DE1420087C - Diphenylamm derivatives substituted in the position of a phenyl radical and process for the preparation of the same - Google Patents

Description

NH-

in which R is an alkyl mercapto or alkoxy group with 1 to 6 carbon atoms, the benzyl mercapto, Denotes phenoxy or benzyloxy group.

2. A method for the preparation of compounds according to claim 1, characterized in that a secondary amine of the general formula II

in which R has the above meaning, in a manner known per se in the presence of an inert organic solvent and an alkaline condensing agent at an elevated temperature with a piperidine derivative of the general formula III

CH ₂ H ₂ C CH ₂

-NH-

in which R has the above meaning, in per se known Manner in the presence of an inert organic solvent and an alkaline condensing agent at elevated temperature with a piperidine derivative of the general formula III

CH ₂

H ₂ C

₂
\
CH ₂

Hal-CH ₂ -CH ₂ -HC CH ₂ (III)

CH,

in which shark means a chlorine or bromine atom, condensed.

3. Medicinal product consisting of a compound according to claim 1 and pharmaceutically acceptable Fillers or carriers.

The invention relates to an e'henyl radical in the m-position substituted diphenylamine derivatives of the general formula I.

in which R is an alkyl mercapto or alkoxy group with up to 6 carbon atoms, the benzyl mercapto, Hal - CH ₂ - CH ₂

HC CH ₂ N CH ₁

in which shark means a chlorine or bromine atom, condensed.

The invention also relates to medicaments which are made from a compound according to the invention and pharmaceutically harmless fillers or carriers.

The compounds according to the invention are prepared by using a secondary amine of the general Formula II, dissolved in a suitable solvent such as benzene, toluene or xylene, under Stirring and adding a suitable condensing agent, e.g. B. alkali hydroxide, alkali amide, alkali carbon nat or copper powder, with a piperidine halogen derivative of the general formula III at elevated temperature is implemented. After the reaction has ended, the reaction product is obtained by working up of the reaction mixture and distillation in vacuo. Further purification can be carried out by transferring take place in an acid addition salt and recovery of the free base.

The compounds according to the invention are oily or crystalline at room temperature and form with Solid salts resistant to acids. They possess pharmacological properties that make them valuable and versatile make usable drugs.

Namely, it has been found that the diphenylamine derivatives of the present invention are more general Formula I have a strong fungicidal effect with low toxicity and therefore good tolerance. Your effect z. B. on Candida albicans, the causative agent of most epidermophytias, exceeds the of the previously known fungicides. The new connections can be per os or parenterally, but also locally, e.g. B. by brushing on their alcoholic solutions or the aqueous solutions of their salts with acids. The compounds also have a spasmolytic and antihistaminic effect.

They can therefore also be used as antispasmodics and antihistamines can be used therapeutically.

The following examples illustrate the invention.

example 1

N- [m-methylmercapto-phenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline

M-Methylmercapto-aniline (boiling point) is condensed. 163 to 165 ° C / 16mm Hg) with the potassium salt of ο-chloro-benzoic acid and decarboxylates the resulting N - (m - methylmercapto - phenyl) - anthranilic acid (melting point 1.39 to 141 ° C.) by heating and then Distillation to give N- (m-methyl mercaptophenyl) aniline (melting point 59 to 6 ° C).

15 g of N- (m-methylmercapto-phenyl) -aniline are dissolved in 75 cc of absolute xylene, treated with 3.26 g of finely powdered sodium amide and heated for 2 hours at a bath temperature of 180 ⁰ C to reflux. It is allowed without having to interrupt heating, Vf within ₂ hours, 12.7 g of 2 - (N - methyl - piperidyl - T) - 1 - {chloroethane bp. 84 ° C / 10 mm Hg (cf. TR N ο rt ο η and coworkers, J. Amer. Chem. Soc, 68 [1946], 1573)}, dissolved in 12 ecm of absolute xylene, added dropwise and heated without stirring to interrupt, the mixture to boiling for a further 3 hours. It is then cooled and the excess sodium amide is decomposed by adding 5 g of ammonium chloride. The xylene solution, washed three times with 25 ecm of water each time, is extracted once with 30 ecm, then three times with 10 ecm 3 of η-acetic acid each time. The combined acetic acid extracts are shaken out with 50 ecm of ether and they are made with 16 ecm of conc. Sodium hydroxide solution, phenolphthalein-alkaline. The solution of the precipitated oily base in 100 ecm benzene is shaken out with 30 ecm water, dried over potash, filtered and evaporated under reduced pressure. The residue is distilled in a high vacuum, the main fraction passing over below 0.01 mm Hg at 215 to 218 ° C. being collected. The analytically pure N - [m - methylmercapto - phenyl] - N - [2 - (N '- methylpiperidyl - 2') - ethyl - (I)] - aniline has a boiling point of 216 ° C. at 0.01 mm Hg.

