US 7,622,486 B2Granted

Pyridine compounds, process for their preparation and compositions containing them

AssigneeReddy US Therapeutics, Inc.

InventorsManojit Pal, Christopher W. Alexander, Ish Khanna, Javed Iqbal, Ram Pillarisetti, Santanu Maitra, Gayla W. Roberts, Lavanya Sagi, Chintakunta Vamsee Krishna, Jennepalli Sreenu

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Abstract

The present invention provides new heterocyclic compounds, particularly substituted pyridines, methods and compositions for making and using these heterocyclic compounds, and methods for treating a variety of diseases and disease states, including atherosclerosis, arthritis, restenosis, diabetic nephropathy, or dyslipidemia, or disease states mediated by the low expression of Perlecan.

Claims24

Dependent claims

A compound having the formula:

or a salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, or a racemic mixture thereof;
wherein:
Y2 is selected independently from —NR5;
R5 is hydrogen or methyl;
R1 and R2 are selected independently from a substituted or an unsubstituted alkyl, cycloalkyl, aryl, or heterocyclyl or heteroaryl comprising at least one heteroatom or heterogroup selected from —O—, —N—, —S—, —CO or —SO2, any of which having up to 10 carbon atoms;
or
Y2R2 is independently selected from a substituted or an unsubstituted morpholinyl, piperazinyl, piperidinyl, or pyrrolidinyl;
R4 is selected from a substituted or an unsubstituted aryl, or a substituted or an unsubstituted heterocyclyl or heteroaryl comprising at least one heteroatom or heterogroup selected from —O—, —N—, —S—, or —CO, any of which having up 10 carbon atoms;
R1 and R2 are optionally substituted with at least one group independently selected from:
1) an alkyl, an alkoxy, a haloalkyl, a haloalkoxy, —COR9, —CO2R8, —CONR82, —SO2R9, —NHSO2R9, or —SO2NR82, any of which having up to 10 carbon atoms;
or 2) halogen, —OCH2O—, cyano, or hydroxyl;
R8 in each occurrence, is selected independently from:
1) an alkyl, a haloalkyl, or an aryl, any of which having up to 10 carbon atoms;
or 2) hydrogen;
R9, in each occurrence, is selected independently from an alkyl, a haloalkyl, an aryl, or a heterocyclyl or heteroaryl comprising at least one heteroatom selected from —O— or —N—, any of which having up to 10 carbon atoms;
and
R4 is optionally substituted with at least one group independently selected from:
1) an alkyl, a haloalkoxy, an alkoxy, —COR9, —CONR82, —SO2R9, —SO2NR102, or —NR102, any of which having up to 10 carbon atoms;
or 2) halogen, cyano, or hydroxyl;
and
R10 in each occurrence, is selected independently from:
1) an alkyl, an aryl, or a heterocyclyl comprising at least one heteroatom selected from —O— or —N—, any of which having up to 10 carbon atoms;
or 2) hydrogen.

20 more elements

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound having the formula:

wherein:
Y2 is selected independently from —NR5;
R5 is hydrogen or methyl;
R1 and R2 are selected independently from a substituted or an unsubstituted alkyl, cycloalkyl, aryl, or heterocyclyl or heteroaryl comprising at least one heteroatom or heterogroup selected from —O—, —N—, —S—, —CO or —SO2, any of which having up to 10 carbon atoms;
or
Y2R2 is independently selected from a substituted or an unsubstituted morpholinyl, piperazinyl, piperidinyl, or pyrrolidinyl
R4 is selected independently from:
1) a substituted or an unsubstituted aryl, or a substituted or an unsubstituted heteroaryl or heterocyclyl comprising at least one heteroatom or heterogroup selected from —O—, —N—, —S—, or —CO, any of which having up to 10 carbon atoms;
wherein any of R1 or R2, is also optionally substituted with at least one group independently selected from:
1) an alkyl, an alkoxy, a haloalkyl, a haloalkoxy, —COR9, —CO2R8, —CONR82, —SO2R9, —NHSO2R9, or —SO2NR82, any of which having up to 10 carbon atoms;
or 2) hydroxyl, halogen, —OCH2O—, or cyano;
R8, in each occurrence, is selected independently from:
1) an alkyl, a haloalkyl, or an aryl, any of which having up to 10 carbon atoms;
or 2) hydrogen;
R9, in each occurrence, is selected independently from an alkyl, a haloalkyl, an aryl, or a heterocyclyl or heteroaryl comprising at least one heteroatom selected from —O—, or —N—, any of which having up to 10 carbon atoms,
R4 is optionally substituted with at least one group selected independently from:
1) an alkyl, an alkoxy, a haloalkoxy, —COR9, —CONR82, —SO2R9, —SO2NR102, —NR102, any of which having up to 10 carbon atoms;
or 2) halogen, cyano, or hydroxyl;
and
R10, in each occurrence, is selected independently from:
1) an alkyl, an aryl, or a heterocyclyl comprising at least one heteroatom selected from —O— or —N—, any of which having up to 10 carbon atoms;
or 2) hydrogen;
or a pharmaceutically acceptable salt, a prodrug, a diastereomeric mixture, an enatiomer, a tautomer, or a racemic mixture thereof.

20 more elements

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound selected from:

[6′-(4-Fluoro-phenyl )-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-yl]-(4-trifluoromethoxy-phenyl)-amine;
(4-Trifluoromethoxy-phenyl)-[6′-(4-trifluoromethoxy-phenyl )-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-yl]-amine;
(6′-Phenyl-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-yl )-(4-trifluoro-methoxy-phenyl)-amine;
[6′-(3-Methanesulfonyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-yl]-(4-trifluoromethoxy-phenyl)-amine;
4-[6′-(4-Fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-ylamino]-N-methyl-benzenesulfonamide;
1-[4-(4-Hydroxy-6′-phenyl-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-2′-ylamino)-phenyl]-ethanone;
(6-Phenyl-4-pyrrolidin-1-yl-pyridin-2-yl)-(4-trifluoromethoxy-phenyl)-amine;
[6-(4-Fluoro-phenyl)-4-pyrrolidin-1-yl-pyridin-2-yl]-(4-trifluoromethoxy-phenyl)-amine;
N-Methyl-4-[4-pyrrolidin-1-yl-6-(4-trifluoromethoxy-phenyl)-pyridin-2-ylamino]-benzenesulfonamide;
N-Methyl-4-[4-(4-methyl-piperazin-1-yl)-6-(4-trifluoromethoxy-phenylamino)-pyridin-2-yl]-benzenesulfonamide;
[6-(3-Methanesulfonyl-phenyl)-4-morpholin-4-yl-pyridin-2-yl]-(4-trifluoromethoxy-phenyl)-amine;
N-Methyl-4-[4-morpholin-4-yl-6-(4-trifluoromethoxy-phenylamino)-pyridin-2-yl]-benzenesulfonamide;
(4-Fluoro-phenyl)-[6-(4-trifluoromethoxy-phenyl )-pyridin-2-yl]-amine;
or any combination thereof;
or a pharmaceutically acceptable salt, a prodrug, a diastereomeric mixture, an enantiomer, a tautomer, or a racemic mixture thereof.

12 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/234,257Filed 23 Sep 2005 · us provisional application
Priority: 23 Sep 2004
Published: US 2006/0084644 A120 Apr 2006
Granted: 24 Nov 2009
Term ends: Not estimatedThe source records don’t support an estimate.

Classification19 codes

C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents