4 is independently selected from the group comprising hydrogen, or Ci-6 straight chain or branched chain alkyl which may be further substituted with halogen or Ci-6 alkyl,;

[0015] n is 0, 1, 2 or 3.

[0016] A is selected from

[0017] B is be selected from

and pharmaceutically acceptable salts, hydrates and stereoisomers thereof.

[0018] In one embodiment, there are provided compounds having the formula (II):

[0019] Individually comtemplated are compounds wherein A is

Individually contemplated are compounds wherein A is

Individually contemplated are compounds wherein A is

[0022] Also individually contemplated are compounds wherein A is

^Κ>

[0023] In a variant, the invention provides compounds having significant dose dependent glucose reduction at both 3mpk and lOmpk in oral glucose tolerance test in rat model.

[0024] In another variant, the invention provides compounds showing significant dose dependent glucose reduction at both 3mpk and lOmpk in oral glucose tolerance test in mice.

[0025] In another cariant, the invention provides compounds showing active GLP-1 secretion greater than -lfold with respect to the vehicle.

[0026] In another aspect, the invention provides a method of treating diabetes comprising administering compounds of all embodiments and variants of the invention.

Detailed description of the Invention

[0027] A. Compounds of the present invention

[0028] The term "alkyl" refers to a linear or branched saturated monovalent hydrocarbon, wherein the alkylene may optionally be substituted as described herein. The term "alkyl" also encompasses both linear and branched alkyl, unless otherwise specified. In certain embodiments, the alkyl is a linear saturated monovalent hydrocarbon that has the specified number of carbon atoms, or branched saturated monovalent hydrocarbon of specified number of carbon atoms. As used herein, linear CI- C6 and branched C3- C6 alkyl groups are also referred as "lower alkyl. "Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl (including all isomeric forms), ^-propyl, isopropyl, butyl (including all isomeric forms), «-butyl, isobutyl, sec-butyl,t-buty\, pentyl (including all isomeric forms), and hexyl (including all isomeric forms). For example, CI - C6 alkyl refers to a linear saturated monovalent hydrocarbon of 1 to 6 carbon atoms or a branched saturated monovalent hydrocarbon of 3 to 6 carbon atoms.

[0029] The term "alkoxy" refers to the group R'O— wherein R' is alkyl. The term "lower alkoxy" refers to alkoxy groups having from 1 to 3 carbon atoms; examples include methoxy, ethoxy, isopropoxy, and the like.

[0030] The term "aralkyl" or "aryl-alkyl" refers to a monovalent alkyl group substituted with aryl. In certain embodiments, the alkyl and aryl moieties are optionally substituted as described herein.

[0031] The term "halogen", "halide" or "halo" refers to fluorine, chlorine, bromine, and iodine.

[0032] The term "heteroatom" as used herein means an atom of any element other than carbon or hydrogen. Preferred heteroatoms are nitrogen, oxygen, sulfur, phosphorus and selenium.

[0033] The term "optionally substituted" is intended to mean that a group, such as an alkyl, alkylene, alkenyl, alkenylene, alkynyl, alkynylene, alkoxy, alkylamino, dialkylamino, carboxamido,cycloalkyl, cycloalkylene, aryl, arylene, heteroaryl, heteroarylene, heterocyclyl, or heterocyclylene, may be substituted with one or more substituents independently selected from,e.g., (a) CI - C6 alkyl, C2 - C6 alkenyl, C2 - C6 alkynyl, C3 - C7 cycloalkyl, C6 - C14 aryl, C7 - C15aralkyl, heteroaryl, and heterocyclyl, each optionally substituted with one or more substituents; and (b) halo, cyano (-CN), nitro (-N02),-C(O)R3 , -C(0)OR3 , -C(0) RbRC , -C( R3) R)RC , -OR3 , -OC(0)R3 , -OC(0)OR3, -OC(0) RbRC, -OC(= R3) R)RC, -OS(0)R3, -OS(0)2R3, -OS(0)NRbRC, -OS(0)2 RbRc, - RbRc,- R3C(0)Rd„ - R3C(0)ORd, -NR3 C(0) RbRC,- R3 C(= Rd) RbRC, - R3S(0)Rd, - R3S(0)2Rd, - R3S(0) RbRC, - R3S(0) RbRc, -SR3, -S(0)R3, -S(0)2R3, -S(0) RbRC, and -S(0)2 RbRC, wherein each R3, Rb, Re, and Rd is independently (i) hydrogen; (ii) CI - C6 alkyl, C2 - C6 alkenyl, C2 - C6 alkynyl, C3 - C7cycloalkyl, C6 - C14 aryl, C7 - CI 5 aralkyl, heteroaryl, or heterocyclyl, each optionally substituted with one or more substituents; or (iii) Rb and Re together with the N atom to which they are attached form heteroaryl or heterocyclyl, optionally substituted with one or more, in one embodiment, one, two, three, or four,

substituents. As used herein, all groups that may be substituted are "optionally substituted," unless otherwise specified.

[0034] The use of terms "a" and "an" and "the" and similar references in the context of describing the invention (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contraindicated by context.

[0035] The term "salt(s)", as employed herein, denotes acidic and/or basic salts formed with inorganic and/or organic acids and bases.

[0036] The term "pharmaceutically acceptable salts" refers to the acid addition salt compound formed with a suitable acid selected from an inorganic acid such as hydrochloric acid, hydrobromic acid; or an organic acid such as benzene sulfonic acid, maleic acid, oxalic acid, fumaric acid, succinic acid, p-toluenesulfonic acid and malic acid.

