NO321925B1 - 2-Alkyl-19-nor-vitamin D-forbindelser samt anvendelse derav ved fremstilling av farmasoytiske blandinger og slike blandinger - Google Patents
2-Alkyl-19-nor-vitamin D-forbindelser samt anvendelse derav ved fremstilling av farmasoytiske blandinger og slike blandinger Download PDFInfo
- Publication number
- NO321925B1 NO321925B1 NO19994489A NO994489A NO321925B1 NO 321925 B1 NO321925 B1 NO 321925B1 NO 19994489 A NO19994489 A NO 19994489A NO 994489 A NO994489 A NO 994489A NO 321925 B1 NO321925 B1 NO 321925B1
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- Norway
- Prior art keywords
- vitamin
- methyl
- compounds
- dihydroxyvitamin
- group
- Prior art date
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
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- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 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
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/819,694 US5945410A (en) | 1997-03-17 | 1997-03-17 | 2-alkyl-19-nor-vitamin D compounds |
PCT/US1998/002975 WO1998041500A1 (en) | 1997-03-17 | 1998-02-11 | 2-alkyl-19-nor-vitamin d compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
NO994489L NO994489L (no) | 1999-09-16 |
NO994489D0 NO994489D0 (no) | 1999-09-16 |
NO321925B1 true NO321925B1 (no) | 2006-07-24 |
Family
ID=25228795
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19994489A NO321925B1 (no) | 1997-03-17 | 1999-09-16 | 2-Alkyl-19-nor-vitamin D-forbindelser samt anvendelse derav ved fremstilling av farmasoytiske blandinger og slike blandinger |
Country Status (15)
Country | Link |
---|---|
US (3) | US5945410A (ja) |
EP (1) | EP0971888B1 (ja) |
JP (2) | JP3786712B2 (ja) |
KR (1) | KR100345820B1 (ja) |
AT (1) | ATE253046T1 (ja) |
AU (1) | AU714390B2 (ja) |
BR (1) | BR9808010B1 (ja) |
CA (1) | CA2272745C (ja) |
DE (1) | DE69819312T2 (ja) |
DK (1) | DK0971888T3 (ja) |
ES (1) | ES2206893T3 (ja) |
NO (1) | NO321925B1 (ja) |
NZ (1) | NZ337262A (ja) |
PT (1) | PT971888E (ja) |
WO (1) | WO1998041500A1 (ja) |
Families Citing this family (104)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19619036A1 (de) * | 1996-04-30 | 1997-11-13 | Schering Ag | Neue Vitamin D-Derivate mit carbo- oder heterocyclischen Substituenten an C-25, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
US6306844B1 (en) | 1997-03-17 | 2001-10-23 | Wisconsin Alumni Research Foundation | Use of 2α-methyl-19-nor-20(S)-1α, 25-dihydroxyvitamin D3 to increase bone strength |
US6316642B1 (en) * | 1997-03-17 | 2001-11-13 | Wisconsin Alumni Research Foundation | 26,27-Homologated-20-EPI-2alkyl-19-nor-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 |
MA26481A1 (fr) * | 1997-04-21 | 2004-12-20 | Hoffmann La Roche | Derives d'arylsecocholadiene |
US6538145B2 (en) * | 1998-02-24 | 2003-03-25 | Chugai Seiyaku Kabushiki Kaisha | 24-hydroxy vitamin D derivatives |
US6114317A (en) | 1998-05-21 | 2000-09-05 | Wisconsin Alumni Research Foundation | Method of locking 1α-OH of vitamin D compounds in axial orientation |
DE19935771A1 (de) * | 1999-07-23 | 2001-02-01 | Schering Ag | Neue Vitamin D-Derivate mit cyclischen Substrukturen in den Seitenketten, Verfahren und Zwischenprodukte zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
