CA2463505C - Low-calcemic oxime analogs of 1.alpha.,25-dihydroxy vitamin d3 - Google Patents
Low-calcemic oxime analogs of 1.alpha.,25-dihydroxy vitamin d3 Download PDFInfo
- Publication number
- CA2463505C CA2463505C CA2463505A CA2463505A CA2463505C CA 2463505 C CA2463505 C CA 2463505C CA 2463505 A CA2463505 A CA 2463505A CA 2463505 A CA2463505 A CA 2463505A CA 2463505 C CA2463505 C CA 2463505C
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- CA
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- Prior art keywords
- 4alkyl
- 4alkenyl
- 6alkenyl
- compound according
- 6alkyl
- Prior art date
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- GMRQFYUYWCNGIN-CLVAPQHMSA-N (5e)-5-[(2e)-2-[1-(6-hydroxy-6-methylheptan-2-yl)-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2\C1=C\C=C1/CC(O)CC(O)C1=C GMRQFYUYWCNGIN-CLVAPQHMSA-N 0.000 title claims abstract 7
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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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- 239000011148 porous material Substances 0.000 description 1
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- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005797 stannylation reaction Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- UQCWXKSHRQJGPH-UHFFFAOYSA-M tetrabutylazanium;fluoride;hydrate Chemical compound O.[F-].CCCC[N+](CCCC)(CCCC)CCCC UQCWXKSHRQJGPH-UHFFFAOYSA-M 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 150000005671 trienes Chemical group 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical class C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 1
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
- 230000006433 tumor necrosis factor production Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- 239000011782 vitamin Substances 0.000 description 1
- 150000003703 vitamin D2 derivatives Chemical class 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- 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
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
-
- 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
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- 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
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Nutrition Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32842801P | 2001-10-12 | 2001-10-12 | |
| US60/328,428 | 2001-10-12 | ||
| PCT/CA2002/001519 WO2003031400A1 (en) | 2001-10-12 | 2002-10-11 | Low-calcemic oxime analogs of 1alpha, 25-dihydroxy vitamin d3 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2463505A1 CA2463505A1 (en) | 2003-04-17 |
| CA2463505C true CA2463505C (en) | 2011-07-12 |
Family
ID=23280940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2463505A Expired - Lifetime CA2463505C (en) | 2001-10-12 | 2002-10-11 | Low-calcemic oxime analogs of 1.alpha.,25-dihydroxy vitamin d3 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6982258B2 (https=) |
| EP (1) | EP1436257B1 (https=) |
| JP (1) | JP4436674B2 (https=) |
| AT (1) | ATE360000T1 (https=) |
| CA (1) | CA2463505C (https=) |
| CY (1) | CY1106638T1 (https=) |
| DE (1) | DE60219655T2 (https=) |
| DK (1) | DK1436257T3 (https=) |
