WO2000078729A1 - Crystalline forms of lansoprazole - Google Patents
Crystalline forms of lansoprazole Download PDFInfo
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- WO2000078729A1 WO2000078729A1 PCT/PL2000/000042 PL0000042W WO0078729A1 WO 2000078729 A1 WO2000078729 A1 WO 2000078729A1 PL 0000042 W PL0000042 W PL 0000042W WO 0078729 A1 WO0078729 A1 WO 0078729A1
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- Prior art keywords
- lansoprazole
- crystalline form
- methyl
- crystallization
- preparation
- Prior art date
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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 42
- 229960003174 lansoprazole Drugs 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000002329 infrared spectrum Methods 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 description 7
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Definitions
- the object of the invention are crystalline forms of lansoprazole and a method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form.
- Lansoprazole - as a chemical compound - is known from European Patent EP 0174726.
- polymorphism A great number of biologically active compounds crystallizes forming various crystallographic structures. Such a phenomenon is called polymorphism.
- polymorphism may be regarded as a disadvantageous feature.
- Individual polymorphic forms exhibit different chemical stability and reactivity in relation to auxiliary substances and fillers in the finished drug. In some cases considerable differences in their solubility are also observed.
- Infrared spectra (IR, shown in Fig.l) of the two polymorphic forms of lansoprazole made by technique of pressed tablets with potassium bromide (Spectrometer FTIR, Perkin Elmer 1725X) are distinctly different, especially in the range of vibrations that stretch N-H and C-H.
- Powder diffraction patterns (Powder diffraction instrument DRON-4) of both polymorphic forms also substantially differ from each other.
- IR spectra of one of the forms called the crystalline form I indicated that it corresponds to a crystalline form of lansoprazole present in pharmaceutical formulations already approved for therapy, characterized by presence of the following bands in IR spectrum: 3234 (broad band), 2984, 2931, 1581, 1478, 1457, 1402, 1268, 1173, 1119, 1039, 972, 858 , 814 and 750 cm- 1 .
- the crystalline form II is characterized by X-ray powder diffraction pattern shown on Fig.3 and in the corresponding Table 2 as an interdependence of intensities of relative diffraction lines CuK ⁇ , diffraction values ⁇ and interplanar distances d.
- the crystalline form II is stable at temperatures below 0°C. IR spectrum of the form II does not change after one-year storage of samples at temperature -5°C. However, after some period of sample storage at higher temperatures, bands in IR spectra, that are characteristic for the form I of lansoprazole, are observed.
- the crystalline form I of lansoprazole is characterized by high stability. Spectral analysis performed after one-year storage of the substance at room and elevated temperatures exhibited identical spectra IR and powder diffraction patterns. Thus, the crystalline form I is the form pharmaceutically advantageous, stable under conditions of preparation and storage of pharmaceutical formulations containing lansoprazole as an active ingredient.
- a further aspect of the invention is a method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form.
- the method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form I consists in that a crude lansoprazole is subjected to crystallization from aqueous ethanol containing up to 10% water, at temperature from 20°C to 60°C, preferably 55-60°C, and then the resulting lansoprazole (of chromatographic purity of at least 99%) is crystallized from acetone and isolated by a known method.
- the method according to the invention makes it possible to obtain lansoprazole in the stable crystallographic form I, characterized by X-ray powder diffraction pattern consistent with the appended Table 1.
- the method according to the invention may be applied especially for purification of lansoprazole produced in oxydation reaction of 2- ⁇ [3-methyl-4-
- Lansoprazole exhibiting the desired spectral characteristics can be produced by crystallization from acetone of the substance occuring in other, less stable crystalline form or by crystallization of mixture of various crystalline forms of lansoprazole.
- the invention is illustrated by the following examples of embodiments, that are not intended to limit the scope of the invention.
- Example 1 A crude lansoprazole (35 g) , prepared in oxydation reaction of 2- ⁇ [3-methyl-4- (2, 2, 2- trifluoroethoxy) -2-pyridinyl] -methyl ⁇ tio-lH- benzimidazole was added to 300 ml 90% ethanol heated to temperature 55°C. After filtering and cooling the resulting mixture to temp, below 0°C, the precipitate was filtered off and washed with 50% ethanol (50 ml) . The moist precipitate was dried at a temperature not exceeding 50°C, to yield the polymorphic form II with a small amount of the form I. A yield amounted to more than 90% .
