BE807526A - 2-(2-(Hetero)arylvinyl)-3-aminoquinoxalines - with anti-inflammatory activity - Google Patents

Abstract

Compounds of formula (I) and their acid-addn. salts are new: where X is NH(CH2)3NRR1, lower dialkylamino, piperidino, morpholino, or piperazino opt. 4-substd. by lower alkyl or lower hydroxyalkyl; R and R1 are H, lower alkyl or lower hydroxyalkyl, or NRR1 is piperidino, morpholino, or piperazino opt. 4-substd. by lower alkyl or lower hydroxyalkyl; R2 and R3 are H, lower alkyl, lower alkoxy, hexafluoro-2-hydroxy-2-propyl or Cl; R4 is phenyl, thienyl, pyridyl or phenyl substd. by lower alkyl, lower alkoxy, halogen or CF3. Anti-inflammatories, e.g. for treating gout and systemic lupus erythematosus. (I) where R4 is opt. substd. phenyl can be prepd. by reacting 2-hydroxy-3-styryl-quinoxaline (or a ring-substd. deriv. thereof) with POCl3, followed by nucleophilic substitution of the resulting 2-chloro-3-styryl-quinoxaline. When R4 is thienyl or pyridyl, the corresp. 2-chloropyridylethylene- or 2-chlorothienylethylene-quinoxaline is used. (I; R4=phenyl) can also be prepd. by reacting the corresp. 2-methyl cpd. with benzaldehyde in the presence of acid. The residue was recrystd. from i-PrOH to give 145g. 2 3-(4-methyl-1-piperazinyl) propylamino -3-styrylquinoxaline, m.p. 145-147 degrees C.