CN104958276A - Pharmaceutical lansoprazole composition capsule for treating gastric ulcer - Google Patents
Pharmaceutical lansoprazole composition capsule for treating gastric ulcer Download PDFInfo
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- CN104958276A CN104958276A CN201510455166.7A CN201510455166A CN104958276A CN 104958276 A CN104958276 A CN 104958276A CN 201510455166 A CN201510455166 A CN 201510455166A CN 104958276 A CN104958276 A CN 104958276A
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Abstract
The invention relates to a pharmaceutical lansoprazole composition capsule for treating gastric ulcer, and belongs to the technical field of medicines. The composition capsule is prepared from lansoprazole, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyanisole, hydroxypropyl methylcellulose, purified water and talcum powder, wherein the lansoprazole is a novel crystal compound; an X-ray powder diffraction pattern obtained by Cu-Kalpha ray measurement is shown in a figure 1; and the pharmaceutical lansoprazole composition capsule is different from the lansoprazole reported in the prior art. An experiment shows that the lansoprazole crystal compound provided by the invention does not contain an impurity E; the content of the impurity A and the impurity B is significantly reduced; the content change along with the prolonging of the storage time is relatively small; the pharmaceutical lansoprazole composition capsule has excellent liquidity and significantly improved dissolution rate; and the lansoprazole capsule prepared from the crystal form compound is high in dissolution degree, good in stability and low in impurity content.
Description
Technical field
The invention belongs to medical art, relate to a kind of medicine Lansoprazole composition capsule for the treatment of gastric ulcer.
Background technology
The benzimidazoles derivative with antiacid effect that lansoprazole is developed in December, 1991 by Japanese Wu Tian company, it acts on the H+-K+-ATP enzyme of parietal cell, the H+ of parietal cell can not be transported in stomach go, so that gastric acid amount greatly reduces in gastric juice, be used for the treatment of gastric 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 at pyridine ring 4 side chains and have trifluoro ethoxy substituent group, make the comparatively omeprazole raising more than 30% of its bioavailability, lipotropy is also better than omeprazole, therefore this product promptly can play drug effect through parietal cell film changes sulfenic acids and time sulfonyl derivative in acid condition, the bacteriostatic activity of HP is risen to four times of omeprazole.
A lot of crystal formations of lansoprazole are disclosed, as the 1.5 crystal types (II type) of the anhydrous crystal forms (I type) and lansoprazole that disclose lansoprazole in CN1355798A in prior art.Describe lansoprazole A crystal formation and B crystal form in US2009/0018339A1, in fact, B crystal form is unstable, is metastable-state crystal, can experience solid-to-solid transition under certain condition, forms A crystal formation.
CN102558154A discloses a kind of lansoprazole crystalline compounds, and the X ray powder diffraction represented with the 2 θ ± 0.2 ° angle of diffraction demonstrates characteristic diffraction peak at 5.8 °, 7.5 °, 9.1 °, 11.8 °, 12.1 °, 12.8 °, 13.3 °, 15.6 °, 16.7 °, 18.3 °, 20.4 °, 25.7 °, 26.8 ° and 31.5 ° of places.
CN102180866A discloses M crystal formation and the N crystal form of lansoprazole, and wherein the X ray powder diffraction of M crystal formation at angle of diffraction 2 θ is: 6.519,9.373,9.989,10.548,13.123,14.298,14.914,15.642,18.104,18.720,19.672,20.231,24.205,25.492,27.899 time there is characteristic peak; The X-ray powder diffraction of N crystal form at angle of diffraction 2 θ is: 5.438,7.062,8.230,9.216,11.022,11.789,12.610,13.541,20.603,21.862,26.242 time there is characteristic peak.
CN1681802A discloses three kinds of crystalline solid form of lansoprazole, and called after D, E and F type, also discloses the preparation method of these crystalline solid form of lansoprazole simultaneously respectively.
CN103664889A also discloses a kind of Lansoprazole crystal compound.
Lansoprazole has a chiral centre sulphur atom, therefore has two optical isomers.Research shows that the lansoprazole drug effect of (R)-configuration is obviously better than lansoprazole raceme, and optically active lansoprazole toxic and side effects is lower than raceme.
