DE2027593A1 - - Google Patents

Description

The present invention relates to substituted 5-Nitrofaryl derivatives of pyrazoles and processes for their Manufacturing.

The present invention includes 5-nitrofurylpyrazoles of the general formula I.

j_C -C -CO-NH ₂ N C-_NH ₂

• · I '

wherein R is an unsubstituted alkyl group with 1 to 5 Carbon atoms "or one substituted by the hydroxyl group Denotes an alkyl group having 2 to 5 carbon atoms.

If K is an alkyl group, it can be

straight or branched chain alkyl group. It preferably contains up to 3 carbon atoms. Examples such alkyl groups are the methyl, ethyl, n-propyl, Isopropyl, η-butyl, isobutyl, tert. 3utyl and n-pen

009850/2192

BATH ORIGINAL

tyl groups. When R is one substituted by the hydroxyl group Denotes an alkyl group, it preferably contains 2 Με_ 3 Carbon atoms.

The present invention also includes additive salts of 5-citrofurylpyrazoles of the formula I with organic and inorganic Acids. Examples of such acids include:

Hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, Methanesulfonic acid, ethanedisulfonic acid, acetic acid, trichloroesslgic acid, Oxalic acid, succinic acid, maleic acid, fumaric acid, malic acid, 'tartaric acid, citric acid and mandelic acid.

Although the compounds prepared according to the invention are described by the formula I, they can also be described by the following tautomeric formula IA is represented,

_1_ (IA)

- CO-NH ₀

AC = NH

with any particular connection according to the invention in one of. bßidp.n -tsutomeric forms · or in a mixture same can occur. In this description, however, the compounds of the present invention are used for clarity sake described by the formula I and are therefore described and explained as nitrofurylpyrazole derivatives. 5-nitrafuryl-pyrazo compounds of the general formula J

are made by adding a 5-nitrofurylpyrazole derivative of the general formula II

0098 507 2192

BATH ORIGINAL.

V o

χ} '' ■■ «■

2Q27593 - cn _(1I)

ν. ·· · γιμ i. di οι-.ti r:. ·: tr b μ -iod-tung hai, hydrolyzed.

t; \ erf r..nT "η ν? -» »η unl ^τ 'Ί * n i'for α ic hyarolysis usual lit d I r.gui ^ c ii \) i"; ai _; iv.-3ise int..! be, oebeispiel ^ eii: ^ by the lii-MMidlunr; r. with aqueous 'Schwc-föl acid within eino-a icriipf-ruLurüer ^ lch from Ό to] OO ^V C. Preferably, the hydro-, lyre l <Li orhihtor' i "oi: .poratur by ^ t- leads, -wherein a heaktionstciiif ■■ · -rcLur in the a · range from? 0 to 1CO ^C C 'is particularly ■ sweck-wise. Vi) r: a _.; ^r rv-ol r> c the · connection cr Kennel II zui -arnmen with a mixture of koii: ^- -: iit.riertor Cc-hv "relLäuro and ethanol heated, whereby a no hoakt-irn: ·; ·" ^ t for 1 to 7 hours r - '. vxckniässi g. . orhnlteno Koakti-.nsproduKt is tiischjk; ::: · id in oi-non Uebf.rschussan water poured u: r ^da: erwünsent "M irofury] -pyrszol of all go: nc I n ^ n F-.. r: nel 1 als'Niedf.rsohlag;"- i <v \ iu \ tf.n.

Nitrofuiylpyrazüle der all £ i; n! «In ·. : i-r'ormtil 11 vrd-iii prepared by: .ir.n d & s corresponding Ui i r ^ furyl-nitrilimine, whosec-n has a mesomeric form by the following! general. '''crir.el hi can be represented

(HI)

009850/2192 _BAD

■> ι *

with malonic acid dinitrile, where R has the meaning given above Has.