Example 2

N- [m-Ethoxyphenyl] -N- [2-N '-methyl-piperidy 1-2') -ethyl- (1)] - aniline

30 g of N- (m-ethoxyphenyl) aniline (melting point 60 to 62 ° C) dissolved in 150 ecm of absolute xylene, 6.6 g of finely powdered sodium amide and 25.5 g of 2- (N-methylpiperidyl-2 ' ) -l-chloroethane, dissolved in 25 ecm of absolute xylene, result in analytically pure N - [(m-ethoxyphenyl] - N - [2 - (N '- methyl - piperidyl - T)) according to the method described in Example 1 - ethyl - (1)] - aniline with the boiling point 170 ⁰ C at 0.005 mm Hg.

Example 3

N- [m-n-Butoxyphenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyi- (1)] - aniIine

M-Nitro-phenol is butylated with n-butyl bromide in the presence of potassium hydroxide and the nitro group is reduced to the amino group with tin (II) chloride and hydrochloric acid. The resulting m-amino-phenol-n-butyl ether with a bp. 153 ° C./11 mm Hg is condensed with the potassium salt of o-chloro-benzoic acid and the resulting N- (mn-butoxyphenyl) -anthranilic acid is thoroughly decarboxylated heating at 250 ⁰ C for N- (mn-butoxy-phenyl) aniline (mp. 42'bis 46 ° C). 35 g of N- (mn-butoxy-phenyI) -aniline, dissolved in 230 ecm of absolute xylene, 6.8 g of finely powdered sodium amide and 26.4 g of 2- (N-methyI-piperidyl-2 ') - l-chloroethane, dissolved in 30 ecm of absolute xylene, yielding analytically pure N - [m - η - butoxy - phenyl] - N - [2 - (N '- methyl - piperidyl - T) - ethyl - (I)] according to the method described in Example 1 - aniline with a boiling point of 187 ° C at 0.005 mm Hg.

B e i s ρ i e 1 4

N- [m-ethylmercapto-phenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl ( 1)] - aniline

M-Ethylmercapto-aniline (boiling point) is condensed.

147 to 152 ° C / 10 mm Hg) with the potassium salt of o-chlorobenzoic acid and decarboxylates the resulting N - (rii - ethyl mercapto - phenyl) - anthranilic acid (melting point 114 to 116 ° C) by heating and subsequent distillation to give N- ( m-Äthylmercaptophenyl) aniline (bp. 140 ⁰ C at 0.007 mm Hg).

20.12 g of N - (m - ethyl mercapto - phenyl) - aniline, dissolved in 90 ecm of absolute xylene, 4.10 g of finely powdered sodium amide, 15.9 g of 2 - (N - methyl - piperidyl -T) - 1-chlorine Ethane (bp. 84 ° C. at 10 mm Hg), dissolved in 15 ecm of absolute xylene, result in analytically pure N - [m - ethyl mercapto - phenyl] - N - [2 - (N '- methyl) according to the method described in Example 1 - piperidyl- T) -äthyl- (I)] -aniline with the bp. 206 ° C at 0.005mmHg.

