• 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:
    Antibacterial agents in which a pencillin and a beta-lactamase inhibitor are linked by means of a bis- hydroxymethyl carbonate bridge are of the formula and pharmaceutically acceptable acid addition salts thereof, wherein R1 is hydrogen, hydroxy, certain acyloxy or certain alkoxycarbonyloxy groups, a method for their use, pharmaceutical compositions thereof, and intermediates useful in their production.
    公开号:SU1169541A3
    申请号:SU833644103
    申请日:1983-09-20
    公开日:1985-07-23
    发明作者:Сейичи Хаманака Эрнест
    申请人:Пфайзер Инк (Фирма)；
    IPC主号:
    专利说明:

    one . This invention relates to a process for the preparation of a new penillin ester, namely iodonyl 6- (D-2-agido 2-phenylacetamido) penicillanoylloxymethyl carbonate, which is an intermediate in the synthesis of the antibiotic penicillin series. The aim of the invention is to obtain novel intermediates in the synthesis of penidillin antibiotics, which are active against microorganisms, resistant to other types of antibiotics, and possess high activity. Nuclear Magnetic Resonance (NMR) spectra are measured for solutions in deuterated chloroform (CBC1 deuterated dimethyl sulfoxide (flMSO-d), peak points in parts per million in the direction down from tetramethylsilane. Example 1. Bis-Yodmetshtcarbonate. Example 1. bis-Yodmetshtcarbonate. Example 1. Bis. , 7 ml. (15.9 g, 0.1 mol) of bis- (chloromethyl) carbonate in 400 ml of acetone inject 75 g (0.5 mol) of sodium iodide. The mixture is heated under reflux for 2 hours in the atmosphere then left overnight at room temperature. The mixture is filtered and the filtrate is evaporated in Vacuum. Methylene chloride (500 ml) was added to the resulting evaporation product and the resulting mixture was filtered. The filtrate was evaporated to a volume of about 200 ml, 200 ml of water was added and the pH of the aqueous phase was adjusted to 7.5. an aqueous solution of sodium thiosulfate is removed, iodine is removed, the organic phase is separated and dried over sodium sulfate. The dried 1 solution of methylene chloride is evaporated in vacuo to give an oil, which darkens on standing. This oil product is treated with a mixture consisting of 35 ml of hexane and 6 ml of diethyl ether, the crystals formed are filtered, washed with hexane, and dried to give 10.0 g (29%) of a yellowish crystalline product, m.p. . 49-5 Gs. Spectrum H-NMR (CDC1,) cA, ppm: 5.94 S. Infrared spectrum (Nujol), cm 1756, 1775. Example 2. Iodmethyl 6- (D-2-azido-2-phenylacetamido) penicillanoyl oxymeptide carbonate . In the cooled (before) solution. 2.43 g (7.1 mmol) of bis-iodomethyl carbonate in chloroform (16 ml) a solution of 2.19 g (3.5 mmol) of tetrabutylammonium 6- (b-2-azido-2-phenylacetamido) is introduced dropwise penitsllanat in 10 ml of chloroform, after which the reaction mixture is heated to room temperature and hold it overnight. The solvent is evaporated in vacuo and the evaporation residue is subjected to chromatographic separation on silica gel with elution with a mixture of methylene chloride and ethyl acetate in a volume ratio of 3: 1, resulting in 822 mg (40%) of the product. H-NMR spectrum (CDClj) cG, ppm: 1.52 (s, 3N); 1.65 (s, 3N); 4.45 (s, 1H); 5.04 (s, 1H); 5.65 (t, 4H); 5.92 (s, 2H); 7.34 (s, 5H). Infrared spectrum (CHClj) 1770 cm
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING IODOMETHYL 6- (O-2-AZIDO-2-PHENYLACETAMIDO) -PENICYLANOYYloXYMETHYL CARBONATE of the formula ^ COOCHjOCOCHjJ characterized in that the compound of the general formula sn 3 sn 3 'COOM where M is tetrabutylammonium CH, J, O, J is reacted with 0OC, inert under the reaction conditions of an organic solvent at a temperature of from 0 ° C to room temperature.
