DE69433763T2 - Lineare und cyklische peptide zur behandlung oder verhinderung von ekzem und dermatitis - Google Patents
Lineare und cyklische peptide zur behandlung oder verhinderung von ekzem und dermatitis Download PDFInfo
- Publication number
- DE69433763T2 DE69433763T2 DE69433763T DE69433763T DE69433763T2 DE 69433763 T2 DE69433763 T2 DE 69433763T2 DE 69433763 T DE69433763 T DE 69433763T DE 69433763 T DE69433763 T DE 69433763T DE 69433763 T2 DE69433763 T2 DE 69433763T2
- Authority
- DE
- Germany
- Prior art keywords
- thr
- ser
- tyr
- asn
- absent
- 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
- 201000004624 Dermatitis Diseases 0.000 title claims description 26
- 238000011282 treatment Methods 0.000 title claims description 19
- 102000001189 Cyclic Peptides Human genes 0.000 title claims description 5
- 108010069514 Cyclic Peptides Proteins 0.000 title claims description 5
- 230000002265 prevention Effects 0.000 title claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 36
- 208000010668 atopic eczema Diseases 0.000 claims description 25
- 150000001413 amino acids Chemical class 0.000 claims description 16
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000539 amino acid group Chemical group 0.000 claims description 5
- AKWRNBWMGFUAMF-ZESMOPTKSA-N (2s)-n-[(2s)-1-[[(2s,3r)-1-amino-3-hydroxy-1-oxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-2-[[(2s,3r)-2-[[(2s,3r)-2-[[(2s,3r)-2-[[(2s)-2-[[(2r)-2-aminopropanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amin Chemical compound C[C@@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@H](O)C)C(N)=O)CC1=CC=C(O)C=C1 AKWRNBWMGFUAMF-ZESMOPTKSA-N 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- IWHCAJPPWOMXNW-LYKMMFCUSA-N peptide t Chemical compound C[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@H](O)C)C(O)=O)CC1=CC=C(O)C=C1 IWHCAJPPWOMXNW-LYKMMFCUSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- IWHCAJPPWOMXNW-ZESMOPTKSA-N (2s,3r)-2-[[(2s)-2-[[(2s)-4-amino-2-[[(2s,3r)-2-[[(2s,3r)-2-[[(2s,3r)-2-[[(2s)-2-[[(2r)-2-aminopropanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]-3-(4-hydroxyphenyl)pr Chemical compound C[C@@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@H](O)C)C(O)=O)CC1=CC=C(O)C=C1 IWHCAJPPWOMXNW-ZESMOPTKSA-N 0.000 claims description 3
- KVPFYRAFNZKJSD-CPXLMRBJSA-N (2s,3r)-2-[[(2s)-2-[[(2s)-4-amino-2-[[(2s,3r)-2-[[(2s,3r)-2-amino-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)O)C(O)=O)CC1=CC=C(O)C=C1 KVPFYRAFNZKJSD-CPXLMRBJSA-N 0.000 claims description 3
- -1 Thr amide Chemical class 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
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- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000393 L-methionino group Chemical group [H]OC(=O)[C@@]([H])(N([H])[*])C([H])([H])C(SC([H])([H])[H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 17
- 108010071384 Peptide T Proteins 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- 210000003491 skin Anatomy 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000007921 spray Substances 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 206010012438 Dermatitis atopic Diseases 0.000 description 4
- 125000003275 alpha amino acid group Chemical group 0.000 description 4
- 201000008937 atopic dermatitis Diseases 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000729 N-terminal amino-acid group Chemical group 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- 210000001015 abdomen Anatomy 0.000 description 2
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- 208000002352 blister Diseases 0.000 description 2
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- 229960001334 corticosteroids Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 208000021267 infertility disease Diseases 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000007803 itching Effects 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YYSWCHMLFJLLBJ-ZLUOBGJFSA-N Ala-Ala-Ser Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(O)=O YYSWCHMLFJLLBJ-ZLUOBGJFSA-N 0.000 description 1
- 102000004400 Aminopeptidases Human genes 0.000 description 1
- 108090000915 Aminopeptidases Proteins 0.000 description 1
- 102000005367 Carboxypeptidases Human genes 0.000 description 1
- 108010006303 Carboxypeptidases Proteins 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- AYFVYJQAPQTCCC-STHAYSLISA-N D-threonine Chemical compound C[C@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-STHAYSLISA-N 0.000 description 1
- DEFJQIDDEAULHB-IMJSIDKUSA-N L-alanyl-L-alanine Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(O)=O DEFJQIDDEAULHB-IMJSIDKUSA-N 0.000 description 1
- WLJPJRGQRNCIQS-ZLUOBGJFSA-N Ser-Ser-Asn Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(O)=O WLJPJRGQRNCIQS-ZLUOBGJFSA-N 0.000 description 1
- 206010040844 Skin exfoliation Diseases 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
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- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
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- 238000013329 compounding Methods 0.000 description 1
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- 230000037430 deletion Effects 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical class CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000001513 elbow Anatomy 0.000 description 1
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- 210000003414 extremity Anatomy 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
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- 238000012261 overproduction Methods 0.000 description 1
- 238000002638 palliative care Methods 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 239000007929 subcutaneous injection Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/005—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from viruses
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16111—Human Immunodeficiency Virus, HIV concerning HIV env
- C12N2740/16122—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes
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)
- Proteomics, Peptides & Aminoacids (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Gastroenterology & Hepatology (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPM144993 | 1993-09-24 | ||
| AUPM144993 | 1993-09-24 | ||
| PCT/AU1994/000574 WO1995008338A1 (en) | 1993-09-24 | 1994-09-26 | Method for the treatment or prevention of eczema/dermatitis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69433763D1 DE69433763D1 (de) | 2004-06-09 |
| DE69433763T2 true DE69433763T2 (de) | 2005-04-14 |
Family
ID=3777229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69433763T Expired - Fee Related DE69433763T2 (de) | 1993-09-24 | 1994-09-26 | Lineare und cyklische peptide zur behandlung oder verhinderung von ekzem und dermatitis |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5798335A (https=) |
| EP (1) | EP0871466B1 (https=) |
| JP (1) | JP3623231B2 (https=) |
| AU (1) | AU697847B2 (https=) |
| CA (1) | CA2172491A1 (https=) |
| DE (1) | DE69433763T2 (https=) |
| DK (1) | DK0871466T3 (https=) |
| ES (1) | ES2218528T3 (https=) |
| WO (1) | WO1995008338A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025123114A1 (pt) * | 2023-12-15 | 2025-06-19 | Chemyunion Ltda | Composição cosmética, cosmecêutica e/ou farmacêutica, usos e métodos |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4689398A (en) * | 1984-06-20 | 1987-08-25 | Ortho Diagnostic Systems Inc. | HTLV test using synthetic peptides |
| US6242564B1 (en) * | 1986-06-03 | 2001-06-05 | Candace B. Pert | Treatment of tropical spastic paresis with peptide T |
| US5189022A (en) * | 1988-05-27 | 1993-02-23 | The United States Of America As Represented By The Secretary Of Health And Human Services | Composition for the treatment of chronic fatigue syndrome |
| US5063206A (en) * | 1988-12-16 | 1991-11-05 | The United States Of Americas As Represented By The Department Of Health And Human Services | Compositions having use as treatment of neuropsychiatric deficits |
| WO1989012067A1 (en) * | 1988-05-27 | 1989-12-14 | The United States Of America, As Represented By Th | Compositions having use as treatment of psoriasis and neuropsychiatric deficits |
| DK31991D0 (da) * | 1991-02-25 | 1991-02-25 | Carlbiotech Ltd As | Peptid og farmaceutisk praeparat indeholdende et saadant peptid |
| ATE194495T1 (de) * | 1992-03-27 | 2000-07-15 | Advanced Immunit T Inc | T-peptid und damit verwandte peptide in der behandlung von entzündungen einschliesslich der multiplen sklerose |
| US5651993A (en) * | 1992-11-18 | 1997-07-29 | Yale University | Specific immune system modulation |
-
1994
- 1994-09-26 DE DE69433763T patent/DE69433763T2/de not_active Expired - Fee Related
- 1994-09-26 DK DK94928213T patent/DK0871466T3/da active
- 1994-09-26 CA CA002172491A patent/CA2172491A1/en not_active Abandoned
- 1994-09-26 ES ES94928213T patent/ES2218528T3/es not_active Expired - Lifetime
- 1994-09-26 EP EP94928213A patent/EP0871466B1/en not_active Expired - Lifetime
- 1994-09-26 US US08/619,462 patent/US5798335A/en not_active Expired - Fee Related
- 1994-09-26 AU AU77350/94A patent/AU697847B2/en not_active Ceased
- 1994-09-26 WO PCT/AU1994/000574 patent/WO1995008338A1/en not_active Ceased
- 1994-09-26 JP JP50944495A patent/JP3623231B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0871466A1 (en) | 1998-10-21 |
| EP0871466B1 (en) | 2004-05-06 |
| JP3623231B2 (ja) | 2005-02-23 |
| EP0871466A4 (https=) | 1998-11-11 |
| AU7735094A (en) | 1995-04-10 |
| WO1995008338A1 (en) | 1995-03-30 |
| ES2218528T3 (es) | 2004-11-16 |
| AU697847B2 (en) | 1998-10-15 |
| US5798335A (en) | 1998-08-25 |
| JPH09506860A (ja) | 1997-07-08 |
| CA2172491A1 (en) | 1995-03-30 |
| DE69433763D1 (de) | 2004-06-09 |
| DK0871466T3 (da) | 2004-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |