CN101560177A - Preparation method of atorvastatin calcium - Google Patents
Preparation method of atorvastatin calcium Download PDFInfo
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- CN101560177A CN101560177A CNA2008101041569A CN200810104156A CN101560177A CN 101560177 A CN101560177 A CN 101560177A CN A2008101041569 A CNA2008101041569 A CN A2008101041569A CN 200810104156 A CN200810104156 A CN 200810104156A CN 101560177 A CN101560177 A CN 101560177A
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Abstract
The invention relates to a preparation method of atorvastatin calcium which is a compound shown in formula (1). The preparation method comprises the steps of preparing (-) [R-(R<*>, R<*>)]-2-(4-fluorophenyl)-beta-dihydroxy-5-(1-methyl ethyl)-3-phenyl-4-[(phenyl amino) carbonyl]-1H-pyrrole-1-butyl heptanoate and preparing (-) [R-(R<*>, R<*>)]-2-(4- fluorophenyl)-beta-dihydroxy-5-(1-methyl ethyl)-3-phenyl-4-[(phenyl amino) carbonyl]- 1H-pyrrole-1-potassium heptanoate.
Description
Technical field
The present invention relates to the preparation method of atorvastatincalcuim (formula I compound).
Background technology
Atorvastatincalcuim is a medicine complete synthesis, that highly selective suppresses the HMG-CoA reductase enzyme, and U.S. Warner-Lambert (afterwards incorporating Pfizer into) development was gone on the market in Britain, the U.S. with 1997, was third generation statins.
Atorvastatincalcuim is a Statins blood lipid regulation medicine, is used for the treatment of the control of hypercholesterolemia and combined hyperlipidemia familial, coronary heart disease and cerebral apoplexy.Along with the increasing of hyperlipidaemia, coronary heart disease and cerebral apoplexy patient, therefore developing atorvastatincalcuim will bring favorable economic benefit and social benefit in recent years.
Formula I
Bibliographical information the ordinary method of synthetic compound of formula i, as shown below:
This method is in hydrochloric acid and methanol system; (4R-CiS)-and 6-[2-[2-(4-fluorophenyl)-5-(1-sec.-propyl)-3-phenyl-4-[(aniline) carbonyl]-1H-pyrroles-1-yl]-2; 2-methyl isophthalic acid, 3-dioxolane-4-acetate tert-butyl acrylate (abbreviation Compound D) take off the acetone protection and obtain Compound I I.Compound I I reacts in the methanolic sodium hydroxide system and obtains compound III, and adding the overall yield of reaction that calcium acetate obtains the Compound I bibliographical information more only is 50%.
Based on the pharmacy value of atorvastatincalcuim and good market outlook, seeking a kind of can be imperative with the effective ways of the strong synthetic compound of formula i of good yield and controllability.
Summary of the invention
The purpose of this invention is to provide a kind of yield is good, controllability the is strong atorvastatincalcuim and the preparation method of important intermediate thereof.This patent provides the preparation method of compound shown in the formula I.
Formula I
The preparation method of this compound comprises: Compound D is sloughed the acetone protection obtain Compound I I in the presence of organic acid; Compound I I obtains compound III under alcoholic solvent and potassium hydroxide system, compound III and calcium chloride or nitrocalcite reaction production I compound.
Feature of the present invention is, the yield of each step reaction is higher, and controllability is strong, and the cost of product is lower.
Of the present invention open in detail:
1. formula II compound is synthetic
Compound D exists under the system at organic acid (preferred glacial acetic acid), temperature control reaction production II compound, and temperature of reaction is 30～60 ℃, preferred 40～45 ℃; Reaction is added drop-wise to reaction solution in the cold water after finishing, and separating out solid is formula II compound.
2. the formula III compound is synthetic
Alcoholic solvent (preferred alcohol) and formula II compound are heated to dissolving, transfer to the PH=9-11 of reaction solution with the aqueous solution of basic cpd (potassium hydroxide), react the formula III compound.Temperature of reaction is 30 ℃-70 ℃, preferentially selects 38 ℃-55 ℃.
3. formula I compound is synthetic
In above-mentioned formula III reaction solution, add the aqueous solution of 20% calcium salt (preferably calcium chloride), isothermal reaction, temperature of reaction is 30 ℃-70 ℃, preferentially selects 38 ℃-55 ℃.Add gac cooling suction filtration, drip elutriation in the filtrate and go out solid and get formula I compound
Embodiment
Following embodiment is to describe in detail the present invention, and unrestricted the present invention.
