JPS63141955A - Tribenzylamine derivative - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I (R<1> and R<2> are H or 1-3C alkyl; R<3> and R<4> are group shown by formula II, formula III, etc.). USE:A tyrosinkinase inhibitor, ultraviolet light absorber, antimicrobial agent or an intermediate for synthesizing various organic compounds. Useful for treating diseases such as asthma, inflammations, cancers, etc., preventing sunburn, deterioration of organic high polymer material by ultraviolet rays, etc. Shows excellent Gram-positive and Gram-negative bacteria as a fungicide. PREPARATION:An aldehyde shown by formula IV (R<5> and R<6> are H or 1-3C alkyl) is reacted with one or more compounds such as compounds shown by formula V, formula VI, etc., to give a compound shown by formula I. The reaction is carried out by condensation, as necessary in the presence of an acid or base catalyst.

Description

Detailed Description of the Invention (Industrial Application Field) The present invention provides tyrosine kinase inhibitory action, ultraviolet absorption action,
Tribenzylamine derivatives and salts thereof, which have antibacterial effects and are useful as intermediates for many organic compounds, methods for producing the same, and tyrosine kinase inhibitors, ultraviolet absorbers, and antibacterial agents containing this tribenzylamine as an active ingredient. It is something.

(Prior art) The compound according to the present invention is a new compound that has not been described in any literature,
This was synthesized for the first time by the present inventors.

(Problems to be Solved by the Invention) The present inventors have discovered that the novel tribenzylamine derivative according to the present invention is useful as an intermediate for many organic compounds, and that it itself has tyrosine kinase inhibitory activity and ultraviolet light/absorbing activity. They discovered that it has an antibacterial effect and completed the present invention.

(First Means and Effects for Solving the Problems) The novel compound according to the present invention is represented by the following general formula (1).

(In the formula, R1 and R2 represent the same or different hydrates or C1 to C3 alkyl groups, and R3 and R4 are the same.) The compound represented by the formula (1) according to the present invention is a salt with a base or an acid. The salt of the compound according to the present invention includes any salt that can be formed from the compound of the present invention and a base or an acid.Specifically,
Examples of salts with bases include (1) metal salts, especially salts with alkali metals, alkaline earth metals, and aluminum; (2)
ammonium salts, (3) amine salts, especially methylamine,
Ethylamine, diethylamine, triethylamine, pyrrolidine.

piperidine, morpholine, hexamethyleneimine.

There are salts with aniline, pyridine, etc., and as salts with acids,
(1) Inorganic salts, especially hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid.

(2) Organic acids, especially carboxylic acids such as formic acid, acetic acid, propionic acid, succinic acid, oxalic acid, tartaric acid, maleic acid, lactic acid, benzoic acid, anthranilic acid, and salicylic acid, p-toluenesulfone acid.

There are salts with sulfonic acids such as methanesulfonic acid, and amino acids such as glycine, methionine, and lysine.

These salts can be used as tyrosine kinase inhibitors, ultraviolet absorbers,
When used as an antibacterial agent, one should choose one that is physiologically acceptable.

Typical examples of compounds according to the present invention are shown in Table 1.

Examples of methods for synthesizing the compound represented by formula (1) of the present invention include the following. For example, (where R1
, R2, R8, R4 are the same as above), the compound represented by H. Zimmer et al. [Journal of Organic Chemistry (J, Org.

Chem, ), 24.23 (1959): Journal of Heterocyclic Chemistry (J.

f engineering et-Ch5rrr, )p 3 m '171
(1965) -1 etc., general formula (2) (wherein R5 and R6 are the same or different hydrogens or simultaneously double compounds are condensed without catalyst or with acid or base as catalyst) Examples of the acid used as a catalyst include protonic acids such as sulfuric acid, benzenesulfonic acid* p F-luenesulfonic acid, and Lewis acids such as trifluoroheptaboron. Possible bases include ammonia,
piperidine.

Pyrrolidine, diethylamine, triethylamine.

Organic bases such as monoethanolamine, morpholine, pyridine, aniline, 1,3-diazabicycloC3,4,0)undec-7-ene; ammonium acetate.

Contains piperidinium acetate, etc.! 9. 'll Amine salts; Organic acid alkali metal salts such as sodium acetate and potassium acetate; Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; Alkali metal amides such as lithium diisopropylamide; Sodium methylate and sodium ethylate alkali metal alcoholades such as; and alkali metal hydrides such as sodium hydride and potassium hydride.

The compound represented by (R1, R2, R8, R4 are the same as above) is one of the aldehyde represented by general formula (2) (R5, R6 is the same as above) and the ylide represented by general formula (3). (or by reacting two types of compounds at the same time).

This synthesis method uses the so-called Witteigh reaction, but in addition to the compound represented by the general formula (3), ylides derived from trialkylphosphines and triarylarsines can also be used as the ylide to be reacted with the aldehyde. It can be used similarly.

(3) -1 Among the compounds represented by the formula (1),
The compound represented by the general formula (wherein R8, R9 are the same or different hydrogens, each represents a C, to C3 alkyl group, and RIO represents a group to be removed) is the compound represented by the preceding item (1), Formula (5) obtained by methods such as (2) (wherein, R11 and R12 represent the same or different hydrogen or a C1 to C3 alkyl group, and R13 is
It can be synthesized by reacting a compound represented by 'L group) with benzylamine.

(R't R2# R8# R' C) The compound represented by the above formula (6) is represented by the general formula (6) (wherein, B14 represents a C1 to C3 alkyl group, and R
It can be synthesized by reacting a compound represented by (representing a group represented by 15) with benzylamine and formaldehyde. This synthesis method uses the so-called Mannich reaction,
Examples of formaldehyde include formalin solution and paraformaldehyde.

The tribenzylamine derivative represented by the general formula (1) and its salt according to the present invention are tyrosine kinase inhibitors,
It is effective as an ultraviolet absorber and an antibacterial agent.

Due to its tyrosine kinase inhibitory activity, it can be expected to be used as an anti-asthmatic agent, an anti-inflammatory agent, an anti-cancer agent, an anti-carcinogenic agent, an agent for preventing cancer metastasis, a nerve agent, etc.

The tyrosine kinase inhibitory effect of the compound of the present invention is
, Carpenter or S. Cohen et al.'s Tyrosine Kinase Activity Measurement Method [The Journal of
Chemistry in Biology (J, Biol.

Ohem, ), 254.4884 (1979);
Journal of Biological Chemistry (J
, Biol, Chem, ), 257.1523 (
1982)) as a reference.

Human cancer cell-derived established strain A-481 was treated with fetal bovine serum 10% streptomycin (50 μg/ml) and penicillin G (
5 (l basic unit/ml) and kanamycin (50μ (//
The cells were cultured at 37°C under 5% 002 conditions in Dulbecco's modified Eagle medium [Nippon Pharmaceutical ■] containing 1 sl).

The obtained cells were treated according to the method of Cohen or Graham et al. to obtain a membrane preparation containing the epidermal growth factor receptor-tyrosine kinase complex (hereinafter abbreviated as membrane preparation).

This membrane preparation was used for the following measurements without solubilizing it.

N-2-hydroxyethylpiperazino-N'-2-
Ethanesulfonic acid buffer (20mM, pH 7,4),
Mn012 (1mM L bovine serum albumin (7,5μg
), membrane preparation (10 μf protein as a sample dissolved in dimethyl sulfoxide) was added, and after incubation for 5 minutes at 0 °C, epidermal growth factor (hereinafter abbreviated as EGF) (100 ny) was added and incubated at 0 °C. (r-,P)ATP (3
00QC! i/mmol, 0.1 μCi),
The final volume was 70 μl, and after further incubation at O”C for 15 minutes, 50 μl of the reaction solution was impregnated onto Whatman 3MMP paper, and immediately 10% trichloroacetic acid-10 mM
The sodium pyrophosphate aqueous solution reaction was stopped. The filter paper was thoroughly washed with the same wave, then washed with ethanol, dried, and the radioactivity remaining on the filter paper was measured using a liquid scintillation counter, and this value was designated as A. At the same time, as controls, a reaction without the addition of EGF, a reaction without the addition of the sample, and a reaction without the addition of EGF and the sample were performed, and the same measurements were performed.

C2 and D.

The tyrosine kinase inhibition rate was determined by the following formula.

