CN111057044A - Preparation method of single crystal form of pantoprazole sodium sesquihydrate - Google Patents
Preparation method of single crystal form of pantoprazole sodium sesquihydrate Download PDFInfo
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- CN111057044A CN111057044A CN201911317070.9A CN201911317070A CN111057044A CN 111057044 A CN111057044 A CN 111057044A CN 201911317070 A CN201911317070 A CN 201911317070A CN 111057044 A CN111057044 A CN 111057044A
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- pantoprazole sodium
- sesquihydrate
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- YNWDKZIIWCEDEE-UHFFFAOYSA-N pantoprazole sodium Chemical compound [Na+].COC1=CC=NC(CS(=O)C=2[N-]C3=CC=C(OC(F)F)C=C3N=2)=C1OC YNWDKZIIWCEDEE-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 229960005019 pantoprazole Drugs 0.000 title claims abstract description 47
- 239000013078 crystal Substances 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 34
- 238000010438 heat treatment Methods 0.000 claims abstract description 19
- 238000001816 cooling Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000001914 filtration Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 150000004682 monohydrates Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 229960004048 pantoprazole sodium Drugs 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940126409 proton pump inhibitor Drugs 0.000 description 2
- 239000000612 proton pump inhibitor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WHCXDEORRDVLKS-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1h-benzimidazole;sodium Chemical compound [Na].COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC WHCXDEORRDVLKS-UHFFFAOYSA-N 0.000 description 1
- 108091006112 ATPases Proteins 0.000 description 1
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 201000000052 gastrinoma Diseases 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 150000004677 hydrates Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 210000001711 oxyntic cell Anatomy 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- -1 sesquihydrate Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Chemical group 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention belongs to the technical field of chemical pharmacy, and relates to a preparation method of a single crystal form of pantoprazole sodium sesquihydrate. The preparation method comprises the following steps: (1) adding pantoprazole sodium monohydrate and a solvent into a reaction kettle, and heating to dissolve the pantoprazole sodium monohydrate in the solvent; (2) heating the solution in the reaction kettle to 60-65 ℃, adding pantoprazole sodium sesquihydrate seed crystals, heating and cooling by a program, and separating out the pantoprazole sodium sesquihydrate crystals under stirring; (3) centrifuging and drying the separated pantoprazole sodium sesquihydrate crystal. The preparation method of the single crystal form of pantoprazole sodium sesquihydrate, disclosed by the invention, has the advantages of simplicity in operation, low cost, suitability for mass production and high crystal form purity, and is used for preparing the single crystal form of pantoprazole sodium sesquihydrate.
Description
Technical Field
The invention belongs to the technical field of chemical pharmacy, and relates to a preparation method of a single crystal form of pantoprazole sodium sesquihydrate.
Background
Pantoprazole sodium (Pantoprazole sodium), chemical name 5-difluoromethoxy-2- [ [ (3, 4-dimethoxy-2-pyridyl) -methyl ] sulfinyl ] -1H-benzimidazole sodium, is a third generation Proton Pump inhibitor (PPIs, Proton Pump Inhibitors) developed in becton (Byk Gulden) germany, first marketed in 1994, and its structure is shown below:
pantoprazole sodium as prodrug is converted into active form in acidic medium by inhibiting H+/K+ATPase Activity to make H inside parietal cells+And is not transported to the stomach, thereby inhibiting the secretion of gastric acid. Therefore, the medicine is suitable for active peptic ulcer (gastric ulcer, duodenal ulcer), reflux esophagitis and Zollinger-Ellison syndrome.
Pantoprazole sodium has various hydrates and various solvate forms, such as hemihydrate, monohydrate, sesquihydrate, dihydrate and the like, wherein medicinal crystal forms of the monohydrate and sesquihydrate are imported into pharmacopoeia, for example, 2015 edition of pharmacopoeia of the people's republic of China (pharmacopoeia) which is imported into monohydrate, U.S. pharmacopoeia (USP 39) and European pharmacopoeia (EP 9.0) which are imported into sesquihydrate. The domestic enterprises generally produce monohydrate.
The stability of pantoprazole sodium monohydrate and sesquihydrate is researched by 869-874. the results show that the sesquihydrate is more stable than monohydrate under the conditions of illumination, high temperature and high humidity.
Journal of Medicinal Chemistry,1992,35(6): 1049-: adding pantoprazole into a mixed solvent of ethanol and dichloromethane (V/V is 6/1), stirring and dropwise adding a 6N sodium hydroxide solution at 20 ℃, slowly adding diisopropyl ether after 10 minutes until the mixture becomes turbid, continuously stirring for 2 hours, filtering, leaching a filter cake with diisopropyl ether, and drying in vacuum at 40 ℃ to obtain white-like pantoprazole sodium sesquihydrate.
ACS Omega,2017,2(9): 5460-5469A process for the preparation of pantoprazole sodium sesquihydrate is reported: dissolving pantoprazole free base in acetonitrile, dripping into a sodium hydroxide aqueous solution, adding pantoprazole sodium sesquihydrate seed crystal, stirring at 20-25 ℃ for 2h, cooling to 0-5 ℃, stirring for 3h, filtering, washing with cold acetonitrile, and vacuum drying at 35-40 ℃ to obtain white powdery solid, namely pantoprazole sodium sesquihydrate.
The Chinese journal of New medicine 2015,24(8): 869-: adding pantoprazole into ethyl acetate, stirring to uniformly suspend a sample in a solvent, adding 47% sodium hydroxide aqueous solution, stirring overnight at room temperature, filtering, and drying to obtain crystalline powder, namely pantoprazole sodium sesquihydrate.
Other documents, such as US 7081534, US 2004/0186139, PCT WO2007/0117890, etc., all precipitate the sesquihydrate directly in a solvent system after preparation of pantoprazole free base or sodium salt. The methods seem to be in place in one step, but the defects, namely the mixed crystal phenomenon, exist in the actual operation process, and the purity of the crystal form is not high. In most cases, pharmaceutical raw materials need to have a certain crystal form, and mixed crystals may affect the stability of API or dissolution of a preparation.
In conclusion, a stable and high-operability preparation method of the single crystal form of pantoprazole sodium sesquihydrate needs to be researched.
Disclosure of Invention
The invention aims to provide a preparation method of a single crystal form of pantoprazole sodium sesquihydrate, which is simple to operate, low in cost, suitable for mass production and high in crystal form purity.
To achieve this object, in a basic embodiment, the present invention provides a process for the preparation of a single crystalline form of pantoprazole sodium sesquihydrate, said process comprising the steps of:
(1) adding pantoprazole sodium monohydrate and a solvent into a reaction kettle, and heating to dissolve the pantoprazole sodium monohydrate in the solvent;
(2) heating the solution in the reaction kettle to 60-65 ℃, adding pantoprazole sodium sesquihydrate seed crystals, heating and cooling by a program, and separating out the pantoprazole sodium sesquihydrate crystals under stirring;
(3) centrifuging and drying the separated pantoprazole sodium sesquihydrate crystal.
In a preferred embodiment, the invention provides a preparation method of pantoprazole sodium sesquihydrate in a single crystal form, wherein in the step (1), the solvent is a mixed solvent of ethyl acetate and water.
In a more preferred embodiment, the invention provides a preparation method of single crystal form of pantoprazole sodium sesquihydrate, wherein in the step (1), the mass ratio of ethyl acetate to water to pantoprazole sodium monohydrate is 100 (1-5) to 10.
In a more preferred embodiment, the invention provides a preparation method of single crystal form of pantoprazole sodium sesquihydrate, wherein in the step (1), the mass ratio of ethyl acetate to water to pantoprazole sodium monohydrate is 100 (1.5-2.0): 10.
In a preferred embodiment, the present invention provides a method for preparing pantoprazole sodium sesquihydrate in a single crystal form, wherein in step (2), the temperature is increased or decreased by the following steps:
firstly, cooling to 45-50 ℃ within 0.2-1 hour, preserving heat and stirring for 0.2-0.5 hour;
heating to 60-65 ℃ within 0.2-1 hour, keeping the temperature and stirring for 0.2-0.5 hour;
cooling to 45-50 deg.C within 0.2-1 hr, stirring for 0.2-0.5 hr;
heating to 60-65 ℃ within 0.2-1 hour, keeping the temperature and stirring for 0.2-0.5 hour;
cooling to 20-30 deg.C within 2-3 hr, cooling to 0-10 deg.C within 0.2-1 hr, stirring, and crystallizing for 15-20 hr.
In a preferred embodiment, the invention provides a preparation method of the pantoprazole sodium sesquihydrate single crystal form, wherein in the step (3), the drying is vacuum drying.
In a more preferred embodiment, the invention provides a preparation method of the single crystal form of pantoprazole sodium sesquihydrate, wherein in the step (3), the vacuum drying temperature is 60-70 ℃ and the vacuum drying time is 20-30 hours.
The preparation method has the beneficial effects that the preparation method of the single crystal form of the pantoprazole sodium sesquihydrate has the advantages of simple operation, low cost, suitability for mass production and high crystal form purity, and is used for preparing the single crystal form of the pantoprazole sodium sesquihydrate.
Drawings
Fig. 1 is an XRD detection pattern of pantoprazole sodium sesquihydrate prepared in example 1.
Fig. 2 is an XRD detection pattern of pantoprazole sodium sesquihydrate prepared in example 2.
Detailed Description
The following examples further illustrate embodiments of the present invention.
Example 1: preparation of pantoprazole sodium sesquihydrate
(1) Preparation of pantoprazole sodium monohydrate
Adding 900kg of acetone into the reaction kettle, adding 56kg of sodium hydroxide solution (27 kg of sodium hydroxide is dissolved in 29kg of purified water), and stirring; weighing 125kg of pantoprazole free alkali, adding into a reaction kettle, and uniformly stirring; the mixture was heated to reflux and stirred for 30 minutes. Stopping stirring and heating, controlling the temperature to be 0-15 ℃, standing and crystallizing for 15-20 hours. And (4) centrifuging, performing centrifugal filtration, and performing vacuum drying on the filtered substance for 24 hours to obtain the pantoprazole sodium monohydrate. (2) Preparation of pantoprazole sodium sesquihydrate
Adding 110kg of pantoprazole sodium monohydrate prepared in the previous step, 1100kg of ethyl acetate and 22.5kg of purified water into a reaction kettle, uniformly stirring, heating to reflux, and waiting for the solid to be completely dissolved; controlling the temperature of the solution to 60-65 ℃, stirring and adding 0.45kg of pantoprazole sodium sesquihydrate seed crystal, and carrying out temperature rise and fall according to the following procedures:
firstly, cooling to 48 ℃ within 0.5 hour, preserving heat and stirring for 0.5 hour;
heating to 62 ℃ within 0.5 hour, and stirring for 0.5 hour under the condition of heat preservation;
cooling to 48 ℃ within 0.5 hour, and stirring for 0.5 hour under the condition of heat preservation;
heating to 62 ℃ within 0.5 hour, and stirring for 0.5 hour under the condition of heat preservation;
then cooling to 25 ℃ within 2.5 hours, cooling to 5 ℃ within 0.5 hour, and stirring for crystallization for 18 hours.
Centrifugal filtration, washing the filter cake with 40.0kg ethyl acetate, transferring the wet product to a double cone dryer, and drying for 24 hours under vacuum at 65 ℃.
Example 2: preparation of pantoprazole sodium sesquihydrate (control)
(1) Preparation of pantoprazole sodium monohydrate
Adding 900kg of acetone into the reaction kettle, adding 56kg of sodium hydroxide solution (27 kg of sodium hydroxide is dissolved in 29kg of purified water), and stirring; weighing 125kg of pantoprazole free alkali, adding into a reaction kettle, and uniformly stirring; the mixture was heated to reflux and stirred for 30 minutes. Stopping stirring and heating, controlling the temperature to be 0-15 ℃, standing and crystallizing for 15-20 hours. And (4) centrifuging, performing centrifugal filtration, and performing vacuum drying on the filtered substance for 24 hours to obtain the pantoprazole sodium monohydrate. (2) Preparation of pantoprazole sodium sesquihydrate
Adding 1100kg of ethyl acetate, 22.5kg of purified water and 110kg of pantoprazole sodium monohydrate prepared in the previous step into a reaction kettle, and heating until reflux and stirring for 3 hours; cooling to 5 ℃ within 3 hours, and stirring for crystallization for 18 hours. And (4) centrifugal filtration, leaching a filter cake by using ethyl acetate with the weight being 1 time of that of the filter cake, and transferring a wet product into a double-cone dryer to dry for 24 hours at the temperature of 65 ℃ in vacuum.
Example 3: detection of pantoprazole sodium sesquihydrate
The pantoprazole sodium sesquihydrate prepared in example 1 and example 2 was sampled and subjected to XRD detection under the same detection conditions as those specified in USP 39, and the results are shown in fig. 1 and fig. 2, respectively. Based on this test, the comparison of the main diffraction peak positions reported in the sample prepared in example 1, the USP control, and the literature (International Journal of pharmaceuticals, 2005,291:59-68) is shown in Table 1 below.
TABLE 1
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is intended to include such modifications and variations. The foregoing examples or embodiments are merely illustrative of the present invention, which may be embodied in other specific forms or in other specific forms without departing from the spirit or essential characteristics thereof. The described embodiments are, therefore, to be considered in all respects as illustrative and not restrictive. The scope of the invention should be indicated by the appended claims, and any changes that are equivalent to the intent and scope of the claims should be construed to be included therein.
Claims (7)
1. A preparation method of pantoprazole sodium sesquihydrate in a single crystal form is characterized by comprising the following steps:
(1) adding pantoprazole sodium monohydrate and a solvent into a reaction kettle, and heating to dissolve the pantoprazole sodium monohydrate in the solvent;
(2) heating the solution in the reaction kettle to 60-65 ℃, adding pantoprazole sodium sesquihydrate seed crystals, heating and cooling by a program, and separating out the pantoprazole sodium sesquihydrate crystals under stirring;
(3) centrifuging and drying the separated pantoprazole sodium sesquihydrate crystal.
2. The method of claim 1, wherein: in the step (1), the solvent is a mixed solvent of ethyl acetate and water.
3. The method of claim 2, wherein: in the step (1), the mass ratio of the ethyl acetate to the water to the pantoprazole sodium monohydrate is 100 (1-5) to 10.
4. The method of claim 2, wherein: in the step (1), the mass ratio of the ethyl acetate to the water to the pantoprazole sodium monohydrate is 100 (1.5-2.0) to 10.
5. The method according to claim 1, wherein in the step (2), the temperature is increased or decreased by the following steps:
firstly, cooling to 45-50 ℃ within 0.2-1 hour, preserving heat and stirring for 0.2-0.5 hour;
heating to 60-65 ℃ within 0.2-1 hour, keeping the temperature and stirring for 0.2-0.5 hour;
cooling to 45-50 deg.C within 0.2-1 hr, stirring for 0.2-0.5 hr;
heating to 60-65 ℃ within 0.2-1 hour, keeping the temperature and stirring for 0.2-0.5 hour;
cooling to 20-30 deg.C within 2-3 hr, cooling to 0-10 deg.C within 0.2-1 hr, stirring, and crystallizing for 15-20 hr.
6. The method of claim 1, wherein: in the step (3), the drying is vacuum drying.
7. The method of claim 6, wherein: in the step (3), the temperature of the vacuum drying is 60-70 ℃, and the time is 20-30 hours.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114478479A (en) * | 2020-11-13 | 2022-05-13 | 杭州中美华东制药有限公司 | A kind of preparation method of Levopantoprazole sodium disesquihydrate |
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| WO2004080961A2 (en) * | 2003-03-12 | 2004-09-23 | Teva Pharmaceutical Industries Ltd. | Crystalline and amorphous solids of pantoprazole and processes for their preparation |
| US20040186139A1 (en) * | 2002-09-02 | 2004-09-23 | Dr. Reddy's Laboratories Limited | Process for preparation of crystalline form-1 of pantoprazole sodium sesquihydrate |
| WO2006040778A1 (en) * | 2004-10-15 | 2006-04-20 | Matrix Laboratories Ltd | Process for preparations and purification of pantoprazole sesquihydrate |
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2019
- 2019-12-19 CN CN201911317070.9A patent/CN111057044A/en active Pending
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|---|---|---|---|---|
| US20040186139A1 (en) * | 2002-09-02 | 2004-09-23 | Dr. Reddy's Laboratories Limited | Process for preparation of crystalline form-1 of pantoprazole sodium sesquihydrate |
| WO2004056804A2 (en) * | 2002-12-19 | 2004-07-08 | Teva Pharmaceutical Industries Ltd. | Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates |
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| WO2007086077A2 (en) * | 2006-01-24 | 2007-08-02 | Unichem Laboratories Limited | A novel one pot process for preparation of pantoprazole sodium sesquihydrate |
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| Title |
|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114478479A (en) * | 2020-11-13 | 2022-05-13 | 杭州中美华东制药有限公司 | A kind of preparation method of Levopantoprazole sodium disesquihydrate |
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