147118-40-9

Usage

Uses

Used in Pharmaceutical Industry:
Rosuvastatin methyl ester is used as an impurity in the pharmaceutical industry for Rosuvastatin dosage forms. The presence of this impurity is significant as it can impact the efficacy, safety, and quality of the final drug product. It is essential to monitor and control the levels of Rosuvastatin methyl ester during the manufacturing process to ensure the therapeutic benefits of Rosuvastatin are not compromised.
Additionally, understanding the properties and behavior of Rosuvastatin methyl ester can aid in the development of improved drug delivery systems and formulations, potentially enhancing the bioavailability and effectiveness of Rosuvastatin in treating hypercholesterolemia and related cardiovascular conditions.
Used in Research and Development:
Rosuvastatin methyl ester serves as a valuable compound for research and development purposes in the pharmaceutical sector. It can be used to study the degradation pathways of Rosuvastatin, understand the factors that contribute to its formation, and develop strategies to minimize its presence in the final drug product. This knowledge can contribute to the improvement of manufacturing processes, quality control measures, and the overall safety and efficacy of Rosuvastatin-based treatments.

InChI:InChI=1/C23H30FN3O6S/c1-14(2)21-19(11-10-17(28)12-18(29)13-20(30)33-4)22(15-6-8-16(24)9-7-15)26-23(25-21)27(3)34(5,31)32/h6-11,14,17-18,28-29H,12-13H2,1-5H3/b11-10+/t17-,18-/m1/s1

Upstream product

• 147118-39-6 methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate 
• 912337-61-2 methyl (6E)-7-{4-(4-flurophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}(5S)-5-hydroxy-3-oxo-6-heptenoate 
• 147118-35-2 methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate 
• 289042-12-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester 
• 124752-23-4 tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 67-56-1 methanol 
• 503610-43-3 Rosuvastatin lactone 
• 851440-19-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid methyl ester 
• 164576-45-8 (4R-cis)-6-formyl-2,2-dimethyl-1,3-dioxane-4-acetic acid methyl ester 
• 140164-51-8 methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate 
• 171523-71-0 (+)-(3R,5S)-Methyl 6-acetoxy-3,5-(isopropylidenedioxy)hexanoate 
• 391218-16-9 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid methyl ester 
• 147118-38-5 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonamido)-pyrimidin-5-yl)-(3R)-3-tert-butyldimethylsiloxy-5-oxo-(E)-6-heptenoic acid methyl ester 
• 147118-30-7 ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid 

Downstream Products

• 851440-19-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid methyl ester 
• 287714-41-4 rosuvastatin 
• 1353050-09-5 (3R,5S,E)-methyl 3,5-bis(tert-butyldimethylsilyloxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)hept-6-enoate 
• 1353050-10-8 (3R,5S,E)-3,5-bis(tert-butyldimethylsilyloxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)hept-6-enoic acid 
• 1353050-11-9 (3R,5S,E)-((R)-5,6-dinitrooxyhexyl) 3,5-bis(tert-butyldimethylsilyloxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)hept-6-enoate 
• 1353050-31-3 (3R,5S,E)-((R)-5,6-bis(nitrooxy)hexyl) 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-enoate 
• 1374771-96-6 rosuvastatin, S-benzylisothiourea salt 
• 917805-74-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid-2-methylpropan-2-amine 
• 1019876-66-4 (+)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methanesulfonyl-methyl-amino)-pyrimidin-5-yl)-(3R,5S,6E)-dihydroxy-hept-6-enoic acid n-butylamide 
• 503610-43-3 Rosuvastatin lactone 
• 1388654-77-0 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid 4-methylpentan-2-yl ester 
• 1416820-71-7 rosuvastatin (R)-1-(1-naphthyl)ethylamine 
• 1197348-98-3 3-methylbutyl (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate 
• 852820-97-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidine-5-yl]-3,5-dihydroxyhept-6-enoic acid isopropylamine 

Relevant academic research and scientific papers

Synthetic studies on statins. Part 3: A facile synthesis of rosuvastatin calcium through catalytic enantioselective allylation strategy

A concise and stereocontrolled synthesis of rosuvastatin calcium has been accomplished, with the key steps including a Keck enantioselective allylation of chloroacetaldehyde with allyltributylstannane to install 5R-stereocenter and a VO(acac)2-catalyzed syn-diastereoselective epoxidation of (S)-1-chloropent-4-en-2-ol to set the requisite 3R-chirality.

Statins intermediate and its derivatives

The invention discloses a preparation method for a tatin intermediate and derivatives thereof. The compound adopts a structure shown in a formula I (refer to the specification); the preparation method is that a compound shown in a formula II (refer to the specification) and a nucleophile reagent are subjected to the ring-opening reaction, wherein R is a C1-10 alkoxy group. The preparation method has the advantages that the mild conditions are realized, the reaction operation is simple, the reaction time is short, the product transformation ratio is high and the method is suitable for large-scale production.

