DE2521798A1 - DIPHENYLALLYLAMINOAL CANOLS - Google Patents

Description

T 49 887

Applicant: Hokuriku Pharmaceutical Co., Ltd., 1-Chome, 3-14, Tatekawacho, Katsuyamashi, Fukui / Japan

Diphenylallylaminoalkanols

The invention relates to new diphenylallylaminoalkanols of the general formula I.

= CH-CH ₂ -NH- (CH ₂ ) _n -0H (I)

in which η is an integer of 2 or 3, and the corresponding acid addition salts and drugs, which contain these compounds.

The invention also relates to a process for the preparation of compounds of the formula (I), which thereby is characterized in that a ß-phenylcinnamaldehyde Formula II

f- \ ß = CH-CHO (II)

with an aminoalkanol of the general formula III

NH ₂ - (CH ₂ ) _n -0H (III)

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in which η has the definition given above, condenses and the condensation product thus obtained with the aid of. Reducing agents such as alkali borohydride is reduced. Preferably, p-phenylcinnamaldehyde (II) is condensed with an aminoalkanol (III) in an equimolar or excess amount up to a molar ratio of 1: 1.5, optionally in a solvent such as an alcohol. It is then expediently concentrated to dryness under reduced pressure. The condensation product obtained in this way is reduced with sodium borohydride at room temperature, preferably at a temperature between 10 to 20 ^° C., in a solvent such as alcohol, dioxane, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide. The compounds according to the invention can be converted into the corresponding salts with any inorganic or organic acid.

Specific examples of inorganic acids include hydrochloric acid, Hydrobromic acid, sulfuric acid, etc. Organic acids are for example maleic acid, oxalic acid, tartaric acid, Citric acid, succinic acid, etc.

The compounds according to the present invention are valuable drugs with local anesthetic, antileptic, coronary vasodilator and antispasmodic properties. In addition, the compounds according to the invention are valuable intermediates for the preparation of the medicaments, which are the subject of patent 2,350,125 (DT-OS 2,350,125) by the same applicant. The invention is based on the following examples.

example 1

Production of 2- (3 »3-diphenylallylamino) -1-ethanol A solution of 4.16 g / 2-phenylcinnamaldehyde and 1.22 g monoethanolamine in 20 ml of ethanol is under vacuum to dryness

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brought. The residue is dissolved in 10 ml of methanol, and 2.88 g of sodium borohydride are added in portions to the solution, which has been cooled to room temperature. The mixture is then stirred for 4 hours at room temperature. After the reaction was completed and the solvent was distilled off, water was added to the residue and the aqueous solution was made alkaline with potassium carbonate. Then it is extracted with chloroform. After drying the chloroform phase over sodium sulfate and distilling off chloroform, a sticky product was obtained in an amount of 3.98 g (73 % of theory). The product thus obtained was converted into the oxalate with oxalic acid. After recrystallization of the salt from isopropanol / ethanol (1: 1), the product with a melting point of 150 to 151 ° C. is obtained.

Analysis for C ^ 7H ₁₀ ON-C ₂ H ₂ O ^

calcd C 66.46 H 6.16 N 4.08 found C 66.40 H 1.19 N 4.10

Example 2

Production of 3- (3> 3-diphenylallylamino) -1-propanol A solution of 4.16 g of ^ -phenylcinnamaldehyde and 1.50 g of 3-amino-1-propanol in 20 ml of ethanol was reduced under reduced pressure Print dried up. The residue was dissolved in 10 ml of methanol and added to the solution cooled to room temperature 2.88 g of sodium borohydride are added in portions with cooling. After the addition was completed, the reaction mixture became Stirred for 4 hours at room temperature, and after the completion of the reaction, the solvent was distilled off. After the residue was dissolved in water, it was made alkaline with potassium carbonate and extracted with chloroform. To Drying the chloroform phase over sodium sulfate and distilling off the chloroform and recrystallizing the so

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ί - 4 - , 86 H 7.92 N 5.24
, 59 H 7.99 N 5.10 - 15 H 7.30 N 4.61
01 H 7.32 N 4.64 The residue obtained from benzene / n-hexane (1: 1) was the
desired product in an amount of 3.76 g (74 % of theory)
obtained with a mp of 93 to 95 ° C. The base was converted into its hydrochloride. After recrystalline
lization from isopropanol / isopropyl ether (1: 1) was the
Melting point 142-144 ° C. / Claims:
/ Analysis for C ₁₈ H, Analysis for C _1Q H, - 5 - calculated C 80
found C 80 calculated C 71
found C 71,

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Claims (1)

- 5 - Patent claims: (D means, (D formula (III) 2. Process for the production of new diphenylallylamino
alkanols of the general formula I means,
labeling
of formula II Has,
link "^ C = CH-CHg-NH- (CHg) _n -OH (II) - 6 - 1. Diphenylallylamino alcohols of the general formula I in which η is an integer of 2 or 3
and their salts, thereby k
net that one ^ -phenylcinnamaldehyde ^ - C = CH-CH ₂ -NH- (CH ₂ J _n -OH α
/} λ C = CH-CHO in which η is an integer of 2 or 3
and their salts. with an aminoalkanol of the general NH ₂ - (CHg) _n -OH in the η the meaning given above
reductively condensed and the obtained
optionally converted into a salt. 509849/1028 3 _«r drugs consisting of one or more compounds of claims 1 to 2 and conventional auxiliaries and / or carriers TAFFEN®. Dr.T / us 509849/1028