• 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:
    Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives, such as l -N-[3-(2,3-dihydro-1-oxo-1H-inden-5-yl)-2-oxooxazolidin-5-ylmethyl]ace tamide, possess useful antibacterial activity.
    公开号:SU1616518A3
    申请号:SU884356653
    申请日:1988-10-06
    公开日:1990-12-23
    发明作者:Джефрей Уанг Чия-Лин；Арвид Вуонола Марк
    申请人:Е.И.Дюпон Де Немур Энд Компани (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a method for producing new chemical compounds, namely oxazolidinone-2 derivatives, which possess antibacterial action, and can be used in medicine.
    The aim of the invention is to provide a method for producing new oxazolidinone-2 derivatives, possessing higher antibacterial activity in a number of compounds of the indicated class.
    Example 1. Preparation of (1) - N-3- (2,3-dihydro-1-oxo-1H-inden-5yl) -: -oxooxazolidin-5-ylmethyl-acetamide.
    To a solution of chromium (VI) oxide (3.58 g, 35.8 mmol) in acetic acid, lot (35 ml) and water (8.75 ml) are added (l) (2,3-dihydro-1H- Incene
    cm
    5-yl) -2-oxooxazolidin-5-ylmethyl-acetamide (7 g, 25.5 mmol) in acetic acid (35 ml) and acetic anhydride (10.6 ml). The mixture is left under stirring at room temperature overnight and then extracted three times with methylene chloride after adding water. The combined organic layer was washed with a saturated aqueous solution of sodium bicarbonate, brine and dried (MgSO4). Removal of the solvent gives a crude product, after purification of which by express chromatography, a gpchuchuyu column is 2.55 g (35%) (1) (2,3-dihydr & 1-oc 0-1 H-inden-5-yl) -2-oxc ) oxol sol din-5-ylmethyl-acetamide as a white solid, so pl. 163 - 165 s.
    IR spectrum (СНС1,): 1759, 699. 1608
    NMR spectrum (SDSSC): 7.73 (d, 1H), 7.67 (s., 1H), 7.50 (d., 1K), 6.43 (ishrs, 1H), A, 83 (m ,, 1H), 4.13 (t, 1H), 3.88 (dd, 1H), 3.70 (t, 2H), 3.13 (t, 2H), 2, 70 (t., 2H), 2.03 (s., 3N).
    Mass spectrum m / Z: 288, 1116 (M),
    CisH.,
    288, 1 10;
    ).
    calculated for
    D / V -44 ° (from 1
    Example 2. Preparation of (1) -N-3- (2,3-dihydro-1-G1CHRHOXI-1H-inden-5-yl) -2-oxycroxazolidin-5-ylmethane J-acetamide.
    To a solution of (1) (2,3-dihydro-1-oxo-1H-inden-5-yl) -2-oxooxazolidin-5-ylmethyl-11 teramide ((1.5 g, 1.73 mmol) in ethanol (10 ml) and tetrahydrofuran (2 ml) was added sodium borohydride (265 mg, 6.94 mmol). The mixture was stirred at room temperature for 3 hours until peaKJjjin was stopped with 10% hydrochloric acid. Ethanol was removed, the residue diluted with 10% hydrochloric acid and extracted 3 times with hot chloroform. The combined chloroform layer was washed with brine and dried (). Removal of the solvent gave an incomplete product, after purification -chromatography of the column gives 385 mg (7 / 7o) (1) (2.3 dihydro-1-hydroxy-1H-inden-5-yl) -2-oxooxazolidin-5-ylmethyl-acetam1 in the form of a white solid, t mp 158-159 ° C.
    IR (Nujol): 3286, 1737,
    1653.

    five
    0
    five
    35
    40
    NMR spectrum (DMCO - d) S
    (br., 1H), 7.40 (s., (s., 2H), 5.22 (“ms.,
    8.27
    BUT, 7.33 1H), 5.02
    (tf.s.,) 1H), 4.70 (m, 1H), 4.10
    1H), 3.40 (m, 2.72 (m, 1H), (s., 3N), 1.77
    (t.
    1K), 3.73 (t.,
    2H), 2.90 (m, 1H),
    2.33 (m, 1H), 1.83 (m, 1H).
    45
    50
    Mass spectrum m / Z: 290, 1270 (M), accumulated for C, HigNiO, 290, 1267; about (-19 ° (, SKZON).
    Gamime 3. Preparation of (1) -N-G3- (1,2-dihydro-1 - (4-methyl-1-piperaziki; 1n; edno) -1H-inden-5-yl) -2-oxo-oxazolidic-5-ylmethyl-3-acetamide. A mixture of 1} -I- z- (2,3-digndro-1-oxo 1H-11-5-yl) -2-oxooxazopig; h-5-ylmethyl-acetamide (0.2 g, 0.69 g ) and 1-amyl-4-methylpiperazine, - (120 mg, 1.04 mm seam) in dioxane (5 # i), containing trifluoride etherate, and boron (0.05 ml) and molecular sieve 4 X, heated under reflux for half a day (left overnight). The solvent is removed, the residue is chromatographed, and PG is obtained 127 mg (48%) of the title compound, m.p. Higher than 200 ° C (decomposed). NMR spectrum (DMSO-dg) i: 8.27 (Lg.S., 1H), 7.67-7.50 (m., ZN), 4.73 (brs ., 1H), 4.13 (t, 1H), 3.77 (t, 14), 3.40 (m, 2H), 3.00 (m. 2H), 2.80 (m ., 6H), 2.46 (broad s. 4H), 2.18 (s., ZN), 1.83 (s., ZN).
    MS m / z: 385, 2107 (K), calculated for Cj H yNijOj, 385, 2114. Dosage forms. The antibacterial compounds according to the proposed method can be introduced by any means, ensuring that the active ingredient is in contact with the place of action of the antibacterial agent in the mammal and). They can be administered by any known means, suitable for use in combination with melikamment or as separate therapeutic agents, or in combination with other drugs. They may be administered alone, but are usually administered with a pharmaceutical carrier selected depending on the upcoming route of administration and established pharmaceutical practice.
    The dosage administered varies depending on factors such as the pharmacodynamic characteristics of the specific5
    which agent, method and route of administration; the age, health and weight of the recipient; the nature and extent of symptoms; the type of parallel treatment, the frequency of treatment and the desired effect. Typically, the daily dose of the active ingredient may be from 5 to 20 mg / kg body weight.
    If more potent compounds are used, the daily dose is 5–15 mg / kg, preferably 5–7.5 mg / kg, administered by fractional oral dosage 2–4 times a day or in a long-lasting medicine form. is effective in achieving the desired results. These drugs may also be injected parenterally.
    Preferred therapeutic levels should be achieved by oral administration of 5-2 ;; mg / kg given by fractional doses of 2-4 times a day. Dosage may be increased in severe or life-threatening infections.
    Dosage forms (compositors) suitable for internal administration contain about 1.0-500 mg of the active ingredient per unit. In these pharmaceutical compositions, the active ingredient is usually present in an amount of 0.5-95% by weight of the total weight of the composition.
    The active ingredient can be administered orally in solid dosage forms, such as capsules, tablets, or powders, or in dosage forms, such as elixirs, syrups, and suspensions. It may also be administered parenterally in sterile liquid dosage forms.
    Gelatin capsules contain the active ingredient and powdered carriers such as lactose, sucrose, mannitol, starch, cellulose derivatives, magnesium stearate, stearic acid, and the like. Similar diluents can be used to make compressed tablets. Both tablets and capsules can be prepared as permanently drug-releasing products to ensure continuous delivery of the drug into the body for several hours. Extruded tablets may be coated with sugar or film to mask all
    ten
    20
    B5186
    disagreeable taste and tabulation of tableTtcgg from exposure to atmospheric factors or enteric-coated in order to selectively decompose the dosage form in the gastrointestinal tract.
    Liquid dosage forms for oral administration may contain coloring and corrective substances for better patient perception.
    In general, water, suitable oil, saline; Hydrocarbide, aqueous dextrose 15 (glucose) and related sugar solutions and glycols, such as propylene glycol or polyethylene glycols, are suitable carriers for parenteral solutions. Solutions for parenteral administration preferably contain a water-soluble salt of the active ingredient, suitable stabilizing agents and, if necessary, buffering agents. Anti-oxidants such as sodium bisulfate, sodium sulfite, or ascorbic acid, either alone or in combination, are suitable stabilizing agents. Citric acid and the sodium salt of ethylenediaminetetraacetic acid are also used. In addition, parenteral formulations may also contain preservatives, such as chlorine-Thrfi, benzalkonium, methyl- or propyl-paraben, and chlorbutanol. Capsules
    A large number of individual capsules are prepared by zapstneniem standard, consisting of 2 parts of gelatin capsules, each of which contains, mg: powdered active ingredient 75; lactose 150; talc 24; magnesium stearate 6.
    Soft gelatin capsules. The mixture of active ingredient in soybean oil is prepared and injected using a piston pump into gelatin to obtain gelatin capsules containing 75 mg of the active ingredient. The capsules are washed and existed. Pills.
