WO2008035359A2

WO2008035359A2 - Oximinophenoxyalkanoic acid and phenylalkanoic acid derivatives

Info

Publication number: WO2008035359A2
Application number: PCT/IN2007/000226
Authority: WO
Inventors: Braj Bhushan Lohray; Vidya Bhushan Lohray; Harikishore Pingali; Pankaj Ramanbhai Patel
Original assignee: Cadila Healthcare Limited
Priority date: 2006-06-12
Filing date: 2007-06-05
Publication date: 2008-03-27
Also published as: WO2008035359A3

Abstract

The present invention discloses oximinophenoxyalkanoic acid and phenylalkanoic acid of the general formula (I) their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, methods for their preparation, use of these compounds in medicine and the intermediates involved in their preparation.

Description

OXIMINOPHENOXYALKANOIC ACID AND PHENYLALKANOIC ACID DERIVATIVES

FIELD OF INVENTION The present invention relates to novel oximinophenoxyalkanoic acid and phenylalkanoic acid of the general formula (I), their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, methods for their preparation, use of these compounds in medicine and the intermediates involved in their preparation.

The compounds of the general formula (I) lower blood glucose, lower or modulate triglyceride levels and/or cholesterol levels and/or low-density lipoproteins (LDL) and raises the high-density lipoproteins (HDL) plasma levels and hence are useful in combating different medical conditions, where such lowering (and raising) is beneficial. Thus, it could be used in the treatment and/or prophylaxis of obesity, hyperlipidaemia, hypercholesteremia, hypertension, atherosclerotic disease events, vascular restenosis, diabetes and many other related conditions.

The compounds of general formula (I) are useful to prevent or reduce the risk of developing atherosclerosis, which leads to diseases and conditions such as artereosclerotic cardiovascular diseases, stroke, coronary heart diseases, cerebrovascular diseases, peripheral vessel diseases and related disorders. These compounds of general formula (I) are useful for the treatment and/or prophylaxis of metabolic disorders loosely defined as Syndrome X. The characteristic features of Syndrome X include initial insulin resistance followed by . hyperinsulinemia, dyslipidemia and impaired glucose tolerance. The glucose intolerance can lead to non- insulin dependent diabetes mellitus (NIDDM, Type 2 diabetes), which is characterized by hyperglycemia, which if not controlled may lead to diabetic complications or metabolic disorders caused by insulin resistance. Diabetes is no longer considered to be associated only with glucose metabolism, but it affects anatomical and physiological parameters, the intensity of which vary depending upon stages/duration and severity of the diabetic state. The compounds of this invention are also useful in prevention, halting or slowing progression or reducing the risk of the above mentioned disorders along with the resulting secondary diseases such as cardiovascular diseases, like arteriosclerosis, atherosclerosis; diabetic retinopathy, diabetic neuropathy and renal disease including diabetic nephropathy, glomerulonephritis, glomerular sclerosis, nephrotic syndrome, hypertensive nephrosclerosis and end stage renal diseases, like microalbuminuria and albuminuria, which may be result of hyperglycemia or hyperinsulinemia.

The compounds of the present invention can be useful as aldose reductase inhibitors; for improving cognitive functions in dementia, and in the treatment and/or prophylaxis of disorders such as psoriasis, polycystic ovarian syndrome (PCOS), cancer, osteoporosis, leptin resistance, inflammation and inflammatory bowel diseases, wound healing, xanthoma, pancreatitis, myotonic dystrophy, endothelial cell dysfunction and hyperlipidemia. BACKGROUND OF THE INVENTION

Hyperlipidaemia has been recognized as the major risk factor in causing cardiovascular diseases due to atherosclerosis. Atherosclerosis and other such peripheral vascular diseases affect the quality of life of a large population in the world. The therapy aims to lower the elevated plasma LDL cholesterol, low-density lipoprotein and plasma triglycerides in order to prevent or reduce the risk of occurrence of cardiovascular diseases. The detailed etiology of atherosclerosis and coronary artery diseases is discussed by Ross and Glomset [New Engl. J. Med., 295, 369-377 (1976)]. Plasma cholesterol is generally found esterified with various serum lipoproteins and numerous studies have suggested an inverse relationship between serum HDL- cholesterol level and risk for occurrence of cardiovascular disease. Many studies have suggested an increased risk of coronary artery diseases (CAD) due to elevated LDL and VLDL-cholesterol levels [Stampfer et al, N. Engl. J. Med., 325, 373-381(1991)]. The other studies illustrate protective effects of HDL against progression of atherosclerosis. Thus, HDL has become a crucial factor in treating diseases with increased levels of cholesterol [Miller et. al, Br. Med. J. 282, 1741-1744(1981); Picardo et al, Arteriosclerosis, 6, 434-441 (1986); Macikinnon et al, J. Biol. Chem. 261, 2548-2552 (1986)].

Diabetes is associated with a number of complications and also affect a large population. This disease is usually associated with other diseases such as obesity, hyperlipidemia, hypertension and angina. It is well established that improper treatment can aggravate impaired glucose tolerance and insulin resistance, thereby leading to frank diabetes. Further, patients with insulin resistance and type 2 diabetes often have raised triglycerides and low HDL-cholesterol concentrations and therefore, have greater risk of cardiovascular diseases. The present therapy for these diseases includes sulfonylureas and biguanides along with insulin. This type of drug therapy may lead to mild to severe hypoglycemia, which may lead to coma or in some cases may lead to death, as a result of unsatisfactory glycaemic control by these drugs. Recent addition of drugs in the treatment of diabetes are the thiazolidinediones, drugs having insulin- sensitizing action. Thiazolidinediones like troglitazone, rosiglitazone and pioglitazone are prescribed alone or in combination with other anti-diabetic agents. These are useful in treating diabetes, lipid metabolism but are suspected to have tumor- inducing potential and cause hepatic dysfunction, which may lead to liver failure. Further, serious undesirable side-effects have occurred in animal and/or human studies which include cardiac hypertrophy, hema dilution and liver toxicity in a few glitazones progressing to advanced human trials. The drawback is considered to be idiosyncratic.

Presently, there is a need for a safe and an effective drug, to treat insulin resistance, diabetes and hyperlipidemia.[ Exp. Clin. Endocrinol. Diabetes: 109(4), S548-9 (2001)]

Obesity is another major health problem being associated with increased morbidity and mortality. It is a metabolic disorder, in which excess of fat is accumulated in the body. Although, its etiology is unclear, the general feature includes excess of calorie intake than it is consumed. Various therapies such as dieting, exercise, appetite suppression, inhibition of fat absorption etc. have been used to combat obesity. However, more efficient therapies to treat this abnormality is essential as obesity is closely related to several diseases such as coronary heart disease, stroke, diabetes, gout, osteoarthritis, hyperlipidaemia and reduced fertility. It also leads to social and psychological problems [Nature Reviews: Drug Discovery: 1(4), 276-86 (2002)].

Peroxisome Proliferator Activated Receptor (PPAR) is a member of the steroid/ retinoid/ thyroid hormone receptor family. PPARoc, PPARγ and PPARδ have been identified as subtypes of PPARs. Extensive reviews regarding PPAR, their role in different diseased conditions are widely published [Endocrine Reviews, 20(5), 649-688 (1999); J. Medicinal Chemistry, 43(4), 58-550 (2000); Cell, 55, 932-943 (1999); Nature, 405, 421-424 (2000); Trends in Pharmacological ScI, 469-473 (2000)]. PPARγ activation has been found to play a central role in initiating and regulating adipocyte differentiation [Endocrinology 135, 798-800, (1994)] and energy homeostasis, [Cell, 83, 803-812 (1995); Cell, 99, 239-242 (1999)]. PPARγ agonists would stimulate the terminal differentiation of adipocyte precursors and cause morphological and molecular changes characteristic of a more differentiated, less malignant state. During adipocyte differentiation, several highly specialized proteins are induced, which are being involved in lipid storage and metabolism. It is accepted that PPARγ activation leads to expression of CAP gene [Cell Biology, 95, 14751- 14756, (1998)], however, the exact link from PPARγ activation to changes in glucose metabolism and decrease in insulin resistance in muscle has not been clear. PPARα is involved in stimulating β-oxidation of fatty acids [Trends Endocrine. Metabolism, 4, 291-296 (1993)] resulting in plasma circulating free fatty acid reduction [Current Biol, 5, 618-621 (1995)]. Recently, role of PPARγ activation in the terminal differentiation of adipocyte precursors has been implicated in the treatment of cancer. [Cell, 79, 1147- 1156 (1994); Cell, 377-389 (1996); Molecular Cell, 465-470 (1998); Carcinogenesis, 1949-1953 (1998); Proc. Natl. Acad. ScL, 94, 237-241 (1997); Cancer Research, 58, 3344-3352 (1998)]. Since PPARγ is expressed in certain cells consistently, PPARγ agonists would lead to nontoxic chemotherapy. There is growing evidence that PPAR agonists may also influence the cardiovascular system through PPAR receptors as well as directly by modulating vessel wall function [Med. Res. Rev., 20 (5), 350-366 (2000)]. PPAR δ is broadly expressed in the body and has been shown to be a valuable molecular target for treatment of dyslipidimia, inflammation, wound healing and other diseases. PPAR α agonists have been found useful in the treatment of obesity (WO 97/36579). Dual PPAR α and γ agonists have been suggested to be useful for Syndrome X (WO 97/25042). PPAR delta compound was shown to decrease VLDL and increase HDL in a dose dependent manner (Proc. Natl. Acad. Sci.U.S.A. 98, 5305, 2001).

PPAR γ agonists and HMG-CoA reductase inhibitors have exhibited synergism and indicated the usefulness of the combination in the treatment of atherosclerosis and xanthoma (EP 0753 298). Leptin is a protein when bound to leptin receptors is involved in sending satiety signal to the hypothalamus. Leptin resistance would therefore lead to excess food intake, reduced energy expenditure, obesity, impaired glucose tolerance and diabetes [Science, 269, 543-46(1995)]. It has been reported that insulin sensitizers lower plasma leptin concentration [Proc. Natl. Acad. ScL 93, 5793-5796 (1996): WO 98/02159)].

Several compounds have been reported which are agonists of PPAR in patents WO 2004063166, WO 2004063155, WO 2004048334. However, the therapeutic potential of these compounds to treat diseases has not yet been proved and so there remains the need to develop newer medicines which are better or of comparable efficacy with the present treatment regimes, have lesser side effects and require a lower dosage regime

We herein disclose novel compounds of formula (I) useful as hypocholesterolemic, hypolipidaemic, hypolipoproteinemic, anti-obesity and antihyperglycemic agents which may have additional body weight lowering effect and beneficial effect in the treatment and/or prophylaxis of diseases caused by hyperlipidaemia, diseases classified under Syndrome X, atherosclerosis, inflamation and wound healing and methods for their preparation. PREFERRED EMBODIMENTS OF THE INVENTION

The main objective of the present invention is to provide novel substituted oximinophenoxyalkanoic acid and phenylalkanoic acid and their derivatives represented by the general formula (I), their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, and pharmaceutical compositions containing them or their mixtures thereof.

In an embodiment of the present invention is provided a process for the preparation of novel substituted oximinophenoxyalkanoic acid and phenylalkanoic acid and their derivatives represented by the general formula (I), their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts. In a further embodiment of the present invention is provided pharmaceutical compositions containing compounds of the general formula (I), their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, or their mixtures in combination with suitable carriers, solvents, diluents and other media normally employed in preparing such compositions. DETAILED DESCRIPTION OF THE INVENTION

Accordingly, the present invention relates to compounds of the general formula (I),

their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, and pharmaceutical compositions containing them wherein 'A' represents an optionally substituted single or fused group selected from aryl, heterocyclyl or cycloalkyl groups;

In a preferred embodiment, 'A' is selected from optionally substituted aryl or heterocyclyl groups;

In a further preferred embodiment, the aryl group may be selected from monocyclic or bicyclic aromatic groups; in a still further embodiment, the aryl group is an optionally substituted phenyl group.

The heterocyclyl group may be selected from single or fused mono, bi or tricyclic aromatic or non-aromatic radicals containing one or more hetero atoms selected from

O, N or S; in a preferred embodiment, the heterocyclyl group may be selected from thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, indolinyl, indolyl, pyrazolyl, quinazolinyl, quinazolinonyl, carbazolyl, phenothiazinyl, phenoxazinyl, benzoxazolyl, benzothiazolyl, benzoxazine, benzoxazinone, oxazolidinone groups;

'W represents substituted or unsubstituted linear or branched (Ci-C_ό)alkyl, (C₂-

C₆)alkenyl groups; in a preferred embodiment, 'W is selected from (Ci-C₃)alkyl or (C₂-C₄)alkenyl groups;

Ri represents optionally substituted linear or branched (C]-C₆)alkyl, (C₃-C_ό)cycloalkyl, aryl, aralkyl groups; In a preferred embodiment, the aryl group represents optionally substituted phenyl group;

R₂ represents hydrogen, linear or branched substituted or unsubstituted (Ci-Ce)alkyl ; R₃ at each occurrence independently represents hydrogen, halo, optionally substituted groups selected from linear or branched (Ci-C₃)alkyl, halo(C]-C₃)alkyl, (Ci-C₃)alkoxy, thio(Ci-C₃)alkyl, sulfenyl derivatives, sulfonyl derivatives; R₄ and R₅ may be same or different and independently represents H or (Ci-Ce)alkyl;

X represents either a bond or oxygen or the group -CH₂-; When A or Ri are substituted, the substituents may be independently selected from hydroxyl, oxo, halo, thio, amino, or substituted or unsubstituted groups selected from alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, aryl, aryloxy, aralkyl, aralkoxy, heterocyclyl, acyl, arylamino, aralkylamino, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, aralkoxyalkyl, alkylthio, arylthio, alkylsulfonylamino, alkylsulfonyloxy, alkoxycarbonylamino, aryloxycarbonylamino, aralkyloxycarbonylamino, sulfenyl derivatives, sulfonyl derivatives.

When the substituents on A or Ri are further substituted, the substituents may be independently selected from hydroxyl, oxo, halo, thio, amino, or substituted or unsubstituted groups selected from alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, aryl, aryloxy, acyl, hydroxyalkyl, alkoxyalkyl, alkylthio, arylthio, alkylsulfonyloxy, alkoxycarbonylamino, aryloxycarbonylamino, aralkyloxycarbonylamino, sulfenyl derivatives, sulfonyl derivatives.

