- A epirubicin erythromycin intermediate compound
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The invention belongs to the field of organic chemistry, and in particular discloses a key intermediate epirubicin of erythromycin, its synthetic method and preparing the use of erythromycin in the epirubicin. The one preferred embodiment of this invention to (2 R, 6 S) - 6 - methoxy - 2 - methyl - 6 H - pyran - 3 - ons starting material, through reducing the double bond, halogenated, ammoniation, chiral separation, through the trifluoroacetyl group for protecting amino group, chloro can be obtained after the intermediate VI, with intermediate VI [...] by sodium borohydride reduction, de-trifluoroacetic acyl shall epirubicin than star intermediate body surface daunomycin. The full synthetic route has the short steps, mild reaction conditions, high yield, after treatment is convenient and the like, has good industrial prospects.
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- A epirubicin than star intermediate body surface epidaunorubicin synthetic method (by machine translation)
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The invention belongs to the field of organic synthesis, in particular discloses a epirubicin than star intermediate body surface epidaunorubicin synthetic method. The invention relates to (2 R, 6 S) - 6 - methoxy - 2 - methyl - 6 H - pyran - 3 - ons starting material, through reducing the double bond, halogenated, ammoniation, chiral separation, through the trifluoroacetyl group for protecting amino group, chloro can be obtained after the intermediate VI, with intermediate VI [...] by sodium borohydride reduction, to remove trifluoroacetic acyl shall epirubicin than star intermediate body surface daunomycin. The invention fully synthetic route has the short steps, mild reaction conditions, high yield, after treatment is convenient and the like, has good industrial prospects. (by machine translation)
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- Epirubicin hydrochloride intermediate compound IV
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The invention provides a novel intermediate and a new route for synthesizing epirubicin hydrochloride by using the intermediate. The route is simple, cheap and efficient, and meanwhile, the problems that the intermediate generated by an existing epirubicin hydrochloride synthesis route is instable in water and easy to decompose and the whole route is low in yield are solved. In order to better achieve energy conservation and emission reduction, a cheap and available reagent is utilized by the route; and meanwhile, removable selective protection means are adopted, so that the generated impurities are few, the purity is high and the yield is high.
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- Epirubicin hydrochloride than star-intermediate compound (by machine translation)
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The present invention provides novel intermediates and utilizing the intermediate synthesis than the star of epirubicin hydrochloride new routes. The route is simple, low-cost, high-efficiency, at the same time avoiding the existing epirubicin hydrochloride than star-synthetic route to produce the intermediate with water not stable, easily decomposed, the overall line rate is on the low side, in order to better energy-saving and emission reduction, the routes using low cost and easily obtained reagent; at the same time adopts the removable selective protection means, produce little impurity, high purity, high yield. (by machine translation)
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- A kind of N - trifluoro acetyl epirubicin seleno derivatives of erythromycin, preparation method and application thereof
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The invention discloses a seleno derivative of N-trifluoroacetyl epidaunorubicin, and adopts the structure of a general formula I (shown in the Specification). According to the invention, through the reaction of epidaunorubicin and trifluoroacetyl, an N-trifluoroacetyl epidaunorubicin is generated for reacting with a corresponding substituted seleno acetic acid so as to generate the N-trifluoroacetyl epidaunorubicin seleno derivative, wherein a substituent group being a seleno compound, is introduced through N-trifluoroacetyl epidaunorubicin 4' isotope for synthetizing the N- trifluoroacetyl epidaunorubicin seleno derivative in the hope of screening out anti-cancer drugs good in antitumor activity. The synthesis method provided by the invention is simple and scientific, and facilitates industrial production; the N-trifluoroacetyl epidaunorubicin seleno derivative can be used for the treatment of malignant tumors in the field of medicine.
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Paragraph 0030; 0031; 0032
(2017/07/14)
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- A hydrochloric acid the table is supple than star process for the preparation of intermediates
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The invention relates to a preparation method for an intermediate 4'-epidaunorubicin hydrochloride of epirubicin hydrochloride. The preparation method comprises the steps of trifluoroacetyl protection, oxidation, reduction, hydrolyzation, etc. The method effectively inhibit generation of (methylthio)methyl ether, increases selectivity for sodium borohydride during the reduction process and is mild in reaction conditions. The total yield of the reaction is over 40% (based on epidaunorubicin hydrochloride) and the purity reaches 99.5%.
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- SYNTHESIS OF EPIRUBICIN FROM 13-DIHYDRODAUNORUBICINE
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A method of preparing an anthracyclin such as epirubicin from a starting material comprising 13-dihydrodaunorubicine (13-daunorubicinol). The method comprises producing N-Trifluoroacetyl-13-daunorubicinol from 13-daunorubicinol by acylation. The N-Trifluoroacetyl-13-daunorubicinol is reacted with an aprotic solvent and an acylating agent to produce an intermediate sulfoxy salt which is treated with a strong base to produce 4′-keto-N-Trifluoroacetyldaunorubicin. The 4′-keto-N-Trifluoroacetyldaunorubicin is reacted with a reducing agent, such as borohydride of an alkaline metal, to produce N-Trifluoroacetyl-4′-epi-daunorubicin. The N-Trifluoroacetyl-4′-epi-daunorubicin is hydrolyzed in a basic solution to produce an intermediate compound. The intermediate compound is reacted with a halogenizing agent to produce a 14-Hal-derivative. The 14-Hal derivative is hydrolized in the presence of a formate of an alkaline metal to produce the desired final compound.
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Page/Page column 6
(2008/06/13)
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- EPIMERIZATION OF 4'-C BOND AND MODIFICATION OF 14-CH3-(CO)-FRAGMENT IN ANTHRACYCLIN ANTIBIOTICS
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A method of synthesizing Rl, R2-substituted-4' (ax. or eq.)-OH anthracyclines and their corresponding salts of Formula (1) from daunorubicin or N-Trifluoroacetyl-4- Rl - derivatives of daunorubicin, wherein Rl is defined as H, OH, and 4'-HO is defined as ax[ial]. The method includes producing N-Trifluoroacetyl daunorubicin and treating the N- Trifluoroacetyldaunorubicin or N-Trifluoroacetyl-4-R1 -derivatives of daunorubicin, wherein R1 is defined as H, OH, with dimethylsulfoxide activated by different acylating agents. The attained intermediate product is then treated with a strong base (ex. tertiary amines) resulting in the 4 -keto-N-Trifluoroacetyl-4-R1 daunorubicin wherein Ri is defined as H, OH, OMe. The 4-keto-N-Trifluoroacetyl-4-R1 -daunorubicin is reacted with a reducing agent, a derivative of a borohydride of an alkaline metal MHBL3 ,to produce N- Trifluoroacetyl-4'-epi-4-R1 -daunorubicin. The N-Trifluoroacetyl-4'-epi-4-R1 -daunorubicin undergoes hydrolysis in a basic solution to produce a derivate of an anthoacyclin which is halogenized [by complex halogenidesjto form a 14-Hal-derivative. This result is then hydrolyzed by well-known methods in the presence of a formate of an alkaline metal to form the desired final compound.
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Page/Page column 12
(2008/06/13)
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