JPS6353190B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to novel phenylacetamide derivatives having physiological effects useful as pharmaceuticals and their pharmacologically acceptable acid addition salts. More specifically, the present invention relates to the general formula (R ₁ in the formula is an alkyl group having 1 to 3 carbon atoms, X is an alkoxy group having 1 to 3 carbon atoms, and Y
is a hydrogen atom or an alkoxy group having 1 to 3 carbon atoms, and n is an integer of 0 to 2), and their pharmacologically acceptable acid addition salts. The phenylacetamide derivative of the present invention represented by the above general formula () is a new compound and significantly suppresses the writhing reaction that occurs when acetic acid is administered to mice. This shows that the phenylacetamide derivative of the present invention represented by the above general formula () has strong central depressing action and analgesic action, and is useful as a pharmaceutical. The phenylacetamide derivative of the present invention represented by the general formula () is represented by the general formula (Y and R ₁ in the formula have the same meanings as above)
Compounds represented by and general formula (X and n in the formula have the same meanings as above)
It can be produced by reacting phenylacetic acid represented by phenylacetic acid or a derivative thereof in the presence of a condensing agent. This production method is an amidation reaction that is known per se and can be easily carried out. That is, phenylacetic acid or a derivative thereof represented by the general formula () is dissolved in an inert organic solvent such as benzene, dioxane, toluene, tetrahydrofuran, chloroform, methylene chloride, etc., and then the compound of the general formula () and the like are dissolved. A molar amount to a slight excess of the condensing agent, such as phosphorus oxychloride, is added under ice cooling or stirring at room temperature, and then reacted at room temperature for 30 minutes to 1 hour, followed by equimole to 0.6 mole of the compound of general formula (). An amount of the compound represented by the general formula () is added under ice cooling or at room temperature. The reaction mixture is allowed to react at room temperature for 30 minutes to 1 hour, then heated to 50°C to 100°C for an additional 1 hour to 8 hours, the reaction solution is washed with an aqueous alkaline solution, and the organic layer is concentrated under reduced pressure. The desired product can be obtained by purifying the residue by vacuum distillation and activated alumina column chromatography. Furthermore, the phenylacetamide derivative represented by the general formula () of the present invention is the general formula ()
It can also be produced using reactive functional derivatives thereof in place of phenylacetic acid or its derivatives represented by. For example, a compound represented by the above general formula (), an equimolar to 5 molar amount of a base such as pyridine, triethylamine, etc., and an appropriate amount of 4-(N,N-dimethylamino)pyridine or 4-pyrrolidinopyridine as a catalyst. an inert organic solvent, such as benzene, dioxane,
In addition to toluene, xylene, tetrahydrofuran, chloroform, methylene chloride, etc., then a reactive functional derivative of phenyl acetic acid or its derivative represented by the general formula () in an equimolar to 3 molar amount as the compound of the general formula (). was added under stirring in ice-cooling or room temperature, and then allowed to react at room temperature for 30 minutes to 5 hours. The reaction solution was concentrated under reduced pressure. An aqueous alkali solution was added to the residue, extracted with ether, and the ether layer was removed under reduced pressure. The desired product can be obtained by concentrating and purifying the residue using vacuum distillation and activated alumina column chromatography. In this case, the reactive functional derivative of phenylacetic acid or its derivative represented by the general formula () is acid chloride,
