• 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:
    The present invention provides compounds of the general formula: …<CHEM>… wherein… R<1> is an aryl, ar(lower)alkyl or pyridyl radical, each of which may be substituted by halogen, amino, lower alkyl, lower alkoxy or carboxy(lower)alkyl,… R<2> is a hydrogen or halogen atom,… R<3> is an amino, lower alkylamino, acylamino or nitro radical,… R<4> is a divalent radical of the general formula -CnH2n- in which n is an integer of from 1 to 7, and… A is oxy, thio, sulfinyl, sulfonyl or imino,… the derivatives of the carboxy group, and the pharmaceutically acceptable salts thereof. …<??>The present invention also provides processes for the preparation of these compounds, as well as pharmaceutical compositions containing them.
    公开号:SU1199197A3
    申请号:SU792802251
    申请日:1979-08-07
    公开日:1985-12-15
    发明作者:Уеда Икуо；Ктаура Есихико；Кониси Нобукие
    申请人:Фудзисава Фармасьютикал Ко,Лтд (Фирма)；
    IPC主号:
    专利说明:

    f The invention relates to organic chemistry, specifically to the preparation of new compounds of general formula R; - phenyl, mono- or disubstituted with chlorine or monosubstituted with fluorine or methyl; R is ethoxy or its pharmaceutically acceptable salts. The purpose of the invention is the creation of new derivatives of phenylacetic acid, which have anti-inflammatory and analgesic effects. Getting the initial products; Preparation I. Preparation of 2- 2-nitro-3- (2-fluorophenoxyphenyl acetic acid and ethyl ester. A mixture of ethyl 2- (2-nitro-3-chlorophenyl) acetate {10 g), 2-fluorophenol (5 , 8 g), anhydrous potassium carbonate (8.5 g) and copper oxide (1 g) are stirred for 5 hours at 130 ° C. Concentrated hydrochloric acid and water are added to the reaction mixture and then the mixture is extracted with benzene. . The extract was washed with water, dried with magnesium sulfate, and then evaporated under reduced pressure, resulting in an oily residue of 2- (2-nitro-3- (2-fluorophenoxy) phenyl) acetic acid, IR (kgg) cm: 1710, 1530, 1370, 1290. NMR (DAZO-a), ppm: 3.87 (2H, S 6.90-7.80 (7H, m). Ethanol and a small amount of concentrated sulfuric acid are added to the indicated product. and then the mixture is boiled under heating for 1 hour. The solvent is distilled off from the reaction mixture and water is added to the residue. The mixture is extracted with diethyl ether, the extract is washed with a 5% aqueous solution. The solution is hydroxide sodium and water, dried over magnesium sulfate and evaporated under reduced pressure. The residue is distilled under vacuum to give an oily residue of ethyl-3- (2-fluorophenoxy) phenyl acetate (6.5 g). 972 Bp. 175-185 ° С С / 0.7 mm Hg. IR (film, cm 1740, 1280. NMR (SCC) 5, ppm. 1.23 (ЗН, t, Hz), 3, 61 (2H, S); 4.08 (2H, g, Hz), 6.55-7.55 (7H, t). Preparation 2. Preparation of ethyl 2-2-nitro-3- (3-chlorophenoxy) phenyl adatata. A mixture of 2- (nitro-3-chlorophenyl) acetate (10 g), 3-chlorophenol (7.8 g), anhydrous potassium carbonate (8.5 g) and copper oxide (3 g) is treated similarly, resulting in May / l Nisty residue ethyl 2 - 2-nitro-3- (3-chlorophenoxy) phenyl acetate (4.6 g) oF (film): -1745, 1270. NMR (SCC, S, ppm) , 23 (3N, t, Hz); 3.62 (2H, S); 4.10 (2H, g, 1 7 Hz); 6.68-7.50 (7H, t). Preparation 3. Preparation 2 - 2-nitro-3- (2-chlorophenoxy) phenyl [acetic acid and its ethyl ester. C. mixture of ethyl 27 (2-nitro-3-chlorophenyl) acetate (JS g), 2-chlorophenol GP, 7 g ), anhydrous potassium carbonate (12.8 g) and copper oxide (5.5 g) are processed ayut similarly to afford 2- nitro-2-Z- (2-chlorophenoxy) phenyl acetic acid (4.6 g), m.p. 162-164c. A mixture of polzgchennogo in this way. the product, ethanol and a small amount of sulfurized acid, are treated as in the previous preparations, and an oily residue of ethyl 2-2-nitro-3- (2-chlorfeioxy) phenyl acetate (5 g) is obtained. W (film): 1740, 1270. NMR (ecu), 5 ppm: 1.31 (3N, t, Hz); 3.65 (2H, S); 4.10 (2H, g, Hz); 6.60-7.75 (7H, t). Preparation 4. Preparation of ethyl 2- 2-nitro-3 (3,5-dichlorophenoxy) phenyl | acetate, a mixture of ethyl 2- (2-nitro-3-chlorophenyl) -acetate (IO g), 3,5-dichlorfeiol (7 , 4 g), anhydrous potassium carbonate (8.5 g) and copper oxide (1 g) are treated in the same way, and an oily residue of the indicated compound (7.6 g) is obtained. W (film), cm: 1745, 1270. NMR (CC14), 5 ppm. 1.20 (3N, t, Hz); 3.65 &amp; H, S); 4.12 (2H, g, Hz); 6.55-7.50 (bN, t).
