Novel N'-acylated phenyl-hydrazine and hydrozone derivatives

Details Novel N'-acylated phenyl-hydrazine and hydrozone derivatives Novel N'-acylated phenyl-hydrazine and hydrozone derivatives

1974-02-04

1976-08-10

Weinberger, Lorraine A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260250B, 2602564R, 260295C, 260295H, 260302R, 260302D, 260307R, 260307H, 260309, 260310R, 2603403, 2603405, 2603462R, 2603453, 26032634, 2603322A, 2603473, 260557B, 260557H, 260558H, 260240J, C07D31766

Patent

active

039741451

ABSTRACT:
Novel indolylacetic acid derivatives, which have excellent anti-inflammatory, antipyretic and analgesic activities, represented by the formula, ##SPC1##
Wherein X.sub.1 and X.sub.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.sub.1 and R.sub.2 each is a member selected from the group consisting of hydrogen and alkyl having up to 4 carbon atoms; R.sub.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.sub.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.sub.1, X.sub.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,

REFERENCES:
The Condensed Chemical Dictionary, 8th Ed., Pub. by Van Nostrand Reinhold, p. 26.
Morrison et al., Organic Chemistry, 2nd Ed., (1966), p. 707.
Allinger, et al., Organic Chemistry, (1971), pp. 610-611.

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