GB1381031A - Imidazole derivatives and processes for their production - Google Patents

Abstract

1381031 Phenyl-heteroaromatic substituted imidazole derivatives CIBA-GEIGY AG 28 April 1972 [11 May 1971 22 March 1972] 19781/72 Heading C2C Novel compounds of the Formula I wherein R 1 is C 1-6 alkyl, cycloalkyl or phenyl which is optionally substituted by one or more halogen or C 1-6 alkyl or alkoxy substituents and one of the groups R 2 and R 3 is phenyl optionally substituted by one or more halogen, hydroxy or C 1-6 alkyl, alkoxy, alkylthio or alkylsulphonyl substituents and the other represents a 6-membered heteroaromatic radical containing 1 or 2 ring nitrogen atoms, and N- oxides and salts thereof may be prepared by (a) reacting a diketone II or a mono-oxime or N-oxide thereof with ammonia and an aldehyde R 1 .CHO; (b) reacting an amide V with ammonia; (c) reacting a reactive ester of IIa with an amidine R 1 C(:NH)NH 2 or a salt thereof; (d) reacting an oxazole VII with ammonia and optionally forming an N- oxide or converting an N-oxide to a free compound and/or optionally forming a salt or converting a salt to a free base. The intermediate diketones II may be prepared by oxidation of the monoketones R 2 COCH 2 R 3 or R 2 CH 2 COR 3 , or the olefin R 2 C : CR 3 . The intermediate benzyl pyridyl ketones may be prepared by reaction of a pyridine carboxylic ester with a phenylacetic acid ester in the presence of strong base. Phenyl - (pyrazinyl - 2 - methyl) - ketone may be prepared by reaction of 2-methyl pyrazine with sodamide followed by methyl benzoate. (α - Hydroxyimino - benzyl) - (3 - pyridyl)- ketone may be prepared by reaction of benzyl-(3- pyridyl)-ketone with nitrous acid followed by basicification. Pharmaceutical compositions of the compounds I show anti-inflammatory, antipyretic, antiphlogistic and analgesic activity when administered orally, rectally, parenterally or topically with the usual excipients.