- Preparation method of medicine ezetimibe for treating hyperlipidemia
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The invention discloses a preparation method of a medicine ezetimibe for treating hyperlipidemia, belonging to the field of pharmaceutical synthesis. According to the preparation method, a compound 2is taken as a raw material, and the ezetimibe 1 is prepared by four steps of carbonyl protection, cyclization, carbonyl reduction and oxidation. Compared with the existing method reported by documents, the preparation method provided by the invention avoids the use of a polluting titanium reagent, and is fewer in synthesis steps, higher in process stability and suitable for large-scale production.
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Paragraph 0023; 0030; 0037
(2018/03/26)
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- Preparation method of ezetimibe for treating hyperlipidemia
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The invention discloses a preparation method of ezetimibe for treating hyperlipidemia, and belongs to the field of drug synthesizing. The method is characterized in that a compound 2 is treated as theraw material and subjected to four synthesizing steps to prepare ezetimibe 1, wherein the four steps include the step of protection for carbonyl group, cyclizing, carbonyl reduction and hydrogenationdeprotection. Compared with methods in existing documents, the preparation method has the advantages that the use of polluting titanium agents is avoided; the synthesizing steps are decreased; the technology stability is improved; massive production can be performed.
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Paragraph 0021; 0022; 0030; 0037
(2018/03/25)
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- Preparation method of ezetimibe serving as drug for treating hyperlipidemia
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The invention discloses a preparation method of ezetimibe serving as a drug for treating hyperlipidemia and belongs to the field of drug synthesis. Ezetimibe 1 is prepared by carrying out four synthesis steps including carbonyl protection, cyclization, carbonyl reduction and deprotection on a compound 2 serving as a raw material. Compared with a method reported by an existing document, the preparation method is capable of avoiding using a polluting titanium reagent and reducing the synthesis steps, higher in process stability and suitable for large-scale production.
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Paragraph 0022; 0030; 0037
(2018/05/01)
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- Carbonyl group protection method
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The invention belongs to the technical field of methods for protection of groups in organic chemistry reaction, and particularly discloses a carbonyl group protection method. The response equation is shown in the description, wherein R1 and R2 are alkyl,
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Paragraph 0051; 0052
(2017/02/09)
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- PROCESSES FOR PREPARING INTERMEDIATE COMPOUNDS USEFUL FOR THE PREPARATION OF EZETIMIBE
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The invention relates, in general, to an improved process for the preparation of the compounds (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one and (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-azetidin-2-one, which are key intermediates for the synthesis of ezetimibe, as well as the use of these intermediates for the preparation of ezetimibe.
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Page/Page column 14
(2009/09/26)
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- METHOD OF MANUFACTURING (3R, 4S) -1- (4-FLUOROPHENYL) -3- [ (3S) -3- (4 -FLUOROPHENYL) -3-HYDROXYPROPYL) ] -4- (4-HYD ROXYPHENYL) -2-AZETIDINONE
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A method of manufacturing (3R,4S)-l-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3- hydroxypropyl)]-4-(4-hydroxyphenyl)-2-azetidinone (Ezetimibe) of formula I, starting from the optically active (S)-N-acyl-oxazolidide of formula II, which is reacted with an alkyleneglycol of general formula III, (stage 1), and the obtained acetal-oxazolidide of general formula IV, is subjected to reaction with a silyl-imine of general formula V the produced amino-oxazolidide of general formula VI, (stage 3), and the obtained silylated azetidinone of general formula VII, is desilylated (stage 4), and the ketal of general formula VIII produced this way, is deketalized formula IX is finally reduced.
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Page/Page column 7
(2008/12/07)
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- PROCESS FOR THE PRODUCTION OF EZETIMIBE AND INTERMEDIATES USED IN THIS PROCES
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This invention provides a novel, industrially easily realizable and economical process comprising only few steps, and built on new intermediates for the production of 1-(4-3(R)- [3(S)-(4-fluorophenyl)-3-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone (ezetimibe) according to the following reaction scheme: (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI) wherein, the substances of the general Formulas II, IV, VI, VIII, IX, X and XI are new, Formula III is a non-isolated intermediate, Rl, R2 and R3 are represented by the compounds of Formulas Va-Vd, (Va), (Vb), (Vc), (Vd) and R4 is a silil, e.g. tert.buthyl-dimethyl-silil, tert-buthyl-diphenyl-silil group.
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Page/Page column 16
(2008/06/13)
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