JP2002516307A5 - - Google Patents
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- JP2002516307A5 JP2002516307A5 JP2000550824A JP2000550824A JP2002516307A5 JP 2002516307 A5 JP2002516307 A5 JP 2002516307A5 JP 2000550824 A JP2000550824 A JP 2000550824A JP 2000550824 A JP2000550824 A JP 2000550824A JP 2002516307 A5 JP2002516307 A5 JP 2002516307A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- fluoroalkyl
- fluoroalkenyl
- lower alkyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 description 34
- 125000003709 fluoroalkyl group Chemical group 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 31
- 125000003342 alkenyl group Chemical group 0.000 description 29
- 125000004991 fluoroalkenyl group Chemical group 0.000 description 29
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 26
- 150000002431 hydrogen Chemical group 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
- 229910052717 sulfur Inorganic materials 0.000 description 16
- 239000011593 sulfur Substances 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 239000011710 vitamin D Substances 0.000 description 12
- 229940046008 Vitamin D Drugs 0.000 description 11
- 229930003316 Vitamin D Natural products 0.000 description 11
- 235000019166 vitamin D Nutrition 0.000 description 11
- 201000010099 disease Diseases 0.000 description 8
- 201000002980 hyperparathyroidism Diseases 0.000 description 8
- 210000000988 Bone and Bones Anatomy 0.000 description 7
- 230000028993 immune response Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- -1 vitamin D compound Chemical class 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 230000003463 hyperproliferative Effects 0.000 description 5
- 230000028709 inflammatory response Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000003710 vitamin D derivatives Chemical class 0.000 description 5
- UXFVRWPSABSGRQ-AFWJMSMISA-N (1S,3R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol Chemical group C1C=C2C[C@@H](O)C[C@H](O)[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 UXFVRWPSABSGRQ-AFWJMSMISA-N 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 230000000051 modifying Effects 0.000 description 4
- 201000004681 psoriasis Diseases 0.000 description 4
- 201000000849 skin cancer Diseases 0.000 description 4
- 206010009944 Colon cancer Diseases 0.000 description 3
- 206010060862 Prostate cancer Diseases 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 230000024245 cell differentiation Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 230000003211 malignant Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 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 2
- 0 CC*(*)CC(*C(C)(C)NCC)=C(C)C(C)C(C)=C=CC(C)(CC)C(C)C1=C*1 Chemical compound CC*(*)CC(*C(C)(C)NCC)=C(C)C(C)C(C)=C=CC(C)(CC)C(C)C1=C*1 0.000 description 2
- 206010012601 Diabetes mellitus Diseases 0.000 description 2
- 102000003982 Parathyroid hormone Human genes 0.000 description 2
- 108090000445 Parathyroid hormone Proteins 0.000 description 2
- 210000002307 Prostate Anatomy 0.000 description 2
- 208000006641 Skin Disease Diseases 0.000 description 2
- 206010052779 Transplant rejections Diseases 0.000 description 2
- 230000002708 enhancing Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 239000000199 parathyroid hormone Substances 0.000 description 2
- 229960001319 parathyroid hormone Drugs 0.000 description 2
- 239000008196 pharmacological composition Substances 0.000 description 2
- 230000002829 reduced Effects 0.000 description 2
- 231100000486 side effect Toxicity 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 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 1
- 208000006673 Asthma Diseases 0.000 description 1
- 206010003816 Autoimmune disease Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 206010065687 Bone loss Diseases 0.000 description 1
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 description 1
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 description 1
- 229940107161 Cholesterol Drugs 0.000 description 1
- FMGSKLZLMKYGDP-USOAJAOKSA-N Dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
- DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 description 1
- DNVPQKQSNYMLRS-LNHMRCHQSA-N Ergosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3C([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)=CC=2)CC1 DNVPQKQSNYMLRS-LNHMRCHQSA-N 0.000 description 1
- 206010020583 Hypercalcaemia Diseases 0.000 description 1
- 206010020590 Hypercalciuria Diseases 0.000 description 1
- 206010020707 Hyperparathyroidism primary Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 210000000987 Immune System Anatomy 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 108010081690 Pertussis Toxin Proteins 0.000 description 1
- 206010039073 Rheumatoid arthritis Diseases 0.000 description 1
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H Tricalcium phosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000240 adjuvant Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agents Drugs 0.000 description 1
- 230000001028 anti-proliferant Effects 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011612 calcitriol Substances 0.000 description 1
- 230000003913 calcium metabolism Effects 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,4Z,7S,9Z,12S,13S,14Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 1
- 201000011231 colorectal cancer Diseases 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 230000001969 hypertrophic Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000670 limiting Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000000981 primary hyperparathyroidism Diseases 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Images
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/087,439 US5972917A (en) | 1998-05-29 | 1998-05-29 | 1 α-hydroxy-25-ene-vitamin D, analogs and uses thereof |
| US09/087,439 | 1998-05-29 | ||
| PCT/US1999/012062 WO1999061418A2 (en) | 1998-05-29 | 1999-05-28 | 1α-HYDROXY-25-ENE-VITAMIN D, ANALOGS AND USES THEREOF |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002516307A JP2002516307A (ja) | 2002-06-04 |
| JP2002516307A5 true JP2002516307A5 (US06929797-20050816-C00009.png) | 2006-07-20 |
Family
ID=22205199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000550824A Pending JP2002516307A (ja) | 1998-05-29 | 1999-05-28 | １α−ヒドロキシ−２５−エン−ビタミンＤ、類似体及びその使用 |
Country Status (14)
Families Citing this family (50)
| 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 |
| US20020183288A1 (en) * | 1995-04-03 | 2002-12-05 | Bone Care International, Inc. | Method for treating and preventing hyperparathyroidism |
| US20040043971A1 (en) * | 1995-04-03 | 2004-03-04 | Bone Care International, Inc. | Method of treating and preventing hyperparathyroidism with active vitamin D analogs |
| US20020128240A1 (en) * | 1996-12-30 | 2002-09-12 | Bone Care International, Inc. | Treatment of hyperproliferative diseases using active vitamin D analogues |
| US20030129194A1 (en) * | 1997-02-13 | 2003-07-10 | Bone Care International, Inc. | Targeted therapeutic delivery of vitamin D compounds |
| US6392071B1 (en) * | 1997-03-17 | 2002-05-21 | Wisconsin Alumni: Research Foundation | 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds |
| 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 |
