CA2824870C - 3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses - Google Patents

3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses Download PDF

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Publication number
CA2824870C
CA2824870C CA2824870A CA2824870A CA2824870C CA 2824870 C CA2824870 C CA 2824870C CA 2824870 A CA2824870 A CA 2824870A CA 2824870 A CA2824870 A CA 2824870A CA 2824870 C CA2824870 C CA 2824870C
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Canada
Prior art keywords
group
compound
hydroxy
hydrogen
vitamin
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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 - Fee Related
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CA2824870A
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English (en)
French (fr)
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CA2824870A1 (en
Inventor
Hector F. Deluca
Lori A. Plum
Rafal R. Sicinski
Izabela Sibilska
Margaret Clagett-Dame
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Wisconsin Alumni Research Foundation
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Wisconsin Alumni Research Foundation
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Expired - Fee Related legal-status Critical Current
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2824870A 2011-06-14 2012-06-13 3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses Expired - Fee Related CA2824870C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201161496777P 2011-06-14 2011-06-14
US61/496,777 2011-06-14
US201161550099P 2011-10-21 2011-10-21
US61/550,099 2011-10-21
PCT/US2012/042225 WO2012174095A1 (en) 2011-06-14 2012-06-13 3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses

Publications (2)

Publication Number Publication Date
CA2824870A1 CA2824870A1 (en) 2012-12-20
CA2824870C true CA2824870C (en) 2018-08-14

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA2824870A Expired - Fee Related CA2824870C (en) 2011-06-14 2012-06-13 3-desoxy-2-methylene-19-nor-vitamin d analogs and their uses

Country Status (6)

Country Link
US (1) US8993547B2 (enExample)
EP (1) EP2721004B1 (enExample)
JP (1) JP6035331B2 (enExample)
AU (1) AU2012271759B2 (enExample)
CA (1) CA2824870C (enExample)
WO (1) WO2012174095A1 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2959013A2 (en) 2013-02-25 2015-12-30 Novartis AG Novel androgen receptor mutation
JP6971966B2 (ja) 2015-08-05 2021-11-24 ウイスコンシン アラムニ リサーチ ファンデーション カルシトリオールの２−メチレン類似体および関連化合物の合成および生物活性

