Novel N'-acylated phenyl-hydrazine and hydrozone derivatives

Abstract

Abstract Novel indolylacetic acid derivatives, which have excellent anti-inflammatory, antipyretic and analgesic activities, represented by the formula, ##SPC1## Wherein X 1 and X 2 each is a member selected from the group consisting of oxygen and methylene; A is a member selected from the group consisting of unsubstituted saturated hydrocarbon chain having up to 5 carbon atoms, unsubstituted unsaturated hydrocarbon chain having up to 5 carbon atoms and substituted saturated or substituted ethylenically unsaturated hydrocarbon chain having up to 5 carbon atoms, in which the substituents are selected from the group consisting of halogen or phenyl, the hydrocarbon chain being straight or blanched one; m is 0 or 1; n is 1 or 2; R 1 and R 2 each is a member selected from the group consisting of hydrogen and alkyl having up to 4 carbon atoms; R 3 is a member selected from the group consisting of alkyl having up to 4 carbon atoms, unsubstituted or a lower alkyl-, lower alkoxy-, lower alkylthio-, nitro-, cyano-, methylenedioxy-, ethylenedioxy- or halogen-substituted aryl, each of said alkyl, alkoxy and alkylthio substituents containing up to 4 carbon atoms, or unsubstituted, or halogen-, alkyl- or phenyl-substituted or benzene ring-condensed, saturated or unsaturated mono- or poly-aclicyclic group, or alkyl group substituted by said alicyclic group, or unsubstituted or methyl-, ethyl- or halogen-substituted 5- or 6-membered heterocyclic ring group containing oxygen, sulfur or nitrogen atom; R 4 is a member selected from the group consisting of alkyl having up to 4 carbon atoms or hydrogen, or a group of M (wherein M is a cation). The indolylacetic acid of the formula (I) is prepared by reacting a compound of the formula, ##SPC2## Wherein X 1 , X 2 and n are the same as defined above and B is a member selected from the group consisting of ##EQU1## and Z (wherein Z is a nitrogen protecting system comprising at least one readily removable group), with an acid halide represented by the formula, R.sub.3 --(A).sub.m --CO--hal (V) wherein R 3 , A and m are the same as defined above and hal is halogen, to obtain N 1 -acylated compound of the formula, ##SPC3## Wherein X 1 , X 2 , R 3 , A, B, m and n are the same as defined above, then reacting the resultant N 1 -acylated compound (II) with an aliphatic acid derivative represented by the formula, ##EQU2## wherein R 1 , R 2 and R 4 are the same as defined above.

Inventors

• 👤 Michio Kimura
• 👤 Shigeho Inaba
• 👤 Hisao Yamamoto

Bibliographic Details