CN103012369B - Lansoprazole N crystal form and preparation method and application thereof - Google Patents
Lansoprazole N crystal form and preparation method and application thereof Download PDFInfo
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- CN103012369B CN103012369B CN201210405800.2A CN201210405800A CN103012369B CN 103012369 B CN103012369 B CN 103012369B CN 201210405800 A CN201210405800 A CN 201210405800A CN 103012369 B CN103012369 B CN 103012369B
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- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 229960003174 lansoprazole Drugs 0.000 title claims abstract description 63
- 239000013078 crystal Substances 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 208000007107 Stomach Ulcer Diseases 0.000 claims abstract description 5
- 208000000718 duodenal ulcer Diseases 0.000 claims abstract description 5
- 201000005917 gastric ulcer Diseases 0.000 claims abstract description 5
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims abstract description 5
- 239000012046 mixed solvent Substances 0.000 claims abstract description 5
- 208000000689 peptic esophagitis Diseases 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 31
- 210000001187 pylorus Anatomy 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 241000590002 Helicobacter pylori Species 0.000 abstract 1
- 229940037467 helicobacter pylori Drugs 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229960000381 omeprazole Drugs 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 210000001711 oxyntic cell Anatomy 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000012916 structural analysis Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a lansoprazole N crystal form and a preparation method and application thereof. The X-ray powder diffraction of the lansoprazole N crystal form has characteristic peaks when the diffraction angle 2(theta) is 5.438, 7.062, 8.230, 9.216, 11.022, 11.789, 12.610, 13.541, 20.603, 21.862 and 26.242. The preparation method comprises the following steps of: dissolving lansoprazole in ethyl acetate or a mixed solvent of n-butyl alcohol and water; cooling to separate out crystals; and filtering and drying to obtain the lansoprazole N crystal form. The new lansoprazole crystal form disclosed by the invention is easy to prepare; the preparation method requires little solvent and is simple to operate, and the production cost is low; the reaction conditions are mild, and the control is easy; and the reproducibility is good, and a target product crystal form can be stably obtained. Through the method disclosed by the invention, the prepared lansoprazole crystal form has high purity and low impurity content, maintains all pharmacologic characteristics of lansoprazole, and can be used for treating gastric ulcer, duodenal ulcer and reflux esophagitis and eradicating helicobacter pylori.
Description
Technical field
The present invention relates to lansoprazole new crystal and preparation method thereof.
Background technology
Lansoprazole (Lansoprazole) chemistry is by name: (R)-2-[[[3-methyl-4-(2,2,2-trifluoro ethoxy)-2-pyridyl] methyl] sulfinyl]-1H-benzoglyoxaline, its chemical structural formula is:
Lansoprazole is the benzimidazoles derivative with antiacid effect by the exploitation of Japanese Wu Tian company in December, 1991, and it acts on the H of parietal cell
+-K
+-ATP enzyme, makes the H of parietal cell
+can not be transported in stomach and go, so that in gastric juice, hydrochloric acid in gastric juice amount greatly reduces, be used for the treatment of stomach ulcer, duodenal ulcer and reflux esophagitis, and be used for eliminating pylorus.
Lansoprazole is novel proton pump inhibitor, it is the upgraded product of omeprazole, lansoprazole is because importing fluorine and have trifluoro ethoxy substituting group at 4 side chains of pyridine ring, its bioavailability is improved more than 30% compared with omeprazole, lipotropy is also better than omeprazole, therefore this product can be promptly under acidic conditions sees through parietal cell film and change sulfenic acid and time sulfonyl derivative into and bring into play drug effect, the bacteriostatic activity of HP is risen to four times of omeprazole.
The crystal formation of existing lansoprazole is a lot, but owing to there being the solvate of organic solvent in existing crystal formation, therefore as medicinal lansoprazole crystal formation, only has I type, II type, A type and Type B.
The preparation method of anhydrous crystal forms (I type) and 1.5 crystal types (II type) has been described in CN1355798A.Anhydrous crystal forms (I type) preparation method that this patent is described comprises recrystallization process four times: first amorphous lansoprazole (9.17g) is dissolved in acetone (20mL), under thermal condition, add water (15mL), at room temperature hold over night, add again water (20mL), after supersound process, solid collected by filtration, completes recrystallization for the first time; Then gained solid is dissolved in after acetone (30mL) filters and adds diisopropyl ether (50mL), add crystal seed, mixture is hold over night at room temperature, and filtration drying completes recrystallization for the second time; Gained solid is dissolved in acetone, aqueous precipitation, standing 1h collects solid, and drying under reduced pressure, obtains white solid, completes recrystallization for the third time; Finally gained lansoprazole solid (3.88g) is dissolved in to acetone (4mL), add Di Iso Propyl Ether (14mL), at room temperature standing this solution 30 minutes, filter, the crystallization that collecting precipitation goes out, by Di Iso Propyl Ether (6mL) washed twice, obtain anhydrous crystal forms (I) lansoprazole solid, fusing point: 147.0-148.0 ℃.In this patent, the preparation method of 1.5 crystal types (II type) is: unformed lansoprazole (100mg) is dissolved in ethanol (0.15mL), add water (0.15mL), add after crystal seed, under room temperature standing one hour, collect gained solid, wash twice with water, drying under reduced pressure, obtain 1.5 crystal types (II type) lansoprazole, fusing point: 76.0-80.0 ℃.