[0037] The term "hydrate" as used herein designates a crystalline molecular compound in which water molecules are incorporated into the crystal lattice. Generally speaking, a hydrate thus designates a crystalline form of a molecular compound, whereby the only further molecules incorporated into the crystal lattice are water molecules.

[0038] The term "stereoisomer's" refers to at least two compounds having the same molecular formula and connectivity of atoms, but having a different arrangement of atoms in a three-dimensional space. In view of the present disclosure, a stereoisomer can be, for example, an enantiomer, a diastereomer, or a meso compound.

[0039] The term "GPR119" as used herein refers to the G protein-coupled receptor that in humans is encoded by the GPR119 gene.

[0040] The present invention provides compound represented by formula (1) that act as

GPR119 agonist and is used in the treatment of diabetes, preferably type 2 diabetes mellitus. [0041] The compounds of the present invention may be illustrated but not limited to the examples as provided at Table 1.

Table 1: Illustrative compounds of present invention

isopropyl- 1 ,2,4-oxadiazole

yl)imidazo[2,l- N-O

met y enzenesu onam e

y p per n- -am ne

[0042] The present invention also provides for compounds of formula (1) as below: i. 3,4-bis(4-(lH-tetrazol- 1 -yl)phenoxy)- 1 ,2,5-thiadiazole

ii. 3,4-bis((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-l,2,5-thiadiazole iii. 5-(l-(4-(4-(lH-tetrazol-l-yl)phenoxy)-l,2,5-thiadiazol-3-yl)piperidin-4-yl)-3-isopropyl- 1,2,4-oxadiazole

iv. 3-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-4-(4-(methylsulfonyl)phenyl)-l,2,5- thiadiazole

v. 3-(4-(lH-tetrazol-l-yl)phenoxy)-4-(l-(5-ethylpyrimidin-2-yl)-l,2,3,6-tetrahydropyridin- 4-yl)-l,2,5-thiadiazole

vi. 5-(l-(4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)-l,2,5-thiadiazol-3-yl)piperidin-4- yl)-3-isopropyl-l,2,4-oxadiazole

vii. 3-isopropyl-5-(l-(4-(4-(methylsulfonyl)phenyl)-l,2,5-thiadiazol-3-yl)piperidin-4-yl)- 1,2,4-oxadiazole

viii. (4-(l-(5-ethylpyrimidin-2-yl)-l,2,3,6-tetrahydropyridin-4-yl)-l,2,5-thiadiazol-3- yl)methanol

ix. 5-(l-(4-((4-(lH-tetrazol-l-yl)phenoxy)methyl)-l,2,5-thiadiazol-3-yl)piperidin-4-yl)-3- isopropyl-l,2,4-oxadiazole

x. i sopropyl 4-(4-(4-( 1 H-tetrazol- 1 -yl)phenoxy)- 1,2,5 -thiadiazol-3 -yl)piperazine- 1 - carboxylate

xi. 3,4-bis((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)methoxy)-l,2,5-thiadiazole xii. N-(2-fluoro-4-(methylsulfonyl)phenyl)-4-(4-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin- 1 -yl)- 1 ,2, 5-thiadiazole-3 -carboxamide

xiii. N-(3-fluoro-4-(methylsulfonyl)phenyl)-4-(4-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin- 1 -yl)- 1 ,2, 5-thiadiazole-3 -carboxamide

xiv. 4-(l-(5-ethylpyrimidin-2-yl)- 1,2,3, 6-tetrahydropyridin-4-yl)-N-(2-fluoro-4- (methylsulfonyl)phenyl)-l,2,5-thiadiazole-3-carboxamide

xv. 4-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-N-(2-fluoro-4-(methylsulfonyl)phenyl)-l,2,5- thi adi azol e-3 -carb oxami de

xvi. 3-isopropyl-5-(l-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)piperidin-4-yl)- 1 ,2,4-oxadiazole

xvii. 3-isopropyl-5-(4-(((6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)oxy)methyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

xviii. 3-isopropyl-5-(4-((6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)oxy)piperidin-l-yl)-l,2,4-oxadiazole

xix. 2-(l-benzylpiperidin-4-yl)-6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazole xx. isopropyl-4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)piperazine-l-carboxylate

xxi. isopropyl-4-((6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)amino)piperidine-l-carboxylate

xxii. isopropyl 4-(methyl(6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)amino)piperidine-l-carboxylate

xxiii. N-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-6-(4-(methylsulfonyl) phenyl)imidazo[2,l- b][l,3,4]thiadiazol-2-amine

xxiv. isopropyl-4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)piperidine- 1 -carboxylate

xxv. 4-(methyl(6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2- yl)amino)piperidine- 1 -carboxamide

xxvi . 4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)piperidine- 1 - carboxamide

xxvii. 3-isopropyl-5-(4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

xxviii . 1 -(4-(2-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-6-yl)piperidin- 1 - yl)ethanone

xxix. N-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)-N-methyl-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-amine

xxx. isopropyl-4-(2-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-6- yl)piperidine- 1 -carboxylate

xxxi. 6-(4-(methylsulfonyl)phenyl)-2-(l-(methylsulfonyl)piperidin-4-yl)imidazo[2,l- b][l,3,4]thiadiazole

xxxii. 3-isopropyl-5-(4-(2-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-6- yl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

xxxiii. N,N-dimethyl-4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)piperidine- 1 -carboxamide

xxxiv. isopropyl-4-(2-(4-(dimethylcarbamoyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-6- yl)piperidine- 1 -carboxylate

xxxv. isopropyl-4-(2-(4-((2-methoxyethyl)carbamoyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-6- yl)piperidine- 1 -carboxylate

xxxvi. 4-(2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol- 6-yl)-N,N-dimethylbenzamide

xxxvii . (4-(2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 - b][l,3,4]thiadiazol-6-yl)phenyl)(morpholino)methanone

xxxviii. 2-(l-benzylpiperidin-4-yl)-6-((4-(methylsulfonyl)phenoxy)methyl)imidazo[2,l- b][l,3,4]thiadiazole

xxxix. 4-(2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol- 6-yl)-N-(2-methoxyethyl)benzamide

xl. 3-isopropyl-5-(l-(6-((4-(methylsulfonyl)phenoxy)methyl)imidazo[2, l- b] [ 1 ,3 ,4]thiadiazol-2-yl)piperidin-4-yl)- 1 ,2,4-oxadiazole

xli. isopropyl-4-(6-((4-(methylsulfonyl)phenoxy)methyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)piperidine- 1 -carboxylate

xlii. 3-isopropyl-5-(4-((6-((4-(methylsulfonyl)phenoxy)methyl)imidazo[2, l- b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

xliii . 4-((2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 - b][l,3,4]thiadiazol-6-yl)methoxy)-N,N-dimethylbenzamide

xliv. 5-(l-(5-chloro-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)piperidin-4-yl)-3 -isopropyl- 1,2,4-oxadiazole

xlv. 3 -cyclopropyl-5-( 1 -(6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2- yl)piperidin-4-yl)- 1 ,2,4-oxadiazole

xlvi. 4-(2-(4-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-l-yl)imidazo[2, l-b][l,3,4]thiadiazol- 6-yl)benzonitrile

xlvii. 4-(2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2, l- b][l,3,4]thiadiazol-6-yl)benzonitrile

xlviii. 4-(2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2, l- b][l,3,4]thiadiazol-6-yl)-N,N-dimethylbenzamide

xlix. N,N-dimethyl-4-(2-(l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)imidazo[2,l- b][l,3,4]thiadiazol-6-yl)benzamide

1. 3-isopropyl-5-(4-(l-((6-(pyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

li. 3-isopropyl-5-(l-(6-(pyridin-4-yl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidin-4-yl)- 1,2,4-oxadiazole

Hi. 5-(l-(5-chloro-6-(pyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)piperidin-4-yl)-3- isopropyl-l,2,4-oxadiazole

liii. 4-(2-((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)methoxy)imidazo[2, l- b][l,3,4]thiadiazol-6-yl)benzonitrile

liv. 3 -isopropyl-5-(4-(((6-(pyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2- yl)oxy)methyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

lv. 3-isopropyl-5-(4-(l-((6-(6-(methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazol- 2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

lvi. 2-(l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(pyridin-4-yl)imidazo[2,l- b][l,3,4]thiadiazole

lvii. 3-isopropyl-5-(4-(l-((6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

lviii . (R)-3 -isopropyl-5-(4-( 1 -((6-(6-(methylsulfonyl)pyridin-3 -yl)imidazo[2, 1 - b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

lix. (R)-3 -isopropyl-5-(4-( 1 -((6-(pyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2- yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

lx. (R)-3-isopropyl-5 4-(l-((6-(4 methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

lxi. 5-(4-(l-((5-fluoro-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole

lxii. (R)-2-(l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxiii . 5-(4-( 1 -((5-chloro-6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2- yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole

lxiv. (S)-5-(4-(l -((6-(3 -fluoropyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2- yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole

lxv. (R)-5-(4-(l-((6-(2-fluoropyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole

lxvi. (R)-5-(4-(l-((5-fluoro-6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole

lxvii. (S)-6-(4-(methylsulfonyl)phenyl)-2-(l-(l-(5-propylpyrimidin-2-yl)piperidin-4- yl)ethoxy)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

lxviii. (S)-4-(2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2,l- b] [ 1 ,3 ,4]thiadiazol-6-yl)pyridine 1 -oxide

lxix. 2-(l-(l-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxx. 2-(l-(l-(5-isopropylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxi. (S)-5-(4-(l-((6-(2-chloropyrimidin-5-yl)imidazo[2,l-b][l,3,4]thiadiazol-2- yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole

lxxii. (S)-3-isopropyl-5-(4-(l-((6-(2-(methylsulfonyl)pyrimidin-5-yl)imidazo[2,l- b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole

lxxiii. 2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(pyridin-4- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

lxxiv. 2-(l-(l-(3-(trifluoromethyl)-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxv. 2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2- (methylsulfonyl)pyrimidin-5-yl)imidazo[2,l-b][l,3,4]thiadiazole

lxxvi. 2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(6-chloropyridin-3- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

lxxvii . 2-((R)- 1 -(1 -(3 -(tnfluoromethyl)- 1 ,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxviii. 2-((S)-l-(l-(3-(trifluoromethyl)-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxix. 2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3-fluoro-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxx. 2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(5-chloropyrazin-2- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

lxxxi. 2-((R)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(pyridin-4-yl)imidazo[2,l- b][l,3,4]thiadiazole

lxxxii. 2-((R)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(6- (methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole

lxxxiii. 2-((S)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(3-fluoropyridin-4- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

lxxxiv. 2-((S)-l-(l-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxxv. 2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(6- (trifluoromethyl)pyridin-3-yl)imidazo[2, l-b][l,3,4]thiadiazole

lxxxvi. 2-((S)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxxvii. 2-((S)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

lxxxviii. 2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(5-chloropyrazin- 2-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

lxxxix. 2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

xc. 2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2- methoxypyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazole

xci. 2-((R)-l-(l-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

xcii. 2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-(trifluoromethyl)- 4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

xciii. 2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3- (trifluoromethyl)pyridin-4-yl)imidazo[2, l-b][l,3,4]thiadiazole

xciv. 2-((S)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-methoxypyridin-4- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

xcv. 2-((S)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-methoxypyridin-4- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

xcvi. 2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3-methoxypyridin-4- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

xcvii. 4-(2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2,l- b] [ 1 ,3 ,4]thiadiazol-6-yl)- 1 -methylpyridin-2( lH)-one

xcviii. 2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3-fluoropyridin- 4-yl)imidazo[2,l-b][l,3,4]thiadiazole hydrochloride

xcix. 2-((S)-l-(l-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

c. 4-(2-((R)- 1 -( 1 -(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2, 1 - b][l,3,4]thiadiazol-6-yl)-3-fluorobenzonitrile

ci. 2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-6- (methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole

cii. isopropyl 4-(l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2- yloxy)ethyl)piperidine-l-carboxylate

ciii. 2-((R)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-6- (methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole

civ. 2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-methoxy-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

cv. 2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-methyl-6- (methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole

cvi. 2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4-(lH- tetrazol-5-yl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole hydrochloride

cvii. tert-butyl 4-(l-(6-(6-fluoro-4-(methylsulfonyl)cyclohexa-l,5-dienyl)imidazo[2,l- b][l,3,4]thiadiazol-2-yloxy)ethyl)piperidine-l-carboxylate

cviii. ethyl 4-(l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2- yloxy)ethyl)piperidine-l-carboxylate

cix. isopropyl 4-((S)-l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2,l- b][l,3,4]thiadiazol-2-yloxy)ethyl)piperidine-l-carboxylate

ex. 1 -methyl cyclopropyl 4-(l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, 1- b][l,3,4]thiadiazol-2-yloxy)ethyl)piperidine-l-carboxylate

cxi. 2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(thiazol-5- yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole

cxii. 2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-methyl-4- (methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole

cxiii. ethyl 4-((S)-l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2- yloxy)ethyl)piperidine-l-carboxylate

cxiv. 4-(3-isopropyl-l,2,4-oxadiazol-5-yl)-l-(3-(4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5- yl)piperidine

cxv. 4-(l-(3-(4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5-yloxy)ethyl)-l-(3-isopropyl-l,2,4- oxadiazol-5-yl)piperidine

cxvi. 4-(3-(4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5-yloxy)-l-(3-isopropyl-l,2,4- oxadiazol-5-yl)piperidine

cxvii . 4-((3 -(4-(methylsulfonyl)phenyl)- 1 ,2,4-thiadiazol-5-yloxy)m ethyl)- 1 -(3 -isopropyl- 1 ,2,4- oxadiazol-5-yl)piperidine

cxviii. 5-(3-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-l,2,4-thiadiazol-5- yl)-2-(methylsulfonyl)pyridine

cxix. 5-(3-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yloxy)-l,2,4-thiadiazol-5-yl)-2- (methylsulfonyl)pyridine

cxx. 5-(3-((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)methoxy)-l,2,4-thiadiazol-5- yl)-2-(methylsulfonyl)pyridine

cxxi. 5-(5-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yloxy)-l,2,4-thiadiazol-3-yl)-2- (methylsulfonyl)pyridine

cxxii. 2-(4-(3-(6-(methylsulfonyl)pyridin-3-yl)-l,2,4-thiadiazol-5-yloxy)piperidin-l-yl)-5- ethylpyrimidine

cxxiii. 2-(4-(3-(6-(methylsulfonyl)pyridin-3-yl)-l,2,4-thiadiazol-5-yloxy)piperidin-l-yl)-5- propylpyrimidine

cxxiv. N-(5-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yloxy)-l,2,4-thiadiazol-3-yl)-N- methyl-6-(methylsulfonyl)pyridin-3-amine

cxxv. 2-(4-(3-(2-fluoro-4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5-yloxy)piperidin-l-yl)-5- ethylpyrimidine

cxxvi. l-(3-isopropyl-l,2,4-oxadiazol-5-yl)-N-(3-(6-(methylsulfonyl)pyridin-3-yl)-l,2,4- thiadiazol-5-yl)piperidin-4-amine

cxxvii. l-(3-isopropyl-l,2,4-oxadiazol-5-yl)-N-methyl-N-(3-(6-(methylsulfonyl)pyridin-3-yl)- l,2,4-thiadiazol-5-yl)piperidin-4-amine

[0043] B. Synthesis of compounds of the present invention

The present invention also relates to a process of preparing the compounds of formula (I). The compounds of present invention may be prepared by the schemes as here below:

[0044] Synthetic Scheme 1 :

[0045] Wherein,

[0046] Ri and A is as defined above;

[0047] X5 is CH, N, O, S;

[0048] Rio is H, OH, halogen, Ci-6 alkyl, d-6alkoxy, -(CH2)n, amino, -CO, -CONH, H(Alkyl), -N(Alkyl)2, -NH-aralkyl, -OCH(CH3);

[0049] n is 0, 1, 2 or 3;

[0050] Rii is halogen, H

[0051] Synthetic Scheme 2:

[0052] Wherein,

[0053] Ri and A is as defined above;

[0054] X4 is CH, N, O, S;

[0055] R4 is H, OH, halogen, Ci-6 alkyl, Ci-6alkoxy, -(CH2)n, amino, -CO, -CONH, - NH(Alkyl), -N(Alkyl)2, -NH-aralkyl, -OCH(CH3);

[0056] n is 0, 1, 2 or 3;

[0057] Synthetic Scheme 3 :

Wherein,

[0058] X4 is CH, N, O, S;

[0059] R5 is H, OH, halogen, Ci-6 alkyl, Ci-6alkoxy, -(CH2)n, amino, -CO, -CONH, -

We Claim:

