CA1302253C - Use of tin protoporphyrin and tin mesoporphyrin in the treatment of psoriasis - Google Patents
Use of tin protoporphyrin and tin mesoporphyrin in the treatment of psoriasisInfo
- Publication number
- CA1302253C CA1302253C CA000553714A CA553714A CA1302253C CA 1302253 C CA1302253 C CA 1302253C CA 000553714 A CA000553714 A CA 000553714A CA 553714 A CA553714 A CA 553714A CA 1302253 C CA1302253 C CA 1302253C
- Authority
- CA
- Canada
- Prior art keywords
- tin
- treatment
- psoriasis
- protoporphyrin
- mesoporphyrin
- 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
- 238000011282 treatment Methods 0.000 title claims abstract description 29
- 201000004681 Psoriasis Diseases 0.000 title claims abstract description 21
- LLDZJTIZVZFNCM-UHFFFAOYSA-J 3-[18-(2-carboxyethyl)-8,13-diethyl-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid;dichlorotin(2+) Chemical compound [H+].[H+].[Cl-].[Cl-].[Sn+4].[N-]1C(C=C2C(=C(C)C(=CC=3C(=C(C)C(=C4)N=3)CC)[N-]2)CCC([O-])=O)=C(CCC([O-])=O)C(C)=C1C=C1C(C)=C(CC)C4=N1 LLDZJTIZVZFNCM-UHFFFAOYSA-J 0.000 title claims abstract description 18
- 229950003776 protoporphyrin Drugs 0.000 title claims abstract description 15
- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 title claims abstract description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 8
- 230000002682 anti-psoriatic effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 206010015150 Erythema Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 231100000321 erythema Toxicity 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 208000003251 Pruritus Diseases 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 4
- 229960002311 dithranol Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 229960000485 methotrexate Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 description 2
- 241000101040 Pityriasis Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241001303601 Rosacea Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 210000003128 head Anatomy 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 230000007803 itching Effects 0.000 description 2
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
- 229960003730 methylcellulose (4000 cps) Drugs 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 230000001185 psoriatic effect Effects 0.000 description 2
- 201000004700 rosacea Diseases 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- 206010000349 Acanthosis Diseases 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 241001518643 Erythrodermis Species 0.000 description 1
- 208000035874 Excoriation Diseases 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 206010053240 Glycogen storage disease type VI Diseases 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010062049 Lymphocytic infiltration Diseases 0.000 description 1
- 208000005775 Parakeratosis Diseases 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000027119 bilirubin metabolic disease Diseases 0.000 description 1
- 238000010876 biochemical test Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- VJBCBLLQDMITLJ-UHFFFAOYSA-N chromen-7-one Chemical compound C1=COC2=CC(=O)C=CC2=C1 VJBCBLLQDMITLJ-UHFFFAOYSA-N 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 208000036796 hyperbilirubinemia Diseases 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000002559 palpation Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93882286A | 1986-12-08 | 1986-12-08 | |
| US938,822 | 1986-12-08 | ||
| US07/125,011 US4782049A (en) | 1986-12-08 | 1987-12-02 | Tin protoporphyrin and tin mesoporphyrin in the treatment of psoriasis |
| US125,011 | 1987-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1302253C true CA1302253C (en) | 1992-06-02 |
Family
ID=26823181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000553714A Expired - Lifetime CA1302253C (en) | 1986-12-08 | 1987-12-07 | Use of tin protoporphyrin and tin mesoporphyrin in the treatment of psoriasis |
Country Status (12)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0333831B1 (en) * | 1987-09-08 | 1992-07-15 | The Rockefeller University | Use of metalloporphyrins to reverse the toxic effect of tumor therapy |
| GR1000182B (el) * | 1988-03-28 | 1992-01-20 | Univ Rockefeller | Χρησιμοποιηση πρωτοπορφυρινης κασσιτερου και μεσοπορφυρινης κασσιτερου στην παρασευη φαρμακευτικων συνθεσεων για την αγωγη της ψωριασης. |
| US4997828A (en) * | 1989-02-14 | 1991-03-05 | The Rockefeller University | Method of weight control by low level administration of cobalt protoporphyrin or cobalt mesoporphyrin |
| US5192757A (en) * | 1990-12-20 | 1993-03-09 | Glaxo Inc. | Cobalt porphyrins |
| US5149697A (en) * | 1991-04-18 | 1992-09-22 | Glaxo Inc. | Cobalt porphyrin pharmaceutical compositions |
| WO1995017893A1 (en) * | 1993-12-28 | 1995-07-06 | New York Blood Center | Methods for preventing or treating hiv-1 or hiv-2 infection |
| TW247876B (en) | 1993-12-28 | 1995-05-21 | New York Blood Ct Inc | Pharmaceutical compositions for prevention or treating HIV-1 or HIV-2 infection |
| EP0765161A2 (en) * | 1994-06-02 | 1997-04-02 | Bar-Ilan University | Synergistic antibiotic compositions containing a perphyrin and an antibiotic |
| FR2727862B1 (fr) * | 1994-12-07 | 1997-03-28 | Holzmann Stephane | Produits cosmetiques et/ou d'hygiene corporelle et/ou dermatologiques constitues d'une phase aqueuse isotonique et/ou d'une phase aqueuse osmotique |
| US5929064A (en) * | 1995-08-02 | 1999-07-27 | Warner-Lambert Company | Amino acid complexes of cobalt (III) mesoporphyrin IX and cobalt (III) protoporphyrin IX |
| US7375216B2 (en) * | 2002-06-04 | 2008-05-20 | Infacare Pharmaceutical Corporation | Preparation of metal mesoporphyrin compounds |
| AU2003237349B2 (en) | 2002-06-04 | 2010-06-03 | Infacare Pharmaceutical Corporation | Preparation of metal mesoporphyrin halide compounds |
| US20040097481A1 (en) * | 2002-11-20 | 2004-05-20 | Benjamin Levinson | Water-soluble mesoporphyrin compounds and methods of preparation |
| US20060222668A1 (en) * | 2005-04-01 | 2006-10-05 | Wellspring Pharmaceutical Corporation | Stannsoporfin compositions, drug products and methods of manufacture |
| PT2079472E (pt) * | 2006-10-04 | 2011-11-24 | Infacare Pharmaceutical Corp | Preparação em larga escala de estansoporfina de alta pureza |
| ES2609110T3 (es) | 2011-03-30 | 2017-04-18 | Infacare Pharmaceutical Corporation | Procedimientos de síntesis de mesoporfirinas metálicas |
| AU2015324103C1 (en) | 2014-09-29 | 2020-08-20 | Fred Hutchinson Cancer Center | Compositions, kits, and methods to induce acquired cytoresistance using stress protein inducers |
| CA3225692A1 (en) * | 2021-07-12 | 2023-01-19 | Donald Jeffrey Keyser | Metal protoporphyrin for treatment of bk virus |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4454152A (en) * | 1980-05-07 | 1984-06-12 | Hoffmann-La Roche Inc. | Methoxsalen dosage forms |
| US4657902A (en) * | 1985-03-25 | 1987-04-14 | The Rockefeller University | Therapeutic use of tin mesoporphyrin |
| US4692439A (en) * | 1986-06-20 | 1987-09-08 | The Rockefeller University | Therapeutic use of tin diiododeuteroporphyrin |
-
1987
- 1987-12-02 US US07/125,011 patent/US4782049A/en not_active Expired - Lifetime
- 1987-12-07 AT AT88900434T patent/ATE63815T1/de not_active IP Right Cessation
- 1987-12-07 DE DE8888900434T patent/DE3770465D1/de not_active Expired - Lifetime
- 1987-12-07 EP EP88900434A patent/EP0295280B1/en not_active Expired - Lifetime
- 1987-12-07 KR KR1019880700932A patent/KR920002330B1/ko not_active Expired
- 1987-12-07 JP JP63500719A patent/JPH01501627A/ja active Granted
- 1987-12-07 AU AU10812/88A patent/AU597144B2/en not_active Ceased
- 1987-12-07 CA CA000553714A patent/CA1302253C/en not_active Expired - Lifetime
- 1987-12-07 WO PCT/US1987/003248 patent/WO1988004174A1/en active IP Right Grant
- 1987-12-08 IE IE332387A patent/IE63507B1/en not_active IP Right Cessation
- 1987-12-08 PH PH36181A patent/PH25224A/en unknown
-
1988
- 1988-08-08 DK DK443088A patent/DK443088A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK443088D0 (da) | 1988-08-08 |
| EP0295280A1 (en) | 1988-12-21 |
| AU1081288A (en) | 1988-06-30 |
| IE873323L (en) | 1988-06-08 |
| IE63507B1 (en) | 1995-05-03 |
| EP0295280A4 (en) | 1989-02-21 |
| US4782049A (en) | 1988-11-01 |
| JPH0585523B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-12-07 |
| EP0295280B1 (en) | 1991-05-29 |
| DE3770465D1 (de) | 1991-07-04 |
| ATE63815T1 (de) | 1991-06-15 |
| KR890700026A (ko) | 1989-03-02 |
| WO1988004174A1 (en) | 1988-06-16 |
| JPH01501627A (ja) | 1989-06-08 |
| DK443088A (da) | 1988-08-08 |
| AU597144B2 (en) | 1990-05-24 |
| PH25224A (en) | 1991-03-27 |
| KR920002330B1 (ko) | 1992-03-21 |
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