RU2386637C2 - 15β-ЗАМЕЩЕННЫЕ СТЕРОИДЫ С ИЗБИРАТЕЛЬНОЙ ЭСТРОГЕННОЙ АКТИВНОСТЬЮ - Google Patents
15β-ЗАМЕЩЕННЫЕ СТЕРОИДЫ С ИЗБИРАТЕЛЬНОЙ ЭСТРОГЕННОЙ АКТИВНОСТЬЮ Download PDFInfo
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- RU2386637C2 RU2386637C2 RU2007112939/04A RU2007112939A RU2386637C2 RU 2386637 C2 RU2386637 C2 RU 2386637C2 RU 2007112939/04 A RU2007112939/04 A RU 2007112939/04A RU 2007112939 A RU2007112939 A RU 2007112939A RU 2386637 C2 RU2386637 C2 RU 2386637C2
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- alkyl
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- estrogen
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- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
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- 238000006053 organic reaction Methods 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- PFGVNLZDWRZPJW-OPAMFIHVSA-N otamixaban Chemical compound C([C@@H](C(=O)OC)[C@@H](C)NC(=O)C=1C=CC(=CC=1)C=1C=C[N+]([O-])=CC=1)C1=CC=CC(C(N)=N)=C1 PFGVNLZDWRZPJW-OPAMFIHVSA-N 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
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- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 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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- 238000010992 reflux Methods 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
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- 230000035900 sweating Effects 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Gynecology & Obstetrics (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60850104P | 2004-09-08 | 2004-09-08 | |
| US60/608,501 | 2004-09-08 | ||
| EP04104334 | 2004-09-08 | ||
| EP04104334.0 | 2004-09-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007112939A RU2007112939A (ru) | 2008-11-10 |
| RU2386637C2 true RU2386637C2 (ru) | 2010-04-20 |
Family
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| RU2007112939/04A RU2386637C2 (ru) | 2004-09-08 | 2005-09-05 | 15β-ЗАМЕЩЕННЫЕ СТЕРОИДЫ С ИЗБИРАТЕЛЬНОЙ ЭСТРОГЕННОЙ АКТИВНОСТЬЮ |
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| EP (1) | EP1805201B1 (enExample) |
| JP (1) | JP4889644B2 (enExample) |
| AR (1) | AR050732A1 (enExample) |
| AT (1) | ATE414710T1 (enExample) |
| AU (1) | AU2005281705B2 (enExample) |
| BR (1) | BRPI0514976A (enExample) |
| CA (1) | CA2577497C (enExample) |
| DK (1) | DK1805201T3 (enExample) |
| ES (1) | ES2317312T3 (enExample) |
| NZ (1) | NZ553266A (enExample) |
| PE (1) | PE20060590A1 (enExample) |
| PL (1) | PL1805201T3 (enExample) |
| PT (1) | PT1805201E (enExample) |
| RS (1) | RS51640B (enExample) |
| RU (1) | RU2386637C2 (enExample) |
| SI (1) | SI1805201T1 (enExample) |
| TW (1) | TW200621795A (enExample) |
| UA (1) | UA89964C2 (enExample) |
| WO (1) | WO2006027347A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8030298B2 (en) | 2005-05-26 | 2011-10-04 | Abbott Products Gmbh | 17β-HSD1 and STS inhibitors |
| US8080540B2 (en) | 2006-09-19 | 2011-12-20 | Abbott Products Gmbh | Therapeutically active triazoles and their use |
| US8288367B2 (en) | 2006-11-30 | 2012-10-16 | Solvay Pharmaceuticals Gmbh | Substituted estratriene derivatives as 17BETA HSD inhibitors |
| EP2448901A1 (en) * | 2009-06-29 | 2012-05-09 | Merz Pharma GmbH & Co. KGaA | Method of preparing 3,3,5,5-tetramethylcyclohexanone |
| ES2416462T3 (es) * | 2009-06-29 | 2013-08-01 | Merz Pharma Gmbh & Co. Kgaa | Método de preparación de neramexane. |
| EP2448908B1 (en) * | 2009-06-29 | 2013-09-18 | Merz Pharma GmbH & Co. KGaA | Method of preparing neramexane |
| EP2383279A1 (en) | 2011-07-19 | 2011-11-02 | Pantarhei Bioscience B.V. | Process for the preparation of estetrol |
| AU2012320423C1 (en) * | 2011-10-07 | 2018-01-25 | Estetra Srl | Process for the production of estetrol |
| TW201512215A (zh) | 2013-06-25 | 2015-04-01 | Forendo Pharma Ltd | 治療活性雌三烯噻唑衍生物 |
| JP6456373B2 (ja) | 2013-06-25 | 2019-01-23 | フォレンド ファーマ リミテッド | １７β−ヒドロキシステロイドデヒドロゲナーゼ タイプ１の阻害剤として治療活性のあるエストラトリエンチアゾール誘導体 |
| AU2014300894A1 (en) | 2013-06-25 | 2016-01-28 | Forendo Pharma Ltd | Therapeutically active 17-nitrogen substituted estratrienthiazole derivatives as inhibitors of 17.beta.-hydroxysteroid dehydrogenase |
| US10413557B2 (en) | 2014-12-23 | 2019-09-17 | Forendo Pharma Ltd. | Prodrugs of 17.BETA.-HSD1-inhibitors |
| WO2016102775A1 (en) | 2014-12-23 | 2016-06-30 | Forendo Pharma Ltd | PRODRUGS OF 17β-HSD1 -INHIBITORS |
| MA44206B1 (fr) | 2015-06-18 | 2021-04-30 | Estetra Sprl | Comprimé orodispersible comprenant estetrol |
| CU24523B1 (es) | 2015-06-18 | 2021-06-08 | Estetra Sprl | Unidad de dosificación orodispersable que contiene un componente estetrol |
| LT3310345T (lt) | 2015-06-18 | 2021-06-25 | Estetra Sprl | Burnoje disperguojama tabletė, turinti estetrolio |
| EP3701944B1 (en) | 2015-06-18 | 2021-12-08 | Estetra SRL | Orodispersible dosage unit containing an estetrol component |
| CA3178291A1 (en) | 2016-08-05 | 2018-04-12 | Estetra Srl | Method for the management of dysmenorrhea and menstrual pain |
| SG11201911776PA (en) | 2017-06-08 | 2020-01-30 | Forendo Pharma Ltd | 15.beta.-[3-propanamido]-substituted estra-1,3,5(10)-trien-17-one compounds and their 17-oximes for use in inhibition of 17.beta.-hydroxysteroid dehydrogenases |
| TWI801561B (zh) | 2018-04-19 | 2023-05-11 | 比利時商依思特拉私人有限責任公司 | 化合物及其用於緩解絕經相關症狀的用途 |
| EP3781171B1 (en) | 2018-04-19 | 2022-02-09 | Estetra SRL | Compounds and their uses for alleviating menopause-associated symptoms |
| CA3122049C (en) | 2018-12-05 | 2023-10-17 | Forendo Pharma Ltd | Estra-1,3,5(10)-triene compounds condensed in position 16(17) with a pyrazole ring as inhibitors of 17-hsd1 |
| TWI893101B (zh) | 2020-04-16 | 2025-08-11 | 比利時商埃斯特拉有限責任公司 | 具有降低之副作用之避孕組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5686437A (en) * | 1988-10-31 | 1997-11-11 | Endorecherche Inc. | Estrogen nucleus derivatives for use in the inhibition of sex steroid activity |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| NL226738A (enExample) | 1957-04-11 | |||
| DE1084261B (de) | 1957-04-11 | 1960-06-30 | Syntex Sa | Verfahren zur Herstellung neuer Cyclopentanophenanthrenderivate |
| US3257429A (en) * | 1957-11-12 | 1966-06-21 | Syntex Corp | 16-methylene derivatives of estrone and estradiol |
| US3007946A (en) | 1958-11-06 | 1961-11-07 | Searle & Co | 3-alkoxy-16-methylene-1, 3, 5(10)-estratrien-17-ones |
| US3049555A (en) | 1959-12-22 | 1962-08-14 | Searle & Co | 3-alkoxy-16-methyl-1, 3, 5 (10)-estratrien-17-ones |
| US3092645A (en) | 1961-12-28 | 1963-06-04 | Searle & Co | Esters of 17alpha-alkynylester-5(10)-ene-3beta, 17beta-diols |
| GB1110792A (en) | 1964-04-07 | 1968-04-24 | Res Inst Medicine Chem | Novel 5(10)-dehydro-steroids |
| US3299108A (en) | 1965-10-18 | 1967-01-17 | Searle & Co | 17alpha-alkynyl/alkenyl-13beta-alkyl-11-alkylgona-1, 3, 5 (10)-triene-3, 17beta-diols, ethers and esters thereof and intermediates thereto |
| US3465010A (en) | 1966-11-22 | 1969-09-02 | Searle & Co | 17 - (unsaturated hydrocarbon - substituted) 11,13beta - dialkylgon -4 - ene - 3,17beta-diols and esters thereof |
| US3377366A (en) | 1966-12-02 | 1968-04-09 | Searle & Co | 17alpha-alkynyl/alkenyl-11, 13beta-dialkylgon-5(10)-en-3-ones and esters thereof |
| US3642992A (en) * | 1967-09-08 | 1972-02-15 | Upjohn Co | Organic compounds |
| ZA712312B (en) | 1970-04-28 | 1972-01-26 | Ochsner Med Found Alton | 4,14-estradiene compounds |
| US3652606A (en) | 1970-08-07 | 1972-03-28 | Searle & Co | 3-oxygenated 11beta-methylestr-4-en-17beta-ol and esters thereof |
| US3704253A (en) | 1970-09-23 | 1972-11-28 | American Home Prod | 13 - polycarbonalkyl - 16 - methylgona-1,3,5(10)-trienes and 13-polycarbonalkyl-16-methylgon - 4 - en-3-ones and intermediates for their production |
| US3766224A (en) * | 1971-06-03 | 1973-10-16 | Sandoz Ag | 15-methyl-substituted steroids |
| FR2377419A1 (fr) | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides 11b-substitues 1,3,5 (10) trieniques, leur procede de preparation et leur application comme medicament |
| DE2757157C3 (de) | 1977-12-19 | 1980-10-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von 16 a -alkylierten Steroiden |
| AU572589B2 (en) | 1983-12-14 | 1988-05-12 | Upjohn Company, The | 11(alpha)-difluoromethyl and (e)-and (z)-11-fluoromethylene steroids |
| US5116830A (en) | 1984-08-17 | 1992-05-26 | Sri International | Stereoisomerically pure 17α-ethynyl-estra-2-en-17β-ol and the 17β esters thereof, methods of preparation and uses |
| ZA94715B (en) | 1993-02-08 | 1994-10-24 | Akzo Nv | Steroids for treating menopausal complaints |
| EP0613687B1 (en) | 1993-03-05 | 1999-06-02 | Akzo Nobel N.V. | Use of a pregnane derivatives for the treatment of tumours |
| CA2200423C (en) | 1996-03-26 | 2006-12-19 | Sietse Mosselman | Novel estrogen receptor |
| TW403736B (en) | 1997-02-21 | 2000-09-01 | Akzo Nobel Nv | Steroid compounds having contraceptive and anti-osteoporosis activity |
| CA2319765A1 (en) | 1998-03-09 | 1999-09-16 | Akzo Nobel Nv | New contraceptive kit |
| TR200003743T2 (tr) | 1998-06-19 | 2001-07-23 | Akzo Nobel N.V. | Testosteron türevi. |
| WO2000031112A1 (en) | 1998-11-20 | 2000-06-02 | Akzo Nobel N.V. | Estrogenic estra-1,3,5(10)-trienes with differential effects on the alpha and beta estrogen receptors, having a linear hydrocarbon chain of from 5-9 carbon atoms in position 11 |
| TW548277B (en) | 1999-07-16 | 2003-08-21 | Akzo Nobel Nv | Orally active androgens |
| NZ517281A (en) | 1999-09-06 | 2003-09-26 | Akzo Nobel Nv | Non-aromatic estrogenic steroids with a hydrocarbon substituent in position 11 |
| PT1226155E (pt) * | 1999-11-02 | 2007-07-26 | Bayer Schering Pharma Ag | 18-nor-esteróides como estrogénios selectivamente activos |
| US7696190B2 (en) * | 2000-07-28 | 2010-04-13 | N.V. Organon | 16Alpha-methyl or ethyl substituted estrogens |
-
2005
- 2005-05-09 UA UAA200701655A patent/UA89964C2/ru unknown
- 2005-09-02 TW TW094130148A patent/TW200621795A/zh unknown
- 2005-09-05 PT PT05794597T patent/PT1805201E/pt unknown
- 2005-09-05 BR BRPI0514976-2A patent/BRPI0514976A/pt not_active IP Right Cessation
- 2005-09-05 EP EP05794597A patent/EP1805201B1/en not_active Expired - Lifetime
- 2005-09-05 ES ES05794597T patent/ES2317312T3/es not_active Expired - Lifetime
- 2005-09-05 US US11/662,166 patent/US7838516B2/en active Active
- 2005-09-05 RS RS20070075A patent/RS51640B/sr unknown
- 2005-09-05 RU RU2007112939/04A patent/RU2386637C2/ru not_active IP Right Cessation
- 2005-09-05 NZ NZ553266A patent/NZ553266A/en not_active IP Right Cessation
- 2005-09-05 CA CA2577497A patent/CA2577497C/en not_active Expired - Fee Related
- 2005-09-05 JP JP2007530702A patent/JP4889644B2/ja not_active Expired - Fee Related
- 2005-09-05 AT AT05794597T patent/ATE414710T1/de active
- 2005-09-05 DK DK05794597T patent/DK1805201T3/da active
- 2005-09-05 WO PCT/EP2005/054368 patent/WO2006027347A1/en not_active Ceased
- 2005-09-05 AU AU2005281705A patent/AU2005281705B2/en not_active Ceased
- 2005-09-05 PL PL05794597T patent/PL1805201T3/pl unknown
- 2005-09-05 SI SI200530582T patent/SI1805201T1/sl unknown
- 2005-09-06 PE PE2005001026A patent/PE20060590A1/es not_active Application Discontinuation
- 2005-09-08 AR ARP050103745A patent/AR050732A1/es unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5686437A (en) * | 1988-10-31 | 1997-11-11 | Endorecherche Inc. | Estrogen nucleus derivatives for use in the inhibition of sex steroid activity |
Non-Patent Citations (1)
| Title |
|---|
| FRIED J., EDWARDS J.A. // Organic Reactions in Steroid Chemistry, v 1, 2 N-Y, 1972. * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006027347A1 (en) | 2006-03-16 |
| PT1805201E (pt) | 2008-12-31 |
| TW200621795A (en) | 2006-07-01 |
| AU2005281705B2 (en) | 2011-03-10 |
| US20070254860A1 (en) | 2007-11-01 |
| US7838516B2 (en) | 2010-11-23 |
| SI1805201T1 (sl) | 2009-04-30 |
| BRPI0514976A (pt) | 2008-07-01 |
| AR050732A1 (es) | 2006-11-15 |
| RS51640B (sr) | 2011-10-31 |
| RU2007112939A (ru) | 2008-11-10 |
| PL1805201T3 (pl) | 2009-04-30 |
| AU2005281705A1 (en) | 2006-03-16 |
| RS20070075A (sr) | 2008-09-29 |
| JP4889644B2 (ja) | 2012-03-07 |
| ES2317312T3 (es) | 2009-04-16 |
| EP1805201A1 (en) | 2007-07-11 |
| NZ553266A (en) | 2009-06-26 |
| PE20060590A1 (es) | 2006-07-14 |
| UA89964C2 (ru) | 2010-03-25 |
| EP1805201B1 (en) | 2008-11-19 |
| ATE414710T1 (de) | 2008-12-15 |
| CA2577497A1 (en) | 2006-03-16 |
| JP2008512426A (ja) | 2008-04-24 |
| DK1805201T3 (da) | 2009-01-12 |
| CA2577497C (en) | 2012-03-20 |
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