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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Publication of CA2824870A1 publication Critical patent/CA2824870A1/en
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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)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (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

ID=46331719

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 (https=)
EP (1) EP2721004B1 (https=)
JP (1) JP6035331B2 (https=)
AU (1) AU2012271759B2 (https=)
CA (1) CA2824870C (https=)
WO (1) WO2012174095A1 (https=)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105143463A (zh) 2013-02-25 2015-12-09 诺华股份有限公司 新的雄激素受体突变
CA2991260A1 (en) 2015-08-05 2017-02-09 Wisconsin Alumni Research Foundation Synthesis and biological activity of 2-methylene analogs of calcitriol and related compounds

Family Cites Families (39)

* Cited by examiner, † Cited by third party
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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
EP0619306B1 (en) 1993-04-05 1996-09-11 Wisconsin Alumni Research Foundation 19-Nor-vitamin D3 compounds with substituent at 2-position
US6392071B1 (en) * 1997-03-17 2002-05-21 Wisconsin Alumni: Research Foundation 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds
US5843928A (en) * 1997-03-17 1998-12-01 Wisconsin Alumni Research Foundation 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
NZ524657A (en) * 2000-09-08 2004-12-24 Wisconsin Alumni Res Found 1 alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol and its therapeutic applications
NZ533424A (en) * 2001-12-13 2006-08-31 Wisconsin Alumni Res Found Vitamin D derivative, methods of purifying and uses in treating psoriasis, cancer, autoimmune diseases, inflammatory diseases, skin conidtions and renal ostepdystrophy
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
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
CA2531294A1 (en) * 2003-07-03 2005-02-10 Wisconsin Alumni Research Foundation 2-methylene-19-nor-20(s)-25-methyl-1.alpha.-hydroxycalciferol and its uses
US20050009792A1 (en) * 2003-07-08 2005-01-13 Deluca Hector F. (20S)-1alpha-hydroxy-2-methylene-19-nor-vitamin D3 and its uses
AU2004266706B2 (en) * 2003-08-20 2009-07-30 Wisconsin Alumni Research Foundation 2-methylene-19-nor-vitamin D2 compounds
EP1827452B1 (en) * 2004-11-22 2011-03-02 Wisconsin Alumni Research Foundation 2-methylene-19,21-dinor-1alpha-hydroxy-bishomopregnacalciferol
DE602005021245D1 (de) * 2004-11-22 2010-06-24 Wisconsin Alumni Res Found 2-methylen-19,26,27-trinor-(20s)-1-alpha-hydroxyvitamin d3 and dessen verwendungen
EP1828115A4 (en) * 2004-11-22 2010-05-05 Wisconsin Alumni Res Found 2-METHYLENE-19-NOR (20S) -1ALPHA-HYDROXYTRISHOMOPREGNACALCIFEROL
WO2006086613A2 (en) * 2005-02-11 2006-08-17 Wisconsin Alumni Research Foundation 2-METHYLENE-19-NOR- (20S-24S) - 1α, 25-D IHYDROXYVITAMIN-D2
DK1848442T3 (da) * 2005-02-11 2012-05-29 Wisconsin Alumni Res Found 2-methylene-19-nor-(20s-24epi)-1alfa,25-dihydroxyvitamine-d2
MX2007013558A (es) * 2005-05-03 2008-01-24 Wisconsin Alumni Res Found Compuestos de 19,26,27-trinor-1a,25-dihidroxivitamina d3.
US7803789B2 (en) * 2006-02-02 2010-09-28 Wisconsin Alumni Research Foundation Vitamin D analog—RAK, methods 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.
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
WO2008035207A2 (en) * 2006-04-06 2008-03-27 Wisconsin Alumni Research Foundation 2-methylene-1alpha-hydroxy-19,21-dinorvitamin d3 analogs and uses thereof
RU2440980C2 (ru) * 2006-06-02 2012-01-27 Ниппон Синяку Ко., Лтд. 9,10-секопрегнановое производное и фармацевтические средства
EP2069296B1 (en) * 2006-09-28 2012-04-04 Wisconsin Alumni Research Foundation 2-methylene-(20s,25s)-19,27-dinor-(22e)-vitamin d analogs
AU2007300214A1 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20R,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
EP2240463A2 (en) * 2007-12-28 2010-10-20 Wisconsin Alumni Research Foundation 2-methylene-(20s,25r)-19,26-dinor-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
WO2009086436A1 (en) * 2007-12-28 2009-07-09 Wisconsin Alumni Research Foundation (20s)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-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
US8399439B2 (en) * 2008-07-10 2013-03-19 Wisconsin Alumni Research Foundation 2-methylene-19,26-dinor-(20S,22E,25R)-vitamin D analogs
WO2010120698A1 (en) * 2009-04-17 2010-10-21 Vidasym, Llc Vitamin d receptor agonists and uses thereof
US8642579B2 (en) * 2009-10-02 2014-02-04 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin D analogs and their uses
EP2525799B1 (en) * 2009-10-02 2014-09-03 Wisconsin Alumni Research Foundation (20s,22e)-2-methylene-19-nor-22-ene-1alpha,25-dihydroxyvitamin d3 analogs
MX2012005936A (es) * 2009-11-30 2012-09-07 Wisconsin Alumni Res Found 2-metilen-19,26-nor-(20s)-1a-hidroxivitamina d3.

Also Published As

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

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