• 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:
    This invention relates to indicators of redox reactions and can be used in medical diagnostics. The purpose of the invention is to increase the storage stability of the agent. The agent contains an imidazole derivative which is applied to a carrier. The stability of the funds up to 10 days (prototype - 3 days).
    公开号:SU1496644A3
    申请号:SU853871843
    申请日:1985-03-28
    公开日:1989-07-23
    发明作者:Денеке Ульферт；Гютляйн Вернер；Кур Манфред；Мердес Хартмут；Муравски Ханс-Рюдигер；Вилингер Ханс
    申请人:Берингер Маннхайм Гмбх (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to indicators of redox reactions, in particular, a means for determining the products of the reaction of hydrogen peroxide with peroxidase, which can be used in medical diagnostics.
    The purpose of the invention is to increase storage stability.
    This goal is achieved by the proposed means for the determination of the products of the reaction of hydrogen peroxide with a nepokci schaz containing an imidazole derivative of the general formula.
    2
    E
    ) r1
    AB,
    n
    where R is hydrogen, methyl, hydroxybutyl, tetrahydrofuranyl,
    Toch Leocca
    taledoly.
    (I)
    lt
    Kd, R are the same or different and mean xolidine, tetra-hydroquinoline, substituted by methyl or benzyl, or a residue
    where K is hydroxyl, amino, dimethylamino, amino- (di) -acetic acid, amino-ethanesulfonic acid, amino-ethanephosphonic acid, R and R are the same or different and mean hydrogen, methoxyl, tert-butsh1,
    moreover, R and R cannot simultaneously mean ylolidine or tetrahydroquinoline, substituted by methyl or benzyl, and at least one radical R means hydroxyl, or its
    four
    SB Oi
    about 4
    four;:
     ABOUT
    hydrochloride and additives from solid and liquid carriers in the following ratio of components, May. The imidazole derivative of the general formula (I) or its hydrochloride 0.01-1 Additive from solid and liquid carriers Elastic The proposed remedy is prepared by simply mixing the ingredients The imidazole derivatives of general formula (I) contained in the proposed remedy are new compounds . They are obtained by known methods, for example, by the fact that
    a) oi-diketone General formula
    00
    BP-C-C
    (AND),
    in which R - and R have the specified value, is subjected to condensation with an aldehyde of the general formula
    About CH-R
    (Iii)
    in which R has the indicated meaning and with ammonia in an acidic solution, or
    b) oi-ketoxime General formula
    B, ss
     P II JHOH about
    (Iv)
    in which R "and R have the indicated value,
    subjected to interaction with the aldehyde of the formula (II-I) and ammonia and the resulting compound of the formula
    Rz-n
    LC
    t o
    (V)
    subjected to recovery, or c) the acyl bromide of the general formula
    R,
    CO - CHRBr
    (Vi)
    in which R and R have the indicated meaning, they are reacted with an amidine of the general formula
    .and

    (Vii)
    in which R, has the indicated value, in an alkaline medium.
    The desired product is isolated in free form or as a salt.
    In the examples, the following imidazole derivatives Nr I-XXXI are used:
    2- (3,5-dimethoxy-4-hydroxyphenyl) -4- (5) - (4-dimethylamino-phenyl) -5- (4) -methyl- (1H) -imidazole hydrochloride,
    0 m.pl. 215-219 C (decomposition), 94. 680 nm (25,500);
    2- (4-hydroxyphenyl) -4- - (5) - (4-dimethylaminophenyl) -5- (4) -methyl- (1H) -azole imide hydrochloride, azol, m.p. 242 ° С (time 5LOEN), L;, lax 412 nm (, 1.860)
    2- (3,5-di-tert-butyl-4-hydroxy-1) -4- (5) - (4-dimethyl-aminophenyl) -5- (4) -methyl- (1H) -imidazole III hydrochloride, t. square 255 ° C (decomposition),
    0 nm (41.830);
    IV hydrochloride 2- (4-hydroxyphenyl) - -4- (5) - (3,5-dimethoxy CI-4-hydroxyphenyl) - -5- (4) -methyl- (1H) -imidazole, m.p. 326 ° C (decomposition), A d, aks 533 nm
    5 (e 6,400)
    2- (3,5-di-tert-butyl-4-hydroxyphenyl) -4- (5) - (3,5-dimethoxy-4-hydroxyphenyl) -5- (4) -methyl-V-hydrochloride (1H) - -imidazole, m.p. 296 C (decomposition), Khdlax 673 nm (6 29.800);
    2- (3,5-dimethoxy-4-oxyphen-yl) -4- (5) - (4-hydroxyphenyl) -5 (4) -methyl- (1H) -imidazole VI hydrochloride, m.p. 197-199 with (decomposition), And mdKS
    5,533 nm (g 6,400) i
    VII hydrochloride 2,4- (5) -di- (3,5-dimethoxy-4-hydroxyphenyl) -5- (4) -methyl- - (1H) -imidazole, so pl. 158 ° С (decomposition), „c x 590 nm (6 17.900);
    0 VIII hydrochloride 2- (4-d1shet IL-aminophenyl) -4- (5) - (4-hydroxyphenyl) -5- - (4) -methyl- (1H) -imidazole, t. Pl. 225-230 ° С (decomposition), А „dks 510 nm (6 to, 500) 5 IX hydrochloride 2- (4-dimethylaminophenyl) -4- (5) - (3,5-dimethoxy-4-hydroxy- phenyl) -5- (4) -methyl- (1H) -imidazole, so pl. 182-200 s (decomposition), 71 d, aKS 670 nm (b 10,800);
    2- (6-methyl-1,2,3,4-tetrahydroquinolino) -4- (5) - (3,5-dimethoxy-4-hydroxy-1) -5- (4) -methyl- - ( 1H) -imidazole, so pl. 190 C (decomposition), 7 “and not 700 nm (, 400);
    HI hydrochloride 2- (9-ylolidino) -4-) - (3,5-dimethoxy-4-oxyfensh1) - (4) -metsh1- (1H) -imidazole, so pl. 201 ° C (decomposition), X a 690 nm (at 25.399) i
    0
    five
    XII hydrochloride 2- (4-oxn-3-methoxy-diphenyl) -4- (5) - (4-hydroxyphen-1-l) -5- (4) - -methyl- (1H) -imidazole, m.p. 270 ° С (decomposition),, 502 nm (
     3,730) i
    XIII2- (3,5-di-tert-butyl-4-hydroxyphenyl) -4- (5) - (4-hydroxyphenyl) -5- (4) - -methyl- (1H) -imidazo l, t. P. 200-202 s (decomposition), L 486 nm (,
     6,700) i
    XIV2- (3,5-dimethoxy-4-hydroxyphenyl) -5- (4) -methyl- (1H) -imidazolyl-4- (5) - -phenyl-4-amino-H-ethanesulfonic acid), mp . 260 С (decomposition), Д дgКС
     615 nm (5 27,500) -,
    XV2- (3,5-dimethoxy-4-hydroxyphenyl) -5- (4) -methyl- (1H) -imidazolyl-4- (5) - - (phenyl-4-amino-N-ethanephosphonic acid), t .pl. 250 ° C (decomposition), Lmax 624 nm (25,600),
    XVI2- (3,5-dimethoxy-4-hydroxyphenyl) -5 (4) -methyl- (IO-imidazolyl-4- (5) - (phenyl-4-aminoacetic acid), mp. 124 ° C (decomposition), Am ks 620 nm (e 18.800);
    XVII2- (3,5-di-tert-butyl-4-hydroxyphenyl -) - 4- (5) - (4-aminophenyl) -5- (4) - -methyl- (1H) -imidazole, t. square 228-230 ° C, 576 nm (5 31,200);
    XVIII2- (3,5-di-tert-butyl-4-hydroxy-phenyl) -5- (4) -methyl- (1H) -imidazolyl-4- (5) -phenylaminoacetic acid, amorphous, X dd to c - 614 nm (39.900),
    XIX2- (3,5-di-tert-butyl-4-hydroxy-phenyl) -5- (4) -methyl- (1H) -imidazolyl-4- (5) -phenylamino-diacetic acid), mp. . 225 C (decomposition), Amaks 580 nm (31,700);
    XX2- (1-benzyl-1,2,3,4-tetrahydroquinolino) -4- (5) - (3,5-dimethoxy-4-oxyphenyl) -5- (4) -methyl- (1H) -imidazole, so pl. 190 ° C (decomposition), X ax 705 nm. (b 31,500);
    XXI-hydrochloride 2- (3,5-dimethoxy- -4-hydroxyphenyl) -4- (5) - (4-aminophenyl) - -5- (4) -methyl- (1H) -imidazole, m.p.
