SU1127249A1 - 2-oxy-1,3-diaminopropane-n,n'-tetra (ethyliminodiacetic acid) as antidote of incorporated plutonium - Google Patents

Description

111272492

This invention relates to a new aminopropane-N, N-tetra (ethylimino-chemical compound-2-hydroxy-1,3-diacetic acid) of the formula i HOOSHN; 15CH Hg HOOSNg NCH2.CHCH HOOCHN: CH CH% OH HOOCH

possessing the ability to accelerate the dumping of incorporated plutonium.

Chemically, the analogue of the claimed compound is diethylenetriaminepentaacetic acid (DTPA), which in the form of trisodium calcium salt, called pentachl, is used as an antidote for plutonium, lead and other toxic metals,

The purpose of the present invention is to find new antischows that have the ability to accelerate the elimination of incorporated plutonium.

The goal is achieved 2Oxy-1, 3-diaminopropane-K, K-tetra (ethymophenylacetic acid) of formula 1.

The compound of formula 1 in its antidote activity with respect to PU exceeds the drug pentacin and is less toxic than the latter (see table).

The method for preparing 2-hydroxy-1,3-diamine-propane-N, N-tetra (ethyl amino acid) is based on the known reaction of alkyl halides with bis (benzylidene) diethylenetriamine, followed by hydrolysis and carboxymethylation.

Examples

Preparation of 2-hydroxy-1,3-di inopropan-N, N-tetra (ethylaminodiacetic acid O.

A mixture of 28.9 g of bis (benzylidene) diethylenetriamine, 10 g of triethylamine and 4.86 ml of 1,3-dichloro-2-hydroxypropane is boiled in 100 ml of toluene for 30 hours, the precipitate is filtered off and the toluene is distilled off in vacuo. 80 ml of a water-hydrochloric acid (1: 1) mixture is added to the residue, and the mixture is heated for 1.5 hours at a boss level. The aqueous layer was separated, washed with benzene and evaporated in vacuo. Remainder

treated with absolute alcohol when heated and filtered. After drying, 21 g (83%) of N, N-tetra (2-amino-ethyl) -2oxy-1, 3-diaminopropane hexachlorohydrate is obtained, which is mixed with 41.4 g of monochloroacetic acid without further purification. When heated to within 6. h to

This mixture is poured with a solution of 42 g of NaOH in 200 ml of water, maintaining the pH at about 10. The reaction mass is supplied with coal and passed through a column with cation exchanger KU-2-8 in the H-form, eluting with water and 1% ammonia. After evaporation of the eluate, 13.4 g (43%) of 2-OXY-1,3-diaminopropane-N, N-tetra (ethylaminodiacetic acid) are obtained, m.p. 114 -. Nd,%: C 44.34; H 6.78; N 11.62. Mol. Mass 724.20. Cj7H4 ntO, i. Calculated,%: C 44.62; H 6.38; N 11.56. The molar mass is 726.71.

An experimental study of the antidote activity of the described compound, which was used as an aqueous solution of tetrasodium dicalcium salt and pentacin, was carried out on rats infected with 239pu.fivt

The acute toxicity of the compound was determined in outbred mice according to a conventional method. The results of the experiments are given in the table.

From the data it follows that

2-hydroxy-1, 3-diaminopropan-N, N-tetra (ethylaminodioacetic acid) significantly exceeds pentacin in antidote activity with respect to plutonium under these conditions

less toxic.

As can be seen from the data presented in the table, the described compound significantly reduces the isotope content in the liver and skeleton of infected rats.

when administered simultaneously with a nuclide or as soon as possible. cn cn 2 i СНгСОО СН7.СН9КС

31127249 4

Content 239f (y} in the skeleton and liver of rats three days after i / w administration of antidotes (% of control)

Simultaneous introduction

0.5 h after infection

After 3 hours the infection field

0.5 h after infection

SD50G / KG mouse

21.8t 1.3 1.3.5 ± 1.5 43.6t 2.4 26.1 ± 1.8 51.61 3.5 44.7 ± 2.8 20.5 ± 1.3 15.3 to , 6

5.7

Claims (1)

2-0xy-1, 3-diaminoprdan-Ν, Ν ¹ tetra (ethylaminodiacetic acid) of the formula NOOSSNg NOOSSNg H00SSN _g NOOSSNg NSNgSng nsnsnsn _g n LS _{r r} he removed > CH _g COOH SNoCHNH / Csog \ SNGNGI UNVS UNVS as an antidote of incorporated plutonium. one 1 1127249 2