CA2298624A1 - Ascorbic acid-based formulation having improved colour stability - Google Patents
Ascorbic acid-based formulation having improved colour stability Download PDFInfo
- Publication number
- CA2298624A1 CA2298624A1 CA002298624A CA2298624A CA2298624A1 CA 2298624 A1 CA2298624 A1 CA 2298624A1 CA 002298624 A CA002298624 A CA 002298624A CA 2298624 A CA2298624 A CA 2298624A CA 2298624 A1 CA2298624 A1 CA 2298624A1
- Authority
- CA
- Canada
- Prior art keywords
- preparation according
- weight
- ascorbic acid
- cellulose
- sugar alcohols
- 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.)
- Abandoned
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
- A23G2200/04—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing vitamins, antibiotics, other medicaments
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Physiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Diabetes (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Confectionery (AREA)
Abstract
The invention relates to a novel ascorbic acid-based formulation with an improved flavour, said formulation also being directly compressible and having improved colour stability.
Description
Ascorbic acid-based formulation having improved colour stability The invention relates to a novel ascorbic acid-s based formulation which has an improved taste charac-ter, which is directly compressible and which displays improved colour stability.
In many cases, the taste character experienced by the user gives rise to problems when formulating pharmaceutical compositions which are to be adminis tered orally, with these problems not being confined to liquid administration forms.
A taste which is experienced as being extremely bitter or else. acidic has also proved to be a problem in the case of a very wide variety of active compounds.
Success has not so far been achieved in masking par-ticularly acidic, bitter or chalky active compounds by adding flavourings or aromatizing substances. While it is possible to provide tablets which comprise relevant active compounds with a coating, this method is unsuit-able when the aim is to achieve rapid uptake of the active compound, with this uptake already taking place by way of the oral mucosa when the tablets are chewed.
Special demands are also placed on the surface of tablets which are to be sucked, for example throat tablets. In this case, the need is for the actual tablet to have a smooth surface which is retained during sucking and which does not gradually roughen:
Furthermore, tablets for sucking and, in par ticular, for chewing are nowadays increasingly being offered for sale in the field of nutritional supplemen tation (vitamin and mineral supplementation).
In addition, attempts are being made to employ directly compressible active compounds (DC active com pounds) to an increasing extent when preparing solid formulations in order to lower production costs.
In this context, it has now been found to be a problem, in particular when preparing vitamin-comprising formulations, that ascorbic acid is not commercially available in directly compressible form.
The object of the present invention is there-fore to provide a process by which, on the one hand, ascorbic acid is made available in a directly compres sible form and, on the other hand, the taste character of solid, ascorbic acid-comprising formulations is improved and, at the same time, the oral sensation engendered by the manufactured products is influenced in an advantageous manner.
It has now been found that the taste character of solid, ascorbic acid-comprising preparations, which comprise from 85 to 98% by weight of ascorbic acid, can be improved by converting an aqueous composition, which comprises one or more sugar alcohols in a quantity of from 1.5 to 15% by weight, based on the weighed-in quantity of solid, into a solid form by means of spray granulation or fluidized bed granulation or spray-fluidized bed granulation.
The invention consequently relates to ascorbic acid-comprising preparations which are in directly compressible form and which have an improved taste character.
The invention also relates, therefore, to a process for manufacturing solid, ascorbic acid comprising preparations which are in directly compres sible form and which have an improved taste character, characterized in that . al an aqueous solution comprising - from 85 to 98% by weight of ascorbic acid - from 1.5 to 15% by weight of one or more sugar alcohols - up to 1.2% by weight of a binding agent, with the given percentage quantities of the dissolved substances adding up to 100% by weight, is prepared, b) the resulting solution is atomized in air currents which are at different temperatures between room temperature and up to 180°C, preferably from 60 to 140°C, c) water vapour-comprising air currents are drawn off, and d) the homogeneous particles which form in a fluidized bed which is of low height, and which additionally exhibits a variable height, are carried off as a solid form, and e) up to 1% by weight of the particles which have been formed are returned once again to the process.
