AU2002216042A1 - Freeze-dried pantoprazole preparation and pantoprazole injection - Google Patents
Freeze-dried pantoprazole preparation and pantoprazole injectionInfo
- Publication number
- AU2002216042A1 AU2002216042A1 AU2002216042A AU2002216042A AU2002216042A1 AU 2002216042 A1 AU2002216042 A1 AU 2002216042A1 AU 2002216042 A AU2002216042 A AU 2002216042A AU 2002216042 A AU2002216042 A AU 2002216042A AU 2002216042 A1 AU2002216042 A1 AU 2002216042A1
- Authority
- AU
- Australia
- Prior art keywords
- pantoprazole
- salt
- injection
- freeze
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Description
Freeze-dried Pantoprazole Preparation and Pantoprazole Injection
Technical Field
The present invention relates to the field of pharmaceutical technology and describes freeze-dried 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridinyl)methylsulfinyl]-1 H-benzimidazole preparations and a 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridinyl)methylsulfinyl]-1 H-benzimidazole injection. Furthermore the invention also relates to a process for the production of freeze-dried 5-difluoromethoxy- 2-[(3,4-dimethoxy-2-pyridinyl)methylsulfinyl]-1 H-benzimidazole and a 5-difluoromethoxy-2-[(3,4-dirneth- oxy-2-pyridinyl)methylsulfinyl]-1 H-benzimidazole injection.
Prior art
WO94/02141 describes an injection comprising a 2-[(2-pyridyl)methylsulfinyl]-benzimidazole compound an aqueous solvent added with no nonaqueous solvent, wherein the pH of the injection is not less than 9.5 and not more than 11.5. It is mentioned that said injection does not cause hemolysis and causes less local irritation.
DE 43 24 014 describes the preparation of a lyophilisate of pantoprazole-sodium sesquihydrate in the presence of sucrose as an auxiliary at production temperatures of -25 to -30°C. It is disclosed that the lyophilisate is of improved storage stability and can be stored at room temperature for at least 18 months and is easily reconstituted in liquid form in suitable doses for use.
CN 1235018 describes a freeze-dried injection powder of pantoprazole sodium containing no crystallised water with pH value of 9-12.5, which is composed of pantoprazole sodium, freeze-dried powder supporting agent, metal ion complexing agent and pH regulator.
W099/18959 describes aqueous pharmaceutical compositions which are chemically and physically stable for intravenous injection which comprise anti-ulcerative compound and glycine as stabilizer in carrier.
Description of invention
Reconstitution of lyophilised pharmaceutical compounds with carrier solutions for application may lead to the formation of visible and/or subvisible particles in the solution. Injectable solutions, including solutions constituted from sterile solids intended for parenteral use should be essentially free from particles that can be observed on visual inspection and for patient safety it is also desirable to have a low number of subvisible particles. USP (United States Pharmacopeia) 24 describes physical tests performed for the purpose of enumerating subvisible extraneous particles within specific size ranges and also defines particulate matters limits set forth for the test being applied for large-volume injections for single-dose infusion and small-volume injections (USP 24, <788> Particulate Matter in Injections).
Surprisingly it has now been found that by freeze drying of an aqueous solution of pantoprazole, ethylenediamine tetraacetic acid and/or a suitable salt thereof, and sodium hydroxide and/or sodium carbonate a lyophilisate is obtained having significantly lower number of subvisible particles after reconsti- tuion with a solvent compared to lyophilisates of the state of the art. The lyophilisate according to the invention is very stabile and is easily reconstituted with suitable solvents. In particular the pantoprazole injection according to the invention has less than 130, preferably less than 120 subvisible particles/per vial, the particles having a size equal to or greater as 10μm, the number of particles determined according to USP 24 (<788> Particle Matter in Injections) by light obscuration particle test count.
