• 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:
    Novel pyrazoloindazole derivatives of the formula I wherein R1 is a hydrogen atom, halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxyl group or benzyloxyl group; R2 is a hydrogen atom, a halogen atom, a lower alkyl group or phenyl group; and X6is a halide ion,a hydroxide ion, a methanesulfonate ion, a p-toluenesulfonate ion, a sulfate ion, a nitrate ion, a carbonate ion, an acetate ion, a benzoate ion or a salicylate ion, a process for preparing the derivatives, and a pharmaceutical composition containing the same are disclosed. The derivatives have good bronchodilating action for human without exhibiting substantially bad effects on the functioning of heart, and therefore, they are useful as a drug.
    公开号:SU991950A3
    申请号:SU802948754
    申请日:1980-07-15
    公开日:1983-01-23
    发明作者:Фуюмура Есио；Танака Садао；Матсунага Исао；Сираки Есиуики；Икеда Едо；Емасаки Тамотсу；Охва Есихиро；Хата Син-Иси；Синдо Минору；Сакаи Кацусиге
    申请人:Чугаи Сейяку Кабусики Кайся (Фирма)；
    IPC主号:
    专利说明:

    X-c I® or X-Bg® to another negative ion by treating the resulting compound with an ion exchange resin and isolating the desired product. Example 1 To a solution of 5-benzyloxyindaeol (30 g) in dimethyl form amide (150 ml) was added 50% sodium hydride (6.7 g), and the mixture was stirred at room temperature for 10 minutes. The solution was then added dropwise to 150 ml of dimethylformamide containing 1-bromo-3-chloropropane (30 g), while cooling with ice and after stirring at room temperature for 30 minutes, the mixture was extracted with benzene. The extract is washed with water, dried over anhydrous sodium sulfate, and distilled to remove the solvent used. The remainder of the xp was matched with a column of silica gel to give 16 g of 1- (3-chloropropyl) -5-benzyloxy II-indazole (mp. 65-66 ° C) and 1.5 g of 2- (3-chloropropyl) -5 -benzyloxyindazole (15 g), so pl. 97-98 ° C. The 1- (g-chloropropyl) -5-benzyloxyindazole (15 g) obtained in the previous step is heated to melt. It hardens when cooled. The solidified product is separated, suspended in acetone and separated by filtration to obtain 14.5 g of 2,3-yyhydro-7-benzyloxy-1H-pyrazolo (1,2-a} indazole chloride.) After recrystallization from isobutanol, the product has m. mp 166-168s. Elemental analysis: Calculated,%: C, 67.88; H, 5.70; N, 9.81; PE Found;,%: C, 67.73; H, 5.85; N 9.17. 2. 2- (3-Chloropropyl) -5-benzyloxyindazole (3.5 g), prepared as described in the first stage of Example 1, is treated in the same manner as the second stage of Example 1 to obtain 3 g of 2,3-dihydro-7-benzyloxy-1H -pyrazolo (1,2-a} indazolium chloride. The product is not detected any drops at the melting point, even after it is mixed with the product of example 1. The IR and NMR spectra of the product are the same as the product of example 1. Example 3. Aqueous solution (10 ml) of 2,3-dihydro -7-methyl-α-phenyl-1H-pyra zolo (1.2-3) iidazolium bromide (1 g) obtained in Example 4 is fed to a column filled with 30 g of Amberlite IRA-40I ion-exchange resin (C type), and elk) irate with distilled water (1 l). The eluate is concentrated to give 0.8 g of 2,3-dihydro-7-methyl-9-phenyl-1H-pyrazalo {l, 2-a) indazolychloride After recrystallization from isobutanol, the product has a mp. 178180 ° C. Elemental analysis. Calculated,%: C 69.50; H 6.18; N 9.45. C 7H 7N2CE-1 / 2H20 Found: C, 69.71; H 5.86; N 9.49. Using an ion exchange resin with another type of counter-ion, 2,3-dihydro-7-methyl-9-phenyl-1H-pyrazolo (1,2-a) indazolium methanesulfonate, sulfate, nitrate, carbonate, acetate, para-toluenesulfonate are obtained in the same way, benzon, salicylate or hydroxide. Using a procedure similar to the procedure of example 1, prepare the products shown in table 1, following the general formula: Table 1
    Continued table. one
    If - -2-3 i --- G52. or their mixture, where R and Rj have the indicated values / Y is a halogen atom, is subjected to cyclization, sparing the target product, or the benzyl group is removed by catalytic reduction in an organic 65 solvent medium, or with an x-C1® exchange
    79919508
    X-Bg®; On the other negative ion about- Sources of information,
    by processing the resulting compound ion-taken into account when examining with exchange resin and isolating the target one. England patent 1399651,
    go product. C 07 O 487/04, published 1975.
    权利要求:
    Claims (1)
    [1]
    Claim
    A method of obtaining derivatives of pyrazoloindazole of the General formula where R | - a hydrogen, chlorine or bromine atom, a hydroxyl group, methyl, hydroxymethyl, benzyloxy group;
    , Rj is a hydrogen atom, bromine, lower alkyl with the number of carbon * atoms 1-3 or phenyl, provided that Rjf and Rj cannot simultaneously be hydrogen;
    Χθ - chlorine, bromine, methanesulfonate, I-toluenesulfonate, carbonate, benzoate or salicylate ibn, except for the fact that the compound of the general formula
    CH 2 d% CH 2 Y or a mixture thereof, where R <and Rj have the indicated meanings /
    Y is a halogen atom, cyclized to isolate the desired product, or the benzyl group is removed by catalytic reduction in an organic solvent or by X-C1® or exchange
    X-Bf® to another negative ion by treating the resulting compound with an ion-exchange resin and isolating the desired product.
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    同族专利:
    公开号 | 公开日
    DE3061152D1|1982-12-30|
    HU178886B|1982-07-28|
    CA1151176A|1983-08-02|
    ZA804095B|1981-07-29|
    EP0023633A1|1981-02-11|
    JPS5615287A|1981-02-14|
    EP0023633B1|1982-11-24|
    DK304080A|1981-01-17|
    US4409234A|1983-10-11|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3825556A|1967-12-12|1974-07-23|Tenneco Chem|N1-indazoles|JPS57109787A|1980-12-26|1982-07-08|Chugai Pharmaceut Co Ltd|Pyrazoloindazole derivative|
    US4734429A|1987-01-27|1988-03-29|Merrell Dow Pharmaceuticals Inc.|Cycloalkane[1,2-c:4,3-c']dipyrazoles and their use as bronchodilators|
    US4751002A|1987-01-29|1988-06-14|Baker International Corporation|Cable supported rake arm thickener|
    GB8811299D0|1988-05-12|1988-06-15|Grayshan R|Indazole derivatives|
    GB8916290D0|1989-07-17|1989-08-31|Erba Carlo Spa|Heteroaryl-3-oxo-propanenitrile derivatives useful in stimulating myelopoiesis|
    YU54202A|2000-01-18|2006-01-16|Agouron Pharmaceuticals Inc.|Indazole compounds,pharmaceutical compositions,and methods for mediating or inhibiting cell proliferation|
    DE60234510D1|2001-04-16|2010-01-07|Eisai R&D Man Co Ltd|1H-INDAZONE COMPOUNDS THE JNK HEMMEN|
    US20040178288A1|2003-03-14|2004-09-16|Berger Thomas R.|Switching mechanism for a batch feed waste disposer|
    US7008953B2|2003-07-30|2006-03-07|Agouron Pharmaceuticals, Inc.|3, 5 Disubstituted indazole compounds, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation|
    NZ547689A|2003-11-19|2009-05-31|Signal Pharm Llc|Indazole compounds and methods of use thereof as protein kinase inhibitors|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP8931179A|JPS5615287A|1979-07-16|1979-07-16|Pyrazoloindazole derivative and its preparation|
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