    250 ° С (decomposition), d, d1. 580 nm (6 18.900);
    XXII hydrochloride 2- (3,5-dimethoxy-4-oxyphenyl) -4- (5) - (4-amino-3-metoxyphenyl) -5- (4) -methyl- (1H) -imidazole, m.p. 2l8 ° C (decomposition), Amax 02 nm (6 15,400) j
    XXIII hydrochloride, 2- (4-aminophenyl) -4- (5) - (3,5-dimethoxy-4-oxyphenyl) - (1H) -imidazole, so pl. 285 - 290 ° Sdddd P 560 nm (24,500),
    . XXIV hydrochloride 2- (4-dimesh1-aminophenyl) -4- (5) - (3,5 dimethoxy-4149
    1496644
    -oxiphenyl) - (1H) -im1SCs gzola, so pl. 295-298 seconds ,, (, 626 nm (4.770); XXV hydrochloride from 2,4- (5) -bis- (4-dimethyl-shaminophenyl) - (1H) -imidazole.
    m.p. 233-235 С, А
     The cop
     764 nm (g
     9800);
    XXVI hydrochloride 2- (3,5-dimethoxy-4-hydroxyphenyl) -4- (5) - (4-dimeshtamno-phenyl) -5- (4) - (2-tetrahydrofuryl) - - (1H) - imidazole, so pl. 98/110 С (decomposition) (no clear melting point) Rf 0.36 (silica gel, eluent: chloroform / methanol in a ratio of 5: 1), 9v ax 680 nm, (6 16,700);
    2- (3,5-dimethoxy-4-hydroxyphenyl) -4- (5) - (4-dimethylaminophenyl) -5- (4- (4-hydroxybutyl) - (1H) 0-hydroxychloride, XXVII hydrochloride, t mp 210-212 ° C (decomposition), 7 max 640 nm (, 000);
    XXVIII hydrochloride salt of 2- (3,5-dimethoxy-4-hydroxyphenyl) -4- (5) - (4-dimethyl-amino-phenyl) -4- (5) -methyl- (1H) -imide 5 ash, m.p. 218-219 ° C (decomposition), / L max 680 nm (6 25,500),
    XXIXhydrochloride 2- (3,5-dimethoxy-4-hydroxyphenyl) -4- (5) - (4-dimethylamino-3-methoxy-phenyl-1) -5- (4) -methyl- (1H). - imidazole, so pl. 211 C (decomposition), X Mo.kc 417 nm (28,300);
    XXX2- (3,5-dimethoxy-4-hydroxyphenyl) - -5- (4) -methyl- (1H) -imidazolyl-4- (5) - - (phenyl-4-amino-H-monoethane-2-sulfo - acid) Rf 0.44 (silica gel, eluent: isopropanol / n-butyl ether / water in the ratio 5: 3: 2), o, 620 nm (29,100);
    XXXI2- (3,5-dimethoxy-4-hydroxyphenyl) -5- (4) -methyl- (1H) -im1-adazolyl-4- - (5) - (phenyl-4-amino-H-bis-ethane- 2- -sulfonic acid), Rf 0.28 (silica gel, eluent: isopropanol / simple n-butyl ether / water in a ratio of 5: 3: 2), ax 610 nm (8 28,400).
    Brackets in the names of compounds Nr I-XXXI, numbers 4 and 5, respectively, indicate the corresponding position of the substituent of the tautomeric form.