| ES (1) | ES2283593T3 (https=) |
| PT (1) | PT1436257E (https=) |
| WO (1) | WO2003031400A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6242434B1 (en) | 1997-08-08 | 2001-06-05 | Bone Care International, Inc. | 24-hydroxyvitamin D, analogs and uses thereof |
| US6087350A (en) * | 1997-08-29 | 2000-07-11 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Use of pretreatment chemicals to enhance efficacy of cytotoxic agents |
| EP1301479A2 (en) | 2000-07-18 | 2003-04-16 | Bone Care International, Inc. | STABILIZED 1$g(a)-HYDROXY VITAMIN D |
| US20050059641A1 (en) * | 2003-06-17 | 2005-03-17 | Aphios Corporation | Compositions and methods for treating and preventing cancer using analogs of vitamin D |
| US20050192255A1 (en) * | 2003-07-30 | 2005-09-01 | Jin Tian | Use of Vitamin Ds or Vitamin D analogs to treat cardiovascular disease |
| US20070142339A1 (en) * | 2004-05-10 | 2007-06-21 | Novacea, Inc. | Prevention of arterial restenosis with active vitamin d compounds |
| US7094775B2 (en) | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
| WO2006032299A1 (en) * | 2004-09-24 | 2006-03-30 | Susanna Miettinen | Use of inhibitors of 24-hydroxylase in the treatment of cancer |
| WO2006074227A2 (en) * | 2005-01-04 | 2006-07-13 | Johns Hopkins University | HIGHLY ANTIPROLIFERATIVE, LOW-CALCEMIC, ANALOGS OF THE HORMONE 1α, 25-DIHYDROXYVITAMIN D3 WITH CARBONYL SIDE CHAINS |
| WO2006113990A2 (en) * | 2005-04-25 | 2006-11-02 | Cytochroma Inc. | LOW-CALCEMIC 16,23-DIENE 25-OXIME ANALOGS OF 1α ,25-DIHYDROXY VITAMIN D3 |
| WO2007047327A2 (en) * | 2005-10-12 | 2007-04-26 | Proventiv Therapeutics, Llc | Methods and articles for treating 25-hydroxyvitamin d insufficiency and deficiency |
| SI3095447T1 (sl) * | 2006-02-03 | 2022-02-28 | Opko Renal, Llc | Zdravljenje pomanjkanja vitamina D s 25-hidroksivitaminom D2 in 25-hidroksivitaminom D3 |
| HUE037309T2 (hu) | 2006-06-21 | 2018-08-28 | Opko Ireland Global Holdings Ltd | Terápia D-vitamin telítési szer alkalmazásával és D-vitamin hormon helyettesítõ szer |
| US9481646B2 (en) * | 2007-04-18 | 2016-11-01 | The Johns Hopkins University | Low calcemic, highly antiproliferative, analogs of calcitriol |
| US8592401B2 (en) * | 2007-04-25 | 2013-11-26 | Proventiv Therapeutics, Llc | Methods and compounds for vitamin D therapy |
| PL2148661T3 (pl) | 2007-04-25 | 2013-07-31 | Cytochroma Inc | Doustne kompozycje o kontrolowanym uwalnianiu zawierające związek będący witaminą D i woskowy nośnik |
| PT3335712T (pt) | 2007-04-25 | 2025-10-23 | Opko Renal Llc | Método de tratamento e prevenção seguro e eficaz do hiperparatiroidismo secundário na doença renal crónica |
| DK2148684T3 (da) * | 2007-04-25 | 2013-04-22 | Cytochroma Inc | Fremgangsmåde til behandling af vitamin D-insufficiens og -deficiens |
| US20100048524A1 (en) | 2008-03-14 | 2010-02-25 | Angela Brodie | Novel C-17-Heteroaryl Steroidal CYP17 Inhibitors/Antiandrogens;Synthesis In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity |
| GB2470700B (en) | 2008-03-25 | 2012-08-08 | Univ Maryland | C-17 heteroaryl steroidal CYP17 inhibitors |
| CN102046812A (zh) * | 2008-04-02 | 2011-05-04 | 赛特克罗公司 | 用于维生素d缺乏症和相关障碍的方法、组合物、用途和试剂盒 |
| WO2010091306A1 (en) | 2009-02-05 | 2010-08-12 | Tokai Pharmaceuticals | Novel prodrugs of steroidal cyp17 inhibitors/antiandrogens |
| US20100227414A1 (en) * | 2009-03-05 | 2010-09-09 | Trex Enterprises Corp. | Affinity capture mass spectroscopy with a porous silicon biosensor |
| US9775903B2 (en) | 2010-01-13 | 2017-10-03 | Johns Hopkins University | 1-deoxy analogs of 1,25-dihydroxyvitamin D3 compounds |
| PT2552484T (pt) | 2010-03-29 | 2020-04-03 | Opko Ireland Global Holdings Ltd | Métodos e composições para redução dos níveis de parafróides |
| KR20150127720A (ko) | 2013-03-14 | 2015-11-17 | 유니버시티 오브 매릴랜드, 발티모어 | 안드로겐 수용체 하향 조절제 및 그의 용도 |
| KR101847947B1 (ko) | 2013-03-15 | 2018-05-28 | 옵코 아이피 홀딩스 Ⅱ 인코포레이티드 | 안정화되고 변형된 비타민 ｄ 방출 제형 |
| CA2920317A1 (en) | 2013-08-12 | 2015-02-19 | Tokai Pharmaceuticals, Inc. | Biomarkers for treatment of neoplastic disorders using androgen-targeted therapies |
| US10220047B2 (en) | 2014-08-07 | 2019-03-05 | Opko Ireland Global Holdings, Ltd. | Adjunctive therapy with 25-hydroxyvitamin D and articles therefor |
| CN104557647B (zh) * | 2015-01-13 | 2016-07-06 | 南京理工大学 | 维生素d肟类衍生物、合成方法及其应用 |
| CN104945296B (zh) * | 2015-06-09 | 2016-08-24 | 南京理工大学 | 一类芳香醛腙修饰的维生素d2衍生物、合成及其应用 |
| MY198547A (en) | 2016-03-28 | 2023-09-04 | Opko Ireland Global Holdings Ltd | Methods of vitamin d treatment |
| CN117003679A (zh) * | 2022-04-29 | 2023-11-07 | 南澳大利亚大学 | 新型抑制剂化合物 |
| WO2025094144A1 (en) | 2023-11-02 | 2025-05-08 | Eirgen Pharma Ltd. | Controlling loss of kidney function |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481198A (en) * | 1984-02-13 | 1984-11-06 | Wisconsin Alumni Research Foundation | Vitamin D metabolism inhibitor |
| GB9623569D0 (en) * | 1996-11-13 | 1997-01-08 | Immunodiagnostic Systems Ltd | Vitamin D immumoassay systems |
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2002
- 2002-10-11 JP JP2003534384A patent/JP4436674B2/ja not_active Expired - Fee Related
- 2002-10-11 CA CA2463505A patent/CA2463505C/en not_active Expired - Lifetime
- 2002-10-11 DE DE60219655T patent/DE60219655T2/de not_active Expired - Lifetime
- 2002-10-11 ES ES02767010T patent/ES2283593T3/es not_active Expired - Lifetime
- 2002-10-11 EP EP02767010A patent/EP1436257B1/en not_active Expired - Lifetime
- 2002-10-11 AT AT02767010T patent/ATE360000T1/de active
- 2002-10-11 DK DK02767010T patent/DK1436257T3/da active
- 2002-10-11 WO PCT/CA2002/001519 patent/WO2003031400A1/en not_active Ceased
- 2002-10-11 PT PT02767010T patent/PT1436257E/pt unknown
- 2002-10-15 US US10/270,158 patent/US6982258B2/en not_active Expired - Lifetime
-
2007
- 2007-06-04 CY CY20071100741T patent/CY1106638T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20030171342A1 (en) | 2003-09-11 |
| CA2463505A1 (en) | 2003-04-17 |
| US6982258B2 (en) | 2006-01-03 |
| CY1106638T1 (el) | 2012-01-25 |
| WO2003031400A1 (en) | 2003-04-17 |
| PT1436257E (pt) | 2007-05-31 |
| ATE360000T1 (de) | 2007-05-15 |
| DK1436257T3 (da) | 2007-06-25 |
| EP1436257B1 (en) | 2007-04-18 |
| JP2005536444A (ja) | 2005-12-02 |
| DE60219655D1 (de) | 2007-05-31 |
| DE60219655T2 (de) | 2007-12-27 |
| ES2283593T3 (es) | 2007-11-01 |
| EP1436257A1 (en) | 2004-07-14 |
| JP4436674B2 (ja) | 2010-03-24 |
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