The various groups, radicals and substituents used anywhere in the specification are described in the following paragraphs.

In a further preferred embodiment the groups, radicals described above may be selected from:

- the "alkyl" group used either alone or in combination with other radicals, denotes a linear or branched radical containing one to six carbons, selected from methyl, ethyl, ^-propyl, wo-propyl, n-butyl, sec-butyl, tert-butyl, amyl, /-amyl, «-pentyl, n- hexyl, and the like;

- the "alkenyl" group used either alone or in combination with other radicals, is selected from a radical containing from two to six carbons, more preferably groups selected from vinyl, allyl, 2-butenyl, 3-butenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl and the like; the "alkenyl" group includes dienes and trienes of straight and branched chains;

- the "cycloalkyl", or "alicyclic" group used either alone or in combination with other radicals, is selected from a cyclic radical containing three to six carbons, more preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like; - the "alkoxy" group used either alone or in combination with other radicals, is selected from groups containing an alkyl radical, as defined above, attached directly to an oxygen atom, more preferably groups selected from methoxy, ethoxy, n- propoxy, ώopropoxy, «-butoxy, ^-butoxy, wø-butoxy, pentyloxy, hexyloxy, and the like; the "haloalkyl" group is selected from an alkyl radical, as defined above, suitably substituted with one or more halogens; such as perhaloalkyl, more preferably, perfluoro(Ci-C6)alkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, mono or polyhalo substituted methyl, ethyl, propyl, butyl, pentyl or hexyl groups; the "haloalkoxy" group is selected from suitable haloalkyl, as defined above, directly attached to an oxygen atom, more preferably groups selected from fluoromethoxy, chloromethoxy, fluoroethoxy, chloroethoxy and the like; the "aryl" or "aromatic" group used either alone or in combination with other radicals, is selected from a suitable aromatic system containing one, two or three rings wherein such rings may be attached together in a pendant manner or may be fused, more preferably the groups are selected from phenyl, naphthyl, tetrahydronaphthyl, indane, biphenyl, and the like; the "heterocyclyl" or "heterocyclic" group used either alone or in combination with other radicals, is selected from suitable aromatic or non-aromatic radicals containing one or more hetero atoms selected from O, N or S. The non-aromatic radicals may be saturated, partially saturated or unsaturated mono, bi or tricyclic radicals, containing one or more heteroatoms selected from nitrogen, sulfur and oxygen, more preferably selected from aziridinyl, azetidinyl, pyrrolidinyl, imidazolidinyl, piperidinyl, piperazinyl, 2-oxopiperidinyl, 4-oxopiperidinyl, 2- oxopiperazinyl, 3-oxopiperazinyl, morpholinyl, thiomorpholinyl, 2- oxomorpholinyl, azepinyl, diazepinyl, oxapinyl, thiazepinyl, oxazolidinyl, thiazolidinyl, dihydrothiophene, dihydropyran, dihydrofuran, dihydrothiazole, benzopyranyl, benzopyraηonyl, benzodihydrofuranyl, benzodihydrothienyl, pyrazolopyrimidonyl, azaquinazolinoyl, thienopyrimidonyl, quinazolonyl, pyrimidonyl, benzoxazinyl, benzoxazinonyl, benzothiazinyl, benzothiazinonyl, thieno piperidinyl, and the like; the aromatic radicals, may be selected from suitable single or fused mono, bi or tricyclic aromatic heterocyclic radicals containing one or more hetero atoms selected from O, N or S, more preferably the groups are selected from pyridyl, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, isothiazolyl, imidazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, benzofuranyl, benzothienyl, indolinyl, indolyl, azaindolyl, azaindolinyl, pyrazolopyrimidinyl, azaquinazolinyl, pyridofuranyl, pyridothienyl, thienopyrimidyl, quinolinyl, pyrimidinyl, pyrazolyl, quinazolinyl, pyridazinyl, triazinyl, benzimidazolyl, benzotriazolyl, phthalazynil, naphthylidinyl, purinyl, carbazolyl, phenothiazinyl, phenoxazinyl, benzoxazolyl, benzothiazolyl and the like; the "acyl" group used either alone or in combination with other radicals, is selected from a radical containing one to eight carbons, more preferably selected from formyl, acetyl, propanoyl, butanoyl, wø-butanoyl, pentanoyl, hexanoyl, heptanoyl, benzoyl and the like, which may be substituted; the "mono-substituted amino" group used either alone or in combination with other radicals, represents an amino group substituted with one group selected from (Ci- C_δ)alkyl, substituted alkyl, aryl, substituted aryl or arylalkyl groups as defined earlier, more preferably such groups are selected from methylamine, ethylamine, n- propylamine, »-butylamine, n-pentylamine and the like;

- the "arylamino" used either alone or in combination with other radicals, represents an aryl group, as defined above, linked through amino having a free valence bond from the nitrogen atom, more preferably the groups are selected from phenylamino, naphthylamino, N^Lmethyl anilino and the like; the "ester" group used alone or in combination with other radicals, denotes -COO- group, and includes carboxylic acid derivatives, more preferably the ester moieties are selected from alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, and the like, which may optionally be substituted; aryloxycarbonyl group such as phenoxycarbonyl, napthyloxycarbonyl, and the like, which may optionally be substituted; aralkoxycarbonyl group such as benzyloxycarbonyl, phenethyloxycarbonyl, napthylmethoxycarbonyl, and the like, which may optionally be substituted; heteroaryloxycarbonyl, heteroaralkoxycarbonyl, wherein the heteroaryl group, is as defined above, which may optionally be substituted; heterocyclyloxycarbonyl, where the heterocyclic group, as defined earlier, which may optionally be substituted;

- the "hydroxyalkyl" group used either alone or in combination with other radicals, is selected from an alkyl group, as defined above, substituted with one or more hydroxy radicals, more preferably the groups are selected from hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl and the like;

- the "alkoxyalkyl" group used alone or in combination with other radicals, denotes an alkoxy group, as defined above, attached to an alkyl group as defined above, more preferably the groups may be selected from methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl and the like;

- the "alkylthio" group used either alone or in combination with other radicals, denotes a straight or branched or cyclic monovalent substituent comprising an alkyl group as defined above, linked through a divalent sulfur atom having a free valence bond from the sulfur atom, more preferably the groups may be selected from methylthio, ethylthio, propylthio,

- the "oxo" or "carbonyl" group used either alone (-C=O-) or in combination with other radicals such as alkyl described above, for e.g. "alkylcarbonyl", denotes a carbonyl radical (-C=O-) substituted with an alkyl radical described above such as acyl or alkanoyl;

- the "alkoxycarbonylamino" group used alone or in combination with other radicals, is selected from a suitable alkoxycarbonyl group, as defined above, attached to an amino group, more preferably methoxycarbonylamino, ethoxycarbonylamino, and the like; the "sulfenyl" group or "sulfenyl derivatives" used alone or in combination with other radicals, represents a bivalent group, -SO- or R_xSO, where R_x is an optionally substituted alkyl, aryl, heteroaryl, heterocyclyl, group selected from those described above; - the "sulfonyl" group or "sulfones derivatives" used either alone or in combination with other radicals, with other terms such as alkylsulfonyl, represents a divalent radical -SO₂-, or R_xSO₂-, where R_x is as defined above. More preferably, the groups may be selected from "alkylsulfonyl" wherein suitable alkyl radicals, selected from those defined above, is attached to a sulfonyl radical, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl and the like, "arylsulfonyl" wherein an aryl radical, as defined above, is attached to a sulfonyl radical, such as phenylsulfonyl and the like.

Suitable groups and substituents on the groups may be selected from those described anywhere in the specification. Particularly useful compounds may be selected from Ethyl-[4-( 1 -hydroxyimino-propyl)-phenoxy]-acetate; Ethyl-[4-(l-hydroxyimino-butyl)-phenoxy]-acetate; Ethyl-[4-(l-hydroxyimino-ethyl)-2-methyl-phenoxy]-acetate; Ethyl-[4-(hydroxyimino-phenyl-methyl)-2-methyl-phenoxy]-acetate; 26

Ethyl-[4-(2-cyclohexyl-l-hydroxyimino-ethyl)-2-methyl-phenoxy]-acetate;

Ethyl-[4-(2-cyclopentyl-l-hydroxyimino-ethyl)-2-methyl-phenoxy]-acetate;

Ethyl-[4-(l-hydroxyimino-2-phenyl-ethyl)-2-methyl-phenoxy]-acetate;

Ethyl-[4-(cyclohexyl-hydroxyimino-methyl)-2-methyl-phenoxy]-acetate; Ethyl- [4-( 1 -hydroxyimino-2-thiophen-3 -y 1-ethy l)-2-methyl-phenoxy] -acetate;

Ethyl-{4-[2-(4-chloro-phenyl)-l-hydroxyimino-ethyl]-2-methyl-phenoxy}-acetate;

Ethyl-[4-( 1 -hydroxyimino-ethyl)-phenyl]-acetate.

Ethyl-{4-[l-(3-methyl-4-oxo-3,4-dihydro-quinazolin-2-ylmethoxyimino)-propyl]- phenoxy} -acetate; Ethyl-(4-{l-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxy)-propoxyimino]-2-phenyl- ethyl} -2-methyl-phenoxy)-acetate;

Ethyl-{2-methyl-4-[l-(3-methyl-4-oxo-3,4-dihydro-quinazolin-2-ylmethoxyimino)- ethylj-phenoxy} -acetate;

Ethyl- {4-[ 1 ~(2-p-tolyl-ethoxyimino)-propyl]-phenoxy} -acetate; Ethyl-(4-{ l-[2-(4-methoxy-phenyl)-ethoxyimino] -propyl} -phenoxy)-acetate;

Ethyl-{4-[l-(4-methoxy-benzyloxyimino)-propyl]-phenoxy}-acetate;

Ethyl-(4-{l-[2-(4-trifluoromethyl-phenyl)-ethoxyimino]-propyl}-phenoxy)-acetate;

Ethyl-(4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- propyl} -phenoxy)-acetate; Ethyl-{4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetate;

Ethyl-{4-[l-(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetate;

Ethyl- {4-[ 1 -(2-tert-butyl-5-methyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy} - acetate;

Ethyl- {4-[l -(4-trifluoromethyl-benzyloxyimino)-propyl]-ρhenoxy} -acetate; Ethyl-(2-methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5 ylmethoxyimino]-ethyl}-phenoxy)-acetate;

Ethyl-{2-methyl-4-[l-(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-ethyl]- phenoxy} -acetate;

Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}- acetate;

Ethyl- {2-methyl-4-[l -(4-trlfluoromethyl-benzyloxyimino)-ethyl]-phenoxy} -acetate; Ethyl-(2-methyl-4-{l-[2-(3-oxo-2,3-dihydro-benzo[l,4]oxazin-4-yl)-ethoxyimino]- ethyl} -phenoxy)-acetate; Ethyl- {2-methyl-4-[ 1 -(2-phenoxazin- 10-yl-ethoxyimino)-ethyl]-phenoxy} -acetate;

Ethyl-[2-methyl-4-(l-{2-[2-methyl-5-(4-methylsulfanyl-phenyl)-pyrrol-l-yl]- ethoxyimino} -ethyl)-phenoxy]-acetate;

Ethyl-(2-methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-ethyl} -phenoxy)-acetate;

Ethyl- {4-[ 1 -(2-fluoro-benzyloxyimino)-ethyl]-2-meth^'yl-phenoxy} -acetate;

Ethyl-{4-[l-(2-indol-l-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy}-acetate;

Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy}-acetate;

Ethyl-{4-[l-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxyimino)-ethyl]-2-methyl- phenoxy} -acetate;

Ethyl-{4-[l-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-ylmethoxyimino)-ethyl]-2-methyl- phenoxy} -acetate;

Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-2-phenyl-ethyl]- phenoxy} -acetate; Ethyl- {2-methyl-4-[2-phenyl-l -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} - acetate;

Ethyl- {2-methyl-4-[(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-phenyl-methyl]- phenoxy} -acetate;

Ethyl-(2-methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-2-phenyl-ethyl}-phenoxy)-acetate;

Ethyl-(4-{cyclohexyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-

5ylmethoxyimino]-methyl}-2-methyl-phenoxy)-acetate;

Ethyl-{4-[cyclohexyl-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-methyl]-2- methyl-phenoxy } -acetate; Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}- acetate;

Ethyl-{4-[l-(2-indol-l-yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetate;

Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-butyl]-phenoxy}- acetate; , Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-butyl]-2-methyl-phenoxy}-acetate;

Ethyl-{4-[l-(2-fluoro-benzyloxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetate;

Ethyl- {4-[ 1 -(2-indol- 1 -yl-ethoxyimino)-butyl] -2-methyl-phenoxy}-acetate;

Ethyl-{4-[l-(2-indol-l-yl-ethoxyimino)-propyl]-phenoxy}-acetate;

Ethyl- {4-[cyclohexyl-(2-indol- 1 -yl-ethoxyimino)-methyl]-2-methyl-phenoxy} -acetate; Ethyl-{2-methyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-butyl]-phenoxy}-acetate;

Ethyl-{4-[cyclohexyl-(4-trifluoromethyl-benzyloxyimino)-methyl]-2-methyl- phenoxy} -acetate;

Ethyl-{4-[2-cyclopentyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetate;

Ethyl- {4-[2-cyclohexyl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetate;

Ethyl-{2-methyl-4-[l-(2-oxo-3-phenyl-oxazolidin-5-ylmethoxyimino)-ethyl]- phenoxy } -acetate; Ethyl-{4-[l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenyl}-acetate;

Ethyl-{4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenyl}-acetate;

Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-ethyl]-phenyl}-acetate;

Ethyl- (4-[2-(4-chloro-phenyl)- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetate; Ethyl-{2-methyl-4-[2-thiophen-3-yl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]- phenoxy } -acetate;

{4-[l-(2-p-Tolyl-ethoxyimino)-propyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

(4-{l-[2-(4-Methoxy-phenyl)-ethoxyimino]-propyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(4-Methoxy-benzyloxyimino)-propyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

(4-{ l-[2-(4-Trifluoromethyl-phenyl)-ethoxyimino]-propyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts; (4-{l-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]-propyl}- phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[ 1 -(5-Methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{4-[ 1 -(5 -Methyl-2-phenyl-oxazol-4-ylmethoxyimino)-propyl] -phenoxy} -acetic . acid and its pharmaceutically acceptable salts;