The nitrofuryl-nitrilimine of the general formula III can expediently as it is for the reaction with malonic acid dinitrile

is required, be prepared by adding the corresponding nitrofuryl-or-halohydrazone of the general formula IV

O ₉ N__f \ C__X

where X uin HtIOg ^ nHtOm b-doutot and R has the meaning given above has treated with a base. Treatment is done if desired still carried out in the presence of another customary hydrogen halide acceptor. The one in the halohydrazone Halogen contained in general formula IV is preferably chlorine or bromine. ■

The nitrofuryl-a-halohydrazones of the general formula IV are new compounds and can in turn, for example, by reacting the corresponding hitrofurylhydrazones of the general my Formula Vee

ν ^ Γ "

~ ^ WATCH

009850/2192 bad original

with the corresponding N-halogen compound. The present invention further comprises a second process for the preparation of compounds of the general formula I, ":" ■. ■

O ₀ N - ■ {/ - CC-CO-KH ₀ (I)

• ^{2 x} o / Ii i | ²

NC — NH ₀

V ²

wherein R is an unsubstituted or substituted alkyl group. with 1 to 5 carbon atoms' means, characterized in that one is a connection the · general formula VI. '

ON - / ^ G - C - CN (VI)

^N ° N

■■■■ '"ί" ·'

wherein R _{1 is} an acyl group, hydrolyzed and deacylated by treating the compound with a proton donor in a polar solvent and hydrolyzing the protonated intermediate. ·

The present invention further comprises a third process for the preparation of compounds of the general formula I,

O ₀ N -f \ - C - C-CO-NH ₀ (I).

Ii i

609850/2192

NlI ₂

ones »» ·

wherein R is an alkyl group substituted by the hydroxyl group with 2 to 5 carbon atoms, characterized in that a compound of the general formula VII,

O fi_ / V- C C-CK

² \ o / St.

AOR ₂

where Rp is an acyl group and A is an alkylene group with 2 to 5 Kch-

W lenstoffatomen mean hydrolyzed and deacylated by treating the compound with a proton donor in a polar solvent and hydrolyzing the protonated intermediate.

In the processes mentioned, the preferred reactant is ethanolic hydrochloric acid, suitably in one concentration of 40 wt .- ^ used. Other proton donors such as the Example sulfuric acid in other polar solvents can also be used.

^ Although this second and third inventive method are essentially similar, it is interesting to note how the substituents on the 1-nitrogen atoms of the corresponding Starting materials are influenced differently by the various reaction conditions. In the second method, R is a Alkyl group and remains unchanged; in the third method the substituent itself is deacylated to give a hydroxy-alkyl group form.

Normal catfish of the starting material in both the second and the third _$ erf LnöungsgeHiässen will! Experience with a proton donor, such as ethanolic hydrochloric acid while heated,

t ■

ta «

■ ·

until the reaction has definitely taken place. Arisch] then the heating mixture is cooled and an ice-warmer mixture is added, or the re-organic is poured onto an ice-water mixture in order to precipitate the desired product. This Ve: * - drive can boi Ί empore doors zv; i see -O ⁵ C- and the boiling point of the polar solvent can be listed.

The starting materials of general formula VJ of the second erf indun _f! Rr "Maei £ s proceedings will hire" Deputy t by the resulting .V "rUri'iwngc · !: ^{(i <1} * ιΛ I di ''. U ₁ ^ u Fcrir.nl 11

² ·

- cn

CC
J t

Y * ^m 2 (ID

acyjicrt with an acylation agent containing the acyl group I _1.

The starting materials for the third method according to the invention are in themselves new compounds which themselves aritimikrobiol-Ie Possess properties. This connection i "der allt: r-r." Jnen i · - irine! 'ViI .can be made from the compounds of the general formula II,

₁ y,

- k

wherein R is a HydroXj-Elkylfjrup ^ -3, by acylation with a suitable acylating agent. These compounds of the general formula II can be prepared from an appropriately substituted one analogously to the reaction described above .5-Nj trofurylnitrilimin are produced.

009850/2192

The compounds of the present invention of the general emoinen Formeini and VII have valuable antimicrobial properties, especially antibacterial, anthelmintic, antiprotozoal cells, coccidiostatic, trypanocidal and antirnalaria properties of importance in human and veterinary medicine. The compounds prove to be particularly valuable during treatment infections of the intestinal or urinary tract. You can also protect from hydrophobic or other high molecular weight organic substances that serve the Are subject to decomposition by bacteria or other microbes, whereby these substances are brought together with the compounds, impregnated or otherwise treated. The compounds are also used as growth-promoting additives to animal feed. Turn.

According to the invention, a therapeutic composition of substances is also obtained, that from an antimicrobially effective portion of a 5-liitrofuryl-pyröZolverblndung of the general formula I. or VII and a pharmacologically acceptable solid. Carrier or liquid diluent.

The pharmaceutical compositions of the invention contain at least one compound of general formula I or general formula VI as an active ingredient together with a common phermaceutical carrier. The type of carrier largely depends on the area of application. For external use, for example to disinfect healthy ones Skin as well as for wound disinfection; id used to treat dermatoses and mucosal affections caused by bacteria ointments, powders, tinctures are particularly suitable *

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■■■■; ' ί ¹ - f -j

The bases for ointments can be anhydrous, for example made up of mixtures of wool fat and vaseline, or it can consist of a. are aqueous emulsions in which the active ingredient is suspended. Suitable carriers for powder are, for example, starches such as rice starch, which, if desired, can be made specifically lighter by adding highly dispersed silica or heavier by adding talc. Tinctures contain at least one active ingredient in aqueous, in particular 45-75%, ethanol to which, if desired, 10-20% glycerol is added. In particular, for the disinfection of healthy skin come solu- \ offices in question, which are prepared with the help of polyethylene glycol and other conventional solution promoters and optionally emulsifiers. The active ingredient content of the pharmaceutical compositions for external use is preferably between 0.1 and b%.

For mouth and throat disinfection gargle water or concentrates for their preparation are suitable, in particular alcoholic solutions with 1 - b% active ingredient content, to which glycerine j and / or flavorings can be added, and on the other hand ^

Lozenges, i.e. solid unit doses, preferably with a relatively high content of sugar or similar substances and a relatively low active ingredient content of, for example, 0.2-20% by weight and the usual additives such as binders and flavorings. '

For intestinal infections and for the oral treatment of infections of the urinary tract, solid dosage unit forms such as tablets, dragees and capsules are particularly suitable, which preferably contain between 10% and 90% of an active ingredient of the general formula I in order to facilitate the administration of daily doses between 0.1 and

009850/2192

• ·

2.5 g of adult lenses or of appropriately reduced D-. son to allow children. For the production of tablets and Dr -.- gee cores if the compounds of general formula 1 are combined with solid, powdery! Carriers such as lactose, sucrose, Sorbitol, corn starch, potato starch or amylopectin, cellulose derivatives or gelatin, preferably with the addition of GIoIt-. agents such as magnesium or calcium stearate or polyethylene glycols of suitable molecular weight, coated tablet cores are then coated, for example, with concentrated "sugar solutions, which for example still Arabic Gum.ni, talc and / or titanium dioxide may contain., or with an in volatile organic Solvent or solvent mixtures dissolved paint. Dyes can be added to these coatings Example for labeling different doses of active ingredients «Weiche Gelatin capsules and other closed capsules consist, for example, of a mixture of gelatin and glycerine and can for example mixtures of a compound of formula I with polyethylene glycol. Push-fit capsules contain granules, for example of an active ingredient with solid, powdery carriers, v / ie for example lactose, sucrose, sorbitol, mannitol *, starches, v / ie Potato starch, corn starch or amylopectin} cellulose derivatives and gelatin as well as magnesium stearate or stearic acid.

