CA2440472C - Methods of treating acne - Google Patents
Methods of treating acne Download PDFInfo
- Publication number
- CA2440472C CA2440472C CA2440472A CA2440472A CA2440472C CA 2440472 C CA2440472 C CA 2440472C CA 2440472 A CA2440472 A CA 2440472A CA 2440472 A CA2440472 A CA 2440472A CA 2440472 C CA2440472 C CA 2440472C
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- amino
- halogen
- acne
- dimethylamino
- 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
- 206010000496 acne Diseases 0.000 title claims abstract description 115
- 208000002874 Acne Vulgaris Diseases 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 68
- -1 tetracycline compound Chemical class 0.000 claims abstract description 207
- 239000004098 Tetracycline Substances 0.000 claims abstract description 149
- 235000019364 tetracycline Nutrition 0.000 claims abstract description 148
- 229960002180 tetracycline Drugs 0.000 claims abstract description 130
- 229930101283 tetracycline Natural products 0.000 claims abstract description 127
- 230000003115 biocidal effect Effects 0.000 claims abstract description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 410
- 239000001257 hydrogen Substances 0.000 claims description 410
- 150000002431 hydrogen Chemical group 0.000 claims description 167
- 229910052736 halogen Inorganic materials 0.000 claims description 103
- 150000002367 halogens Chemical class 0.000 claims description 103
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 96
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 150000003522 tetracyclines Chemical class 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 33
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims description 27
- 229960003722 doxycycline Drugs 0.000 claims description 27
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims description 24
- 229960004023 minocycline Drugs 0.000 claims description 24
- 125000004442 acylamino group Chemical group 0.000 claims description 23
- 230000001937 non-anti-biotic effect Effects 0.000 claims description 23
- 239000012954 diazonium Substances 0.000 claims description 21
- 210000002966 serum Anatomy 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 17
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 239000003242 anti bacterial agent Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 230000003325 follicular Effects 0.000 claims description 8
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
- 229940122361 Bisphosphonate Drugs 0.000 claims description 7
- 230000002159 abnormal effect Effects 0.000 claims description 7
- 230000004069 differentiation Effects 0.000 claims description 6
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000004100 Oxytetracycline Substances 0.000 claims description 4
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 claims description 4
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims description 4
- 229960000625 oxytetracycline Drugs 0.000 claims description 4
- 235000019366 oxytetracycline Nutrition 0.000 claims description 4
- 238000013268 sustained release Methods 0.000 claims description 4
- 239000012730 sustained-release form Substances 0.000 claims description 4
- 238000007910 systemic administration Methods 0.000 claims description 4
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims description 4
- NBRQRXRBIHVLGI-OWXODZSWSA-N (4as,5ar,12ar)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=CC=CC(O)=C2C(O)=C(C2=O)[C@@H]1C[C@@H]1[C@@]2(O)C(O)=C(C(=O)N)C(=O)C1 NBRQRXRBIHVLGI-OWXODZSWSA-N 0.000 claims description 3
- XCCHQGIGHCRZOS-KBKZQPOHSA-N (4as,5as,6s,12ar)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@@](C)(O)[C@@H](C[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)C3)(O)C3=O)C3=C(O)C2=C1O XCCHQGIGHCRZOS-KBKZQPOHSA-N 0.000 claims description 3
- GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=C(Cl)C=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 claims description 3
- FMTDIUIBLCQGJB-UHFFFAOYSA-N Demethylchlortetracyclin Natural products C1C2C(O)C3=C(Cl)C=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O FMTDIUIBLCQGJB-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 claims description 3
- 229960002398 demeclocycline Drugs 0.000 claims description 3
- 201000004700 rosacea Diseases 0.000 claims description 3
- MWUTTXATIMURBN-VSAOOKSHSA-N (4aS,5aS,6S,12aR)-3,6,10,11-tetrahydroxy-6-methyl-1,12-dioxo-4a,5,5a,12a-tetrahydro-4H-tetracene-2-carboxamide Chemical compound C[C@]1(O)[C@H]2C[C@H]3CC(O)=C(C(N)=O)C(=O)[C@H]3C(=O)C2=C(O)c2c(O)cccc12 MWUTTXATIMURBN-VSAOOKSHSA-N 0.000 claims description 2
- 208000003911 Acne Keloid Diseases 0.000 claims description 2
- 206010000501 Acne conglobata Diseases 0.000 claims description 2
- 206010000502 Acne cosmetica Diseases 0.000 claims description 2
- 206010000503 Acne cystic Diseases 0.000 claims description 2
- 206010049141 Acne fulminans Diseases 0.000 claims description 2
- 206010000518 Acne varioliformis Diseases 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 208000001348 Chloracne Diseases 0.000 claims description 2
- 239000004099 Chlortetracycline Substances 0.000 claims description 2
- 206010065701 Dermatillomania Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 206010051651 Dermatitis papillaris capillitii Diseases 0.000 claims description 2
- 241001459566 Papulosa Species 0.000 claims description 2
- INEQDRZSMXQXJI-UHFFFAOYSA-N [diazonio(methyl)amino]methane Chemical compound CN(C)[N+]#N INEQDRZSMXQXJI-UHFFFAOYSA-N 0.000 claims description 2
- 210000001193 acne keloid Anatomy 0.000 claims description 2
- 150000004663 bisphosphonates Chemical class 0.000 claims description 2
- 229960004475 chlortetracycline Drugs 0.000 claims description 2
- 235000019365 chlortetracycline Nutrition 0.000 claims description 2
- VCROZLOYPNVPSH-DCKQLXEASA-N cmt-5 Chemical compound N1N=C2C3=C(O)C=CC=C3[C@@](C)(O)C3C2=C1[C@]1(O)C(=O)C(C(N)=O)=C(O)CC1C3 VCROZLOYPNVPSH-DCKQLXEASA-N 0.000 claims description 2
- BVFDLIAWTKFZQD-JXVDNWKRSA-N cmt-8 Chemical compound O=C1C2=C(O)C=CC=C2C(C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)C[C@@H]1C2O BVFDLIAWTKFZQD-JXVDNWKRSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
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- 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims 1
- 238000010255 intramuscular injection Methods 0.000 claims 1
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 238000010253 intravenous injection Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- 125000003118 aryl group Chemical group 0.000 description 20
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- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2719162A CA2719162C (en) | 2001-04-05 | 2002-04-05 | Methods of treating acne |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28191601P | 2001-04-05 | 2001-04-05 | |
| US60/281,916 | 2001-04-05 | ||
| PCT/US2002/010747 WO2002080932A1 (en) | 2001-04-05 | 2002-04-05 | Methods of treating acne |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2719162A Division CA2719162C (en) | 2001-04-05 | 2002-04-05 | Methods of treating acne |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2440472A1 CA2440472A1 (en) | 2002-10-17 |
| CA2440472C true CA2440472C (en) | 2011-01-18 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2719162A Expired - Lifetime CA2719162C (en) | 2001-04-05 | 2002-04-05 | Methods of treating acne |
| CA2440472A Expired - Lifetime CA2440472C (en) | 2001-04-05 | 2002-04-05 | Methods of treating acne |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2719162A Expired - Lifetime CA2719162C (en) | 2001-04-05 | 2002-04-05 | Methods of treating acne |
Country Status (12)
| Country | Link |
|---|---|
| EP (4) | EP1716856A3 (enExample) |