The preparation method of lansoprazole A crystal formation has been described in US 2009/0018339A1: lansoprazole (100g) is dissolved in acetone (1500mL), slow cooling to 0 ℃, cooling 3h, filters, and at 50 ℃, dry 2h, obtains lansoprazole A crystal formation.Lansoprazole (35g) is dissolved in ethanol (300mL) under 55 ℃ of conditions, solution is cooled to 0 ℃, by 50mL washing with alcohol precipitation, the dry B crystal formation that obtains.
Lansoprazole anhydrous crystal forms (I type) preparation method who describes in CN1355798A, successively through four recrystallizations, preparation process complexity, consuming time; The lansoprazole B crystal formation of describing in US 2009/0018339A1 is metastable-state crystal, can experience solid-to-solid transition under certain condition, forms A crystal formation.
Especially; the existing crystal formation preparation method of lansoprazole is all in patent protection period; therefore; exploitation has the lansoprazole new crystal of independent intellectual property right can break the patent monoply that external pharmacy corporation is produced for lansoprazole, produces lansoprazole technical support and assurance are provided for Chinese pharmaceutical enterprises.
Summary of the invention
The object of the present invention is to provide a kind of novel, stable lansoprazole new crystal and preparation method thereof.
Another object of the present invention is to provide this novel rope to draw the application in azoles crystal formation preparation treatment stomach ulcer, duodenal ulcer and reflux esophagitis and eliminating pylorus medicine.
Lansoprazole N crystal formation, its X-ray powder diffraction is in angle of diffraction 2
θfor: 5.438, there is characteristic peak at 7.062,8.230,9.216,11.022,11.789,12.610,13.541,20.603,21.862,26.242 o'clock; Its
1h-NMR (CDCl
3) data are: 8.34 (d, 1H), 7.65 (br., 2H), 7.30 (d, 1H), 6.67 (d, 1H), 4.74 (q, 2H), 4.40 (d, 1H), 4.32 (d, 1H), 2.21 (s, 3H); Its IR (KBr, cm
-1) data are: 3628,3382,3133,3071,2974,2896,2818,1645,1582,1475,1441,1315,1265,1198,1168,1111,1036,972,916,857,744,661.
The preparation method of lansoprazole N crystal formation, comprises the following steps:
1) lansoprazole is dissolved in ethyl acetate, or in propyl carbinol and the water volume ratio mixed solvent that is 10:1;
2) above-mentioned solution is cooled to-20~-10 ℃, crystallize out;
3) crystal is filtered, dry, obtain lansoprazole N crystal formation.
Lansoprazole new crystal of the present invention, is easy to preparation.
Ultimate analysis and nuclear magnetic resonance hydrogen spectruming determining result show that lansoprazole crystal formation purity prepared by the present invention is high, and foreign matter content is low.
The required quantity of solvent of preparation method the present invention relates to is few, low production cost.
The preparation method who the present invention relates to is simple to operate, and reaction conditions gentleness is easily controlled.
The preparation method's favorable reproducibility the present invention relates to, acquisition target product crystal formation that can be stable.
Accompanying drawing explanation
Fig. 1 is the X-ray powder diffraction figure of lansoprazole N crystal formation.
Fig. 2 is the differential scanning calorimeter figure (DSC figure) of lansoprazole N crystal formation.
Fig. 3 is infrared spectra (IR) figure of lansoprazole N crystal formation.
Fig. 4 is scanning electron microscope (SEM) figure of lansoprazole N crystal formation.
Embodiment
Lansoprazole N crystal formation, its X-ray powder diffraction is in angle of diffraction 2
θfor: 5.438, there is characteristic peak at 7.062,8.230,9.216,11.022,11.789,12.610,13.541,20.603,21.862,26.242 o'clock; Its
1h-NMR (CDCl
3) data are: 8.34 (d, 1H), 7.65 (br., 2H), 7.30 (d, 1H), 6.67 (d, 1H), 4.74 (q, 2H), 4.40 (d, 1H), 4.32 (d, 1H), 2.21 (s, 3H); Its IR (KBr, cm
-1) data are: 3628,3382,3133,3071,2974,2896,2818,1645,1582,1475,1441,1315,1265,1198,1168,1111,1036,972,916,857,744,661.
The preparation method of lansoprazole N crystal formation, comprises the following steps:
1) lansoprazole is dissolved in ethyl acetate, or in propyl carbinol and the water volume ratio mixed solvent that is 10:1;
2) above-mentioned solution is cooled to-20~-10 ℃, crystallize out;
3) crystal is filtered, dry, obtain lansoprazole N crystal formation.
Below in conjunction with embodiment, further illustrate the present invention.
lansoprazole N crystal formation preparation method
Embodiment 1
1) 50mg lansoprazole is dissolved in 0.1mL ethyl acetate, filters;
2) settled solution is cooled to-10 ℃, its sufficient crystallising is separated out, filter, dry.
