DE1695910A1 - Process for the preparation of new 2-amino-5-nitro-thiazoles substituted on the amino group - Google Patents

Description

Dr. F. Zunisfein - Dr. E. A ^ smann

... r.L> except

K-J: ic.iv.-ciiits

, Monks 2, B.-äuhaussfrafce 4 / JJJ

Case 5/371
Dr. Bu / Schl

; KARL THOMAE G-KBH. , BIBERAGH M THE RIP

Process for the preparation of new ones substituted on the amino group 2-amino-5-nitro-thiazoles

The invention relates to a method for producing new 2-Amino-5-nitro-t3iiazoles of ™ substituted on the amino group general formula

/ ~ 1 I,

in which the leftovers

R _{1 is} a hydrogen atom, a dialkylaminoalkyl or hydroxyalkyl group,

R _{2 is} a hydrogen atom, a hydroxyl, alkyl, hydroxyalkyl

109819/2178

ORlGlMAl ίΗδΡΕΟΤΕΟ / 2

or carboxyl group, 1695 9 ΊΟ

R is a hydrogen atom, an alkyl or an optionally aryl group substituted by a nitro group and the Symbols

X is an oxygen or sulfur atom or the imino group and η denote the number 2 or 3, as well as their physiologically acceptable acid addition salts with inorganic or organic acids.

According to the invention, the new compounds are obtained by reaction of 2- (bismercapto-methylenamino) -4-nitro-thiazoles of the general formula

.SR II

F = Cr ⁴

in which the radical R has the meanings given above and the radical R. an alkyl, aralkyl, alkenyl, carbalkoxyalky ^ or amino carb onylalky lgruppe, the radical R ₁ - an alkyl, aralkyl or alkenyl group or together with the radical R, an alkylene group of the formula (-CHp-), in which m is the number 1, 2 or 3, with bifunctional nucleophilic compounds of the general formula

HX

HH
1

109819/2178

in the R-,, R _? , X and η are defined as mentioned above, 'obtained.

The reaction is expediently carried out at elevated temperatures in the presence of a solvent, but it can also be carried out in the Melt has been carried out. As a solvent, "are for example water-containing or anhydrous aliphatic alcohols or lower ketones are suitable. The required temperature depends on the reactivity of the bifunctional compound of the formula III and is preferably between 60 and 200 C.

The reaction takes place via an intermediate product of the Formula.

IV

U = C.

R ₁ R ₂

in which the. Radicals R * to R. and X and η are as defined above. However, this compound can usually not be isolated since it is very easily converted into a compound of the formula I by cyclization. When converting compounds of the formula III with lower reactivity, especially those in which X is an oxygen atom, at temperatures below 10O ⁰ C, the compounds of the formula IV can also be isolated, which are then

ring-closed in the presence of a base when temperatures hit preferably above 10O ⁰ C, or / or room temperature. In this case, for example, alkali metal alcoholates or tertiary amines can be used as bases.

109 819 / '? 178

The file Auegangeetoffe used ^ compounds of formula II

are new and can after the German federal patent

(cf. patent application of the same applicant dated the same day with the title ^M Process for the production of new 2- (bismercapto-nieth _u lenamino) -5-nitro-thlaz; olen ", internal designation Case 5/369) described processes are produced,

The compounds of the formula I obtained in this way can be used if desired in i ^ re pharxacologically compatible acid addition salts with inorganic or orange acids transfer according to the usual methods,

The new compounds have valuable pharmacological properties Properties. They and especially antibacterial, trichoffionastatiech and achistoßomicid r.irksair ..

The following examples should be the .rfindunt; closer explain i

1098 19/7 178

Example 1 .-.

2- / T.3-oxazolidinylidene- (2) -amino7-5-nitro-thiazole

10 g (0.04 mol) 2- / l bismethylmercaptomethylene) aminoy ⁷ -5-nitrothiazole are dissolved in 200 ml of n-butanol, 2.4 g (0.04 mol) of ethanol amine are added and the mixture is refluxed for 2 hours . Compartment, the evaporation in a vacuum "remains a black, greasy mass. This mass is dissolved in ethyl acetate, leaving yellow crystals behind.
Melting point: 215 ° £ (dec.); Yield: 1 g ($ 12 of theory).

