CA2562535C - 2-alkylidene-18,19-dinor-vitamin d compounds - Google Patents

2-alkylidene-18,19-dinor-vitamin d compounds Download PDF

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Publication number
CA2562535C
CA2562535C CA2562535A CA2562535A CA2562535C CA 2562535 C CA2562535 C CA 2562535C CA 2562535 A CA2562535 A CA 2562535A CA 2562535 A CA2562535 A CA 2562535A CA 2562535 C CA2562535 C CA 2562535C
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CA
Canada
Prior art keywords
disease
compound
dinor
treatment
methylene
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.)
Expired - Fee Related
Application number
CA2562535A
Other languages
English (en)
French (fr)
Other versions
CA2562535A1 (en
Inventor
Hector F. Deluca
Rafal Barycki
Pawel K. Grzywacz
Lori A. Plum
Rafal R. Sicinski
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Wisconsin Alumni Research Foundation
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Wisconsin Alumni Research Foundation
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Filing date
Publication date
Application filed by Wisconsin Alumni Research Foundation filed Critical Wisconsin Alumni Research Foundation
Publication of CA2562535A1 publication Critical patent/CA2562535A1/en
Application granted granted Critical
Publication of CA2562535C publication Critical patent/CA2562535C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/12Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Hematology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Dermatology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Emergency Medicine (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Oncology (AREA)
  • Biomedical Technology (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2562535A 2004-04-09 2005-02-04 2-alkylidene-18,19-dinor-vitamin d compounds Expired - Fee Related CA2562535C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/821,828 US7713951B2 (en) 2004-04-09 2004-04-09 2-alkylidene-18,19-dinor-vitamin D compounds
US10/821,828 2004-04-09
PCT/US2005/003378 WO2005102995A1 (en) 2004-04-09 2005-02-04 2-alkylidene-18,19-dinor-vitamin d compounds

Publications (2)

Publication Number Publication Date
CA2562535A1 CA2562535A1 (en) 2005-11-03
CA2562535C true CA2562535C (en) 2012-07-10

Family

ID=34960524

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2562535A Expired - Fee Related CA2562535C (en) 2004-04-09 2005-02-04 2-alkylidene-18,19-dinor-vitamin d compounds

Country Status (9)

Country Link
US (2) US7713951B2 (enExample)
EP (1) EP1735277B1 (enExample)
JP (1) JP4988551B2 (enExample)
AT (1) ATE534623T1 (enExample)
AU (1) AU2005235957B2 (enExample)
CA (1) CA2562535C (enExample)
MX (1) MXPA06011499A (enExample)
NZ (1) NZ550234A (enExample)
WO (1) WO2005102995A1 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7834050B2 (en) 2006-03-29 2010-11-16 Duke University Small molecule insulin mimetics absent quinones
JP2009532457A (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−メチレン−1α−ヒドロキシ−18,19,21−トリノルビタミンD3類縁体およびその使用
US7704981B2 (en) * 2006-04-06 2010-04-27 Wisconsin Alumni Research Foundation 2-methylene-1alpha,25-dihydroxy-18,19,21-trinorvitamin D3 and uses thereof
US20110274743A1 (en) * 2009-01-16 2011-11-10 Pharmaceutical Compounding Nz Limited Medicament for the Treatment of Pain and Inflammation
CA2777938C (en) * 2009-10-21 2017-11-14 Wisconsin Alumni Research Foundation Method of preventing type 1 diabetes
US8664206B2 (en) 2010-03-23 2014-03-04 Wisconsin Alumni Research Foundation Diastereomers of 2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D3
JP5931845B2 (ja) * 2010-03-23 2016-06-08 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−22−メチル−1α,25−ジヒドロキシビタミンD3のジアステレオマー
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
JP5930467B2 (ja) * 2012-12-14 2016-06-08 花王株式会社 ニトリル化合物

