Heterocyclic compounds suitable for the treatment of dyslipidemia

1. A compound of formula (I)

including its tautomeric form, its steroisomer, and its pharmaceutically acceptable salt.

wherein ‘A’ represents an optionally substituted single or fused group selected from arly, heterocyclyl and cycloalky groups;

wherein ‘Y’ represents either (i) a bond or (ii) a moiety selected from a substituted or unsubstituted, linear or branched (C 1 -C 6 )alkyl group, a substituted or unsubstituted, linear or branched (C 2 -C 6 )alkenyl group, and a group represented by ‘—U(CH 2 ) m -’ wherein U represents a moiety selected from O, S(O) o , and NR 4 and ‘m’ represents integers from 2 to 4, and wherein ‘o’ in S(O) o represents an integer from 0 to 2 and R 4 in NR 4 represents a moiety selected from H and a substituted or unsubstituted linear or branched (C 1 -C 6 )alkyl group;

wherein ‘Z’ represents an optionally substituted single or fused group selected from aryl, heterocyclyl and cycloalkyl groups;

wherein ‘X’ represents either (i) a bond, or (ii) is selected from O, S(O) o or NR 4 ; wherein ‘o’ in S(O) o represents an integer from 0 to 2 and R 4 in NR 4 is a moiety slected from H and a substituted or unsubstituted linear or branched (C 1 -C 6 alkyl group;

wherein ‘W’ represents a moiety selected from a substituted or unsubstituted linear or branched (C 1 -C 6 )alkyl group, and a substituted or unsubstituted linear or branched (C 2 -C 6 ) alkenyl group;

wherein R 1 represents hydrogen, or a group selected from a (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, aryl, heterocyclyl, aralkyl, and heterocyclylalkyl, each of which may be optionally substituted; R 2 represents hydrogen, or a group selected from (C 1 -C 6 )alkyl, aryl, heterocyclyl, aralkyl, heterocyclylalkyl, (C 1 -C 6 )alkoxy, hydroxyalkyl, thio(C 1 -C 6 )alkyl, amino, aminoalkyl, and alkylamino, each of which may be optionally substituted; with the proviso that R 1 and R 2 together may optionally form a 4 to 7 membered saturated or partially saturated ring containing from 0-2 additional heteroatoms selected from the group of N, O, and S(O) o , wherein ‘o’ in S(O) o represents an integer from 0 to 2; R 3 at each occurrence independently represents a moiety selected from hydrogen, halogen, an (C 1 -C 3 )alkyl group, a halo(C 1 -C 3 )alkyl group, a (C 1 -C 3 )alkoxy group, a thio(C 1 -C 3 )alkyl group, a sulfenyl derivative, and a sulfonyl derivative; and

wherein ‘n’ represents integer from 0-3.

2. The compound as claimed in claim 1 wherein ‘A’ is selected from an optionally substituted aryl group or an optionally substituted heterocyclyl group.

3. The compound as claimed in claim 1 wherein when ‘A’ represents an aryl group, the aryl group being selected from a substituted or unsubstituted monocyclic or bicyclic aromatic group.

4. The compound as claimed in claim 3 wherein the aryl group is an optionally substituted phenyl group.

5. The compound as claimed in claim 1 wherein when ‘A’ represents a heterocyclyl group, the heterocyclyl group is selected from a single or fused, mono, bi or tricyclic aromatic or non-aromatic group containing one or more hetero atoms selected from O, N or S.

6. The compound as claimed in 5 wherein the heterocyclyl group is selected from a 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, thiazepinyl, oxazolidinyl, thiazolidinyl, dihydrothiophene, dihydropyran, dihydrofuran, dihydrothiazole, benzopyranyl, benzopyranonyl, benzodihydrofuranyl, benzodihydrothienyl, pyrazolopyrimidonyl, azaquinazolinoyl, thienopyrimidonyl, quinazolonyl, pyrimidonyl, benzoxazinyl, benzoxazinonyl, benzothiazinyl, benzothiazinonyl, and thieno piperidinyl group.

7. The compound as claimed in claim 1 wherein Z represents a group selected from an optionally substituted aryl group an optionally substituted heterocyclyl group.

8. The compound as claimed in claim 7 wherein the aryl group is selected from a substituted or unsubstituted monocyclic or bicyclic aromatic group.

9. The compound as claimed in claim 8 wherein the aryl group is an optionally substituted phenyl group.

10. The compound as claimed in claim 7 wherein the heterocyclyl group is selected from a single or fused mono or bi cyclic aromatic group containing one or more hetero atoms selected from O, N or S.

11. The compound as claimed in claim 10 wherein the aromatic heterocyclic group is selected from a 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, and benzothiazolyl group.

12. The compound as claimed in claim 1 selected from

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-(1-(((4-(trifluoromethyl) benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-(1-(((4-(trifluoromethyl) benzyl)oxy)imino)ethyl)pyridin-2-yl)amino)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenyl)amino)acetamide;

2,2′-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)bis(N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide);

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((1-(4-(trifluoromethyl)benzyl)-3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)acetamide;

2-(2-methyl-4-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-phenyl-1-(((3-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-(pyridin-4-yl)-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-morpholino-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-(4-(2-thiomorpholino-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)acetamide;

2-(2-methyl-4-(2-(thiophen-3-yl)-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-(4-((((4-(trifluoromethyl) benzyl)oxy)imino)methyl)phenoxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-((((4-(trifluoromethyl) benzyl)oxy)imino)methyl)pyridin-2-yl)oxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((4-(1-(((4-(trifluoromethyl) benzyl)oxy)imino)ethyl)phenyl)amino)acetamide;

2-((5-(1-(((4-cyanobenzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)pyridin-2-yl)oxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)pyridin-2-yl)amino)acetamide;

2-((5-(1-((benzyloxy)imino)propyl)pyridin-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(1-(((4-methylbenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(1-(((4-methoxybenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(1-(((4-fluorobenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(1-(((4-cyanobenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(2-methyl-4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)butyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-methoxy-1-(((4(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-hydroxy-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(2-methyl-4-(1-(((4-methylbenzyl)oxy)imino)-2-phenylethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-methylbenzyl)oxy)imino)-2-phenylethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-fluorobenzyl)oxy)imino)-2-phenylethyl)-2-methylphenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-fluorobenzyl)oxy)imino)-2-phenylethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-chlorobenzyl)oxy)imino)-2-phenylethyl)-2-methylphenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-chlorobenzyl)oxy)imino)-2-phenylethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(2-methyl-4-(2-phenyl-1-(((4-(trifluoromethoxy)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-phenyl-1-(((4-trifluoromethoxy)benzyl)oxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-methoxybenzyl)oxy)imino)-2-phenylethyl)-2-methylphenoxy)-N-((tetrahydro-2′-1-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-methoxybenzyl)oxy)imino)-2-phenylethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((4-(methylsulfonyl)benzyl)oxy)imino)propyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(2-phenyl-1-((pyridin-2-ylmethoxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-((2-(1H-indol-1-yl)ethoxy)imino)propyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((5-ethylpyrimidin-2-yl)oxy)imino)propyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((5-methyl-2-phenyloxazol-4-yl)methoxy)imino)propyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-(((3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)methoxy)imino)propyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-(((4-(trifluoromethyl)benzyl)oxy)imino)-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)acetamide;

2-((5-(((4-chlorobenzyl)oxy)imino)-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(((4-cyanobenzyl)oxy)imino)-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(((4-methoxybenzyl)oxy)imino)-5,6,7,8-tetrahydronaphthalen-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

Methyl 3-((((6-(2-oxo-2-(((tetrahydro-2H-pyran-4-yl)methyl)amino)ethoxy)-3,4-dihydronaphthalen-1(2H)-ylidene)amino)oxy)methyl)benzoate;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)quinolin-8-yl)oxy)acetamide;

2-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)-2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)propanamide;

2-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)-2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)phenoxy)propanamide;

2-(4-(1-(((tetrahydro-2H-pyran-4-yl)methoxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-((cyclohexylmethoxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-(4-(1-((naphthalen-2-ylmethoxy)imino)ethyl)phenoxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

2-((5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((3-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)-1H-indol-5-yl)oxy)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((3-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)-1H-indol-5-yl)oxy)acetamide;

2-((3-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)-1H-indol-5-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-3-(5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyrimidin-2-yl)propanamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-3-(5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)pyrimidin-2-yl)propanamide;

3-(5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyrimidin-2-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)propanamide;

N-((tetrahydro-2H-pyran-4-yl)methyl)-2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)quinolin-8-yl)oxy)acetamide; and

2-((5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)quinolin-8-yl)oxy)-N-((tetrahydro-2H-pyran-4-yl)methyl)acetamide.

13. A pharmaceutical composition containing the compound as claimed in claim 1 .

14. A pharmaceutical composition for the treatment of hyperlipidemia, dyslipidemia and other similar diseases comprising the compound of formula (I) as claimed in claim 1 and at least one pharmaceutically active agent.

15. A pharmaceutical composition as claimed in claim 13 , further comprising at least one pharmaceutically active agent selected from the group consisting of insulin, insulin derivatives and mimetics, insulin secretagogues, insulin sensitizers, biguanide agents, alpha-glucosidase inhibitors, insulinotropic sulfonylurea receptor ligands, meglitinides, GLP-1 (glucagon like peptide-1), GLP-1 analogs, DPPIV (dipeptidyl peptidase IV) inhibitors, GPR-119 activators, sodium-dependent glucose co-transporter (SGLT2) inhibitors, PPAR modulators, non-glitazone type PPAR delta agonist, HMG-CoA reductase inhibitors, cholesterol-lowering drugs, rennin inhibitors, anti-thrombotic and anti-platelet agents and anti-obesity agents and pharmaceutically acceptable salts thereof.

16. An intermediate for the preparation of compound of formula (I) as claimed in claim 1 selected from

2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetic acid;

2,2′-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetic acid;

2-((1-(4-(trifluoromethyl)benzyl)-3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)acetic acid;

2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)quinolin-8-yl)oxy)acetic acid;

2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)amino)acetic acid;

2-((5-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(1-(((4-cyanobenzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)pyridin-2-yl)amino)acetic acid;

2-((5-(1-((benzyloxy)imino)propyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(1-(((4-methylbenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(1-(((4-methoxybenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(1-(((4-fluorobenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(1-(((4-cyanobenzyl)oxy)imino)propyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetic acid;

2-((5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)amino)acetic acid;

2-((3-((((4-(trifluoromethyl)benzyl)oxy)imino)methyl)-1H-indol-5-yl)oxy)acetic acid;

2-((3-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)-1H-indol-5-yl)oxy)acetic acid;

2-((3-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)-1H-indol-5-yl)oxy)acetic acid;

2-((3-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)-1H-indol-5-yl)oxy)acetic acid;

3-(5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyrimidin-2-yl)propanoic acid;

3-(5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)pyrimidin-2-yl)propanoic acid;

3-(5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyrimidin-2-yl)propanoic acid;

2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)quinolin-8-yl)oxy)acetic acid;

2-((5-(2-phenyl-1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)quinolin-8-yl)oxy)acetic acid.