Pyrrolo (3,4-b) pyridines and methods for their preparation

C - Chemistry – Metallurgy – 07 – D

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C07D 471/04 (2006.01) C07D 207/34 (2006.01)

Patent

CA 1049017

ABSTRACT OF THE DISCLOSURE This invention relates to a process for preparing compounds of formula Image I wherein the substituents R through R5 are defined as follows: R represents hydrogen, (C1-4)alkyl, benzyl or chloro-substituted benzyl; R1 is selected from hydrogen,(C1-4)alkyl, phenyl and methyl-substituted phenyl; R2 represents (C1-4)alkyl or hydroxy; R3 stands for (C1-4)alkyl or (C1-4)alkoxy or phenyl; R4 represents hydrogen, (C1-4)alkyl or phenyl and R5 represents a (C1-4)alkyl group; and pharmaceutically acceptable salts thereof with acids, which comprises reacting an aminopyrrole of formula Image or an acid salt thereof, in which R, R1 and R5 are defined as above and R6 represents an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, or phenyl with a compound selected from diketene or a .beta.- dicarbonyl derivative of formula X-COCH2CO-R3 wherein R3 is defined as above and X stands for an alkyl group of 1 to 4 carbon atoms, phenyl or, when R3 represents (C1-4)alkoxy, a halogen atom and cyclising the intermediate so formed. It also relates to the products of this process which are of interest because of their very interesting pharmacological properties. In particular these are active as antiinflammatories and as prostaglandin synthetase inhibitors.

222572

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