DE1768370C - Diethyl alpha- (2-dibenzofuranyl) malonate - Google Patents

Description

The invention relates to diethyl-a- (2-dibenzo " funwyO-malonat the formula

COOC _{2 HY}

CH

COOC ₂ H ₅

It has been found that the compound and anliphlogisticum containing it is a very interesting is anti-inflammatory agent. The anti-inflammatory effect was determined by the Proceedings Society Experimental Biology Medicine, 111: 544 (1962), induced by carrageenan Edema test determined. For this purpose, female rats from the Wistar strain were used, which were between 120 and weighed 150 g. The compound was administered orally in a suspension of a 10% acacia gum solution administered in various dosages.

Furthermore, the anti-inflammatory active wedge was determined by the granuloma bead test (R. Meier, W. Schuler, P. Desaules, Experientia, 6 [1950],

5. 1469) checked. Wistar rats were used for this used, in which two cotton balls were placed under the skin. The attempt was made performed on groups of seven animals for each dose used. The connection to be tested was taken orally and in a suspension of a 0.5% aqueous methyl cellulose solution, namely Administered once a day for 6 days. At the end of

On the 6th day after the rats were sacrificed, the decrease in volume of the granulomas was determined.

In the above experiments, acetylsalicylic acid was used as a comparison substance. The results achieved here and the LD ₅₀ values are given below.

connection Dose at
Rails,
per os
mg / kg Carrageenin
Udem,
percentage
acceptance
of the edema cotton
globules,
percentage
Weight
decrease of the
Granuloma Diethyl-a- (2-di-
benzofuranyl) -
malonat 50
100
200 16.7
27.8
48.6 18.8
24.9
38.6 Acetylsalicylic
acid 20th
50
100 11.4
21.4
38.6 15.2
19.0
30.8

LD, _n values

connection Mii
ip
mg / kg use
per os
mg / kg Ri
ip
mg / kg kill
orally Diethyl
a- (2-dibenzo-
furanyl) -
malonat 1330 to
1430 10,000 1195. > 5000 Acetylsalicylic
acid 319 1 100 500 1360

The values found show that the diethyl u- (2-dibenzofuranyl) molonate is the comparative substance is significantly superior

The DlU (hyl - «- C2-dlbcnzofiirunyl) -malonal takes place as s active ingredient in a therapeutic agent Use. Excellent results have been obtained in treating some skin diseases, for example of eczema and allergy dermatitis, achieved by the application of ointments that range from 0.1 to ίο 1% of the diethyl a- (2-dibenzofuranyl) -malonate in mixture with conventional pharmaceutical excipients.

Furthermore, the diethyl α- (2-dibenzofuranyl) malonate is also very effective in curing, for example rheumatoid fever, chronic rheumatoid arthritis, rheumatoid arthritis and gout, the results with the usual forms of administration, such as oral, intramuscular and rectal Gabe were satisfactory.

The diethyl a- (2-dibenzofuranyl) malonate is thereby produced that ethyl 2-dibenzofuranylacetate in a known manner with 1 to 1.5 mol Sodium ethylate dissolved in a more than equimolar excess of diethyl carbonate is heated.

example

8.6 g of sodium are dissolved in 240 ecm of anhydrous ethanol and then the solvent is distilled off on an oil bath. The residue of sodium ethylate is now dissolved in 250 ecm of diethyl carbonate and then slowly added in the course of 2.5 hours with a solution of 69 g of ethyl 2-dibenzofuranyl acetate in 250 ecm of diethyl carbonate. The bath temperature is then increased to 150 ^° C. until the solvent has been completely removed. The mixture is then poured into ice water, acidified with hydrochloric acid and extracted 3 to 4 times with diethyl ether. The combined ether extracts are dried over sodium sulfate and then evaporated to dryness. The residue is recrystallized from isopropyl ether, 6.7 g of diethyl a- (2-dibenzofuranyl) malonate having a melting point of 84.5 ° to 85 ° C. are obtained.

Claims (3)

Patent claims: 1. Diethyl - «- (2-dibenzofuranyl) malonate of the formula COOC ₂ H ₅ 2. Antiphlogisticum, characterized by a content of diethyl a- (2-dibenzofuranyl) malonate according to claim 1 in addition to customary inert carriers. 3. Antiphlogisticum according to claim 2, characterized in that it contains 0.1 to 1% diethyl a- (2-dibenzofuranyl) malonate contains.