But according to the chemical constitution feature of lansoprazole, lansoprazole is being produced, is being deposited easy generation following impurity A, impurity B and impurity E in process, and these trace impurities can affect drug quality.Although some crystal formation of above-mentioned lansoprazole improves its hygroscopicity, dissolubility or stability to a certain extent, the present inventor's its result after the impurity of some crystal formation above-mentioned being carried out to investigation is unsatisfactory.
The present inventor starts with from the research of lansoprazole solid chemical substance existence, has prepared a kind of new compound of Lansoprazole crystal through a large amount of tests.
The lansoprazole of prior art, owing to having stronger hygroscopicity, causes its mobility bad, is unfavorable for the operation of production process; And due to almost insoluble in water, belong to low solubility, Thief zone class medicine, dissolution rate is the rate-limiting step that it absorbs.Directly affect the speed of onset, the power of drug effect due to dissolution rate and hold time, therefore, the dissolution rate improving insoluble drug usually becomes the first step improving its oral administration biaavailability.The present invention finds by test the dissolution that Lansoprazole crystal compound provided by the present invention has good mobility and significantly improves further.
Some crystal formation of the lansoprazole that the preparation method that prior art provides obtains improves from stability, hygroscopicity or dissolubility aspect mostly.But according to the chemical constitution feature of lansoprazole, lansoprazole in production, deposit in process and easily produce impurity A, impurity B and impurity E, these trace impurities can affect the quality of medicine, and the impurity A of the lansoprazole that the method for prior art obtains, impurity B and impurity E are not effectively controlled.
The present inventor is after having carried out large quantifier elimination to it, obtain above-mentioned preparation method, and surprisingly find the Lansoprazole crystal compound E free from foreign meter that the above-mentioned preparation method of employing is obtained, and the content of impurity A and impurity B significantly reduces, and along with its changes of contents of prolongation of period of storage less.
The dissolution that Lansoprazole crystal compound provided by the present invention has good mobility and significantly improves is found further by test.
Compared with prior art, tool of the present invention has the following advantages:
Lansoprazole crystal compound provided by the invention E free from foreign meter, and the content of impurity A and impurity B significantly reduces, and along with its changes of contents of prolongation of period of storage is less, the dissolution that there is excellent mobility and significantly improve, the lansoprazole capsule dissolution utilizing this crystal-form compound to make is high, good stability, impurity content is low.
Summary of the invention
Goal of the invention of the present invention is to provide a kind of medicine Lansoprazole composition capsule for the treatment of gastric ulcer.
In order to complete object of the present invention, the technical scheme of employing is:
The present invention relates to a kind of medicine Lansoprazole composition capsule for the treatment of gastric ulcer, described composition capsule is made up of lansoprazole, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyarisol, hypromellose, purified water, Pulvis Talci; Described lansoprazole is crystal, and the X-ray powder diffraction pattern that the measurement of use Cu-K alpha ray obtains as shown in Figure 1.
First optimal technical scheme of the present invention is: with parts by weight, and described composition capsule is made up of the lansoprazole of 0.10-0.20 weight portion, the lactose of 1-1.8 weight portion, the calcium sulfate of 0.4-0.6 weight portion, the polyvinylpolypyrrolidone of 0.3-0.4 weight portion, the butylated hydroxyarisol of 0.15-0.25 weight portion, the hypromellose of 0.04-0.06 weight portion, the purified water of 0.7-0.9 weight portion, the Pulvis Talci of 0.02-0.04 weight portion.
Second optimal technical scheme of the present invention is: with parts by weight, and described composition capsule is made up of the lansoprazole of 0.15 weight portion, the lactose of 1.4 weight portions, the calcium sulfate of 0.5 weight portion, the polyvinylpolypyrrolidone of 0.35 weight portion, the butylated hydroxyarisol of 0.2 weight portion, the hypromellose of 0.05 weight portion, the purified water of 0.8 weight portion, the Pulvis Talci of 0.03 weight portion.
