KR860000297A - Method for preparing thiazolidine derivatives - Google Patents

Abstract

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Description

Method for preparing thiazolidine derivatives

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Claims (14)

The thiazolidine derivatives of the general formula (II) or salts thereof are reacted with the piperazine derivatives of the general formula (III) or salts thereof, or the thiazolidine derivatives or salts thereof of the general formula (IV) Reacted with a piperazine derivative of formula (V) or a salt thereof, or a thiazolidine derivative or salt thereof of the following general formula (VI) with a compound of the general formula (VII), or Characterized in that the thiazolidine derivative of or a salt thereof is reacted with an amine compound of formula (III) or a salt thereof and, if necessary, the product is converted into a pharmaceutically acceptable salt thereof. A process for preparing a thiazolidine derivative of the general formula (I) or a pharmaceutically acceptable salt thereof. Wherein, R ¹ is a phenyl group unsubstituted or substituted, Q is a single bond, a lower alkylene group or lower alkenylene group, R ² is R ³ are the same or different and are each a hydrogen atom, lower alkyl group, a cycloalkyl An alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a benzoyl group, a phenyl group, or a di (lower alkyl) phosphazole group, Alk is a lower alkene group, and Y and Z are the same or , And are each an oxygen atom or a sulfur atom, and X ¹ , X ² , X ³ and X ⁴ are reactive moieties. The thiazolidine derivative of formula (I-b) or a salt thereof is reacted with a glycid compound of formula (VII) to obtain a compound of formula (I-a), or the following formula (VI) A thiazolidine derivative of or a salt thereof is reacted with a compound of formula (XI) to obtain a compound of formula (Ic), or a thiazolidine derivative of formula (Ie) or a salt thereof Reacting with a compound of formula (XII) to obtain a compound of formula (Id), or hydrolyzing a thiazolidine derivative or a salt thereof of formula (XIII) to obtain a compound of formula (If) And hydrolyzing the tazolidine derivative (If) or a salt thereof to give a compound of the general formula (Ig), and if necessary, converting the product into a pharmaceutically acceptable salt thereof. And the thiazole of the following general formula (I) Process for preparing a salt of derivatives or a pharmaceutically acceptable thereof. Wherein, R ¹ is a phenyl group unsubstituted or substituted, Q represents a single bond, a lower alkylene group or a group of lower alkenyl, R ² is R ³ are the same or different, each represent a hydrogen atom, lower alkyl group Is a cycloalkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a benzoyl group, a phenyl group, or a di (lower alkyl) phosphosol group, Alk is a lower alkene group, and Y and Z are The same or different and each is an oxygen atom or a sulfur atom, R ⁴ is a lower alkyl group or a substituted or unsubstituted phenyl group, R ⁵ is a lower alkyl group, R ²¹ is a lower alkyl group, R ³¹ is a lower alkyl group, Cycloalkyl group, lower alkanoyl group, lower alkoxycarbonyl group, lower alkylsulfonyl group, benzoyl group, phenyl group, X ⁵ is a reactive moiety, R ²² is lower alkanoyl group, lower alkoxycarbonyl group, lower Alkylsulfo A group or benzoyl group. 3. A compound according to claim 1 or 2, wherein R ¹ is phenyl unsubstituted or substituted with one or more substituents selected from the group consisting of halogen atoms, lower alkyl, lower alkylthio, lower alkoxy and nitro, and R ² is an inner atom, lower Alkyl, cycloalkyl, lower alkanoyl, lower alkoxycarbonyl, lower alkylsulfonyl, benzoyl or phenyl or di (lower alkyl) phosphoryl and R ³ is hydrogen atom or lower alkyl, or R ² is lower alkyl, R ³ Is lower alkanoyl or benzoyl. The compound of claim 1 or 2, wherein R ¹ is substituted with at least one substituent selected from the group consisting of chlorine, fluorine, alkyl having 1 to 3 carbon atoms, alkoxy having 1 to 3 carbon atoms, alkylthio having 1 to 3 carbon atoms, and nitro group. Or unsubstituted phenyl, Q is a single bond, alkylene or propenylene having 1 to 3 carbon atoms, Alk is alkylene having 2 to 5 carbon atoms, R ² is a hydrogen atom, alkyl having 1 to 4 carbon atoms, Cycloalkyl of 4 to 6, alkanoyl of 2 to 5 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms, benzoyl, phenyl or di (alkyl) phosphoryl having 2 to 6 carbon atoms, R ³ is a hydrogen atom or 1 to C Or tetraalkyl or R ² is C 1 to C 3 alkyl and R ³ is alkanoyl or benzoyl having 2 to 5 carbons. 5. A compound according to claim 4, wherein R ¹ is phenyl, fluorophenyl, chlorophenyl, methylphenyl or methoxyphenyl, Q is a single bond, Alk is ethylene or trimethylene, R ² is a hydrogen atom or a carbon atom of 1 to 3 Alkyl and R ³ is a hydrogen atom, alkyl having 1 to 3 carbon atoms or alkanoyl having 2 to 4 carbon atoms. The method of claim 4, wherein R ¹ is phenyl, fluorophenyl or methylphenyl, Q is a single bond, Alk is ethylene, R ² is a hydrogen atom or methyl, and R ³ is a hydrogen atom, methyl or acetyl. 7. The method of claim 6, wherein Y is an oxygen atom and Z is an oxygen atom or a sulfur atom. 7. The method of claim 6, wherein R ¹ is phenyl or fluorophenyl, R ² is methyl, R ³ is hydrogen or acetyl and Y and Z are oxygen atoms. 8. A compound according to claim 7, wherein N-methyl-2- {2- [2- (4-phenylpiperazin-1-yl) ethyloxy] phenyl} thiazolidine-3-carbonioamide or a pharmaceutically acceptable thereof How to prepare a salt. 8. A compound according to claim 7, wherein N-methyl-2- {2- [2- (4- (2-fluorophenyl) piperazin-1-yl) ethyloxy] phenyl} thiazolidine-3-carbothioamide or To prepare a pharmaceutically acceptable salt thereof. The compound according to claim 8, wherein N-2- {2- [2- (4-methylphenylpiperazin-1-yl) ethyloxy] phenyl} thiazolidine-3-carboxamide or a pharmaceutically acceptable salt thereof How to manufacture. The compound according to claim 8, wherein (-)-N-methyl-2- {2- [2- (4-phenylpiperazin-1-yl) ethyloxy] phenyl} thiazolidine-3-carboxoamide or its Method for preparing a pharmaceutically acceptable salt. The compound according to claim 8, wherein (+)-N-methyl-2- {2- [2- (4-phenylpiperazin-1-yl) ethyloxy] phenyl} thiazolidine-1-carboxamide or a pharmaceutical thereof Methods of preparing salts that are generally acceptable. The compound according to claim 8, wherein N-acetyl-N-2- {2- [2- (4- (3-fluorophenyl) piperazin-1-yl) ethyloxy] phenyl} thiazolidine-3-carbox A method of making an amide or a pharmaceutically acceptable salt thereof. ※ Note: The disclosure is based on the initial application.