    SU m l 169541>
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    同族专利:
    公开号 | 公开日
    KR860001362B1|1986-09-16|
    HU188825B|1986-05-28|
    FI824408L|1983-06-23|
    NO824304L|1983-06-23|
    AU560708B2|1987-04-16|
    JPS58116490A|1983-07-11|
    DD208621A5|1984-04-04|
    PL248638A1|1985-05-07|
    DD222315A5|1985-05-15|
    ES524779A0|1985-01-01|
    US4359472A|1982-11-16|
    NO160300C|1989-04-05|
    NO160300B|1988-12-27|
    JPH0119394B2|1989-04-11|
    AU535634B2|1984-03-29|
    GR77097B|1984-09-06|
    PL140375B1|1987-04-30|
    PT76011B|1985-12-13|
    NZ202855A|1985-09-13|
    ES518490A0|1984-02-01|
    ES8402157A1|1984-02-01|
    EP0082666B1|1986-02-05|
    NO832871L|1983-06-23|
    PL239590A1|1985-01-16|
    FI75570C|1988-07-11|
    YU280082A|1985-04-30|
    DK565582A|1983-06-23|
    PL140731B1|1987-05-30|
    SU1217261A3|1986-03-07|
    FI824408A0|1982-12-21|
    ZA829375B|1983-10-26|
    IE54334B1|1989-08-30|
    AT17853T|1986-02-15|
    YU42823B|1988-12-31|
    PH18490A|1985-08-02|
    IL67523A|1986-04-29|
    IE823035L|1983-06-22|
    FI75570B|1988-03-31|
    EG15866A|1986-09-30|
    PT76011A|1983-01-01|
    ES8502443A1|1985-01-01|
    AU9172282A|1983-08-04|
    ES524778A0|1984-12-16|
    DD216024A5|1984-11-28|
    IL67523D0|1983-05-15|
    CS236779B2|1985-05-15|
    EP0082666A1|1983-06-29|
    DE3269029D1|1986-03-20|
    AU2367284A|1984-05-10|
    ES8502119A1|1984-12-16|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    NL299897A|1962-11-02|
    US2985648A|1958-10-06|1961-05-23|Doyle Frank Peter|Alpha-aminobenzylpenicillins|
    US3520876A|1967-11-01|1970-07-21|American Home Prod|Process for the preparation of 6-penicillanic acids|
    BE784800A|1971-06-15|1972-10-02|Yamanouchi Pharma Co Ltd|PROCESS FOR PREPARING NEW OXYMETHYL ESTERS OF PENICILLIN AND CEPHALOSPORIN|
    GB1425827A|1972-03-13|1976-02-18|Astra Laekemedel Ab|Penicillins and cephalosporins|
    ES436565A1|1974-06-05|1977-04-01|Bristol Myers Co|Enzymatic preparation of 6-d--' -amino-' -penicillin acid|
    US4234579A|1977-06-07|1980-11-18|Pfizer Inc.|Penicillanic acid 1,1-dioxides as β-lactamase inhibitors|
    IE49881B1|1979-02-13|1986-01-08|Leo Pharm Prod Ltd|B-lactam intermediates|
    BE881675A|1979-02-13|1980-08-12|Leo Pharm Prod Ltd|B-LACTAMS DERIVED FROM PENICILLANIC ACID, THEIR PREPARATION AND THEIR THERAPEUTIC USES|
    US4244951A|1979-05-16|1981-01-13|Pfizer Inc.|Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide|
    US4359472A|1981-12-22|1982-11-16|Pfizer Inc.|Bis-hydroxymethyl carbonate bridged antibacterial agents|US4359472A|1981-12-22|1982-11-16|Pfizer Inc.|Bis-hydroxymethyl carbonate bridged antibacterial agents|
    US4434173A|1982-08-23|1984-02-28|Pfizer Inc.|Bis-esters of 4,5-di-2-oxo-1,3-dioxole as antibacterial agents|
    US4448732A|1982-09-07|1984-05-15|Pfizer Inc.|2-Oxo-1,3-dioxol-4-ylmethyl esters of penicillanic acid 1,1-dioxide|
    US4530792A|1982-11-01|1985-07-23|Pfizer Inc.|Process and intermediates for preparation of 1,1-dioxopenicillanoyloxymethyl 6-beta-aminopenicillanate|
    CN112724162A|2020-12-28|2021-04-30|华南农业大学|Synthesis method and application of amoxicillin-sulbactam hybrid molecule|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US06/334,017|US4359472A|1981-12-22|1981-12-22|Bis-hydroxymethyl carbonate bridged antibacterial agents|
    AU23672/84A|AU560708B2|1981-12-22|1984-01-20|Penicillin intermediates|
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