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL67153A (en) 1981-11-02 1986-12-31 Res Inst Medicine Chem Intermediates in the production of vitamin d analogues and method for their production
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
EP0474517B1 (en) 1990-09-07 1998-11-18 Wisconsin Alumni Research Foundation Novel use of 1alpha-hydroxylated-19-nor-vitamin D compounds to treat psoriasis
US5086191A (en) 1991-05-28 1992-02-04 Wisconsin Alumni Research Foundation Intermediates for the synthesis of 19-nor vitamin D compounds
AU650751B2 (en) 1991-05-28 1994-06-30 Wisconsin Alumni Research Foundation Novel synthesis of 19-nor vitamin D compounds
DE69400495T2 (de) 1993-04-05 1997-04-30 Wisconsin Alumni Res Found 19-Nor-vitamin-D3-Verbindung mit einem Substituent an die 2. Stelle
JP4235256B2 (ja) * 1993-07-09 2009-03-11 カー・イュー・ルーベン・リサーチ・アンド・ディベロップメント 新規ビタミンd構造類似体
WO1996001811A1 (en) 1994-07-11 1996-01-25 The Johns-Hopkins University 2-substituted 1,25-dihydroxyvitamin d3 derivatives
BR9509739A (pt) 1994-11-21 1997-10-21 Wisconsin Alumni Res Found Compostos 18,19-dinor-vitamina d
US5661140A (en) * 1994-11-21 1997-08-26 Wisconsin Alumni Research Foundation 18-nor-vitamin D compounds
US5877168A (en) 1995-02-10 1999-03-02 Chugai Seiyaku Kabushiki Kaisha Vitamin D derivative with substituent at the 2β-position
IL118156A (en) 1995-05-09 2001-08-26 Duphar Int Res Vitamin d compounds, their preparation and pharmaceutical compositions containing them
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
US6114317A (en) * 1998-05-21 2000-09-05 Wisconsin Alumni Research Foundation Method of locking 1α-OH of vitamin D compounds in axial orientation
US5972917A (en) * 1998-05-29 1999-10-26 Bone Care Int Inc 1 α-hydroxy-25-ene-vitamin D, analogs and uses thereof
TW396427B (en) * 1998-12-16 2000-07-01 United Microelectronics Corp Method for fabricating double gates in semiconductor
WO2001092221A1 (en) * 2000-05-31 2001-12-06 Wisconsin Alumni Research Foundation 2-ethyl and 2-ethylidene-19-nor-vitamin d compounds
CA2416194C (en) * 2000-07-14 2009-10-06 Wisconsin Alumni Research Foundation Use of 2-methylene-19-nor-20(s)-1.alpha.,25-dihydroxyvitamin d3 to increase bone strength
ATE273709T1 (de) * 2000-09-08 2004-09-15 Wisconsin Alumni Res Found 1alpha-hydroxy-2-methylene-19-nor- homopregnacalciferol und seine therapeutische verwendungen
BR0307896A (pt) * 2002-03-29 2004-12-07 Wisconsin Alumni Res Found Método de produção de 1(alfa)-hidroxi-2-metileno-19-nor-homopregnacalcif erol
EP1559708A4 (en) * 2002-10-10 2006-07-19 Wisconsin Alumni Res Found 2,2-DISUBSTITUTED 1A, 25-DIHYDROXY-19-NORVITAMINE D DERIVATIVE
JP5005340B2 (ja) * 2003-04-10 2012-08-22 ウィスコンシン・アルムニ・リサーチ・ファウンデーション 2−プロピリデン−19−ノル−ビタミンd化合物
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
AU2004266706B2 (en) * 2003-08-20 2009-07-30 Wisconsin Alumni Research Foundation 2-methylene-19-nor-vitamin D2 compounds
US7214670B2 (en) * 2003-09-24 2007-05-08 Wisconsin Alumni Research Foundation Use of 2-methylene-19-nor-20(S)-1α,25-dihydroxyvitamin D3 to increase the life expectancy of human beings
MXPA06005887A (es) * 2003-11-25 2006-06-27 Wisconsin Alumni Res Found Analogos de vitamina d para la prevencion y el tratamiento de la obesidad.
US7053075B2 (en) * 2003-11-25 2006-05-30 Deluca Hector F Methods for reducing body fat using vitamin D compounds
EP1817278B1 (en) * 2004-11-22 2010-06-30 Wisconsin Alumni Research Foundation 2-methylene-18,19-dinor-1alfa-hydroxy-homopregnacalciferol and its uses
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
DK1848442T3 (da) * 2005-02-11 2012-05-29 Wisconsin Alumni Res Found 2-methylene-19-nor-(20s-24epi)-1alfa,25-dihydroxyvitamine-d2
US7241909B2 (en) * 2005-05-03 2007-07-10 Wisconsin Alumni Research Foundation 19,26,27-trinor-1α,25-dihydroxyvitamin D3 compounds

Also Published As

Publication number Publication date
CA2562535A1 (en) 2005-11-03
EP1735277A1 (en) 2006-12-27
AU2005235957B2 (en) 2011-08-04
WO2005102995A1 (en) 2005-11-03
ATE534623T1 (de) 2011-12-15
US7713951B2 (en) 2010-05-11
US20100179344A1 (en) 2010-07-15
EP1735277B1 (en) 2011-11-23
MXPA06011499A (es) 2007-01-16
JP2007532540A (ja) 2007-11-15
US20050227950A1 (en) 2005-10-13
AU2005235957A1 (en) 2005-11-03
JP4988551B2 (ja) 2012-08-01
NZ550234A (en) 2010-07-30

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Effective date: 20200204