{4-[l-(2-tert-Butyl-5-methyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(4-Trifluoromethyl-benzyloxyimino)-propyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts; (2-Methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- ethyl} -ρhenoxy)-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts; {2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

(2-Methyl-4-{ 1 -[2-(3-oxo-2,3-dihydro-benzo[ 1 ,4]oxazin-4-yl)-ethoxyimino]-ethyl} - phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(2-phenoxazin-10-yl-ethoxyimino)-ethyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

[2-Methyl-4-(l -{2-[2-methyl-5-(4-methylsulfanyl-phenyl)-pyrrol- 1 -yl]-ethoxyimino} - ethyl)-phenoxy]-acetic acid and its pharmaceutically acceptable salts; (2-Methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- ethyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Fluoro-benzyloxyimino)-ethyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Indol-l-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Carbazol-9-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-tert-Butyl-5-methyl-oxazol-4-ylmethoxyimino)-ethyl]-2-methyl-phenoxy}- acetic acid and its pharmaceutically acceptable salts; {4-[l-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-ylmethoxyimino)-ethyl]-2-methyl- phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-2-phenyl-ethyl]- phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[2-phenyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-phenyl-methyl]- phenoxy} -acetic acid and its pharmaceutically acceptable salts;

(2-Methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]-2- phenyl-ethyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts; (4-{Cyclohexyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- methyl}-2-methyl-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[Cyclohexyl-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-methyl]-2-methyl- phenoxy} -acetic acid and its pharmaceutically acceptable salts; {4-[l-(2-Carbazol-9-yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[ 1 -(2-Indol- 1 -yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy } -acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[ 1 -(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-butyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Carbazol-9-yl-ethoxyimino)-butyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Fluoro-benzyloxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts; {4-[l-(2-Indol-l-yl-ethoxyimino)-butyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[Cyclohexyl-(2-indol- 1 -yl-ethoxyimino)-methyl]-2-methyl-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-butyl]-phenoxy} -acetic . acid and its pharmaceutically acceptable salts;

{4-[Cyclohexyl-(4-trifluoromethyl-benzyloxyimino)-methyl]-2-methyl-phenoxy}- acetic acid and its pharmaceutically acceptable salts;

{4-[2-Cyclopentyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl-phenoxy}- acetic acid and its pharmaceutically acceptable salts; {4-[2-Cyclohexyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl-phenoxy}- acetic acid and its pharmaceutically acceptable salts;

{4-[l-(4-Trifluoromethyl-benzyloxyimino)-ethyl]-phenyl}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(5-Methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenyl}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Carbazol-9-yl-ethoxyimino)-ethyl]-phenyl} -acetic acid and its pharmaceutically acceptable salts;

(4-{l-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxy)-propoxyimino]-2-phenyl-ethyl}-2- methyl-phenoxy)-acetic acid and its pharmaceutically acceptable salts; {4-[2-(4-Chloro-phenyl)-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetic acid and its pharmaceutically acceptable salts; {2-Methyl-4-[2-thiophen-3-yl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} - acetic acid and its pharmaceutically acceptable salts.

The novel compounds of this invention may be prepared using the reactions and techniques described in the following section. The reactions are performed in solvents appropriate to the reagents and materials employed and are suitable for the transformations being effected. It is understood by those skilled in the art that the nature and order of the synthetic steps presented may be varied for the purpose of optimizing the formation of the compounds of the present invention. Scheme: 1 The compounds of general formula (I) wherein all the symbols are as defined earlier, may be prepared by reactions outlined in Scheme 1 below which comprises:

i. Reacting compounds of general formula (II) where all symbols are as defined earlier and L represents a suitable leaving group such as halogen, mesylate, tosylate, triflate and the like with compounds of general formula (III), where all symbols are as defined earlier and R₂ represent alkyl to yield compound of general formula (Ia) where all symbols are as defined earlier and R₂ represent alkyl. ii. Hydrolysis of compound of general formula (Ia) wherein R₂ is alkyl and all other symbols are as defined earlier to yield compound of general formula (I) wherein R₂ is H and all other symbols are as defined earlier. iii. The compounds of formula (I) may optionally be converted to its pharmaceutically acceptable salts by techniques known in the art.

Scheme:2 The intermediate of general formula (III) wherein all the symbols are as defined earlier, may be prepared by reactions outlined in Scheme 2 below which comprises

i. Reacting compounds of general formula (IV) where all symbols are as defined earlier and X represents oxygen with compounds of general formula (V), where all symbols are as defined earlier and L represents a suitable leaving group such as halogen, mesylate, tosylate, triflate and the like to yield compound of general formula (VT) where all symbols are as defined earlier; ii. Reacting the intermediate (VI) where all the symbols are as defined earlier with hydroxylamine hydrochloride to yield the intermediate (III), where all the symbols are as defined earlier. Method A: The compound of formula (Ia) may be prepared by reacting compound of formula (II) with compound of formula (III) under suitable conditions. The reaction may be carried out in presence of solvent(s) such as acetone, tetrahydrofuran, dimethyl sulfoxide, dioxane, acetonitrile, dimethyl formamide, dimethoxy ethane, benzene, toluene, petroleum ether, heptane, hexane, 2-butanone, xylene, alcohols such as methanol, ethanol, propanol, butanol, iso-butanol, tert-butanol, pentanol and the like or mixtures thereof. Base(s) such as alkali metal carbonates such as K2CO3, Na₂CO₃, CsCO₃, and the like; or alkali metal hydroxides such as NaOH, KOH and the like, may be used during this reaction. Alkali metal hydride(s) such as NaH, KH can be used whenever solvent employed is not protic or contain carbonyl group. The reaction may be carried out at a temperature in the range 0 ⁰C to reflux temperature of the solvent(s) used and the reaction time may range from 1 to 48 hours.

Method B: The compound of formula (Ia) may be hydrolysed to compound of formula (I) using suitable base(s) e.g., NaOH, LiOH, KOH and the like. Reaction may be conducted in suitable solvents e.g., alcohols like methanol, ethanol and the like, THF, water or the mixtures thereof. The reaction may be carried out at a temperature in the range 20 ⁰C to reflux temperature of the solvent(s) used and the reaction time may range from 1 to 48 hours. Method C: The intermediate of the formula (VI) may be converted to its corresponding oxime (III) by treating with hydroxylamine hydrochloride in the presence of a base(s) like NaOH, NaOAc and the like. Reaction may be conducted in a suitable solvent system which is preferably a mixture of water and alcohol(s) like ethanol. Reaction may be carried out at a temperature in the range of 20 ⁰C to reflux temperature of the solvent(s) used and the reaction time may range from 1 to 48 hours. The invention is explained in greater detail by the examples given below, which are provided by way of illustration only and therefore should not be construed to limit the scope of the invention.

IH NMR specfral data given in the examples (vide infra) are recorded using a 300 MHz spectrometer (Bruker AVANCE-300) and reported in δ scale. Until and otherwise mentioned the solvent used for NMR is CDCI₃ using tetramethyl silane as the internal standard.

Example 1

Ethyl-[4-( 1 -hydroxyimino-propyl)-phenoxy]-acetate

To a solution of ethyl-(4-propionyl-phenoxy)-acetate (3.0 g) in ethanol (10 niL) was added an other solution of hydroxylammonium chloride (1.7 g) and sodium acetate

(2.0 g) in water and the reaction mixture was heated to reflux for a period of about 2 hours. Rection mixture was cooled and diluted with water. Solid separated was filtered and dried under vaccum to yield 2.7 g of product.

¹H NMR: 1.16 (3H, t, J =7.5 Hz), 1.3 (3H, t, J = 7.1 Hz), 2.8 (2H, q, J = 7.6 Hz), 4.3 (2H, q, J = 7.1 Hz), 4.64 (2H, s), 6.9 (2H, dd, J = 1.9 and 6.9 Hz), 7.5 (2H, dd, J = 1.9 and 6.9 Hz).

Yield: .86.5% The following compounds were prepared by procedure similar to that described in Example 1 with appropriate variations of reactants, reaction conditions and quantities of reagents

Example 2 Ethyl[4-(l-Hydroxyimino-butyl)-2-methyl-phenoxy]-acetate

¹H NMR: 0.97 (3H, t, J=7.41 Hz), 1.30 (3H, t, J=7.14 Hz), 1.51-1.64 (2H, m ), 2.30 (3H, s), 2.74 (2H, t, J=7.62 Hz), 4.27 (2H, q, J=15.5 and 7.14 Hz), 4.65 (2H, s), 6.70 (IH, d, J=8.52 Hz), 7.37 (IH, dd, J=2.5and8.5Hz), 7.43 (IH, s). Yield: 91.75% Example 3

Ethyl-[4-(l-hydroxyimino-ethyl)-2-methyl-phenoxy]-acetate

¹H NMR: 1.3 (3H, t, J = 7.1 Hz), 2.25 (3H, s), 2.31 (3H, s), 4.2 (2H, q, J =7.1 Hz), 4.65 (2H, s), 6.7 (IH, d, J =8.5 Hz), 7.37 (IH, dd, J = 8.5 and2.0 Hz), 7.45 (IH, s). Yield: 70.51% Example 4

Ethyl-[4-(hydroxyimino-phenyl-methyl)-2-methyl-phenoxy]-acetate

¹H NMR: 1.30 (3H, t, J=14.91 Hz), 2.31 (3 H, s), 4.27 (2H, q, J = 16.59 and 9.31 Hz),

4.63 (2H, s), 6.64 (IH, d, J= 8.07 Hz), 7.16-7.55 (7H, m).

Yield: 55% Example 5

Ethyl-[4-(2-cyclohexyl-l-hydroxyimino-ethyl)-2-methyl-phenoxy]-acetate 1H NMR: 1.0-1.1 (6H, m), 1.3 (3H, t, J=6.6 Hz), 1.6 (5H, m), 2.3 (3H, s), 2.6 (2H, d, J=7.0 Hz), 4.2 (2H, q, J=7.1 Hz), 4.5 (2H, s), 6.6 (IH, d, J=8.5 Hz), 7.3 (IH, dd, J=2.5and8.5 Hz), 7.4 (IH, s). Yield: 77.24%

Example 6

Ethyl-[4-(2-cyclopentyl-l-hydroxyimino-ethyl)-2-methyl-phenoxy]-acetate 1H NMR: 1.2 (2H, m), 1.3 (3H, t, J=7.1 Hz), 1.4 (2H, m), 1.6 (4H, m), 2.0 (I H, m), 2.3 (3H, s), 2.8 (2H, dd, J=7.4 and 2.2 Hz), 4.2 (2H, q, J=7.1 Hz), 4.6 (2H, s), 6.7 (I H, dd, J=8.6 and 2.2 Hz), 7.3 (IH, dd, J=8.6 and 2.2 Hz), 7.5 (IH, s). Yield: 69%

Example 7 Ethyl-[4-(l-hydroxyimino-2-phenyl-ethyl)-2-methyl-phenoxy]-acetate ¹H NMR: 1.3 (3H, t, J=7.1 Hz), 2.3 (3H, s), 4.2 (2H, s), 4.3 (2H, q, J=7.1 Hz), 4.6 (2H, s), 6.6 (2H, d, J=8.8 Hz), 7.2 (2H, m), 7.3 (2H, d, J=8.5 Hz), 7.5 (2H, s). Yield: 90 %

Example 8 Ethyl-[4-(cyclohexyl-hydroxyimino-methyl)-2-methyl-phenoxy]-acetate.

¹H NMR: 1.1 -1.3 (9H, m), 1.6 (IH, m), 1.7-1.8 (4H, m), 2.3 (3H, s), 4.2 (2H, q, J=7.1 Hz), 4.6 (2H, s), 6.7 (IH, d, J=8.1 Hz), 7.0 (2H, m). Yield: 65.9%

Example 9 Ethyl-[4-(l-hydroxyimino-2-thiophen-3-yl-ethyl)-2-methyl-phenoxy]-acetate.

¹H NMR: 1.2 (3H, t, J=7.1 Hz), 2.3^'(3H, s), 4.0 (2H, s), 4.3 (2H, q, J=7.1 Hz), 4.6 (2H, s), 6.6 (IH, d, J=8.4 Hz), 7.0 (2H, m), 7.2 (IH, m), 7.3 (IH, m), 7.5 (IH, s). Yield: 50%

Example 10 Ethyl- {4-[2-(4-chloro-phenyl)- 1 -hydroxyimino-ethyl]-2-methyl-phenoxy} -acetate.

¹H NMR: 1.2 (3H, t, J=6.8 Hz), 2.2 (3H, s), 4.1 (2H, s), 4.2 (2H, q, J=7.2 Hz), 4.6 (2H, s), 6.6 (IH, d, J=4.8 Hz), 7.1 (2H, m), 7.2 (2H, m), 7.3 (IH, m), 7.4 (IH, d, 3=1.6 Hz). Yield: 79.36%

Example 11 Ethyl-[4-( 1 -hydroxyimino-ethyl)-phenyl]-acetate.

¹H NMR: 1.25 (3H, t, J=5.4 Hz), 2.28 (3H, s), 3.62 (2H, s), 4.14 (2H, q, J=7.1 Hz), 7.29 (2H, d, J=6.3 Hz), 7.57 (2H, d, J=6.3 Hz). Yield: 100%

Example 12 Ethyl-{4-[l-(3-methyl-4-oxo-3,4-dihydro-quinazolin-2-ylmethoxyimino)-propyl]- phenoxy } -acetate.

A mixture of 2-chloromethyl-3-methyl-3H-quinazolin-4-one (1.0 g),' Ethyl-[4-(l- hydroxyimino-propyl)-phenoxy]-acetate (1.1 g) and potassium carbonate (1.22 g) in anhydrous dimethyl formamide (10 mL) was stirred at 60 ⁰C for about 18 hours in an inert atmosphere. The reaction mixture was cooled to ambient temperature, poured into ice cold water and extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried over sodium sulphate and evaporated under reduced pressure. Crude product was flash chromatographed over silica gel using 7% ethyl acetate in petroleum ether as eluent to obtain 0.9 g of pure product. ¹H NMR: 1.13 (3H, t, J = 7.6 Hz), 1.29 (3H, t, J = 7.1 Hz), 2.77 (2H, q, J= 7.6 Hz), 3.74

(3H, s), 4.27 (2H, q, J = 7.1 Hz), 4.62 ( 2H, s), 5.31 (2H, s), 6.89 (2H, d, J = 8.7 Hz),

7.50 (IH, m), 7.57 (2H, d, J = 8.7 Hz), 7.78 (2H, m), 8.31 (IH, d, J = 7.86 Hz).

