DE69316207T2 - Verfahren zur herstellung eines molkenproteinhydrolysates und hydrolysat - Google Patents
Verfahren zur herstellung eines molkenproteinhydrolysates und hydrolysatInfo
- Publication number
- DE69316207T2 DE69316207T2 DE69316207T DE69316207T DE69316207T2 DE 69316207 T2 DE69316207 T2 DE 69316207T2 DE 69316207 T DE69316207 T DE 69316207T DE 69316207 T DE69316207 T DE 69316207T DE 69316207 T2 DE69316207 T2 DE 69316207T2
- Authority
- DE
- Germany
- Prior art keywords
- process according
- protein hydrolysate
- whey protein
- carried out
- stage
- 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.)
- Expired - Fee Related
Links
- 239000003531 protein hydrolysate Substances 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 108010009736 Protein Hydrolysates Proteins 0.000 title claims description 14
- BHCBLTRDEYPMFZ-UHFFFAOYSA-N 5-acetamido-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound CC(=O)NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I BHCBLTRDEYPMFZ-UHFFFAOYSA-N 0.000 title 1
- 239000000413 hydrolysate Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 46
- 108010046377 Whey Proteins Proteins 0.000 claims abstract description 40
- 102000007544 Whey Proteins Human genes 0.000 claims abstract description 40
- 235000021119 whey protein Nutrition 0.000 claims abstract description 38
- 230000007062 hydrolysis Effects 0.000 claims abstract description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 12
- 239000007858 starting material Substances 0.000 claims abstract description 8
- 239000005018 casein Substances 0.000 claims abstract description 6
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000021240 caseins Nutrition 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000002779 inactivation Effects 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 108091005804 Peptidases Proteins 0.000 claims description 8
- 229940088598 enzyme Drugs 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000004365 Protease Substances 0.000 claims description 6
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 238000000108 ultra-filtration Methods 0.000 claims description 5
- 238000001728 nano-filtration Methods 0.000 claims description 4
- 238000010979 pH adjustment Methods 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000012466 permeate Substances 0.000 claims description 3
- 238000001223 reverse osmosis Methods 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 241000194108 Bacillus licheniformis Species 0.000 claims description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 2
- 102000035195 Peptidases Human genes 0.000 claims description 2
- 102000004142 Trypsin Human genes 0.000 claims description 2
- 108090000631 Trypsin Proteins 0.000 claims description 2
- 239000005862 Whey Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000003916 acid precipitation Methods 0.000 claims description 2
- 238000010306 acid treatment Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000001471 micro-filtration Methods 0.000 claims description 2
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 claims description 2
- 239000012465 retentate Substances 0.000 claims description 2
- 239000012588 trypsin Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 238000001556 precipitation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- 238000012360 testing method Methods 0.000 description 12
- 108090000765 processed proteins & peptides Proteins 0.000 description 10
- 102000004196 processed proteins & peptides Human genes 0.000 description 8
- 235000018102 proteins Nutrition 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 235000020183 skimmed milk Nutrition 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- GNNALEGJVYVIIH-UHFFFAOYSA-N benzene-1,2-diamine;hydrochloride Chemical compound Cl.NC1=CC=CC=C1N GNNALEGJVYVIIH-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- 230000002009 allergenic effect Effects 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 230000000890 antigenic effect Effects 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 235000020247 cow milk Nutrition 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 2
- 102000003992 Peroxidases Human genes 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 102000005158 Subtilisins Human genes 0.000 description 2
- 108010056079 Subtilisins Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000013566 allergen Substances 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 108040007629 peroxidase activity proteins Proteins 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229910017917 NH4 Cl Inorganic materials 0.000 description 1
- 229910021204 NaH2 PO4 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 108010009355 microbial metalloproteinases Proteins 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003118 sandwich ELISA Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
- C12Y304/21—Serine endopeptidases (3.4.21)
- C12Y304/21004—Trypsin (3.4.21.4)
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J3/00—Working-up of proteins for foodstuffs
- A23J3/30—Working-up of proteins for foodstuffs by hydrolysis
- A23J3/32—Working-up of proteins for foodstuffs by hydrolysis using chemical agents
- A23J3/34—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes
- A23J3/341—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes of animal proteins
- A23J3/343—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes of animal proteins of dairy proteins
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Wood Science & Technology (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Dairy Products (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK92712A DK71292D0 (enExample) | 1992-05-27 | 1992-05-27 | |
| PCT/DK1993/000182 WO1993024020A1 (en) | 1992-05-27 | 1993-05-26 | Method for production of a whey protein hydrolyzate and a whey protein hydrolyzate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69316207D1 DE69316207D1 (de) | 1998-02-12 |
| DE69316207T2 true DE69316207T2 (de) | 1998-06-25 |
Family
ID=8096674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69316207T Expired - Fee Related DE69316207T2 (de) | 1992-05-27 | 1993-05-26 | Verfahren zur herstellung eines molkenproteinhydrolysates und hydrolysat |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0642307B1 (enExample) |
| JP (1) | JP3230681B2 (enExample) |
| AT (1) | ATE161689T1 (enExample) |
| AU (1) | AU668400B2 (enExample) |
| CA (1) | CA2136610C (enExample) |
| DE (1) | DE69316207T2 (enExample) |
| DK (2) | DK71292D0 (enExample) |
| ES (1) | ES2114055T3 (enExample) |
| GR (1) | GR3026293T3 (enExample) |
| NZ (1) | NZ253019A (enExample) |
| WO (1) | WO1993024020A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5405637A (en) * | 1993-06-30 | 1995-04-11 | Bristol-Myers Squibb Company | Milk protein partial hydrolysate and infant formula containing same |
| US5618689A (en) * | 1995-05-25 | 1997-04-08 | Nestec S.A. | Enhanced procedures for preparing food hydrolysates |
| AU761477B2 (en) | 1998-06-17 | 2003-06-05 | New Zealand Dairy Board | Bioactive whey protein hydrolysate |
| NZ506866A (en) * | 2000-09-11 | 2003-05-30 | New Zealand Dairy Board | Bioactive whey protein hydrolysate free of bitter flavours wherein the enzyme used is a heat labile protease |
| WO2003059083A1 (de) * | 2002-01-21 | 2003-07-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Molkenproteinhydrolysate und peptidfraktionen aus molkenprotein mit bioaktiver wirkung aus hydrolysen mit proteasen |
| PL368179A1 (en) * | 2004-05-24 | 2005-11-28 | Sgp & Sons Ab | Proteollytic method for processing proteins and protein hydrolysis products, enriched with exogenous, semi-exogenous and conditionally exogenous amino acids for making therapeutic preparation used in normal and medicinal diets |
| DE102008032828A1 (de) * | 2008-07-02 | 2010-01-07 | Technische Universität Dresden | Tryptophanhaltige Peptide aus alpha-Lactalbumin mit blutdrucksenkender und vasoprotektiver Wirkung für biofunktionelle Lebensmittel |
| US9055752B2 (en) | 2008-11-06 | 2015-06-16 | Intercontinental Great Brands Llc | Shelf-stable concentrated dairy liquids and methods of forming thereof |
| CN105661553A (zh) * | 2009-04-02 | 2016-06-15 | 诺维信公司 | 用于制备基于乳的蛋白质水解产物的方法 |
| UA112972C2 (uk) | 2010-09-08 | 2016-11-25 | Інтерконтінентал Грейт Брендс ЛЛС | Рідкий молочний концентрат з високим вмістом сухих речовин |
| KR101698379B1 (ko) * | 2015-09-17 | 2017-01-20 | 삼육대학교산학협력단 | 산양유 단백질 가수분해물, 그것의 제조방법 및 그것의 식품에 사용하는 용도 |
| RU2663583C2 (ru) * | 2015-12-30 | 2018-08-07 | Федеральное государственное бюджетное научное учреждение "Федеральный научный центр пищевых систем им. В.М. Горбатова" РАН | Способ производства гидролизата сывороточных белков |
| JP2019513380A (ja) | 2016-04-08 | 2019-05-30 | フラウンホッファー−ゲゼルシャフト ツァ フェルダールング デァ アンゲヴァンテン フォアシュンク エー．ファオ | マメ科植物又は脂肪種子由来の技術機能的な植物タンパク質画分 |
| WO2019141662A1 (en) | 2018-01-16 | 2019-07-25 | Frieslandcampina Nederland B.V. | Hypoallergenic infant formula and methods for preparing the same |
| ES2964808T3 (es) * | 2019-05-29 | 2024-04-09 | Arla Foods Amba | Hidrolizados de proteína de suero de la leche extensamente hidrolizados apetecibles |
| US20240150418A1 (en) | 2021-03-02 | 2024-05-09 | Arla Foods Amba | Immunogenic protein hydrolysate with reduced allergenicity |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2459620B1 (fr) * | 1979-06-26 | 1983-08-05 | Agronomique Inst Nat Rech | Hydrolisat enzymatique total de proteines de lactoserum, obtention et application |
| EP0065663A1 (en) * | 1981-05-11 | 1982-12-01 | Miles Laboratories, Inc. | Method for the preparation of a protein hydrolyzate from whey protein |
| FR2608051B1 (fr) * | 1986-12-15 | 1989-04-07 | Bellon Labor Sa Roger | Procede de fabrication d'un hydrolysat enzymatique de proteines riche en di- et tri-peptides, utilisable notamment en nutrition artificielle et en dietetique |
| BE1003298A3 (nl) * | 1990-01-12 | 1992-02-18 | Tessenderlo Chem Nv | Werkwijze voor het bereiden van een enzymatisch hydrolysaat. |
| US5866357A (en) * | 1990-03-09 | 1999-02-02 | Novo Nordisk A/S | Method for hydrolyzing proteins with gluyasp specific protease |
| DK3991D0 (da) * | 1991-01-10 | 1991-01-10 | Novo Nordisk As | Fremgangsmaade til fremstilling af et proteinhydrolysat |
| AU656977B2 (en) * | 1991-05-31 | 1995-02-23 | Danmark Protein A/S | Method for production of a whey protein hydrolyzate |
| AU2468292A (en) * | 1991-08-30 | 1993-04-05 | Teagasc, The Agriculture And Food Development Authority | Hypoallergenic whey protein hydrolysate |
-
1992
- 1992-05-27 DK DK92712A patent/DK71292D0/da unknown
-
1993
- 1993-05-26 DK DK93912667T patent/DK0642307T3/da active
- 1993-05-26 AU AU43099/93A patent/AU668400B2/en not_active Ceased
- 1993-05-26 EP EP93912667A patent/EP0642307B1/en not_active Expired - Lifetime
- 1993-05-26 DE DE69316207T patent/DE69316207T2/de not_active Expired - Fee Related
- 1993-05-26 CA CA002136610A patent/CA2136610C/en not_active Expired - Fee Related
- 1993-05-26 JP JP50009794A patent/JP3230681B2/ja not_active Expired - Fee Related
- 1993-05-26 AT AT93912667T patent/ATE161689T1/de not_active IP Right Cessation
- 1993-05-26 WO PCT/DK1993/000182 patent/WO1993024020A1/en not_active Ceased
- 1993-05-26 ES ES93912667T patent/ES2114055T3/es not_active Expired - Lifetime
- 1993-05-26 NZ NZ253019A patent/NZ253019A/xx not_active IP Right Cessation
-
1998
- 1998-03-06 GR GR980400464T patent/GR3026293T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4309993A (en) | 1993-12-30 |
| ATE161689T1 (de) | 1998-01-15 |
| EP0642307A1 (en) | 1995-03-15 |
| DE69316207D1 (de) | 1998-02-12 |
| EP0642307B1 (en) | 1998-01-07 |
| JPH07506971A (ja) | 1995-08-03 |
| AU668400B2 (en) | 1996-05-02 |
| CA2136610A1 (en) | 1993-12-09 |
| NZ253019A (en) | 1995-12-21 |
| DK0642307T3 (da) | 1998-09-07 |
| ES2114055T3 (es) | 1998-05-16 |
| CA2136610C (en) | 2004-10-05 |
| WO1993024020A1 (en) | 1993-12-09 |
| GR3026293T3 (en) | 1998-06-30 |
| DK71292D0 (enExample) | 1992-05-27 |
| JP3230681B2 (ja) | 2001-11-19 |
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