In all application forms, compounds of general formula I or general formula VII can be present as the sole active ingredients or else "combined with other known pharmacologically active, in particular antibacterial and / or antimycotic or other antimicrobial active ingredients, for example to broaden the field of application. They can, for example, with 5,7-dichloro-2-m ^r ithyl-8-quinolinol or other derivatives of 8-quinol inol, with Su! fanierazine or

00985Ό72192

BATH

I I

Kulfafura: ^f , ol or other derivatives of suIfanil amide, with chloramph <nicol or tetracycline or enieren antioiotics, with 3,4 ', t>-' I rj bromosalicylanilid or Enderoii halogoniorten salicylanilidone, with h: .logoniorton Carbi niliden.aiitcntlog 3e.nzoxa - ", olen odor Bnrr /. .Χί. · Ions, joined rolychlor-hydrcxydiphenylincthanen, with HsIogon-dihyärcxy-dlphenyl-sulfiden, with i, '1'-ÜLchlor-2-hydroxy-di- ]))] ' ny I-iither or 2', 4,4 '-Trichlcr-2-hydrcvxydipheny3äther odor ■ siKit.Ti-n i'vly}) al ■ - ■ {' · .nliydroxydiphenyläthei-n oricr with bsktoriniden quilt rrnärverbiiiäunr'- ' n od-.:r: iät gi-v. ^r irseri Dithioccrbami nnäureder 1 vatcn, vie 'ietrfircolhyl-thiurair.clisulfid, connected v; ground. It can Giu- !; Ira', · first; i'i'e, the self-valid ph ^ r: i; ii; (.- logisc} ie E Igen-Schauten lesit; fn vie zxx'm 3eispi (1 Schofel as r'ulveT'br.sls or Zinkst carat air a K'3 ":! i} -onent -" the ilalbonbaron, be used. "

The Krfinuunt; see also- an '»orfcthicn to the Schulz of organisclu-n, Bi i'ul 1 by bacteri · η cdcr cndcre microbes tiusgoselEten Substances that are characterized by the fact that the Substances with a kltrofuryl-pyrazole of the al lru ::. ^ Inen formula I or VIl to be treated. The orpani sch · '; Fabric can for example a natural or synthetic p., ly.v ..: r (s .- '. alerial, a protein-containing or carbohydrate content Substatir. or one of these Natural or synthetic substances produced or textile material.

According to the invention, animal feed is also obtained Composition, which is a nitrofuryl-pyrazole of all l ^ eir.einer Formula I or "VII contains in sufficient quantity to the creature = -, to promote the turn of the animal fed with the composition of matter.

The following examples explain the present Lrfin- " dung continues. Percentages are related to-des i-ev / jcht, if not

differently indicated ^ eb..n.

009850/2192

• ■ ι · ι ί -

! • ti * fl

Example 1

a) Concentrate to a mixture of <10 ml. Sulfuric acid and

40 m] ethano], 20 g of 5-amino-4-cyano-1-niethyl-3 - (5-r] itro-2-furyl) -pyra: ', ol are added and the mixture obtained is at stirred on a steam bath for 90 ° to 100 ⁰ C. The reaction mixture is diluted thinly with 500 ml of water and stirred further until the crystallization has ended. The crude product is taken up, washed with "water" and filtered from water.

The product, 5-Arn.i ηο-Ί-carbamoyl-l-methyl-3- (5-nitro-2-furyl) pyrazole has a Schmolz point of 242 ⁰ C with decomposition.

b) The ^ -Amlno-i-cyan .-; -! · methyl-3- (5-ni tro-2-i'uryl) -pyrazole v; iru prepared as follows:

To oinor gerührton solution of JG, 9 g of 5-nitro ~ 2-furaldohyd-lv '-: r, othy] hydrazone dissolved in 100 ml of dimethylformamide, was at 2'f bi s 3O ⁰ C was slowly added 17.8 g K rfromsuccinimide given.

After further. Stirring the mixture to ⁰ C gekühl Iu t.

Stirred to dor -n mixture is then 6.6 g of time on säurc-dini tril, gef ilgt by slow addition oin ^ri r mixture of 10.1 g 'Lriäthylariiin and 2b nJ Dine thy] formamide hei 10 "to? 0 ^(J C given.

