DE69508890T2 - Verwendung eines Dekapeptids mit benzodiazepinischer Wirkung zur Herstellung von Arzneimitteln und Diätzusätzen - Google Patents
Verwendung eines Dekapeptids mit benzodiazepinischer Wirkung zur Herstellung von Arzneimitteln und DiätzusätzenInfo
- Publication number
- DE69508890T2 DE69508890T2 DE69508890T DE69508890T DE69508890T2 DE 69508890 T2 DE69508890 T2 DE 69508890T2 DE 69508890 T DE69508890 T DE 69508890T DE 69508890 T DE69508890 T DE 69508890T DE 69508890 T2 DE69508890 T2 DE 69508890T2
- Authority
- DE
- Germany
- Prior art keywords
- decapeptide
- casein
- hydrolysate
- amino acid
- trypsin
- 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 - Lifetime
Links
- 235000015872 dietary supplement Nutrition 0.000 title claims abstract description 7
- 229940049706 benzodiazepine Drugs 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 230000000694 effects Effects 0.000 title description 12
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 title description 2
- 239000003814 drug Substances 0.000 title description 2
- 229940079593 drug Drugs 0.000 title 1
- 239000000413 hydrolysate Substances 0.000 claims abstract description 37
- 235000013305 food Nutrition 0.000 claims abstract description 5
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 4
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 4
- 102000009366 Alpha-s1 casein Human genes 0.000 claims description 35
- 108050000244 Alpha-s1 casein Proteins 0.000 claims description 35
- 102000004142 Trypsin Human genes 0.000 claims description 27
- 108090000631 Trypsin Proteins 0.000 claims description 27
- 239000012588 trypsin Substances 0.000 claims description 27
- 206010010904 Convulsion Diseases 0.000 claims description 14
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 230000036506 anxiety Effects 0.000 claims description 9
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 7
- 150000001557 benzodiazepines Chemical class 0.000 claims description 6
- 230000036461 convulsion Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 235000005911 diet Nutrition 0.000 claims description 4
- 230000037213 diet Effects 0.000 claims description 4
- 208000007101 Muscle Cramp Diseases 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
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- 102100038920 Alpha-S1-casein Human genes 0.000 abstract 1
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- 101000741048 Homo sapiens Alpha-S1-casein Proteins 0.000 abstract 1
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- 238000000034 method Methods 0.000 description 16
- 238000012360 testing method Methods 0.000 description 14
- 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 description 12
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- 239000005018 casein Substances 0.000 description 8
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 8
- 229960003529 diazepam Drugs 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 6
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- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 5
- 108010033276 Peptide Fragments Proteins 0.000 description 5
- 102000007079 Peptide Fragments Human genes 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 229940021722 caseins Drugs 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
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- PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 229960002200 flunitrazepam Drugs 0.000 description 4
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- 210000004080 milk Anatomy 0.000 description 4
- 229960005152 pentetrazol Drugs 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 108050001786 Alpha-s2 casein Proteins 0.000 description 3
- 206010009346 Clonus Diseases 0.000 description 3
- 102000004300 GABA-A Receptors Human genes 0.000 description 3
- 108090000839 GABA-A Receptors Proteins 0.000 description 3
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
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- 230000007717 exclusion Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052722 tritium Inorganic materials 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- 235000021247 β-casein Nutrition 0.000 description 3
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
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- 238000000605 extraction Methods 0.000 description 2
- 238000010265 fast atom bombardment Methods 0.000 description 2
- 238000001641 gel filtration chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000000384 rearing effect Effects 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
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- 239000006228 supernatant Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 235000021246 κ-casein Nutrition 0.000 description 2
- 102100022681 40S ribosomal protein S27 Human genes 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 101710099484 Aminopeptidase T Proteins 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108091006146 Channels Proteins 0.000 description 1
- 108010062745 Chloride Channels Proteins 0.000 description 1
- 102000011045 Chloride Channels Human genes 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 101000678466 Homo sapiens 40S ribosomal protein S27 Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 102000014171 Milk Proteins Human genes 0.000 description 1
- 108010011756 Milk Proteins Proteins 0.000 description 1
- 208000021966 Motor seizure Diseases 0.000 description 1
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- 241000700157 Rattus norvegicus Species 0.000 description 1
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- 239000012634 fragment Substances 0.000 description 1
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- 230000003371 gabaergic effect Effects 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
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- 239000007928 intraperitoneal injection Substances 0.000 description 1
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- 208000018883 loss of balance Diseases 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229940080237 sodium caseinate Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
- C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
- C07K14/4732—Casein
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9414362A FR2727315A1 (fr) | 1994-11-30 | 1994-11-30 | Utilisation d'un decapeptide a activite de type benzodiazepine pour la preparation de medicaments et de complements alimentaires |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69508890D1 DE69508890D1 (de) | 1999-05-12 |
| DE69508890T2 true DE69508890T2 (de) | 1999-10-07 |
Family
ID=9469315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69508890T Expired - Lifetime DE69508890T2 (de) | 1994-11-30 | 1995-11-30 | Verwendung eines Dekapeptids mit benzodiazepinischer Wirkung zur Herstellung von Arzneimitteln und Diätzusätzen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5846939A (enExample) |
| EP (1) | EP0714910B1 (enExample) |
| JP (1) | JP3973244B2 (enExample) |
| AT (1) | ATE178615T1 (enExample) |
| DE (1) | DE69508890T2 (enExample) |
| DK (1) | DK0714910T3 (enExample) |
| ES (1) | ES2135023T3 (enExample) |
| FR (1) | FR2727315A1 (enExample) |
| GR (1) | GR3030650T3 (enExample) |
| SI (1) | SI0714910T1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6465432B1 (en) * | 2000-08-28 | 2002-10-15 | Kraft Food Holdings, Inc. | Isolated antioxidant peptides form casein and methods for preparing, isolating, and identifying antioxidant peptides |
| EP1275308A1 (en) * | 2001-07-13 | 2003-01-15 | The Procter & Gamble Company | Food composition offering stress relaxation to mammals |
| NL1032322C2 (nl) * | 2006-08-15 | 2008-02-18 | Friesland Brands Bv | Slaapmelk. |
| FR2909879B1 (fr) * | 2006-12-13 | 2009-03-13 | Lorraine Inst Nat Polytech | Utilisation d'un heptapeptide a activite anxiolytique pour la preparation de medicaments et de complements alimentaires |
| FR2932090B1 (fr) * | 2008-06-06 | 2012-09-14 | Lorraine Inst Nat Polytech | Compositions anxiolytiques comprenant des peptides derives de la caseine alpha s1 |
| WO2012103411A2 (en) | 2011-01-28 | 2012-08-02 | Zx Pharma, Llc | Controlled-release melatonin composition and related methods |
| US9532952B2 (en) | 2011-01-28 | 2017-01-03 | Physician's Seal, LLC | Controlled-release compositions of melatonin combined with sedative and/or analgesic ingredients |
| KR20190008265A (ko) | 2016-05-06 | 2019-01-23 | 피지션즈 씰, 엘엘씨 | 발레리안 조성물 및 관련 방법 |
| US10980269B2 (en) * | 2016-12-12 | 2021-04-20 | Mead Johnson Nutrition Company | Protein hydrolysates and methods of making same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208240A (en) * | 1991-03-12 | 1993-05-04 | Merrell Dow Pharmaceuticals Inc. | 8-substituted purines as selective adenosine receptor agents |
| JPH06239888A (ja) * | 1993-02-18 | 1994-08-30 | Kanebo Ltd | 新規ペプチド及び鎮静剤並びに精神安定用食品 |
-
1994
- 1994-11-30 FR FR9414362A patent/FR2727315A1/fr active Granted
-
1995
- 1995-11-27 US US08/562,979 patent/US5846939A/en not_active Expired - Lifetime
- 1995-11-30 EP EP95402697A patent/EP0714910B1/fr not_active Expired - Lifetime
- 1995-11-30 ES ES95402697T patent/ES2135023T3/es not_active Expired - Lifetime
- 1995-11-30 DK DK95402697T patent/DK0714910T3/da active
- 1995-11-30 DE DE69508890T patent/DE69508890T2/de not_active Expired - Lifetime
- 1995-11-30 JP JP31317695A patent/JP3973244B2/ja not_active Expired - Lifetime
- 1995-11-30 SI SI9530273T patent/SI0714910T1/xx unknown
- 1995-11-30 AT AT95402697T patent/ATE178615T1/de active
-
1999
- 1999-06-30 GR GR990401736T patent/GR3030650T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE178615T1 (de) | 1999-04-15 |
| EP0714910A1 (fr) | 1996-06-05 |
| JP3973244B2 (ja) | 2007-09-12 |
| US5846939A (en) | 1998-12-08 |
| GR3030650T3 (en) | 1999-10-29 |
| DE69508890D1 (de) | 1999-05-12 |
| FR2727315B1 (enExample) | 1997-02-14 |
| JPH08268903A (ja) | 1996-10-15 |
| EP0714910B1 (fr) | 1999-04-07 |
| FR2727315A1 (fr) | 1996-05-31 |
| DK0714910T3 (da) | 1999-10-18 |
| ES2135023T3 (es) | 1999-10-16 |
| SI0714910T1 (en) | 1999-10-31 |
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Owner name: INGREDIA, ARRAS, FR |