CN105481832A - (S)-pantoprazole sodium tetrahydrate and preparation method and application thereof - Google Patents
(S)-pantoprazole sodium tetrahydrate and preparation method and application thereof Download PDFInfo
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- CN105481832A CN105481832A CN201610034697.3A CN201610034697A CN105481832A CN 105481832 A CN105481832 A CN 105481832A CN 201610034697 A CN201610034697 A CN 201610034697A CN 105481832 A CN105481832 A CN 105481832A
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The invention discloses an (S)-pantoprazole sodium tetrahydrate. The (S)-pantoprazole sodium tetrahydrate is characterized in that the chemical name of the (S)-pantoprazole sodium tetrahydrate is (S)-5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl0-methyl]sulfinyl]-1H-benzimidazole, and the chemical formula is as shown in the description. The invention also discloses a preparation method and application of the (S)-pantoprazole sodium tetrahydrate. The (S)-pantoprazole sodium tetrahydrate and the preparation method and application thereof have the advantages that the structure is stable, the hygroscopicity is very low, the water content is stable, the preparation technology is simple and the operation is easy to control.
Description
Technical field
The present invention relates to pharmacy field, particularly relate to a kind of Levpantoprazole Sodium tetrahydrate, preparation method, application.
Background technology
S-pantoprazole chemistry (S)-5-difluoro-methoxy-2-[[(3 by name; 4-dimethoxy-2-pyridinyl)-methyl] sulfinyl]-1H-benzoglyoxaline; the acutes hemorrhage of upper gastrointestinal tract such as S-pantoprazole is applicable to duodenal ulcer, stomach ulcer, AGML, plyability stomach ulcer.
Levpantoprazole Sodium has the function of gastric acid secretion inhibiting, is typically used as anti ulcer agent, and can contain the crystal water of some amount under normal circumstances in Levpantoprazole Sodium, general structure is as follows:
S-pantoprazole is dextral-pantoprazole enantiomorph, and dextral-pantoprazole does not have activity substantially.US Patent No. 588535 discloses Levpantoprazole Sodium to be had than racemize pantoprazole and the stronger gastric acid secretion inhibiting effect of dextral-pantoprazole.Wherein the preparation method of sodium salt adds sodium hydroxide to stir to clarify rear cooling and obtain after S-pantoprazole is dissolved in organic solvent.Whether this patent gained Levpantoprazole Sodium water content changes between 2 ~ 12%, not mentioned containing crystal water.US Patent No. 2008234326 discloses the preparation of the salt such as zinc, calcium, lithium, potassium having prepared S-pantoprazole with Levpantoprazole Sodium sesqui hydrate.The hydrate of dihydrate and sodium salt that Chinese patent application CN1312150 discloses L-pantoprazole magnesium is prepared and purposes.The preparation of its Levpantoprazole Sodium hydrate is dissolved in by S-pantoprazole after methyl iso-butyl ketone (MIBK) stirs adding aqueous sodium hydroxide solution, continues to stir to clarify rear cooling crystallization gained.The Levpantoprazole Sodium hydrate obtained is not a stable crystal formation, and its crystal water content changes because of ambient moisture, between 2 ~ 12%.
Chinese patent application CN200810024533.8 discloses a kind of unbodied Levpantoprazole Sodium solid, and moisture 0.1 ~ 1.9%.Method adds solid sodium hydroxide stirring after S-pantoprazole is dissolved in tetrahydrofuran (THF), then is added in the ether that industrial production cannot use in a large number, namely has unbodied Levpantoprazole Sodium solid to separate out.In its X-ray powder diffraction figure, display does not have the characteristic peak that can characterize crystal habit.Chinese Patent Application No. 201110456843.9 discloses a kind of preparation for the treatment of the compound of gastrointestinal illness, this compound is three times of water Levpantoprazole Sodiums, preparation method is: aqueous sodium hydroxide solution S-pantoprazole being dropped into proper volume, proper concn, adds or does not add solubility promoter, stirring and dissolving under proper temperature, filter, filtrate temperature control concentrates, cooling crystallization, filters, drying, obtains Levpantoprazole Sodium three times of crystal of hydrate.
The Levpantoprazole Sodium described in above technology or its hydrate are hydrate crystal forms or unformed, and its preparation method mainly utilizes the Levpantoprazole Sodium character that solubleness is poor in the organic solvent that polarity is less, separate out and obtain from organic solvent.
Summary of the invention
The object of the invention is to provide the Levpantoprazole Sodium tetrahydrate that a kind of Stability Analysis of Structures, water absorbability are very little, water content is stablized, preparation technology is simple, easy to control.
The present invention solves the problems of the technologies described above by the following technical solutions: a kind of Levpantoprazole Sodium tetrahydrate; chemistry (S)-5-difluoro-methoxy-2-[[(3 by name of described hydrate; 4-dimethoxy-2-pyridinyl)-methyl] sulfinyl] tetrahydrate of-1H-benzoglyoxaline, its chemical structural formula is:
Preferably: the characteristic X-ray powder diffraction peak of described hydrate has the diffraction peak at the 2 θ angles of 6.09 ± 0.20,9.96 ± 0.20,11.87 ± 0.20,12.11 ± 0.20,15.32 ± 0.20,17.86 ± 0.20,19.42 ± 0.20,22.82 ± 0.20,24.59 ± 0.20,25.73 ± 0.20,26.46 ± 0.20,29.29 ± 0.20,29.91 ± 0.20,32.82 ± 0.20,34.09 ± 0.20,35.73 ± 0.20,36.61 ± 0.20,37.89 ± 0.20.
Prepare a method for above-mentioned Levpantoprazole Sodium tetrahydrate, comprise the following steps:
(1) S-pantoprazole, sodium hydroxide are added stirring reaction in purified water, the sodium hydroxide added and S-pantoprazole mol ratio are 1 ~ 4:1, and the volume of the purified water added is 2 ~ 25 times of S-pantoprazole weight;
(2) stirring and dissolving at 10 ~ 40 DEG C, filter, filtrate 30 ~ 60 DEG C of temperature control concentrating under reduced pressure, separate out to there being solid; Stop distillation, slow cooling to 0 ~ 25 DEG C, crystallization 2 ~ 48 hours; Suction filtration, with a small amount of cooled water washing filter cake, 30 ~ 60 DEG C of normal pressures or drying under reduced pressure 5 ~ 48 hours, obtain product.
Preferably, the solubility promoter added in described step (1), described solubility promoter is a kind of in acetone, tetrahydrofuran (THF), ethanol, methyl alcohol, propyl alcohol, Virahol, acetonitrile or two or more mixed solvent arbitrarily.
Preferably, described solubility promoter add-on is 0 ~ 3 times of S-pantoprazole weight.
Preferably, the sodium hydroxide added in described step (1) and S-pantoprazole mol ratio are 1.4 ~ 1.6:1, and the volume of the purified water added is 2 ~ 6 times of S-pantoprazole weight.
The present invention also discloses the application that Levpantoprazole Sodium tetrahydrate is used for the treatment of relevant disease disorderly with gastric acid secretion.
The invention has the advantages that: Stability Analysis of Structures, water absorbability are very little, water content stable, preparation technology is simple, easy to control.
Accompanying drawing explanation
Fig. 1 is Levpantoprazole Sodium tetrahydrate X-diffracting spectrum of the present invention
Fig. 2 is Levpantoprazole Sodium tetrahydrate thermogravimetric collection of illustrative plates (TGA) of the present invention
Fig. 3 is Levpantoprazole Sodium tetrahydrate differential scanning calorimetric analysis (DSC) of the present invention
Fig. 4 is Levpantoprazole Sodium tetrahydrate crystal accumulation figure of the present invention
Embodiment
The present invention discloses a kind of Levpantoprazole Sodium tetrahydrate; chemistry (S)-5-difluoro-methoxy-2-[[(3 by name of described compound; 4-dimethoxy-2-pyridinyl)-methyl] sulfinyl] tetrahydrate of-1H-benzoglyoxaline, its chemical structural formula is:
Embodiment 1
By S-pantoprazole 40.5g, the 800ml aqueous solution being dissolved with 6gNaOH drops in reaction flask, and stirring at room temperature is dissolved completely to material, filters feed liquid, underpressure distillation at feed liquid temperature control 35 DEG C.Stopping distillation when there being solid to separate out in feed liquid, being placed in 0 DEG C of refrigeration and leaving standstill crystallization 48 hours.Filter feed liquid, a small amount of cooled water washing of filter cake, 50 DEG C of constant pressure and dries 6 hours, obtain Levpantoprazole Sodium tetrahydrate solid 42g, yield 87%.Adopting expense Xiu Shi method mensuration moisture to be 15.10%, HPLC mensuration related substance is 99.95%.