Example 5

N- [m-Isopropylmercapto-phenyl] -N- [2- (N'-methylpiperidyl-2 ') -ethyl- (1)] - aniline

Is reduced m-isopropylmercapto-nitrobenzene (bp. 148 to 15O ⁰ C at 11 mm Hg) with tin (II) chloride or iron filings and hydrochloric acid to m-isopropylmercapto-aniline (bp. 142-144 ° C at 10 mm Hg) , which is condensed with potassium o-chlorobenzoate to form N- (m-isopropylmercapto-phenyl) -anthranilic acid (boiling point 114 to 116 ° C). This compound is decarboxylated by heating and subsequent distillation to give N- (m-isopropylmercapto-phenyl) -aniline (bp 143 ° C. at 0.005 mm Hg). 30.0 g of N- (m-isopropylmercapto-phenyl) -aniline dissolved in 135 ecm of absolute xylene, 5.77 g of finely powdered sodium amide and 22.4 g of 2 - (N-methyl-piperidyl-2 ') -1-chlorine - Ethane (bp. 84 ° C at 10 mm Hg), dissolved in 25 ecm of absolute xylene, result in reacted according to Example 1, analytically pure N- [m-isopropylmercapto-phenyl] -N- [2- (N'-methyl-piperidyl) -2 ') - ethyl- (l)] - aniline with the bp. 204 ⁰ C at 0.005 mm Hg.

Examples

N- [m-phenoxyphenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline

M-Amino-diphenyl ether with a bp. 190 to 191 ° C. is condensed at 14 mm Hg, melting point 37 ° C., with the potassium salt of o-chlorobenzoic acid, and the N- (m-phenoxyphenyl) anthranilic acid formed is decarboxylated (mp 131 to 133 ° C.) by heating to 250 ⁰ C. the mixture is then distilled, the resulting N- (m-phenoxy-phenyl) aniline in a high vacuum. Bp 165 ° C at 0.01 mm Hg. M.p. 77 to 79 ° C.

20.0 g of N- (m-phenoxyphenyl) -aniline, dissolved in 100 ecm of absolute xylene, 3.58 g of finely powdered Na-

triumamide, 14.0 g of 2- (N-methyl-piperidyl-2 ') - l-chloroethane, dissolved in 15 ecm of absolute xylene, result in analytically pure according to the method described in Example 1 N- [m-phenoxyphenyl] -N- [2- (N'-methyl-pipcridyl-2 ') - ethyl- (1)] - aniline with a bp. 195 ° C at 0.003 mm Hg.

The hydrochloride is prepared by dissolving 14.22 g of the base in 60 ecm of absolute ethanol and adding ethanolic hydrochloric acid until the Congo acidic reaction occurs. The analytically pure hydrochloride of N - [m - phenoxy - phenyl] - N - [2 - (N '- methylpiperidyl-2') - ethyl (l)] - aniline has mp 169 to 17TC after sintering from 165 ⁰ C. (from absolute ethanol).

Example 7

N- [m-Benzyloxyphenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline

The action of benzyl chloride on the sodium salt of 3-oxy-diphenylamine gives N- (m-benzyloxyphenyl) -aniline with a boiling point of 2O2 ° C. at 0.05 mm Hg ). 25.0 g of N- (m-benzyloxyphenyl) aniline, dissolved in 100 ecm of absolute xylene, 4.25 g of finely powdered sodium amide, 16.5 g of 2- (N-methyl-piperidyl-2 ') - l- Chlorethane, dissolved in 15 ecm of absolute xylene, result in analytically pure N - [m - benzyloxy - phenyl] - N - [2 - (N'-methylpiperidyl-2 ') - ethyl- (l)] - according to the method described in Example 1 aniline with bp 210 ^° C at 0.002 mm Hg.

Example 8

N- [m-n-Propoxyphenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline

Mn-propoxy-aniline bp 135 ° C. is condensed with the potassium salt of o-chlorobenzoic acid at 10 mm Hg and the resulting N- (mn-propoxyphenyl) -anthranilic acid (melting point 112 ° to 114 ° C.) is decarboxylated by heating to 250 ⁰ C. Subsequently, the resulting N- (mn-propoxy-phenyl) aniline distilled (bp. 202 ° C at 11 mm Hg).

18.95 g of N- (m-n-propoxyphenyl) aniline, dissolved in 100 ecm of absolute xylene, 3.90 g of finely powdered sodium amide, 15.13 g of 2- (N-methyl-piperidyl-2 ') -1-chloroethane, dissolved in 15 ecm of absolute xylene, result in the method described in Example 1, analytically pure N - [m - η - propoxy - phenyl] - N - [2 - (N '- methyl-piperidyl - 2 ') - ethyl- (I)] - aniline with the bp. 174 ° C at 0.005 mm Hg.

