KR890013010A - Benzoxazide compounds, preparation methods thereof and preparation compositions containing the same - Google Patents

Abstract

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Description

Benzoxazide compounds, preparation methods thereof and preparation compositions containing the same

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Claims (15)

Benzoxazide compounds of the general formula (I) (Wherein R ¹ represents a hydrogen atom or an alkyl group, R ² represents a hydrogen atom, an alkyl group, a cyanoalkyl group, an alkenyl group, an alkynyl group or an aralkyl group). The benzoxazine compound according to claim 1, wherein R ¹ in General Formula (I) represents an alkyl group having 1 to 4 carbon atoms. The benzoxazine compound according to claim 1, wherein R ² in General Formula (I) represents an alkyl group having 1 to 8 carbon atoms. The benzoxazide according to claim 1, wherein R ² in formula (I) represents a cyanoalkyl group having an alkyl moiety of 1 to 4 carbon atoms. The benzoxazide according to claim 1, wherein R ² in General Formula (I) represents an alkenyl group having 3 to 6 carbon atoms. The benzoxazide according to claim 1, wherein R ² in General Formula (I) represents an alkynyl group having 3 to 6 carbon atoms. The benzoxazide according to claim 1, wherein R ² in General Formula (I) represents an aralkyl group having 7 to 10 carbon atoms. After reducing the nitro group of the oxazolidinedione compound of the following general formula (II), condensation reaction of the produced amino group and its ester group produces the compound of the following general formula (I '), and the benzoxazide compound A method for preparing a compound, wherein the benzoxazide of formula (I ″) is characterized by reacting in the presence of a compound of formula (III) with a base: (Wherein R ¹ represents a hydrogen atom or an alkyl group, R ^{2 ′} represents an alkyl group, a cyanoalkyl group, an alkenyl group, an alkynyl group or an aralkyl group, R ³ represents a hydrogen atom or a lower alkyl group, and Y represents a leaving group) . The production method according to claim 8, wherein the reduction of the nitro group of oxazolidinedione of general formula (II) is carried out in acetic acid or in a mixed solvent of acetic acid and ethyl acetate. The production method according to claim 8, wherein the leaving group represented by Y is selected from the group consisting of iodine atom, bromine atom, chlorine atom, tolylsulfonyl group, phenylsulfonyloxy group and methylsulfonyloxy group. The method of claim 8, wherein the base is selected from the group consisting of alkyl lithium, alkali metal hydrides and inorganic bases. A method for producing a compound, wherein the benzoxazide of formula (I) is characterized by reacting a carbamic acid ester of formula (VI) with a base. (Wherein R ¹ represents a hydrogen atom or an alkyl group, R ² represents a hydrogen atom, an alkyl group, a cyanoalkyl group, an alkenyl group, an alkynyl group or an aralkyl group, and R ⁴ represents a lower alkyl group). 13. A process according to claim 12 wherein the base is selected from the group consisting of tertiary amines, aromatic amines, alkali metal alkoxides, alkali metal hydrides, inorganic bases and carboxylic acid metal salts. A preparation composition characterized in that it contains a compound or a pharmaceutically acceptable carrier or diluent and at least one benzoxazide of formula (I): (Wherein R ¹ represents a hydrogen atom or an alkyl group, and R ² represents a hydrogen atom, an alkyl group, a cyanoalkyl group, an alkenyl group, an alkynyl group or an aralkyl group). The formulation of claim 14 wherein the composition is in the form of a wettable powder, emulsion powder or granules. ※ Note: The disclosure is based on the initial application.