5-Pyridyl-1,3-thiazole derivatives, their production and use

Claim 2

A compound of the formula: wherein R stands for an optionally substituted alkyl group, alkenyl group, aryl group, aralkyl group, cycloalkyl group, heterocyclic group having carbon as the bonding hand or amino group, R 2 stands for a pyridyl group which may be substituted with alkyl group, and R 3 stands for an optionally substituted aryl group, or a salt thereof.

Claim 3

A compound as claimed in claim 1, wherein the salt is a pharmacologically acceptable salt.

Claim 4

A compound as claimed in claim 1, wherein R is (1) an alkyl group having 1 to 10 carbon atoms, which may be substituted with hydroxyl, amino, a lower alkylamino having 1 to 4 carbon atoms, carboxyl or a lower alkoxycarbonyl having 2 to 5 carbon atoms, (2) an alkenyl group having 2 to 4 carbon atoms, which may be substituted with hydroxyl, carboxyl or a lower alkylamino having 1 to 4 carbon atoms, (3) an aryl group which may have 1 to 3 substituents selected from the group consisting of carboxyl, halogen, 2-carboxyethenyl, 2-carboxy-l-propenyl, acetoxy and lower alkyl having 1 to 4 carbon atoms, (4) an aralkyl group having 7 to 12 carbon atoms, which may be substituted with methoxy or halogen, (5) cycloalkyl having 3 to 7 carbon atoms, which may be substituted with alkyl having 1 to 3 carbon atoms, (6) heterocyclic group containing in its ring one or two hetero atoms selected from the group consisting of sulfur, oxygen and nitrogen, which may be substituted with methyl, acetoxy, benzoyl or nicotinoyl, (7) an amino group which may have one or two substituents selected from the group consisting of lower alkyl having 1 to 4 carbon atoms, aralkyl having 7 to 10 carbon atoms, phenyl, pyridyl, 5-methyl-3-pyridyl, 4-methyl-2-pyridyl, lower alkoxycarbonylacetyl having 4 to 7 carbon atoms, lower alkylcarbonyl having 2 to 5 carbon atoms, carboxycarbonyl, lower alkoxycarbonylcarbonyl having 3 to 6 carbon atoms, lower alkoxycarbonyl having 2 to 4 carbon atoms, and halogenoalkoxycarbonyl having 2 to 5 carbon atoms, or (8) 5- or 6-membered cyclic amino, R 2 is a pyridyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, and R 3 is a phenyl group which may have 1 to 3 substituents selected from the group consisting of lower alkoxy having 1 to 4 carbon atoms, lower alkyl having 1 to 4 carbon atoms, hydroxyl, halogen, trimethylene and methylene-dioxy.

Claim 5

A compound as claimed in claim 1, wherein R 2 is 3 - pyridyl group which may be substituted with methyl.

Claim 6

A compound as claimed in claim 1, wherein the compound is 4-(4-methoxyphenyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazole.

Claim 7

A compound as claimed in claim 1, wherein the compound is 4-(4-fluorophenyl)-2-methylamino-5-(3-pyridyl)-l,3-thiazole.

Claim 8

A compound as claimed in claim 1, wherein the compound is 4-(3,4-methylenedioxyphenyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazole.

Claim 9

An analgesic, anti-pyretic, anti-inflammatory and anti-ulcer pharmaceutical composition, which comprises as an active ingredient, an effective amount of a compound of the formula: [wherein R 1 stands for an optionally substituted alkyl group alkenyl group, aryl group, aralkyl group, cycloalkyl group, heterocyclic group having carbon as the bonding hand or amino group, R 2 stands for a pyridyl group which may be substituted with alkyl group, and R 3 stands for an optionally substituted phenyl group] or a salt thereof, and a pharmaceutically acceptable carrier therefor.

Claim 10

An analgesic, anti-pyretic, anti-inflammatory and anti-ulcer pharmaceutical composition, which comprises as an active ingredient, an effective amount of a compound of the formula: [wherein R 1 stands for an optionally substituted alkyl group alkenyl group, aryl group, aralkyl group, cycloalkyl group, heterocyclic group having carbon as the bonding hand or amino group, R 2 stands for a pyridyl group which may be substituted with alkyl group, and R 3 stands for an optionally substituted phenyl group] or a salt thereof, and a pharmaceutically acceptable carrier therefor.

Claim 14

A method as claimed in claim 1, wherein the salt is a pharmacologically acceptable salt.

Claim 15

A method as claimed in claim 1, wherein R l is (1) an alkyl group having 1 to 10 carbon atoms, which may be substituted with hydroxyl, amino, a lower alkylamino having 1 to 4 carbon atoms, carboxyl or a lower alkoxycarbonyl having 2 to 5 carbon atoms, (2) an alkenyl group having 2 to 4 carbon atoms, which may be substituted with hydroxyl, carboxyl or a lower alkylamino having 1 to 4 carbon atoms, (3) an aryl group which may have 1 to 3 substituents selected from the group consisting of carboxyl, halogen, 2-carboxyethenyl, 2-carboxy-l-propenyl, acetoxy and lower alkyl having 1 to 4 carbon atoms, (4) an aralkyl group having 7 to 12 carbon atoms, which may be substituted with methoxy or halogen, (5) cycloalkyl having 3 to 7 carbon atoms, which may be substituted with alkyl having 1 to 3 carbon atoms, (6) heterocyclic group containing in its ring one or two hetero atoms selected from the group consisting of sulfur, oxygen and nitrogen, which may be substituted with methyl, acetoxy, benzoyl or nicotinoyl, (7) an amino group which may have one or two substituents selected from the group consisting of lower alkyl having 1 to 4 carbon atoms, aralkyl having 7 to 10 carbon atoms, phenyl, pyridyl, 5-methyl-3-pyridyl; 4-methyl-2-pyridyl, lower alkoxycarbonylacetyl having 4 to 7 carbon atoms, lower alkylcarbonyl having 2 to 5 carbon atoms, carboxycarbonyl, lower alkoxycarbonylcarbonyl having 3 to 6 carbon atoms, lower alkoxycarbonyl having 2 to 4 carbon atoms, and halogenoalkoxycarbonyl having 2 to 5 carbon atoms, or (8) 5- or 6-membered cyclic amino, R 2 is a pyridyl group which may be substituted with alkyl group having 1 to 4 carbon atoms, and R 3- is a phenyl group which may have 1 to 3 substituents selected from the group consisting of lower alkoxy having 1 to 4 carbon atoms, lower alkyl having 1 to 4 carbon atoms, hydroxyl, halogen, trimethylene and methylene-dioxy.

Claim 16

4 . A method as claimed in claim 1, wherein R 2 is 3-pyridyl group which may be substituted with methyl.

Claim 17

A method as claimed in claim 1, wherein the compound is 4-(4-methoxyphenyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazole.

Claim 18

A method as claimed in claim 1, wherein the compound is 4-( 4 -fluorophenyl) - 2-methylamino - 5-(3 - pyridyl) - 1,3-thiazole.

Claim 19

A method as claimed in claim 1, wherein the compound is 4-(3,4-methylenedioxyphenyl)-2-methylamino-5-(3-pyridyl)-1,3-thiazole.

Claim 20

An analgesic, anti-pyretic, anti-inflammatory and anti-ulcer pharmaceutical composition, which comprises as an active ingredient, an effective amount of a compound of the formula: [ wherein R stands for an optionally substituted alkyl group alkenyl group, aryl group, aralkyl group, cycloalkyl group, heterocyclic group having carbon as the bonding hand or amino group, R 2 stands for a pyridyl group which may be substituted with alkyl group, and R stands for an optionally substituted phenyl group] or a salt thereof, and a pharmaceutically acceptable carrier therefor.

Claim 21

An analgesic, anti-pyretic, anti-inflammatory and anti-ulcer pharmaceutical composition, which comprises as an active ingredient, an effective amount of a compound of the formula: [ wherein R stands for an optionally substituted alkyl group alkenyl group, aryl group, aralkyl group, cycloalkyl group, heterocyclic group having carbon as the bonding hand or amino group, R 2 stands for a pyridyl group which may be substituted with alkyl group, and R stands for an optionally substituted phenyl group] or a salt thereof, and a pharmaceutically acceptable carrier therefor.