    A large number of tablets are prepared by conventional methods so that the dosage unit contains, mg: active ingredient 75; colloidal silica 0.2; magnesium stearate 5; microcrystalline cellulose 250; corn starch 11; lactose
    thirty
    five
    0
    five
    0
    five
    98.8. There may be 1 suitable coatings applied to enhance the taste or prolong the absorption and
    Injei 1 preplr you.
    A parenteral 1 cch composition suitable for administering an injection is prepared by mixing 1.5% by weight of the active ingredient in 10% by volume of propylene glycol and water. The solution is made isotonic with h.aoritic sodium and sterilized.
    Suspensions.
    Aqueous suspensions are prepared for oral administration so that every 5 ml contains, mg: finely dispersed active ingredients / 5; sodium carboxymethylcellulose 20G :; sodium benzoate 5; sorbitol solution according to pharmacopoeia CLIiA I g; vanillin 0,025 mp.
    The minimum inhibition of PP1E con- centrations in vitro during the multiplication of microorganisms in a liquid medium is given in Table. one .
    The compounds produced by the proposed method are biologically active against gramopaque eaicTepnA, including some 1) antibiotic-resistant strains of staphylococci and streptococci. These compounds are potentially useful for the treatment of bacterial infections in both humans and animals, including diseases of the respiratory, gastrointestinal, urogenital systems, blood, interstitial fluid and soft tissues.
    From Table 1 it follows that the compounds of formula (I) exhibit an antibacterial effect in vitro. Standard culture methods were used to test the sensitivity of bacteria growing aerobically using the Müller-Hinton thinning medium to determine 24-hour minimum inhibitory concentrations for the tested strains of Staphyrosococcus aureus and Escherichia coli.
    The activity of compounds in vivo against Staphy1ococcus aureus in acute lethal M1, Delhi in mice is summarized and presented in Table 2.
    The in vivo activity was determined in mice, which were injected intraperitoneally with cultures of infectious microorganisms diluted to obtain 100%
    0
    five
    0
    five
    0
    five
    0
    five
    of the controversial animals for 11 hours. Kul1) S. aureus Tour, used 1 tolonga for infection of twelve Dusts of bacteria / Tensusable bacteria (, density using 3% water mucous membrane) a pig secretion; the compounds were dissolved or suspended in a 0.25% aqueous method (Methocel®: hydroxypropylmethylcellulose .5 premium Dow's company) mpani) for use by individual or sterile fox; tilirovannogo water containing L% l. methylpacaphyphoxide for subcutaneous administration, Mypia received a dose after 1 h and 4 h after Agen. Deaths were registered daily during the seven days of the experiment after the incineration. The number of vokokivany in the treated group on the seventh day after infection was used in the calculations of the 50% effective dose, i.e. doses of the compound that is lai DiiuaeT 50% death rate.
    In Tables 1 and 2, for a comparative analysis of antifactic activity, the data on minimum inhibitory concentrations and ED are presented, for (1) (4- (1-oceanopropyl) -pepsyl) -2-oxo-5-oxazolidinmethyl-acetamide (compound 1) and (DNp- (4- (1-hydroxypropyl) -1 1henyl-2-oxo-5-oxazolidinmethyl-acetote fl da (compound Ie 2)) is close to B1x structure-1 analogue of the compounds according to the proposed method. Compound in example 1, it is more effective (}) effective than compound 1 in an in vivo test, and coupling in example 2 is more effective than compound 2 in an in vitro test, and in vivo.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining oxazolidinone-2 derivatives of formula
    Cho
    50
    ABOUT
    CH,
    3
    in the form of 1-isomers,
    rde R is a hydrogen atom; ;
    R, - r vdpoksigruppa or R, and together oxygen or a group
    Mm (Y-CHZ,
    Rj is C-C4 alkyl, characterized by a compound of formula
    by that
    About CH -NHC-Rj
    in the form of a 1-isomer,
    where R has the above values,
    exposed to oxide
    chromium (VI) in a mixture of acetic acid and acetic anhydride and cicl
    and R together
    the left product, where R forms oxygen, or, if necessary, it is treated with an alkali metal borohydride to obtain the desired product, where R is a hydrogen atom and Rjt is a hydroxy group or 1-amino-4-methyl piperazine is refluxed with obtaining the desired product, where R1 and R are together a group
    N-NQN-CH3
    -SIXShAS
    Table 1
     128
    32
    128
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US07/106,358|US4801600A|1987-10-09|1987-10-09|Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents|
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