• 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:
    Prodn. of guanidine derivs. of formula (I) comprises reacting a mercaptan deriv. of formula Het-(CH2)m-SM (III) is reacted with a guanidine of formula (IV). In the formulae, Het is opt. substd. 5- or 6-membered heterocyclic residue with 1 or 2 N-atoms; m is 1,2,3 or 4; R1 is H or 1-4C alkyl; R2 is CN or NO2; M is H or alkali metal; and Y is 2-oxo-3-oxazolidinyl, ethyleneimino or 2-haloethylamino. The intermediates 4-methyl-5-mercaptomethyl-imidazole and 1-(N-methyl-N'-cyano-carboxamido) -azinidine are also new. (I) are histamine H2 receptor blockers useful against gastric ulcers.
    公开号:SU1077570A3
    申请号:SU782704652
    申请日:1978-12-28
    公开日:1984-02-29
    发明作者:Бодэ Пьер；Рикар Жан-Поль；Шультесс Адриан
    申请人:Лаборатуар Ом Сосьете Аноним (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of a guanidine derivative of the formula. NK-SYa Н-ц-СНг-З-СНг which possesses medicinal properties, and can be used in medicine in the treatment of stomach ulcers, blocking histamine H2 receptors. There is a known method for producing a guanidine derivative of formula (1) by the interaction of H-cyan-N - f2 - | 4-methyl-5-imidazolyl) -methylmer capto ethyl-5-methylisothiourea with a 33% solution of methylamine in ethanol. The reaction mixture is kept at room temperature for 2.5 hours. After evaporation under reduced pressure, the residue is recrystallized twice from isopropanol / lithroleate ether. The yield of 8.6 g or 90% | l. The disadvantage of this method is the inaccessibility of the initial reagent and the need for double recrystallization of the target product to obtain a pure substance. The purpose of the invention is to simplify the process. This goal is achieved by the fact that according to the method for producing a guanidine derivative of formula (1) using derivatives. The imidazole imidazole hydrochloride of the formula K CK2-SH is removed by reaction with azyryne of the formula CN-CH3 1G-C “H in an aqueous medium in the presence of an inert atmosphere. Example N-methyl-K cyano-2 -2- {4-methyl-5-imidazolyl) methylthio) ethyl guanidine. To a solution of 16.45 g of 4-methyl-5-methylmercaptoimidazole hydrochloride and -12.4 g, N-C-methyl-N-cyano-carboxamidino) -aziridine in 100 ml of distilled water in a stream of nitrogen, equals 4.4 g of J4 Caller ID, maintaining an inert atmosphere throughout the reaction. After 20 hours at ordinary temperature, the crystalline phase of the product which crystallizes in acetonitrile, m.p. 142-143®C. Yield 90%. The initial products are prepared in the following way. 1. 4-methyl-5-methyl mercaptoimidazole hydrochloride. Within 6 hours, through a solution of 8.7 g of 4-methyl-5- (ethoxydithio-formyl) -imidazole in 100 ml 12 and. hydrochloric acid is passed through a countercurrent of nitrogen, the solvent is removed under reduced pressure, and the solid precipitate is crystallized cold in butanol-2, recrystallized in butanol-2, so pl. 208-210 C. Yield 90%. 2. 4-methyl-5-methylmercaptoimidazole hydrochloride. To a solution of 16.5 g of 4-methyl-5-chloromethylimidazole hydrochloride in 70 ml of ethyl alcohol is added 29.6 g of potassium ethyl xanthate and maintain the flow for 3 hours. The residue after evaporation is placed in 100 ml of 12N. Sulfuric acid in a stream of nitrogen for 6 hours. The solvent is removed under reduced pressure and the solid residue is crystallized cold in butanol-2, recrystallized in butanol-2, so pl. 208-210 C. Yield 80%. Thus, the proposed method allows to obtain the desired product from available starting materials, for example, aziridine, a multi-tonnage product, which is widely used in the paper industry. In addition, the reactivity of aziridium is so high, and the reaction proceeds in such mild conditions that no by-products are formed and the target product does not require recrystallization.
    权利要求:
    Claims (2)
    [1]
    METHOD OF OBTAINING PRODUCTION OF 1 HUANIDANINE FORMULA
    „ΝΗ-СНз
    CH 2 "5-en., - CH G BN-sC and
    SNS
    I
    n
    using imidazole derivatives, characterized in that, in order to simplify the process, imidazole hydrochloride of the formula
    OS
    | SNS-NS!
    subjected to interaction with the formula azyridine
    n sG - ™ -sn,
    in aqueous medium in the presence of NaOH in an inert atmosphere.