3rd optimal technical scheme of the present invention is: the preparation method of described composition capsule comprises the following steps:
1) supplementary material process: raw material lansoprazole is crossed 80 mesh sieves with oscillating sieving machine, pulverizes calcium sulfate with pulverizer and crosses 120 mesh sieves;
2) weigh according to technology preparation amount;
3) prepare binding agent: the purified water of getting 70-80 DEG C of recipe quantity is placed in stainless steel cask, adds hypromellose while stirring, be stirred to all be uniformly dissolved stand-by;
4) mixing granulation: the lansoprazole of recipe quantity, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyarisol are added in wet mixing pelletizer, open stirring motor and be dry mixed 10 minutes, add the binder solution prepared, wet mixing 90-120 soft material second, 16 order nylon wires are arranged in oscillating granulator granulates;
5) dry: arranging boiling drier inlet temperature is 50 DEG C, is added by wet granular, is dried to moisture < 3.5%, select 16 order nylon wires to be arranged on granulate in oscillating granulator after dry;
6) always mix: the Pulvis Talci of the dry granule after granulate and recipe quantity is joined in mixer, motor rotation frequency 200r/min is set, open mixer and mix 15 minutes;
7) capsule-filling: select enteric glue shell, use Autocapsulefillingmachine fill, controls content uniformity and meets inner quality standard;
8) pack.
According to the chemical constitution feature of lansoprazole, lansoprazole in production, deposit in process and easily produce impurity A, impurity B and impurity E, these trace impurities can affect the quality of medicine.Prior art provide some crystal formation of lansoprazole mostly improve from stability, hygroscopicity or dissolubility aspect, its impurity is not effectively controlled.
The present inventor is after having carried out large quantifier elimination to it, obtain a kind of lansoprazole crystal compound, and surprisingly find described compound of Lansoprazole E free from foreign meter, and the content of impurity A and impurity B significantly reduces, and along with its changes of contents of prolongation of period of storage less.
The dissolution that compound of Lansoprazole provided by the present invention has good mobility and significantly improves is found further by test.
The preparation method of the lansoprazole crystal in the present composition comprises the following steps:
(1) lansoprazole crude product being joined volume is in 95% alcoholic solution of 6 times of lansoprazole weight, is warming up to 35 DEG C, is stirred to and dissolves completely;
(2) frequency be 30KHz, under output is the sound field of 45W, add the mixed solution of water that volume is lansoprazole weight 8 times, acetone, acetonitrile while stirring, the volume ratio of water, acetone, acetonitrile is 4:2:1, and mixing speed is 130 revs/min, and adding speed is 90 ml/min;
(3) after the mixed solution of water, acetone, acetonitrile adds, frequency be 25KHz, under output is the sound field of 40W, be cooled to-5 DEG C with 10 DEG C/h, growing the grain 2 hours, washing, vacuum drying, obtains compound of Lansoprazole.
Accompanying drawing explanation
Fig. 1 is the X-ray powder diffraction that the lansoprazole crystal of the embodiment of the present invention 1 preparation uses the measurement of Cu-K alpha ray to obtain.
Detailed description of the invention
Below by specific embodiment, summary of the invention of the present invention is described in further detail, but does not therefore limit content of the present invention.
embodiment 1:the preparation of lansoprazole crystal
(1) lansoprazole crude product being joined volume is in 95% alcoholic solution of 6 times of lansoprazole weight, is warming up to 35 DEG C, is stirred to and dissolves completely;
(2) frequency be 30KHz, under output is the sound field of 45W, add the mixed solution of water that volume is lansoprazole weight 8 times, acetone, acetonitrile while stirring, the volume ratio of water, acetone, acetonitrile is 4:2:1, and mixing speed is 130 revs/min, and adding speed is 90 ml/min;
(3) after the mixed solution of water, acetone, acetonitrile adds, frequency be 25KHz, under output is the sound field of 40W, be cooled to-5 DEG C with 10 DEG C/h, growing the grain 2 hours, washing, vacuum drying, obtains compound of Lansoprazole.
The X-ray powder diffraction pattern that the lansoprazole crystal prepared uses the measurement of Cu-K alpha ray to obtain as shown in Figure 1.
embodiment 2:the preparation of lansoprazole capsule
Prescription: with parts by weight, Lansoprazole crystal compound 0.15 part, lactose 1 part, 0.4 part, calcium sulfate, polyvinylpolypyrrolidone 0.3 part, butylated hydroxyarisol 0.15 part, hypromellose 0.04 part, purified water 0.7 part, Pulvis Talci 0.02 part that embodiment 1 is obtained.
Preparation method:
1) supplementary material process: raw material lansoprazole is crossed 80 mesh sieves with oscillating sieving machine, pulverizes calcium sulfate with pulverizer and crosses 120 mesh sieves;
2) weigh according to technology preparation amount;
3) prepare binding agent: the purified water of getting 70-80 DEG C of recipe quantity is placed in stainless steel cask, adds hypromellose while stirring, be stirred to all be uniformly dissolved stand-by;
4) mixing granulation: the lansoprazole of recipe quantity, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyarisol are added in wet mixing pelletizer, open stirring motor and be dry mixed 10 minutes, add the binder solution prepared, wet mixing 90-120 soft material second, 16 order nylon wires are arranged in oscillating granulator granulates;
5) dry: arranging boiling drier inlet temperature is 50 DEG C, is added by wet granular, is dried to moisture < 3.5%, select 16 order nylon wires to be arranged on granulate in oscillating granulator after dry;
6) always mix: the Pulvis Talci of the dry granule after granulate and recipe quantity is joined in mixer, motor rotation frequency 200r/min is set, open mixer and mix 15 minutes;
7) capsule-filling: select enteric glue shell, use Autocapsulefillingmachine fill, controls content uniformity and meets inner quality standard;
8) pack.
embodiment 3:the preparation of lansoprazole capsule
Prescription: with parts by weight, Lansoprazole crystal compound 0.15 part, lactose 1.4 parts, 0.5 part, calcium sulfate, polyvinylpolypyrrolidone 0.35 part, butylated hydroxyarisol 0.2 part, hypromellose 0.05 part, purified water 0.8 part, Pulvis Talci 0.03 part that embodiment 1 is obtained.
Preparation method:
1) supplementary material process: raw material lansoprazole is crossed 80 mesh sieves with oscillating sieving machine, pulverizes calcium sulfate with pulverizer and crosses 120 mesh sieves;
2) weigh according to technology preparation amount;
3) prepare binding agent: the purified water of getting 70-80 DEG C of recipe quantity is placed in stainless steel cask, adds hypromellose while stirring, be stirred to all be uniformly dissolved stand-by;
4) mixing granulation: the lansoprazole of recipe quantity, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyarisol are added in wet mixing pelletizer, open stirring motor and be dry mixed 10 minutes, add the binder solution prepared, wet mixing 90-120 soft material second, 16 order nylon wires are arranged in oscillating granulator granulates;
5) dry: arranging boiling drier inlet temperature is 50 DEG C, is added by wet granular, is dried to moisture < 3.5%, select 16 order nylon wires to be arranged on granulate in oscillating granulator after dry;
6) always mix: the Pulvis Talci of the dry granule after granulate and recipe quantity is joined in mixer, motor rotation frequency 200r/min is set, open mixer and mix 15 minutes;
7) capsule-filling: select enteric glue shell, use Autocapsulefillingmachine fill, controls content uniformity and meets inner quality standard;
8) pack.
embodiment 4:the preparation of lansoprazole capsule
Prescription: with parts by weight, Lansoprazole crystal compound 0.15 part, lactose 1.8 parts, 0.6 part, calcium sulfate, polyvinylpolypyrrolidone 0.4 part, butylated hydroxyarisol 0.25 part, hypromellose 0.06 part, purified water 0.9 part, Pulvis Talci 0.04 part that embodiment 1 is obtained.
Preparation method:
1) supplementary material process: raw material lansoprazole is crossed 80 mesh sieves with oscillating sieving machine, pulverizes calcium sulfate with pulverizer and crosses 120 mesh sieves;
2) weigh according to technology preparation amount;
3) prepare binding agent: the purified water of getting 70-80 DEG C of recipe quantity is placed in stainless steel cask, adds hypromellose while stirring, be stirred to all be uniformly dissolved stand-by;
4) mixing granulation: the lansoprazole of recipe quantity, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyarisol are added in wet mixing pelletizer, open stirring motor and be dry mixed 10 minutes, add the binder solution prepared, wet mixing 90-120 soft material second, 16 order nylon wires are arranged in oscillating granulator granulates;
5) dry: arranging boiling drier inlet temperature is 50 DEG C, is added by wet granular, is dried to moisture < 3.5%, select 16 order nylon wires to be arranged on granulate in oscillating granulator after dry;
6) always mix: the Pulvis Talci of the dry granule after granulate and recipe quantity is joined in mixer, motor rotation frequency 200r/min is set, open mixer and mix 15 minutes;
7) capsule-filling: select enteric glue shell, use Autocapsulefillingmachine fill, controls content uniformity and meets inner quality standard;
8) pack.
test example 1:determination of foreign matter in stability test
Prepare 3 batch samples according to embodiment 1, be numbered 001,002,003
Reference substance 1: according to " improvement in synthesis of lansoprazole " [Liu Yanfei, Li Yongxin etc. the improvement in synthesis [J] of lansoprazole, fine-chemical intermediate, 2011, the lansoprazole fine work of method synthesis 41(3): 26-28 and 42], m.p.169-171 DEG C (decomposition).
Reference substance 2: according to the lansoprazole form D that the method for CN1681802A embodiment 2 is obtained;
Reference substance 3: commercially available lansoprazole bulk drug
Determination of foreign matter method: with reference to " in lansoprazole intestine dissolving capsule the structural identification of impurity, inspection and control " [Xia Guimin, Deng. the structural identification of impurity, inspection and control in lansoprazole intestine dissolving capsule. pharmaceutical analysis impurity, 2012,32(6): 1022-1027] in method measure each impurity content in each sample.The results are shown in Table shown in 1:
Determination of foreign matter in table 1, lansoprazole stability test
test example 2: fluidity test
Method: prepare 3 batch samples according to embodiment 1, be numbered 001,002,003, sample respectively, adopt fixed funnel method, funnel is placed in the suitable height on graph paper, lansoprazole is freely flowed down from bell mouth, until the cone top formed contacts with bell mouth, measures hypotenuse and the horizontal angle (θ angle of repose) of lansoprazole accumulation horizon.The results are shown in Table shown in 2:
The fluidity test result of table 2, lansoprazole
As seen from Table 2, the mobility of lansoprazole prepared of the present invention is better.
test example 3: Dissolution Rate Testing
Prepare 3 batch samples according to embodiment 1, be numbered 001,002,003
Reference substance 1: according to " improvement in synthesis of lansoprazole " [Liu Yanfei, Li Yongxin etc. the improvement in synthesis [J] of lansoprazole, fine-chemical intermediate, 2011, the lansoprazole fine work of method synthesis 41(3): 26-28 and 42], m.p.169-171 DEG C (decomposition).
Reference substance 2: according to the lansoprazole form D that the method for CN1681802A embodiment 2 is obtained;
Reference substance 3: commercially available lansoprazole bulk drug
Method: different lansoprazoles is investigated dissolution according to Pharmacopoeia of the People's Republic of China version in 2010 two annex X C method second methods.With pH6.8 phosphate buffer 900mL for dissolution medium, temperature is 37 DEG C, and rotating speed is 75rmin
-1, the medication amount in each testing sample is 30mg.Adopt ultraviolet spectrophotometry to carry out dissolution determination respectively at 5,10,15,20 and 30min sampling, determined wavelength is 284nm, at 5-25mgL
-1internal linear relation is good, and the response rate, Precision Experiment all meet methodology requirement.The results are shown in Table 3:
The dissolution of table 3, lansoprazole investigates result
As can be seen from Table 3, the water solublity of lansoprazole of the present invention is significantly higher than reference substance, brings conveniently to preparation preparation.
Claims (5)
1. treat a medicine Lansoprazole composition capsule for gastric ulcer, it is characterized in that: described composition capsule is made up of lansoprazole, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyarisol, hypromellose, purified water, Pulvis Talci; Described lansoprazole is crystal, and the X-ray powder diffraction pattern that the measurement of use Cu-K alpha ray obtains as shown in Figure 1.
2. the medicine Lansoprazole composition capsule for the treatment of gastric ulcer according to claim 1, it is characterized in that: with parts by weight, described composition capsule is made up of the lansoprazole of 0.10-0.20 weight portion, the lactose of 1-1.8 weight portion, the calcium sulfate of 0.4-0.6 weight portion, the polyvinylpolypyrrolidone of 0.3-0.4 weight portion, the butylated hydroxyarisol of 0.15-0.25 weight portion, the hypromellose of 0.04-0.06 weight portion, the purified water of 0.7-0.9 weight portion, the Pulvis Talci of 0.02-0.04 weight portion.
3. the medicine Lansoprazole composition capsule for the treatment of gastric ulcer according to claim 1, it is characterized in that, with parts by weight, described composition capsule is made up of the lansoprazole of 0.15 weight portion, the lactose of 1.4 weight portions, the calcium sulfate of 0.5 weight portion, the polyvinylpolypyrrolidone of 0.35 weight portion, the butylated hydroxyarisol of 0.2 weight portion, the hypromellose of 0.05 weight portion, the purified water of 0.8 weight portion, the Pulvis Talci of 0.03 weight portion.
4. prepare a method for the medicine Lansoprazole composition capsule of the arbitrary described treatment gastric ulcer of claim 1-3, it is characterized in that comprising the following steps:
1) supplementary material process: raw material lansoprazole is crossed 80 mesh sieves with oscillating sieving machine, pulverizes calcium sulfate with pulverizer and crosses 120 mesh sieves;
2) weigh according to technology preparation amount;
3) prepare binding agent: the purified water of getting 70-80 DEG C of recipe quantity is placed in stainless steel cask, adds hypromellose while stirring, be stirred to all be uniformly dissolved stand-by;
4) mixing granulation: the lansoprazole of recipe quantity, lactose, calcium sulfate, polyvinylpolypyrrolidone, butylated hydroxyarisol are added in wet mixing pelletizer, open stirring motor and be dry mixed 10 minutes, add the binder solution prepared, wet mixing 90-120 soft material second, 16 order nylon wires are arranged in oscillating granulator granulates;
5) dry: arranging boiling drier inlet temperature is 50 DEG C, is added by wet granular, is dried to moisture < 3.5%, select 16 order nylon wires to be arranged on granulate in oscillating granulator after dry;
6) always mix: the Pulvis Talci of the dry granule after granulate and recipe quantity is joined in mixer, motor rotation frequency 200r/min is set, open mixer and mix 15 minutes;
7) capsule-filling: select enteric glue shell, use Autocapsulefillingmachine fill, controls content uniformity and meets inner quality standard;
8) pack.
5. the medicine Lansoprazole composition capsule for the treatment of gastric ulcer according to claim 1, it is characterized in that, the preparation method of the crystal of described lansoprazole comprises the following steps:
(1) lansoprazole crude product being joined volume is in 95% alcoholic solution of 6 times of lansoprazole weight, is warming up to 35 DEG C, is stirred to and dissolves completely;
(2) frequency be 30KHz, under output is the sound field of 45W, add the mixed solution of water that volume is lansoprazole weight 8 times, acetone, acetonitrile while stirring, the volume ratio of water, acetone, acetonitrile is 4:2:1, and mixing speed is 130 revs/min, and adding speed is 90 ml/min;
(3) after the mixed solution of water, acetone, acetonitrile adds, frequency be 25KHz, under output is the sound field of 40W, be cooled to-5 DEG C with 10 DEG C/h, growing the grain 2 hours, washing, vacuum drying, obtains compound of Lansoprazole.
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| CN102180866A (en) * | 2011-05-23 | 2011-09-14 | 中山大学 | New crystal form of lansoprazole and preparation method and application thereof |
| CN102399212A (en) * | 2010-08-23 | 2012-04-04 | 江苏豪森医药集团有限公司 | Dexlansoprazole crystal form and preparation method thereof |
| CN102558154A (en) * | 2012-02-24 | 2012-07-11 | 海南锦瑞制药股份有限公司 | Lansoprazole crystalline compound, enteric capsule thereof and preparation method of Lansoprazole crystalline compound |
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2015
- 2015-07-30 CN CN201510455166.7A patent/CN104958276A/en not_active Withdrawn
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1000943A1 (en) * | 1998-11-16 | 2000-05-17 | Eisai Co., Ltd. | Sulfoxide compounds and acetone complexes, and a process for producing the same |
| WO2000078745A2 (en) * | 1999-06-17 | 2000-12-28 | Takeda Chemical Industries, Ltd. | Crystalline form of (r)-2-[[[3-methyl- 4- (2,2,2,- trifluoroethoxy) -2- pyridinyl] methyl] sulfinyl] -1h-benzimidazole |
| WO2000078729A1 (en) * | 1999-06-18 | 2000-12-28 | Instytut Farmaceutyczny | Crystalline forms of lansoprazole |
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