Thiazoloisoquinolines, and process for their preparation

Details Thiazoloisoquinolines, and process for their preparation Thiazoloisoquinolines, and process for their preparation

C - Chemistry, Metallurgy

07

D

260/271.3

C07D 513/04 (2006.01)

Patent

CA 1037042

ABSTRACT OF THE DISCLOSURE The invention relates to new thiazoloisoquinolines of the general formula (I), or salts thereof, Image (I) wherein: A stands for a group of the formula - S - ? - , R1 represents hydroxy or alkoxy of 1 to 4 carbon atoms; R2 represents hydroxy or alkoxy of 1 to 4 carbon atoms; R3 represents hydrogen, alkyl of 1 to 4 carbon atoms, phenyl, nitro, cyano, carboxy, or carboxamido; Y represents oxygen, sulphur or a group = N - R4; and R4 represents hydrogen, alkyl of 1 to 4 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms, phenyl, monohalophenyl, benzoyl, toluene sulphonyl, or acyl of 2 to 4 carbon atoms. These new compounds can be used in practice as heart medicines or respiratory analeptics. The new compounds according to the invention can be prepared as follows: an isoquinoline of the general formula (II) or a salt thereof Image (II) wherein: R5 represents hydrogen, hydroxy, alkoxy or aralkoxy; R6 represents hydrogen, hydroxy, alkoxy or aralkoxy; R7 represents hydrogen, alkyl, aryl, carboxy or a carboxy deriva- tive; and X represents hydrogen, halogen or mercapto, is reacted with a reactive carbonic acid derivative, provided that at least one of the reactants contains a sulfur atom, and/or an isoquinoline of the general formula (III) Image (III) wherein R5, R6 and R7 each have the same meanings as defined above, and Y' stands for oxygen, sulfur or a group of the formula = N - R8, wherein R8 represents hydrogen, alkyl, aryl, acyl, arylsulfonyl or alkylsulfonyl, is oxidized, and/or substituents A', R5, R6 and R7 of the obtained thiazolo- isoquinoline of the general formula (IA) Image (IA) wherein A' stands for a group of the formula - S - ? - , and R5, R6, R7 and Y' each have the same meanings as defined above, is (are) converted into those required in the end-products.

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