| JP (3) | JP2004536046A (enExample) |
| KR (1) | KR100926326B1 (enExample) |
| AT (1) | ATE330615T1 (enExample) |
| AU (1) | AU2002303250B2 (enExample) |
| CA (2) | CA2719162C (enExample) |
| DE (1) | DE60212613T2 (enExample) |
| DK (1) | DK1383508T3 (enExample) |
| ES (1) | ES2266499T3 (enExample) |
| NZ (1) | NZ528197A (enExample) |
| PT (1) | PT1383508E (enExample) |
| WO (1) | WO2002080932A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2311799A1 (en) * | 2002-01-08 | 2011-04-20 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| US8192749B2 (en) | 2003-04-16 | 2012-06-05 | Galderma Laboratories Inc. | Methods of simultaneously treating ocular rosacea and acne rosacea |
| CA2476792A1 (en) * | 2002-04-16 | 2003-10-30 | Collagenex Pharmaceuticals, Inc. | Methods of simultaneously treating ocular rosacea and acne rosacea |
| PT1615622E (pt) | 2003-04-07 | 2012-10-17 | Supernus Pharmaceuticals Inc | Formulações de doxiciclinas de dose única diária |
| CN103040773A (zh) | 2003-07-25 | 2013-04-17 | 沃纳奇尔科特有限责任公司 | 多西环素金属络合物固体剂型 |
| EP1684768A4 (en) * | 2003-11-06 | 2007-06-06 | Univ New York State Res Found | METHOD FOR TREATING ECCEM |
| US7544373B2 (en) | 2007-04-02 | 2009-06-09 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| US7541347B2 (en) | 2007-04-02 | 2009-06-02 | Medicis Pharmaceutical Coropration | Minocycline oral dosage forms for the treatment of acne |
| US8252776B2 (en) | 2007-04-02 | 2012-08-28 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| US9192615B2 (en) | 2008-08-06 | 2015-11-24 | Medicis Pharmaceutical Corporation | Method for the treatment of acne and certain dosage forms thereof |
| US7919483B2 (en) | 2005-06-24 | 2011-04-05 | Medicis Pharmaceutical Corporation | Method for the treatment of acne |
| US7704959B2 (en) * | 2006-10-03 | 2010-04-27 | Dow Pharmaceutical Sciences | Azithromycin for the treatment of nodular acne |
| CN102688492A (zh) * | 2007-03-23 | 2012-09-26 | 分子研究中心公司 | 包含四环素类的抗炎组合物及其用途 |
| WO2008121107A1 (en) * | 2007-04-02 | 2008-10-09 | Medicis Pharmaceutical Corporation | Minocycline oral dosage forms for the treatment of acne |
| EP2288349A1 (en) * | 2008-05-16 | 2011-03-02 | Galderma Research & Development | Therapy regimen for treating acne related diseases |
| US9561241B1 (en) | 2011-06-28 | 2017-02-07 | Medicis Pharmaceutical Corporation | Gastroretentive dosage forms for minocycline |
| BR112014025980A2 (pt) * | 2012-04-19 | 2018-04-17 | Galderma Sa | método para o tratamento da acne |
| RU2557991C1 (ru) * | 2014-05-19 | 2015-07-27 | Вячеслав Владимирович Чеботарёв | Способ лечения больных вульгарными угрями (акне), страдающих дисплазией соединительной ткани |
| CO2017001953A1 (es) * | 2017-02-27 | 2018-08-31 | Corporacion Univ Lasallista | Método de encapsulación de tetraciclinas |
| EP3654988B1 (en) * | 2017-07-21 | 2023-09-06 | Almirall, LLC | Sarecycline for the treatment of non-inflammatory acne lesions |
| EP3735249A1 (en) * | 2018-01-07 | 2020-11-11 | Dr. Reddy's Laboratories Ltd. | Minocycline for treating inflammatory skin conditions |
| AU2019419387B2 (en) * | 2019-01-04 | 2025-09-25 | Dermata Therapeutics, Inc. | Compositions and methods for the treatment of skin conditions |
| WO2021215405A1 (ja) * | 2020-04-20 | 2021-10-28 | 国立大学法人大阪大学 | 免疫賦活化剤、及び治療又は予防用組成物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0086228B1 (en) * | 1981-08-27 | 1988-05-11 | Soft Sheen Products, Inc. | Use of carbamide peroxide for the manufacture of a medicament for treatment of acne vulgaris |
| US5122519A (en) * | 1989-06-27 | 1992-06-16 | American Cyanamid Company | Stable, cosmetically acceptable topical gel formulation and method of treatment for acne |
| WO1992003133A1 (en) * | 1990-08-16 | 1992-03-05 | Bloom, Leonard | Topical treatment of blepharitis |
| US5674539A (en) * | 1994-12-09 | 1997-10-07 | Tomas; Robert E. | Method of treating skin and composition |
| FR2730930B1 (fr) * | 1995-02-27 | 1997-04-04 | Oreal | Utilisation d'inhibiteurs de no-synthase pour diminuer l'effet irritant cutane de produits utilises dans le domaine cosmetique ou pharmaceutique |
| US5827840A (en) * | 1996-08-01 | 1998-10-27 | The Research Foundation Of State University Of New York | Promotion of wound healing by chemically-modified tetracyclines |
| US5789395A (en) * | 1996-08-30 | 1998-08-04 | The Research Foundation Of State University Of New York | Method of using tetracycline compounds for inhibition of endogenous nitric oxide production |
| US5908838A (en) * | 1998-02-19 | 1999-06-01 | Medics Pharmaceutical Corporation | Method for the treatment of acne |
| US6432934B1 (en) * | 1998-08-06 | 2002-08-13 | Advanced Vision Research | Methods and compositions for topical treatment of eye surface inflammation and related dry eye disease |
| US6015804A (en) * | 1998-09-11 | 2000-01-18 | The Research Foundation Of State University Of New York | Method of using tetracycline compounds to enhance interleukin-10 production |
| JP2002525299A (ja) * | 1998-09-28 | 2002-08-13 | ザ リサーチ ファウンデーション オブ ステイト ユニヴァーシティ オブ ニューヨーク | 新規白内障形成抑制剤 |
| US5998390A (en) * | 1998-09-28 | 1999-12-07 | The Research Foundation Of State University Of New York | Combination of bisphosphonate and tetracycline |
| DE69932846T2 (de) * | 1998-11-18 | 2007-03-15 | Collagenex Pharmaceuticals, Inc. | Neue 4-dedimethylaminotetracyclinderivate |
| JP2001072660A (ja) * | 1999-09-08 | 2001-03-21 | Welfide Corp | ＴＮＦ−α産生抑制剤および／またはＩＬ−１０産生促進剤 |
-
2002
- 2002-04-05 EP EP06076250A patent/EP1716856A3/en not_active Withdrawn
- 2002-04-05 EP EP02731267A patent/EP1383508B1/en not_active Expired - Lifetime
- 2002-04-05 NZ NZ528197A patent/NZ528197A/en not_active IP Right Cessation
- 2002-04-05 JP JP2002578971A patent/JP2004536046A/ja active Pending
- 2002-04-05 WO PCT/US2002/010747 patent/WO2002080932A1/en not_active Ceased
- 2002-04-05 PT PT02731267T patent/PT1383508E/pt unknown
- 2002-04-05 DE DE60212613T patent/DE60212613T2/de not_active Expired - Lifetime
- 2002-04-05 DK DK02731267T patent/DK1383508T3/da active
- 2002-04-05 EP EP06076249A patent/EP1712236A3/en not_active Withdrawn
- 2002-04-05 CA CA2719162A patent/CA2719162C/en not_active Expired - Lifetime
- 2002-04-05 CA CA2440472A patent/CA2440472C/en not_active Expired - Lifetime
- 2002-04-05 KR KR1020037012965A patent/KR100926326B1/ko not_active Expired - Lifetime
- 2002-04-05 AU AU2002303250A patent/AU2002303250B2/en not_active Expired
- 2002-04-05 ES ES02731267T patent/ES2266499T3/es not_active Expired - Lifetime
- 2002-04-05 EP EP10159154A patent/EP2221056A1/en not_active Withdrawn
- 2002-04-05 AT AT02731267T patent/ATE330615T1/de active
-
2009
- 2009-12-10 JP JP2009280436A patent/JP2010053155A/ja active Pending
-
2011
- 2011-05-24 JP JP2011115785A patent/JP2011168613A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1716856A2 (en) | 2006-11-02 |
| EP1716856A3 (en) | 2009-02-18 |
| EP1383508A4 (en) | 2005-07-06 |
| DK1383508T3 (da) | 2006-12-27 |
| AU2002303250B2 (en) | 2006-05-25 |
| JP2011168613A (ja) | 2011-09-01 |
| JP2010053155A (ja) | 2010-03-11 |
| CA2440472A1 (en) | 2002-10-17 |
| WO2002080932A1 (en) | 2002-10-17 |
| PT1383508E (pt) | 2006-11-30 |
| ATE330615T1 (de) | 2006-07-15 |
| JP2004536046A (ja) | 2004-12-02 |
| ES2266499T3 (es) | 2007-03-01 |
| DE60212613T2 (de) | 2007-05-24 |
| EP1383508B1 (en) | 2006-06-21 |
| KR100926326B1 (ko) | 2009-11-12 |
| CA2719162A1 (en) | 2002-10-17 |
| EP1712236A3 (en) | 2008-05-28 |
| EP2221056A1 (en) | 2010-08-25 |
| CA2719162C (en) | 2014-12-23 |
| EP1383508A1 (en) | 2004-01-28 |
| KR20040007488A (ko) | 2004-01-24 |
| EP1712236A2 (en) | 2006-10-18 |
| NZ528197A (en) | 2007-04-27 |
| DE60212613D1 (de) | 2006-08-03 |
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