DE1695689C3 - 3- (5-Nitro-2-thenylideneamino) oxazolidone (2) derivatives - Google Patents

Description

get the following results:

Η, Ν —Ν Ο (II) »5

Test compound extent of infection by days

in which R is a morpholino or piperidino group

represents, condensed and, if desired, the 30 3_ (5 "Nitro-2-thenyl-2.3 1.6 0.6 0.2 0.4
obtained compound of the general formula idenamino) -5-morpho converted into a salt by _{treatment with an inorganic or] i no methyl-oxazoliorganischen acid.} don- (2)

3. Medicinal product consisting of a compound

according to claim 1 and conventional carriers 35 N- (5-nitro-2-furfu 2.2 2.0 1.6 1.6 2.4
and / or diluents and / or auxiliary ryliden) -3-amino substances. 5-methylmercapto-

methyl-oxazolidone- (2)
(laid out documents
₄ o of the Belgian patent
6 35 608)

Control experiment 2.4 2.2 2.0 1.8 2.2

The invention relates to the in the claims from the table is the significant effect of

marked object. compound according to the invention (Example 1) apparent

The starting compounds in the invention Hch. The known comparison compound has only

3-Amino-oxazolidone- (2) -ring activity that can be used as a method.

derivatives of the general formula II are used after 50 The acute toxicity (mouse, oral, LD ₅₀ ) of the d-iso-

in the US-PS 28 02 002 described method is her- mers of the compound according to the invention

placed. 897 mg / kg, the 1-isomer 1449 mg / kg and the

In the process according to the invention, the reactive slip compound 4500 mg / kg,

tion participants at room temperature in a solution The examples illustrate the invention,

solvents, such as alcohol, take a short time to react 55

brought. The crude product precipitates and is filtered off .... .

triert. The compound can be prepared by the usual acid-base example l

Purified extraction and removed from solvents such as 3- (5-Nitro-2-thenylidenamino) -5-morpholino-

Acetonitrile, ethanol or mixtures thereof, recrystalline methyl-oxazolidone- (2)

be sated. 60

Inorganic A solution of 8.1 g of S-Amino-S-morpholino-

Acids such as hydrochloric acid, hydrobromic acid or methyl-oxazolidone- (2) in 120 ml of ethanol will quickly

Sulfuric acid, or organic acids used as and with stirring with a solution of 6.3 g of 5-nitro

Acetic acid, fumaric acid, tartaric acid, malic acid, 2-thiophenecarboxaldehyde added in 50 ml of ethanol,

ionic acid, succinic acid or maleic acid. 65 The precipitate obtained is filtered off and, in mixed

The compounds of the invention are antiparasitic agents dissolved in dilute hydrochloric acid. After filtration, the

and have an antibacterial effect. They are particularly acidic filtrate with 5% aqueous sodium carbonate

active against Trichomonas fetus and salmonella solution made alkaline. The product obtained will

filtered off and recrystallized from a mixture of acetonitrile and ethanol. The pure compound melts at 203 to 204 ⁰ C.

The hydrochloride is made by suspending the Base prepared in alcohol and addition of concentrated hydrochloric acid. The precipitate obtained is filtered off and recrystallized.

Example 2

The condensation of 3-amino-5-piperidinomethyl-oxazolidone- (2) with S-nitro- ^ - thiophenecarboxaldehyde according to Example 1 gives 3- (5-nitro-2-thenylideneamino> 5-piperidinomethyl-oxazolidone- (2) , M.p. 270-271 ° C (dec.).

Claims (2)

Bacteria. Compared to the corresponding known patent claims · nitrofuran compounds, they are distinguished by a considerably lower toxicity. The preferred one 1. 3 <5-Nitro.2.thenylidenamino> oxazolidone- (2) - according to the invention, ^ rgftelkeV ^ bmdu ^ gJst 3- (5-Nj- derivatives of the general formula I ⁵ this compound on mice infected with a lethal Trichomonas fetus infection in Doses from 12.5 to 250 mg per kilogram and per π _N _M ^ -CH = NN O (1) "> day, there was 60 to 100% survival ü, Nx _s / -LH N in υ Ii oral administration of 100 mg / kg to mice ^L -CH ₂ - R _erga l, jjejjie deaths during an administration of 400 mg / kg of the corresponding nitrofuran compound in which R a morpholino or piperidino group led to the death of all test animals
represents, and their salts with acids. * 5 Hamsters were also given intravagmally with 2. Process for the preparation of the compounds monas fetus infected. The Verbinnach to be examined Claim 1, characterized in that fertilizers were given orally on four consecutive given in a manner known per se 5-nitro-2-thio days at a dose of 200 mg / kg. 24 stunphencarboxaldehyde with a 3-amino-oxazolidene after each dose, vagmal absjxiche became don- (2) -derivative of the general formula II * °. With the partings, breeding ground was be vaccinated, and after appropriate incubation, the O number of trichomonads read off. There were fol-