• 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:
    Amidinoformic acids and amidinosulphinic acids which are histamine H2-antagonists. A specific compound of this invention is N-[2-(3-(1,2,5)-thiadiazolylmethylthio)ethyl]amidinoformic acid.
    公开号:SU814274A3
    申请号:SU772460625
    申请日:1977-03-11
    公开日:1981-03-15
    发明作者:Джон Дьюрант Грэхэм；Робин Ганнелин Чарон；Кристофер Янг Родни
    申请人:Смит Клайн Энд Френч Лабора-Ториз Лимитед (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of new amidino formic acid derivatives which may be used in the chemical and pharmaceutical industry. The interaction of amines with sulfur-containing compounds is known. 1 The purpose of the invention is to obtain new compounds with valuable pharmaceutical properties. This goal is achieved by the method of obtaining compounds of the general formula (iOOH (1) is non-b) (where Bet is an imidazole or thiazole ring, substituted or unsubstituted by methyl T, hydrogen or methyl, which consists in reacting the compound of the general formula - COOH, (11) where R is as defined above with an amine of the formula Het CHaSCH2CH, NH2, (HI) and the resulting desired product is isolated. Lead orthoplumbate is added to accelerate the reaction. Example 1 (5-Methyl-4 imidazolylmethylthio) ethyl) aminidine formic acid. Ortoplumbat lead (43 g) ext is a solution of thioxamic acid (4.9 g) and 2- (5-methyl-4-imidazolylmethylthio) -ethylamine (8.0 g) in methanol (200 ml). The mixture is stirred at room temperature for 4 hours and filtered , separation of the lead compound. The product is purified on a chromatographic column, and traces of impurities are removed by boiling in acetonitrile. .pl. 174176 ° С (with decomposition). The yield is 25%,
    Found,% C, 47; H 6.8; N 20.3; S And, 3.
    С9 Н „N40aS (CtHB), iO).
    Calculated,%: C 47.3; H 6.8; N 20.1; S 11.5.
    Example 2, L-methyl-L-2- (5-methyl-4-ymidazolylmethylthio) ethyl amidinvolume acid hydrochloride.
    Lead orthoplumbate (50 g) is added to a solution of N-methylthioxamic acid (4.7 g) and 2- (5-methyl-4-imidazolylmethylthio) ethylamine (6.0 g) in water (150 ml). The mixture was stirred at room temperature for 2 days and then filtered. The filtrate is passed through a column with AmberEite.
    1RC-50 and then eluted with water, acidified with hydrochloric acid to pH 3. Water is distilled off under reduced pressure, and the residue is recrystallized twice:) T from methanol. The yield of the desired product is 0.7 g (4%). M.p. 158-159 C (with decomposition
    Found,%: C 39.0; H 5.8; N 20.0; S 22,8,
     N4 0232Calculated,%: C 31.1: H 5.8; N 20.3 S 23.2.
    Example 3. H, H-5is-2- (5-Methyl-4-imidazolylmethylthio) ethyl) amidinoformic acid.
    2- (5-Methyl-4-imidazolylmethylthio) ethylamine is added to a solution of potassium thioxamate in water. The solution is kept for 2 hours at room temperature and acidified with hydrochloric acid. (5-methyl-4-imidazolylmethylthio) ethylamino-thioxamic acid is obtained. The resulting material is reacted with 2- (5-methyl-4-imidazolylmethylthio) ethylamine and lead orthoplumbate for
    2 days, as in Example 2, and N, N-5uc- 2- (5-methyl-4-imidazolyl Methylthio) ethyl amidinomurate acid is obtained. The yield is 3%.
    Example 4.N (2-Thiazolylmethylthio) ethyl amidinoformic acid.
    As described in example 1, 2- (2-thiazolllmethylthio) -thylamine is reacted with thiooxamic acid and the desired product is isolated with mp. 152-154 p.
    Found,%: C 39.2; it 4,5; N 17.2, S 26.01,
    , CgH N, 04 S.,
    Calculated,%: with 39.2; H 4.5; N 17.1; S 26.1.
    The compounds of general formula (I) can be used as inhibitors of histamine-stimulated gastric acid.
