KR850008154A - N, 3-disubstituted 2-oxyindole-1-carboxamide - Google Patents

Abstract

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Description

N, 3-disubstituted 2-oxyindole-1-carboxamide

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Claims (9)

The compound of formula (IV) is reacted with an isocyanate of the formula R ² -H = C = O in an inert solvent, or the compound of formula (V) is formula R ¹ -C (= O)-in an inert solvent. A process for preparing a 2-oxyindole-1-carboxamide compound of formula (I) or a pharmaceutically acceptable salt thereof, characterized by reacting with an active derivative of a carboxylic acid of OH. Wherein X is hydrogen, polouro, bromo, C1-C4 alkyl, C3-C7 cycloalkyl C1-C4 alkoxy, C1-C4 alkylthio, tripololomethyl , Alkylsulfinyl having 1 to 4 carbon atoms, alkylsulfonyl having 1 to 4 carbon atoms, nitro, phenyl, alkanoyl having 2 to 4 carbon atoms, benzoyl, tennoyl, alkanamido having 2 to 4 carbon atoms, benzamido or each C1-C3 alkyl group , -Dialkylsulfamoyl: Y is hydrogen, polouro, chloro, bromo, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, Or tripololomethyl: or X and Y together are 4,5-, 5,6- or 6,7-methylenedioxy groups or 4,5-, 5,6- or 6,7-ethylenedioxy Or when X and Y are bonded to adjacent carbon atoms together, they form a radical Z (wherein Z is And W is oxygen or sulfur): R ¹ is alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, cycloalkenyl having 4 to 7 carbon atoms, phenyl substituted phenyl, and alkyl moiety. A phenylalkyl having 1 to 3 carbon atoms, an alkyl moiety having 1 to 3 carbon atoms (substituted phenyl), a phenoxyalkyl having 1 to 3 carbon atoms, an alkyl moiety having 1 to 3 carbon atoms (substituted phenoxy) Alkyl, (thiophenoxy) alkyl having 1 to 3 carbon atoms, naphthyl bicyclo [2.2.1] heptan-2-yl, bicyclo [2.2.1] hept-5-en-2-yl, or- (CH ₂ ) nQR ⁰ : wherein the substituents on substituted phenyl, (substituted phenyl) alkyl and (substituted phenoxy) alkyl are poloo, chloro, bromo, alkyl of 1 to 4 carbon atoms, 1 to 4 carbon atoms Alkoxy or tripololomethyl of 4: n is 0,1 or 2: Q is furan, thiophene, pyrrole, pyrazole, imidazole , Thiazole, isothiazole, oxazole, isoxazole, 1,2,3-thiadiazole, 1,3,4-thiadiazole, 1,2,5 thiadiazole, tetrahydrofuran, tetrahydro A divalent radical derived from a compound selected from the group consisting of thiophene, tetrahydropyran, tetrahydropyran, pyridine, pyrimidine, pyrazine, benzo [b] furan and benzo [b] thiophene: R ⁰ is hydrogen or carbon number Alkyl of 1 to 3: R ₂ is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, benzyl, furyl, thienyl, pyridyl or formula (Wherein R ³ and R ⁴ are each hydrogen, polouro, chloro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or tripoloromethyl). 2. A compound according to claim 1, wherein X is in the 5-position or 6-position and is hydrogen, polouro, chloro, bromo or tripoloromethyl; Y is hydrogen and R ¹ is alkyl having 1 to 6 carbons, cycloalkyl having 3 to 7 carbons, furyl, thienyl, phenylalkyl having 1 to 3 carbon atoms in the alkyl moiety, furylmethyl, thienylmethyl or tripolo Romethyl; R ² represents an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 7 carbon atoms, or a 2-oxyindole-1-carboxamide compound of formula (I) which is a group of the following general formula: or a pharmaceutically acceptable salt thereof. How to manufacture. (Wherein R ³ and R ⁴ are hydrogen, polouro, chloro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or tripoloromethyl, respectively.) The compound of formula (IV) is reacted with an isocyanate of general formula R ³ -N = C═O in an inert solvent at a temperature in the range of 50 to 150 ° C. Characterized by. Wherein X, Y, R ¹ and R ² are as defined in claim 1 or 2. The process according to claim 3, wherein the aliphatic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, ethers, , Dimethylformamide, , The reaction is carried out in a solvent selected from dimethylacetamide, N-methylpyrrolidone and dimethyl sulfoxide. The compound of formula (V) according to claim 1 or 2, wherein the compound of formula (V) is dissolved in an inert solvent in the presence of 1 to 4 molar equivalents of basic agent at a temperature in the range of -10 to 25 ° C. Reacting with an active derivative of a carboxylic acid of the general formula R ¹ -C (═O) —OH. Wherein X, Y, R ¹ and R ² are as defined in claim 1 or 2. 6. The process of claim 5 wherein the active derivative is an acid chloride and the reaction is in a polar, aprotic solvent. The method according to any one of claims 1 or 3 to 6, wherein Y is hydrogen and X is hydrogen, 5-chloro, 6-chloro, 5-fluoro or 6-fluoro. 8. A process according to claim 7, wherein R ¹ is benzyl, 2-furyl, 2-thienyl, (2-furyl) methyl or (2-thienyl) methyl. The method of claim 8, wherein X is 5-chloro, R ¹ is 2-furyl and R ² is t-butyl. ※ Note: The disclosure is based on the initial application.