KR850003720A - Method for preparing ureido derivative - Google Patents

Abstract

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Description

Method for preparing ureido derivative

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Claims (13)

After ringing the compound of formula (IV) or reacting a compound of formula (V) with a compound of formula (VI), the protected functional group is converted into a free functional group and, if necessary, generated. Converted compounds into other compounds of general formula (I), and / or convert the resulting free compounds into salts and / or the resulting salts into free or other salts, and / or the resulting isomeric mixture, if necessary. Isolating the individual isomers thereof to prepare compounds of formula (I) and salts thereof. Wherein Ar is a monocyclic or optionally partially saturated bicyclic carbocyclic or heterocyclic aromatic radical; R is hydrogen, alkanoyl or alloyl and R ¹ and R ² are independently hydrogen or lower alkyl, or R ¹ and R ² are bonded together and two nitrogens attached to them by 2 to 4 carbon atoms Alkylene having 2 to 7 carbon atoms separating the atoms; R ³ and R ⁴ are independently hydrogen or lower alkyl; X is soxo or thio; In formula (IV), one of the radicals X ¹ and X ² is hydrogen and the other one is the acyl, radical of the carboxylic acid semi-derivative; In formulas (V) and (VI), R ¹ and X ¹ together represent a group of formula = C = X (IVa), X ² is hydrogen and R ³ is hydrogen or lower alkyl, or R ² and R ² together represent a group of formula = C = X (IVa), X ¹ is hydrogen, R ¹ is hydrogen or lower alkyl and participates in the reaction in compounds of formulas (IV), (V) and (IV) Unfunctional groups may exist in protected form. The acyl radical X ¹ of the carboxylic acid semi-derivative according to claim 1, in which R ¹ and R ² together form a alkylene group, preferably as defined in claim 1, in the starting material of formula (IV). Or X ² is the corresponding radical of carboxylic acid half-ester, carboxylic acid half-halide or carboxylic acid half-amide. The method of claim 1 wherein, X ¹ and X ² are both alkylene groups, such as the hydrogen in the starting material of formula (Ⅳ) with is reacted with a carbonic acid reactive derivative, R ¹ and R ² defined in claim 1 Process for preparing a starting material of the general formula (IV) to form a in situ. 4. The corresponding diester of claim 3, wherein the reactive derivative of carbonic acid is a di-lower alkyl-carbonate, a dihalide such as phosgene, a halogeno-carboxylic acid ester such as lower alkylhalogenocarbonate, a carbasan halide or , Carboxylic acid di-amides such as N, N′-carbonyl-diimidazole. The compound of claim 1, wherein Ar is optionally substituted phenyl, pyridyl, naphthyl, tetrahydronaphthyl, 3,4-dihydro-1 (2H) -naphthalenonyl, 3,4- Dihydro-2 (1H) -quinoloyl, 3,4-dihydro-1 (2H) -isoquinoloyl, indolyl or 1,2,5-thiadiazolyl, R, R ₁ , R ² , R ³ , R ⁴ and X are processes for preparing compounds of formula (I) or salts thereof as defined in claim 1. The compound of claim 1, wherein Ar is phenyl, or lower (alkyl, alkenyl, alkynyl, alkanoyl, mono- or di-alkyl amino, alkanoylamino, alkylsulfonylamino, alkoxycarbonyl, Alkylcarbamoyl, alkylsulfamoyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyloxy and alkynyloxy), hydroxy, cyano, haloranono, pyrrolyl, amino, 5-7 member- Alkylene-, oxaalkylene-, thiaalkylene-) imino, benzyloxy, phenyl, 5- to 7-membered cycloalkyl, carbamoyl, sulfamoyl and 3- to 7-membered cycloalkyl-, phenyl-, hydroxy-, To one to three substituents selected from lower alkoxy, lower alkoxycarbonylamino-, lower alkylthio-, lower alkylsulfinyl-, lower alkylsulfonyl-, and carbamoyl-substituted (lower alkyl and lower alkoxy) Phenyl substituted by; R is hydrogen, lower alkanoyl or aroyl and R ¹ and R ² are hydrogen or lower alkyl, or R ¹ and R ² are bonded together and two nitrogen atoms attached to them by 2 to 4 carbon atoms A process for preparing a compound of formula (I) or a salt thereof, wherein alkylene having 2 to 5 carbon atoms, R ³ and R ⁴ are hydrogen or lower alkyl, and X is O or S. The compound according to any one of claims 1 to 4, wherein Ar is as defined in claim 6, R is hydrogen, and R ¹ and R ² are bonded together to represent alkylene having 2 to 4 carbon atoms. Or a 7-membered ring, wherein R ³ and R ⁴ are hydrogen or lower alkyl and X is O or S. The process according to any one of claims 1 to 4, wherein the compound of formula (II) or a salt thereof is prepared. Wherein R is hydrogen or lower alkanoyl, R ¹ and R ² are hydrogen, or R ¹ and R ² are bonded together to represent straight chain alkylene having 2 to 4 carbon atoms, R ³ and R ⁴ independently Hydrogen or lower alkyl, R ⁵ and R ⁶ are each independently hydrogen, lower (alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy), hydroxy, cyano, halogeno, amino, lower (Mono- or di-ylalkylamino, alkanoylamino, alkylsulfonylamino, alkylthio, alkylsulfinyl or alkylsulfonyl), morpholino, 1- or 2-pyrrolyl, phenyl, 5- or 7-membered cycloalkyl , Lower alkanoyl, lower alkoxycarbonyl, carbamoyl or sulfamoyl, R ⁶ is also cycloalkyl, phenyl, lower alkoxy, hydroxy, lower alkoxycarbonylamino, lower alkyl- (thio, Sulfinyl and sulfonyl) or lower (alkyl or alkoxy) substituted with carbamoyl And, X is O or S. 5. The compound of claim ¹ , wherein R, R ¹ and R ² are as defined in claim 8, R ³ , R ⁴ and R ⁵ are hydrogen, R ⁶ is lower alkyl, lower alkenyl, lower Alkynyl, lower alkyl (thio, sulfinyl or sulfonyl), lower alkoxy, lower alkenyloxy, cyano, lower alkoxycarbonyl, carbamoyl, lower alkanoylamino, morpholino, pyrrolyl, 5- to 7-membered Cycloalkyl, R ⁶ is also lower (alkyl or alkoxy) substituted with cycloalkyl, phenyl, lower alkoxy or carbamoyl having 3 to 5 carbon atoms, and X is 0, and the general formula (II) according to claim 8 Method for preparing a compound or a salt thereof. The process according to any one of claims 1 to 4, wherein the compound of formula (III) or a salt thereof is prepared. Wherein R ³ is hydrogen or lower alkyl, R ⁷ is cyano, lower alkoxycarbonyl, pyrrolyl, morpholino, alkenyloxy having 3 to 6 carbon atoms, ilkynyloxy having 3 to 6 carbon atoms, Or alkoxy having 1 to 3 carbon atoms substituted with cyclopropyl. The cis-1- ｛4-[[3- (2-allyloxy-phenoxy) -2-hydroxy-propyl] -amino] -cyclohexyl-2--2-imide according to any one of claims 1 to 4. A process for preparing dazolidinones or salts thereof. The cyclohexyl -2--2- of any one of claims 1 to 4, wherein cis-l- 4- [[3- (2-cyclopropylmethoxy) -2-phenoxyhydroxy-propyl] -amino] -cyclohexyl-2--2- Process for preparing imidazolidinone or salts thereof. (S) -cis-1-'4- [C3- (2-cyclopropylmethoxy-phenoxy) -2-hydroxy-propyl] -amino] -cyclohexyl according to any one of claims 1 to 4. VII-2-imidazolidinone or a method for producing a salt thereof. ※ Note: The disclosure is based on the initial application.