5-Difluoromethoxy-2-[(3,4-dimethoxy-2-pyridinyl)methylsulfinyI]-1 H-benzimidazole (INN: pantoprazole, in connection with the invention also referred to as pantoprazole) is known from EP-A-0 166 287. Pantoprazole is a chiral compound. In connection with the invention the term pantoprazole also includes the pure enantiomers of pantoprazole and their mixtures in any mixing ratio. (S)-pantoprazoIe [(-)-pantoprazole] may be mentioned by way of example. Pantoprazole is present here as such or preferably in the form of it's salt with a base. Examples of salts with a base which may be mentioned are sodium, potassium, magnesium and calcium salts. Pantoprazole and/or a salt thereof may contain, various amounts of solvent when isolated in crystalline form. In connection with the invention pantoprazole also refers to all solvates and in particular to hydrates of 5-difluoromethoxy-2-[(3,4-dimethoxy-2- pyridinyl)methylsulfinyl]-1 H-benzimidazole and salts thereof. Such a hydrate of the salt of pantoprazole with a base is disclosed, for example, in WO91/19710. Expediently pantoprazole refers to pantoprazole sodium sesquihydrate (= pantoprazole sodium x 1.5 H20) and pantoprazole magnesium dihydrate.
According to the invention the pantoprazole solution used in the freeze drying process can be obtained by addition of ethylenediamine tetraacetic acid and/or a suitable salt thereof, and sodium hydroxide and/or sodium carbonate to an aqueous solvent. Suitable salts of ethylenediamine tetraacetic acid which may be mentioned in connection with the invention by way of example are ethylenediamine
tetraacetic acid disodium salt, ethylenediamine tetraacetic acid calcium disodium salt ethylenediamine tetraacetic acid trisodium salt and ethylenediamine tetraacetic acid tetrasodium salt. The proportion by weight of ethylenediamine tetraacetic acid and/or a suitable salt thereof, based on the amount of pantoprazole used is from 0.05 to 25 % preferably from 0.25 to 12.5 % or particular preferred from 1 to 5 %. The aqueous solvent preferentially is water for injection. Subsequently pantoprazole is added to the solution and dissolved by stirring. It is preferred to have a solution wherein the proportion of weight (m/m) of pantoprazole is 0.5 to 10 %, particularly preferred 1 to 6 %. In a further preferred embodiment of the invention the pH of the solution used in the freeze drying process is 8 or above 8, particularly preferred the pH is in the range from 10 to 13. Then this solution is filtered for sterilization and charged in vials. The solution is then freeze dried by a method known per se.
A pantoprazole injection according to the invention can be produced by dissolving the lyophilized product thus obtained in a suitable solvent for example physiological saline, aqueous solution of 5% glucose, or distilled water for injection. Preferably the pantoprazole injection according to the invention is used in the form of intravenous injection.
The lyophilised product and pantoprazole injection according to the invention preferably contain pantoprazole in the dose customary for the treatment of the respective disease. The lyophilised product and pantoprazole injection according to the invention can be employed for the treatment and prevention of all the diseases which are regarded as treatable or avoidable by the use of pyridin-2-ylmethylsulfinyl- 1 H-benzimidazoles. In particular, the lyophilised product and pantoprazole injection according to the invention can be employed in the treatment of stomach disorders. The lyophilized products in particular contain between 5 and 150 mg, preferably between 5 and 60 mg, of pantoprazole. Examples which may be mentioned are lyophilized products or injections which contain 10, 20, 40, 50 or 96 mg of pantoprazole. The administration of the daily dose (e.g. 40 mg of active compound) can be carried out, for example, in the form of an individual dose or by means of a number of doses of the administration forms according to the invention (e.g. 2 times 20 mg of active compound). The concentration of pantoprazole in the injection according to the invention may vary depending upon the administration route and generally ranges in a proportion of 0.05-10 mg/ml, preferably 0.1 to 5 mg/ml on a free compound basis. For example for bolus administration 20 to 120 mg of lyophilized product according to the invention can be reconstituted with 10 ml physiological saline.
The production of the lyophilized product and pantoprazole injection is described by way of example below. The following examples illustrate the invention in greater detail, without restricting it.
Examples
Production of a lyophilized pantoprazole preparation
Example 1
Under nitrogen atmosphere, 0.276 g Ethylenediamine tetraacetic acid disodium salt and 6.7 g sodium hydroxide (1 aqueous solution) are added to 480 g water for injection of 4°C to 8°C. 12.47 g pantoprazole sodium sesquihydrate is added while stirring to give a clear solution. The weight of the solution is adjusted to 500 g by addition of water for injection. The pH of the solution is 11.76. The solution is filtered through a 0.2 μm membrane filter and filled in glass vials (1.81 g by vial). Filled vials are semi- stoppered and put into a freeze-dryer (GT4 Edwards/Kniese or GT8 Amsco) for lyophilisation. The vials are cooled to -45°C, then the temperature is raised to -20 to -5°C under vacuum (0.1 to 0.5 mbar) for drying. After finishing main drying the temperature is raised to 30°C, the vacuum is adjusted to 0.01 mbar and drying is continued for an additional 3 hours. An off-white lyophilized product is obtained which is easily reconstituted with physiological saline to give a clear solution.
Comparative Examples
Example 2
Under nitrogen atmosphere, 12.47 g pantoprazole sodium sesquihydrate is added to 480 g water for injection of 4°C to 8°C while stirring to give a clear solution. The volume of the solution is adjusted to 500 g by addition of water for injection. The pH of the solution is 10.85. The solution is filtered through a 0.2 μm membrane filter and filled in glass vials (1.81 g by vial). Filled vials are semi-stoppered and put into a freeze-dryer (GT4 Edwards/Kniese or GT8 Amsco) for lyophilisation. The vials are cooled to -45°C, then the temperature is raised to -20 to -5°C under vacuum (0.1 to 0.5 mbar) for drying. After finishing main drying the temperature is raised to 30°C, the vacuum is adjusted to 0.01 mbar and drying is continued for an additional 3 hours. An off-white lyophilized product is obtained.
Example 3
Under nitrogen atmosphere, 2.45 g sodium hydroxide (1 N aqueous solution) is added to 480 g water for injection of 4°C to 8°C. 12.47 g pantoprazole sodium sesquihydrate is added while stirring to give a clear solution. The weight of the solution is adjusted to 500 g by addition of water for injection. The pH of the solution is 12.02. The solution is filtered through a 0.2 μm membrane filter and filled in glass vials (1.81 g by vial). Filled vials are semi-stoppered and put into a freeze-dryer (GT4 Edwards/Kniese or GT8 Amsco) for lyophilisation. The vials are cooled to -45°C, then the temperature is raised to -20 to -
5°C under vacuum (0.1 to 0.5 mbar) for drying. After finishing main drying the temperature is raised to 30°C, the vacuum is adjusted to 0.01 mbar and drying is continued for an additional 3 hours. An off- white lyophilized product is obtained.
Example 4
Under nitrogen atmosphere, 0.05 g Ethylenediamine tetraacetic acid disodium salt is added to 480 g water for injection of 4°C to 8°C. 12.47 g pantoprazole sodium sesquihydrate is added while stirring to give a clear solution. The weight of the solution is adjusted to 500 g by addition of water for injection. The pH of the solution is 10.2. The solution is filtered through a 0.2 μm membrane filter and filled in glass vials (1.81 g by vial). Filled vials are semi-stoppered and put into a freeze-dryer (GT4 Edwards/- Kniese or GT8 Amsco) for lyophilisation. The vials are cooled to -45°C, then the temperature is raised to -20 to -5°C under vacuum (0.1 to 0.5 mbar) for drying. After finishing main drying the temperature is raised to 30°C, the vacuum is adjusted to 0.01 mbar and drying is continued for an additional 3 hours. An off-white lyophilized product is obtained.
Light obscuration particle test count
Particulate matter/per vial in solutions constituted from the lyophilized products obtained according to Examples 1 to 4 were determined according to USP 24 (<788> Particulate Matter in Injections) by light obscuration particle test count.
The number of extraneous particles per vial having a size equal to or greater as 10 μm detected are summarized in Table 1. As may be evident from table 1 , the number of subvisible particles per vial (equal to or greater as 10μm) in solutions constituted from products obtained according to the invention (EXAMPLE 1 ) is lower than for products obtained by methods which differ from the present invention (EXAMPLES 2 to 4).
Table 1:
Claims (10)
1. Process for the production of a freeze-dried preparation comprising 5-difluoromethoxy-2-[(3,4-di- methoxy-2-pyridinyl)methylsulfinyl]-1 H-benzimidazole (pantoprazole), a salt thereof, a solvate of pantoprazole or a salt thereof, comprising freeze-drying of an aqueous solution of pantoprazole, a salt thereof, a solvate of pantoprazole or a salt thereof, ethylenediamine tetraacetic acid and/or a suitable salt thereof, and sodium hydroxide and/or sodium carbonate.
2. Process according to claim 1, comprising dissolution of ethylenediamine tetraacetic acid and/or a suitable salt thereof in water, adjusting pH of the solution to 8 or above 8 by addition of sodium hydroxide and/or sodium carbonate and addition of pantoprazole, a salt thereof, a solvate of pantoprazole or a salt thereof, to the thus obtained solution.
3. Process according to claim 1 , wherein the proportion by weight of ethylenediamine tetraacetic acid and/or a suitable salt thereof, based on the amount of pantoprazole present is from 0.05 to 25 %, from 0.25 to 12.5 %, or from 1 to 5 %.
4. Process according to claim 1 , wherein pantoprazole is pantoprazole sodium sesquihydrate.
5. Process according to claim 1 wherein the pH of the aqueous solution is in the range from 10 to 13.
6. Lyophilized pantoprazole preparation obtainable by a process according to claims 1 to 5.
7. Pantoprazole injection for bolus administration obtainable by reconstitution of the pantoprazole preparation according to claim 6 in a suitable solvent.
8. Pantoprazole injection according to claim 7, wherein the solvent is physiological saline.
9. Injection kit comprising a lyophilized pantoprazole preparation according to claim 6 and a solvent suitable for bolus administration.
10. Pantoprazole injection having less than 130, preferably less than 120 subvisible particles/per vial, the particles having a size equal to or greater as 10 μm, the number of particles determined according to USP 24 (<788> Particle Matter in Injections) by light obscuration particle test count.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2006235847A AU2006235847C1 (en) | 2000-11-22 | 2006-11-03 | Lyophilized pantoprazole preparation |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00125569.4 | 2000-11-22 | ||
| EP00125569 | 2000-11-22 | ||
| PCT/EP2001/013296 WO2002041919A1 (en) | 2000-11-22 | 2001-11-17 | Freeze-dried pantoprazole preparation and pantoprazole injection |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006235847A Division AU2006235847C1 (en) | 2000-11-22 | 2006-11-03 | Lyophilized pantoprazole preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002216042A1 true AU2002216042A1 (en) | 2002-08-08 |
| AU2002216042B2 AU2002216042B2 (en) | 2006-08-03 |
Family
ID=8170452
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU1604202A Pending AU1604202A (en) | 2000-11-22 | 2001-11-17 | Freeze-dried pantoprazole preparation and pantoprazole injection |
| AU2002216042A Expired AU2002216042B2 (en) | 2000-11-22 | 2001-11-17 | Freeze-dried pantoprazole preparation and pantoprazole injection |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU1604202A Pending AU1604202A (en) | 2000-11-22 | 2001-11-17 | Freeze-dried pantoprazole preparation and pantoprazole injection |
Country Status (40)
| Country | Link |
|---|---|
| US (3) | US6780881B2 (en) |
| EP (2) | EP1339430B1 (en) |
| JP (1) | JP4886158B2 (en) |
| KR (2) | KR100910607B1 (en) |
| CN (1) | CN1250292C (en) |
| AR (2) | AR034277A1 (en) |
| AT (1) | ATE381946T1 (en) |
| AU (2) | AU1604202A (en) |
| BG (1) | BG66329B1 (en) |
| BR (1) | BRPI0115483B8 (en) |
| CA (2) | CA2428870C (en) |
| CY (1) | CY1107896T1 (en) |
| CZ (1) | CZ304348B6 (en) |
| DE (1) | DE60132108T2 (en) |
| DK (1) | DK1339430T3 (en) |
| EA (1) | EA007602B1 (en) |
| EC (1) | ECSP034613A (en) |
| EE (1) | EE05236B1 (en) |
| ES (1) | ES2298295T3 (en) |
| GE (1) | GEP20053461B (en) |
| HK (1) | HK1060848A1 (en) |
| HR (1) | HRP20030410B1 (en) |
| HU (1) | HUP0303278A3 (en) |
| IL (2) | IL155601A0 (en) |
| IS (1) | IS2971B (en) |
| ME (1) | ME00556A (en) |
| MX (1) | MXPA03004548A (en) |
| MY (1) | MY137726A (en) |
| NO (1) | NO332937B1 (en) |
| NZ (1) | NZ525911A (en) |
| PE (1) | PE20020582A1 (en) |
| PL (1) | PL201188B1 (en) |
| PT (1) | PT1339430E (en) |
| RS (1) | RS52024B (en) |
| SI (1) | SI1339430T1 (en) |
| SK (1) | SK287993B6 (en) |
| TW (1) | TWI284041B (en) |
| UA (1) | UA80961C2 (en) |
| WO (1) | WO2002041919A1 (en) |
| ZA (1) | ZA200303593B (en) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY137726A (en) * | 2000-11-22 | 2009-03-31 | Nycomed Gmbh | Freeze-dried pantoprazole preparation and pantoprazole injection |
| US20050287231A1 (en) * | 2002-06-21 | 2005-12-29 | Nussen Kenneth H | Method and apparatus for oral hygiene products with green tea extract |
| WO2004037224A1 (en) * | 2002-10-25 | 2004-05-06 | Pfizer Products Inc. | Depot formulations of arylheterocyclic active agents in the form of a suspension |
| AU2003241150A1 (en) * | 2003-05-06 | 2004-11-26 | Hetero Drugs Limited | Novel polymorphs of pantoprazole sodium |
| CL2004000983A1 (en) * | 2003-05-08 | 2005-03-04 | Altana Pharma Ag | ORAL PHARMACEUTICAL COMPOSITION IN THE FORM OF A TABLET THAT INCLUDES DIHYDRATED MAGNETIC PANTOPRAZOL, WHERE THE TABLET FORM IS COMPOSED BY A NUCLEUS, A MIDDLE COAT AND AN OUTER LAYER; AND USE OF PHARMACEUTICAL COMPOSITION IN ULCERAS AND |
| CN1791406A (en) * | 2003-05-19 | 2006-06-21 | 普利瓦研究与发展有限公司 | Solid state forms of 5-(difluoro-methoxy)-2-((3,4-dimethoxy-2-pyridinyl)-methyl) sulfinyl]-1H-benzimidazole sodium aquo complexes |
| AR045258A1 (en) * | 2003-08-21 | 2005-10-19 | Altana Pharma Ag | A PHARMACEUTICAL PRODUCT FOR INJECTION |
| WO2005070426A1 (en) * | 2004-01-27 | 2005-08-04 | Altana Pharma Ag | Freeze-dried (-)-pantoprazole preparation and (-)-pantoprazole injection |
| DE102004007854A1 (en) * | 2004-02-17 | 2005-09-01 | Hexal Ag | Aqueous composition containing a benzimidazole derivative, particularly omeprazole, useful for treating ulcers, is adjusted to weakly basic pH and contains no organic solvent |
| US20060085924A1 (en) * | 2004-10-13 | 2006-04-27 | Gaelle Brun | Coloring composition comprising at least one pigment and at least one electrophilic cyanoacrylate monomer |
| CN1293879C (en) * | 2005-01-20 | 2007-01-10 | 杭州华东医药集团生物工程研究所有限公司 | Freeze-dried powder injection of pantoprazole sodium and its preparation |
| CA2624179A1 (en) * | 2005-10-06 | 2007-04-12 | Auspex Pharmaceuticals, Inc. | Deuterated inhibitors of gastric h+, k+-atpase with enhanced therapeutic properties |
| WO2009001163A1 (en) * | 2006-06-01 | 2008-12-31 | Combino Pharm, S.L. | Lyophilized preparations of pantoprazole sodium for injection |
| EP2340846A1 (en) | 2006-07-26 | 2011-07-06 | Sandoz Ag | Caspofungin formulations |
| US7979200B2 (en) * | 2006-11-20 | 2011-07-12 | Lockheed Martin Corporation | Managing an air-ground communications network with air traffic control information |
| EP2106788A1 (en) * | 2008-04-04 | 2009-10-07 | Ipsen Pharma | Liquid and freeze dried formulations |
| CN101744777B (en) * | 2009-12-30 | 2012-09-26 | 北京四环科宝制药有限公司 | Omeprazole sodium freeze-dried powder injection, as well as preparation method and quality control method thereof |
| CN101961309B (en) * | 2010-09-15 | 2012-06-27 | 河南辅仁怀庆堂制药有限公司 | Process for preparing pantoprazole sodium for injection |
| CN102000034B (en) * | 2010-10-13 | 2011-12-21 | 江苏奥赛康药业股份有限公司 | S-pantoprazole sodium composite for injection and preparation method thereof |
| CN102225063B (en) * | 2011-05-10 | 2012-10-10 | 江苏奥赛康药业股份有限公司 | Pantoprazole sodium composition for injection |
| TR201108946A2 (en) * | 2011-09-12 | 2012-04-24 | World Medicine İlaç Sanayi̇ Ve Ti̇caret Li̇mi̇ted Şi̇rketi̇ | Freeze-dried ATP, vitamin B complex preparation and injection. |
| WO2014003199A1 (en) * | 2012-06-27 | 2014-01-03 | Takeda Pharmaceutical Company Limited | Liquid preparations of amines and organic acids stabilized by salts |
| CN104000786A (en) * | 2013-02-25 | 2014-08-27 | 杭州赛利药物研究所有限公司 | Lyophilized pantoprazole sodium preparation and preparation method thereof |
| CN104414979A (en) * | 2013-08-21 | 2015-03-18 | 哈药集团三精制药股份有限公司 | Pantoprazole sodium freeze-dried powder injection and preparation method thereof |
| CN104019635B (en) * | 2014-06-19 | 2015-05-27 | 上海慈瑞医药科技有限公司 | Drying process for lansoprazole bulk drug |
| CN104055791A (en) * | 2014-07-10 | 2014-09-24 | 北京人福军威医药技术开发有限公司 | Application of cydiodine to treatment of keratoconjunctivitis |
| CN104055792A (en) * | 2014-07-10 | 2014-09-24 | 北京人福军威医药技术开发有限公司 | Application of cydiodine to treatment of otitis media |
| BE1021311B1 (en) * | 2014-07-31 | 2015-10-28 | Neogen N.V. | METHOD FOR MAKING A POWDERED PROTON PUMP INHIBITOR COMPOSITION, MENTIONED COMPOSITION AND USE |
| EP3288556A4 (en) | 2015-04-29 | 2018-09-19 | Dexcel Pharma Technologies Ltd. | Orally disintegrating compositions |
| US10076494B2 (en) | 2016-06-16 | 2018-09-18 | Dexcel Pharma Technologies Ltd. | Stable orally disintegrating pharmaceutical compositions |
| CN111643460A (en) * | 2020-06-30 | 2020-09-11 | 武汉九州钰民医药科技有限公司 | Pantoprazole sodium freeze-dried preparation, preparation method thereof and injection preparation prepared from pantoprazole sodium freeze-dried preparation |
| US12102624B2 (en) | 2020-08-26 | 2024-10-01 | Nivagen Pharmaceuticals, Inc. | Pantoprazole compositions and methods |
| CN112274481A (en) * | 2020-10-27 | 2021-01-29 | 海南卫康制药(潜山)有限公司 | Pantoprazole sodium composition for injection and preparation method thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8301182D0 (en) * | 1983-03-04 | 1983-03-04 | Haessle Ab | NOVEL COMPOUNDS |
| IL75400A (en) | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5223515A (en) * | 1988-08-18 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Injectable solution containing a pyridyl methylsulfinylbenzimidazole |
| DK399389A (en) | 1988-08-18 | 1990-02-19 | Takeda Chemical Industries Ltd | INJECTABLE SOLUTIONS |
| DE4035455A1 (en) | 1990-11-08 | 1992-05-14 | Byk Gulden Lomberg Chem Fab | ENANTIOMER SEPARATION |
| ATE144421T1 (en) | 1992-07-28 | 1996-11-15 | Astra Ab | INJECTABLE DRUG AND PACKAGE CONTAINING OMOPRAZOLE OR RELATED COMPOUNDS |
| CA2161256C (en) * | 1993-04-27 | 2004-06-29 | Nancy M. Gray | Methods and compositions for treating gastric disorders using optically pure (-) pantoprazole |
| DE4324014C2 (en) | 1993-07-17 | 1995-06-08 | Byk Gulden Lomberg Chem Fab | Process for the preparation of a preparation reconstitutable in water |
| TW280770B (en) * | 1993-10-15 | 1996-07-11 | Takeda Pharm Industry Co Ltd | |
| FR2740686B1 (en) * | 1995-11-03 | 1998-01-16 | Sanofi Sa | STABLE LYOPHILIZED PHARMACEUTICAL FORMULATION |
| HU224987B1 (en) | 1995-11-03 | 2006-05-29 | Sanofi Aventis | Stable freeze-dried pharmaceutical formulation |
| US5980882A (en) | 1997-04-16 | 1999-11-09 | Medeva Pharmaceuticals Manufacturing | Drug-resin complexes stabilized by chelating agents |
| DK1039905T3 (en) | 1997-10-14 | 2006-11-06 | Eisai Co Ltd | Pharmaceutical formulation comprising glycine as a stabilizer |
| DE19843413C1 (en) * | 1998-08-18 | 2000-03-30 | Byk Gulden Lomberg Chem Fab | New salt form of pantoprazole |
| WO2000026185A2 (en) | 1998-10-30 | 2000-05-11 | The Curators Of The University Of Missouri | Omeprazole solution and method of using same |
| US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| CN1235018A (en) * | 1999-04-22 | 1999-11-17 | 沈阳东宇药业有限公司 | Preparation of freeze-dried pantoprazole injection and preparing method thereof |
| SE9903831D0 (en) | 1999-10-22 | 1999-10-22 | Astra Ab | Formulation of substituted benzimidazoles |
| AU2001278755A1 (en) * | 2000-08-18 | 2002-03-04 | Takeda Chemical Industries Ltd. | Injections |
| MY137726A (en) | 2000-11-22 | 2009-03-31 | Nycomed Gmbh | Freeze-dried pantoprazole preparation and pantoprazole injection |
| AR045258A1 (en) | 2003-08-21 | 2005-10-19 | Altana Pharma Ag | A PHARMACEUTICAL PRODUCT FOR INJECTION |
-
2001
- 2001-10-19 MY MYPI20014865A patent/MY137726A/en unknown
- 2001-11-06 TW TW090127545A patent/TWI284041B/en not_active IP Right Cessation
- 2001-11-17 EE EEP200300182A patent/EE05236B1/en not_active IP Right Cessation
- 2001-11-17 EA EA200300501A patent/EA007602B1/en not_active IP Right Cessation
- 2001-11-17 EP EP01997314A patent/EP1339430B1/en not_active Revoked
- 2001-11-17 SK SK606-2003A patent/SK287993B6/en not_active IP Right Cessation
- 2001-11-17 ES ES01997314T patent/ES2298295T3/en not_active Expired - Lifetime
- 2001-11-17 PL PL361118A patent/PL201188B1/en unknown
- 2001-11-17 CA CA002428870A patent/CA2428870C/en not_active Expired - Lifetime
- 2001-11-17 CA CA002541946A patent/CA2541946A1/en not_active Abandoned
- 2001-11-17 PT PT01997314T patent/PT1339430E/en unknown
- 2001-11-17 RS YU37703A patent/RS52024B/en unknown
- 2001-11-17 CN CNB01819379XA patent/CN1250292C/en not_active Expired - Lifetime
- 2001-11-17 BR BRPI0115483A patent/BRPI0115483B8/en not_active IP Right Cessation
- 2001-11-17 UA UA20040705223A patent/UA80961C2/en unknown
- 2001-11-17 NZ NZ525911A patent/NZ525911A/en not_active IP Right Cessation
- 2001-11-17 KR KR1020077027736A patent/KR100910607B1/en active IP Right Grant
- 2001-11-17 HU HU0303278A patent/HUP0303278A3/en unknown
- 2001-11-17 GE GE5180A patent/GEP20053461B/en unknown
- 2001-11-17 SI SI200130816T patent/SI1339430T1/en unknown
- 2001-11-17 AU AU1604202A patent/AU1604202A/en active Pending
- 2001-11-17 DK DK01997314T patent/DK1339430T3/en active
- 2001-11-17 DE DE60132108T patent/DE60132108T2/en not_active Expired - Lifetime
- 2001-11-17 AT AT01997314T patent/ATE381946T1/en active
- 2001-11-17 IL IL15560101A patent/IL155601A0/en unknown
- 2001-11-17 WO PCT/EP2001/013296 patent/WO2002041919A1/en active IP Right Grant
- 2001-11-17 EP EP06123558.6A patent/EP1762249A3/en not_active Ceased
- 2001-11-17 KR KR1020037006675A patent/KR100910606B1/en active IP Right Grant
- 2001-11-17 CZ CZ2003-1416A patent/CZ304348B6/en not_active IP Right Cessation
- 2001-11-17 JP JP2002544096A patent/JP4886158B2/en not_active Expired - Fee Related
- 2001-11-17 AU AU2002216042A patent/AU2002216042B2/en not_active Expired
- 2001-11-17 MX MXPA03004548A patent/MXPA03004548A/en active IP Right Grant
- 2001-11-17 ME MEP-696/08A patent/ME00556A/en unknown
- 2001-11-19 PE PE2001001153A patent/PE20020582A1/en active IP Right Grant
- 2001-11-19 AR ARP010105391A patent/AR034277A1/en not_active Application Discontinuation
-
2002
- 2002-07-15 US US10/195,062 patent/US6780881B2/en not_active Expired - Lifetime
-
2003
- 2003-04-28 IL IL155601A patent/IL155601A/en active IP Right Grant
- 2003-05-09 ZA ZA200303593A patent/ZA200303593B/en unknown
- 2003-05-19 EC EC2003004613A patent/ECSP034613A/en unknown
- 2003-05-19 IS IS6820A patent/IS2971B/en unknown
- 2003-05-20 BG BG107828A patent/BG66329B1/en unknown
- 2003-05-21 NO NO20032303A patent/NO332937B1/en not_active IP Right Cessation
- 2003-05-21 HR HR20030410A patent/HRP20030410B1/en not_active IP Right Cessation
-
2004
- 2004-05-28 HK HK04103845A patent/HK1060848A1/en not_active IP Right Cessation
- 2004-05-28 US US10/855,703 patent/US7351723B2/en not_active Expired - Lifetime
-
2008
- 2008-01-22 US US12/010,124 patent/US8754108B2/en not_active Expired - Lifetime
- 2008-02-28 CY CY20081100226T patent/CY1107896T1/en unknown
-
2013
- 2013-08-21 AR ARP130102967A patent/AR092374A2/en not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8754108B2 (en) | Freeze-dried pantoprazole preparation and pantoprazole injection | |
| AU2002216042A1 (en) | Freeze-dried pantoprazole preparation and pantoprazole injection | |
| US5589491A (en) | Injection and injection kit containing omeprazole and its analogs | |
| EP1694296A1 (en) | Injectable composition | |
| WO2009001163A1 (en) | Lyophilized preparations of pantoprazole sodium for injection | |
| AU2006235847B2 (en) | Lyophilized pantoprazole preparation | |
| GB2404856A (en) | Stable pharmaceutical composition of rabeprazole |