CN102875530A - (R)-lansoprazole tert-butylamine salt and crystal form and preparation method thereof - Google Patents
(R)-lansoprazole tert-butylamine salt and crystal form and preparation method thereof Download PDFInfo
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- CN102875530A CN102875530A CN2011101992000A CN201110199200A CN102875530A CN 102875530 A CN102875530 A CN 102875530A CN 2011101992000 A CN2011101992000 A CN 2011101992000A CN 201110199200 A CN201110199200 A CN 201110199200A CN 102875530 A CN102875530 A CN 102875530A
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Abstract
The invention discloses a (R)-lansoprazole tert-butylamine salt and a crystal form and a preparation method thereof. The general formula of the (R)-lansoprazole tert-butylamine salt is shown as a formula 1. The crystal form has peaks in a spectrum of x-ray powder diffraction using a Cu-K alpha 1 radiation source at the diffraction angle 2 theta which is 6.81, 7.31, 7.97, 9.96, 12.42, 13.48, 14.32, 16.03, 18.38, 19.89, 20.29, 20.89, 22.85, 24.09, 24.85, 26.00, 29.47 and 29.77, and the value error of the angle 2 theta ranges from minus 0.3 to plus 0.3. The preparation method comprises the following steps: under heating conditions, dissolving (R)-lansoprazole in an organic solvent, adding tert-butylamine, uniformly mixing, cooling to a temperature below 5 DEG C for crystallizing, and separating an obtained crystal solid. The (R)-lansoprazole tert-butylamine salt has better physicochemical properties, better flowability, better water solubility, lower hygroscopicity and higher stability and is favorable to application in preparation technologies. The formula 1 is as follows.
Description
Technical field
The present invention relates to a kind of (R)-lansoprazole tert-butylamine salt and crystal formation and preparation method.
Background technology
Lansoprazole in December, 1991 by the exploitation of Japanese Wu Tian company, went on the market in Japan in 1992.It is after omeprazole, the proton pump inhibitor of second listing.Compare omeprazole, owing to introduced fluorine atom, the thermodynamics of lansoprazole and oxidative stability increase, and have greatly improved biological activity.
The chemical name of lansoprazole is 2-[[[3-methyl-4-(2,2,2-, three fluoro-oxyethyl groups)-2-pyridyl] methyl] sulfinyl]-the 1H-benzoglyoxaline, its structural sulphur atom is chiral centre, therefore has two optical isomers.The chemical structure of its dextrorotatory form (i.e. (R)-lansoprazole) is as follows:
For the raceme of commercially available lansoprazole, the side effect of clinical report mainly contains headache, diarrhoea, feel sick etc., takes for a long time and also may form hepatoma and stomach class tumour.And for (R)-lansoprazole, be easier to be absorbed than raceme when oral, play a role more rapidly, have in vivo higher Cmax (blood peak concentration of drug) and larger AUC (area under plasma drug level-time curve), not only drug effect obviously is better than its raceme, and toxic side effect is also less.Therefore (R)-lansoprazole has good clinical value as active medicine.
But, (R)-and lansoprazole solubleness in water is less, and water absorbability is stronger, and the easy variable color of medicine, loss of stability and decomposition are unfavorable for the operation of preparation process after the moisture absorption.Thus, it is good to be necessary to develop physico-chemical property, is beneficial to (R)-lansoprazole salt type of preparation preparation.But have not yet to see the report of relevant (R)-lansoprazole salt type.
Summary of the invention
Technical problem to be solved by this invention is for (R)-lansoprazole poorly water-soluble, poor stability, poor fluidity, strong to humidity sensitive, water absorbability, be applied in the preparation process, make operation easier large, production cost is higher, and the not high defective of formulation products stability, and provide a kind of physico-chemical property better, mobile better, water-soluble higher, water absorbability is lower, stability is higher, is beneficial to (the R)-lansoprazole salt type and crystal formation and the preparation method that are applied to preparation process.
The inventor finds that the alkaline matter that adopts great majority pharmaceutically to commonly use can only obtain jelly, oily matter or amorphous substance etc., is difficult to obtain salts substances in the research of preparation (R)-lansoprazole fatty amine salt.By many experiments, the inventor finds unexpectedly, adopts TERTIARY BUTYL AMINE, and controls especially the temperature of cooling crystallization, can obtain good (the R)-lansoprazole of physico-chemical property tert-butylamine salt.