    1077570
    one
    1077570
    [2]
    2
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    同族专利:
    公开号 | 公开日
    IT7831392D0|1978-12-28|
    JPS6140667B2|1986-09-10|
    ES476707A1|1979-06-01|
    PL212223A1|1979-08-27|
    DE2855836C2|1989-09-28|
    IL56265D0|1979-03-12|
    CS208770B2|1981-09-15|
    IL56265A|1982-08-31|
    NL184832C|1989-11-16|
    JPS5827792B2|1983-06-11|
    IT1102776B|1985-10-07|
    NL7812600A|1979-07-02|
    RO76087A|1981-02-28|
    FI74954C|1988-04-11|
    JPS5962572A|1984-04-10|
    YU41138B|1986-12-31|
    FI74954B|1987-12-31|
    DE2855836A1|1979-07-12|
    YU308478A|1983-01-21|
    PL115042B1|1981-03-31|
    FI783990A|1979-06-29|
    JPS54130566A|1979-10-09|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    IE36050B1|1971-03-09|1976-08-04|Smith Kline French Lab|Ureas thioureas and guanidines|
    GB1533380A|1974-09-02|1978-11-22|Smith Kline French Lab|Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines|
    GB1531231A|1974-09-02|1978-11-08|Smith Kline French Lab|Process for the production of cyanoguanidine derivatives|
    JPS5817511B2|1975-10-03|1983-04-07|Sekisui Chemical Co Ltd|
    MW5076A1|1975-12-29|1978-02-08|Smith Kline French Lab|Pharmacologicalle active compounds|
    JPS6148297B2|1977-09-07|1986-10-23|Seikosha Kk|
    IL56265A|1977-12-28|1982-08-31|Om Lab Sa|Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor|
    JPS5742068A|1980-08-27|1982-03-09|Ricoh Co Ltd|Solvent recovering device for wet type electronic copying machine|
    JPS6011994B2|1981-08-10|1985-03-29|Ikeda Hiromi|
    JPS622588B2|1981-11-19|1987-01-20|Fujimoto Seiyaku Kk|IL56265A|1977-12-28|1982-08-31|Om Lab Sa|Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor|
    NO784350L|1977-12-30|1979-07-03|Crc Ricerca Chim|PROCEDURE FOR ALKYLATION OF 4-MERCAPTOMETHYL-IMIDAZOLES WITH AZIRIDINE DERIVATIVES|
    YU40332B|1978-04-26|1985-12-31|Lek Tovarna Farmacevtskih|Process for preparing n-cyano-n'-methyl-n''--methylthio)ethyl)-guanidine|
    LU81178A1|1978-05-12|1979-09-10|Crc Ricerca Chim|NEW THIOLD DERIVATIVES OF IMIDAZOLE|
    US4222845A|1978-12-13|1980-09-16|Gulf Oil Corporation|Integrated coal liquefaction-gasification-naphtha reforming process|
    JPS56500174A|1979-02-14|1981-02-19|
    CH642068A5|1979-03-14|1984-03-30|Rech Syntheses Organ|THERAPEUTICALLY ACTIVE CYANO-UREA AND CYANO-THIOURAE.|
    PT72320B|1980-01-08|1982-07-23|Glaxo Group Ltd|Process for preparation of a furan derivative|
    YU41689B|1980-01-14|1987-12-31|Lek Tovarna Farmacevtskih|Process for preparing imidazole derivatives|
    DE3014353A1|1980-04-15|1982-01-21|Bayer Ag, 5090 Leverkusen|TRISUBSTITUTED CYANGUANIDINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES|
    JPS622588B2|1981-11-19|1987-01-20|Fujimoto Seiyaku Kk|
    JPS622591B2|1983-01-14|1987-01-20|Tokawa Tetsuo|
    JPS6170789U|1984-10-16|1986-05-14|
    GB8502446D0|1985-01-31|1985-03-06|Smith Kline French Lab|Preparing aziridine derivative|
    YU45030B|1987-01-23|1991-06-30|Lek Tovarna Farmacevtskih|Process for preparing crystalline cimetidine|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    CH1612677A|CH626353A5|1977-12-28|1977-12-28|Process for the preparation of a guanidine|
    CH1247778A|CH636348A5|1978-12-07|1978-12-07|Process for the preparation of guanidine derivatives|
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