Acid anhydrides, mixed acid anhydrides, esters, etc. can be used, and these can be easily produced according to conventional methods. For example, acid chloride can be produced by reacting a compound of general formula () with thionyl chloride. In this production method, the compound represented by the general formula () used as a raw material is a new compound, and the compound represented by the general formula Phenylethylamine or a derivative thereof represented by (Y in the formula has the same meaning as above) is reacted with chloroacetic acid chloride in water-dioxane in the presence of sodium bicarbonate, and then the resulting amide is reacted with alcohol- In the presence of potassium carbonate in water, the formula By reacting with an amine represented by the general formula After obtaining a compound represented by (Y in the formula has the same meaning as above), this compound is reacted with formic acid-formalin or an alkyl halide having 2 to 3 carbon atoms, and the product is hydrogenated in ether. It can be produced by reduction using lithium aluminum. In the present invention, these compounds include N-2-phenylethyl-N'-methyl-N'-tetrahydrofurfurylethylenediamine, N-2-phenylethyl-N'-ethyl-N'-tetrahydrofurfurylethylenediamine, N-2-phenylethyl-N'-ethyl-N'-tetrahydrofurfurylethylenediamine, -2-phenylethyl-N'-propyl-N'-tetrahydrofurfurylethylenediamine, N-2-(4-methoxyphenyl)ethyl-N'-methyl-N'-tetrahydrofurfurylethylenediamine, N-2- (4-methoxyphenyl)ethyl-N'-ethyl-N'-tetrahydrofurfurylethylenediamine, N-2-(4-
methoxyphenyl)ethyl-N'-propyl-
N'-tetrahydrofurfurylethylenediamine, N-2-(4-ethoxyphenyl)ethyl-
N'-Methyl-N'-tetrahydrofurfurylethylenediamine, N-2-(4-ethoxyphenyl)ethyl-N'-ethyl-N'-tetrahydrofurfurylethylenediamine, N-2-(4-ethoxyphenyl)ethyl-N'-ethyl-N'-tetrahydrofurfurylethylenediamine, enyl)ethyl-N'-propyl-N'-
Tetrahydrofurfurylethylenediamine, N
-2-(4-propoxyphenyl)ethyl-
N'-Methyl-N'-tetrahydrofurfurylethylenediamine, N-2-(4-propoxyphenyl)ethyl-N'-ethyl-N'-tetrahydrofurfurylethylenediamine, N-2-(4-
propoxyphenyl)ethyl-N'-propyl-
N′-tetrahydrofurfurylethylenediamine and the like can be used. In addition, phenylacetic acid or phenylacetic acid derivatives represented by the general formula () are known compounds and can be easily produced by methods described in the literature; examples thereof include phenylacetic acid, 2-, 3- or 4-methoxy Phenylacetic acid, 2-, 3- or 4-ethoxyphenylacetic acid, 2-, 3- or 4-propoxyphenylacetic acid, 2,3-, 2,4-, 2,5-,
2,6-,3,4- or 3,5-dimethoxyphenylacetic acid, 2,3-,2,4-,2,5-,
2,6-,3,4- or 3,5-diethoxyphenylacetic acid, 2,3-,2,4-,2,5-,
Examples include 2,6-, 3,4- or 3,5-dipropoxyphenylacetic acid. In the phenylacetamide derivative represented by the above general formula () of the present invention, the free form of the compound is an oily substance, and it can be dissolved in common organic solvents such as methanol, ethanol, chloroform, methylene chloride, ether, ethyl acetate, benzene, etc. It is soluble. These free-form compounds can be converted into acid addition salts according to conventional methods. For example, the free form of the phenylacetamide derivative represented by the general formula () can be dissolved in ether, and then an appropriate amount of hydrochloric acid gas is added to this solution to form the hydrochloride. Acid addition salts include hydrochloride,
Sulfates, sulfonates, benzoates, citrates, tartrates, succinates, etc., and these acid addition salts are colorless crystalline or glassy substances, and the corresponding free forms It has a strong central depressant effect and analgesic effect similar to the compound. The phenylacetamide derivative of the present invention represented by the general formula () is a new compound that has not been described in any literature, and has a strong central depression effect and analgesic effect, and is useful as a pharmaceutical. Reference examples and examples are shown below to further explain the present invention in detail. Note that the boiling points of the compounds in Reference Examples and Examples are uncorrected. Reference Example 1 59.5 g of 2-(4-methoxyphenyl)ethylamine hydrochloride and 120 g of sodium hydrogen carbonate were dissolved in a mixed solvent of 800 ml of dioxane and 1000 ml of water, and 60 g of chloroacetic acid chloride was added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. do. The reaction solution was concentrated under reduced pressure, water was added to the residue, and the crystals were collected by filtration. Crystals in chloroform-n
-Recrystallize from hexane to obtain 50.5 g of N-[2-(4-methoxyphenyl)ethyl]chloroacetamide.
get. 20.6 g of this product, 10.2 g of tetrahydrofurfurylamine, and 13.8 g of potassium carbonate were dissolved in a mixed solvent of 100 ml of ethanol and 50 ml of water, and heated under reflux for 6 hours. The reaction solution was concentrated under reduced pressure to give a residue of 10%
% aqueous sodium hydroxide solution and extracted with ether. After washing the ether layer with water and drying, the solvent was distilled off and N
-2-(4-methoxyphenyl)ethyl-α-
25.6 g of (tetrahydrofurfurylamino)acetamide are obtained. Add 20 ml of formic acid and 30 ml of 35% formalin aqueous solution to this, and heat at 100°C to 110°C for 5 hours. The reaction solution was concentrated under reduced pressure, a 10% aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted with ether.