Yield: 41 % The following compounds were prepared by procedure similar to that described in

Example 12 with appropriate variations of reactants, reaction conditions and quantities of reagents.

Example 13

Ethyl-{2-methyl-4-[l-(3-methyl-4-oxo-3,4-dihydro-quinazolin-2-ylmethoxyimino)- ethyl]-phenoxy} -acetate.

¹H NMR: 1.28 ( 3H, t, J=7.11 Hz), 2.24 (3H, s), 2.28 ( 3H, s), 3.74 (3H, s), 4.25 ( 2H, q, J=14.28 and 7.14 Hz), 4.64 (2H, s), 5.32 (2H, s), 6.65 (IH, d, J=8.58 Hz), 7.36 (IH, dd, J=8.52 and 2.16 Hz), 7.48 -7.52 (2H, m), 7.74 (2H, m), 7.30 (IH, d, J==8.01 Hz).

Yield: 37 % Example 14

Ethyl- {4-[ 1 -(2-p-tolyl-ethoxyimino)-propyl]-phenoxy } -acetate.

¹H NMR: 1.1 (3H, t, J = 7.5 Hz), 1.3 (3H, t, J = 7.1 Hz), 2.3 (3H, s), 2.7 (2H, q, J = 7.6

Hz), 3.0 (2H, t, J = 7.0 Hz), 4.2 - 4.36 (4H, m), 4.63 (2H, s), 6.8 (2H, d, J = 8.8 Hz), 7.1

(4H, m), 7.6 (2H, d, J = 8.8 Hz). Yield: 68 %

Example 15

Ethyl-(4- { 1 -[2-(4-methoxy-phenyl)-ethoxyimino]-propyl} -phenoxy)-acetate.

¹H NMR: 1.05 (3H, t, J = 7.6 Hz), 1.30 (3H, t, J = 7.1 Hz), 7.70 (2H, q, J = 7.6 Hz),

2.97 (2H, t, J = 6.9 Hz), 3.79 (3H, s), 4.3 (4H, m), 4.63 (2H, s), 6.82 - 6.92 (4H, m), 7.1 (2H, d, J = 8.55 Hz), 7.5 (2H, d, J = 8.55 Hz).

Yield: 32 %

Example 16

Ethyl- {4-[ 1 -(4-methoxy-benzyloxyimino)-propyl]-phenoxy} -acetate.

¹H NMR: 1.09 (3H, t, J = 7.5 Hz), 1.29 (3H, t, J =7.2 Hz), 2.73 (2H, q, J =7.4 Hz), 3.81 (3H,s), 4.26 (2H, q, J = 7.7 Hz), 4.63 (2H, s), 5.12 (2H, s), 6.9 (4H, d, J = 8.46 Hz),

7.33 (2H, d, J = 8.46 Hz), 7.56 (2H, d, J = 8.4 Hz).

Yield: 58 %

Example 17

Ethyl-(4-{ l-[2-(4-trifluoromethyl-phenyl)-ethoxyimino]-propyl}-phenoxy)-acetate. ¹U NMR: 1.0 (3H, t, J = 7.6 Hz), 1.3 (3H, t, J = 7.1 Hz), 2.65 (2H, q, J = 7.6 Hz), 3.1 (2H, t, J = 6.57 Hz), 4.25 (2H, q, J = 7.1 Hz), 4.4 ( 2H₅ 1, J = 6.8 Hz), 4.63 (2H, s), 6.91 (2H, d, J = 8.8 Hz), 7.3 (2H, d, J = 7.98 Hz), 7.5 (4H, m). Yield: 10 % Example 18

Ethyl-(4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- propyl} -phenoxy)-acetate.

¹H NMR: 1.1 (3H, t, J = 7.5 Hz), 1.3 (3H, t, J = 7.1 Hz), 2.54 (3H, s), 2.7 (2H, q, J =

7.6 Hz), 4.3 (2H, q, J = 7.1 Hz), 4.64 ( 2H, s), 5.31 (2H, s), 6.92 (2H, d, J = 8.86 Hz), 7.59 - 7.67 (4H, m), 7.5 (2H, d, J = 8.19 Hz).

Yield: 66 %

Example 19

Ethyl-{4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetate. ¹H NMR: 1.1 (3H, t, J = 7.5 Hz), 1.3 (3H, t, J = 7.1 Hz), 2.38 (3H, s), 2.46 (3H, s), 2.74 (2H, q, J = 7.5 Hz), 4.3 (2H, q, J = 7.1 Hz), 4.62 ( 2H, s), 5.29 (2H, s), 6.90 (2H, d, J =

8.7 Hz), 7.24 (2H, d, J = 8.1 Hz), 7.59 (2H, d, J = 8.7 Hz), 7.91 (2H, d, J = 8.1 Hz). Yield: 45 %

Example 20

Ethyl-{4-[l-(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetate. ¹H NMR: 1.07 (3H, t, J = 7.6 Hz), 1.27 (3H, t, J = 7.1 Hz), 2.47 (3H, s), 2.79 (2H, q, J

= 7.6 Hz), 4.28 (2H, q, J = 7.1 Hz), 4.68 ( 2H, s), 5.29 (2H, s), 6.9 (2H, d, J = 8.7 Hz),

7.44 (3H, m), 7.60 (2H, d, J = 8.7 Hz), 8.02 (2H, m).

Yield: 59 %

Example 21 Ethyl-{4-[l-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}- acetate.

¹H NMR: 1.1 (3H, t, J = 7.3 Hz), 1.3 (3H, t, J = 7.1 Hz), 1.36 (9H, s), 2.35 (3H, s), 2.73

(2H, q, J = 7.6 Hz), 4.3 (2H, q, J = 7.1 Hz), 4.63 ( 2H, s), 5.0 (2H, s), 6.90 (2H, d, J =

8.8 Hz), 7.6 (2H, d, J = 8.8 Hz). Yield: 44 %

Example 22 Ethyl-{4-[l-(4-trifluoromethyl-benzyloxyimino)-propyl]-phenoxy}-acetate. ¹H NMR: 1.14 (3H, t, J = 7.6 Hz), 1.3 (3H, t, J = 7.1 Hz), 2.78 (2H, q, J = 7.6 Hz), 4.28 (2H, q, J = 7.1 Hz), 4.63 ( 2H, s), 5.25 (2H, s), 6.90 (2H, d = 8.9 Hz), 7.5 (2H, d, J = 8.1 Hz), 7.6 (4H, m). Yield: 19 % Example 23

Ethyl-(2-methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-ethyl}-phenoxy)-acetate.

¹H NMR: 1.3 (3H, t, J = 7.1 Hz), 2.2 (3H, s), 2.31 (3H, s), 2.54 (3H, s), 4.27 (2H, q, J = 7.14 Hz), 4.65 (2H, s), 5.32 ( 2H, s), 6.7 (IH, d, J = 8.5 Hz), 7.4 (lH,m), 7.44 (IH, s), 7.65 (2H, d, J = 8.2 Hz), 8.0 (2H, d, J = 8.1 Hz). Yield: 66 %

Example 24

Ethyl- { 2-methyl-4- [ 1 -(5 -methyl-2-phenyl-oxazol-4-ylmethoxyimino)-ethyl] -phenoxy } - acetate. 1H NMR: 1.3 (3H, t, J = 7.1 Hz), 2.1 (3H, s), 2.3 (3H, s), 2.48 (3H, s), 4.26 (2H, q, J = 7.1 Hz), 4.64 (2H, s), 5.12 ( 2H, s), 6.68 (IH, d, J = 8.5 Hz), 7.35 - 7.49 (5H,m), 8.0 (2H, m). Yield: 52 %

Example 25 Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}- acetate.

¹H NMR: 1.3 (3H, t, J= 7.1 Hz), 2.2 (3H, s), 2.3 (3H, s), 2.41 (3H, s), 2.47 (3H, s) 4.27 (2H, q, J = 7.1 Hz), 4.64 (2H, s), 5.11 ( 2H, s), 6.68 (IH, d, J = 8.5 Hz), 7.22 (2H, d, J = 8.1 Hz), 7.4 (IH, dd, J = 2.0 and 8.5 Hz), 7.49 (IH, d, J = 1.35 Hz ), 7.92 (2H, d, J = 8.1 Hz). Yield: 61 %

Example 26

Ethyl-{2-raethyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy}-acetate. 1H NMR: 1.2 (3H, t, J=7.1 Hz), 2.20 (3H, s), 2.30 (3H, s), 4.0 (2H, q, J=7.1 Hz), 4.65 (2H, s), 5.25 (2H, s), 6.65 (IH, d, J=8.5 Hz), 7.30 (IH, d, J=I .9 Hz), 7.52 (3H, m), 7.60 (2H, d, J=8.1 Hz). Yield: 24.832%

Example 27 Ethyl-(2-methyl-4-{l-[2-(3-oxo-2,3-dihydro-benzo[l,4]oxazin-4-yl)-ethoxyimino]- ethyl } -phenoxy)-acetate.

¹H NMR: 1.25 (3H, t), 2.0(3H, s), 2.3 (3H, s), 4.2 (4H, m), 4.4 (2H, t, J=5.4 Hz), 4.60 (2H, s), 4.72 (2H, s), 6.6 (IH, d, J=8.4 Hz), 6.67 (3H, s), 7.15 (IH, m), 7.40 (IH, d, J=8.4 Hz), 7.50 (IH, s). Yield: 84%

Example 28

Ethyl- {2-methyl-4-[ 1 -(2-phenoxazin- 10-yl-ethoxyimino)-ethyl] -phenoxy} -acetate. ¹H NMR: 1.30 (3H, t, J=7.11 Hz), 2.13 (3H, s), 2.32 (3H, s), 3.89 (2H, m), 4.27 (2H, q, J=14.09 and 7.11Hz), 4.39 (2H, t, J=6.06 Hz), 4.66 (2H, s), 6.62-6.76 (9H, m), 7.39 (IH, d, J= 9.03 Hz), 7.50 (IH, s). Yield: 43 %

Example 29

Ethyl-[2-methyl-4-(l-{2-[2-methyl-5-(4-methylsulfanyl-phenyl)-pyrrol-l-yl]- ethoxyimino}-ethyl)-phenoxy]-acetate.

¹H NMR: 1.30 (3H, t, J=7.11 Hz), 2.08 (3H, s), 2.30 (3H, s), 2.35 (3H, s), 2.45 (3H, s), 4.20-4.30 (6H, m), 4.65 (2H, s), 5.95 (IH, d, J=3.3 Hz), 6.00 (IH, d, J=3.39 Hz), 6.67 (IH, d, J=8.55 Hz), 7.22-7.35 (5H, m), 7.39 (IH, s). Yield: 24 % Example 30

¹H NMR: 1.3 (3 H, t, J = 7.1 Hz), 2.2 (3H, s), 2.31 (3H, s), 2.54 (3H, s), 4.27 (2H, q, J = 7.14 Hz), 4.65 (2H, s), 5.32 ( 2H, s), 6.7 (IH₅ d, J = 8.5 Hz), 7.4 (lH,m), 7.44 (IH, s), 7.65 (2H, d, J = 8.2 Hz), 8.0 (2H, d, J = 8.1 Hz). Yield: 66.26%

Example 31

Ethyl-{4-[l-(2-fluoro-benzyloxyimino)-ethyl]-2-methyl-phenoxy}-acetate. 1H NMR: 1.29 (3H, t, J= 7.125 Hz), 2.24 (3H, s), 2.26 (3H, s), 4.25 (2H, q, J= 7.12 Hz), 4.64 (2H, s), 5.29 (2H, s), 6.66 (IH, d, J= 8.52 Hz), 7.02-7.15 (2H, m), 7.29-7.42 (2H, m), 7.46 (2H, m) Yield: 73.3%

Example 32 Ethyl-{4-[l-(2-indpl-l-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy}-acetate. ¹H NMR: 1.30 (3H, t, J=7.12 Hz), 2.09 (3H, s), 2.31 (3H, s), 4.26 (2H, q, J=7.119 Hz), 4.47 (4H, s), 4.65 (2H, s), 6.50 (IH, d, J= 2.967m Hz), 6.67 (IH, d, J=8.52 Hz), 7.07- 7.21(3H, m), 7.37 (2H, d, J-8.199 Hz), 7.44 (IH, s), 7.62 (IH, d, J=7.75 Hz). Yield: 51.62% . Example 33

Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy}-acetate. 1H NMR: 1.30 (3H, t, J=7.14 Hz), 1.93 (3 H, s), 2.31 (3H, s), 4.27 (2H, q, J=14.09 and 7.11Hz).4.56 (2H, t, J=5.04 Hz), 4.64 (4H, m), 6.67 (IH, d, J=8.55 Hz), 7.21 (2H, m), 7.35 (IH, d, J=8.28 Hz), 7.43 (5H, m), 8.00 (2H, d, J=7.683 Hz)₁ Yield: 45 %

Example 34

Ethyl-{4-[l-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxyimino)-ethyl]-2-methyl- phenoxy } -acetate.

¹H NMR: 1.29 (3H, t, J=7.11 Hz), 1.36 (9H, s), 2.19 (3H, s), 2.30 (3H, s), 2.36 (3H, s), 4.26 (2H, q, J=14.25 and 7.17 Hz), 4.64 (2H, s), 5.03 (2H, s), 6.66 (IH, d, J=8.52 Hz), 7.39 (IH, d, J=8.34 Hz), 7.48 (IH, s). Yield: 66 %

Example 35

Ethyl-{4-[l-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-ylmethoxyimino)-ethyl]-2-methyl- phenoxy} -acetate.

¹H NMR: 1.2 (3H, t, J=7.1 Hz), 1.3 (9H, s), 2.2 (3H, s), 2.3 (3H, s), 2.4 (3H, s), 4.2 (2H, q, J=7.1 Hz), 4.6 (2H, s), 5.1 (2H, s), 6.4 (IH, s), 6.7 (IH, d, J=8.5 Hz), 7.2 (2H₅ m), 7.4 (4H, m). Yield: 93% Example 36

Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-2-phenyl-ethyl]- phenoxy} -acetate.

¹H NMR: 1.2 (3H, t, J=7.1 Hz), 2.2 (3H, s), 2.39 (3H, s), 2.41 (3H, s), 4.1 (2H, s), 4.2 (2H, q, J=7.1 Hz), 4.6 (2H, s), 5.3 (2H, s), 6.6 (IH, d, J=8.5 Hz), 7.1-7.2 (2H, m), 7.3 (5H, m), 7.4 (IH, d, J=8.2 Hz), 7.5 (IH, s), 7.9 (2H, d, J=7.9 Hz). Yield: 86%

Example 37

Ethyl- {2-methyl-4-[2-phenyl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} - acetate. ¹H NMR: 1.3 (3H, t, J=7.1 Hz), 2.3 (3H, s), 4.1 (2H, s), 4.2 (2H, q, J=7.1 Hz), 4.6 (2H, ■ s), 5.3 (2H, s), 6.6 (IH, d, J=8.5 Hz), 7.1-7.2 (5H, m), 7.3 (3H, m), 7.4 (IH, s), 7.5 (2H, d, J=7.9 Hz). Yield: 58% Example 38

Ethyl-{2-methyl-4-[(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-phenyl-methyl]- phenoxy} -acetate.

¹H NMR: 1.26 (3H, t, J=7.1 Hz), 2.26 (3H, s), 2.38 (3H, s), 2.42 (3H, s), 4.2 (2H, q, J=7.1 Hz), 6.64 (2H, d, J=6.57 Hz), 5.11 (2H, d, J=6.06 Hz), 6.63 (IH, dd, J=25.0 and 9.18 Hz), 7.14-7.37(8H, m), 7.45 (IH, d, J=7.83 Hz), 7.87 (2H, dd, J=8.01 and 5.7 Hz). Yield: 81 %

Example 39

Ethyl-(2-methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-2-phenyl-ethyl}-phenoxy)-acetate. 1U NMR: 1.3 (3H, t, J=7.1 Hz), 2.3 (3H, s), 2.5 (3H, s), 4.1 (2H, s), 4.2 (2H, q, J=7.1 Hz), 4.6 (2H, s), 5.3 (2H, s), 6.6 (IH, d, J=8.5 Hz), 7.1-7.2 (5H, m), 7.4 (IH, d, J=8.4 Hz), 7.5 (IH, s), 7.6 (2H, d, J=8.1 Hz), 8.0 (2H, d, J=8.0 Hz). Yield: 73%

Example 40 Ethyl-(4-{cyclohexyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol- 5ylmethoxyimino]-methyl}-2-methyl-phenoxy)-acetate.

¹H NMR: 1.26-1.31 (9H, m), 1.67-1.79 (4H, m), 2.28 (3H, s), 2.46 (4H, s), 4.26 (2H, q, J=7.11 Hz), 4.63 (2H, s), 5.13 (2H, s), 6.66 (IH, d, J=8.1 Hz), 6.99 (2H, m), 7.67 (2H, d, J=8.2 Hz), 8.02 (2H, d, J=8.1 Hz). Yield: 31.26%

Example 41

Ethyl-{4-[cyclohexyl-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-methyl]-2- methyl-phenoxy} -acetate. .

¹H NMR: 1.2-1.3 (9H, m), 1.7 (5H, m), 2.2 (3H, s), 2.3 (3H, s), 2.3 (3H, s), 4.2 (2H, q, J=7.1 Hz), 4.6 (2H, s), 4.9 (2H, s), 6.6 (IH, d, J=8.1 Hz), 7.0 (2H, m), 7.2 (2H, s), 7.8 (2H, d, J=8.0 Hz) Yield: 58 %

Example 42 Ethyl- {4-[ 1 -(2-carbazol-9-yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy } - acetate.

¹H NMR: 1.3 (3H, t, J=7.1 Hz), 2.3 (3H, s), 3.8 (2H, s), 4.2 (2H, q, J=7.1 Hz), 4.6-4.7

(6H, m), 6.6 (IH, d, J=8.5 Hz), 7.0 (2H, m), 7.1 (3H, m), 7.3 (3H₅ m), 7.4 (5H, m), 8.0 (2H, d, J=7.7 Hz).

Yield: 35%

Example 43

Ethyl-{4-[l-(2-indol-l-yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetate.

¹H NMR: 1.3 (3H, t, J=7.1 Hz), 2.3 (3H, s), 4.0 (2H, s), 4.2 (2H, q, J=7.1 Hz), 4.5 (4H, m), 4.6 (2H, s), 6.5 (IH, d, J=2.8 Hz), 6.6 (IH, d, J=8.5 Hz), 7.0 (IH, d, J=3.0 Hz), 7.1

(3H, m), 7.2 (4H, m), 7.3 (2H, m), 7.5 (IH, s), 7.6 (IH, d, J=7.8 Hz).

Yield:60%

Example 44

Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-butyl]-phenoxy}- acetate.

¹H NMR: 0.91 (3H, t, J=7.29 Hz), 1.29 (3H, t, J=7.14 Hz), 1.48-1.62 (2H, m), 2.71

(3H, s), 2.30 (3H, s), 2.46 (3 H, s), 2.67 (2H, t, J= 6.6 Hz), 4.26 (2H, q, J=I 4.46 and

7.16 Hz), 4.64 (2H, s), 5.30 (2H, s), 6.65 (IH, d, J=8.52 Hz), 7.23 (2H, m), 7.37 (IH, d,

J=8.4 Hz), 7.46 (IH, s), 7.90 (2H, d, J=8.07 Hz). Yield: 62.4%

Example 45

Ethyl- {4-[ 1 -(2-carbazol-9-yl-ethoxyimino)-butyl]-2-methyl-phenoxy} -acetate.

¹U NMR: 0.76 (3H, t, J=7.32 Hz), 1.27 (5H, m), 2.26 (3H, s), 2.44 (2H, t, J=7.65 Hz),

4.26 (2H, q, J=14.52 and 7.11 Hz), 4.54 (2H, t, J=5.16 Hz), 4.65 (4H, m), 6.67 (IH, d, J=8.52 Hz), 7.20-7.24 (2H, m), 7.31-7.34 (IH, d, J=14.64 Hz), 7.43-7.47 (5H, m), 8.09

(2H, d, J=7.72 Hz).

Yield: 40%

Example 46

Ethyl-{4-[l-(2-fluoro-benzyloxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetate. ¹H NMR: 1.27 (3H, t, J=7.11 Hz), 2.25 (3H, s), 4.12 (2H, s), 4.24 (2H, q, J=7.11 Hz),

4.61 (2H, s), 5.31 (2H, s), 6.6 (IH, d, J=8.52 Hz), 7.2 (2H, m), 7.2 (5H, m), 7.3 (3H, m).

Yield: 64.64%

Example 47 Ethyl-{4-[l-(2-indol-l-yl-ethoxyimino)-butyl]-2-methyl-phenoxy}-acetate. 1H NMR: 0.87 (3H, t, J=7.32 Hz), 1.30 (3H, t, J=7.14 Hz), 1.40-7.47 (2H, m), 2.31 (3H, s), 2.58 (2H, t, J=7.44 Hz), 4.26 (2H, q, J=14.22 and 7.08 Hz), 4.46 (4H, s), 4.65 (2H, s), 6.50 (IH, d, J=2.97 Hz), 6.67 (IH, d, J=8.52 Hz), 7.07-7.12 (2H, m), 7.17-7.20 (IH, m), 7.33-7.42 (3H, m), 7.63 (IH, d, J=7.86 Hz). Yield: 24%

Example 48

Ethyl-{4-[l-(2-indol-l-yl-ethoxyimino)-propyl]-phenoxy}-acetate. 1H NMR: 1.0 (3H, t, J = 7.6 Hz), 1.3 (3H, t, J = 7.1 Hz), 2.63 (2H, q, J = 7.6 Hz), 4.26 (2H, q, J = 7.1 Hz), 4.46 (4H, s), 4.64 (2H, s), 6.5 (IH, d, J = 2.97 Hz), 6.91 (2H, dd, J = 2.0 and 6.9 Hz), 7.11 (2H, m), 7.19 (IH, m), 7.36 (IH, d, J = 8.16 Hz). 7.55 (2H, d, J = 2.0 and 6.9 Hz), 7.6 (IH, d, J = 7.86 Hz). Yield: 31 %

Example 49 Ethyl- {4-[cyclohexyl-(2-indol- 1 -yl-ethoxyimino)-methyl] -2 -methyl -phenoxy} -acetate. ¹H NMR: 1.23-1.32 (9H, m), 1.76 (4H, m), 2.21 (3H, s), 2.36 (IH, m), 4.26 (4H, m), 4.37 (2H, t, J=5.20 Hz), 4.61 (2H, s), 6.46 (IH, m), 6.58 (IH, d, J-8.06 Hz), 6.83 (2H, m), 7.01 (IH, m), 7.05-7.20 (2H, m), 7.32 (IH, d, J=8.1 Hz), 7.61 (IH, d, J=7.74 Hz). Yield: 22.16% Example 50

Ethyl- {2-methyl-4-[ 1 -(4-trifluoromethyl-benzyloxyimino)-butyl]-phenoxy} -acetate ¹H NMR: 0.95 (3H, t, J=7.50 Hz), 1.29 (3H, t, J=7.11 Hz), 1.50-1.60 (2H, m), 2.29 (3H, s), 2.73 (2H, t, J=7.53 Hz), 4.26 (2H, q, J-14.25 and 7.11 Hz), 4.64 (2H, s), 5.24 (2H, s ), 6.64 (IH, d, J=8.52 Hz), 7.36 (IH, dd, J=8.52 and 2.1 Hz), 7.43-7.50 (3H, m), 7.61 (2H, d, J=8.16 Hz). Yield: 90%

Example 51

Ethyl-{4-[cyclohexyl-(4-trifluoromethyl-benzyloxyimino)-methyl]-2-methyl- phenoxy} -acetate. 1H NMR: 1.08-1.32 (9H, m), 1.75 (4H, m), 2.29 (3H, s), 2.40 (IH, m), 4.27 (2H, q, J=7.12 Hz), 4.64 (2H, s), 5.08 (2H, s), 6.68 (IH, d, J=8.92 Hz), 7.01 (2H, m), 7.36 (2H, d, J=8.03 Hz), 7.56 (2H, d, JN8.09 Hz). Yield: 45.2377%

Example 52 Ethyl-{4-[2-cyclopentyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetate.

¹H NMR: 1.1-1.2 (2H, m), 1.3 (3H, t, J=7.2 Hz), 1.4 (2H, m), 1.6 (4H, m), 2.0 (IH, m),

2.3 (3H, s), 2.8 (2H, d, J=7.6 Hz), 4.2 (2H, q, J=7.2 Hz), 4.6 (2H, s), 5.2 (2H, s), 6.6 (IH, d, J=8.8 Hz), 7.3 (IH, dd, J=8.6 and 2.2 Hz), 7.4 (IH, d, J=2.0 Hz), 7.5 (2H, d,

J=8.4 Hz), 7.6 (2H, d, J=8.4 Hz).

Yield: 78%

Example 53

Ethyl-{4-[2-cyclohexyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetate.

¹H NMR: 1.0 (2H, m), 1.1 (2H, m), 1.3 (3H, t, J=7.2 Hz), 1.6 (7H, m), 2.3 (3H, s), 2.7

(2H, d, J=7.2 Hz), 4.2 (2H, q, J=7.2 Hz), 4.6 (2H, s), 5.2 (2H, s), 6.6 (IH, d, J=8.8 Hz),

7.3 (IH, dd, J=8.8 and 2.4 Hz), 7.4-7.5 (3H, m), 7.6 (2H, d, J=8.0 Hz).

Yield: 70% Example 54

{2-Methyl-4-[l-(2-oxo-3-phenyl-oxazolidin-5-ylmethoxyimino)-ethyl]-phenoxy}- acetate

¹H NMR: 1.3 (3H, t, J=7.1 Hz), 2.1 (3H, s), 2.3 (3H, s), 4.0 (IH, m), 4.1 (IH, t, J=8.8

Hz), 4.2 (2H, q, J=7.1 Hz), 4.4 (2H, m), 4.6 (2H, s), 5.0 (IH, m), 6.6 (IH, d, J=8.5 Hz), 7.1 (IH, t, J=7.3 Hz), 7.3-7.4 (4H, m), 7.5 (2H, d, J=7.9 Hz).

Yield: 40%

Example 55

Ethyl-{4-[l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenyl}-acetate.

¹HNMR: 1.24 (3H, t, J=7.2 Hz), 2.27 (3H, s), 3.61 (2H, s), 4.14 (2H, q, J=7.2 Hz), 5.27 (2H, s), 7.25 (2H, m), 7.50 (2H, m), 7.57-7.63 (4H, m).

Yield: 37.533%

Example 56

Ethyl-{4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenyl}-acetate.

¹H NMR: 1.24 (3H, t, J=5.4 Hz), 2.23 (3H, s), 2.38 (3H, s), 2.47 (3H, s), 3.61(2H, s), .14 (2H, q, J=IO and 5.4 Hz), 5.13 (2H, s), 7.23 (2H, d, J=6.0 Hz), 7.27 (2H, d, J=6.3

Hz), 7.60 (2H, d, J=6 Hz), 7.90 (2H, d, J=6.3 Hz).

Yield: 16.4%

Example 57

Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-ethyl]-phenyl}-acetate. ¹H NMR: 1.26 (3H, t, J=5.4 Hz), 1.94 (3H, s), 3.63 (2H, s), 4.15 (2H, q, J=I 0.5 and 5.1 Hz), 4.57 (2H, t, J=3.9 Hz), 4.65 (2H, t, J=4.2 Hz), 7.20-7.24 (2H, m), 7.29 (2H, d, JM6.0 Hz), 7.40- 7.45 (4H, m), 7.54 (2H, d, J=6.3 Hz), 8.10 (2H, d, J=6.3 Hz). Yield: 50% Example 58

Ethyl- {4-[2-(4-chloro-phenyl)- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-niethyl- phenoxy } -acetate.

¹H NMR: 1.28 (3H, t, J=7.0 Hz), 2.26 (3H, s), 4.08 (2H, s), 4.24 (2H, q, J=7.2 Hz), 4.26 (2H, s), 5.26 (2H, s), 6.62 (IH, d, J=8.8 Hz), 7.08 (2H, d, J=8.4 Hz), 7.17-7.21 (2H, m), 7.32-7.35 (IH, m), 7.4 (2H, d, J=8.0 Hz), 7.46-7.47 (IH, m), 7.58 (2H, d, J=8.0 Hz). Yield: 40.72%

Example 59

Ethyl-{2-methyl-4-[2-thiophen-3-yl-l-(4-trifluoroniethyl-benzyloxyimino)-ethyl]- phenoxy} -acetate. 1H NMR: 1.3 (3H, t, J=7.2 Hz), 2.2 (3H, s), 4.1 (2H, s), 4.2 (2H, q, J=7.2 Hz), 4.6 (2H, s), 5.3 (2H, s), 6.6 (IH, d, J=8.8 Hz), 6.9 (2H, m), 7.2 (IH, m), 7.4 (3H, m), 7.5 (IH, d, J=I.6 Hz), 7.6 (2H, d, J=8.0 Hz). Yield: 68%

Example 60 {4-[l -(2 -p-Tolyl-ethoxyimino)-propyl]-phenoxy} -acetic acid.

To a solution of ethyl-{4-[l-(2-p-tolyl-ethoxyimino)-propyl]-phenoxy}-acetate (prepared in Example 14) (1.9 g) in a mixture of tetrahydrofuran (30 mL) and methanol (10 mL) was added another solution Of LiOH-H₂O (430 mg) in water (10 mL) and the reaction mixture was stirred at ambient temperature for about 16-18 hours. Solvent was evaporated under reduced pressure, water was added to the residue, acidified with IN HCl to pH 6 and extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried over sodium sulphate and evaporated under reduced pressure. Crude product was chromatographed (flash) over silica-gel using 25 % ethyl acetate in hexane as an eluent to obtain 1.6 g of pure product. 1H NMR: 1.1 (3H, t, J = 7.6 Hz), 2.32 (3H, s), 2.7 (2H, q, J = 7.6 Hz), 3.0 (2H, t, J= 7.0 Hz), 4.34 (2H, t, J = 7.0 Hz), 4.6 (2H, s), 6.9(2H, d, J = 8.8 Hz), 7.1 (4H, m), 7.6 (2H, d, J = 8.8 Hz). Yield: 91 % The following compounds are prepared by procedure similar to that described in example 60 with appropriate variations of reactants, reaction conditions and quantities of reagents

Example 61 (4- { 1 -[2-(4-Methoxy-phenyl)-ethoxyimino]-propyl} -phenoxy)-acetic acid.

¹H NMR: 0.95 (3H, t, J = 7.4 Hz), 2.6 (2H, q, J = 7.5 Hz), 2.87 (2H, t, J = 6.7 Hz), 3.69

(3H, s), 4.2 (2H, t, J = 6.7 Hz), 4.3 (2H,s), 6.84 (4H, m), 7.1 (2H, d, J = 8.5 Hz), 7.5

(2H, d, J = 8.8 Hz).

Yield: 92 % Example 62

{4-[l-(4-Methoxy-benzyloxyimino)-propyl]-phenoxy}-acetic acid.

¹H NMR: 1.0 (3H, t, J = 7.4 Hz), 2.65 (2H, q, J = 7.4 Hz), 3.72 (3H, s), 4.3 (2H, s), 5.04

(2H, s), 6.83 (2H, d, J = 8.8 Hz), 6.92 (2H, d, J = 8.6 Hz), 7.3 (2H, d, J = 8.6 Hz), 7.5

(2H, d, J = 8.8 Hz). Yield: 95 %

Example 63

(4- { 1 - [2-(4-Tr ifluoromethy l-phenyl)-ethoxyimino] -propyl } -phenoxy)-acetic acid.

¹H NMR: DMSO-D6, 0.91 (3H, t, J = 7.4 Hz), 2.60 (2H, q, J = 7.4 Hz), 3.06 (2H, t, J -

6.3 Hz), 4.32 (2H, t, J = 6.4 Hz), 4.61 (2H, s), 6.9 (2H, d, J = 8.68 Hz), 7.46 - 7.54 (4H, m), 7.65 (2H, d, J = 8.04Hz).

Yield: 85 %

Example 64

(4-{l-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]-propyl}- phenoxy)-acetic acid. 1H NMR: DMSO-D6, 1.00 (3H, t, J = 7.4 Hz), 2.4 (3H, s), 2.66 (2H, q, J = 7.4 Hz), 4.7

(2H, s), 5.35 (2H, s), 6.95 (2H, d, J = 8.7 Hz), 7.6 (2H, d, J = 8.7 Hz), 7.83 (2H, d, J =

8.3 Hz), 8.1 (2H, d, J = 8.2Hz).

Yield: 88 %

Example 65 {4-[l-(5-Methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetic acid.

¹H NMR: DMSO-D6, 1.00 (3H, t, J = 7.4 Hz), 2.34 (3H, s), 2.43 (3H, s), 2.67 (2H, q, J

= 7.4 Hz), 4.69 (2H, s), 5.35 (2H, s), 6.9 (2H, d, J = 8.79 Hz), 7.3 (2H, d, J = 8.1 Hz),

7.59 (2H, d, J = 8.79 Hz), 7.821 (2H, d, J = 8.1Hz).

Yield: 90 % Example 66

{4-[l-(5rMethyl-2-phenyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetic acid.

¹H NMR: DMSO-D6, 1.0 (3H, t, J = 7.4 Hz), 2.45 (3H, s), 2.67 (2H, q, J = 7.4 Hz),

4.69 (2H, s), 5.04 (2H, s), 6.90 (2H, d, J = 8.79 Hz), 7.50 (3H₅ m), 7.59 (2H, d, J = 8.79 Hz), 7.93 (2H, m).

Yield: 79 %

Example 67 ' {4-[ 1 -(2-tert-Butyl-5-methyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy} -acetic acid.

¹H NMR: DMSO-D6, 0.99 (3H, t, J = 7.4 Hz), 1.27 (9H, s), 2.30 (3H, s), 2.65 (2H, q, J = 7.4 Hz), 4.68 (2H, s), 4.91 (2H, s), 6.9 (2H, d, J = 8.8 Hz), 7.58 (2H, d, J = 8.8 Hz).

Yield: 71 %

Example 68

{4-[ 1 -(4-Trifluoromethyl-benzyloxyimino)-propyl]-phenoxy} -acetic acid.

¹H NMR: DMSO-D6, 1.0 (3H, t, J = 7.48 Hz), 2.76 (2H, q, J = 7.48 Hz), 4.67 (2H,s), 5.25 (2H, s), 6.9 (2H, d, J = 8.78 Hz), 7.5 - 7.6 (4H, m), 7.74 (2H, d, J = 8.1Hz).

Yield: 95 %

Example 69

(2-Methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- ethyl}-phenoxy)-acetic acid. 1H NMR: DMSO-D6, 1.89 (3H,s), 1.96 (3H, s), 2.46 (3H. s), 4.66 (2H, s), 5.33 (2H, s),

6.8 (IH, d, J = 8.6 Hz), 7.41 (IH, d, J = 8.5 Hz), 7.47 (IH, s), 7.8 (2H, d, J = 8.3 Hz),

8.0 (2H, d, J = 8.1Hz).

Yield: 92 %

Example 70 {2-Methyl-4-[l-(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}-acetic acid.

¹H NMR: DMSO-D6, 2.14 (3H, s), 2.21 (3H, s), 2.47 (3H, s), 4.73 (2H, s), 5.05 (2H, s),

6.85 (IH, d, J = 8.6 Hz), 7.4 (IH, d, J = 8.6 Hz), 7.5 (4H, m), 7.95 (2H, m).

Yield: 94 % Example 71

{2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}-acetic acid. ¹H NMR: DMSO-D6, 2.13 (3H, s), 2.20 (3H, s), 2.35 (3H, s), 2.46 (3H, s), 4.73 (2H, s),

5.0 (2H, s), 6.85 (IH, d, J = 8.6 Hz), 7.33 (2H, d, J = 7.98 Hz), 7.44 (IH, d, J = 8.6 Hz),

7.49 (IH, s), 7.84 (2H, d, J = 8.0 Hz).

Yield: 92 % Example 72

{2-Methyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy}-acetic acid.

¹H NMR: 2.15 (3H, s), 2.17 (3H, s), 4.46 (2H, s), 5.23 (2H, s), 6.58 (IH, d), 7.26 (2H, s), 7.50 (2H, d), 7.6 (2H, d).

Yield: 46% Example 73

(2-Methyl-4-{l-[2r(3-oxo-2,3-dihydro-benzo[l,4]oxazin-4-yl)-ethoxyimino]-ethyl}- phenoxy)-acetic acid.

¹H NMR: 2.0 (3H, s), 2.2 (3H, s), 4.25 (2H, t, J=6.3 Hz), 4.40 (2H, t, J=6.3 Hz), 4.5

(2H, s), 4.6 (2H, s), 6.60 (IH, d, J=8.5 Hz), 6.90 (3H, s), 7.15 (IH, t), 7.30 (IH, d), 7.50 (IH, s).

Yield: 66.99%

Example 74

{2-Methyl-4-[l -(2-phenoxazin-10-yl-ethoxyimino)-ethyl]-phenoxy}-acetic acid. .

¹H NMR: 2.11(3H, s), 2.29 (3H, s), 3.87 (2H, t, J=6.27 Hz), 4.38 (2H, t, J=6.33 Hz), 4.67(2H, s), 6.59-6.78 (9H, m), 7.39 (IH, d, J= 8.49 Hz), 7.49 (IH, s).

95 %

Example 75

[2-Methyl-4-(l-{2-[2-methyl-5-(4-methylsulfanyl-phenyl)-pyrrol-l-yl]-ethoxyimino}- ^■ ethyl)-phenoxy] -acetic acid. 1H NMR: 2.08 (3H, s), 2.30 (3H, s), 2.34 (3H, s), 2.45 (3H, s), 4.22 (4H, m), 4.70 (2H, s), 5.96 (IH, d, J=3.09 Hz), 6.00 (IH, d, J=3.33 Hz), 6.69 (IH, d ,J= 8.61 Hz), 7.21-

7.34 (5H, m), 7.38 (IH, s).

Yield: 11 %

Example 76 {4-[l-(2-Fluoro-benzyloxyimino)-ethyl]-2-methyl-phenoxy}-acetic acid.

¹U NMR: 2.22 (3H, s), 2.30 (3H, s), 4.70 (2H, s), 5.29 (2H, s), 6.71 (IH, d, J= 8.58

Hz), 7.03-7.15 (2H, m), 7.41-7.48 (3H, m), 7.49 (IH, s)

Yield: 38.74%

Example 77 {4-[l-(2-Indol-l-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy} -acetic acid.

¹H NMR: 2.09 (3H, s), 2.30 (3H, s), 4.46 (4H, s), 4.69 (2H, s), 6.50 (IH, d, J=3.18 Hz),

6.711 (IH, d, J=8.55 Hz), 7.07-7.21 (3H, m), 7.37 (2H, d, J=8.22 Hz), 7.44 (IH, s),

7.62 (IH, d, J=7.74 Hz) Yield: 59.75%

Example 78

{4-[l -(2-Carbazol-9-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy} -acetic acid.

¹H NMR: 1.79 (3H, s), 2.16 (3H, s), 4.46 (2H, t, J=4.74 Hz), 4.70 (4H, s), 6.77 (IH, d,

J=8.49 Hz), 7.17 (2H, t, J=7.44 Hz), 7.27 (2H, m), 7.39 (2H, t, J=7.89 Hz), 7.57 (2H d, J=8.19 Hz), 8.13 (2H, d, J=7.65 Hz).

Yield: 61 %

Example 79

{4-[l-(2-tert-Butyl-5-methyl-oxazol-4-ylmethoxyimino)-ethyl]-2-methyl-phenoxy}- acetic acid. 1H NMR: 1.32 (9H, s), 2.13 (3H, s), 2.27 (3H, s), 2.35 (3H, s), 4.56 (2H, s), 5.04 (2H, s), 6.56 (IH, d, J=8.55 Hz), 7.30 (IH, m), 7.45 (IH, s).

Yield: 80 %

Example 80

{4-[l-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-ylmethoxyimino)-ethyl]-2-methyl- phenoxy} -acetic acid.

¹H NMR: 1.3 (9H, s), 2.2 (3H, s), 2.3 (3H, s), 2.4 (3H, s), 4.6 (2H, s), 5.1 (2H, s), 6.4

(IH, s), 6.7 (IH, d, J=8.5 Hz), 7.2 (2H, m), 7.4 (4H, m).

Yield: 88 %

Example 81 {2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-2-phenyl-ethylj- phenoxy} -acetic acid.

¹H NMR: 2.23 (3H, s), 2.38 (3H, s), 2.4 (3H, s), 4.0 (2H, s), 4.6 (2H, s), 5.1 (2H, s), 6.5

(IH, d, J=8.5 Hz), 7.1 (4H, m), 7.2 (3H, m), 7.3 (IH, d, J=8.4 Hz), 7.5 (IH, s), 7.9 (2H, d, J=7.9 Hz). Yield: 58 %

Example 82

{2-Methyl-4-[2 -phenyl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} -acetic acid. ¹H NMR: 2.2 (3H, s), 4.1 (2H, s), 4.6 (2H, s), 5.2 (2H, s), 6.6 (IH, d, J=8.5 Hz), 7.2

(5H, m), 7.4 (3H, m), 7.5 (IH, s), 7.5 (2H, m).

Yield: 53 %

Example 83 {2-Methyl-4-[(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-phenyl-methyl]- phenoxy} -acetic acid.

¹H NMR: 2.25 ( 3H, s), 2.37 (3H, s), 2.45 (3H, s), 4.57 (2H, s), 5.11 (2H, s), 6.72 (IH, d, J=8.68 Hz), 7.12 (3H, s), 7.29-7.32 ( 4H, m), 7.45 ( 2H, d, J=7.5 Hz), 7.88 (2H, d,

J=7.65 Hz). Yield: 16 %

Example 84

(2-Methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]-2- phenyl-ethyl}-phenoxy)-acetic acid.

¹H NMR: 2.2 (3H, s), 2.5 (3H, s), 4.0 (2H, s), 4.6 (2H, s), 5.3 (2H, s), 6.6 (IH, d, J=8.5 Hz), 7.1 (5H, m), 7.4 (IH, d, J=8.4 Hz), 7.5 (IH, s), 7.6 (2H, d, J=8.1 Hz), 8.0 (2H, d,

J=8.1 Hz).