| AUPP405098A0 (en) * | 1998-06-12 | 1998-07-02 | Access Pharmaceuticals Australia Pty Limited | Novel methods of preparation of vitamin b12 derivatives suitable for conjugation to pharmaceuticals |
| ATE309820T1 (de) * | 1999-09-20 | 2005-12-15 | Lilly Co Eli | Verwendung einer parathyroidhormone zur reduktion des krebsrisikos |
| WO2002006218A2 (en) * | 2000-07-18 | 2002-01-24 | Bone Care International, Inc. | STABILIZED 1α-HYDROXY VITAMIN D |
| US7129230B2 (en) | 2001-03-12 | 2006-10-31 | Nestec S.A. | Method and product for treating cancer in pets |
| US6465446B1 (en) * | 2001-03-12 | 2002-10-15 | John C. Dykstra | Treatment of dermatitis by the topical application of Δ5-androstene-3β-ol-7,17 dione and metabolizable precursors thereof |
| US20030191093A1 (en) * | 2001-12-03 | 2003-10-09 | Novacea, Inc. | Pharmaceutical compositions comprising active vitamin D compounds |
| ATE420855T1 (de) * | 2001-12-26 | 2009-01-15 | Hiroaki Takayama | 2-substituierte vitamin-d-derivate |
| KR20040095237A (ko) * | 2002-03-29 | 2004-11-12 | 위스콘신 얼럼나이 리서어치 화운데이션 | 1α-히드록시-2-메틸렌-19-노르-호모프레그나칼시페롤의합성 방법 |
| US7148211B2 (en) * | 2002-09-18 | 2006-12-12 | Genzyme Corporation | Formulation for lipophilic agents |
| US20040058895A1 (en) * | 2002-09-18 | 2004-03-25 | Bone Care International, Inc. | Multi-use vessels for vitamin D formulations |
| US20040053895A1 (en) * | 2002-09-18 | 2004-03-18 | Bone Care International, Inc. | Multi-use vessels for vitamin D formulations |
| EP1556345B1 (en) * | 2002-10-23 | 2010-12-15 | Leo Pharma A/S | Vitamin d analogues, compositions comprising said analogues and their use |
| WO2004047673A2 (en) * | 2002-11-21 | 2004-06-10 | Novacea, Inc. | Treatment of liver disease with active vitamin d compounds |
| CA2528359A1 (en) * | 2003-06-11 | 2004-12-23 | Novacea, Inc. | Treatment of cancer with active vitamin d compounds in combination with radiotherapeutic agents and treatments |
| AU2004247108A1 (en) * | 2003-06-11 | 2004-12-23 | Novacea, Inc | Treatment of immune-mediated disorders with active vitamin D compounds alone or in combination with other therapeutic agents |
| SG110107A1 (en) | 2003-09-24 | 2005-04-28 | Bioxell Spa | Compound and use in treatment |
| 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 |
| US7713951B2 (en) * | 2004-04-09 | 2010-05-11 | Wisconsin Alumni Research Foundation | 2-alkylidene-18,19-dinor-vitamin D compounds |
| WO2005117542A2 (en) * | 2004-05-10 | 2005-12-15 | Novacea, Inc. | Treatment of pancreatic cancer with active vitamin d compounds in combination with other treatments |
| 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 |
| EP1883626B1 (en) | 2005-04-25 | 2017-10-11 | OPKO Ireland Global Holdings, Ltd. | Low-calcemic 16,23-diene 25-oxime analogs of 1alpha,25-dihydroxy vitamin d3 |
| AU2006298960B2 (en) * | 2005-10-06 | 2011-05-12 | Nestec S.A. | Probiotic enterococci for improved immunity |
| US8318459B2 (en) | 2011-02-17 | 2012-11-27 | Purecircle Usa | Glucosyl stevia composition |
| US9392799B2 (en) | 2011-02-17 | 2016-07-19 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US9107436B2 (en) | 2011-02-17 | 2015-08-18 | Purecircle Sdn Bhd | Glucosylated steviol glycoside as a flavor modifier |
| US9386797B2 (en) | 2011-02-17 | 2016-07-12 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| US8257948B1 (en) | 2011-02-17 | 2012-09-04 | Purecircle Usa | Method of preparing alpha-glucosyl Stevia composition |
| US20100009949A1 (en) * | 2006-03-24 | 2010-01-14 | Bioxell S.P.A. | Novel method |
| KR20170096238A (ko) | 2009-01-27 | 2017-08-23 | 베르그 엘엘씨 | 화학요법과 연관된 부작용을 경감시키기 위한 비타민 ｄ３ 및 이의 유사물 |
| JP5978130B2 (ja) | 2009-08-14 | 2016-08-24 | バーグ エルエルシー | 脱毛症を治療するためのビタミンｄ３およびその類似体 |
| WO2011112892A1 (en) | 2010-03-12 | 2011-09-15 | Purecircle Usa Inc. | High-purity steviol glycosides |
