CA2121147C - Synthetic lung surfactant having antioxidant properties - Google Patents
Synthetic lung surfactant having antioxidant properties Download PDFInfo
- Publication number
- CA2121147C CA2121147C CA002121147A CA2121147A CA2121147C CA 2121147 C CA2121147 C CA 2121147C CA 002121147 A CA002121147 A CA 002121147A CA 2121147 A CA2121147 A CA 2121147A CA 2121147 C CA2121147 C CA 2121147C
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- CA
- Canada
- Prior art keywords
- leu
- amino acid
- lys
- group
- glu
- 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.)
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 1
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- SIGOIUCRXKUEIG-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylacetate Chemical compound COC(=O)CP(=O)(OC)OC SIGOIUCRXKUEIG-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- HEGSGKPQLMEBJL-RKQHYHRCSA-N octyl beta-D-glucopyranoside Chemical compound CCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HEGSGKPQLMEBJL-RKQHYHRCSA-N 0.000 description 1
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- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 208000005333 pulmonary edema Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- OTKJDMGTUTTYMP-ZWKOTPCHSA-N sphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO OTKJDMGTUTTYMP-ZWKOTPCHSA-N 0.000 description 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- RLNWRDKVJSXXPP-UHFFFAOYSA-N tert-butyl 2-[(2-bromoanilino)methyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CNC1=CC=CC=C1Br RLNWRDKVJSXXPP-UHFFFAOYSA-N 0.000 description 1
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical group C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 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
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 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
- C07K14/785—Alveolar surfactant peptides; Pulmonary surfactant peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- 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)
- Pulmonology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Gastroenterology & Hepatology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US789,918 | 1991-11-04 | ||
| US07/789,918 US5272252A (en) | 1991-11-04 | 1991-11-04 | Synthetic lung surfactant having antioxidant properties |
| PCT/US1992/008728 WO1993008824A1 (en) | 1991-11-04 | 1992-10-13 | Synthetic lung surfactant having antioxidant properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2121147A1 CA2121147A1 (en) | 1993-05-13 |
| CA2121147C true CA2121147C (en) | 2002-12-10 |
Family
ID=25149105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002121147A Expired - Fee Related CA2121147C (en) | 1991-11-04 | 1992-10-13 | Synthetic lung surfactant having antioxidant properties |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US5272252A (https=) |
| EP (1) | EP0666754B1 (https=) |
| JP (1) | JPH07502500A (https=) |
| KR (1) | KR100250847B1 (https=) |
| AT (1) | ATE175116T1 (https=) |
| AU (1) | AU667200B2 (https=) |
| CA (1) | CA2121147C (https=) |
| DE (1) | DE69228077T2 (https=) |
| DK (1) | DK0666754T3 (https=) |
| ES (1) | ES2127764T3 (https=) |
| FI (1) | FI942032A7 (https=) |
| GR (1) | GR3029279T3 (https=) |
| HU (1) | HUT66424A (https=) |
| NO (1) | NO941616D0 (https=) |
| WO (1) | WO1993008824A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE36460E (en) * | 1990-10-10 | 1999-12-21 | Life Science Holdings, Inc. | Method of providing circulation via lung expansion and deflation |
| US5653685A (en) * | 1990-10-10 | 1997-08-05 | Lrt, Inc. | Method of providing circulation via lung expansion and deflation |
| US5272252A (en) * | 1991-11-04 | 1993-12-21 | Merrell Dow Pharmaceuticals Inc. | Synthetic lung surfactant having antioxidant properties |
| AU664112B2 (en) * | 1992-07-31 | 1995-11-02 | Merrell Dow Pharmaceuticals Inc. | Synthetic peptide lung surfactants having covalently bonded antioxidants |
| DE69620801T2 (de) * | 1995-11-20 | 2002-10-10 | Ortho Mcneil Pharm Inc | Verfahren zur solubisierung des pulmonnären oberflächeraktiven peptides |
| EP0910423A4 (en) * | 1996-03-08 | 1999-12-29 | Life Resuscitation Tech | LIQUID VENTILATION METHOD AND DEVICE |
| WO2002006301A2 (en) * | 2000-06-30 | 2002-01-24 | University Of Cincinnati | Peptides with antioxidant and antimicrobial properties |
| GB2368339B (en) | 2000-10-26 | 2002-09-18 | Yissum Res Dev Co | Complex incorporating a plurality of antioxidants |
| AU2002357168A1 (en) * | 2001-12-12 | 2003-07-09 | Penn State Research Foundation | Surfactant prevention of lung complications from cancer chemotherapy |
| AU2003223718B2 (en) * | 2002-04-25 | 2007-08-16 | The Scripps Research Institute | Treatment and prevention of pulmonary conditions |
| US7290197B2 (en) * | 2003-06-03 | 2007-10-30 | Quantum Corporation | Correcting data using redundancy blocks |
| EP1809272A4 (en) * | 2004-10-18 | 2008-01-02 | Maroon Biotech Corp | METHOD AND COMPOSITIONS FOR TREATING DAMAGES THROUGH FREE RADICALS |
| US7582312B2 (en) * | 2004-11-15 | 2009-09-01 | Discovery Laboratories, Inc. | Methods to produce lung surfactant formulations via lyophilization and formulations and uses thereof |
| US7464012B2 (en) * | 2004-12-10 | 2008-12-09 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Simplified process simulator |
| SI1841458T1 (sl) | 2005-01-06 | 2012-04-30 | Discovery Lab Inc | Zdravljenje s predpisanim odmerjanjem surfaktanta za zdravljenje ali preprečevanje bronhopulmonalne displazije |
| JPWO2007001094A1 (ja) * | 2005-06-29 | 2009-01-22 | 相男 李 | 人工肺サーファクタント組成物 |
| EP2063903A1 (en) * | 2006-09-19 | 2009-06-03 | Discovery Laboratories, Inc. | Pulmonary surfactant formulations and methods for promoting mucus clearance |
| WO2013188016A2 (en) | 2012-05-04 | 2013-12-19 | Discovery Laboratories, Inc. | Surfactant therapy for exposure to ionizing radiation |
| KR102221365B1 (ko) * | 2019-05-07 | 2021-03-02 | (주)케어젠 | 트롤록스-펩타이드 결합체 및 그의 용도 |
| CN111568853B (zh) * | 2020-04-30 | 2023-07-28 | 杭州濡湜生物科技有限公司 | 一种新型肺部智能释药系统 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4643988A (en) * | 1984-05-15 | 1987-02-17 | Research Corporation | Amphipathic peptides |
| US4933280A (en) * | 1984-12-11 | 1990-06-12 | California Biotechnology Inc. | Recombinant DNA sequence encoding Alveolar Surfactant Protein |
| US4912038A (en) * | 1984-12-11 | 1990-03-27 | California Biotechnology Inc. | Recombinant DNA sequence encoding alveolar surfactant protein |
| US5104853A (en) * | 1984-12-11 | 1992-04-14 | California Biotechnology Inc. | Alveolar surfactant proteins having cys to ser mutations |
| US4659805A (en) * | 1984-12-11 | 1987-04-21 | California Biotechnology, Inc. | Recombinant alveolar surfactant protein |
| US4705684A (en) * | 1985-05-31 | 1987-11-10 | The University Of Tennessee Research Corporation | Synthetic M proteins - streptococci type 6 |
| FR2586587B1 (fr) * | 1985-08-30 | 1987-10-23 | Adir | Nouveaux surfactants artificiels, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| US4918161A (en) * | 1985-09-26 | 1990-04-17 | Genetics Institute, Inc. | Low molecular weight pulmonary surfactant proteins |
| US5055553A (en) * | 1985-09-26 | 1991-10-08 | Genetics Institute Inc. | Low molecular weight pulmonary surfactant proteins |
| US4882422A (en) * | 1985-10-24 | 1989-11-21 | Genetics Institute, Inc. | Pulmonary surfactant proteins |
| WO1987006943A1 (en) * | 1986-05-06 | 1987-11-19 | Children's Hospital Medical Center | Pulmonary hydrophobic surfactant-associated protein of 6,000 daltons molecular weight and multimers thereof |
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| JPH01501282A (ja) * | 1986-12-08 | 1989-05-11 | ホイツトセツト，ジエフリー エイ． | 肺胞疎水性界面活性物質関連タンパク質 |
| WO1989000167A1 (en) * | 1987-07-01 | 1989-01-12 | Kabigen Ab | Proteins and protein compositions and their use |
| ATE163013T1 (de) * | 1987-11-04 | 1998-02-15 | Byk Gulden Lomberg Chem Fab | Alveolare oberflächenaktive proteine |
| US5164369A (en) * | 1988-01-06 | 1992-11-17 | The Scripps Research Institute | Pulmonary surfactant protein and related polypeptide |
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| SE8803713D0 (sv) * | 1988-10-18 | 1988-10-18 | Kabigen Ab | Biologically active lipoprotein and its use |
| US5006343A (en) * | 1988-12-29 | 1991-04-09 | Benson Bradley J | Pulmonary administration of pharmaceutically active substances |
| US5134129A (en) * | 1989-03-15 | 1992-07-28 | Board Of Regents, The University Of Texas System | Methods employing unique mixtures of polar and neutral lipids for surfactant replacement therapy |
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| DE69125750D1 (de) * | 1990-05-21 | 1997-05-28 | Abbott Lab | Fettsäure-Oberflächenaktives-Lungenprotein Konjate |
| US5272252A (en) * | 1991-11-04 | 1993-12-21 | Merrell Dow Pharmaceuticals Inc. | Synthetic lung surfactant having antioxidant properties |
-
1991
- 1991-11-04 US US07/789,918 patent/US5272252A/en not_active Expired - Fee Related
-
1992
- 1992-10-13 FI FI942032A patent/FI942032A7/fi unknown
- 1992-10-13 EP EP92921892A patent/EP0666754B1/en not_active Expired - Lifetime
- 1992-10-13 AT AT92921892T patent/ATE175116T1/de not_active IP Right Cessation
- 1992-10-13 DE DE69228077T patent/DE69228077T2/de not_active Expired - Fee Related
- 1992-10-13 AU AU27783/92A patent/AU667200B2/en not_active Ceased
- 1992-10-13 CA CA002121147A patent/CA2121147C/en not_active Expired - Fee Related
- 1992-10-13 DK DK92921892T patent/DK0666754T3/da active
- 1992-10-13 HU HU9401293A patent/HUT66424A/hu unknown
- 1992-10-13 WO PCT/US1992/008728 patent/WO1993008824A1/en not_active Ceased
- 1992-10-13 KR KR1019940701486A patent/KR100250847B1/ko not_active Expired - Fee Related
- 1992-10-13 JP JP5508432A patent/JPH07502500A/ja not_active Ceased
- 1992-10-13 ES ES92921892T patent/ES2127764T3/es not_active Expired - Lifetime
-
1994
- 1994-05-03 NO NO941616A patent/NO941616D0/no not_active Application Discontinuation
-
1995
- 1995-05-25 US US08/450,427 patent/US5683982A/en not_active Expired - Fee Related
-
1999
- 1999-02-03 GR GR990400359T patent/GR3029279T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1993008824A1 (en) | 1993-05-13 |
| CA2121147A1 (en) | 1993-05-13 |
| EP0666754A1 (en) | 1995-08-16 |
| HUT66424A (en) | 1994-11-28 |
| KR100250847B1 (ko) | 2000-09-01 |
| FI942032L (fi) | 1994-05-03 |
| US5272252A (en) | 1993-12-21 |
| DE69228077T2 (de) | 1999-07-08 |
| US5683982A (en) | 1997-11-04 |
| NO941616L (https=) | 1994-06-24 |
| DK0666754T3 (da) | 1999-08-30 |
| ES2127764T3 (es) | 1999-05-01 |
| ATE175116T1 (de) | 1999-01-15 |
| FI942032A0 (fi) | 1994-05-03 |
| HU9401293D0 (en) | 1994-08-29 |
| EP0666754B1 (en) | 1998-12-30 |
| GR3029279T3 (en) | 1999-05-28 |
| DE69228077D1 (de) | 1999-02-11 |
| EP0666754A4 (en) | 1996-06-26 |
| AU2778392A (en) | 1993-06-07 |
| FI942032A7 (fi) | 1994-05-03 |
| AU667200B2 (en) | 1996-03-14 |
| NO941616D0 (no) | 1994-05-03 |
| JPH07502500A (ja) | 1995-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20051013 |