Yield: 91 %

Example 85

(4-{Cyclohexyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- methyl} -2 -methyl -phenoxy)-acetic acid.

¹H NMR: 1.25 (6H, m), 1.71 (4H, m), 2.22 (3H, s), 2.47 (4H, m), 4.57 (2H, s), 5.10

(2H, s), 6.67 (IH, d, J=8.34 Hz), 6.97 (2H, s), 7.65 (2H, d, J=8.25 Hz), 7.98 (2H, d,

J=7.98 Hz).

Yield: 62.5% Example 86

{4-[Cyclohexyl-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-methyl]-2-methyl- phenoxy} -acetic acid.

¹H NMR: 1.23 (8H, m), 2.16 (3H, m), 2.32 (3H, s), 2.34 (3H, s), 2.36 (3H, s),4.88 (2H, s), 5.01 (2H, s), 6.66 (IH, m), 6.9 (IH, m), 7.0 (IH, m), 7.1 (2H, m), 7.78 (IH₅ m), 7.88 (IH, d, J=7.62 Hz)

Yield: 80 %

Example 87

{4-[l-(2-Carbazol-9-yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetic acid. ¹H NMR: 2.0 (3H, s), 3.8 (2H, s), 4.6 (6H, m), 6.6 (IH, d, J=8.5 Hz), 6.9 (2H, m), 7.1

(3H, m), 7.2-7.3 (3H, m), 7.4 (5H, m), 8.0 (2H, d, J=7.7 Hz).

Yield: 90 %

Example 88 {4-[l-(2-Indol- 1 -yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetic acid.

¹H NMR: 2.1 (3H, s), 3.9 (2H, s), 4.1 (2H, s), 4.46 (4H. m), 6.4 (IH, d, J=2.4 Hz), 6.6

(IH, d, J=8.5 Hz), 7.0-7.1 (7H, m), 7.2-7.3 (3H, m), 7.4 (IH, d, J=8.1 Hz), 7.5 (IH, d,

J=7.7 Hz).

Yield: 75% Example 89

{2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-butyl]-phenoxy}-acetic acid.

¹H NMR: 0.91(3H, t, J=7.32 Hz), 1.49 (2H, m), 2.30 (3H, s), 2.39 (3H, s), 2.46 (3H,s),

2.68 (2H, t, J=7.5 Hz), 4.66 (2H, s), 5.11(2H, s), 6.67 (IH, d, J= 8.53 Hz), 7.22 (2H, s), 7.37 (IH, d, J=8.46 Hz), 7.46 (IH, s), 7.89 (2H, d, J=8.04 Hz).

Yield: 68 %

Example 90

{4-[ 1 -(2-Carbazol-9-yl-ethoxyimino)-butyl]-2-methyl-phenoxy} -acetic acid.

¹H NMR: 0.76 (3H, t, J=7.32 Hz), 1.28 (2H, m), 2.30 (3H, s), 2.44 (2H, t, J=7.92 Hz), 4.54 (2H, t, J=5.01Hz), 4.65 (2H, t, J=5.37 Hz), 4.70 (2H, s), 6.70 (IH, d, J= 8.53 Hz),

7.19-7.24 (2H, m), 7.33 (IH, d, J=8.58 Hz), 7.39 (IH, s), 7.44 (4H, m), 8.10 (2H,d,

J=7.77Hz).

Yield: 85 %

Example 91 {4-[l-(2-Fluoro-benzyloxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetic acid.

¹H NMR: 2.22 (3H, s), 4.12 (2H, s), 4.60 (2H, s), 5.31 (2H, s), 6.59 (IH, d, J=8.53 Hz),

7.0-7.2 (1OH, complex), 7.4 (IH, s).

Yield: 36 %

Example 92 {4-[l-(2-Indol-l-yl-ethoxyimino)-butyl]-2-methyl-phenoxy}-acetic acid.

¹H NMR: 0.85 (3H, t, J=7.29 Hz), 1.38-1.46 (2H, m), 2.28 (3H, s), 2.57 (2H, t, J=7.47

Hz), 4.44 (4H, s), 4.65 (2H, s), 6.48 (IH, d, J= 2.91 Hz), 6.69 (IH, d, J=8.49 Hz), 7.07-

7.12 (2H, m), 7.19 (IH, t, J=7.5 Hz), 7.33-7.41 (3H, m), 7.63 (IH, d, J=7.4 Hz).

Yield: 59 % Example 93

{4-[Cyclohexyl-(2-indol- 1 -yl-ethoxyimino)-methyl] -2-methyl-phenoxy} -acetic acid.

¹H NMR: 1.13 (8H, m), 1.23-1.30 (2H, m), 2.20 (3H, s), 2.38 (IH, m), 4.28 (2H, t,

J=5.14 Hz), 4.37 (2H, t, J=5.02 Hz), 4.63 (2H, s), 6.46 (IH, m), 6.62 (IH, d, J=8.28 Hz), 6.80-6.85 (2H, m), 7.01 (IH, m), 7.05-7.20 (2H, m), 7.32 (IH, d, J=8.07 Hz), 7.61

(IH, d, J=7.44 Hz).

Yield: 88.71%

Example 94

{2-Methyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-butyl]-phenoxy} -acetic acid. ¹H NMR: 0.85 (3H, t, J=7.05 Hz), 1.49-1.62 (2H, m), 2.29 (3H, s), 2.73 (2H, t, J=7.53

Hz), 4.69 (2H, s), 5.24 (2H, s), 6.69 (IH, d, J=8.49 Hz), 7.37 (IH, d, J=8.49), 7.48 (3H, m), 7.61(2H, d, J=8.13 Hz).

Yield: 83%

Example 95 {4-[Cyclohexyl-(4-trifluoromethyl-benzyloxyimino)-methyl]-2-methyl-phenoxy}- acetic acid.

¹H NMR: 1.1-1.3 (6H, m), 1.7-1.9 (4H, m), 2.28 (3H, s), 2.40 (IH, m), 4.68 (2H, s),

5.07 (2H, s), 6.71 (IH, d, J=8.88 Hz), 7.00 (2H, m), 7.36 (2H, d, J=7.92 Hz), 7.56 (2H, d, J=8.05 Hz). Yield: 98.4%

Example 96

{4-[2-Cyclopentyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl-phenoxy}- acetic acid. ,

¹H NMR: 400MHz, 1.1 (2H, m), 1. (2H, m), 1.6 (4H, m), 2.0 (IH, m), 2.3 (3H, m), 2.8 (2H, d, J=7.6 Hz), 4.7 (2H, s), 5.2 (2H, s), 6.7 (IH, d, J=8.4 Hz), 7.3 (IH, dd, J=8.4 and

2.0 Hz), 7.4 (IH, d, J=I.6 Hz), 7.5 (2H, d, J=8.0 Hz), 7.6 (2H, d, J=8.4 Hz).

Yield: 73%

Example 97

{4-[2-Cyclohexyl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl-phenoxy} - acetic acid.

¹H NMR: 400MHz, 1.0 (2H, m), 1.1 (3H, m), 1.6 (6H, m), 2.3 (3H, m), 2.7 (2H, d,

J=6.8 Hz), 4.7 (2H, s), 5.2 (2H, s), 6.7 (IH, d, J=8.4 Hz), 7.3 (IH, dd, J=8.4 and 2.0

Hz), 7.4 (IH, d, J=1.6 Hz), 7.5 (2H, d, J=8.0 Hz), 7.6 (2H, d, J=8.0 Hz).

Yield: 59% Example 98

{4-[l-(4-Trifluoromethyl-benzyloxyimino)-ethyl]-phenyl}-acetic acid.

¹H NMR: 400MHz, 2.25 (3H, s), 3.62 (2H, s), 5.27 (2H, s), 7.24 (2H, s), 7.49 (2H, d,

J=8.0 Hz), 7.59 (4H, t, J=8.6 Hz). Yield: 73.27%.

Example 99

{4-[l-(5-Methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenyl}-acetic acid.

¹H NMR: 400MHz, 2.20 (3H, s), 2.38 (3H, s), 2.46 (3H, s), 3.64 (2H, s), 5.12 (2H, s),

7.23 (2H, d, J=6 Hz), 7.27 (2H, d, J=6.6 Hz), 7.59 (2H, d, J=6.0 Hz), 7.89 (2H, d, J=6.3 Hz).

Yield: 80%

Example 100

{4-[ 1 -(2 -Carbazol-9-yl-ethoxyimino)-ethyl]-phenyl} -acetic acid.

¹H NMR: 400MHz, 1.96 (3H, s), 3.68 (2H, s), 4.57 (2H, t, J=7.5 and 3.6 Hz), 4.65 (2H, t, J=7.5 and 3.6 Hz), 7.25 (2H, m), 7.30 (2H, d, J=6.3 Hz), 7.42 (4H, m), 7.56 (2H, d,

J=6.3 Hz), 8.09 (2H, d, J=0.6 Hz)

Yield: 51%

Example 101

(4-{l-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxy)-propoxyimino]-2-phenyl-ethyl}-2- methyl-phenoxy)-acetic acid.

¹H NMR: 400MHz, 0.94 (3H, t, J=5.7 Hz), 1.28 (4H, m), 2.19 (2H, t, J= 4.5 Hz), 2.26

(3H, s), 2.56 (3H, s), 4.03 (2H, t, J=4.8 Hz), 4.090 (2H, s), 4.39 ( 2H, t, J=4.5 Hz), 4.60

(2H, s), 6.33 (IH, d, J=6.6 Hz), 6.66 (IH, d, J=6.6 Hz), 7.19 (5H, m), 5.41 (IH, d,

J=1.5 Hz), 7.52 (2H, dd, J=10.5 and 3.9 Hz), 12.73 (IH, s). Yield: 53%

Example 102

{4-[2-(4-Chloro-phenyl)-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetic acid.

¹H NMR: 400MHz, 2.25 (3H, s), 4.08 (2H, s), 4.65 (2H, s), 5.26 (2H, s), 6.64 (IH, d, J=8.8 Hz), 7.07 (2H, d, J=8.4 Hz), 7.20 (2H, d, J=8.4 Hz), 7.33-7.36 (IH, m), 7.4 (2H, d, J=8.0 Hz), 7.47 (IH, m), 7.58 (2H, d, J=8.4 Hz).

Yield: 81.39%

Example 103 {2-Methyl-4-[2-thiophen-3-yl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy}- acetic acid.

¹H NMR: 400MHz, 2.2 (3H, s), 4.1 (2H, s), 4.6 (2H, s), 5.3 (2H, s), 6.6 (2H, d, J=8.4

Hz), 6.9 (2H, m), 7.2 (IH, m), 7.4 (2H, d, J=8.0 Hz), 7.5 (IH, d, J=I.2 Hz), 7.6 (2H, d, J=8.0 Hz).

Yield: 60%

Example 104

Sodium salt of {2-Methyl-4-[2-phenyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]- phenoxy} -acetic acid. To a solution of {2-Methyl-4-[2-phenyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]- phenoxy} -acetic acid (prepared in Example 82) (100 mg) in methanol (2 niL) was added sodium methoxide (11.8 mg) and stirred at 30 ^°C for 0.5 hour. Solvent was evaporated under reduced pressure on a rotavapor, residue was triturated with diethyl ether, filtered and dried under vacum to yield 80 mg of salt. Melting Point 190 ^°C.

Example 105

L-Arginine salt of (2-Methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-ethyl} -phenoxy)-acetic acid.

To a suspension of (2-Methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-ethyl}-phenoxy)-acetic acid (prepared in example 69) (150 mg) in ethanol (10 mL) was added a solution of L-Arginine (52 mg) in water (2 mL) and the reaction mixture was refluxed for 8 hours. Reaction mixture was cooled to 30° C and solid separated was filtered and dried under vacuum to obtain 110 mg of the salt

Melting Point 220 ^°C

Efficacy of the compounds:

Invitro hPPAR α, hPPARγ and hPPARδ activities were determined as per in-house protocols and the results of representative compounds are provided in table 1 below as a proof of the efficacies of the novel class of compounds disclosed above. Table 1

The compounds of the present invention are therefore suitable as hypocholesterolemic, hypolipidaemic, hypolipoproteinemic, anti-obesity and antihyperglycemic agents which may have additional body weight lowering effect.

The pharmaceutical composition is provided by employing conventional techniques. Preferably the, composition is in unit dosage form containing an effective amount of the active component, that is, the compounds of formula (1) according to this invention.

The quantity of active component, that is, the compounds of formula (1) according to this invention, in the pharmaceutical composition and unit dosage form thereof may be varied or adjusted widely depending upon the particular application method, the potency of the particular compound and the desired concentration. Generally, the quantity of active component will range between 0.5% to 90% by weight of the composition.

Claims

Claims:

1. Compounds of the general formula (I),

their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, wherein

'A' represents an optionally substituted single or fused group selected from aryl, heterocyclyl or cycloalkyl groups;

'W represents substituted or unsubstituted linear or branched (d-C₆)alkyl, (C₂- C₆)alkenyl groups, Ri represents optionally substituted linear or branched (C]-C₆)alkyl, (C₃-Ce)cycloalkyl, aryl, aralkyl groups; R₂ represents hydrogen, linear or branched substituted or unsubstituted (Ci-C₆)alkyl ;

R₃ at each occurrence independently represents hydrogen, halo, optionally substituted groups selected from linear or branched (Ci-C₃)alkyl, halo(Ci-C₃)alkyl, (C]-C₃)alkoxy, thio(C]-C₃)alkyl, sulfenyl derivatives, sulfonyl derivatives; R₄ and R₅ may be same or different and independently represents H or (Ci-Ce)alkyl; X represents either a bond or oxygen or the group '-CH₂-'.

2. A compound as claimed in claim 1, wherein 'A' is preferably selected from optionally substituted aryl or heterocyclyl groups.

3. A compound as claimed in claims 1 or 2 wherein the aryl group is selected from a monocyclic or bicyclic aromatic groups.

4. A compound as claimed in claims 1-3 wherein aryl group is an optionally substituted phenyl group.

5. A compound as claimed 1 or 2 wherein the heterocyclcyl group is selected from single or fused mono, bi or tricyclic aromatic or non-aromatic radicals containing one or more hetero atoms selected from O, N or S.

6. A compound as claimed 1, 2 or 5 wherein the heterocyclcyl group is selected from thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, indolinyl, indolyl, pyrazolyl, quinazolinyl, carbazolyl, phenothiazinyl, phenoxazinyl, benzoxazolyl, benzothiazolyl, benzoxazine, oxazolidinone groups.

7. A compound as claimed in claim 1 wherein 'W is selected from (CVC₃)alkyl or (C₂-C₄)alkenyl groups

8. A compound as claimed in any preceding claims, wherein the substituents on 'A' or 'R₁' are independently selected from hydroxyl, oxo, halo, thio, amino, or substituted or unsubstituted groups selected from alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, aryl, aryloxy, aralkyl, aralkoxy, heterocyclyl, acyl, arylamino, aralkylamino, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, aralkoxyalkyl, alkylthio, arylthio, alkylsulfonylamino, alkylsulfonyloxy, alkoxycarbonylamino, aryloxycarbonylamino, aralkyloxycarbonylamino, sulfenyl derivatives, sulfonyl derivatives.

9. A compound as claimed in any preceding claims, wherein the substituents on the substituents on 'A' or 'R₁' are independently selected from hydroxyl, oxo, halo, thio, amino, or substituted or unsubstituted groups selected from alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, aryl, aryloxy, acyl, hydroxyalkyl, alkoxyalkyl, alkylthio, arylthio, alkylsulfonyloxy, alkoxycarbonylamino, aryloxycarbonylamino, aralkyloxycarbonylamino, sulfenyl derivatives, sulfonyl derivatives.

10. A compound as claimed in any preceding claim selected from Ethyl-{4-[l-(3-methyl-4-oxo-3,4-dihydro-quinazolin-2-ylmethoxyimino)-propyl]- phenoxy} -acetate; Ethyl-(4-{ 1 -[3-(4-acetyl-3-hydroxy-2-propyl-phenoxy)-propoxyimino]-2-phenyl- ethyl}-2-methyl-phenoxy)-acetate;

Ethyl-{2-methyl-4-[l-(3-methyl-4-oxo-3,4-dihydro-quinazolin-2-ylmethoxyimino)- ethyl]-phenoxy} -acetate;

Ethyl- {4-[ 1 -(2-p-tolyl-ethoxyimino)-propyl]-phenoxy}-acetate; Ethyl-(4-{l-[2-(4-methoxy-phenyl)-ethoxyimino]-propyl}-phenoxy)-acetate;

Ethyl-{4-[l-(4-methoxy-benzyloxyimino)-propyl]-phenoxy}-acetate;

Ethyl- {4-[ 1 -(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy} -acetate;

Ethyl-{4-[l-(2-tert-butyl-5-methyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}- acetate;

Ethyl-{4-[l-(4-trifluoromethyl-benzyloxyimino)-propyl]-phenoxy}-acetate; Ethyl-(2-methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5 ylmethoxy im ino] -ethyl } -phenoxy)-acetate;

Ethyl-{2-methyl-4-[l-(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-ethyl]- phenoxy } -acetate; Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}- acetate;

Ethyl-{2-methyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy}-acetate;

Ethyl-(2-methyl-4- { 1 -[2-(3-oxo-2,3-dihydro-benzo[ 1 ,4]oxazin-4-yl)-ethoxyimino]- ethyl} -phenoxy)-acetate; Ethyl- {2-methyl-4-[ 1 -(2-phenoxazin- 10-yl-ethoxyimino)-ethyl] -phenoxy} -acetate;

Ethyl-[2-methyl-4-(l-{2-[2-methyl-5-(4-methylsulfanyl-phenyl)-pyrrol-l-yl]- ethoxyimino}-ethyl)-phenoxy]-acetate;

Ethyl-(2-methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-ethyl}-phenoxy)-acetate; Ethyl- {4-[ 1 -(2-fluoro-benzyloxyimino)-ethyl]-2-methyl-phenoxy} -acetate;

Ethyl- {4-[ 1 -(2-indol- 1 -yl-ethoxyimino)-ethyl]-2-methyl-phenoxy} -acetate;

Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-ethyl]-2-methyl-phenoxy}-acetate;

Ethyl- {4-[ 1 -(2-tert-butyl-5-methyl-oxazol-4-ylmethoxyimino)-ethyl]-2-methyl- phenoxy} -acetate; Ethyl-{4-[l-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-ylmethoxyimino)-ethyl]-2-methyl- phenoxy} -acetate;

Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-2-phenyl-ethyl]- phenoxy } -acetate;

Ethyl- {2-methyl-4-[2 -phenyl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} - acetate;

Ethyl-{2-methyl-4-[(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-phenyl-methyl]- phenoxy} -acetate;

Ethyl-(2-methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5- ylmethoxyimino]-2-phenyl-ethyl}-phenoxy)-acetate; Ethyl-(4-{cyclohexyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-

5ylmethoxyimino]-methyl}-2-methyl-phenoxy)-acetate;

Ethyl- {4-[ 1 -(2-indol- 1 -yl-ethoxyimino)-2-phenyl-ethyl] -2-methyl-phenoxy} -acetate;

Ethyl-{2-methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-butyl]-phenoxy}- acetate;

Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-butyl]-2-methyl-phenoxy}-acetate;

Ethyl- {4-[l -(2-indol- 1 -yl-ethoxyimino)-butyl]-2-methyl-phenoxy} -acetate;

Ethyl- {4-[ 1 -(2-indol- 1 -yl-ethoxyimino)-propyl] -phenoxy } -acetate; Ethyl- {4-[cyclohexyl-(2-indol- 1 -yl-ethoxyimino)-methyl]-2-methyl-phenoxy} -acetate;

Ethyl-{2-methyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-butyl]-phenoxy} -acetate;

Ethyl-{4-[cyclohexyl-(4-trifluoromethyl-benzyloxyimino)-methyl]-2-methyl- phenoxy } -acetate;

Ethyl-{4-[2-cyclohexyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy } -acetate;

Ethyl- {2-methyl-4-[ 1 -(2-oxo-3-phenyl-oxazolidin-5-ylmethoxyimino)-ethyl]- phenoxy } -acetate; Ethyl-{4-[l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenyl}-acetate;

Ethyl-{4-[l-(2-carbazol-9-yl-ethoxyimino)-ethyl]-phenyl}-acetate;

Ethyl-{4-[2-(4-chloro-phenyl)-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy } -acetate; Ethyl-{2-methyl-4-[2-thiophen-3-yl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]- phenoxy } -acetate;

{4-[l-(4-Methoxy-benzyloxyimino)-propyl]-phenoxy}-acetic _acjd and its pharmaceutically acceptable salts;

(4-{ 1 -[2-(4-Trifluoromethyl-phenyl)-ethoxyimino]-propyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts; (4-{l-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]-propyl}- phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(5-Methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts; {4-[ 1 -(5-Methyl-2-phenyl-oxazol-4-ylmethoxyimino)-propyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{4-[l-(4-Trifluoromethyl-benzyloxyimino)-propyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

(2-Methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- ethyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[ 1 -(5-methyl-2-phenyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts; {2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[ 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} -acetic acid and ' its pharmaceutically acceptable salts;

(2-Methyl-4-{l-[2-(3-oxo-2,3-dihydro-benzo[l,4]oxazin-4-yl)-ethoxyimino]-ethyl}- phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(2-phenoxazin-10-yl-ethoxyimino)-ethyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts; ■ [2-Methyl-4-(l-{2-[2-methyl-5-(4-methylsulfanyl-phenyl)-pyrrol-l-yl]-ethoxyimino}- ethyl)-phenoxy]-acetic acid and its pharmaceutically acceptable salts; (2-Methyl-4- { 1 -[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- ethyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Fluoro-benzyloxyimino)-ethyl]-2-methyl-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-2-phenyl-ethyl]- phenoxy} -acetic acid and its pharmaceutically acceptable salts; {2-Methyl-4-[2 -phenyl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

(2-Methyl-4-{l-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]-2- phenyl-ethyl}-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

(4-{Cyclohexyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxyimino]- methyl}-2-methyl-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Indol-l-yl-ethoxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(5-methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-butyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Fluoro-benzyloxyimino)-2-phenyl-ethyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts; {4-[l-(2-Indol-l-yl-ethoxyimino)-butyl]-2-methyl-phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{4-[Cyclohexyl-(2-indol-l-yl-ethoxyimino)-methyl]-2-methyl-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[l-(4-trifluoromethyl-benzyloxyimino)-butyl]-phenoxy}-acetic acid and its pharmaceutically acceptable salts;

{4-[2-Cyclopentyl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl-phenoxy}- acetic acid and its pharmaceutically acceptable salts; {4-[2-Cyclohexyl- 1 -(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl-phenoxy} - acetic acid and its pharmaceutically acceptable salts;

{4-[l-(4-Trifluoromethyl-benzyloxyimino)-ethyl]-phenyl}-acetic acid and its pharmaceutically acceptable salts; {4-[l-(5-Methyl-2-p-tolyl-oxazol-4-ylmethoxyimino)-ethyl]-phenyl}-acetic acid and its pharmaceutically acceptable salts;

{4-[l-(2-Carbazol-9-yl-ethoxyimino)-ethyl]-phenyl}-acetic acid and its pharmaceutically acceptable salts;

(4- { 1 - [3 -(4-Acety 1-3 -hydroxy-2-propyl-phenoxy)-propoxy imino] -2-phenyl-ethyl } -2- methyl-phenoxy)-acetic acid and its pharmaceutically acceptable salts;

{4-[2-(4-Chloro-phenyl)-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-2-methyl- phenoxy} -acetic acid and its pharmaceutically acceptable salts;

{2-Methyl-4-[2-thiophen-3-yl-l-(4-trifluoromethyl-benzyloxyimino)-ethyl]-phenoxy}- acetic acid and its pharmaceutically acceptable salts.

11. A pharmaceutical composition which comprises compounds of formula (I), as claimed in any preceding claims and a pharmaceutically acceptable carrier, diluent or excipients.

12. A method of preventing or treating diseases caused by hyperlipidaemia, hypercholesteremia, hyperglycemia, obesity, impaired glucose tolerance, leptin resistance, insulin resistance, diabetic complications, inflammation comprising administering an effective, non-toxic amount of compound of formula (I) or suitable pharmaceutical composition as defined in any preceding claims to a patient in need thereof.

13. The method according to any preceding claims, wherein the disease is type 2 diabetes, impaired glucose tolerance, dyslipidaemia, hypertension, obesity, atherosclerosis, hyperlipidaemia, coronary artery disease, cardiovascular disorders and other diseases wherein insulin resistance is the underlying pathophysiologal mechanism.

14. A medicine for treating/reducing any of the disease conditions described in any preceding claims which comprises administering a compound of formula (I), as defined in any preceding claims and a pharmaceutically acceptable carrier, diluent or excipients to a patient in need thereof.

15. Use of compounds of formula (I), their pharmaceutical compositions and medicines containing them as defined in any previous claims as a medicament suitable for the treatment of diseases mentioned in any of the aforesaid claims.

16. A process for preparing compounds of formula (I) as claimed in claim 1, comprising: i. reacting compounds of general formula (II) where all symbols are as defined earlier and L represents a suitable leaving group selected from halogen, mesylate, tosylate, triflate, with compounds of general formula (III), where all symbols are as defined earlier and R₂ represent alkyl group to yield compound of general formula (Ia) where all symbols are as defined earlier and R₂ represent alkyl.

ii. hydrolysis of compound of general formula (Ia) wherein R₂ is alkyl and all other symbols are as defined earlier to yield compound of general formula (I) wherein R₂ is H and all other symbols are as defined earlier.

17. Intermediate of the formula (III)

wherein

Ri represents optionally substituted linear or branched (Ci-Ce)alkyl, (C₃-C₆)cycloalkyl, aryl, aralkyl, heterocyclyl groups; R₂ represents hydrogen, linear or branched substituted or unsubstituted (Ci-C₆)alkyl ; R₃ represents hydrogen, halo, (Ci-C₃)alkyl, halo(Ci-C₃)alkyl, (Ci-C₃)alkoxy, thio(Ci-C₃)alkyl, sulfenyl derivatives, sulfonyl derivatives; R₄ and R₅ may be same or different and represents H or linear or branched (Ci-C₆)alkyl; X represents a bond or oxygen or the group -CH₂-.

18. A compound as claimed in claim 17 wherein when Ri is substituted, the substituents are independently selected from hydroxyl, halo, thio, amino, or substituted or unsubstituted groups selected from alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, aryl, aryloxy, aralkyl, aralkoxy, acyl, arylamino, aralkylamino, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, aralkoxyalkyl, alkylthio, arylthio, alkylsulfonylamino, alkylsulfonyloxy, alkoxycarbonylamino, aryloxycarbonylamino, aralkyloxycarbonylamino, sulfenyl derivatives, sulfonyl derivatives.

19. A compound as claimed in claims 17 or 18 selected from Ethyl-[4-(l-hydroxyimino-propyl)-phenoxy]-acetate;

Ethyl-[4-(l-hydroxyimino-butyl)-phenoxy]-acetate;

Ethyl-[4-( 1 -hydroxyimino-ethyl)-2-methylτphenoxy]-acetate;

Ethyl-[4-(hydroxyimino-phenyl-methyl)-2-methyl-phenoxy]-acetate;

Ethyl-[4-(2-cyclohexyl-l-hydroxyimino-ethyl)-2-methyl-phenoxy]-acetate; Ethyl- [4-(2-cyclopentyl- 1 -hydroxyimino-ethyl)-2-methyl-phenoxy] -acetate ;

Ethyl-[4-(l-hydroxyimino-2-phenyl-ethyl)-2-methyl-phenoxy]-acetate;

Ethyl-[4-(cyclohexyl-hydroxyimino-methyl)-2-methyl-phenoxy]-acetate;

Ethyl-[4-(l-hydroxyimino-2-thiophen-3-yl-ethyl)-2-methyl-phenoxy]-acetate;

Ethyl- {4-[2-(4-chloro-phenyl)- 1 -hydroxyimino-ethyl]-2-methyl-phenoxy} -acetate; Ethyl-[4-( 1 -hydroxyimino-ethyl)-phenyl]-acetate.

20. A process for preparing the intermediates of formula III as claimed in claims 17- 19 comprising reacting the intermediate (VI) where all the symbols are as defined earlier with hydroxylamine hydrochloride to yield the intermediate (III) where all the symbols are as defined earlier.