• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    A sulfamoyl-substituted phenethylamine derivate represented by the general formula …<CHEM>… wherein R1 represents an amino group or a mono- or di-lower alkylamino group; R2 represents a hydroxyl group, a lower alkyl group, or a lower alkoxy group; R3 represents hydrogen, halogen, a lower alkyl group, a lower alkoxy group, a phenylthio group, or a phenylsulfinyl group; R4, R5, R6, R7, R8 and R9 are selected independently from hydrogen and lower alkyl groups; R10 represents hydrogen, a lower alkyl group, or a lower alkoxy group; and Y represents oxygen or a methylene group and is oxygen when R2 is a hydroxyl group; or a salt thereof. The compounds exhibit alpha -adrenergic blocking action and are useful as antihypertensive agents and for the treatment of congestive heart failure. In the preferred compounds according to the invention R3 is hydrogen or lower alkyl.
    公开号:SU1181540A3
    申请号:SU823379949
    申请日:1982-01-21
    公开日:1985-09-23
    发明作者:Имаи Казуо；Ниигата Кунихиро；Фудзикура Такаси；Хасимото Синати；Такенака Тоити
    申请人:Яманути Фармасьютикал Ко Лтд (Фирма)；
    IPC主号:
    专利说明:

    b). S02NH2
    O-CH-CHi N CH2CH20
    OSSN
    4.35 g (0.01 mol) of 5 {1-chloro-C2- (2-methoxyphenoxy) ethylamino-ethyl) -2-metshenbenzenesulfonamide hydrochloride are suspended in 50 MP of ethyl acetate, and then 50 cl are added to the prepared suspension with stirring 10% aqueous solution of sodium carbonate. After further vigorous stirring overnight, the reaction mixture is separated by decantation. After removing the inorganic material by passing the ethyl acetate layer thus passed through a silica gel column (50 mp silica gel), the reaction product is dried to dryness, resulting in a yield of 8.2 g (88%) of colorless resin-like 5- {2- 2-metoxyphenoxy-) ethylJ -aziridin-2-yl1-methylbenzenesulfonamide
    The resulting product is an amorphous material.
    Calculated,%: C 59.65, H 6.12, N 7.73.
    “No. ° Found, t: t 59.37, H 6.12,
    N 7.61.
    NMR spectrum (СДС1з), 1.74 and
    7
    1.95 (1H + 1H, d, N-CHg 2.43
    H
    V
    1 2.55 (ZN, S,
    sq.,
     /
    N
    -ethyl-aziperidin-2-yl-2-methylbenzenesulfonamide and after adding 1 g of concentrated to this solution
    hydroiodic acid mixture is stirred overnight. After completion of the reaction, the solvent is distilled off under reduced pressure, and the residue is washed three times with 30 ml of water, and then washed twice with 200 ml of diethyl ether and crystallized by the addition of ethyl acetate. The resulting crystals are separated by filtration, washed with water and dried to obtain 1.7 g of 4- {1-iodo-2-C2- (2-methoxy) -ethylamino j-ethyl-2-methylbenzenesulfonamide hydrochloride, m.p.
    155 ° C.
    Calculated,%: C 34.97, H 3.91, N4.53.
    S, H jN O SI-HI
    Found,%: C 35.07, H 3.98, N 4.39.
    NMR spectrum, f-: (ZN, s ..
    3.54 (2H, t., -CHj-N-); 4.30 (2H, t ,, -CH-0), 5.55 (1H, t., CH-1). PRI me R 2.
    CHZ-CH-CH WHCH CHr 0 OSNE
    2.5 g of 5- {1- 2- (2-methoxyphenoxy) etch1 aziridin-2-yl1-2-methylbenzenesulfonamide is dissolved in 50 ml of methanol and, after adding 1 g of thiophenol to the prepared solution and stirring the solution overnight at room temperature methanol is distilled off at its temperature. The residue is passed through a silica gel chromatography column, from which the product is eluted with a mixed solvent of 9 parts by volume. chloroform and 1 rpm, h.
    methanol to give 2.4 g of 5- {2- 2- (2-methoxyphenoxy) ethylamino-1-phenylethylethyl | -2-methylbenzenesulfonamide as a viscous oil-like product, representing
    is an amorphous material.
     Calculated,%: C 60.99, H 5.97, N 5.93.