After washing the ether layer with water and drying, the solvent was distilled off under reduced pressure and N
-2-(4-methoxyphenyl)ethyl-α-
[(N′-methyl-N′-tetrahydrofurfuryl)
Obtain 21.3 g of [amino]acetamide. 10g of lithium aluminum hydride in ether
Add N-2-(4-
An ether solution of 21.3 g of methoxyphenyl)ethyl-α-[(N'-methyl-N'-tetrahydrofurfuryl)amino]acetamide was added dropwise, stirred at room temperature for 1 hour, and then heated under reflux overnight. Cool the reaction solution, add an appropriate amount of 10% aqueous sodium hydroxide solution, separate the ether layer, dry it, and then concentrate. The residue was distilled under reduced pressure (204-207℃/3mmHg) and N-2-
(4-methoxyphenyl)ethyl-N'-methyl-
14.7 g of N'-tetrahydrofurfurylethylenediamine is obtained. (Colorless oily substance) Infrared absorption spectrum (liquid film) νNH: 3300 cm ^-1 Elemental analysis value C ₁₇ H ₂₈ N ₂ O ₂ C% H% N% Theoretical value 69.82 9.65 9.58 Actual value 70.01 9.66 9.54 Nuclear magnetic resonance spectrum ( CDCl ₃ ) δ: 1.3~2.1 (m, 4H), 2.23~3.0 (m, 17H),
3.77 (s, 3H), 6.8 (d, 2H), 7.1 (d,
2H) The following compounds can be produced by similar operations.

[Table] Example 1 N-2-phenylethyl-N'-methyl-N'-
Tetrahydrofurfuryl ethylenediamine 7.9
g, 10 ml of triethylamine, 190 mg of 4-(N,N-dimethylamino)pyridine and 100 ml of methylene chloride.
Dissolve in and stir under ice cooling. A solution of 6.5 g of 4-methoxyphenylacetic acid chloride in 20 ml of methylene chloride was added dropwise and stirred at room temperature for 1 hour. Add 10% aqueous sodium hydroxide solution to the reaction solution and separate the methylene chloride layer. After washing with water, drying and concentrating under reduced pressure, the residue was distilled under reduced pressure (243-245°C/0.2 mmHg) and converted into N-2-phenylethyl-N-[2-(N'-methyl-N'-tetrahydrofurfuryl). 9 g of aminoethyl]-4-methoxyphenylacetamide is obtained. Infrared absorption spectrum (liquid film) νCO: 1635 cm ^-1 Elemental analysis value C ₂₅ H ₃₄ N ₂ O ₃ C% H% N% Theoretical value 73.14 8.35 6.82 Actual value 73.09 8.15 6.89 Nuclear magnetic resonance spectrum (CDCl ₃ ) δ: 1.2-4.15 (m, 22H), 3.77 (s, 3H), 6.7
~7.4) (m, 9H) Example 2 5 g of 3,4-dimethoxyphenylacetic acid is dissolved in 20 ml of benzene, 4 g of phosphorus oxychloride is added dropwise thereto, and the mixture is stirred at room temperature for 30 minutes. A solution of 4.6 g of N-2-phenylethyl-N'-methyl-N'-tetrahydrofurfurylethylenediamine in 20 ml of benzene was added dropwise under ice cooling, stirred at room temperature for 30 minutes, and heated under reflux for an additional 3 hours. After cooling, add 10% aqueous sodium hydroxide solution, separate the benzene layer, wash with water, and dry. The solvent was distilled off under reduced pressure, and the residue was purified by activated alumina column chromatography (benzene-ethyl acetate) to give N-2-phenylethyl-N-[2-N'-methyl-N] as a pale yellow oil. 5.3 g of '-tetrahydrofurfuryl)aminoethyl]-3,4-dimethoxyphenylacetamide is obtained. Infrared absorption spectrum (liquid film) νCO: 1640 cm ^-1 Elemental analysis value C ₂₆ H ₃₆ N ₂ O ₄ C% H% N% Theoretical value 70.88 8.24 6.36 Actual value 70.97 8.22 6.21 Nuclear magnetic resonance spectrum (CDCl ₃ ) δ: 1.30~4.0 (m, 22H), 3.85 (s, 3H), 3.88
(s, 3H), 6.6-7.4 (m, 8H) Example 3 N-2-(4-methoxyphenyl)ethyl-
N'-methyl-N'-tetrahydrofurfurylethylenediamine 2.9 g, triethylamine 5 ml,
Dissolve 50 mg of 4-(N,N-dimethylamino)pyridine in 50 ml of methylene chloride, stir under ice cooling, and add 2 g of phenyl acetate chloride and 10 ml of methylene chloride to this solution.