- IR (KBr) cm-1 3062-2608 (a broad band with multiple maxima), 1580, 1476, 1459, 1436, 1268, 1173, 1115,
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
According to the invention, a phenomenon of polymorphism of 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl}-sulfinylo-1H-benzimidazole (lansoprazole) is disclosed. The crystalline forms I and II of lansoprazole were obtained and identified and a method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form I was developed. The form I finds application as an active ingredient of pharmaceutical compositions.
Description
Crystalline forms of lansoprazole
The object of the invention are crystalline forms of lansoprazole and a method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form.
Lansoprazole - 2- { [3-methyl-4- (2, 2, 2, -trifluoro- ethoxy) -2-pyridinyl] methyl }-sulfinyl-lH-benzimidazole, is known from pharmaceutical practice as a drug inhibiting secretion of gastric juice, used in the treatment of gastric and duodenal ulcers.
Lansoprazole - as a chemical compound - is known from European Patent EP 0174726.
In European Patent EP 0302720 a method of preparation of lansoprazole consisting in reaction of oxydation of 2- { [3-methyl-4- (2, 2, 2-trifluoroethoxy) -2- pyridinyl ] methyl } tio-lH-benzimidazole - with the use of hydrogen peroxide in the presence of catalytic amounts of vanadium pentoxide - is disclosed. The resulting crude lansoprazole is purified by crystallization from aqueous ethanol (90%), to yield the product containing more than 99% of the main compound.
Another method of preparation of lansoprazole, described in European Patent EP 0174726 and in a
publication [Chem.Pharm.Bull . 38(10), 2853(1990)] consists in the use of m-chloroperbenzoic acid as an oxydation agent. The crude product is purified on a column (silica gel, eluent: ethyl acetate), and then subjected to crystallization from a mixture of solvents: acetone-ethyl ether-hexane .
In the above-mentioned patent specifications as well as in chemical literature no reports concerning polymorphic forms of lansoprazole have been found. A great number of biologically active compounds crystallizes forming various crystallographic structures. Such a phenomenon is called polymorphism. In case of pharmaceuticals polymorphism may be regarded as a disadvantageous feature. Individual polymorphic forms exhibit different chemical stability and reactivity in relation to auxiliary substances and fillers in the finished drug. In some cases considerable differences in their solubility are also observed. Possibility of conversion of one crystalline form into another depending on conditions of preparation, storage or use of a pharmaceutical formulation, that contains one of polymorphic forms of a compound in question as an active ingredient, involves problems as regards prediction of stability and bioavailability of that active ingredient, which guarantees therapeutic effect, and causes that in therapy only one of the polymorphic forms of the substance in question is used.
During our experimental work we haave found that
carrying out the oxydation reaction of 2- { [3-methyl-4- (2,2, 2-trifluoroethoxy) -2-pyridinyl] -methyl } tio-lH- benzimidazole as a step of the method described in European Patents Nos. EP 0302720 and EP 0174726, and purifying the crude product by crystallization, depending on a solvent used for crystallization and on a method of carrying out crystallization, lansoprazole of high degree of chromatographic purity (more than 99%) is produced, but in various crystallographic forms, defined hereafter as the form I or form II, or as a mixture of the forms I and II, possibly as a solvate of one of the forms with a molecule of a solvent .
Infrared spectra (IR, shown in Fig.l) of the two polymorphic forms of lansoprazole made by technique of pressed tablets with potassium bromide (Spectrometer FTIR, Perkin Elmer 1725X) are distinctly different, especially in the range of vibrations that stretch N-H and C-H. Powder diffraction patterns (Powder diffraction instrument DRON-4) of both polymorphic forms also substantially differ from each other.
Analysis of IR spectra of one of the forms called the crystalline form I indicated that it corresponds to a crystalline form of lansoprazole present in pharmaceutical formulations already approved for therapy, characterized by presence of the following bands in IR spectrum: 3234 (broad band), 2984, 2931, 1581, 1478, 1457, 1402, 1268, 1173, 1119, 1039, 972,
858 , 814 and 750 cm- 1 .
The crystalline form I is characterized by X-ray powder diffraction pattern shown on Fig.2 and in the corresponding Table 1 as an interdependence of intensities of relative diffraction lines CuKα at the wavelength λ=1.541 A, diffraction values θ and interplanar distances d. Table 1.
In the case of the form I measurements by differential scanning calorimetry (DSC) exhibited a maximum at 183.57°C.
In IR spectra (Fig. lb) of the polymorphic form II presence of the following bands is found: a broad band with multiple maxima in the range 3062-2608, 1580, 1476, 1459, 1436, 1268, 1173, 1115, 1019, 974, 858, 812, 744 cm"1.
The crystalline form II is characterized by X-ray
powder diffraction pattern shown on Fig.3 and in the corresponding Table 2 as an interdependence of intensities of relative diffraction lines CuKα, diffraction values θ and interplanar distances d.
Table 2
It has been found that the resulting crystalline form of lansoprazole depends on a method used for purification of crude lansoprazole produced by oxydation of 2- { [3-methyl-4- (2, 2, 2-trifluoroethoxy-2- pyridinyl] methyl } tio-lH-benzimidazole .
When purifying crude lansoprazole by crystallization from aqueous ethanol (up to 10% water content), the crystalline form II is obtained, characterized by X-ray powder diffraction pattern according to Table 2. Measurements by differential scanning calorimetry (DSC) exhibited a presence of maximum at 182.38°C.
The crystalline form II is stable at temperatures
below 0°C. IR spectrum of the form II does not change after one-year storage of samples at temperature -5°C. However, after some period of sample storage at higher temperatures, bands in IR spectra, that are characteristic for the form I of lansoprazole, are observed.
The crystalline form I of lansoprazole is characterized by high stability. Spectral analysis performed after one-year storage of the substance at room and elevated temperatures exhibited identical spectra IR and powder diffraction patterns. Thus, the crystalline form I is the form pharmaceutically advantageous, stable under conditions of preparation and storage of pharmaceutical formulations containing lansoprazole as an active ingredient.
A further aspect of the invention is a method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form.
The method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form I consists in that a crude lansoprazole is subjected to crystallization from aqueous ethanol containing up to 10% water, at temperature from 20°C to 60°C, preferably 55-60°C, and then the resulting lansoprazole (of chromatographic purity of at least 99%) is crystallized from acetone and isolated by a known method.
The method according to the invention makes it possible to obtain lansoprazole in the stable
crystallographic form I, characterized by X-ray powder diffraction pattern consistent with the appended Table 1.
The method according to the invention may be applied especially for purification of lansoprazole produced in oxydation reaction of 2- { [3-methyl-4-
(2,2, 2-trifluoroethoxy) -2-pyridinyl] -methyl } tio-lH- benzimidazole, but it is not limited to that method of the substance synthesis. Lansoprazole exhibiting the desired spectral characteristics can be produced by crystallization from acetone of the substance occuring in other, less stable crystalline form or by crystallization of mixture of various crystalline forms of lansoprazole. The invention is illustrated by the following examples of embodiments, that are not intended to limit the scope of the invention.
Example 1. A crude lansoprazole (35 g) , prepared in oxydation reaction of 2- { [3-methyl-4- (2, 2, 2- trifluoroethoxy) -2-pyridinyl] -methyl } tio-lH- benzimidazole was added to 300 ml 90% ethanol heated to temperature 55°C. After filtering and cooling the resulting mixture to temp, below 0°C, the precipitate was filtered off and washed with 50% ethanol (50 ml) . The moist precipitate was dried at a temperature not exceeding 50°C, to yield the polymorphic form II with a small amount of the form I. A yield amounted to more
than 90% .
IR (KBr) cm-1: 3062-2608 (a broad band with multiple maxima), 1580, 1476, 1459, 1436, 1268, 1173, 1115,
1019, 974, 858, 812, 744. DSC-max 182.38°C. H20 content: 0.08%.
Example 2.
Lansoprazole prepared as in Example 1 (100 g) was dissolved at boiling temperature in 1500 ml of acetone. After filtration the solution was cooled to room temperature, and then slowly cooled for 3 hours to attain temperature 0°C . After filtering off, the resulting precipitate was dried for 2 hours at temperature below 50°C, to yield lansoprazole in the crystallographic form I . Yield >95% . IR (KBr), cm-1: 3234 (broad band), 2984, 2931, 1581,
1478, 1457, 1402, 1268, 1173, 1119, 1039, 972, 858,
814 and 750.
DSC-max 183 . 57°C . H20 content : 0 . 08 % .
Claims
1. Crystalline form I of lansoprazole characterized by the following X-ray powder diffraction pattern showing interdependence of intensities of relative diffraction lines CuKα, diffraction values θ and interplanar distances d:
2. Crystalline form I of lansoprazole according to Claim 1, characterized by IR spectrum shown in Fig. la.
3. Crystalline form II of lansoprazole characterized by the following X-ray powder diffraction pattern showing interdependence of intensities of relative diffraction lines CuKα, diffraction values θ and interplanar distances d: 
4. Crystalline form II of lansoprazole according to Claim 3, characterized by IR spectrum shown on Fig. lb.
5. Method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form I, wherein the crude lansoprazole is subjected to crystallization from ethanol containing up to 10% water, at a temperature from 20°C to 60°C, preferably 55-60°C, and then the resulting lansoprazole of chromatographic purity of at least 99% is crystallized from acetone and isolated by a known method.
6. Method of preparation of lansoprazole in the pharmaceutically advantageous crystalline form I, wherein the lansoprazole resulting from oxydation reaction of 2- { [3-methyl-4- (2, 2, 2-trifluoroethoxy) -2- pyridinyl] -methyl } tio-lH-benzimidazole is subjected to crystallization.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PLP.333847 | 1999-06-18 | ||
| PL99333847A PL333847A1 (en) | 1999-06-18 | 1999-06-18 | Crystalline forms of lansoprozole and method of obtaining lansoprazole in pharmacologically advanthageous crystalline form |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2000078729A1 true WO2000078729A1 (en) | 2000-12-28 |
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ID=20074597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/PL2000/000042 WO2000078729A1 (en) | 1999-06-18 | 2000-06-15 | Crystalline forms of lansoprazole |
Country Status (2)
| Country | Link |
|---|---|
| PL (1) | PL333847A1 (en) |
| WO (1) | WO2000078729A1 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003082857A3 (en) * | 2002-03-27 | 2003-12-18 | Teva Pharma | Lansoprazole polymorphs and processes for preparation thereof |
| KR100433735B1 (en) * | 2001-06-27 | 2004-06-04 | 주식회사 씨트리 | Preparation method of Lansoprazole having crystalline form I |
| EP1681056A1 (en) * | 2005-01-14 | 2006-07-19 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
| KR100758600B1 (en) | 2006-01-05 | 2007-09-13 | 주식회사 대웅제약 | Method for preparing lansoprazole crystalline form A |
| WO2008077866A1 (en) * | 2006-12-22 | 2008-07-03 | Recordati Industria Chimica E Farmaceutica Spa | Process for manufacturing microcrystalline lansoprazole form i |
| US7435825B2 (en) | 2001-08-17 | 2008-10-14 | Grunenthal Gmbh | Hydrates of optionally substituted 2-(2-pyridinyl) methylthio-1H-benzimidazoles and process for the production thereof |
| EP2663306A1 (en) * | 2011-01-12 | 2013-11-20 | Hetero Research Foundation | Polymorphs of dexlansoprazole salts |
| CN104829594A (en) * | 2015-05-15 | 2015-08-12 | 苗怡文 | Pharmaceutical lansoprazole compound for treating gastric ulcer |
| CN104958276A (en) * | 2015-07-30 | 2015-10-07 | 青岛蓝盛洋医药生物科技有限责任公司 | Pharmaceutical lansoprazole composition capsule for treating gastric ulcer |
| 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 |
