CN1304412A - Process for preparing crystalline salts of amoxycillin - Google Patents
Process for preparing crystalline salts of amoxycillin Download PDFInfo
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- CN1304412A CN1304412A CN99806927A CN99806927A CN1304412A CN 1304412 A CN1304412 A CN 1304412A CN 99806927 A CN99806927 A CN 99806927A CN 99806927 A CN99806927 A CN 99806927A CN 1304412 A CN1304412 A CN 1304412A
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- salt
- amoxycilline trihydrate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/04—Preparation
- C07D499/14—Preparation of salts
- C07D499/16—Preparation of salts of alkali or alkaline earth metals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A novel process for preparing a crystalline alkali metal salt of amoxycillin is dislcosed.
Description
The right of the U.S. Provisional Application 60/087,554 that the application submitted on June 1st, 1.
The present invention relates to prepare the beta-lactam antibiotics amoxycilline Trihydrate bp is 6-{[amino (4-hydroxy phenyl) ethanoyl]-amino }-3, the method for 3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid crystal salt.The present invention be more particularly directed to prepare the method for crystallization amoxycilline Trihydrate bp sodium salt.
Crystallization amoxycilline Trihydrate bp sodium salt is that known substance and its preparation method are disclosed in the present technique field.For example EP 0131147A discloses the method that Utimox is converted into the recrystallisation solvent thing of amoxycilline Trihydrate bp sodium salt and therefrom removes the desolvation solvent.In an EXPERIMENTAL EXAMPLE of the disclosure content, Utimox is suspended in the methyl acetate, in this suspension, add the solution of triethylamine and 2 ethyl hexanoic acid sodium mixture then.In EP 0596262A, Utimox is dissolved in methyl acetate/isopropyl alcohol/triethylamine mixture, then this solution is joined in the solution of 2 ethyl hexanoic acid sodium in the methyl acetate/methanol mixture.The recrystallisation solvent thing that it is believed that the amoxycilline Trihydrate bp sodium salt crystallizes out from reaction mixture, therefrom removes the desolvation solvent.In WO 97/15579, Utimox is joined a kind of solution that reacts with 2 ethyl hexanoic acid sodium subsequently of formation in ethanol/triethylamine mixture in ethanolic soln, obtain crystallized product.In US 4737585, Utimox is suspended in the mixture of aprotic solvent such as methylene dichloride and lower alcohol, uses low molecular weight amine to make the amoxycilline Trihydrate bp dissolving, in this mixture, add diethyl oxosuccinic acid sodium salt.Be settled out the amoxycilline Trihydrate bp sodium salt by adding more aprotic solvent then.
In the method for preparing crystallization amoxycilline Trihydrate bp sodium salt, wish the solvent for use amount is reduced to productive rate and purity minimum and the raising product.Therefore in present method improvement, exist problem.What an object of the present invention is to provide preparation crystallization amoxycilline Trihydrate bp sodium salt a kind ofly substitutes and improves one's methods.Other purpose of the present invention and advantage are conspicuous in the following description.
According to the invention provides a kind of method for preparing crystallization amoxycilline Trihydrate bp an alkali metal salt, wherein:
In first kind of organic solvent, form the suspension of amoxycilline Trihydrate bp amine salt;
This suspension mixed with second kind of organic solvent and amine salt is entered in the mixture solution of first kind and second kind organic solvent of formation like this;
Make the reaction of amine salt and alkali-metal salt-forming compound;
The amoxycilline Trihydrate bp an alkali metal salt that so forms is separated from solution as crystallized product.
Be considered in the methods of the invention that amine salt forms suspension in first kind of solvent and when second kind of organic solvent 1-5 sneaks into the quick dissolving of this salt make the decomposition of amoxycilline Trihydrate bp reduce, so improved the productive rate and the purity of crystallized product.In the methods of the invention, reagent is shaped as solution, this help sterile filtration and subsequently this product as the application of injectable drug product.But the inventive method can without sterile filtration be used to equally effectively to prepare can be oral crystallization amoxycilline Trihydrate bp sodium salt.
Preferably the crystallization amoxycilline Trihydrate bp an alkali metal salt by the inventive method preparation is a crystallization amoxycilline Trihydrate bp sodium salt.
Preferred amoxycilline Trihydrate bp amine salt is three of amoxycilline Trihydrate bp-or the salt of two-(C1-51-5) alkylamines such as triethylamine, diethylamine or Diisopropylamine, particularly triethylamine.Can use the mixture of the salt of amine salt mixture such as amoxycilline Trihydrate bp and triethylamine and Diisopropylamine.Other suitable amine salt comprises the salt with dicyclohexyl amine.
Preferred first kind of organic solvent is (C1-51-5) alkyl (C1-51-5) alkane carboxylicesters, and preferably this class ester is (C1-51-5) alkyl acetates, particularly methyl acetate.First kind of organic solvent can comprise a kind of solvent or solvent mixture, for example the mixture of the mixture of described ester or described ester and other cosolvent.
Preferably at first by in first kind of organic solvent, forming the amoxycilline Trihydrate bp, the suspension of preferred Utimox form, mixed amine and this suspension make amine and amoxycilline Trihydrate bp reaction formation amine salt form suspension subsequently.This reaction preferably for example is lower than 10 ℃ being lower than envrionment temperature, particularly carries out under 0-5 ℃.Utimox is suspended in a large amount of methyl acetates and suits, the weight of Utimox and the volume ratio of methyl acetate are approximately 1: 1-1: 2.5, for example be generally 1: 1.7-1: 2, and this suspension can mix with the triethylamine that surpasses with the stoichiometric amount in amoxycilline Trihydrate bp, amoxycilline Trihydrate bp for example: the mol ratio of triethylamine is 1: 1-1: 2, for example be generally 1: 1.3-1: 1.5.
The amine salt suspension suitable second kind of organic solvent of blended with it is (C1-51-5) alcohol, and as methyl alcohol, it is preferred or ethanol, propyl alcohol such as Virahol or butanols such as isopropylcarbinol.Second kind of organic solvent can comprise a kind of solvent or solvent mixture, the mixture of for example described alcohol or described alcohol and other cosolvent.
Second kind of solvent mixed making salt enter solution with the suspension of amine salt in first kind of solvent, and the volume of used second kind of solvent such as alcohol can be by the experiment decision, for reaching the minimum volume of the necessary second kind of solvent of this purpose.Generally when first kind of solvent be above-mentioned ester and second kind of solvent when being above-mentioned alcohol, find ester: pure volume ratio is approximately 1, and: 0.3-0.6 will be suitable, for example about 1: the methyl acetate of 0.4-0.5: methyl alcohol.If the methyl alcohol of this volume ratio is mixed with the triethylamine salt suspension of above-mentioned amoxycilline Trihydrate bp, then generally will dissolve once stirring this salt.
The amoxycilline Trihydrate bp amine salt solution that so forms in this stage can for example be filtered and/or by other standard purification step as handling with other material processing of Dai Kalite or selectivity absorption impurity.If filtering solution, then available subsequently more second kind of solvent such as pure washing and filtering medium, for example with respect to the amount 0.5-1.0 of salt solution mix amount doubly.
Suitable salt-forming compound is pharmaceutically acceptable suitable basic metal salt-forming compound, the sodium salt of organic compound for example, for example alkoxide is as (C1-51-5) alkoxide such as methylate and/or ethylate, or organic acid the alkane carboxylate salt such as the 2-ethylhexoate that replace as the salt such as the alkyl of (C1-121-5) carboxylic acid.In the situation of preparation crystallization amoxycilline Trihydrate bp sodium salt, 2 ethyl hexanoic acid sodium is preferred salt-forming compound.
The reaction of amine salt is by mixed amine salts solution and salt-forming compound solution and suitably carry out.It is suitable that salt-forming compound is present in the solution of solvent mixture, solvent mixture comprises above-mentioned first kind and second kind of organic solvent, for example above-mentioned (C1-51-5) alkyl (C1-51-5) alkane carboxylicesters and (C1-51-5) alcohol, the methyl acetate that for example mainly comprises ester: carbinol mixture, 9-12 for example: 1 v: v, as 10-11: 1 v: v methyl acetate: carbinol mixture.Use is with respect to the amoxycilline Trihydrate bp and the excessive salt-forming compound of stoichiometry is suitable, and for example mol ratio is 1.5-2.5: 12 ethyl hexanoic acid sodium: amoxycilline Trihydrate bp.Suitably can use 2 ethyl hexanoic acid sodium concentration in above-mentioned solvent mixture to be the solution of about 1.8-2.5 M.This solution can be filtered before reacting with the amoxycilline Trihydrate bp and/or other suitable purification step of process.
Be preferably being reflected between salt compound and the amoxycilline Trihydrate bp and be lower than envrionment temperature and for example be lower than 10 ℃, particularly under 0-5 ℃, carry out.Preferably amine salt solution is joined in the salt-forming compound solution,, be about to salt-forming compound solution and join in the amine salt solution, or mix simultaneously although can use opposite adding pattern.Being blended under the quick stirring of preferred two kinds of solution carried out as quickly as possible.
But reaction product spontaneous crystallization, but preferably after mixing, in reaction mixture, add crystal seed immediately at solution, for example the solvate of crystallization amoxycilline Trihydrate bp sodium salt or some crystallization Equivalent such as crystallization amoxycilline Trihydrate bp sodium salt brings out crystallization.In order further to promote crystallization, can add some above-mentioned first kind of organic solvents in addition as (C1-51-5) alkyl (C1-51-5) alkane carboxylicesters such as methyl acetate and reaction mixture, preferably use excessive reaction medium volume such as excessive 1.5-2.0 reaction medium volume doubly.This mixing of first kind of organic solvent can for example approximately be finished in the 30-40 branch than the slow-motion row.With this in addition after first kind of solvent of amount, can be with mixture restir for some time, for example about 1 hour, preferably for example be lower than 10 ℃ being lower than envrionment temperature, particularly under 0-5 ℃, carry out.
The available standards method is as filtering and with suitable washing lotion, preferred first kind of organic solvent washing separated crystallized product from reaction medium after this stage.
The crystallized product of Huo Deing is considered to the solvate of crystallization amoxycilline Trihydrate bp sodium salt by this way, methyl acetate solvate for example, can therefrom remove the desolvation solvent by drying means such as the disclosed method of EP 0131147A, be incorporated herein this patent content as a reference.This drying process can be preferable over high temperature such as 50-65 ℃ in a vacuum and carry out obtaining crystalline amoxycilline Trihydrate bp an alkali metal salt to remove remaining reaction medium solvent, washing lotion and solvation solvent under 60-65 ℃.
Crystallization amoxycilline Trihydrate bp sodium salt by the inventive method preparation can be used as for example medicine antibiotic product of injection-type.Can be contained in the sterile vials of sealing for this reason and supply with.Perhaps use with dosage forms such as oral preparations such as tablet, pill, syrup, and needn't require sterile preparation for oral application by the amoxycilline Trihydrate bp sodium salt of the inventive method preparation.As the salt of the preferred crystallization of antibiotic product amoxycilline Trihydrate bp an alkali metal salt product and pharmaceutically acceptable beta-lactamase inhibitor such as clavulanic acid particularly clavulanic acid potassium unite use.
To the present invention be described by the mode of non-limiting example now.
Embodiment 1: the dissolving of laboratory scale 1.12-Sodium Ethylhexanoate
2-ethyl acid sodium (160g) is dissolved in the mixture of methyl acetate (310ml) and methyl alcohol (30ml).Until dissolving fully, remove muddy thing at this mixture of stirring at room by No. 1 filter paper filtering solution of Whatman.Solution is transferred in the crystallisation vessel, used methyl acetate (210ml) flushing then and in 0-5 ℃ of stirring.This solution is the 2 ethyl hexanoic acid sodium of 2.15M thus.1.2 the dissolving of Utimox
With Utimox (250g) slurryization in methyl acetate (450ml).Triethylamine (120ml) is joined generation heavy-gravity suspension in the slurry.Add methyl alcohol (200ml), the amoxycilline Trihydrate bp triethylamine salt dissolves immediately.Adding Dai Kalite (10g) before with solution stirring 5 minutes and allow mixture restir 5 minutes.Subsequently by No. 1 filter paper filtering solution of Whatman, use methyl alcohol (120ml) to wash and transfer to then to fill in the crystallisation vessel from above-mentioned 1.1 2 ethyl hexanoic acid sodium.1.3 reaction and crystallization
Mixture in 0-5 ℃ of vigorous stirring crystallisation vessel also adds amoxycilline Trihydrate bp sodium salt crystal seed (1g).Crystallization began the back and added methyl acetate (2300ml) in 30-40 minute.Mixture was stirred 1 hour at 0-5 ℃.Filtration product is also with methyl acetate (750ml) flushing then.1.4 it is dry
Will be from 1.3 crystallized product under 50-55 ℃ of vacuum dry 36 hours, perhaps 65 ℃ of down dry 16 hours short periods.The quality of discovery product is not subjected to the influence of drying temperature.By chemical analysis, infrared spectra and X-ray powder diffraction proof product is crystallization amoxycilline Trihydrate bp sodium salt.
The amoxycilline Trihydrate bp content of products therefrom is 91.0%, and content of impurities is 2.13-2.16%.
Embodiment 2; Experimental amount is amplified the dissolving of 2.1 2 ethyl hexanoic acid sodium
Methyl acetate (124L) is joined in the 2 ethyl hexanoic acid sodium (64kg), and stirring down, adding methyl alcohol (12L) dissolves up to 2 ethyl hexanoic acid sodium.Solution is filtered and transfers in the crystallisation vessel, with methyl acetate (84L) flushing.2.2 the dissolving of Utimox
Methyl acetate (124L) joined in the Utimox (87.1kg) and with gained suspension be cooled to 0-5 ℃.Join triethylamine (48.1L) in the slurry and stirred slurry 5 minutes.Add that methyl alcohol (80L) makes amoxycilline Trihydrate bp triethylamine salt dissolving and with solution stirring 5 minutes.Add Dai Kalite (2kg) and with mixture restir 5 minutes.Subsequent filtration solution is also used methyl alcohol (48L) flush cake.2.3 reaction and crystallization
To join from 2.2 amoxycilline Trihydrate bp triethylamine salt solution as early as possible from being cooled to 0-5 ℃ in 2.1 the 2 ethyl hexanoic acid sodium solution and with mixture.Add amoxycilline Trihydrate bp sodium salt crystal seed (400g).Speed with 27 liters of per minutes adds methyl acetate (921L).Mixture was stirred 1 hour at 0-5 ℃.Then slurry is transferred to Nutrex
TMIn the mixing tank and filtrated stock.With methyl acetate (84L) flushing product.2.4 it is dry
To dry up from 2.3 crystallized product and dry under 60-65 ℃ of vacuum subsequently with nitrogen.
The amoxycilline Trihydrate bp content of products therefrom is 89.7-93.6%, and content of impurities is 1.72-1.42%.
Claims (16)
1. method for preparing crystallization amoxycilline Trihydrate bp an alkali metal salt, wherein:
In first kind of organic solvent, form the suspension of amoxycilline Trihydrate bp amine salt;
This suspension mixed with second kind of organic solvent and amine salt is entered in the mixture solution of first kind and second kind organic solvent of formation like this;
Make the reaction of amine salt and alkali-metal salt-forming compound;
The amoxycilline Trihydrate bp an alkali metal salt that so forms is separated from solution as crystallized product.
2. according to the process of claim 1 wherein that the crystallization amoxycilline Trihydrate bp an alkali metal salt by described method preparation is a crystallization amoxycilline Trihydrate bp sodium salt.
3. according to the process of claim 1 wherein that the amoxycilline Trihydrate bp amine salt is triethylamine, diethylamine or the diisopropyl amine salt of amoxycilline Trihydrate bp.
4. according to the process of claim 1 wherein that first kind of organic solvent is (C1-51-5) alkyl (C1-51-5) alkane carboxylicesters.
5. according to the method for claim 4, wherein (C1-51-5) alkyl (C1-51-5) alkane carboxylicesters is a methyl acetate.
6. according to the process of claim 1 wherein that amine salt suspension is by at first forming Utimox suspension and subsequently amine being mixed with this suspension so that amine and amoxycilline Trihydrate bp reaction formation amine salt form in first kind of solvent.
7. according to the process of claim 1 wherein that second kind of organic solvent is (C1-51-5) alcohol.
8. according to the method for claim 7, wherein (C1-51-5) alcohol is methyl alcohol.
9. according to the process of claim 1 wherein that salt-forming compound is the sodium salt of organic compound.
10. according to the method for claim 9, wherein salt-forming compound is (C1-51-5) sodium alkoxide or (C1-121-5) carboxylate salt.
11. method according to Claim 8, wherein salt-forming compound is a 2 ethyl hexanoic acid sodium.
12. according to the process of claim 1 wherein that the reaction of amine salt undertaken by mixed amine salts solution and salt-forming compound solution.
13. according to the method for claim 10, wherein salt-forming compound is present in the solution of the solvent mixture that comprises first kind and second kind organic solvent.
14. according to the method for claim 13, wherein solvent mixture is for mainly comprising the methyl acetate of methyl acetate: carbinol mixture.
15., wherein amine salt solution is joined in the salt-forming compound solution according to the method for claim 12.
16. crystallization amoxycilline Trihydrate bp an alkali metal salt is for requiring the product of any method according to aforesaid right.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8755498P | 1998-06-01 | 1998-06-01 | |
| US60/087,554 | 1998-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1304412A true CN1304412A (en) | 2001-07-18 |
| CN1182138C CN1182138C (en) | 2004-12-29 |
Family
ID=22205864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998069272A Expired - Fee Related CN1182138C (en) | 1998-06-01 | 1999-06-01 | Process for preparing crystalline salts of amoxycillin |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1086109A4 (en) |
| JP (1) | JP2002517398A (en) |
| KR (1) | KR20010043942A (en) |
| CN (1) | CN1182138C (en) |
| AU (1) | AU760934B2 (en) |
| BR (1) | BR9910804A (en) |
| CA (1) | CA2333943A1 (en) |
| HU (1) | HUP0102008A3 (en) |
| IL (1) | IL139736A (en) |
| NO (1) | NO20006073D0 (en) |
| NZ (1) | NZ508179A (en) |
| PL (1) | PL344348A1 (en) |
| TR (1) | TR200003517T2 (en) |
| WO (1) | WO1999062910A1 (en) |
| ZA (1) | ZA200006946B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633663B (en) * | 2009-08-28 | 2011-12-21 | 沈阳顺旺动物药业有限公司 | Method for synthesizing penicillin sodium salt and potassium salt |
| CN102971328A (en) * | 2010-06-16 | 2013-03-13 | 瓦尔德曼化学科技股份有限公司 | Improved process for preparing amoxicillin sodium |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6294199B1 (en) | 1999-04-13 | 2001-09-25 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising administering amoxycillin |
| US6878386B1 (en) | 1999-04-13 | 2005-04-12 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising amoxycillin and potassium clavulanate |
| EP1838287B1 (en) * | 2005-01-07 | 2012-05-23 | Sandoz Ag | Process for preparing granulates comprising amoxicillin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8606871A1 (en) * | 1985-10-21 | 1986-06-01 | Antibioticos Sa | A process for the preparation of sodium amoxycillin. |
| IT1255716B (en) * | 1992-10-05 | 1995-11-10 | PROCEDURE FOR THE PREPARATION OF STERILE BETA-LACTAMIC ANTIBIOTICS | |
| TW347383B (en) * | 1995-10-26 | 1998-12-11 | Biochemie Gmbh | A process for the production of a crystalline sodium salt of amoxicillin in ethanol as solvent |
-
1999
- 1999-06-01 TR TR2000/03517T patent/TR200003517T2/en unknown
- 1999-06-01 AU AU43216/99A patent/AU760934B2/en not_active Ceased
- 1999-06-01 KR KR1020007013513A patent/KR20010043942A/en not_active Application Discontinuation
- 1999-06-01 CN CNB998069272A patent/CN1182138C/en not_active Expired - Fee Related
- 1999-06-01 HU HU0102008A patent/HUP0102008A3/en unknown
- 1999-06-01 BR BR9910804-6A patent/BR9910804A/en not_active IP Right Cessation
- 1999-06-01 PL PL99344348A patent/PL344348A1/en not_active Application Discontinuation
- 1999-06-01 CA CA002333943A patent/CA2333943A1/en not_active Abandoned
- 1999-06-01 EP EP99955267A patent/EP1086109A4/en not_active Withdrawn
- 1999-06-01 NZ NZ508179A patent/NZ508179A/en unknown
- 1999-06-01 IL IL13973699A patent/IL139736A/en not_active IP Right Cessation
- 1999-06-01 WO PCT/US1999/011991 patent/WO1999062910A1/en not_active Application Discontinuation
- 1999-06-01 JP JP2000552121A patent/JP2002517398A/en not_active Withdrawn
-
2000
- 2000-11-27 ZA ZA200006946A patent/ZA200006946B/en unknown
- 2000-11-30 NO NO20006073A patent/NO20006073D0/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101633663B (en) * | 2009-08-28 | 2011-12-21 | 沈阳顺旺动物药业有限公司 | Method for synthesizing penicillin sodium salt and potassium salt |
| CN102971328A (en) * | 2010-06-16 | 2013-03-13 | 瓦尔德曼化学科技股份有限公司 | Improved process for preparing amoxicillin sodium |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9910804A (en) | 2001-02-13 |
| HUP0102008A2 (en) | 2001-12-28 |
| IL139736A0 (en) | 2002-02-10 |
| ZA200006946B (en) | 2002-01-28 |
| CA2333943A1 (en) | 1999-12-09 |
| NO20006073L (en) | 2000-11-30 |
| HUP0102008A3 (en) | 2002-07-29 |
| EP1086109A4 (en) | 2001-12-19 |
| NO20006073D0 (en) | 2000-11-30 |
| TR200003517T2 (en) | 2001-06-21 |
| AU760934B2 (en) | 2003-05-22 |
| KR20010043942A (en) | 2001-05-25 |
| NZ508179A (en) | 2002-10-25 |
| WO1999062910A1 (en) | 1999-12-09 |
| AU4321699A (en) | 1999-12-20 |
| EP1086109A1 (en) | 2001-03-28 |
| PL344348A1 (en) | 2001-11-05 |
| IL139736A (en) | 2004-02-19 |
| JP2002517398A (en) | 2002-06-18 |
| CN1182138C (en) | 2004-12-29 |
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Granted publication date: 20041229 |