Example 2

a) 2- ₍ / Ethanolamino-methylmercaptomethylene) -amino7-5-nitro-thiazole

10 g (0.04 mol) of 2- ^ bismethylmercaptomethylene) amino7-5-nitrothiazole are dissolved in 500 ml of ethanol, 2.42 g (0.04 mol) of ethanolamine are added and the solution is refluxed for 2 hours. After evaporation, a dark, greasy residue remains. The residue is extracted with ethyl acetate, the solution is treated with charcoal, filtered and concentrated. Yellow crystals precipitate. Me crystals are recrystallized three times from ethyl acetate. Melting point: 156-158 ⁰ G; Yield: 5.8 ($ 55 of theory).

b) 2- / T, 3-0xazolidinylidene- (2) -amino7-5-nitro-thiazole

5.3 g (0.02 mol) 2- / TA'thanolamino-methylmercapto-methylene) -amino7-5-nitro-thiazole (Example 2a) are dissolved in 150 ml of ethanol and a solution of 0.46 g of sodium in 50 ml of ethanol is added. The solution is left to stand at room temperature overnight. The solution is evaporated to dryness, the residue redissolved in water and cooled with acetic acid

/ 6 109819/7 178

neutralized. Yellow crystals of 2- / 1.3-0xazolidinylidene- (2) -amino7-5-nitro-tniazole precipitate, which are filtered off with suction, dried and washed with ethyl acetate.
Melting point: 215 ° (decomp.); Yield: 4.2 g (97% of theory).

Example 3

2- / T3-methyl-l. 3-oxazolidinylidene- (2) -amino7-5-nitro-thiazole

10 g (0.04 mol) 2- / bismethyl mercaptomethylene) -amino7-5-nitro-. thiazole are dissolved in 500 ml of acetone, 3 g (0.04 mol) of N-methylethanolamine are added and the mixture is refluxed for 2 hours. The acetone is distilled off, the residue is triturated with methanol and filtered off with suction. The preparation, which was very sparingly soluble, was boiled twice more with methanol.
Melting point: 281 ° (dec.); Yield: 6.3 g (69 $ of theory).

Example 4

2- / TN-ß-hydroxypropyl-l. 3-oxazolidinylidene- (2) -amino7-5-nitrothiazole

10 g (0.04 mol) of 2- / r-bismethylmercaptomethylene) amino7-5-nitrothiazole and 4.76 g of ethanol-isopropanolamine are dissolved in 300 ml of butanol and refluxed for 2 hours. After the butanol has been distilled off in vacuo, a viscous black residue remains. By triturating with a little propanol and cooling with ice, dark yellow crystals are obtained. The crystals are made three times from propanol. recrystallized.
Melting point: 148-150 ⁰ C; Yield: 2.4 g ($ 22 of theory).

/ v

1098 19 / 217-8

Example 5

2- / lN-3-HyG.roxypropyl-l.3-oxazolidinylidene- (2))

thiazole '

10 g (0.04 · mol) 2- / TBismethylinercapto-inethylene) -ainino7-5-nitrothiazole and 4 »8 g (0.04 mol) ethanol-n-propanolamine are dissolved in 350 ml n-propanol and mixed for 2 hours Refluxed. After concentrating, a black oil remains. When triturated with ethyl acetate and left to stand for a long time, the oil partially crystallizes. The crystals are recrystallized twice from Propanoi. Melting point: 151 to 153 ⁰ C; Yield: 3.2 g ( $ 29 of theory).

Example 6 '".

2- / ß-ß-RjäT oxypropyl-2-methyl-1,3-oxazolidinylidene- (2)) - amino / -

5-nitro-thiazole

10 g (0.04 mol) 2- (r-bismethylmercapt (O-methylene) -amino7-5-n-itrothiazole are with 5.32 g (0.04 mol) of Ui-isopropanolamine in 200 ml Butanol for 2 hours. Refluxed. A viscous red-brown oil is obtained on evaporation. The crude product was on a Silica gel column chromatography with methanol as the eluent. After evaporation of the methanol, an oil remained, which with Trituration with a little ethyl acetate crystallized. The preparation was Recrystallized three times from ethyl acetate. Melting point: 139 ° C; Yield: 1.5 g ($ 13 of theory).

Example. 7 -

2- / C --- ß ~ Hydroxyethyl- !. 3-oxazolidinylidene (2) thiazole

² »5 3 (0, Ol mol) 2- (bismethylmercaptomethylene-amino) -5-nitro-

thiazole and 1.1 g of diethanolamine (0.01 mol) are in 50 ml of Propanoi

1098 19/7178

Heated under reflux for 2 hours. The resulting solution will concentrated and sucked off and out of the precipitated product Recrystallized water with the addition of activated charcoal. Yield: 1.8 g (64 $ of theory) sintered from 160 ° u. Decomp. from 260 °.

Example 8

2- / X "li-2-Hydroxyäthyl-1.3-ozazolidinyliden- (2)) - ajiiiiio7-4-methyl- 5-nitro-thiazole

from isopropoxyethanolamine and 2- (bismethylmercapto-methylenamino) -5-nitro-thiazole.
Melting point: 192 ° (decomp.).

Example 9
. 2- / T ^ -B en zy 1-1.3-oxazolidinylidene- (2) -amino / ^ - nitro-thiazole from benzylethanolamine and 2- (bismethylmercapto-methylenamino) -5-nitro-thiazole.
Melting point: 14O ⁰ G (decomp.).

Example 10

L-2 - / "[" 4-Ca ^ OXy-1.3-oxazolidinyl'idene- (2)) - aminoZ-S-nitro-thiazole 2.5 g (0.01 mol) 2- (bismethyl mercapto-methylenamino ) -5-nitrothiazole, 1, 1 g (0.01 mol) of I-serine, and 1.4 ml of triethylamine are boiled for 3 hours under reflux _s in a mixture of 100 cc of methanol and 25 cc .Water. The methanol is drawn off, replaced with water, filtered off from undissolved material, carefully acidified with 2N acetic acid, centrifuged off from the precipitate which has separated out and the aqueous solution is evaporated in a rotary evaporator. The residue is rubbed with n-propanol, the crude product (Ig) is filtered off with suction and recrystallized from water.
Felty lemon yellow needles; Melting point: 211 ⁰ C (dec.).

BAD ORIGINAL 1098 19/71 7 8. - ~ "/ 9

Example II

L-2 _< /T4-Cc.r boxy-1.3 ~ thiazolidinylidene- (2)) - a: .ii: io7-5-nitro-thiazole

Analogously to Example 10, however, instead of S-serine with! -Cysteine. Yield: $ 45; Melting point: 238 ° (decomp.).

Example 12

2— ^ Cw- (2-hydroxyethyl) -1.3-thiazolidi; aylidene- (2)) - amino / -5-nitro-

thiazole . '".- ■

14.95 g (0.06 mol) 2- (bismethylmercapto-methylenamino) -5-nitrothiazole are placed in 100 ml of methanol and 7.27 g (0.06 mol) 2- (ethanol-amino) -ethane- thiol was added dropwise and refluxed for 2 1/2 hours. Huh. Cooling crystallize out 13.6 g (83 $ of theory) of a yellow product. Melting point: 179-18O ⁰ G from ethanol.

Example 13

2- (1.3-'I ': iiazOlidinyliden- (2) -amino) -5-nitro-thiazole from 2-mercapto-ethylamine and 2- (bismethylmercapto-methylenainino) -5-nitrothia ^ ol, yield: 91 $ of theory; Melting point: 261 ⁰ C.

14th

2- / 4- (Methoxycarbonyl) -1.3-thiazolinylidene- (2) -amino7-5-nitro thiazole from L-2-amino-3-mercap-co-propionic acid methyl ester and 2- (bismethylmercaptomethylenaciino) - 5- ⁱ nitro-thiazole. Yield: $ 52 of theory; Melting point: 170 - 171 ⁰ C.

/ 10

BADORiQlNAU. 109819/2178

Example 15 . ·.

2- (1.3-I * ~ idazolidinylia3n- '2) -pr-js, o) -5-niiro-thiazole

2.5 g (0.01 mol) of 2- (bismethylmsreapto-methylenamlno) -5-nitrothiazole and 1 g of ethylenediamine are refluxed in 30 ecm of ethanol for 10 minutes and the crystals obtained are filtered off with suction after cooling.
Yield: 2 g (94% of theory); Melting point: 273 ° 0 (dec.) · Or

a) 4 g (0.01 mol) 2- (Bisbehzylmercapto-methylenar ^ ino) -5-nitro-

thiazole and 0.6 g (0.01 iiol) of ethylenediamine are boiled under reflux for 1 hour in 50 ecm of methanol. After cooling, it is filtered off with suction and uricrystallized from dimethylformamide. Yield: 1.2 g ($ 56 of theory),
or

b) 2.5 g (0.01 mol) 2- / Tl.3-dithiacyclopentylidene- (2)) -amino7-5-nitro-thiazole and 0.6 g (0.01 iiol) ethylenediamine are in 30 ecm Butanol heated under reflux for 30 minutes. After cooling, it is used washed with methanol and then with ether. Yield: 1.7 g ($ 80 of theory).

Example Ic . . ...

2 - / ^ - (2-Hydroxyethyl) ~ 1,3-imidazolidinylidene- (2) -amino7-5-nitro thiazole

Analogous to Example 15, but with! ■ .lonoethanol-ethylenediamine. Yield: $ 76 of theory; Melting point: 152-153 ⁰ O. '

17th

2- / l ^; ; Iexahy.dro-pyrimidinyliden- (2)) -aminoT'-S-nitro-thiazole

2.5 g (0.01 mol) 2- / l ["bismethylmercaptomethylene) -amino7-5-nitro- • chic-zol are mixed with-lgp _ro - _o / ylenediamine in 30 ml acetone overnight

109819/2178 / l

BADORLGiNAL

"left to stand at room temperature. The acetone is distilled off, the residue revealed with a little ethanol and filtered off with suction. Melting point: 264 "- 266 ° (dec.)» Yield: 1.5 g (67 $ of theory)

Example 18
2 - / ^ - hydroxymethyl-l _t 3-oxazölid-ynyliden- (2)) - amiito7- '

5-nitro-thiaz oil

2.5 g (0.01 liol) 2- (bismethylmercapto-methylenamino) -5-nitrothiazole and 0.9 g of 3-AmirxO-1,2-propanediol (0.01 mol) are refluxed in methanol for 3 hours. The unusual one Product is filtered off with suction and recrystallized from JSu ^ anol. ' Yield: 58 ^ of theory; Melting point: 209 ° G * ^

19th

2- _i / Jii-3'-hydroxyethyl-1.3 -oxazolidinylidene- (2)) thiazole-hydrοchloride

25.8 g 2- / XSi-β-hydroxyethyl-1,3-oxazolidinylidene- (2)) -amino7-5-nitro-xhiazole are in the industry in as little methanol as possible dissolves and excess methanolic hydrochloric acid is added. The resulting hydrochloride is then precipitated with a lot of ether. Yellow crystals, yield: 23 gr ($ 78 of theory.).

Melting point: 132-133 ⁰ C.

BATH

10 9819/2178

. The compounds of the general formula I according to the invention can be used for pharmaceutical use in combination with other antibacterial, antiprotozootic and / or anthelmintic compounds into the usual pharmaceutical Incorporate preparations. The single dose is for adults 20 to 400 mg, preferably 50-250 mg. The examples below describe the manufacture of some pharmaceutical products Forms of preparation.

Example I.

Tablets with 100 mg 2- / rN-ß-hydroxyethyl-1,3-oxazolidinylidene- (2)) -aminoT'-S-nitro-thiazole.

Composition:

1 tablet contains:

2-ZTN-ß-hydroxyethyl-1,3-oxazolidinylidene- (2)) -

100.0 mg

Milk sugar 50.0 mg

Potato starch 42.0 mg

Polyvinylpyrrolidone -6.0 mg

Cellulose microcrystalline 20.0 mg

Magnesium stearate '2.0 mg

220.0 mg

A manufacturing process:

The active substance is mixed with the lactose and the potato starch and granulated with a 12.5 mm $ strength by weight ethanolic solution of the polyvinylpyrrolidone through a sieve of mesh width 1.5, dried at 40 ⁰ C. and again rubbed through a sieve of mesh width 1.0 mm. The granulate obtained in this way is mixed with cellulose and magnesium stearate and compressed into tablets.

Table ttengewich'ti 220.0 mg punch 9 mm

/ 13

10 98197-178

IU-JJvJ IU

Example II

Dragees with 100 mg 2- / Tli-ß-hydroxyethyl-1,5-oxazolidinylidene- (2)) -amino7-5-nitro-thiazole.

The tablets produced according to Example I are coated according to a "known process with a shell consisting essentially of sugar and talc". The finished coated tablets are made with the help of
Beeswax polished.

Dragee weight 300.0 mg

Example III

Oblate capsules with 200 mg 2 - / [N- (2-hydroxyethyl) -1, 3-thiazolidinylidene- (2)) - amino7-5-nitro-thiazole.

1 cachet contains:

- (2-Hydroxyethyl) -1,3-thiazolidinylidene- (2)) - amino7-5-nitro-thiazole 200.0 mg

Corn starch 50.0 mg

250.0 mg

Production method;

The active ingredient is intensively mixed with the corn starch and used in Oblaxen capsules of suitable size filled.

Capsule filling: 250.0 mg

Example IV

Dragees with 150 mg of 2- / 1 "N- (2-hydroxyethyl) -1, 3-thiazolidinylidene- (2)) - amino7-5-nitro-thiazole.

1 tablet core contains 2- / TN- (2-hydroxyethyl) -l, 3-thiazolidinylidene- (2)) - amino7-5-nitro-thiazole 150.0 mg

Corn starch 109R13 // M78 60.0 mg

Gelatin 4.0 mg

J-t

Carry over 214.0 mg

Carboxymethyl cellulose 4.0 mg

highly viscous

Magnesium stearate 2.0 mg

220.0 mg

Production method;

The mixture of active substance and corn starch is granulated with a 10 ^ strength aqueous gelatin solution through a sieve with a mesh size of 1.5 mm, dried at 45 ° C. and again through rubbed a sieve with a mesh size of 1.0 mm. The granules are mixed with carboxymethyl cellulose and with magnesium stearate and pressed the mixture for tablet cores.

Core weight: 220.0 mg
Stamp: 9 mm, domed '

The tablet cores produced in this way are made according to a known method covered with a shell consisting essentially of sugar and talc. The finished coated tablets are made with the help of beeswax polished.

Dragee weight: 300.0 mg

Example T.

Gelatine capsules with 100 mg 2- / N- (2-hydroxyethyl) -l, 3-imidazoli ~ dinylidene- (2) -amino7-5-nitro-thiazole.

Composition:

1 gelatin capsule contains:

2- / N- (2-hydroxyethyl) -1,3-imidazolidinylidene- (2) amino7-5-nitro-thiazole 100.0 mg

Aerosil R 972 1.0 mg

101.0 mg 10 9 8 19/7178 _{/ l5}

Production method; .

The active ingredient is intensively mixed with Aerosil and placed in gelatine capsules Bottled of suitable size.

Capsule filling: 101.0 mg

Example VI .

Tablets with 200 mg 2- / l ^! - (2-Hydroxyethyl) -l, 3-imidazolidinylidene- (2) -amino7-5-nit.ro-thiestol.

Composition ^::

1 tablet contains:

2- / 1- (2-Hydroxyethyl) -1,3-imidazolidinylidene- (2) -amino7-5 ⁱ -nitro-thiazole 200.0 mg

Milk sugar 110.0 mg

Potato starch 70.0 mg

Polyvinylpyrrolidone 10.0 mg

Aerosil 5.0 mg

Magnesium stearate 5.0 mg

400.0 mg

Production method:

The active ingredient mixed with milk sugar and potato starch
is granulated with a 10 ^ igen ethanol solution of polyvinylpyrrolidone through a sieve with a mesh size of 1.5 mm, at
Dried at 45 ° and rubbed through the above sieve again. That so
The granulate obtained is mixed with Aerosil and magnesium stearate. The mixture is compressed into tablets »

Tablet weight: 400.0 mg
Stamp: 11 mm, flat = - ■

/ 16 109819/7178

Claims (1)

P at e nt to s p e ch e 1.) Process for the preparation of new substituted on the amino group 2-Amino-5-nitro-thiazoles of the general formula = 1 in which the leftovers R, a hydrogen atom, a dialkylaminoalkyl or Hydroxyalkyl group, R _{2 is} a hydrogen atom, a hydroxyl, alkyl, hydroxyalkyl or carboxyl group, R, a hydrogen atom, an alkyl group or an aryl group optionally substituted by a nitro group and the symbols X is an oxygen or sulfur atom or the imino group and η denotes the number 2 or 3, as well as their acid addition salts with inorganic or organic acids, characterized in that a 2- (bismercaptomethyleneamino) -4 - nitrothiazole the general formula II, 1098 19/9178 in which the radical R, has the meanings given above, R a Alkyl, aralkyl, alkenyl, carbalkoxyalkyl or aminocarbonylalkyl group, R, -. an alkyl, aralkyl or alkenyl group or, together with the radical R., an alkylene group of the formula (-CHp) -, in which m is the number 1, 2 or 3, with a compound of the general formula HX (CH ₂ ) -H ₂ in the R ,, Rp 'and X have the meanings given above η, _s is reacted at elevated temperatures which, in general, an intermediate of general formula IV, a. v vün / Λα R ₁ R ₂ forms in which the radicals R- to R «_ and X and η are those mentioned above Have meanings which can be obtained without prior isolation by further heating or by adding a base cyclized and the compound thus obtained by means of inorganic or organic acids is converted into their acid addition salt. / 18th 9 8-1-9 /> 1 7 8 - XO - 2.) The method according to claim 1, characterized in that the Implementation is carried out in the melt. 3.) The method according to claim 1, characterized in that the Reaction is carried out in an inert solvent. 4.) The method according to claim 1, 2 or 3 »characterized in that the reaction is carried out at temperatures between 60 and 200 ⁰ G. 5.) Process according to claims 1-4 »characterized in that in the reaction with a compound of formula III with low reactivity, especially with a compound in which X is an oxygen atom, at temperatures below 100 ° o the intermediately formed intermediate product of the formula R- * IV, Il ■ '-... 1 Rp in which the radicals R, to R, and X and η, the above-mentioned meanings, is isolated and then eyelisiert by heating to temperatures preferably above 10O ⁰ G or by treatment with a base at room temperature. 6.) Method according to claim 5, characterized in that as Base, an alkali alcoholate or a tertiary amine is used 7.J. Newly substituted 2-aiaino-5-nitro-thiasols on the amino group the general formula '■ ". / 19 109819 / ^ 178. - ι? - ■ M _A 1 γ (GH ₉ ) - in which the leftovers> R _{1 is} a hydrogen atom, a dialkylaminoalkyl or hydroxyalkyl group, R _{2 is} a hydrogen atom, a hydroxyl, alkyl, hydroxyalkyl or carboxyl group, R, a hydrogen atom, an alkyl group or an aryl group optionally substituted by a hydrogroup and the Symbols. X is an oxygen or sulfur atom or the imino group and η denotes the number 2 or 3, as well as their acid addition salts with inorganic or organic acids. 8.) 2- / Cii-3-hydroxyethyl-1,3-oxazolidinylidene- (2)) -f nitro-thiazole and its acid addition salts with inorganic ones or organic acids. 9.) 2- / rN- (2-hydroxyethyl) -1, 3-thiazolidinylidene- (2) -amino7-5-nitro-thiazole and its acid addition salts with inorganic ones or organic acids. 10.) 2- / rK- (2-hydroxyethyl) -1, 3-imidazolidinylidene- (2)) - amino7-5-nitro-thiazole and its acid addition salts with inorganic or organic acids. 2- ^ g-Hydroxymethyl-1,3-oxazolidinylidene- (2)) - ϊΧ ^ χ: ΐ & Χ5Χ5} 3! Ε) Εβ6ϊ ^ £ .aino7-5-nitro-thiazole and its acid addition salts with cj-inorganic or organic acids. 10 9819/7178 / 20 ■ - ■ 20 - 169591D 12), 2- (l, 3-hiiazolidinylidene- (2) -amino) -5-nii; ro-thiazole and whose acid addition salts with inorganic or organic " see acids. 13) 2- / l, 3-oxazolidinylidene- (2) -amino7-5-nitro-thiazole and its Acid addition salts with inorganic or organic acids. 14) 2- / TN-β-hydroxypropyl-1,3-oxazolidinylidene- (2)) -amino7-5-nitro-thiazole and its acid addition salts with inorganic or organic acids. 15) 2- / ΓΝ-3-hydroxypropy1-1,3-oxazolidinylidene- (2)) - amino / -!? - nitro-thiazole and its acid addition salts with inorganic or organic acids. 16) 2- / TM'-ß-hydroxypropyl-2-meth.yl-l _i 3-oxazolidinylidene- (2)) - aminoZ-S-nitro-thiazole and its acid addition salts with inorganic or organic acids. 17) Pharmaceutical preparations, with antibacterial, antiprotozootic and / or anthelmintic effectiveness by a content of active substance of the general formula I. " 18) Pharmaceutical preparations according to claim 17, characterized in that that in addition to an active substance of the general formula I, other antibacterial, antiprotozootic and / or anthelmintic effective compounds are included. 19/7178