Obtain off-white color crystalline powder 42.7mg, productive rate 85.4%.
Embodiment 2
1) 100mg lansoprazole is dissolved in 0.5mL ethyl acetate, filters;
2) settled solution is cooled to-10 ℃, its sufficient crystallising is separated out, filter, dry.
Obtain off-white color crystalline powder 79.6mg, productive rate 79.6%.
Embodiment 3
1) 100mg lansoprazole is dissolved in 0.5mL ethyl acetate, filters;
2) settled solution is cooled to-15 ℃, its sufficient crystallising is separated out, filter, dry.
Obtain off-white color crystalline powder 82.9mg, productive rate 82.9%.
Embodiment 4
1) 1g lansoprazole is dissolved in 1mL ethyl acetate, filters;
2) settled solution is cooled to-20 ℃, its sufficient crystallising is separated out, filter, dry.
Obtain off-white color crystalline powder 0.853g, productive rate 85.3%.
Embodiment 5
1) 1g lansoprazole is dissolved in 1mL ethyl acetate, filters;
2) settled solution is cooled to-20 ℃, its sufficient crystallising is separated out, filter, dry.
Obtain off-white color crystalline powder 0.838g, productive rate 83.8%.
Embodiment 6
1) 100mg lansoprazole is dissolved in to 0.1mL propyl carbinol: water=10:1(volume ratio) mixed solvent in, filter;
2) settled solution is cooled to-10 ℃, its sufficient crystallising is separated out, filter, dry.
Obtain off-white color crystal type powder 87.5mg, productive rate 87.5%.
Get embodiment 4 and obtain off-white color crystalline powder and carry out structural analysis, its result is as follows:
The angle of diffraction 2 of X-ray powder diffraction
θfor: 5.438,7.062,8.230,9.216,11.022,11.789,12.610,13.541,20.603,21.862,26.242, its X-ray powder diffraction figure is as shown in Figure 1;
Results of elemental analyses is: C(%): 48.43, N(%): 10.47, H(%): 4.50;
1h-NMR (CDCl
3) data are: 8.34 (d, 1H), 7.65 (br., 2H), 7.30 (d, 1H), 6.67 (d, 1H), 4.74 (q, 2H), 4.40 (d, 1H), 4.32 (d, 1H), 2.21 (s, 3H);
Its differential scanning calorimeter figure (DSC figure) as shown in Figure 2;
IR (KBr, cm
-1) data are: 3628,3382,3133,3071,2974,2896,2818,1645,1582,1475,1441,1315,1265,1198,1168,1111,1036,972,916,857,744,661, its infrared spectra (IR) is schemed as shown in Figure 3;
Its scanning electron microscope (SEM) is schemed as shown in Figure 4.
The results of structural analysis of embodiment 1~3,5,6 and the results of structural analysis no significant difference of embodiment 4.
Lansoprazole new crystal of the present invention, has retained all pharmacological properties of lansoprazole, has in vivo the effect identical with existing crystal formation, can be used for treating in stomach ulcer, duodenal ulcer and reflux esophagitis and eliminating pylorus.
Claims (5)
1. lansoprazole N crystal formation, its X-ray powder diffraction is in angle of diffraction 2
θfor: 5.438, have characteristic peak at 7.062,8.230,9.216,11.022,11.789,12.610,13.541,20.603,21.862,26.242 o'clock, X-ray powder diffraction figure is substantially as shown in Figure 1.
2. lansoprazole N crystal formation according to claim 1, its
1h-NMR (CDCl
3) data are: 8.34 (d, 1H), 7.65 (br., 2H), 7.30 (d, 1H), 6.67 (d, 1H), 4.74 (q, 2H), 4.40 (d, 1H), 4.32 (d, 1H), 2.21 (s, 3H).
3. lansoprazole N crystal formation according to claim 1, its IR (KBr, cm
-1) data are: 3628,3382,3133,3071,2974,2896,2818,1645,1582,1475,1441,1315,1265,1198,1168,1111,1036,972,916,857,744,661.
4. the preparation method of lansoprazole N crystal formation claimed in claim 1, comprises the following steps:
1) lansoprazole is dissolved in ethyl acetate, or in propyl carbinol and the water volume ratio mixed solvent that is 10:1;
2) above-mentioned solution is cooled to-20~-10 ℃, crystallize out;
3) crystal is filtered, dry, obtain lansoprazole N crystal formation.
5. the application of lansoprazole N crystal formation claimed in claim 1 in preparation treatment stomach ulcer, duodenal ulcer and reflux esophagitis and eliminating pylorus medicine.
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CN103254174B (en) * | 2013-06-05 | 2014-06-11 | 湖北济生医药有限公司 | Lansoprazole compound and pharmaceutical composition thereof |
CN104997738A (en) * | 2015-08-10 | 2015-10-28 | 青岛蓝盛洋医药生物科技有限责任公司 | Medicine lansoprazole compound dry suspension treating gastropathy |
CN107011328B (en) * | 2017-05-05 | 2019-10-15 | 广州大光制药有限公司 | A kind of crystal form and its crystallization preparation method of compound of Lansoprazole |
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