The solution was added dropwise and stirred for 1 hour under ice cooling and then for 2 hours at room temperature. The solvent was distilled off from the reaction solution under reduced pressure, and 10% aqueous sodium hydroxide solution was added to the residue, extracted with ether, washed with water, and dried.The solvent was distilled off under reduced pressure, and the residue was subjected to activated alumina column chromatography. (benzene-ethyl acetate) and N-2-
(4-methoxyphenyl)ethyl-N-[2-
(N′-methyl-N′-tetrahydrofurfuryl)
Obtain 2.8 g of [aminoethyl]phenylacetamide (pale yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1640 cm ^-1 Elemental analysis value C ₂₅ H ₃₄ N ₂ O ₃ C% H% N% Theoretical value 73.14 8.35 6.82 Actual value 73.22 8.31 6.91 Nuclear magnetic resonance spectrum (CDCl ₃ ) δ: 1.1 to 4.3 (m, 22H), 3.87 (s, 3H), 6.65
~7.65 (m, 9H) Example 4 N-2-phenylethyl-N'-methyl-N'-
Tetrahydrofurfurylethylenediamine 4.5
Dissolve 5 ml of triethylamine and 50 mg of 4-(N,N-dimethylamino)pyridine in 50 ml of methylene chloride, stir under ice cooling, and add 4.3 g of 2.5-dimethoxyphenylacetic acid chloride to 10 ml of methylene chloride.
The solution was added dropwise and stirred for 1 hour under ice-cooling, and further stirred for 1 hour at room temperature. The solvent of the reaction mixture was distilled off under reduced pressure, and a 10% aqueous sodium hydroxide solution was added to the residue, followed by extraction with ether. After washing the ether layer with water and drying, the solvent was distilled off under reduced pressure, and the residue was purified by activated alumina column chromatography (benzene-ethyl acetate) to obtain N-2-phenylethyl-N-[2-
(N′-methyl-N′-tetrahydrofurfuryl)
4.3 g of aminoethyl]-2,5-dimethoxyphenylacetamide is obtained. (Pale yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1640 cm ^-1 Elemental analysis value C ₂₆ H ₃₆ N ₂ O ₄ C% H% N% Theoretical value 70.88 8.24 6.36 Actual value 70.69 8.33 6.32 Nuclear magnetic resonance spectrum (CDCl ₃ ) δ: 1.2 to 4.3 (m, 22H), 3.75 (s, s, 3H,
3H), 6.6-7.45 (m, 8H) Example 5 N-2-phenylethyl-N'-methyl-N'-
Tetrahydrofurfurylethylenediamine 5
Dissolve 5 ml of triethylamine, 50 mg of 4-(N,N-dimethylamino)pyridine in 50 ml of methylene chloride, stir under ice cooling, and add 4.2 g of 3-methoxyphenylacetic acid chloride and 20 ml of methylene chloride to this solution.
The solution was added dropwise and stirred for 1 hour under ice cooling and for 2 hours at room temperature. The reaction solution was concentrated under reduced pressure, and a 10% aqueous sodium hydroxide solution was added to the residue, extracted with ether, washed with water, and dried. Ether was distilled off under reduced pressure, and the residue was purified by activated alumina column chromatography (benzene-ethyl acetate) to obtain N-2-phenylethyl-N-[2-(N'-methyl-N'-tetrahydro). 5.3 g of furfuryl) aminoethyl]-3-methoxyphenylacetamide are obtained. (Pale yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1635 cm ^-1 Elemental analysis value C ₂₅ H ₃₄ N ₂ O ₃ C% H% N% Theoretical value 73.14 8.35 6.82 Actual value 73.22 8.29 6.81 Nuclear magnetic resonance spectrum ( _CDCl3 ) δ: 1.1-4.2 (m, 22H), 3.77 (s, 3H), 6.45
~7.45 (m, 9H) Example 6 N-2-(4-methoxyphenyl)ethyl-
N'-methyl-N'-tetrahydrofurfurylethylenediamine 5g, triethylamine 5ml, 4
- Dissolve 50 mg of (N,N-dimethylamino)pyridine in 50 ml of methylene chloride, and add 5.5 g of 2-methoxyphenyl acetic acid chloride and 10 g of methylene chloride to this solution.