Therefore, the present invention relates to following technical proposals:
The present invention relates to (R)-lansoprazole tert-butylamine salt as shown in Equation 1.
The invention still further relates to a kind of (R)-lansoprazole tert-butylamine salt crystal formation, it is using source of radiation to be Cu-K α
1Powder x-ray diffraction spectrum in, in diffraction angle 2 θ=6.81,7.31,7.97,9.96, there is the peak at 12.42,13.48,14.32,16.03,18.38,19.89,20.29,20.89,22.85,24.09,24.85,26.00,29.47 and 29.77 degree places; 2 θ value limit of error are ± 0.3, and better is ± 0.2.
The invention further relates to the preparation method that above-mentioned (R)-lansoprazole uncle decides the amine salt crystal formation, it comprises the steps: under heating condition, (R)-lansoprazole is dissolved in the organic solvent, adding TERTIARY BUTYL AMINE mixes, be cooled to afterwards crystallization below 5 ℃, separating obtained crystal gets final product.
Wherein, described (R)-lansoprazole can be by existing method preparation, such as document CN1355798A.
Wherein, described heating condition can make (R)-lansoprazole be dissolved in organic solvent fully and be as the criterion for being heated above envrionment temperature, preferably is heated to 20 ℃～80 ℃, and more preferably 40 ℃～70 ℃, most preferably 40 ℃～60 ℃.
Wherein, described organic solvent is the organic solvent that can dissolve (R)-lansoprazole, is generally C
3～C
6Esters solvent, one or more in ethyl acetate, methyl acetate, propyl acetate and the butylacetate.The amount of described organic solvent is as the criterion can dissolve (R)-lansoprazole, and general concentration is 30～500mg/ml.Better, the solution that (R)-lansoprazole is dissolved in the organic solvent gained carries out subsequent operations after with filtering with microporous membrane again.The aperture of described millipore filtration routinely condition is selected, and is generally 0.22～0.8 μ m, preferred 0.45 μ m.
Wherein, the consumption of described TERTIARY BUTYL AMINE is generally 1～10 times of molar weight of (R)-lansoprazole, and better is 1～5 times, and better is 1～2 times.The temperature that described adding TERTIARY BUTYL AMINE mixes is generally 20～80 ℃, and more preferably 30～70 ℃, most preferably 35～50 ℃.Described mixing can be adopted this area common method, such as vortex, magnetic agitation or concussion etc.The time of described mixing is generally 5-40 minute and is advisable, preferred 20～30 minutes.
Wherein, described be cooled to below 5 ℃ better for being cooled to-25～5 ℃, better for being cooled to-20～5 ℃.The time of described cooling is as the criterion with crystallize out, and better is to cool off more than 1 hour, and better is that cooling is more than 1～12 hour.
In the method for the present invention, what described dissolving and mixing step were better carries out under agitation condition, and wherein, the better stirring of cooling crystallization can make the solution of top and the bottom in the container keep the temperature uniformity, is conducive to the consistence of crystal.
(R)-and after lansoprazole tert-butylamine salt crystal formation is separated out, can separate by this area ordinary method, be generally filtration, washing and dry.Described drying can adopt this area ordinary method, such as constant pressure and dry or drying under reduced pressure etc.
On the basis that meets this area general knowledge, but above-mentioned each optimum condition arbitrary combination namely gets the preferred embodiments of the invention.
Agents useful for same of the present invention and raw material be commercially available getting all.
Positive progressive effect of the present invention is: the present invention successfully makes (R)-lansoprazole tert-butylamine salt first, its crystal formation has good physico-chemical property, water-soluble higher, flowability is good, water absorbability is low, stability is high, is particularly useful for preparing (R)-lansoprazole pharmaceutical preparation of various formulations.Preparation method of the present invention is simple to operation, is fit to suitability for industrialized production.
Description of drawings
Fig. 1 is the XRD figure of effect embodiment 1 (R)-lansoprazole tert-butylamine salt.
Fig. 2 is the XRD figure of effect embodiment 1 (R)-lansoprazole raw material.
Fig. 3 is the polarization microscope figure of effect embodiment 2 (R)-lansoprazole tert-butylamine salt.
Fig. 4 is the polarization microscope figure of effect embodiment 2 (R)-lansoprazole raw material.
Fig. 5 is the constant temperature sucting wet curve figure of effect embodiment 3 (R)-lansoprazole tert-butylamine salt.
