• 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 invention relates to novel quinoxaline-2-yl ethenyl ketones, their preparation and compositions containing them. The novel quinoxaline-2-yl ethenyl ketones of the general formula I <IMAGE> (I) wherein R1 represents an aryl group or a heterocyclic group comprising one or more nitrogen and/or oxygen and/or sulfur atoms wherein both the aryl and heterocyclic groups are optionally substituted by one or more identical or different substituents, R2 stands for a hydrogen atom or a C1-4 alkyl group, are prepared by reacting an acetylquinoxaline derivative of the general formula II <IMAGE> (II) wherein R2 is as stated above, with an aldehyde of the general formula III R1-CHO (III) wherein R1 is as stated above. The novel compounds of the general formula I possess valuable antibacterial effect and promote the growth of animals. Thus, the novel compounds can be incorporated in animal feeds.
    公开号:SU1192621A3
    申请号:SU813292503
    申请日:1981-06-03
    公开日:1985-11-15
    发明作者:Бенко Пал；Божинг Даниель；Гундель Янош；Мадьяр Карой
    申请人:Эдьт Дьердьсерведьесети Дьяр (Инопредприятие)；
    IPC主号:
    专利说明:

    one
    This invention relates to a process for producing new substituted quinoxes. ii-2-yl-ethenyl ketones that exhibit antibacterial activity and have the ability to increase the weight of animals, and may find application in medicine and in animal husbandry.
    The purpose of the invention is the preparation of new substituted quinoxalin-2-yl-ethenyl ketonor with improved antibacterial activity.
    Example 1. Preparation of {2-methyl-quinoxalin-2-yl-1, 4-dioxide) - (phenyl) ethenyl ketone.
    21.8 g (0.1 mol) of 3-methyl-2-acetyl-quinoxaline-1, 4-dioxide was heated for 20 hours at 50 ° C with 10.6 g (0.1 mol) of benzaldehyde in 250 ml. isopropanol in the presence of 0.85. (0.01 mol) piperidine. After cooling the mixture, the precipitated product from -, fillet three ali.
    It was obtained 23.9 g (78% of Otheory) (3-methyl-quinoxalin-2-yl-1, 4-dioxide) - (phenyl) ethenyl ketone with T.Sh1. 187-188 ° C.
    Example 2. Obtaining (3-methyl-quinoxalin-2-sh1-1, 4-dioxide-quinoxalin-2-yl-1, 4 dioxide) ethenyl ketone.
    3-Metsh1-2-acetyl-quinoxaline-1,4-dioxide is heated with 2-formyl-quinoxaline-1, 4-dioxide, as described in example 1, for 8 hours. In this case, (3-metsh-1-quinoxaline- 2-yl-1, 4-dioxide) - (quinoxalin-2-yl-1, 4-dioxide-ethynyl) ketone with so pl. 340 C.
    Example 3. Preparation of (3-methyl-quinoxalin-2-yl-1, 4-dioxo1) - (para-methoxyphenip) ethenyl ketone.
    H-Methyl-2-acetyl-quinoxaline-1, 4-dioxide is heated with parametoxybenzaldehyde, as described in Average daily weight gain of the experimental group Average daily weight gain of the control group
    The amount absorbed during the test was divided by the gain obtained during the experiments and the resulting quotient was compared with the quotient, which was calculated similarly for the control group. The result is expressed as a percentage.
    26212
    measure 1. This gives 3-methyl-quinoxalin-2-yl-1, 4-dioxide - (para-methoxy-feiyl-ethenyl) ketone, m.p. 186 187 ° C. The yield is 86% of
    5 theories.
    New compounds of general formula (IJ. Can be used for the prevention and treatment of various bacterial (1 infections either locally or systematically. These compounds are effective against various gram-positive and gram-negative bacteria, in particular against the following types of bacteria: Entero 5 bacteriaceae, for example, Pseudomonas aeruginosa, Microcouaceae, for example, Staphylococcus aureus table. l).
    The minimum inhibitory concentration of the various compounds of formula (l) against the bacterial strains found is between 0.5 and 100 µg / ml.
    The weight-gaining efficacy of the new Compounds was confirmed by the results
    25 tatami experiences. Pigs were used as experimental animals. Six animals were selected for each dose, which were divided into groups and each experiment was repeated two
    30 times. The feed used for feeding pigs contained 50 mg / kg of quinoxalin-2-yl-ethenyl ketone, described by the general formula II.
    The animals were fed under identical conditions and all groups of animals consumed the same amount of feed of identical composition. The control group received feed in the same amount, but without quinoxalin-2-yl-ethenyl ketone.
    Weight gain was recorded daily and the average daily weight gain was calculated using the following formula:
    X 100.
    showed each amount of feed causing a weight gain of 1 kg and compared with the results obtained for the 55 control group.
    Obtained according to example 2, the compound gave the results shown in Table 2.
    From the above results it can be seen that when using new compounds of formula (D) for feeding animals, a significantly higher weight gain is observed than for animals in the control group. At the same time, this weight gain is achieved with a significantly smaller amount of feed, which indicates its best absorption.
    A significant advantage of new quinoxaline-2-sh1-ztenyl ketones is that they are very quickly removed from the body of animals. This means that the duration of care for livestock when using new compounds is significantly shorter.
    The predated compounds are so low toxic to domestic animals that they can practically be considered non-toxic.
    LDjo compounds of example 1 4600 mg / kg P.O.
     Example 2 compounds 3200 mg / kg P.O.
    LDcg of Example 3 15000 mg / kg P.O.
    The antibacterial activity of the known methyl- (quinoxalin-2-yl-methylene) -carbazate-i, 4-dioxide (l) compound and the proposed compounds was compared.
    The antibacterial activity of the compounds was confirmed by the values of MUS - minimal inhibitory concentration (Table 1).
    Table 1
    Continued. one
    five
    0
    25
    25
    100
    100
    Table 2
    e mean
    1 kg per day weight per percentage overweight
     (3-Methyl-quinox-LIN-2-Sh1-1,4-dioxid) - (quinoxalin-2-yl-1, 4-dioxide) -ethenyl122, 6
    80.9 ketone
    Control group without test100
    100 my connections
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING SUBSTITUTED CHINOXALIN-2-IL-1,4-DIOXIDE-ETHENYLKETOIOV of formula I a ^ CO-Cti ’^ CH-R,
    Oh where is R | - a phenyl group substituted by an alkoxy group with 1-4 carbon atoms, or quinoxaline-1,4-dioxide;
    R 2 “is an alkyl group with 1-4 carbon atoms, characterized in that the compound of the formula where Rg has the indicated meanings, is reacted with an aldehyde of the general formula
    R ( - CHO where R, has the indicated meanings, in the presence of piperidine.
    >
    类似技术:
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    CH507292A|1971-05-15|Cephalosporin cpds.:- R1, R2=H, monovalent hydrocarbon or C-bound heterocyclic gp. opt. substd. or R1 + R2 = divalent hydrocarbon gp. opt. interrupted by hetero
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    同族专利:
    公开号 | 公开日
    NL8102659A|1982-01-04|
    JPS5714582A|1982-01-25|
    BR8103476A|1982-02-24|
    DE3121977A1|1982-04-15|
    AR229796A1|1983-11-30|
    ES8203353A1|1982-04-01|
    DK241381A|1981-12-04|
    CA1165319A|1984-04-10|
    PL137173B1|1986-05-31|
    GB2076819A|1981-12-09|
    GR75691B|1984-08-02|
    AU7125681A|1982-08-26|
    BE889049A|1981-12-02|
    CH651299A5|1985-09-13|
    SE8103471L|1981-12-04|
    FR2483415A1|1981-12-04|
    ES502682A0|1982-04-01|
    IT1167782B|1987-05-13|
    US4373101A|1983-02-08|
    IT8122083D0|1981-06-02|
    CS228509B2|1984-05-14|
    GB2076819B|1983-11-02|
    FR2483415B1|1985-06-28|
    PL231452A1|1982-03-15|
    DK148979B|1985-12-09|
    HU184292B|1984-07-30|
    FI811703L|1981-12-04|
    AU550919B2|1986-04-10|
    YU139481A|1983-09-30|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3818007A|1970-03-18|1974-06-18|Pfizer|Hydroxyalkyl esters of quinoxaline-di-n-oxide-2-carboxylic acid|
    CH575213A5|1972-09-05|1976-05-14|Ciba Geigy Ag|
    US4097668A|1974-11-21|1978-06-27|Egyt Gyogyszervegyeszeti Gyar|2- -hydrazono-formyl!-quinoxaline-1,4-dioxide|
    US4038392A|1975-10-14|1977-07-26|Pfizer Inc.|3- quinoxaline-1,4-dioxides|
    DE2631520A1|1976-07-14|1978-01-19|Bayer Ag|-Methyl -amino-methylcarbamoyl quinoxaline -dioxides - for use as antibacterial agents|
    US4303657A|1979-05-21|1981-12-01|International Minerals & Chemical Corp.|Nitrohydroxyalkyl-substituted quinoxaxiline dioxides and alkanoic acid esters thereof|DE3340931A1|1983-11-11|1985-05-23|Bayer Ag, 5090 Leverkusen|DUST-FREE CHINOXALIN-1,4-DI-N-OXIDE|
    AU623026B2|1989-07-12|1992-04-30|Help Enterprises|Mail boxes|
    JP2963299B2|1993-03-31|1999-10-18|三菱電機株式会社|Peripheral device of programmable controller and internal information setting method|
    CN102408384B|2011-10-25|2014-03-05|湖南科技大学|Improved synthesis method of quinocetone|
    CN102329272B|2011-11-01|2013-09-11|荆州市新元生物科技有限公司|Method for preparing quinocetone|
    CN103420928A|2012-12-17|2013-12-04|华中农业大学|Preparation method of tritium and deuterium labeled quinocetone|
    CN103145631B|2013-03-18|2015-08-19|广州英赛特生物技术有限公司|Germ resistance quinoxaline-1, the derivative of 4-dioxide and the application in animal productiong thereof|
    CN104447587B|2013-03-18|2017-02-08|广州英赛特生物技术有限公司|Application of quinoxaline-1,4-dioxide in animal production|
    CN103664807A|2013-12-02|2014-03-26|河北美荷药业有限公司|3-methyl-2--quinoxaline-1,4-dioxide, and preparation method and application thereof|
    CN104672155B|2013-12-03|2017-11-07|中牧实业股份有限公司黄冈动物药品厂|A kind of synthetic method for improving quinocetone|
    CN103724284A|2013-12-13|2014-04-16|河北美荷药业有限公司|3-methyl-2--quinoxaline-1, 4-dioxide as well as preparation method and application thereof|
    CN105153050A|2015-10-21|2015-12-16|莱阳市盛华科技有限公司|Quinocetone derivative and preparation method thereof|
    CN105418520B|2015-11-16|2018-10-30|吉林化工学院|A kind of synthetic method of 3- methyl -2-quinoxaline -1,4- dioxide |
    CN105566234A|2015-12-24|2016-05-11|南阳市天华制药有限公司|Quinocetone preparation method|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    HU801385A|HU184292B|1980-06-03|1980-06-03|Process for preparing quinoxalinyl-ethenyl ketones|
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