As shown in Figure 1, carry out analysis and characterization by X-ray powder diffraction and distinguished with other forms of Levpantoprazole Sodium, the crystallization of Levpantoprazole Sodium tetrahydrate provided by the invention, it is characterized in that in X-ray powder diffraction, represent that there is following characteristics peak with 2 θ: 6.09 ± 0.20, 9.96 ± 0.20, 11.87 ± 0.20, 12.11 ± 0.20, 15.32 ± 0.20, 17.86 ± 0.20, 19.42 ± 0.20, 22.82 ± 0.20, 24.59 ± 0.20, 25.73 ± 0.20, 26.46 ± 0.20, 29.29 ± 0.20, 29.91 ± 0.20, 32.82 ± 0.20, 34.09 ± 0.20, 35.73 ± 0.20, 36.61 ± 0.20, 37.89 ± 0.20.
As shown in Figure 2, in thermogravimetric analysis collection of illustrative plates, show crystal water dehydration temperature within the scope of 80 ~ 120 DEG C, weightless 15.08%.
As shown in Figure 3, in differential scanning calorimetric thermogram spectrum, the endothermic peak of crystal water dehydration is at 80 ~ 120 DEG C, slow decomposes 200 DEG C time, decomposition temperature is higher, and when illustrating that this compound is heated, its structure is highly stable, so store highly stable at ambient temperature.
Levpantoprazole Sodium tetrahydrate and Levpantoprazole Sodium three water crystallization compound structure are stablized, water content is low, the advantage that related substance is few, and preparation scheme provided by the invention is simple and easy to get, easily controls, and are applicable to the large production of industry.The crystal formation of this crystal-form compound and commercially available Levpantoprazole Sodium trihydrate, water-absorbent and stability are compared, are listed as follows:
Table 1 Levpantoprazole Sodium tetrahydrate compares with a Levpantoprazole Sodium times hemihydrate crystal formation
Levpantoprazole Sodium tetrahydrate has the X-ray powder diffraction feature being obviously different from commercially available trihydrate crystal formation.
The moisture determination result of table 2 Levpantoprazole Sodium tetrahydrate and Levpantoprazole Sodium trihydrate height wet test
As can be seen from Table 2, comparatively Levpantoprazole Sodium three times of water crystallizations speed that wets is obviously low for Levpantoprazole Sodium tetrahydrate form.This experimental result illustrate Levpantoprazole Sodium tetrahydrate of the present invention in moisture absorption comparatively Levpantoprazole Sodium three times of water crystallization forms to some extent obviously improve.
Table 3 Levpantoprazole Sodium tetrahydrate compound and Levpantoprazole Sodium trihydrate accelerated test are investigated
As can be seen from Table 3, Levpantoprazole Sodium tetrahydrate form comparatively Levpantoprazole Sodium three times of water crystallization physics and chemical property has clear improvement, highly stable.
Embodiment 2
By S-pantoprazole 40.5g, be dissolved with the 800ml aqueous solution of 10.4gNaOH, 800ml acetone drops in reaction flask, and temperature control 5 DEG C is stirred to material and dissolves completely, filters feed liquid, underpressure distillation at feed liquid temperature control 40 DEG C.Stopping distillation when there being solid to separate out in feed liquid, being placed in 10 DEG C of refrigerations and leaving standstill crystallization 24 hours.Filter feed liquid, a small amount of cooled water washing of filter cake, 40 DEG C of constant pressure and dries 10 hours, obtain Levpantoprazole Sodium tetrahydrate solid 43.5g, yield 90%.Adopting expense Xiu Shi method mensuration moisture to be 15.08%, HPLC mensuration related substance is 99.91%.
Embodiment 3
By S-pantoprazole 40.5g, be dissolved with the 160ml aqueous solution of 3.6gNaOH, 60ml methyl alcohol drops in reaction flask, and temperature control 25 DEG C is stirred to material and dissolves completely, filters feed liquid, underpressure distillation at feed liquid temperature control 30 DEG C.Stopping distillation when there being solid to separate out in feed liquid, being placed in 5 DEG C of refrigerations and leaving standstill crystallization 8 hours.Filter feed liquid, a small amount of cooled water washing of filter cake, 40 DEG C of constant pressure and dries 8 hours, obtain Levpantoprazole Sodium tetrahydrate solid 42.5g, yield 88%.Adopting expense Xiu Shi method mensuration moisture to be 15.08%, HPLC mensuration related substance is 99.92%.
Embodiment 4
By S-pantoprazole 40.5g, be dissolved with the 160ml aqueous solution of 3.6gNaOH, 40ml ethanol drops in reaction flask, and temperature control 25 DEG C is stirred to material and dissolves completely, filters feed liquid, underpressure distillation at feed liquid temperature control 35 DEG C.Stopping distillation when there being solid to separate out in feed liquid, being placed in 0 DEG C of refrigeration and leaving standstill crystallization 8 hours.Filter feed liquid, a small amount of cooled water washing of filter cake, 40 DEG C of constant pressure and dries 8 hours, obtain Levpantoprazole Sodium tetrahydrate solid 43g, yield 89%.Adopting expense Xiu Shi method mensuration moisture to be 15.09%, HPLC mensuration related substance is 99.97%.
Embodiment 5
By S-pantoprazole 40.5g, be dissolved with the 80ml aqueous solution of 16.8gNaOH, the mixed solution of 40ml ethanol and acetone drops in reaction flask, and temperature control 10 DEG C is stirred to material and dissolves completely, filters feed liquid, underpressure distillation at feed liquid temperature control 45 DEG C.Stopping distillation when there being solid to separate out in feed liquid, being placed in 25 DEG C of refrigerations and leaving standstill crystallization 2 hours.Filter feed liquid, a small amount of cooled water washing of filter cake, 30 DEG C of constant pressure and dries 5 hours, obtain Levpantoprazole Sodium tetrahydrate solid 43g, yield 90%.Adopting expense Xiu Shi method mensuration moisture to be 15.09%, HPLC mensuration related substance is 99.97%.
Embodiment 6
By S-pantoprazole 40.5g, be dissolved with the 1000ml aqueous solution of 3.6gNaOH, 40ml methyl alcohol, ethanol, tetrahydrofuran (THF) mixed solution are fed in reaction flask, and temperature control 30 DEG C is stirred to material and dissolves completely, filter feed liquid, underpressure distillation at feed liquid temperature control 60 DEG C.Stopping distillation when there being solid to separate out in feed liquid, being placed in 0 DEG C of refrigeration and leaving standstill crystallization 10 hours.Filter feed liquid, a small amount of cooled water washing of filter cake, 60 DEG C of constant pressure and dries 48 hours, obtain Levpantoprazole Sodium tetrahydrate solid 43.5g, yield 90%.Adopting expense Xiu Shi method mensuration moisture to be 15.07%, HPLC mensuration related substance is 99.93%.
Embodiment 7
By S-pantoprazole 40.5g, be dissolved with the 160ml aqueous solution of 3.6gNaOH, the mixed solution of 60ml methyl alcohol, Virahol, acetonitrile drops in reaction flask, and temperature control 40 DEG C is stirred to material and dissolves completely, filters feed liquid, underpressure distillation at feed liquid temperature control 30 DEG C.Stopping distillation when there being solid to separate out in feed liquid, being placed in 5 DEG C of refrigerations and leaving standstill crystallization 8 hours.Filter feed liquid, a small amount of cooled water washing of filter cake, 40 DEG C of constant pressure and dries 8 hours, obtain Levpantoprazole Sodium tetrahydrate solid 42.5g, yield 88%.Adopting expense Xiu Shi method mensuration moisture to be 15.08%, HPLC mensuration related substance is 99.92%.
Levpantoprazole Sodium tetrahydrate provided by the invention can be used for the association areas such as treatment gastrointestinal tract disease.
Acidity (pH value) in stomach determines the topmost factor of medicine to gastroesophageal reflux disease and Peptic Ulcers curative effect, it is generally acknowledged, in most time, pH should remain on 4.0 or more, and the healing pH of digestive tract ulcer need 3.5 or more.Every strong to hydrochloric acid in gastric juice suppression, the medicine that the time is long, its curative effect is also best.Pantoprazole Sodium improves stomach inner pH value rapidly, meets needed for curative effect of disease.
With Levpantoprazole Sodium tetrahydrate for pharmaceutical composition prepared by active substance is mainly used in the acutes hemorrhage of upper gastrointestinal tract such as duodenal ulcer, stomach ulcer, AGML, plyability stomach ulcer; The generation of ulcerative hemorrhage under the acute gastric mucosal lesion that non-steroidal anti-inflammatory drugs causes and stress situation; General anesthesia or major operation and weak comatose patient prevent regurgitation of gastric juice from merging induction type pneumonia; The ulcer that medicine and alcohol cause: alcohol stimulates and NSAID (non-steroidal anti-inflammatory drug), cause during the pharmacological agent of cortex aldoketones can not oral administration time reflux esophagitis, peptide ulceration treatment, better to the patient's curative effect infected with HP (Hp).
The foregoing is only the preferred embodiment of the invention; not in order to limit the invention; the any amendment done within all spirit in the invention and principle, equivalently to replace and improvement etc., within the protection domain that all should be included in the invention.