Example 9

N- [m-Isopropoxyphenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline

M-Isopropoxy-aniline (bp. 126 ° to 129 ° C. at 10 mm Hg) is condensed with the potassium salt of o-chlorobenzoic acid and the N - (m - isopropoxyphenyl) - anthranilic acid formed (m.p. 88 to 90 ° C.) is decarboxylated ) by heating to 250 ⁰ C. Subsequently, the resulting N- (m-isopropoxyphenyl) aniline distilled. Bp 194 ° C at 10 mm Hg.

17.61 g of N- (m-isopropoxyphenyl) aniline, dissolved in 100 ecm of absolute xylene, 3.63 g of finely powdered sodium amide, 14.10 g of 2- (N-MethyI-piperidyl-2 ') -1-chloroethane, dissolved in 15 ecm of absolute xylene, result in the method described in Example 1, analytically pure N - [m - isopropoxy - phenyl] - N - [2 - (N'-methylpiperidyl-2 ') - ethyl (1)] - aniline with bp 172 ° C at 0.005 mm Hg.

B e i s ρ i e 1 10

N- [m-Benzylmercapto-phenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline

It condenses m-Benzylmercapto-aniline from

. ίο b.p. 163 ° C at 0.06 mm Hg with the potassium salt of o-chlorobenzoic acid and decarboxylated, the resulting N - (m - benzylmercapto - phenyl) - anthranilic acid by heating at 250 ⁰ C. (mp 137 to 139 ° C.) The resulting N- (m-benzylmercapto-phenyl) -aniline is then distilled in a high vacuum, bp 214 ° C. at 0.02 mm Hg, melting point 61 to 63 ° C.

25.0 g of N - (m - Benzylmercapto - phenyl) - aniline, in 120 ecm of absolute xylene dissolved, 4.02 g of finely powdered sodium amide and 15.6 g of 2- (N-methyl-piperidyl-2 ') - l-chloroethane, dissolved in 16 ecm of absolute xylene, result in analogy to that described in Example 1 Process wherein the extraction of the crude product with 15% tartaric acid instead of 3 n-acetic acid takes place, analytically pure N- [m-Benzylmercapto-phenyI] -N- [2- (N'-methyl-piperidyl-2 ') - ethyl- (1)] - aniline with bp 215 ° C at 0.005 mm Hg.

Example 11

N- [m-n-Propylmercapto-phenyl] -N- [2- (N'-methylpiperidyl-2 ) -ethyl- (1)] - aniline

It is reduced in - η - propylmercapto - nitrobenzene (bp. 163 to 165 ° C at 11 mm Hg) with tin (II) chloride and hydrochloric acid to give mn-propylmercapto-aniline (bp. 154 to 157 ° C at 11 mm Hg) . This is condensed with the potassium salt of o-chlorobenzoic acid and decarboxylated, the resulting N- (mn-propylmercapto-phenyl) -anthranilic acid by heating and subsequent distillation to N (mp 99-101 ⁰ C.) - (m - η - propylmercapto - phenyl ) - aniline (bp 170 to 172 ° C at 0.01 mm Hg).

30.0 g of N- (mn-propylmercapto-phenyl) -aniline dissolved in 150 ecm of absolute xylene, 5.8 g of finely powdered sodium amide and 22.4 g of 2- (N-methyl-piperidyl-2 '> 1-chloro- Ethane, dissolved in 20 ecm of absolute xylene, give analytically pure N - [m - η - propylmercapto - phenyl] - N - [2 - (N '- methyl - piperidyl - T) - ethyl - (I )] - aniline with a bp. 198 ° C at 0.01 mm Hg.

When moving a cooled to 0 ⁰ C solution of 27.5 of the free base in 100 cc of isopropyl alcohol with hydrochloric acid isopropylalkoholischer g precipitates the hydrochloride which is recrystallized from 700 cc of boiling acetone. The analytically pure hydrochloride of N- [mn-propylmercapto-phenyl] -N - [2 - (N '- methyl - piperidyl - 2') - ethyl - (I)] - aniline has the constant melting point 135 to 137 ° C ( Vesicles).