ml solution was added dropwise, and the mixture was stirred for 1 hour under ice-cooling, and further stirred for 1 hour at room temperature. Concentrate the reaction solution under reduced pressure to give a residue of 10%.
Add aqueous sodium hydroxide solution, extract with ether, wash the ether layer with water, and dry. The solvent was distilled off under reduced pressure, and the residue was purified by activated alumina column chromatography (benzene-ethyl acetate).
-(4-methoxyphenyl)ethyl-N-[2-
(N′-methyl-N′-tetrahydrofurfuryl)
5.1 g of aminoethyl]-2-methoxyphenylacetamide is obtained. (Pale yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1635 cm ^-1 Elemental analysis value C ₂₆ H ₃₆ N ₂ O ₄ C% H% N% Theoretical value 70.88 8.24 6.36 Actual value 70.89 8.27 6.38 Nuclear magnetic resonance spectrum (CDCl ₃ ) δ: 1.0 to 4.2 (m, 22H), 3.77 (s, s, 3H,
3H), 6.6-7.4 (m, 8H) Example 7 N-2-phenylethyl-N'-methyl-N'-
Tetrahydrofurfurylethylenediamine 5
g, 5 ml of triethylamine, and 30 mg of 4-(N,N-dimethylamino)pyridine were dissolved in 50 ml of methylene chloride, stirred under ice cooling, and a solution of 5 g of phenylacetic acid chloride in 10 ml of methylene chloride was added dropwise to this solution under ice cooling for 1 hour. The mixture is further stirred at room temperature for 2 hours. Methylene chloride was distilled off under reduced pressure, and a 10% aqueous sodium hydroxide solution was added to the residue, followed by extraction with ether. After washing the ether layer with water and drying, the ether is distilled off.
The residue was purified by activated alumina column chromatography (benzene-ethyl acetate) to give N-2-phenylethyl-N-[2-(N'-methyl-N'-
Obtain 3.7 g of (tetrahydrofurfuryl) aminoethyl]phenylacetamide (yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1635 cm ^-1 Elemental analysis value C ₂₄ H ₃₂ N ₂ O ₂ as C% H% N% Theoretical value 75.75 8.48 7.36 Actual value 75.82 8.52 7.41 Nuclear magnetic resonance spectrum ( _CDCl3 ) δ: 1.1-4.15 (m, 22H), 6.6-7.7 (m, 10H) Example 8 N-2-(4-methoxyphenyl )ethyl-
N'-methyl-N'-tetrahydrofurfurylethylenediamine 5g, triethylamine 5ml, 4
- Dissolve 30 mg of (N,N-dimethylamino)pyridine in 50 ml of methylene chloride, stir under ice cooling, and add 7.8 g of 4-n-propoxyphenylacetic acid chloride to this solution.
A 20 ml methylene chloride solution of g was added dropwise to the mixture, and the mixture was stirred for 1 hour under ice cooling and further stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, a 10% aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted with ether. After washing the ether layer with water and drying, the ether was distilled off and the residue was purified by activated alumina column chromatography (benzene-ethyl acetate) to obtain N-2-(4-methoxyphenyl)ethyl-N-[ 2-(N′-methyl-N′-
Tetrahydrofurfuryl) aminoethyl]-4
- Obtain 5.8 g of n-propoxyphenylacetamide. (Yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1635 cm ^-1 Elemental analysis value C ₂₆ H ₄₀ N ₂ O ₄ C% H% N% Theoretical value 71.76 8.60 5.98 Actual value 71.82 8.80 5.77 Nuclear magnetic resonance spectrum ( CDCl ₃ ) δ: 1.0 (t, 3H), 1.2 to 4.3 (m, 26H), 3.73
(s, 3H), 6.55-7.25 (m, 8H) Example 9 N-2-phenylethyl-N'-n-propyl-N'-tetrahydrofurfurylethylenediamine 5g, triethylamine 5ml, 4-(N,N
-dimethylamino)pyridine 50mg in methylene chloride
Dissolve in 50 ml and stir under ice-cooling. To this solution, a solution of 8 g of phenyl acetic chloride in 20 ml of methylene chloride is added dropwise, and the mixture is stirred for 30 minutes under ice-cooling and then at room temperature for 1.5 hours.