A compound of the formul

wherein,

Xi, X2, X3, X4 and X5 are each indepedently N, O, S or CH; and

X4 and X5 may optionally combine to form a five membered ring comprising one or more of heteroatoms each independently selected from N, O and S and the additional five membered ring may be further optionally substituted with one or more of group selected from F, CI, Br, I, CF3and Ci-6 alkyl;

Riand R2 is independently selected from the group comprising -H, -O, Ci-6 alkyl, Ci. ealkoxy, -(CH2)n, amino, -CO, -CO H, - H(Alkyl), -N(Alkyl)2, - H-aralkyl, -CH20, -OCH(CH3), halogenCOOR3, -CO R3R4, R3COR4;

R3 and R4 is independently selected from the group comprising hydrogen, or Ci-6 straight chain or branched chain alkyl which may be further substituted with halogen or Ci-6 alkyl,;

n is 0, 1, 2 or 3.

A is selected from

B is be selected from

2. The compound of claim 1 having the formula (II):

3. The compound of claim 2, wherein A is

4. The compound of claim 2, wherein A is

5. The compound of claim 2, wherein A is

6. The compound of claim 2, wherein A is

7. The compound of claim 2 having significant dose dependent glucose reduction at both 3mpk and lOmpk in oral glucose tolerance test in rat model.

8. The compound of claim 2 showing significant dose dependent glucose reduction at both 3mpk and lOmpk in oral glucose tolerance test in mice.

9. The compound of claim 2 showing active GLP-1 secretion greater than -lfold with respect to the vehicle.

10. The compound of claim 1 having the structure:

1009 5-(l-(4-((4-(lH-tetrazol- 1- yl)phenoxy)methyl)- l,2,5-thiadiazol-3- yl)piperidin-4-yl)-3 - isopropyl-1,2,4- oxadiazole

1010 i sopropyl 4-(4-(4-(lH- tetrazol-1- yl)phenoxy)- 1,2,5 - thiadiazol-3- yl)piperazine-l- carboxylate

11. The compound of claim 1 having the structure:

3 -carboxamide 1016 3-isopropyl-5-(l-(6-(4- (methylsulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)piperidin-4-yl)- 1,2,4-oxadiazole

1017 3 -i sopropyl-5 -(4-(((6-(4- (methylsulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)oxy)methyl)piperi din-l-yl)-l,2,4- oxadiazole

1018 3 -i sopropyl-5 -(4-((6-(4- (methylsulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)oxy)piperidin-l- yl)-l,2,4-oxadiazole

1019 2-(l-benzylpiperidin-4- yl)-6-(4- (methyl sulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazole

1020 isopropyl 4-(6-(4- (methylsulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)piperazine-l- carboxylate

1026 4-(6-(4- (methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)piperidine-l- carboxamide

1027 3-isopropyl-5-(4-(6-(4- (methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)piperidin-l-yl)- 1,2,4-oxadiazole

1028 l-(4-(2-(4- (methylsulfonyl)phen

yl)imidazo[2, l- - O~CM b][l,3,4]thiadiazol-6- yl)piperidin-l- yl)ethanone

1029 N-(l-(3-isopropyl-l,2,4- oxadiazol-5- yl)piperidin-4-yl)-N- methyl-6-(4- (methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- amine

The compound of claim 1 having the structure:

1038 2-(l-benzylpiperidin-4- yi)-6-((4- (methyl sulfonyl)phen

oxy)methyl)imidazo[

2, 1- b] [ 1 ,3 ,4]thiadiazole

1039 4-(2-(4-(3-isopropyl- l,2,4-oxadiazol-5- yl)piperidin-l- yl)iidazo[2,l- b][l,3,4]thiadiazol-6- yl)-N-(2- methoxyethyl)benza

mide

1040 3-isopropyl-5-(l-(6-((4- (methylsulfonyl)phen

oxy)methyl)imidazo[ 0 2, 1- b][l,3,4]thiadiazol-2- yl)piperidin-4-yl)- 1,2,4-oxadiazole

1041 isopropyl 4-(6-((4- (methylsulfonyl)phen

oxy)methyl)imidazo[

2, 1- b][l,3,4]thiadiazol-2- yl)piperidine-l- carboxylate

1042 3-isopropyl-5-(4-((6-((4- (methylsulfonyl)phen

oxy)methyl)imidazo[

2, 1- b][l,3,4]thiadiazol-2- yl)oxy)piperidin- 1 - yl)-l,2,4-oxadiazole

1043 4-((2-(4-(3-isopropyl- l,2,4-oxadiazol-5- yl)piperidin-l- yl)imidazo[2, l- b][l,3,4]thiadiazol-6- yl)methoxy)-N,N- dimethylbenzamide

1044 5-(l-(5-chloro-6-(4- 1 ci

(methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)piperidin-4-yl)-3 - isopropyl- 1,2,4- oxadiazole

1045 3-cyclopropyl-5-(l-(6-(4- (methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yl)piperidin-4-yl)- 1,2,4-oxadiazole

6-yl)benzamide The compound of claim 1 having the structure:

oxadiazole

1,2,4-oxadiazole

b][l,3,4]thiadiazole The compound of claim 1 having the structure:

b][l,3,4]thiadiazole

b][l,3,4]thiadiazole 1089 2-((S)-l-(l-(3-isopropyl- l,2,4-oxadiazol-5- yl)piperidin-4-
yl)ethoxy)-6-(2- methoxypyridin-4- yl)imidazo[2, l- b][l,3,4]thiadiazole

1090 2-((R)-l-(l-(5- chloropyrimidin-2- yl)piperidin-4- yl)ethoxy)-6-(2- fluoro-4- (methylsulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazole

1091 2-( 1 -( 1 -(3 -i sopropyl- l,2,4-oxadiazol-5- yl)piperidin-4-
yl)ethoxy)-6-(2- (trifluoromethyl)-4- (methylsulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazole

1092 2-( 1 -( 1 -(3 -i sopropyl- l,2,4-oxadiazol-5- yl)piperidin-4- yl)ethoxy)-6-(3- (trifluoromethyl)pyri din-4-yl)imidazo[2, 1 - b][l,3,4]thiadiazole

one 1097 2-((S)-l-(l-(3-isopropyl- l,2,4-oxadiazol-5- yl)piperidin-4-
yl)ethoxy)-6-(3- fluoropyridin-4- yl)imidazo[2, l- b][l,3,4]thiadiazole hydrochloride

1098 2-((S)-l-(l-(5- (trifluoromethyl)pyri midin-2-yl)piperidin- 4-yl)ethoxy)-6-(2- fluoro-4- (methylsulfonyl)phen yl)imidazo[2, l- b][l,3,4]thiadiazole

1099 4-(2-((R)-l-(l-(3- isopropyl- 1,2,4- oxadiazol-5- yl)piperidin-4- yl)ethoxy)imidazo[2, l-b][l,3,4]thiadiazol- 6-yl)-3- fluorobenzonitrile

15. The compound of claim 1 having the structure:

1106 tert-butyl 4-(l-(6-(6- fluoro-4- (methylsulfonyl)cycl O — ' N F ohexa-1,5- dienyl)imidazo[2, 1 - b][l,3,4]thiadiazol-2- yloxy)ethyl)piperidin

e-l-carboxylate

1107 ethyl 4-(l-(6-(2-fluoro-4- (methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- °>

yloxy)ethyl)piperidin

e-l-carboxylate

1108 isopropyl 4-((S)-l-(6-(2- fluoro-4- (methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yloxy)ethyl)piperidin

e-l-carboxylate

1109

1110 1 -methyl cyclopropyl 4- (l-(6-(2-fluoro-4- (methylsulfonyl)phen

yl)imidazo[2, l- b][l,3,4]thiadiazol-2- yloxy)ethyl)piperidin

e-l-carboxylate

5-yl)piperidine

ine 5 -(3 -( 1 -(3 -i sopropyl- l,2,4-oxadiazol-5- yl)piperidin-4-yloxy)- l,2,4-thiadiazol-5- yi)-2- (methylsulfonyl)pyrid ine

The compound of claim 1 having the structure:

1125 2-(4-(3-(2-fluoro-4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5- yloxy)piperidin- 1 -yl)-5-ethylpyrimidine

1126 l-(3-isopropyl-l,2,4-oxadiazol-5-yl)-N-(3-(6-(methylsulfonyl)pyridin-3- yl)-l,2,4-thiadiazol-5-yl)piperidin-4-amine

1127 l-(3-isopropyl-l,2,4-oxadiazol-5-yl)-N-methyl-N-(3-(6- (methylsulfonyl)pyridin-3-yl)-l,2,4-thiadiazol-5-yl)piperidin-4-amine

17. The compound of claim 1, which is

3,4-bis(4-(lH-tetrazol-l-yl)phenoxy)-l,2,5-thiadiazole;

3,4-bis((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)oxy)-l,2,5-thiadiazole; 5-(l-(4-(4-(lH-tetrazol-l-yl)phenoxy)-l,2,5-thiadiazol-3-yl)piperidin-4-yl)-3-isopropyl-1,2,4-oxadiazole;

3-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-4-(4-(methylsulfonyl)phenyl)-l,2,5-thiadiazole;

3-(4-(lH-tetrazol-l-yl)phenoxy)-4-(l-(5-ethylpyrimidin-2-yl)-l,2,3,6-tetrahydropyridin-4-yl)-l,2,5-thiadiazole;

5-(l-(4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)-l,2,5-thiadiazol-3-yl)piperidin-4-yl)-3-isopropyl-l,2,4-oxadiazole;

3-isopropyl-5-(l-(4-(4-(methylsulfonyl)phenyl)-l,2,5-thiadiazol-3-yl)piperidin-4-yl)-1,2,4-oxadiazole;

(4-(l-(5-ethylpyrimidin-2-yl)-l,2,3,6-tetrahydropyridin-4-yl)-l,2,5-thiadiazol-3-yl)methanol;

5-(l-(4-((4-(lH-tetrazol-l-yl)phenoxy)methyl)-l,2,5-thiadiazol-3-yl)piperidin-4-yl)-3-isopropyl-l,2,4-oxadiazole;

isopropyl 4-(4-(4-(lH-tetrazol-l-yl)phenoxy)-l,2,5-thiadiazol-3-yl)piperazine-l-carboxylate;

3,4-bis((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)methoxy)-l,2,5-thiadiazole;

N-(2-fluoro-4-(methylsulfonyl)phenyl)-4-(4-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-1 -yl)- 1 ,2, 5-thiadiazole-3 -carboxamide;

N-(3-fluoro-4-(methylsulfonyl)phenyl)-4-(4-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-1 -yl)- 1 ,2, 5-thiadiazole-3 -carboxamide;

4-(l-(5-ethylpyrimidin-2-yl)-l,2,3,6-tetrahydropyridin-4-yl)-N-(2-fluoro-4-(methylsulfonyl)phenyl)-l,2,5-thiadiazole-3-carboxamide;

4-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-N-(2-fluoro-4-(methylsulfonyl)phenyl)-l,2,5-thiadiazole-3-carboxamide;

3-isopropyl-5-(l-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidin-4-yl)- 1 ,2,4-oxadiazole;

3-isopropyl-5-(4-(((6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)oxy)methyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

3- isopropyl-5-(4-((6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)oxy)piperidin-l-yl)-l,2,4-oxadiazole;

2-(l-benzylpiperidin-4-yl)-6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazole.