    C24H28 "20452; Found: C 60.72, H 6.11, N 5.71. - NMR spectrum (SDS1e): 2.58 (3N, s., / OU-CH3 6.74 (3N, s., 0-CH3), 3.98 (2H, t.,), 4.35 ( 1H, t., CH-S). Example 3. 3 O) -CHCHCH2 HCHHCH O — S OCHZOCH, 2.5 5- {1-C2- (2-methoxyphenoxy) -ethyl-Jazyridin-2 is dissolved in 50 MP of methanol -yl -2-methylbenzenesulfonamide and, after adding the boron trifluoride-diethyl ether complex to the prigränted solution at room temperature, the reaction mixture is stirred overnight. Thereafter, methanol is distilled off under reduced pressure and the residue is passed through a chromatographic column with a snigel. The product is further eluted using a mixed solvent which contains 9 parts by volume, chloroform and 1 parts by volume. methanol, resulting in 1.5 g of colorless viscous oil-suitable material. The product is then crystallized by adding 5 ml of methanol-a and a few drops of an aqueous ammonia solution. The crystals are separated by filtration, washed with water and dried, resulting in 1.2 g of 5-1 methoxy -2- 2- (2-methoxyphenoxy) ethylamino } -Ensh1 y-2 methylbenzenesul fonamida, so pl. T50-152C. Calculated,%: C 57.85, H 6.64, N 7.10. Found,%: C 57.58, H 6.79, N 7.24. Nuclear Magnetic Resonance Spectrum (CfljOfl), ff 3.65 (ZN / OVCH3 2.98 (2H, t. OCHz, 3.80 (ZN, s .. 3.26 (ZN, s., - CH-GCHj), 4 , 10 (2H, t.,), 4.40 (1H,). Example 4. SOjWHj) - CH-CH TCHNSngSn0S-0OHCH3 in 2 ml of acetic acid is dissolved in 2 g of 5- {2- 2- (2- methoxyphenoxy) -3 tilamino -1-phenylthioethyl J-2-methylbenzenesulfonamide m after adding 0.5 ml of 30% hydrogen peroxide to the prepared solution, keeping the mixture at 50-60 seconds for 3 hours. After adding 100 ml of water to the mixture the reaction mixture is subjected to an extraction treatment with 200 ml of ethyl acetate. The ethyl acetate extract is washed with a 1% aqueous solution of sodium carbonate and ethyl acetate is then distilled off under reduced pressure. The residue is passed through a silica gel chromatography column, from which the product is eluted with a mixed solvent containing 9 parts by volume of chloroform and 1 part by volume of methanol, and the viscous oil thus obtained is recrystallized by addition of ethyl acetate. The resulting crystals are separated by filtration, resulting in 1.3 g of 5- {2- 2- (2-methoxyphenoxy) -etcpamino-D-1-phenylsulfinyl ethyl -2-methylbenzenesulfonamide, m.p. 139-14lc. Calculated,%: C 59.00, H 5.78, N 5.73. (H NjOjSa Found, T: C 58.91, H 5.74, N 5.72. The pharmacological activity is determined as follows. A. ui-adrenoblocking effect. In rats anesthetized with urethane and treated with pentolini, blood pressure is measured pressure Next, the effects of the test specimens were measured (by intravenous administration), causing opposition to the hypertensive reaction caused by exposure to phenylfrin (by intravenous injection at a dosage of 10 µg / kg live weight). The results obtained are tabulated.
    C-Adrenoceptor blocker E / Lv, mg / kg, with intravenous administration
    0.071
    0.18
    0,0085
    1.8
    0.061
    for0, 0091
    The clinical introduction into the body of compounds of the formula II is usually practiced by intravenous injection or orally in the form of free bases or acid addition salts (e.g., hydrochlorides, sulfates.
    maleates, acetates, furarates, lactates, citrates). Acceptable results are achieved when administered as a single dosage from 10 ng to 1 mg.
    the compound several times a day in the case of intravenous injection and 0.1-100 mg of the compound two to three times a day in the case of oral administration.
    Based on compounds of the formula II, preparations in the form of usual doses are prepared, for example, in the form of tablets, capsules, pills, solutions, and medicines for this purpose are prepared according to known methods using conventional medical excipients (carriers).
    The proposed method allows to obtain compounds of the formula II possessing only o6-adreno-blocking activity, which allows using them without limitation as antihypertensive agents and agents for treating congestive heart failure.
    权利要求:
    Claims (1)
    [1]
    A method of producing a sulfamoyl substituted phenethylamine derivative of the general formula
    Ry ^ -CH-C-NH-C-CB-Y-iQj
    Rj Rs Rt Rfl where Ry is an amino group,
    R 2 is a lower alkyl radical,
    R 3 is iodine, phenylsulfinyl group, lower alkoxy group, phenylthio group,
    R 4 -R s is hydrogen,
    Ry is hydrogen or a lower alkoxy group, y is an oxygen atom, and also an acid salt thereof, characterized in that the compound of the general formula
    SOaRi Its R 6 k. | 4 | υ / “V * R9 θ / he R5 R7 Re ο δ
    where R 1 , R 2 , R 4 , R 5 - R g have the indicated meanings, with a halogenating agent in an organic solvent medium to obtain a halogenated product, which is then subjected to treatment with an alkaline agent in an organic solvent medium to obtain a product which is reacted with iodine hydrogen or a lower alcohol in the presence of boron trifluoride or with thiophenyl in an organic solvent to obtain the target product and, if necessary, the corresponding corresponding feyailthiobenzoyl sulfamide oxidizes perki Sue of hydrogen in an organic solvent.
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    申请号 | 申请日 | 专利标题
    JP55014382A|JPS6252742B2|1980-02-08|1980-02-08|
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