US20030188756A1 (en) * | 2002-08-19 | 2003-10-09 | Cantorna Margherita T | Treatment of inflammatory bowel disease with vitamin d compounds |
EP1284259A4 (en) * | 2000-05-23 | 2009-11-11 | Hiroaki Takayama | 5,6-TRANS-2-alkyl-vitamin D derivatives |
IL152942A (en) * | 2000-05-31 | 2007-09-20 | Wisconsin Alumni Res Found | Compounds 2 - Ethyl and 2 - Ethylaidine - 19 - Nur - Vitamin D and pharmaceutical preparations containing them |
EP1524264A3 (en) * | 2000-05-31 | 2010-01-20 | Wisconsin Alumni Research Foundation | 2-ethylidene-19-nor-vitamin D compounds |
JP4022144B2 (ja) | 2000-09-08 | 2007-12-12 | ウィスコンシン・アルムニ・リサーチ・ファウンデーション | 1アルファ−ヒドロキシ−2−メチレン−19−ノル−ホモプレグナカルシフェロール及びその療法的適用 |
US6627622B2 (en) * | 2002-02-18 | 2003-09-30 | Wisconsin Alumni Research Foundation | (20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses |
US6566352B1 (en) | 2002-02-18 | 2003-05-20 | Wisconsin Alumni Research Foudation | 1 α-hydroxy-2-methylene-19-nor-pregnacalciferol and its uses |
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 |
EP1490332B1 (en) | 2002-03-29 | 2006-11-29 | Wisconsin Alumni Research Foundation | Method of synthesizing 1-alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol |
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 |
US6723755B2 (en) | 2002-06-12 | 2004-04-20 | Piotr Chomczynski | Method of treating rosacea |
JP2006506445A (ja) | 2002-08-28 | 2006-02-23 | ホリス − イーデン ファーマスーティカルズ、 インコーポレイテッド | 治療処置の方法 |
US7402688B2 (en) * | 2002-10-10 | 2008-07-22 | Wisconsin Alumni Research Foundation | 2,2-Di-substituted 1alpha,25-dihydroxy-19-norvitamin D derivative |
BRPI0407104A (pt) * | 2003-01-30 | 2006-01-24 | Teijin Pharma Ltd | Composto, agente terapêutico, composição farmacêutica, e, processo para sintetizar um composto |
WO2004067504A1 (ja) * | 2003-01-31 | 2004-08-12 | Chugai Seiyaku Kabushiki Kaisha | 2位置換ビタミンd誘導体 |
JP4469794B2 (ja) | 2003-02-25 | 2010-05-26 | 神戸天然物化学株式会社 | ビタミンd誘導体を合成するための新規な中間体 |
AU2004230948A1 (en) * | 2003-04-10 | 2004-10-28 | Wisconsin Alumni Research Foundation | 2-propylidene-19-nor-vitamin D compounds |
US20070032461A1 (en) * | 2003-04-30 | 2007-02-08 | Bioxell S.P.A. | 1,3 Aclyated 24-keto-vitamin d3 compounds and methods of use thereof |
US20050059641A1 (en) * | 2003-06-17 | 2005-03-17 | Aphios Corporation | Compositions and methods for treating and preventing cancer using analogs of vitamin D |
US6894037B2 (en) * | 2003-07-03 | 2005-05-17 | Wisconsin Alumni Research Foundation | 2-methylene-19-nor-20(S)-25-methyl-1α-hydroxycalciferol and its uses |
MXPA06000060A (es) * | 2003-07-03 | 2006-04-07 | Wisconsin Alumni Res Found | 2-metilen-19-nor-20(s)-25-metil-1alfa-hidroxicalciferol y sus usos. |
ATE537834T1 (de) * | 2003-08-20 | 2012-01-15 | Wisconsin Alumni Res Found | 2-methylen-19-nor-vitamin d2-verbindungen |
US8188064B2 (en) * | 2003-11-25 | 2012-05-29 | Wisconsin Alumni Research Foundation | Vitamin D analogs for obesity prevention and treatment |
US7053075B2 (en) * | 2003-11-25 | 2006-05-30 | Deluca Hector F | Methods for reducing body fat using vitamin D compounds |
US7915242B2 (en) * | 2004-02-17 | 2011-03-29 | Wisconsin Alumni Research Foundation | Vitamin D receptor antagonists and their use in treating asthma |
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 |
US7812057B2 (en) * | 2004-08-25 | 2010-10-12 | Molecular Research Center, Inc. | Cosmetic compositions |
AU2005309791A1 (en) * | 2004-11-22 | 2006-06-01 | Wisconsin Alumni Research Foundation | 2-methylene-19,26,27-trinor-(20S)-1alpha-hydroxyvitamin D3 and its uses |
DE602005026694D1 (de) * | 2004-11-22 | 2011-04-14 | Wisconsin Alumni Res Found | 2-methylen-19,21-dinor-1alpha-hydroxy-bishomopregnacalciferol |
US7238681B2 (en) * | 2004-11-22 | 2007-07-03 | Wisconsin Alumni Research Foundation | 2-Methylene-18,19-dinor-1α-hydroxy-homopregnacalciferol and its uses |
CA2588406A1 (en) * | 2004-11-22 | 2006-06-01 | Wisconsin Alumni Research Foundation | 2-.alpha.-methyl and 2-.beta.-methyl analogs of 19,26,27-trinor-(20s-1.alpha.-hydroxyvitamin d3 and their uses |
US8222235B2 (en) * | 2004-11-22 | 2012-07-17 | Wisconsin Alumni Research Foundation | 2-methylene-19-nor-(20R)-1α-hydroxy-bishomopregnacalciferol |
MX2007006096A (es) * | 2004-11-22 | 2007-07-11 | Wisconsin Alumni Res Found | 2-metilen-19-nor-(20s)-1a-hidroxi-trishomopregnacalciferol. |
DE602005021702D1 (de) * | 2004-11-22 | 2010-07-15 | Wisconsin Alumni Res Found | 2-methylen-19-nor-1alpha-hydroxy-17-enhormopregnacalziferol und anwendungen davon |
NZ555279A (en) * | 2004-11-22 | 2010-12-24 | Wisconsin Alumni Res Found | 2alpha-methyl-19-nor-1alpha-hydroxy-homopregnacalciferol and its uses |
MX2007006542A (es) * | 2004-11-22 | 2007-07-25 | Wisconsin Alumni Res Found | 2a-metil-19-nor-(20s)-1a-hidroxi-bishomopregnacalciferol y sus usos. |
WO2006086613A2 (en) * | 2005-02-11 | 2006-08-17 | Wisconsin Alumni Research Foundation | 2-METHYLENE-19-NOR- (20S-24S) - 1α, 25-D IHYDROXYVITAMIN-D2 |
JP5036565B2 (ja) * | 2005-02-11 | 2012-09-26 | ウイスコンシン アラムニ リサーチ ファンデーション | 2−メチレン−19−ノル−(20S−24エピ)−1α,25−ジヒドロキシビタミン−D2 |
JP4961562B2 (ja) * | 2005-03-04 | 2012-06-27 | 国立大学法人 東京医科歯科大学 | 19−ノルビタミンd誘導体 |
AU2006230296B2 (en) * | 2005-03-29 | 2011-07-07 | Wisconsin Alumni Research Foundation | 2-methylene-19-nor-(23s)-25-dehydro-1alpha-hydroxyvitamin D3-26,23-lactone and 2-methylene-19-nor-(23R)-25-dehydro-1alpha-hydroxyvitamin D3-26,23-lactone |
JP2008542201A (ja) * | 2005-05-03 | 2008-11-27 | ウイスコンシン アラムニ リサーチ ファンデーション | 19,26,27−トリノル−1α,25−ジヒドロキシビタミンD3化合物 |
NZ567015A (en) * | 2005-08-30 | 2010-12-24 | Wisconsin Alumni Res Found | Des-C,D analogs of 1alpha,25-dihydroxy-19-norvitamin D3 |
AU2006295085A1 (en) * | 2005-09-22 | 2007-04-05 | Wisconsin Alumni Research Foundation | 19,23,24,25,26,27-hexanor-1alpha-hydroxyvitamin D3 |
US7528122B2 (en) * | 2006-02-02 | 2009-05-05 | Wisconsin Alumni Research Foundation | Vitamin D analog—NEL, methods and uses thereof |
US7803789B2 (en) | 2006-02-02 | 2010-09-28 | Wisconsin Alumni Research Foundation | Vitamin D analog—RAK, methods and uses thereof |
MX2008012701A (es) * | 2006-04-05 | 2009-01-07 | Wisconsin Alumni Res Found | Compuestos de 1-alfa-hidroxi-2-(3'-hidroxipropiliden)-19-nor-vitam ina d y metodos de elaboracion y tratamiento de los mismos. |
US20090281340A1 (en) * | 2006-04-05 | 2009-11-12 | Deluca Hector F | 1alpha-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin d compounds and methods of making and treatment thereof |
EP2021320A2 (en) | 2006-04-06 | 2009-02-11 | Wisconsin Alumni Research Foundation | 2-substituted-1alpha, 25-dihydroxy-19,26,27-trinor vitamin d analogs and uses thereof |
JP2009532459A (ja) * | 2006-04-06 | 2009-09-10 | ウイスコンシン アラムニ リサーチ ファンデーション | 1,2または3,2複素環を有する19−ノル−ビタミンdアナログ |
WO2008035206A2 (en) * | 2006-04-06 | 2008-03-27 | Wisconsin Alumni Research Foundation | 2-methylene-1 alpha-hydroxy-18,19,21-trinorvitamin d3 analogs and uses thereof |
MX2008012913A (es) * | 2006-04-06 | 2009-03-06 | Wisconsin Alumni Res Found | 2-metilen-1a,25-dihidroxi-18,19,21-trinorvitamina d3 y sus usos. |
WO2008035207A2 (en) * | 2006-04-06 | 2008-03-27 | Wisconsin Alumni Research Foundation | 2-methylene-1alpha-hydroxy-19,21-dinorvitamin d3 analogs and uses thereof |
US8193169B2 (en) * | 2006-04-06 | 2012-06-05 | Wisconsin Alumni Research Foundation | (20R)-2α-methyl-19,26,2-trinor-vitamin D analogs |
JP2010505739A (ja) * | 2006-04-06 | 2010-02-25 | ウイスコンシン アラムニ リサーチ ファンデーション | 2−メチレン−1α,25−ジヒドロキシ−19,21−ジノルビタミンD3類縁体およびその使用 |
ATE496885T1 (de) * | 2006-04-10 | 2011-02-15 | Wisconsin Alumni Res Found | 1-alpha-hydroxy-2-(3'-hydroxypropyliden)-19-nor vitamin-d-verbindungen mit einer 1,1- dimethylpropyl-seitenkette |
EP2069297A1 (en) * | 2006-09-28 | 2009-06-17 | Wisconsin Alumni Research Foundation | 2-methylene-(20r,25s)-19,27-dinor-(22e)-vitamin d analogs |
ATE552238T1 (de) * | 2006-09-28 | 2012-04-15 | Wisconsin Alumni Res Found | 2-methylen-(20s,25s)-19,27-dinor-(22e)-vitamin- - analoga |
MX2010007264A (es) * | 2007-12-28 | 2011-03-15 | Wisconsin Alumni Res Foundation Star | Análogos de vitamina d 2-metilen-(20s, 25r)-19, 26-dinor. |
JP2011507965A (ja) * | 2007-12-28 | 2011-03-10 | ウィスコンシン アラムナイ リサーチ ファンデーション | 2−メチレン−(20s,25s)−19,26−ジノル−ビタミンd類縁体 |
JP2011508743A (ja) * | 2007-12-28 | 2011-03-17 | ウィスコンシン アラムナイ リサーチ ファンデーション | (20s)−23,23−ジフルオロ−2−メチレン−19−ノル−ビスホモプレグナカルシフェロール−ビタミンd類縁体 |
MX2010007265A (es) * | 2007-12-28 | 2010-11-30 | Wisconsin Alumni Res Found | Análogos de vitamina d-(20r)-23, 23-difluoro-2-metilen-19-nor-bish omopregnacalciferol. |
CA2710977C (en) * | 2007-12-28 | 2015-02-17 | Wisconsin Alumni Research Foundation | 2-methylene-20-methyl-19,24,25,26,27-pentanor-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 |
US8222236B2 (en) * | 2008-07-10 | 2012-07-17 | Wisconsin Alumni Research Foundation | 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs |
US7879829B2 (en) * | 2008-07-10 | 2011-02-01 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D analogs with 1,2-dihydrofuran ring |
US7713953B2 (en) * | 2008-07-10 | 2010-05-11 | Wisconsin Alumni Research Foundation | 2-methylene-(22E)-25-(1-methylene-hexyl)-26,27-cyclo-22-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 |
US8399439B2 (en) * | 2008-07-10 | 2013-03-19 | Wisconsin Alumni Research Foundation | 2-methylene-19,26-dinor-(20S,22E,25R)-vitamin D analogs |
US8193170B2 (en) * | 2008-07-10 | 2012-06-05 | Wisconsin Alumni Research Foundation | 2-methylene-19,26-dinor-(20R,22E,25R)-vitamin D analogs |
US7648974B1 (en) * | 2008-07-10 | 2010-01-19 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D analogs with 3,2-dihydrofuran ring |
CA2981549A1 (en) | 2009-01-27 | 2010-08-05 | Berg Llc | Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy |
SG10201404883YA (en) | 2009-08-14 | 2014-10-30 | Berg Llc | Vitamin d3 and analogs thereof for treating alopecia |
US8445468B2 (en) | 2009-10-02 | 2013-05-21 | Wisconsin Alumni Research Foundation | (20S,22E)-2-methylene-19-nor-22-ene-1α,25-dihydroxyvitamin D3 |
US8217023B2 (en) | 2009-10-02 | 2012-07-10 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D analogs with 1,2- or 3,2-cyclopentene ring |
CA2776464C (en) | 2009-10-02 | 2017-10-24 | Wisconsin Alumni Research Foundation | 1-desoxy-2-methylene-19-nor-vitamin d analogs and their uses |
WO2011050163A1 (en) | 2009-10-21 | 2011-04-28 | Wisconsin Alumni Research Foundation | Method of preventing type 1 diabetes |
CA2794006C (en) * | 2010-03-23 | 2017-11-28 | Wisconsin Alumni Research Foundation | (20s)-2-methylene-19-nor-22-dimethyl-1.alpha.,25-dihydroxyvitamin d3 and (20r)-2-methylene-19-nor-22-dimethyl-1.alpha.,25-hydroxyvitamin 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 |
US8664206B2 (en) | 2010-03-23 | 2014-03-04 | Wisconsin Alumni Research Foundation | Diastereomers of 2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D3 |
US8754067B2 (en) | 2010-11-12 | 2014-06-17 | Wisconsin Alumni Research Foundation | 22-haloacetoxy-homopregnacalciferol analogs and their uses |
US9290447B2 (en) | 2011-05-03 | 2016-03-22 | Wisconsin Alumni Research Foundation | (20R) and (20S)-24-(p-toluenesulfonyloxy)-25,26,27-trinorvitamin D3 analogs and their uses |
WO2012158794A1 (en) | 2011-05-17 | 2012-11-22 | Wisconsin Alumni Research Foundation | N-cyclopropyl-(20r)-2-methylene-19,26,27-trinor-25-aza-vitamin d analogs and their uses |
AU2012262174B2 (en) | 2011-06-03 | 2016-12-01 | Wisconsin Alumni Research Foundation | (22E)-2-methylene-26,27-cyclo-22-dehydro-1alpha-hydroxy-19-norvitamin D3 derivatives |
US8993547B2 (en) | 2011-06-14 | 2015-03-31 | Wisconsin Alumni Research Foundation | 3-desoxy-2-methylene-19-nor-vitamin D analogs and their uses |
US10479764B2 (en) | 2011-06-28 | 2019-11-19 | Wisconsin Alumni Research Foundation | 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs |
US20130178449A1 (en) | 2011-07-18 | 2013-07-11 | Wisconsin Alumni Research Foundation | 2-Methylene-20(21)-Dehydro-19,24,25,26,27-Pentanor-Vitamin D Analogs |
CA2851275C (en) | 2011-10-21 | 2020-07-14 | Wisconsin Alumni Research Foundation | 2-methylene-vitamin d analogs and their uses |
JP6114292B2 (ja) | 2011-10-21 | 2017-04-12 | ウイスコンシン アラムニ リサーチ ファンデーション | 2−メチレン−ビタミンd類似体およびそれらの使用 |
US8729054B2 (en) | 2011-10-21 | 2014-05-20 | Wisconsin Alumni Research Foundation | 3-desoxy-2-methylene-vitamin D analogs and their uses |
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 |
US8785422B2 (en) | 2012-06-06 | 2014-07-22 | Wisconsin Alumni Research Foundation | A-ring modified 19-nor-vitamin D analogs and their uses |
US9416102B2 (en) | 2013-01-23 | 2016-08-16 | Wisconsin Alumni Research Foundation | (22E)-2-methylene-22-dehydro-1α,24,25-trihydroxy-19-nor-vitamin D3 analogs |
AU2014274099A1 (en) | 2013-05-29 | 2015-12-24 | Berg Llc | Preventing or mitigating chemotherapy induced alopecia using vitamin D |