18. The compound of claim 1, which is

isopropyl-4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperazine-l-carboxylate;

isopropyl-4-((6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)amino)piperidine-l-carboxylate;

isopropyl 4-(methyl(6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)amino)piperidine-l-carboxylate;

N-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-6-(4-(methylsulfonyl) phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-amine;

isopropyl-4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidine- 1 -carboxylate;

4- (methyl(6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)amino)piperidine- 1 -carboxamide;

4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)piperidine- 1 -carboxamide;

3-isopropyl-5-(4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

1 -(4-(2-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-6-yl)piperidin- 1 -yl)ethanone;

N-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)-N-methyl-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-amine;

isopropyl-4-(2-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-6-yl)piperidine- 1 -carboxylate;

6-(4-(methylsulfonyl)phenyl)-2-(l-(methylsulfonyl)piperidin-4-yl)imidazo[2,l-b][l,3,4]thiadiazole;

3- isopropyl-5-(4-(2-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-6-yl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

N,N-dimethyl-4-(6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidine- 1 -carboxamide;

isopropyl-4-(2-(4-(dimethylcarbamoyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-6-yl)piperidine- 1 -carboxylate;

isopropyl-4-(2-(4-((2-methoxyethyl)carbamoyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-6-yl)piperidine- 1 -carboxylate;

4- (2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-6-yl)-N,N-dimethylbenzamide;

(4-(2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 -b][l,3,4]thiadiazol-6-yl)phenyl)(morpholino)methanone;

2-(l-benzylpiperidin-4-yl)-6-((4-(methylsulfonyl)phenoxy)methyl)imidazo[2,l-b][l,3,4]thiadiazole;

4-(2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-6-yl)-N-(2-methoxyethyl)benzamide.

19. The compound of claim 1, which is

3-isopropyl-5-(l-(6-((4(methylsulfonyl)phenoxy)methyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)piperidin-4-yl)-l,2,4-oxadiazole;

isopropyl-4-(6-((4-(methylsulfonyl)phenoxy)methyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidine- 1 -carboxylate;

3- isopropyl-5-(4-((6-((4-(methylsulfonyl)phenoxy)methyl)imidazo[2, l-b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

4- ((2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 -b][l,3,4]thiadiazol-6-yl)methoxy)-N,N-dimethylbenzamide;

5- (l-(5-chloro-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidin-4-yl)-3 -isopropyl- 1,2,4-oxadiazole;

3 -cyclopropyl-5-( 1 -(6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)piperidin-4-yl)- 1 ,2,4-oxadiazole;

4-(2-(4-(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin- 1 -yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-6-yl)benzonitrile;

4-(2-( 1 -( 1 -(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2, 1 -b][l,3,4]thiadiazol-6-yl)benzonitrile;

4- (2-( 1 -( 1 -(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2, 1 -b][l,3,4]thiadiazol-6-yl)-N,N-dimethylbenzamide;

N,N-dimethyl-4-(2-(l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)imidazo[2,l-b][l,3,4]thiadiazol-6-yl)benzamide;

3-isopropyl-5-(4-(l-((6-(pyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

3- isopropyl-5-(l-(6-(pyridin-4-yl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)piperidin-4-yl)-1,2,4-oxadiazole;

5- (l-(5-chloro-6-(pyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)piperidin-4-yl)-3-isopropyl-l,2,4-oxadiazole;

4- (2-((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)methoxy)imidazo[2, l-b][l,3,4]thiadiazol-6-yl)benzonitrile;

3 -isopropyl-5-(4-(((6-(pyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)methyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

3-isopropyl-5-(4-(l-((6-(6-(methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

2-(l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(pyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazole;

3 -isopropyl-5-(4-( 1 -((6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

(R)-3-isopropyl-5-(4-(l-((6-(6-(methylsulfonyl)pyridin-3-yl)imidazo[2,l-b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

(R)-3 -isopropyl-5-(4-( 1 -((6-(pyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole.

20. The compound of claim 1, which is

(R)-3-isopropyl-5-(4-(l-((6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole;

5-(4-(l-((5-fluoro-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazol-2-yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole;

(R)-2-(l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

5-(4-( 1 -((5-chloro-6-(4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole;

(S)-5-(4-(l -((6-(3 -fluoropyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole;

(R)-5-(4-(l-((6-(2-fluoropyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole;

(R)-5-(4-(l-((5-fluoro-6-(4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole;

(S)-6-(4-(methylsulfonyl)phenyl)-2-(l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

(S)-4-(2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2,l-b] [ 1 ,3 ,4]thiadiazol-6-yl)pyridine 1 -oxide;

2-(l-(l-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-(l-(l-(5-isopropylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

(S)-5-(4-(l-((6-(2-chloropyrimidin-5-yl)imidazo[2,l-b][l,3,4]thiadiazol-2-yl)oxy)ethyl)piperidin-l-yl)-3-isopropyl-l,2,4-oxadiazole;

(S)-3-isopropyl-5-(4-(l-((6-(2-(methylsulfonyl)pyrimidin-5-yl)imidazo[2,l-b] [ 1 ,3 ,4]thiadiazol-2-yl)oxy)ethyl)piperidin- 1 -yl)- 1 ,2,4-oxadiazole.