Table 2 shows the tyrosine kinase inhibitory effects of the compounds according to the present invention. This result shows that the compound according to the present invention strongly inhibits tyrosine kinase. Note that the compound numbers correspond to those in Table 1.

In addition, the compound of the present invention has an ultraviolet absorbing action, and this action prevents solar erythema (commonly referred to as sunburn) in living organisms, and is effective against organic polymer materials (e.g. plastics,
It is expected to be used as an ultraviolet absorber for the purpose of preventing the deterioration of materials (rubber, paint, etc.) due to ultraviolet rays, and preventing discoloration of photographic images due to ultraviolet rays.

The ultraviolet absorption spectrum of the compound of the present invention was measured by a conventional method using methanol as a bath medium, and the molar extinction coefficient was calculated. The results are shown in Table 3.

This result shows that the compound according to the present invention absorbs ultraviolet rays quite strongly.

Table 3: The antibacterial activity of the compounds of the present invention against Durham-positive bacteria and Durham-negative bacteria was determined by a method according to the standard method of the Japanese Society of Chemotherapy (Journal of the Japanese Society of Chemotherapy; Vol. 29, p. 76 (1981)). It was measured.

In other words, for Durham-positive bacteria and Durham-negative bacteria,
Mueller-Hlnton brother (Di
After culturing in fco) medium, the number of bacteria was reduced to approximately 106/
The solution prepared in 1/1 was used as a bacterial solution for inoculation. Separately Muel
ler-Hlnton Agar (Difco)
This compound was added to the culture medium at 2-fold dilution to each concentration to prepare an agar plate medium, and this was streaked with a 2att probe using a nichrome wire loop (inner diameter IM@after) using the above-mentioned inoculation method. .

The agar plate plate smeared with each test bacterium as described above was heated at 37°.
The cells were cultured at C for 18 to 20 hours, and the growth of the test bacteria was determined.

The MIC value was determined as the lowest concentration at which the growth of the test bacteria was completely inhibited.

As a result, compound 2 was obtained from Bacillus subtilis (Bacillus subtilis).
I F O3134
Compound 3 has a MIC of 50 μy/ml.
us) I F 013867, Bacillus subtilis (Bacillus subtilis) I F
O8184, Staphyocoticus aureus (5ta
phylococcus aureus ) IFO12
732, respectively, M I O6, 25 μg/shoulder l
Hereinafter, 25μDa/shoulderl, 25μDa/1xls and Compound 5 are Klebsiella pneumoniae (Klebsiella pneumoniae).
la pneumoniae) I FO3512, the compound according to the present invention was found to be useful against Durham-positive bacteria and Durham-negative bacteria.

Acutely toxic ICR male mice (body weight 23 to 26 years) were used, with 6 mice per group. Compounds (1) to (5) were suspended in a 2.5% gum arabic bath solution containing 0.2% Tween 80 and administered orally at a rate of 0.1 me/10 da body weight.

Two weeks after administration, we observed symptoms of stiffness and -5 administration, determined the number of deaths/tested cases, and determined that the 50% lethal dose was LD5°C! ! /kq
) was estimated. As a result, compounds (1) to (5) of the present invention were obtained.
), no deaths were observed even after 9 administrations to 50011F//, and the LD50 of compounds (1) to (5) was 500 mq/k.
It was estimated that the toxicity was higher than q, and it was found to be of low toxicity.

Preparation and Dosage As the tyrosine kinase inhibitor or antibacterial agent according to the present invention, any of the formulations administered by intraoral administration, intragut administration, or parenteral administration can be selected. Specific formulations include tablets, capsules, granules, syrups, herbal medicines, ointments, injections, and the like.

The carrier for the formulation of the antibacterial agent or tyrosine kinase inhibitor according to the present invention may be an organic or inorganic solid or liquid carrier suitable for oral, rectal or other parenteral administration.
Usually an inert pharmaceutical carrier material is used. Specifically, for example, crystalline cellulose, gelatin, lactose, starch,
Magnesium stearate, talc, vegetable and animal fats and oils, gums, polyalkylene gellicols.

The ratio of the antibacterial agent or tyrosine kinase inhibitor of the invention to the carrier in the formulation can vary between 0.2 and 100%. Antimicrobial agents or tyrosine kinase inhibitors useful in the present invention may also include compatible antimicrobial agents or tyrosine kinase inhibitors and other pharmaceutical agents. In this case, it goes without saying that the antibacterial agent or tyrosine kinase inhibitor of the present invention does not need to be the main ingredient in the preparation.

The antibacterial agent or tyrosine kinase inhibitor according to the present invention is
It is administered at a dose that achieves the desired effect per dose without any side effects. The specific value should be determined by a doctor, but in general, it is 11,011 per day for an adult.
It will usually be administered at a dosage of about t to 10 da, preferably about 20 r4 to 5 da. The antibacterial agent or tyrosine kinase inhibitor of the present invention can be administered as a pharmaceutical preparation containing 1M9 to 5f, preferably 3M9 to 1f, as an active ingredient.

(Example) Next, the present invention will be specifically explained with reference to production examples of the compounds of the present invention, but these Examples are not intended to limit the present invention.

Example 1 Synthesis of Compound 1 5.5'-(((phenylmethyl)imino]bis(methylene)]]bis-3-ethoxy4-hydroxybenzaldehyde 1.35F), α-cyanoacetamide (0
, 5 da], and a catalytic amount of piperidine in benzene ('1
0 ml)-acetic acid (0.5 t) in a mixed solvent, and while dehydrating using a Digi-Stark type water separator,
Heat at reflux for an hour. Cold immersion, reaction solution in chloroform 15
Dilute with 0.0ml and wash with water. After drying the orange layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. When the resulting residue was recrystallized from a benzene-acetone mixed solvent, the compound l
(1,621 yield 93%) was obtained as yellow needles.

Example 2 Synthesis of Compound 2 5.5'-(((phenylmethyl)imino)bis(methylene)]]bis-3-ethoxy4-hydroxybenzaldehyde 0.98i, 1-phenyl-3,5-pyrazolidinedione (0.7 g) and a catalytic amount of pyridine were added to a mixed solvent of benzene (70 #I/) and acetic acid (0.5 t) for 5 hours while dehydrating using a Dieg-Stark type water separator. Heating under reflux. Cooling, precipitated crystals were prepared, and recrystallization from ethanol yielded compound 2 (0,
94f, yield 60%) was obtained as reddish brown needles.

Example 3 Synthesis of Compound 8 5.5'-(((phenylmethyl)imino]bis(methylene)]]bis-3-nitoxy4-hydroxybenzaldehyde 8f), rhodanine C4,61), and a catalytic amount of piperidine. Benzene (200sr/)-acetic acid<
0.5 ytl) of a mixed solvent, and heated under reflux for 5 hours while dehydrating using a Digi-Stark type water separator. After cooling, the precipitated crystals were separated and recrystallized from a benzene-acetone mixed solvent to obtain compound 8<7.9f, yield 6.
6%) were obtained as yellow needles.

Example 4 Synthesis of compound 4 5.5'-((phenylmethylfimino]bis(methylene)]]bis-3-ethoxy4-hydroxybenzaldehyde 0.93f), oxindole (0,58
2), and a catalytic amount of piperidine in benzene C70rC
It is added to a mixed solvent of 70r acetic acid (0.5M?) and heated under reflux overnight while being dehydrated using a Digi-Stark type water separator. After cooling, the precipitated crystals were harvested and recrystallized from ethanol to obtain Compound 4 (0.8f, yield 22%) as pale yellow needle crystals.

Example 5 Preparation of Compound 5 Compound 3 (1 g) and benzylamine (065y) are added to ethanol (50 m/) and heated to reflux overnight.

Cool immersion and remove the solvent under reduced pressure. The resulting residue was subjected to silica gel column chromatography (CHCl3:MeOH=100:2
) and recrystallized from ethanol.
Compound 5 (0,23y, yield 18%) was obtained as yellow needles.

Claims (19)

[Claims] (1) Tribenzylamine derivatives represented by the following general formula (1) and salts thereof. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R^1 and R^2 represent the same or different hydrogens or alkyl groups of C_1 to C_3, and R^3, R
^4 are the same or different ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) The tribenzylamine derivative and its salt according to claim 1, wherein R^1 and R^2 are both ethyl groups. (3) The tribenzylamine derivative and its salt according to claim 1, wherein both R^3 and R^4 are ▲a numerical formula, a chemical formula, a table, etc.▼. (4) The tribenzylamine derivative and its salt according to claim 1, wherein both R^3 and R^4 are ▲a numerical formula, a chemical formula, a table, etc.▼. (5) The tribenzylamine derivative and its salt according to claim 1, wherein both R^3 and R^4 are ▲a numerical formula, a chemical formula, a table, etc.▼. (6) The tribenzylamine derivative and its salt according to claim 1, wherein both R^3 and R^4 are ▲a numerical formula, a chemical formula, a table, etc.▼. (7) The tribenzylamine derivative and its salt according to claim 1, wherein both R^3 and R^4 are ▲a numerical formula, a chemical formula, a table, etc.▼. (8) Claims 1, 2, or 3 expressed by the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
Tribenzylamine derivatives and salts thereof as described in 1. (9) Claims 1, 2, or 4 expressed by the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
Tribenzylamine derivatives and salts thereof as described in 1. (10) Claims 1, 2, or 5 expressed by the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
Tribenzylamine derivatives and salts thereof as described in 1. (11) Claims 1, 2, or 6 expressed by the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
Tribenzylamine derivatives and salts thereof as described in 1. (12) Claims 1, 2, or 7 expressed by the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
Tribenzylamine derivatives and salts thereof as described in 1. (13) A tyrosine kinase inhibitor containing a tribenzylamine derivative represented by the following general formula (1) or a physiologically acceptable salt thereof as an active ingredient. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R^1 and R^2 represent the same or different hydrogens or alkyl groups of C_1 to C_3, and R^3, R
^4 are the same or different ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (14) An ultraviolet absorber containing a tribenzylamine derivative represented by the following general formula (1) or a salt thereof as an active ingredient. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R^1 and R^2 represent the same or different hydrogens or alkyl groups of C_1 to C_3, and R^3, R
4 are the same or different ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (15) An antibacterial agent containing a tribenzylamine derivative represented by the following general formula (1) or a physiologically acceptable salt thereof as an active ingredient. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R^1 and R^2 represent the same or different hydrogens or alkyl groups of C_1 to C_3, and R^3, R
^4 are the same or different ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (16) General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) (In the formula, R^1 and R^2 represent the same or different hydrogens or alkyl groups of C_1 to C_3, and R^ 3.R
^4 are the same or different ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
A method for manufacturing a compound represented by the general formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) (In the formula, R^5 and R^6 represent the same or different hydrogens or C_1 to C_3 alkyl groups) and compounds ▲Mathematical formulas, chemical formulas There are , tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
Or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A method for producing tribenzylamine derivatives characterized by reacting one type of compound, or two types of compounds at the same time. (17) General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) (In the formula, R^1 and R^2 represent the same or different hydrogens or alkyl groups of C_1 to C_3, and R^ 3.R
^4 are the same or different ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
A method for manufacturing a compound represented by the general formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (2) (In the formula, R^5 and R^6 represent the same or different hydrogen or C_1 to C_3 alkyl groups) and the general formula (3) (Ar)_3-R^7(3) (In the formula, Ar is an aryl group, R^7 is ▲ mathematical formula, chemical formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. , or a method for producing a tribenzylamine derivative, characterized by reacting two types of compounds at the same time. (18) General formula (4) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (4) (In the formula, R^8 and R9 represent the same or different hydrogens or C_1 to C_3 alkyl groups, and R^10 is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ This is a method for producing a compound represented by the general formula (5) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (5) (In the formula, R^1^1 and R^1^2 represent the same or different hydrogen or an alkyl group of C_1 to C_3, and R
^1^3 is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
A method for producing a tribenzylamine derivative, which is characterized by reacting a compound represented by ▼ or ▲ representing a group represented by a mathematical formula, chemical formula, table, etc. with benzylamine. (19) General formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1) (In the formula, R^1 and R^2 represent the same or different hydrogens or alkyl groups of C_1 to C_3, and R^ 3.R
^4 are the same or different ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
A method for producing a compound represented by the general formula (6) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(6) (In the formula, R^1^4 represents an alkyl group of C_1 to C_3, and R^1^5 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
A method for producing a tribenzylamine derivative, which is characterized by reacting a compound represented by ▼ or ▲ representing a group represented by a mathematical formula, chemical formula, table, etc.) with benzylamine and formaldehyde.