Pyridine derivatives

1. A pyridine derivative of the formula (I)

wherein —R 1 represents

in which R 11 is hydrogen, C 1-6 alkyl, halogen, hydroxy, C 1-12 alkoxy, nitro, amino, C 1-6 alkylsulfonylamino, C 1-6 alkoxycarbonyl, C 1-6 alkylamino, di (C 1-6 alkyl)amino, C 1-6 alkanoylamino, phenyl C 1-6 alkylamino, phenylsulfonylamino, or —O—(CH 2 ) n —R 111 ,

wherein n represents an integer selected from 0 to 6, and R 111 is C 2-6 alkenyl, benzoyl, diphenylmethyl, di (C 1-6 alkyl)amino, C 1-6 alkanoyl, C 1-6 alkoxycarbonyl, or a 3 to 10 membered saturated or unsaturated ring having 0 to 3 heteroatoms selected from the group consisting of S, O and N as heteroatoms and is optionally substituted by C 1-6 alkyl, mono or di halogen, halogen substituted C 1-6 alkyl, nitro, cyano, C 1-6 alkoxycarbonyl, phenyl, hydroxy, amino, C 1-6 alkylamino, di (C 1-6 alkyl)amino, C 1-6 alkanoylamino, C 1-6 alkoxy, or carbamoyl;

R 2 represents hydrogen or halogen;

R 3 represents hydrogen or,

—CR 31 R 32 R 33 ,

wherein R 31 is hydrogen or C 1-6 alkyl,

R 32 is hydrogen, α-aminobenzyl, C 1-6 alkyl optionally substituted by one or two substituents selected from the group consisting of hydroxy, amino, amino substituted phenyl, phenyl, halogen substituted phenyl, and C 1-6 alkoxysubstituted phenyl, or a 5 to 8 membered saturated ring having 0 to 3 atoms selected from the group consisting of S, O and N as heteroatoms and optionally substituted by C 1-6 alkyl, and

R 33 is hydrogen, amino, C 1-6 alkoxycarbonylamino, C 2-6 alkenyloxycarbonylamino, or piperidino-C 1-6 alkylcarbonylamino, or

R 4 represents hydroxycarbonyl, C 1-6 alkanoyl, carbamoyl, cyano, nitro, carboxyl, C 1-6 alkoxycarbonyl, C 1-6 alkylcarbamoyl, C 1-6 alkylamino, 5 to 10 membered heteroaryl (hydroxy) methyl, 5 to 10 membered heteroaryl-C 1-6 alkyl, or methyl substituted by hydroxy and a 5 to 7 membered saturated cyclic ring, C 1-6 alkyl optionally substituted by one selected from the group consisting of hydroxy, C 1-6 alkoxy, C 1-6 alkylsulfonylamino, C 1-6 alkylcarbonylamino, C 5-10 aryl, C 5-10 arylsulfonyl, C 5-10 arylsulfanyl, C 5-10 aryloxy, imidazolyl, or dioxo substituted pyrolidino-oxy,

—(CH 2 ) p NHCOR 41 , —(CH 2 ) p NHC(═S)R 41

wherein p represents any of integer from 1 to 6 and R 41 represents C 1-6 alkoxy, amino, phenylamino, C 1-6 alkyl, C 1-6 alkylamino, di(C 1-6 alkyl)amino, C 3-10 cycloalkylamino,

R 5 represents NR 51 R 52 ,

wherein R 51 is hydrogen, C 1-6 alkyl,

R 52 is hydrogen, C 1-6 alkyl, phenyl, benzyl, C 1-6 alkanoyl, or NR51 R52 may form saturated 5-6 membered ring optionally contain NH or O as other heteroatom than the adjacent N atom,

or a salt thereof.

2. The compound or a salt thereof as claimed in claim 1 , wherein:

—R 1 represents

in which R 11 is hydrogen, C 1-6 alkyl, halogen, hydroxy, C 1-12 alkoxy, amino, C 1-6 alkanoylamino, phenyl C 1-6 alkylamino, phenylsulfonylamino, or —O—(CH 2 ) n —R 111 ,

wherein n represents an integer selected from 1 to 6, and R 111 is C 2-6 alkenyl, benzoyl, diphenylmethyl, di (C 1-6 alkyl)amino, C 1-6 alkanoyl, C 1-6 alkoxycarbonyl, or a 3 to 10 membered saturated or unsaturated ring having 0 to 3 heteroatoms selected from the group consisting of S, O and N as heteroatoms and is optionally substituted by C 1-6 alkyl, mono or di halogen, halogen substituted C 1-6 alkyl, nitro, cyano, C 1-6 alkoxycarbonyl, phenyl;

R 2 represents hydrogen;

R 3 represents hydrogen or

—CR 31 R 32 R 33 ,

wherein R 31 is hydrogen or C 1-6 alkyl,

R 32 is hydrogen, α-aminobenzyl, C 1-6 alkyl optionally substituted by one or two substituents selected from the group consisting of hydroxy, amino, amino substituted phenyl, phenyl, halogen substituted phenyl, and C 1-6 alkoxysubstituted phenyl, or a 5 to 8 membered saturated ring having 0 to 3 atoms selected from the group consisting of S, O and N as heteroatoms and optionally substituted by C 1-6 alkyl, and

R 33 is hydrogen, amino, C 1-6 alkoxycarbonylamino, C 2-6 alkenyloxycarbonylamino, piperidino-C 1-6 alkylcarbonylamino, or

R 4 represents hydroxycarbonyl, C 1-6 alkanoyl, carbamoyl, cyano, carboxyl, C 1-6 alkoxycarbonyl, C 1-6 alkylcarbamoyl, C 1-6 alkylamino, 5 to 10 membered heteroaryl (hydroxy) methyl, 5 to 10 membered heteroaryl-C 1-6 alkyl, or methyl substituted by hydroxy and a 5 to 7 membered saturated cyclic ring, C 1-6 alkyl optionally substituted by one selected from the group consisting of hydroxy, C 1-6 alkoxy, C 1-6 alkylsulfonylamino, C 1-6 alkylcarbonylamino, C 5-10 aryl, C 5-10 arylsulfanyl, C 5-10 arylsulfenyl, C 5-10 aryloxy, imidazolyl, or dioxo substituted pyrolidino-oxy,

—(CH 2 ) p NHCOR 41 , —(CH 2 ) p NHC(═S)R 41

wherein p represents any of integer from 1 to 6 and R 41 represents C 1-6 alkoxy, amino, phenylamino, C 1-6 alkyl, C 1-6 alkylamino, di(C 1-6 alkyl)amino, C 3-10 cycloalkylamino,

R 5 represents NR 51 R 52 ,

wherein R 51 is hydrogen, C 1-6 alkyl, and

R 52 is hydrogen, C 1-6 alkyl, phenyl, benzyl, C 1-6 alkanoyl, or NR 51 R 52 may form piperidino

or a salt thereof.

3. The compound or a salt thereof as claimed in claim 1 , wherein:

—R 1 represents

in which R 11 is hydrogen, C 1-12 alkoxy, or —O—(CH 2 ) n —R 111 ,

wherein n represents an integer selected from 1 to 6, and R 111 is phenyl, C 3-8 cycloalkyl;

R 2 represents hydrogen;

R 3 represents

—CR 31 R 32 R 33 ,

wherein R 31 is hydrogen,

and

R 4 represents cyano, C 1-6 alkyl optionally substituted by hydroxy or C 1-6 alkoxy, or

—(CH 2 ) p NHCOR 41 , —(CH 2 ) p NHC(═S)R 41

wherein p represents any of integer from 1 to 6 and R 41 represents C 1-6 alkoxy, amino, phenylamino, C 1-6 alkyl, C 1-6 alkylamino, di(C 1-6 alkyl)amino, C 3-10 cycloalkylamino; and

R 5 represents amino

or a salt thereof.

4. The compound or a salt thereof as claimed in claim 1 , wherein

—R 1 represents

in which R 11 is hydrogen, C 1-6 alkoxy, or —O—CH 2 —R 111 ,

wherein R 11 is phenyl, C 3-4 cycloalkyl;

R 2 represents hydrogen;

R 3 represents

—CR 31 R 32 R 33 ,

wherein R 31 is hydrogen,

R 4 represents cyano, hydroxymethyl, or —CH 2 NHCOR 41 ,

wherein R 41 represents C 1-6 alkoxy, amino, phenylamino, C 1-6 alkyl, C 1-6 alkylamino, di(C 1-6 alkyl)amino, C 3-10 cycloalkylamino; and

R 5 represents amino

or a salt thereof.

5. A pharmaceutical composition comprising a compound or a salt thereof as claimed in claim 1 plus a pharmaceutically acceptable carrier.

6. A pharmaceutical composition comprising a compound or a salt thereof as claimed in claim 1 together with one or more pharmaceutically acceptable excipients.

7. A method for treating an inflammatory disease in a mammal comprising administering a compound or a salt thereof as claimed in claim 1 .

8. The method as claimed in claim 7 , wherein said disease selected from the group consisting of asthma; allergic rhinitis; atopic dermatitis; hives; conjunctivitis; vernal catarrh; chronic arthrorheumatism; systemic lupus erythematosus; psoriasis; diabrotic colitis; systemic inflammatory response syndrome (SIRS); sepsis; polymyositis; dermatomyositis (DM); Polyaritis nodoa (PN); mixed connective tissue disease (MCTD); Sjoegren's syndrome; and gout.

9. A method of promoting immunosuppression in a mammal comprising administering a compound or a salt thereof as claimed in claim 1 .

10. A method for treating ischemia in a mammal comprising administering a compound or a salt thereof as claimed in claim 1 .

11. A method for treating tumors in a mammal comprising administering a compound or a salt thereof as claimed in claim 1 .