21. The compound of claim 1, which is

2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(pyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-(l -( 1 -(3 -(trifluorom ethyl)- 1 ,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-(methylsulfonyl)pyrimidin-5-yl)imidazo[2,l-b][l,3,4]thiadiazole;

2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(6-chloropyridin-3-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-((R)- 1 -(1 -(3 -(tnfluoromethyl)- 1 ,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(3-(trifluoromethyl)-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(5-chloropyrazin-2-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-((R)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(pyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazole;

2-((R)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(6-(methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(3-fluoropyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-((S)-l-(l-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(6-(trifluoromethyl)pyridin-3-yl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(5-chloropyrazin-2-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-methoxypyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-((R)-l-(l-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-(trifluoromethyl)-4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3-(trifluoromethyl)pyridin-4-yl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-methoxypyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-((S)-l-(l-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-methoxypyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3-methoxypyridin-4-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

4-(2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2,l-b] [ 1 ,3 ,4]thiadiazol-6-yl)- 1 -methylpyridin-2( lH)-one;

2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(3-fluoropyridin-4-yl)imidazo[2,l-b][l,3,4]thiadiazole hydrochloride;

2-((S)-l-(l-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

4-(2-((R)- 1 -( 1 -(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)imidazo[2, 1 -b][l,3,4]thiadiazol-6-yl)-3-fluorobenzonitrile;

2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-6-(methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole;

isopropyl 4-(l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yloxy)ethyl)piperidine- 1 -carboxylate;

2-((R)-l-(l-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-6-(methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-methoxy-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)imidazo[2,l-b][l,3,4]thiadiazole;

2-((R)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-fluoro-4-(lH-tetrazol-5-yl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole hydrochloride;

tert-butyl 4-( 1 -(6-(6-fluoro-4-(methylsulfonyl)cyclohexa- 1 ,5-dienyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yloxy)ethyl)piperidine- 1 -carboxylate;

ethyl 4-( 1 -(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazol-2-yloxy)ethyl)piperidine- 1 -carboxylate;

isopropyl 4-((S)-l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2,l-b] [ 1 ,3 ,4]thiadiazol-2-yloxy)ethyl)piperidine- 1 -carboxylate;

1 - methyl cyclopropyl 4-(l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2, l-b] [ 1 ,3 ,4]thiadiazol-2-yloxy)ethyl)piperidine- 1 -carboxylate;

21.. The compound of claim 1, which is

2- (l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(thiazol-5-yl)imidazo[2, 1 -b] [ 1 ,3 ,4]thiadiazole;

2-((S)-l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-6-(2-methyl-4-(methylsulfonyl)phenyl)imidazo[2, l-b][l,3,4]thiadiazole;

ethyl 4-((S)-l-(6-(2-fluoro-4-(methylsulfonyl)phenyl)imidazo[2,l-b][l,3,4]thiadiazol-2-yloxy)ethyl)piperidine- 1 -carboxylate;

4-(3-isopropyl-l,2,4-oxadiazol-5-yl)-l-(3-(4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5-yl)piperidine;

4-(l-(3-(4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5-yloxy)ethyl)-l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidine;

4-(3 -(4-(m ethyl sulfonyl)phenyl)- 1 ,2,4-thiadiazol-5-yloxy)- 1 -(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidine;

4- ((3 -(4-(methylsulfonyl)phenyl)- 1 ,2,4-thiadiazol-5-yloxy)m ethyl)- 1 -(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)piperidine;

5- (3-(l-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-l,2,4-thiadiazol-5-yl)-2-(methylsulfonyl)pyridine;

5-(3-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yloxy)-l,2,4-thiadiazol-5-yl)-2-(methylsulfonyl)pyridine;

5-(3-((l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yl)methoxy)-l,2,4-thiadiazol-5-yl)-2-(methylsulfonyl)pyridine;

5-(5-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yloxy)-l,2,4-thiadiazol-3-yl)-2-(methylsulfonyl)pyridine;

2-(4-(3-(6-(methylsulfonyl)pyridin-3-yl)-l,2,4-thiadiazol-5-yloxy)piperidin-l-yl)-5-ethylpyrimidine;

2-(4-(3-(6-(methylsulfonyl)pyridin-3-yl)-l,2,4-thiadiazol-5-yloxy)piperidin-l-yl)-5-propylpyrimidine;

N-(5-(l-(3-isopropyl-l,2,4-oxadiazol-5-yl)piperidin-4-yloxy)-l,2,4-thiadiazol-3-yl)-N-methyl-6-(methylsulfonyl)pyridin-3-amine.

2-(4-(3-(2-fluoro-4-(methylsulfonyl)phenyl)-l,2,4-thiadiazol-5-yloxy)piperidin-l-yl)-5-ethylpyrimidine;

1 -(3 -isopropyl- 1 ,2,4-oxadiazol-5-yl)-N-(3 -(6-(m ethyl sulfonyl)pyridin-3 -yl)- 1 ,2,4-thiadiazol-5-yl)piperidin-4-amine;

l-(3-isopropyl-l,2,4-oxadiazol-5-yl)-N-methyl-N-(3-(6-(methylsulfonyl)pyridin-3-yl)-l,2,4-thiadiazol-5-yl)piperidin-4-amine.

22. A method of treating diseases and conditions mediated through GPR119 comprising administering the compound of claim 1 to a patient in need thereof.

23. A method of treatment diseases and conditions mediated through GPR119 comprising administering the compound of claim 2 to a patient in need thereof.

24. The method of claim 22, wherein said disease is metabolic disorder.

25. The method of claim 23, wherein said disease is metabolic disorder.

26. The method of claim 24, wherein said disease is diabetes.

27. The method of claim 25, wherein said disease is diabetes.

28. The method of claim 26, wherein said disease is Type II diabetes.

29. The method of claim 27, wherein said disease is Type II diabetes.