US20170296558A1 (en) | 2016-04-18 | 2017-10-19 | Wisconsin Alumni Research Foundation | Use of 2amd and 2md to treat fibrosis |
US10548908B2 (en) | 2016-09-15 | 2020-02-04 | Nostopharma, LLC | Compositions and methods for preventing and treating heterotopic ossification and pathologic calcification |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3276167D1 (en) * | 1981-11-02 | 1987-06-04 | Res Inst Medicine Chem | Intermediates in the synthesis of vitamin d derivatives |
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 |
CA1333616C (en) * | 1989-03-09 | 1994-12-20 | Hector F. Deluca | 19-nor-vitamin d 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 |
AU649057B2 (en) * | 1990-08-24 | 1994-05-12 | Wisconsin Alumni Research Foundation | Methods and compositions containing vitamin D compounds for improvement of skin conditions |
DK0474517T3 (da) * | 1990-09-07 | 1999-08-02 | Wisconsin Alumni Res Found | Hidtil ukendt anvendelse af 1alfa-hydroxyleret-19-nor-vitamin D- |
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 |
ZA924811B (en) | 1991-06-28 | 1993-12-29 | Endorecherche Inc | Controlled release systems and low dose androgens |
JP3213092B2 (ja) * | 1991-11-01 | 2001-09-25 | 中外製薬株式会社 | 2β位に置換基を有するビタミンD誘導体 |
DE69400495T2 (de) * | 1993-04-05 | 1997-04-30 | Wisconsin Alumni Res Found | 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle |
WO1996001811A1 (en) * | 1994-07-11 | 1996-01-25 | The Johns-Hopkins University | 2-substituted 1,25-dihydroxyvitamin d3 derivatives |
CA2206876A1 (en) | 1994-11-21 | 1996-05-30 | Wisconsin Alumni Research Foundation | 18,19-dinor-vitamin d compounds |
US5877168A (en) | 1995-02-10 | 1999-03-02 | Chugai Seiyaku Kabushiki Kaisha | Vitamin D derivative with substituent at the 2β-position |
CA2175881A1 (en) | 1995-05-09 | 1996-11-10 | Andrzej Kutner | Vitamin d compounds and methods of preparing these compounds |
ATE289199T1 (de) | 1995-06-06 | 2005-03-15 | Merck & Co Inc | Formulierungen mit dem wasserfreien mononatriumsalz von alendronat und deren verwendung zur behandlung von knochenkrankheiten |
US5843928A (en) * | 1997-03-17 | 1998-12-01 | Wisconsin Alumni Research Foundation | 2-alkylidene-19-nor-vitamin D compounds |
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NO994489L (no) | 1999-09-16 |
CA2272745C (en) | 2005-12-06 |
US6277837B1 (en) | 2001-08-21 |
DE69819312T2 (de) | 2004-07-29 |
NZ337262A (en) | 2000-09-29 |
EP0971888A1 (en) | 2000-01-19 |
JP2000513010A (ja) | 2000-10-03 |
NO994489D0 (no) | 1999-09-16 |
AU6280098A (en) | 1998-10-12 |
US6127559A (en) | 2000-10-03 |
ATE253046T1 (de) | 2003-11-15 |
EP0971888B1 (en) | 2003-10-29 |
JP4035143B2 (ja) | 2008-01-16 |
BR9808010A (pt) | 2000-03-08 |
DK0971888T3 (da) | 2004-03-08 |
JP2006096759A (ja) | 2006-04-13 |
CA2272745A1 (en) | 1998-09-24 |
KR20000076303A (ko) | 2000-12-26 |
AU714390B2 (en) | 1999-12-23 |
DE69819312D1 (de) | 2003-12-04 |
WO1998041500A1 (en) | 1998-09-24 |
BR9808010B1 (pt) | 2013-11-26 |
JP3786712B2 (ja) | 2006-06-14 |
KR100345820B1 (ko) | 2002-07-24 |
US5945410A (en) | 1999-08-31 |
PT971888E (pt) | 2004-03-31 |
ES2206893T3 (es) | 2004-05-16 |
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