After further torr. Stir the mixture with 500 ml Ice water diluted, and the precipitate Fosamrr.e] t, with V / assrr Washed and dried, tor-dried. Solids are removed Ethyl acetate u: .iKri crystallized.

The product obtained is 5-amino- ^/ 1-cyano-l-mothyl-3- (5-ni tro-2-furyl) pyrazole with a 3ch; re] zpunkt of 25ü ^'J C under Zori; ot. ". 'in".

0 0 9 8 5 0/2192

_ PT - ■ ·

In an analogous way the following are obtained:

c) 5-amino-1-cyano-1-isopropyl-3- (5-nitro-2-furyl) pyrazole;

d) 5-amino-4-cyano-1- (n-pentyl) -3- (5-nitro-2-furyl) pyrazole;

e) the 5-Am: Lno-4-cyano-1- (2-hydroxyethyl) -3- (i> nitro-2-furyl) pyrazole, m.p. 216 ⁰ C ₅

f) 5-Ämino-4-cyano-l-ethyl-3- (5-nitro-2-furyl) pyrazole, mp 189 ^0C.;

g) 5-amino-4-cyano-3- (5-nitro-2-furyl) -l-n-propyl-pyrazole, M.p. 163 °;

Example 2 .

The process described in Example la) is carried out using 5-amino-4-cyano-1-isopropyl-3- (5-nitro-2-furyl) pyrazole instead of 5-amino-4-cyano-1-methyl-3- (5-nitro-2-furyl) pyrazole as the starting material, the reaction conditions being essentially the same.

The product obtained is 5-amino-4-carbamoyl-1-isopropyl-3- (5-ni tro-2-. furyl) pyrazole.

Example 3

The procedure described in Example la) is carried out

using 5-amino-4-c; yano-1-Cn-pentyl) -3- (5-nitro-2-furyl ) -pyra; 'ul instead of 5-Am'ino-4-cy & no-l-me-thy.l-3- (5-nLtro-

2-furyJ.) - pyrazole as a starting point, where αίο heaktionsn ^ uruiori in v / eyentliehen the same slru.

Ali; Pr-j-jukt. Is obtained ^ -AniLiio - ^ - carbaraoyl-l-Cn-pfintyl) - '- -r \ ' I i'-j -? - {"uryL) -pyrazr / 1.

009850/2192 bathroom

t

• ff t

• · »t · I

Bo i game 4

Mar. performs the procedure described in example la) unt-τ Use of 5-amino-4-ey3no-1- (2-hyäroxyäthyl) -3- (5-riitiO-2-furyl) -pyrazole instead of S-Arfiino - ^ - cy & no-l-methyl-S - ^ - nitro-2-furyl) pyrazole as a starting material, whereby uie heaktionsbüdbedingungen are essentially the same.

As a product to 202 ⁰ C., 5-Ainino --- 1-carbamoyl-l- (2-hydrjxyäthyl) -3- (5-nitro-2-furyl) pyrazole, mp.

Example 5

a) A mixture "of 10 g of 5-amino-4-cyano-1- (2-hydroxyethyl) -3- (5-nitro-2-furyl) pyrazole and 200: nl acetic acid hydride v / earth

heated under reflux for 4% hours and then evaporated to dryness under reduced pressure. The solid residue provides, after recrystallization from aqueous dimethylformamide containing 5-acetamido-l- (2-acetoxyethyl) -4-cyano-3- (5-nitro-2-furyl) pyrazole, mp. 191 ⁰ C.

b) A mixture of 12.0 g of 5-acetamido-1- (2-acetoxyethyl) -4-cyano-3- (5-nitro-2-furyl) pyrazole and 50 ml of ethanolic hydrochloric acid (40 wt .- ^) is refluxed for 15 minutes heated and cooled.

100 ml of ice water are then added to the mixture, and the precipitated solid is taken up and recrystallized from water and dried. The product obtained is 5-amino-4-carbamoyl-1- (2-hydroxyethyl) -3- (5-nitro-2-furyl) pyrazole, M.p. 2 ° C

009850/2192

BATH ORIGINAL.

ill '9

«F - i

ti ' ir r: ·· ■ Γ,

To oli.c ·! - Lö.'Miir ν- η 23.3 £ ^t '- / _i mino-4-cy &no-l-rii'.thyl-3 - (!. · - !. i ■ Γ ·. · -? - Γυ2 · ;,]) -i yi sz A, gelo :: t in "inor.-Ii schung from 7G ml Ktri'-t .. '<] yjr (^ ^v : .-. A: r .! ii ur.; i 70 ir.l Pyridlu, v.-or-dui 7.8 g acctylchloride '/.uf-ViisA- un ^r i πει: healitlonsgctKi seh v. ^r äi »rc ι.- : 2'hours under hü \ "-; H \ r? Erhitri. I.cch i '-. I.-i abbreviation'ii'.i. Becomes ck.s Go;: ii5; ch with IM) ml ΐ · 'ϊ ^-w;: si -I ^- vcr iiirj'it UNJ d:: .- fu ^ ff' ^ ll ^r n ^r 5> Ac · :. tLi: a do-Ί-cy;;..! > -l -mcli.yl - :-( ί · -ΐ: ίir ) -2-i'uryl) -py! · - ..: · '..' /] ί; αΓ ^ · η ·? :: . ::. ^ η, with V.'ui; rcT f-oviii ^ clicn \ i.ii t ^; tr · eicn ^r t, Gnif.? .5C C.

Ap-ii Führi ci-.i: In i-ri.spiel b bc rc; ji'i {i-nn <) Vcrföliren im ti r V (iv; tn (Uii :; ^r wii O-Acu t b'Miuc - * -cy ur.n - \ -ii; othyl -3- (l-ni tro-2-fur.yl) -pyr £ i, 'io.l ; · λ.ϊΛ -jUc of 5 La . -t & T »Ido-l- (2-c.cctf»: yäthy3) -1-c: yanü-3- (b-nit rc-2-fury]) -pyra. ". Cl as Aur ^ arifTr-tofi ¹ diircli, woboi din hoakti: - nsbf.-diii ^ UMKC η im v. '.' i: i? r: i 1 iclu-n diesel uon are.

The product obtained is ^t jh ::.: Ii.) - ^ - c.ai.K.imy1-2 "- rn *. Inyl -": - (5-ni.tro-2-furyl) -pyiT ^ o ], C: np. ? - ',' j ^: f :.

i3ej sp: ο ! 7th

The 5-1

pyl) -pyrazole CSinp. 2Ib ⁰ C) v; ird anal '.- £ d · ;;? in Example 6 Lr-schrieoenon 5-AcetamidO - ^ - c-yano-li: iothyl - 3- (i> -nitro-2-furyl) pyrazoles prepared, starting from: 5-amino - 1 - cycn;) - 3 - (i> -ni t.-c-2-furyl) -1 - (n-propyl) -pyrazole.

The procedure described in Example b is carried out using 5-acetamido- <1-eyano-3- (5-nitro-2-fury]) -l- (n-propyl) -pyrazole instead of i> -acotamido-] - (2-acotoxyethyl) -

■ 1 - cyano-3- (5-nitro-2-furyl) -pyra ::. Jl i; ls Aur. ^ Angsstoff durdi, where the res; <ti onf conditions 3: n v: csf? ntl! clien dieseltr π sii.d.

009850/2192

III · t »

I I · ·

IS · ·

As a product obtained men 5-Arnino-4-carbanioyl ~ 3- (5> -rue .tro-2-furyl) -l- (n-propyl) pyrazole, mp. 198 ⁰ C.

Example 8

5-Acotamido-4-cyano-1-ethyl-3- (5-nitro-2-furyl) 'pyrazole is analogous to the 5-acetamido-4-cyano-1-methyl-3- (5-nitro ~ 2-furyl) -pyrazole described in Example 6 prepared, starting from 5-atnino-5-cyano-ethyi-3- (5 "-nitro-2-furyl) -pyra7, ol,

• The procedure described in Example 5 is carried out using 5-acetamido-4-cyano-1-ethyl-3- (5-nitro-2-furyi) pyrazole instead of 5-acetamido-1- (2'-ncetoxyethyl ) -4-cyano-3- (5-nitro-2-furyl) pyrazole as the starting material, the reaction conditions being essentially the same.

As a product to 210 ⁰ C. receives S-Arnino ^ -carbanioyl-l-ethyl-S- (5-nitro-2-furyl) pyrazole, mp.

Example 9

The ancestor described in example la) is used Use of 5-amino-4-cyano-1-ethyl-3- (5-nitro-2-furyl) pyrazole instead of 5-amino-4-cyano-1-methyl-3- (5-n3 tro-2-fü-ry]) -pyracol as a starting material, whereby the Reektiorisbedingurjgen essentially the same find.

The product obtained is i> -Amirio-4-cörbaÄoyl-l-ethyl-3- (5-nitro-2-furyl) pyrazole, ßmp. 210 ⁰ C.

Example 10

The procedure described in Example Ift) is carried out using 5-aalno-4-cyeno-1 * (n-propyl) -3- (5-nitro-2-fury?; - pyratol instead of 5-amino-4 -cyenp-l-mt ^> thyl> 3- (5-nltro-2-furyl ⁱ ) -

BAD ORtQINAL '

pyrazole as the starting material, the reaction conditions being essentially the same.

As Prodi; kt, 5-amino-4-carbamoyl-l- (n-propyl) -3- (5-nitro-2-i'uryl) pyrazole, mp 198 ⁰ C ·.

0 0 9 8 5 0/2192 ORiGiNAt inspected

Claims (1)

Claims , VK Process for the preparation of a 5-nitrofuryl-pyrazole compound of the general formula I O ₀ N χ V— C- ² \ ii -CO-NH ₉ (I) Ii H ² NC — NH ₀ N-I v; orin R is an unsubstituted Q alkyl group with 1 to 5 carbon atoms or an alkyl group having 2 to 5 carbon atoms substituted by the hydroxyl group is thereby characterized in that one has a nitrofuryl-pyrazole derivative of the general Formula II C-C-CH a ti k wherein H has the meaning given above, hydrolyzed. ?. Process for the preparation of 5-nitrofuryl-pyrazole compounds the general formula I defined in claim 1, wherein R is an unsubstituted alkyl group having 1 to 5 carbon atoms means, characterized in that a compound of the general formula VI C__C_CN (VI) H H η η fs "'- ■ 009a50 / 2192 • • (II · ' where R, denotes an acyl group, hydrolyzed and deacylated, by treating the compound with a proton donor in a polar solvent and hydrolyzing the protonated intermediate. 3. The process Eur Preparation of 5-Nitrofuryl-pyrazole compounds of the general formula I ₁ defined in claim 1 wherein R is a means by the hydroxyl group substituted alkyl group having 2 to b carbon atoms, characterized in that a compound of the formula VII 0 _u - / "" Λ— C— C -CK (VlI) 2 \ / jk H W ₂ where Ii _{2 is} an acyl group and A is an alkylene group with 2 to b carbon atoms, hydrated and deacylated by treating the compound with a proton donor in a polar solvent and hydrolyzing the protonated intermediate. A. Nitrofuryl-pyrazole-compounds-of-the-general-form! I. θ / fj ^w " ^Π 2- U) where R is an unsubstituted alkyl group? «With 1 to 5 carbon atoms or represents an alkyl group having 2 to 5 carbon atoms substituted by the hydroxyl group. 5. Use of therapeutic preparations with antimicrobial effectiveness, characterized by the content of a compound of the general formula I defined in claim 1, in which R and h _{2 have} the meanings given there, in combination with an inert iFrägersiaff and optionally other additives. \ - - ■ 009850/2192 BATH ORIGINAL