Fig. 6 is the constant temperature sucting wet curve figure of effect embodiment 3 (R)-lansoprazole raw material.
Embodiment
Mode below by embodiment further specifies the present invention, but does not therefore limit the present invention among the described scope of embodiments.
Among the following embodiment, (R)-lansoprazole can be prepared according to document CN1355798A.
The preparation of embodiment 1 (R)-lansoprazole tert-butylamine salt crystal formation
(R)-lansoprazole (249.2mg) is dissolved in the ethyl acetate (5mL), is heated to fully dissolving under 60 ℃ of magnetic agitation, the millipore filtration (nylon membrane) of sample solution with 0.45 μ m filtered, obtain settled solution.On 37 ℃ of warm tables, slowly add the TERTIARY BUTYL AMINE solution (72 μ L) of equimolar ratio under the magnetic agitation.After 37 ℃ of lower magnetic forces stir 10min, solution is placed-20 ℃ of lower 1h, separate out solid matter.With the product filtration under diminished pressure, obtain white solid, with the normal heptane washing that lets cool 3 times, then product is placed vacuum drying oven, 40 ℃ of lower drying under reduced pressure spend the night, thereby obtain the finished product.
The preparation of embodiment 2 (R)-lansoprazole tert-butylamine salt crystal formation
(R)-lansoprazole (250.0mg) is dissolved in the methyl acetate (5mL), is heated to fully dissolving under 20 ℃ of magnetic agitation, the millipore filtration (nylon membrane) of sample solution with 0.22 μ m filtered, obtain settled solution.On 20 ℃ of warm tables, slowly add the TERTIARY BUTYL AMINE solution (72 μ L) of equimolar ratio under the magnetic agitation.After 20 ℃ of lower magnetic forces stir 40min, solution is placed-10 ℃ of lower 4h, separate out solid matter.With the product filtration under diminished pressure, obtain white solid, with the normal heptane washing that lets cool 3 times, then product is placed vacuum drying oven, 40 ℃ of lower drying under reduced pressure spend the night, thereby obtain the finished product.
The preparation of embodiment 3 (R)-lansoprazole tert-butylamine salt crystal formation
(R)-lansoprazole (300.2mg) is dissolved in the propyl acetate (2mL), is heated to fully dissolving under 50 ℃ of magnetic agitation, the millipore filtration (nylon membrane) of sample solution with 0.45 μ m filtered, obtain settled solution.On 40 ℃ of warm tables, slowly add the TERTIARY BUTYL AMINE solution (426.9 μ L) of 5 times of amounts under the magnetic agitation.Behind 40 ℃ of lower concussion 30min, solution placed spend the night under 0 ℃, separate out solid matter.With the product filtration under diminished pressure, obtain white solid, with the Skellysolve A washing that lets cool 3 times, then product is placed stink cupboard, constant pressure and dry, thus obtain the finished product.
The preparation of embodiment 4 (R)-lansoprazole tert-butylamine salt crystal formation
(R)-lansoprazole (300.0mg) is dissolved in the butylacetate (1.0mL), is heated to fully dissolving under 80 ℃ of magnetic agitation, the millipore filtration (nylon membrane) of sample solution with 0.8 μ m filtered, obtain settled solution.On 60 ℃ of warm tables, slowly add the TERTIARY BUTYL AMINE solution (853.8 μ L) of 10 times of amounts under the magnetic agitation.Behind 60 ℃ of lower vortex 5min, solution placed under 5 ℃ spend the night, separate out solid matter.With the product filtration under diminished pressure, obtain white solid, with the normal hexane washing that lets cool 3 times, then then product is placed product is placed stink cupboard, constant pressure and dry, thus obtain the finished product.
The preparation of embodiment 5 (R)-lansoprazole tert-butylamine salt crystal formation
(R)-lansoprazole (30mg) is dissolved in the ethyl acetate (1mL), be heated to fully dissolving under 40 ℃ of magnetic agitation, the millipore filtration (nylon membrane) of sample solution with 0.45 μ m filtered, obtain settled solution, on 35 ℃ of warm tables, slowly add the TERTIARY BUTYL AMINE solution (8.64 μ L) of equimolar ratio under the magnetic agitation.Behind 35 ℃ of lower stirring 20min, solution is placed spend the night under-20 ℃, separate out solid matter.With the product filtration under diminished pressure, obtain white solid, with the octane washing that lets cool 3 times, then product is placed vacuum drying oven, 40 ℃ of lower drying under reduced pressure spend the night, thereby obtain the finished product.