Preparation process of rosuvastatin calcium preparation

The invention provides a preparation process of a rosuvastatin calcium preparation, and belongs to the technical field of pharmaceutical preparations. With (3R)-tert-butyldimethylsiloxy-5-oxy-6-triphenylphosphoranylidene methyl caproate and 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amino)pyridine-5-formaldehyde as initial raw materials, wittig reaction, deprotection reaction, chiral reduction reaction, hydrolysis reaction and purification are carried out so as to obtain a rosuvastatin calcium crude drug; then the rosuvastatin calcium crude drug is uniformly mixed with a diluent, a disintegrating agent, a stabilizing agent and a lubricant so as to obtain a mixture, and then the mixture is tabletted so as to obtain the rosuvastatin calcium preparation. The preparation process of the rosuvastatin calcium preparation disclosed by the invention has the advantages of simple operation, high yield, low cost and stable quality.

Method for the preparation of high purity Rosuvastatin Calcium salt

The present invention relates to a method for manufacturing a Rosuvastatin calcium salt by using a Rosuvastatin tert-butyl amine salt, and to a method for manufacturing a high purity Rosuvastatin calcium salt, which has impurities less than 0.1% of a diastereomer. The manufacturing method of a high purity Rosuvastatin calcium salt comprises the steps of: 1) manufacturing a compound represented by chemical formula III by reducing a compound represented by chemical formula IV; 2) manufacturing a compound represented by chemical formula II by adding t-butyl amine; and 3) manufacturing a compound represented by chemical formula I by adding a calcium ion to the compound represented by chemical formula II.COPYRIGHT KIPO 2016

3,5-dihydroxyhept-6-enoic acid derivative preparation method

The invention relates to a preparation method of 3, 5-dihydroxy-6-heptenoic acid derivatives. The preparation method comprises the steps of hydrolyzing crude statin ester to form a water-soluble alkali metal salt, extracting by using a solvent to remove impurities which cannot be dissolved into water, and converting at high yield to form ester with relatively high purity; then, purifying the ester by using a recrystallization way to obtain pure statin ester; and finally, converting the pure statin ester at high yield to form statin calcium, namely the 3, 5-dihydroxy-6-heptenoic acid derivatives. The 3, 5-dihydroxy-6-heptenoic acid derivatives, namely rosuvastatin calcium and pitavastatin calcium, synthesized by using the preparation method are high in purity and total yield, relatively low in cost and beneficial to mass production.

Rosuvastain calcium intermediate crystallization method

The invention discloses a crystallization method of a rosuvastatin calcium intermediate. The crystallization method comprises the following steps: (1) adding the prepared grease of an intermediate H3 to a mixed solvent composed of an ester solvent, an alkane solvent and an ether solvent, performing primary pulping and evaporating out one part of the mixed solvent under reduced pressure; (2) adding the ether solvent and performing secondary pulping; (3) adding the alkane solvent; (4) adding the seed crystal of the intermediate H3; and (5) adding the ether solvent, performing third pulping, and separating out solid to obtain the solid product of the intermediate H3. According to the crystallization method of the rosuvastatin calcium intermediate, the mixed solvent is adopted to crystallization step by step so as to guarantee smooth separation of the rosuvastatin calcium intermediate H3 in the solid form and the obtained intermediate H3 is high in purity; and meanwhile, the operating method is simple, good in repeatability and suitable for industrial production.

Synthetic method for rosuvastatin methyl ester

The invention provides a synthetic method for rosuvastatin methyl ester. According to the method, protected butyl ester is used as a raw material and esterified again in presence of a catalyst to prepare rosuvastatin methyl ester. The method is low in cost and high in yield, and a new valuable path is provided for synthesis of rosuvastatin methyl ester.

Synthetic method of rosuvastatin

The invention provides a synthetic method of rosuvastatin. The method is characterized in that butyl rosuvastatin is esterified in the presence of a neutral titanate catalyst to prepare methyl rosuvastatin. The method has the advantages of low cost and high yield, and provides a new valued approach for synthesis of the methyl rosuvastatin.

PROCESS FOR PREPARING ROSUVASTATIN CALCIUM THROUGH NOVEL AMINE SALT

The present invention provides a process for preparing pure rosuvastatin of formula I, or pharmaceutically acceptable salts thereof through rosuvastatin l-(l-naphthyl)ethyl salt of formula II wherein wavy line (>~w) represent (R), (S) stereochemistry or racemate thereof.

PROCESS FOR THE PREPARATION OF ROSUVASTATIN CALCIUM VIA NOVEL AMINE INTERMEDIATE

The present invention, relates to novel amine salts of rosuvastatin and its process for the preparation. Moreover, the present invention also relates to improved process for the preparation of rosuvastatin calcium, employing novel amine salts as an intermediate.