AU750197B2 - Mixed micellar pharmaceutical delivery system and method of preparation - Google Patents
Mixed micellar pharmaceutical delivery system and method of preparation Download PDFInfo
- Publication number
- AU750197B2 AU750197B2 AU25053/99A AU2505399A AU750197B2 AU 750197 B2 AU750197 B2 AU 750197B2 AU 25053/99 A AU25053/99 A AU 25053/99A AU 2505399 A AU2505399 A AU 2505399A AU 750197 B2 AU750197 B2 AU 750197B2
- Authority
- AU
- Australia
- Prior art keywords
- formulation
- concentration
- acid
- insulin
- absorption enhancing
- 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.)
- Revoked
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 197
- 238000009472 formulation Methods 0.000 claims abstract description 139
- -1 alkali metal salicylate Chemical class 0.000 claims abstract description 70
- 238000010521 absorption reaction Methods 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 58
- 230000002708 enhancing effect Effects 0.000 claims abstract description 56
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims abstract description 49
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 38
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229940009662 edetate Drugs 0.000 claims abstract description 38
- 239000000787 lecithin Substances 0.000 claims abstract description 38
- 235000010445 lecithin Nutrition 0.000 claims abstract description 38
- 229940067606 lecithin Drugs 0.000 claims abstract description 38
- 239000008177 pharmaceutical agent Substances 0.000 claims abstract description 36
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims abstract description 35
- 229920002674 hyaluronan Polymers 0.000 claims abstract description 35
- 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 35
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 20
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 20
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000005642 Oleic acid Substances 0.000 claims abstract description 20
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 20
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 20
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- 229910021653 sulphate ion Inorganic materials 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 240000008067 Cucumis sativus Species 0.000 claims abstract description 12
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- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims abstract description 12
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 12
- 235000020221 chamomile extract Nutrition 0.000 claims abstract description 12
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- 239000000284 extract Substances 0.000 claims abstract description 12
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- 229920000656 polylysine Polymers 0.000 claims abstract description 12
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims abstract description 12
- 229940117972 triolein Drugs 0.000 claims abstract description 12
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims abstract description 11
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- 235000021313 oleic acid Nutrition 0.000 claims abstract description 10
- 235000019198 oils Nutrition 0.000 claims abstract description 5
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 190
- 102000004877 Insulin Human genes 0.000 claims description 100
- 108090001061 Insulin Proteins 0.000 claims description 100
- 229940125396 insulin Drugs 0.000 claims description 95
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical group [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 claims description 42
- 229960004025 sodium salicylate Drugs 0.000 claims description 42
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical group [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 35
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 35
- 239000004141 Sodium laurylsulphate Substances 0.000 claims description 34
- 229920002385 Sodium hyaluronate Polymers 0.000 claims description 33
- 229940010747 sodium hyaluronate Drugs 0.000 claims description 33
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 claims description 32
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- 108090000623 proteins and genes Proteins 0.000 claims description 21
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- 229960002969 oleic acid Drugs 0.000 claims description 19
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 claims description 16
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- 235000008524 evening primrose extract Nutrition 0.000 claims description 15
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- 150000002605 large molecules Chemical class 0.000 claims description 15
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- 238000002156 mixing Methods 0.000 claims description 14
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 12
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- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 8
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Landscapes
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- Otolaryngology (AREA)
- Neurology (AREA)
- Anesthesiology (AREA)
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- Proteomics, Peptides & Aminoacids (AREA)
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Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU68143/00A AU763251B2 (en) | 1998-02-10 | 2000-08-25 | Mixed micellar pharmaceutical delivery system and method for preparation |
| AU2002301424A AU2002301424B2 (en) | 1998-02-10 | 2002-10-10 | Mixed micellar pharmaceutical delivery system and method of preparation |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/021,114 US6017545A (en) | 1998-02-10 | 1998-02-10 | Mixed micellar delivery system and method of preparation |
| US09/021114 | 1998-02-10 | ||
| US09/216,733 US6231882B1 (en) | 1998-02-10 | 1998-12-21 | Mixed micellar delivery system and method of preparation |
| US09/216733 | 1998-12-21 | ||
| PCT/CA1999/000106 WO1999040932A1 (en) | 1998-02-10 | 1999-02-05 | Mixed micellar pharmaceutical delivery system and method of preparation |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
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| AU68143/00A Division AU763251B2 (en) | 1998-02-10 | 2000-08-25 | Mixed micellar pharmaceutical delivery system and method for preparation |
| AU2002301424A Division AU2002301424B2 (en) | 1998-02-10 | 2002-10-10 | Mixed micellar pharmaceutical delivery system and method of preparation |
Publications (2)
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|---|---|
| AU2505399A AU2505399A (en) | 1999-08-30 |
| AU750197B2 true AU750197B2 (en) | 2002-07-11 |
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| AU25053/99A Revoked AU750197B2 (en) | 1998-02-10 | 1999-02-05 | Mixed micellar pharmaceutical delivery system and method of preparation |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US6017545A (https=) |
| EP (1) | EP1053011B1 (https=) |
| JP (1) | JP4499282B2 (https=) |
| AT (1) | ATE378062T1 (https=) |
| AU (1) | AU750197B2 (https=) |
| BR (1) | BR9804295A (https=) |
| DE (1) | DE69937546T2 (https=) |
| DK (1) | DK1053011T3 (https=) |
| ES (1) | ES2296380T3 (https=) |
| NZ (1) | NZ506024A (https=) |
| PT (1) | PT1053011E (https=) |
| WO (1) | WO1999040932A1 (https=) |
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2686899B1 (fr) * | 1992-01-31 | 1995-09-01 | Rhone Poulenc Rorer Sa | Nouveaux polypeptides biologiquement actifs, leur preparation et compositions pharmaceutiques les contenant. |
| US6017545A (en) * | 1998-02-10 | 2000-01-25 | Modi; Pankaj | Mixed micellar delivery system and method of preparation |
| US6350458B1 (en) | 1998-02-10 | 2002-02-26 | Generex Pharmaceuticals Incorporated | Mixed micellar drug deliver system and method of preparation |
| AU763251B2 (en) * | 1998-02-10 | 2003-07-17 | Generex Pharmaceuticals Inc. | Mixed micellar pharmaceutical delivery system and method for preparation |
| US6221378B1 (en) * | 1998-02-10 | 2001-04-24 | Generex Pharmaceuticals Incorporated | Mixed micellar delivery system and method of preparation |
| US7070799B1 (en) * | 1998-02-10 | 2006-07-04 | Generex Pharmaceuticals, Inc. | Method for administering insulin to the buccal region |
| US6193997B1 (en) * | 1998-09-27 | 2001-02-27 | Generex Pharmaceuticals Inc. | Proteinic drug delivery system using membrane mimetics |
| US6290987B1 (en) * | 1998-09-27 | 2001-09-18 | Generex Pharmaceuticals, Inc. | Mixed liposome pharmaceutical formulation with amphiphiles and phospholipids |
| US6635617B1 (en) * | 1998-10-16 | 2003-10-21 | Novo Nordisk A/S | Insulin preparations for pulmonary delivery containing menthol |
| EP1338272A1 (en) * | 1998-12-21 | 2003-08-27 | Generex Pharmaceuticals Inc. | Aerosol formulations for buccal and pulmonary application comprising chenodeoxycholate or deoxycholate |
| US6271200B1 (en) * | 1998-12-21 | 2001-08-07 | Generex Pharmaceuticals Inc. | Proteinic drug delivery system using aerosolized membrane-mimetic amphiphiles |
| US6375975B1 (en) * | 1998-12-21 | 2002-04-23 | Generex Pharmaceuticals Incorporated | Pharmaceutical compositions for buccal and pulmonary application |
| US7087215B2 (en) * | 1998-12-21 | 2006-08-08 | Generex Pharmaceuticals Incorporated | Methods of administering and enhancing absorption of pharmaceutical agents |
| US6451286B1 (en) * | 1998-12-21 | 2002-09-17 | Generex Pharmaceuticals Incorporated | Pharmaceutical compositions for buccal and pulmonary administration comprising an alkali metal alkyl sulfate and at least three micelle-forming compounds |
| US6312665B1 (en) * | 1998-12-21 | 2001-11-06 | Generex Pharmaceuticals Incorporated | Aerosol formulations for buccal and pulmonary application |
| AU2006200276B2 (en) * | 1998-12-21 | 2007-11-29 | Generex Pharmaceuticals Inc. | Micellar pharmaceutical compositions for buccal and pulmonary application |
| US6294153B1 (en) * | 1998-12-21 | 2001-09-25 | Generex Pharmaceuticals, Inc. | Aerosol pharmaceutical formulation for pulmonary and nasal delivery |
| US6436367B1 (en) * | 1998-12-21 | 2002-08-20 | Generex Pharmaceuticals Inc. | Aerosol formulations for buccal and pulmonary application |
| US6849263B2 (en) * | 1998-12-21 | 2005-02-01 | Generex Pharmaceutical Incorporated | Pharmaceutical compositions for buccal delivery of pain relief medications |
| US20040258763A1 (en) * | 1999-02-03 | 2004-12-23 | Bell Steve J.D. | Methods of manufacture and use of calcium phosphate particles containing allergens |
| CA2361421A1 (en) | 1999-02-03 | 2000-08-10 | Biosante Pharmaceuticals, Inc. | Therapeutic calcium phosphate particles and methods of manufacture and use |
| US20020054914A1 (en) * | 1999-02-03 | 2002-05-09 | Tulin Morcol | Compositions and methods for therapuetic agents complexed with calcium phosphate and encased by casein |
| US7258869B1 (en) | 1999-02-08 | 2007-08-21 | Alza Corporation | Stable non-aqueous single phase viscous vehicles and formulations utilizing such vehicle |
| US7919109B2 (en) | 1999-02-08 | 2011-04-05 | Intarcia Therapeutics, Inc. | Stable non-aqueous single phase viscous vehicles and formulations utilizing such vehicles |
| NZ514319A (en) * | 1999-03-19 | 2002-11-26 | Generex Pharm Inc | Proteinic pharmaceutical agent solubilized in aerosol propellant in a pressurized container |
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- 1998-10-27 BR BR9804295-5A patent/BR9804295A/pt not_active IP Right Cessation
- 1998-12-21 US US09/216,733 patent/US6231882B1/en not_active Expired - Fee Related
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1999
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- 1999-02-05 AU AU25053/99A patent/AU750197B2/en not_active Revoked
- 1999-02-05 NZ NZ506024A patent/NZ506024A/en not_active IP Right Cessation
- 1999-02-05 DE DE69937546T patent/DE69937546T2/de not_active Expired - Lifetime
- 1999-02-05 EP EP99904638A patent/EP1053011B1/en not_active Expired - Lifetime
- 1999-02-05 ES ES99904638T patent/ES2296380T3/es not_active Expired - Lifetime
- 1999-02-05 AT AT99904638T patent/ATE378062T1/de active
- 1999-02-05 WO PCT/CA1999/000106 patent/WO1999040932A1/en not_active Ceased
- 1999-02-05 PT PT99904638T patent/PT1053011E/pt unknown
- 1999-02-05 DK DK99904638T patent/DK1053011T3/da active
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Also Published As
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|---|---|
| DK1053011T3 (da) | 2008-03-25 |
| JP4499282B2 (ja) | 2010-07-07 |
| EP1053011A1 (en) | 2000-11-22 |
| AU2505399A (en) | 1999-08-30 |
| NZ506024A (en) | 2002-02-01 |
| US6017545A (en) | 2000-01-25 |
| EP1053011B1 (en) | 2007-11-14 |
| DE69937546T2 (de) | 2008-05-29 |
| JP2003522096A (ja) | 2003-07-22 |
| PT1053011E (pt) | 2008-02-14 |
| ES2296380T3 (es) | 2008-04-16 |
| WO1999040932A1 (en) | 1999-08-19 |
| US6231882B1 (en) | 2001-05-15 |
| WO1999040932A9 (en) | 2000-03-30 |
| ATE378062T1 (de) | 2007-11-15 |
| DE69937546D1 (de) | 2007-12-27 |
| BR9804295A (pt) | 2000-03-28 |
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