Claims (7)
1. a Levpantoprazole Sodium tetrahydrate; it is characterized in that: chemistry (S)-5-difluoro-methoxy-2-[[(3 by name of described hydrate; 4-dimethoxy-2-pyridinyl)-methyl] sulfinyl] tetrahydrate of-1H-benzoglyoxaline, its chemical structural formula is:
2. a kind of Levpantoprazole Sodium tetrahydrate according to claim 1, is characterized in that: the characteristic X-ray powder diffraction peak of described hydrate has the diffraction peak at the 2 θ angles of 6.09 ± 0.20,9.96 ± 0.20,11.87 ± 0.20,12.11 ± 0.20,15.32 ± 0.20,17.86 ± 0.20,19.42 ± 0.20,22.82 ± 0.20,24.59 ± 0.20,25.73 ± 0.20,26.46 ± 0.20,29.29 ± 0.20,29.91 ± 0.20,32.82 ± 0.20,34.09 ± 0.20,35.73 ± 0.20,36.61 ± 0.20,37.89 ± 0.20.
3., as a preparation method for a kind of Levpantoprazole Sodium tetrahydrate according to any one of claim 1-2, it is characterized in that, comprise the following steps:
(1) S-pantoprazole, sodium hydroxide are added stirring reaction in purified water, the sodium hydroxide added and S-pantoprazole mol ratio are 1 ~ 4:1, and the volume of the purified water added is 2 ~ 25 times of S-pantoprazole weight;
(2) stirring and dissolving at 10 ~ 40 DEG C, filter, filtrate 30 ~ 60 DEG C of temperature control concentrating under reduced pressure, separate out to there being solid; Stop distillation, slow cooling to 0 ~ 25 DEG C, crystallization 2 ~ 48 hours; Suction filtration, with a small amount of cooled water washing filter cake, 30 ~ 60 DEG C of normal pressures or drying under reduced pressure 5 ~ 48 hours, obtain product.
4. the preparation method of a kind of Levpantoprazole Sodium tetrahydrate according to claim 3, it is characterized in that, in described step (1), add solubility promoter, described solubility promoter is a kind of in acetone, tetrahydrofuran (THF), ethanol, methyl alcohol, propyl alcohol, Virahol, acetonitrile or two or more mixed solvent arbitrarily.
5. the preparation method of a kind of Levpantoprazole Sodium tetrahydrate according to claim 3, is characterized in that, described solubility promoter add-on is 0 ~ 3 times of S-pantoprazole weight.
6. the preparation method of a kind of Levpantoprazole Sodium tetrahydrate according to claim 2, it is characterized in that, the sodium hydroxide added in described step (1) and S-pantoprazole mol ratio are 1.4 ~ 1.6:1, and the volume of the purified water added is 2 ~ 6 times of S-pantoprazole weight.
7. a kind of Levpantoprazole Sodium tetrahydrate according to any one of claim 1-2 is used for the treatment of the application of relevant disease disorderly with gastric acid secretion.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114195765A (en) * | 2021-12-17 | 2022-03-18 | 湖南赛隆药业有限公司 | Levo-pantoprazole sodium crystal form A and preparation method and application thereof |
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| CN102199145A (en) * | 2010-03-23 | 2011-09-28 | 山东新时代药业有限公司 | Compound for the treatment of gastrointestinal disease |
| CN102584790A (en) * | 2011-12-31 | 2012-07-18 | 江苏奥赛康药业股份有限公司 | S-pantoprazole sodium trihydrate, and preparation method and application thereof |
| CN103242294A (en) * | 2013-03-23 | 2013-08-14 | 广东华南药业集团有限公司 | (S)-pantoprazole sodium dihydrate and preparation method thereof |
| CN103467451A (en) * | 2012-06-07 | 2013-12-25 | 上海汇伦生命科技有限公司 | Preparation method for S-pantoprazole sodium |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1369491A (en) * | 2002-02-10 | 2002-09-18 | 沈阳药科大学 | Chiral pantorazole salt and its preparing process |
| CN102199145A (en) * | 2010-03-23 | 2011-09-28 | 山东新时代药业有限公司 | Compound for the treatment of gastrointestinal disease |
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| CN103467451A (en) * | 2012-06-07 | 2013-12-25 | 上海汇伦生命科技有限公司 | Preparation method for S-pantoprazole sodium |
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| CN114195765A (en) * | 2021-12-17 | 2022-03-18 | 湖南赛隆药业有限公司 | Levo-pantoprazole sodium crystal form A and preparation method and application thereof |
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Application publication date: 20160413 |