WO2002013755A1 - Procede de fabrication de capsule sans soudure - Google Patents
Procede de fabrication de capsule sans soudure Download PDFInfo
- Publication number
- WO2002013755A1 WO2002013755A1 PCT/JP2001/007054 JP0107054W WO0213755A1 WO 2002013755 A1 WO2002013755 A1 WO 2002013755A1 JP 0107054 W JP0107054 W JP 0107054W WO 0213755 A1 WO0213755 A1 WO 0213755A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- liquid
- nozzle
- flow
- curing
- seamless capsule
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61J—CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE
- A61J3/00—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms
- A61J3/07—Devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms into the form of capsules or similar small containers for oral use
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5089—Processes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
Definitions
- the present invention relates to a method for producing a spherical seamless capsule in which a filling substance composed of a medicine, a fragrance, a spice, a fragrance and the like is coated with a coating substance composed of gelatin or the like.
- the aerial nozzle method deforms droplets cut in the air by dropping and colliding with the liquid surface of the hardening liquid, so that the sphericity of the manufactured seamless capsules varies. there were.
- a main object of the present invention is to provide a seamless capsule manufacturing method for obtaining seamless capsules of good quality without variation.
- the lower end of the concentric multi-nozzle be immersed in a curing liquid to allow a concentric cylindrical merged liquid flow to flow out of the curing liquid through the lower end opening.
- This submerged nozzle method was found to cause an S-shaped scratch on the surface of the seamless capsule. Therefore, the present inventors have conducted various studies, It has been found that the occurrence of S-shaped flaws is due to moisture mixed and dispersed in the curing liquid. That is, the moisture in the hardening solution adheres to the outer surface of the lower end of the high-temperature concentric multi-nozzle immersed in the hardening solution and condenses, and this gradually grows into a large droplet.
- the present invention based on this finding provides a method of manufacturing a seamless capsule in which a filling material is coated with a film material, comprising: a central nozzle; and a concentric multiple nozzle having an annular nozzle concentrically surrounding the central nozzle. Disposing the liquid filling material to the center nozzle of the concentric multi-nozzle, and supplying the liquid coating material to the concentric multi-nozzle.
- a concentric cylindrical shape composed of a thread to be supplied to the annular nozzle, a flow of the liquid filling substance flowing out of the central nozzle, and a liquid film substance flowing out of the annular nozzle and flowing around the flow of the filling substance.
- this method is not a method of dropping a droplet onto a curing liquid, the droplet does not deform due to collision with the liquid surface.
- the tip of the concentric multi-nozzle is located above the liquid level of the curing liquid, the water contained in the curing liquid does not adhere to the nozzle surface and does not enter the combined liquid flow. . Therefore, occurrence of S-shaped scratches can also be prevented.
- means for forming droplets means for applying vibration to the combined liquid flow is preferable.
- the immersion position of the combined liquid flow is a position eccentric from the center of the forming tube. In this case, since there is a difference in the flow rate of the curing liquid between the inner side and the outer side in the forming tube, the droplet is rotated, and However, the shape of the droplet becomes good.
- the outer diameter of the seamless capsule is d, it is effective to set the distance between the tip of the concentric multi-nozzle and the liquid level of the hardening liquid within the range of 0, 5 d or 3 d. .
- FIG. 1 is a schematic diagram showing a system for implementing a method for producing a seamless capsule according to the present invention.
- FIG. 2 is a partially enlarged view showing a concentric multiple nozzle used in the system of FIG. 1 and its vicinity.
- FIG. 3 is an enlarged schematic diagram of the combined liquid flow.
- FIG. 4 is a diagram showing the relationship between the distance between the nozzle tip and the liquid surface and the sphericity.
- FIG. 5 is a diagram showing the relationship between the distance between the nozzle tip and the liquid surface and the eye diameter.
- FIG. 6 is a diagram showing the relationship between the distance between the nozzle tip and the liquid surface and the degree of eccentricity.
- FIG. 7 is an explanatory diagram showing a seamless capsule having poor sphericity.
- FIG. 8 is an explanatory diagram showing the eyes of the seamless capsule.
- FIG. 9 is an explanatory diagram showing a seamless capsule having poor eccentricity.
- FIG. 1 schematically shows a system for carrying out a method for manufacturing a seamless force busel according to the present invention
- FIG. 2 shows an enlarged view of a concentric multiple nozzle used in the system and a configuration around the nozzle. ing.
- reference numeral 1 denotes a chemical tank storing a liquid filling substance (hereinafter simply referred to as a chemical) composed of a medicine, a fragrance, a spice, a fragrance, and the like.
- the chemical liquid in the chemical liquid reservoir 1 is extracted by a variable discharge type chemical liquid pump 3 through a pipe 33, and supplied to a concentric multiple nozzle 4 through a pipe 23. Since it is desirable that the flow of the chemical solution to the concentric multiple nozzle 4 is as stable as possible, the chemical solution pump 3 A type that does not pulsate the flow is preferred.
- reference numeral 5 denotes a substance having a property of gelling from a sol state, for example, a substance such as gelatin, agar, carrageenan or alginic acid, or a gum such as guar gum or xantham gum.
- the figure shows a gelatin tank (first tank) 5 that stores a liquid film material (hereinafter simply referred to as a gelatin solution).
- the gelatin solution While the gelatin solution is stored in the gelatin tank 5, the gelatin solution is heated by a warm water circulating in a warm water jacket 9 provided around the gelatin tank 5 to maintain a certain temperature, for example, 50 ° C. Has been maintained.
- the temperature of the ⁇ _ ⁇ ⁇ which has dropped during the circulation in the hot water jacket 9 passes through the pipe 36 and becomes the first constant temperature bath.
- the gelatin solution in the gelatin tube 5 is extracted through the inner tube 14 a of the double tube 14 by the variable discharge type gelatin pump 15 which does not form a pulsation in the flow, and the inner tube of the double tube 16 is extracted.
- 16 a, the spiral tube 6 a of the intermediate heater 6, the inner tube 17 a of the double tube 17, and the pipe 19 are supplied to the concentric multi-nozzle 4 in this order.
- Hot water as a heating fluid is introduced into the annular space between the inner tube 14a and the outer tube 14b of the double tube 14 from an inflow port provided at the end on the gelatin tank 5 side.
- the hot water which was heated by the heater 13 in the second constant temperature bath 12 and maintained at a constant temperature, was heated by the second hot water pump 13 through the pipe 39 and the pipe 40 to form the double pipe 1. 4 will be supplied.
- the warm water flowing between the inner tube 14a and the outer tube 14b heats the gelatin solution flowing through the inner tube 14a of the double tube 12.
- the warm water in the double tube 16 enters the intermediate heater 6 via the tube 42, and heats the gelatin solution flowing in the spiral tube 6a in the process of flowing around the spiral tube 6a.
- the hot water flowing out of the intermediate heater 6 enters the annular space between the inner tube 17a and the outer tube 17b of the double tube 17 via the tube 43, and in the process of flowing through this space. Heat the gelatin solution flowing in the inner tube 17a. Thereafter, the hot water flows out of the double pipe 17 and returns to the second constant temperature bath 12 via the pipe 44 where it is heated again.
- the gelatin solution is heated by hot water 50 ° while flowing through the transfer tubes 14a, 16a, 6a, and 17a from the gelatin nozzle 5 to the concentric multi-nozzle 4.
- the temperature gradually increases from C to a predetermined temperature, for example, 80 ° C., and flows into the concentric multiple nozzle 4.
- the concentric multi-nozzle 4 includes a central nozzle 4a that opens downward and an annular nozzle 4b that concentrically surrounds the central nozzle 4a.
- the tip of 4b is arranged above the liquid level of the curing liquid in the forming tube 20.
- the hardening solution hardens the gelatin solution by touching the gelatin solution, and can be appropriately selected from medium chain fatty acid triglyceride, water, liquid paraffin, calcium solution, and vegetable oil such as soybean oil and purified oil. .
- a movable wall 4 d made of a flexible film or the like that defines a part of the wall of the chamber 4 c is provided above the chamber 4 c in the concentric multi-nozzle 4 through which the chemical solution is guided through the pipe 23. Is provided.
- the movable wall 4d is moved up and down by the vibrator 11 so that the chemical solution in the chamber 4c can be vibrated at a predetermined cycle and amplitude. Therefore, a pulsating wave propagating downward is generated in the chemical solution by this operation of the movable wall 4d.
- the chemical supplied to the concentric multi-nozzle 4 flows downward from the central nozzle 4a, and at the same time, the gelatin solution supplied to the concentric multi-nozzle 4 surrounds the flow of the chemical and the annular nozzle 4b Spills downward from
- the concentric multi-nozzle 4 is composed of a chemical solution and a gelatin solution covering the outer periphery thereof.
- the concentric columnar merged liquid flow continuously flows out, and the lower end of the merged liquid flow is immersed in the squeeze liquid in the forming pipe 20.
- This immersion position is a position eccentric from the center of the forming tube 20.
- the forming tube 20 is a tubular body that has a vertical portion that extends vertically and has an open upper end, and is concentric with the vertical portion of the forming tube 20.
- a reserve tank 32 is formed around the forming tube 20, and the curing liquid is supplied into the reserve tank 32. Therefore, the curing liquid in the reservoir 32 flows into the forming tube 20 from the open upper end of the forming tube 20 and flows downward through the inside.
- the vibration of the movable wall 4d is transmitted to the combined liquid flow via the chemical solution, whereby the combined liquid flow is sequentially cut from the tip in the hardening liquid, whereby the liquid obtained by coating the chemical solution with the gelatin solution is applied. Drops are formed.
- the droplets drop due to the gravity acting on the droplets and the hardening liquid flowing downward in the forming tube 20. Since the flow rate of the curing liquid in the forming tube 20 is faster at the center and becomes slower toward the tube wall, the droplet immersed at a position eccentric from the center of the forming tube 20 and cut off is The droplet is rotated by the flow velocity difference between the curing liquid flowing outside (the tube wall side) and the curing liquid flowing inside (the center side of the forming tube 20).
- the gelatin solution on the surface of the droplet is cooled by contact with the hardening solution, and gradually hardens by reacting with Z or the hardening solution.
- the effect of improving the appearance quality of the seamless capsule by the rotation inside the forming tube 20 is not only when the droplet is formed below the liquid surface of the curing liquid, but also when it is formed above the liquid surface. It is also obtained when it is dropped into a curing liquid.
- the lower part of the forming tube 20 is curved in the horizontal direction. The opening 20a at the end (lower end) of the curved part is immersed in the curing liquid stored in the curing tank 21. Have been.
- the forming tube 20 is rotatably supported around a vertical axis, and is driven to rotate by a motor (not shown).
- a motor not shown
- the forming tube 20 is gently rotated around the vertical axis, the hardening liquid and the accompanying liquid droplets in the forming tube 20 flow out of the opening 20a in the horizontal direction.
- the droplets are dispersed in the curing liquid stored in the curing tank 21 on a circumference slightly larger in diameter than the turning trajectory of the opening 20a, and then gradually descend in the curing liquid.
- the gelatin solution hardens sufficiently to form a simple capsule.
- Sent into 2 3 A sieve plate 24 made of a perforated plate, a net, or the like is arranged at an upper part of Separete Night 23 in an inclined manner. Since the size of the sieve plate 24 is smaller than the outer diameter of the sheathless capsule, when the hardening liquid and the seamless capsule flow into the separator 23, the hardening liquid passes through the sieve plate 24 and passes through the separator 23.
- the seamless capsules fall to the bottom and are stored here, and the seamless capsules roll on the sieve plate 24, fall through the gutter 25 into the collection container 26, and are stored here.
- the cooler 27 is immersed in the hardening liquid stored at the bottom of the Severe overnight 23, and the refrigerant cooled by the refrigerator 28 in the heat transfer tube 27a of the cooler 27 Circulates. Accordingly, the hardening liquid is cooled by exchanging heat with the refrigerant circulating in the heat transfer tube 27a of the cooler 27 while being stored at the bottom of the separator 23.
- the hardening liquid stored in Separete overnight 23 is extracted from the bottom of Separete overnight 23 through a filter medium 29 made of silica gel, etc., and the hardening liquid pipe 30 and the hardening liquid interposed in it
- the pump 31 enters the reservoir 32 installed around the forming tube 20 through the pump 31, and then flows into the forming tube 20 beyond the upper edge of the reserve tank 32.
- the highest position of the transfer pipe 22, that is, the inverted U-shaped part 2 2 a is lower than the liquid level of the curing liquid in the reservoir tank 32, but this inverted U-shaped part 2 2 up and down a It is moved up and down by the moving unit 34 to adjust the difference between the inverted U-shaped part 2 2 a and the level of the hardening liquid in the reserve tank 32, so that the conveying pipe passes from the forming pipe 20 through the hardening tank 21. It is possible to adjust the flow rate of the hardening liquid flowing in the inside of 22.
- reference numeral 35 denotes a temperature sensor
- FIG. 3 shows an observation result of a concentric cylinder-shaped combined liquid flow flowing out of the concentric multi-nozzle 4 with vibration applied.
- the outer diameter d of the seamless capsule is substantially determined by the flow velocity and vibration timing of the combined liquid flow from the nozzle. Also, the viscosity of the combined liquid stream and the nozzle diameter have almost no effect on the outer diameter d of the seamless capsule.
- the combined liquid flow expands at the tip of the concentric multi-nozzle 4 due to its viscoelasticity or normal stress hardening due to the paras effect and becomes large in diameter. For this reason, the distance from the nozzle tip to the distance of about 2 d gradually decreases, the distance gradually increases from this point to a distance of about 3.3 d, the distance gradually decreases from this point to a distance of about 4.6 d, and the distance from here decreases again. It becomes thicker up to a distance of 6 d and gradually narrows from here to a distance of about 7.3 d, immerses in the hardening liquid, after which the tip of the combined liquid stream is cut off.
- FIGS. 4, 5, and 6 show the seamless capsules while changing the distance D (see FIG. 2) between the tip of the concentric multi-nozzle 4 and the surface of the curing liquid in the forming tube 20. It shows the results of measuring sphericity, eye diameter and eccentricity.
- the difference between the major axis L 1 and the minor axis L 2 of the seamless capsule is small, sphericity seamless power capsule is good, if a large difference, as shown in FIG. 7, the sphericity is determined to be bad, As can be understood from FIG. 4, the difference between the major axis L and the minor axis 1 ⁇ 2 of the seamless capsule increases sharply when the distance D exceeds 3 d, and the sphericity deteriorates.
- the eye diameter that is, the seamless force shown in FIG.
- the diameter Id of the chemical solution mass (the so-called eyes) S formed in the capsule film increases with a sharp curve drawn at the point where the distance D becomes 3 d.
- lumps S called eyes are generated.
- Henshindo i.e. the ratio of the thickness W 2 of the thickness and the thick portion of the thin part fraction of film of the seamless capsule as shown in FIG. 9 (W Increases gradually until the distance D becomes 2 d, is almost constant from 2 d to 3 d, and decreases sharply from 3 d.
- W Increases gradually until the distance D becomes 2 d, is almost constant from 2 d to 3 d, and decreases sharply from 3 d.
- the distance D was in the range of 0.5 d to 3 d
- the distance D was in the range of 0.5 d to 3 d
- the eye diameter is 500 ⁇ m or less
- the eccentricity is 0.5 or more
- the sphericity is 150 m or less
- the weight deviation RSD is 0.35% or less.
- a seamless capsule could be manufactured.
- in appearance inspection it was possible to produce a seam capsule in which the appearance frequency of the egg-shaped deformation force capsule and the S-shaped wound capsule was 1 or 0 around 240.000 pieces.
- the distance D is 2 d, that is, in the first stage from the top in the combined liquid flow, or in the narrow-diameter portion, the squeezing portion collides with the liquid surface and the spheroidization proceeds from this squeezing portion. Hindered. As a result, the moldability deteriorates and the dispersion of the coating weight increases, so that the distance! Is desirably in the range of 0.5 d to 1.5 d.
- Test 1, Test 2 and Test 3 were performed by operating the apparatus shown in FIGS. 1 and 2 under the conditions shown in Table 2 using the chemical solution and the gelatin solution having the formulation shown in Table 1. The results of the implementation will be described. Note that Test 1 is an example of the present invention, and Test 2 and Test 3 are comparative examples. table 1
- the eccentric distance of the nozzle refers to the horizontal distance between the central axis of the concentric multiple nozzle and the central axis of the vertical portion of the forming tube.
- Test 1 the distance between the tip of the concentric multiple nozzle and the liquid level of the curing liquid was set to 1 d.
- Test 2 the tip of the concentric multi-nozzle was immersed in the dangling solution.
- Test 3 the distance between the tip of the concentric multi-nozzle and the liquid level of the curing liquid was set to 5 d.
- Table 3 shows the results of the evaluation of the physical properties of the seamless capsules obtained by such tests 1, 2 and 3, and Table 4 shows the results of the appearance inspection.
- n 1 0
- Test 3 in which the distance between the nozzle tip and the liquid surface of the curing liquid was set to 5 d, all the physical properties were inferior to those in Test 1, and an egg-shaped deformed capsule was also observed.
- the tip of the concentric multi-nozzle since the tip of the concentric multi-nozzle is arranged above the liquid surface of the curing liquid, unlike the conventional submerged nozzle method, it condenses on the outer surface of the lower end of the concentric multi-nozzle. The water droplets that have grown grow into the merged liquid flow and
- S-shaped scratches can be reliably prevented.
- the tip of the concentric multi-nozzle is arranged downward, and the lower end of the concentric cylindrical merging liquid flow that is continuously discharged from the concentric multi-nozzle is immersed in the curing liquid and merged in this curing liquid. Since the liquid flow is interrupted, unlike the conventional aerial nozzle method, deformation caused by the droplets that have been interrupted falling in the air and colliding with the liquid surface of the curing liquid, that is, the sphericity and eccentricity of the seamless capsule Deterioration can be prevented.
- the outer diameter of the seamless capsule is d and the distance between the tip of the concentric multi-nozzle and the liquid level of the curing liquid is set in the range of 0.5 d to 3 d, the sphericity and the eyes It is possible to obtain a seamless capsule that sufficiently satisfies all of the process standards such as diameter and eccentricity.
- the defect-free seamless capsule can be manufactured efficiently. Therefore, the present invention can be widely used in the manufacturing industries such as pharmaceuticals, confectionery and foods. ⁇
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Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60140874T DE60140874D1 (de) | 2000-08-17 | 2001-08-16 | Verfahren zum herstellen einer nahtlosen kapsel |
AU2001278747A AU2001278747A1 (en) | 2000-08-17 | 2001-08-16 | Method of manufacturing seamless capsule |
EP01956914A EP1310229B1 (en) | 2000-08-17 | 2001-08-16 | Method of manufacturing seamless capsule |
US10/344,677 US7112292B2 (en) | 2000-08-17 | 2001-08-16 | Method of manufacturing seamless capsule |
AT01956914T ATE452618T1 (de) | 2000-08-17 | 2001-08-16 | Verfahren zum herstellen einer nahtlosen kapsel |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000247878 | 2000-08-17 | ||
JP2000-247878 | 2000-08-17 |
Publications (1)
Publication Number | Publication Date |
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WO2002013755A1 true WO2002013755A1 (fr) | 2002-02-21 |
Family
ID=18737880
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2001/007054 WO2002013755A1 (fr) | 2000-08-17 | 2001-08-16 | Procede de fabrication de capsule sans soudure |
Country Status (7)
Country | Link |
---|---|
US (1) | US7112292B2 (ja) |
EP (2) | EP1310229B1 (ja) |
JP (1) | JP4778639B2 (ja) |
AT (2) | ATE544440T1 (ja) |
AU (1) | AU2001278747A1 (ja) |
DE (1) | DE60140874D1 (ja) |
WO (1) | WO2002013755A1 (ja) |
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US9676150B2 (en) | 2011-08-10 | 2017-06-13 | British American Tobacco (Investments) Limited | Capsule formation |
JP2018051421A (ja) * | 2016-09-26 | 2018-04-05 | 国立研究開発法人農業・食品産業技術総合研究機構 | マイクロカプセルの製造装置 |
US10238141B2 (en) | 2011-08-10 | 2019-03-26 | British American Tobacco (Investments) Limited | Capsule formation |
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US20070027047A1 (en) * | 2003-10-31 | 2007-02-01 | Earth Chemical Co., Ltd. | Material in gel state |
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FR2939012B1 (fr) * | 2008-12-01 | 2015-03-27 | Capsum | Procede de fabrication d'une serie de capsules, et serie de capsules associee |
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- 2001-08-16 JP JP2001246899A patent/JP4778639B2/ja not_active Expired - Lifetime
- 2001-08-16 AT AT08169858T patent/ATE544440T1/de active
- 2001-08-16 EP EP01956914A patent/EP1310229B1/en not_active Expired - Lifetime
- 2001-08-16 AT AT01956914T patent/ATE452618T1/de not_active IP Right Cessation
- 2001-08-16 AU AU2001278747A patent/AU2001278747A1/en not_active Abandoned
- 2001-08-16 WO PCT/JP2001/007054 patent/WO2002013755A1/ja active Application Filing
- 2001-08-16 US US10/344,677 patent/US7112292B2/en not_active Expired - Lifetime
- 2001-08-16 DE DE60140874T patent/DE60140874D1/de not_active Expired - Lifetime
- 2001-08-16 EP EP08169858A patent/EP2052710B1/en not_active Expired - Lifetime
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9676150B2 (en) | 2011-08-10 | 2017-06-13 | British American Tobacco (Investments) Limited | Capsule formation |
US10238141B2 (en) | 2011-08-10 | 2019-03-26 | British American Tobacco (Investments) Limited | Capsule formation |
CN102556921A (zh) * | 2012-02-23 | 2012-07-11 | 浙江大学 | 滴液漏斗 |
JP2018051421A (ja) * | 2016-09-26 | 2018-04-05 | 国立研究開発法人農業・食品産業技術総合研究機構 | マイクロカプセルの製造装置 |
Also Published As
Publication number | Publication date |
---|---|
ATE452618T1 (de) | 2010-01-15 |
US7112292B2 (en) | 2006-09-26 |
US20030180485A1 (en) | 2003-09-25 |
EP2052710A3 (en) | 2010-11-03 |
EP1310229A1 (en) | 2003-05-14 |
EP1310229B1 (en) | 2009-12-23 |
AU2001278747A1 (en) | 2002-02-25 |
EP2052710A2 (en) | 2009-04-29 |
JP4778639B2 (ja) | 2011-09-21 |
JP2002136576A (ja) | 2002-05-14 |
EP1310229A4 (en) | 2007-08-01 |
EP2052710B1 (en) | 2012-02-08 |
DE60140874D1 (de) | 2010-02-04 |
ATE544440T1 (de) | 2012-02-15 |
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