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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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)
  • 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
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
US9688596B2 (en) 2015-08-05 2017-06-27 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
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
US5945410A (en) 1997-03-17 1999-08-31 Wisconsin Alumni Research Foundation 2-alkyl-19-nor-vitamin D compounds
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
US6382071B1 (en) 2000-08-07 2002-05-07 Gilbert A. Bertani Bola capturing apparatus
AU7544501A (en) 2000-09-08 2002-03-22 Wisconsin Alumni Res Found 1alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol and its therapeutic applications
US6627622B2 (en) 2002-02-18 2003-09-30 Wisconsin Alumni Research Foundation (20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses
WO2003051828A2 (en) * 2001-12-13 2003-06-26 Wisconsin Alumni Research Foundation (20s)-1alpha-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
ATE346839T1 (de) * 2002-03-29 2006-12-15 Wisconsin Alumni Res Found Ein verfahren zur herstellung von 1-alpha-hydroxy-2-methylen-19-nor-homopregnacal iferol
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
NZ545862A (en) * 2003-08-20 2010-01-29 Wisconsin Alumni Res Found 2-Methylene-19-nor-vitamin D2 compounds
EP1828115A4 (en) * 2004-11-22 2010-05-05 Wisconsin Alumni Res Found 2-METHYLENE-19-NOR (20S) -1ALPHA-HYDROXYTRISHOMOPREGNACALCIFEROL
AU2005309820B2 (en) * 2004-11-22 2011-06-23 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
US7511030B2 (en) * 2005-02-11 2009-03-31 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20S-24epi)-1α,25-dihydroxyvitamin D2
CA2597624C (en) * 2005-02-11 2012-08-14 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24s)-1.alpha.,25-dihydroxyvitamin-d2
AU2006242184A1 (en) * 2005-05-03 2006-11-09 Wisconsin Alumni Research Foundation 19,26,27-trinor-1alpha,25-dihydroxyvitamin D3 compounds
US7803789B2 (en) * 2006-02-02 2010-09-28 Wisconsin Alumni Research Foundation Vitamin D analog—RAK, methods and uses thereof
JP2009532460A (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 ２−置換−１α，２５−ジヒドロキシ−１９，２６，２７−トリノルビタミンＤ類縁体およびその使用
NZ570814A (en) * 2006-04-06 2011-11-25 Wisconsin Alumni Res Found 2-methylene-1alpha-hydroxy-19,21-dinorvitamin D3 analogs and uses thereof
ATE523487T1 (de) * 2006-04-06 2011-09-15 Wisconsin Alumni Res Found 2-methylen-1-alpha-dihydroxy-19,21-dinor-vitami - d3-analoga und ihre anwendung
JP5176956B2 (ja) * 2006-06-02 2013-04-03 日本新薬株式会社 ９，１０−セコプレグナン誘導体及び医薬
AU2007300214A1 (en) * 2006-09-28 2008-04-03 Wisconsin Alumni Research Foundation 2-methylene-(20R,25S)-19,27-dinor-(22E)-vitamin D analogs
JP2010504994A (ja) * 2006-09-28 2010-02-18 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−（２０ｓ，２５ｓ）−１９，２７−ジノル−（２２ｅ）−ビタミンｄ類縁体
WO2008089093A2 (en) * 2007-01-12 2008-07-24 Quatrx Pharmaceuticals Company Efficient processes 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
CA2710954C (en) * 2007-12-28 2015-07-21 Wisconsin Alumni Research Foundation (20s)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-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
EP2240440A2 (en) * 2007-12-28 2010-10-20 Wisconsin Alumni Research Foundation 2-methylene-(20s,25s)-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
NZ595727A (en) * 2009-04-17 2013-11-29 Vidasym Inc Vitamin d receptor agonists and uses thereof
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
AU2010300539B9 (en) * 2009-10-02 2018-07-19 Wisconsin Alumni Research Foundation 1-desoxy-2-methylene-19-nor-vitamin D analogs and their uses
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
JP6035331B2 (ja) 2016-11-30
AU2012271759A1 (en) 2013-08-01
EP2721004A1 (en) 2014-04-23
AU2012271759B2 (en) 2017-02-02
JP2014523419A (ja) 2014-09-11
EP2721004B1 (en) 2017-07-26
WO2012174095A1 (en) 2012-12-20
US20120322775A1 (en) 2012-12-20
US8993547B2 (en) 2015-03-31
CA2824870A1 (en) 2012-12-20

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