DE60127964T2 - Verwendung von 2-alpha-methyl-19-nor-20(s)-1-alpha,25-dihydroxyvitamin als knochenersatz - Google Patents
Verwendung von 2-alpha-methyl-19-nor-20(s)-1-alpha,25-dihydroxyvitamin als knochenersatz Download PDFInfo
- Publication number
- DE60127964T2 DE60127964T2 DE60127964T DE60127964T DE60127964T2 DE 60127964 T2 DE60127964 T2 DE 60127964T2 DE 60127964 T DE60127964 T DE 60127964T DE 60127964 T DE60127964 T DE 60127964T DE 60127964 T2 DE60127964 T2 DE 60127964T2
- Authority
- DE
- Germany
- Prior art keywords
- bone
- methyl
- compound
- dihydroxyvitamin
- activity
- 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
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- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000011612 calcitriol Substances 0.000 claims description 21
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- 238000004519 manufacturing process Methods 0.000 claims description 3
- 210000003127 knee Anatomy 0.000 claims description 2
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- 239000011575 calcium Substances 0.000 description 27
- 229910052791 calcium Inorganic materials 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 12
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- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 10
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 10
- 210000002966 serum Anatomy 0.000 description 10
- 239000011710 vitamin D Substances 0.000 description 10
- 235000019166 vitamin D Nutrition 0.000 description 10
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- GMRQFYUYWCNGIN-ZVUFCXRFSA-N 1,25-dihydroxy vitamin D3 Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-ZVUFCXRFSA-N 0.000 description 9
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- PKFBWEUIKKCWEW-WEZTXPJVSA-N (1r,3r)-5-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol Chemical class C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1C[C@@H](O)C[C@H](O)C1 PKFBWEUIKKCWEW-WEZTXPJVSA-N 0.000 description 2
- 208000010392 Bone Fractures Diseases 0.000 description 2
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- 208000029725 Metabolic bone disease Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 206010047626 Vitamin D Deficiency Diseases 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
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- HKXBNHCUPKIYDM-CGMHZMFXSA-N doxercalciferol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C HKXBNHCUPKIYDM-CGMHZMFXSA-N 0.000 description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
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- GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 description 1
- ZGLHBRQAEXKACO-XJRQOBMKSA-N 1alpha,25-dihydroxyvitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@H](C)C(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C ZGLHBRQAEXKACO-XJRQOBMKSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OZPNRDQPQFOURL-QVRMMZLXSA-N C[C@@H](CCCC(C)(C)O)C(CC1)[C@@](C)(CCC2)C1/C2=C/C=C(\C[C@H]([C@H]1C)O)/C[C@H]1O Chemical compound C[C@@H](CCCC(C)(C)O)C(CC1)[C@@](C)(CCC2)C1/C2=C/C=C(\C[C@H]([C@H]1C)O)/C[C@H]1O OZPNRDQPQFOURL-QVRMMZLXSA-N 0.000 description 1
- 208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 description 1
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- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 description 1
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- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical group OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- 208000032349 type 2B vitamin D-dependent rickets Diseases 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22D—CASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
- B22D17/00—Pressure die casting or injection die casting, i.e. casting in which the metal is forced into a mould under high pressure
- B22D17/20—Accessories: Details
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
-
- 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
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22D—CASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