Example 1 12

N- [m-n-Butylmercapto-phenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline

M-n-Butylmercapto-aniline (boiling point) is condensed. 172 to 176 ° C at 13 mm Hg) with the potassium salt of o-chlorobenzoic acid and decarboxylates the resulting N - (m - η - butyl mercaptophenyl) anthranilic acid (melting point 77 to 79 ° C) by heating and

final distillation (bp. 168 to 172 ° C at 0.01 mm Hg) to N- (m-n-Butylmercapto-phenyl) -ani-Hn. Mp. 30 to 32 ° C from petroleum ether (40 to 60 ° C).

50.0 g of N - (m - η - butylmercapto - phenyl) - aniline, dissolved in 220 ecm of absolute xylene, 9.10 g of finely powdered sodium amide and 35.4 g of 2- (N-methyl-piperidyl-2'H- Chlorine-ethane, dissolved in 35 ecm of absolute xylene, result in analytically pure N- [mn-butylmercapto-phenyl] - N - [2 - (N '- methyl - piperidyl - T) - ethyl - (1) ] -aniline with bp 204 ° C at 0.01 mm Hg.

When moving a cooled to 0 ⁰ C solution of 51.2 of the free base in 150 cc of absolute alcohol g with ethanolic hydrogen chloride, the hydrochloride precipitates, which is again recrystallized from 110 cc of boiling absolute alcohol. The analytically pure hydrochloride of N- [mn-butylmercapto - phenyl] - N - [2 - (N '- methyl - piperidyl - T) - ethyl (1)] - aniline has the constant melting point 112 to

Example 13

N- [m-methoxyphenyl] -N- [2- (N'-methylpiperidyl-2 ') - ethyl- (1)] - aniline ·

The reaction of 2- (N-methyl-piperidyl-2 ') - 1-chloro-ethane with N- (m-methoxy-phenyl) aniline following the same procedure (bp 196 mm to 200 ⁰ C at 13 Hg.) provides N - [m - methoxy - phenyl] - N - [2 - (N '- methyl - piperidyl - T) - ethyl - (1)] - aniline, bp 174 ° C / 0.01 mm Hg.

Test report
- A. Spasmolytic effect

Some typical representatives of the compounds according to the invention were examined for their barium chloride-inhibiting effect on the isolated small intestine of the guinea pig using the customary method. Papaverine was chosen as the standard substance (BaCl ₂ -inhibiting effect = 1).

The following connections were examined:

I: N- [m-n-Propoxyphenyl] -N- [2- (N'-methyl-

piperidyl-2 ') - ethyl- (1)] - aniline (cf. Example 8);
II: N- [m-phenoxyphenyl] -N- [2- (N '-methyl-

piperidyl-2 ') - ethyl- (1)] - aniline (cf. Example 6);
III: N- [m-Benzyloxyphenyl] -N- [2- (N'-methyl-

piperidyl-2> ethyl- (1)] aniline (see Example 7);
IV: N- [m-ethylmercapto-phenyl] -N- [2- (N'-methyl-piperidyl-2 ') -ethyl- (1)] -aniline
(see Example 4);

V: N- [m-Isopropylmercapto-phenyl] -N- [2- (N'-methyl-piperidyl-2 ') - ethyl- (1)] - aniline
(see example 5).

Served as comparison substance

VI: N - (/? - Piperidino-ethyl) -di-o-tolylamine-

hydrochloride. Table 1 BaCI ₂ inhibition
(Papaverine = I) Substance no. 23 times stronger T 35 times stronger II 45 times stronger ITT

Substance no.

IV

V
VI

BaCI, inhibition
(Papaverine = 11

30 times stronger
25 times stronger
13 times stronger

From these data it can be seen that all the substances tested have a significantly stronger BaCl ₂ -inhibiting effect than the comparison substance V1.

They thus show a spasmolytic effect 1.8 to 3.5 times stronger than the comparison substance No. VI and an effect 34 to 45 times stronger than the standard preparation papaverine.

B. Toxicity

The toxicity of a prototype, namely substance (IV) (N - [m - ethyl mercapto - phenyl] - N - [2 - (N '- methyl - piperidyl - T) - ethyl - (1 )] - aniline) and compared with the toxicity of the reference substance (VI) [N - (ß - piperidino - ethyl) - df - ο - tolylamine - hydrochloride]. For substance (IV) it is 84 mg / kg, intravenously. The corresponding infusion toxicity value of the reference substance (VI) is 88 mg / kg, intravenously.

They differ in terms of compatibility

the two substances are not significantly different from each other.

The pharmacological analysis of the spectrum of activity of the compounds according to the invention has shown that their therapeutically desirable effects are of the order of magnitude for the products of the process Have a therapeutic index calculated that is clearly superior to that of the reference substance is, d. i.e., a smaller fraction of the toxic dose is used to achieve the same therapeutic effect necessary than with the reference substance. Substance (IV) can be used in a dose that is 2.3 times smaller to produce the same spasmolytic effect as the comparator preparation (VI).

The better compatibility of the compounds according to the invention is even more pronounced the comparison substance when testing for histamine inhibition.

C. Antihistamine Action

The connections were used as prototypes

IV: N- [m-ethylmercapto-phenyl] -N- [2- (N '-methyl-piperidyl-2') - ethyl- (l)] - aniline, process product of Example 4, and
VII: N- [m-methylmercapto-phenyl] -N- [2- (N'-me-

'thyl-piperidyl-2') - ethyl- (l)] - aniline, process product of Example 1,

with respect to their histamine-inhibiting effect on the isolated guinea pig small intestine compared with the comparison substance VI. The unit chosen was 1 - methyl - 4 - amino - N '- phenyl - N' - {Τ - thenyl) piperidine, a commercially known antihistamine.

309 623/107

Table 2

substance

VII
VI

Histamine inhibition

1-methyl-

4-amino-

N'-phcnyl-

N '- (2'-thcnyl) -

pipcridin = 1

0.25
0.17
0.025

Compensation Subsidy
VI = 100
(relative
Effect)

1000
680
100

Toxicity

Infusion

melhode.

mouse

mg / kg, i. v.

76 84

88

Relative toxicity of comparison substance VI = 100

116

105 100

.5

Although the toxicity values do not differ significantly from one another (Col. 4) are those according to the invention Compounds clearly superior to comparison substance VI; because substance VII can be in 6.8 times smaller and substance IV even 10 times A smaller dose can be used in order to achieve the same histamine-inhibiting effect as the comparison substance.

Therapeutic range: From the relative values in Table 2 (Col. 3 and 5), the so-called "Therapeutic breadth," d. H. the quotient

30 relative effect

relative toxicity

determine. This shows that substances IV and VII are 6.5 to 8.6 times more therapeutic Possess breadth than the reference substance.

D. Antifungal effect in vitro

two strains of Candida albicans

(Strain No. 121 and 122)

A sterile dilution series in the appropriate nutrient solution was prepared from the substance to be tested from diluted beer wort (original wort diluted 1: 8 with tap water) and 1% glucose, manufactured. Each 5 ecm of these solutions were diluted 1:50 in test tubes with one drop each and 16 hour old culture of the Candida albicans strains. The incubation took place at 37 ° C, the growth reading after 24 hours. The following connections were examined:

VII: N- [m-benzylmercapto-phenyl] -N- [2- (N'-methyJ-pipcridyl-2 ') - ethyl- (1)] - aniline
(see Example 10);

VIII: N-fm-n-butylmercapto-phenyI] -N- [2- (N'-methyl-piperidyl-2 ') - ethyl - (!)] - aniline
(see example 12).

Served as comparison substance

IX: 2,2'-Dioxy-5,5'-dichloro-diphenyl sulfide.

Table 3 Total growth Candida aibicans inhibition up to 1: Trunk no. 80Ό00 VI (21 64'00O 122 80Ό00 VIII 121 80ΌΟ0 122 64'0OO IX 121 64'00O 122

Claims (1)

Patent claims:
1. Compounds of the general formula I denotes phenoxy or benzyloxy groups. The compounds of the general formula I according to the invention are obtained by adding a secondary amine of the general formula II