The preparation of embodiment 6 (R)-lansoprazole tert-butylamine salt crystal formation
(R)-lansoprazole (5.0g) is dissolved in the methyl acetate (10mL), be heated to fully dissolving under 70 ℃ of magnetic agitation, the millipore filtration (nylon membrane) of sample solution with 0.45 μ m filtered, obtain settled solution, on 50 ℃ of warm tables, slowly add the TERTIARY BUTYL AMINE solution (1423 μ L) of equimolar ratio under the magnetic agitation.After 50 ℃ of lower magnetic forces stir 20min, solution is placed under-20 ℃ and spend the night, separate out solid matter.With the product filtration under diminished pressure, obtain white solid, then the ethyl acetate washing that lets cool under being used for-20 ℃ 3 times places vacuum drying oven with product, and 40 ℃ of lower drying under reduced pressure spend the night, thereby obtain the finished product.
Effect embodiment 1X-ray powder diffraction method detects to be identified
(R)-lansoprazole tert-butylamine salt crystal formation of 1, sample: embodiment, 1～6 preparation reaches (R)-the lansoprazole raw material.
2, X-ray powder diffraction testing conditions: X-ray source is Cu-K α
1(wavelength is
); Operating voltage: 40KV; Working current intensity: 40mA; Detector: PSD detector; Scanning angle: 4～40 ° (2 θ); Step value: 0.05 °; Sweep velocity: 1 second/step-length.
3, experimental result
The XRD figure spectrum of (R)-lansoprazole tert-butylamine salt crystal formation of embodiment 1～6 preparation as shown in Figure 1.As seen from Figure 1, (R)-position of the diffraction peak of the X-ray diffractogram of lansoprazole tert-butylamine salt has the data of the following stated of being selected from: diffraction angle 2 θ=6.81,7.31,7.97,9.96,12.42,13.48,14.32,16.03,18.38,19.89,20.29,20.89,22.85,24.09,24.85,26.00,29.47 and 29.77.The peak position numerical reference is as shown in the table in the corresponding diagram:
| The peak position |
2 θ values | The peak position |
2 |
| 1 | 6.81 | 11 | 20.29 |
| 2 | 7.31 | 12 | 20.89 |
| 3 | 7.97 | 13 | 22.85 |
| 4 | 9.96 | 14 | 24.09 |
| 5 | 12.42 | 15 | 24.85 |
| 6 | 13.48 | 16 | 26.00 |
| 7 | 14.32 | 17 | 29.47 |
| 8 | 16.03 | 18 | 29.77 |
| 9 | 18.38 | -- | -- |
| 10 | 19.89 | -- | -- |
(R)-XRD figure of lansoprazole raw material spectrum is as shown in Figure 2.As seen from Figure 2, (R)-position of the diffraction peak of the X-ray diffractogram of lansoprazole raw material has the data of the following stated of being selected from: diffraction angle 2 θ=6.79,8.34,9.30,10.07,11.10,12.47,13.50,14.88,15.08,15.80,16.39,16.61,17.77,18.57,19.90,20.14,20.80,21.83,23.31,23.85,24.44,25.01,25.56,25.94,26.72,27.76,28.83,29.16,30.16,31.26,31.78,33.49,34.06,35.29,35.63,35.92,37.12,37.69,38.08 and 38.62.The peak position numerical reference is as shown in the table in the corresponding diagram:
| The peak position |
2 θ values | The peak position |
2 θ values | The peak position |
2 |
| 1 | 6.79 | 15 | 19.90 | 29 | 30.16 |
| 2 | 8.34 | 16 | 20.14 | 30 | 31.26 |
| 3 | 9.30 | 17 | 20.80 | 31 | 31.78 |
| 4 | 10.07 | 18 | 21.83 | 32 | 33.49 |
| 5 | 11.10 | 19 | 23.31 | 33 | 34.06 |
| 6 | 12.47 | 20 | 23.85 | 34 | 35.29 |
| 7 | 13.50 | 21 | 24.44 | 35 | 35.63 |
| 8 | 14.88 | 22 | 25.01 | 36 | 35.92 |
| 9 | 15.08 | 23 | 25.56 | 37 | 37.12 |
| 10 | 15.80 | 24 | 25.94 | 38 | 37.69 |
| 11 | 16.39 | 25 | 26.72 | 39 | 38.08 |
| 12 | 16.61 | 26 | 27.76 | 40 | 38.62 |
| 13 | 17.77 | 27 | 28.83 | -- | -- |
| 14 | 18.57 | 28 | 29.16 | -- | -- |
(R)-lansoprazole tert-butylamine salt crystal formation of 1, sample: embodiment, 1～6 preparation reaches (R)-the lansoprazole raw material.
2, polarizing microscope testing conditions: eyepiece amplifies 10 times, the object lens magnify 20.
3, experimental result
The polarization microscope figure of (R)-lansoprazole tert-butylamine salt crystal formation of embodiment 1～6 preparation as shown in Figure 3.As seen from Figure 3: crystal has obvious birefringent phenomenon; Its crystal habit is the irregular particle shape; Its particle diameter is in 10～50 mu m ranges.
(R)-the polarization microscope figure of lansoprazole raw material is as shown in Figure 4.As seen from Figure 4, (R)-lansoprazole has birefringent phenomenon, and its crystal habit is needle-like; Its particle diameter is in 10～200 mu m ranges.
By upper contrast as seen, compare with the needle-like crystal of (R)-lansoprazole raw material, the flowability of the particulate state crystal habit of the present invention (R)-lansoprazole tert-butylamine salt crystal formation is better, is convenient to carrying out smoothly of preparation process.
(R)-lansoprazole tert-butylamine salt crystal formation of 1, sample: embodiment, 1～6 preparation reaches (R)-the lansoprazole raw material.
2, water absorbability detection method: instrument adopts dynamic moisture content moisture absorption instrument (DVS Advantage, Surface Measurement System Ltd.); Experimental temperature: 25 ℃; The relative humidity of humidity range of DO: 0-95%; Step value: 5% relative humidity; The weightening finish tension metrics: changes in weight is less than 0.01% in 5 minutes; The longest starting time: 120 minutes.
3, experimental result
The constant temperature sucting wet curve figure of (R)-lansoprazole tert-butylamine salt crystal formation of embodiment 1～6 preparation as shown in Figure 5, (R)-the constant temperature sucting wet curve figure of lansoprazole raw material is as shown in Figure 6.
As seen from Figure 5, initial mass 11.8674mg, relative humidity is from 0～95%RH, (R)-lansoprazole tert-butylamine salt weightening finish 4.8%, but only having 2.3% from weightening finish between 5～80% the relative humidity, is attainable and be controlled at production from the humidity between 5～80% the relative humidity.
As seen from Figure 6, initial mass 9.5115mg, (R)-and when the lansoprazole raw material is 5～10% in relative humidity, absorb rapidly about 3.5% moisture, become monohydrate; Relative humidity absorbs rapidly again moisture (increasing weight approximately 7.3%) 40～45% the time, becomes 1.5 hydrates.Thus explanation, (R)-the lansoprazole raw material is to moisture-sensitive.
By upper contrast as seen, (R)-lansoprazole tert-butylamine salt water absorbability of the present invention is lower, has clear superiority.
(R)-lansoprazole tert-butylamine salt crystal formation of 1, sample: embodiment, 1～6 preparation reaches (R)-the lansoprazole raw material.
2, solubility test method: precision takes by weighing each sample of 2-3mg in bottle respectively, it is an amount of to add ultrapure water, so that aimed concn is 2.0mg/mL, in 25 ℃ of lower balances 18 hours, no longer change to solubleness, HPLC measures drug level, by the solubleness of preparation standard curve calculation medicine.
The HPLC condition determination: instrument adopts Agilent 1200HPLC chromatographic instrument; Chromatographic column is Zorbax Bonus-Rp (3.5 μ m, 4.6 * 75mm), SN:USTM002141; Mobile phase A is 0.1% (v/v) TFA aqueous solution (mixing in the 3ml TFA adding 3L Milli-Q water), Mobile phase B is 0.1% (v/v) TFA acetonitrile solution (mixing in the 4ml TFA adding 4L acetonitrile), mobile phase A: Mobile phase B=79: 21 (volume ratio), 25 ℃ of column temperatures; Detect wavelength 283nm; Sampling volume 2 μ L; Flow velocity 1mL/min; Detection time 10min; t
0=0.9min, t
R=3.1min, K '=2.4, tailing factor 1.0.
3, experimental result
Table 1 (R)-lansoprazole tert-butylamine salt and (the R)-solubleness of lansoprazole raw material in ultrapure water
By as seen from Table 1, (R)-lansoprazole tert-butylamine salt of the present invention has better water-soluble.
Claims (10)
1. (R)-lansoprazole tert-butylamine salt as shown in Equation 1,
Formula 1.
2. (R)-lansoprazole tert-butylamine salt crystal formation as claimed in claim 1, it is characterized in that: it is using source of radiation to be Cu-K α
1X-ray powder diffraction spectrum in, in diffraction angle 2 θ=6.81,7.31,7.97,9.96, there is the peak at 12.42,13.48,14.32,16.03,18.38,19.89,20.29,20.89,22.85,24.09,24.85,26.00,29.47 and 29.77 degree places; 2 θ value limit of error are ± 0.3, and better is ± 0.2.
3. the preparation method of (R)-lansoprazole tert-butylamine salt crystal formation as claimed in claim 2, it is characterized in that: it comprises the steps: under heating condition, (R)-lansoprazole is dissolved in the organic solvent, adding TERTIARY BUTYL AMINE mixes, be cooled to afterwards crystallization below 5 ℃, separating obtained crystal gets final product.
4. preparation method as claimed in claim 3 is characterized in that: described heating condition is for being heated to 20 ℃～80 ℃, and preferred 40 ℃～70 ℃, more preferably 40 ℃～60 ℃; Described organic solvent is C
3～C
6Esters solvent, one or more in ethyl acetate, methyl acetate, propyl acetate and the butylacetate; The amount of described organic solvent is 30～500mg/ml.
5. preparation method as claimed in claim 3 is characterized in that: the described solution that (R)-lansoprazole is dissolved in the organic solvent gained carries out subsequent operations after with filtering with microporous membrane again; The aperture of described millipore filtration is 0.22～0.8 μ m, preferred 0.45 μ m.
6. preparation method as claimed in claim 3 is characterized in that: the consumption of described TERTIARY BUTYL AMINE is 1～10 times of the molar weight of (R)-lansoprazole, and better is 1～5 times, and better is 1～2 times; The temperature that described adding TERTIARY BUTYL AMINE mixes is 20～80 ℃, preferred 30～70 ℃, and more preferably 35～50 ℃.
7. preparation method as claimed in claim 3 is characterized in that: described mixing employing vortex, magnetic agitation or concussion; The time of described mixing is 5-40 minute, preferred 20～30 minutes.
8. preparation method as claimed in claim 3 is characterized in that: described being cooled to below 5 ℃ as being cooled to-25～5 ℃, and better for being cooled to-20～5 ℃; The time of described cooling, better was that cooling is more than 1～12 hour in order to cool off more than 1 hour.
9. preparation method as claimed in claim 3, it is characterized in that: described dissolving and mixing step carry out under agitation condition.
10. preparation method as claimed in claim 3 is characterized in that: described (R)-lansoprazole tert-butylamine salt crystal formation is separated out rear filtration, washing and dry; Described dry constant pressure and dry or the drying under reduced pressure of adopting.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980250A (en) * | 2014-04-22 | 2014-08-13 | 江苏奥赛康药业股份有限公司 | Lansoprazole compound and its pharmaceutical composition |
| CN104130244A (en) * | 2014-07-29 | 2014-11-05 | 上海右手医药科技开发有限公司 | R-lansoprazole methylamine salt compound and preparation method and pharmaceutical composition thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1355798A (en) * | 1999-06-17 | 2002-06-26 | 武田药品工业株式会社 | Benzimidazole compound crystal |
| WO2010079504A2 (en) * | 2008-05-14 | 2010-07-15 | Watson Pharma Private Limited | Stable r(+)-lansoprazole amine salt and a process for preparing the same |
-
2011
- 2011-07-15 CN CN2011101992000A patent/CN102875530A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1355798A (en) * | 1999-06-17 | 2002-06-26 | 武田药品工业株式会社 | Benzimidazole compound crystal |
| WO2010079504A2 (en) * | 2008-05-14 | 2010-07-15 | Watson Pharma Private Limited | Stable r(+)-lansoprazole amine salt and a process for preparing the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980250A (en) * | 2014-04-22 | 2014-08-13 | 江苏奥赛康药业股份有限公司 | Lansoprazole compound and its pharmaceutical composition |
| CN104130244A (en) * | 2014-07-29 | 2014-11-05 | 上海右手医药科技开发有限公司 | R-lansoprazole methylamine salt compound and preparation method and pharmaceutical composition thereof |
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Application publication date: 20130116 |