DE2351942A1 - NEW QUATERNAERE AMMONIUM DERIVATIVES, THEIR PRODUCTION AND THE COMPOSITIONS THAT CONTAIN THEM - Google Patents

Description

Qr. F. Zumstein Sr. - Or. E. Assmann Dr. R. Koenigsbergar - Dipl.-Phys. R. Holzbauer - Dr. F. Zumaieln Jun.

PATENT LAWYERS

TELEPHONE: COLLECTIVE NO. 225341; TELEGRAMS: ZUMPAT POST CHECK ACCOUNT: IvlÜNCHEN 91139

BANK ACCOUNT: BANK H. HOUSES

8 MUNICH 2.

SC 4145

RHOITS-POUTiEITO S.A. , Pariah, France

Today quaternary ammonium derivatives, their manufacture and the compositions they contain

The present invention relates to new, quaternary ammonium derivatives that. calibrated, disinfectant properties, their manufacture, as well as the disinfecting compositions for general use and therapeutic Compositions containing them.

It is already known that quaternary ammonium compounds: the one or two alkyl radicals with at least 8 carbon! contain atoms bound to the nitrogen atom, have disinfectant properties. Under these guaterriären ammonium compounds the Lauryldimeth.Ylbenzylammonium- chloride or Benzalkoniumehlorid is to a large · _Number: effect of germs * This chloride is, however, as a bactericide against the Gram-negative bacteria are much less effective than against the Gram-positive bacteria, which do so. . leads to only use this product in concentrations that are effective against the most resistant bacteria, for the sake of making the latter easy to select. Among these, Pseudomonas aeruginosa or Bacillus pyocyaneus is known to numerous. Cases of infection in surgical and medical practice and even of entire operating blocks that:

409817/1183

make it necessary to close them in order to disinfect them.

The products according to the invention correspond to the general ' formula

CH,

">>> - WH-CO-CHp-W-H

I.
CH,

(D

in the

R is an alkyl radical with 7 to 16 carbon atoms in a straight line or branched chain means and

X ^> a monovalent, inorganic or organic anion represents from the group of anions, of which is known that they give quaternary ammonium derivatives.

The symbol R means in particular one of the following radicals: n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, 2 ~ »ethylhexyl or a radical which is one or more Has methyl groups, the total number of carbon atoms being between 7 and 16 and this radical being the alkyl part of alcohols with 7 to 16 carbon atoms, which are obtained by oxo synthesis from petroleum olefins. One preferred class of products according to the invention consists of 3 the products of the general formula I, for which R is a Denotes an alkyl radical with 8 to H carbon atoms in a straight chain. The type of anion it / does not matter. The! Solubility of the products of general formula I in water however, varies depending on the kind of the anion. In general, the chlorides are more soluble than the bromides and methosulfs ate, while the iodides and nitrates are insoluble or are practically insoluble. Generally speaking, chlo rides are suitable for the different uses of the products.

According to the invention, the products of general formula I be manufactured by one of the following processes:

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If _{the anion Xw β} ± μ is kalogenide ion in the general formula I, a 4-fluoro-, carbanilinorietlian derivative of the general formula is used

' (II)

with a product of the general formula X ₂ - CH, (III)

in which X .. is a halogen atom and at the same time X _{2 is} the radical U (CH,) R, in which R has the meaning given above, or X _{1 is} the radical U (CH,) R, in which R is the above has given meaning, represents and at the same time X _{2 represents} a halogen atom.

In general, the reaction will take place in one under working conditions inert organic solvent, such as a ketone, especially acetone or methyl ethyl ketone, or an ether such as butyl ether ^ at a temperature between about 20 ° C and the reflux temperature of the reaction mixture carried out. One can work even in the absence of a solvent at a temperature between 20 and 120 ° C. -

The products of the general formula II, for which X ₁ - is a halogen atom, can be obtained by reacting a haloacetyl halide with 4 ** fluoroaniline.

The products of the general formula III for which X _{2 is} a radical ir (CH,) R, as defined above, - can be prepared by one of the following methods

a) By reacting formaldehyde and formic acid with an amine of the general formula

.R-IIH ₂ (17); ' ■

in-the R- has the meaning given above,

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b) by methylation of an amine of the general formula

'- R - 33H - CH ₅ ' (V) "':

in which R has the meaning given above, according to
the usual methods, this amin by reacting methylamine with an alkyl halide of the general formula. ·

R-shark. (VI);

in which R has the meaning given above and Hai:

represents a halogen atom, or by reacting;

Methylamine with an aldehyde of the general formula i

"'R ^f - CHO (VII) I

. ι

in which R ¹ denotes such an alkyl radical that R ^f -CH ₂ - ^! represents the alkyl radical R as defined above,

can be obtained. - |

- ■■■■. \.

The products of the general formula II, for which X .. j is a radical N (CH ₅ ) R, as defined above,)

can by reacting an amine of the general formula!

V, in which R has the meaning given above, with |

a product of the general formula II, in which X. i

represents a halogen atom. i

2. If the anion Xw in the general formula I is different!

Is anion as a chloride ion, one puts a metal salt;

i an inorganic or organic acid, whose 'monovalent'

1 y

j ges anion is another anion al3 a chloride ion, with j

j a product of the general formula I, for which Xw j! a chloride ion means to, with this product in what-
ι ser is solved. Generally one uses a sodium

salt, also in aqueous solution, the anion of which is advantageous;

overall j ■ way legally under the bromide, iodide and nitrate ions \

i chooses is. . i

i · ■ ι

; 3. One uses an alkyl ester of the general formula '

'R-X (VIII):; "

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in which R has the meaning given above and X is the monovalent radical corresponding to the anion X ^ - ', with the product of the formula

CH,
NH-CO-OH ₂ -N (IX)

'around. -

The product of the general. F ormel IX can be implemented through implementation

by Dime thy laniin with a product of the general formula

II, for which X _{1 represents} a halogen atom, can be prepared. . .

.

j The following examples are provided for further explanation

the invention. .

Example 1 '■

A mixture of 39.55 g of 4-fluoro-carbanilino-chloromethane, 51.85% IT-T-dimethyraeptylamine and 60% methyl ethyl ketone is heated to 100 ° C. for 15 minutes while stirring. The solid substance that hardens in the course of the heating is ground in the solvent and. then separated by filtration and dried at 45 ° C. under reduced pressure. Are thus obtained 82 g of ^4-i-1 luor carbanilino-methyl-heptyl-dimethylammoniumehlorid in the form of a white powder F = 115 ⁰ C.

The 4 "-]? Luoro-carbanilino-chloro-i-methane" used as starting material can be prepared in the following way: To a ί mixture of t20 g of 4-fluoro-aniline, 120 g of triethylarain and 1150 ecm of benzene, which at JO is kept to 35 ° C, are employed within 2 hours under agitation 140.5 g of chloroacetyl chloride ·. After complete addition, the reaction mixture is maintained for 1 hour at 30 to 35 ° 0, and then off to about 20 ° C ^[ After adding 300 ecm of water, the suspension obtained is stirred vigorously for 15 minutes The solid substance remaining in suspension is filtered off, one after the other at 250 ecm

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Washed water and then 250 ecm of benzene and dried under reduced pressure at 50 to 55 ° C. 168 g are obtained in this way
4-fluoro-carbanilino-chloromethane.

This product can also be obtained by reacting chloroacetyl chloride with 4-fluoroaniline in dichloroethane.

The H, Ή— Dimethyl- ι heptylamine also used as starting material can be prepared in the following way: To -! 460 g of formic acid are slowly added with stirring and cooling: 230 g of n-heptylanine. To the solution obtained is nan \ with further stirring, 530 cc of commercial aqueous foramen \ aldehyde to. The resulting mixture is gradually heated. At about 60 ° C, carbon dioxide begins to j corresponds wickeln- The temperature of the reaction mixture is advancing "- · tend brought to 90 ° G, and the mixture is stirred at this tem- \ pera door 1 1/2 hours (15 minutes after the Gasent- '. wiclclung) held. After cooling, the reaction mixture is renewed by adding 250 g of sodium hydroxide in the form of bubbles; tralisiart, whereby the temperature is kept below 45 ° G. _; The organic phase was separated ird ^ ^1, washed twice with a total of \ \ 100 cc water, dried and then ^verininder-: distilled system pressure. 180 g of Η, ίΙ-dimethylheptyl- I aiain are obtained in this way. (Bp ₂ c = 77 ° C). ■

Example 2

A mixture of 31.4 g of "Η ', ϊ'Τ'-dimethyloetylamine,
37.5 g of 4-fluorine-c; arbanilinO'-chloromethane and 100 ecm of acetone
2 hours with stirring under reflux. When cooling to 5 °
A precipitate forms, which is filtered off and placed under
dried under reduced pressure at 50 ° C. Sq 52 g is obtained
4-5 ^l luor-earbanilinomethyl-octyl-dimethylammonium chloride in
ίΌηη of a white powder of I ¹ = .136 ° G.

Hah. will get the same end product when you do as above, however
in the absence of acetone, works. . .

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The!, IT-DImethyloctylanin used as the starting substance can in a manner analogous to that in Example 1 for the ΙΙ, ίί-diniethylheptylamine mentioned.

Example 3 ■

Heating a mixture of 24.4 g of 4-I ^1-luor carbanilino-Ghlormethan, 20.4 g K, U-dimethyl-2-äthylhexyl'-amine and 50 cc. Methyl ethyl ketone with stirring under reflux for 4 1/2 hours. The reaction mixture is cooled to about 20 ° 0 and kept stirring for 14 hours. The precipitate formed is filtered off and dried at 50 ° C. under reduced pressure. This gives 38 g of 4 ~] pluoro-earbanilino-methyl'-2 ~ ethylhexyl-dimethylammonium-chloride in the form of a white powder of F = HO ⁰ O.-.

The IT used as the starting product, N- * DiT3ethyl-2-ethylhexyl - amine can be prepared in a manner analogous to that mentioned in Example 1 for ϊί, Η-dimethylheptylamine *

Example. 4th

Man. holds a mixture of 31.25 g of 4-3? luor-carbanilxno-.chloromethane and 30.87 g of N, E-] 3-dimethyldecylamine for 1 1/2 hours with stirring. The temperature of the reaction mixture, which is about 20 ° 0 at the beginning, increases spontaneously and progressively bx3. To 50 to 55 ° C, and the structure solidifies at the end of the stirring, after crushing the powder substance, 62g of 4-fluoro-carbanilino are obtained -methyl-decyl-dimethylammonium chloride in the form of a white powder from i ¹ = 50 ° G.

The!, N-dimethyldecylainin used as the starting substance can be used in a manner analogous to that in Example 1 for the ir, 3f methylheptylamine called.

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Example 5

Han holds a mixture of 19.7 g 4HE ^> luor ~ earbanilino-ehlor- <ißthane, 20.6 g Κ, Ν-Diinethyldec.ylamin and 100 eem butyl ether at a temperature of 45 to 50 ° C with stirring, flat 1— hours of heating the mixture becomes oily and after 2 hours a progressive precipitate appears. Da3 heating is maintained for a total of 4 hours. The reaction mixture is then cooled ^{to about 20 ° C.} The precipitate is filtered off, washed twice with a total of 120 ecm of hexane and then dried at 40 ° C. and then at 50 ° C. under reduced pressure. This gives 37.1 g of 4-fluoro-earbanili, nomethyl-decyl-dimethylammonium chloride in the form of a white powder with a P = 112 ° G. The difference in melting point with the product of the preceding example is explained by the fact that the product is beaaer is crystallized.

Example 6

A mixture of 48.2 g of 4-3? Luor ~ carbenilino «is heated chloromethane and 5? »5 g of N, N ~ bimethyllaurylaisin 9 1/2 hours at 120 ° G with stirring. To the cooled reaction device 500 ecm of acetone are added and the Geraisch bia I is then heated for the complete dissolution of the Peataubetanz. The received j The solution is cooled and the precipitate formed is filtered off trated and dried at 40 ° G under reduced bridge. j This gives 20 g of 4-iluoro-garbaniline / diethyl-dodecyl-diethyl. ammonium chloride in the form of a white powder of ΊΡ- = * 95 ° 0 ·

The same product is obtained if one is without a solvent and works at a temperature between 20 and 50 ° C

3) KtH-Iftmethyllaurylaain used as the starting product can be used in a manner analogous to that in Example 1 for the Β, ΙΓ-Di— methylheptylamine described are produced »

Example 7

Heating a mixture of 15 ^»l 6g 4'-S ^ carbanilino luor-'Chlor- and 21.2 g N, H" dimethyltetradecylamine 9 hours at

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~ 9-

120 ° G with stirring. The reaction is then dissolved in the minimum amount of acetone in the heat. The solution will be at about; 20 ° G cooled. The precipitate formed is filtered off and dried at 50.degree. C. under reduced pressure. ■ obtained as 25 g of 4 '3? Luor-carbanilinomethyl-tetradeGyl-dimethylammoniuin-? chloride in the form of a white EuIvers from 3? = 115 ° C.

Example 8 . ;

A solution of 8.7 g is added over the course of one hour to a solution obtained by heating a mixture of 5.8 g of 4-fluoro-carb: anilinomethyl-decyl-dimethylammonium dichloride and 80 ecm of water to 50 to 55 ° C. with stirring Sodium bromide dihydrate in 30 pcm of water is added. When the addition is complete, the reaction mixture is stirred for hours at 50 to 55 ° C. and then 60 ecm of diehlorethane is added, stirring being continued for 15 minutes and the temperature being maintained at 50 to 55 ° C. The organic phase is separated off, washed 4 times with a total of 240 ml of water and then concentrated to dryness under reduced pressure, the temperature being kept below 45 ° C. The residue is taken up in 60 ml of hexane and the crystals are filtered off, washed with hexane and dried under reduced pressure at 50 ° C. 5.55 g of 4 -]? luoro ~ carbanilinomethyl ~ deeyl ~ dimethylammonium bromide are thus obtained in 3? form of a white powder of] ?. · = 110 ° C. ■ . - ■ ^: ■ ■ - ■ ■ ■ ". '■

j Example 9 ■ · ■ ·.

j A mixture of 14.8 g is heated. 4- \ fluoro-carbanilino-bromraethane, 15.2 g of dimethyldecylamine and 100 cem of butyl ether for 4 hours with stirring at 45 to 50 ° C. The after cooling to about

! 20 ° C formed precipitate is filtered off, twice with a total of 100 ecm of hexane and washed at 50 ° C under reduced

! dried under pressure. This gives 26 g of 4-5'luoro-carbanilinomethyl-decyl-dimethylammonium bromide in Porra of a white powder with a P = 112 ° C ^Λ

j -The 4-fluorocarbanilino ~ bromo- '' used as the starting substance methane kanxi can be produced in the following way: to one

40981771183

"■ ■. - ίο -

Mixture of 48.7 g of bromoacetic acid, 500 com dichloroethane and

: a few drops of dimethylformamide heated to 60 ° G,

if 63 g are set with stirring within about 1 hour

_: ohlorid too. The reaction mixture is then 2 hours

! heated under reflux and then under reduced pressure until

: restricted to achieve a residual volume of 100 ecm. The ■

: The solution obtained in this way becomes a product within 1 hour

; Mix of 33.8 g of 4-luoro aniline _t 300 ecm dichloroethane and

; 36 g Uatriuracarbonat added, the temperature of this

; the latter mixture during the entire evening train duration

j is kept at 35 ° C. The Seaktionsgsmisch is then

i refluxed for 2 hours. Then the failed

S Mineral salts separated by filtration. The organic PiI

! stepped four times with a total of 1600 ecm V / water of 70 ° C

I wash and then cooled to 20 ° C. The educated

j blow is filtered off and then from dichloroethane. recrystalline

! ■ lized. After filtering off the crystals and drying "at 50 ° C

j under reduced pressure, 40 g of 4-fluorine-earbanilino

I bromine than. . "-". '

j Example 10

I zu.einer by heating a mixture of 12 g of 4-IPluor-earbj anilinomethyl-decyl-dimethylaammonium chloride and 120 ecm of water A solution of 9.7 g of sodium iodide in 30 ecm of water is added within 1 hour to the solution obtained from 50 to 55 ° G j to. When the addition is complete, the reaction mixture is left for 2 hours j stirred at 50 to 55 ° G and then with 100 ecm dichloroethane ! added, stirring continued for 15 minutes and; the temperature is kept at 50 to 55 ° 0- The organic · Phase is separated off, three times with a total of 300 ccn water

washed and then evaporated to dryness under reduced pressure ^; concentrated, the temperature being kept below 45 ° C. The _; yellow solid residue is taken up in 60 ecm hexane, and the crystals are filtered off and dried at 60 ° G under reduced pressure. This gives 12.8 g of 4-fluorocarbanilino-methyl-de-cyl-dime thy! Ammonium;} odide in ΙΌηπ of a yellow powder ^! from f . = 98 ° C..

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Example ti .

j To one by heating a g-emig of 6 g of 4-Pluor-carb-! anilinoxethyl-säecyl-aiaethylamraoniumchlorid and 80 ecm of water to 50 to 55 ° G obtained solution are set within! 1 hour a solution of 4.1 g of sodium nitrate in 20 ecm of water. After the initial addition, the reaction mixture is stirred for 2 hours at 50 to 55 ° G and then mixed with 60 ecm of dichloroethane! continues, stirring for 15 minutes and maintaining the temperature between 50 and 55 ° G. The organic phase is removed, washed three times with a total of 180 ecm of water and then concentrated to dryness under reduced pressure, the temperature being kept below 45.degree. The oily residue obtained is triturated with hexane. This is thrown off by baking. The residue is rubbed in again with hexane, causing it to solidify almost completely. The hexane is separated off again by decanting, and the residue is dried under reduced pressure at about 20 ° σ and then at 50 ° G; - This gives 6 g of 4-i ¹ luor - rcarbanilino-inetb, yl-decyl--

The products of general formula I have interesting germicide.properties. on. In particular, they are against that gram ^ neg ^ rfciven batteries and especially against Pseudomonas aeruginosa «irlaaa. They also have good fungicidal properties eligibility: and a very low toxicity. ·

These different properties were determined in the following manner proven: "" ...- ..---, ■, -. · ".- '-...

It was found in the mouse when administered by the subcutaneous route the acute toxicity of the compounds of Examples 4 (4-Pluorcarbanilimoaetliyl-decyl- ^ diniethylammoniumchlorid) ,, 6 (4-PluorcarbaniliäaTastbyl-dodeeyl-dimethylammoniumchlorid) and 7 (4-luoro-carbaniliHLOiJiethyl-tetradecyl-diethylammonium chloride} with that of 2 known disinfectant quaternaries Ammonium compounds, namely benzalkonium chloride and cetrimonium bromide, compared »The products were in a

4098 17/1 183 _BA o

4 $ aqueous solution was injected and it became lethal observed for 7 days. The results obtained are the following:

product

always tolerated, always fatal maximum dose kinimal dose

= ¹⁰⁰ °

by jjei-
game 7 ? 1000 mg / kg Benz
alkonium ~
chloride 50 mg / kg Cetri-
monium
bromide 100 ng / kg

Lethality

80 mg / kg

250 mg / kg

DL-5O

> 1000 ng / kg

65 mg / kg

I35 ing / kg

• Local tolerance - drop in the eye

; Daily instillation of a solution containing 1 / 4OOO of the above Products during 5 days gave no irritation at all

nings.

Local tolerance ~ application to the skin

Solutions with 2/1000 of the The above products are applied to the previously epilated skin on the back of groups of rats, with simultaneous brushing (twice back and forth) was made with a liylon brush. The rats treated in this way showed no signs of irritation on"

These tests show that the local compatibility of the products according to the invention as well as for the two methods same products. ,

bath

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Balvt sr 103 tatis chg Bi- ^ enaι cha ft en

Si © - was »by the usual methods by successive-; ^: . Equal dilution in agarms was determined for 23 bacterial specimens ^, • and was S gram ^ positive for bacteria:. _:

; Bacillus subtilis (sporeg) ATCO 6633!

; Bacillus oeraus (gppres) ATGO 9634 '

J Streptococcus faecalis A 2 C C 9854

ί Saroins Xutea ATOC 9341 - -;

52Ί6 ■ =. . ^;

ϊί ^θ 1057
n ° 1086

and 15 gram ^ n ^ gativgn bacteria: '

Salmonella typhi

eoli

oolt 111%

audoraqnag aerugingsa ATQ0 902.7

Pon.

aaruginpsa Mqu,
glueidolytiea vap. nqn
Iwpffi yar "

. At agn gram-pQ9ii.tiveia falcterifn bi # carries dif
<3a.r Examples 4 «6 and 7-less a

, Bai dan -gra-m ^ ne ^ aIIiYen Baiitarian possess the pradulcte dar

; Bsicjpiale 4 and 6 HamniWirlcung with a consantration under

\ 100 / ig / ml and the product of Example "7 has a hemavirectic effect

; at a concentration below 100 jtfg / nil in most '

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Cases and below 1000 µg / ml for some st auras.

For comparison purposes, it should be noted that hexachlorophene one hemi.wirlcang kai less than 10 / ig/nil in the gram-positive

; Bacteria developed, however, at less than 1000 / ag / ml ■ does not affect the gram-negative bacteria.

' Bactericidal Gigenschaf tenjL

They were found in particular in Pseudomonas aeruginosa (ATCG 9027) : because of the known! resistance of this bacterium to a '' studied large numbers of disinfectants.

[Well, the usual methods in bacteriology are used by following the bactericidal action on the bacteria! a predetermined number of outlines: 1, 2, 5, 30 and 60 minutes, ■ withdraws. One determines in ? O the number of survivors

Germs, the bactericidal activity is believed to be good, ; if at most $ 0.01 surviving germs remain.

5 After i-minute contact, remain at a dose of 250 pg / ml of the product of Example 4 or a dose of

500 jug / ml of the product from Example 6 less than 0.01 ?> i surviving seimes.

In comparison, the bactericidal doses (calculated for the 100 fSige product) of the two known quaternary ; ren amconium derivatives, which are used as specialties for medical j use are used, 1000 ug / ml and 1500 jig / rnl.

Effectiveness; . - ■

They are determined by the customary methods by diluting them in Sabouraud medium. · "

The fungicidal immunity of the products was found in both of them ,. determined by the following tribes: "

: _Aspargillus niger «ubiquitous PiIa . Tricophyton mentagrophytes: Dermatophy't.

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The straight fungicidal DoseVi are the following:

- A-Spergillus tricophyton

Tii-ger me ti ta gr ophyt es

Product of Example 2 1000 mg / ml 1000 mg / ml

Product of Example 3 4000 μ © / ιη1 4000 jug / ml '·. '.

Product of Example 4 500 µg / ml 250- µg / ml "

Product of Example 7 "4000 / ig / ml 4-00 mg / ml

These different properties of the products according to the invention make them industrial as disinfectants Use and medical use, suitable.

They can be used as disinfectants for industrial use in domestic hygiene, for disinfecting dishes, sanitary facilities and floors, in laundry for disinfecting Laundry, especially hospital linen and baby diapers, in the food industry for disinfection νσα collected kitchen appliances and general · of appliances and in the textile industry used to prevent fungi attacks. -

In general, washing is preferred for disinfecting and the treatment of textiles to use the products of general formula I that have low solubility in water, whereby this has a certain substantivity towards textiles have, which enables permanent disinfection.

The disinfectant, bactericidal, bactericidal, fungicidal and general germicidal compositions for general use which have at least one product as the active ingredient of the general Pormsl I included represent another 'Subject matter of the invention. These compositions can be solid or liquid. Powders or granules can be mentioned as solid compositions. In these compositions is the inventive., effective, product with a or more inert compatible diluents and optionally substances other than diluents,

4098 1.7 / 1 183

such as, for example, various shredding agents and detergents that work with the Products of the general formula I are compatible, mixed compositions of this type are particularly suitable for disinfecting sanitary devices. You can also used for any other purpose after dissolving in water will.

Liquid compositions can be diluted ".-. ■. or use concentrated solutions or suspensions that contain inert diluents and substances other than the ■ thinners, such as wetting agents, detergents or flavorings which are compatible with the products of general formula I contain. The concentrated liquid Compositions can be diluted with water at the time of use. Such liquid compositions are suitable particularly suitable for use in the home, for treating textiles and for disinfecting floors.

These wet or liquid disinfecting compositions J can optionally contain one or more other disinfectants which are compatible with the products of the general formula I, and diluents and adjuvants . .-.- * - ;. '■

The following examples serve to further illustrate disinfecting compositions according to the invention in general Use. . . "

Example A. . ■ - - -

A powder of the following is prepared according to the usual technique Composition ago:

BADORK ₃₁ NAL * ^09817/1183

chloride 50 g

ethoxylated nonylphenoT. . , 75 g

Sodium Carbonate Anhydrous -: 200 g ^;

Trinabriuaphosphate TOO g. ^

Tetranatriuinpyrophosphate 575 g,

. The composition obtained can be used as such for disinfection used by sanitary facilities.

Example B. '■ ■ ".

A powder of the following is prepared according to the usual technique; Composition ago:. "" .. j

4-I ¹ IuOr-carbanilinomethjl-decyl-dimethy.lammoniuTa-t · ■; ;

'chloride 3 "0 g ■.'

ethoxylated itonylphenol 50 g

anhydrous sodium carbonate '450 g ]

Eatrium bicarbonate 4.7O g

This composition can be dissolved in water in an amount of 50; up to 300 g per 100 l of water for use as a disinfectant ' j medium diluted in the dairy industry. ,

Example Q · '- -. ·;

A solution of the following is made according to the usual technique
Composition ago:. ;

4-fluoro-carbanilinomethyl-decyl ^ ^{_{dimethylammonium:}}

Chloride - 50 g

ethoxylated uronylphenol; '' - 200 g ^;

distilled water '■ Q.s 1000 ecm ·

By diluting 1 to 3 ecm of this concentrated solution
on 1 1 one obtains one which can be used in household hygiene, for example for the disinfection of dishes
. Solution.

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: As a disinfectant for medical or surgical

■ G@bra.uch to the products of general formula I for ^Des;

: injection of wounds and burns, in the treatment of

. infected derraatoses, mycoses and ITlceratioöen, for disinfection

'tion of operating fields, in gynecology for treatment

! of vulvo-vaginal affections, in ophthalmology as an anti-

: septicum in eye treatment products and for rinsing hands:

ι be used by medical staff. ;

The pharmaceutical compositions that can be used in therapy! ι settlements that are at least a product of the general
; common formula I. contain a further subject _; ; of the invention. These compositions can be liquids! {or ointments in which the products of the general formula * ·

! j

! I in dissolved form or in dispersed form in compatible;

- I.

; Excipients, such as, for example, polyglycols or fatty alcohols . 'len, available. These compositions can also contain other substances than the diluents, such as, for example, aromatic products which are compatible with the products of the general formula: ·

These compositions are used by topical application and '■ j depending on the degree of infection of the subject to be treated, "where;

the doctor determines the frequency of use. j

The following example serves to further explain the invention. · therapeutic compositions according to the invention. . S.

example

A solution of the following is prepared according to the usual technique
Composition ago:

4-Pluoro-carbanilinomethyl-decyl-dirr, ethylaianionium- '.

Chloride 0.25 g

70 volatile alcohol. Q.s 100 ocm

This solution is used to disinfect small injuries,
Cuts, burns and used for disinfecting operating fields. . .

_409817/1183

Claims (1)

. - 19 - Claims 1. Compounds of the general formula EH-C 0-CH ₉ -IR C- I ¹ CH 3_ in which R is an alkyl radical with .7 to 15 carbon atoms in j straight or branched chain and X ^ a monovalent inorganic or organic anion from the group the anions that give quaternary ammonium compounds. ! - - represents. - - ■ - - - ■ · j: "i 2. Compounds according to claim 1, characterized in that i the anion X- "a Chloricl-, Bromid-, Jodid- ^ or Methosul-:! fation is. · 5- A method for producing a compound according to claim 1, for which the anion X ^ is a halide ion, characterized in that a 4-fluoro-carbanilinomethane derivative is used the general formula ff ■ - ^ ~~~ ^ y— HH-C Q-CHp-X ₁
..with a product of. general formula in which X ₁ denotes a halogen atom and at the same time X ₂ denotes Re3t Sr (CH,) R, in vrelehem R has the meaning given above, or X ₁ denotes Re3t IJ (CH ^) R, in which R the has the meaning given above, and at the same time represents X ₂ ^{9 in a} halogen atom. 4. The method according to claim 3, characterized in that one a 4-fluoro-oxanilinomethane derivative of the general formula N >> M-CO-CH ₂ -X ₁ in which X _{1 means} a chlorine or bromatoin, with a 409817 / 1.183 J: jl ^ fliCJ. C-- ^? · "^ Product of the general formula Z ₂ -GH ₅ in which X _{2 represents a} radical 2T (CH 1) E, in which R has the meaning given above. 5. The method according to claim 3 »characterized in that one a "4-fluoro-carbanilinomethane derivative of the general formula HH-CO-CH ₂ -X ₁ in which X ₁ denotes the radical JT (GH _x ) R, in which R has the meaning given above ", reacts with methyl chloride." 6. A method for producing a product according to claim 1, for which the ion X ^ another ion al3 is a chloride ion, characterized in that a metal salt of an inorganic or organic acid whose monovalent anion is a different anion than the chloride ion with one . Product according to claim 1, for which X® represents a chloride ion ;. represents, converts, whereby this product is in. Solution in Was- ! ser is located. , ■ ■ j 7- method according to claim 6, characterized in that one ! sodium bromide, iodide or nitrate used as the metal salt. 8. Process for the preparation of a product according to claim 1, characterized in that an alkyl ester of the general formula in which R has the meaning given above and X the corresponding to the anion X ^ as defined above is monovalent radical, with the product of the formula CH ₅ MC C-CH ₀ -IT ; - implements. ■ -. 409817/1183 BAD ORiOiMAL 23B1942 9 »Disinfectant composition for general use., characterized by a content of at least one product according to claim 1 or 2 ala active substance. 10. Pharmaceutical composition that can be used in therapy, ' ■ identified by a content of at least one product according to claim 1 or 2 as active substance » 409817/1183