Embodiment 1
(-) [R-(R
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-preparation of 1H-pyrroles-1-enanthic acid tert-butyl ester
Stir and in the 2L there-necked flask, add the 800ml glacial acetic acid down, 100g (4R-CiS)-6-[2-[2-(4-fluorophenyl)-5-(1-sec.-propyl)-3-phenyl-4-[(aniline) carbonyl]-1H-pyrroles-1-yl]-2, the 2-methyl isophthalic acid, 3-dioxolane-4-acetate tert-butyl acrylate, heating, solid is molten entirely in the time of T=40 ℃.Temperature control drips 200ml water at T=40-45 ℃ in reaction solution, dripped complete in about 25 minutes.Continue about 2 hours of reaction.The TLC monitoring stops heating, is cooled to room temperature naturally.Add the water of 0-5 ℃ of 3000ml in the 5L there-necked flask, temperature control is added drop-wise to reaction solution in the water at 0-5 ℃, and the adularescent solid is separated out, and drips complete in about 30 minutes.Temperature control is T=0-5 ℃ of stir about 30 minutes, suction filtration, and filter cake washes with water to neutrality.30 ℃ of dryings of solid vacuum, 45 ℃ of dryings of convection oven 6 hours after 12 hours.Get pink solid 91g, yield 98.9%.
Embodiment 2
(-) [R-(R
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-preparation of 1H-pyrroles-1-enanthic acid tert-butyl ester
Stir and in the 2L there-necked flask, add the 900ml propionic acid down, 100g (4R-CiS)-6-[2-[2-(4-fluorophenyl)-5-(1-sec.-propyl)-3-phenyl-4-[(aniline) carbonyl]-1H-pyrroles-1-yl]-2,2-methyl isophthalic acid, 3-dioxolane-4-acetate tert-butyl acrylate, heating, solid is molten entirely in the time of T=40 ℃.Temperature control drips 200ml water at T=40-45 ℃ in reaction solution, dripped complete in about 20 minutes.Continue about 2 hours of reaction.The TLC monitoring stops heating, is cooled to room temperature naturally.Add the water of 0-5 ℃ of 3300ml in the 5L there-necked flask, temperature control is added drop-wise to reaction solution in the water at 0-5 ℃, and the adularescent solid is separated out, and drips complete in about 30 minutes.Temperature control is T=0-5 ℃ of stir about 30 minutes, suction filtration, and filter cake washes with water to neutrality.30 ℃ of dryings of solid vacuum, 45 ℃ of dryings of convection oven 6 hours after 12 hours.Get pink solid 89.5g, yield 97.2%.
Embodiment 3
(-) [R-(R
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-preparation of 1H-pyrroles-1-enanthic acid tert-butyl ester
Stir and in the 2L there-necked flask, add the 1000ml phenylformic acid down, 100g (4R-CiS)-6-[2-[2-(4-fluorophenyl)-5-(1-sec.-propyl)-3-phenyl-4-[(aniline) carbonyl]-1H-pyrroles-1-yl]-2, the 2-methyl isophthalic acid, 3-dioxolane-4-acetate tert-butyl acrylate, heating, solid is molten entirely in the time of T=38 ℃.Temperature control drips 200ml water at T=38-45 ℃ in reaction solution, dripped complete in about 20 minutes.Continue about 2 hours of reaction.The TLC monitoring stops heating, is cooled to room temperature naturally.Add the water of 0-5 ℃ of 3600ml in the 5L there-necked flask, temperature control is added drop-wise to reaction solution in the water at 0-5 ℃, and the adularescent solid is separated out, and drips complete in about 30 minutes.Temperature control is T=0-5 ℃ of stir about 30 minutes, suction filtration, and filter cake washes with water to neutrality.30 ℃ of dryings of solid vacuum, 45 ℃ of dryings of convection oven 6 hours after 12 hours.Get pink solid 89g, yield 96.7%.
Embodiment 4
(-) [R-(R
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-preparation of 1H-pyrroles-1-enanthic acid tert-butyl ester
Stir and in the 2L there-necked flask, add 300ml enanthic acid and 500ml acetate down, 100g (4R-CiS)-6-[2-[2-(4-fluorophenyl)-5-(1-sec.-propyl)-3-phenyl-4-[(aniline) carbonyl]-1H-pyrroles-1-yl]-2, the 2-methyl isophthalic acid, 3-dioxolane-4-acetate tert-butyl acrylate, heating, solid is molten entirely in the time of T=40 ℃.Temperature control drips 200ml water at T=40-45 ℃ in reaction solution, dripped complete in about 20 minutes.Continue about 2 hours of reaction.The TLC monitoring stops heating, is cooled to room temperature naturally.Add the water of 0-5 ℃ of 3000ml in the 5L there-necked flask, temperature control is added drop-wise to reaction solution in the water at 0-5 ℃, and the adularescent solid is separated out, and drips complete in about 30 minutes.Temperature control is T=0-5 ℃ of stir about 30 minutes, suction filtration, and filter cake washes with water to neutrality.The empty 30 ℃ of dryings of solid 45 ℃ of dryings of convection oven 6 hours after 12 hours.Get pink solid 90g, yield 97.8%.
Embodiment 5
The preparation of atorvastatincalcuim crude product
Stir down and add 300ml dehydrated alcohol, 30g (-) [R-(R to the 1L there-necked flask
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-1H-pyrroles-1-enanthic acid tert-butyl ester, heating, solid molten entirely (pale yellow solution) in the time of T=50 ℃.Temperature control stops to drip when dripping 10% potassium hydroxide to reaction solution PH=9-11 for T=40 ℃, and temperature control is about 1 hour of T=50-55 ℃ of reaction, the TLC monitoring, (-) [R-(R
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-solution of 1H-pyrroles-1-enanthic acid potassium.Temperature control drips 20% calcium chloride solution 77.5g at T=50-55 ℃ in reaction solution, drips to finish back continuation reaction 30 minutes.Add 1.5g activated carbon constant temperature and stirred 30 minutes, stop heating, be cooled to 38 ℃-42 ℃ beginning suction filtrations, stir and in filtrate, drip 300ml water down, dropwised a large amount of white solids in about 20 minutes and separate out, static crystallization 2 hours is centrifugal, filter cake with 1L wash white solid.35 ℃ of vacuum-dryings of filter cake got white solid 27.5 grams in 20 hours, and yield is 95%.
Embodiment 6
The preparation of atorvastatincalcuim crude product
Stir down and add 300ml dehydrated alcohol, 30g (-) [R-(R to the 1L there-necked flask
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-1H-pyrroles-1-enanthic acid tert-butyl ester, heating, solid molten entirely (pale yellow solution) in the time of T=50 ℃.Temperature control stops to drip when dripping 10% potassium hydroxide to reaction solution PH=9-11 for T=40 ℃, and temperature control is about 1 hour of T=50-55 ℃ of reaction, the TLC monitoring, (-) [R-(R
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-solution of 1H-pyrroles-1-enanthic acid potassium.Temperature control drips 20% ca nitrate soln 103g at T=50-55 ℃ in reaction solution, drips to finish back continuation reaction 30 minutes.Add 1.5g activated carbon constant temperature and stirred 30 minutes, stop heating, be cooled to 38 ℃-42 ℃ beginning suction filtrations, stir and in filtrate, drip 300ml water down, dropwised a large amount of white solids in about 20 minutes and separate out, static crystallization 2 hours is centrifugal, filter cake with 1L wash white solid.35 ℃ of vacuum-dryings of filter cake got white solid 28 grams in 20 hours, and yield is 96.8%.
Embodiment 7
The preparation of atorvastatincalcuim crude product
Stir down and add 300ml Virahol, 30g (-) [R-(R to the 1L there-necked flask
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-1H-pyrroles-1-enanthic acid tert-butyl ester, heating, solid molten entirely (pale yellow solution) in the time of T=50 ℃.Temperature control stops to drip when dripping 10% potassium hydroxide to reaction solution PH=9-11 for T=40 ℃, and temperature control is about 1 hour of T=50-55 ℃ of reaction, the TLC monitoring, (-) [R-(R
*, R
*)]-2-(4-fluorophenyl)-beta-dihydroxyl-5-(1-first and second bases)-3-phenyl-4-[(phenyl amino) carbonyl]-solution of 1H-pyrroles-1-enanthic acid potassium.Temperature control drips 20% calcium chloride solution 77.5g at T=50-55 ℃ in reaction solution, drips to finish back continuation reaction 30 minutes.Add 1.5g activated carbon constant temperature and stirred 30 minutes, stop heating, be cooled to 38 ℃-42 ℃ beginning suction filtrations, stir and in filtrate, drip 300ml water down, dropwised a large amount of white solids in about 20 minutes and separate out, static crystallization 2 hours is centrifugal, filter cake with 1L wash white solid.35 ℃ of vacuum-dryings of filter cake got white solid 26 grams in 20 hours, and yield is 90%.
Claims (10)
1. a method for preparing atorvastatincalcuim (formula I compound) is characterized by in the formula III compound solution, adds the aqueous solution of calcium salt, isothermal reaction, and the cooling suction filtration drips elutriation and goes out solid and obtain in the filtrate.
2. according to the preparation method of claim 1, it is characterized in that described formula III compound solution by alcoholic solvent and formula II compound are heated to dissolving, obtains with the reaction of basic cpd aqueous solution accent Ph value.
3. according to the preparation method of claim 2, it is characterized in that described formula II compound passes through (4R-CiS)-6-[2-[2-(4-fluorophenyl)-5-(1-sec.-propyl)-3-phenyl-4-[(aniline) carbonyl]-1H-pyrroles-1-yl]-2, the 2-methyl isophthalic acid, 3-dioxolane-4-acetate tert-butyl acrylate, under there is system in organic acid, the temperature control reaction, reaction solution is added drop-wise in the cold water, separates out solid and obtains.
4. method according to claim 3, wherein said organic acid acid is selected from C
1-C
10Organic acid, tartrate, oxalic acid, phenylformic acid, Whitfield's ointment and wherein any two kinds of mixtures.
5. method according to claim 3, wherein the temperature of reaction span of control is 30 ℃-60 ℃.
6. method according to claim 2, wherein said basic cpd are potassium hydroxide.
7. method according to claim 2, wherein used alcoholic solvent are ethanol, methyl alcohol, Virahol, propyl carbinol or its mixed solvent.
8. method according to claim 2, wherein the temperature of reaction span of control is 30 ℃-70 ℃.
9. method according to claim 1, wherein used calcium salt are calcium chloride, nitrocalcite.
10. method according to claim 1, wherein the span of control of temperature of reaction is 30 ℃-70 ℃.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351771A (en) * | 2011-08-11 | 2012-02-15 | 天津市汉康医药生物技术有限公司 | Atorvastatin calcium compound with high bioavailability |
| CN109280024A (en) * | 2018-10-09 | 2019-01-29 | 河南师范大学 | A kind of preparation method of the high purity atorvastatin tert-butyl ester |
| CN109293548A (en) * | 2018-10-09 | 2019-02-01 | 河南师范大学 | A kind of preparation method of high-quality HMG-CoA reductase inhibitor Atorvastatin calcium |
| CN113861092A (en) * | 2021-09-26 | 2021-12-31 | 江苏阿尔法药业股份有限公司 | Method for synthesizing atorvastatin calcium by using continuous flow tubular reactor |
| CN114213308A (en) * | 2021-12-17 | 2022-03-22 | 江苏阿尔法药业股份有限公司 | Method for synthesizing atorvastatin ester by using continuous flow tubular reactor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1727795E (en) * | 2004-03-17 | 2012-04-11 | Ranbaxy Lab Ltd | Process for the production of atorvastatin calcium in amorphous form |
| SI21745A (en) * | 2004-04-09 | 2005-10-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Polymorphs of 1-pyrrol-1-heptanoic acid derivative, intermediat for preparation of atorvastatin |
-
2008
- 2008-04-16 CN CN200810104156A patent/CN101560177B/en active Active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102351771A (en) * | 2011-08-11 | 2012-02-15 | 天津市汉康医药生物技术有限公司 | Atorvastatin calcium compound with high bioavailability |
| CN102351771B (en) * | 2011-08-11 | 2013-07-03 | 天津市汉康医药生物技术有限公司 | Atorvastatin calcium compound with high bioavailability |
| CN109280024A (en) * | 2018-10-09 | 2019-01-29 | 河南师范大学 | A kind of preparation method of the high purity atorvastatin tert-butyl ester |
| CN109293548A (en) * | 2018-10-09 | 2019-02-01 | 河南师范大学 | A kind of preparation method of high-quality HMG-CoA reductase inhibitor Atorvastatin calcium |
| CN113861092A (en) * | 2021-09-26 | 2021-12-31 | 江苏阿尔法药业股份有限公司 | Method for synthesizing atorvastatin calcium by using continuous flow tubular reactor |
| CN114213308A (en) * | 2021-12-17 | 2022-03-22 | 江苏阿尔法药业股份有限公司 | Method for synthesizing atorvastatin ester by using continuous flow tubular reactor |
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| CN101560177B (en) | 2012-10-03 |
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