    权利要求:
    Claims (1)
    [1]
    1. Weigand - Hilgetag. Methods. Experiment in organic chemistry.
    I I
    1968, p. 513.
    Chem
    M.,
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    同族专利:
    公开号 | 公开日
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    IT1075494B|1985-04-22|
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    ZM2677A1|1978-07-21|
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    NO770854L|1977-09-13|
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    AT358576B|1980-09-25|
    RO73006A|1982-04-12|
    BE852324A|1977-09-12|
    ES456735A1|1978-06-01|
    IE44786B1|1982-03-24|
    FR2343730B1|1980-01-11|
    IN147036B|1979-10-27|
    NL7702533A|1977-09-13|
    MW977A1|1978-08-09|
    CS196352B2|1980-03-31|
    HU176611B|1981-03-28|
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    SE7702771L|1977-09-14|
    US4395419A|1983-07-26|
    NZ183396A|1979-03-28|
    LU76930A1|1977-07-12|
    GR62562B|1979-05-10|
    PL105620B1|1979-10-31|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    BE758146A|1969-10-29|1971-04-28|Smith Kline French Lab|AMIDINE DERIVATIVES|
    US3808336A|1970-06-25|1974-04-30|Smithkline Corp|Pharmaceutical compositions and methods of inhibiting histamine activity with thiourea derivatives|
    US3734924A|1970-10-14|1973-05-22|Smith Kline French Lab|Carboxamidines|
    GB1338169A|1971-03-09|1973-11-21|Smith Kline French Lab|Ureas thioureas and guanidines|
    US4056620A|1973-02-08|1977-11-01|Smith Kline & French Laboratories Limited|Sulphoxides|
    GB1421999A|1973-02-08|1976-01-21|Smith Kline French Lab|Heterocyclic containing sulphoxides|
    US4140783A|1976-05-24|1979-02-20|Smith Kline & French Laboratories Limited|Isothiazole and isoxazole sulphoxides|
    US4046907A|1973-05-17|1977-09-06|Smith Kline & French Laboratories Limited|Imidazole alkylaminoethylene compounds|
    US4025527A|1973-07-13|1977-05-24|Smith Kline & French Laboratories Limited|Certain thiazoles and oxazoles|
    GB1533380A|1974-09-02|1978-11-22|Smith Kline French Lab|Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines|
    GB1602458A|1977-05-05|1981-11-11|Smith Kline French Lab|Bisamidines as histamine h2-antagonists|US4210658A|1977-09-08|1980-07-01|Smith Kline & French Laboratories Limited|Amidinosulphonic acid derivatives|
    EP0006679B1|1978-05-24|1982-07-21|Imperial Chemical Industries Plc|Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them|
    IL57415A|1978-05-30|1984-08-31|Smith Kline French Lab|Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them|
    US4282213A|1978-06-06|1981-08-04|Smith Kline & French Laboratories Limited|Amidino and guanidino phosphonates|
    US4242351A|1979-05-07|1980-12-30|Imperial Chemical Industries Limited|Antisecretory oxadiazoles and pharmaceutical compositions containing them|
    IT8020734D0|1980-03-18|1980-03-18|Turconi Franco|SQUARE-TYOMETHYLIVERS OF 4-METHYL-5 OPEN PAR.CLOSED PAR. SQUARE-IMIDAZOLE THERAPEUTIC ADAPTITY.|
    US4375547A|1980-10-02|1983-03-01|Eli Lilly And Company|N-Methyl-N'-2--4-thiazolyl]methylthio)ethyl 2-nitro-1,1-ethenediamine|
    US4382090A|1980-10-02|1983-05-03|Eli Lilly And Company|N-Thiazolylmethylthioalkyl-N'alkylamidines and related compounds|
    IT1201523B|1982-05-18|1989-02-02|Angeli Inst Spa|HETEROCYCLYLPHENYLPHOMRAMIDIN, PROCESSES FOR THEIR PREPARATION AND THEIR PHARMACEUTICAL USE|
    US5399706A|1993-03-02|1995-03-21|H. B. Fuller Licensing & Financing, Inc.|Imidazolidinone diamine and derivatives thereof|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB9750/76A|GB1574214A|1976-03-11|1976-03-11|Amidines|
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