DE1468088C - Triphenylalkenamino ethers and processes for their preparation - Google Patents

Description

^ N- (CH ₂ ) "- O-

in which R ₁ , R ₂ and π have the meaning given above, R being the same

- C (OH) (C ₆ H ₅ ) -CH (C ₆ H ₅ ) - R ₃
or .

. - CH (C ₆ H ₅ ) - C (OH) (C ₆ H ₅ ) - R ₃

and R _{3 has} the meaning given above, in the presence of an acidic catalyst such as hydrochloric, hydrobromic, phosphoric acid or formic acid, splitting off water or that one
b) an aminoalkyl halide of the general formula

_; /; X.,. R ₁ -N (R ₂ XCHj) ₁₁ -X.

in which R ₁ , R ₂ and η have the meaning given above and X is a halogen atom, with a compound of the general formula:

MO-

-C (C ₆ H ₅ ) = C (C ₆ H ₅ ) -R ₃

From U.S. Patents 2,914,529, 2,914,561 and 2,914,563 it is known that a number of 1,1,2-triphenylethylene or l, l, 2-triphenyl-2-halogenethylene derivatives, which has a dialkylaminoalkoxy substituent on one of the phenyl radicals in the 1-position and usually a methyl, methoxy or have halogen substituents on one of the other phenyl radicals, have an anti-estrogenic effect own. The present invention is based on the finding that a group of 1,1,2-triphenylalkene derivatives, which has a dialkylaminoalkyl substituent on one of the phenyl radicals in the p-position and have no substituents on the other phenyl radicals, are very effective anti-estrogens, and at the same time have a comparatively much lower estrogenic effect than those previously known Links. Accordingly, the use of the compounds according to the invention as antiestrogens Means accompanied by a lower incidence of estrogenic side effects than when using the previously known compounds is the case.

The invention relates to triphenylalkeneamino ethers of the general formula
R, "■ ■" ■■ '' ^■: ■ ''.

N- (CH ₂ ) ,, - O-

-C (C ₆ H ₅ ) = C (C ₆ H ₅ ) -R ₃

converts, in which M is hydrogen or an alkali metal atom and R _{3 has} the meaning given above,

and that optionally the resulting triphenylalkenamino ethers with an inorganic or organic acid converted into their salts.

where R ₁ and R _{2 are the} same and methyl or ethyl

■ · ■ radicals or together with the adjacent nitrogen atom form a piperidine, morpholine or pyrrolidine group, η is 2 or 3 and R _{3 is} an alkyl radical with not more than 3 carbon atoms, as well as salts of these compounds. .

A particularly suitable substituent for R ₃ is an ethyl or n-propyl radical, and a particularly preferred compound of the invention is 1- (p- / S-dimethylaminoethoxyphenyl) -l, 2-diphenylbut-1-ene.

Preferred salts of compounds of the invention are hydrochlorides, sulfates, phosphates, acetates, tartrates, Oxalates or citrates, of which the citrates are particularly suitable.

The invention also relates to a process for the preparation of the specified triphenylalkenamino ethers, which is characterized in that in a known manner. .

^ a) from an alkanol compound of the general formula

The invention relates to triphenylalkenamino ethers which have valuable therapeutic properties

mti \ f \ - & \

sit.

in which R ₁ , R ₂ and η are those given above

Have meaning, R equals

- C (OH) (C ₆ H ₅ ) - CH (C ₆ H ₅ ) - R ₃
or

- CH (C ₆ H ₅ ) - C (OH) (C ₆ H ₅ ) - R ₃

and R _{3 has} the meaning given above, in the presence of an acidic catalyst such as hydrochloric, hydrobromic, phosphoric acid or formic acid, splitting off water or that one

b) an aminoalkyl halide of the general formula

Ri- N (R ₂ XCH ₂ ) ,, - X

in which R ₁ , R ₂ and η are as defined above and X is a halogen atom, with a compound of the general formula

MO-

C (C ₆ H ₅ ) = C (C ₆ H ₅ ) -R ₃

converts, in which M is hydrogen or an alkali metal atom and R _{3 has} the meaning given above,

and that optionally the resulting triphenylalkenamino ethers converted into their salts with an inorganic or organic acid.

The dehydration reaction (a) is preferably carried out by heating the starting materials in an inert solvent such as ethanol, and the alkylation reaction (b) is preferred carried out in the presence of a base when M. is a hydrogen atom. .

