KR830001197A - △2-11-Desoxy-PGF₂ or PGE₂prostaglandin derivative production method and its use as a drug - Google Patents

Abstract

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Description

△2-11-Desoxy-PGF2 or PGE2 series prostaglandin derivatives production method and use thereof as a drug

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Claims (1)

The aldehyde of the following structural formula (II) was reacted with the Grignard reagent of the following structural formula (III) to obtain an alcohol of the following structural formula (IV), and ignited by hydrolyzing the three protecting groups in the alcohol of the obtained structural formula (IV). The aldehyde of structural formula (V) was obtained, and the obtained aldehyde of structural formula (V) was reacted with the ylide of structural formula (VI) to obtain a compound of structural formula (VII), and the obtained keto-ester of structural formula (VII) was obtained. Hydrolysis to convert to a compound of formula (I) (R ¹ is hydrogen, X ¹ and Y ¹ are together oxygen, X ² and Y ² are different from each other, hydrogen or hydroxyl, R ² is as described below) and obtained The resulting compound is reduced to a compound of the structural formula (I) (X ¹ and Y ¹ and X ² and Y ² are different from each other, hydrogen or hydroxyl, R ¹ is hydrogen and R ² is as described below) using a metal complex hydride. Or reducing the obtained keto-ester of the structural formula (VII) using a metal complex hydride, and hydrolyzing the obtained compound in the same manner as d) or oxidizing the alcohol of the structural formula (IV) to obtain the following structural formula (VIII). It was converted into a compound and separated by acid decomposition of the three protecting groups in the obtained keto compound of the structural formula (VIII) to obtain a compound of the following structural formula (IX), and the obtained keto-aldehyde of the structural formula (IX) was obtained according to step c). By reacting with the ylide of the structural formula (VI) to obtain a compound of the following structural formula (X), and by acidic decomposition of the obtained keto-ester of the structural formula (X), the compound (R ² ) of the structural formula (I) is as described below, and R ¹ is hydrogen and X ¹ and Y ¹ and X ² and Y ² together represent oxygen) and optionally, X ¹ , X ² , Y ¹ , Y ² and R ² are as described below and R ¹ is hydrogen By esterification of the compound of the phosphorus structural formula (I), X ¹ , Y ¹ , X ² , Y ² and R ² to obtain a compound of the structural formula (I) in which R ¹ to be described later is not hydrogen, and optionally, X ¹ , X ² , Y ¹ , Y ² and R ² will be described later A method for producing a compound of the following structural formula (I), characterized in that the compound of the structural formula (I), wherein R ¹ is hydrogen, is converted into a physiologically non-toxic metal or an amine salt. T-1 In the above structural formula X ¹ and Y ¹ and X ² and Y ² are the same or different, and together are oxygen or each hydrogen or hydroxyl R ¹ is hydrogen or a straight or branched chain of up to 10 carbon atoms, saturated or unsaturated, aliphatic or cycloaliphatic hydrogen radical, or derived from a physiologically non-toxic metal ion or NH ₄ ± ion, or primary, secondary or tertiary amine Ammonium ion, R ² is a straight-chain or branched, saturated or unsaturated, aliphatic hydrocarbon radical of up to 7 carbon atoms (non-terminal CH ₂ group may be substituted with oxygen) or a cycloalkyl radical having 3 to 7 carbon atoms R ³ is a prone group Z ¹ is a -CH ₂ group, -CCCH ₃ ) ₂ group or a single bond Z ² is a -CH ₂ group, -CCCH ₃ ) ₂ group or a single bond Hal is chlorine, bromine and iodine R ⁴ are the same or different and are straight-chain C ₁ -C ₄ alkyl or phenyl. ※ Note: It is disclosed according to the contents of the initial application.