CA2246306A1 - Use of lipophilic antioxidant compounds to prevent retinoid induced, uva-mediated oxidative reactions - Google Patents
Use of lipophilic antioxidant compounds to prevent retinoid induced, uva-mediated oxidative reactions Download PDFInfo
- Publication number
- CA2246306A1 CA2246306A1 CA002246306A CA2246306A CA2246306A1 CA 2246306 A1 CA2246306 A1 CA 2246306A1 CA 002246306 A CA002246306 A CA 002246306A CA 2246306 A CA2246306 A CA 2246306A CA 2246306 A1 CA2246306 A1 CA 2246306A1
- Authority
- CA
- Canada
- Prior art keywords
- retinoid
- lipid peroxidation
- induced
- skin
- retinoids
- 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.)
- Abandoned
Links
- 150000004492 retinoid derivatives Chemical class 0.000 title claims abstract description 45
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 22
- 230000001404 mediated effect Effects 0.000 title claims abstract description 22
- 230000001590 oxidative effect Effects 0.000 title claims abstract description 19
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 18
- 230000003859 lipid peroxidation Effects 0.000 claims description 72
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 11
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 11
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 11
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 11
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 9
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000003974 emollient agent Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000004530 micro-emulsion Substances 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 38
- 210000004027 cell Anatomy 0.000 description 26
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 25
- 229930002330 retinoic acid Natural products 0.000 description 24
- 210000003491 skin Anatomy 0.000 description 24
- 238000001228 spectrum Methods 0.000 description 24
- 229960001727 tretinoin Drugs 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 17
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 16
- 235000006708 antioxidants Nutrition 0.000 description 15
- 210000002950 fibroblast Anatomy 0.000 description 15
- 230000003595 spectral effect Effects 0.000 description 15
- 238000009826 distribution Methods 0.000 description 13
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 12
- 238000002835 absorbance Methods 0.000 description 11
- 230000001965 increasing effect Effects 0.000 description 10
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 9
- 238000001720 action spectrum Methods 0.000 description 9
- 230000002500 effect on skin Effects 0.000 description 9
- 238000005502 peroxidation Methods 0.000 description 9
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 7
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 7
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 7
- 230000004792 oxidative damage Effects 0.000 description 7
- 235000010323 ascorbic acid Nutrition 0.000 description 6
- 229960005070 ascorbic acid Drugs 0.000 description 6
- 239000011668 ascorbic acid Substances 0.000 description 6
- 230000001419 dependent effect Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 235000020944 retinol Nutrition 0.000 description 6
- 239000011607 retinol Substances 0.000 description 6
- 229960003471 retinol Drugs 0.000 description 6
- 235000019173 retinyl acetate Nutrition 0.000 description 6
- 239000011770 retinyl acetate Substances 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229960000342 retinol acetate Drugs 0.000 description 5
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 238000004113 cell culture Methods 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 229940118019 malondialdehyde Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000037380 skin damage Effects 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 2
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 231100000762 chronic effect Toxicity 0.000 description 2
- 230000002301 combined effect Effects 0.000 description 2
- 210000004748 cultured cell Anatomy 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000678 effect on lipid Effects 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 231100000589 photocarcinogenesis Toxicity 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000003642 reactive oxygen metabolite Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 235000019155 vitamin A Nutrition 0.000 description 2
- 239000011719 vitamin A Substances 0.000 description 2
- 229940045997 vitamin a Drugs 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 102000052812 Ornithine decarboxylases Human genes 0.000 description 1
- 108700005126 Ornithine decarboxylases Proteins 0.000 description 1
- 206010051246 Photodermatosis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 229930003471 Vitamin B2 Natural products 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940100609 all-trans-retinol Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000010630 lipid peroxidation (MDA) assay Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- -1 pantothenic Natural products 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008845 photoaging Effects 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229940108325 retinyl palmitate Drugs 0.000 description 1
- 235000019172 retinyl palmitate Nutrition 0.000 description 1
- 239000011769 retinyl palmitate Substances 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 210000001626 skin fibroblast Anatomy 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 230000005740 tumor formation Effects 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/004—Aftersun preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76278496A | 1996-12-10 | 1996-12-10 | |
| US08/762,784 | 1996-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2246306A1 true CA2246306A1 (en) | 1998-06-18 |
Family
ID=25066031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002246306A Abandoned CA2246306A1 (en) | 1996-12-10 | 1997-12-08 | Use of lipophilic antioxidant compounds to prevent retinoid induced, uva-mediated oxidative reactions |
Country Status (11)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2801790B1 (fr) * | 1999-12-03 | 2002-01-18 | Fabre Pierre Cosmetique | Association retinal et aldehydes, composition cosmetique la contenant, a titre de medicament l'association retinal et aldehydes, et procede de preparation de cette association |
| DE10012151A1 (de) * | 2000-03-13 | 2001-09-27 | Gsf Forschungszentrum Umwelt | Mittel zur Behandlung von Erkrankungen des Tracheo-Brochialtraktes, insbesondere der COPD |
| JP5728152B2 (ja) * | 2008-07-07 | 2015-06-03 | 株式会社ファンケル | 乾燥リポソーム製剤 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3372843D1 (en) * | 1982-05-15 | 1987-09-10 | Beecham Group Plc | Skin treatment compositions |
| JP3280712B2 (ja) * | 1992-07-13 | 2002-05-13 | 株式会社資生堂 | 皮膚外用剤 |
| FR2718021B1 (fr) * | 1994-04-05 | 1996-06-28 | Fabre Pierre Cosmetique | Composition topique à base de rétinal. |
| US6461622B2 (en) * | 1994-09-07 | 2002-10-08 | Johnson & Johnson Consumer Companies, Inc. | Topical compositions |
| US5747010A (en) * | 1996-06-12 | 1998-05-05 | Johnson & Johnson Consumer Products, Inc. | Photoprotective lipophilic antioxidant compounds and their use to prevent UVA-mediated lipid peroxidation |
-
1997
- 1997-12-04 IN IN2285CA1997 patent/IN187969B/en unknown
- 1997-12-08 CN CN97193683A patent/CN1215328A/zh active Pending
- 1997-12-08 WO PCT/US1997/022441 patent/WO1998025587A1/en not_active Application Discontinuation
- 1997-12-08 CA CA002246306A patent/CA2246306A1/en not_active Abandoned
- 1997-12-08 IL IL12570097A patent/IL125700A0/xx unknown
- 1997-12-08 KR KR1019980706143A patent/KR19990082411A/ko not_active Withdrawn
- 1997-12-08 AU AU55188/98A patent/AU5518898A/en not_active Abandoned
- 1997-12-08 JP JP10526847A patent/JP2000505816A/ja active Pending
- 1997-12-08 BR BR9707630A patent/BR9707630A/pt not_active Application Discontinuation
- 1997-12-08 EP EP97951582A patent/EP0914089A1/en not_active Withdrawn
- 1997-12-10 ID IDP973852A patent/ID18520A/id unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0914089A1 (en) | 1999-05-12 |
| JP2000505816A (ja) | 2000-05-16 |
| AU5518898A (en) | 1998-07-03 |
| IN187969B (enrdf_load_stackoverflow) | 2002-08-03 |
| ID18520A (id) | 1998-04-16 |
| IL125700A0 (en) | 1999-04-11 |
| CN1215328A (zh) | 1999-04-28 |
| WO1998025587A1 (en) | 1998-06-18 |
| BR9707630A (pt) | 1999-07-27 |
| KR19990082411A (ko) | 1999-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |