Über neue 3,5‐Dioxo‐pyrazolidine

Abstract

Volurneii XXXVI, Fasciculus I (1953) -KO. 10-11. 75 tlinationsverbindungen liess sich zcigen, dass auch solche unter den gewahlten Bedingungen reduktiv aufgespalten werden.Bei A. E i n l e i t u n g . Die Entnicklung der Arzneimittel aus der Gruppe dcr von Knorrz) cntdeckten P y r a z o l o n e war in den letzten Jahrzehnten zu eincm gewissen Stillstand gekommen.Seit der Einfuhrung des 4-Dimethylamino-antipyins oder P y r a m i d o n s (I)3), das noch lieute als das beste Arzneimittel dieser Stoffklasse gelten kann, wurde immer wieder versucht, die geringe Loslichkeit dieser Substanz zu verbessern, da fur die moderne perorale Stosstherapie nur Produkte mit guter Wasserloslichkeit in Frage kommen. Wohl wurden im Verlauf dcr Zeit verschiedene Pyrazolon-Derivate mit verbesserter Wasserloslichkeit cntmiclrelt, doch geniigtcn deren pharmakologische Eigenschaften nicht, um die klinische Bedeutimg des Pyramidons zu erreichen. 1) Jurg Ammann, ,,Synthesen in der Pyrazol-3,5-dion-Reihc", Diss.

Synthesis and Bioassay of Amino-pyrazolone, Amino-isoxazolone and Amino-pyrimidinone Derivatives

“…16) The cyclocondensation of 1, 7 and 8 with hydrazine hydrate in the presence of piperidine in ethanol afforded 5-amino-4,4-bis-(2Ј-phenylsulfonylethyl)-pyrazol-3-one (2), 5-amino-4-(2Ј-arylsulfonyl-1Ј-arylethyl)-pyrazol-3-one (9) and 5-amino-4-(2Ј-arylmethylsulfonyl-1Ј-arylethyl)-pyrazol-3-one (10). Similarly, 3-amino-4,4-bis-(2Ј-phenylsulfonylethyl)-isoxazol-5-one (3), 3-amino-4-(2Ј-arylsulfonyl-1Ј-arylethyl)-isoxazol-5-one (11) and 3-amino-4-(2Ј-arylmethylsulfonyl-1Ј-arylethyl)-isoxazol-5-one (12) are obtained by treating 1, 7 and 8 with hydroxylamine hydrochloride.…”

“…7,8) Besides this, pyrazole and isoxazole derivatives possess bacteriostatic, antidiabetic, analgesic, antiarrhythmic, anti-inflammatory, antifungal and antiviral properties. [9][10][11][12][13][14] Celecoxib, a pyrazole derivative, and valdecoxib, an isoxazole derivative are now being used as anti-inflammatory drugs. 15) A continuoues effort is maintained in our laboratories for the development of biologically potent heterocycles.…”

Disposition of [4-14C]mofebutazone in the rat

“…58-62. 0-4400 MUNSTER, Federal Republic of Germany with phenylhydrazine hydrochloride (7). The labelled malonic ester was prepared by treating the thallium salt of labelled malonic acid diethyl ester with butyl iodide; the method was similar to that described by Taylor,Hawks and McKillop (8).…”

Synthesis of Derivatives of Pyrazolin-1H-3-ones from 2′-N-Substituted Monohydrazides of Cyclohexenedicarboxylic Acids

“…After the Knorr synthesis of antipyrine (2,3-dimethyl-1-phenylpyrazolin-5-one) [1] work continued on the preparation of new pyrazolin-5-ones, since many of them are widely used in color photography and are applied in medicine as pharmacological preparations with analgesic and antipyretic action [2][3][4].…”

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Keywords: hydrazide, ethoxymethylenemalonic acid diethyl ester, pyrazoline, pyrazolin-5-one, cyclohexenecarboxylic acid.After the Knorr synthesis of antipyrine (2,3-dimethyl-1-phenylpyrazolin-5-one) [1] work continued on the preparation of new pyrazolin-5-ones, since many of them are widely used in color photography and are applied in medicine as pharmacological preparations with analgesic and antipyretic action [2][3][4].Results are given in the present paper on a study of the possibility of obtaining pyrazolin-5-ones from 2'-N-(2,2-dicarbethoxyethylenyl)monohydrazides of 6-aryl-4-methylcyclohex-3-ene-1,1-dicarboxylic acids 1a-e, synthesized by us previously by condensing monohydrazides of 6-Ar-4-methylcyclohex-3-ene-1,1-dicarboxylic acids with diethyl ethoxymethylenemalonate [5].One of the methods of obtaining pyrazolin-5-ones is based on the cyclization of N-substituted hydrazides obtained analogously to compound 1 [6-9]. Reaction is effected in a melt at 170-175°C [6], on boiling in water [7, 8], or ethanol [9] in the presence of potassium carbonate [8,9], sodium carbonate [7], or sodium ethylate [9].

Attempts by us to cyclize monohydrazides 1a-e under the conditions indicated above were unsuccessful.

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