• 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:
    7 beta -Acylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carbo ylic acid antibiotic compounds, esters and salts thereof, and the corresponding 7-amino and protected 7-amino 1-carbacephalosporins are provided. The 3-trifluoromethylsulfonyloxy-substituted 1-carbacephalosporins also are useful in a process for preparing 3-halo-1-carbacephalosporins which comprises displacing the 3-trifluoromethylsulfonyloxy ester group with halide ion in an aprotic polar solvent.
    公开号:SU1579460A3
    申请号:SU874202676
    申请日:1987-06-05
    公开日:1990-07-15
    发明作者:Алберт Эванс Дэвид；Брайан Съерген Эрик
    申请人:Президент Энд Феллоуз Оф Гарвард Калледж (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to the preparation of new substituted 7-amino-3-hydroxy-1-carba (1-child) -3-cephem-4-carboxylate of the general formula
    RiCONH.,
    COOR
    where R4 C (-C43alkoxy or phenoxymethyl;
    RZ-tert.butyl- or p-nitrobenzyl group, in the form of cis-enantomer, which can be used as intermediates in the synthesis of AND-lactam antibiotics.
    R
    The aim of the invention is to develop a method for producing new compounds, the use of which as an intermediate in products allows to significantly simplify the synthesis of lactam antibiotics.
    Pr im. Rubs GVTHTT- / 3-ter. Butyloxycarbonylamino-3-hydroxy-1-carba () -3-cephem-4-carboxylate.
    To a solution of 4.4 g (9.47 mmol) of 1- -tert-butyloxycarbonyl-methyl-3 | 3- -t-butyloxycarbonylamino-43- (2- -phenyl iocarbonylethyl) azetidin-2-one in 100-br dry tetrahydrofuran 29.3 ml (3.12 mmol) was added to aTMorr iepe argogg at -78 ° C
    4j

    s
    31
    lasanliti. After about 15 min, the mixture was drunk in 750 ml of an aqueous solution of ammonium chloride (50% of saturation) and the pH of the mixture was set to 3 with 1 n. hydrochloric acid The acidified mixture was extracted three times with 50 ml portions of methylene chloride. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated by evaporation. Concentrates exposed
    galy chromatography on dioxide cream.
    nor using as a eluent a mixture of hexane and ethyl acetate in a volume ratio of 1: 1. The eluate was evaporated to dryness, resulting in a target compound.
    Calculated,%: C 57.61; H 7.39; N 7.90.
    CnHe6N4Oe
    Found,%: N 7.69.
    Mass spectrum:
    IR and lactamcarbonyl: 1768.
    Similarly, p-nitrobenzyl ester of 7-phenoxy-acetylamino-3-β-hydroxy-1-carba (child) -3-cephem-4-carboxylic acid was obtained.
    Calculated,%: C 59.10; H 4.53; N 8.99.
    C 57.42; H 7.18; M4 354.
    Sgeang, S, 08
    Found,%: C 59.10; N 8.96.
    H 4.47;
    579460
    Mass spectrum (desorption by field): M-1 467.
    UV spectrum: max 275 nm; b 17.034;
    , c269 nm; 6
    IR spectrum: A-lactamcarbonyl:
    1766 cmH
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining substituted 7-amino-3-hydroxy-1-carba (1-child) -3-cephem-4-carboxylate of the general formula
    R, CONHv
    SOOVg
    where R (- C (-C-alkoxy or phenoxymethyl;
    R is a t-butyl and p-nitrobenzyl group, in the form of a cis-en-antiomer, characterized in that the compound of the general formula
    RiCONH. " CH2CH2COS- (Q
    CH2-COORa
    | where R {and Kg. have the indicated values "- 1 neither,
    subjected to interaction with hexamethyldisilazhenieMo
    Editor A. Dolinich
    Compiled by I. Bocharova
    Tehred L. Oliynyk Proofreader M. Samborska
    Order 1925
    Circulation 317
    VNIIPI State Committee for Inventions and Discoveries at the State Committee on Science and Technology of the USSR 113035, Moscow, Zh-35, Raushsk nab. 4/5
    Subscription
    类似技术:
    公开号 | 公开日 | 专利标题
    SU1579460A3|1990-07-15|Method of obtaining substituted 7-amino-3-oxy-1-carba |-3-cephem-4-carboxylate in form of cis-enathiomer
    FI103973B|1999-10-29|A method for purifying impure clavulanic acid
    JP5184465B2|2013-04-17|Method for producing potassium clavulanate
    SK61684A3|1998-03-04|D-2-aminoacyl-3-|-propenyl cephalosporine derivatives, a method of preparation and pharmaceutical compositions containing the same
    SU923365A3|1982-04-23|Process for producing prostane derivatives or their salts
    Hirama et al.1983|Enantiospecific syntheses of trifunctional |-3-hydroxy esters by baker's yeast reduction
    SU542474A3|1977-01-05|The method of obtaining derivatives of 7-amino-3-cephem-3 -4-carboxylic acid or their salts
    JP3073437B2|2000-08-07|Method for producing 3-formyl-cephem derivative
    Nudelman et al.1978|Novel 7-pyrrolocephalosporins
    Yanagisawa et al.1976|Synthesis of 7α-substituted cephalosporins. V Novel oxidation procedure for syntheses of 7α-methoxycephalosporins and 6α-methoxypenicillins
    FI57418B|1980-04-30|FOERFARANDE FOER FRAMSTAELLNING AV ANTIBIOTIKUMET 6-ACYLAMIDO-6-SUBSTITUERAD-PENICILLANSYRA
    US4159272A|1979-06-26|Process for 2-chlorosulfinylazetidin-4-ones
    SU878198A3|1981-10-30|Method of purifying mercaptan-containing oil distillate
    NL8000337A|1980-07-29|CEPHALOSPORINE DERIVATIVES AND METHODS FOR PREPARING AND USING THESE DERIVATIVES.
    CN104910164A|2015-09-16|Method for synthesizing 3,6-dichloroimidazo[1,2-b]pyridazine
    SU1039444A3|1983-08-30|Process for preparing 1-oxadethia cephalosporin
    KR830001969B1|1983-09-29|6- ｛D-| α- | phenyl | acetamido peniclanic acid and a method for preparing the salt thereof
    US3821208A|1974-06-28|Recovery of cephalosporin c and derivatives thereof
    JP4209022B2|2009-01-14|Process for producing isocyanoacetic acid alkyl esters
    D'Ascoli et al.1980|One-pot syntheses of cyclopent-2-enones from furan derivatives
    DE2841363C2|1988-08-04|
    US4446069A|1984-05-01|Process for the preparation of β-lactam antibiotics
    KR100202279B1|1999-06-15|Process for preparing cefuroxime ester derivatives
    DE2456528C2|1986-01-16|Process for the production of cephalosporins
    CH617437A5|1980-05-30|
    同族专利:
    公开号 | 公开日
    HUT41786A|1987-05-28|
    PT82989B|1989-01-30|
    IE861900L|1987-01-17|
    KR870001193A|1987-03-12|
    DK173456B1|2000-11-27|
    EP0209352B1|1991-05-02|
    HU906465D0|1991-04-29|
    AR243186A1|1993-07-30|
    US4665171A|1987-05-12|
    CN86104783A|1987-02-04|
    JPS6242985A|1987-02-24|
    AU619938B2|1992-02-06|
    DK335686D0|1986-07-15|
    ES2000516A6|1988-03-01|
    JPH0762015B2|1995-07-05|
    JP2634775B2|1997-07-30|
    AT63118T|1991-05-15|
    RU1794079C|1993-02-07|
    NZ216871A|1989-10-27|
    KR900005257B1|1990-07-21|
    EP0209352A2|1987-01-21|
    AU4793490A|1990-05-10|
    CN1015178B|1991-12-25|
    DK16096A|1996-02-15|
    AU6016686A|1987-01-22|
    ZA865274B|1988-02-24|
    EP0362902A3|1990-08-01|
    DK335686A|1987-02-25|
    IL79420A|1992-01-15|
    AU595216B2|1990-03-29|
    DE3650474T2|1996-06-13|
    AT133172T|1996-02-15|
    DE3650474D1|1996-02-29|
    IE58997B1|1993-12-15|
    EP0209352A3|1988-04-20|
    HK1007140A1|1999-04-01|
    HU201931B|1991-01-28|
    PT82989A|1986-08-01|
    GR861857B|1986-11-18|
    DE3679002D1|1991-06-06|
    ES2005752A6|1989-03-16|
    CA1310323C|1992-11-17|
    EP0362902A2|1990-04-11|
    EP0362902B1|1996-01-17|
    JPH07300476A|1995-11-14|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US4226866A|1972-11-06|1980-10-07|Merck & Co., Inc.|Novel antibiotic analogues of cephalosporins|
    US4166816A|1975-05-05|1979-09-04|Smithkline Corporation|Methods and intermediates for preparing cis-4-oxoazetidine intermediates|
    US4200572A|1975-09-03|1980-04-29|Smithkline Corporation|Substituted azetidinones|
    ZA766941B|1975-11-21|1978-06-28|Merck & Co Inc|3-cephalosporins,derivatives and nuclear analogues thereof|
    US4174316A|1978-08-14|1979-11-13|Merck & Co., Inc.|4-Iodomethylazetidin-2-one|
    US4472576A|1982-12-03|1984-09-18|Merck & Co., Inc.|Processes for the production of antibiotic 1-oxadethiacephalosporins|
    US4502994A|1982-12-09|1985-03-05|Hoffmann-La Roche Inc.|Enantiomeric synthesis of 3-amino-4-carbamoyloxymethyl-2-azetidonone-1-sulfate|
    US4751299A|1983-11-18|1988-06-14|Takeda Chemical Industries, Ltd.|Optically active β-lactams and method of their production|
    US4673737A|1985-08-02|1987-06-16|Harvard University|7-acylamino--3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylic acids and esters thereof|US4870169A|1985-07-17|1989-09-26|President And Fellows Of Harvard College|Intermediates for beta-lactam antibiotics|
    US4673737A|1985-08-02|1987-06-16|Harvard University|7-acylamino--3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylic acids and esters thereof|
    US4734498A|1986-07-10|1988-03-29|Eli Lilly And Company|3β-succinimidoazetidinones as chiral intermediates|
    CA1323370C|1986-09-12|1993-10-19|Davis H. Crater|Fluorochemical oxazolidinones|
    US4782144A|1987-09-14|1988-11-01|Eli Lilly And Company|1-carba-3-hydroxy-3-cephem ester crystalline and crystalline solvate thereof|
    US5019571A|1988-01-25|1991-05-28|Eli Lilly And Company|1-carbacephalosporin antibiotics|
    US4855418A|1988-03-23|1989-08-08|Eli Lilly And Company|Process for production of ceophalosporins|
    US4820832A|1988-03-23|1989-04-11|Eli Lilly And Company|Process for preparing 3-unsubstituted cephalosporins and 1-carbacephalosporins|
    JPH0225462A|1988-06-06|1990-01-26|Eli Lilly & Co|Preparation of beta-lactam antibiotic and intermediate thereof|
    US4885362A|1988-06-06|1989-12-05|Eli Lilly And Company|Azetidinone intermediates for 1-carbacaphalosporins|
    JPH0225463A|1988-06-06|1990-01-26|Eli Lilly & Co|Production of intermediate of 1-carba-3-cephem-4-carboxylic acid|
    JP2809711B2|1988-06-22|1998-10-15|イーライ・リリー・アンド・カンパニー|Intermediate of 1-carbacephalosporin|
    US5453503A|1988-10-11|1995-09-26|Eli Lilly And Company|Azetidinone intermediates to carbacephalosporins and process|
    KR0169096B1|1988-10-11|1999-01-15|리로이 휘테커|Azetidinone omtermediates to carbacephalosporins and process|
    US4931557A|1988-10-17|1990-06-05|Eli Lilly And Company|Method of resolving cis 3-amino-4-vinyl)-1-methoxycarbonylmethyl-azetidin-2-one and di-p-toluoyl-tartaric acid salts thereof|
    US4931556A|1988-10-17|1990-06-05|Eli Lilly And Company|Method of resolving cis 3-amino-4-eth-1-yl)-methoxycarbonylmethyl-azetidin-2-one and malic acid salts thereof|
    JPH02252648A|1989-03-27|1990-10-11|Naomi Iwagou|Ion-eluting sintered product|
    US5106475A|1989-09-20|1992-04-21|Eli Lilly And Company|Process for preparing 4-substituted azetidinones|
    US4992545A|1989-09-20|1991-02-12|Eli Lilly And Company|Process for preparing 4-substituted azetidinones|
    US5030725A|1990-02-06|1991-07-09|Eli Lilly And Company|Method of resolving cis 3-amino-4-[2-eth-1-yl]-1-methoxycarbonylmethyl-azetidin-2-one using -DAG|
    US5051502A|1990-06-06|1991-09-24|University Of Notre Dame Du Lac|Rhodium catalyzed cyclization process for bicyclic β-lactams|
    EP0479431B1|1990-09-13|1999-12-08|Eli Lilly And Company|Intermediates to 1-carbacephalosporins and process for preparation thereof|
    US5089610A|1991-04-25|1992-02-18|Eli Lilly And Company|Ring-closure method for 1-carbacephalosporin six-membered ring|
    US5521307A|1992-02-18|1996-05-28|Eli Lilly And Company|Methods and compounds for the preparation of carbacephems|
    CA2246753C|1996-02-23|2005-05-10|Robert Frederick Bruns Jr.|Non-peptidyl vasopressin v1a antagonists|
    JP2002535680A|1999-01-27|2002-10-22|ファルマシア・アンド・アップジョン・カンパニー|Assay method for elongation factor p activity modulator|
    JP4916929B2|2007-03-23|2012-04-18|ヤマハ発動機株式会社|Cartesian robot|
    CA2711957C|2007-10-11|2019-03-19|The Regents Of The University Of California|Use of inhibitors of n-acylethanolamine-hydrolyzing acid amidase as anti-inflamatory medicaments|
    RU2623209C9|2010-07-01|2018-01-22|Азеван Фармасьютикалз, Инк.|Method for ptsd treatment|
    WO2014144836A2|2013-03-15|2014-09-18|The Regents Of The University Of California|Carbamate derivatives of lactam based n-acylethanolamine acid amidaseinhibitors|
    WO2014144547A2|2013-03-15|2014-09-18|The Regents Of The University Of California|Amide derivatives of lactam based n-acylethanolamine acid amidaseinhibitors|
    US20190321363A1|2016-06-20|2019-10-24|Dr. Reddy's Laboratories Limited|Process for the preparation of elagolix sodium and its polymorph|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US06/755,982|US4665171A|1985-07-17|1985-07-17|Process and intermediates for β-lactam antibiotics|
    [返回顶部]