KR840004115A - Method for preparing cefuroxime derivative - Google Patents

Abstract

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Description

Method for preparing cefuroxime derivative

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Claims (26)

(6R, 7R) -3-carbamoyloxymethyl-7-2- (fur-2-yl) -2-methoxyiminoacetamido-3-cepem-4 represented by the general formula (II). -Carboxylic acid (geometric isomer). In the above general formula, R ¹ , R ² , R ³ and R ⁴ are primary or secondary alkyl groups having 1-3 carbon atoms and R ⁴ may be a hydrogen atom. The derivative according to claim ¹ , wherein R ¹ , R ² and R ³ are methyl groups and R ⁴ is a methyl group. (6R, 7R) -3-carbamoyloxymethyl-7-2- (fur-2-yl) -2-methoxyiminoacetamido-3-cefe-4-carboxylic acid Method of preparing the derivatives of claim 1, wherein the halogenated ester of III) is prepared in the form of an alkali metal salt, alkaline earth metal salt or ammonium salt. In the general formula, X represents a halogen atom. 4. The process of claim 3, wherein the reaction is carried out in an inert organic base in the presence of a weak inorganic base in the temperature range of -50 ° to + 150 ° C. 5. The process according to claim 4, wherein the weak inorganic base is an alkali metal carbonate and it is added to the reaction mixture before introducing the halogenated ester (III). The method of claim 4, wherein the inert organic solvent is selected from N, N-dimethylformamide, acetone, dimethyl sulfoxide and acetonitrile. The method of claim 4, wherein the reaction temperature is a temperature in the range of -10 ℃ to +50 ℃. The method of claim 7, wherein the reaction temperature is a temperature in the range of -10 ℃ to +20 ℃. The method of claim 3, wherein the halogenated ester is used in an amount of about 10-15% greater than the stoichiometric ratio. 4. A process according to claim 3, wherein a phase inversion catalyst is added to the reaction mixture. The method according to claim 10, wherein the phase inversion catalyst is a tetrabutylammonium salt. Claim 1 Claim 1 characterized by acylating a compound represented by the following general formula (IV) or one of its reaction derivatives with an acid in its geometric isomeric form represented by the following general formula (V) Process for the preparation of derivatives by Wherein R ¹ , R ² , R ³ and R ⁴ are as defined in claim 1. 13. The method according to claim 12, wherein the reaction derivative of the compound represented by the general formula (VI) is an acid addition salt thereof or -NH ₂ silylated derivative thereof. The method according to claim 13, wherein the acylation reaction is carried out using a reaction derivative in an aqueous or non-aqueous medium in the presence of a base which is the acceptor within a temperature range of −50 ° C. to + 50 ° C. The method of claim 14 wherein the reaction temperature is a temperature in the range of -20 ℃ to +30 ℃. 15. The method of claim 14, wherein said receptor is a tertiary amine. The method of claim 16 wherein said tertiary amine is selected from triethylamine and N, N-dimethylaniline. 15. The method of claim 14, wherein said receptor is an inorganic base. 19. The method of claim 18, wherein the inorganic base is selected from carbonates and bicarbonates of alkali metals. 13. A process according to claim 12, wherein the acylation reaction is carried out as acid (V) in the presence of an acylating agent in anhydrous medium. 21. The method of claim 20, wherein said acylating agent is selected from bicyclohexyl carbodiimide and carbonyldiimidazole. 21. The method of claim 20, wherein the reaction is received in a solvent selected from methylene chloride, N, N-dimethylformamide and acetonitrile. 13. The process according to claim 12, wherein the acylation reaction is effectively carried out as a symmetric or mixed anhydride of the acid represented by the general formula (V). The method of claim 23, wherein the mixed anhydride is prepared in situ by reacting an acid (V) with a reagent selected from pivaloyl chloride, alkylhalogenoformate, and phosphoric acid. Claim 1, characterized in that the carbamoylation reaction represented by the general formula (VI) is carried out with a reagent selected from chlorosulfonyl isocyanate and trichloroacetyl isocyanate in anhydrous medium and an organic solvent. Method for producing a derivative by A pharmaceutical composition for oral administration comprising the derivative of claim 1 as an active ingredient and a mixture of a common carrier, whole body, filler and the like. ※ Note: The disclosure is based on the initial application.