The invention furthermore relates to directly compressible ascorbic acid-comprising preparations which, in addition to at least one sugar alcohol, comprise up to 1.5% by weight of one or more binding agents selected from the group cellulose, methyl cellulose, hydroxymethylpropyl cellulose, carboxymethyl cellulose, starch, maltodextrin and gum arabic.
In this context, the total quantity of sugar alcohol employed is to be selected such that from 1.5 to 15% by weight, in particular from 2 to 10% by weight, is present in the pulverulent substance mixture which is produced by means of the novel process.
According to the invention, sugar alcohols from the C4-C12 sugar alcohol group are suitable for produc ing the ascorbic acid-comprising preparations. Particu larly suitable sugar alcohols are, in particular, those selected from the group erythritol, xylitol, mannitol and lactitol.
According to the invention, 1 part of mannitol or lactitol, based on from 0.5 to 2.0 parts of sorbitol, can be present in the preparations.
The novel composition can therefore be obtained by dissolving at least one sugar alcohol in water and dissolving or suspending the ascorbic acid, and atomiz ing the resulting aqueous mixture in an air current which is at a temperature of from room temperature to 180°C, preferably from 60 to 140°C, drawing off water vapour-comprising air currents and carrying out a fluidized bed treatment, with the fluidized bed exhi-biting a low, and at the same time, variable, height.
The homogeneous particles which are formed are carried off in solid form. Up to 1% by weight of the particles which have been formed are returned once again to the process.
However, it is also possible to vortex the aqueous mixture which has been prepared in an air current at a temperature of from 40 to 120°C and subject it to a simple spray granulation. It has been found, however, that the initially described combined spray-fluidized bed granulation yields products having particularly advantageous properties.
Solid administration forms, such as com primates, can, per se, be produced from the above described novel preparations without any further work ing up, directly by compression. The solid ascorbic acid preparations which can be obtained by spray granu lation or spray-fluidized bed granulation can also be readily mixed with one or more active compounds and processed into tablet formulations. In particular, these formulations can be processed into products which can be sold to the customer for self medication. These also include, inter alia, analgesics in tablet form, and remedies against colds, such as throat tablets, including lozenges. In these lozenges, the improved properties manifest themselves in a smoother surface, which is evident not only directly after production but also during sucking.
In this context, the novel formulations can particularly advantageously be incorporated into cor-responding tablets for chewing, since, on the one hand, they can be compressed without any great expenditure of energy and, on the other hand, they give rise to an improved chewing quality as a result of the improvement in the taste character.
The novel preparations can also be used for producing nutrition supplementation preparations in a simple manner, both in tablet form and in any other manner known to the skilled person. However, the pulverulent, directly compressible ascorbic acid pre-parations can also be incorporated into a very wide variety of confectionery, such as sucking sweets, chew-s ing gum or other types of confectionery.
It has been found that, in addition to an improved taste character and the direct compres-sibility, the novel ascorbic acid formulations also result in the manufactured products having improved stability during storage. Normally, tablet formulations which comprise ascorbic acid, and to which a binding ' agent has been added in order to achieve adequate tablet hardness, tend to turn yellow. By contrast, cor responding products which have been manufactured using the novel preparations do not exhibit any discoloration even after having been stored for several months. This is in particular the case when non-hygroscopic sugar alcohols, such as mannitol, are used for producing the preparations. In addition, satisfactory tablet hard-nesses are achieved without adding binding agents. Use of the novel preparations results in products which, in experiments, exhibit reduced abrasion as compared with conventionally prepared tablets comprising a high pro-portion of ascorbic acid.
In many cases, the taste character experienced by the user gives rise to problems when formulating pharmaceutical compositions which are to be adminis tered orally, with these problems not being confined to liquid administration forms.
A taste which is experienced as being extremely bitter or else. acidic has also proved to be a problem in the case of a very wide variety of active compounds.
Success has not so far been achieved in masking par-ticularly acidic, bitter or chalky active compounds by adding flavourings or aromatizing substances. While it is possible to provide tablets which comprise relevant active compounds with a coating, this method is unsuit-able when the aim is to achieve rapid uptake of the active compound, with this uptake already taking place by way of the oral mucosa when the tablets are chewed.
Special demands are also placed on the surface of tablets which are to be sucked, for example throat tablets. In this case, the need is for the actual tablet to have a smooth surface which is retained during sucking and which does not gradually roughen:
Furthermore, tablets for sucking and, in par ticular, for chewing are nowadays increasingly being offered for sale in the field of nutritional supplemen tation (vitamin and mineral supplementation).
In addition, attempts are being made to employ directly compressible active compounds (DC active com pounds) to an increasing extent when preparing solid formulations in order to lower production costs.
In this context, it has now been found to be a problem, in particular when preparing vitamin-comprising formulations, that ascorbic acid is not commercially available in directly compressible form.
The object of the present invention is there-fore to provide a process by which, on the one hand, ascorbic acid is made available in a directly compres sible form and, on the other hand, the taste character of solid, ascorbic acid-comprising formulations is improved and, at the same time, the oral sensation engendered by the manufactured products is influenced in an advantageous manner.
It has now been found that the taste character of solid, ascorbic acid-comprising preparations, which comprise from 85 to 98% by weight of ascorbic acid, can be improved by converting an aqueous composition, which comprises one or more sugar alcohols in a quantity of from 1.5 to 15% by weight, based on the weighed-in quantity of solid, into a solid form by means of spray granulation or fluidized bed granulation or spray-fluidized bed granulation.
The invention consequently relates to ascorbic acid-comprising preparations which are in directly compressible form and which have an improved taste character.
The invention also relates, therefore, to a process for manufacturing solid, ascorbic acid comprising preparations which are in directly compres sible form and which have an improved taste character, characterized in that . al an aqueous solution comprising - from 85 to 98% by weight of ascorbic acid - from 1.5 to 15% by weight of one or more sugar alcohols - up to 1.2% by weight of a binding agent, with the given percentage quantities of the dissolved substances adding up to 100% by weight, is prepared, b) the resulting solution is atomized in air currents which are at different temperatures between room temperature and up to 180°C, preferably from 60 to 140°C, c) water vapour-comprising air currents are drawn off, and d) the homogeneous particles which form in a fluidized bed which is of low height, and which additionally exhibits a variable height, are carried off as a solid form, and e) up to 1% by weight of the particles which have been formed are returned once again to the process.
The invention furthermore relates to directly compressible ascorbic acid-comprising preparations which, in addition to at least one sugar alcohol, comprise up to 1.5% by weight of one or more binding agents selected from the group cellulose, methyl cellulose, hydroxymethylpropyl cellulose, carboxymethyl cellulose, starch, maltodextrin and gum arabic.
In this context, the total quantity of sugar alcohol employed is to be selected such that from 1.5 to 15% by weight, in particular from 2 to 10% by weight, is present in the pulverulent substance mixture which is produced by means of the novel process.
According to the invention, sugar alcohols from the C4-C12 sugar alcohol group are suitable for produc ing the ascorbic acid-comprising preparations. Particu larly suitable sugar alcohols are, in particular, those selected from the group erythritol, xylitol, mannitol and lactitol.
According to the invention, 1 part of mannitol or lactitol, based on from 0.5 to 2.0 parts of sorbitol, can be present in the preparations.
The novel composition can therefore be obtained by dissolving at least one sugar alcohol in water and dissolving or suspending the ascorbic acid, and atomiz ing the resulting aqueous mixture in an air current which is at a temperature of from room temperature to 180°C, preferably from 60 to 140°C, drawing off water vapour-comprising air currents and carrying out a fluidized bed treatment, with the fluidized bed exhi-biting a low, and at the same time, variable, height.
The homogeneous particles which are formed are carried off in solid form. Up to 1% by weight of the particles which have been formed are returned once again to the process.
However, it is also possible to vortex the aqueous mixture which has been prepared in an air current at a temperature of from 40 to 120°C and subject it to a simple spray granulation. It has been found, however, that the initially described combined spray-fluidized bed granulation yields products having particularly advantageous properties.
Solid administration forms, such as com primates, can, per se, be produced from the above described novel preparations without any further work ing up, directly by compression. The solid ascorbic acid preparations which can be obtained by spray granu lation or spray-fluidized bed granulation can also be readily mixed with one or more active compounds and processed into tablet formulations. In particular, these formulations can be processed into products which can be sold to the customer for self medication. These also include, inter alia, analgesics in tablet form, and remedies against colds, such as throat tablets, including lozenges. In these lozenges, the improved properties manifest themselves in a smoother surface, which is evident not only directly after production but also during sucking.
In this context, the novel formulations can particularly advantageously be incorporated into cor-responding tablets for chewing, since, on the one hand, they can be compressed without any great expenditure of energy and, on the other hand, they give rise to an improved chewing quality as a result of the improvement in the taste character.
The novel preparations can also be used for producing nutrition supplementation preparations in a simple manner, both in tablet form and in any other manner known to the skilled person. However, the pulverulent, directly compressible ascorbic acid pre-parations can also be incorporated into a very wide variety of confectionery, such as sucking sweets, chew-s ing gum or other types of confectionery.
It has been found that, in addition to an improved taste character and the direct compres-sibility, the novel ascorbic acid formulations also result in the manufactured products having improved stability during storage. Normally, tablet formulations which comprise ascorbic acid, and to which a binding ' agent has been added in order to achieve adequate tablet hardness, tend to turn yellow. By contrast, cor responding products which have been manufactured using the novel preparations do not exhibit any discoloration even after having been stored for several months. This is in particular the case when non-hygroscopic sugar alcohols, such as mannitol, are used for producing the preparations. In addition, satisfactory tablet hard-nesses are achieved without adding binding agents. Use of the novel preparations results in products which, in experiments, exhibit reduced abrasion as compared with conventionally prepared tablets comprising a high pro-portion of ascorbic acid.
Claims (12)
1. Ascorbic acid-comprising preparation which can be obtained by the fluidized-bed granulation of a mixture which comprises a) from 85 to 98% by weight of ascorbic acid, b) from 1.5 to 15% by weight of one or more sugar alcohols.
2. Ascorbic acid-comprising preparation according to Claim 1 in directly compressible form and having an improved taste character.
3. Preparation according to Claim 1, comprising up to 1.5% by weight of one or more binding agents selected from the group cellulose, methyl cellulose, hydroxymethylpropyl cellulose, carboxymethyl cellulose, starch, maltodextrin and gum arabic.
4. Preparation according to Claims 1 to 3 comprising one or more sugar alcohol(s) selected from the group of the C4 to C12 sugar alcohols,
5. Preparation according to Claim 4 comprising one or more sugar alcohol(s) selected from the group erythritol, xylitol, mannitol and lactitol.
6. Preparation according to Claims 4 to 5 comprising 1 part of mannitol or lactitol based on from 0.5 to 2.0 parts of sorbitol.
7. Comprimates, comprising a preparation according to one or more of Claims 1 to 6.
8. Tablets, comprising a preparation according to one or more of Claims 1 to 6.
9. Nutrition supplementation preparations, comprising a preparation according to one or more of Claims 1 to 6.
10. Chewing gum, comprising a preparation according to one or more of Claims 1 to 6.
11. Confectionery, comprising a preparation according to one or more of Claims 1 to 6.
12. Process for producing a preparation according to one or more of Claims 1 to 6, characterized in that a) an aqueous solution comprising - from 85 to 98% by weight of ascorbic acid - from 1.5 to 15% by weight of one or more sugar alcohols - up to 1.2% by weight of a binding agent, with the given percentage quantities of the dissolved substances adding up to 100% by weight, is prepared, b) the resulting solution is atomized in air currents which are at different temperatures between room temperature and up to 180C, preferably from 60 to 140C, c) water vapour-comprising air currents are drawn off, and d) the homogeneous particles which form in a fluidized bed which is of low height, and which additionally exhibits a variable height, are carried off as a solid form, and e) up to 1% by weight of the particles which have been formed are returned once again to the process.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19733094A DE19733094A1 (en) | 1997-07-31 | 1997-07-31 | Formulation based on ascorbic acid with improved color stability |
| DE19733094.0 | 1997-07-31 | ||
| PCT/EP1998/004556 WO1999006029A1 (en) | 1997-07-31 | 1998-07-21 | Ascorbic acid-based formulation with improved colour stability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2298624A1 true CA2298624A1 (en) | 1999-02-11 |
Family
ID=7837556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002298624A Abandoned CA2298624A1 (en) | 1997-07-31 | 1998-07-21 | Ascorbic acid-based formulation having improved colour stability |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1007007A1 (en) |
| JP (1) | JP2001511442A (en) |
| CN (1) | CN1265584A (en) |
| CA (1) | CA2298624A1 (en) |
| DE (1) | DE19733094A1 (en) |
| WO (1) | WO1999006029A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE250415T1 (en) | 1999-12-22 | 2003-10-15 | Hoffmann La Roche | MEDICINAL COMPOSITION CONTAINING ASCORBIC ACID AND PECTIN |
| SE0100822D0 (en) * | 2001-03-09 | 2001-03-09 | Astrazeneca Ab | Method II to obtain microparticles |
| SE0100824D0 (en) * | 2001-03-09 | 2001-03-09 | Astrazeneca Ab | Method III to obtain microparticles |
| US20050008692A1 (en) | 2001-09-03 | 2005-01-13 | Chyi-Cheng Chen | Compositions comprising pectin and ascorbic acid |
| DE102008004893A1 (en) | 2008-01-17 | 2009-07-23 | Add Technologies Ltd. | Carrier pellets, process for their preparation and their use |
| EP3770145A1 (en) | 2019-07-24 | 2021-01-27 | Basf Se | A process for the continuous production of either acrolein or acrylic acid as the target product from propene |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3293132A (en) * | 1963-03-25 | 1966-12-20 | Merck & Co Inc | Spray dried vitamin compositions and method of preparation |
| NL184308C (en) * | 1975-07-24 | 1989-06-16 | Takeda Chemical Industries Ltd | PROCESS FOR PREPARING L-ASCORBIC ACID GRANULES. |
| DE2706660A1 (en) * | 1977-02-17 | 1978-08-24 | Merck Patent Gmbh | GRANULATES CONTAINING ASCORBIC ACID AND THE PROCESS FOR THEIR MANUFACTURING |
| JPS5759803A (en) * | 1980-09-30 | 1982-04-10 | Takeda Chem Ind Ltd | Granule of l-sodium ascorbate, its preparation, and tablet comprising it |
| CA1279574C (en) * | 1985-04-17 | 1991-01-29 | Jeffrey L. Finnan | Process for lubricating water-soluble vitamin powders |
-
1997
- 1997-07-31 DE DE19733094A patent/DE19733094A1/en not_active Withdrawn
-
1998
- 1998-07-21 JP JP2000504844A patent/JP2001511442A/en active Pending
- 1998-07-21 WO PCT/EP1998/004556 patent/WO1999006029A1/en not_active Application Discontinuation
- 1998-07-21 CN CN98807777A patent/CN1265584A/en active Pending
- 1998-07-21 CA CA002298624A patent/CA2298624A1/en not_active Abandoned
- 1998-07-21 EP EP98943755A patent/EP1007007A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999006029A1 (en) | 1999-02-11 |
| DE19733094A1 (en) | 1999-02-04 |
| EP1007007A1 (en) | 2000-06-14 |
| CN1265584A (en) | 2000-09-06 |
| JP2001511442A (en) | 2001-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |