2-Alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido (3,4-b) indole-3-carboxylic acid esters/amides useful as antithrombotic agents

A process for the preparation of a 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid ester of formula 1

• wherein R is selected from methyl ester and amide;
• and R1 is selected from the group consisting of alkyl, aryl, and heteroaryl moiety, the process comprising condensing an alkyl or aryl sulphonyl chloride with dimethyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylate Formula 2
• in the presence of a base and an organic solvent to obtain a corresponding 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole -3-carboxylic acid ester of formula 1.

A method for the preparation of 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid amides comprising reacting a 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid ester with methanolic ammonia for 24 to 48 hours hrs to obtain the corresponding 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid amide.

A pharmaceutical composition comprising a pharmaceutically effective amount of 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid ester/amide of formula 1

• wherein R is selected from methyl ester and amide;
• and R1 is selected from the group consisting of alkyl, aryl and heteroaryl moiety, and a pharmaceutically acceptable carrier.

A method for the treatment of intravascular thrombosis in mammals comprising administering to a patient in need thereof a therapeutically effective amount of a pharmaceutical composition consisting of a pharmaceutically effective amount of 2-alkyl/aryl sulphonyl-1,2,3,4tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid amide of formula 1

• wherein R is selected from methyl ester amide;
• and R1 is selected from group consisting of alkyl, aryl, and heteroaryl moiety, with a pharmaceutically acceptable carrier.

A method for the treatment of myocardial ischemia in mammals, comprising by administering to a patient in need thereof a therapeutically effective amount of a pharmaceutical composition consisting of a pharmaceutically effective amount of 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid ester/amide of formula 1

• wherein R is selected from methyl ester and amide;
• and R1 is selected from the group consisting of alkyl, aryl, and heteroaryl moiety, with a pharmaceutically acceptable carrier.

A method for the treatment of stroke in mammals, comprising administering to a patient in need thereof a therapeutically effective amount of a pharmaceutical composition consisting of a pharmaceutically effective amount of 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid ester/amide of formula 1

• wherein R is selected from methyl ester and amide;
• and R1 is selected from the group consisting of alkyl, aryl, and heteroaryl moiety, with a pharmaceutically acceptable carrier.

Use of of 2-alkyl/aryl sulphonyl-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indole-3-carboxylic acid ester/amide of formula 1

• wherein R is selected from methyl ester and amide;
• and R1 is selected from the group consisting of alkyl, aryl, and heteroaryl moiety, with or without a pharmaceutically acceptable carrier, for the treatment of myocardial ischemia, intravascular thromboses and stroke.