    Example 1. Filter paper is impregnated with an aqueous or methanol solution containing 0.01, 0.1 or 1.0 wt.% Of the imidazole derivative, dried and cut into pieces, one part of which is used to determine the products of hydrogen peroxide with peroxidase immediately, the second part - after storage at a temperature of 35 ° C and relative humidity.
    five
    0
    five
    0
    five
    50% of air for 3 days, and a third after storage under specified conditions for 10 days. To carry out the test, the paper impregnated with a solution of an imidazole derivative is moistened with a solution of 0.5 g of hydrogen peroxide and 0.1 g of peroxidation with 100 mP of water and after 5 minutes the color of the paper in% reflection at 550 nm is measured using a photometer compared to control paper ( ie paper not moistened with an aqueous solution of hydrogen peroxide and peroxidase).
    The results of the experiment are summarized in table 1
    Comparison of data table. 1 suggests that the proposed agent exhibits better storage stability, expressed in lower reflection losses.
    Example 2. Reactive film for detecting hydrogen peroxide.
    To a reactive film film (about 99.5 wt.%), Consisting of 18 g of a dispersion of a plastic copolymer of vinyl acetate and vinyl propionate, 1.38 g of alginate, 69 g of tris-citrate buffer with a pH of 7.5 (0.45 mol (l), 0.025 g of 1- (3-chlorophenyl) -polucarbacid, 0.025 g of MgK edtu 21CO, 0.05 g of triton X 100, 0.6 g of hexanol, and 200 copper ammonia peroxidase, 0.47 g (about 0.5 wt.%) 2- (3-dimethoxy-4-hydroxyphenyl) -4- - (5) - (4-dimethylaminophenes1) -5- (4) - -methyl- (1H) -imidazole hydrochloride (compound of formula I).
    This coating composition is applied to a transparent film with a wet film thickness of 200 Cm and dried. This half-layer thus is applied a second layer as an optically white background of the composition with a layer thickness of 200 cm and dried: 52 ml of 0.1 m triscitrate buffer with pH 7.0, 5.5 g of titanium dioxide: 2.7 g of diatomaceous soil, 0.4 g of alginate, 1.4 g of dispersion of plastic additives copolymer of vinyl acetate and vinyl propionate, as well as 0.2 g of Triton X 100.
    The swelling and suction film obtained in this way and the reactive film are processed for testing. To detect hydrogen peroxide, 30 | M 1 of the test solution is applied to the Dosing Zone. After 1 min
    five
    0
    five
    The gray valve is pressed, and after another 2 minutes the resulting color is measured by a diffuse reflection photometer. From the previously established reference curve, the peroxide hydrogen concentration data is read.
    In tab. 2 shows the data for the reference curve.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    Means for determining the reaction products of hydrogen peroxide with peroxidase, containing an imidazole derivative and an additive from solid and liquid carriers, characterized in that, in order to increase the storage stability, it contains a compound of general formula (I) as an imidazole derivative
    2N - N
    . .XlH
    where R is hydrogen, methyl, hydroxybutyl, tetrahydrofuranyl,
     AT
    R
    And R is the same or different.
    and mean lulolidine, tetrahydroquinoline, substituted by methyl or benzyl, or a residue
    0
    0
    five
    where RA is hydroxyl, amino group, methylamino group, amino- (di) -acetic acid, amino-ethanesulfonic acid, amino-ethanephosphonic acid, R and R e- are the same or different and
    mean hydrogen, methoxyl, t-butyl,
    moreover, R and R cannot simultaneously mean lulolidine or tetrahydroquinoline, substituted by methyl or benzyl, and at least one radical R means hydroxyl, or its hydrochloride in the following ratio, wt.%: Compound of formula (I) or its hydrochloride 0.01-1.0 Solid or liquid media Rest
    filter paper or a swellable, respectively suction reactive film is used as a solid carrier, and water or methanol is used as a liquid carrier.
    Table 1
    A - known compound 2,4-di- (4-dimethylamino-3,5-dimethoxyphenyl) -5- - (4-hydroxyphenyl) -imidazole
    B — the hydrochloride of the known compound Aj — the reflection cannot be measured because of the strong intrinsic color.
    P
    Hydrogen peroxide concentration, mg / l
    4.2
    7.3
    12.4
    18.4
    1496644.
    Table
    L 2
    Diffuse reflection,%
    53.0 40.3 35.0 19.8
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    法律状态:
    优先权:
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