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4666634A (en) 1984-12-05 1987-05-19 Chugai Seiyaku Kabushiki Kaisha vitamin D3 derivatives having a substituent at 2-position
US5086191A (en) 1991-05-28 1992-02-04 Wisconsin Alumni Research Foundation Intermediates for the synthesis of 19-nor vitamin D compounds
JP2898882B2 (ja) 1993-04-05 1999-06-02 ウイスコンシン アラムナイ リサーチ フオンデーシヨン ２−位に置換基を有する１９−ノル−ビタミンｄ３ 化合物
US5843928A (en) * 1997-03-17 1998-12-01 Wisconsin Alumni Research Foundation 2-alkylidene-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
US5945410A (en) 1997-03-17 1999-08-31 Wisconsin Alumni Research Foundation 2-alkyl-19-nor-vitamin D compounds
US6382071B1 (en) 2000-08-07 2002-05-07 Gilbert A. Bertani Bola capturing apparatus
BR0113703A (pt) * 2000-09-08 2003-07-22 Wisconsin Alumni Researcg Foun Compostos e métodos de tratamento de psorìase, leucemia, câncer do cólon, do seio ou da próstata, osteodistrofia renal, de doenças auto-imune, inflamatória e de condição de pele
US6627622B2 (en) 2002-02-18 2003-09-30 Wisconsin Alumni Research Foundation (20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses
PT1453798E (pt) * 2001-12-13 2009-01-23 Wisconsin Alumni Res Found (20s)-1alfa-hidroxi-2-metileno-19-nor-bishomopregnacalciferol e suas utilizações
US6566352B1 (en) * 2002-02-18 2003-05-20 Wisconsin Alumni Research Foudation 1 α-hydroxy-2-methylene-19-nor-pregnacalciferol and its uses
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
ATE350043T1 (de) * 2003-07-03 2007-01-15 Wisconsin Alumni Res Found 2-methylen-19-nor-20(s)-25-methyl-1alpha- hydroxycalciferol und seine verwendungen
US20050009792A1 (en) * 2003-07-08 2005-01-13 Deluca Hector F. (20S)-1alpha-hydroxy-2-methylene-19-nor-vitamin D3 and its uses
ATE537834T1 (de) * 2003-08-20 2012-01-15 Wisconsin Alumni Res Found 2-methylen-19-nor-vitamin d2-verbindungen
ATE499942T1 (de) * 2004-11-22 2011-03-15 Wisconsin Alumni Res Found 2-methylen-19,21-dinor-1alpha-hydroxy- bishomopregnacalciferol
US7244719B2 (en) * 2004-11-22 2007-07-17 Wisconsin Alumni Research Foundation 2-methylene-19,26,27-trinor-(20S)-1α-hydroxyvitamin D3 and its uses
JP2008520709A (ja) * 2004-11-22 2008-06-19 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）−１α−ヒドロキシ−トリスホモプレグナカルシフェロール
EP1848442B1 (en) * 2005-02-11 2012-04-25 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24epi)-1alpha,25-dihydroxyvitamine-d2
CA2597624C (en) * 2005-02-11 2012-08-14 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24s)-1.alpha.,25-dihydroxyvitamin-d2
EP1877063A4 (en) * 2005-05-03 2009-11-04 Wisconsin Alumni Res Found 19,26,27-TRINOR-1ALPHA, 25-DIHYDROXYVITAMINE-D3 COMPOUNDS
US7803789B2 (en) * 2006-02-02 2010-09-28 Wisconsin Alumni Research Foundation Vitamin D analog—RAK, methods and uses 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
MX2008012673A (es) * 2006-04-06 2008-10-15 Wisconsin Alumni Res Found Analogos de 2-metilen-1a-hidroxi-19, 21-dinorvitamina d3 y sus usos.
AU2007234717B2 (en) * 2006-04-06 2012-04-19 Wisconsin Alumni Research Foundation 2-methylene-1alpha,25-dihydroxy-19,21-dinorvitamin D3 analogs and uses thereof
KR20160112018A (ko) * 2006-06-02 2016-09-27 니뽄 신야쿠 가부시키가이샤 9,10-세코프레그난 유도체 및 의약
EP2069297A1 (en) * 2006-09-28 2009-06-17 Wisconsin Alumni Research Foundation 2-methylene-(20r,25s)-19,27-dinor-(22e)-vitamin d analogs
CA2662864A1 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20s,25s)-19,27-dinor-(22e)-vitamin d analogs
US20080171728A1 (en) * 2007-01-12 2008-07-17 Quatrx Pharmaceuticals Co. Efficient Process for Preparing Steroids and Vitamin D Derivatives With the Unnatural Configuration at C20 (20 Alpha-Methyl) from Pregnenolone
US8377913B2 (en) * 2007-11-20 2013-02-19 Abbvie Inc. Vitamin D receptor activators and methods of making
AU2008345082B2 (en) * 2007-12-28 2014-03-06 Wisconsin Alumni Research Foundation (20S)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-vitamin D analogs
WO2009086439A2 (en) * 2007-12-28 2009-07-09 Wisconsin Alumni Research Foundation 2-methylene-(20s,25s)-19,26-dinor-vitamin d analogs
US8609643B2 (en) * 2007-12-28 2013-12-17 Wisconsin Alumni Research Foundation 2-methylene-(20S,25R)-19,26-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
EP2419403B1 (en) * 2009-04-17 2016-09-07 Vidasym, Inc. Vitamin d receptor agonists and uses thereof
WO2011041590A2 (en) * 2009-10-02 2011-04-07 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin d analogs and their uses
MX2012003883A (es) * 2009-10-02 2012-06-27 Wisconsin Alumni Res Found Analogos de (20s,22e)-2-metileno-19-nor-22-ene-1a,25-dihidroxovita mina d3.
AU2010324596A1 (en) * 2009-11-30 2012-06-14 Wisconsin Alumni Research Foundation 2-methylene-19,26-nor-(20S)-1alpha-hydroxyvitamin D3

Also Published As

Publication number Publication date
EP2721004A1 (en) 2014-04-23
US20120322775A1 (en) 2012-12-20
CA2824870A1 (en) 2012-12-20
AU2012271759A1 (en) 2013-08-01
US8993547B2 (en) 2015-03-31
JP2014523419A (ja) 2014-09-11
AU2012271759B2 (en) 2017-02-02
EP2721004B1 (en) 2017-07-26
JP6035331B2 (ja) 2016-11-30
WO2012174095A1 (en) 2012-12-20

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Effective date: 20170613

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Effective date: 20210614