| LT2552484T (lt) * | 2010-03-29 | 2020-04-27 | Opko Ireland Global Holdings, Ltd. | Būdai ir kompozicijos, skirti paratiroidų lygiams sumažinti |
| US9029426B2 (en) | 2010-12-13 | 2015-05-12 | Purecircle Sdn Bhd | Highly soluble Rebaudioside D |
| US9510611B2 (en) | 2010-12-13 | 2016-12-06 | Purecircle Sdn Bhd | Stevia composition to improve sweetness and flavor profile |
| US9052308B2 (en) | 2011-01-07 | 2015-06-09 | The General Hospital Corporation | Assays and methods of treatment relating to vitamin D insufficiency |
| EP2661632B1 (en) | 2011-01-07 | 2018-03-07 | The General Hospital Corporation | Assays and methods of treatment relating to vitamin d insufficiency |
| WO2014179737A2 (en) | 2013-05-03 | 2014-11-06 | The General Hospital Corporation | Assays and methods of treatment relating to vitamin d insufficiency |
| MX362676B (es) | 2011-02-10 | 2019-01-31 | Purecircle Usa | Composición de estevia. |
| US9474296B2 (en) | 2011-02-17 | 2016-10-25 | Purecircle Sdn Bhd | Glucosyl stevia composition |
| DE102011112532B4 (de) | 2011-09-05 | 2019-03-21 | Audi Ag | Prüfeinrichtung und Verfahren zum Prüfen von Batteriezellen |
| CN103974628B (zh) | 2012-05-22 | 2019-04-05 | 谱赛科有限责任公司 | 高纯度的甜菊醇糖苷 |
| US9370527B2 (en) * | 2012-12-28 | 2016-06-21 | The Regents Of The University Of Michigan | Amelioration of intestinal fibrosis and treatment of Crohn's disease |
| EP3003497B1 (en) | 2013-05-29 | 2024-02-14 | BPGbio, Inc. | Preventing or mitigating chemotherapy induced alopecia using vitamin d |
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| US4202829A (en) * | 1978-01-05 | 1980-05-13 | Wisconsin Alumni Research Foundation | Process for preparing 1α-hydroxylated compounds |
| US4260549A (en) * | 1979-05-21 | 1981-04-07 | Wisconsin Alumni Research Foundation | Process for preparing 1α-hydroxylated compounds |
| US4195027A (en) * | 1978-01-16 | 1980-03-25 | Wisconsin Alumni Research Foundation | Process for preparing 1α-hydroxylated compounds |
| US4225596A (en) * | 1978-10-13 | 1980-09-30 | Wisconsin Alumni Research Foundation | Method for treating calcium imbalance and improving calcium absorption in mammals |
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| DK160817C (da) * | 1979-10-23 | 1991-10-07 | Teijin Ltd | Fremgangsmaade til fremstilling af vitamin d3 forbindelser |
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| US4689180A (en) * | 1984-01-30 | 1987-08-25 | Wisconsin Alumni Research Foundation | 1α,25-dihydroxy-22Z-dehydroxyvitamin D compound |
| US4481198A (en) * | 1984-02-13 | 1984-11-06 | Wisconsin Alumni Research Foundation | Vitamin D metabolism inhibitor |
| US4555364A (en) * | 1984-11-01 | 1985-11-26 | Wisconsin Alumni Research Foundation | Method for preparing 1-hydroxyvitamin D compounds |
| US4554106A (en) * | 1984-11-01 | 1985-11-19 | Wisconsin Alumni Research Foundation | Method for preparing 1α-hydroxyvitamin D compounds |
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| US5250523A (en) * | 1988-04-29 | 1993-10-05 | Wisconsin Alumni Research Foundation | Side chain unsaturated 1α-hydroxyvitanim D homologs |
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| US5098899A (en) * | 1989-03-06 | 1992-03-24 | Trustees Of Boston University | Method for therapeutically treating psoriatic arthritis using vitamin D analogues and metabolites |
| CA1333616C (en) * | 1989-03-09 | 1994-12-20 | Hector F. Deluca | 19-nor-vitamin d compounds |
| GB2229921B (en) * | 1989-04-05 | 1992-12-16 | Chugai Pharmaceutical Co Ltd | Treatment for hyperparathyroidism with use of vitamin d derivatives |
| GB8915770D0 (en) * | 1989-07-10 | 1989-08-31 | Leo Pharm Prod Ltd | Chemical compounds |
| US5518725A (en) * | 1989-09-25 | 1996-05-21 | University Of Utah Research Foundation | Vaccine compositions and method for induction of mucosal immune response via systemic vaccination |
| US5562910A (en) * | 1989-09-25 | 1996-10-08 | University Of Utah Research Foundation | Vaccine compositions and method for enhancing an immune response |
| DE69033541D1 (de) * | 1989-09-25 | 2000-06-15 | Univ Utah Res Found | Verwendung von steroidhormonen in zubereitungen zur induzierung von t-zell-lymphokin-erzeugung |
| US5260290A (en) * | 1990-02-14 | 1993-11-09 | Wisconsin Alumni Research Foundation | Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives |
| GB9007236D0 (en) * | 1990-03-30 | 1990-05-30 | Leo Pharm Prod Ltd | Chemical compounds |
| ES2073661T3 (es) * | 1990-04-27 | 1995-08-16 | Duphar Int Res | Metodo para la isomerizacion fotoquimica de compuestos organicos bajo la influencia de un fotosensibilizador. |
| ES2140433T3 (es) * | 1992-02-27 | 2000-03-01 | Duphar Int Res | Metodo de preparar esteroides 9beta, 10alfa-5,7-dienicos. |
| DE4220757A1 (de) * | 1992-06-24 | 1994-01-05 | Schering Ag | Derivate in der Vitamin D-Reihe mit Modifikationen in der 20-Position, Verfahren zu ihrer Herstellung, Zwischenprodukte für dieses Verfahren, diese Derivate enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| GB9220439D0 (en) * | 1992-09-28 | 1992-11-11 | Leo Pharm Prod Ltd | Chemical compounds |
| US5753638A (en) * | 1992-10-07 | 1998-05-19 | Hoffmann-La Roche Inc. | Method of treating hyperproliferative skin disease with Vitamin D3 fluorinated analogs |
| GB9223061D0 (en) * | 1992-11-04 | 1992-12-16 | Leo Pharm Prod Ltd | Chemical compounds |
| US5449668A (en) * | 1993-06-04 | 1995-09-12 | Duphar International Research B.V. | Vitamin D compounds and method of preparing these compounds |
| US5665387A (en) * | 1994-09-01 | 1997-09-09 | K.U. Leuven Research & Development | Methods and compositions for primary and secondary prevention of autoimmune diabetes |
| US5559107A (en) * | 1994-10-20 | 1996-09-24 | Gates; Stephen | Regulation of immune response |
| CZ291915B6 (cs) * | 1995-06-14 | 2003-06-18 | Schering Aktiengesellschaft | Deriváty vitaminu D se substituenty v poloze C-25, způsob jejich výroby, meziprodukty pro tento způsob, jakož i jejich použití pro výrobu léčiv |
| GB9524812D0 (en) * | 1995-12-05 | 1996-02-07 | Leo Pharm Prod Ltd | Chemical compounds |
| US5716946A (en) * | 1996-02-13 | 1998-02-10 | Wisconsin Alumni Research Foundation | Multiple sclerosis treatment |
-
1998
- 1998-05-29 US US09/087,439 patent/US5972917A/en not_active Expired - Fee Related
-
1999
- 1999-05-28 ES ES99928357T patent/ES2211107T3/es not_active Expired - Lifetime
- 1999-05-28 BR BR9910672-8A patent/BR9910672A/pt not_active Application Discontinuation
- 1999-05-28 DE DE69912598T patent/DE69912598T2/de not_active Expired - Lifetime
- 1999-05-28 DK DK99928357T patent/DK1082298T3/da active
- 1999-05-28 CN CNB998067873A patent/CN1238341C/zh not_active Expired - Fee Related
- 1999-05-28 EP EP99928357A patent/EP1082298B1/en not_active Expired - Lifetime
- 1999-05-28 AT AT99928357T patent/ATE253554T1/de not_active IP Right Cessation
- 1999-05-28 PT PT99928357T patent/PT1082298E/pt unknown
- 1999-05-28 CA CA002333270A patent/CA2333270A1/en not_active Abandoned
- 1999-05-28 JP JP2000550824A patent/JP2002516307A/ja active Pending
- 1999-05-28 AU AU45445/99A patent/AU754211B2/en not_active Ceased
- 1999-05-28 IL IL13935399A patent/IL139353A/xx not_active IP Right Cessation
- 1999-05-28 WO PCT/US1999/012062 patent/WO1999061418A2/en active IP Right Grant
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