- B22D17/00—Pressure die casting or injection die casting, i.e. casting in which the metal is forced into a mould under high pressure
- B22D17/20—Accessories: Details
- B22D17/22—Dies; Die plates; Die supports; Cooling equipment for dies; Accessories for loosening and ejecting castings from dies
- B22D17/2236—Equipment for loosening or ejecting castings from dies
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22D—CASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
- B22D17/00—Pressure die casting or injection die casting, i.e. casting in which the metal is forced into a mould under high pressure
- B22D17/20—Accessories: Details
- B22D17/22—Dies; Die plates; Die supports; Cooling equipment for dies; Accessories for loosening and ejecting castings from dies
- B22D17/24—Accessories for locating and holding cores or inserts
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Mechanical Engineering (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/616,778 US6306844B1 (en) | 1997-03-17 | 2000-07-14 | Use of 2α-methyl-19-nor-20(S)-1α, 25-dihydroxyvitamin D3 to increase bone strength |
| US616778 | 2000-07-14 | ||
| PCT/US2001/021660 WO2002005824A1 (en) | 2000-07-14 | 2001-07-10 | USE OF 2α-METHYL-19-NOR-20(S)-1α,25-DIHYDROXYVITAMIN D3 TO INCREASE BONE STRENGTH |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60127964D1 DE60127964D1 (de) | 2007-05-31 |
| DE60127964T2 true DE60127964T2 (de) | 2008-01-17 |
Family
ID=24470903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60127964T Expired - Lifetime DE60127964T2 (de) | 2000-07-14 | 2001-07-10 | Verwendung von 2-alpha-methyl-19-nor-20(s)-1-alpha,25-dihydroxyvitamin als knochenersatz |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US6306844B1 (https=) |
| EP (1) | EP1305030B1 (https=) |
| JP (1) | JP4955895B2 (https=) |
| KR (1) | KR100572958B1 (https=) |
| CN (1) | CN1250225C (https=) |
| AT (1) | ATE359796T1 (https=) |
| AU (2) | AU7330301A (https=) |
| BR (1) | BR0112453A (https=) |
| CA (1) | CA2416187A1 (https=) |
| DE (1) | DE60127964T2 (https=) |
| DK (1) | DK1305030T3 (https=) |
| ES (1) | ES2286129T3 (https=) |
| IL (2) | IL153908A0 (https=) |
| MX (1) | MXPA03000405A (https=) |
| NZ (1) | NZ524018A (https=) |
| WO (1) | WO2002005824A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6392071B1 (en) * | 1997-03-17 | 2002-05-21 | Wisconsin Alumni: Research Foundation | 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds |
| MXPA03000406A (es) * | 2000-07-14 | 2003-06-06 | Wisconsin Alumni Res Found | Uso de 2-metilen-19-nor-20(s)-1 alfa,25-dihidroxivitamina d3 para incrementar la resistencia de los huesos. |
| US7858602B2 (en) * | 2000-10-16 | 2010-12-28 | Rodriguez Victorio C | Therapeutic and prophylactic uses of cell specific carbonic anhydrase enzymes in treating aging disorders due to oxidative stress and as growth factors of stem cells |
| US20030195175A1 (en) * | 2002-03-25 | 2003-10-16 | Deluca Hector F. | Use of carbon-2-modified-vitamin D analogs to induce the formation of new bone |
| HK1079766B (zh) | 2002-03-29 | 2007-05-25 | 威斯康星校友研究基金会 | 合成1α-羟基-2-亚甲基-19-去甲-高孕钙化醇的方法 |
| US6846811B2 (en) * | 2002-04-22 | 2005-01-25 | Wisconsin Alumni Research Foundation | (20S) 1α-hydroxy-2α-methyl and 2β-methyl-19-nor-vitamin D3 and their uses |
| WO2004076468A1 (ja) | 2003-02-25 | 2004-09-10 | Kobe Tennenbutsu Kagaku Kabushiki Kaisha | ビタミンｄ誘導体を合成するための新規な中間体 |
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| US7214671B2 (en) * | 2004-02-19 | 2007-05-08 | Wisconsin Alumni Research Foundation | Use of 2-methylene-19-nor-20(S)-1α,25-dihydroxyvitamin D3 for the prophylaxis of bone diseases |
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| NZ570711A (en) | 2006-04-06 | 2012-10-26 | Wisconsin Alumni Res Found | 2-Substituted-1alpha, 25-dihydroxy-19,26,27-trinor vitamin D analogs and uses thereof |
| MX2008012912A (es) * | 2006-04-06 | 2008-11-26 | Wisconsin Alumni Res Found | Analogos de 2-metilen-1a,25-dihidroxi-19,21-dinorvitamina d3 y sus usos. |
| EP2021321B1 (en) * | 2006-04-06 | 2012-06-20 | Wisconsin Alumni Research Foundation | 2-methylene-1alpha,25-dihydroxy-18,19,21-trinorvitamin d3 and uses thereof |
| WO2008035207A2 (en) * | 2006-04-06 | 2008-03-27 | Wisconsin Alumni Research Foundation | 2-methylene-1alpha-hydroxy-19,21-dinorvitamin d3 analogs and uses thereof |
| NZ570712A (en) * | 2006-04-06 | 2011-11-25 | Wisconsin Alumni Res Found | 2-methylene-1alpha-hydroxy-18,19,21-trinorvitamin D3 analogs and uses thereof |
| EP2001860A2 (en) * | 2006-04-06 | 2008-12-17 | Wisconsin Alumni Research Foundation | 19-nor-vitamin d analogs with 1,2,or 3,2 heterocyclic ring |
| EP2004597B1 (en) * | 2006-04-10 | 2011-01-26 | Wisconsin Alumni Research Foundation | 1alpha-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin d compounds with a 1,1-dimethylpropyl side chain |
| US20080031957A1 (en) * | 2006-05-15 | 2008-02-07 | Deluca Hector F | Pulmonary delivery of 1alpha,25-dihydroxyvitamin D3 and co-administration of parathyroid hormone or calcitonin |
| US8222236B2 (en) * | 2008-07-10 | 2012-07-17 | Wisconsin Alumni Research Foundation | 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs |
| US7888339B2 (en) * | 2008-07-10 | 2011-02-15 | Wisconsin Alumni Research Foundation | 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs |
| US7893043B2 (en) * | 2008-07-10 | 2011-02-22 | Wisconsin Alumni Research Foundation | 2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-vitamin D analogs |
| AU2010281391B2 (en) * | 2009-08-03 | 2015-05-07 | Wisconsin Alumni Research Foundation | Method of preventing renal disease and treating symptoms thereof |
| CA2777938C (en) | 2009-10-21 | 2017-11-14 | Wisconsin Alumni Research Foundation | Method of preventing type 1 diabetes |
| US8604009B2 (en) * | 2010-03-23 | 2013-12-10 | Wisconsin Alumni Research Foundation | (20S)-2-methylene-19-nor-22-dimethyl-1α,25-dihydroxyvitamin D3 and (20R)-2-methylene-19-nor-22-dimethyl-1α,25-hydroxyvitamin D3 |
| US8664206B2 (en) | 2010-03-23 | 2014-03-04 | Wisconsin Alumni Research Foundation | Diastereomers of 2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D3 |
| CA2793727C (en) * | 2010-03-23 | 2017-01-03 | Wisconsin Alumni Research Foundation | Diastereomers of 2-methylene-19-nor-22-methyl-1.alpha.,25-dihydroxyvitamin d3 |
| US20130295083A1 (en) * | 2012-05-02 | 2013-11-07 | Wisconsin Alumni Research Foundation | 2a-Methyl-19-nor-(20S)-1a,25-dihydroxyvitamin D3 (2AMD) or 2 methylene-19-nor-(20S)-1a,25-dihydroxyvitamin D3 (2MD) Support Survival and Function of Transplanted Islet Cells In Type 1 Diabetes |
| CN104394871A (zh) | 2012-06-29 | 2015-03-04 | 威斯康星旧生研究基金会 | 2-亚甲基-19-去甲-(20S)-1α,25-二羟基维生素D3治疗继发性甲状旁腺功能亢进的用途 |
| US10369161B2 (en) | 2014-12-30 | 2019-08-06 | Wisconsin Alumni Research Foundation | Use of 2-methylene-19-NOR-(20S)-1-alpha,25-dihydroxyvitamin D3 to treat primary hyperparathyroidism |
| US9539264B2 (en) | 2014-12-30 | 2017-01-10 | Wisconsin Alumni Research Foundation | Use of 2-methylene-19-nor-(20S)-1-alpha,25-dihydroxyvitamin D3 to treat secondary hyperparathyroidism in patients previously treated with calcimimetics |
| WO2017184262A1 (en) * | 2016-04-18 | 2017-10-26 | Wisconsin Alumni Research Foundation | Use of 2amd and 2md to treat fibrosis |
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| IL67153A (en) | 1981-11-02 | 1986-12-31 | Res Inst Medicine Chem | Intermediates in the production of vitamin d analogues and method for their production |
| US4666634A (en) | 1984-12-05 | 1987-05-19 | Chugai Seiyaku Kabushiki Kaisha | vitamin D3 derivatives having a substituent at 2-position |
| GB8904154D0 (en) | 1989-02-23 | 1989-04-05 | Leo Pharm Prod Ltd | Chemical compounds |
| NZ232734A (en) | 1989-03-09 | 1991-11-26 | Wisconsin Alumni Res Found | 19-nor vitamin d derivatives and pharmaceutical compositions |
| US5246925A (en) | 1989-03-09 | 1993-09-21 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D compounds for use in treating hyperparathyroidism |
| CA1333616C (en) | 1989-03-09 | 1994-12-20 | Hector F. Deluca | 19-nor-vitamin d compounds |
| AU649057B2 (en) | 1990-08-24 | 1994-05-12 | Wisconsin Alumni Research Foundation | Methods and compositions containing vitamin D compounds for improvement of skin conditions |
| ES2123505T3 (es) | 1990-09-07 | 1999-01-16 | Wisconsin Alumni Res Found | Nuevo uso de compuestos de 19-nor-vitamina d 1alfa-hidroxilada para tratar la psoriasis. |
| AU650751B2 (en) | 1991-05-28 | 1994-06-30 | Wisconsin Alumni Research Foundation | Novel synthesis of 19-nor vitamin D compounds |
| US5086191A (en) | 1991-05-28 | 1992-02-04 | Wisconsin Alumni Research Foundation | Intermediates for the synthesis of 19-nor vitamin D compounds |
| EP0619306B1 (en) | 1993-04-05 | 1996-09-11 | Wisconsin Alumni Research Foundation | 19-Nor-vitamin D3 compounds with substituent at 2-position |
| WO1996001811A1 (en) | 1994-07-11 | 1996-01-25 | The Johns-Hopkins University | 2-substituted 1,25-dihydroxyvitamin d3 derivatives |
| US6316642B1 (en) * | 1997-03-17 | 2001-11-13 | Wisconsin Alumni Research Foundation | 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds |
| US5945410A (en) * | 1997-03-17 | 1999-08-31 | Wisconsin Alumni Research Foundation | 2-alkyl-19-nor-vitamin D compounds |
| US5962707A (en) * | 1998-08-18 | 1999-10-05 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D3 compounds with calcemic activity |
-
2000
- 2000-07-14 US US09/616,778 patent/US6306844B1/en not_active Expired - Lifetime
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2001
- 2001-07-10 AU AU7330301A patent/AU7330301A/xx active Pending
- 2001-07-10 AT AT01952566T patent/ATE359796T1/de active
- 2001-07-10 ES ES01952566T patent/ES2286129T3/es not_active Expired - Lifetime
- 2001-07-10 AU AU2001273303A patent/AU2001273303B8/en not_active Ceased
- 2001-07-10 DK DK01952566T patent/DK1305030T3/da active
- 2001-07-10 DE DE60127964T patent/DE60127964T2/de not_active Expired - Lifetime
- 2001-07-10 EP EP01952566A patent/EP1305030B1/en not_active Expired - Lifetime
- 2001-07-10 CN CNB018155332A patent/CN1250225C/zh not_active Expired - Fee Related
- 2001-07-10 KR KR1020037000542A patent/KR100572958B1/ko not_active Expired - Fee Related
- 2001-07-10 MX MXPA03000405A patent/MXPA03000405A/es active IP Right Grant
- 2001-07-10 JP JP2002511756A patent/JP4955895B2/ja not_active Expired - Fee Related
- 2001-07-10 BR BR0112453-6A patent/BR0112453A/pt not_active Application Discontinuation
- 2001-07-10 NZ NZ524018A patent/NZ524018A/en not_active IP Right Cessation
- 2001-07-10 CA CA002416187A patent/CA2416187A1/en not_active Abandoned
- 2001-07-10 WO PCT/US2001/021660 patent/WO2002005824A1/en not_active Ceased
- 2001-07-10 IL IL15390801A patent/IL153908A0/xx unknown
- 2001-10-19 US US10/045,941 patent/US20020151528A1/en not_active Abandoned
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2003
- 2003-01-13 IL IL153908A patent/IL153908A/en not_active IP Right Cessation
- 2003-09-29 US US10/673,618 patent/US6939868B2/en not_active Expired - Lifetime
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|---|---|
| DK1305030T3 (da) | 2007-09-17 |
| JP4955895B2 (ja) | 2012-06-20 |
| DE60127964D1 (de) | 2007-05-31 |
| US20020151528A1 (en) | 2002-10-17 |
| HK1066487A1 (en) | 2005-03-24 |
| US20040072804A1 (en) | 2004-04-15 |
| CN1501803A (zh) | 2004-06-02 |
| CA2416187A1 (en) | 2002-01-24 |
| KR100572958B1 (ko) | 2006-04-24 |
| ATE359796T1 (de) | 2007-05-15 |
| JP2004509853A (ja) | 2004-04-02 |
| NZ524018A (en) | 2006-06-30 |
| AU2001273303B2 (en) | 2006-02-02 |
| CN1250225C (zh) | 2006-04-12 |
| KR20030016402A (ko) | 2003-02-26 |
| US20060003973A1 (en) | 2006-01-05 |
| AU2001273303B8 (en) | 2006-03-09 |
| AU7330301A (en) | 2002-01-30 |
| US6306844B1 (en) | 2001-10-23 |
| EP1305030A1 (en) | 2003-05-02 |
| ES2286129T3 (es) | 2007-12-01 |
| EP1305030B1 (en) | 2007-04-18 |
| IL153908A0 (en) | 2003-07-31 |
| WO2002005824A1 (en) | 2002-01-24 |
| MXPA03000405A (es) | 2003-06-06 |
| IL153908A (en) | 2009-08-03 |
| BR0112453A (pt) | 2003-08-19 |
| US6939868B2 (en) | 2005-09-06 |
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