    31
    Preparation 5.
    Preparation of ethyl 2- 2-nitro-3- (o-tolyloxy) phenyl acetate.
    A mixture of o-cresol (4.9 g), ethyl 2- (2-nitro-3-chlorophenyl) acetate (10.0 g), potassium carbonate (8.5 g), and copper oxide (1 g) is treated as avalegically as a result receive specified connection (3.4 g).
    Bp 173-176 ° С 0.2-0.4 mmHg
    IR (film), 1741, 1530.
    NMR (CC} 4), ppm: 1.30 (3N, t, Hz), 2.25 (3H, S); 3.63 (2H, S); 4.17 (2H, g, 1 7 Hz); 6.577, 57 (7H, m).
    Obtaining the target product.
    Example 1: Preparation of ethyl 2-2-amino-3- (2-fluorophenoxy) phenyl acetate.
    A mixture of iron porous (b g), ammonium chloride (0.6 g) ethanol (40 ml) and water (20 ml) and ethyl 2 - 2-nitro-3 - 2-fluorophenoxy) phenyl acetate (6.5 g) in for 5 minutes at low boiling conditions, they are mixed, and then the mixture is stirred for 1.5 hours at the same temperature. The reaction mixture is filtered off with heating and the ethanol is distilled off from the filtrate under vacuum. To the rest. water is poured in and the mixture is extracted with dithyl ether. The extract was washed with water and dried with magnesium sulfate, and diethyl ether was distilled off under vacuum to give an oily residue of the indicated compound (5.7 g).
    W (film), cm: 3450, 3400, 1730, 1260.
    NMR (DM50-a), 5 ppm: 1.18 (3N, t, Hz), 3.67 (2H, S); 4.13 (2H, g, 1 7 Hz), 4.85 (2H, S); 6,507,60 (7H, m).
    Example 2. Preparation of ethyl 2- 2-amino-3 (3-chlorophenoxy) phenyl acetate.
    A mixture of iron powder (3.8 g), a1 n4oni chloride (0.4 g), ethanol (40 ml) and water (20 ml) and ethyl 2- 2-nitro-3- (3-chlorophenoxy) phenyl acetate (4 , 6 g) are treated as in Example 1, in the resultant an oily residue of the indicated compound (0.4 g) is obtained.
    IR (film), cm: 3450, 3400, 1730, 1230.
    Example 3. Preparation of ethyl 2- 2-amino-3- (2-chlorophenoxy) phenyl acetate.
    974
    A mixture of iron powder (4.2 g), ammonium chloride (o, 42 g), ethanol (60 ml) and water (30 ml) and ethyl 2- 2-nitro-3- (2-chlorophenoxy) phenyl acetate (5 g ) is processed as described in Example 1, and an oily residue of the said compound (4.3 g) is obtained.
    IR (film), cm: 3450, 3400, 1730.
    Example 4. Obtaining ethyl 2 - 2-amino-Z- (3,5-dichlorophenoxy) phenyl acetate.
    A mixture of iron powder (7 g), ammonium chloride (0.7 g), ethanol (80 ml) and water (40 ml) and ethyl 2 - 2-nitro-3- / 3, 5-dichlorophenoxy phenyl acetate (7.6 g a) is treated as in example 1, the result is a specified connection (6.9 g).
    IR (film): 3450, 3400, 1730.
    PRI me R 5. Preparation of ethyl -2 -2-amino-3- (o-tolyloxy) phenyl acetate.
    A mixture of iron powder (2.1 g), ammonium chloride (o, 21 g), ethanol (40 ml) and water (20 ml) and ethyl 2 2-nitro-3- (o-tolyloxy) phenyl acetate (3.4 g) is treated as in example 1 as a result of the indicated compound (3.1 g).
    IR (film), cm: 3470, 3400, 1730.
    NMR (SCC-D O); S, ppm: 1.27 (3N, t, 1 7 Hz), 2.27 (3H, S); 3.53 (2H, S); 4.12 (2H, q, 1 7 Hz); 6.437, 27 (7H, p).
    Example 6. A solution of ethyl 2- 2-nitro-3- (2-fluorophenoxy) phenyl acetate in methanol (50 ml) was added to a solution of potassium hydroxide (20 g) in methanol (50 ml) with stirring and cooling on ice, after the mixture was stirred at room temperature for 30 minutes. Water (700 ml) is added to the reaction mixture and the resulting aqueous solution is acidified with concentrated hydrochloric acid to pH 2.0. The precipitated crystals are filtered, washed with water and recrystallized from a mixture of ethyl acetate and n-hexane (1: 1), as a result 2- 2-nitro-3- (2-fluorophenoxy phenyl acetic acid (31.9 g) is obtained, mp. U4-146 ° C. 5 IR (Had, KBr): 1710, 1590 0530, 1500, 1460 , 1280. NMR (DM80-1); S, ppm: 3.80 (2H, S); 6.85-7.80 (7H, m). Example 7, 1. Mixture of ethyl 2-2 -nitro-3- (2-chloro-phenoxy-phenyl-acetate and sodium hydroxide in water boil for 5 hours with stirring. Reaction see cooled to room temperature and washed with diethyl ether. Diethyl ether is added to the solution and the mixture is adjusted to pH 4 with 5% sulfuric acid. The diethyl ether layer is separated, washed with water and dried with magnesium sulfate and then the solvent is evaporated at The residue is recrystallized from a mixture of benzene and n-hexane, and 2- 2-nitro-3- (2-chlorophenoxy) phenylJ acetic acid is obtained. The compound thus obtained is dissolved in a solution of sodium bicarbonate (537 mg) in water (50 ml) and filtered. The filtrate is lyophilized to give 2-2 cytro-3- (2-chlorophenoxy) phenyl 3 sodium acetate, 2. The 2- 2-nitro-3- (2-chlorophenoxy) phenyl sodium acetate thus obtained is subjected to catalytic reduction by Rane nickel, and 2-2-amino-3- (2-chlorophenoxy) phenyl acetate acetate W (KBr) is obtained, : 3350, 3200, 1570, NMR (DM80-a.), S, h, ppm: 3.38 (2H, S); 5, 10 G2N, wide S); 6.53-7.70 (7H, m), The following compounds were prepared in the same manner as in Example 7, Sodium 2-2-amino-3- (2-fluorophenoxy) phenyl acetate, t, mp, 123133 ° C. ItK (: nujol), cm: 3450, 3350, 1570. NMR (daZO-db), ppm: 3.34 (2H, s); 5.30 (2H, shir, s); 6.407, 45 (7H, m). Sodium 2- 2-amino-3- (W-chlorophene si) phenyl acetate, IR (Nujol), cm-: 3450, 3350, 1580, NMR (flMSO-dj), ppm: 3.39 (2H, with); 5.27 (2H, LSr, s.); 6,447, 40 (7H, m) -, 976 Sodium 2-2-amino-3- (3,5-dichlorophenoxy phenyl 1 acetate, mp: 184-191 ° C. IR (Nujol), cm: 3450, 3380, 3300, 1590, 1580, 1570. NMR (DM50-), ppm: 3.33 (2H, s); 5.47 (2H, brs); 6.437, 30 (6H, m ) .. Sodium 2-2-amino-3- (o-tolyloxy) phenyl acetate, mp 150 C, IR (nujol): 3600, 3340, 3180, 1570. NMR (flM80-db), h , ppm: 2.27 (AH, s); 2.23 (2H, s)} 5.50 (2H, broad singlet), 6.40-7.40 (.7H, m), Effect on acute inflammation. In each test group, ten male Hartley rats, 5 weeks old weighing approximately 350 g, are used. Hair is removed from the back of each test animal 24 hours before the test, hair is removed, three-dimensional tape small holes 9 mm in diameter are placed on the animal's skin without hair and then exposed to UV light from a UV lamp (500 W, manufactured by Zagelgard Hanovi Inc.) at a distance of 13 cm for 80 s. After 2 h, the degree of erythema is assessed using the following rating system: 1.0 - erit “and with a clearly defined border; 0.5 - erythema without clearly marked border; 0,0 - weak erythema. Drugs are considered effective, and when the sum of all three points is lower than 1.5, each dosage of the test compound is administered orally in the form of a suspension in 20 ml of a 0.5% aqueous solution of methyl cellosolve. Half of the test specimen is applied one hour before irradiation and the remainder immediately after irradiation. The results of the tests are shown in the table. Test compounds: 1) 2- (2-amino-5-phenoxyphenyl sodium acetate; 2) 2- (2-amino-3-chloro-6-phenoxyphenyl) sodium acetate; 3) 2- (2-amino-3-phenylthiophenyl) sodium acetate; 4) 2- (2-acetamido-3-phenoxyphenyl) acetic acid;
    71
    5) 2-2-amino-3-2-pyridyloxy) phenyl sodium acetate;
    6) 2- 2-nitro-3- (2 fluorophenoxy phenyl acetic acid;
    7) 2-2-amino-3- (2-chlorophenoxy) phenyl sodium acetate;
    8) 2-2-amino-3- (2-fluorophenoxy) phenyl sodium acetate;
    9) 2-2 amino-3- (o-tolyloxy) phenyl sodium acetate;
    10) 2-2-amino-3- (3-chlorophenoxy) phenyl sodium acetate.
    Comparative compounds.
    Anti-inflammatory, inhibitory effect on prostaglandin biosynthesis.
    In Spraque-Donoly rats, the stomachs were removed with an eeso of approximately 180 g after the animals were caged overnight. A strip of gastric bottom is suspended at an initial load of 0.6 g in a 10 ml bath containing Tyrode's solution.
    Arachidonic acid (l, 0 x) is used as a spasmogen.
    99197 8
    Certain doses of the test compound are added to the contents of the individual trays 15 minutes before adding arachidonic acid. 5 The arachidonic acid-induced contraction value of the sample is measured, and the dose-response curve is plotted. AU value for each test compound is given
    10 by dose-activity curve interpolation.
    Test compounds 1-4 - (comparative):
    1) 2- (2-amino-3-phenoxyphenyl) ac15 sodium tat;
    2) 2-2-amino-3-phenylthiophenyl sodium acetate;
    3) 2- (2-acetoamido-3-phenoxyphenyl) acetic acid;
    4) 2-2-amino-3- (2-pyridyloxy) phenyl sodium acetate;
    5) 2-2-amino-3- (2-chlorophenoxy) phenyl sodium acetate;
    6) 2-2-amino-3- (2-fluorophenoxy) phenyl sodium adatate; g
    25
    7) 2- | 2-amino-3- (o-tolylox1 enyl1 sodium acetate;
    c) 2-2-amino-3-3-chlorophenoxy) phenyl sodium acetate;
    9) 2-2-amino-3- (3, 5-dichlorophenok30 si) phenyl sodium acetate.
    Added results per ml / ml:
    ED
    us below
    GO 1
    3.8x10
    35 5.2x10
    .-S
    3 4 5 6 7 8 9
    4,0x10
    g
    4,0x10
    .-6
    1,3x10
    .b
    1.6x10
    , -6
    2.5x10
    , -6
    1,7x10
    .-6 0.16x10
    Analgesic effect.
    Male mice strain ddy weighing 24.0-32 g are used. Each test group consists of 10 animals. Pain syndrome is created by the intraperitoneal injection of 20 ml / kg 0, fe% acetic acid. The pain of each animal on the dish is from 3 to 13 minutes after the administration of acetic acid. 60 minutes before the introduction of acetic acid (Moral), a medicine is used. The frequency of pain syndrome in 10 min in treated animals is compared with the frequency in the control group. Control animals receive an inactive compound. Test compounds were suspended in 0.5% methylcellulose. The ED value is calculated according to the Litchfield-Wilcoxon method. The test substance administered orally, depending on the dose used, has an inhibitory effect on the pain syndrome caused by the action of acetic acid. Test compounds (1-3 comparative) g 1) 2- (2-amino-3-phenoxyphenyl sodium acetate; 2) isoprofen; 3) INDOMETACIN; 4) 2-2-amino-3- (2-chlorophenoxy) phenylJ sodium acetate. Test results, EDj-., Mg / kg: .199.0
    权利要求:
    Claims (1)
    [1]
    (54) (57) METHOD FOR PRODUCING Phenylalkane Acid Derivatives of General Formula 1 SOU-CH g -C0H g X where Rj is phenyl mono- or disubstituted with chlorine or monosubstituted with fluorine or methyl;
    R 2 is an ethoxy or a pharmaceutically acceptable salt residue, wherein the derivative of the general formula where R. and R have the indicated meanings, is reduced with Raney nickel or iron in the presence of ammonium chloride in an aqueous-alcoholic medium, followed by isolation of the products. .
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    DE1072998B|1960-01-14|Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius &. Brüning, Frankfurt/M|Process for the preparation of substituted diphenyl ethers|
    FR1657M|1961-01-14|1963-02-15|Merck Ag E|5-ALEOXY-OXINDOLES|
    FR1516142A|1967-01-24|1968-03-08|Rhone Poulenc Sa|New process for the preparation of phenothiazine derivatives|
    US3981905A|1970-03-16|1976-09-21|Boots Pure Drug Company Limited|2- propionic acids|
    JPS512358Y2|1971-05-08|1976-01-23|
    BE795159A|1972-02-08|1973-08-08|Thomae Gmbh Dr K|NEW BUTENDIIC ACIDS, SALTS AND DERIVATIVES OF THESE ACIDS AND METHODS FOR PREPARING THEM|
    CH569013A5|1972-07-21|1975-11-14|Hoffmann La Roche|
    US4006161A|1973-12-26|1977-02-01|Eli Lilly And Company|Thio-substituted 2-oxo-indolines|
    JPS511442A|1974-06-19|1976-01-08|Fujisawa Pharmaceutical Co| Fuenokishifuenirusakusanruino seizoho |
    JPS511441A|1974-06-19|1976-01-08|Fujisawa Pharmaceutical Co| Fuenokishifuenirusakusanjudotaino seizoho |
    JPS5487136A|1977-12-23|1979-07-11|Fujitsu Ltd|Coupler between channels|US4333951A|1977-11-15|1982-06-08|A. H. Robins Company, Inc.|2-Amino-6-biphenylacetic acids|
    US4477556A|1982-08-18|1984-10-16|E. I. Du Pont De Nemours And Company|Acidic o-nitroaromatics as photoinhibitors of polymerization in positive working films|
    JPS61206716A|1985-03-12|1986-09-13|Sato Hisao|Transport roll|
    US4911754A|1987-07-16|1990-03-27|American Cyanamid Company|Herbicidally active aryloxy saturated 5-membered benzo fused hetero-cyclic compounds|
    ES2058024B1|1992-11-10|1995-05-01|Menarini Lab|NEW ARILPROPIONIC DERIVATIVE, MANUFACTURING PROCEDURE OF THE SAME AND ITS USE AS AN ANALGESIC.|
    WO1994029291A1|1993-06-07|1994-12-22|Zeneca Limited|Aniline derivatives|
    AT448194T|2000-08-29|2009-11-15|Biocon Ltd|USE OF A PHARMACEUTICAL COMPOSITION COMPRISING A PARA-AMINOPHENYL ACIDIC ACID DERIVATIVE FOR THE TREATMENT OF INFLAMMATORY DISEASES OF THE MAGNETIC STRENGTH|
    US8048924B2|2001-08-29|2011-11-01|Biocon Limited|Methods and compositions employing 4-aminophenylacetic acid compounds|
    US7186745B2|2001-03-06|2007-03-06|Astrazeneca Ab|Indolone derivatives having vascular damaging activity|
    DK1773767T3|2004-07-07|2016-03-21|Biocon Ltd|Synthesis of azo bound in immune regulatory relations|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB7832609|1978-08-08|
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