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|---|---|---|---|---|
| EP0302720A1 (en) * | 1987-08-04 | 1989-02-08 | Takeda Chemical Industries, Ltd. | Production of 2-(2-Pyridylmethylsulfinyl)-benzimidazole compounds |
| WO1998021201A1 (en) * | 1996-11-14 | 1998-05-22 | Takeda Chemical Industries, Ltd. | Crystals of benzimidazole derivatives and their production |
-
1999
- 1999-06-18 PL PL99333847A patent/PL333847A1/en unknown
-
2000
- 2000-06-15 WO PCT/PL2000/000042 patent/WO2000078729A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0302720A1 (en) * | 1987-08-04 | 1989-02-08 | Takeda Chemical Industries, Ltd. | Production of 2-(2-Pyridylmethylsulfinyl)-benzimidazole compounds |
| WO1998021201A1 (en) * | 1996-11-14 | 1998-05-22 | Takeda Chemical Industries, Ltd. | Crystals of benzimidazole derivatives and their production |
Non-Patent Citations (4)
| Title |
|---|
| KOTAR B ET AL: "study of polymorphism of a novel antiulcer drug", EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 4 (Supplement), September 1996 (1996-09-01), pages S182, XP000052903 * |
| KUBO K ET AL: "Synthesis of 2-[[(4-fluoroalkoxy-2-pyridyl)methyl] sulfinyl]-1H-benzimidazoles as antiulcer agents", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 38, no. 10, October 1990 (1990-10-01), pages 2853 - 2858, XP002150630 * |
| SITAR CURIN A ET AL: "Study of crystal modifications of lansoprazole using FT-IR spectroscopy, solid-state NMR spectroscopy and FT-Raman spectroscopy", FARMACEVTSKI VESTNIK, vol. 48, 1997, Lubljana, pages 290 - 291, XP000946953 * |
| VRECER F ET AL: "Study of influence of temperature and grinding on the crystalline state of lansoprazole", FARMACEVTSKI VESTNIK, vol. 48, 1997, Ljubjana, pages 242 - 243, XP000946952 * |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100433735B1 (en) * | 2001-06-27 | 2004-06-04 | 주식회사 씨트리 | Preparation method of Lansoprazole having crystalline form I |
| US7435825B2 (en) | 2001-08-17 | 2008-10-14 | Grunenthal Gmbh | Hydrates of optionally substituted 2-(2-pyridinyl) methylthio-1H-benzimidazoles and process for the production thereof |
| US7557218B2 (en) | 2001-08-17 | 2009-07-07 | Grunenthal Gmbh | Hydrates of optionally substituted 2-(2-pyridinyl) methylthio-1H-benzimidazoles and process for the production thereof |
| WO2003082857A3 (en) * | 2002-03-27 | 2003-12-18 | Teva Pharma | Lansoprazole polymorphs and processes for preparation thereof |
| EP2308492A1 (en) * | 2005-01-14 | 2011-04-13 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for preparing lansoprazole |
| EP1681056A1 (en) * | 2005-01-14 | 2006-07-19 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
| WO2006074952A1 (en) * | 2005-01-14 | 2006-07-20 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
| EA015043B1 (en) * | 2005-01-14 | 2011-04-29 | Крка, Товарна Здравил, Д.Д., Ново Место | Process for preparing lansoprazole |
| US7662968B2 (en) | 2005-01-14 | 2010-02-16 | KRKA tovarna zdravil, d.d.. | Process for preparing lansoprazole |
| KR100758600B1 (en) | 2006-01-05 | 2007-09-13 | 주식회사 대웅제약 | Method for preparing lansoprazole crystalline form A |
| WO2008077866A1 (en) * | 2006-12-22 | 2008-07-03 | Recordati Industria Chimica E Farmaceutica Spa | Process for manufacturing microcrystalline lansoprazole form i |
| EP2663306A1 (en) * | 2011-01-12 | 2013-11-20 | Hetero Research Foundation | Polymorphs of dexlansoprazole salts |
| EP2663306A4 (en) * | 2011-01-12 | 2014-01-01 | Hetero Research Foundation | Polymorphs of dexlansoprazole salts |
| CN104829594A (en) * | 2015-05-15 | 2015-08-12 | 苗怡文 | Pharmaceutical lansoprazole compound for treating gastric ulcer |
| CN104958276A (en) * | 2015-07-30 | 2015-10-07 | 青岛蓝盛洋医药生物科技有限责任公司 | Pharmaceutical lansoprazole composition capsule for treating gastric ulcer |
| 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 |
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