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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- 238000006146 oximation reaction Methods 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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- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
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- 201000001514 prostate carcinoma Diseases 0.000 description 1
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- 229940070891 pyridium Drugs 0.000 description 1
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- 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
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- 210000002966 serum Anatomy 0.000 description 1
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- 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
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- 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
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 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
-
- 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
-
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Nutrition Science (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (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 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1436257B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP4436674B2 (cg-RX-API-DMAC10.html) |
| AT (1) | ATE360000T1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2463505C (cg-RX-API-DMAC10.html) |
| CY (1) | CY1106638T1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE60219655T2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK1436257T3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2283593T3 (cg-RX-API-DMAC10.html) |
| PT (1) | PT1436257E (cg-RX-API-DMAC10.html) |
| WO (1) | WO2003031400A1 (cg-RX-API-DMAC10.html) |
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 |
| JP2004504295A (ja) | 2000-07-18 | 2004-02-12 | ボーン ケア インターナショナル インコーポレイテッド | 安定化１α−ヒドロキシビタミン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 |
| JP2007537263A (ja) * | 2004-05-10 | 2007-12-20 | ノバセア インコーポレイティッド | 活性ビタミンｄ化合物による動脈再狭窄の予防法 |
| 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 |
| US20070122477A1 (en) * | 2005-10-12 | 2007-05-31 | Cytochroma, Inc. | Methods and articles for treating 25-hydroxyvitamin D insufficiency and deficiency |
| PT3095447T (pt) | 2006-02-03 | 2022-01-24 | Opko Renal Llc | Tratamento da insuficiência e deficiência de vitamina d com 25-hidroxivitamina d2 e 25-hidroxivitamina d3 |
| DK2037936T3 (da) | 2006-06-21 | 2014-09-22 | Opko Renal Llc | Fremgangsmåde til behandling og forebyggelse af sekundær hyperparathyroidisme |
| WO2008131267A2 (en) * | 2007-04-18 | 2008-10-30 | Johns Hopkins University | Low calcemic, highly antiproliferative, analogs of calcitriol |
| CA2683628C (en) * | 2007-04-25 | 2018-03-06 | Cytochroma Inc. | Method of treating vitamin d insufficiency and deficiency |
| EP2148685A4 (en) * | 2007-04-25 | 2010-07-28 | Cytochroma Inc | METHODS AND COMPOUNDS FOR THERAPY BASED ON VITAMIN D |
| ES3047207T3 (en) | 2007-04-25 | 2025-12-03 | Opko Renal Llc | Method of safely and effectively treating and preventing secondary hyperparathyroidism in chronic kidney disease |
| KR101691876B1 (ko) | 2007-04-25 | 2017-01-02 | 사이토크로마 인코포레이티드 | 비타민 ｄ 화합물과 밀랍성 담체를 포함하는 경구 조절성 방출 조성물 |
| 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 |
| WO2009120565A2 (en) | 2008-03-25 | 2009-10-01 | University Of Maryland, Baltimore | Novel prodrugs of c-17-heteroaryl steroidal cyp17 inhibitors/antiandrogens: synthesis, in vitro biological activities, pharmacokinetics and antitumor activity |
| ES2593356T3 (es) | 2008-04-02 | 2016-12-07 | Opko Ireland Global Holdings, Ltd. | Métodos, composiciones, usos y kits útiles para la deficiencia de la vitamina D y trastornos relacionados |
| EP2393827B1 (en) | 2009-02-05 | 2015-10-07 | Tokai Pharmaceuticals, Inc. | 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 |
| WO2011088209A2 (en) | 2010-01-13 | 2011-07-21 | Cytochroma Inc. | 1-deoxy analogs of vitamin d-related compounds |
| US11672809B2 (en) | 2010-03-29 | 2023-06-13 | Eirgen Pharma Ltd. | Methods and compositions for reducing parathyroid levels |
| CA2904170A1 (en) | 2013-03-14 | 2014-09-25 | University Of Maryland, Baltimore | Androgen receptor down-regulating agents and uses thereof |
| KR101847947B1 (ko) | 2013-03-15 | 2018-05-28 | 옵코 아이피 홀딩스 Ⅱ 인코포레이티드 | 안정화되고 변형된 비타민 ｄ 방출 제형 |
| KR20160058774A (ko) | 2013-08-12 | 2016-05-25 | 토카이 파마슈티컬, 아이엔씨. | 안드로겐-표적 치료제를 이용하는 종양 질환 치료를 위한 바이오마커 |
| 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 |
| KR20180123100A (ko) | 2016-03-28 | 2018-11-14 | 옵코 아일랜드 글로벌 홀딩스 리미티드 | 비타민 d 치료 방법 |
| 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 DK DK02767010T patent/DK1436257T3/da active
- 2002-10-11 AT AT02767010T patent/ATE360000T1/de active
- 2002-10-11 JP JP2003534384A patent/JP4436674B2/ja not_active Expired - Fee Related
- 2002-10-11 DE DE60219655T patent/DE60219655T2/de not_active Expired - Lifetime
- 2002-10-11 PT PT02767010T patent/PT1436257E/pt unknown
- 2002-10-11 WO PCT/CA2002/001519 patent/WO2003031400A1/en not_active Ceased
- 2002-10-11 CA CA2463505A patent/CA2463505C/en not_active Expired - Lifetime
- 2002-10-11 EP EP02767010A patent/EP1436257B1/en not_active Expired - Lifetime
- 2002-10-11 ES ES02767010T patent/ES2283593T3/es not_active Expired - Lifetime
- 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 |
|---|---|
| US6982258B2 (en) | 2006-01-03 |
| CY1106638T1 (el) | 2012-01-25 |
| JP2005536444A (ja) | 2005-12-02 |
| CA2463505A1 (en) | 2003-04-17 |
| DE60219655D1 (de) | 2007-05-31 |
| JP4436674B2 (ja) | 2010-03-24 |
| ES2283593T3 (es) | 2007-11-01 |
| US20030171342A1 (en) | 2003-09-11 |
| WO2003031400A1 (en) | 2003-04-17 |
| PT1436257E (pt) | 2007-05-31 |
| EP1436257A1 (en) | 2004-07-14 |
| ATE360000T1 (de) | 2007-05-15 |
| DE60219655T2 (de) | 2007-12-27 |
| EP1436257B1 (en) | 2007-04-18 |
| DK1436257T3 (da) | 2007-06-25 |
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