- The convergent synthesis of CI-981, an optically active, highly potent, tissue selective inhibitor of HMG-CoA reductase
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The synthesis of CI-981 is described starting from isobutyrylacetanilide (3) and the key chiral intermediate 2.
- Baumann,Butler,Deering,Mennen,Millar,Nanninga,Palmer,Roth
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Read Online
- Preparation method of atorvastatin calcium isomers
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The invention relates to a preparation method of atorvastatin calcium isomers [R-(R*,R*)]-2-(3-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-2-phenyl-4-[(aniline)carbonyl]-1H-pyrrole-1-calciumenanthate salt (IMP-1 for short) and [R-(R*,R*)]-3-(2-fluorophenyl)-beta, delta-dihydroxyl -5-(1-Methylethyl)-3-phenyl-4-[(anilino)carbonyl]-1H-pyrrole-1- calcium enanthate salt (IMP-2 for short). According to the preparation method, a preparation method of a reference substance is provided for the quality research of drugs, and an important guiding significance is provided for the safe medicationof atorvastatin calcium.
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- Preparation method of atorvastatin calcium
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The invention belongs to the technical field of medicine preparation and particularly relates to a patent application about a novel preparation method of atorvastatin calcium. The method includes steps of preparing intermediates including: 2-methyl-3-carbonyl-methyl pentanoate, 2-methyl-3,5-dicarbonyl-5-anilino-butane, 4-methyl-3-oxo-N-phenyl-2-benzylidene pentanamide, 4-(4-fluorophenyl)-2-(2-methylpropionyl)-4-oxo-N-beta-diphenyl butyrylamide. The preparation method employs cheap and easy-to-obtained raw materials, has simple reactions and operations, and has great industrial application prospect. In conclusion, the preparation method has high reaction efficiency and product yield, is good in repeatability, is suitable for industrial production and has great application value and promotion and application significance.
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- α-Unsubstituted Pyrroles by NHC-Catalyzed Three-Component Coupling: Direct Synthesis of a Versatile Atorvastatin Derivative
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A practical one-pot cascade reaction protocol provides direct access to valuable 1,2,4-trisubstituted pyrroles. The process involves an N-heterocyclic carbene (NHC)-catalyzed Stetter-type hydroformylation using glycolaldehyde dimer as a novel C1 building-block, followed by a Paal-Knorr condensation with primary amines. The reaction makes use of simple and commercially available starting-materials and catalyst, an important feature regarding applicability and utility. Low catalyst loading under mild reaction conditions afforded a variety of 1,2,4-substituted pyrroles in a transition-metal-free reaction with high step economy and good yields. This methodology is applied in the synthesis of a versatile Atorvastatin precursor, in which a variety of modifications at the pyrrole core structure are possible.
- Fleige, Mirco,Glorius, Frank
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p. 10773 - 10776
(2017/08/22)
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- The total synthesis of calcium atorvastatin
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A practical and convergent asymmetric route to calcium atorvastatin (1) is reported. The synthesis of calcium atorvastatin (1) was performed using the remote 1,5-anti asymmetric induction in the boron-mediated aldol reaction of β-alkoxy methylketone (4) with pyrrolic aldehyde (3) as a key step. Calcium atorvastatin was obtained from aldehyde (3) after 6 steps, with a 41% overall yield.
- Dias, Luiz C.,Vieira, Adriano S.,Barreiro, Eliezer J.
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p. 2291 - 2296
(2016/03/01)
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- Ionic tagged amine supported on magnetic nanoparticles: Synthesis and application for versatile catalytic Knoevenagel condensation in water
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Propylamine modified with imidazolium ionic moiety grafted onto magnetic nanoparticles (MNPs) was prepared and evaluated as a catalyst for Knoevenagel condensation in water at room temperature. The catalyst was efficient in the reaction to give the condensation products in good yields. It is worth noting that the ionic-tagged catalyst performed significantly better than its ionic tag-free counterpart. Finally, the catalyst could be reused for 8 times with a slight loss in its catalytic activity. the Partner Organisations 2014.
- Ying, Anguo,Qiu, Fangli,Wu, Chenglin,Hu, Huanan,Yang, Jianguo
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p. 33175 - 33183
(2014/08/18)
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- Synthesis and antimicrobial activities of some novel 4-substituted pyrazoline derivatives
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A series of 5-aryl-3-isopropyl-4-[N-phenyl-aminocarbonyl]-4,5-dihydro-1H- pyrazoles were synthesized by the reaction between 3-aryl-2-isobutanoyl-N- phenyl-acrylamide with hydrazine hydrate in acetic acid as solvent gives acetyl pyrazoline. All the compounds have been evaluated for their in vitro biological assay like antibacterial activity towards Gram-positive and Gram-negative bacterial strains and antifungal activity towards Aspergillus niger at a concentration of 40 μg. The biological activities of synthesized compounds were compared with standard drugs.
- Godhasra,Patel,Kansagara,Thanki,Shah
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experimental part
p. 495 - 499
(2011/07/31)
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- Process for the synthesis of atorvastatin form v and phenylboronates as intermediate compounds
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The present invention discusses a novel process for the synthesis of [R-(R*,R*)]-2-(4-fluorophenyl)-B,D-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemi calcium, atorvastatin. The compound so prepared is useful as inhibitor of the enzyme HMG-CoA reductase and may thus be used as hypolipidemic and hypocholesterolemic agent.
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- Synthesis of deuterium-labeled atorvastatin and its metabolites for use as internal standards in a LC/MS/MS method developed for quantitation of the drug and its metabolites in human serum
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D5-labeled isotopomers of atorvastatin, atorvastatin lactone and its hydroxy metabolites were synthesized as internal standards for use in a LC/MS/MS method developed for the simultaneous quantitative determination of atorvastatin and its hydroxy metabolites in human serum. d5-Atorvastatin and d5-atorvastatin lactone were prepared from d5-aniline whereas their corresponding hydroxy metabolites were synthesized using d5-benzaldehyde.
- Chen, Bang-Chi,Sundeen, Joseph E.,Guo, Peng,Bednarz, Mark S.,Hangeland, Jon J.,Ahmed, Syed Z.,Jemal, Mohammed
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p. 261 - 270
(2007/10/03)
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- Process for the synthesis of protected esters of (S)-3,4-dihydroxybutyric acid
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The invention is an improved process for the preparation of a compound of formula I wherein R and R1 are each independently alkyl of from 1 to 3 carbon atoms; and R2 is alkyl of from 1 to 8 carbon atoms. STR1
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