The starting materials for process (a) can by reacting a Grignard compound of the general formula

R,

R ₂

N- (CH ₂ J _n -O-

wherein X is a chlorine or bromine atom with an α-alkyldeoxybenzoin derivative of the general formula · ·. .. ■■ - _; ■■■ '■■■ ■' ■: ■. ·;. ■.: -: -. · .- · ... Γ: ■ - ·.

C ₆ H ₅ CO CHR ₃ - C ₆ H ₅ -

or by reacting a carbonyl compound of the general formula ■ ;; -

N- (CH ₂ J _n -O-

-CO-CH (C ₆ Hj) -R ₃

with Phenylmagnesiumbrpmid: The Carbpnylverbiridungen are by alkylating a 4-Hydroxya-alkyldeoxybenzoins receive. ; :.

In the present description, the following numbering of the deoxybenzoin nuclei is used for the deoxybenzoin derivatives: ',

3 2

5 6

COCH ₂

6 '5'

The compounds according to the invention are valuable in that they have an anti-estrogenic effect and this is of value in the treatment of endocrine disruptions caused by hormones Tumors and in the regulation of the sexual cycle and deviations from it.

The compounds according to the invention are in the form of pharmaceutical compositions of matter used, which contain the usual additives and according to the usual procedure getting produced. Preferred pharmaceutical compositions of matter are tablets that be prepared in the usual way with an inert carrier, binders and lubricants.

The invention is illustrated in the following examples

explained in more detail. ". . . _Λ ■ ". '■■■■

For example. L

6.45 parts of 1 - (p - β - diethylaminoethoxyphenyl) -1,2-diphenylpropan-l-ol are dissolved in 50 parts of ethanol, and the solution is acidified with concentrated hydrochloric acid. The solution is heated for 3 hours under reflux at 10O ⁰ C and then evaporated under reduced pressure to dryness. The residue is dissolved in water and the solution is made alkaline with concentrated sodium hydroxide solution. The reaction mixture is extracted twice with 100 parts of ether, the combined ether extracts are dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is dissolved in as little acetone as possible, and a saturated solution of 12 parts of citric acid in acetone is added. The mixture is filtered off and the solid residue is recrystallized from acetone. The 1 - (p- ß- diethylaminoethoxyphenyl) -1,2-diphenylprop -1-en-citrate dihydrate of melting point 118 to is obtained

120 ° C. ;;; - ■.;: ■ - '/:> ■■ *: r ^: ': - ■ '■ -: - ^: -. ■■■■. "'^ - ■■ ■ / ■■ - ■■ ■■■

The l- (p - /? - Di-

ethylaminoethoxyphenyl) -1,2 - diphenylpropane -1 - oil can be made as follows:

From 3.9. Parts of magnesium and 45 parts of p- / 3-diethylaminoethoxybromobenzene in 80 parts of tetrahydrofuran, the Grignardyer bond is formed in the usual way manufactured, and; this solution is at 20. to 25 ° C with a solution of 16.8 parts of a-methyldeoxybenzöin added in 70 parts of tetrahydrofuran. The reaction mixture is refluxed for 3 hours and then cooled to room temperature Then a solution of 200 parts of ammonium chloride added in 500 parts of water, shaken the mixture and then; separated: both phases are kept. The aqueous phase is extracted twice with 100 parts of ether. The ether and Tetrahydrofuran solutions "are combined over dried anhydrous magnesium sulfate and evaporated to dryness. The i- (p - /? - diethylaminoethoxyphenyl) -l, 2-diphenylpropan-l-ol is obtained.

■ '.- ■■ ^; 'Y.;. · / Example 2 ' ^: -: [/ '.'"'.'"'/.'■■.

1.43 parts of 1 - ρ - hydroxyphenyl -1,2 - diphenylprop-1-ene are dissolved in a solution of 0.15 parts of sodium in 20 parts of ethanol. The solution is evaporated to dryness, and the sodium salt of 1-p-hydroxyphenyl-1,2-diphenylprop-1-ene remains. 2 parts of β- diethylaminoethyl chloride hydrochloride are dissolved in water and the solution is made alkaline with sodium hydroxide solution. The mixture is extracted with 50 parts of toluene, and the toluene extract is dried over potassium hydroxide

and then added to the aforementioned sodium salt. The reaction mixture is refluxed and stirred for 8 hours. After cooling and filtering, the filtrate is evaporated to dryness under reduced pressure. To yield the l- (p - / -? Diäthylaminoäthoxyphenyl) -1,2 - diphenylprop - 1 - ene, which according to Example 1 in the citrate dihydrate, mp 118 is converted to 12O ⁰ C,. Further drying provides the corresponding sesquihydrate with a melting point of 124 to 126 ° C.

The 1-p-hydroxyphenyl-1,2-diphenylprop-1-ene used as the starting compound can be made as follows:

The Grignard compound is prepared in the customary manner from 3.9 parts of magnesium and 30 parts of p-bromanisole in 100 parts of ether, and a solution of 16.8 parts of a-methyldeoxybenzoin in 70 parts of ether is added to the resulting solution. The reaction mixture is stirred at room temperature for 1 hour and then refluxed and stirred for 3 hours. The reaction mixture is cooled and a solution of 200 parts of ammonium chloride in 500 parts of water is added. The mixture is separated and the ethereal solution is dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is fractionally distilled in vacuo. The at 182-200 ⁰ C (0.3 Torr) boiling fraction is collected and recrystallized from petroleum ether, bp. 60 to 80 ⁰ C. The l-p-methoxyphenyl-l ^ -diphenylpropan-l-ol with a melting point of 86 ° to 87 ° C. is obtained.

A solution of 2 parts of 1-p-methoxyphenyl-1,2-diphenylpropan-1-ol and 5 parts of concentrated hydrochloric acid in 20 parts of ethanol is refluxed for 3 hours. The mixture is evaporated to dryness under reduced pressure and the residue is recrystallized from methanol. The 1-p-methoxyphenyl-1,2-diphenylprop-1-ene is obtained with a melting point of 131 to 133 ^° C.

3 parts of 1 - ρ - methoxyphenyl -1,2 - diphenyl - prop-1-ene and 10 parts of pyridine hydrochloride are refluxed for 1 hour. The reaction mixture is cooled, mixed with 50 parts of water and 50 parts of ether and then extracted by shaking. The mixture is separated and the ether solution extracted with 50 parts of 10% sodium hydroxide solution. The alkaline extract is acidified with hydrochloric acid and the mixture obtained is extracted twice with 50 parts of ether. The combined ether extracts are dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is recrystallized from petroleum ether, bp. 100 to 120 ⁰ C. The 1-p-hydroxyphenyl-l ^ -diphenylprop-1-ene is obtained with a melting point of 122 ° to 124 ° C.

B e i s ρ i e 1 3

In a manner similar to Example 2, using a solution of 1.22 parts of γ-dimethylaminopropyl chloride in 40 parts of benzene on the part of the solution of / S-diethylaminoethyl chloride l- (p-γ-dimethylaminopropoxyphenyl) -1,2-diphenylprop-l-ene oxalate in toluene from m.p. 110 to 111 ° C

receive. . ...

Example 4

The procedure described in Example 1 is repeated with the modification that the product by steam distillation of the basicized reaction mixture before the extraction of the not volatile residue is isolated with ether. In this way, from the corresponding triphenylalkan-1-ols receive:

1 - (p - /? - diethylaminoethoxyphenyl) -1,2-diphenylbut-1-ene citrate, Mp. 138 to 140 ° C, or

1 - (p- / 3-diethylaminoethoxyphenyl) - 1,2-diphenylpent-1-ene citrate, Mp. 141 to 142 ° C.

The triphenylalkan-1-ols used as starting material are made by reacting the Grignard compound from p-j9-diethylaminoethoxy-bromobenzene with a-ethyldeoxybenzoin or a-n-propyldeoxybenzoin in tetrahydrofuran under reflux during

Prepared for 3 hours, whereupon ammonium chloride was added and the solid residue was extracted with ether and is filtered. After evaporation of the ether, the desired triphenylalkan-1-ol is obtained.

B e i s ρ ie I 5

2.15 parts of 1 - (p - β - dimethylaminoethoxyphenyl) -1,2-diphenylbutan-1-ol, 25 parts of ethanol and 0.8 part of 10N salt acids are refluxed for 3 hours. The 'solution is evaporated to dryness under reduced pressure and the residue is extracted with methylene chloride. The methylene chloride extract is decolorized with activated charcoal and then evaporated to dryness. The residue is dissolved in 100 parts of water, the solution is made alkaline with sodium hydroxide solution and the precipitated solid is extracted three times with 50 parts of ether each time. The combined extracts are washed with anhydrous sodium. sulfate dried and then evaporated. The residue is recrystallized from hydrous methanol

'. <- sated. The l- (p - /? - Dimethylaminoethoxyphenyl) -l, 2-diphenylbut-l-ene is obtained from m.p. 95 to 96 ° C. 2 parts of this compound are stirred with a solution of 2 parts of citric acid in 10 parts of acetone. The mixture is filtered off and the solid residue is recrystallized from acetone. You get the corresponding citrate, m.p. 140 to 142 ° C. The treatment of the crude base, d. H. the connection, which is obtained from aqueous methanol before recrystallization, with citric acid gives * a mixture produced by fractional crystallization into the aforementioned citrate of melting point 140 to 142 ° C and an isomeric citrate of melting point 126 to 128 ° C can be separated.

The l- (p - /? - Di- * methylaminoethoxyphenyl) - 1,2-diphenylbutane-1 oil can be made as follows:

The Grignard compound is made from 0.59 parts of magnesium, 3.95 parts of bromobenzene and 50 parts of ether produced, which then with 7.5 parts

4 - (ß - Dimethylaminoethoxy) - α - ethyldeoxybenzoin in 50 parts of ether is added. After refluxing for 3 hours, the mixture is decomposed with a solution of 60 parts of ammonium chloride in 150 parts of water. The mixture is separated and the ether solution is dried with anhydrous sodium sulfate and the ether is evaporated. The residue is recrystallized from methanol. 1 - (P - ß - dimethylaminoethoxyphenyl) -1,2 - diphenylbutan-1-ol with a melting point of 120 ° to 121 ° C. is obtained.

4 - (/ 5-Dimethylaminoethoxy) -a-ethyldeoxybenzoin (Bp. 162 ° C / 0.075 Torr) can be obtained by demethylation obtained from 4-methoxy-a-ethyldeoxybenzoin, namely by heating with pyridine chloride under reflux for 30 minutes to α-ethyl

4-hydroxydeoxybenzoin (m.p. 122-124 ° C) result, which is then in the form of the sodium salt with ß-dimethylaminoethyl chloride in benzene under reflux 16 hours is implemented. The reaction mixture is concentrated and the residue in Dissolved 2N hydrochloric acid. The solution is filtered, made alkaline and extracted with ether, whereupon the extract is then evaporated and the residue is distilled to give the desired 4 - (, δ-dimethylaminoethoxy) -a-ethyldeoxybenzoin to surrender.

In a manner similar to that described above for the preparation of 1 - (p - β - Dimethylaminoä thoxyphenyl) -1,2-diphenylbut-1-ene citrate, 1,2-diphenyl-1 - (p- ^ -pyrrolidinoäthoxyphenyl) -but-1-en-citrate, mp. 144 to 146 ° C, which l- (py-Dimethylaminopropoxyphenyl) -l, 2-diphenylbut-1-ene-oxalate, mp. 146-147 ⁰ C, or The 1,2-diphenyl-l- (p - ^ - piperidinoethoxyphenyl) -but-l-ene hydrochloride, melting point 185 to 186 ° C, starting from l- (p - /? - pyrrolidinoethoxyphenyl) -l, 2 -diphenylbutan-l-ol, m.p. 110 to 112 ⁰ C, 1 - (p - y - dimethylaminopropoxyphenyl) -1,2 - diphenylbutane -1 - oil or 1 - (p - β - piperidinoethoxyphenyl) -1,2- . diphenylbutane-l-ol, m.p. 140 to 142 ⁰ C. The latter three compounds can be prepared from a-ethyl-4 - (ß - pyrr'olidinoäthoxy) - desoxybenzoin, b.p. _{0> 02} 5176-182 ⁰ C, A-. ethyl-4- (y-dimethylamino) -desoxybenzoin, mp 58 to 6O ⁰ C, bp _0, 7 ₅ 165 ° C, or α -.. ethyl - 4 - (ß - piperidinoäthoxy) - desoxybenzoin, b.p.-0, 05 188 ° C, according to procedures analogous to them are described above for the preparation of l- (p- / 3-Dimethylaminoä thoxyphenyl) -1,2 - diphenylbutane -1 - oil. The last-mentioned deoxybenzoin derivatives can in turn be prepared from α-ethyl-4-hydroxydeoxybenzoin in a manner analogous to that described above.

B e i s ρ i e 1 6

The Grignard compound is prepared from 1.46 parts of magnesium and 4.71 parts of bromobenzene in 70 parts of ether, and a solution of 10 parts of 4 - (ß - diethylaminoethoxy) - α - ethyldeoxybenzoin in 80 parts of ether is added. After refluxing for 3 hours, the mixture is decomposed with a solution of 100 parts of ammonium chloride in 250 parts of water. The mixture is filtered off and the filtrate is separated. Both phases are saved. The aqueous phase is extracted twice with 50 parts of ether and the extracts are combined with the non-aqueous phase. The solution is dried over anhydrous sodium sulfate and the solvent is evaporated. The residue consists of 1 - (p - β - diethylaminoethoxyphenyl) -1,2 - diphenylbutane-1-oil. This compound is dissolved in 60 parts of alcohol and the solution is acidified to Congo red by adding 6 parts of 10 η hydrochloric acid. The mixture is refluxed for 3 hours, then the ethanol is evaporated off under reduced pressure. The residue is extracted with 100 parts of methylene chloride and the methylene chloride extract is decolorized with activated charcoal and the solvent is evaporated off under reduced pressure. The residue is dissolved in 200 parts of water and the solution is made alkaline with 10 η sodium hydroxide solution. The mixture is extracted three times with 50 parts of ether, the combined ether extracts are dried over anhydrous sodium sulfate and the solvent is evaporated off. The residue is l- (p- / 5-diethylaminoethoxyphenyl) -1,2-diphenylbut-1-ene.

9 parts of this connection are made with 9 parts

Citric acid stirred in 50 parts of acetone. The mixture is filtered off and the solid residue is recrystallized from acetone. The corresponding citrate of melting point 138 to 140 ^° C. is obtained.

The 4 - (ß - Diäthylaminoäthoxy) - α -. Äthyldesoxybenzoin, Kp _0, 2175 ⁰ C, can be made of a-ethyl-4-hydroxydeoxybenzoin in an analogous manner as described in Example 5 to produce the corresponding dimethylamino derivatives, prepared .

In a manner similar to that described above for the preparation of 1 - (p - β - diethylaminoethoxyphenyl) -1,2 - diphenylbut - 1 - ene citrate, 1 - (p - β - diethylaminoethoxyphenyl) - 3 - methyl-1, 2-diphenylbut-l-en-citrate, m.p. 118-120 ° C, and the 1 -. (p - γ - Diäthylaminopropoxyphenyl) -1,2 - diphenylprop-1 -en-citrate, mp 110 to 11Γ C from. 4 - (/ 9-Diethylaminoethoxy) -a-isopropyldeoxybenzoin, b.p. _O8 190 to 193 ° C, or 4- (a-diethylaminopropoxy) -a-methyldeoxybenzoin, _{b.p. 0-75} 182 ⁰ C. The last-mentioned compounds can be found in analogous manner as described in example 5 for the preparation of 4- _(3-j Dimethylaminoäthoxy) - α - methyldesoxybenzoin described, from 4-hydroxy-a-isopropyldesoxybenzoin, m.p. 126 to 128 ⁰ C, and 4-hydroxy-a-methyldesoxybenzoin. , getting produced. 4-hydroxy-a-isopropyldesoxybenzoin can as in Example 5 for the preparation of 4 in an analogous manner - described (/ J-Dimethylaminoäthoxy) -a-äthyldesoxybenzoin, methoxydesoxybenzoin 4-a-isopropyl-out Kp _{0> 3} 150 ⁰ C. , Mp. 48 to 50 ⁰ C, are produced. The last-mentioned compound can be prepared from 4-methoxydesoxybenzoin in a manner analogous to that described in Example 5, by alkylation with isopropyl bromide.

The following comparative tests were carried out to demonstrate the technical progress achieved by the invention accomplished.

The estrogenic effectiveness and anti-implantation effectiveness of the products manufactured according to the invention and of known compounds, which have an estrogenic effect were determined by the following procedures.

a) estrogenic effects ν

Each test compound was administered to each animal of a group of six once a day for 3 days Orally administered to adult female rats with their ovaries removed. have been. At the depths vaginal swabs were taken on the fourth day in the morning and in the afternoon and on fifth and sixth day of the experiment in the afternoon. The smears were examined and those which partially and / or completely keratinized tissue and containing no leukocytes were considered keratinized classified. The experiment was then repeated using different ones Doses of each test compound, the daily dose (expressed as mg / kg of body weight) was calculated, which was required in at least 50% of the animals at least one Smear with keratinized tissue. This dose (MCD) is shown in the table.

b) Anti-implantation effectiveness

The test compound was administered orally three times a day to each animal in a group of four rats, on the second, third and fourth days of pregnancy. The rats were on the eighth

209542/563

ίο

Search day killed, dissected and plotted the number of implantation sites with reference to the number of rejected eggs (number of Corporalutea). The experiment was repeated with different amounts of testy binding and the daily dose (in mg / kg of body weight) which caused a loss of 50% of the eggs prior to implantation was then calculated. This dose (MED _AI ) is given in the table.

The compounds examined corresponded to the following formula:

Tested connection MCD MED _A , ratio of
MCD 4,4'-dihydroxy
α, / 3-diethyl stilbene
Until - (/? - brompro-
pionate) of 4,4'-Di- '
hydroxy-a, | S-diethylT \
stilbene
Dienestrol ■■ 0.0062
'0.014
0.004 0.0135
0.032
0.024 MED _A , 0.5
0.4
0.2

- (CH ₂ ) _n - O- <f Vc (C ₆ Hs) = C (C ₆ Hs) -R ₃ _. ". ,. . . . _,. _

ν ζ / η \ _ / ν & 5 / ν 6 _{5/3 Ι5 The} test results show that the invented

^ the compounds according to the invention the previously known

^<2 estrogenic agents are superior by using

Doses at which no estrogenic activity is produced, an anti-implantation effect produce.

Comparative experiments

Based on the experimental conditions given above, the following compounds were obtained those described in U.S. Patents 2,914,529, 2,914,561, and 2,914,563 are. These compounds correspond to the following general formula

Examined .. R. R ₂ . η R ₃ connection No. CH ₃ CH ₃ 2 QH ₅ 1 CH ₃ CH ₃ 3 QH ₅ 2 QH ₅ QH ₅ 2 QH ₅ 3 QH ₅ QH ₅ 2 nC ₃ H ₇ 4th QH ₅ QH ₅ 2 ISO-C ₃ H ₇ 5 QH ₅ QH ₅ 3 CH ₃ 6th C. 2 QH ₅ 7th c 2 QH ₅ 8th

30th

R ₁

C (RJ = C (R ₅ ) R ₃

When these compounds were tested according to the procedures described above, so the following results were obtained:

Examined MCD MED _A1 . 0.022 ratio of connection ■ 0.011 MCD No. 9.5 0.058 MED _AI 1 1.2 0.116. 431 2 ': 4.3 0.096 109 3 17.1 0.022 74 4th 2.2 0.070 147 5 0.7 0.036 23 6th 4.9 32 7th 25.7 70 8th 711

35 1
Compare
Verb. Ri R ₂ η R ₄ R ₅ R ₃ ⁴⁰ A QH ₅ QH ₅ 2 CH ₃ O - ^ y- C ₆ H ₅ H B. QH ₅ QH ₅ 2 C ₆ H ₅ C ₆ H ₅ H C.
45
D. QH ₅
QH ₅ QH ₅
QH ₅ (N (N C ₆ H ₅
CH ₃ O- / ~ \ - ^ C ₆ H ₅
C ₆ H ₅ Cl
Cl

With these compounds, the following results were found:

55

The following compounds known to have estrogenic activity were also subjected to the investigations described and the following results were obtained achieved:

MCD MED _AI ratio of Comp.-
Verb. MCD 16.9 1.2 MED _AI A ϊ > 50 about 5.5 14th B. 0.3 0.046 > 10 C. 0.49 0.047 6.5 D. 10

Claims (3)

Claims: 1. Triphenylalkenamino ethers of the general formula N- (CH ₂ J _n -O -C (C ₆ H ₅ ) -C (C ₆ H ₅ ) R ₃ where R ₁ and R _{2 are the} same and are methyl or ethyl radicals or together with the adjacent nitrogen atom form a piperidine, morpholine or pyrrolidine group, η is 2 or 3 and R _{3 is} an alkyl radical with not more than 3 carbon atoms, and Salts of these compounds. 2.1 - (p - β - Dimethylaminoethoxy phenyl) -1,2-diphenylbut-1-en and its salts. 3. A method for the preparation of triphenylalkenamino ethers according to claim 1, characterized in that that one in a known manner a) from an alkanol compound of the general formula R,