The reaction solution is concentrated under reduced pressure, 10% aqueous sodium hydroxide solution is added to the residue and extracted with ether. The ether layer is washed with water and dried, and then the ether is distilled off under reduced pressure. The residue was purified by activated alumina column chromatography (benzene-ethyl acetate) and N
-2-Phenylethyl-N-[2-(N'-n-
5.5 g of propyl-N'-tetrahydrofurfuryl)aminoethylphenylacetamide is obtained.
(Yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1640cm ^-1 Elemental analysis value C ₂₆ H ₃₆ N ₂ O ₂ C% H% N% Theoretical value 76.43 8.88 6.86 Actual value 76.61 9.03 6.90 Nuclear magnetic resonance spectrum ( CDCl ₃ ) δ: 0.85 (t, 3H), 1.1~4.2 (m, 23H), 6.7~
7.7 (m, 10H) Example 10 Dissolve 5 g of N-2-phenylethyl-N'-n-propyl-N'-tetrahydrofurfurylethylenediamine and 50 mg of 4-(N,N-dimethylamino)pyridine in 50 ml of methylene chloride. A solution of 9.7 g of 4-methoxyphenyl acetic acid chloride in 15 ml of methylene chloride was added dropwise to this solution, and the mixture was stirred for 1 hour under ice cooling, and then for 2 hours at room temperature. The reaction solution was concentrated under reduced pressure, and a 10% aqueous sodium hydroxide solution was added to the residue, followed by extraction with ether. After washing the ether layer with water and drying, the ether is distilled off. The residue was purified by activated alumina column chromatography (benzene-ethyl acetate) to give N-2-phenylethyl-N-[2-(N'-n-propyl-N'-
Tetrahydrofurfuryl) aminoethyl]-4
- Obtain 4.5 g of methoxyphenylacetamide.
(Yellow oily substance) Infrared absorption spectrum (liquid film) νCO: 1635 cm ^-1 Elemental analysis value C ₂₇ H ₃₈ N ₂ O ₃ C% H% N% Theoretical value 73.94 8.73 6.39 Actual value 74.03 8.81 6.33 Nuclear magnetic resonance spectrum ( CDCl ₃ ) δ: 0.85 (t, 3H), 1.1~4.2 (m, 23H), 3.75
(s, 3H), 6.5-7.5 (m, 9H) Example 11 N-2-phenylethyl-N-[2-(N'-
Dissolve 1 g of methyl-N'-tetrahydrofurfuryl)aminoethyl]-4-methoxyphenylacetamide in 20 ml of ether, and blow an appropriate amount of hydrochloric acid gas into this solution. The reaction solution was concentrated under reduced pressure to obtain a colorless and transparent glassy substance N-2-phenylethyl-N-[2-(N'-methyl-N'-tetrahydrofurfuryl)aminoethyl]-4-methoxyphenyl. 1 g of acetamide hydrochloride is obtained.

Claims (1)

[Claims] 1. General formula (R ₁ in the formula is an alkyl group having 1 to 3 carbon atoms, X is an alkoxy group having 1 to 3 carbon atoms, and Y
is a hydrogen atom or an alkoxy group having 1 to 3 carbon atoms, and n is an integer of 0 to 2), and pharmacologically acceptable salts thereof. 2 formulas The phenylacetamide derivative according to claim 1, which is represented by: 3 formulas The phenylacetamide derivative according to claim 1, which is represented by: 4 formula The phenylacetamide derivative according to claim 1, which is represented by: 5 formula The phenylacetamide derivative according to claim 1, which is represented by: 6 formula The phenylacetamide derivative according to claim 1, which is represented by: 7 formula The phenylacetamide derivative according to claim 1, which is represented by: 8 formula The phenylacetamide derivative according to claim 1, which is represented by: 9 formula The phenylacetamide derivative according to claim 1, which is represented by: 10 formula The phenylacetamide derivative according to claim 1, which is represented by: 11 formula The phenylacetamide derivative according to claim 1, which is represented by: